A Proper Fitting For A Sissy

A Proper Fitting for a Sissy

My name is Tiffany Johnson.
I’m 29 years old and I work at Chastity Services, along with my best friend, Ariel. Primarily what we do, is to fit males for chastity devices, sometimes willingly, other times…not so much. But either way, any male coming into my shop will leave with his little penis imprisoned and secured under lock and key.

I deal with a lot of sissies in my profession. I find that they tend to have a fascination with panties, or dressing up like women, or some other such perverted fetish. We get geeky guys coming in on their own and they’re curious about the concept of chastity and I’m only too happy to help them out. They’re often shy and easily intimidated so that’s just what I do. Its fun to watch them blush and squirm in my office, especially since I’ve always had a thing for dressing provocatively, wearing low cut tops that display my big breasts and snug skirts to show off plenty of leg.
I like to question them bluntly about their masturbating habits, how often they do it, as well as what they masturbate to. They always blush furiously when I question them but they’re too weak-willed to actually get up and leave.

The fact is, I can spot a sissy from a mile away and I love nothing more than to humiliate them in any way I can. I’ve been that way for as long as I can remember, all through out my junior and high schools, but truth be told, I started even before that, in grade school.

Of course, a proper fitting for a chastity device means having them drop their drawers so I can measure their pathetic little penises. They probably come in thinking I’ll be very clinical and dry like a professional nurse but in fact, I’m just the opposite. It’s inevitably a mortifying experience for the guy, and I take every opportunity to embarrass him, making disparaging comments about his size and telling him just what a pansy he is. I also make sure to tell all of them that I assume they’re virgins and that they’ve never been with a girl before.

With regards to the devices themselves, its surprising, but what a lot of women don’t realize is just how small of one you can stuff a guy’s penis into. I don’t want these sissies to have so much as a millimeter to be able to grow in, so I always make a point of fitting them in the smallest chastity device I can get them into. Fortunately, we have lots of the smaller, harder to find sizes than you can’t get online, so the sissy boy is usually both shocked and ashamed at what we can fit him for.

We also talk to a lot of our manufacturers, giving them constant feedback and as a consequence, almost all of them now offer pink versions of their devices. And we make a point of pushing that color as a choice for most of our males, browbeating the wimps until they finally cave in. Believe me–nothing looks more pathetic than a male wearing a pink chastity cage around his tiny package and shaved crotch. No woman will ever take him seriously after they see that.

One of my favorite tricks is to fit them for a device, lock them into it, and at the end of the sale, I appear to hand over the keys.
Little do they realize that the keys I gave them aren’t the real ones, since I always keep those in a safe, secret location, but they don’t find that out until they get home, and sometimes, not even for several days. After that, I screen my calls, just to ensure the little sissies will squirm with panic and fear. I want them to experience at least a full week of real chastity, outside of their control–not knowing if they’ll ever be able to touch their pathetic wee-wees again.

It never ceases to amaze me what you can make a locked, desperate sissy do, just to get access to the real keys. And I make sure that whatever I demand of them will be extremely humiliating for him to endure.

In high school, I was something of a bully to the weaker guys and I’ve only become more determined to put these wimps in their place in my professional life. At 5′ 10″, I am on the tall side, and in my 5″ heels, I tower over most guys, especially sissies. My haughty, imperious nature is more than enough to make them tremble but being tall also helps.

Growing up, I was an early bloomer and I was already sporting a generous C cup by my 14th birthday. By 18, I was outgrowing my DD bras from Victoria’s Secret. Nowadays, I have to order my bras online from specialty stores to get ones that will fit. A 34EE size cup just isn’t to be found at Nordstrom’s.

All too often, these pervs coming into our shop try to steal glances down my low cut tops when they think I’m not looking, but I always catch them and scold them mercilessly, making the little creep blush bright red with shame.

The other day, I had an interesting visit from a couple that I think is worth relating.

A husband and wife came into our office last week and right away, I could tell the guy was a sissy. He seemed really nervous, and had difficulty making eye contact with me. Instead, his gaze would dart anxiously around the room, as if he were trying to find some way of an escape.
By contrast, the woman was cool and collected, confident and self assured–everything her husband wasn’t. She looked to be in her mid-thirties, with jet black hair and a slim, yet curvy figure. She dressed smartly, with a close-fitted blouse and a skirt that showcased her long legs.

I have an eye for detail, and looking at her fidgeting husband, I felt certain that he was wearing diapers underneath his trousers. He seemed very self conscious, and he shifted in his seat, as if desperately trying to hide his childish underwear.
Definitely a sissy.

After sitting them down in my office, I offered her coffee (purposely ignoring him) and took a seat before them, crossing my legs in a deliberate manner to test her sissy husband’s reaction. Sure enough, although he tried to hide it, his eyes couldn’t avoid staring as my short skirt rode up my thighs.

“Tell me how I can be of assistance,” I said, smiling pleasantly as I looked the wife in the eyes.

“My name is Leanne and this is my husband, Conrad,” she said, referring to her spouse with a dismissive thrust of her extended thumb.
“He has a chronic masturbating habit and I want to put a stop to it.”

“That’s disgusting,” I said firmly as I looked him up and down with disdain.

His face went bright red and he looked away, tugging at his collar anxiously.

“How often do you play with yourself, Conrad?” I asked him point blank.

His mouth opened, but it seemed there was no dignified way to answer the question, especially with his domineering wife right next to him.

“Every chance he gets,” she immediately replied without hesitation, “I make him wear diapers because of his nightly bedwetting, and Cassie simply can’t resist the soft cotton Birdseye I pin him into.”

I shook my head and stared hard at her wilting husband.

“I thought as much…am I right that he’s wearing his diapers now?”

“Yes he is–he made a fuss about coming down here today so after a trip over my knee, he got to wear his nighttime diapers instead of his regular underwear.
“Cassie–why don’t you show Ms. Johnson here your pampers?”

Her hubby shot a panicked look back at her and he shook his head pleadingly, silently beseeching her for mercy.

“Cassie? Do you need another dose of the hairbrush? Because I’ll do it right here and now if you want to push me.”

The color drained out of her hubby’s face and with a sob of shame, he slowly stood up. Fumbling with his zipper and clasp, he clumsily managed to undo them and his trousers slid down his slim, hairless thighs, revealing his prissy, embarrassing diapers. Obviously designed to ensure maximum humiliation for the wearer, Leanne had chosen a pair of pink nursery print plastic panties with babyish white ruffles around the legs and waistband.

“Well–I see who wears the pants in this relationship,” I snickered, “Are you wet, sissy boy?”

Conrad shook his head miserably but didn’t look up at me.

“Answer her when you are spoken to,” his wife barked.

“N-no Ma’am,” he whispered meekly.

“Good, let’s try to keep it that way,” I told him, “You might as well take those pants all the way off, you won’t be needing them for a while anyway.”

Conrad bit his lip and slowly removed his pants, folding them neatly and putting them on my desk. He looked absolutely ridiculous in his polo and bulky pink diapers and I noticed he took his seat gingerly, presumably because his bottom was still smarting from his earlier spanking.

Returning my attention to Leanne, I gave her my usual sales pitch.
“Now–I have a number of chastity devices for you to choose from for your little sissy here,” I explained to her, “Depending on his size and your preferences, we have steel, plastic, and a number of colors, although I think pink would suit Cassie here the best.”

“I agree,” she replied, “More than anything, I want it to be super secure so that’s there’s no chance he can escape from it or have access to his little penis.”

“Oh–absolutely. Trust me when I tell you that after today, your sissy’s masturbating days are over for good,” I assured her.

Out of the corner of my eye, I could see her hubby cringe with fear.

“Now–we have two kinds of devices–those with spikes and those without.”

“Spikes?” she asked in confusion.

“Oh yes, some of our devices have spikes inside, to discourage any sort of arousal from the wearer. They’re very good at making him focus on other things–like his chores around the house, for instance,” I explained.
“They’re usually not a problem for everyday wear, until he starts getting turned on, that is. At that point, the head of his penis will begin pushing against the spikes, quickly discouraging any further thoughts of naughty behavior,” I said, eyeing her fidgeting sissy with a knowing grin.

“Oh–that would be perfect,” Leanne agreed, “That way, when my boyfriend is over, Cassie will be less interested in what’s happening to me and more focused on his mopping duties.”

“Oh–you have a boyfriend?” I asked intrigued.

“Absolutely. This sissy here is completely incapable of satisfying me so I did what any sane woman would do–I went out and got myself a real man to take care of my needs.”

I smiled broadly at her.

“Good for you! Although I’m hardly surprised. I’m finding that most women in your place are doing the exact same thing. Why be stuck with a bedwetting sissy in diapers who can’t perform–when you can have a real man in your bed every night who knows just how to satisfy you?”

“Exactly. I leave Cassie to enjoy the wet diapers and crib sheets while I get to enjoy a nice big cock every night, reaching places that he never could. I can’t tell you the kind of mind-blowing orgasms I enjoy nowadays. Its so night and day from when I used to let Cassie into my bed,” she explained with another thumb pointed at her blushing, diapered hubby.

Cassie was fidgeting uncomfortably with all this humiliating talk about his shortcomings and it was clear he wished he could be anywhere but in this room.

“Well, I think its time now that we introduced your sissy to a life without orgasms of any kind, don’t you? Should we take some measurements?” I offered.

“Absolutely. Cassie–Pull your diapers down. I know its not much, but it’s time to show Ms. Johnson just how pathetic you are.”

With a sob of shame, her husband reluctantly began lowering his shameful diapers down his thighs.
And even though I’ve seen a hundred little peckers like his, I swear–every time its still a bit shocking.
Cassie’s penis looked like a little nub, no more than an inch, protruding from a small set of balls the size of marbles.

I couldn’t help it.
I burst out laughing, covering my mouth as I looked from his ridiculous “manhood”, up to his beet red face and then back down at his crotch.

Oh-my-god,” I said astounded, “You weren’t kidding–that thing is absolutely pathetic. And you’ve definitely made the right decision in locking it up–such a tiny little thing like that has no business being free. It needs to be locked up tight, where he can’t get at it or play with it.”

“I’m glad you agree with me,” Leanne concurred, nodding her head.

“Oh yes, believe me–I’ll make sure this little bedwetter can never play with himself again,” I said, filled with determination.

“You hear that, Cassie?” Leanne said, “I hope your last orgasm in your sissy diapers was a good one because it’ll be your last.”

Cassie winced and bit his lip, squirming in place while I began taking measurements of his tiny nub. It still had a slight coating of baby powder and in fact, if I hadn’t known better, I could have easily believed I was measuring a three year-old, diaper-dependant toddler, instead of a grown man.

“Its good you came here,” I told his wife, “Getting devices that will fit for a penis of his size are really hard to find. Fortunately, we deal with a lot of sissies so I know I’ll have something that will work.”

“That’s a relief,” Leanne confessed.

Going over to the wall behind my desk, I opened several drawers until I found what I was looking for. It was a small pink device, much like a CB6000S, but smaller and with short spikes on the inside of the tube near its tip.
I held it up for her inspection.

Leanne took it in her hands and a big smile crossed her attractive face.

“Yes…yes, this is just what my little sissy needs,” she said nodding her head in agreement, “This should keep you focused on your work instead of rubbing your diapers all the time.”

After handing it back to me, I disassembled it, and then knelt before her nervous hubby to begin fitting him for his permanent chastity. Quickly, I removed all the spacers and taking the cuff ring, I slipped it behind his little sack.

“This is the part I like,” I said winking over at Leanne.

“Say hello to your new best friend, Cassie,” I smirked as I held the short pink tube positioned before his penis and spat on his pathetic nub. With a quick, non-sexual stroke, I covered his shaft with the saliva and pushed it forcefully into the pink tube, quickly mating the holes in the base with the pins on the cuff ring. Taking the small brass lock, I deftly slipped it through the central pin and snapped it shut with a crisp flourish.

“There you are–another helpless sissy boy made chaste,” I said brushing my hands in a gesture of finality.

“Perfect!” Leanne exclaimed, clapping her hands with glee, “That looks wonderful. And the pink is so appropriate for him.”

“I couldn’t agree more. And its good you keep him shaved down there–he doesn’t have any need of pubic hair anyway,” I told her.

“Yes, I had it laser removed years ago when I first started putting him in diapers. It makes it so much more hygienic.”

Cassie was staring down at his little caged package, still trying to come to terms with what a future without sexual gratification would be like.

“What’s it like knowing you can’t play with your pathetic pecker any more?” I asked the squirming sissy.

“I don’t like it,” he bleated weakly, his cheeks blazing with shame.
“The only one having orgasms in your house from now on will be your wife and her lover. Your little sissy stick will stay soft and caged, just as it should be.”

Reaching over, Leanne grasped the device and gave it a solid shake, causing Cassie to whimper with anguish. It was obvious the device was on for good, until such time as she decided to unlock it.

“How does it feel, baby?” she asked her cowering hubby.

He shifted his feet and grasped the device gingerly, twisting it a bit in a futile attempt to remove it.

“Can you feel the spikes?” Leanne asked.

With his lower lip trembling in a pout, he shook his head.

“N-not yet,” he quivered fearfully.

“I think you can put his diapers back on,” I told her, “If you like, I can give you a quick demonstration of the power of the spikes.”

While a look of abject fear crossed Cassie’s face, his wife smiled wickedly and nodded her head.

“Oh yes–please do.”

After his prissy pink diapers were back in place, I sat him down in the chair and spread his legs slightly, bending over him and smiling warmly into his face. With my left hand, I began casually but sensually stroking the silky skin on the tops of my exposed breasts, right where the plump, curvy mounds pushed against each other.

“Do you like big breasts, Cassie?” I whispered in his ear seductively as my other hand reached down and lightly rubbed the front of his diapers. It was soft and cushiony and I could understand why he would be tempted to rub them so much.
Cassie was obviously feeling overwhelmed and he shifted nervously in his seat. Nevertheless, his gaze unerringly fell upon my cleavage and his breathing became heavy and labored. I stroked the shiny plastic front of his diapers lightly–after all, it only takes a little effort to get the right effect.
Sure enough, in just a few moments, he began shifting uncomfortably and a groan of pain escaped his lips.

“Owww!!” he suddenly cried, hastily shoving his hand down the front his diaper to wrestle with his package.
I stood back and watched him, looking down at him with satisfaction as he struggled to extricate his captured wiener from the device. Of course it was quite hopeless and no matter how he pulled or tugged, his penis continued to push urgently against the sharp spikes, making him writhe with pain and discomfort.

Leanne and I laughed and she clapped her hands again, immensely pleased with the results.

“Sold!!” she exclaimed happily.

I nodded and smiled, handing over the keys to her as Cassie bunched his fists in mute frustration.

“Be very careful where you put these,” I warned her, “I would recommend taking them to your work, or some other inaccessible location. If you hide them in the house, eventually, he’ll turn it upside down in order to find them.”

“You know what?–I think I’ll give them to my boyfriend. He can decide when or if the little sissy ever gets any satisfaction.”

“Excellent choice,” I commended her.

“Tell me–what’s the best way to relieve the built up pressure in his balls?” she asked, “I assume he needs to be ‘milked’, or something like that.”

“Yes, there are a number of ways you can do it. Some people use a device called an Aneros tool to massage his prostate gland. It can be a tedious process but eventually, you can completely empty his balls of any fluid that has built up over the course of a month.
“Some women use a strap-on and they have a once per month session with their sissy to drain him that way. And that’s also a memorable way to re-assert your dominance over him.
“Then again, other women just let their boyfriends bend him over a couch and have their way with him–it’s totally up to you.”

Leanne nodded in understanding.

“Most sissies are very resistant to getting their asses fucked by another man, but after a while, when they realize its the only kind of sex they’re ever going to get, they begin looking forward to having a nice big cock filling them up inside.
“In any case, there’s usually no need to remove his chastity device, it will all come out anyway.”

“Well,” Leanne said as she stood up, “I can’t say how happy I am that I found you. Your business is an absolute godsend!”

I smiled proudly, extending my hand to shake hers.
“I’m only too happy to provide a valuable service, locking up the pathetic dicks of sissies like Cassie here.”

As she took out her credit card for payment, she nodded absently to her hubby.

“Cassie–thank Ms. Johnson here for giving you the chastity device you so obviously needed.”

By now, his little penis had subsided, and he was no longer feeling the sharp spikes within his device.

Clearing his throat, he blushed and shuffled his feet, staring at the floor.

“Th-thank you, Ms. Johnson,” he mumbled, his cheeks burning with humiliation.

“Thank you for what?” Leanne prompted him.

“Th-thank you for fitting me for the ch-chastity device I needed,” he stumbled submissively.

“You’re quite welcome, sissy boy,” I said as condescendingly as I could.

Leanne and I shared another laugh at his expense and after ringing her up, I said my goodbyes.

Just another day’s job, well done, here at Chastity Services.


Barbara’s Baby Girl–Three Years Later

Chapter One

The last flush of the toilet signaled to Barbara–my de facto mommy, that I was finished in the bathroom, having finally spent the warm, soapy two-quart enema she’d administered twenty minutes earlier.
This was all the more obvious, since the door was wide open as it was required to be on those rare occasions when I was allowed into the bathroom.
Stepping out sheepishly, I looked up into the lovely blue eyes of Barbara.
“All done, Sweety?” she asked pleasantly.
“Yes Mommy,” I replied.
Daily enemas were Barbara’s way of avoiding messy diapers with me and the truth was, I couldn’t remember the last time I’d had a normal bowel movement. I was afraid to imagine how weak my muscles might have become should I ever go a morning without an enema. After living three years in Barbara’s house, I was now hopelessly incontinent and diapers were an absolute necessity.
Having pulled off the pair that I had soaked last night to give me my enema, I was now naked except for my fuzzy Strawberry Shortcake diaper shirt and frilly pink anklets.
Barbara reached down and grasped my hand, leading me firmly back to my nursery.
“How’s mommy’s little girl today?” she asked brightly.
“Good, Mommy,” I replied, gripping her warm hand tightly.
I felt not only naked but somewhat vulnerable outside of my nursery and I was anxious to get back to where my toys and stuffed animals awaited me.
Padding down the hall, we entered the bright and warmly lit room that was home for me 95% of the time. The morning sunlight streamed into the room through soft, gauzy pink curtains, filling the nursery with the makings of a new, happy day.
My room was decorated much like any little toddler’s, with soft pastel colors and a wonderful Disney Princess theme throughout. A large pink and white baby’s crib dominated the room, now open and revealing the nursery print waterproof mattress cover that helped guard against leaks during the night. To the right was my changing table, a slightly raised surface also covered with a practical vinyl plastic for my frequent diaper changes. On the other side stood my pink dresser with my extensive doll collection arranged across the top. Inside the drawers were a vast collection of diaper shirts, onesies, frilly anklets, and bonnets.
On the opposite side was my playpen with its soft padded rails and plastic lined floor where I spent most of my afternoons when Barbara was busy. A large diaper pail sat nearby and even though the lid was tightly sealed, a distinctive aroma of stale pee nevertheless pervaded into the room, serving as a constant reminder of my childish incontinence. Nobody visiting could fail to notice that this was the room of a bedwetter.
Stepping over to the changing table, Barbara helped me to take my place upon its shiny plastic surface, gathering a fresh set of diapers for my morning use.
“Looks like your diaper rash is much better this morning, Chrissey,” Barbara observed happily.
“Yes, Mommy,” I replied, relieved that the generous slathering of ointment she had applied to my bottom the last few days had done it’s trick.
Lifting my legs by my ankles, she slid a thick trio of bunny soft cloth diapers under my upturned rump.
“Say hello to your diapers, Babygirl,” she said with her beautiful smile.
I giggled merrily as she powdered me generously, filling the air around me with that all too familiar but wonderfully babyish scent. Breathing deeply, I sighed with pleasure as I watched Barbara select a pair of Duckie headed diaper pins.
Today she was wearing a short skirt that showed much of her fabulous thighs–firm thighs that I was frequently bent over, either for my morning enema or more rarely, for a sound spanking. Fortunately, the latter had become much more infrequent although there were still occasions in which she felt my behavior warranted a session with her hard, unforgiving oak paddle. Not one to tolerate any nonsense, Barbara wouldn’t hesitate to punish me, whether alone or in front of company if she felt I deserved it. Her spankings never failed to leave me sobbing like a baby with tears streaming down my face and incoherent apologies tumbling out of my mouth.
But today she was happy and I was happy to be her baby. I couldn’t imagine a life without her.
As she bent forward to pin the side of my diapers, I gazed in admiration down the front of her nearly see-thru blouse. This morning, she was wearing a snow white top that her big, round, milk-laden breasts filled to capacity, straining mightily against the buttons. I smiled as I noted the smooth edge of her bra, plainly visible from my vantage point.
Barbara was a goddess by any standards. Although she was in her late thirties, she was in far better shape than many girls in their teens. Tall in stature, with a skinny waist and massive, jaw-dropping breasts, she inevitably turned heads wherever she went. All that and a face that stopped traffic with her pretty brown eyes had me head-over-heels in love with her years ago.
But as she bent forward to pin the other side of my diapers closed, I couldn’t help but be entranced by the heavy sway of her beautiful bosom. Any other guy of 17 would be rock hard at the sight but that was quite impossible for me. Years ago, when Barbara had first taken me in to become her baby girl, she had immediately taken the measure of placing my little penis into a foolproof chastity device which has remained forever locked since that first fateful day. Since then, I haven’t been able to get hard, play with myself, or have an orgasm of any kind, regardless of the circumstances. So despite the fantastic view that was before me, my insignificant noodle remained imprisoned and controlled, just as every other aspect of my life was controlled by Barbara.
With both pins now in place, the thick cloth of the triple diapers forced my legs apart which I knew from experience would cause me to waddle as I toddled around the nursery. This was not really much of an issue, since there was virtually no place for me to walk to. Confined to the inside of Barbara’s house, I spent most of my time crawling around from one side of my nursery to the other. Even some parts of the house were off limits to me, like the garage, the spare bathroom, and of course, Barbara’s master bedroom. And with the sole exception of my nursery, Barbara never let me out of her sight for one minute. Even when I was allowed out into the living room, more often than not, I was restricted to the playpen she kept there so she could keep an eye on me.
She was humming to herself now as she sifted through the overflowing drawer of plastic panties.
“Let’s see…what does mommy have for her precious little babykin’s…” she mused aloud, “How about these?”
Stretching a pair of semi-translucent pink panties with bunnies on it between her fingers, she beamed down at me expectantly.
“Uh-huh,” I nodded breathlessly.
I loved the super soft vinyl of these cute panties which were heaven to wear.
Gathering them at the legholes, she worked them over my feet and slid them up my calves. I mewled babyishly as she raised them up my skinny thighs and began tugging them up and over the thick, yet comforting bulk of my diapers. Once it was enclosed, she worked her manicured fingers around the elastic waistband making sure all the cloth was on the inside and then did the same with the leg holes. I shivered with delight as her silky fingers touched the sensitive skin of my inner thighs.
As a finishing touch, she powdered between my legs, leaving a whitish layer between my skin and the vinyl of the panties.
“Well–just look at you, Miss Prissy Pants!” she exclaimed eagerly, “All diapered and ready for the day.”
I blushed slightly and looked away, even though my sense of safety and security felt palpable now that I had been changed.
“Now we just have to find a sweet baby dress for mommy’s little sissy,” she said as she patted the fat front of my diaper playfully.
Standing up, she went over to my open closet and began carefully looking through the vast selection. There were countless dresses and rompers, most in pink, yellow, white, or baby blue.
After moving through the first third, she selected a white sailor suit with soft pink satin lace and a big pink floppy bow over the traditional bodice.
“How about this, sailor sissy?” she asked enthusiastically, “Are you ready for the high seas?”
Despite the beguiling smile on her pretty face, her tone was one reserved for toddlers and children and I couldn’t help but hear what sounded like sarcasm.
“Yes Mommy!” I replied immediately. Even though it was still humiliating after all this time, I still enjoyed playing her game if only to bask in her intoxicating beauty.
Dropping the light frilly garment over my head, she turned me slightly and as my arms went through the short, puffy sleeves, she zipped up the back behind my neck. I felt so girly as I felt the delicate pink lace around the short hem and admired the big floppy pink bow underneath the Peter Pan collar.
Kneeling down, Barbara took my Mary Janes and buckled them over my feet which were still wearing the frilly white anklets. Taking my hand, she gently stood me up and had me look at the large, full length mirror permanently mounted to the opposite wall.
As I gazed at my sissyish reflection, I was amazed at how babyish I looked. My hair was short and curly, with a Shirley Temple style Barbara had permed years ago. The sailor dress was so short it barely covered the waistband of my plastic panties, leaving my babyish thick diapers fully on display. And my soft, smooth legs seem to compliment my girlish appearance, lacking any muscle tone or hair at all. If they had ever looked boyish before (and I couldn’t remember them being so), they certainly weren’t now.
Turning around, I admired the perfect round curve of my thickly padded and pantied bottom. I sighed with satisfaction as Barbara bent down to softly pat my seat.
“Aren’t you just the CUTEST little girl on the block?” she whispered with a proud smile.
I blushed again, embarrassed at my own sissyishness.
Still looking at our mutual reflection in the mirror, Barbara bent down slightly to speak closer at my level.
“Do you want to wear some rumba panties with your dress or leave your plastic panties on display?” she asked with interest.
“Umm, I think I’ll go with just these,” I said shyly, casting my eyes at the floor.
“Can you tell mommy why you don’t want some rumba panties? ” she asked softly.
“Ummm,” I said hesitantly, “cause I um…like the bunnies,” I said barely audibly as I pointed at the colorful yellow bunnies decorating the shiny pink vinyl panties.
“Okay Chrissey,” she said with a giggle that made me blush crimson, “you can wear these pretty panties by themselves.”
As she gently stroked the soft, thick seat of my diapers, her beautiful bosom jiggled and I shivered with delight.
“I love you Mommy!” I suddenly blurted out, throwing my arms around her slim waist. Because she was so much taller than I was, I found my face mashed against her big, pillowy breasts.
“Mommy loves you too, Sweety,” she said with amusement, hugging me in return.
“And mommy has a special surprise in store for her baby girl,” she said as she led me over to the side of my crib. Sitting down on the edge of the plastic lined mattress, she guided me next to her and produced a slim catalog with a sexy woman on the cover dressed like a baby.
“My little sweety’s birthday is coming up and I thought you’d like to pick out some new baby outfits,” she explained as she put her arm around me. It always gave me an electric thrill to have her touching me, partly because I’d never been touched by a female except for my real mom, but also because she was so incredibly sexy. Sitting next to her on the edge of the crib mattress, I had the opportunity to gaze surreptitiously at her tremendous breasts that were threatening to burst out of her snug top. Barbara didn’t like me staring at them, and in fact, she’d spanked me in the past for doing it blatantly but at the moment, there was no way to avoid it.
“Oh yes, Mommy!” I exclaimed, “That would be wonderful!”
I was used to Barbara making every conceivable decision for me, whether it was what I was to wear, eat, or when my bedtimes were, so this was an extraordinary privilege.
Flipping past the first few pages to a section on dresses, she smoothed the catalogue out over our laps.
“Here’s a lovely play dress,” she pointed out, indicating a cute little dress with designs of ducks and bunnies on the bodice.
“How do you like that, Chrissey?” she asked.
“I like it very much, Mommy,” I admitted shyly.
“And here’s one in pretty pastel yellow–just look at all that lace, Honey!” she exclaimed.
“Uh-huh,” I acknowledged.
Between the cute, babyish clothes and the warm proximity of Barbara’s sexy body, I was starting to become very aroused. My tiny penis was starting to throb anxiously and I tried hard not look at the luscious curves of her breasts that were each, nearly the size of my head.
Flipping the page, she pointed out a diaper shirt and chuckled with amusement.
“Oh–here’s one that’s just right for you, Chrissey–see what it says on the chest? ‘Still a bedwetter’.”
I blushed with embarrassment.
“Yes Mommy,” I whispered.
“Would you like that top, Baby?” she asked in a seductive voice.
“No Mommy,” I shook my head.
“Who’s the little baby bedwetter in this room?” she nudged me.
“I am, Mommy,” I mumbled as my cheeks reddened.
“You certainly are–I think we’ll get it anyway–its so perfect for my little sissy.”
Sometimes Barbara asked me questions for which I knew she’d already decided the answer beforehand. This was apparently one of those times.
“I just love these tops with the cute phrases,” she continued, “here’s another one…read what it says, Chrissey…” she prompted me.
I cleared my throat and paused awkwardly.
“Sissies wear diapers,” I squeaked.
“Wouldn’t that be a perfect shirt for you, Chrissey?” she asked eagerly.
“Umm…I guess so,” I replied uncertainly.
“Chrissey–you’re mommy’s special little sissy and you’ll always be in diapers,” she assured me confidently.
Looking up into her gorgeous, smiling face, I felt her love for me and I sighed happily.
“Yes, Mommy.”
I’m so glad we could share this mother-daughter moment,” she said as she hugged me closely. I savored the feel of her plump breasts pressing against my cheek.
“Me too, Mommy,” I agreed.
Flipping the page, we got to my favorite section, the page with the panties.
“Baby likes her pretty panties, doesn’t she?” Barbara cooed.
“Yes Mommy,” I admitted.
Truth was, I’d always had a secret fetish for girl’s panties and though it was unlikely I’d ever get to wear them, my preference had shifted to baby panties and diaper covers.
“Ohh, now look what they have here,” she said, “It looks like you can get lace around the legs and waistband of any of these plastic panties. Wouldn’t that be cute?”
“Uh-huh,” I agreed.
Suddenly, and without any warning at all, I felt the cloth between my thighs growing warm and wet. I was peeing freely with a strong surge and I only barely managed to stop the flow. Even so, a few good squirts still managed to add to the already saturated cloth, before I could bring it to a halt.
“M-Mommy!” I squealed, “I just wet my diapers!”
Barbara looked up from the page and casually placed her hand on the warm, cushiony front of my vinyl panties.
“That’s okay, Honey,” she said calmly, “It can still take quite a bit more–I’ll just change you after breakfast, okay?”
I sniffled and nodded, knowing she was right. Even my daytime diapers were extra thick, enabling multiple wettings before a change was necessary. The down side of that was that I was often wearing a wet diaper more often than not.
“Now–tell me which panties you’d like to get for your birthday,” she urged me.
“Umm…I kinda like these,” I said, pointing to a pair of nursery print plastic panties with clowns and blocks.
“Oh yes, those are very cute, aren’t they,” she concurred, “would you like lace around the legs too?”
“Uh-huh,” I said, too embarrassed to look her in the eye.
“How about some satin rumba panties? Do you like the pink ruffles on this one?” she asked.
My little penis was starting to throb inside the chastity tube although at this point, it wasn’t too painful, just a growing ache that was making me conscious of my ever present need to cum.
“Mm-hm,” I nodded.
“These would look super special with the pink party dress Pamela got you, don’t you think?”
I blushed beet red at the mention of my real mom. Years ago, before she sent me to live with Barbara, I used to manipulate her at my whim. Now the roles were reversed and she never hesitated to humiliate me whenever she came to visit.
“Yes Mommy,” I mumbled as I looked away.
“You know, I’ve got another surprise for you Chrissey,” she said excitedly, “Today I’m going to take you to the park and let you play in the kiddie’s sandbox–won’t that be fun?”
My mouth hung open in shock as I turned to look up into her beaming smile. Suddenly, I felt another strong flow of pee soaking the cloth between my legs again and I cried out in angst.
“Oh!” I whimpered in my high-pitched girlish voice.
Barbara’s face took on a look of confusion.
“What’s the matter Sweety? Don’t you want to play outside? I thought you’d be dying to get back out again after all this time.”
It was true that I hadn’t been outside for nearly three years. Barbara had kept me cooped up inside here for so long I had forgotten what it was like in the outside world. At first, I’d been deeply resentful and thrown numerous temper tantrums to force her to my will. Without fail, these always resulted in my being pulled over her lap for a blistering spanking. After becoming intimately familiar with her unforgiving wooden paddle, and after countless tears had been shed, I learned not to question her rules.
Some time later, after I got settled into a lifestyle befitting a toddler, I tended to forget about my previous life and in fact, after my initial bout of resistance, I actually came to enjoy being babied.
Now she was talking about taking me not only outside, but out in public where others would see me.
“Am…am I gonna go out d-dressed like this?” I asked with a shaking voice.
“Oh course, Honey, what else would you wear?”
“B-but–everyone will see me–you know…dressed as a b-baby.”
“That’s because you ARE a baby, Chrissey. How else would you be dressed?”
She seemed honestly perplexed at my question.
Looking down at my bare legs, my bulging diaper and the lacey hem of my sissy pink sailor suit, I was terrified to think what people would say if they saw me in the park.
“No Mommy–I can’t!” I squealed.
Barbara reached forward and calmly grasped the large pink rubber pacifier that was permanently kept on a loop around my neck.
“Open up Chrissey,” she said with her classic, confident smile.
In my rising panic, I felt another strong surge of pee soaking my already soaking wet diapers.
“No Mommy–no!” I cried just as Barbara pushed the familiar object between my pouting, quivering lips, stifling any further argument from me.
“There,” she grinned triumphantly as she patted me on the head condescendingly, “I just know you’ll have a wonderful time.”

Chapter Two

About an hour later, I found myself strapped into a carseat in the back of Barbara’s minivan, making our way across town. Every stoplight we came to brought fresh stares at the oversize baby sitting in back wearing a white and pink sailor suit and diapers. At a distance of three feet, it was plainly obvious that I was a 17 year-old guy dressed as a toddler, rather than a bonafide baby.
I blushed vividly as a pair of high school girls rolled down their window and made sneering comments at me, asking me humiliating questions that made me squirm with discomfort. I tried to look the opposite way but there was little escaping their laughing and condescending remarks until our van finally turned down a different street.
Although it had been three years since I’d been outside, I was now more than ever filled with apprehension about the day and Barbara’s plans for me.
“Mommy, I wanna go home,” I whimpered miserably, but the words were completely unintelligible with the fat rubber pacifier filling my mouth.
“Now Chrissey,” Barbara chided me as she guessed my fears, “you’ll feel much better when we get to the park. Aren’t you looking forward to playing in the sandbox?”
“Uh-uh,” I whined, shaking my head.
“Don’t worry, Sweety, you’ll have a great time today–you just wait.”
I slumped down in the raised carseat, although that did little to hide my appearance from the people in the cars that kept coming by all around us. Looking down at my colorful, shiny plastic panties, bulging from the fresh diapers Barbara had recently changed me into, I now regretted my earlier choice of panties. Not that the rumba panties she had in mind for me would have made me look any more adult. But there was certainly no mistaking the look of nursery print plastic panties and it spoke volumes about what I’d become. I was foolishly trying to hang on to the fantasy that I was a still a regular guy. The fact was, I was a big sissy who couldn’t keep his pants dry for more than an hour and I needed diapers just like the baby I was dressed up as.
As we pulled into the parking lot, I was still hoping against hope that nobody would be there but as Barbara started driving slowly down the rows of cars, I realized to my dismay that the place was packed. We were driving slow enough, occasionally stopping, that everyone walking alongside could take a good, long look at me. My breathing increased and my hands grew clammy as mothers stared in at me, not knowing what to make of the teenager sucking feverishly on his pink pacifier.
Loud, urgent sucking noises could be heard from the backseat as I whimpered and whined, fidgeting nervously against the harness that held me in so securely.
Up ahead, a car was pulling out and Barbara had stopped while waiting to take the vacating car’s spot. An attractive girl in her twenties passed by our van and as she looked at me oddly, I felt my bladder’s floodgates suddenly bursting open without warning.
Hot, urgent pee flooded into my diapers uncontrollably, soaking them in moments as I squirmed and shook my fists in frustration. Not again! I was really hoping to get through this outing without a humiliating diaper change. My hopes were dashed as the pooling wetness seeped thoroughly into my seat and upwards into my crotch. Suddenly, I couldn’t take it anymore. As my pacifier tumbled out of my mouth, I burst into tears, wailing an incomprehensible deluge of regrets.
Barbara had just parked and shut down the car when she turned to face me, motherly concern all over her pretty face.
“What’s the matter, Baby?” she blurted out in surprise.
Without waiting for an answer, she jumped out of the driver’s seat and ran around the front of the van, yanking the sliding side door open as if I were choking to death.
With her maternal instincts spot on, she bent over me, her soft hand going down between my legs and cupping the fat bulk of my diapers.
“Aww, mommy’s little baby just wet herself, that’s all,” she cooed as she scooped up my pacifier and pushed it back between my trembling lips. With her gorgeous face just inches from my own, she leaned forward and kissed me tenderly on the cheek.
“Don’t you worry, little sugarplum–mommy’s going to change you into a nice fresh set of diapers in no time!”
I was mortified at the thought of her changing me here where so many people were walking by and I stomped my feet in frustration and anger.
“No! No! No!” I wailed but of course, it sounded more like ‘wo-wo-wo’ instead.
Barbara beamed at me with what looked like pride as she unbuckled the harness holding me in. Pulling me out of the seat, I could feel the familiar wet, sticky feeling of a soaked diaper clinging to my backside.
In between the front seat and the bench seat I was on, the floor was at least three feet wide and after laying a vinyl changing blanket down over the carpet, Barbara set me down upon it.
I was still whimpering loudly, waiting impatiently for Barbara to close the door but she made no move to do so. Before I knew it, she was tugging my clinging plastic panties over and off my diaper and down my skinny thighs. Knowing there was absolutely nothing I could do to stop her, I cried tears of shame as my pee soaked diaper came into view.
Without a second thought, Barbara shook the vinyl panties out over the edge of the van and folded them up before putting them in a plastic bag. Humming to herself, she busied herself with unpinning the diapers themselves and pulling them back. Until now, this had all seemed like a bad dream but as I felt the cool air against my smooth, hairless crotch, the reality of it all hit me like a stack of bricks.
“No Mommy–no!!
My pacifier fell once more from my mouth.
Without a moment’s hesitation, Barbara grasped my ankles and lifted them up high, abruptly exposing my bare bottom to the entire outside world. I squealed in dismay as her other hand came swooping down to deliver a sharp, punishing swat to my bare, dampened cheeks.
“OWWW!!!” I wailed, loud enough to attract the attention of another mother and her kids. I tried to kick my feet but her grip holding my ankles was like steel and she delivered another stinging swat right on top of the first reddening handprint.
“Time for you to settle down, young lady!” she scolded me as she wagged her long finger in my tear-stained face.
I sobbed in shame as she pushed my pacifier back into my pouting mouth, muffling my whimpering protestations. Then, as if nothing had happened, she began her usual task of wiping my diaper area clean with some baby wipes when a voice of greeting was heard behind her.
“Barb? Is that you?”
Barbara popped the baby wipe in the plastic bag and turned to face the young woman coming up behind her. There was only a brief pause before Barbara recognized her friend.
“Hello, Norah!” she exclaimed eagerly, “How have you been?”
An attractive woman about 30ish strode up and threw her lithe arms around Barbara. My eyes just about bugged out as I observed her giant breasts mashing against Barbara’s own huge melons. The scene made me stop crying and I gaped in amazement at the voluptuous woman.
“Its been what–two years? Since I last saw you?” her friend inquired.
“Yes–yes. How have you been?” she asked excitedly.
It was apparent that I was immediately forgotten in the course of Barbara getting re-acquainted with her sexy friend. At home, I would have hardly minded but here in the middle of a parking lot with my hairless and locked genitals displayed for everyone to see, I was aghast with embarrassment. Trying desperately to cover my shame, my hands flew down to cover my crotch.
“Simmer down, Missy,” Barbara said as she absently slapped my hands away, “If I have to tell you again, I’ll be putting you over my knee.”
In mute frustration, I was forced to keep my hands by my side, although Barbara didn’t appear to be in any particular hurry to finish changing me. On the contrary, other than an occasional glance in my direction to make sure I was behaving, she completely ignored me.
Her friend was nothing short of incredible, with a big, beautiful bosom barely contained by the tight lemon colored top she was wearing. Her long brunette hair spilled over soft shoulders, fortuitously leaving an unobstructed view of her fabulous curves. I momentarily forgot my exposed circumstances as my penis struggled to become hard.
“So this must the little sissy you’re taking care of,” Norah said as she finally took notice of me with a broad smile upon her beautiful face.
“Yes, Norah–this is Chrissey–Chrissey, meet my good friend Norah.”
Without removing my pacifier, it was quite impossible to articulate any sort of greeting. Instead, my muffled response sounded like more babyish gibberish.
“Aww, he’s so cute,” she said as she beamed down on me.
I blushed at the unwanted attention and tried to will her to go away so Barbara would finally finish changing me.
“Well, and what do we have here?” she asked excitedly as she caught sight of the small, clear device encasing my penis. Bending down, she held the hard plastic chastity tube in between her slim fingers.
“That’s just a little something I had custom made for Chrissey when I first started taking care of her. She was a chronic masturbator when she arrived and that little gem solved the problem once and for all,” Barbara replied proudly.
Norah’s pretty features furrowed slightly as she looked closer at my diminutive, captive penis.
“Oh my–I’ve never seen such a tiny wee-wee except on real babies. Did it shrink after you locked it up?”
Obviously, she had a hard time believing a 17 year-old guy could have such a small wiener.
“Just a little, but it was half sized even when I met her. That’s why I had to get the device custom made–she would have fallen out of the normal ones.”
Norah kept handling my package as she examined it with obvious fascination from all angles. She was gentle in her handling but it was mortifying to be examined in such an impersonal manner.
“What’s the relief schedule you have him on, Barb? Once a month? Every other month?”
For a second, a look of confusion crossed Barbara’s face but she quickly recovered.
“Oh no, silly,” she giggled, “Chrissey here hasn’t had an orgasm in three years–babies don’t have orgasms–that kind of pleasure is only for adults and as you can see, Chrissey is certainly no adult,” she said emphatically.
Norah smiled and nodded in complete understanding.
“But isn’t it harmful to keep all that um…fluid, trapped inside him?”
“That’s true,” Barbara acknowledged, “which is why she gets milked once a month. As a matter of fact, Chrissey here is due to be milked this very afternoon.” I sucked anxiously on the fat piece of rubber filling my mouth.
“Do you have to remove his chastity device for that?”
“No, not at all. I have a slim rubber tool that I slide into her bottom to massage the prostate gland with. In about three minutes, she starts dripping like a faucet. It takes about ten minutes to drain her completely but you’d be surprised at the quantity,” Barbara remarked.
“I see,” Norah nodded with interest, “I can’t imagine a real man letting someone take control of his orgasms like that–my husband certainly wouldn’t tolerate it for one second.”
“No, of course not. No real man would ever let that happen but Chrissey here isn’t a real man–not by a long shot. She’s the prissiest little sissy I’ve ever come across. She just loves dressing up in her frilly dresses and panties and being a sassy toddler girl–don’t you, Sugarplum?”
I blushed a deep shade of bright red and looked the other way as I chewed on my pacifier anxiously.
“No…Chrissey here knows that she’ll always be my precious little baby girl and that means she’ll never have another orgasm again. Of course, that’s the way it should be for all sissies, don’t you agree?”
“Oh, without a doubt,” Norah nodded, “I think this was the best thing you could do for him. By locking up his little nub, he won’t be tempted to play with it as so many sissies are,” she reasoned.
“Exactly. And sissies don’t need to cum anyway–they get enough satisfaction just from dressing the part.”
Norah nodded again as she looked down and saw the object of my distracted gaze.
“You know, your little baby here seems very interested in my breasts,” she said as she dangled her slim, manicured hand over her bosom and giggled with amusement, “His little package has been twitching and he can’t seem to take his eyes off my cleavage.”
Barbara chuckled.
“Oh, don’t be concerned about that, Chrissey is breastfeeding everyday and she’s naturally entranced by well-endowed women.”
Norah stood back, placing her hands on her hips which only caused her big, plump breasts to thrust out even more prominently.
“Ha ha! Sorry to disappoint you Chrissey, but only real men get to touch these. I’m afraid this is as close as you’ll ever get to them.”
Her haughty, superior attitude hurt my feelings and I choked back a tear of shame and envy. Despite her rejection of me, I still found her incredibly sexy and appealing and her denial of me only made me want her more.
“Well, I better get back to putting Chrissey’s diapers on–she really has no control and I’m afraid she might wet herself as we speak,” Barbara explained.
“Of course,” Norah agreed, “No sisssy should be without his diapers.”
Taking a thick stack of fresh ‘Bedwetters’ from my Minnie Mouse diaper bag, Barbara slid them under my upraised bottom and then set my legs back down.
“He must be a heavy wetter, hm?” Norah remarked as she gazed down at the soft, bulky Birdseye cloth that Barbara was pulling between my widely spread legs.
“Oh my–yes,” Barbara exclaimed, “these are Bedwetters brand–they have a nice thick soaker pad sewn in down the middle and as you can see, each individual diaper is very thick on its own.”
“So soft too,” Norah said appreciatively, “I’ll bet you’re little baby just LOVES wearing these.”
“Oh yes,” she agreed, “She certainly does. Chrissey loves anything that makes her look and feel more babyish, but truth be told, she’s wearing these diapers out of necessity, not preference. The little sissy wets so much that anything less than three diapers and she risks leaking. So all her plastic panties are nice and snug to make sure her wetting stays right where it belongs.”
My cheeks blazed crimson with shame as I lay there, helpless to deny her remarks.
Barbara was snaking up a pair of see-thru polka dot plastic panties over my diaper as an older lady happened to walk by.
“Excuse me, but…isn’t he a little old to still be wearing diapers?” she asked skeptically.
“Oh no–some boys never outgrow the need for diapers and plastic panties,” Barbara replied without a moment’s hesitation.
The lady didn’t seem entirely convinced and she shook her head as she strode off without any further comment.
Barbara giggled to herself but I whimpered with embarrassment at all the exposure I was getting. She proceeded to powder between my legs and then she announced me ready to go.
“There you are Sweety, all safe and secure again.”
I blushed as Norah giggled at my appearance.
“Well, I better be getting on,” she told Barbara.
“It was great to see you. Stop by the house sometime, I’ll show you Chrissey’s nursery.”
“I’d love that,” Norah replied eagerly, “See you next time, Chrissey.”
I waved feebly, still laying on my back with the bulk of my diapers forcing my legs apart.
After Norah left, Barbara helped me climb into the oversize stroller she had brought in the back of the minivan. I still didn’t know how I was going to cope with people seeing me dressed the way I was. I could only hope the canopy top would provide some measure of anonymity to me as she pushed me along the path. Nervously, I suckled from my pacifier as she pushed me along.
About five minutes down the mostly deserted path, Barbara got a call on her cell phone and she halted our movement long enough to take it. I sat in place, completely incapable of going anywhere due to the construction of the stroller. Not only was it awkward to get in and out of, but Barbara had taken the extra precaution of having a seatbelt installed so that I wouldn’t be able to climb out on my own. It secured to a locking clip located on the back of the stroller and was totally out of my reach. Like it or not, I was staying put until she decided to release me.
With little else to do, I sat and watched the only thing of interest in my field of view, a young couple sitting on a park bench, their attention completely devoted to each other. The girl looked to be about my age or slightly older, a pretty blonde wearing a clinging pink crop top which revealed a firm and tanned tummy. My penis twitched with interest as I took in the perfect round curves of her breasts and her narrow waist that complimented her perfect body. How I envied the guy that was stroking her bare thigh! What I would have given to be in his place!
I watched in vicarious angst, as his hand slid slowly up, caressing her curvy hips and then moving on to her sexy waist. My wiener was throbbing now, my libido raging as I watched and wished it were me doing the touching. His hand moved up from her waist now, cupping those full, perfect breasts one by one. I chewed my pacifier anxiously and whimpered as she sighed with pleasure and kissed him passionately in return.
By now, Barbara had finished her phone call and she appeared before me with a large baby bottle in her hand, partially blocking my limited view.
“I’ll bet mommy’s baby is thirsty now, hmm?” she asked as she bent down before me. I had just been able to discern the cute blonde’s perky nipples poking through the thin material of her snug top as a result of her boyfriend’s attentions when Barbara proceeded to completely obstruct the love fest taking place a short distance away.
I squirmed and whimpered, trying to crane my head to see the sexy girl but Barbara was holding the bottle poised before my mouth.
“Open up Sweety, time for num-nums,” she said with an accomodating smile.
Apparently oblivious of my distraction, Barbara removed my pacifier and as a string of saliva followed the rubber soother, she pushed the warm and dripping rubber nipple of my baby bottle into my open mouth.
“Owmmph,” I squealed as I pulled away trying to avoid her ministrations. Unfortunately there was nowhere to go and as my head found the back of the canopy, Barbara held the bottle in place making sure I nursed from the warm breastmilk milk she’d pumped earlier.
“That’s my baby,” she cooed.
I squirmed in my seat, frustrated that I couldn’t see the sexy girl not twenty feet away. My little penis was still throbbing from the image burned into my memory of her incredible body and I pouted helplessly.
It was times like this that I hated my life as a baby. Yes, I had lots of fun normally, wearing my sissy dresses and wetting myself without a care in the world but this was the reverse side of that coin. I was so horny I couldn’t stand it and there was absolutely nothing I could do about it.
The guy that was fondling that girl would be getting his rocks off in no time, probably within the hour, if he played his cards right. And I’d still be here, horny and frustrated, wishing I could do something as simple as rub myself to an orgasm. Full time chastity was one facet of my life I could never quite get used to. If it wasn’t Barbara herself that was constantly arousing me, it was someone else, like this girl on the park bench. And it wasn’t like I could get some quick relief and then be done with it. I was forced to endure my frustration, day after day, without any hope of respite. It was so cruel!

Chapter Three

I was still thinking about the amorous couple at the park when we came back home an hour later. With all the visual stimulation I’d received, I was desperate to try and alleviate my horniness but I was completely at Barbara’s mercy and in the last three years, she’d shown me none at all in that department. Strapped into my carseat, I was re-living in my mind for the thousandth time, the scene of the couple making out when I saw my mom’s car pull up behind us in the street.
That was all I needed. It used to be that I had the upper hand with my mom, manipulating her with my whining and complaining but now the tables had been irrevocably turned. Barbara had seen to that. And now my mom reveled in her ability to make me do her bidding, ordering me around and using her new authority to emphasize my subservience.
Anxiously, I wondered what it was that had prompted her visit today. Barbara closed the driver’s door and came around to open the sliding side door, just as a cool breeze blew the short, frilly hem of my sailor suit up.
I squealed loudly, although the fat rubber pacifier filling my mouth muffled my cries considerably. I struggled to push the hem back into place but it really made little difference. With the cross straps of the childseat buckled in place, my bulging diapers were on full display no matter what I did. And needless to say, I didn’t dare touch them. The last time I had unbuckled myself, Barbara had pulled me over her lap, taking only enough time to pull down my diapers before she blistered my bottom. I could still remember her lecture on ‘safety’ as she gave me swat after stinging swat of her paddle…
Just then, Barbara caught sight of my Mom.
“Hello Pamela, great to see you again!”
They said their hellos while I squirmed uncomfortably, knowing there was nothing I could do that was going to get me inside any faster.
After an interminable conversation, Barbara finally unbuckled me and led me inside.
“You’re just in time, Pam,” Barbara told her as she put her purse and keys away, “Chrissey’s due for her milking today–you’d asked to watch next time I did it.”
“Yes! Well, what a wonderful coincidence!” my mom exclaimed.
Barbara was still holding my hand, afraid to let me be free even for one moment until she’d put me in my highchair, playpen, or the nursery. So despite the fact that we were home, I had to stand there, a virtual prisoner, to wait until Barbara decided what she wanted to do with me.
Knowing what was in store for me, I shifted my feet and visibly pouted. I really resented getting milked and as I stood in place, I stamped my feet in bitter frustration. It meant that all the built up cum that was driving my libido would be drained from me, while I’d get no satisfaction whatsoever. It had to be one of the most emasculating experiences to have my balls drained by a woman determined to prevent me from cumming.
Barbara ignored my fussiness as she led me into the nursery and placed me into my playpen. It was a net sided box of sorts, very much like a real toddler’s except that the sides were about three and a half feet tall. I could just barely climb into it and Barbara had placed bells around the edges as a precaution so she’d hear me if I tried to get out by myself.
Sitting on the soft, cushioned vinyl surface of the playpen, I watched sullenly through the mesh netting as Barbara got a few things together.
“So as I recall, you said that this is the only time his chastity device ever comes off right?” my mom inquired.
“Yes, it’s also a good time to make sure she’s nice and clean down there–and after we’re done, I’ll be sure to lock her little thing right back up again,” Barbara replied.
“I think you were so smart to do that–he really shouldn’t have free access to his willie,” my mom praised her.
“You’re very kind, Pam. It’s always been my rule with sissies to put them under strict chastity at the very first opportunity. We were only delayed in Chrissey’s case because she was so small, I had to have her device custom made.”
“Those are worth their weight in gold. And you just need to milk him every month for health reasons then?” she asked.
“Yes, I’ve found once a month is more than adequate. She gets edgy and fussy if I go longer than that,” Barbara explained.
It was bad enough that I had to endure this humiliating routine but it was rubbing salt in the wound to have my mom here to watch the whole thing. I took one of my dolls and slammed it down on the padded floor but it went unnoticed by the other two.
“Okay Chrissey, let’s get started,” Barbara finally told me.
Reaching down, she pulled me out of the playpen and stood me up.
“Did you wet your pampers, Chrissey?’ she asked me pointedly.
Blushing with embarrassment, my pacificer still in my mouth, I shook my head no. Sometimes it seemed like every word out of her mouth was specifically intended to humiliate me.
I felt her cool fingertips slip inside the elastic waistband of my plastic panties and pull them down, working them off the bulging cloth and then down my smooth, hairless legs. I whimpered in protest, knowing the fuel for an explosive orgasm would all too soon be taken from me against my will.
With little effort, she pushed my thick diapers down around my ankles and helped me to step out of them. I knew very well the procedure and without being told, I stood in place while Barbara recovered the small key. Bending over me, I gazed idly down the front of her blouse, marvelling at her yawning cleavage and her big, beautiful breasts. Her skin was so smooth and creamy…it was impossible to not be distracted by her.
“Didn’t you glue that lock shut some time ago?” my mom asked.
“Yes, but I found I really couldn’t keep her as clean as I wanted–and we want our baby girl to always be squeaky clean–don’t we sissy?” Barbara asked as she looked directly into my eyes.
I nodded my head obediently in response.
“So I had the lock removed and I got a custom titanium one made. As you can see, it’s super small and it can’t be picked–not like Chrissey would ever have the opportunity to do it anyway.”
My mom chuckled as she came closer to look down at my miniscule caged penis.
Slipping the narrow, uniquely shaped key into the bottom of the lock, Barbara twisted it and freed the hasp after which she removed it and placed it on the dresser top. Gently, she grasped the clear plastic tube of my chastity device and pulled it away from the pins that kept it in position. My penis was already in an excited state from earlier and staring at Barbara’s big, round breasts made it spring to life as she pulled the tube away from the rest of the device. She chuckled as she held my little wiener in her hand, watching as it grew to its full length of about an inch.
“Looks like you’ve lost another quarter inch since the start of the year, Chrissey,” she said smiling eagerly.
I gasped in angst and bunched my fists in mute frustration. When I first met Barbara, my penis was already undersized, for reasons I never knew–it just seemed to stop growing when I got into grade school. But since it had been kept under lock and key within the restrictive confines of my chastity device, it had begun to gradually shrink over the course of time. Now, it truly looked ridiculous as I gaped at the twitching pencil stub in her warm hand.
“Is that as big as it gets?” my mom asked incredulously. Her wide eyed expression showed that she was clearly having difficulty believing what she was seeing.
“That’s it,” Barbara laughed, “Honestly, I think Chrissey really was born the wrong gender, but as you can see, we’re making steady progress towards correcting that mistake.”
The two laughed together and my cheeks blazed with shame.
Her demeaning comments were also having a negative impact on my erection, despite my horny state, and it gradually began to wilt before the two of them. I squirmed uncomfortably, blushing with embarrassment as it shrivelled even smaller, to half its size, looking like no more than a small nub in between Barbara’s larger thumb and forefinger. I bit my lip anxiously as I was made to stand there while they examined my diminutive organ.
“Okay, Sweety, let’s get down to business,” Barbara said as she led me over to the crib and had me kneel down before the open side. A vinyl changing pad had been placed on the floor between my legs to catch the eventual discharge. Placing my hands on the nursery print waterproof mattress cover, I breathed deeply from the smell of stale pee that had gradually permeated the plastic surface over time. I soon felt Barbara’s soft hands guiding me and positioning my rump so that it faced outward to them at the proper angle. In my embarrassed state, I clutched my big pink teddy bear for comfort.
My mom watched closely as Barbara slipped a rubber glove on and dipped her finger into a jar of Vasoline to get a good dollop of lube.
“Spread your legs, Baby girl,” Barbara instructed me as she knelt down behind me.
I complied with reluctance and felt her other hand on the side of my hip to steady me.
No matter how much she gave me advance warning, I still winced when I felt the cold gooey tip of her finger invade my backhole.
“Ohh!” I squealed as my pacifier tumbled out of my mouth.
My sphincter puckered as she slid her slippery finger deep into my rectum, twirling it around to give me a good coating. My little penis twitched nervously in anticipation and then when she was satisfied, I felt her withdrawing her finger.
Out of the corner of my eye, I saw Barbara reach down to pick up the milking tool she always used.
“This little item is called an Aneros,” Barbara told my mom, holding the smooth, thumb-shaped dildo in her hand. It was about three and a half inches long with two tabs that extended 90 degrees off the end and formed a handle of sorts. Rolling it into the jar of Vasoline, she coated it liberally before positioning it back at my bashful, quivering hole.
“Sit still and take it like a good girl,” my mom commanded me unneccessarily.
“Here it comes, Baby,” Barbara sang gleefully.
I knew better than to resist her but I didn’t want to entirely submit without a fight.
I felt the first indication of pressure against my anus by the slippery tool.
“No…mommy…unh…wait–” I whimpered weakly.
Barbara ignored me and she gently pushed the greasy rubber phallus deeply into my back passage.
“OHHH!!!” I cried and I gripped teddy tightly as I felt my hole suddenly being filled by the soft, pliable invader.
Within seconds she established a consistent rhythm and as she found my prostate, I slowly relaxed and began to breathe heavier. Her ministrations were soon bringing waves of pleasure to me and her other hand gently patted the buns of my spread cheeks.
For once, my tiny penis was free, and now that it was no longer restrained by my chastity device, it grew to a full erection (or as full as mine ever got). Oh, how I longed to reach back and give it several satisfying strokes! I even leaned back out of instinct, my right hand surrepticiously slipping ever lower but Barbara saw the movement right away.
“Hands back in front, Chrissey,” she commanded me firmly.
In utter frustration, I fussily complied and knelt there captive as she pumped me rhythmically and steadily, massaging my prostate and causing my penis to harden even further. For her, it was a completely non-sexual activity, like kneading bread, and just a routine that needed to be done once a month for my own good.
In my excitable state, I knew it would only take a few quick rubs against the waterproof mattress cover to blow my accumlated load of a month but with Barbara’s paddle in such close proximity, I didn’t dare to try it.
“You know what to do, Chrissey,” she said with calm confidence.
My mom looked at her quizzically until Barbara explained.
“As I massage his prostate gland, Chrissey here gets very close to ejaculating…but she knows she has to tell me before it happens so I can stop the massage and let her cool down.”
My mom giggled at her control over me.
“Ohhhhh….” I moaned weakly, the waves of pleasure washing over me. A drop of precum appeared at the tip of my tiny tool and I clutched my teddy bear close for security.
My penis throbbed urgently and the vision of the blond girl from this afternoon floating back into my consciousness. God, she had a fantastic body, I reflected and as I felt an explosive orgasm bubbling up from deep within me, I moaned helplessly again.
“Oh–ohhhhhh,” I cried, “M-Mommy…I…I…”
Barbara stopped her rhythm and my penis, without anything to further sustain it, throbbed and flexed, unable to reach climax.
It was maddening and I grit my teeth, anger replacing my frantically horny feeling as I waited impatiently for Barbara to resume. As usual, she was in no hurry and instead, she slowly rubbed and squeezed my bottom, holding the Aneros in place, buried to the hilt with her free hand.
At long last, she began slowly pumping me again and my eyes rolled into the back of my head.
“Ohhh…,” I moaned.
I felt drunk from the sensations she was making and I couldn’t keep my eyes open. My penis was once again rock hard and throbbing and I wanted to cum more than I’d ever wanted anything in my life.
“M-Mommy…I-I-I have to…to…I have to cum,” I mumbled deliriousily.
Barbara stopped immediately and she gently rubbed my buns again, my penis twitching miserably with impotence.
One yank and I’d blast a shot of cum like nobody’s business but I knew Barbara would never let it happen.
I pouted and quivered with anger–it was so unfair!! Every other guy was free to cum and cum and cum til he couldn’t cum any more. But not me! I was to be denied that most basic of human functions, for the rest of my life!
In frustrated anger, I slapped the smooth surface of my crib mattress, making a loud ‘whap!’ against the vinyl covering.
“Its not fair!” I whined miserably, trying to grind my hips against the stationary dildo buried deep inside me, hoping for just enough stimulation to bring about an orgasm.
“Chrissey!” my mom snapped, shocked at my display of disrespect.
“It’s okay Pam,” Barbara assured her, “we’re about halfway done here and then Chrissey will be going over my lap for a much deserved spanking.”
I winced at her casual statement and a tear of frustration trickled down my cheek. Not only was my orgasm to be taken from me but now I was going to get paddled on top of it!
“We’re just about there…” Barbara said as she carefully reached between my legs and grasped my tiny twitching penis. She could read my erection like a book and she knew I’d already gone past the point of imminent climax. Putting her thumb and index finger together to form a ring, she slowly pulled it down the inch length of my shaft towards the jelly bean-sized tip. At first nothing happened but by her second attempt, a long string of semi-clear fluid began to dribble down from the end.
I gasped in dismay as I felt my orgasm being inexorably extracted from me while I knelt there, docile with lamb-like compliance as I whimpered and clutched my stuffed bear. When the first stream of semen petered out, she resumed her rhythmic ministrations with the dildo; in and out and around in a circle…
I moaned helplessly and this time, my penis didn’t grow nearly as hard.
“See that?” Barbara smiled, “I should be able to get at least two more squirts out of her and then she’ll be done.”
After a couple of minutes, she once more ran the ring of her fingers down, tugging on my organ and being rewarded with another thicker stream of gooey cum.
“So he’s not feeling any sort of climax during this?” my mom asked skeptically.
“Oh no–not at all,” Barbara said as she carefully pulled another stream of sticky gunk from my penis, “Its almost as if she’s just peeing, and there’s not the sort of pleasureable reaction that would normally happen during ejaculation.”
“Oh…oh…nooo…” I protested weakly as I felt the last bit of cum gradually being milked from my softening penis.
“There, that should do it,” Barbara said satisfied as she gave my noodle one last tug to be sure. A large pool of goo had accumulated on the pad between my legs and I looked down at it filled with regret and an acute sense of loss.
Setting the Aneros down, Barbara helped me to my feet and then led me over to the spanking stool which was kept in the corner. Pulling it out away from the wall, Barbara casually picked up the paddle and took a seat, smoothing her skirt down with her usual meticulous care.
“Chrissey, do you know why you’re getting a spanking today?” she asked.
I nodded my head sadly, my heartbeat increasing rapidly.
“Tell Pamela why you’re going to get your bottom spanked,” she instructed me in her usual condescending manner.
I blushed hotly and stared at Barbara’s smooth, silky thighs, unable to face my mom.
“Be-because I complained during my milking,” I mumbled.
“That’s right Sissy, and you know what happens to babies who complain about getting milked, don’t you?” she said as more of a statement than a question.
“They-they get spanked,” I said bitterly.
“Yes, they do–they get spanked hard,” she told me firmly as she looked me hard in the face.
I began whimpering and fidgeting as she carefully pulled me over her lap, moving me into a helpess position where my feet and outstretched hands could barely touch the ground. Tears were filling my eyes and I sniffled in anguish about my imminent punishment.
“Say you’re sorry to your mommy,” Barbara told me as she gently rubbed the hard wooden paddle across my soft, bare buns.
“I-I-I’m s-sorry Mommy,” I babbled nervously, dreading that first, terrible swat.
It came before my mom could respond, smacking both my tender cheeks with a harsh, blistering impact.
“OOOWWWW!!!” I wailed, just as a steady succession of hard, crisp swats came raining down after the first.
I kicked and sobbed, flailing my hands in the air as Barbara paddled me soundly and without pause. Tears streamed down my face in endless profusion and I cried unashamedly like a baby. Despite the fact that I was seventeen now, I felt as childish as a toddler, lying passively over Barbara’s lap as she spanked me vigorously, taking little effort to hold me in place. I knew better than to try to get up, which would have been futile in any case. In the three years since I had come to live with her, my physical strength hadn’t increased measurably–in fact, I was probably weaker and more delicate, due to my inactive and sedentary lifestyle. To be sure, I was no match for Barbara who was both taller, stronger, and in perfect physical shape.
As she continued to thoroughly pepper the entire surface of my bottom with her hard paddle, I slapped my hands on the floor, helplessly bawling as I received my just punishment. Five minutes ago, I was angry about being deprived of an orgasm but now that paled in comparision to my urgent desire to have this terrible spanking end. Of course, that wasn’t going to happen until Barbara was sure I’d learned my lesson and been thoroughly punished.
Finally, after what seemed like forever, her paddle seared itself one last time upon my flaming red bottom. I was hoarse from crying and my breath came in ragged gasps. Setting the paddle down, she helped me to my shaky feet and led me over to the changing table. I was loathe to sit down on anything, even the padded vinyl surface of my changing table but Barbara didn’t offer me any choice.
Picking up the tube of my chastity device she’d set aside earlier, she knelt down to mate it with the cuff ring that was still in place around the base of my genitals. My shriveled penis easily slipped back into the familiar tube and Barbara threaded the lock into the front pin, pushing it closed with a crisp click. My chest was still heaving from my crying as she pushed a thick stack of soft diapers beneath my cherry red rump and then powdered me with a thick coating of baby powder. The infantile scent surrounded me once more as she pulled a pair of white nursery print plastic panties over my feet and up my skinny legs. Still sobbing, I leaned back on my elbows as she worked them over the fat, bulky cloth and fitted the snug elastic wasitband to ensure everything was fully encased.
With a look of maternal concern, my mom came over and took my hand, gently lifting me up and leading me over to the loveseat that was used exclusively for my breastfeeding sessions.
Wiping my arm across my wet, tear-stained face, I tried to say some words of protest but it all sounded incoherent with my uncontrollable, childish sobbing. With nothing but love for me, she sat down and laid me across her lap on my back, so that her big, swollen breasts were mere inches from my face.
“Don’t cry little baby,” she cooed softly as she unbuttoned her blouse, “Mommy’s got a nice warm surprise for her little sissy.”
I shook my head trying to dissuade her–unlike being breastfed by Barbara which happened on a daily basis, nursing from my biological mother did nothing for me. I hated being forced to do it and it reinforced not only my submissiveness, but the transformed relationship between us in which I was at her mercy.
With her buttons undone, she pulled her top aside, exposing her plump, milk-laden breasts within the silk cups of her nursing bra. I mewled and shook my head but she undid the flap in front and revealed her damp nipple, hard and pink as if impatient to be suckled from. With tears still trickling down my face, she brought my cradled head up and forced me to accept her breast. With a sob of defeat, I opened my mouth and wrapped my lips around her warm areola.
Almost immediately, I was rewarded with a steady stream of her mammary milk, filling my mouth as I swallowed gulp after gulp. I continued to fidget and fuss until she gave my bare thigh a stinging slap.
“That should quiet her right down,” Barbara said with an approving smile.
Helpless to resist her, I settled down and began nursing without protest. I still whimpered weakly but my mom smiled down on me with obvious pleasure.
“It’s such a wonderful transformation you’ve made with Chrissey,” she marveled, “And these hormones you recommended have kept my breasts practically bursting–its quite a relief to finally have him taking some of the strain off them.”
“I know exactly how you feel,” Barbara concurred, “And don’t let her fussiness deceive you–she loves suckling from the real thing much more than any bottle.”
“Oh yes, I’m sure of it,” my mom agreed.
“Please feel free to stop by anytime when she’s not in her crib–Chrissey’s naptime is from 2 to 5 and her bedtime is 7:30.”
“Thank you, I think every three days or so, I’ll need to stop by so he can nurse from me, given all the milk I’m producing now,” my mom told her.
“It’s just what a pampered sissy needs,” Barbara assured her.
Pulling her right breast from my puckering mouth, she positioned the left one which was still straining from the milk inside.
I shook my head no and closed my mouth but my mom looked down on me disapprovingly.
“You’re not done yet, baby–you still have a ways to go,” she said with a smile as she rubbed the dripping nipple across my pursed lips. I squealed timidly but did nothing as she pushed her bursting nipple past my lips. In moments, I obediently resumed my nursing as she dried my face of spent tears.
“That’s mommy’s baby…” she whispered, “that’s it…get your fill of mommy’s milk. Diaper wetting sissies need to breastfeed just like little babies, don’t they?”
I blushed but kept up a steady pace until I felt my belly growing full.
“I think we’ll put Chrissey down for her nap early today,” Barbara announced, “that way, we can have a chance to catch up over coffee.”
“Uh-uh,” I moaned, although it was completely muffled by the nipple filling my mouth, sounding more like ‘muh-muh’.
“That would be great,” my mom said eagerly, ignoring my disgruntled face.
Ever so gently, she pulled her big breast out of my mouth and pulled the flap back over her nipple. Barbara helped me up and I stood fussily, pouting that my day was being cut short so soon. Normally, I would have an hour or two to play with my toys but now Barbara was sending me to my crib early. I wanted to say something in protest but my bottom was still blazing from the five alarm fire of my recent paddling.
With businesslike efficiency, Barbara removed my sailor suit top and pulled a fuzzy pink fleece diaper shirt over my outstretched arms.
“What does that say?” my mom asked as she looked closer at the script on the top of my shirt.
” ‘Bedwetter in Training’ ,” she read for herself and let out a delighted giggle.
I blushed again as my lower lip trembled with frustration. This day had started out so good!
Without any further delay, she turned to my crib and pulled the Disney Princess blankets down, revealing the crinkly nursery print waterproof sheet underneath.
“Beddie-bye time, Chrissey,” she sang merrily, guiding me firmly into the crib.
Sniffling in defeat, I crawled into bed as Barbara pulled the baby blankets back over me.
“Here’s your teddy bear, Sweety,” she said warmly as she tucked my stuffed bear under my arm.
I accepted it passively, not looking forward to another long afternoon in my crib. The only break I could expect in the tedious boredom would be when I inevitably wet myself and I stared miserably up at Barbara as she eased my pink rubber pacifier between my lips.
“Sweet dreams, Chrissey,” Barbara said as she brought the side of the crib up and closed it with a click.
I sniffled with resentment as the two walked out of the nursery, closing the door behind them. The light went out and I was left to ponder my life, not as a 17 year-old guy, but a baby toddler girl who couldn’t keep his diapers dry for one hour.

Barbara’s New Baby Girl

Chapter One The Store

My mom’s 20 year-old Honda Accord made its way, wheezing tiredly but steadily across town with myself as its reluctant passenger. Sitting in the back seat, I sulked in silence, unhappy with my situation in which I was being forced to accompany my dumb sister to get some girly clothes. My mom had insisted I come along because she didn’t want me home by myself, despite the fact that I was all of 13 years old now, going on fourteen. It was mortifying to still be treated like a snot-nosed kid at my age.
To show my general disapproval of my mom’s plans, I let out a loud and dreary sigh. This went unnoticed so I did it again until I saw my mom look up at me in the rear view mirror.
“Why do I hafta spend all day at this lame store?” I whined miserably.
“It’s not all day, Chris, she said tiredly, “It’s just long enough to get Lindsey a dress and then we’re done.”
“But I don’t wannnna go,” I complained bitterly, not for the first time.
My mom sighed in resignation.
“Tell you what Chris, once we finish at the store, I’ll take you to get some ice cream. How about that?” she offered, hoping desperately to placate me.
Fact was, my mom was easily pushed around. And truth be told, I knew just how to do it, through pleading, whining, and complaining until she eventually capitulated.
“Okay,” I replied sullenly, although I was secretly pleased to have wrung a concession out of her.
We pulled into the parking lot of the store a short time later and as I craned my neck, I could read the pink cursive writing on the neon sign. It said Missy’s Dresses and Apparel and I cringed at the thought of spending more than five minutes as a captive within it’s walls.
On the way over, we’d stopped for lunch at Chuck-E-Cheese and my sister and I still carried our disposable soda cups with our leftover drinks. Personally, I hated Chuck-E-Cheese because it catered to such a juvenile crowd but that was one contest I had decided to let my mom win.
As I got out of the car, I was crunching some of the ice from my cup, having discarded the lid somewhere in the back of the car.
“Chris, put the lid back on,” my mom told me, “I don’t want you to spill anything in the store.”
“Aww Mom,” I started, “I’m not gonna spill anything,” I said as I kicked a stray rock in the parking lot.
“Chris, just do it this time, okay? Just once I’d like to have you do something without a major ordeal,” she muttered in exasperation.
“I’m not gonna spill anything–I promise,” I said, my voice approaching it’s maximum tone of whininess.
My mom sighed heavily, finally giving up and I strode behind her, noisily crunching my ice as I chocked up yet another victory.
My sister Lindsey was eight and very excited to be able to pick out a dress of her own. Apparently, this store was known for it’s fancy, frilly dresses, the kind like you’d see at an Easter party or something. Personally, I couldn’t care less so the sooner I could get them out of there, the better.
Walking in through the main doors, I stopped my crunching of ice and suddenly swallowed hard. Standing before us, was an absolutely breathtaking woman who smiled down upon us, greeting us into her establishment.
“Well hello!” she beamed enthusiastically at us, “Welcome to Missy’s Dresses!”
My sister was grinning ear to ear and bubbling with excitement but I was finding my mouth going dry as I stared openly at this stunning angel from heaven. Immediately capturing my full attention and right at eye level, I gaped in awe and amazement at this gorgeous woman’s deep, plunging line of cleavage, disappearing down into the V cut of her silk top that was stretching mightly to contain her massive breasts. They were round, perfectly shaped, and in all honesty, huge! I had never seen boobs so big in all my life, especially on a woman so slim. My heart thumped within my chest and I felt a familiar stirring in my groin as I stood there mesmerized.
She had a snug pencil skirt that wrapped around her curvy hips and seemed to accent her narrow waist and hourglass figure. Her long, silky blonde hair was pulled back, not severely, but in a very feminine way that emphasized her very pretty face. Full, luscious lips and delicate, yet commanding eyes that held me in their gaze, prevented me from evaluating her further. I felt instinctively that here was a woman of presence, so completely night and day from my own weary mother.
“And what’s your name, Young Man,” she said as she bent down slightly to speak to me.
Her cleavage yawned before me and I licked my dry lips as I stared at her soft twin mounds of feminine glory.
“C-C-Chris,” I stuttered uncertainly. I felt my cheeks glowing red at being the center of attention of this goddess and I was forced to look down at the floor.
“Hello Chris–Let’s see…I’m guessing you’re about ten, right?”
My face flushed with embarrassment at her gross underestimation of me. It’s true that I was short with somewhat effeminate features but I always thought of myself as a guy’s guy.
“I-I’m thirteen!” I protested.
“Oh!” she exclaimed, putting her slim, manicured hand in front of her mouth, “I’m sorry, I had no idea!”
“And are you here to get something pretty?” she asked in her syrupy voice.
I had no idea why she’d draw that kind of conclusion about me but it was enough to allow me to finally regain my composure.
“No way!” I snapped, “We’re here for my dumb sister.”
I pointed at Lindsey who was staring with star struck eyes at the vast selection of frilly, girly clothes all around us.
“Well I know we’ll find just what it is you’re looking for,” the lady said, focusing in on my sister, “My name is Barbara, and this is my store.”
She gave us all eye contact and when her gaze fell upon me, I practically shivered. I think I was in love! What a total babe!
My mom explained the type of dress they were looking for and Barbara led them to a different section of the store where they might find it.
All the while, I took the opportunity to drink in her sexy, adult curves. What a woman! From every angle, she was incredible. She wore high heeled pumps that matched the silky top she was wearing and her snug skirt went no further than the top of her knees, allowing me to admire her smooth, shapely legs.
Following behind her, I was looking her up and down, when she suddenly turned around to make sure I hadn’t become lost. Unprepared for her about face, I stumbled forward and ran right into her, my face mashing against her soft pillowy breast.
“Oh! I’m so sorry!” she exclaimed, although she was wearing a knowing smile as I blushed furiously from my clumsiness. Despite my embarrassment, my penis was rock hard and I was already thinking of ways to relieve it the second I got home. To be sure, this woman would feature prominently in my fantasies for quite some time.
My sister began picking out dresses, far more than I knew we could afford, or would have time to try on and when Barbara went to help out another customer, I quickly began to get bored.
“Mom? How long is this gonna take?” I whined pitifully.
“Just a little bit longer Chris, try to be patient,” she chided me.
“But this is soooo boring,” I complained, making myself a complete nuisance.
“Chris, why don’t you go amuse yourself somewhere in the store–we’ll find you when we’re done,” she told me tiredly.
Muttering to myself, I shuffled off, knowing I was going to be bored to tears no matter where I was in the store.
I spied Barbara about twenty feet away, talking to what I assumed was her assistant, a real knockout from what I could see. While not as curvy as her boss, this woman looked to be about 19 or 20, with long, straight blonde hair and a body that looked like had been sculpted in a gym. She looked like a real hottie!
Totally distracted, I set my drink down on one of the store’s fixtures, not even paying attention to what I was doing. I just wanted to spy on these two while they were unaware of my attention.
All of a sudden, I heard the contents of my drink spill noisily as the cup fell about a foot off the ledge I’d set it on. Looking down, I gasped in shock as the red liquid splattered all over several fancy white dresses that had been laid out on the next shelf down.
Oh my god! What a huge mess!
Looking around, I saw that no one had yet witnessed my blunder and taking in the scene of disaster, panic filled me and rendered me incapable of rational thought. The only thing that occurred to me was to flee and right away! If only I could get my mom to leave before it was discovered, I might escape punishment.
Barbara and her assistant were still occupied with their conversation so I scurried back to where my mom was evaluating my sister’s latest choice.
“Oh that’s lovely, Dear,” she remarked, “What do you think?”
“I think I like the pink one better, Mommy,” she replied.
“Do you?” she asked.
It was obvious they were in no hurry to get going and I fidgeted nervously, shifting my weight from one foot to another as I bit my lip in angst.
“Are you guys about done?” I asked anxiously.
Oblivious to my state of panic, my mom hardly looked my way.
“Chris I thought you were going to occupy yourself until we came and got you.”
“How much longer is this gonna take?” I pleaded with her.
“For heaven’s sakes, Chris, you’re really becoming a trial,” she replied with annoyance. Of course, she always said that but what grated at me now was that she used to it delay whatever it was I wanted at the moment and what I wanted right now was to get out of there fast!
From behind me, I heard the distinctive sound of approaching high heels; a ‘click-click-click’ that announced my moment of retribution was at hand.
“Excuse me, Ma’am,” the commanding voice spoke from behind me and I knew with sinking certainty it belonged to Barbara.
It was only with great effort I was able to turn around to face her and I saw she was holding my empty Chuck-E-Cheese cup in her lovely slim hand.
The blood drained from my face and my palms felt suddenly clammy.
“Does this cup belong to one of your children?”
I resented being classified as a child but that was the least of my worries as my mom looked from the cup and over to me.
“Why yes it is, did Chris neglect to throw it away when he was done?” she asked, innocently unaware of what I’d done.
“Will you come with me a moment?” Barbara asked. Her voice was friendly but firm and it filled me with dread.
As we followed along behind her, my mind raced with any possible excuses as to how I could talk my way out of this. The problem was, I simply couldn’t think straight. Somehow, I knew this woman wouldn’t tolerate being manipulated like I was used to with my mom–she’d see right through me.
When we got to the scene of my spill, my mom’s face showed both horror and dismay. This was exactly what she had warned me about before coming in and my blithe dismissal was still ringing in my ears.
“I found this mess just now and I recognized the cup from the ones your children were drinking from,” Barbara explained, “Would anyone like to own up to what happened here?”
My sister was still holding her cup with it’s lid still on and there could be absolutely no doubt as to who the culprit was. Still, I kept my silence with my eyes downcast, hoping somehow, by some miracle, this would all be forgotten. Barbara stood towering over me, her hands on her curvy hips as she waited for an answer with growing impatience.
“Young Man,” she addressed me sternly, “Is there something you want to tell me?”
A bead of sweat trickled down the side of my forehead and I absently wiped it away.
“It wasn’t me,” I bleated weakly, but it was quite obvious no one believed me.
“Chris, I am very disappointed in you,” my mom said with uncharacteristic authority.
“But it wasn’t my fault,” I began to whine. This tactic had always served me well and I hoped it would serve me again or maybe at least lessen my punishment.
“I’m sorry, but these were very expensive dresses,” Barbara informed my mom, “Something will have to be done.”
My heartbeat was thumping in my chest as I glanced anxiously up at the store manager. Despite the fact that she was incredibly sexy, I feared her on a level I didn’t fully understand and she looked capable of just about anything.
“I’m so sorry,” my mom said, a look of anxiety and worry creasing her face, “He’s just more than I can handle these days. I honestly don’t know what to do with him anymore.”
“If you will allow me, I will see to it that he is properly punished, and then we can make arrangements for him afterwards.”
My mom appeared immensely relieved, probably because she had no means of paying for the damaged goods. She was also glad, I think, to have someone who would finally be able to give me the discipline she was incapable of providing.
“Yes, by all means,” she quickly agreed.
“But Mom,” I whimpered piteously, “it wasn’t my fault!”
“Come along Young Man,” Barbara said as she snatched my wrist with surprising strength, “You’re going to be taking a trip over my lap.”
“Huh?” I gasped.
I gulped in fear and tried to wrench my hand from her grip but her hold was like steel.
“No!” I squealed, “You can’t spank me! Mom!”
I was sure my mom would intercede on my behalf, after all, I hadn’t been spanked since kindergarten and that was by my teacher. My mom would never allow me to be given such a childish punishment by a total stranger! Not at my age!
To my surprise and chagrin, my mom not only didn’t stop her but she added a few words of her own.
“Chris, you’ve had this coming for a long time now. I think this is exactly what you need and deserve.”
I pouted and whimpered as Barbara dragged me into her spacious back room, opening a drawer from a tidy desk against the wall. She deftly retrieved a stout, oval shaped wooden paddle with nickel sized holes in it’s face.
Panic seized me and I stomped my feet frantically.
“No…no….please–please, I didn’t mean to–I–I was just…” I pleaded.
Barbara took a seat in a straight backed chair and faced me as she began unbuttoning my shorts.
“I don’t like liars, Young Man,” she told me in no uncertain terms, “I’m going to give you a good, hard spanking and teach you a lesson you won’t soon forget.”
By now, tears had formed in my eyes and I tried to stop her hands from pulling down my shorts.
“Oh–oh–no! Wait! P-please–please don’t spank me!” I wailed.
This woman was implacable and she was completely ignoring my whining pleas for her to stop.
Her beautiful features were set firmly as she went about her serious business, slapping my hands away and as she yanked my shorts down, her tremendous breasts defiantly teased me as they jiggled within her tight silk top. Without the slightest pause, she yanked my Superman underpants down and jerked me over her toned lap.
“No–no–please–please don’t!” I wailed as the first tear spilled down my trembling, panicky face.
With her high heeled pumps, I found myself lifted completely off the ground, off balance and all too helpless in her steely grasp.
The hard oak paddle seared itself across both my soft, youthful buns and I howled out in angst and surprise at the ferocity of her first swat.
Tears poured down my face now as I began bawling like a child instead of the teenager that I was.
Looking up, I could see Barbara in a nearby mirror as she paused long enough to look back into my eyes.
“You really are a sissy, aren’t you?” she said as she shook her head disapprovingly.
Desperate to make her believe I was tougher than I really was, I shook my head vigorously.
“No–no Ma’am!” I cried between sobs.
“Well, I know a sissy when I see one and you have sissy written all over you. You’re not the first little boy who’s felt the sting of my paddle but you can be sure you’ll get what’s coming to you,” she said tersely, finishing her sentence with another pair of hard, angry swats to my defenseless buns.
I kicked and swung my hands wildly in the air, gasping for breath as her vengeful paddle came down again and again. Looking up briefly in the mirror, I saw a blurry image through the tears flooding my eyes and streaming down my face. I looked like a naughty little boy being punished by his babysitter as her fierce paddle swatted me repeatedly with impunity.
I kept waiting for her to stop, after all–she’d taught me a lesson and then some–but she just kept up an even rhythm, slapping one tender cheek, then the other, then the side of one rosy cheek that had escaped her attentions. My pliant, stinging buns danced under her ferocious assault, flattening briefly under the impact and then jumping back up to receive another dose of her unyielding wood.
I cried like I’d never cried in my life, snot dribbling down my face and tears spilling down my cheeks as I shook my fists in helpless futility.
At last, she stopped and pulled me to my feet, staring down suspiciously at my damp, limp genitals.
“Did you wet yourself on my lap?!” she asked incredulously.
I was so distraught all I could do was bawl incoherently and dance in place as she held my wrist captive.
Taking my lack of denial for a confession, she wrenched me around and landed another harsh, stinging swat on my bright red bottom.
I howled again and bucked forward but could go no more than a few inches due to her iron grip on my arm.
“You belong in diapers, you little sissy,” she informed me as she looked down on me coldly, “But I have something here that will do temporarily.”
I could do little but focus on the blistering inferno blazing across my bottom and I hopped from one foot to another as the tears poured down my ashen face.
“I want you to place your hands on the desk here,” she commanded me, “And if I see you move either one, I’m going to pull you right back over my lap–understood?”
“Y-y-yes M-Ma’am,” I bawled.
Doing as I was told, I sobbed and felt sorry for myself as I stared at the near wall. In my present position, bent over slightly as I was, my bright red bottom stuck out like a beacon of shame for everyone to witness. As if to heap further humiliation on my situation, the backroom door opened up and Barbara’s stunning blonde assistant came in. Her gaze fell from my tear-stained face, down to my candy-apple cheeks before she smirked knowingly.
“Looks like you found the one who made that mess,” she remarked.
“Yes I did, and as you can see, he’s one sorry little boy now for causing all the trouble,” Barbara replied.
The cute blonde chuckled, her lack of sympathy obvious.
“I’ll say, maybe that’ll teach you a lesson,” she said to me before going back out onto the salesfloor.
I was mortified, having to stand there, nude from the waist down, and so obviously punished, although at least I’d managed to keep my privates hidden from Barbara’s assistant.
Offering my mom a place to sit, Barbara turned to face her directly.
“So, tell me Mrs…”
“–Schaaf,” my mom replied, “but please just call me Pamela.”
She seemed eager to work with this stern woman which made me all the more nervous.
“Thank you Pamela, I’m very pleased to meet you,” Barbara said cordially as she extended her hand.
“I’m wondering if you might tell me a little about your son,” she began “I have my own ideas from what little I’ve observed on my own, but I’d like to get your own impressions of him.”
“Of course, I’m only too happy to help,” she answered.
“Has he always been this bratty? He seems inclined to try and get his way by whining and being a general pest.”
“Oh yes–very much so,” my mom replied quickly, “And it’s only gotten worse over the last couple of years–its gotten so he’s constantly fighting me on every little point, doing anything to avoid being responsible.”
“Mm hm, I thought so. And would you say he tends to stay indoors a lot? I’m guessing he doesn’t have many friends and he’s disinclined towards sports.”
“Yes…yes, now that I think about it, that’s exactly right.”
“Mm-hm, now tell me, when I first saw him, he looked more like a little girl in boy’s clothing than a young man of thirteen. I know that any girl would die for his smooth hairless legs and soft features. Does he get pushed around a lot at school because of his looks?”
“Mm, I’m afraid so,” my mom answered, “I guess they don’t see him as much of a guy’s guy. In fact, some even call him a sissy.”
“I can certainly see why,” Barbara responded.
“I’m not a sissy!” I interrupted them as I sobbed in desperation.
Barbara tried valiantly to hide the smirk on her face before pressing on.
“Let’s see…I imagine that he spends a lot of time masturbating too…am I right?”
My face blazed scarlet and even my mom’s face showed a little color as she nodded her head in dismay.
“Yes, its really become quite a problem,” she explained, “He’s constantly in his room with his underwear around his ankles, stroking himself to god-only-knows what. I’ve tried everything I can but I’m just not having any effect on his behavior.”
“That’s a lie!” I hollered angrily, my face still wet with tears.
“Young man,” Barbara said firmly, “I’m this close to pulling you over my lap again for another spanking—is that what you want?”
“No!” I sobbed petulantly.
Barbara and the others went back to ignoring me and she crossed her arms over her big, curvy chest.
“It’s clear I have a lot of work to do,” she announced authoratively.
“I have a proposal to suggest which will take care of the damage your son has caused and erase any financial obligations for you.”
“Oh–anything,” my mom quickly agreed. It was clear she was only too happy to have someone else deal with me.
“I suggest you drop off Chrissie here after school and he can work for me until he’s paid off his debt for the damage that he’s done.”
“It’s very kind of you to offer that–of course we’ll do that. Just tell me when.”
I groaned inwardly. As if her spanking wasn’t punishment enough, I was going to be under this terrible woman’s thumb for who knows how long! And who knew what further humiliations she had in store for me…
“How about a week from Monday?” Barbara asked, “There are a few things I’d like to have ready for him when he arrives for his first day of work.”
I could only imagine what those were but I held my tongue in silence.
“Oh yes–certainly,” my mom hastened to agree.
“Good–then it’s settled,” Barbara announced with pleasure,
“Chrissie? Since you seem to have trouble keeping your pants dry, I’ve got a little something that might help in the short term.”
Barbara went to a set of drawers and brought forth a white and pink set of underwear. Wiping the tears away from my face, I saw that they were actually thickly padded training pants, with a Barbie motif on the front and seat. Normally, I would never have submitted to such an indignity but there was no way I was going to stand up to this woman.
“Come here, Chrissie,” she ordered me, “That’s a good boy. Now step into your new panties.”
I whimpered and continued to sob as I gingerly lifted my legs one at a time into the childish trainers she was holding open for me. Wavering uncertainly before her, I had to reach up to her shoulders to help steady me. All too slowly, she pulled them up my smooth, skinny legs and pulled them around my hips. Her big, sexy round breasts were mere inches from my face but now I was regretting having ever set eyes on them.
The trainers were soft and comforting, at least upon my genitals, but the seat felt like sandpaper as soon as it made contact with my hot, stinging buns. I let out fresh sobs of defeat as she pulled them snugly into place but I also managed to breathe in the scent of her perfume as I stared down the front of her silky top at her incredible cleavage.
Scooping up my shorts, I thought she was going to put them on me but instead, she handed them to my mom.
“I suggest you leave these off until later,” she told her matter-of-factly to which my mom nodded.
I was going to make some sort of protest, but then I thought better of it–I certainly didn’t want to go over this stern woman’s lap again!
Towering over me in her heels, Barbara turned to face me once more.
“Can you do your best to keep those training panties dry until next Monday?”
My cheeks burned with shame as I stared at the floor and nodded reluctantly.
“Okay Sweety?” she repeated, as if she hadn’t seen my first response.
“I will,” I sobbed anew as I blushed again.
“That’s a good boy,” she replied as she smiled down at me, “I have the feeling we’re going to get along, just fine…”

Chapter Two Chris’ New Home

For the next two weeks, I could think of little else, other than Barbara. And my situation was made worse by the fact that I was helplessly caught between two diametrically opposed emotions–shame and lust.
On one hand, every time I thought of the buxom store manager, I blushed furiously as I re-lived my painful and humiliating punishment at her hands. Never had I met such a powerful, strong woman, so stern and strict, who insisted on dealing with me like I were nothing but a small child. I hated her total confidence and absolute authority, not to mention the fact that she was a lot stronger than me.
On the other hand, when I saw her in my mind’s eye, I couldn’t help getting intensely aroused, despite my burning anger towards her. That voluptuous body and pretty face; her long, shapely legs and silky brunette hair. She was sooo sexy! Putting aside my smoldering resentment toward her, I found myself masturbating shamelessly several times a day as I hungrily fantasized about her. I hated myself for giving in to the temptation when she’d shown me nothing but humiliation and a blazing bottom but I couldn’t stop no matter how hard I tried. After dreaming about her delicious curves, my mind focused on her incredible bosom. Imagining being able to touch those soft, fabulous breasts sent me over the edge of orgasmic ecstasy every time…
But today, I was sitting in class, trying to scheme some ploy in which I could foil my mom’s plans to take me back to that woman’s store. I had in mind my usual whining and complaining, hoping to wear her down until she finally gave up. I was fairly certain I could put a wrench in her plans when suddenly, I heard a very distinctive sound coming up from behind me.
Click, click, click, click…
“Who’s that?” I heard someone nearby whisper in awe.
My hair stood up on end as I slowly turned around, dread filled certainty washing over me like an icy bath.
“Hello Chrissie,” Barbara said in her melodious, yet commanding voice.
I felt myself wilting as my heart began beating wildly in panic. I hadn’t anticipated this turn of events at all!
Standing tall over me in her high heels, I stared up at the object of my anger and lust, my mouth hanging open stupidly. She was wearing a very short skirt and a snug, form-fitting button top that clung tightly to her proud, eye-popping breasts. It took my breath away and my mouth was suddenly parched.
“Your mommy has given me permission to pick you up myself, Chrissie,” she told me with a knowing smile, “And your teacher has graciously decided to let you out of class early.”
“B-b-but…I-I-I don’t–” I stuttered.
“Come along Chrissie,” she said in a friendly, yet firm tone, using her name for me that I detested, “I’m your babysitter now and it’s time for us to go.”
Without waiting for an answer, she reached down and took hold of my hand, standing me up like I were a toddler. With every one of my classmates now staring at us, her other meticulously manicured hand reached down and squeezed my bottom inquiringly.
“Not wearing your training panties today?” she asked, loud enough to make sure that everyone could hear.
“She-she’s just kidding, fellas,” I croaked with a nervous laugh, hoping to defuse her comment and minimize the intense humiliation she was causing me.
“Well I just hope you can keep from wetting your pants long enough before I can get you over to the store and put you into some diapers and plastic panties,” she announced merrily.
I felt the blood rushing to my face as the word ‘diapers’ got repeated by everyone around me. Blushing furiously, I couldn’t help but hear a chorus of giggles erupt from around the class.
“Wa-wait!” I squealed anxiously, “Y-you can’t take me with you.”
I struggled to free myself from her grip but only succeeded in making myself look weak and foolish.
“Perhaps I should tell your classmates of our last meeting, Chrissie,” she smiled with mischievious sweetness.
Abruptly, I stopped all resistance. I couldn’t risk her telling everyone how she’d spanked me like a child and then left me to stand there, my bright red bottom on display for all to see.
“Mmm-hm. I thought so,” she said smugly, “Come along now.”
Defeated and shamed, my world was a blur as I hung my head low and walked along behind her. Taking me by the hand, she led me out of the classroom as everyone openly stared at me. My face burned with shame at being treated like a child in front of all my peers–I’d never live this down!
As we went out into the parking lot, Barbara led me to a white, late model minivan. I was about to take a seat in the front when she held me back and opened the sliding rear door instead.
“No, sissies sit in the back,” she instructed me and before I knew it, she was pushing me into an oversized child’s seat that was secured to the bench seat.
“Wha-what are you doing?” I protested.
Out of the corner of my eye, I could see a group of sophmore cheerleaders stopping to take in this strange scene–a 13 year-old being strapped into a child’s seat by what looked like his mommy. I blushed again heatedly as Barbara quickly secured the seatbelts and straps holding me in place, all while I whined desperately for her to leave me be. Once she finished, she stepped inside and closed the door, at least providing us with a welcome sense of anonymity as she took a seat next to me.
Barbara was all smiles as she cozied up close to me, her big breasts jiggling within her thin top. I felt a little nervous, alone with this incredibly sexy woman who was much older than me and trapped in her car as I was, I felt like her captive. As I gazed over her enticing, bountiful curves, my hands felt clammy and I became aware of a nervous buzz in my stomach.
“Chrissie, I think we may have gotten off on the wrong foot,” she said in a warm, friendly way. Her voice was soft now, soothing and pleasant to my ears.
“We-we did?” I said, my voice breaking. It suddenly felt very warm in the van.
“Yes, but I can’t tell you how excited I am that you’re going to be spending time with me. We’re going to have so much fun together! I even bought you a special present.”
I was completely taken aback. I was expecting more of the same stern, disciplinarian that I’d encountered at her store. This side of her made me feel at ease, although her smoothering sexy presence so close to me continued to make me nervous.
Slowly, I watched as she undid the upper button of her snug, straining top, revealing the lacey clasp of her bra underneath. My heart was pounding in my chest wildly now as I stared at her big soft breasts, pushed together and displayed before me in a way I couldn’t ignore. Her scoop necked top was plungingly low as it was and this exposed yet another inch of her smooth, plump bosom. My little penis reacted instantly and it strained urgently within my underwear. She was even more incredible than my imagination remembered her!
I licked my dry lips and tried to breathe normally as I saw her produce a small box, wrapped with babyish gift wrap. Placing it in my hand, she beamed down at me, as if this was some wonderful present that I had been waiting all my life for.
“Go ahead, Chrissie, open it up–it’s especially for you,” she told me encouragingly, her beautiful smile overwhelming me.
I was at a loss for words as I slowly undid the pink silk ribbon and tore away the childish nursery print wrapping paper. I couldn’t imagine what it was she could have gotten me, nor why she chose to wrap it like something for a baby shower.
Inside was an oversized rubber pacifier, still in its orginal see-thru plastic packaging and the label that identified it as a ‘Sissy-Paci’.
With a confused look on my face, I held it in my hand while Barbara suddenly drew closer to me. Taking her slim hand, she held my face gently as she slowly and deliberately planted a big wet kiss right on my quivering lips!
If I was breathing hard before, now I was ready to hyperventilate!
I’d never kissed a girl in my whole life and now this stunning babe had just kissed me in the most erotic way!
With her rose colored lipstick still upon my lips, I stared dumbfounded at her, although my throbbing erection didn’t have to be told that I was the luckiest teenager in the world.
“You see?” she said sweetly, “You and I are going to get along just fine.”
I still didn’t know what to say but her smile was infectious and it made me swoon with desire.
“Now…this baby pacifier is very special–it’s made specifically for big sissies like you that are going to be nursing soon,” she said cryptically as she opened the package and took the pacifier in her creamy hand.
“Open up Chrissie,” she said softly as she positioned it before my lips.
I didn’t know what she was doing and I was completely confused. What did she mean by “nursing soon”?
“No–no…” I squirmed but the straps holding me in made it difficult to struggle.
“Open up Sissy,” she smiled as she gently rubbed the big rubber nipple against my trembling lips. Just as I managed to bleat out another protest, she pushed it past my parted lips and into my mouth, stifling my words.
“Mmrphh,” I whimpered as the pliable rubber object filled my mouth completely. Sucking on a soft, flexible rubber nipple suddenly brought back long forgotten memories, making me feel very babyish.
“There you are,” she said happily, “It’s perfect for you.”
I shook my head in protest, the large pink plastic ring in front jiggling, but Barbara continued to smile broadly at me.
“Now I know today is going to be a lot for you to take in Chrissie,” she said as she passed the plastic loop over my head and around my neck, “I know right now, you’re feeling confused and a little unsure. But first, I want you to understand that this is your very own pacifier and you must never take it out. Ever. Okay? Do you understand? Because if I see you take it out, I’ll have to pull down your pants and give you another spanking, except this time, it’ll make your last trip over my lap seem like love taps.”
I felt a shiver of fear ripple through me as I stared back into her pretty piercing eyes while she explained all this to me. Her voice was still warm and friendly but it carried a firmness that left no doubt about her willingness to enforce her rules.
“I don’t want to have to spank you again but I will if you make me…and you don’t want to cry like a little baby again, now do you, Sweety?” She asked tenderly.
I shook my head slowly feeling numb all over.
“That’s good,” she said reassuringly. I felt her soft hand on my thigh now and she gently began stroking me as she talked. I was so confounded and bewildered I was paralyzed with indecision but there was no mistaking the incredible hard-on that was tenting my trousers.
“You see, I recognized right off that you were a big sissy. You’re actually a little baby girl in a big boy’s body, desperately trying to get out, but no one will let you,” she said in cutesy voice designed for talking to toddlers, “But now that’s all going to change.”
I shook my head no but she just ignored me and plowed on like she couldn’t see me.
“Oh yes, because from now on, you’re going to be my precious little baby girl–I have so many plans for you–I can’t tell you how excited I am to show you everything that’s waiting for you back at my place,” she gushed, “You’re just going to love the cute, prissy outfits I’ve got for you–you’ll have a wonderful time!”
I was aghast at the picture she was painting for me but it was obvious she was truly thrilled about her plans and it was equally apparent she expected me to feel the same.
“And I know a big sissy like you must feel truly naked without a thick pair of diapers and plastic baby panties–but don’t you worry–we’ll soon take care of that problem,” she giggled.
I shook my head and whimpered pleadingly.
“Now–you just keep that pacifier in your little mouth–okay Sweety? Don’t even think of taking it out–all little babies need their pacis and you’ll come to love yours–I just know it!”
Rising up, Barbara moved past me and opened up the door–just in time for a pair of high school girls who were walking past at that moment to look in and see me, sucking my pacifier with its big pink plastic ring on the mouthguard. I blushed in shame as they giggled and walked past, too late for me to take it out, even if I’d had the courage to do so.
Barbara closed the sliding door and went around to get in the driver’s seat, buckling herself in as she looked back at my panicky face.
“Don’t worry Chrissie, everything’s going to be just fine from now on.”
The thought occurred to me to spit out the pacifier, undo the seatbelts and bolt out of the car. And I almost did, but the van was already moving and my window of opportunity was gone.
It didn’t take long to reach her store, and once again, she insisted on holding my hand like a child all the way in. To be honest, I wasn’t sure how I was going to deal with her once we got there but now that we had arrived, I still didn’t have a good plan. I felt like a fool as I walked through the store, a fat pink pacifier stuffed in my mouth, as shoppers stared at me openly. I did my best to look the other way but their whispers followed me relentlessly.
“I’m sure you must be feeling very insecure without some diapers and plastic panties on but don’t worry, Chrissie–I’ll get you changed in no time,” she assured me.
Butterflies buzzed in my stomach as I searched around for some sort of escape. This was all happening too fast!
Taking me through a back door, we walked down a short, well tended pathway that led to the front door of her house. Without pausing to tell me what was going on, she ushered me into her home, a modest but immaculately clean single story house. Passing a large living room area, she wasted no time taking me down a brightly lit hallway.
“And down here is going to be your new bedroom Chrissie, or should I say, your nursery. I know you’ll just be thrilled when you see it,” she waxed enthusiastically.
Opening the door, Barbara practically pushed me inside but as she stood behind me, she brought her head down to my level to speak closer to my ear.
“You see, Chrissie?” she said softly, “there ‘s everything a little sissy could ever hope for–over there is your dresser, which I’ve stocked with lots and lots of plastic panties, rumba panties, diaper shirts and sissy tops. And you have your very own crib to sleep in, with a nice waterproof vinyl mattress cover in case your diapers ever leak. I’ve collected a big assortment of baby dresses that I know you’ll just love–see all the colors and styles? All in pretty pastel colors, although as you can see, pink has always been my favorite, just as I’m sure it’s yours too.”
My head was swimming as she extolled the many wonderful items of this babyish room, which looked to all intentions to be that for a two or three year-old toddler, rather than a young man of thirteen. The walls were papered with a nursery print design of giraffes and bunnies over a pink and lilac background. There were dollies arranged next to a box of plastic building blocks and next to the crib was a vinyl covered changing table, large enough to accomodate my semi-adult frame.
Sucking nervously on my pacifier as I tried to take all this in, I suddenly felt Barbara’s hands on my waist as she began pulling my shirt up and off of my torso without warning. I squealed in protest which was dutifully muffled by the pacifier filling my mouth but nevertheless, in seconds, I was shirtless. No doubt, any other young man would have spit out the pacifier at that point but I obediently kept it in my mouth which made me look like a petulant toddler.
“Its time to get you changed, Chrissie,” she announced happily, “I’m sure you must be very anxious to be pinned into your new diapers.”
I shook my head and tried to stop her but she was both quick and deft and despite my efforts to stop her, she got my pants unbuttoned and was bringing them down quicker than I thought possible. My struggling caused me to stumble and I fell over, landing with an unceremonious thud on the carpeted floor.
“Careful Chrissie, you don’t want to hurt yourself do you?” she said as she succeeded in removing my shoes and pants.
All the time I was whimpering and protesting, trying to communicate my desire to keep my clothes on but she only ignored my muffled jabbering.
“I have a lovely top that I just know you’ll think is the cutest thing,” she said as she picked up a white and pink t-shirt sort of garment.
“And after we’ve got you all dressed and diapered for beddie-bye, we can do some coloring in your Barbie coloring books–would you like that?” she asked hopefully.
I shook my head but she was already pulling the soft fuzzy top over my arms. It had short, puffy, elasticized pink sleeves and birdseye lace around the cropped hem. But what really made me cringe was the cartoon applique on the front and word ‘Princess’ in childish writing on the chest.
“Oh, that looks just wonderful on you,” she enthused, “but these ugly underwear simply won’t do.”
“Come look at your new underwear, Chrissie,” she said as she had me step over to the changing table, “Stacks and stacks of bunny soft diapers, for you to wear and wet from now on. No more pretending to be a big boy anymore. And there’re all kinds of plastic panties in the cutest designs so no need to worry about leaking either.”
That was it. I had reached as far as I could go with this crazy woman. There was no way she was going to dress me up like a baby, put me in diapers and do whatever it was she wanted with me. I had no plan in mind, only that I was going to get out of here and run as fast as my legs could carry me. I was reasonably sure I could outrun her in those heels of hers, I just needed to get a head start.
“Stop it!!” I shouted angrily as I finally spit out that accursed pacifier, “I’m not wearing any damn diapers and you can go to hell!” I shouted indignantly.
Barbara’s face registered genuine shock, but she quickly recovered and steeled herself for a confrontation. It was only then that I noticed she was blocking my way to the door, to say nothing of the fact that my pants were still on the ground.
“Chrissie, you’ll learn that I do not tolerate misbehavior or any cursing of any kind in my house.
“I was hoping we could get through a day without you going over my lap but I guess I was wrong,” she told me sternly. Standing before me authoritatively with her slim hands on her hips, her big breasts seemed to thrust out defiantly.
With a swiftness I was unprepared for, she suddenly clenched my wrist in her hand and jerked me over to the crib which had one side already open. Taking a seat on the edge of the plastic covered mattress, she flung me over her lap and yanked my Batman underwear down.
“NOOOOO!!!” I cried as I saw her reach in front of me to snatch her wooden paddle.
“Chrissie, I hope your little tantrum was worth the tears you’re about to shed,” she said tersely, “I’m going to give you the spanking you so richly deserve.”
Before I could think how to respond, I felt her paddle slap my bottom with the scorching wallop of buckshot.
I howled out and kicked instinctively just as she swatted me again even harder.
Unable to maintain my composure a second longer, I burst into tears just as her paddle rained down on my defenseless cheeks again and again. With crisp, angry swats, she spanked me with a vengence, turning my pale cheeks from pink to a bright fire-engine red in a matter of seconds. She peppered my bottom, swinging her wooden paddle in a punishing rhythm as I wailed helplessly and shook my fists in frustration. I saw now how foolish I had been, thinking I could stand up to her. Her sexy nature automatically made one inclined to underestimate her but I wasn’t underestimating her now!
Bawling like a baby, my legs scissored in the air as I my underwear went flying into another corner of the room. Through eyes brimming with tears, I gazed back at her high heeled sandals, spread slightly apart to support my weight as she held me securely with one hand and spanked me mercilessly with the other. Every cruel slap of her paddle on my soft, tender cheeks reduced my will to resist her until I was willing to do anything–anything in the world, just to make the terrible spanking stop.
Her fearsome paddle seared itself across my cheeks like a swarm of hornets as I sobbed and cried helpessly against her superior will and strength.
At long last, she stopped my painful punishment.
I lay over her lap, too weak to get up, my face wet with tears as I bawled like a naughty toddler.
“Are you ready to behave yourself now?” she asked patiently.
Howling miserably, I did my best to respond in the affirmative.
“That’s a good little boy,” she said, all traces of anger suddenly gone.
Helping me to my wobbly feet, she hugged me to her big cushiony bosom, rubbing my back and speaking softly into my ear.
“There there, Baby, its all over now, everything’s going to be okay….”
I shifted my feet from one to another as I practically danced in her arms but my buns stung so much I couldn’t stop crying. My tears splashed down onto the exposed buttery skin of her soft breasts, trickling down the deep crevice of her cleavage.
“There there, little sissy,” she cooed as she kissed my ear, “Go ahead and cry, it’ll do you good.”
I hated the fact she had such complete control over me and I bawled in frustration, even as I felt her big, warm, soft breasts pressing against my chest.
She continued to stroke my back and comfort me, occasionally kissing a tear from my cheek tenderly.
“Thaaat’s it, Chrissey,” she whispered, “Get it all out….cry like the little sissy you are…”
She talked to me warmly and without anger, although I found her words extremely humiliating to have to hear.
With the loving care of a mother, she started gently rocking me as she began softly singing a lullabye in my ear; “Mommy’s going to put her little baby in diapers…diapers…diapers to keep her dry…”
I certainly didn’t want to wear diapers but I wasn’t about to try and stand up to her again.
Stepping back from her, I wiped the tears from my face with a swipe of my arm as I gazed at her pretty face. Still sobbing uncontrollably, with my breath heaving in my chest, I looked into her deep, captivating eyes. I saw nothing but love and affection, motherly love that I hadn’t felt for many years but the pain that was raging across my backside still filled me with anger and resentment towards her.
“Come along Chrissie, it’s time for us to get you changed into your diapers and plastic panties now.”
Gently, she led me over to the wide vinyl covered changing table and set me down where I winced in pain as my hot bottom came into contact with it. A fresh set of tears burst from my eyes and Barbara responded by smiling understandingly and pushing my pacifier gently back into my mouth.
“Now, I know you want to act like you don’t like this but we both know you do,” she told me in no uncertain terms, “All sissies love their diapers and in no time–you’ll feel naked without them.
“But don’t worry–I want you to know that from now on, you’ll never be without them. And you are never to touch them either–understand? The only ones who have permission to change you or touch your diapers in any way are adults–okay, Chrissie?”
I nodded miserably as she smiled with satisfaction down on me.
“That’s mommy’s good little girl,” she said to me.
She took a trio of cloth diapers that were stacked neatly next to the table and positioned them below me. Lifting me up easily by the ankles, she slide them under and began working them around beneath me for a proper fit.
I protested weakly and incoherently as she smeared diaper rash creme across my hot, stinging buns, then set me down on the soft, pillowy mass of cotton.
“You don’t have to worry about wetting anymore Chrissie,” she said cheerfully as if it were a big problem for me, “See the extra soaker pads that are sewn into these? They’ll be sure to hold all your pee, even after a long night of wetting. They’re even called Bedwetters, and they were specifically designed for big sissies like you that wet a lot.”
I felt so childish as she sprinkled fragrant baby powder all over my loins and even up onto my chest. The infantile scent assailed my nostrils and breathing deeply of it, I felt transported back to my childhood.
“Here’s one pink bunny pin,” she announced merrily as she held the bulky sides together and pushed the safety pin into the cloth to secure it.
“And here’s the other,” she said, doing the same with the other side.
“There! Look at you!” she exclaimed as her long-nailed creamy hand gently patted the front of my now thickly diapered crotch, “Your very first diaper since your mommy potty trained you. Now, all you need is a pretty pair of plastic baby panties!”
Sucking anxiously on my pacifier, I squirmed nervously as she leaned over and began sifting through my new dresser for a covering.
What would my friends say if they were to see me now?
“Here we are!” she said brightly, “Perfect for a sissy’s first day in diapers!”
Holding them before me, I gazed in dismay at the white translucent plastic panties decorated with blocks and rattles. Pink birdseye lace lined the legs and waist and without delay, she began working them over my feet and down my legs towards my hips.
“See how these are partially clear?” she asked, “That way, Mommy can tell when her little baby girl has wet herself.”
I shuddered at the thought even as I noticed her subtle change of pronouns when she referred to me.
Bending over me as she went about her business, I gazed absently at her big sexy breasts within her tight top as they swung ponderously before me.
Tugging the soft waterproof panties up my legs, she worked them over the thick, bulging diaper until the elastic waistband was hugging my skin. Taking the baby powder, she powdered between my legs and then softly rubbed it into my tender skin.
“Oh my, you look soo cute,” she gushed happily, “So completely natural in diapers, just like a perfect little sissy girl.”
I blushed hotly and whimpered around my pacifier as she helped me to stand up. The thick bulk between my legs felt awkward and I was forced to stand with my legs slightly apart.
“Come take a look at yourself in the mirror, Chrissie,” she said as she led me over to a full length mirror in the corner of the room, “You’re so cute I just want to eat you up!”
She emphasized her point by squeezing the thick seat of my diapers, making me squeal with surprise like a girl.
Looking at my childish reflection, I blushed fiercely as I beheld myself for the first time. My legs, which had always been smooth and free of any hair, only added to my babyish appearance and with my pink sissy top and bulging diapers, I truly looked like a toddler. And the fact that I was still sniffling around the big rubber pacifier stuffed in my mouth served to complete my humiliating look.
“Now I’m afraid since you acted up earlier, Mommy’s going to have to put you down for your naptime now,” Barbara said, a trace of disappointment in her voice.
Leading me over to the crib, she helped me in and tucked me in tenderly, pulling the baby blankets up and putting a teddy bear under one of my arms. She raised the side bars and then to my surprise, lowered a closing top which made the crib a veritable cage! Taking a stout lock, she fed it through a hasp at the edge and locked it shut.
“That should keep baby in her place,” she said, “Now you just hold still, and Mommy will get you your bottle, Honey.”
Instinctively, I reached out and felt the wooden bars that surrounded my new prison–they were strong and quite secure.
Before long, Barbara returned with an extra large baby bottle in her hand.
“Here you are, Chrissie, a nice big bottle of warm milk. Now I want you to make sure you completely finish that before I come in again for you,” she warned me with a wag of her long nailed finger, “Little sissies that do what they’re told get treats but those that disobey get spanked. Okay Sweety?”
I nodded my head sullenly as I took the bottle from her.
Reaching between the bars, she pulled my pacifier out and pushed the big rubber nipple of the bottle between my lips.
“That’s a good baby,” she cooed musically, “Nurse on your ba-ba.”
She stood there to watch me for a bit, just to make sure I was going to do as I was told and then she turned to go, making sure the Care Bears nightlight was on.
“Sweet sissy dreams, Chrissie,” she sang out as she softly closed the door.
Quickly removing the bottle from my mouth, I set it down next to me, pouting miserably in frustration. Never in my entire life had I been so completely humiliated! Oh, how I hated this woman! She’d punished me far worse than anyone had ever come close, and yet, I was so helpess before her! My cheeks burned with shame over my babyish outfit, even as my bottom cheeks burned from the recent paddling. To think I was wearing diapers and plastic pants! How had this even happened to me?
One thing was for sure–as soon as my mom found out, there would be hell to pay. I intended to explain everything to her–well, maybe not everything. I’d do my best to down play certain things. I had no intention of describing the diapers I was forced to wear for instance. But I’d be sure to tell her this crazy woman had done everything humanly possible to humiliate me. She’d be as indignant as I was and then I’d never have to see Barbara again.
Lying back in the semi darkness, I sighed in frustration.
On the other hand, who was I kidding? My mom would probably applaude Barbara for so thoroughly punishing me. Maybe she’d even agree to some long term arrangement for me to stay here. God, how terrible would that be?
Pouting to myself in misery, my mind began wandering and I found myself once again thinking about Barbara’s tremendous curvy breasts. Man oh man, they were huge, I thought to myself. Her skin was so soft and her round boobs so plump and sexy. Without warning, my penis sprang to attention and I reached down to it without thinking. Unfortunately, my hand was seperated by the snug plastic panties I was wearing and several thick layers of cushiony cotton diaper.
Impatient to stroke myself, I began rubbing the soft pliable front of my diapers, which resulted in a wonderful, pleasurable massage of my aching penis. Waves of ecstasy washed over me as I used the other hand to join in. Much as I hated my humiliating new underwear, I had to admit they felt fantastic between my hands and my hard on. Spreading my legs, it only took a moment before I had one of the most powerful orgasms of my entire young life, making me shudder with joy in the crib. It left me gasping for air and it was several seconds before my eyes finally uncrossed.
As I lay there, coming down from the high of my climax, the full weight of my shame hit me like a stack of bricks. Here I was, dressed like a little baby girl and I had just used my diapers to masturbate into. Worse yet–it had felt better than anything I’d ever experienced. As hard as I tried to, I couldn’t stop Barbara’s words from ringing in my head: “All sissies love their diapers and in no time–you’ll feel naked without them…All sissies love their diapers and in no time–you’ll feel naked without them…”
Was I really a sissy? I despised myself for proving her right. Looking down in the soft light at the shiny plastic of my bulging diapers, a new wave of humiliation swept through me. Only a complete sissy would be caught wearing these! And yet, they felt cozy and wonderful. I was so confused! In my angst, I cried myself to sleep.

Chapter Three A Visit From Melissa

I slept the better part of the afternoon, despite the unfamiliar, awkward bulk between my legs and the crinkly vinyl waterproof mattress cover I was lying against.
In my dreams, Barbara was letting me kiss her wonderful big breasts, unbuttoning her tight top to reveal more and more of her soft, silky smooth skin. She smelled lovely and I luxuriated in her intoxicating closeness.
I woke up slowly and as I did, I found myself rubbing the front of my diapers with eager abandon. Once again, I found the combination of soft, comforting cotton to be more than I could stand, and in no time, I came explosively as visions of Barbara swam before my blurred, half closed eyes.
Like deja vu, once the rush of the orgasm had faded, I was crushed by shame. Here I was, fantasizing about my arch foe–a woman who had reduced me into a simpering, sissy baby girl! How low had I sunk? Yet, I was a helpless slave to my lustful desires. There was no denying Barbara’s beauty and incredible sex appeal. How could anyone resist such a woman? Subconsciously, I realized it was just one more weapon in her arsenal that she used against weak willed guys like me. And I was completely defenseless against her!
Out of the corner of my eye, I saw the nursery room door open and recognized the hourglass silhouette of Barbara coming in.
“Hello Chrissie,” she called out softly, “Is my little baby awake?”
“Uh-huh,” I answered.
She turned on the light and came over to the crib, bending over to look in on me. I took the opportunity to stare down the front of her low cut top and I gaped at her magnificent boobs. Even having cum so recently, I felt my little penis beginning to stiffen within my diapers.
“Chrissie? Did you finish your milk like I told you?” she asked suspiciously.
I had completely forgotten about it and bleated out a nervous ‘oops’ as she picked it up.
“You’re a naughty little sissy!” she scolded me but I sensed she wasn’t really angry, “I’m going to re-warm this and then you are to finish it immediately. I’ll let you get away with this on this occasion but the next time is going to cost you a spanking.”
I gulped hard as she strode out of the room, determined to avoid another blistering session with her paddle.
It wasn’t long before she returned and after handing me the bottle, she unlocked my crib top and lowered the side rail. I wasted no time in nursing from the bottle and as she helped me up, she squeezed the thick seat of my diapers.
“Did mommy’s baby wet her pampers?” she asked in a syrupy voice.
“Un-uh,” I mumbled and I blushed nervously, hoping she wouldn’t put her hand down the front and discover the big gooey wet spot from where I had cum twice. That would be a sure way to end up taking another trip over her lap.
“Okay, well, we can wait on changing your diapers, let’s find a pretty outfit for you to wear,” she said eagerly as she took my hand and led me over to the closet.
I was amazed at all the frilly dresses and rompers she had, and I suspected some of them must have come from her store. Her hands stopped at a silky lilac colored dress and she pulled it out, putting up before me to see how it would look.
“Oh, that will be just darling, she exclaimed with great enthusiasm, “the purple in this dress goes just perfect with your baby blue eyes–you’ll be just the prettiest little thing!”
I blushed in embarassment and she helped me out of the sissy top I had worn for my nap. Holding my arms up dutifully, she brought the dress over my head and fitted it into place. It was made of soft, purplish-lilac silk material with a Peter Pan style collar and a white frilly bodice. Short puffy sleeves ended with elasticized delicate lace, causing them to billow out on either side of my shoulders and masking my boyish torso. The hem, which I soon discovered was extremely short, barely came down past the waistband of my diapers.
“These are all cut very short, so that diaper changes are much easier,” she explained as she buttoned it up in back, “And they all have a secure tie string in back, which prevents any unauthorized removal–this dress will stay on until I decide to take it off.”
I had to stand patiently while she fastened it up carefully, tying the back in a knot I knew I’d never be able to reach, never mind undo. Taking me back over to the crib, she sat me on the edge of the mattress while she went back to the dresser and retrieved some socks.
“Aren’t these special?” she asked, “Look at the cute purple lace around the ankles and the little plastic pacifiers–they jingle like bells when you walk around.”
I groaned inwardly, even as I did my best to finish the big bottle of warm milk. I hated milk, especially warm, but I knew better than to make an issue of it. Unfortunately, between having already drank quite a bit and cumming twice, I was starting to feel a real need to pee. I wasn’t about to use my diapers and I figured I could just wait until my mom came by for me. It shouldn’t be long now, I reasoned.
After putting the frilly, purple trimmed anklets on me, Barbara knelt down to buckle a pair of glossy black Mary Janes onto my feet.
“You’re going to be the cutest little baby girl ever!” she gushed proudly.
“I think the next item I need to get for you is a little purse,” she said as she looked me over critically.
“Okay, I’m sure you’re getting hungry–let’s get you ready for dinner,” she remarked as she stood me up.
Taking my hand, she led me down the hall and into her spacious kitchen. The fat diaper forced me to waddle and I was unacustomed to feeling the slippery plastic bulk brushing against my inner thighs. The dress swished noisily and it made it impossible for me to forget I was dressed like a little baby girl.
Once we got into the kitchen, Barbara helped me up into a sturdy pink highchair, much bigger than a normal one and apparently made for someone of my size. As soon as I was seated, she removed the step I had used to get into the chair which left my feet swinging uselessly. There was a matching tray that she brought over and slid into the sides of the chair where it clicked with a locking sound. If I didn’t already feel helpess with that, she began securing my wrists with two pink velcro straps.
“That’s just so baby doesn’t interfere with her feeding,” she told me as she beeped my nose playfully.
With the tray against my abdomen and my wrists restrained against the sides, I was completely at her mercy.
“Now, we certainly don’t want to mess up your pretty dress so here’s a nice baby bib for you.”
She came around behind me and tied a big plastic Dumbo bib around my neck, carefully smoothing it down over my chest.
“That’s a good baby,” she said, “now you’re all ready for num-nums!”
She wasted no time in emptying several jars of baby food onto a green plastic divided plate and with a large spoon in hand, she brought it over and set it on the tray in front of me.
I started to squirm uncomfortably because my need to pee was getting more urgent and I wasn’t sure how much longer I could hold it. At the same time, none of the slop she was about to feed me looked in the least bit appetizing and I wasn’t looking forward to this meal.
“Here we go, Chrissie, din-din time!” she sang merrily.
Scooping up a big spoonful of something yellow, she brought it up to my lips but I blanched at the smell.
“Un-uh,” I balked weakly.
“Open up Sissy, baby needs her veggies,” she urged me.
I turned my head but she followed my lips with the heaping spoon of slop. I was keeping my lips pursed shut but then she pinched my nose with her free hand and held it closed, smiling down on me as she waited patiently. In no time at all, I gasped for breath and she rewarded me with the entire spoonful of pureed corn. Most of it got in, although some slopped on the side of my mouth. I nearly choked on the foul tasting glop but I managed to gulp it down nonetheless.
I wanted to wipe the food off the side of my mouth but I couldn’t move my hands and Barbara was already bringing another heaping spoonful up to my face.
“Here comes the train…into the tunnel!” she sang in some sort of nursery song.
“Nooo–” I whimpered but she shoved it into my mouth anyway.
“MMRPHH,” I gurgled and it was all I could do not to spit it out.
Barbara was ready with another spoonful, this time of a green colored food. I shook my head no but once again, she held my nose and forced it into my mouth. Half of it spilled down my chin and plopped onto the front of my bib.
“Oh, you’re a messy eater,” Barbara chided me.
Scooping up the slop from my bib, she combined it with another spoonful of something else and brought it up to my face.
“Open up Chrissie, this is good for you,” she assured me confidently.
I was squirming in my seat, struggling to get away but the velcro straps kept me securely in place. On top of that, my bladder was aching and ready to burst. It was all I could do to fight Barbara’s frenetic feeding pace but the need to pee was becoming even more critical. And everytime I opened my mouth enough to cry out, she filled it with more slop. By now, my chin and mouth were covered with different colors of baby food, yet she still kept bringing more to my lips. My stomach was turning somersaults and I felt queezy from the nasty food I was forced to gulp down.
I shook my head no but once again, she held my nose closed until I was forced to gasp for breath.
“Here you go!” she sang with a big smile as she poured another heaping spoonful of mashed peas into my open mouth.
Struggling helplessly against my bonds, I suddenly felt the dam burst. With a plaintive cry, I felt a strong surge of hot pee flooding into my diapers. I wriggled in place and cried out, only to have Barbara shove another spoonful of slop into my mouth, muffling my wail of desperation. Another strong surge followed the first, and the warm wetness spread rapidly across the front of my diaper. I sobbed in despair and gave up in defeat, capitulating to nature’s call as millions of babies had done before me. My bladder had been holding a day’s worth of pee and there was no stopping it now. After soaking the front of the thick cotton cloth of my diaper, the warm pee seeped back between my legs, quickly saturating my seat. More pee followed the beginning surge, creating a warm yellow puddle between my legs. In helpless frustration, I burst into tears, the food in my mouth spilling over my jaw and down my chin.
Barbara stopped momentarily to look down at me in sympathy.
“Awww, what’s da matter Sweety?” she said in her cutsey baby’s voice, “Is Cwissie having a bad day?”
The tears streaked down my cheeks and into the slop that was caked all over my face. My pee was still running strong and I feared it would leak out the sides and onto the seat of my highchair. Shifting in my chair, I felt the warm wet cloth squishing and clinging stubbornly to my bottom. I felt so babyish, having been forced to wet my diapers like an infant and I bawled uncontrollably.
Barbara lowered her head sideways and gazed at the darkened front of my diapers.
“Ahhh, I see,” she beamed at me with a look of pride, “Mommy’s little girl just wet her diapers!”
I shook my wrists in frustration but the velcro straps held me all too well.
With the palm of her hand, she placed it against the warm front of my diapers to feel my wetness.
“Oh my, you are quite the little wetter, aren’t you?” she giggled, “I’m glad I triple diapered you, but don’t worry Honey, those plastic panties will keep it all in.
“Tell you what,” she suggested, “We’ll finish up dinner and then I’ll get you into a nice, fresh set of pampers, okay?”
Without reponding, I just sat there and cried like a toddler. Ever since I had seen her, Barbara had been forcing me to her will and I was sick of it. I was so angry I wanted to scream and I hated myself for crying but I couldn’t seem to stop. Once started, I could no more stop my crying than I could my wetting.
Just then, the doorbell rang and I froze in position.
“You just stay right there,” she said unnecessarily as she set the spoon and plate down on the tray, “I’ll be right back.”
I watched with trepidation as she sauntered off, her sexy bottom sashaying and her high heels clicking across the hardwood floor as she went to the front door. I was terrified of being seen like this and I kicked my feet helplessly as I struggled in futility to free myself. What was I going to do if someone saw me in this position? With my soaking wet diapers, baby food caked face, and the fact that I’d obviously been crying, I looked no better than a crabby two year-old.
Opening the door, Barbara stood aside as she greeted her caller in a friendly voice.
“Hello Melissa!” she exclaimed as she gave her friend a big hug, “Come in, come in!”
I watched in horrified panic as a tall, raven haired woman stepped into the entranceway. She was quite a looker and she was dressed smartly as well. Black leather high heeled boots accented her skin tight pants showing off her fabulous physique. She had a white blouse, unbuttoned to the waist and underneath, what looked like a black corset that pushed her sexy breasts into two exciting mounds of feminine glory.
But right now, I sat cringing as she turned to face me, the look of disapproval plain to see on her pretty face. I had never felt more like a complete loser in all my life.
“I hope I haven’t come by at a bad time,” she said cautiously to Barbara.
“No, not at all! In fact, you’re timing couldn’t be better. Chrissie was just finishing up his dinner and he’s already wet himself so I was just going to change him. I’ll get him cleaned up before you start so it’s a perfect time to get his measurements,” she explained.
My face, already covered with colorful baby food, just turned another shade of deep red.
Melissa came over to get a better look at me and I sat there sniffling, puffy eyed, with slop caked all over my face. She shook her head at what she saw–a teenaged guy wearing a dress and wet diaper who looked helpless without his mommy.
“What a sissy,” was all she said as she shook her head.
“He certainly is,” Barbara confirmed, “I knew right off when I first saw him he was either a panty thief or momma’s boy. I was able to get some information from his mother and when I brought him over, I put him straight into diapers and baby clothes. I think this stage suits his immature, whiny personality the best–dressed like a two-year old toddler. No bras and panties for him–it’ll be diapers and onesies from now on,” she chuckled smugly.
I felt myself blushing all the way to my ears at her humiliating appraisal of me.
Melissa had crossed her slim, toned arms over her prominent bosom as she watched Barbara take a warm washcloth and wipe my face of food and the tears I’d cried. I was devastated to be seen like this and I kept my eyes on the floor, unable to look this tall, strong woman in the face.
When Barbara was finished and my bib had been removed, she undid the velcro straps around my arms and pulled out the locking tray in front of me.
“Come on Chrissie,” she said brightly, “Let’s go get those wet diapers changed.”
She emphasized her point by giving my thickly diapered seat a slap which landed with a dull thud.
I trudged along behind her as she held my hand and led me back to the nursery, Melissa coming along behind us.
“D-does she hafta watch?” I whimpered in my pleading voice.
Barbara turned to look at me in surprise.
“Don’t you worry your pretty little head about that, Sweety, you’ll be seen by all my friends sooner or later so this is something you’ll just have to get used to.”
I pouted and stamped my feet in frustration over the unfairness of it all.
“There’s no point in getting fussy, Chrissie–you can bet some of them will want to change you themselves, once they see you what a big baby you really are.”
Sitting me down on the changing table, Barbara pushed the short lacey hem of my dress up my chest, further exposing my sopping wet diapers. I blushed hotly with shame as Melissa stared down at me hard, not a trace of sympathy to be found on her stern face.
With Barbara’s long glossy fingernails, she reached into the clinging elastic waistband of my plastic panties and began tugging them down over the wet cotton cloth.
“As you can see, a big sissy wets quite a lot; I’m using triple thick diapers with a soaker pad for him which is just what he needs–that, and a good snug pair of plastic panties.”
Melissa started fishing in her purse and she got out a pen and paper, along with a small measuring tape. I hadn’t the slightest idea what she had in mind but to be honest, that was the last thing on my mind. Not only was this strange woman seeing me with wet diapers, she was also about to discover just how small my weiner was.
My penis had always been an acute source of embarrassment for me. It seemed that after about the second grade, it had just stopped growing and it was by any standards, tiny. While the rest of my body had grown more or less normally, my penis remained stunted and disproportionately small. I had always hoped that puberty would spur the growth somehow but so far, I hadn’t seen any evidence of that.
I squirmed in embarrassment as Barbara unpinned the sides of my diaper and peeled the soaking wet cloth back.
“OH-MY-GOD,” Melissa exclaimed in shock, “Is that thing real?”
Barbara stopped my changing as she burst into laughter, her hand coming to rest on her friend’s shoulder as she shook with amusement.
“Yes, that’s all there is,” she said as soon as she could talk again, “Do you see what I meant about needing a custom device?”
“Oh my god–yes,” Melissa nodded her head, “I’ve never seen a penis that small! It must be an inch or so!”
Without waiting, she held her tape measure down next to my wilted, humiliated member, scrutinizing the size carefully.
“Yes, that’ll be a total custom order for sure,” she affirmed.
“Can you do it?” Barbara asked hopefully, “Even the Birdlocked Mini will be way too big for him.”
“Oh yes, way too big,” she agreed, “No, this one will be completely hand made to fit him.”
I had no clue what they were talking about but I wished Barbara would finish and cover me back up. It was mortifying laying here while these two made fun of my diminutive weiner.
“What are you measuring for?” I asked uncertainly in a small, feeble voice.
Barbara just smiled down at me before taking my pacifier and pushing back it into my protesting mouth.
“There you are Sweety, this is just grown-up talk that doesn’t concern you. You just suck on your paci.”
I pouted in frustration and did as I was told, but I wished I knew what they were talking about.
“Do you shave his legs and crotch?” Melissa asked in wonder.
“No, not at all,” Barbara laughed, “Amazing, isn’t it? This is how he came to me, bald as a baby, even around his little package here.”
I blushed hotly at her keen observation.
“His legs are so girlish,” Melissa remarked disparagingly, “I thought maybe you’d waxed them or something.”
Barbara giggled and shook her head as she removed the heavy wet diaper from underneath me, plopping it into a sturdy plastic bin.
Melissa took her tape and ran it around the base of my genitals, noting the figure on her pad.
“I’ll have to get a measurement of him erect–can you do that?” she asked.
“Sure thing,” Barbara replied and she picked up a bottle of baby lotion that was next to the changing table. Squeezing some in her hand, she began rubbing it gently around my shrivelled, embarrassed penis.
“Do you like big breasts, Chrissie?” she said as she undid the uppermost button on her top.
I was extremely humiliated with what was taking place but as I stared at the perfectly round shapes of her sexy bosom, my weiner responded all too predictably. In no time, it was stiff and hard, throbbing within her soft, sensuous grip as she smiled down upon me.
I groaned with desire and yearning for a third orgasm even though a part of me was saying I should show some dignity to resist her.
“There you are,” she said as she released my slick penis, “I think that’s as big as it’s going to get.”
Melissa just shook her head in amazement.
“Unbelievable, it looks like a stubby crayon.”
Afraid it would collapse without further stimulation, Melissa hurried to measure it with her tape, jotting down the last figure on her pad.
“Got it,” she said with finality, “So, does he masturbate quite a lot then?”
I shook my head no and bleated out a muffled protest but they both ignored me as if I didn’t exist.
“His mother told me he’s a chronic masturbator, that’s why I wanted to get this as soon as possible,” Barbara informed her.
“Yes, he looks like a little masturbator, I’ll bet he does it several times a day.”
It was clear she thought of me as a nasty little perv and I blushed, shaking my head vigorously in disagreement.
“I’m sure of it,” Barbara agreed, “Is there any way you can put a rush on that?”
“How about a week?” she responded, “This one is going to take longer than usual due to how tiny he is.”
“I understand, do what you can,” Barbara told her.
If only I knew what they were talking about!
Barbara had slid another tall stack of fresh diapers beneath me and she pinned them around my hips as they made small talk between themselves. I was totally forgotten as they laughed and talked about the men in their life–real men, they emphasized, and it made me jealous as hell to have to sit there getting my diapers changed like a toddler and act like I couldn’t hear them.
Barbara finished my changing as she pulled a pair of soft pink plastic panties up my legs.
“Here you are, Chrissie, all diapered and ready for bed. I’ll just get you some jammies to wear.”
I whimpered around my pacifier and made it obvious my disapproval.
“No, it’s 7:30, Chrissie. That’s bedtime for sissies who wear diapers,” she told me firmly.
Moving behind me, she began untying the knot she’d made earlier at the back of my dress and she pulled it over my head. After she hung it back up, she brought over a fuzzy white onesie with bunny designs decorating it. I fussed crankily as she worked it over my head and pulled it down over my chest and waist. It had a big row of pink ruffles around the elasticized waist with smaller matching ruffles around the leg openings. Reaching between my legs, she snapped closed the four metal snaps between the legs, making the soft fuzzy fabric cling snugly to my bulging diapers. Somehow, I found this babyish garment even more humiliating to be dressed in–maybe because it also signified my early bedtime and the crib I’d soon be sleeping in.
Catching sight of myself in the full length mirror, I couldn’t believe how sissyish I looked. My fat diapers gave me a distinctive bell shape with the big ruffles looking like a sissy belt. My glossy Mary Janes only added further to the effect although Barbara soon removed them and put them away.
“I’m going to get you your bedtime bottle and then it’s off to the crib for you, Missy,” she said as she rose to her feet.
I chewed the fat rubber nipple that filled my mouth in acute frustration as Melissa ignored me and made a call on her cell phone, telling someone about the measurements she’d just taken. I was impatiently waiting for my mom who should have come over by now and I didn’t understand what was taking her so long. If she didn’t come over soon, I’d be in bed already and I was afraid she’d leave me here.
Melissa left without so much as a goodbye and while I thought she had a sexy body, I was very intimidated by her and was relieved to see her go.
Barbara soon returned with the bottle of warm milk and she guided me to my crib with stern admonitions to drink it all or I’d start off tomorrow with another sore bottom. As soon as the pacifier was out of my mouth, I began squealing for an end to this.
“When’s my mom gonna come get me?” I whined, “I don’t wanna play baby anymore.”
Barbara was very patient and she sat me down on the edge of the crib mattress while she picked up the teddy bear that was lying there.
“Chrissie, it’s time for you to face a few facts. Your mommy isn’t coming to get you…not tonight, and not anytime in the future. We’ve talked about your behavior and it’s been decided that you’ll be staying with me from now on.”
My jaw dropped open in shock as I tried to digest this devastating news.
“I know this must seem like a lot to take in one day, Chrissie, but believe me, it’s all for the best,” she continued.
I shook my head in disbelief as I struggled for words to say.
“I can see you’re upset but there’s nothing to worry about, Honey. Nothing at all. Because I’m going to make sure you’re the cutest, best behaved little baby girl any mother could hope for.
“Don’t you see how this is what you really need? We both know that deep inside, you’re just a little sissy that’s dying to get out. And I’m going to make that happen for you. You don’t have to worry about being a tough little guy anymore, trying to act like something you’re not and you don’t have to be responsible anymore…I’m you’re new mommy and I’m taking away all your responsibilites from now on.
“I’ve got lots of fun toys for you to play with, some cute dollies and coloring books, some big plastic building blocks and tommorrow, I’m getting a big playpen so you can play in the living room while I’m entertaining my girlfriends.”
She told this to me like it was something I really wanted but it was all horrifying news to me. All this time, I had been waiting and counting on my mom to come rescue me from this domineering, controlling woman. I still couldn’t believe she wasn’t coming.
“But I don’t want any of that!” I whined strenuously, “I’m not a baby and I don’t wanna wear diapers anymore.”
Despite my best efforts to give the appearance of being strong, hot tears, brought on by panic, began brimming in my eyes.
“You poor little sissy,” Barbara said soothingly, “I know this must seem rather unfair and a bit overwhelming…after all, just this morning you were a big teengage boy in class and now you’re a diaper wetting baby being put to bed in your crib.
“But it’s really all for the best, Honey, believe me,” she repeated, “Your mom and I talked it over and we agreed this is just what you need. You don’t belong in school, wearing your jeans and trying to fit in with the other guys. Where you belong is in a nursery, wearing diapers and dresses and that’s just what I’m going to do for you. You won’t have to figure out what to wear anymore because I’ll do that for you. I’ll dress you in the morning–after I’ve changed your wet diapers that is–and I’ll decide what to feed you. I’ll decide where you can play with your toys and I’ll decide when your naptime is.”
I was shaking my head silently as the tears spilled down my face. My shoulders began to shake as the finality of my situation came crashing down on my like an iron portcullis. Barbara was too strong for me to face physically and she’d already shown that I was no match for her mentally either.
Taking the bottle out of my hand, Barbara gently stood me up and led me over to a plush love seat situated in the corner of the room.
“There, there, Baby,” she said in her soothing voice, “Don’t cry now…tell you what–I know just what baby needs, you come right over here.”
I didn’t want anything to do with her but I didn’t fight her as she sat down and guided me into a lying position over her lap. As I looked up into her pretty eyes, her massive bosom was just inches from my face and I sucked my breath in as I gaped at it’s fabulous shape. Barbara smiled down on me as she saw I was momentarily distracted and I watched as she slowly undid the first button on her top. I knew she was manipulating me–it was only too obvious, and I hated her for it. Yet, there was no way I could resist her either. Even as the tears trickled down my cheeks, my penis was hardening and becoming erect within the soft, comforting folds of my diaper. I was angry with her for what she was doing to me but I was completely powerless to hold back my libido.
I watched in captive fascination as she undid the next straining button, and then the next, until her clinging top was pulled aside and the front of her white lacy bra was exposed before me. I had never seen a bra this close, not even my mom’s, since she made a point of hiding them from me. Of course, I’d masturbated to pictures in magazines before but this was the real deal!
I found my breath becoming labored as I greedily took in the unbelievable sight before me. The smooth, satiny cups of her bra were so sexy, and my eyes were riveted, taking in every feminine detail for the first time.
My lips were dry and I licked them nervously as Barbara used her lovely manicured fingers to undo the clasp that held her two huge cups together.
“Don’t cry, Chrissie…Mommy’s going to give you something all little babies need.”
Having been shy all my life and having never kissed a girl prior to this morning, I was quite overwhelmed with my present circumstances. My face was flushed and my heart was pounding in my chest as I squirmed uncomfortably on her lap. As she eased her right cup away, I stared dumbfounded as she pulled it back, revealing more and more of her incredible plump breast. It was as big as my head!
“These are just bursting with milk, Chrissie,” she beamed down at me, “And I’m going to make sure you get your fill everyday.”
I whimpered weakly, pleading with her that I wasn’t ready for this. She smiled warmly and cupped her big round mammary in her small hand, positioning her large pink areola in front of my face.
“This is what you need, little sissy, a nice warm nipple and mommy’s milk to sooth you.”
I shook my head and closed my eyes in panic but I felt the damp tip brush against my lips.
“No…no…please…” I whimpered as I blinked back more tears.
“There, there, little baby, open up for mommy now…” she urged me softly, “Take mommy’s pink nipple….time to suckle….open up my little sissy.”
I felt her gently pressing it against my lips as her other hand reached around to cradle my head, effectively trapping me. I squirmed and squealed but I couldn’t escape. I felt her firm, urgent nipple between my lips and as I struggled and pleaded with her, she gently pushed it into my mouth, filling it and muffling any further complaints. A sob was stifled as I tasted her warm nipple on my tongue. Still trying to speak, the movements of my jaws flexing around her breast brought forth a stream of strange tasting liquid to my mouth and my eyes popped open in surprise.
“That’s right baby,” she said as she smiled down on me knowingly, “Mommy’s got her own milk for you.”
I whimpered weakly as she gently stroked the back of my head and without thinking, I began nursing like an infant.
“Thaaat’s a good baby,” she whispered softly to me, “That’s mommy’s little baby.”
My face was red with embarassment at this uniquely infantile act but despite that, my penis was rock hard in my diapers.
“This is what you’re going to get everyday from now on, because all babies need their milk,” she cooed gently in my ear, “And guess what? Some of my friends are lactating too so you’ll get the chance to nurse from them as well.”
I sucked feverishly now and was rewarded with a steady stream of her maternal nectar. I swallowed it and hungrily sucked harder, my head spinning at what was taking place. Never in my wildest imaginings would I have pictured what I was doing. It was humiliating in the extreme, yet my heart was pounding with excitement. Barbara’s big breast tasted wonderful in my mouth and the scent of her skin was like ambrosia. As I nursed like a baby from her bountiful bosom, I felt a sexual wave swelling within me and my penis throbbed mightily. I could feel my blood coursing through me like electricity and I was breathing heavily through my nose. At the same time, my cum was bubbling up, closer and closer and there was nothing I could do to stop it.
With an inevitablity I knew I couldn’t resist, I climaxed with an explosive force in my diapers. Howling noisily, Barbara kept my mouth firmly in place with her big nipple filling my mouth like a gag as I moaned deliriously. My eyes crossed and my head swam as I tried to cope with the magnitude of my incredible orgasm while my body convulsed and shuddered in ecstasy. I could feel a big gooey wet spot forming in the front of my diaper and I marveled at the fact I hadn’t even touched myself.
Barbara smiled down on me with what looked like pride on her beautiful face. Or maybe it was the smug look of her knowing she’d bent me to her will but either way, I didn’t care. Right now, I was riding the delightful wave of post-orgasmic bliss, feeling my hard-on gradually beginning to soften slowly as it began shrinking down to it’s usual limp form.
For a moment, Barbara pulled her breast out of my mouth as I lay there, gasping for breath. My face was flushed and I looked up at her through half closed eyelids, suddenly feeling very sleepy.
“Well, I think that took all of thirty seconds,” she told me, “You really don’t have much control do you?”
I swallowed and looked away, extremely embarrassed with myself. It was true I had very little staying power but I’d never really given it much thought.
“But that’s okay because with aunt Melissa’s help, we’re going to take care of that little problem next week.”
“Wha-what do you mean?” I croaked as my breathing began to become normal again.
“No need to worry about that, Chrissie, Mommy’s got everything under control. And very soon, you will be too,” she giggled.
I sensed danger in her vague statement and felt I should press her further.
“What do you mean? What’s going to be under control?” I asked again.
Without answering, Barbara reached over and brought the baby bottle to my mouth, easing it between my lips as she shushed me.
“Hushhh little baby,” she whispered, “It’s beddie bye time for mommy’s sissy girl.”
I hated being denied anything, and her ignoring my questions left me frustrated and resentful.
Standing me up, she led me back over to the crib and tucked me in, placing the teddy bear under my free arm as she pulled the soft fuzzy blankets up around my chest.
“There, there, Chrissie, Baby’s had a big day but it’s time to go to sleep now.”
Closing the top of my crib, she slipped the lock in the hasp and clicked it shut, sealing my prison for the night. The Barbie clock on the dresser read 7:32 pm.

Chapter Four A Baby Shower For Chrissie

Barbara peeled the soaking wet diaper off my bottom and plopped it into the big rubber bin behind her. Even though she made a point of washing my soiled diapers on a daily basis, the nursery had begun to take on that distinctive smell of a toddler’s room who frequently wets–it was the pungent calling card that let everyone know the diapers I were wearing weren’t just for looks.
After the first day, I resolved to hold off my urge to go until the very last minute–that was–when I knew Barbara would be changing me anyway. It was my only means of rebelling, however small, against her implacable rule. Of course, sometimes it didn’t work and I was forced to wear a wet diaper for some time before she eventually changed me. And there were times when she’d just changed me and only minutes later, I’d have an urgent need to pee that I couldn’t hold. That was the worst and often, even when I told her about it, she’d still make me wear them until my usual changing time. her usual response being to tell me that “all babies need to get used to wearing wet diapers” and that it would “do me good”. Nevertheless, I resented having to wear a wet diaper around for several hours at a time, especially when they were trapped inside a snug pair of plastic pants.
Fortunately for me, I had been thus far, completely successful in hiding my frequent masturbatory activities from her. As far as I could tell–she was none the wiser that I was playing myself three to four and sometimes five times a day. And in my defense, there was little else of interest to do–it was either that, or play with her baby toys she had all over the house. But I was also convinced that it was a physical necessity as well. Barbara never wore anything that didn’t show her big luscious boobs in the most flattering way possible and even after I’d cum, the sight of her in a tight, clinging top never failed to make my penis begin to harden all over again.
And during the afternoon, she’d sit down on the couch and let me breastfeed from her which inevitably resulted in another orgasm for me. Truth be told, my sex life had never been so active, although it was still entirely one-sided.
I watched Barbara carefully now as she wiped my damp buns with a baby wipe. Her side to side movements made her big round breasts sway and jiggle in the most erotic way and my penis stiffened immediately. I had stopped trying to hide my sexual attraction towards her, despite what she’d reduced me to. Of course, it would have been impossible in any event, because she saw my physical reactions every time she changed my diapers. For her part, she often ignored my hard-on or giggled to herself as she powdered it and pulled my diapers back up to pin them closed. And I knew I’d be masturbating furiously without fail, the moment her back was turned so I had learned to be patient.
We seemed to have arrived at a sort of understanding between each other. Or rather more accurately, I’d learned to obey her without question. In any case, it had been two days since she’d taken me over her lap to give me one of her blistering spankings. I certainly wasn’t anxious for another.
“Let’s see…” she mused as she sifted through my bulging drawer of plastic panties, “We want something extra special for my little baby today, and do you know why?”
I shook my head as my pacifer was in its usual place, filling my mouth with soft, pliable rubber.
“It’s your very own baby shower, Sweety!” she said merrily as she playfully beeped my nose, “Your going to have so much fun!”
I gulped hard and squirmed uncomfortably as I pondered the implications of what she had in mind.
“After I get you all dressed up, we’re going over to my good friend Emily’s house where we’re throwing a baby shower, just for you!” she gushed, “Everyone’s bringing presents and I know you’ll have the most wonderful time.”
She told me this as if she expected that it was the best possible news for me to hear.
I shook my head desperately in protest. So far, my humiliating babyish treatment had been seen by only one other person, Barbara’s friend Melissa, and I didn’t want it going beyond those two.
“I’ve got a very special baby outfit for you today–your very own sissy sailor suit–what do you think of that?”
She pulled out my pacifier just long enough to get a response.
“Noo!” I squealed, “P-please don’t take me over there!”
Barbara smiled down at me and pushed the warm nipple of a big bottle of milk in between my trembling lips, stifling any further argument from me.
“Don’t worry Babykins,” she assured me, “I know you’re very shy but my friends just can’t wait to see how much of a sissy you really are.”
I whimpered in vain as I nursed from the big bottle she was holding in place before me. It was my second today and unconsciously, I knew I was going to have a tough time holding all this liquid back for long.
“Let’s see…” she said, returning to the drawer of baby pants after making me hold the bottle for myself, “…Here we are–aren’t these scrumptious?”
She held a pair of white nursery print plastic panties with colorful bunnies and flowers on it before me.
I swallowed weakly, knowing there was little point of fighting her.
She worked the soft, shiny panties over my feet and down my legs, surrounding the big, bulging cloth of my diapers as she carefully fitted them around my hips.
“Oh yes, these will be just perfect with the see-thru rumba panties I have in mind,” she commented.
I nursed from my bottle as she went over to the closet and began poking around until she produced a white, frilly lace top. Bringing it over, she held it before me as if expecting me to show my unbridled enthusiasm for it. It was mostly white, with pink and baby blue accents around the short, puffy sleeves and hem. A big pink satin sash was tied in a bow across the bodice in sailor fashion and I cringed at the layered pink rows of lace along the short hem. Raising it over my head, she pulled my arms through and down over my torso. There were a pair of matching frilly panties on the hanger and she took them off to hold them open for me.
“Here you are, Baby,” she said encouragingly as she fed my feet through and worked them up my skinny legs. They were made of a soft, stretchy, see-thru material that glittered and I noted the fuzzy pink ruffles around the leg and waist. I’d never seen anything so babyish in my entire life but as she pulled them over my diapers, I realized the nursery print of my plastic panties could easily be seen through the material.
“Oh–that is just the cutest thing,” Barbara remarked glowingly.
“Do you know you have the smoothest legs of any boy I’ve ever met? Just like a baby’s,” she remarked as she stroked my bare thigh.
I shook my head but I don’t think she was really expecting a response.
Before long, she was pulling some pink lacey anklets over my feet and buckling my shiny black Mary Janes. I squirmed and whimpered as I contemplated being seen dressed like this. My stomach was turning somersaults and I was tense with nervousness.
“And now, we’ll do your nails in a pretty matching pink–won’t that be fun?” she asked cheerfully.
Sitting me down on the edge of my crib, she took a bottle of pink glossy nail polish and began carefully painting my fingernails, humming to herself as she worked.
“I wish your hair was longer so we could put in curls, Chrissie,” she remarked, “But don’t worry, it won’t be long before that happens.”
I nursed my bottle, switching hands when she’d finished the first one. Then she applied some light blusher to my cheeks and some glossy pink lipstick as I pouted for her. Finally, she sprayed me with a small bottle that said Nursery Nights on it. It smelled like a combination of things; baby powder, soft nursery scents, and somethng else indefinable. In any event, I smelled so babyish, it seemed to eradicate any trace of boyishness I’d ever possesed.
“Take a look at yourself now, Chrissie,” she said in an almost taunting manner as she held my hand and stood me before the full length mirror.
I stared in awestruck silence as I gazed at the sissyish reflection in the mirror. With my slick glossy lips and light make-up, I actually looked quite attractive, albeit in a prissy kind of way. My bare legs and lacey panties and top made me look like an overgrown toddler and there was no mistaking my big, bulging diapers that announced I wasn’t ready for regular underwear yet. I blushed hotly as I quivered in anticipation of someone else seeing me like this.
“You see?” Barbara said as she bent over next to me and we looked at my reflection together, “This is the real you. This is how you should be dressed all the time. Not in some nasty boy’s clothes where you don’t belong. A cute little sissy like you should be dressed prettily, in prissy clothes that allows him to show the world who he really is.
“Of course, you’re more than just a sissy–you’re really just a big baby who isn’t ready to grow up. And believe me, I’ll make sure you don’t. You’re going to be my little baby girl from now on, wearing your diapers and dresses, just like a little toddler girl should.”
I gulped nervously at the picture she was painting. While I could grudgingly admit my features lent themselves well to a sort of prissier side, I didn’t want to dress like this all the time.
“Come along now Sissy,” she said taking my hand, “Here’s your purse with a few things I put in there just in case you need them later. But we have to be going–your new friends are all waiting for you.”
Before I could say another word, she was dragging me out the door and into her minivan, securing me in that oversized carseat in back. By now, I’d finished my bottle and she’d pushed my pacifier back into my mouth before closing the door. I squirmed helplessly, knowing there wasn’t a damn thing I could do about her plans for me.
It didn’t take long before we reached our destination. Her friend Emily’s house was just over in the adjacent neighborhood. As we pulled into the spacious driveway, I noted the large number of cars parked nearby, obviously from the other people who were here to see me. Looking down at my fat, frilly diapers and bare, hairless legs, I whimpered loudly to Barbara.
Opening the sliding side door, she began unbuckling me which also provided me with another opportunity to stare down her top at her big, beautiful breasts. But unfortunately, that was the last thing on mind at the moment. The full force of what was about to happen struck me with all it’s gravity and I struggled to stay where I was. There was no way I was going to let her drag me into this stranger’s house so they could look at me dressed like a baby girl!
As Barbara reached in to pull me out of the seat, I resisted her efforts, my muffled protests sounding babyish, just like my appearance. My pacifier fell out of my mouth and I tried to push her hands away to prevent her from getting me out of the van.
“Noo!” I whined, “I don’t wanna go!”
Barbara slapped my bare thigh with her immaculately manicured hand.
“Oww!” I cried.
“Chrissie–it’s time to mind your mommy and do as you’re told.”
“But I don’t wannnna!” I whimpered piteously.
She slapped my thigh again sharply and although it wasn’t that hard, I cried out in pain, tears brimming my eyes.
“Come along now, Sissykins,” she said firmly, “There are a lot of nice people waiting for you and you’re being rude to make them wait.”
Stuffing my pacifier back into my mouth, Barbara pulled me out of the seat and as I exited the van, I saw several women peering out through the living room window at me and smiling. I whimpered and balled my fists in frustration when all of a sudden, I felt a stream of wetness escape into the front of my diaper. I squealed in panic, my free hand going down to cover my humiliating accident, although it was doubtful that it could actually be seen. Still, the fact that I’d already wet myself would only show these women what a sissy I was and that I really did need diapers. On the way over, it occurred to me that the best plan would be to hold it until we were leaving but now that was clearly going to be pointless. Sooner or later, my accident would be discovered and Barbara would have an opportunity to heap yet further shame on me.
The front door opened before us and a gorgeous woman in her late thirties stood framed in the threshold, a big smile on her face as she looked down on me.
“Hello little Chrissie!” she beamed warmly, “My name is Aunt Emily–welcome to my home.”
Sweeping my up into her arms, she hugged me closely, mashing my face against her incredibly bountiful bosom. I could barely breath but for the moment, I wasn’t complaining. Her hand reached back and gently patted the ruffled seat of my diapers as she kissed me on the cheek.
Releasing me from her wonderful embrace, Barbara and her were soon hugging and chatting eagerly between each other. They ushered me in and I was taken into her large living room, now filled with a handful of beautiful women. They were dressed in various styles, from casual to what looked like business attire although they were all very attractive and sexy, most wearing heels and enticing clothes.
“Come in, come in,” Aunt Emily said as she gently but firmly beckoned me into the middle of the room. My face went three shades of red as these hotties stared at me and giggled, one feeling the lace on the hem of my sailor suit top, another rubbing my smooth thighs while another brazenly squeezed the thick seat of my diapers. I squealed in fright that she’d discover my accident and my pacifier dropped out of my mouth.
“Awww, the little sissy lost his paci,” one of the women said with mock sincerity as she patted me consolingly on my shoulder.
“Ladies,” Barbara said in a louder voice, “This is my new sissy baby, Chrissie–Chrissie, say hi to these nice ladies.”
My mouth was parched as I looked around in panic and my heart was racing as I barely prevented another stream of pee from escaping. I couldn’t speak a word!
Aunt Emily could see the terror in my eyes and she bent down before me, looking into my eyes with maternal warmth as she took my hands into hers.
“Hello there, Chrissie,” she said softly, “Did you know you’re the prettiest little sissy I’ve ever seen?” Her voice was musical, sexual, and filled with kindness all at the same time. In addition, I couldn’t help but stare at her wonderful, plump breasts, barely contained within a tight form-fitting top
I’d never been called pretty before and it gave me a strange sensation–I wasn’t sure whether to be proud or angry.
Still holding my hands in hers, she looked deep into my eyes, her attractive face just inches from my own.
“Chrissie? Are your diapers wet?” she asked full of concern, “Do you need me to take you into my nursery to be changed?”
“Uh-uh,” I croaked hoarsely. My face blushed an even deeper red as I feared she could read my mind and already knew the truth.
“Are you sure?’ she asked, a growing smile on her face.
I shook my head vigorously as the heat went all the way down my neck to my chest. I had never been so humiliated in all my life!
The women continued to giggle at my discomfort and I was unable to even raise my head to return their stares.
One of the women spread out a baby blanket on the floor and she beckoned me to sit down upon it. Awkwardly, I sat down, unsure of how best to position myself, keenly aware of how obvious my fat diapers were to everyone present. All around me, the comfortably seated women looked down on me and I could see them holding gifts that were wrapped in pastel paper with nursery designs. Looking up at their crossed legs, their high heels dangling before me while I sat on the ground, gave me a feeling of inferiority that I couldn’t shake.
“Here Chrissie, here’s a little present I know you’ll enjoy, ” a cute younger woman said, “–My name is Sarah,” she added as an afterthought.
Nervously, I licked my lips as I tore open the small, odd shaped package in a wrapping paper with building blocks on it. I saw a pink plastic ring about the size of a silver dollar and it was attached to a large rubber pacifier. Except the pacifier was shaped like a big, fat penis, not the usual elongated nipple. I blushed anew as everyone burst into laughter, obviously greatly amused with Sarah’s gift for me.
“I’ll bet you’d much rather have that in your mouth than your old pacifier,” she chuckled in a condescending manner. My face reddening, I tried to put it aside but Sarah stood up and came over to retreive it, picking it up and removing the plastic packaging. Tossing it aside, she forcefully pushed it between my quivering lips, forcing it deep into the back of my mouth. I gagged and threw my hands up, squealing like a little girl as everyone laughed at my emasculating predicament. This woman had a cruel look in her eyes, totally unlike Aunt Emily’s and I feared her instantly even as my lips submissively wrapped themselves around the big rubber cock filling my mouth.
Sucking noisily on the fat rubber phallus, I squirmed helplessly as she smirked down on me with a smug look on her face.
“I’ll bet that feels natural in your mouth–hm, Chrissie?” she asked.
Afraid to oppose her, I nodded and hung my head low.
“Awww you poor little thing,” Aunt Emily said sypathetically as she quickly came over and pulled the pacifier out of my mouth. She didn’t however, remove it entirely and instead, she looped the strap around my neck for later use, “Here Honey, now here’s something I know you’ll just adore.”
She presented her own gift that was delicately wrapped, and it too was in nursery print wrapping paper. I gritted my teeth as I ripped it open, to discover an elaborate pink and white dress, with yards of frilly lace and bows decorating it. It was obviously expensive and Barbara knelt down to feel it herself.
“Oh my!” she exclaimed, “Isn’t it beautiful, Chrissie?”
I nodded numbly, wondering how I’d ever come to be in this place, dressed like a baby and opening gifts made for a sissy.
“Now thank Aunt Emily for your wonderful dress, Chrissie,” she prodded me.
I was anything but grateful but I didn’t want to make Barbara angry either.
Clearing my throat, I coughed nervously.
“Thank you,” I practically whispered.
“Thank you–Aunt Emily,” Barbara corrected me.
“Thank you Aunt Emily,” I mumbled.
“Thank you for…” Barbara pressed.
“Thank you Aunt Emily for the pretty pink dress,” I finally blurted out, much to my embarrassment and everyone’s giggles.
“Well you’re quite welcome, Sugarplum,” she cooed, “And I’m very much looking forward to seeing you in it.”
Just then, a tall, dark haired woman with her hair pulled back in a severe bun stepped forward and thrust her own flat shaped package into my hands. It was long and narrow and looked suspiciously familiar.
“My name is Mrs. Sterne,” she said with an authoritative voice that could have cut through hardened steel, “And I run the Francis Merrimont Boys School.”
If Sarah had put me on edge–this woman was terrifying. Her dark eyes drilled through me like I were butter and I squirmed under her intense stare. She was quite attractive, but the firm set of her delicate jaw and the steely look in her eyes told me she meant business.
Swallowing hard, I slowly unwrapped the gift. It was a black oak Spencer paddle with a custom leather-wrapped handle and dime sized holes cut throughout it’s length. My heart pounded anxiously in my chest as I chewed my lower lip.
Everyone else oohed and ahhed but I was afraid to look the woman in the eye.
“I think we should give that one a try right now,” she stated firmly.
So certain was I that this forceful woman would get her way that I turned to Barbara, my eyes pleading with her for mercy.
“Don’t worry Chrissie,” she chuckled, “There will be plenty of opportunities for using that later.”
While not the answer I was exactly looking for, I was nonetheless relieved that she wouldn’t be using it right now.
Looking up, I noticed a younger female that had so far, said very little. She was devastatingly pretty, like Megan Fox, with bewitching eyes and round, perfectly shaped breasts. Her long, raven colored hair spilled over her soft bare shoulders and framed her toned, athletic body. The low cut halter top she wore was achingly taut against her perky bosom and below the cropped hem, I noted her washboard flat tummy.
I was in awe of her beauty and a little disappointed she’d been practically ignoring me thus far.
“I know,” aunt Emily suddenly suggested, “Why don’t we have Chrissie sit on Victoria’s lap while he opens the rest of his presents?”
I could tell from the young woman’s general demeanor that she had no interest in our proceedings and in all likelihood, she probably thought I was creepy. As if to confirm my suspicions, the dark haired beauty rolled her eyes and shook her head at aunt Emily.
“Look, I just came along ’cause I’m friends with Barbara,” she stated as she held her long nailed finger up in protest, “I don’t get what you guys are into with this sissy kid and his weird party.”
The way she said ‘sissy kid’ so dismissively was almost worse than Sarah’s overt condescending attitude towards me, maybe because she was the youngest one there and closest to my age, although she looked to be in her twenties. But to be so callously disregarded by such a pretty woman really hurt my feelings.
“Now Victoria,” Barbara interjected, “You’ll be having your own baby soon. You really should try to nurture your maternal instincts with Chrissie here. He may be a lot older than most boys who wear diapers but he’s really just a big baby deep inside.”
I tried to contradict the impression she was giving but the fat rubber pacifier only muffled my words and she talked right over me.
“Why don’t you just let him sit on your lap for a moment?”
While they were engaged in this discussion, I felt a strong surge in my bladder, signaling that Mother Nature was ready to make a call in a big way. The last thing I wanted was for this hottie to discover my wet diapers, but how could I avoid it?
“Naah, you hold him on your lap,” Victoria countered, “I’m not into sissies–I have a real man waiting for me at home.”
“Now Victoria…” aunt Emily said persuasively, “Just humor us this one time…he won’t bite–I promise you.”
“Yes, he’s really the best behaved little baby you could ever ask for,” Barbara added, “You haven’t even given the little sweety a chance…”
Victoria rolled her eyes again in apparent resignation.
“I know that Chrissie would just be thrilled to sit on the lap of a pretty young woman like you,” aunt Emily said with flattery, “Won’t you grant his wish this one time?”
Victoria exhaled audibly as Barbara took my hand and lifted me up. I shook my head and tried to tell her under my breath not to do it but she only ignored me, patting my diapered bottom and ushering me over. This was incredibly awkward and even though Victoria was stunningly beautiful, her obvious lack of interest in me made me loathe to be so near to her. But worse than that was my growing need to pee–I was flexing my fists and clamping my legs together just to keep it in but I knew I couldn’t hold out for much longer. How would I hide it if I were sitting on her lap?
Barbara sat me down and my bare thighs crossed Victoria’s which were exposed from the short shorts she was wearing. The touch of skin to skin made me feel prickly all over and as I looked into her pretty face, her drop-dead gorgeous eyes regarded me with indifference.
Another attractive young woman–also in her twenties–approached with a gift in her hands and she handed it over to me sweetly.
Still tense from struggling to keep from peeing, I took the package with trembling hands and opened it anxiously. Inside were a pair of frilly rumba panties, with multiple rows of fancy ruffles across the seat and leg openings. One was pink with white lace while other was baby blue with white accents.
As I fumbled uncertainly with the panties, the woman came over and put a comforting hand on my shoulder.
“Don’t worry Sissy–they’re cut full enough to fit comfortably over diapers even as big as yours,” she assured me.
Before I could think of some sort of response, a powerful urge gripped me to pee and I barely managed to resist it. However, I sensed that some had manged to leak out just as I relaxed my muscles. I squirmed on Victoria’s lap and whimpered helplessly but her only response seemed to be annoyance with me. Aunt Emily came over with another package and I knew I wasn’t going to make it. With a gasp and a sob, the floodgates opened with a vengeance. A strong, hot stream of pee surged unstoppable into my diapers, saturating the front instantly. Without thinking, my hand dropped to my crotch in a futile attempt to halt the flow but my actions only served to bring attention to what was happening. Another powerful surge came on the heels of the first and Victoria was starting to realize what was taking place. My pee was already soaking into the section between my legs and seeping back into my seat, giving direct evidence to Victoria as she felt the growing heat against her legs.
“Oh my god!! Are you peeing your diapers?!” she demanded.
My lip trembled in fear as I beheld her angry expression but before I could respond, she dumped me unceremoniously on the floor.
“Eww!! That is so gross!” she exclaimed.
Looking at her tall, strappy heels, up the length of her long, toned legs, the look on her face made me afraid she was going to reach down and slap me.
Without batting an eye, aunt Emily reached down and squeezed the thick seat of my diapers, even as I released another powerful stream. At this point, there was really no stopping it and I didn’t even try.
“It’s okay,” she said assuringly, “It’s just a wet diaper…He can’t help it–he really has no control.”
Despite myself, I felt hot tears of shame filling my eyes and one trickled down my cheek as Victoria stared down at me in disgust. Aunt Emily was running her finger around the leg holes of my rumba panties, checking for wetness as the last bit of pee flowed freely out of my bladder.
“You see? No leaks at all,” she proclaimed proudly, “His snug plastic panties kept it all in.”
“Aww, you poor thing,” Sarah said with her mock sympathy.
She was sitting closest to us and she reached down and grasped my new pacifier, stuffing the big rubber cock back into my mouth.
Victoria was shaking her head as she stared down at me coldly.
“That is so gross,” she repeated.
“Aww, come here,” Aunt Emily said, genuine concern in her voice, she bent down and wrapped her arms around me, hugging me close as she consoled me in her motherly way. She buried my head into her soft, cushiony bosom and my cheeks were surrounded by her big round breasts. Her hand patted my back and then reached down, patting my well padded posterior.
“Shushhh Baby,” she cooed, “Mommy’s going to change her baby’s diapers–don’t you worry.”
I sniffled and felt another tear tumble down my face as waves of shame washed over me. Any kind of speech was quite impossible with Sarah’s penis pacifier filling my mouth but inexplicably, I made no move to take it out. Sarah stood up and came to my side and together, they lifted me to my feet, checking once again to make sure I wasn’t leaking.
“Come on Chrissie, let’s get those wet diapers changed,”aunt Emily said as she took me by the hand and led me out of the room. I waddled between them, feeling very helpless and childish as the warm, soaked cloth clung stubbornly to my seat and between my thighs.
They took me back to another room, one made up very much like my own nursery at Barbara’s house. At first, I assumed aunt Emily had a baby of her own but then I noticed that everything was oversized in the same manner mine was; the crib, changing table, even the playpen looked like it were made for a small adult. I also recognized the faint but ever present odor of stale diapers, which made me wonder who else was being treated like me. Could there really be another teenager that was being dressed like a baby day after day?
Aunt Emily sat me down on the changing table, a low fixture that was padded and had nursery print vinyl stretched over the surface. But as she reached for the waistband of my rumba panties, I squirmed in resistance, whimpering as I vigorously shook my head. I didn’t want this pretty stranger to discover how small my little wee-wee was!
“Don’t worry Chrissie, I’ve changed plenty of sissy’s diapers in my time, there’s nothing you have that will surprise me, believe me,” she said as she tugged the flimsy rumba panties down off my diaper. I kicked and fidgeted, whining through my pacifier and wishing Barbara had come back to change me, maybe she would have interceded but now there was nothing to prevent aunt Emily from pulling my rumbas down my legs, revealing the big wet spot visible through my waterproof panties.
“My, you’re quite a wetter, aren’t you,” she commented as she reached under the elastic waistband of my vinyl panties and began working them down over the wet cloth.
My muffled protests did nothing to dissuade her or make her think I was anything other than an incontinent sissy. She snaked the panties down and proceeded to unpin my heavy wet diapers.
“Sarah–can you grab a pair of plastic panties for me? Joshy’s should fit him just fine–they look about the same size.”
Who was Joshy, I wondered. It felt doubly odd to be wearing baby pants from someone else my own age. And the thought I’d be wearing plastic pants that had been wet in by someone else bothered me too.
After sliding the soiled diapers from beneath me, Emily began wiping my groin and bottom with baby wipes. I blushed a hot red as she held my little penis like a crayon and began rubbing my tiny sack clean with the wipe. There was nothing the least bit sexual about her actions–it was simply a mother carefully cleaning her friend’s baby.
“Well,” she said as she slide one of the cool cloths down the length of my stiffening willie, “Looks like this sissy is still roaming free.”
“Not for long, I heard,” Sarah interjected as she handed aunt Emily a pair of pink polka dot vinyl pants, “That’ll be taken care of on Monday, I think Barbara said.”
What did she mean by that, I wondered. Once again, these enigmatic references to my penis caused me to be nervous about what she had in store for me.
“All I can say is enjoy it for now, Sissy,” aunt Emily said as she slid a thick stack of soft diapers under my rump.
“How long has it been for Joshy now,” Sarah inquired as she held the diaper pins for Emily.
“Oh…six, maybe seven months now, but I think he’s come to terms with it,” she responded.
Did she mean being treated like a baby or was there something else to her remark, I wondered.
Taking a big container of baby powder, aunt Emily began shaking it generously over my crotch and stomach. I kept waiting for her to stop but she just kept going, shaking more on me and rubbing it all the way up to my chest. The babyish scent assaulted my nostrils and I whimpered and fussed but she just smiled down on me and continued as before.
After pinning both sides of my diapers snugly into place, aunt Emily slid the soft but noisy plastic pants up my legs and worked them over the thick, bulging cloth.
“A big baby needs a big diaper–hm, Sugarplum?” she asked as she patted the shiny front of my fat diapers.
“And you know what?” Sarah asked as she beamed down on my prone form, “Its feeding time for my little baby–but today’s a special day for sissykins, you know why?”
I shook my head wordlessly.
“Because today, you get to pick which of these ladies you’d like to breastfeed from, won’t that be fun?” she said without waiting for an answer.
I sucked desperately on the fat penis pacifier in my mouth as I blushed anew and looked in panic from Sarah to aunt Emily. Why did Barbara have to tell them about that?
I whimpered in muffled futility but Emily wasn’t even paying attention.
“I know who he’ll want…” she said conspiratorily, “This little sissy here has a crush on Victoria.”
Sarah looked down at me as if she’d just been made privy to a naughty secret.
“You think so?” she asked intrigued.
“Oh yes–I saw the look in his eyes when he first saw her–the pretty young thing. I could tell he was hoping to make a good impression on her before he had his little accident…but I guess its a little late for that now.”
Sarah giggled with glee at the picture her friend was painting.
“Well we certainly can’t deny our little sweety her wish, now can we?” she replied.
Standing me up, Sarah held my hands in hers as she bent over to look me in the face.
“Chrissie, now that you’re wearing fresh diapers, I want you to go back out into the living room and ask Victoria if she’ll let you breastfeed from her.”
She finished her command by popping the pacifier from out of my mouth.
“N-no way,” I rmumbled, “I d-don’t wanna do that.”
She had to be deaf and dumb to think Victoria would give me the time of day–never mind let me suckle from her sexy boobs.
“Now Chrissie–this is for your own good. You march yourself right out there and do as I tell you,” she said firmly.
As if that were the end of the conversation, she turned me around and swatted my thickly padded rump, causing me to stumble forward in the direction of the hallway.
“No!” I argued, balling my fists in defiant fury.
No possible good could come from my asking Victoria what Sarah was suggesting and I knew my only chance to stop her was here and now. Holding my ground, I placed my feet apart in a stance of rebellious obstinacy. I knew I must look silly, standing there in my Mary Janes, fat diapers and a pink sailor suit and expecting to be taken seriously.
“Chrissie…you will go out there, and you will ask Victoria in a polite manner to please give you your feeding–do you understand me?” Sarah said, her voice taking on a menacing new edge.
“Uh-uh,” I replied stubbornly. I wasn’t willing to budge an inch.
“Chrissie, I’m going to give you three seconds to walk out that door or so help me, I’m going to pull you over my lap and blister your bottom–its that simple.”
I bit my lip anxiously as I considered my position. This woman looked determined to do what she was threatening and I didn’t doubt her ability in the least. Like everyone else here, she was taller, even without her high heels, and I knew she would be stronger than me as well, even without aunt Emily’s help.
“–Okay, I’ll do it!” I suddenly blurted out in panic.
Sarah reached into her purse and produced a hard, oval shaped wooden paddle with the words ‘For sissy bottoms only’ in red across its face.
“Do you need a hand?” aunt Emily asked casually, her face showing amusement at my impending punishment.
“Oh no, this little sissy looks as weak as a lamb,” she said calmly, “But he’s about to find out what happens when he doesn’t do as he’s told.”
“No–no wait!” I pleaded as she snatched my wrist in her iron grip, “I said I’d do it!”
Without paying me any heed, Sarah dragged me over to a straight backed chair in the room and took a seat.
“Time for a little lesson in manners, Sissy-boy,” she told me.
“No…no….no,” I pouted as I stamped my feet in frustration.
Sarah tugged my pink polka dot plastic pants back down and then forcibly jerked me over her lap as a new set of tears spilled down my cheeks.
“Wait! Please–please don’t spank me!” I cried.
“If you had done as I’d asked of you, you could’ve been nursing from pretty Victoria by now but instead, you’re going to get your little sissy bottom paddled,” Sarah said as she unpinned either side of my diapers.
I kicked and fidgeted, pleading with her to give me one more chance.
“B-b-but you didn’t even get to three!” I wailed in consternation.
As if in answer, her paddle swooped down and landed with a loud crisp SMACK! on my raised bottom. My argument ended in a burst of tears that immediately began streaming down my face.
Swat after punishing swat landed on my defenseless fanny. The nursery door was wide open and I knew my crying and sobbing would be clearly heard by everyone still in the living room. Not only that, the loud, angry slaps of Sarah’s paddle reverberated in the room as it impacted my soft, youthful buns and I knew the women could hear every stinging swat, each time it landed with impunity. Everyone would know the childish punishment I was receiving and there was nothing I could do about it!
My Mary Janes were drumming a frantic rhythm on the floor as Sarah methodically ensured that every square inch of my rear received it’s scorching, blistering reward. Bawling loudly, I beat my fists on the floor as I lay there, helplessly enduring each swat of the paddle as it seared itself into my skin.
When she at last finished, she put the paddle back in her purse and pulled the back of my diaper up into position. I looked down through tear filled eyes upon aunt Emily’s high heeled sandals as she handed my diaper pins to Sarah.
“There…I don’t think we’ll be getting any more arguments from Chrissie today,” Sarah stated smugly.
“Are you ready to be a good sissy now?” she asked me.
I howled out and nodded my head emphatically as she helped me to stand. The inferno on my rump caused me to dance in place and I stamped my feet in pain and frustrated anger.
“Stand still Chrissie, so I can pull up your baby panties,” she chided me.
As I fidgeted in place, Sarah snaked the cheerful polka dot panties up my quivering, skinny legs and worked them over the bulky cotton cloth. Once again, I felt the temperature rise about twenty degrees as she sealed the smoldering heat inside my diaper.
“Maybe that’ll teach you a lesson, next time you get sassy with me,” she scolded me firmly, “When I tell you to do something, you’ll do it without question, and without any backtalk–you got that?”
I cried even harder as I nodded me head, keeping my eyes submissivley downcast so as not to anger her any further. This woman was strict!
While I cried unashamedly, aunt Emily looked down and smiled at me. Oh, how I hated her now! She’d done nothing to stop my humiliating punishment and if anything, seemed happy to have taken part!
Standing up, Sarah took my hand and led me out of the room, looking like a punished toddler as I sniffled and wiped my hands across my wet face. To make matters worse, she wasn’t even giving me the chance to get my crying under control before everyone saw me, looking like a naughty little crybaby.
“Come along Sweety, there’s something I know you want to ask Victoria.”
I realized there was no getting out of this and the only thing to do was play along and be humiliated in front of everyone. How could things possibly get any worse for me?
Waddling into the living room, everyone grew silent and their eyes were upon me as I sniffed and did my best to act brave. It was obvious that everyone could see my puffy eyes, wet cheeks, and it was certainly no secret as to what just happened.
“Looks like a certain sissy just got his bottom spanked,” Mrs. Sterne remarked in her smug, superior tone.
“If you’re trying to potty train him–I fully agree with your methods,” she told aunt Emily, “A good hard spanking always does a sissy a world of good. Maybe next time, he’ll tell you before he decides to wet himself.”
“Oh no, it wasn’t that,” Sarah smiled, “We just had to settle a little disagreement but its all resolved now.”
With her hands on my shoulders, Sarah walked me over to Victoria, who was still sitting on the couch, filing her long, French manicured nails. Her long, sexy legs were crossed again and her high heel dangled over the floor.
“Um…” I began uncertainly.
I was used to being ignored by the hot girls at my school and this only brought that feeling of inferiority back with a vengeance. Victoria barely looked up from her nails to acknowledge my presence.
I was hesistant to say anything further but Sarah nudged me in the shoulder blades.
Clearing my throat, I began again.
“Um…Miss Victoria?” I began in a small voice, “…Um, do you think I could-um…kinda..um, n-nurse from you t-today?”
For the first time, she peered up from what she was doing to look me in the eye.
“You want to do what?” she asked incredulously.
My face reddened hotly at her blunt reply.
“Um…I mean…can I…I mean…do you think…” I stammered as I looked into her cold, piercing eyes, my face burning with shame, “Could I b-b-breastfeed from you?”
“Are you freakin’ kidding??” she demanded, “Get away from me you little twerp.”
Hot tears of shame filled my eyes as the other women giggled merrily with amusement. This was far worse than any dismissal I’d received from any schoolgirl, anywhere.
“You poor little sissy,” aunt Emily said as she came over to my side.
Taking me by the hand, she plopped me over her lap so abruptly, I landed face up, my legs sprawled across the love seat she had taken a seat on.
“Don’t you worry Babykins,” she said in a voice designed for addressing toddlers, “Aunt Emily’s going to make sure you get your fill and then some.”
I gasped in shock as she unbuttoned her snug top and revealed two giant globes of femininity, straining desperately within a smooth, satin white bra. I began fidgeting and whimpering, shaking my head as she undid the clasp in front and releasing her heavy breasts from their cups. Her pink nipple was staring me straight in the face and I gaped at it and then up into aunt Emily’s beautiful grinning face.
“Its milk time, Chrissie,” she said cheerily and without waiting for a reaction she mashed my face against her giant breast.
I squealed loudly but in opening my mouth, her firm nipple slipped in and my cries were soon completely muffled. Whining and fussing, I struggled in her lap but soon settled down, to nurse from the steady stream of milk flowing into my mouth.
Flush with victory, aunt Emily beamed down on me as she stroked my cheek softly.
“Thaaat’s it Baby….take all you want…there’s plenty for a thirsty sissy here…”
Looking over at her other plump breast, I had no doubt she was correct. The one in my mouth seemed to have an endless supply and I suckled away for some time until my jaw began to get sore. By now, the other women had begun talking amongst themselves, having completely forgotten about me. In their minds, I was just another baby getting breastfed by his aunt who was in no danger of running out of milk. After getting my fill of her right breast, aunt Emily switched me over to the other one, working her leaking nipple across my pursed lips until I finally capitulated and surrendured to her will. It was another long fifteen minutes before she finally eased her nipple from my sore mouth and helped me to sit up.
My stomach was full and I could feel the liquid sloshing around in my belly. I felt both dizzy and a bit queazy as I fought back a burp and looked up at Barbara through half closed eyes.
“Well, its Chrissie’s naptime, girls,” she said as she took my hand, “Tell everyone thank you for a wonderful afternoon, Chrissie.”
Unaware of the milk that had dribbled down my chin and dried during the course of my breastfeeding, I mumbled out my thanks to everyone under my breath.
“Nighty-nite, Chrissie,” one of them said and I waddled along as Barbara took my back to the nursery.
Taking only enough time to remove my Mary Janes, she lowered the crib side and helped me in, pulling the baby blankets back up as I settled in. I had to admit I was rather tired from everything that had happened although I still resented having to take a nap like a little baby. And the waterproof vinyl sheet I was laying on smelled slightly of stale pee which only humiliated me more. After all, I wasn’t a bedwetter so why did I have to sleep in a bedwetter’s bed?
After Barbara had gone, and the crib top was locked in place, I began feeling the first stirrings that all that milk was having on my system. I fought it, squirming and fidgeting as long as I could until nature finally won the battle. Lying on my back and staring up at baby’s mobile above the crib, I relaxed and wet my diapers heavily, hoping my plastic pants would be able to hold it all in again. Sobbing in defeat, I hugged my teddy bear closely as I softly cried myself to sleep knowing I’d probably only wet some more while I slept.

Chapter Five Chrissie’s Present

Monday morning, I woke up with a very wet diaper. This was a disturbing trend that had started a few days ago with just some dampness in the morning that at the time, I’d dismissed as an accident. But then the next night, the cloth between my legs had been wet and cool when I woke up and today, my diapers were completely soaked. I hadn’t wet the bed for years and I had no idea why it was happening now. Could wearing diapers 24/7 have had some subliminal effect on my system?
This was normally the time in which I’d masturbate at a nice, relaxed pace before Barbara came in to get me. I always woke up horny, and the cushiony soft, comforting cotton of my diapers was simply too tempting to ignore. Truth be told, I was beginning to develop a secret appreciation for them. The male side of me told me that I should despise the babyish underwear and realize they were part of Barbara’s cruel design to sissify me. But the physical side of me was growing to love their soft comfy hug around my loins and bottom. When I walked, or rather, waddled, the plastic panties slid pleasantly between my inner thighs which I had come to enjoy. But more than anything else, the pillowy folds of bunny soft cotton made for a perfect means to massage my perpetually horny penis, so I could indirectly stroke it to orgasm after shattering orgasm.
Fact was, I’d never played with myself so much in my life. Part of that was because of the diapers but another part was being in such close proximity to a sexy woman like Barbara. Yes, I resented the hell out of her for turning me into her baby girl, but my penis didn’t care that I was wearing a dress most of the time. All it knew was that Barbara had the sexiest boobs I’d ever laid eyes on and they were all the inspiration I needed to stroke myself to a eye crossing climax, day after day.
This morning however, the fact that I’d wet myself so thoroughly was distracting me from my usual activity. I rubbed the front of my diapers but all that pee it was holding had taken away some of the cushiony feel I had taken for granted. And it was still nagging me as to why and how it’d happened. Waves of guilt washed over me as I lay there, staring through the pink bars of my crib. My body was punishing me for accepting my babyish status–that had to be it. I’d come to accept and even secretly enjoy my diapers and now my body was telling my brain it didn’t have to give me any notice if I needed to pee. Was I destined to wet the bed from now on? And what about during the day? Would I just find myself wetting my diapers without any prior indication?
Even as I rubbed the soft, smooth vinyl covering of my diaper, trying to get some relief, these thoughts kept intruding on my conscience.
Suddenly, the nursery door opened and in walked Barbara which forced me to stop masturbating as well as distract me from my line of guilty reservations.
“How’s mommy’s little baby?” Barbara asked sweetly.
She was wearing tight white shorts and a breathtaking button up top that displayed her plump, sexy breasts to great effect.
I was ashamed to admit I’d wet my diapers but at the same time, I wanted her to change me because they were getting cool and clammy.
“Um…I um…” I stammered uncertainly.
“Yes, Sweety?” she said as she unlocked the top of the crib and pulled it back. Looking down on me, her big, mouthwatering breasts hung before my eyes and my penis began to harden all over again. It was a sight I never tired of gazing upon and I felt an electric wave of horniness ripple through me. I was going to enjoy my morning stroke when she finished changing me.
With her infallible instincts, she put her hand down against the front of my diaper and gently squeezed it. I wasn’t concerned about her detecting my hard on because my penis was far too small to be felt or seen in my thick diapers.
“Aww, did mommy’s little baby wet her diapers?” she asked in her honey voice.
“Uh huh,” I mumbled as I blushed a little.
“Don’t you worry Sugarplum, because we’re going to get you changed right away. Today’s a big day for you because aunt Melissa dropped off her special present. I just can’t wait to show you–its just what you need,” she gushed.
“Wha-what is it?” I asked, somewhat apprehensively. I had become increasingly skeptical of Barbara’s special presents.
“You’ll see very soon, don’t you worry Sissikins,” she told me as she reached down and grasped the pacifier that was looped around my neck. Holding it before my lips, she began rubbing it against them until I reluctantly submitted and let her push it into my mouth.
“That’s a good girl,” she commended me, “Now, its very important that your pacifier stays in this morning, okay Chrissie?”
I nodded my head in ackowledgement; it wasn’t a big deal with me. Hopefully, in less than an hour, she’d be done with whatever she had in mind and I’d be able to stroke myself to another dizzying orgasm. I don’t know why, but looking at the smooth skin on the round curves of her beautiful bosom was making me especially horny this morning.
“Its very important that you don’t take it out because if you do, I’m afraid I’ll have to give you a nice hard spanking and you don’t want that, do you, Baby?”
I shook my head slowly in silence, idly wondering why it was so important to keep my pacifier in.
Taking my hand, she raised me up in the crib so I was on my knees and my hands were resting on the side rail.
“And just to make today even more special, you have two visitors that are here to see you,” she said as she patted my arm in a motherly way. The last thing I wanted was to be seen by anyone new but I was hardly in a position to argue with her about it.
Stepping back, Barbara put her head outside the nursery and beckoned to someone out in the hallway.
“Come on in Pamela, your baby son’s awake and eager to see you.”
My eyes grew as big as saucers as my mom and sister strode into the room. My mouth dropped open in utter shock but Barbara was quick to hold my pacifier in place. In a fit of panic, a strong, hot stream of pee surged into my diaper, making me whimper around the rubbery nipple filling my mouth.
“Well!” my mom exclaimed happily, “What a change you’ve made in so little time!”
“You’ll find Chrissie is just the best behaved little baby anyone could ask for,” Barbara boasted.
My mom came over and looked me up and down, obviously very pleased with my infantile attire. This morning I was wearing a fuzzy soft Strawberry Shortcake top in pink and white with short, puffy shoulders. The hem came down just past my navel leaving my babyish pink plastic panties fully on display.
“Has he been using his diapers, or are they just for looks?” she asked curiously.
“Oh–he uses them alright, every day–several times a day. As a matter of fact, Chrissie’s wetting the bed regularly now so there’s really no going back now for him. Feel for yourself.”
My mom reached over and felt my diapers, immediately sensing the wet warmth beneath my plastic pants.
“My little baby boy!” she cried wistfully. It was if she were happy to have me back as a baby again.
I sucked desperately on my pacifier, blushing fiercely and making panicky slurping sounds as she looked me over. I wanted to say something, but I didn’t dare risk Barbara’s wrath with her paddle. Out of the corner of my eye, I saw my little sister approach and stare up at me in wonderment.
“Mommy? Why is Chris wearing diapers?” she asked innocently.
“Because he has no self control,” Barbara quickly replied, “And because he’s a sissy and all sissies need diapers or they’ll pee their pants.”
That seemed to satisfy her for the moment and she smiled up at me, not a little surprised at what she saw.
“You look like a baby girl,” she said in her little childish voice.
I hung my head in shame at being the center of attention. Trapped in my crib, with no where to go–this was absolutely mortifying!
Barbara unlatched the crib rail and lowered it to help me out.
“You’re right on time Pamela, because I was just about to change Chrissie’s diapers, would you like to lend a hand?”
My mom sighed with maternal contentment.
“I haven’t changed Chris’ diapers for…”
“–Mommy–can I help too?” Lindsey interrupted impatiently.
“I don’t see why not,” she replied, “Why don’t you pick out his plastic panties, Dear.”
“Okay!” she cried with glee.
Barbara led me over to my changing table as Lindsey began excitedly thumbing through the drawer that contained my waterproof pants.
“Is it hard to find baby clothes for a boy of his size?” my mom inquired with interest.
“Oh no–not at all,” Barbara told her emphatically, “And Chrissie has taken to them like a fish to water. As a matter of fact, he wet himself the very first day and hasn’t had a dry night since. I know he was glad to finally be rid of his boy clothing and he just loves the feel and comfort of wearing soft diapers and his other baby things. He’s so much happier getting to dress up every day and he looks forward to seeing which outfits I’m going to pick out for him. His favorites are always the most babyish, frilliest ones, usually in pink or other girly colors.”
“Oh my,” my mom murmured in wonder.
I shook my head trying to deny what was being said but she wasn’t paying attention.
“So I guess all this time, he’s just been acting like he enjoyed boy’s activities, but in reality, he probably just wanted to be a little girl again,” my mom reasoned.
“Yes…but in Chrissie’s case, the fact is, he’s not yet ready for dresses and panties–he still very much needs his diapers and plastic panties–as you can see for yourself.”
As I lay on the vinyl covered table, Barbara pulled down my clinging baby pants to reveal the sopping wet diaper underneath.
“Basically, your son here is a little sissy that just refuses to grow up. I think if he had it his way, he’d stay a baby girl for the rest of his life.”
I whimpered around my pacifer in mute protest.
“Well, the change has certainly done him a world of good,” my mom agreed wholeheartedly, “I think this is the best thing that’s ever happened to him.”
I winced in frustration at this humiliating discussion concerning me.
“And if I may, I think you should stop thinking of him as your son. Chrissie wants nothing more than to be a good little baby girl and I’m going to give him–or should I say her–that chance.”
“Yes…I guess I always knew he’d never amount to much of a man, if and when he ever grew up. With his soft, smooth legs, lack of pubic hair and his sissyish ways, it looks like he was always meant to be a toddler girl.”
“That’s what I thought, the first time I saw him. It really is the best for him.”
“Seeing him now in his baby clothes and wet diapers–I’m certain of it,” my mom concurred, “Lindsey, you may have lost a brother but you gained a baby sister.”
My sister giggled merrily in response.
Barbara had removed my diaper and was cleaning my bottom and genitals as Lindsey brought over a pair of plastic pants. Just as I feared, they were the most girliest ones that were there; pink with white bunnies and frilly eyelet lace around the legs.
“Mommy? Are these panties okay?” she inquired earnestly.
“Yes Honey, thank you,” my mom said accepting them.
“Chrissie, I want you to hold these while we’re getting your diapers ready,” my mom told me.
I was crushed with humiliation, having my mom treat me like a child again and a tear of shame trickled down my cheek as I sucked miserably on my pacifier. In helpless frustration, I took the panties and held them to my chest while Barbara slid another fresh stack of diapers beneath my rump.
“He really does need thick diapers, doesn’t he?” my mom asked.
“She certainly does, and there’s really no reason to try and hide them or be discreet about it–everyone knows she needs them and I don’t want there to be any doubt about what she’s wearing. In addition, I’ve made sure her outfits are all cut short so her sissy diapers can be seen by everyone and actually, it makes changing her that much easier too.”
“And now we’re ready for Chrissie’s special present,” Barbara announced dramatically.
Lindsey’s brow creased slightly as it seemed like I was getting all the attention and she wasn’t getting any. That was the last thing I wanted!
Barbara turned briefly and when she came back around, she was holding a small white box in her hand. From inside it, she produced a strange semi-clear looking device that was shaped more or less like a penis except that it had a wide collar of some sort near the base and I could tell it was made of a slightly flexible material.
“Is that what you were telling me about before?” my mom asked with interest.
“Yes, Pam. This little gem will put an end to your son’s masturbating habit–once and for all.”
Barbara unwound a circular plastic strap that went around the thicker silicone collar and put it down next to me. I tried to pick it up to get a closer look but she slapped my hand away brusquely.
“That’s not for you to play with, Chrissie” she chided me, “Only grown-ups can touch this.”
“How does it work?” my mom questioned her.
“Chrissie’s little sack and penis go through this collar and then her willie goes into this tube. As you can see, this extension piece draws her little penis down and between her balls which prevents her from getting an erection. Also, the size of the tube limits how much her wiener can grow so that she won’t be able to get hard anymore. She won’t be able to touch or stimulate it, which means she won’t be able to stroke herself and masturbation will now be a thing of the past.”
“Does it really work effectively?” my mom asked in amazement.
“Oh yes–it’s quite foolproof. Once this collar is locked in place, there’s absolutely no way she can pull her pee-wee through or get access to it,” she said simply.
“But will it hurt him?’ she asked concerned.
“Oh no–not in the least. It’s comfortable enough to stay on 24 hours a day, seven days a week–after a while, she won’t even know she’s wearing it. And sissies really don’t need to cum, so she’s not losing anything there, either.
“You see, one problem with sissies who wear diapers is that the diapers themselves can be a tremendous temptation. The soft, cushiony cloth feels wonderful on their little penises and they can’t seem to control themselves. Chrissie here has been no exception–she’s been playing with herself nonstop since she arrived.”
I gasped in shock–how could she have known??
Looking back down on me, Barbara smiled with a smug grin.
“Oh yes, baby girl–I’ve known all about your little masturbating activities from your first night here. You thought you were keeping it a secret but I’ve known all along. And now I’m putting a stop to it. I hope you had a good orgasm last night while rubbing your diapers because its going to be your last one.”
A shiver of fear and trepidation raced through me as I contemplated the terrifying magnitude of her words.
“This will keep her from being naughty, and make her the best possible sissy any mommy could ask for,” she said as she turned back to face my mom.
“If only I’d had this a year ago,” my mom lamented.
“Better late than never,” Barbara replied, “Now Chrissie, I want you to ask your mommy if she’ll be so kind as to put your chastity device on for you.”
Hearing all this, I was completely aghast. How could such a diabolical device exist? How was I going to go without cumming–ever again?
When Barbara pulled the pacifier out of my mouth, the panic induced words tumbled out of me like apples from a barrel.
“Mom! You’ve got to get me out of here! I don’t wanna dress like a baby–I don’t wanna wear that thing! Pleeaasse–please Mom–don’t let her do this to me!”
My pleading turned into a whining, babbling cascade of noise that was quickly becoming unintelligable.
They both looked down on me but neither showed the least signs of sympathy.
“Mom!–She made me wet my diapers!–This wasn’t my idea–please take me home–I don’t wanna stay here anymore,” I pleaded desperately.
“Hmmph,” she sniffed, “It’s just like you said he’d be–acting like he doesn’t like his diapers and baby treatment.
“I don’t believe you for a second. The amount of time you’ve spent masturbating in them proves beyond a shadow of doubt how much you like them, Chrissie.”
I blushed red with shame, realizing that at least on some level, there was a kernel of truth to her accusation. If only I’d had more restraint! But what could I say now?
“Oh no, ever since you were a little boy, I’ve suspected you were nothing but a sissy. And remember that time aunt Holly caught you playing dress up with her daughter? You tried to tell me it was her idea than as well.
“Oh no Mister–you’re staying right where you are. I knew when I first walked in and saw you in your wet diaper and sissy top that Barbara had pegged you exactly right. You are a sissy and you do need diapers. Not only that, you need a secure chastity device to put an end to your constant masturbating. Its a disgusting habit and I won’t put up with it another minute.”
I’d never seen my mom so full of conviction and authority in all my life and I was temporarily at a loss for words. Barbara, on the other hand, was smiling with cool, smug satisfaction. Everything had gone exactly as she’d planned.
Taking a bottle of baby oil, she squeezed some out onto my small, hairless genitals, rubbing it all over my little sack. Despite my shock and confusion, her gentle, soft touch felt wonderful and as I gazed numbly at her big beautiful breasts, jiggling sexily within her snug top, my wiener automatically stiffened to attention.
Grasping the silicone device in one hand, Barbara began working each of my balls carefully through the collar until both were on the other side together. With the container of baby oil, she dribbled a little more and stroked my wiener with it.
“We want to get you all nice and slippery for your new home, Chrissie,” she said sweetly as she smiled down on me.
I began whimpering helplessly as she pushed my wiener down through the collar so that my whole package was now on the one side of the device and the collar ran around the base of my genitals.
“No…no…please…mommy!” I protested weakly.
Grasping my slippery wiener between her thumb and index finger, Barbara poised it before the opening in the penis shaped tube.
“Say hello to your new friend, Chrissie, you two are going to become very well aquainted,” she gloated.
I squirmed and whimpered, too much in a daze to interfere as she pushed my hard-on into the snug, restrictive tube.
“Need this?” my mom asked as she held a bag of frozen peas in her hand. I had seen them earlier but didn’t understand why she had brought them in.
“Yes, thank you,” she replied as she took the bag and held them up firmly against my scrotum.
“AGGHH!!” I cried as the frozen bag hugged my balls.
Barbara smiled down on me with satisfaction as she held them in place.
“It’s okay, Sissy, just a little coldness to take away your last erection so we can get you all locked up properly.”
I squirmed and thrashed on the table, trying to get away from the bag but she followed my movements and held it cruelly in place. I could feel my hard-on inexorably losing the battle and shrinking down; in just a moment, my little penis was once again, limp as a noodle.
“There you are,” she beamed down at me, obviously happy with the results.
Now that my wiener was no longer stiff, Barbara tucked it, now trapped inside the tube, down and between my balls where the locking strap came up and around the collar. My willie was now positioned straight down and unable to move.
“No…please Mommy, don’t let her do this to me,” I begged her piteously as I stared down at this evil, devilish device.
Ignoring my protests, Barbara wrapped the locking strap around the collar and joined both ends, pushing the locking pin into the holes on either end. From somewhere below me, she produced a small lock and I watched in horror as she slipped it through the pin, and snapped it shut with a crisp click.
“There,” she said with tremendous satisfaction, “That’s put an end to your masturbating, once and for all.”
I looked up at her with horror and shock on my face.
“Chrissie. I told your mom I’d stop your masturbating and now I have, permanently. This will stay locked in place under your diapers from now on except for periodic cleaning and a milking once a month. Now you’ll be using your diapers for their intended purpose, just like a sissy should,” she told me.
Looking down at my caged penis, I watched it wriggling like a trapped fish as I flexed my muscles, unable to get hard within the snug confines of this dreaded silicone chastity device.
“Its not fair!” I wailed as I brought my fists down on the table in sissyish frustration. A tear trickled down my cheek and I angrily swiped it away.
Barbara giggled merrily, obviously quite pleased to see me so thoroughly controlled.
More tears tumbled down my face as I grabbed the device and struggled to get it off. The design of it was ingenious however and I couldn’t even get to a part of my penis to extract it from its rubbery prison. Nor was it possible to slip my balls back out now that the collar was locked in place.
Waves of panic swept over me as I saw my last avenue of pleasure closing like an iron door.
“Okay Chrissie, finished playing with it? Because now its diaper time for you,” Barbara said nonchalantly as she began positioning the stack of fresh diapers beneath my rear.
“Noooo! Noooo!” I wept bitterly as she lifted my kicking legs and powdered my rump generously.
“Chrissie? Do you need your bottom spanked before I put your diapers on?” she asked as she paused her ministrations.
“No!!” I snapped angrily, knowing she held all the cards now and I was helpess to do whatever she demanded.
“Good, because you’re going to do as I say or I’ll pull you over my lap for a good hard paddling.”
My mom grinned with a smug look I wasn’t used to seeing as I pouted in frustrated silence, my lower lip thrust out like a petulant toddler. She knew I was beaten and completely at this strict woman’s mercy.
“That’s right, Sissy, better hold that tongue if you know what’s good for you,” she taunted me as she pinned the diapers up snugly. I sniffled impotently as she took the plastic panties I was holding and began snaking them up my legs.
My mom reached over and grasped my pacifier, holding it before my face.
“Open up, Chrissie, here’s your paci,” she said.
I burned with frustration over this complete reversal of power but I knew I had no choice but to submit. Choking back a sob, I opened my mouth and was rewarded with a large rubber nipple.
Looking down, I watched as Barbara shook baby powder between my inner thighs.
“And now, I think we’ll give your new friend it’s first test,” Barbara announced, “You see, in addition to being a chronic masturbator, Chrissie here is also a premature ejaculator. I’ve been nursing her like the big baby she is but she can hardly stand it for more than two minutes before she cums in her soft, fluffy diapers. She really has no control at all. But now that her little penis is locked down, we’ll see if she can’t stay for her entire fill.”
“I didn’t know you were lactating,” my mom exclaimed with amazement.
“Oh yes, I was helping out a friend who just had her own baby but then I met Chrissie here, and I realized a sissy like her should be weaned at least once a day, as part of her discipline program. She enjoys it immensely, until she cums that is, and then she starts to fuss like a whiny baby with a wet diaper.”
“I can imagine that all too easily,” my mom concurred.
“Come along, Chrissie, it’s time for your breakfast…come to mommy,” Barbara said as she took my hand and led me over to the loveseat she used expressly for that purpose.
Reluctantly, I took my place across her lap, face up, as she made herself comfortable, unbuttoning her low cut top. I was angry as hell with her but my horniness had suddenly reasserted itself and the sight of her big, succulent melons being further exposed somehow managed to push my resentment onto a back burner. She cradled my head gently and with her free hand, gently undid the clasp holding her two giant mammaries in the cups of her satin bra.
“Here you are Sissy, time for yum-yums…”
I was ashamed to be such a willing participant in her childish game and I pursed my lips in a pathetic show of defiance.
“Open up Baby, mommy’s got her milk for her sweet little sissy,” she sang.
With her usual patience, Barbara simply pinched my nose as I stared at the large, dripping pink nipple poised before my lips. I squirmed and whined, shaking my head but she only smiled down at me and waited. At last, I gasped for breath and was quickly rewarded with her warm, milky nipple. I tried not to think about it, but my entire field of vision was filled with Barbara’s soft, sexy boobs, one in which I had my mouth clamped onto and the other, still partially contained by the silky cup of her bra. My penis had a mind of it’s own and it throbbed wildly now in it’s new prison, struggling frantically to become erect and hard. I fought the urge to nurse but then Barbara slapped my bare thigh with her hand. Dutifully, I began suckling, the firm nipple filling my mouth as streams of milk started to flow.
“Thaaat’s my good girl,” she cooed, “That’s a good baby.”
My horniness was building inside and I felt my heart pounding within my chest. My wiener was flexing and doing everything it could to break through the silicone tube it was trapped inside but it was quite impossible. I whimpered weakly as I tried to get some satisfaction but my penis couldn’t feel a thing. Normally, just a little friction inside my diaper was enough to make me explode but the chastity device was preventing any kind of contact. Meanwhile, Barbara was giving me encouragement, softly stroking my head and telling me what a good job I was doing. I felt so babyish but I was also so horny I could cry!
My mom had taken a seat next to us and while I couldn’t see her directly (all I could see were breasts!), I sensed she was watching me with intrigue.
“So does he nurse everyday?” she asked Barbara.
“Oh yes, without fail. The problem before was her premature ejaculating but now, we seem to have that all under control–don’t we Sugarplum?” she said in her syrupy voice reserved for toddlers.
She seemed eager to explain her methods for dealing with me as she continued;
“I produce enough milk of my own that–now that we’re not having to stop early–I know she’ll be able to get a full meal from each nursing session,” Barbara said with a trace of pride.
“Yes, I can well imagine,” my mom said appreciatively. It certainly wasn’t hard to believe, given the tremendous size of her breasts.
“But I also have a couple friends who happen to be lactating–I’m planning on bringing them over so she can get some extra breastfeeding from them,” she explained, “I want her diet to have a large liquid intake which will also help break down years of trained continence. It’s already having quite an effect.”
I felt completely excluded from the conversation, just as a baby would who’s mommy was breastfeeding it.
“A sissy needs breastmilk, and it helps to reinforce her position mentally that she’s still just a baby. Making the adjustment from a grown boy to a helpess baby girl can be somewhat stressful and this helps to keep her calm and mold her into her new role. I’ve also found that regular breastfeeding makes a sissy more docile and easy to control. They fuss less, and naptimes are less of a trauma. They really become quite submissive.
“Another side effect seems to be incontinence. I’m not sure why, but when a sissy begins breastfeeding again, they tend to lose control of their wetting. I’ve found many become bedwetters in just a couple days and they begin wetting their diapers during the day, shortly thereafter.”
I cringed and whimpered at the thought of what she was saying. Could it really be true? It sure seemed like it in my case.
Barbara gently pulled my suckling lips from around her nipple.
“Okay Sweety, time for the other breast now.”
I whined some more as the wet nipple was pulled away from me but in moments, she had positioned her other one before my still mewling mouth. It was huge, like the other, pink and glistening with milk.
“Open up Chrissie,” she whispered, “Breakfast time.”
My wiener was aching with desire and I felt dizzy from my futile efforts to achieve an orgasm. Hungrily, I gobbled at her nipple, sucking it hard in my desperation. Subconsciously, I think I believed that if I could just get a little more milk, I’d be able to get that elusive orgasm.
“Gently Honey…gently,” Barbara chided me.
I fought to control myself and I tried surrepticiously to reach down with my hand to rub the front of my fat diapers, oblivious to the fact my mother and sister was watching me closely. Ordinarily, I would never have done something so blatant but my sex drive was making me crazy to get satisfaction.
“Now, now, Chrissie, keep those naughty hands where they belong, they can’t do anything for you now.”
I whimpered as I swallowed another warm mouthful of milk. I wanted so badly to cum–it was so unfair! I would have killed to be able to climax in my cozy diapers at that moment but she had made it totally impossible!
As I nursed from her giant right breast, I was feeling my tummy getting full from all that milk. Much as I hoped to be able to achieve an orgasm from my continued efforts at her breast, it was becoming increasingly clear that I was no closer to cumming than when I started.
“How’s that, Sweety? Did mommy’s baby girl get her fill today?” she beamed down on me.
I nodded weakly, my penis still throbbing in frustration.
“Don’t you worry Honey, mommy’s going to make sure you get as much as you can take from now on.”
Gently, she pulled her swollen nipple out of my mouth and I squealed in angst. My heart was still beating wildly and I very badly wanted to cum.
Seeming to sense this, Barbara turned to my mom.
“You see, Chrissie’s little device is working just fine, no more sticky messes in her diapers and no more naughty behavior when mommy’s back is turned.
“I’m very impressed,” my mom marveled, “That chastity device is really a godsend–perfect for masturbating sissies like Chrissie.”
Carefully lifting me up, Barbara took me over to my playpen where she put me inside.
“Now you stay right there and play with your dollies, Chrissie. If you need me for anything you just call. Your mommy and I are going to be in the kitchen having grown-up talk but I’ll be able to hear you with the baby monitor when you wet yourself.”
“And don’t even think of getting out–I don’t want you hurting yourself or getting into any trouble. Everything you need is right here in your playpen.”
I resented both the fact that she took as a given I was going to wet my diapers and also for some reason, being excluded from her “adult” conversation.
Pushing my fat rubber pacifier in my mouth, Barbara led my mom into the other room. I watched her go, my eyes riveted to her sexy, pert bottom, but the moment they were out of the room, I began rubbing my diapers furiously, trying to relieve my pent up sexual need.
Although outwardly, my actions felt the same as always, my penis was only getting about five percent of the physical contact it was used to. My diapers felt soft and comfy as they always did but now, none of that was being transmitted to my needy wiener. I rubbed and rubbed, trying to make it work but all I succeeded in doing was getting myself even more worked up.
I slammed my fists onto the soft, padded rail of the playpen in bitter frustration.
Again, I rubbed frantically, hoping to somehow defeat the device my penis was trapped in but it was no use. I fought back tears of resentment and anger–there had to be a way!
I found I was breathing hard and a fine patina of sweat had appeared on my forehead but that was all I had to show for my efforts. At last, I gave up and sat back against the netted sides of the playpen to pout, my anger focused on Barbara. I had been willing to play along with her weird game of babying me but with this new, evil twist–she’d gone too far. It wasn’t fair! And the tantalizing softness of my prissy diapers seemed to mock me–letting me touch and stroke them but denying me anything further.
In a fit of rage, I threw one of the dolls at the far wall. I barely managed to bite back the curse upon my lips, knowing Barbara would hear me and probably paddle me for it. Her control over me was now complete and absolute.
I wanted to destroy everything here; rip off my diapers, flip the playpen upside down and make my escape but where would I go? More immediately, what would I wear? There were no clothes anywhere in the house that were made for a guy and I couldn’t very well go out nude.
I sighed heavily and sat back down in a huff. Who was I kidding? At the first sign of a tantrum, Barbara would be in here and I’d find myself over her lap, getting the daylights spanked out of me.
I hated the fact that she was stronger than me, both physically and mentally but worse than that was that I still lusted after her–despite everything she’d done to me. It was infuriating! Even now, I could see the soft, smooth skin of her curvy breasts, as she gazed down on me with her smothery, maternal love. She did love me and as much as I hated to admit it–I was starting to love her, although I had to admit my emotions were still in a chaotic, confused state.
All of a sudden, and without warning, I felt a strong, warm stream of pee surge into the front of my diaper.
“Oh!!” I squealed, just as I caught it in time to stop it.
Feeling gingerly, I placed my hand on the front of my diaper. I could feel the warmth spread over most of my crotch and a surprising amount of wetness had saturated the cloth.
I choked back a sob as I wondered what was happening to me. Was Barbara right? Was my urgent need to breastfeed from her causing me to lose control over my bladder? I was becoming more of a baby with every passing day.
Just as I was contemplating that terrible thought, another stream of pee flooded into my diaper. I was able to stop it, just barely, but now I could feel there was plenty more behind it. Gripping the side of the playpen, I felt like I was holding back the Mississippi. With a sob of shame, I let go and let it flow uninhibited. Hot pee splashed into my diapers, soaking back between my legs and deep into my seat. I was kneeling on my knees, afraid to sit down for fear it would leak out the sides. On and on it went, seemingly without end as I soaked my thick diapers completely and thoroughly. I felt so helpless, unable to prevent wetting myself and I felt the heat in my cheeks as I imagined what my friends would say if they could see me now.
As I knelt there, gripping the rail with one hand, my other went back curiously to feel the warm pee-soaked seat of my diaper over my plastic pants. I caught a sight of myself in the wall mirror and I blushed with shame. I’d never felt so babyish before, my pacifier still in my mouth as I looked at myself, a big sissy baby who’d just wet his diapers like an infant.
A tear trickled down my face as I stared back at my reflection. Barbara had been right about everything–she had been right and I had been wrong. Looking at myself, I knew I could never be a real guy. It just wasn’t in me. What I wanted and what I needed was a mommy, a mommy like Barbara that was willing to care for me and love me for what I was–a whiny, weak-willed sissy who belonged in diapers and baby clothes. I was beginning to understand why she had paddled me over the last week. In my heart of hearts I knew I deserved it and needed it.
But what I needed right now was a change. My diapers were completely soaked and they were sticking stubbornly to my rump and hips.
My voice quavered as I gripped the side rail weakly.

Chapter Six Back to School for Chrissie

Strapped into the carseat in the back of Barbara’s minivan, I sucked nervously on the fat pink pacifier filling my mouth to capacity. Today I was headed back to school, although what kind of school–I wasn’t exactly sure. I was dressed no differently than a three year-old baby girl so I dreaded the prospect of being seen by anyone, regardless of the type of school. Barbara had picked out a delicate white baby dress, generously trimmed with pink eyelet lace and a big decorative pink bow on it’s Peter Pan bodice. She had me in glittery white tights and my fat, embarrassing diapers were covered with a set of fancy pink rumba panties which had three sassy white ruffles crossing the seat. My stockinged feet had pink anklets and my ever present glossy black Mary Janes. Lastly, Barbara had pulled my growing hair into two pigtails and secured them with pink satin bows. She’d also applied a light coating of blush to my cheeks but I was already blushing at the thought of others seeing me like this.
On top of that, my enforced chastity certainly wasn’t making my situation any easier. I’d woken up several times during the night with painful attempted erections that my body still hadn’t learned were now forbidden. But worse than that was my time during the day when I was fully awake and aware of my surroundings. Maybe it was just me, but it seemed like Barbara was dressing even more provocatively than before. She constantly teased me with her form-fitting clothes and plunging, low cut tops. I had been on edge all week as I gazed hungrily at her jaw-dropping body, my little penis throbbing desperately in it’s device but unable to get any relief. At times, I felt light headed and physically weak with desire, at other times, I felt ready to explode with frustration. It was so unfair!! I found that after a day of constant stimulation, the precum would begin to ooze uselessly from the end of my chastity device, partially draining me but still leaving me horny and completely unsatisfied.
I was starting to suspect that it had been Barbara’s plan all along to get me to first accept, and then even want to wear diapers, because of their soft, comforting embrace. I’d never known such an exciting, pleasurable outlet for sexual relief and I was sure she known from the start I’d come to find them irresistible. She’d given me a taste of how wonderful they felt for a chronic masturbator, only to cruelly take that pleasure away.
And every day, Barbara would smile sweetly at me, her touch gentle and loving, as she let me nurse like a baby from her big bountiful breasts. Sometimes I’d literally cry with pent-up desire as she forced me to suckle from her firm, milky nipple but she’d only giggle at my predicament and softly pat the front of my sissy diapers as if to mock my desperation. She knew without question that she had me completely under her control and there was nothing I could do about it.
All this receded into unimportance as we pulled into a parking spot in front of the Francis Merrimont Boy’s School. I could see normal guys my age, milling about as they talked amongst themselves while they got ready to go inside. I whimpered nervously as I frantically sucked on my pacifier, terrified at having to walk past them in my prissy baby outfit.
Barbara came around to my side of the van and after opening the sliding door, unbuckled my carseat straps.
I shook my head and looked at her pleadingly but she only smiled down on me with her usual warm, yet dismissive look.
“I know this is going to be hard at first, Chrissie, but it’s important for you to completely accept what you are and be seen as the sissy baby we both know you are deep inside. You see, you’re still clinging to an image of yourself as a boy but the fact is, you know and I know that’s not the real you. You’re just a little baby that needs his diapers and his mommy–and the sooner you accept that, the easier it’ll be for you.”
I shook my head, even as a tear of shame tumbled down my cheek. And as if to verify what she said, as she helped me out of the seat and onto the sidewalk, I felt a sudden, strong, hot stream of pee escape into my diapers. Squealing helplessly, I dropped my hands down as if that might be able to prevent it but the damage was already done. Of course, between the rumba panties, tights, and my usual plastic panties, there was no visible evidence of my accident but the warm wetness inside only added to my feelings of babyishness.
No sooner was I standing in the open sunlight when several guys looked my way and began pointing at me. Their jeers and laughter washed over me and my cheeks burned hotly. Barbara responded by taking my hand and forcing me to wave back at them, even as I stared at the ground in utter shame.
“Say hi to those big strong boys, Chrissie,” she said encouragingly.
I think she sensed I was about to burst into tears because she closed the van door behind me and took my hand, leading me into the big main doors of the building. The guys continued to make mocking comments although as we got closer, Barbara’s sexy body tended to have it’s usual distracting effect on them. She smiled coyly back at them, her high heels clicking confidently and crisply on the concrete steps before we went inside.
I was looking around feverishly, only to find more guys staring at me in disbelief as Barbara led me through another door and into a separate room. I was vastly relieved to be away from their staring, contemptuous faces and alone for the moment but for how long? Barbara removed my pacifier and just then, the other door in the room opened and a drop-dead gorgeous woman in her late twenties sauntered in.
She was a smoldering blonde with unbelievable pretty green eyes, a cute button nose and full, luscious lips. She wore a tight wrap around top that hugged her full sexy bosom and showed off a deep line of cleavage that was impossible to ignore. Her short, summery skirt left much of her smooth, firm thighs exposed which was emphasized by her strappy high heels.
“So this is the pretty little sissy girl you were telling me about!” she exclaimed excitedly.
My face went a deep shade of crimson as she bent down to look closer at me. I’d always been intimidated by beautiful women and as usual, I couldn’t hold her gaze. I was staring at the floor, too shy to look up when her long nail reached down and lifted my chin to look up into her gorgeous eyes.
“My, you certainly are a pretty one, aren’t you Little Miss Priss?” she asked sweetly.
I felt a mixture of emotions, mostly shame at being called pretty but I also guiltily felt some small measure of pride by the compliment being paid to me by this incredibly stunning female. I really didn’t like being thought of as pretty but if that was what made this babe like me, how could I complain?
“Chrissie, say hello to your new teacher–her name is Ms. Taylor,” Barbara said as she patted me on the thick, ruffled seat of my diapered bottom.
Forced to look at the arresting features of her face, my cheeks burned brightly.
“H-h-hi,” I croaked nervously and I swallowed hard.
She smiled a devastating smile that washed over me like a warm bath and made my toes tingle. What a hottie she was!
“Hello Chrissie, welcome to my nursery,” she said in a light, sexy feminine voice, “My, my…I think you’re going to make all the other sissies jealous with your cute, girly looks–you’re not really a boy under all those frills are you?”
Still blushing three shades of red, I nodded in confusion.
“Uh-huh,” I squeaked weakly.
Ms. Taylor laughed musically.
“I don’t believe it! You’re the prettiest little girl I’ve ever seen, but I better keep my eyes on you–some big strong boy is going to want to kiss you!”
I blushed furiously at her words as Barbara laughed with Ms. Taylor delightedly.
“Now that I could see all too easily!” Barbara added, “Do you think you would you like it if one of those boys outside gave you a nice big kiss?”
“No!” I snapped petulantly but I couldn’t stop blushing.
I felt so sissyish that it was easy to imagine one of them forcing his will upon me.
“And it looks like your mommy’s got you very well diapered–is she a big wetter?” Ms. Taylor asked Barbara.
“Oh my–yes,” she replied, “But her next change isn’t due until lunchtime and her diapers can hold any accidents she may have for awhile yet.”
“Don’t you worry Sugarplum,” Ms. Taylor smiled down at me, “I’ve got plenty of diapers and plastic panties for sissies like you who have no control. I’ll take very good care of you.”
I hated being thought of as having no control but I guess it was to be expected in my present outfit.
“Well, since that’s all set then…I better be going, I have to be heading back to work now,” Barbara said as she pulled her keys out of her purse, “You be a good little girl for Ms. Taylor–she has my permission to spank you if you misbehave, you know.”
Between the two of them, I was crushed with humiliation, but I was even more distraught at being left alone in this strange place, with a bunch of strange people. Even though Ms. Taylor was a major knockout, I was terrified of the unknown humiliations that were almost certainly awaiting me here.
“Mommy–don’t go,” I pleaded anxiously with her.
“I’m sorry Sweety, but mommy has to go to work–you’ll be just fine here,” she assured me, “Don’t you worry about a thing.”
In my rising panic, I felt a hot stream of pee suddenly released from my bladder. Stamping my Mary Jane-clad feet in frustration, I stood helplessly as yet another, even stronger surge quickly soaked the front of my diapers in a humiliating display of my lack of control. My lower lip trembled and I looked up in panic at Barbara as I felt my diapers being flooded uncontrollably.
The combination of everything was too much for my fragile temperament and I abruptly burst into tears.
“Nooo!” I wailed as even more warm pee flowed freely into my diaper.
I threw my arms around Barbara’s neck and hugged her tightly as the pee quickly saturated my seat and began soaking the surrounding cloth. My tights and rumba panties conspired to make sure the drenched cloth hugged my buns and inner thighs in a sopping wet embrace.
“Don’t leave me Mommy!” I wailed as tears streamed down my face.
My shoulders heaved and my breathing was labored as I sobbed like a baby on her shoulder.
Barbara sighed and helped me over to a seat behind a desk, sitting down and then taking me upon her lap. In moments, her blouse was undone, her delicate bra unclasped and her big, plump breast was put before me. Easing her firm, milky nipple in between my trembling lips, she pulled me gently to her as she wiped a tear away from my cheek.
“There, there now Baby….everything’s going to be okay…Mommy’s only going to be gone for a little while today…you’ll be just fine with Ms. Taylor here.”
I sobbed helplessly and nursed feverishly on the big nipple filling my mouth, quickly being rewarded with a steady stream of warm milk.
“Aww…you poor little thing,” she said soothingly, “Mommy’s little baby girl is just having a terrible first day already, hmm?”
I sobbed again and sucked even harder on her nipple, trying to regain my composure.
“Oh my…Chrissie’s already wet herself, I’m afraid,” Barbara informed Ms. Taylor as the warmth of my bottom gradually made itself felt on her thighs.
“That’s no problem,” Ms. Taylor replied, “I’ll be happy to give her an early change in the nursery, it’ll give us a chance to do a little bonding.”
“I’m afraid when she gets this upset, the only thing that will soothe her is a nipple…I’m sorry to make such a fuss,” Barbara said as she gently patted my head and encouraged my nursing from her breast.
“Oh, don’t even mention it, perhaps I can be of help here.”
Ms. Taylor pulled up another chair and undid the knot holding her wrap around top in place.
“Are–are you…?” Barbara queried.
“Yes,” Ms. Taylor giggled, “I’m lactating too so I can take over any time you’re ready.”
“Oh, that’s wonderful,” Barbara said, much relieved, “I usually let her nurse until she stops crying–you should be fine with her pacifier after that.”
Barbara helped shift me over to Ms. Taylor’s lap and I whimpered as her firm nipple was taken from my mouth. Whining miserably, I watched in captivation as Ms. Taylor opened the front clasp of her silky smooth satin bra to reveal a perfect, flawless breast; full and heavy with milk.
“Come here Chrissie, I’ve got a nice warm nipple for you to suckle from.”
I whimpered in embarrassment but soon began nursing from her breast.
Using her long, slim finger, she brushed away another of my tears and beamed down on me with satisfaction.
“That’s a good baby,” she cooed, “You take all you need my pretty little sissy.”
There she said it again. Was I really pretty, I wondered? I’d always known I had rather feminine features…could it be that with my baby dress, tights, sissy shoes, and a little make-up that I actually looked pretty? It gave me a strange feeling inside. It also gave me a familiar feeling inside my chastity device. My poor little penis was starting to strain mightily against it’s silicone prison in angst. Was it because a beautiful woman was letting me nurse from her awe-inspiring breast? Or was it something more?
Assured that I had finally settled down, Ms. Taylor returned her attention to Barbara.
“Does she need an enema today?”
“No, thanks though–she had one this morning during her diaper change,” Barbara replied.
She remained a little longer but when it was apparent I had stopped my crying, she made her goodbyes and left us alone. I continued to nurse until I’d had my fill from Ms. Taylor’s succulent breast.
Easing her nipple out of my mouth, Ms. Taylor gently pushed my pacifier in between my lips.
“There you are Chrissie. Are you ready to have your pampers changed?”
I sniffed and nodded weakly as she helped me up and took my hand in hers. Leading me through the door she came in, we entered a large room, that looked like a cross between a kindergarten classroom and a baby’s nursery. The walls were decorated with cartoon characters and several cribs were in a group at the far corner. I recognized a changing table with stacks of cloth diapers and a dresser nearby containing plastic panties and other supplies. On one side of the room were several desks at which two boys my age were sitting. One was an obvious sissy, dressed much like myself and it was strangely gratifying to see someone in the same predicament as I was. The other was another guy, dressed in a little boy’s romper with a white t-shirt and baby blue shorts and suspenders. At first glance, he didn’t appear to be diapered, although it was hard to tell and I thought I discerned a bulge around his hips.
As for the other sissy, he was very clearly diapered, wearing nursery print plastic panties over a fat, bulky diaper, much like mine. His short party dress was lilac and patterned with flowers and lace and I could see his legs were smooth to the touch. Upon seeing my arrival, he beamed happily, and skipped over to see me.
“Hi there–my name’s Joshy–what’s your name?” he asked enthusiastically in a high pitched, feminine voice.
I was still a bit taken aback by my circumstances and the appearance of another sissy but Ms. Taylor answered for me.
“Joshy, this is your new sissy playmate, Chrissie, although I rather think ‘Little Miss Priss’ is a better name–don’t you, Chrissie?” she asked me as she bent down to look me in the eye.
I wasn’t used to this kind of attention from such a gorgeous woman and I blushed shyly, unable to speak.
“I just know you two are going to have all kinds of fun together,” Ms. Taylor gushed.
Before I could respond, Joshy came over and hugged me close, nuzzling my neck with his nose in an all too friendly way.
“Wow–you sure are pretty!” he exclaimed cheerfully, as she stood back to look me over, “Do you want me to show you how to do your make-up?”
My face went red at the compliment and offer, as I tried to reconcile my confused feelings inside. Growing up as a boy, I had always wanted to be considered handsome and now that I was being thought of as pretty, I felt sort of indignant and humiliated, yet at the same time, my craving to be accepted made me inclined to be receptive. I was so befuddled and mixed up–I didn’t know what to think!
“Matty, come over and say hi to your new playmate,” Ms. Taylor told the other boy.
“Hey,” he said without rising, and none too eagerly. He was playing with some blocks and seemed altogether disinterested in my arrival.
Oddly enough, I felt a strange compulsion to want to know him, unlike the overly enthusiastic sissy Joshy, who from all appearances, seemed to have an immediate crush on me. There were other differences as well between the two–whereas Joshy had an obvious femmy nature about him, Matty seemed rather out of place here–he looked like a boy’s boy, with muscular legs and an undefinable rough edge to him. I could easily picture him tearing down a transmission in the auto shop or playing football on the school team.
I felt strangely disappointed that he was openly dismissive toward me. Why did it matter? I didn’t know. But for some reason, I wanted to be accepted by him and more than that, I wanted him to like me.
“Come along girls,” Ms. Taylor said as she took Joshy’s and my hands, Chrissie needs her diapers changed and then you two sissies can get to know each other better.”
I felt a little frustration at being lumped together as a “girl” but then I had to admit it wasn’t an unreasonable expectation either. And despite myself, Joshy’s enthusiasm was becoming infectious. As he skipped along gaily, I felt a lighthearted sashay start to enter into my own gait. Deep down–something felt tremendously liberating to be girlish and carefree and I still enjoyed the bulky feeling of my diapers between my thighs, despite my frustrating chastity device.
We entered another room, this one even more nursery-ish than the other, larger room and I saw more baby supplies and furniture arranged within it. Ms. Taylor guided me to a low, vinyl covered changing table and sat me down gently, while motioning Joshy to sit on the floor next to us.
“Joshy, why don’t you help me get Little Miss Priss here undressed so I can change her diapers?” she asked sweetly.
Like mommy’s little helper, Joshy enthusiastically agreed and they began unbuckling my Mary Janes and removing my lacey anklet socks. Soon, my ruffled rumba panties and glittery tights were being peeled down my legs and Ms. Taylor asked Joshy to get the baby bottle she had in the warmer.
“Oh my–look at these smooth legs of yours,” Ms. Taylor exclaimed as she stroked my bare thigh with her soft, slim hand. It send an electric thrill through me to have her touch me and I couldn’t prevent a shy smile from breaking across my face. I was used to being self conscious of my lack of hair but now, it was actually gaining me attention unexpectedly from this pretty teacher.
Joshy came back and–far from being jealous of the attention I was receiving–he bent down to stroke my thigh himself.
“Oh my gosh!” he gasped, “So soft and smooth! You are sooo lucky!”
For some reason, my penis was once again throbbing in it’s prison and I blushed with pride and excitement.
Joshy handed over the bottle and Ms. Taylor eased it between my lips.
“There you are Sweety–all my babies get a bottle when they get their diapers changed.”
My embarrassment returned and I watched closely as Ms. Taylor unpeeled the clinging plastic panties off of my sodden diaper and brought them down my legs. She tossed them into a large bin behind her and then unpinned either side of my diaper, pulling it down to expose my hairless crotch and tiny captive penis.
Both of them beamed cheerfully at me as they gazed down at my restrained, childish genitals.
“Aww, looks like someone’s been a naughty little girl,” Ms. Taylor said in a voice meant for a toddler, “Did my wittle Miss Pwiss get in trouble for pwaying wiff hersewf?”
My face burned with shame and I looked the other way as I sucked desperately on my bottle. Ms. Taylor giggled and pulled my heavy, wet diapers out from beneath me and then began wiping my buns and crotch with cool baby wipes.
“Don’t you worry Babykins, Joshy’s little pee-pee is locked up too,” she assured me as she sprinkled baby powder over my chest and tummy, “Little sissies like you two just can’t be trusted not to play with their wiennies.”
I was mortified to have her talking to me like this but there was zero I could do about it.
“Tell you what–I have something that I’m sure will make you feel better. You won’t be able to cum but it might give you a little relief, okay?”
I whimpered with anticipation at anything she might be able to do to relieve my poor aching penis. This had to be my lucky day!
Reaching behind me, Ms. Taylor brought forth a strange looking object that looked like a streamlined dildo. Looking prettily like an angel from heaven, she smiled down at me enigmatically as she carefully coated it with KY. Her smile alone was enough to make me hard but there was also something indefinable in her feminine demeanor–so subtly sexy it made my heart beat wildly within my chest. Her finger probed my hole and I gasped again, even as my cheeks burned with desire and shame. Very gently, she began pushing the dildo object into my puckered hole, never forcefully, but with loving care as she slowly eased it past my bashful sphincter. I whimpered weakly, my breathing labored as I watched her through half closed eyes while she alternately twirled and slide the dildo inside me. I moaned like a little girl and she began a tortuously erotic rhythm, smiling down at me knowingly as she slowly plunged it in deeply and made me gasp like the virgin I was. I let out a small sigh of pleasure as she eased it out, only to push it in again.
Joshy was captivated with watching me but my eyes were closing again as I moaned weakly. Waves of pleasure were washing over me–I’d never felt anything so wonderful in my life and my hole craved the slippery pliable rubber of her dildo, yet at the same time, my penis ached painfully as it surged and throbbed frantically within my chastity device.
With my eyes still closed, I suddenly felt warm lips kissing my own.
Opening my eyes in surprise, I was shocked to see Joshy amorously and eagerly locking his lips to mine while he held my wrists to the changing table. I squealed loudly and squirmed beneath him, my shock competing in confusion with the erotic bliss I was receiving from Ms. Taylor. Joshy’s eyes opened and he smiled at me, even as he kissed me hard again.
I wriggled like an imprisoned fish and he finally let go of my arms, sitting back with a happy, contented smile on his cherubic face.
“I’m sorry Chrissie–you’re so pretty, I just had to kiss you!” he giggled.
My face flushed even redder than it already was as I stammered incoherently. Whatever reply I was attempting to make was cut off as Ms. Taylor plunged the slippery dildo deep once more inside of me. I moaned deliriously and gazed weakly up at her pretty face. As my eyes wandered down, I drank in the soft, silky smooth skin of her breasts, full and round like two honeydew melons. I helplessly straddled the line of being tortuously close to cumming as she continued her erotic ministrations. I moaned again, unable to speak, and I shuddered with ecstasy everytime she pushed the dildo back inside me. I felt wonderfully emasculated and feminine, savoring the feeling of having my own hole so deliciously filled. Yet at the same time, I also craved that orgasm that felt so tantalizingly close. I was desperate to cum!
Looking down at my penis, I could see a fair sized pool of cum dribbling out from the tip. It was dribbling down between my legs in a steady drip, and Ms. Taylor used her free hand to coat my pacifier with it before easing it between my lips. I whimpered weakly as I tasted my first semen, blushing with guilt as I passively and submissively humiliated myself before her.
A random thought entered my mind; could this be what Matty’s cum tasted like? I blushed hotly at the thought, even as other, even more forbidden fantasies swam into my imagination. What would it be like to have Matty’s cock in my mouth, I wondered. I pictured myself, reverently on my knees before him as he drove his manly tool deep into my mouth while I did my best to please him. Would I be able to satisfy him? Would he like me then, I wondered.
Finally, Ms. Taylor slid the dildo out and she put it aside. My own penis throbbed weakly within it’s prison, deprived of a mighty, earth-shaking orgasm, yet fully drained of my joy juices. It was so frustrating, I felt on the verge of crying!
Still breathing heavily, I whimpered impotently as Ms. Taylor lifted my ankles and slid a thick stack of bunny soft diapers beneath me. Sprinkling baby powder on me, she smiled down on me sweetly as she pulled the cloth around my hips.
“These are extra thick down the center, Chrissie, for heavy wetters like you.”
I fought back the urge to cry, even as the tears filled my eyes. It was all so unfair! Why couldn’t I be allowed to cum??
Looking down, my imprisoned penis was soon buried in the soft, thick folds of her triple layered diaper as she pinned either side with pink headed safety pins. Taking a pair of clear plastic panties with colorful polka dots in her hands, Ms. Taylor shook them out in front me.
“Aren’t these cute, Chrissie?” she asked brightly, “I think they’ll look just perfect with your frilly baby dress.”
As I sucked on my semen coated pacifier, she gathered the leg holes and began working them up my hairless legs.
“You know, I can’t really blame Joshy here for kissing you,” she chuckled as she began working them over the bulging cloth of my diaper, “With girly smooth legs like yours, all the boys here are going to be hot to try and make a pass at you.”
I wasn’t so sure, but then, I wasn’t sure about anything anymore.
“There you are, my Little Miss Priss,” she declared cheerfully as she gently patted the fat front of my diaper, “All diapered and ready for the day!”
I blushed again at being called her little nickname. It was bad enough having to dress like this without her heaping even more shame upon me.
Ms. Taylor lifted me to my feet just as her phone rang from the other room.
“Now, you two girls be good while I go get that,” she said as she winked mischievously at me. I watched her saunter out of the room, my eyes lingering on her perfectly shaped rear and long, sexy legs but once she was gone, my attention returned to Joshy.
Without another thought, I reached out and slapped him on the face. I meant to hit him hard but somehow, it came across weak and ineffectual.
“How dare you kiss me!” I cried indignantly.
Joshy’s smile evaporated and he looked back at me in shock as tears brimmed in his eyes.
“I-I’m sorry Chrissie…please don’t be mad at me,” he whined in his little voice. A tear trickled down his cheek as he held it tenderly, obviously hurt by my attack, although it was probably more emotionally than physically.
I was still feeling humiliated by the whole experience and I crossed my skinny arms over my chest petulantly. I knew I must look like a fussy little girl in my prissy white and pink baby dress and bulging diapers but I did my best to appear macho.
“I don’t even know you!” I continued, although no sooner were the words out than I regretted them. It wasn’t because of my lack of familiarity with this sissy–I was trying to show him I was still a guy’s guy!
My words obviously had the wrong effect because Joshy came over to put his hands on my shoulders in a gesture of warmth and caring.
“I know that Chrissie–but I want to get to know you and be your friend,” he emphasized strenuously, “Will you please forgive me?”
Still feeling huffy, I brushed off his hands warily.
“I don’t know…”
“Please?” he begged me.
I sighed wearily. Today had already been so trying for me and I had no fight left in me.
“…Okay…” I finally replied without returning his anxious gaze.
“Oh–thank you!” he exclaimed as he threw his arms around me and hugged me tightly, “I’m going to be your very best friend!”
Ms. Taylor strode back into the room, only to find us hugging like lovers as Joshy fondled the thickly padded seat of my diapers.
“Well…I see I can’t leave you two girls alone for a minute,” she giggled, “But I guess sissies will be sissies.”
I blushed and pushed my way out of Joshy’s clingy embrace, unsure how best to respond to her implied accusation.
“Oh my gosh–I almost forgot your shoes, Sweety!” Ms. Taylor exclaimed, “You just sit your pretty little bottom down and I’ll get you all fixed up.”
Sitting back down on the changing table, Ms. Taylor helped put my lacey anklets back on, followed by my Mary Janes.
“I thought your pink tights were really cute but it seems a shame to cover such silky smooth legs like yours–don’t you think, Chrissie?” she asked me.
“I guess so,” I mumbled, although Joshy seemed to be in complete agreement with her.
“Joshy, why don’t you show Chrissie here your collection of dollies–And I’m sure she’d just love to see your dollhouse.”
“Okay!” Joshy replied happily.
Taking my hand, he tugged at me eagerly to guide me into the adjoining room. Ms. Taylor took a moment to go and check on Matty before taking a seat at her desk. Her workspace was nothing special, except that it was open to view from the front and I watched in fascination as she slowly crossed her lovely legs, letting her high heel dangle over the floor. I sighed in admiration at her incredible beauty and sexiness. She was such a total babe!
Joshy continued to blabber on, oblivious to my lack of interest, telling me all about his doll collection, wearing make-up, styling hair and games of hopscotch and cat’s cradle. My attention varied between making noncomittal grunts to Joshy and dividing my gaze between Ms. Taylor and Matty. The latter had short hair, beautiful blue eyes and a boyish, pug nose. I felt strong feelings of envy for him as another guy, although our shared gender was where our similiarities ended. Clearly, he was everything I was not, nor would ever be. I sighed in resignation at the thought.
I hoped he would come over and talk to me but that seemed highly unlikely. Other than staring at Ms. Taylor’s fabulous body, he rarely looked up from what he was doing and seemed hardly aware we were in the same room.
I was distracted by the sound of Ms. Taylor’s cell phone ringing and she answered it with a musical greeting that made my heart skip a beat. I tried not to be obvious and stare at her but it was impossible to ignore the happy expression on her pretty face as she talked to whomever it was on the other end. A closer listen revealed that it was a man, and most likely a boyfriend.
Given her incredible beauty, it shouldn’t have come as a shock that she had a lover but for some reason, it did. I seethed with irrational jealousy that someone else would be enjoying her considerable charms and I hated myself for giving in to the emotion.
Before long, the conversation ended and she hung up, a happy smile lingering on her gorgeous face. Leaning forward on her desk, she pressed a button on the school wide intercom.
“Yeah?” came the casual reply.
“Would you mind covering me for my lunchbreak?” Ms. Taylor asked.
“Sure thing Hon–I’ll be right there.”
“Girls–I’m going to be gone for about an hour–maybe more,” she giggled, as if she were privy to some private joke, “But Sarah will be here to take care of you, okay?”
The others answered, although none too enthusiastically, and I felt a shiver of anxiousness based on their reactions. Of course, it was easy to imagine that whoever Sarah was–she was not Ms. Taylor. That alone would make me regret her departure, but I sensed an uneasiness that went beyond our being deprived of our smoldering hot teacher.
When the far door opened, I began to understand why they had been less than receptive to our substitute. I recognized Sarah from my baby shower all too well–she was the one who had paddled me so fiercely after my diaper change. Not only that, the only side I had ever seen of her was her cruelty. Her arrival certainly boded ill, for me at least.
Ms. Taylor grabbed her purse and car keys and was out the door in a flash, leaving us alone with this vengeful vixen.
“Well, well, well…” she said as she came over to look down on me, “If it isn’t Barbara’s little sissy…Chrissie, isn’t it?”
“Uh-huh,” I mumbled nervously, my heartbeat quickening perceptibly.
Her slim hand was out like lightning and she slapped my cheek harshly before I could so much as blink.
“Yes Ma’am,” she corrected me, as she towered over me with her hands on her curvy hips, “You will answer me with a ‘yes ma’am’ or ‘no ma’am’–understood?”
“Yes Ma’am,” I quickly replied as a tear tumbled down my reddening cheek. It stung painfully and I realized belatedly that I had woefully underestimated her despite my initial assessment.
“Well, since you’re here now, it’s time you understood a few things. First, we don’t tolerate any backsass or horseplay–got it?”
“Yes Ma’am,” I immediately replied in a whimper.
“Second off, we don’t allow any hanky-panky between any of the students–or by themselves. You got that one?”
“Yes Ma’am,” I answered her, even as my cheeks reddened. Was she somehow aware that I used to be a chronic masturbator?
“The school principal at Francis Merrimont Boys School is Mrs. Sterne. The boys all fear her, and for good reason, but she especially puts the fear of god in prissy little sissies like you.”
“Yes Ma’am,” I responded, even though she hadn’t actually asked me a question.
“But rather than give you a speech about who she is, I think we should introduce you to her, personally.”
The way she said ‘personally’, made me doubly nervous but I was afraid to try and stand up to her. And to be sure, the days of whining my way out of a situation I didn’t find agreeable were long gone–Barbara had seen to that.
“Come along, Chrissie,” she instructed me, “It’s time you met Mrs. Sterne.”
Snatching my hand in hers, she dragged me into a different room where she knocked on a closed door with a small plaque saying ‘Principal Mrs. Sterne’ on it. Ordinarily, I would have wet my diapers in fear at this point but I had just gone a little while previously and didn’t need to go.
“Enter,” a firm, yet feminine voice replied.
Sarah opened the door to a spartan office, minimally furnished, with a large mahogany desk set off to one side. Behind the desk, sat the imposing figure of Mrs. Sterne, the severe looking brunette lady who’d given me the Spencer paddle as a gift at the baby shower. I just about choked with fear as she looked up at me, her eyes registering both recognition and contempt on her beautiful face.
“Barbara has enrolled Chrissie here in Ms. Taylor’s class,” Sarah said by way of introduction.
Without a word and without taking her eyes off me, Mrs. Sterne slowly rose and smoothed the tiniest of wrinkles from her immaculate grey pencil skirt. I felt as small and insignificant as a lowly bug as she gracefully came around the desk to look down on me, her gaze cold and steely.
“Yes indeed,” she said simply, although my stomach was doing somersaults as I tried to return her attention.
Given how close she was to me, I was forced to look up into her darkly beautiful countenance, although I couldn’t help but notice her wonderfully big breasts thrusting proudly against the pristine white fabric of her businesslike satin blouse.
For a moment, nobody spoke (I was too terrified) and my eyes drifted down to her rising chest, which expanded outward magnificently with every breath she took. I licked my lips anxiously as my eyes took in the delicate lace on the huge cups of her bra, clearly visible beneath the thin, silky top it was trying so hard to burst out of.
Suddenly and without warning, I felt the scalding sting of her steel-like hand as she slapped my cheek hard enough to make me see stars.
“Don’t you ever let me catch you staring at my breasts–do you understand me?” she barked viciously.
I burst into tears and gripped the sore side of my face tenderly.
“Y-y-yes Ma’am!” I bleated repentfully.
She most definately lived up to her namesake–of that, there was no doubt! I’d never met someone so hot, yet so intimidating!
Like her assistant, she placed her slim, perfectly manicured hands on her broad, curvy hips and stared down at me remorselessly, daring me to challenge her.
“When you enter my office, it will only be for one thing,” she informed me in clipped tones, “And that is to receive the painful and humiliating punishment you have so richly earned for yourself.”
I quailed at the thought of facing her under those circumstances.
“When that happens, you will have the opportunity to become better acquainted with the paddle I call the ‘Sissy Tamer’,” she said as if describing a sacred and noble sword.
Reaching over, she picked up a long, black wooden Spencer paddle, much like the one she’d given me as a present, and hefted it in her hands. It looked light as balsa wood, given the ease in which she handled it but when she slapped it against the palm of her free hand, I nearly gasped with the impact.
“I apply this to bare bottoms, especially sissy bare bottoms, who badly need to feel the harsh slap of oak from time to time.”
“I-I-I p-promise I’ll b-be good,” I stuttered in terror.
An evil glint appeared in her dark eyes and she smiled the briefest smile before it vanished like a winter wind.
“Yes you will,” she replied, “And you’ll be one sorry little sissy after you’ve been over my lap.”
I gulped hard, desperate to escape such a fate.
“But I promise!” I bleated, “I promise to be good!”
“You know,” she said ignoring my response, “I’ve paddled more sissies than I can count and watched them all cry like babies…but you have to be the prissiest, most frou-frou sissy I’ve ever laid eyes upon.”
“Y-yes Ma’am,” I said, afraid to disagree with her.
“Some of the sissies here “graduate”, if you can call it that–and are sent to live with strict women who have their own purposes for them, although what someone would do with a limp-wristed, pansy such as yourself, I have no idea.”
I wilted miserably under her scolding lecture.
“You should be very grateful you’re under the care of someone like Barbara who is willing to mollycoddle you…if you were living under my roof, you’d receive nothing but the strictest discipline, and you’d learn what real obedience means.”
I had no doubt in my mind she meant every word of what she was telling me.
“Y-yes Ma’am,” I responded reflexively.
Turning around, she retraced her steps back around her desk to take her seat, with the poise and grace of a panther.
“That will be all for now,” she said dismissing me, “I’ll look forward to giving you your first taste of the Sissy Tamer.”
Sarah reached down and snatched my hand, jerking me around as she led me out through the door we had come in. My head was still spinning after my perilous encounter with Mrs. Sterne. I made a mental note to seek out Joshy’s advice later on and find out how to avoid her terrible wrath.

Once back in the Nursery, Sarah called Joshy over, almost as if she had been reading my mind.
“Joshy, I want you to do Chrissie’s make-up for her, just like you’ve done your own,” Sarah ordered him.
I could sense his nervousness and as he began applying pink glossy lipstick to my lips, we shared a look of mutual fear. What did she have in mind, I wondered. It couldn’t be good.
I could tell by the care and skill that Joshy did my make-up that he obviously had a lot of experience with it. At least that was something I could take pride in–only a true sissy would have developed such girlish skills.
“Make sure you give her plenty of lipstick,” Sarah instructed him, although she didn’t elaborate as to what her reasons were.
Joshy dutifully twisted the cylinder of glossy pink lipstick to expose more of the rose scented material. With careful precision, he ran it across my puckered lips and then back again, ensuring a thick, slick coating.
Just then, a large man wearing a yellow polo shirt and khaki shorts entered the room, his presence exuding male confidence from every pore on his ripped, imposing body. Sarah’s eyes lit up immediately at his handsome appearance and she grinned amorously at him, moving over and taking his big, muscular arm in hers. He eyed us strangely, looking us over carefully as if looking for some special attribute, although I couldn’t imagine what a man like that would want with either Joshy or I.
“Okay everyone, line up here. Coach Saunders wants to get a better look at you,” Sarah instructed us.
It was easy to believe this guy was a coach, and I suspected he was actively involved with the school’s football team. His physique was without peer, and his ice blue eyes drilled into us from his manly, rugged face. His square jaw and close cropped sandy hair made me think that even Sarah–who was no slouch in the looks department–must have felt lucky to have this guy as her boyfriend.
I saw Matty come over but Coach Saunders quickly put up his meaty hand to stop him.
“Not you son–just the sissies.” he said in a gruff voice.
Matty complied and Joshy and I stood in place, nervous and fearful about what they wanted of us. I squirmed in my frilly short baby dress and diapers, acutely aware of how sissyish and feminine I looked. My hairless legs felt painfully exposed and unconsciously, I pulled the hem of my short dress down in a futile attempt to hide my embarrassing sissy diapers.
Why would a coach for the school possibly have any interest in us? Could it be they wanted to parade us before the rest of the school to humiliate us? After meeting Mrs. Sterne firsthand, I was willing to do anything to avoid a return trip to her office.
“Hmm,” the coach said, “This one must be new here,” he said, thrusting a huge calloused thumb in my general direction.
“Yes, the prissy thing just started today,” Sarah informed him.
Stepping closer to me, he gave Joshy a rude push, who fell backwards awkwardly.
“That one’s no where near as girly as this one,” he said to Sarah as he inspected me closely.
I felt hurt by his appraisal but my instinctive fear for this rough man overrode my wounded pride.
Looking up into his steely cobalt eyes, I saw what I thought was lust beginning to glaze them over.
“Oh yes, this one will be just fine for what I have in mind…” he said ambiguously.
My eyes fell to the growing bulge in his pants and my heartbeat quickened in fear.
“Ever sucked a cock, Sissy?” he asked me bluntly.
I blushed bright red with embarrassment.
“N-no Sir,” I replied meekly, although I felt sure he didn’t believe me.
“Well today’s your big day,” he chortled, ” ‘Cause you’re gonna suck my cock and swallow my load–whaddya think about that?”
I couldn’t believe my ears. Was this guy really talking about making me suck him off?
“B-but I’m n-not even g-gay,” I stammered uncertainly.
“You’re a sissy and all sissies suck cock,” he informed me in no uncertain terms, “You should consider yourself lucky I’m allowing you to wrap those pink lips of yours around my tool.”
I felt anything but lucky–I was terrified of this brute!
Unbuttoning his shorts, he rested his hands on his waist and looked down upon me brazenly.
“Get down on your knees,” he commanded me.
“Y-yes Sir,” I quivered.
“Unzip my shorts.”
With trembling hands, I did as I was told, trying desperately to think of a way out of this. Obviously, I couldn’t confront him physically–he looked like he could snap me in two!
“Now, pull them down.”
I reached around his solidly built hips and worked his shorts down the tree trunks of his legs. His underwear were already tented in front and I stared with awe and trepidation at the massive bulge growing like some giant beast.
“Now pull my underwear down, sissy-boy.”
“Y-yes Sir,” I replied squeamishly.
As the elasticized waistband of his boxers came down, I gasped in shock at the leviathan it had been covering. His cock was truly massive, eight or nine inches in length and unbelievably fat. I had no idea they could be so big. I gulped hard as I stared at the huge pink head, a dribble of precum already oozing out of it’s tip and the scent of his cologne filled my nostrils heavily. I found myself breathing harder in anticipation of what was about to happen. Was I really going to have to put this throbbing monster into my mouth?
“Take it in your hands and kiss the head,” he ordered me.
“P-please don’t, I-I don’t think I–”
His big hand reached forward and pulled my head toward his cock brusquely.
“Kiss it, you sniveling sissy,” he demanded gruffly.
“But I-I-I–”
He grabbed my head and pulled it forward until my shiny wet lips touched the tip of his warm tool. It left a glossy pink imprint against his hard, firm flesh.
Whimpering weakly, I gave it a little frightened kiss.
“Ha ha!” he bellowed, “You even kiss like a sissy.
“Now I want you to ask me politely if you can suck my cock…go ahead sissy–ask me.”
I looked around the room as if expecting someone to intervene on my behalf but nobody was moving. Joshy was watching in horror and Sarah was looking down on me with an evil smirk on her face.
“Um…I um…” I stuttered haltingly.
His hand reached down and he swatted the top of my head roughly.
“Look up at your betters when you ask them a question,” he barked.
I certainly didn’t want to make this brute angry!
I sniffled and cleared my throat nervously.
“Um…Sir? May I um…please suck your, um, penis, please?” I said hesitantly.
“Its a cock, you little faggot,” he sneered, “now open wide.”
Fearfully, I did as I was told but I was too afraid to keep my eyes open. No sooner had my pink glossy lips parted when I was rewarded with his meaty battering ram. He shoved it deep into my mouth, ramming it all the way in until it bottomed out at the back of my throat. My eyes flew open and I gagged reflexively, my hands waving the air in front of me as I tried to put a stop to his abuse. He pulled it out, just enough to give me a good taste of his firm, throbbing head, before plunging it back in again. I felt like I was choking on a baseball bat! I’d never had anything this big in my mouth in my entire life and my jaws hurt just trying to take it all in.
I squealed like a girl as he gripped the sides of my head firmly and began pumping me forcefully. I could already taste his copious precum and it coated my mouth with salty slickness as his fat head slipped in and out between my wide open jaws. My cheeks were stretched to the limit as I struggled to accommodate his mighty thrusting pole. I squealed helplessly, waving my hands again for him to stop but he showed no signs of hesitating.
“Suck on it good, sissygirl,” he said in a husky voice as he energetically plunged it deep into my mouth again.
My gagging only made him chuckle with glee at my plight and he widened his stance to give himself a better balance. I was forced to take a hold of the base of his cock but my small hands only went halfway around it’s massive girth.
“Look up at your Master when you have his boner in your mouth,” he demanded.
My eyes fluttered upwards to gaze upon his handsome, mocking features.
“That’s better,” he said smugly, “I want you to see who it is that’s gonna fill your mouth full of cum.”
I was terrified at the thought of having his semen in my mouth. It was only a week ago that I kissed my first girl and now I was being forced to give this brute a sloppy blowjob! I prayed he wouldn’t really cum in my mouth but instead pull it out. Maybe he was just trying to frighten me.
Would there be much, I wondered. I certainly hoped not.
“You know, I recognized right off that your sissy faggot friend was just a guy wearing a dress and diapers but I really thought you were a girl,” he admitted to me.
My face went red with shame as he pumped his hard cock in and out of my slick mouth.
“But with pouty, dick-sucking lips like yours, you better count on some guy wanting to ram his cock down your throat everyday. I’m gonna teach you the fine art of sucking a real man dry if it’s the last thing I do.”
He laughed heartily as he looked down on me, slamming his big fat member deep into my throat and making me gag on it again.
I squealed weakly in protest, unable to defend myself verbally.
Already, my jaw was hurting and my muscles were sore as I silently prayed for him to stop his brutalizing of me. Nevertheless, the sooner I could get him to cum, the sooner I would be finished here, or at least, that’s how I rationalized it to myself. Unconsciously, I sucked and slobbered with determination and diligence, trying to manipulate his mighty shaft into releasing it’s liquid treasure.
Suddenly, I felt him grab my ears so hard I thought I’d cry out with pain. Inexplicably, he paused his rhythm for a moment before jamming his shaft as far in as it would go.
With a heavy guttural grunt, he exploded in orgasm, blasting a huge creamy load right down my throat. I was forced to swallow it in one gulp and as he eased his cock out slightly, I thought he was done but then he quickly flooded my mouth with another warm, creamy batch of his thick semen. With my mouth still crammed full of cock, I squealed loudly and shook my fists in frustration, struggling to swallow the latest salty load he’d given me. No sooner did it get past my larynx when he blew a third and equally large load, filling my mouth again completely with more sticky cum. I felt like I was drinking from a fire hose–was there no end to this man’s semen?
At last, he eased it out of my aching mouth and I gasped for breath, even as his cum dribbled past my lips and down my chin. Halfway down the shaft of his gigantic member, I could see a pink ring left by my lipstick.
Coach Saunders was breathing heavily and he used my head to steady himself as he swayed uncertainly. A large pearl of cum appeared at the tip of his throbbing cock and grasping his tool in his hand, he shoved it back in my warm, wet mouth.
“There’s still more to come,” he said breathlessly.
Sure enough, one last bit of ejaculate spilled onto my tongue and I dutifully swallowed it, desperate for this terrible ordeal to be over with.
“Now, kiss it and say thank you sir,” he ordered me as his chest heaved from his exertions.
Blushing hotly, I reached forward and kissed his reddened and pulsing head tenderly before looking up into his leering face.
“Thank you Sir,” I said, almost in a whisper, “for letting me suck your cock.”
“Not bad for your first try,” he said ruefully, “You’ve got a long ways to go, but I’ll make sure you get plenty of chances to practice.”
I blushed hot red as he openly humiliated me before the others and I felt I had to say something.
“But I..I don’t want to do it again,” I stammered.
“Yes you do. And you better not breathe a word of this to anyone, if you ever want to kiss my cock again–got it?”
I was both shocked and ashamed that he would make such assumptions about me but I was too afraid to contradict him. Looking up at his manly, confident face, I felt powerless to defy him.
After pulling up his underwear, he zipped up his shorts and tucked his polo shirt back in.
“If you’re good, maybe I’ll let you have some more cock tomorrow,” he snorted as he turned to go.
I wiped the cum off my chin resentfully and licked my lips to get the last of it. Was this what it was going to be like for me at this school? I felt so used and the shame I felt was crushing me like a boulder. My face burned hotly even as I licked my lips of the last bit of his salty cum and swallowed it as Joshy watched me closely.
I wanted to shout at him that I wasn’t a cocksucker and that I’d been forced to do this against my will. But somehow, I felt my explanation would fall on deaf ears.
The coach gave Sarah a peck on the cheek and he left us without a further word.

I still couldn’t believe what just happened. I could still taste his slick cum coating the inside of my mouth and I felt so violated and humiliated. Why had he picked me over Joshy, I wondered?
“Now that you’ve had your lunch, it’s naptime for you sissies,” Sarah announced as the door closed.
The other two were still looking at me and I blushed in embarrassment, wondering what they must think of me, a prissy sissy who had willingly swallowed so much cum.
Sarah escorted us to our cribs and helped us in, before shutting out the lights and leaving us alone.
Clutching my soft teddy bear to my chest, I looked out the short distance between my own crib and Joshy’s. He was still watching me and I sensed he wanted to talk to me badly.
“Gosh Chrissie, that coach sure has a big wiener, huh?” he said breathlessly. “I’ve never seen anything so big!”
I sighed heavily as I lay against my pillow, still ashamed at what just happened.
“Have you ever seen a penis that big? I can’t believe you even got it in your mouth.”
Was that a trace of envy I was discerning in his voice?
“I didn’t want to, you know,” I snapped angrily.
“Yeah, but still…I can’t believe you swallowed all his cum. What was that like?” he asked earnestly.
“Huh? What do you mean?”
“I mean, I’ve never done–you know–had a man’s penis in my mouth…what was it like to use your tongue to please him?”
I blushed furiously at his line of questioning. He seemed to take for granted that I was a cocksucker and that I did this sort of thing all the time.
“Well it wasn’t like I was trying or anything,” I retorted defensively, “Anyway–he made me do it–I didn’t want to do it.”
“Was it hard to swallow all that cum? It looked like he really came a lot,” he said excitedly.
For a moment, I just stared at him, wondering if he could see how red my face was.
“You don’t mind me asking do you Chrissie? We’re best friends–remember?” he entreated.
“I thought I was going to drown,” I replied honestly, “I was swallowing as fast as I could.”
“I wish he would have picked me,” Joshy sighed longingly, “I would have taken longer, just so I could savor the feeling of having his big wiener filling my mouth….Do you think he’ll let you suck him again?”
“I don’t want to suck him again!” I tried to explain, “I’m not gay or anything!”
“Yeah but still,” he repeated, ignoring my response, “I would love just to kiss his tool…” he sighed again like a star-crossed lover, “And you had it all in your mouth! I’m sooo jealous!”
I shook my head in consternation.
“What did his cum taste like?” he pressed.
“I don’t know,” I said in exasperation, “I can’t describe it.”
“I wish he would have picked me,” he said, his voice heavy with desire and regret, “but I know why he picked you–it’s cause you look like a real girl.”
The way he said it sounded so petulant and accusing, a surge of anger burned inside me.
“No I don’t!–You do,” I replied in a snotty fashion.
“Oh no, did you see how quickly he picked you? It was because you have those girly legs and pouty lips…any guy would want to have you.”
I sensed jealousy and resentment from him but also genuine admiration and it made me stop and think for a moment. Did guys really look at me like that? Was I desirable and sexy to some of them? The idea of having sex appeal made me feel strangely excited and to my surprise, I felt my own penis starting to harden.
“Do you mean that?” I asked tentatively in a whisper.
“Oh yes Chrissie–you’re so lucky. Guys like me have to really try hard to be prissy and femmy but you’re a natural. That’s why I couldn’t resist kissing you when I first saw you.”
He sighed again and leaned back in his crib.
“I guess I have a sissy crush on you, Chrissey,” he admitted.
I was lost in thought as I contemplated being the focus of lust and desire for a segment of the male population….what would that be like, I wondered to myself.
Suddenly, the door opened and Sarah thrust her head in, a shaft of bright light shining upon our cribs.
“Do I hear talking in here?” she demanded accusingly, “Because if I hear one more peep out of you, you’ll both be taking a visit to Mrs. Sterne’s office.”
We cowered in our cribs and tried to act like we were sleeping, fearful she might not wait for any further provocation.
At last, without another word, she stalked out of the room.
I closed my eyes and thought further about the notion of being pretty and desirable, an unfamiliar feeling to be sure.

I woke up some time later to find the lights were still turned out in the Nursery. Everything was quiet, although I could hear faint, indistinct sounds from one of the classrooms nearby.
I became instantly aware of the cool, clammy embrace of my diapers pressing against my hips and buns. With my hands, I made a furtive investigation which quickly revealed, to my utter dismay, that somewhere in the course of my nap, I’d completely soaked my diapers. Why hadn’t I woken up??
Worse than that, the clinging rumba panties Ms. Taylor had dressed me in combined with my plastic panties to ensure the sopping wet cloth remained annoyingly and persistently pressed against my skin. I tried rolling over and assuming several different positions but it made no difference–these wet diapers were going to continue to remind me of my incontinence no matter what I did.
Just then, the door opened and Ms. Taylor strolled in airily, a pleasant smile on her pretty face. Clicking on the light, she came over and reached into Joshy’s crib, squeezing the thick seat of his diapers.
“I don’t know why I even check you anymore,” she said, smiling with mock irritation, “Your diapers are always soaking wet after naptime.”
Joshy giggled merrily as he looked up at her shyly.
Rising out from under the baby blankets, I gripped the wooden rail of my own crib as I waited impatiently for her to come over to see me. I felt so childish, my own pee-soaked diapers clinging stubbornly to me–a clear example of my own lack of self control. I had wanted so badly to make a good impression on Ms. Taylor but it was clear she saw me as nothing more than a big baby and I knew this would only confirm it.
The day’s humiliations came rushing back at me as I re-lived the shame of having Coach Saunder’s big cock rammed in my mouth, and along with my unexpected accident, it was all too much for my fragile ego.
A sob quivered up through my throat and my lip trembled as I fought back a flood of confused emotions.
“I-I wet m-my diaper!” I wailed miserably.
Tears tumbled down my cheeks as Ms. Taylor’s gorgeous face transformed into one of heartfelt sympathy.
“Ohh, my poor little sissy girl!” she exclaimed as she came over and swept me up in her arms. Resting my head on her soft, bare shoulder, her slim hand reached back and squeezed the saturated thick seat of my diapers.
“Oh my yes–you’ve really soaked yourself haven’t you?”
Unable to speak, I could only sob incoherently as I buried my nose into the fragrant softness of her hair and neck, luxuriating in the wonderful scent of her perfume.
“Don’t you worry, little Sugarplum, I’ll get you all changed and into a nice dry diaper in no time.”
I felt a little relieved, albeit embarrassed but I was happy to have her focusing her attention on me as she opened my crib and let me out. I sniffled and and waited helplessly as she turned to Joshy’s crib and opened the side rail as well. I watched in indignation as she led the simpering sissy over to the changing table and sat him down with the obvious intention of changing him first. My impatience getting the better of me, I stamped my feet and shook my fists in frustration.
“But I need my diapers changed!” I whined urgently.
Ms. Taylor turned to me and she bent over slightly to grasp my pink rubber pacifier in her elegantly manicured hand. Momentarily transfixed by her sexy adult cleavage, inches in front of my face, I gazed foolishly as she positioned the pacifier before my lips.
“Open up, Chrissie,” she urged me with her million dollar smile.
“Uh-uh,” I whined, turning my head away.
I didn’t want to suck on my pacifier–I wanted her to change my wet diaper!
“Open up, Chrissie,” she said, ignoring my protestations, “time for your paci…”
I didn’t like being ignored and frankly, I was tired of being treated like a two-year old.
“I don’t wanna,” I replied stubbornly and I crossed my skinny arms over the pink ruffles on my chest.
“You didn’t mind it when you had some of your gooey-goo on it–is that what you’re trying to get me to do again?” she asked with a coy smile.
I blushed hotly as I recalled what she had done to me earlier and she took advantage of my shock to push the pacifier into my gaping mouth.
“Now, its good experience for sissies like you to learn certain girl skills, like caring for babies. So today, you’re going to be my teacher’s pet and help my change Joshy’s diapers.”
I sucked my pacifier in defeat as Ms. Taylor went about her duty, first peeling off Joshy’s plastic panties and then unpinning his heavy wet diaper.
“Okay Honey, why don’t you put these in the diaper pail, okay?” she asked sweetly.
I felt a certain revulsion about touching something Joshy had peed in but my distaste vied for the frustration I felt with being taught “girl skills”.
Gingerly, I took the wet diaper and panties and carried them over to the big rubber diaper bin, holding my breath as I opened the lid. My efforts notwithstanding, I was assailed by the pungent smell of stale diapers until the lid fell back into place. I was ashamed to be a contributor to that smell and I knew it only added to Ms. Taylor’s infantile assessment of me.
She was already positioning a new stack of diapers beneath Joshy and I took a moment to stare down at his hairless crotch. His minuscule penis was caged in a similiar chastity device to mine, although his was made of clear acrylic. Still, it was obvious that it rendered his wiener just as useless and inaccessable as mine and I felt a twinge of sympathy for the smiling sissy. Joshy giggled, oblivious of my concern as he stared up at Ms. Taylor and her beautiful big breasts.
“Chrissie? Be a good little girl and go and pick out a nice pair of plastic panties for Joshy. Oh, and you might as well pick out a pair for yourself too. But if it’s not feminine enough, I’ll have to spank your bottom,” she chuckled with amusement.
I caught my breath until I realized she was just joking. Yet despite her sweet nature, I could nonetheless visualize her paddling one of us all too easily over her firm, sexy thighs.
I went over to the panty drawer and began thumbing through them carefully. To my surprise, I felt a strange tingle in my groin, and an electric buzz of excitement as I sorted through the colorful plastic panties. There were all kinds of panties, in every pastel color one could imagine although most were pink, lilac, lemon yellow, or baby blue. Several were white with pink accents and a large number were nursery print. I gazed in interest at a pink pair with designs of bunnies and blocks and three rows of playful ruffles across the seat. For some reason, as I held them in my hands, my penis throbbed in my chastity device and I felt my heart rate quicken. Selecting the pink pair for myself, I picked out a plain pair of yellow ones for Joshy and brought them over to Ms. Taylor.
“That’s mommy’s little girl,” she said brightly as she accepted them, “And now you get to put them on your little baby friend here.”
“M-me?” I stammered uncertainly. It felt weird to be getting so intimate with another boy.
“Yes Chrissie, someday you may have your own baby to take care of–pull Joshy’s panties up for him,” she instructed me patiently.
Feeling timid, I awkwardly pulled the soft panties over his feet and up his skinny legs. It took some effort, but I was able to work them over his fat, bulging diaper and then the elastic waistband was circling his waist.
Joshy hugged me gratefully as I circled his waist with my fingers to make sure all the cloth got inside the panties.
“Thank you, Chrissie,” he said tenderly in my ear and he kissed me on the cheek with affection.
“What a good little girl you are,” Ms. Taylor beamed proudly at me.
I glowed with pride at being the object of her praise and I blushed shyly, very pleased with myself.
“And now it’s time to get my Little Miss Priss changed–don’t you think?” she inquired.
“Yes, Ms. Taylor,” I said blushing.
Joshy and I traded places and Ms. Taylor began taking my rumba panties down. I was very glad to at last see my own damp plastic panties being peeled off my diaper and tugged down my legs. With a few deft movements, she unpinned my diapers and slid them out from under me. I drank in her delicious curves and pretty smile as she gently and lovingly wiped my bottom and hips with baby wipes.
“I see the cute panties you pick out,” she said with a playful wink that made my heart stop, “I’ll bet you picked them because of the ruffles and lace.”
Reluctant to say anything in opposition to this beauty, I nodded in agreement.
“It’s important for a prissy little girl to have cute panties–isn’t it?” she said accomodatingly.
“Uh-huh,” I said, even as I blushed.
With a new stack of fluffy, soft diapers beneath my rump, Ms. Taylor powdered and pinned them into place, her movements practiced and graceful. After pulling the plastic panties over my feet, I stood up and let her pull them up my smooth thighs. I felt a certain giddy helplessness as she tugged them up around my bulky diaper and I hugged her to maintain my balance. Every moment spent close to her was like a slice of heaven and I sighed happily as I looked up into her gorgeous green eyes.
“There you are Sugarplum,” she said as she beeped my nose, “All ready for your mommy.”
Reaching down to buckle my Mary Janes back on, the far door opened and Barbara came walking in wearing her jacket and purse. She opened her arms wide and called to me with maternal love written all over her attractive face.
“Chrissie!” she called out to me.
My heart leaped with joy and I waddled briskly over and let her swoop me up in her arms. She kissed my cheek affectionately and reached down to squeeze my thickly diapered seat.
“You’re still dry?” she asked in amazement.
I blushed hotly at her assumption that I couldn’t keep my diapers dry for any length of time.
“Uh-huh,” I admitted shyly.
“I just changed him,” Ms. Taylor clarified, deflating my balloon, “I only woke Joshy and Chrissie from their naps about ten minutes ago and she was completely soaked.”
Barbara looked down at me, with a look of knowing as she nodded in understanding. I could only blush as Ms. Taylor explained how I’d wet my diapers during my nap and was on the verge of tears just minutes before.
“But now you’re all pinned back into a nice fresh set of diapers, aren’t you, Chrissie?” she said as if that was the only thing standing between me and a happy life.
“Yes Ma’am,” I replied meekly.
“Did you have a good time today in your first day at school?” Barbara asked eagerly.
I thought back and re-lived the memory of coach Saunders thrusting his monstrous cock into my mouth and my struggle as he exploded his incredible quantity of cum down my throat. I wanted to tell her about how I was abused and at the mercy of cruel women like Sarah and Mrs. Sterne but for some reason, the words wouldn’t come. For some reason, some small part of me looked upon the coach with admiration and envy–he was the epitome of a man I would never be in a million years. Our differences were so great that I guess it didn’t surprise me that he’d treat me like his plaything. It would be absurd to think he’d look at me with respect. Perhaps a part of me felt that what he did to me was what I should expect from a man who was my polar opposite.
Still, I knew that I was avoiding the 800 lb. gorilla in the room. In some deep recess of my mind, I knew there was some secret part of me that had enjoyed pleasing him, even if I wasn’t ready to admit it, even to myself.
In any event, I merely shuffled my Mary Jane clad feet and said little about the day’s activities.
“Uh-huh,” I said without much conviction.
“And it looks like you’ve made a new sissy friend too,” she said brightly as she looked over at Joshy.
The object of her attention beamed back at her and came over to drape his skinny arm over my shoulder.
“That’s right, Ma’am,” he said enthusiastically, ” Chrissie’s my new best friend!”
“Well give your little sissy friend a hug Chrissie, it’s time to go home.”
I sighed and did as I was told. Joshy held me close and nuzzled his cheek against mine.
“Bye-bye, Chrissie,” he bade me tenderly.
“Bye Joshy,” I said in return.
At least I had one friend that I’d made today, even if he was as big a sissy as I was.
“Goodbye, Babykins,” Ms. Taylor said as she waved her hand at me like I were a toddler.
“Bye, Ms. Taylor,” I said as my cheeks reddened again bashfully.
“I’m sure you’ll have even more fun tomorrow,” she said with a wink in her eye.
That thought lingered in my mind as Barbara took my hand and led me out to her minivan for the ride home.

Chapter Seven A Birthday to Remember

Sitting in the center of the playpen in my nursery, I looked out through the mesh that made up the sides of the enclosure at the TV located on the far wall. A Barney DVD was on continuous loop and the dialogue had already become well memorized by me earlier this morning. It was Barbara’s way of keeping me “entertained” although it was starting to get annoying.
I was sitting cross legged, Indian style as I fumbled with one of baby dolls that comprised my immediate selection of toys. I was forbidden by Barbara from getting out of the playpen and what aggravated me was the ease in which I could do it, if I so chose. It would be a simple matter of stepping over the side but I didn’t dare risk it. My new mommy had an uncanny ability to know when I’d done something I wasn’t supposed to and she’d often burst into my nursery without notice. Being a woman of her word, it was rare that I didn’t find myself face down over her lap getting my bottom paddled for some infraction she’d warned me against. I knew she kept my baby monitor on continuously and if I didn’t know better, I would have believed she had a hidden cam somewhere in the room to spy on me when she wasn’t around.
It was a level of precaution that was completely consistent with the way she treated me. She didn’t trust me to even walk to the living room without her holding my hand and anytime she wasn’t doing anything specific with me, I was either placed in my playpen (I had three) or my crib. These were the places I spent the vast majority of my time and it was only broken up by events like mealtimes in the highchair and diaper changes. It was routines like these that made me resent my life under Barbara’s rule.
On the other hand, my new regime definitely had it’s advantages.
Unlike when I used to live with my mom, everything was done for me now. I didn’t have to make any decisions and there was zero stress in my life. It had always been tough at school for me, trying to live up to people’s expectations. I was never tough enough to hang out with the guys and the girls all thought I was just a big sissy. I guess in retrospect, they hadn’t been too far from the truth. Looking down at my present outfit, it was certainly hard to deny it. Barbara had dressed me today in a frilly pink and white Alice in Wonderland baby dress with a girlish gingham print and scalloped lace around the short hem. I was wearing knee socks with pink satin bows adorning the tops and my glossy black Mary Janes. She intended for me to wear the matching set of lace rhumba panties for this dress but I had slopped baby food on them at breakfast so now my pink nursery print plastic panties were on display instead.
And as I shifted my weight on the padded surface inside the playpen, I realized I’d wet myself at some time during the morning without knowing it. The triple thick layers of my diapers were warm, wet, and spongy against my buns, giving me a constant reminder why I couldn’t be trusted without them.
This seemed to happen more often than not these days–I just peed without even thinking about it and I didn’t really notice when my diapers had become wet, unless they got heavy or had had the chance to cool down. Whining came naturally to me and I found Barbara was usually pretty quick to change me unless she had something important occupying her attention. In those cases, I just had to sit there in my wet clammy diapers, waiting for when she could make time for me.
The last two weeks at school had followed closely the routine of my first day at the Francis Merrimont Boy’s School. Most days, Sarah brought Coach Saunders by who inevitably wanted me to service him like I did the first day. He was determined to give me an education, although what he wanted to teach me had nothing to do with P.E. Through his usual method of slapping, grunting, and explaining, he taught me how to take as much of his monster cock into my mouth and how to cope with swallowing his huge loads of cum which signaled the end of my lessons. It was still quite a challenge but I was getting better and more confident every day. I think even he was amazed at how much I could swallow without gagging. Secretly, that had become a small source of pride for my shattered ego.
By all rights, I should have despised him for what he was doing to me but for some reason, I just didn’t. I guess I felt oddly flattered that he picked me out over all the other sissies and in any case, it was easy to admire him for his physical looks and natural charisma. I never told Barbara about my daily oral duties but I often found myself looking forward to the opportunity to bring about the coach’s next orgasm. Being deprived of any sexual relief meant I looked for in it other ways–in this case, giving the coach the best blowjob I could.
As far as my own orgasms, I had nearly forgotten what they felt like. And perhaps it was that same lack of relief that made me so eager to please the coach. To be sure, I wasn’t getting any myself, even though I’d since discovered that the pre-cum I generated from being sexually stimulated tended to dribble uselessly into my diapers. But an hour never passed in which I thought about what it would be like to be able to masturbate like I used to.
With little else to do, I amused myself with trying different outfits on my dollie which I had secretly given the name of Priscilla. I had laid out a number of them on the floor of the playpen and I was having my own private fashion show when Barbara walked into the nursery.
“Hello Chrissie, how’s mommy’s little baby girl?” she asked sweetly.
“Hi Mommy!” I cried out, happy to have her attention. Truth was, I felt starved for attention, or at least companionship. Certainly, I couldn’t consider Barbara any kind of peer, but I did enjoy her company, if for no other reason than the fact that she was both beautiful and sexy and she seemed to genuinely love me for who I was.
As usual, her hand slipped down to squeeze the seat of my fat diapers where she discovered my wetness.
“Hmm,” she mused as she flipped up the short hem of my baby dress and pulled back the waistband of my nursery print plastic panties, “Not too wet, looks like…I think we’ll wait to change you.”
“Yes Mommy,” I replied obediently as I stared down her low cut top. Her delicious bosom was displayed in the most alluring fashion for me and I took advantage of her position to drink it all in. She was wearing a tight white tank top under a loosely fitted blouse and I reveled in her fabulous curves.
“I have a special surprise for you Chrissie,” she announced as she straightened up, “Today, you have a special playmate to keep you company.”
“I do?” I asked with amazement.
“That’s right, Honey, this afternoon, you’re little friend Matty from school is going to be spending some time with you. Maybe you can show him your dollies and show him your collection of sissy outfits. Won’t that be wonderful?”
Obviously, Barbara had never met Matty or she’d know that he had zero interest in such things. For that matter, he’d never shown any interest in me either and I felt a growing sense of apprehension at the thought of him being forced to spend time with me.
“Oh,” was all I said.
Barbara’s smile vanished as she perceived my apparent lack of interest in her proposal.
“What’s the matter, Baby–don’t you like Matty?”
“Oh yes, Mommy, but I don’t think he likes me,” I replied honestly.
“Aw, Sweety…well that’s just because he doesn’t know you yet,” she blithely assured me, “I’m sure once you two have had the opportunity to get to know each other, he’ll want to be your best little friend in the whole wide world.”
I wasn’t so sure but I didn’t say so and right at that moment, the doorbell rang.
“That must be them now,” she said, her initial excitement having returned.
Turning on her heel, she strode out of the nursery and I heard her go to answer the door. A moment later, I heard her greeting what must be Matty’s mother and then the three of them coming down the hall.
Even though Matty had seen me in my most sissyish outfits and acting like nothing more than a big priss, I still found myself blushing at the thought of him seeing me in my “bedroom” which reflected who I really was–a diaper dependent sissy baby. Here, he would be seeing “the real me” and I cringed at how he’d respond. What would he think of me when he saw how I really lived?
As the three of them entered the open doorway, I tried to hide the little dresses and baby clothes of Priscilla hoping maybe he wouldn’t see them.
“Matty–you remember Chrissie from school don’t you?” Barbara asked as she swept her manicured hand in my direction.
“Yeah,” he said sullenly. It was obvious he had been coerced into coming over here and I couldn’t help but wonder if maybe he’d even been spanked to make him more amenable.
“Chrissie? Say hi to your little playmate,” Barbara beamed down at me.
“Hi Matty!” I said, trying to put the best face on the situation. Even though I’d tried and failed to get him to like me at school, perhaps in these circumstances I could hope to influence his opinion of me for the better.
“Chrissie, maybe you can show Matty here the lovely outfits you were dressing your dollie in,” Barbara suggested cheerfully.
I groaned inwardly and wilted under her ignorance of our true relationship.
“Oh, um…it’s nothing really…” I mumbled trying to minimize my willingness to play with dolls.
Matty rolled his eyes as Barbara reached down and picked up a few frilly dresses that belonged to Priscilla.
“Aren’t these lovely?” she said as she showed them to Matty.
I blushed hotly as his brow furrowed and his opinion of me visibly sank even further.
“So tell me, Sharon,” Barbara said as she turned to his mom, “How often do you normally change Matty? Has he already wet today?”
Stifling a giggle, she shook her head.
“Oh no, Matty here is just in trainers. I’ve been threatening him with diapers if his behavior doesn’t improve but for now he’s just in trainers. He should be fine for the afternoon and if he needs to use the bathroom, he knows to ask you.”
Matty’s face showed his look of smug superiority that he wasn’t required to be diapered like me.
Barbara had a look of surprise, but she smiled down at him in admiration and nodded with understanding.
“So I’ll be back at Chrissie’s naptime to pick Matty up–he’s got soccer practice later on,” Sharon explained.
“That sounds great,” she said, “I normally change Chrissie’s diapers around two and then put her down for her nap, unless she’s been otherwise naughty.”
I blushed at her explanations of my babyish treatment which contrasted so greatly with Matty’s own routine.
Sharon said her goodbyes and then Barbara left the two of us to be alone in the nursery. I felt very awkward, having never been with Matty by myself and it was made worse by the fact that I knew he wanted nothing to do with me. Nevertheless, I admired him for being the guy I could never hope to be and I tried to think of some way to make him accept me as his friend.
“I…I didn’t know you played soccer…I’ll bet you’re really good, huh?” I asked timidly.
Matty only grunted in response. It was clear he had no intention of making idle conversation with me so I decided on a different tactic.
“Um…I don’t get why you’re wearing trainers…do you wet your pants sometimes?” I asked hopefully. If he had bladder issues, at least we’d have that in common.
“Are you kidding? I’m not a sissy like you,” he snapped defensively.
I winced inwardly but continued in my obtuse way.
“Yeah, but your wearing trainers…do the other guys on your team wear them too?”
This seemed to strike sensitive nerve with him and his cheeks reddened noticeably.
“No–of course not. I’m only wearing them because I made problems for my mom at home.”
“Ahh…” I said in new found understanding, and with a trace of pride, “Sounds just like me…my mom sent me here because I was always getting in trouble.”
I hoped he wouldn’t see through my boasting and would instead see a kindred spirit in me but he only snickered at my attempt to compare myself to him.
“I’m nothing like you. You’re a sissy and always have been. I’m not and never will be,” he replied curtly.
Even though I couldn’t help but acknowledge the truth of his words, it stung nonetheless and I felt a vast gulf between us. Yet, how I wished I could be more like him!
For a while, I remained silent, my feelings hurt as Matty trudged around my nursery, amazed and at the same time disgusted at my living arrangements.
“Man, you really are a baby aren’t you?” he sneered, “lookit all these baby toys.”
I blushed in embarrassment and stepped out of my playpen, even though I knew I wasn’t supposed to.
“Aw, that’s just stuff Barbara got me–but I don’t actually play with it,” I lied unconvincingly.
Matty’s silence told me he didn’t believe me but he didn’t even care enough to bother trying to contradict me.
“But you’re the only baby I’ve ever seen that sucks cocks,” he goaded me in a challenging tone as he turned abruptly to face me.
My face was beet red as I tried desperately to think of a way of explaining that one.
“Well…it’s not like I want to…” I replied feebly, “Coach Saunders makes me suck him off.”
Matty crossed his arms over his chest and looked at me with his superior air.
“Doesn’t look to me like you put up too much of a fight. And it looks to me like he’s got you pretty well trained,” he said smugly, “Hmm…Maybe you should try out those skills on me?”
For a moment I was speechless as I stared back at Matty, wondering what to say. Should I keep up the charade about my unwillingness to blow the coach? I didn’t think he believed any of my attempts to diminish what a sissy I was and it might even make him more hostile towards me.
On the other hand, a part of me thought this might be the one and only way I might win him over to actually start liking me.
I really wanted Matty as a friend. He had obvious charisma and I knew even under different circumstances he’d wouldn’t normally associate with me.
Taking a deep breath, I summoned what little courage I had.
“I-if you’d like…” I offered meekly.
Standing with his chest thrust out, he put his hands on his hips in a defiant and confident pose.
“Come over and unzip my jeans,” he ordered me in a cocky manner.
My heart skipped a beat and nervously, I stepped over and hesitantly reached down to unbutton his pants. I sure hoped Barbara wouldn’t decide to walk in right about now. I could only imagine how furious she’d be!
Matty pushed me down on my knees forcefully as he grinned deviously at me.
“That’s where you belong, Sissy-boy,” he told me.
My cheeks reddened again and I unzipped his jeans, pushing them down past his trainers. Seeing the Transformers design on his training pants, I stifled a giggle as I looked back up at him. He seemed embarrassed about them and he hurriedly pushed them down himself to avoid any further discussion of them. Grabbing his limp willie in his hand, he wiggled it in front of my face like a piece of sausage.
“You know know what to do with this,” he said gruffly.
His cock was not the beast that coach Saunders possessed but it was impressive nonetheless. Even though it wasn’t erect at the moment, I could see it was thick and about five inches long.
Knowing that time wasn’t on my side, I quickly stuffed the head of his cock into my mouth, swirling my tongue around the underside of it. To my relief, he responded immediately and I felt it becoming firmer as his tool began to lengthen.
I heard him exhale as he made his pleasure apparent and I began working more of it deeper into my mouth, teasing the sensitive underside with my tongue as my lips wrapped around the widening girth. In no time at all, he was fully erect and my hands went to grip the base of his tool, helping to steady my efforts.
“I can see why the coach picks you all the time,” he said breathlessly.
Judging by the difficulty he had in speaking, it seemed apparent that he was enjoying my blowjob immensely.
My head was bobbing up and down now and his hands went to the top of my scalp to adjust me to his own particular rhythm.
“I’m gonna blow my load in your mouth, Chrissie,” he said in a husky voice, “M-make sure you swallow it all.”
This was going quicker than I expected and I could sense his cock growing more firm in my mouth, like a cat ready to pounce on it’s prey.
Matty’s breath was coming in short heaves and although I couldn’t see his face, I knew it must be taunt and flushed, ready for a big climax. Certainly, this had to be making a good impression on him.
Somehow, it felt so natural to have his thick, throbbing tool slipping in and out of my mouth. I loved the taste and feel of his hard, masculine erection stretching my cheeks to capacity and I longed for him to reward me with his gooey seed.
“I…I…” he was trying to say something but was he was lost in ecstasy and I knew his moment was at hand. I prepared my throat to receive a massive load of warm, creamy cum.
Just then, at the most inconvenient moment, Barbara barged into the nursery, followed by both Matty’s and my mom, their mouths dropping open in collective shock. Matty was too far gone to put the genie back in it’s bottle and he came with a loud groan, laced with grief and dismay as he took in their stern demeanors. His cock flew out of my mouth even as he sprayed my face with a rope of his pearly semen. I gasped in panic as I gaped wide-eyed up at Barbara standing before me, her face a picture of fury.
“WHAT IS GOING ON IN HERE?!?” she demanded in a voice that set my every hair on end.
“I-I-I-um-” I babbled incoherently as my mom came around to get a better look at me.
“I can’t believe it,” she said in utter shock and disapproval, “My son is a cocksucker.”
“I leave you alone for five minutes and this is what you do?!?” Barbara screeched.
“B-b-but, I-I-um,” I stammered, trying to find words to extricate me from this terrible predicament.
A sticky glob of semen dribbled down from my upper lip and unconsciously, my tongue reached out to lick it up.
“Young lady–this is totally unacceptable behavior,” Barbara said tersely, her raging anger barely under control.
“B-bu-but…I was so, you know…I was so horny, Mommy,” I whined in desperation. I knew she didn’t like to hear that word but it was the absolute truth–I was going crazy not being allowed to cum.
“I don’t care what you were, you little sissy, that is an adult activity that you have no business engaging in. You are in so much trouble, you are going to be one sorry little baby when I’m through with you.”
A shiver of real fear rippled through me and I felt a strong stream of pee flooding into my already damp diaper. I stamped my Mary Jane clad feet in anxious trepidation.
Barbara took the few shorts steps over to my pink dresser and snatched the dreaded wooden paddle hanging up on the peg. How many times had I felt it’s painful sting on my bare bottom?
“No-no-no-Mommy!” I wailed miserably.
Waving my hands in front of me, she grabbed my left wrist harshly and yanked me over to her as she took a seat on the edge of the vinyl covered crib mattress. At the same time, Matty’s mother was hauling him over to the only chair in the room, my “spanking chair” that Barbara used expressly for that purpose. She flipped him over her lap before he could even say anything in defense and he landed unceremoniously, only a couple of feet away from me.
Even though my diapers were pretty wet, Barbara was so worked up, she didn’t even take the time pull her skirt out of the way. Instead, she jerked my plastic panties down in three quick movements and threw me over her lap.
“Pu-please Mommy!” I sobbed, “Please don’t spank me!”
“I’m going to blister your little sissy bottom–and that’s only going to be the beginning for you,” she snapped as she unpinned my diapers and pulled them back between my legs to expose my terrified, twitching buns. Looking up in panic, I saw Matty’s face with an expression I’d never seen–genuine fright. His mom had produced a large flat-backed hairbrush and I watched as she ripped his trainers off with a vengeance and threw them aside contemptuously.
“Mama! No!” he cried.
This was a side of him I’d never seen and I could tell his mom was no pushover. He was about to get spanked, and spanked hard!
I whimpered and squirmed but it did me no good.
Barbara’s paddle seared both my bare cheeks with a fiery impact and I gasped in shock, my breath momentarily taken away. She followed her first swat with another, equally harsh one right in the same exact place.
At last, I found my breath and I wailed at the top of my lungs.
Barbara didn’t pause and her angry paddle rained down over and over like the holy sword of vengeance, first one defenseless cheek, then the other, and then back to the first one. I never knew which one she was going to swat and I kicked and sobbed as she spanked me with a severity I’d never seen. My soft, youthful bottom jiggled and shook under the constant battering it was getting from her oaken paddle. I beat my fists on the ground, even as I saw Matty bawling directly in front of me. I struggled and squirmed trying to escape her terrible wrath but she grabbed a fistful of the back of my Alice in Wonderland dress and effectively prevented me from wriggling off.
My face was wet with tears and I sobbed like a baby. Not only was I upset about being caught and punished by Barbara, but I could hear Matty’s mom telling him between the harsh slaps of her hairbrush that she’d be taking him out of our school and enlisting in some boot camp, far away from me and my “bad” influence. So much for my hopes of having him as my boyfriend!
It was no consolation for me to witness his being punished and brought down to my level–my own bottom was blazing and Barbara’s paddle felt like a red hot frypan against my burning, crimson cheeks. I still squirmed over her lap but nothing prevented her paddle from scalding my soft, helpless buns.
As the tears streamed endlessly down my wet face, I knew I wouldn’t be able to sit for several days.
Finally, Barbara stopped and she held the paddle firmly as she scolded me further.
“You are NOT to play with other boy’s pee-pees!” she snapped angrily, emphasizing her point with a savage, blistering swat on my red, stinging bottom.
I tried to articulate my willingness to comply but I couldn’t verbalize anything through my uncontrolled, ragged sobbing.
“And I’d better NEVER find out you’ve had one in your mouth again–do you understand me?” she growled.
I nodded my head, even as more tears spilled down my cheeks. All I wanted was to get off her lap and away from that paddle!
With quick, haphazard movements, Barbara pinned my cool, wet diapers back in place although not with the usual care. With an abruptness I wasn’t used to, she stood me up and placed the paddle on my mattress. Just as quickly, she laid me down in my crib on my back and I assumed she was going to change me, although she almost always used my changing table for that.
“Don’t you move so much as an inch!” she warned me as she shook her long nailed finger at me.
Without another word, she stalked out of the nursery and into the nearby bathroom where I soon heard running water. Meanwhile, Matty was having his trainers and pants pulled back up by his mom as he stood there, crying unashamedly before me. They walked out of the room, saying a few brief words to Barbara before letting themselves out the front door.
Barbara returned with an big red enema bag bursting with hot, soapy water, except that it wasn’t my usual enema bag but a larger one.
I gulped in fear as I looked at the volume of it–and all of it destined for my rear end!
“You’ve got some very naughty ideas that someone put into your head and I’m going to flush them right out of you,” she explained as she positioned the heavy bag on a hook put into the nearby wall. I was still crying as I watched her attach a thick, penis shaped nozzle to the end and briefly test the flow. A strong squirt of water and bubbles burst out of the end and dribbled down the shaft, reminding me of coach Saunder’s semen. Then she leaned forward and unpinned my diapers, pulling the soaking wet front down and exposing my tiny caged penis in it’s chastity prison. Normally, I would have enjoyed seeing the view down her snug top but I was too frightened by what was about to happen to appreciate her big breasts.
“Since you seem to like boy’s penises, I’m going to see that you get one with your daily enema, Chrissie–starting right now,” she explained as she pushed my knees apart.
“No…no…please, Mommy,” I begged her between sobs.
Dipping the fat dildo nozzle into my Vasoline jar, she brought it down and poised it at my shy back hole.
“Spread your legs and open up Chrissie–you’re getting this whether you like it or not.”
I moaned and whined as she pushed the thick, blunt tip determinedly against my anus, using ever greater pressure as I gripped the sidebars of my crib and squirmed on the vinyl crib sheet.
“No…no Mommy,” I quailed as I felt the greasy nozzle end prodding my quivering hole looking for entry.
“OHH!!” I squealed as I lost the battle and the big warm tip suddenly slid past my sphincter.
Barbara smiled grimly as she gently pushed it further in, twisting it and easing it in as I gasped from the fullness of it.
“How does that feel, Sissykins?” she asked with a smug look, “Do you like having a nice big cock filling up your pussy?”
My face burned with shame as she slowly pushed it in and pulled it out slightly, only to push it back again until it bottomed out. Looking up at my real mom, I saw a look of immense satisfaction on her face as she watched me being impaled by this rubber leviathan.
I moaned like a little girl as I looked back at Barbara, knowing I was helpless to do anything about what was happening. She was so powerful and I was so weak, a true baby by comparison to her.
“One thing is for sure–I’m pulling you out of that school before the day’s over. It’s obvious that you’re not ready to enter a world with other boys–never mind grown-ups. I can see that I need to keep a very close eye on you. You are going to stay in this house, except for occasional, short, supervised trips outside when I need you to go somewhere. And you can bet your sweet little sissy bottom that the number of babysitters I’ll approve of is very short indeed.”
I could see my world closing in to these four walls, rarely to step outside, with my nursery becoming the center of my universe.
“Baby girls have no business playing with boys and I’ll make sure you’re never exposed to them again,” she continued.
Reaching up, she undid the clip and I felt a strong force of hot, soapy water invade my bowels.
“Uhhngg,” I wailed.
“Let that be a lesson to you,” Barbara said as she looked down into my tear-stained face.
My mom gazed down at me with a look of disapproval clearly written on her face.
“And here I thought you were behaving yourself under Barbara’s care. To think you’ve just been scheming for ways to suck other boy’s cocks…You barely made it through potty training the first time–what made you think you were mature enough to handle sex at your age now?”
Barbara pinched the clip shut and waited for the water to settle before resuming my enema.
“You are not an adult who plays with guy’s penises–you are a little baby girl–do you understand me?” she said as she glared down at me.
“Ye-yes, Mommy,” I squealed miserably.
“You are a little sissy baby who wets her diapers and likes to wear baby girl clothes,” she continued relentlessly.
“Yes-yes, Mommy,” I agreed.
I squealed and whimpered with each new surge of water, trying in vain to pinch my scalded cheeks together to try and stop the endless flow. Barbara towered over me like an all-powerful goddess, deciding when I should receive more of the enema and when I should get a break. My complaints fell on deaf ears and she continued to drain the enema bag into my puckering, protesting hole.
“My tummy’s cramping, Mommy,” I moaned as I felt the water filling me heavily.
“Good. You’re going to take every drop or we’ll just start right back over again,” she told me firmly.
“Ohhhhh,” I moaned again.
“Tell me what you are, Chrissie,” she said as she released the clip again.
“Ohhhh—I-I…(gulp) I’m a sissy baby g-girl,” I admitted.
“Are you ever going to put another boy’s penis in your mouth again?”
“N-no-no, Mommy,” I whimpered, “ohhhhhh.”
Taking her time, Barbara manipulated the clip, allowing more of the water to flow into my helpless back passage as my sphincter gripped the massive rubber nozzle tightly.
I had never taken this much water before and I felt ready to explode.
“Well now,” Barbara said with a wicked smile, “When I take this out, you’re going to go back over my lap and I’m going to finish your spanking. Are you ready Little Miss Priss?”
“No–no…” I whimpered weakly.
“Okay, I can see you need some more soapy water,” she said as she released the clip again.
“Noo!” I cried as I squirmed helplessly, “I’m ready–I’m ready!”
Barbara snapped the clip shut and gripped the fat base of the rubber nozzle.
“Alright Sissy, I’m going to pull this out and if you spill one drop, just one drop, I’m going to push it back in and we’ll resume where we left off.”
I cried softly as she gently pulled the mammoth dildo from my anus and set it aside. I wheezed and moaned as the large rubber head slid past my sore, protesting hole but I pinched my cheeks together, desperate to prevent any loss of liquid. Pulling my wet diapers back up, she pinned the clammy cloth together which made for an unwelcome embrace of my hips and burning cheeks.
Looking around, she located my plastic panties that had been kicked aside when she was spanking me earlier. Gathering the leg holes together, she worked them over my Mary Janes and up my slim, hairless legs.
Pl-please–please don’t spank me,” I begged her weakly but she ignored me as she worked the clinging nursery print plastic panties over my soggy diaper.
Helping me to my feet, I swayed uncertainly and sniffled, the heavy liquid cramping uncomfortably inside my bowels.
“Chrissie, you were a very, very naughty little girl today. This is what happens when you disobey your mommy,” she said in a calm, rational voice.
“Please…” I whimpered as she lowered me over her lap.
Taking the paddle in her hand, she rubbed it against the smooth plastic of the baby panties covering my bottom.
“Let this be a lesson to you next time you try and act like an adult,” she said evenly.
The paddle swooped up and then came down again with a loud splat against my diapered rump. The thick cloth did much to alleviate the stinging impact although the conditioning she’d already done pretty much cancelled any advantage I had there.
Again and again, she swatted me harshly and once more, I burst into fresh tears. Not only did the slaps of her paddle really hurt, I was losing control of all that water trapped in me. Slowly at first, I felt it leaking inexorably out of my hole but what started as a trickle soon turned into a messy deluge. It gushed out even as Barbara’s hard paddle slapped my spongy, expanding diaper. I wailed miserably as the sludgy fluid emptied in a flood against my punished cheeks and was quickly slapped hard and flat against my skin. Eventually it seeped down my front and I cringed against the disgusting mess.
Beating my fists on the floor, I wailed and cried in helpless frustration.
Finally, the humiliating spanking was over and Barbara set my paddle down on the mattress in front of me. Helping me to my feet, she stood me up and wrapped her arms around me, hugging me close. Hot tears of pain and remorse spilled down my cheeks and onto the soft skin of her bosom where they disappeared down the front of her blouse.
She began shushing my crying and kissing me gently, telling me my punishment was finally at an end.
I felt completely defeated by this buxom, authoritarian woman but at the same time, strangely, I felt a closeness I’d never felt with anyone else. I knew that as strict as her punishments were, she really cared for me and wanted what was best. As she pushed my fat pink pacifier into my mouth, I looked up into her beautiful eyes and I knew she was right. I hugged her tightly and she kissed my forehead lightly.
“It’s all over, Chrissie,” she assured me, “Mommy loves her little baby girl.”
I felt like a very messy baby and my buns twitched as the warm, sticky material of my diapers clung tenaciously to my scalded rump.
“Okay, it’s time to get you cleaned up and into a fresh set of diapers, Sweetie-pie,” she said as she guided me to my changing table.
Much as I enjoyed having Matty’s cock in my mouth, I knew I’d never risk it again while under Barbara’s roof. However it was that she did it, there was no escaping her constant, omniscient attention.
For the better part of the next fifteen minutes, Barbara cleaned the nasty mess of my diaper area before declaring me ready for my change. Taking a thick stack of soft, fresh diapers, Barbara positioned them under my still stinging buns.
“This is what all sissies want, don’t they Chrissie,” Barbara asked of me.
“Yes, Mommy, I just want to be back in my diapers again,” I admitted weakly but truthfully.
“It’s what you need, isn’t it?” she prodded as she sprinkled fragrant baby powder all over my caged loins and chest.
“Yes, Mommy,” I replied deferentially as I breathed deeply of the baby powder. And in fact, I knew all too well I couldn’t last an hour anymore without helplessly wetting myself. Like it or not, I was going to need diapers and plastic pants for the forseeable future, if not forever. Barbara gently pulled the pillowy soft cloth of my diaper and as I continued to sniffle, I reflected on how much I’d come to love this ritual of ours. Barbara was always so tender with me, making sure she never pricked me with the diaper pins and as she lovingly pulled the cloth snug around my hips, I adored the soft, comforting embrace. I felt so secure, not only because it protected me from accidents but also because the whole process made me feel safe and sheltered from harm. No bullies would ever taunt me again so long as I lived under Barbara’s roof and in her care. All I wanted was to be her little toddler.
After pinning my comfy diapers closed, Barbara took a pair of cute polka dot side snap baby panties and pulled them over my feet, working them up my smooth legs to enclose the bulging cloth within. While Barbara was cleaning and diapering me, she was also discussing some related matters with my mom.
“So Pamela, how have those hormones been working out for you?”
“Oh, faster than I expected,” she said excitedly, “As a matter of fact, I think I’m ready to give Chrissie his first wet nursing in ten years.”
“Ten years?” Barbara asked quizzically, “How long were you breastfeeding Chrissie the first time?”
“Oh, until he was four years old, at least,” she admitted, “He’d cry and fuss whenever I tried to give him a bottle and it took forever to get him weaned.”
“I can so easily imagine that,” Barbara nodded.
She picked me up and gently led me over to the love seat where my mom was already sitting.
“Now there’s just one thing, Pamela,” Barbara hedged, “You really shouldn’t think of Chrissie in those masculine terms anymore.”
“Ah yes,” she remembered.
“There’s really nothing left of “his” boyhood to justify terms like ‘his’ or ‘him’. And it’ll only become more so as time goes on. When I locked up her little penis, she soon learned that she wouldn’t be able to act sexually as a boy anymore. And as you’ve unfortunately already observed, Chrissie feels naturally compelled to please other boys with her mouth. I’m sorry you had to see that, but I guess I should have seen it coming. As time goes on, she relates more and more to her feminine side and I’m doing everything I can to encourage it–With the exception of letting her have sexual relations, of course,” she added quickly.
“Of course,” my mom repeated, “I’m in complete agreement.”
Pouting in frustration, my lower lip puffed out a typical sissy display of displeasure.
“You see these things so clearly,” my mom gushed in admiration for Barbara, “Looking back in retrospect, I don’t know why I didn’t see it myself. I almost feel guilty for trying to raise him–I mean her, as a boy. It’s obvious to me now that she always wanted to be a little sissy girl and the diapers and baby treatment are the crowning touch. You were right all along.”
“Thank you,” Barbara replied gracefully, “My little buttercup here knows that she just wants to be mommy’s little baby girl now–don’t you Chrissie?”
I nodded in acceptance of her truth.
“I’m just so impressed by the transformation you’ve made–and it’s such a relief to be free of her whiny, pestering tantrums.”
“The only tantrums our little baby has anymore is whether she has creamed corn or spinach for dinner,” Barbara chuckled with amusement.
My mom giggled, even as she marvelled at Barbara’s complete authority over me.
“How about we have Chrissie take her lunch directly from her former mommy now?” Barbara suggested.
My mom smiled down on me happily as she opened her blouse to reveal her swollen breasts. They had obviously grown quite a bit since I last saw her and now I understood the reference to the hormone treatment. The wet spot on her bra confirmed my suspicions. My mom was actually lactating again!
“Come on now, Chrissie, show Mommy what aunt Barbara has taught you,” she said as she brought my head up to her dribbling nipple.
I was distinctly uncomfortable with the notion of breastfeeding from my real mom–after all, my previous desire with Barbara had been borne out of my lust for her fabulous bosom. I harbored no such feelings for my mom.
“Uh-uh,” I whimpered as I pulled my face away.
“Chrissie,” Barbara admonished me in a sharper tone, “You know better than to act like that.”
“But I don’t wanna,” I whined pitifully.
“In situations like this, it’s better just to take the intitiative with her–just push your nipple into her mouth and she’ll begin nursing,” Barbara coached her.
My mom complied willingly and brought my face up until her dripping nipple was brushing between my lips.
“Open up, Chrissie,” she instructed me.
With a small slap on my bare thigh, Barbara caused me to yelp and open my mouth which my mom quickly filled with her engorged nipple. My mouth clamped down and I accepted her breast, albeit unwillingly.
“That’s better,” Barbara commended her, “she needs to understand that the choice isn’t hers and that this isn’t sexual in any way–it’s simply a mother giving her the nursing she needs.”
“Mmm…yes,” my mom concurred as she looked down at me with happiness written all over her face.
“This is right where you belong, Sweetie,” she told me, “Now you’re the baby I always knew you were.”
I whimpered helplessly as I drank in the slightly different taste of my own mother’s milk.
Although she wasn’t as endowed as Barbara was, she still had a considerable quantity of milk to provide. I was nearly full when she switched me over to her left breast which I took with less resistance than previously.
“Thaaat’s mommy’s baby,” she cooed down at me.
I blushed and realized that perhaps more than anything else, my mom’s acceptance and encouragement of my new baby status was perhaps the final nail on the coffin of my boyhood. But somehow, it no longer distressed me. Two months ago, I would have agonized over being called a sissy by the girls at school. Now, I realized it was the truth–not only that–but I enjoyed being a sissy baby. Deep down, under the thin, fragile veneer of my maleness, I knew a prissy, feminine sissy had always been there, waiting to come out. And Barbara had known right from the beginning. I felt a fresh surge of affection for that woman, who even now was looking down on me with her overwhelming maternal love.
I had finished my mom’s other breast and was now full and ready for my nap but Barbara slipped in next to my mom on the loveseat and she began moving me into position over her lap.
“No…no, Mommy,” I whimpered weakly as I saw belatedly what she had in mind.
With her lovely, creamy fingers, she deftly unbuttoned her straining top to expose her big, beautiful breasts.
“Here you are Chrissie, time for more nursing,” she smiled down on me.
“Uh-uh,” I shook my head, “I’m full,” I whimpered.
She shushed my pleading with her gorgeous smile even as she guided my face towards her left breast.
“Baby girls need looots of milk, Chrissie,” she told me as she unclasped the front of her lace bra, “And I’m going to make sure you get it.”
“Uh-uh,” I squealed but as usual, Barbara only ignored my protests and pushed her big, firm nipple past my lips. Even though my stomach was sloshing uncomfortably with milk, I began nursing by instinct, using my lips and tongue to suck the warm, familiar milk from Barbara’s bursting breast.
“That’s it, Sissy,” she smiled, “Baby doesn’t decide when to nurse–Mommy does.”
Looking up over the soft upper curve of her tremendous bosom, I looked into her pretty green eyes which glittered with firm, motherly love. And now that I was suckling from Barbara’s breast again, I felt my sexual desire starting to rise, if not my penis.
Barbara’s hand had shifted to the soft, cushiony front of my diaper and she was softly rubbing it now. I could hear the plastic crinkling under her touch and feel the wonderful sensations reaching me, even though my wiener was completely enclosed in it’s silicone cage. Closing my eyes, I drifted off into a world of pleasure as I luxuriated in Barbara’s delightful ministrations. As I continued to slowly nurse from her plump breast, she reached down and began unsnapping the side snaps one by one on my plastic panties. My heart skipped several beats as my mind began racing at the possibilities of what she had in mind, her beautiful smile washing over me like a warm bath and before long, I felt her unpinning the front of my diapers.
“Baby Chrissie needs her mommy, doesn’t she?” she whispered in her voice reserved for infants.
“Mm-hm,” I mewled as I sucked on her sweet, firm nipple.
She slowly pushed the front of my diaper down between my legs and began softly stroking my hairless balls in the most electrifying fashion imaginable.
“You know you’re always going to be my baby, don’t you Sugarplum?” she asked.
My heart was pounding in my chest as I looked up into those twin pools of emerald comfort. I nodded fervently back at her in reply.
“Now…real babies don’t get to have orgasms, you know that right, Chrissie?”
Huh? My head was swimming with desire and confusion. On one hand, her soft, slow caressing of my balls was driving me wild with sexual excitement. And as usual, the sight of her luscious, big breasts against my face had me already up against the edge of what would otherwise be a powerful orgasm. Her skin smelled wonderful and the silky smoothness of her bosom only added to her powerful attraction. But I felt a strong desire to be agreeable with her, in what I only now realized was a deep seated streak of submissiveness. Worse than that, my pounding, sexual excitement was pushing me against my will to agree with her terrifying premise.
Slowly, and contrary to my better judgement, I found myself nodding in agreement.
From behind her, I saw her reach over and when her hand came back into view, it was holding a small tube of superglue. She looked down at me with that warm, loving smile that said she’d never do anything to harm me.
“Now you know that I know what’s best for you, right Sweetie?” she murmured in her syrupy, sexy voice.
I paused, my heart thudding loudly in my chest, before slowly nodding.
Barbara bent down and kissed me tenderly on the forehead as her hand softly and sensuously stroked my excited balls. Inside my tube, my little penis throbbed violently against it’s implacable prison, fighting frantically for release.
“Sooo…” she began breathlessly, “I think it’s only for the best that I fill the keyhole of your chastity lock with this glue…what do you think, Chrissie?”
I could feel the cum building in my balls, waiting impatiently to explode in a massive ejaculation of climax. But by some perverse twist of biology, my own burning libido was encouraging me to go along with her. How could I say no to this beautiful woman I was in love with? My submissiveness was warring with my desire to achieve sexual release. I couldn’t think straight! And her sensuous massage of my balls wasn’t making it any easier!
Slowly and deliberately, Barbara pulled my puckering lips from her milky breast.
“Say ‘yes mommy’,” she smiled down at me.
“Oh–oh–bu–but,” I whimpered.
“Say ‘yes mommy’,” she repeated as she unscrewed the cap of the dreaded superglue.
“M–m–mommy,” I mewled weakly.
“Say ‘yes mommy’,” she said again as she leaned forward to bring her beautiful face closer to mine. Her rose colored lipstick shimmered in the soft light of my nursery and I felt my resolve crumbling.
I looked from the long line of her sexy cleavage, to the delicate lace cups of her bra, and then lastly, into her firm, pretty green eyes that were imploring me to agree to something that went against everything I knew.
“M–m–m…y-yes, Mommy,” I croaked in barely a whisper.
She smiled broadly and placed the thin nozzle of the tube of glue to the keyhole on the lock securing my chastity device. With a small squeeze, I watched in mute horror as the glue seeped into the lock effortlessly, quickly filling the tumblers and rendering them unable to open ever again. In seconds, I saw the glue glaze over the hole as it inexorably began to harden.
What had I done???
“Now you’ll be my baby girl forever, Chrissie,” she said as she gave me a warm, wet kiss right on the mouth.

The End

Josh’s New Home

It was a cold, grey day and the rain was coming down in sheets, heaping only further misery upon me as I trudged slowly and alone through the downpour.
Three weeks ago, I had been recently orphaned, due to a tragic car wreck involving both of my parents, and my arranged social worker recently set up living accommodations at my aunt’s house, some 80 miles from where I’d lived for the last twelve years of my life. It had been a trying ordeal for me and after the last horrific month of trying to cope with being without them, I was beginning to think that I could not possibly be more alone in the world.
Unfortunately, I had only spotty memories of my mom’s younger sister, Aunt Emily. The last time I had been there, I had only been five at the time and it had ended on a bad note for everyone involved. She seemed nice enough, and as I recalled, and she was quite pretty, or at least, she was at the time.
For some reason on that occasion—perhaps because there were no other toys around–I had found myself playing with a collection of Barbie dolls my Aunt had left in a room. She had come in unexpectedly while doing some laundry and discovered me on the floor but instead of teasing me, as I would have expected, she sat down and joined in as if it were perfectly natural. Things had continued quite pleasantly that afternoon until my dad came to pick me up to go home. To my shock and horror, my father was livid with what he called my “sissy” behavior and he let me know in no uncertain terms by pulling my pants down and spanking the daylights out of me. After that painful experience, I was absolutely forbidden to have anything to do with Aunt Emily and I had kept my word for the last seven years.
That traumatic episode, early in my impressionable young life, caused me to be all the more uncomfortable about going to live with Aunt Emily. Would she be wary of me now? Maybe she resented my moving in so unexpectedly? But I had nowhere else to go—there were simply no other relatives for me to turn to.
My shoulders trembled as I choked back a sob of self pity. The walk from the bus stop to Aunt Emily’s house had left me soaked and chilled and I was feeling little incentive to move in with my enigmatic aunt, a person who was still little more than a stranger to me.
The heavy suitcase I was carrying was beginning to hurt my arm so I set it down momentarily to shift it to the other side. As I did so, I pulled out the crumpled note the social worker had given me with Aunt Emily’s address written in the lady’s elegant cursive writing. As I smoothed it out to re-read it, the rain immediately began to make the ink start to run and I feared I’d lose the information forever. In my anxiety and panic, I burst into tears and scanned the nearby houses, searching desperately for the address while I could still make it out on the slowly disintegrating paper.
To my utter relief, I saw behind a nearby white picket fence, the five numbers that corresponded to the address I’d been given. Wiping my face of rain and tears, I re-shouldered my burden and went up the path to the large, ornate wooden door. A glazed window was next to the door but warm light was spilling out through it and it beckoned from inside, seeming to invite me to inquire further. With my heart in my throat, I knocked uncertainly and waited for what fate had in store for me.
Barely three seconds had passed when I heard the unmistakable crisp sound of heels steadily approaching from inside. I bit my lip nervously as the big door swung open to reveal my aunt standing before me.
“Joshy!!” she exclaimed with unrestrained affection.
Without waiting for a response, she bent down and threw her arms around me, locking me in a warm hug, filled with love and promise. Stopping only long enough to plant a wet, lipstick-covered kiss on my cheek, she pulled me inside and began immediately shedding the sopping wet clothes off my body.
It seemed like it had been a lifetime since I had seen my aunt but now that I was seeing her again, I was very pleasantly surprised. Aunt Emily was like an angel from heaven—tall, slim and pretty, with long sensuous legs that she showed off to great effect between her high heels and the snug skirt that clung to her curvy hips. Her long brunette hair spilled over soft shoulders but did nothing to hide the bountiful, plump bosom she could barely contain within the snug top that wrapped around her chest like a second skin. This was an aspect of my aunt I had apparently forgotten but I certainly wouldn’t forget it now, for as long as I lived!
For some reason, I had always had a strange fascination for big breasts, or at least since the time I had begun noticing the opposite sex during the last few years. And it seemed that well endowed, busty women struck a visceral nerve within me, on a level even I didn’t understand.
Now, as I gazed in bashful silence at my stunning aunt, I was captivated by her plump, sexy bosom, causing my little wiener to rise up in salute to this devastating creature before me.
“You are absolutely soaked!” she gushed in a voice that was like the playful notes of a happy song.
She removed my jacket and shoes and then began taking off my dripping socks as well. Leading me into an immaculate, tile covered bathroom, she continued undressing me even though I had thus far, been unable to utter a word!
Being shy by nature, I was quite unused to being around such a striking woman as aunt Emily, to say nothing of being undressed by her! Finally, I found my voice and I croaked out a greeting as best I could in a small, shaky voice.
“H-hi, Aunt Emily,” I said, a tentative smile coming to my face for the first time.
“Well hello, Honey-bunch!” she said gleefully as she gave my cheek an affectionate squeeze, “It’s been a long time, hasn’t it?”
I was relieved beyond words that my aunt seemed pleased to see me and my tension began slipping away like the wet clothes gathering in a pile at my feet.
“I was just about to take a bath when I heard you knock at the door, but you are obviously in greater need of it than I am—let me just get you out of these freezing clothes,” she explained.
The steam was rising visibly above the huge layer of bubbles that covered the surface of the tub but when my shirt was removed and my aunt began to unbutton my pants, I suddenly put my hands down to stop her.
“Oh…I-um, I can take it from here,” I stammered.
“Nonsense Silly,” she scolded me in a friendly tone, “I used to help change your diapers so you needn’t be concerned—I’ve seen every inch of your little body.”
I blushed hotly but I only vaguely remembered being around my aunt during my preschool years and I was reaching the age now where I was extremely self conscious of my body. The last thing I wanted was for my ravishing aunt to see my wiener, particularly since it was stubbornly refusing to go down!
Before I could say another word, Aunt Emily unzipped my pants and tugged them down my clammy, hairless legs, exposing my small erect penis within my clinging underwear.
“Oh my,” Aunt Emily said with amused surprise, barely suppressing a giggle, “looks like someone’s a little excited.”
My face turned beet red and I grabbed hold of the waistband of my underwear in an attempt to prevent any further undressing but my aunt was undeterred. Her hands were slim and beautifully manicured with long nails done in the French style of a model. She slapped my hands lightly and in my surprise, I jerked them away, just long enough for her to tug my damp underwear down my legs.
Now it was impossible to hide my erection and it stood proudly, if not insubstantially, since it was no more than an inch and a half in length, even by generous measurements. Aunt Emily giggled again but paid it no more attention as she led me into the tub where I gratefully sank into the mass of fragrant bubbles.
Taking a rose scented bar of soap, Aunt Emily began lathering it up and she started to rub it over my youthful body while she hummed a pleasant tune. I tried once to take it from her, but again, she merely pushed my meddling hand back down and resumed her ministrations as if I weren’t even there.
Washing me as if I were just an infant made me feel all the more helpless, and despite the fact my privates were now hidden, I still felt a sense of embarrassment.
“I can remember giving you a bath when you were just a baby—do you remember Joshy?” she asked sweetly.
I didn’t know why she insisted on calling me Joshy but I wasn’t prepared to make an issue of it so early in my new relationship with her. In any event, I was still too distracted by her loveliness and charm to think of arguing with her. In addition, it felt wonderful to have such a gorgeous woman using her soft, creamy hands to wash my sensitive skin. It tingled like electricity at her caressing touch and my erection certainly hadn’t gone down—if anything, it was raging even harder! I was gazing down between the two huge globes beneath her thin, stretching top as her slippery hand suddenly found itself down between my legs. She squeezed my boner briefly and then began slowly massaging it with the bar of soap, sending shivers of excitement down my spine. Breathing hard now, I stared up into her pretty brown eyes, while my own were glazed with lust and pent up energy. Between her stunning face and her massive, beautiful breasts, I couldn’t take anymore.
Suddenly, I experienced an earth shattering explosion of ecstasy unlike any I’d ever had in my entire life. My eyes crossed and I gasped for breath as I struggled to understand the wonderful feeling rippling through my body. Waves of pleasure washed over me and I went weak, the intense image of my delicious aunt swimming before me as my head rolled lazily.
Aunt Emily smiled warmly down at me, a look of understanding upon her gorgeous face.
“Looks like my little baby likes his bath,” she cooed softly.
I was still drooling foolishly as I slowly began to recover from my very first orgasm. If ever there was a case for love at first sight—this had to be it. I was utterly captivated by my sexy aunt and I knew I was going to be in heaven staying as her guest.


It had not been more than a week since I had settled into Aunt Emily’s wonderful home that I had made several observations.
First of all was the fact that I noticed a total absence of anything manly, anywhere in the house. On the other hand, feminine touches seemed to grace everything, from her bedroom, to the kitchen, and even to the living room with its soothing pastel colors.
But more than anything in the house was Aunt Emily herself. I had never met a more “girly-girl” than her. She had an air about her that was indescribable, yet always present. Her make-up was always flawless, emphasizing her devastating brown eyes with her long feminine lashes and her full, luscious lips that seemed ready to kiss me at any moment. I had come to savor those kisses, even if they were completely platonic.
She walked with a delicate, sashaying grace, especially in her high heels and her voice was of a musical quality that sent shivers down my spine. Her very femininity seemed to suck the manliness out of me, making me feel out of place in my new home.
But I also found myself gaping like an idiot at her lovely, mouth watering breasts on a regular basis. She seemed to be totally unaware that she was driving me insane with her tight blouses and low cut tops. Maybe it was because I was too young for her to think of me in that way. I certainly didn’t know much about women’s bodies and I wouldn’t have known what to do with their breasts even if they were made available, but they excited me anyway. I found myself masturbating furiously several times a day to try and get some kind of relief from the constant visual image of Aunt Emily that teased me on a daily basis. I had never met a woman like her in my life and she had me under an intoxicating hypnosis of sexual temptation.
The other thing I discovered was that Aunt Emily seemed to want to treat me as if I were still a little child. I didn’t mind, really, it just seemed a little eccentric though. It didn’t help that I was naturally short and Aunt Emily very tall, at least taller than any other woman I’d ever met. In her heels, she towered over me and I found myself staring at her prominent bosom which was usually at eye level for me. Several times, she had smiled down at me, placed a long nailed finger under my chin and raising it, forcing me to re-focus on her pretty face. ‘I’m up here, Sweety’, she’d tell me with a giggle and a knowing look. This only made me blush all the more, and I’d hope she wasn’t aware that my little wiener was getting stiff, yet again.
I still had a hard time holding eye contact with my aunt, primarily because I felt so intimidated by her. I had always felt that way about gorgeous women and Aunt Emily’s poise, confidence, and height, all conspired to make me feel like a helpless little boy, unworthy of her many kindnesses. I wanted desperately to please her in any way I could and I had unwittingly humiliated myself several times in my eagerness to do so. But Aunt Emily would always giggle good-naturedly when that happened and I would feel better afterwards.
My aunt seemed, for the most part, to be willing to give me free run of her entire home, a house which was substantially bigger than where I used to live. The one exception was a room at the end of the hall with a brightly painted pink door that had thus far, remained closed. My aunt had instructed me that it was off limits and because I was so infatuated with her, I respected her wishes, even though I was still very curious to know what was in it and why she wouldn’t grant me access.
I surmised that Aunt Emily had very sexy tastes in her more private clothes because I had discovered several catalogues lying around end tables in her living room. I found Victoria’s Secret, Frederick’s, and several others I’d never seen before. They excited me almost as much as my aunt, although I spent a considerable amount of my time imagining her in various states of undress, wearing the exciting underwear pictured in the catalogues. I had no idea what her bra size was but I figured it had to be incredible. This was a question that occupied my mind on a regular basis and every time I saw Aunt Emily, I found myself in a near constant state of arousal.
I also had a budding fetish with panties and besides enjoying seeing them on women, I secretly harbored a shameful fantasy of wearing them myself. I knew it was wrong but I couldn’t help myself and I often gazed at the pictures wondering what it would be like to wear a particularly frilly pair.
It was on one evening that I came across a catalogue I hadn’t seen before called Prissy’s Fashions, lying face down under some others, almost as if it had been deliberately hidden. Intrigued, I picked it up with unrestrained interest and began thumbing through it. Glancing over my shoulder, I verified that my aunt was still occupied in the kitchen preparing dinner, before devoting my full attention to the fascinating magazine.
Turning the pages, I found myself enraptured by some of the unique items they sold. In the first section, labeled Sissywear, I saw youths wearing articles of clothing that were clearly designed to look feminine and well, sissyish. My heart started thumping in my chest as I gazed breathlessly at the pretty panties they wore, hugging their round, firm young bottoms. I knew this went against everything my father had taught me, but the images made me rock hard and excited, striking a nerve I had tried many times before to deny.
So caught up was I in the catalogue before me, that I was completely unaware of the fact that Aunt Emily had walked out of the kitchen and was now standing behind me, observing me in silence.
Slowly, she bent over the back of the couch so she could practically whisper in my ear.
“Looks like my little boy likes panties, hmm?”
I was so surprised that the magazine fell out of my hand abruptly and I jerked around to face my aunt, red faced and ashamed.
“Oh no! No Aunt Emily—honest!” I blurted out, but my reddening face belied the truth.
My aunt smiled knowingly, her pretty eyes dancing with delight. With her usual grace, she walked around and sat down beside me, while I trembled with fear and mortal shame. As she settled next to me, her skirt rode upwards, exposing her smooth, firm thighs to the nervous boy next to her. A bead of sweat trickled down the side of my forehead as I contemplated what my stunning aunt would do to me.
“Joshy, are you a sissy?” she asked me softly.
‘N-no—no Ma’am,” I spluttered, hoping the added formality would placate her. I couldn’t face to look at her and my cheeks were burning red as it was, so I stared down at the floor in front of me, trying to ignore the expanse of smooth bare skin next to my own.
Aunt Emily smiled warmly and placed her slim, soft hand on my chin, turning me to face her.
“Joshy, are you a sissy?” she asked me again.
I could feel my cheeks blazing and I felt unable to resist this very adult woman’s intentions.
“N-no—Hon-honest!” I bleated.
“Its okay, Joshy,” she said, her voice lowering to almost a whisper, “I don’t mind if you want to wear panties.”
I was too ashamed to utter a word. I stared at the floor, clenching and unclenching my hands, wishing the couch would swallow me up and take me away from here.
Aunt Emily smiled and slowly reached down, unbuttoning the straining top button on her halter as if she were suddenly too hot. My gaze shifted as I tried to sneak a look down her top at the deep cleavage now even more exposed.
I had never seen this much of a real woman before and my heartbeat was racing like a panicked horse. The warm light of the fireplace cast deep shadows in the soft cleft between Aunt Emily’s tremendous boobs but I could still make out the clasp of her lacey white bra that was now partially visible. I could see that the fullness of her breasts were causing them to mash against one another and I gulped hard with excitement.
Reaching down, she picked up the catalogue and placed it on my lap, opening it back up to the page I had been looking at.
“Why don’t you show me which panties you like,” she softly suggested, her manner warm and comforting.
I was far too embarrassed to do any such thing and I tried to clear my throat, unable to speak coherently.
Sensing my intense embarrassment, Aunt Emily pointed out a pair of pink panties that were see-thru and decorated with frilly lace around the legs openings.
“How about these?” she asked softly, “Do you like them?”
I could feel my boner raging within my pants and I nodded my head even as I blushed further.
“Mm-hm,” she said, “and how about these?’ she asked, pointing out as pair of ruffled rhumba panties in baby blue.
I nodded again, wishing I could run away but also wishing I could reach down and stroke my poor throbbing peanut.
Aunt Emily flipped a page and seemed to be scanning the other choices available.
“These sure are cute,” she commented as she pointed her long, manicured nail at a pair of yellow flowered panties.
I merely nodded my head in silence, regretting that I didn’t have the courage to tell her that I loved them all.
“Well I think I’ll just order these and you can have all kinds of fun trying them on—what do you think of that?”
I was panting with excitement, both at the prospect of her suggestion, but also because I knew there was a strong possibility I might have to show my pretty aunt what they looked like on me. It was one thing to wear them in the privacy of my bedroom—something I’d only fantasized about until now—but to wear them in front of my aunt? The thought was too much for me to handle. My boner throbbed relentlessly in my pants, craving attention desperately.
With a smile, Aunt Emily hugged my face to her soft, plump bosom, patting my head reassuringly.
“Don’t you worry my little baby,” she whispered in his ear, “Aunt Emily’s going to take good care of you.”


Day by day, I found myself falling inexorably under Aunt Emily’s spell. She quickly had me under her thumb and I was finding myself unable to deny her anything. It might have been different if she weren’t so incredibly lovely, with a body that would make any grown man cry, but she was both of those and more. And she cunningly used her beauty and charms in a subtle strategy to begin molding me into a different person.
She continued to insist on bathing me like a baby, dismissing my protests by claiming that she just wanted to make sure I got “thoroughly” clean. She also instituted other changes to my living that seemed more appropriate for a child, rather than a budding man, which was how I pictured myself.
Aunt Emily insisted on an 8:30 pm bedtime and she enjoyed reading stories to me before turning out the lights. If anyone else had done that, I would have screamed bloody murder but it at least gave me an opportunity to stare uninhibited at her big, plump breasts while she was occupied with the book. After she had left my room and turned out the lights, I’d visualize her lingering image and eagerly masturbate until I had my nightly orgasm. At my youthful age, these amounted to no more than dry climaxes, with no real ejaculation, but that took nothing from the enjoyment I experienced. From time to time, I reflected that I was masturbating far more than I ever had at home, although under the present circumstances, I figured it seemed only reasonable. It also occurred to me that I might be acquiring some sort of addiction to wanking but the pleasure it provided always conveniently pushed that thought out of my head.
At some point, I had politely informed my aunt that I wanted to be called ‘Josh’ and not ‘Joshy’, but Aunt Emily only giggled and beeped my nose good-naturedly. An hour later she was calling me ‘Joshy’ again as if nothing had ever been said. Similarly, when I had asked for her to read me something a little more mature at bedtimes, she merely smiled and continued as before. It seemed that once she’d made up her mind about something, there was little I could do to dissuade her and I was increasingly getting the feeling that she saw me as no more than a four year old child.
Despite my differences with the way she was treating me, I was still having a wonderful time staying in her home. I might not get her to see my way about things but she was never mean to me.
Not long after I’d been there a few days, I had seen a long, rectangular wooden paddle hanging on the wall in the kitchen but I hadn’t given it too much thought. I knew it wasn’t a cheese serving tray because of the large holes cut in its surface. But Aunt Emily was far too nice to use something like that and anyway, I’d done everything she asked with only a little grumbling. It was pretty hard to imagine her using such a fearsome instrument for disciplining anyone, although if push came to shove, I was pretty sure who would win in a physical match and it wasn’t me.
I knew this for a fact when one weekend, we’d gotten into a play wrestling match. She’d quickly gotten me down on my back and pinned my arms on the ground beside my head. Happily, this had also resulted in a very close encounter with her big, soft breasts as she mashed them against my face while she kept me pinned. I had never been so close to cumming and I only barely avoided it when Aunt Emily suddenly decided to yank my pants down to embarrass me and show me who the victor was. I blushed beet red as my hard little penis was once again exposed to her attention. In her usual way, she just giggled at me and let me get up, but not before giving my rump a good slap just for the fun of it.
I had been embarrassed by the experience but also tremendously turned on and I immediately went into the bathroom to alleviate my pent up horniness. I could still recall the wonderful scent of her bosom as I sat there on the toilet, blissfully stroking myself as I masturbated to another earth-shattering orgasm.

I watched impatiently, day after day, for my panties to arrive in the mail. I couldn’t wait to actually wear the pretty, silky items under my regular clothes and I was especially looking forward to my nightly masturbation sessions in them. Unfortunately, I was far too ashamed to ask my aunt directly as to when they would arrive so I tried to do it in a oblique way, hoping she wouldn’t catch on to how important they were to me.
“Aunt Emily, did the mail come yet today?” I had asked once when I couldn’t find it on the table.
“Yes, Sweety—and no, your panties haven’t arrived yet.”
My face burned red as her giggle filled my ears and I hurried out of the room in embarrassment.
Other things were arriving as well; large and small boxes, and other things that Aunt Emily whisked away as soon as they arrived to take to her private room behind the pink door. It bothered me to no end that she had forbidden me from going in there and being the ever curious boy—I was desperate to find out what was inside.
One time, when I was walking past it, I paused outside and came close to putting my hand on the doorknob. As fate would have it, just then, Aunt Emily caught sight of me from down the hall and she gave me a brief frown of disapproval.
“Little boys that go in there get spanked,” she said simply, and I laughed nervously, trying to shrug it off as if it had been intended as a joke. However, as I wandered into my bedroom, I wasn’t so sure and I began to wonder if she were really serious. Would she spank me, if pushed? It was hard to imagine but I didn’t want to find out. The thought of having my pants pulled down and taken over her lap made me strongly reconsider opening that door. She was much taller than I was and I didn’t doubt for a minute she’d be able to hold me in place as she slapped my bare bottom repeatedly with that paddle. Nor did I want to be put in such a shameful position to receive such a childish punishment. Bent over her firm thighs, my own legs kicking wildly as she smacked my bare cheeks again and again, making me cry like a baby…I was determined to see that spankings were a thing of my distant past, particularly with my stunning aunt.
Still, the boxes and the room continued to haunt me. In those times where I’d been able to see the sending labels, I’d seen names like Babyland and Sissy World on them which made my heart flutter. What purpose could Aunt Emily possibly have for such items? I couldn’t imagine.
Finally, a week later, Aunt Emily came into my bedroom with a package in her hand and a smile on her face.
“Look what came in for my little boy,” she cooed musically.
I blushed and knew immediately that my panties had finally arrived. I was tremendously embarrassed but also extremely excited to see them first hand.
Aunt Emily unwrapped the package and carefully pulled out a pair of silky pink panties, lined with delicate lace and a three rows of soft ruffles across the seat.
“Oh—these are just adorable—aren’t they Joshy?” she asked with more enthusiasm than was necessary.
“Um-hm,” I mumbled under my breath. I had been rather hoping that she’d leave them on my bed and let me discover them in my own time but it was not to be.
“Why don’t you try these on,” she recommended excitedly.
“Um, okay…but, can I do it later?” I asked hesitantly.
“But I want to see them on you now, Joshy,” she countered, “Come on, lets get those shoes off.”
Before I knew it, she had sat me onto the bed and was untying my shoe laces.
“I-I can do it,” I tried to offer but she had my shoes off in no time and was already tugging my pants down. A moment later, I was sitting there, red-faced as Aunt Emily used her long nails to reach under the waistband of my underwear and pull them down my thighs. I grimaced as my tiny wiener came into view and I rushed to cover it with my hands.
Tossing my boy’s underwear haphazardly in the trash, Aunt Emily took the new pink panties and held them in front of my legs, beckoning me to step into them. Blushing furiously and making small sounds of weak protest, I gingerly placed my feet through the open leg holes to which Aunt Emily immediately pulled them up my thighs. I felt an electric sexual charge as the silky panties slide softly up my smooth legs. Aunt Emily was all smiles as she snugged them up my hips and positioned them around my waist. They clung wonderfully to my diminutive genitals, caressing my stiffening penis with a delicate embrace. Despite myself, I couldn’t prevent my erection from betraying my true feelings about the panties.
As Aunt Emily rose up to stand over me, she turned me around to look at my round, panty clad bottom. The panties were sheer so the crack of my fanny could clearly be seen through the material.
“Well,” Aunt Emily said with immense satisfaction, “looks like these fit you perfectly.”
I nodded in embarrassed silence, unable to look her in the eye.
With a casual stroke of her creamy hand over the fabric covering my straining erection, Aunt Emily smiled down at me.
“How do you like your new panties, Joshy?”
I was too ashamed to speak and I merely nodded as I looked away, hoping she’d leave me to get dressed by myself.
“Don’t you worry Joshy—this’ll be our little secret—okay?” she asked as she bent down to look me in the face.
I glanced into her pretty eyes only briefly before nodding my head vigorously and then looking away again.
Aunt Emily patted me on my bottom again and then left my bedroom, leaving me alone to savor my new and delightful gifts.

I enjoyed the panties thoroughly and I spent a good deal of my time, relishing their soft, silky feeling. And I would have been quite content to leave it at that, wearing them around the house but always under my regular pants, so that no one could tell. But one day, Aunt Emily accidentally spilled some spaghetti sauce on my jeans and at the time, the rest of my pants were in the washing machine being cleaned.
“Don’t worry Honey,” she quickly assured me, “You just take those off and we’ll throw them in the washing machine with the rest of your clothes.”
I wasn’t thrilled with the idea of removing my pants, and thus leaving myself exposed in my panties, but Aunt Emily was undeterred once again.
“Honestly Joshy,” she chided me, “it’s only the two of us and no one will ever see you in your cute panties.”
I was persuaded this time but a few days later, my aunt informed me that several of my pants had somehow been ripped up in the dryer, rendering them into little more than rags. I thought that was a little odd but I didn’t say anything about it. Also at about the same time, my supply of regular underwear seemed to be mysteriously dwindling. I had no idea where they had gone and I didn’t want to ask Aunt Emily since she always made such a big deal about keeping track and taking care of your things. I was afraid she’d accuse me of being careless and I didn’t want her to be angry with me. I wanted so badly to impress her with how much of a manly guy I was becoming and I was trying to get her to look at me as an equal, rather than just her young nephew.
But the end result was that I found himself more and more often wearing nothing but my panties and a t-shirt when I was hanging around the house. This was farther than I wanted to take my fetish and it was even worse after I’d masturbated. I discovered that I could suppress my shameful feelings about wearing girl’s panties while I was turned on but once I’d had my orgasm, my sense of manly responsibility came crashing down on me and I wanted nothing better than to tear off the humiliating undies and be a grown up guy again. This worked initially when I still had all my regular clothes but as time went on, I found myself having to go around the house more and more exposed. I asked Aunt Emily about getting some more clothes for me but she said we’d “just have to make due for the time being”.
One time, a week later, Aunt Emily suggested we play house together. This was another one of the activities that she enjoyed doing with me but to be honest, I was bored to tears by it—I just wanted to go outside and run and play with my friends. But Aunt Emily was insistent and she decided that for today, I would look good as her little girl. From somewhere, she produced a sissy looking top with puffed sleeves and a short hem that barely extended past my navel. It was pink with white lacey accents and I nearly threw a fit when she tried to put it on me. However, in the end, Aunt Emily managed to sweet talk me, assuring me that it would be our secret game and no one would ever find out. Between that heart stopping smile and her big, round breasts, I just couldn’t say no to her.
That day, I stayed inside, wearing only the sissy top, my rhumba panties and my sneakers. Aunt Emily was delighted with my appearance and she suggested we do some sewing as part of our activities.
Bringing out a needle and some thread, Aunt Emily sat me down at the table and gave me a piece of vinyl fabric to work with. Turning it over, I recognized it instantly as being a baby’s bib and I protested indignantly about it.
“Aww, Aunt Emily,” I whined, “don’t you have anything else I can sew?”
“Now Joshy,” she smiled, “this is going to be a very special bib for someone who is really close to me—I’m sure they’d be ever so happy if you were to put the finishing touches on it.”
The finishing touches consisted of putting a strip of eyelet lace around the lower edges of the infantile garment. I felt like an absolutely sissy, as I held the baby bib in my hands and careful began attaching the lace. I could only imagine what my friends would say if they were to see me now—dressed in a sissy top and rhumba panties, sewing a baby’s bib like a happy little girl. Worse yet, I was particularly horny this morning and Aunt Emily was wearing one of my favorite tops—a thin white halter edged with lace that hugged her magnificent chest in the most delightful way.
I kept sneaking peeks over at her as she hummed a song to herself, sitting across the table from me and sewing another piece of babywear. When we finished, Aunt Emily suggested we go out and sit by the pool since it was a beautiful day out. I was very apprehensive about it, even though her backyard was surrounded by a substantial wooden fence. Just the idea of being outside made me scared, given the girly clothes I was in at present.
Aunt Emily came over to my side of the table and bent over, giving me an outstanding view of her deep cleavage.
“C’mon Joshy,” she said sweetly, “there’s no way anyone can see us and it would be nice to get outside for a change.”
I licked my dry lips as I stared at the two huge melons pushed together in front of me. I could make out her nipples, poking through the fabric like two peas and my heart rate began accelerating faster. I wanted so badly to reach out and touch her soft skin but I would never dare to do something so bold. Predictably, my little wiener rose to the occasion and it strained mightily in its silky prison.
“Tell you what,” she said conspiratorially, “if you go out and wait for me, I’ll bring you out a surprise…”
I couldn’t imagine what it might be but I was so worked up by the sight of my delicious aunt that I couldn’t think clearly.
“O-okay,” I agreed shakily.
“Great!” she exclaimed as she clapped her hands together, “You go outside and I’ll be right there.”
I waited until my aunt had walked out of the room so she wouldn’t see the hard-on in my panties before I stood up and exited through the sliding glass door. I felt utterly exposed to be outside wearing such a sissyish ensemble but a part of me felt a tinge of mischievousness. It almost seemed like I were getting away with something totally forbidden and sense of naughtiness pervaded my being.
As I sat down on one of the pool chairs, I took a moment to re-picture my aunt in my mind and I stroked my little hard-on with boyish abandon. I was very close to cumming when I heard the sliding glass door open and I quickly assumed a pose of nonchalance and innocence.
But my casual look was quickly taken away when I saw what my aunt was wearing. As she gaily sauntered over to where I was sitting, I gaped open mouthed at her ravishing appearance.
She was wearing a light pink string bikini that covered precious little of her utterly flawless body. The small bottom piece below her washboard tummy covered her feminine patch and it tied on either side of her sexy, curvy hips. I was amazed at how tiny her waist was but what took my breath away and riveted my attention were her tremendous curvy breasts, jiggling heavily within the two pink triangles of her bikini top. I had never seen my aunt in so little clothes and I was completely speechless.
Aunt Emily smiled coyly at me, holding her hand behind her back which only made her big beautiful breasts stand out even more prominently.
“Look what I have for you,” she said in a playful, sing-song voice as she brought her hand out from behind her.
I took my eyes off her magnificent chest long enough to see a new pair of yellow colored ruffled panties in her hand. A single pink flower adorned the front of the waistband and along with the see-thru shimmery fabric, it screamed out little girl, making me feel the thunder of my heart in my chest.
“Stand up Joshy,” she invited me, “Let’s see how these look on you.”
My eyes clouded with lust, I tried to stand up so my raging erection wouldn’t be seen by my aunt but it was quite impossible. She giggled as she looked down upon it but she didn’t say anything further as she held the new pair of panties open for me to step into. My face reddened but I quickly jerked my own panties down and threw them on the grass next to me. I had to steady myself on Aunt Emily’s shoulders as I lifted first one leg and then the other to get into the new panties. Even as I did, I stared down at my aunt’s awe inspiring breasts that were stretching her bikini top to its limits. My boner was so hard that it hurt and I found myself panting from the excitement. With excruciating slowness, Aunt Emily carefully pulled the panties up my slim legs, past my knees and up my hairless thighs. All the time, my eyes were glued to my aunt’s big succulent bosom, taking in every detail from my wonderful vantage point. As she pulled the soft, silky panties over my hips, her sexy breasts came right up to my face, no more than two inches away.
I couldn’t take it any longer. As the girlish panties caressed my hard little peanut, I gasped and came with a groan that escaped from my lips. So intense was my orgasm that I could barely stand and I wavered in front of Aunt Emily, my eyes rolling around in my head. Aunt Emily was smiling down at me until her gaze fell down to my crotch. Still in a foggy haze, I lazily looked down to see what she was looking at.
“Oh my!” she said, a new look of shock and concern appearing on her face.
I was certainly dazed and confused but when I looked at my crotch, I saw there was now an obvious wet spot in front.
“Oh my,” Aunt Emily repeated and she carefully sat me back down on the pool chair.
“You sit right there, Joshy—I’ll take care of this right away—I have just the thing.”
I was confused but I was also lingering in the pleasant afterglow of my mind-numbing orgasm. Presumably, my aunt had gone off to get a tissue to help me clean up the mess. I relaxed and reflected on what bliss my busty aunt had given me.
She returned quickly and she had a small white box in her hand, the size of a jewelry box. Kneeling down next to me, I caught the inscription on its face that said CB-6000s, whatever that meant. Still oblivious, I sat with curiosity as Aunt Emily opened the box and began taking out several clear pieces made of hard plastic.
“Don’t you worry Joshy; this will take care of that little problem just perfectly.”
I didn’t know how this thing that resembled a puzzle was supposed to clean me up but I remained silent and watched in bemused silence as my aunt busied herself opening a large rounded split ring. Taking down my sticky panties, Aunt Emily used them to wipe away any excess semen (which wasn’t much) and then set them down beside her.
“Spread your legs Joshy,” she instructed me.
As I happily complied, my aunt took the ring and placed it behind my little balls, circling it around so it was flush against my body.
“This is the smallest ring they supplied so I hope it’ll fit,” she said, half to herself.
Holding the molded ring together, Aunt Emily fitted the pin from the back side that prevented the ring from being opened and she placed a small spacer over the end of the pin. I was enjoying having my buxom aunt manipulating my genitals and I happily watched her as I continued to steal looks at her big round breasts. If only she knew how I was taking advantage of her, I was sure she’d be plenty angry.
“It looks like you’re a premature ejaculator, Joshy. I know those are big words but don’t worry; this will really help you with your little problem,” she told me.
With the cuff ring in place behind my sack, Aunt Emily took a clear, cock shaped tube with three small holes at its base and carefully placed my tiny flaccid penis inside. Then she mated the pins on the cuff ring with the tube and closed them up so that the first pin protruded only about 1/4 of an inch out the front. Seeing she had a good fit, she took a small master lock from the box and slipped the hasp through the exposed hole at the end of the pin. With an audible click, she closed the lock shut and sat back to observe her handiwork.
“There. You’re all set,” she said happily, “That’ll keep your little pee-pee safely locked up and it’ll also prevent you from being able to get any more erections,” she explained to me while I was only now starting to fathom what was taking place.
“Wha-what’s happening?” I stuttered uncertainly.
“This is a CB-6000s chastity device, Joshy. It’ll help you to control your urges so you won’t have any more accidents like what just happened.”
My mouth hung open as I stared down at my now imprisoned penis. Still in shock, I reached down and tried to pull the device off but the cuff ring prevented me from being able to remove it. Seeing that there was no way I could pull it off, I started to try and extract my limp penis but I couldn’t get a hold of enough of it to get it out.
“Oh, I wouldn’t bother trying that, Joshy,” Aunt Emily advised me, “These are quite escape proof, even for young boys with little penises like yours.”
“B-but—ho-how will I be able to pee?” I asked quizzically.
Red flags and alarm bells were going off in my head as I began to understand just what this would mean.
“Don’t worry about that—that’s why there’s a slot at the bottom of the tube, to allow you to pee without removing the device. However, you’ll probably find that you’ll have to sit down like a girl to use the toilet now, due to the angle of the wee-wee tube—that is, until we make other arrangements,” she giggled.
I was still too shocked to pick up on my aunt’s enigmatic reference as I pondered what it would be like being unable to stroke my cock anymore.
“B-but how long…how long will I have to wear this?” I asked nervously.
“Oh, I think until you’re about 18 should be okay. Then we can think about whether to let you out or leave it on longer.”
I didn’t know what to say and I stared at her with my mouth open as she calmly gathered the items on the ground together and stood up to take them inside. The idea of doing without masturbation was beyond imagining for me and I knew right then and there I’d have to find some way to defeat this devilish device. It would be my quest and I promised myself I wouldn’t stop until I had figured a way out of the implacable contraption.


I never realized just how much I’d been masturbating until the option was forever taken away from me by Aunt Emily. She was right that I could continue to go pee without any difficulty but I was no longer able to touch my penis in any way and it was driving me crazy. Nor could I manipulate the tube to try and induce enough friction to achieve an orgasm. At best, all I could do was to get myself excited which only made me more frustrated.
My situation was made worse by my aunt who thought nothing of walking around the house in her skimpy clothes. Now that summer was in full swing and the temperatures were getting hotter, she’d often be doing her housework in nothing but a short pair of shorts and her tiny bikini top. I’d gaze at her in utter frustration, going out of my mind with lust as I stared at her mouthwatering curves. She seemed to be totally oblivious of my situation and she’d think nothing of standing there, her big boobs staring me in the face as she explained some detail or another about a subject that I wasn’t listening to. My little peanut strained miserably in its hard plastic prison, unable to attain an erection which by now, was more often than not in my pretty panties. Only thing was, I could no longer feel the soft fabric caressing my penis anymore. I could still feel it rub and stroke my balls but that only added to my sense of frustration.
Countless times, I tried rubbing my balls, hoping it would cause me to cum but I only succeeded in getting myself even more worked up than before with nothing to show for it. After several days of this, I was sure I wouldn’t be able to take it for another week but I had no idea how I could approach Aunt Emily to take it off. It was obvious she didn’t want me playing with myself and I knew she’d never agree to remove the chastity device simply to let me relieve my ever present horniness.
I tried desperately to think of something else and sometimes that would work for a while, but Aunt Emily would always foil my efforts in the end. For instance, I might be sitting on the floor of my bedroom playing with my toys when she’d come in and bend over to talk to me. Her massive breasts would hang there, barely contained in her skin tight top, tempting me with their fantastic size and shape and my little penis would expand painfully in its prison until I groaned with discomfort. I found myself worshipping her and hating her at the same time. I was so confused!
One day, a week later, I couldn’t find one of my shoes and I searched everywhere in vain, unable to locate it. I had no idea how I could have lost it but after looking all over the house, I finally gave up and went to tell Aunt Emily. I found her, sitting in her bedroom on the bed and going over some bills. She was wearing a short skirt and a wrap around top that revealed every delicious curve of her huge, round breasts. I gulped and swallowed hard as my peanut began its inevitable rise to futility.
“A-Aunt Emily?” I asked hesitantly.
Oblivious of my lustful frustration, she looked up from her work and beamed warmly at me.
“What is it, Sweety?” she asked pleasantly.
The light of her bedroom lamp was shining off the soft plump skin at the top of her exposed bosom, making my mouth suddenly dry.
“Um, I-I can’t find one of my shoes,” I said, trying to will myself, not to be distracted by her fabulous body.
“Don’t you have another pair, Joshy?” she asked, although something told me she already knew the answer.
“No, I only had the one pair when I got here,” I explained.
Aunt Emily nodded her pretty head and looked thoughtfully at me for a moment.
“I think I have something you can wear,” she said suddenly.
Going to her large walk-in closet, she bent down, giving me an outstanding view of her firm, pert behind. I could see every outline of her sexy panties as they hugged her perfect derriere. When she stood back up, she was holding a pair of white girl’s Ked’s shoes.
“I think these might fit you,” she offered.
They looked very sissyish to me and I was reluctant to accept them but I didn’t know what choice I had.
“Don’t you have anything else?” I complained.
“I’m sorry Sweety, but I don’t,” she replied sympathetically.
I sighed and put the shoes on but I felt like a little girl wearing such prissy footwear.
“They make me look like a sissy,” I whined.
“Aww, now don’t you worry, Honey,” she said trying to console me, “No one will see you and anyways, I think they look just fine.”
I wasn’t convinced but I didn’t see what else to do.
“Okay,” I said, although I wasn’t too happy about the situation, “but can we get some new shoes for me soon?”
“We’ll see,” she said as she returned to her bills although I’d learned by now that that response pretty much meant no to whatever I was asking for.
Looking one more time at my reflection in the mirror, I was struck by how much I looked like a little girl. My hair was growing longer and with my exposed pink panties and white Ked’s, I was really starting to look just like a little schoolgirl. I blushed and hurried out of her bedroom to escape my embarrassing image.

A week later, Aunt Emily succeeded once more in convincing me to dress up in a sissy outfit that had me cringing uncomfortably with embarrassment. I was wearing my sheer yellow panties again, but this time she wanted me to try out a lacey white top with pink accents. She said it meant a lot to her to see me wearing it because it used to belong to a niece she hadn’t seen for ten years. I was a little surprised by that because it looked to me like it was brand new. However, she insisted I was mistaken and she explained its condition by saying it had been carefully stored over the years.
In any event, the short, puffy sleeves and Peter Pan bib-type collar gave it a decidedly infantile, girlish look, and it only came down to just cover my navel. On the chest was an appliqué of a pink bunny surrounded by building blocks with letters on them. There was plenty of eyelet lace around the edges of the garment, including the frilly hem that I kept trying in vain to pull down. Aunt Emily just giggled and playfully squeezed my buns through the thin fabric of my panties making me feel like a total sissy.
She also told me she had some special socks she wanted me to try, saying that I was “just going to love them”. They turned out to be delicate white anklets with three rows of yellow lace circumnavigating their short tops. Over those, she added my now compulsory white Ked’s sneakers which completed my look, or least, I thought it did until she took me into her bedroom to sit me at her vanity.
“I’m going to make you look very special today, Joshy,” she said excitedly as she began brushing my longish hair into two pigtails. She placed a big pink floppy bow on each side and then bent down behind me to share my reflection in the mirror.
“You really do look so sweet, Joshy,” she cooed.
I was squirming uncomfortably, not the least of which was because Aunt Emily was displaying a lot of cleavage due to the plunging scoop-necked top she was wearing. I could see a lot of soft skin and the twin mounds of her bosom was driving me crazy, as usual.
Suddenly, seemingly as an afterthought, she reached over and picked up her perfume bottle. Before I could react, she sprayed me several times with it, giggling with amusement at my discomfort.
“Hey!” I cried out.
Now, I smelled as girly as I looked and I looked very girly!
“That’s a little thing called Little Missy,” she giggled.
“I don’t want to do this anymore,” I whined in an upset tone.
“Wait Joshy—I bought you a little gift,” she said as she turned around to get something. Spinning back around, she handed me a glittery pink purse with Hannah Montana and several stars adorning its sides. It looked like it was made for a five year-old girl to put her faux make-up in and I had no idea what she wanted me to do with it. I stared back at her sheepishly but she beamed down at me like it was a gift I’d been waiting all my life for.
“It’s just for today, Joshy,” she explained, “I just thought it would go really cute with your outfit.”
“But I don’t wanna dress like a girl,” I complained.
“Oh, but you make just the cutest little thing, Joshy,” she gushed enthusiastically. She placed the purse on my arm and then stood me up, squeezing my bottom affectionately which only made my penis try and get hard all over again.
I was very confused, having various different conflicting feelings coursing through me at the same time. On one hand, I was tremendously embarrassed by my sissyish outfit and wanted nothing better than to rip them off. On the other hand, being in such close proximity to my aunt was also making me incredibly horny, a fact that was exacerbated by the fact I hadn’t been able to masturbate for over a week.
I guess there was no harm in playing along with her, I reasoned, considering how important it seemed to be to her. And truth be told, I was completely powerless to deny her anything when she smiled at me like she was doing now. My heart would always skip a beat and I somehow forgot for the moment that I looked just like a girl out of kindergarten.
Obviously pleased that she had convinced me, she informed me it was lunch time and that we would be enjoying it outside on the patio, since the sun was out and warm. As usual, I was a little nervous about going outside like this, but then, I remembered last time we were outside and everything had turned out fine.
We headed out of the bedroom together but then my aunt stopped me in the living room.
“Can you skip, Joshy?” she asked me suddenly.
“Huh?” I asked, momentarily confused.
“Sure—you know, skip along like this–”
Aunt Emily demonstrated for me what she had in mind, skipping her way toward the sliding glass door, before turning to face me. For some reason, she looked so utterly hot—looking as if she were nothing but a happy little girl–and her ravishing face was devastatingly beautiful.
Oh well, I guess I could play that game too.
Swinging my arms, I skipped along quite gaily, as if I didn’t have a care in the world. Aunt Emily opened the door for me and I skipped right out and onto the patio—where I stared open-mouthed at four of her girlfriends sitting around the pool table!
They turned as one to face me and they burst into smiles and then open laughter. In an instant, my face blushed beet red as I stopped dead in my tracks at this unexpected audience.
“Hi Joshy!” one of them cried in a delighted voice.
“Come here, little Sweety!” called another.
I took a step backward in a panic and nearly wet myself as I tried to deal with the magnitude of my humiliation, but I backed right into Aunt Emily.
“Its okay, Joshy, these are just a few of my friends,” she told me, as if nothing were out of the ordinary.
“This is Lauren, Vanessa, Jessica, and Jennifer,” she said as she gestured to each one of her cute friends.
Despite my smoldering shame, I could acknowledge–if only to myself–that Aunt Emily’s friends were hot in every sense. All of them were good looking, slim, and in great shape, wearing clothes that showed off their fabulous bodies to good effect.
I could see that Jennifer was wearing a snug workout outfit that clung to her firm body and she struck me as very athletic. The two in the middle, Vanessa and Jessica, were wearing shorts and halters but their friend Lauren was the one who really caught my eye. She was wearing thin white shorts that hugged her sexy hips and a flimsy see-thru cover up that did nothing to hide her incredible bosom. I could plainly see her big, bountiful breasts, barely restrained by a neon yellow bikini top that pushed them up and together into a glorious display of erotic female curvature. She was definitely all woman, and her intent stare at me only made me feel like more of an effeminate sissy.
“Come here, Joshy, and sit on my lap,” she beckoned to me.
I bite my lip in angst as I stared back at the four of them.
“Go ahead Joshy,” my aunt encouraged me, “she won’t bite.”
“I don’t know…” Lauren added with a giggle, “This little sweetie looks good enough to eat!”
My face was blazing like a five alarm fire as these babes enjoyed teasing me about my state of dress.
“What a cute purse you have, Joshy,” Jessica said in a condescending voice, “Is that where you put your make-up, Sissykins?”
I shook my head no as the blood sang in my ears.
“What on earth is that you’ve got in your panties?” Vanessa asked abruptly as she pointed at my crotch.
My CB-6000s could be easily seen through the sheer yellow fabric of my panties and I suddenly tried to cover the embarrassing device with both my hands.
However, Aunt Emily gently pulled my hands behind me and prompted me to walk closer so everyone could get a closer look. Holding my hands together with one of hers, she used her free hand to pull my panties down in front, showing the fascinated women exactly what it was I was wearing.
“Joshy’s been starting to get erections, I’m afraid to say. But I wasn’t too concerned about it until the other day, when he had a little, um—accident, in his panties,” she explained patiently.
“Accident?” Jessica asked puzzled.
“Mm-hm…Joshy, would you like to explain it to the ladies?” my aunt asked me in a soft voice.
My ears and chest reddened to match the crimson color of my face but I shook my head adamantly.
“Well…the poor little thing seems to be a premature ejaculator and he simply lost control, making a nasty mess in his panties–isn’t that right Joshy?” she said, patting me sympathetically on the head.
It sounded to me like she were describing a four year-old, not a budding teenager.
“Sounds like this little sissy needs to be put back into diapers,” Vanessa observed disdainfully.
“Oh, he wil–” my aunt stopped herself in mid-sentence and let out a giggle that seemed to be covering up for her slip of the tongue, “I mean, we’ve got that all taken care of now—haven’t we Joshy?”
Bending down to look me in the face from the side, my aunt was prompting me to agree with her but I couldn’t take anymore of this kind of attention. I abruptly wrenched my hands free and stormed off into the house, determined to tear up all the embarrassing sissy clothes I was wearing. Going through the living room, I threw the pink purse on the couch and ran into my bedroom, slamming the door behind me in an angry huff.
My face was still burning with shame and when I noticed my reflection in the full length mirror in my room, I nearly burst into tears. How would I ever live this down? How had I gotten myself into such a humiliating situation?
Looking at myself, I looked like a five year-old girl about to cry her little eyes out. My lower lip trembled and I fought the urge with all my twelve tears of experience, even as my vision became blurry with tears.
I was just about to strip off my top when the door suddenly opened and Aunt Emily’s friend Lauren strode into the room like she owned it. I was a little intimidated by her since she was much taller than I was and obviously, a lot older. For some reason, her big breasts also added to her very adult persona and I hesitated uncertainly before her.
She beamed down at me and shook her pretty head sympathetically.
“There-there,” she said as she swept over and hugged me to her soft, cushiony chest, “no one meant to hurt you Baby.”
I wanted to speak but a tear trickled down my cheek and my throat was choked with emotion.
“I-I was so–” I sobbed as my shoulders shook uncontrollably.
She stroked my head affectionately as I nuzzled blissfully against her exciting bosom.
Slowly, Lauren led me gently over to the bed where she sat down on it, taking me carefully and positioning me up onto her lap.
“Hey…shhh,” she whispered in a warm, consoling voice, “there, there…don’t cry, Joshy.”
Even though she seemed to mean well, her words and childish treatment of me only made me feel even more like a baby and another set of tears tumbled down my face before I could stop them. I was tired of people treating me like a girl and a sissy and no one wanted to give me the respect of the young man that I knew I was.
“Don’t be so sad, Joshy…” she comforted me, “You’re a cute little boy, you know.”
I sniffled and felt a least a little better about that remark. I liked the idea of her thinking of me as cute although I took issue with the ‘little boy’ part. I was almost a teenager, for crying out loud!
“How about if I gave you a little kiss—hmm?” she offered in a sweet voice.
I looked at her uncertainly, my face wet with tears as I sat in her lap like a child. She was very pretty and her full, luscious lips shined with a glossy, wine colored lipstick. Without a doubt, she was drop-dead gorgeous and I wasn’t about to turn her down.
Without waiting for an answer, she leaned forward and, closing her eyes briefly, kissing me gently on the lips.
Wow!! I couldn’t believe it! My first kiss and it was with a real knock-out!
My head was spinning and I felt that familiar pain starting to grow in my crotch as my wiener struggled to grow harder.
“You know,” she began, “you missed out on a nice lunch your aunt had planned for everyone. But don’t you worry, I’ve got something even better that I think you’ll like,” she said eagerly in that soft, conspiratorial voice of hers.
I was still staring at her enticing lips when she began stroking the plump mounds of her big breasts, caressing them with her sexy manicured hands. This was really something for me to watch and my heart skipped a beat as it raced into full speed ahead.
She slid me off her lap and then onto the bed face up so that I was now positioned directly in front of her massive bosom which was tightly stretching the fabric of her bikini top in the most erotic way.
“It just so happens that I’m lactating so I can promise you a nice full meal, Joshy,” she said, her voice getting thick with desire.
I was starting to get an idea where this was heading and suddenly I grew nervous, feeling like I was in over my head. At my age, I liked the idea of kissing girls and maybe an experimental fondle here and there, but I was totally unprepared for anything more. I swallowed hard as Lauren slowly unclipped the front of her straining bikini, releasing her huge melons from their smooth cups. I stared dumbfounded as she cupped the left one and brought it forward to position it before my face. I’d never seen a woman’s nipple in my life and here was one right in front of my face! It stuck out, about the thickness of my finger and I saw the tiny hole in which liquid was already seeping out.
“N-no, please–” I stammered, “I-I’m-not sure I–”
“Shhhhh,” she shushed me, “this is just what my little baby needs.”
“Uh-uh,” I bleated and I shook my head no, trying to dissuade her but she only smiled down at me undaunted. Taking her big firm nipple between her slim finger and thumb, she gently squeezed it and I watched in awe as a small dribble of breast milk leaked out.
“Open up, Sissykins,” she insisted with a big smile.
I struggled on her lap but she put her other hand behind my head and forced me to face her gigantic breast.
“No—p-please!” I whined pathetically but she only smiled and brought my head up to meet her nipple. I felt my lips brush against it and she rubbed it across from side to side, working it slowly inside.
“Take it in, baby Joshy,” she whispered softly.
With a sob of defeat, my mouth opened and her big nipple quickly filled my mouth. Instinctively, I began submissively nursing and I was quickly rewarded with a steady stream of warm, odd tasting milk.
“That’s a good boy…that’s my little baby,” she cooed softly to me.
I whimpered helplessly as I sucked like an infant from her tremendous, milk laden breast, feeling more babyish than ever.
Lauren’s hand shifted to pat my panty clad bottom in a soft, maternal gesture.
“You know, Vanessa was right,” she said, practically in a whisper, “I think you do belong in diapers and plastic panties.”
I tried to shake my head in disagreement but Lauren wouldn’t allow it.
“You just keep nursing, Baby,” she told me, “I’ll tell you when you’ve finished,” she said firmly.
Not wanting to cross her, I did as I was told, closing my eyes as I sucked mouthful after mouthful of warm breast milk. I was so absorbed by what I was doing that I failed to notice when Aunt Emily came into the room, unannounced.
“I think your baby here is going to need to be put into diapers before you lay him down for his nap,” Lauren said with a big smile.
I opened my eyes to see my aunt gazing down at me, my mouth full of Lauren’s plump boob, sucking like a newborn infant.
“Well, if I had known my little sissy was a breast feeder, I would have put him into diapers a long time ago,” Aunt Emily remarked.
I mewled in protest but Lauren was making sure I couldn’t pull away from her massive breast.
“I came in here and the poor little sissy was crying his eyes out,” Lauren explained, “The only way I could get him to stop blubbering was to offer him some mother’s milk, straight from the source.”
“Is that so?” Aunt Emily mused.
“Oh yes, he really is a needy little child, but giving him a nipple to nurse from seemed to calm him down right away—isn’t that right, Sugarplum,” she said in a mocking voice used with toddlers.
I tried to shake my head no but Lauren was gripping my neck firmly from behind and I squealed ineffectually with my mouth full.
“Joshy, why didn’t you tell me you were still breast feeding? Were you too embarrassed?” Aunt Emily asked innocently.
I tried to speak to counter Lauren’s lies but I was hopelessly gagged.
“Don’t you worry, Honey, we’ll take care of all your little baby needs,” she said confidently, “From now on, you’ll be my little sweet toddler, and I’ll make sure you get all the breast milk you can handle. Fortunately for you, I’ve also got plenty of diapers and baby clothes that I know you’ll absolutely adore!”
Suddenly, I felt like I was falling slowly down a mine shaft, unable to stop my fall. Somehow, I knew intuitively that my aunt had plans to take my emasculation process further by treating me like a baby and I knew I had to stop her, and stop her right now!
I jerked my head away from Lauren’s breast and stumbled up awkwardly from the bed.
“No!” I shouted, “I’m not going to wear diapers and baby clothes!”
My aunt looked mildly surprised but not shocked as she crossed her slim arms over her big breasts.
“I’m tired of being treated like a girl and a sissy!” I continued my tirade, “From now on, I’m going to wear what I want to wear.”
For a moment, a tense silence filled the room with none of us speaking.
“All finished?” Aunt Emily asked curtly, an icy tone putting an edge to her voice, “Are you done with your little temper tantrum?”
Still simmering, I nodded sulkily but I looked away, unsure of just what I’d done.
“Good, because you’re coming with me, Little Boy,” she said and she reached down to snatch my wrist.
“Wha-where are we g-going?” I asked as she jerked me out unceremoniously into the hallway and down toward the bedrooms.
“I know you’ve just been dying to see what’s behind this door so now you’re going to find out,” she replied, her voice filled with determination, “Oh yes, you’ve had this coming and now you’re going to get it in spades.”
I pouted and whimpered as she opened the forbidden pink door and pulled me inside. As she flipped on the light, I saw a baby’s nursery that looked like it had been decorated for a toddler girl. Pink and white wallpaper patterned with playing animals covered the walls and a large crib dominated the room. Frilly pink curtains softened the sunlight coming into the room and a dresser, also in pink, stood next to the crib. On the floor was a low changing table, its padded surface covered with nursery print vinyl plastic and next to it were tall stacks of thick cloth diapers.
My stomach buzzed nervously as I took all this in but I didn’t have time to absorb it all before I saw Aunt Emily reach for a stout wooden paddle much like the one in the kitchen.
“I-I I didn’t mean to–” I babbled nonsensically.
I gulped in fear as she lowered the crib bars on one side and took a seat on the waterproof sheeted mattress.
“Its time for you to learn a little lesson in manners,” she said evenly as she pulled me over to her side. Wearing only my panties and the sissy top, I felt naked and defenseless as I trembled before her.
“No-no–” I stammered weakly as she wrestled me over her bare lap.
I fell face forward and found myself staring at a diapered yellow teddy bear on the floor in front of me.
“Wait! Please! I’ll be good—honest!” I pleaded.
Aunt Emily moved her high-heeled feet slightly apart and rubbed the smooth paddle against my pantied bottom as I whimpered fearfully.
“Its time you learned who makes the rules in this house, Young Man,” she lectured me, “You need to learn that I know what’s best for you and if that means putting you back in diapers, that’s what’s going to happen.”
“P-please Aunt Emily, please don’t sp-spank me,” I wailed piteously.
Ignoring my whining, she raised the paddle high up over her head and then brought it swooping down, to land with a deafening SMACK!! across both of my unprotected cheeks. I howled out and kicked my feet, just in time for her to grip my torso to hold me securely in place and prevent my escape.
“We both know you’re a little sissy who belongs in diapers and plastic pants and that’s just what you’ll wear from now on.”
The paddle seared itself with a terrifying impact, flattening my round, youthful cheeks with impunity before they bounced back up in place, ready for another blistering swat. I immediately burst into tears, acutely aware that the door was open and everyone outside would be able to hear me. Here I was, a twelve year-old guy, being given a spanking over my aunt’s lap like an errant child and told that I’d have to wear diapers from now on. It was mortifying!
“You may have thought you were coming here to be able to wear panties but clearly, diapers are more appropriate for you.”
She delivered two stinging, punishing swats to each cheek.
“You’ll wear what I tell you and do it without question—do I make myself clear?”
Before I could reply, the hard wooden paddle came swooping down again, slapping my frilly pantied cheeks with angry, fierce determination.
Suddenly, I felt her long fingernail reach inside the waistband of my prissy undies and jerk them downwards, to frame my soft, bare buns for more of her harsh discipline.
I was sobbing like a baby as the paddle rained down again and again, slapping my exposed bottom with a terrible vengeance. I kicked frantically and pounded my bunched fists on the floor, wailing at the top of my lungs in anguish.
Being made of hard oak, the wooden paddle was uncompromising as it blistered my tender, round cheeks mercilessly. The hard, crisp swats filled the room like thunderclaps, mixed with the continuous sound of my crying unashamedly. There could be no mistaking the sound of a naughty little boy getting his bottom spanked, and spanked hard.
Lauren was avidly watching my punishment closely and a small smile had formed on her cute face, showing her obvious satisfaction at what was taking place. Occasionally, she’d nod in agreement as a particularly harsh slap caused me to buck and cry out louder.
I couldn’t believe how hard my aunt could spank and if her arm was tiring, she certainly didn’t show it. She was determined to teach me a lesson and my bottom was getting its full measure and then some.
At long last, my aunt stopped spanking me and she began rubbing my blazing, throbbing cheeks again with her paddle.
“Is baby Joshy ready to be put into his diapers?” she asked innocently.
I was too busy blubbering to make a coherent reply so I nodded my head and said the closest thing I could articulate to a yes.
“I didn’t hear you Joshy…are you ready to be a good little baby now?”
I cried out in pain and anguish, another set of fresh tears spilling down my face.
“Y-y-yes Ma’am!” I cried miserably.
“Good. That’s mommy’s little baby,” she said, apparently satisfied.
Setting the dreaded paddle on the crib mattress next to her, she reached down and helped me to stand, although I was a total wreck and I wavered before her on unsteady feet. I was too ashamed to look at her directly and I stared at the floor instead, crying openly like a little child. Being disciplined by my beautiful aunt was more than I could stand and I was mortified beyond belief. All my dreams and aspirations of being considered as an equal had gone up in a poof of smoke. All along, I had been fooling myself, believing that I was an adult on par with her. She had clearly established her absolute authority in the house and I felt chastened and defeated.
Aunt Emily took me in her arms and began patting me on the back, saying soft, soothing things in my ear.
“There, there Baby…it’s all over now,” she told me in her usual sultry voice, “Your spanking’s finished and everything’s going to be okay Sweety.”
I sobbed uncontrollably and my tears fell from my cheek to drop down onto her bare back.
“There, there Joshy,” she said cradling my head, “Shushhh….shush now. Mommy’s going to make everything all better.”
I wasn’t sure what to make of her assurances but I certainly wanted to be in her good graces again. I hugged her tightly and I could feel her big soft breasts pressing against my own chest. She waited a little while longer for my sobbing to subside before she began again.
“Joshy? Mommy needs to put you into your diapers now…but don’t worry Honey—I’ll make sure you have the cutest plastic panties on so you don’t have to be concerned about that—okay?”
Her voice was one of soothing comfort and I felt a strong sense of protection from her, like she was going to protect me from the rest of the world.
Gently, she pulled me away from her embrace and stood me before her, using her finger under my chin to make me look her in the eyes. Tears were still spilling down my cheeks and I had to wipe the goo dribbling from my nose.
“Joshy, I know you think you’re a big boy now but I’m a lot older and wiser than you are and I know you’re just not ready for big boy underwear yet. Maybe someday—but not yet. You need the safety and security of a nice thick diaper and waterproof panties. You can trust me because I love you—you know that don’t you? I love you very much and I know this is what’s best for you.”
I was ashamed to hear these words from my aunt–words that said I was nothing but a baby—and it only made me want to cry harder. Ironically, I also knew my crying was making me look even more childish but I couldn’t stop myself. Looking at her mature, pretty face, I knew she held all the cards and that I was a helpless pawn for her plans. Our relationship had undergone a huge and irrevocable power shift–she was in charge now and I had no choice but to follow her directions.
“Now…I know this is going to be hard for you, but the first step for you to take is to admit that you’re a sissy. It’ll make things go much easier from here on if you do. Understand Joshy? You and I both know it, but I think it would be best if you were to say it out loud.
“Can you do that for me Honey?” she asked in her sweetest voice.
My face was beet red and it was impossible for me to say the humiliating words, especially with Lauren standing right there, so instead, I just nodded my head.
“Go ahead, Joshy—tell us what you are,” her friend prompted me.
My bottom felt like someone was holding a red hot skillet to it and I was more than terrified of going back over Aunt Emily’s lap.
“I-I’m a s-sissy,” I mumbled, barely audible.
“You can do better than that, Joshy,” Aunt Emily chided me good-naturedly.
I cleared my throat.
“I’m a-a sissy,” I said with more authority and certainty.
“That’s better baby,” she said, obviously happier with my performance, “And now it’s time to put you into your new underwear. As you can see, I’ve got stacks and stacks of soft, cuddly diapers for you to wear and wet, and plenty of cute plastic panties in all sorts of colors. They’re just what every sissy needs to keep himself protected. And don’t worry Baby, before long–you won’t even notice you’re wearing them.
“So–we have a few new rules now–from now on, I want you to ask me to change you when you’re wet but since this is your first time, you can just ask to be put into your diapers—okay Joshy?”
My cheeks were buzzing with shame as I looked furtively at Lauren, hoping maybe she was making ready to leave. Unfortunately, she was still keenly interested in my situation and she was only too happy to see me humiliate myself.
“Go ahead, Honey, ask for your di-dees,” she said to me encouragingly.
Swallowing hard, I fidgeted nervously, shuffling my feet as I stalled. I didn’t want to be humiliated with wearing diapers but my bottom was burning like a furnace.
Aunt Emily reached down and brought my face back up to look her in the eyes again.
I cleared my throat again nervously.
“Will you p-please put me in my d-diapers, Aunt Emily?” I stammered, blushing furiously. I had never been so ashamed in my entire life.
Her pretty face broke into a ravishing grin.
“Well since you asked so nicely, how could I refuse such a request?
“Oh, and one more thing–I want you to start calling me ‘Mommy’ from now on, because I’m going to be your mommy from here on. No more ‘Aunt Emily’—its ‘Mommy’ for my little Diaperkins, okay?”
I blushed hotly and nodded my head in shameful agreement.
She led me over to the changing table and set me down on it carefully although despite the cool vinyl surface, it hurt terribly on my scorched, blazing backside. I let out a cry of pain and unsuccessfully fought back a pair of tears that trickled down my face.
“Poor little baby,” Aunt Emily said sympathetically, “I’ll rub some diaper rash ointment on your warm little fanny.”
True to her word, she squeezed a large handful of the creamy substance into the palm of her hand and began applying it across my hot, stinging cheeks. With one hand, she held my ankles up high, exposing my bright red bottom to Lauren as she slowly rubbed the soothing crème into my skin. I whimpered with pain and humiliation as she finished her task and then slid three thick diapers under my raised rump. With a deft movement, she tugged my yellow panties down my legs and threw them into the trash without a word. I was devastated to think that I’d never wear soft, silky panties again and I fought against the tears that threatened to spill down my cheeks anew.
Laying me down gently, she picked up the baby powder and began shaking it generously over my crotch and belly. Taking her time, she rubbed the sweetly scented powder all over, from my chest all the way down to between my legs. The familiar scent brought surprisingly strong memories of babyhood flooding back and I balled my fists in mute frustration. Softly rubbing the silky powder into my swollen, cum-filled balls, she seemed to take an especially long amount of time and looking up at her big boobs barely contained in her top, my penis throbbed in futile frustration within its hard plastic prison.
I squirmed in silence as she hummed a pleasant tune and finally pulled the soft, bulky cloth up between my legs, pinning either side around my hips with pink bunny-headed safety pins.
“That’s my little baby,” she said encouragingly as she beeped my wet nose.
My only consolation was that I hoped my new attire would remain a secret between these two women—I sure didn’t want anyone else finding about what had happened.
“Now—let’s pick out an extra special pair of plastic panties for our little princess,” she said gaily.
Opening up the dresser drawer, she sifted through stacks of neatly arranged plastic pants until she pulled out a white pair with pink polka dots. I saw that they had lilac lace around the legs with a single fancy bow on the waistband.
“Here you are, Joshy!” she exclaimed, “I think these will be just perfect for your first day in diapers.”
She made it sound like a momentous occasion like I were heading off to grad school or something. Instead, she was putting the final touch on my transition to babyhood.
I cringed as she gathered the leg openings and began snaking them up over my ankles.
“These will make sure you don’t have any ‘accidents’ or wet the furniture,” she assured me with confidence.
I gulped as she pulled the noisy panties up my smooth legs and began working them over the embarrassing, fat diaper I was wearing. Tugging and using her fingernails, she worked the panties up and around, making sure she got a perfect fit around my hips and thighs.
“There!” she said happily, “You’re all diapered and ready for your nap!”
I really didn’t want to take a nap but I sure didn’t want to end up over her lap again. I whimpered and pouted, showing my displeasure not unlike many a toddler being sent to bed for his daily nap.
“Aww, mommy’s baby wants to stay up, does he?” she asked with mock concern, “Here you go Joshy, maybe this will make you feel better.”
She took a large pink rubber pacifier and pushed it against my lips, forcing it inside until I found myself passively sucking on it. I felt so utterly babyish as I looked down at the shiny white and pink vinyl panties surrounding my bulging diapers while I sucked helplessly on the rubber nipple filling my mouth.
“We just need a comfy sleeper outfit for you and you’ll be all ready for your crib,” she informed me.
Walking over to the closet, my aunt sorted through the various dresses and rompers until she found a soft, fuzzy Care Bears onesie, with ruffled sleeves and leg openings. Bringing it over, she helped me out of my sissy top and slipped the plush, cozy garment over my head. She pulled the stretchy fabric down over my chest and I noticed there was some sort of elastic in the waist that hugged me, yet allowed for freedom of movement and comfort. The bottom half was cut large enough to allow for a big, thirsty diaper, even one as oversized as mine was. Aunt Emily continued humming to herself as she drew the front and back sections together between my legs and secured the four snaps shut.
Even though it fit me remarkably well, I could still see glimpses of my shiny plastic panties underneath at the leg holes and the elastic waist ensured my bell shape would be unmistakable to anyone seeing me. It was obvious there would be no doubt that I was very well diapered underneath this babyish outfit.
“Stand up Joshy, so we can take a look at you,” Aunt Emily said enthusiastically.
With great reluctance, I got to my feet and soon realized I couldn’t stand in my normal fashion due to the thick, but soft bulk between my legs.
“Oh my!” Aunt Emily exclaimed as she put her slim hand in front of her mouth, “Aren’t you just the cutest thing in the world!”
I blushed anew and realized the rest of my look coincided perfectly with the onesie and diapers. My hair was still in pigtails, held up by the pink bow and my Keds with the white anklets added further to my babyish appearance.
“Come along now Joshy,” she said as she patted my fat diapered bottom, “Let’s go say goodbye to your guests and then its beddie-bye time for you.”
I shook my head anxiously and muffled a protest but the pacifier in my mouth prevented me from speaking clearly.
“Here you go Joshy—and here’s a cuddly teddy bear for my little princess to hold onto,” she said, placing the diapered bear in my arms like it was perfectly normal.
I pouted and sulked as she led me out of the nursery and back outside again where my aunt’s friends were talking amongst themselves. It was a strange and unfamiliar feeling as I waddled behind my aunt, the thick diaper rubbing softly between my thighs.
As we came out before her friends, my face and chest flashed crimson all over again as the women turned to face me in my most recent ensemble.
“Well, that’s quite an improvement,” Vanessa remarked dryly, “I see you put your sissy back into his diapers again.”
I resented her remark, if for no other reason than it implied I had been in diapers recently before today but it was their giggles and laughter that really burned me up.
“Yes, it’s been long overdue, but Joshy will be spending his days and nights diapered and dressed like a proper baby girl from now on. We got off to a bit of a rough start, but after putting him over my lap, we got things squared away in no time, didn’t we Joshy?”
The girls laughed in amusement and I felt my eyes brimming with tears of humiliation. I could tell by the looks on their faces that they’d heard every slap of Aunt Emily’s paddle on my bottom, not to mention, my bawling like a baby.
“Apparently,” Lauren told them, “Joshy here hasn’t been properly weaned because the only way I could quiet him down was to breastfeed him like a little baby.”
Hot waves of shame rolled over me as they looked at me like a childish toddler in need of his mommy.
“Did he actually nurse from you then?” Jessica asked, a little surprised.
“Just like a newborn baby,” Lauren replied, “I could hardly get my nipple out of his mouth without him whimpering and carrying on—it looks like I’ll have to make regular visits here so I can satisfy his need for breast milk.”
The girls shook their heads and stared at me while I wilted with embarrassment.
“Say goodbye to your guests now Joshy, and then it’s off to your crib for the afternoon,” Aunt Emily told me.
I wasn’t sure what to do until my aunt took my hand and made me wave at her gathered friends, a childish gesture that brought forth even more giggles at my expense.
Their laughter followed me and rang in my ears as I trudged back down the hall, Aunt Emily holding my hand as if I were a child.
“I know this has been a big day for you Joshy, but don’t worry—you’ll feel much better after a nice, long nap,” she told me as she led me into the nursery. I was still on the verge of tears and frustrated that there didn’t seem to be anything I could do to change my circumstances. Perhaps I could escape, once she’d let me alone in the crib, I mused.
Pulling back the baby blankets, Aunt Emily patted the smooth, shiny waterproof mattress covering and beckoned me to lie down. Reluctantly, I waddled onto it and she drew the soft, fuzzy baby-blue blanket over my body.
“That’s a good baby,” she commended me as she pulled the side of the crib bars up to snap into place.
She bent over the top, giving me a fabulous view of her massive breasts as she stretched to reach something. However, to my surprise and dismay, I saw that the crib had a locking top that folded with an additional set of bars over the upper rim, making the crib a veritable cage. I was trapped like an animal!
Aunt Emily beamed down on me like a proud mother as she clicked the locking top shut and blew me a kiss.
“Happy sissy dreams, Joshy,” she bade me, “When you wet your diapers—you just call out and I’ll come and change you—okay Sugarplum?”
I couldn’t believe that! There was no way I was going to purposely wet my diapers for her.
Stopping at the door long enough to turn out the lights, Aunt Emily waved me goodbye and then closed the door part way behind her.
There was only a Cinderella night light to provide illumination but the sunlight coming from the single window removed any sense that it was bedtime for me. Somewhere outside, my friends were playing rough and causing trouble while I was locked up in this nursery, diapered like a baby and helpless to do anything about it.
I could vaguely hear the laughter and conversation of Aunt Emily’s friends and I was sure they were enjoying themselves and making smug comments at my expense. My aunt had made very clear who was in charge here and I smoldered with resentment and humiliation. I had let her trick me all along and now I was her obedient child, subject to her every perverse whim. It was infuriating because she was “only” a woman and guys my age were supposed to be tougher than that. No self-respecting guy would let a woman push her around like that. The unfairness of it all burned at me like a hot coal.
It was all the more grating that Aunt Emily and her friends were a group of hot babes, totally untouchable by me. They were sexy and pretty, yet I was denied the satisfaction of even masturbating to their memories! It was too much to bear! And now they knew I had been paddled for misbehavior and put into diapers. What could possibly be worse? Could I possibly sink any lower as a guy?
Reaching down, I could barely feel my privates, so thick were my diapers. It sure didn’t help any that I was still horny as all hell. It had been nine days now since I had last cum, and I was frantic for some relief. I had tried over and over, but in the end, all my efforts to find a way out of my cursed chastity device had met with abysmal failure. I was becoming resigned to being subject to Aunt Emily’s rigid control over my sexuality, to say nothing of my attire but I still hated it.
I tried to blank out the memories of their mocking laughter and their superior expressions but I just couldn’t. These women would never forget that I had been spanked, breastfed, and dressed like a baby by my aunt, turned into a sissy infant who hadn’t fought back in the slightest. I blushed anew, every time I relived the mortifying experience in my mind.
Finally, after an hour of bored tossing and turning, I fell asleep.

“Hi Joshy,” my aunt whispered at me.
I opened up my eyes to see my aunt’s pretty features glowing happily as she bent over the opened crib to look down at me. Her big breasts were pressed together, looking as if they were going to burst out of her snug white top at any moment. In her slim hand, she held a large baby bottle filled with milk and she was lowering it down towards my face. I could see a drop of milk about to drip from the end of the brown rubber nipple, threatening to spill on my face.
“Time to wake up, Sweety,” she sang as she positioned the warm nipple at my lips.
“Uh-uh,” I protested weakly and I tried to move my head away but Aunt Emily reached down with her free hand and pinched my nose just enough to prevent my movement. I saw little more than her exquisitely manicured long nails as I struggled briefly.
“Open up, Baby,” she smiled and as soon as I opened my mouth for air, she pushed the wet nipple into my mouth.
“That’s a good baby girl,” she cooed, “Drink your ba-ba like a good baby.”
I squealed and felt the warm milk trickling into my mouth, despite my efforts to the contrary. The rubber nipple felt oddly familiar against my tongue and it compounded my feeling of babyishness. Aunt Emily smiled with satisfaction and her other hand reached down to gently squeeze the front of my crotch.
“Did baby wet herself during her nap?” she asked, using a pouty voice reserved for toddlers.
“Uh-uh,” I tried to say but it was muffled as I swallowed another mouthful of warm milk. I hated drinking milk–if for no other reason than I associated it with my infancy and nursing it from a bottle certainly reinforced that feeling in me.
“Good for you,” she congratulated me, although her tone lacked sincerity, “Now you make sure you drink it all down—I don’t allow any wasting in this house.”
Not surprisingly, my bottom was still sore from earlier and I certainly didn’t want to risk another trip over her lap. Since there was no way I could overcome my aunt physically, I reasoned that my best bet lay in cooperating and trying to get back on her good side again. Maybe there was still some hope of convincing her to let me return to my previous status as a young man. To that end, I finished the bottle submissively as she held it and supervised my efforts. While I drank the milk, I also drank in her luscious curves which was hard not to do, considering her big, mouthwatering breasts filled my immediate view. She was wearing a snug halter top with spaghetti straps that clung deliciously to her wonderful bosom.
Suddenly, I found myself ravenously horny. Looking into her pretty, loving eyes and then down to the soft, smooth skin of her twin melons hanging before my face, she was the very picture of sexual motherhood. I wanted desperately to stroke my penis for all it was worth and it twitched frantically in my diaper. I felt it grow and it quickly found the limits of my CB, preventing any further growth. Squirming uncomfortably, I nursed passively at the bottle as my wiener fought in futility against its implacable plastic prison. Oh, how I hated that damn thing!
“You’re almost finished Joshy, just the other half to go,” Aunt Emily said, misunderstanding my fidgeting.
I whimpered helplessly at her total control over me, even as I submissively nursed on the baby bottle. Finally, I finished and Aunt Emily pulled the bottle out of my mouth.
“That’s a good baby,” she said happily.
Standing up, she took my hand and helped me out of the crib.
I was still unaccustomed to the feeling of the thick bulk of my diapers between my legs and around my hips, and it reminded me constantly of my infantile status.
“You can play with your toys for another hour while I make dinner—okay Joshy?” she told me.
“Okay,” I replied, although I certainly had no intention of playing with the Barbie dolls or teddy bears scattered throughout the nursery. As my aunt walked out of the room, I suddenly became aware of a strong need to take a pee.
Walking out of the softly lit nursery, I went down the hall to the bathroom, but found the door closed. I knocked curiously but couldn’t hear anyone inside so I tried the knob, only to find it locked. Not believing my own senses, I tried it again but it was, without a doubt, very locked.
I looked around but I knew there was only one way to get in. I went into the kitchen where Aunt Emily was making dinner and stood uncertainly before her.
“Umm, Aunt Emily?–”
“It’s ‘Mommy’ now—remember?” she interrupted as she looked over briefly to see what I wanted.
I cleared my throat to say the unfamiliar term again.
“M-Mommy?” I asked tentatively, “For some reason, the bathroom door seems—um, to be locked…”
“Yes, I know,” she said simply, without looking up from what she was doing.
“But…I can’t get in there to go to the bathroom,” I said insistently.
“Mm-hm, that’s right,” she continued with apparent indifference.
“But how am I going to go pee?” I asked in exasperation, “I hafta go–bad!”
Finally, she turned to face me. Crossing her slim arms over her fabulous chest, she smiled knowingly at me.
“That’s what your diapers are for Sweety-pie,” she told me, “Just relax and let what comes natural happen.”
“But couldn’t I just take my diapers down and go real quick?” I pleaded, trying to win her over with my adolescent logic.
“Its time we set a few rules here, Joshy,” Aunt Emily said firmly as she turned and stood over me, “First off—you must never touch your diapers, only mommy and her adult friends can do that—do you understand me?”
“I-I…” I wasn’t sure what to say and visions of her hot friends pulling my wet diapers down to change me filled me with dread.
“Joshy? Do you understand?” she repeated, “Babies don’t change their own diapers—only adults do.”
I felt like arguing that I was almost an adult but my bottom was still sore from earlier. And I still resented the hell out of being forced into this position of being a diaper dependant toddler but I couldn’t see any way out at the moment.
“O-Okay,” I said without conviction.
“Good. Now the other thing is that you don’t have to go poo-poo in your di-dees. When you feel the need for that, you just call me and I’ll take you in and pull your diapers down for you. Okay, Sweety?”
I blushed at the thought of her taking my diapers down in the bathroom while I stood there helplessly.
“Okay, I guess. But what about now?” I pressed her, “I hafta go pee now—real bad!”
Aunt Emily reached down and took my hand, gently leading me into the living room where she sat us both down at the couch together.
“Sometimes the first time can be kind of difficult,” she said as she looked at me and held my hand in hers. Even through the tension of my angst, I still felt an electric sensation at the feminine softness of her hand and I blushed as I returned her intent gaze.
“It’s okay Joshy,” she said in that sweet voice of hers, “All babies wet their diapers—soon, you won’t even realize you’re doing it.”
“But I’m not a baby,” I protested.
“Have you looked in a mirror anytime recently? You look to me like a sissy toddler girl.”
I blushed deeply, knowing she was exactly right. And for a moment, I forgot about the fact that she had been the architect of my infantile appearance.
“I could tell from the first moment I saw you at my door that you belonged in diapers and baby clothes,” she said, smiling warmly again, “You have such a naturally prissy side to your personality…I’m sure you’ll find your nursery much more to your liking than your old bedroom.”
My face reddened at her assumptions of me and I looked away, at a sudden loss for words. I hated the fact that my beautiful aunt though of me as nothing but a natural sissy who belonged in diapers and dressed as a baby.
At the same time, my bladder was now sending me an urgent appeal to do something about my need.
“Aunt Emily—I gotta go pee!” I complained.
“Go ahead Sissy,” she said patting my hand gently, “Show mommy what a big baby you are.”
I bit my lip and shifted in my seat, trying to will my bladder into submission but I could tell it was a losing battle. The pressure was so great, I reasoned that maybe if I just let out a little, I could contain the rest without humiliating myself in front of Aunt Emily. To my frustration, she was watching me with great patience, in no particular hurry for me to do my business before her.
I relaxed my muscles just for an instant and felt a strong squirt of pee come out. But it was like holding back a breaking dam. I was forced to release another stream and suddenly, it was like the door had been knocked down by a bulldozer. I whimpered weakly as a third, especially strong stream flowed forth, soaking the front of my diaper.
Aunt Emily was watching me knowingly and I could tell she was aware of exactly what was happening.
“That’s my little baby…” she cooed, “Just relax and let it all flow.”
Tears of shame filled my eyes and I sniffed miserably. Now that the front of my diapers were thoroughly soaked, there seemed little point in trying to hold back any further. I relaxed and felt strong streams of warm pee filling my waiting diaper, only to be followed by even more. I couldn’t believe how much I had to go!
Aunt Emily was beaming at me like a proud parent and she reached forward to pat the front of my diaper in a congratulatory fashion.
“The first time is always a little difficult but after that, you’ll find you don’t even have to think about it,” she said happily, “Most sissies are chronic bedwetters anyway so this should come as second nature for you.”
I whimpered helplessly as I shifted in my seat in embarrassment while I continued peeing strongly. I could feel a warm, wet pool of unabsorbed pee surrounding my crotch, waiting to soak into the layers of absorbent cloth and I worried about leaking on the couch.
“A-Aunt Emily–” I started, my voice rising in panic, “I think I-I’m going to leak on the cushions.”
I was about to get up but she held me gently in place.
“Shushh,” she soothed me, “You’re wearing very thick diapers made for a heavy wetter. And your plastic panties are nice and snug so I know they won’t leak. You’ll do just fine, Joshy,” she assured me.
I felt the cloth between my legs soaking up the pee and seeping up into the seat of my diapers, making me feel even more babyish, if that were even possible.
At last, the flow abated and I felt a few residual squirts release the last of my pee before my penis finally relaxed.
Aunt Emily seemed to sense what was happening and she asked me to be sure.
“All finished?”
I hung my head in shame and nodded slowly.
“Okay, well I’m going to finish up in the kitchen now,” she said, getting up from the couch.
“Bu-but, don’t you think—I mean—shouldn’t I get a change or something?” I stammered.
“Oh, I don’t think so,” she said with a casual wave of her hand, “I think it’ll be good for you to get used to the feel of wet diapers.
“We’ll have dinner and then I’ll change you before your beddie-bye, okay?”

I couldn’t believe she was going to make me sit through dinner wearing a soaking wet diaper under my onesie. And how early was I going to have to go to bed, anyways? I wanted to argue with her but I bit my tongue instead. She was too tall, too strong, and too quick to pull me over her lap to spank me. I knew I couldn’t take that again.
Instead of answering her directly, I muttered under my breath and went off in a pout. I was angry and frustrated with my situation and I hated being told what to do.
It felt very odd to feel the clammy wet embrace of my diapers as I waddled down the hall and the soft, fuzzy onesie I was wearing only conspired to press the warm cloth closer to my skin. I definitely didn’t like it. Only yesterday, I had had the freedom to wear whatever I wanted and now that had been taken away from me completely.
I trudged into the nursery whose door was now open all the time (if only I’d known what was inside there—I never would have tried to get in!). I saw the same diapered teddy bear on the floor where he’d fallen out of the crib and all my pent-up resentment focused on him. Suddenly, I stepped over and kicked him viciously against the far wall. He hit the wall with a soft thud and then dropped to the floor, looking up at me with his happy, forgiving eyes.
Filled with depression, I sank down to take a seat on the edge of the crib. I could feel the sopping wet cloth clinging miserably to me from all sides now. Trapped by the plastic pants, the moisture had worked its way all around, even up to the upper sides of the diaper.
I felt so babyish sitting in a wet diaper with no way to change my circumstances…But wait! Maybe I could change this part of it.
Not four feet from me were two big stacks of cloth diapers and I knew the dresser held plenty of plastic pants. Thinking for a moment, I figured I probably wouldn’t be able to find the exact same kind of panties but that wasn’t important—the important thing was to get out of this wet diaper. Filled with determination, I went over to look out the door and see if my aunt was anywhere in sight.
I could still hear her in the kitchen, busily making dinner. If I could do this quickly—maybe she’d never be the wiser! A part of me felt sneaky and conspiratorial, part of a secret plot that would, in its own way, undermine my aunt’s total control over me. She might think she could control me but she hadn’t reckoned with my clever mind! I half giggled to myself as I looked around for what I needed.
I’d never spent any time as a babysitter and I had no experience whatsoever changing babies. I had never really given any thought as to how a diaper was fastened but it seemed to me that all I really needed was the diapers themselves—everything else that I was wearing was more or less, reusable. I plopped myself down on the changing table and began fumbling clumsily at the crotch snaps on my onesie. I was amazing how awkward it was and it took several attempts before I finally got them all undone.
The stretchy material popped back and up towards my waist, at least making the rest of my job easier. Putting my thumbs inside the plastic baby pants, I worked them off of the pee-soaked cloth and down the rest of my legs. Working quickly, I unpinned either side, removing the pins, and pulled the heavy cloth away from my crotch.
Suddenly, I heard my aunt calling my name.
“Joshy!” she called from the kitchen.
I froze in panic. What terrible timing!!
“Joshy!” she called again, in an inviting voice that told me dinner was ready. However, I thought it sounded as I she were nearer than the first time and I gulped in fear. I had to get changed and do it fast! Every second counted now!
With blinding speed, I yanked the bulky wet cloth out from under me and tossed it aside, frantically grabbing a few fresh diapers from behind me. I threw them down on the changing table but they became misaligned in my rush, the corners pointing in different directions.
I could hear my aunt’s approaching footsteps, with the characteristic sound of her high heels clicking on the hardwood floor of the hallway.
She would be here any second!
Now in a frenzy, I dropped myself onto the skewed diapers and hastily grabbed the front section, pulling it up and back over my groin. Aunt Emily’s footsteps were quickly getting nearer and with a sinking feeling, I realized I’d never make it. Just as I was about to jab the cloth with one of the diaper pins, my aunt opened the door and stepped into the room.
Her look was one of utter shock as she took in the scene before her. Her pretty mouth dropped open and she stared aghast at the sight of me fumbling clumsily with my diapers.
In an instant, her delicate eyebrows arched in anger and she fixed me with a withering glare that almost made me wet myself all over again.
“I-I-I-,” was all I managed to babble as she swiftly crossed the room and snatched up the paddle.
“N-No-no, Aunt Emily!” I cried as I struggled to get up from the changing table.
Just as I was about to get to my feet, Aunt Emily grabbed me by the wrist and yanked me over to her, sending me tumbling off balance.
“Looks like I didn’t spank you hard enough this afternoon,” she said grimly as she pushed me over her lap.
I landed with a squeal of fear and anguish against her bare thigh, only to have her jerk the diapers away I had clumsily started to put on. With my fanny now clear, Aunt Emily raised the paddle up high and brought it down with a scalding slap.
“YEOOWW!!!” I wailed and instantly I burst into tears.
Two crisp, well delivered swats landed on each pink cheek, leaving a crimson, rectangular pattern by the Spencer paddle. My feet scissored in the air wildly as I bawled like a baby. The paddle came down again and again, slapping both tender cheeks vigorously and making me shriek with pain.
Her hard wooden paddle was as unforgiving as it was inflexible and my buns were certainly paying the price for it. I realized belatedly that having sat in a pee soaked diaper had contributed to make my bottom all the more tender but Aunt Emily was showing no mercy at all. I pounded my fists on the floor and sobbed uncontrollably as she kept up a steady rhythm on my behind.
I tried squirming in her lap but she could sense my efforts to position my bottom in such a way as to take the attention away from a particularly painful spot. She responded by gripping me firmly and slapping that spot with even greater vigor.
Finally, the terrible punishment was over and I lay in place, gasping for air and sobbing like a baby.
“I can see that stronger measures are going to be necessary to keep you from meddling with your diapers,” Aunt Emily said as she brusquely helped me up to my feet. For the moment, I simply ignored what she was saying; shaking my fists and stomping my feet on the ground in frustration. I cried vocally and loudly, looking very much like a punished, spoiled toddler. My aunt ignored me, standing up and hanging the paddle back up on the wall where it belonged. Going over to the pink dresser, she opened one of the drawers to locate something. I saw her carefully sifting through some of the babyish clothing and then she came back over with a pair of soft, fuzzy white mittens, and a roll of duct tape. Taking one of my hands, she balled it into a fist and then placed a piece of duct tape over it to keep it closed. Then she placed one of the mittens over it and buttoned the row of tiny buttons that held it snugly in place around my wrist. I couldn’t stop crying as I tried to understand what she was doing to me and I watched helplessly as she repeated her maneuver with the other hand.
“There—that should keep you out of trouble,” she said with a smug smile.
I looked at my captive hands, holding them up before me in disbelief as I tried unsuccessfully to remove the mittens.
A fresh torrent of tears streamed down my face as I realized she’d won again and I was even more helpless than before. I would be totally dependent on her for everything now and I sobbed disconsolately.
Aunt Emily’s face lost its angry look and she now gazed at me with sympathetic understanding.
“Now, now…I know this a lot to take in, all in one day, Joshy,” she said trying to console me, “Hopefully, I won’t have to spank you like that ever again. Now that you understand that I’m the boss around here, I’m sure we won’t have any more misbehavior.”
I burned with resentment at her superior tone; haughty and confident and knowing there wasn’t a thing I could do to oppose her. Sniveling and sobbing, I looked up into her beautiful eyes and I hated her. I hated her for humiliating me, for spanking me, for lording over me with her rules, but most of all, I hated her because she was so pretty and sexy and totally unreachable by me. I hated the fact that even through my resentment and anger, I still wanted her worse than ever and I detested myself for being so weak.
But that wasn’t the worst of it. The worst part about it, was that she knew I wanted her and wanted her bad. I could see it in her eyes and it only increased her sense of superiority over me. She didn’t need me but I desperately needed her and she knew it. She had that smug confidence that I found so irritating, hidden behind a veneer of kindness and understanding.
How could a woman have such a hold over another person? It didn’t seem possible. She was like a mother/babysitter/idol that I never had.
“Come on Joshy, let’s get you changed for bedtime. What kind of mommy would I be if I left you without any ‘protection’?”
Her smile had returned to her face and once again, I was helpless to resist her. She sat me down on the changing table then suddenly hurried out of the room to get something. She returned in less than a minute with another big baby bottle full of what looked like milk which she positioned at my lips.
“Open up, Baby,” she sang, “Maybe this will make you feel better.”
I was in no mood to argue and I accepted the warm rubber nipple into my mouth, only to be rewarded with warm formula this time. It tasted horrible and I tried to voice my displeasure but Aunt Emily took my mitten and brought it up to support the bottle.
“There—you try and hold that while I change your diaper—okay Honey?” she said encouragingly, “I know that probably doesn’t taste so good but you’ll get used to it—all babies need their formula—and I’m going to make sure you get some each and every day.”
I whimpered in defeat and choked back another sob as I sucked from the heavy bottle balanced in my hands.
“I also put a little something in that one to help you sleep. It’ll help relax you and get you started on the right path of wetting the bed regularly. Tomorrow, you’ll wake up with a very wet diaper, as you will every morning from now on,” she assured me.
Tears were still trickling down my face and Aunt Emily could see I was distraught as she coated my stinging bottom with diaper rash crème. Out of the corner of my eye, I saw her reach over and pull a small, narrow looking rubber implement, shaped like a sausage from the shelf.
“You poor little thing–Maybe I’ll just help ease your burden a bit here.”
With those enigmatic words, she coated the strange looking tool and began gently rubbing it against my back hole. I squirmed in protest and whimpered, trying to prevent her from pushing it inside me as I could feel her trying to do.
“Just relax, Joshy…relax and open up for Mommy…” she whispered in her sweet voice.
The soft, pliable device suddenly slipped past my sphincter with surprising ease and I squealed with distress. My eyes went wide as I felt something that was so obviously foreign invading my hole but Aunt Emily merely smiled down at me. She let the device rest there for a moment, allowing me to get used to the feel of it. I felt emasculated and helpless, being violated by my aunt in this intimate manner but then she started to slowly move the thing in and out. At first, I didn’t know what to make of the strange sensation and then unfamiliarity soon turned to pleasure. She began softly rubbing it across a sensitive nerve inside me and I moaned involuntarily.
“Mm-hm,” she said as she beamed down at me knowingly.
She continued her rhythm and I closed my eyes as I relaxed and gave in to her ministrations. Like a big circuit breaker being thrown, I found myself instantly horny again. I gazed up at my sexy aunt through half closed eyelids, reveling in the ecstasy she was providing.
“Most sissies take to this right away and they soon begin to crave it,” she whispered softly.
I was delirious with pleasure and my penis was fighting frantically within its prison. In no time at all, I was breathing heavily and I gazed up at Aunt Emily with unconcealed lust. Staring at her big, round breasts within her snug white halter top, I licked my dry lips in sexual avarice.
“That’s mommy’s little baby,” she said in that sultry, sexy voice, “Take it like a good little girl.”
I was only too happy to comply with that instruction except my wiener was starting to ache pretty badly. She had brought me to the precarious edge of cumming like I’d never cum in my life but my chastity device was preventing it from happening.
Aunt Emily reached down with her free hand and gently squeezed my swollen, cum-filled balls, smiling sweetly at me. I moaned as the sensations swept through my body, filling me with unrequited pleasure.
Taking the nipple from my mouth for a moment, I looked up at Aunt Emily with a look of desperate pleading.
“Mo-Mommy, p-please…will you please take off my chastity device, just this one time?”
Without answering me, she smiled warmly at me and gently pushed the big rubber nipple back into my mouth, denying me any chance of satisfaction. I whimpered in defeat and tears of frustration spilled down my face.
“Sorry little sissy, your little peanut has to stay where it belongs, locked and caged.”
She continued for about another five minutes, making me gasp and moan from the torturously erotic sensations. I kept flexing my aching penis, hoping somehow the stimulation she was providing could take me over the edge. I felt like I was so close—so desperately close to an earth-shattering orgasm but I just couldn’t take it that last millimeter. Panting and moaning, I surrendered to the waves of pleasure rippling through me as she kept up her maddening sexual torment. Suddenly, without any warning at all, she pulled out the slippery tool and put it aside.
“Okay, that’s enough for now…maybe it’ll give my baby something to dream about when she’s in her crib tonight,” she told me with a giggle.
I let out a cry of anguish and beat my mittened fists on the floor in utter frustration. I had never been so incredibly aroused in all my life. My penis was still throbbing out of control and I would have been willing to cut off my ear to have an orgasm at that moment.
After a quick dusting of baby powder, Aunt Emily quickly and efficiently pinned up my diapers and put another pair of plastic pants on me. I was beside myself with horniness and I wanted nothing else than for her to stick that tool back inside me and stimulate me some more. In desperation, I sucked feverishly on my bottle, swallowing large gulps of the disgusting tasting formula to assuage my frustration.
“That’s a good little girl, drink it all up,” she said as she saw me finishing the bottle.
“And now let’s just get you changed into a fresh nightey and then it’ll be beddie-bye time for mommy’s baby.”
Aunt Emily looked so sexy to me that I literally drooled at her with lust. My penis ached painfully in its cage as it continued to struggle in futility to get a hard-on. Seeing my look of sexual craving, Aunt Emily winked playfully at me and then she popped a large pink pacifier into my mouth. I squealed in surprise but she giggled and sat me on the edge of the crib mattress.
“There you go little sissy, suck on that while mommy finds you a nightey to wear,” she remarked.
I pouted in silence, wearing just my diapers and Ked’s as she sifted through the closet looking for a particular outfit. Soon, she came over with a soft, flimsy pink nightey with layers of ruffles along the hem and short sleeves. Within a matter of moments, I found myself becoming sleepy and I began to waver before her as she removed my onesie and drew the nightey down over my raised arms. My eyelids grew heavy and a blanket of weariness descended over me.
I was only vaguely aware as Aunt Emily tucked me into my crib for the night. She placed my teddy bear under my arm and drew the baby blankets up around my shoulders. My pacifier had fallen out on the vinyl surface of the mattress and she eased it back into my mouth before beeping me on the nose.
“Sweet dreams, my little baby girl,” she whispered, “sweet, wet dreams for mommy’s little sissy.”

That night I dreamt of Aunt Emily.
In the strange, subconscious world of dreams in which we have no control, my anger and resentment towards her were absent. Thus unrestrained, my subconscious longing for her met no obstacle and I was openly in awe of her, hiding none of my feelings. I dreamed we were kissing, nothing more, but passionately enough that nothing else mattered in the world for me. She was so pretty, and her body so enticing, all I wanted to do was go on kissing her soft, full lips. I had to stand on my tip-toes in order to reach up to her and I felt all the more inferior as a result. Still, it was turning me on incredibly and my heart was racing as our tongues intertwined with erotic abandon.
I woke up to the dull ache of my penis, fighting to get hard in my chastity device, once again. Unfortunately, there was little I could do, once it had gotten to this state of excitement, other than to grit my teeth and wait impatiently for the inevitable while trying my best to withstand the pain. Eventually, as it always did, my penis lost the battle and it subsided in ignominious defeat, filling the tube but no longer straining to the point of agony.
Besides the fact that I was no longer able to achieve an orgasm anymore, it frustrated me to no end that I couldn’t get a basic erection. Just a simple stretch of my organ to feel like a man again, but, like everything else, that had been taken away from me by Aunt Emily. And the longer I went without feeling the mundane pleasure of a hard-on, the more I felt feminized and controlled.
As it was, that sensation was soon overshadowed by a new and unfamiliar one this morning. After I got over the pain of my failed erection, I suddenly became aware of the fact I was wearing a very wet diaper. I had slept so soundly, I hadn’t even been aware of a need to pee but the cool, clammy embrace against my hips and loins told me sometime during the night, I had wet, and wet heavily. It made me feel very childish; all the more so since there was nothing I could do about it until Aunt Emily came in to let me out of the crib.
I still couldn’t believe everything that had happened yesterday. Had it all been a dream? I blushed hotly as I re-lived the experience of being led out to the lawn table, in that fuzzy Care Bears onesie with my fat diapers obvious to everyone. I could still remember their mocking laughter and teasing as I stood there like a punished toddler who had just been given a humiliating spanking over his mommy’s lap. Except that I was almost thirteen years old now and ready to start junior high school. I would never forget that devastating experience as long as I lived and I’d never forgive Aunt Emily for subjecting me to it.
My mind naturally turned to re-live the two blistering spankings I had received at my aunt’s determined hand as well. Never in a million years would I have thought she could paddle like that! My bottom was still sore this morning and I knew it would hurt every time I sat down for the foreseeable future. One thing was for certain—she was definitely the boss around here–no way was I going to argue with her anymore.
This morning, as I had done thousands of other mornings, my hands went down instinctively to rub the front of my crotch, only to realize they were still trapped by the restrictive mittens she had put on me. I slammed them down hard on the crib mattress in mute frustration. I was so helpless! I’d never experienced anything like this in my whole life!
Just then, the door to the nursery slowly opened and I saw Aunt Emily’s pretty face peek in, followed by the rest of her breathtaking body as she glided gracefully into the room, a full baby bottle in her hand.
“Joshy? Are you up yet?” she asked in a whisper.
“Yes, Aunt—I mean Mommy,” I replied respectfully. I wanted to stay on her good side today and do anything necessary to avoid any more trips over her lap if at all possible.
“Hello, little Sugarplum!” she said brightly, “How’s my little baby girl this morning?”
“Okay,” I replied neutrally. I don’t know why she insisted on referring to me as a girl–even though I had been dressed like one for the last 24 hours—but it still annoyed me.
She quickly unlocked the crib top and swung it back, after which she unlatched the side and brought it down. This morning, she was wearing a snug, pink top that was so low cut I could see the sexy white lace of her push-up bra partially exposed at the edges. I swallowed hard at the sight and tried to fight it but it was hopeless–my penis had a mind of its own. In no time at all, it was struggling to get hard again and I winced from the pain.
“Here you go Baby,” she said as she handed me the baby bottle and helped me out of the crib.
It was difficult to hold the bottle with my mittens and several times, I came close to dropping it. Leading me over to the changing table, she sat me down and placed her slim hand on my crotch.
“Looks like mommy’s little baby had a very wet night,” she said with a gleam in her eye, “but don’t you worry—I’ll get you changed into a nice fresh diaper right away. You’ll be all safe and secure in just a jiffy!”
I began dutifully nursing on the bottle of warm milk as Aunt Emily busied herself, pulling down my clinging plastic panties and throwing them in the diaper pail. My heavy wet diapers soon followed and Aunt Emily began gently cleaning my rump and between my legs with a baby wipe.
I nursed from the bottle in frustration as I gazed at her huge, pendulous breasts, jiggling and swaying within her tight, tantalizing top. She was so unbelievably sexy, I wanted to cry!
“Up you go, Sweety,” she said as she lifted my ankles and slid a fresh trio of soft diapers under my sore bottom. Taking a big handful of diaper rash crème in her delicate hand, Aunt Emily began smoothing the cool substance across my buns in a comforting, circular pattern.
“Baby’s bottom looks sore from her spankings yesterday,” she commented, using that third person vernacular one would expect from a mother, “Does your little fanny still hurt?”
I nodded as I nursed from the warm milk.
“Well, hopefully, that’s all behind us,” she said, giggling at her own pun.
I certainly hoped so, I thought as she shook the baby powder between my legs and over my chastity device. Pulling the thick cloth up, she snicked a pin through one side and then the other.
“There you are Joshy!” she exclaimed, quite happy with her handiwork, “A nice, fresh diaper for you. Now all you need is your plastic panties and you’ll be ready to take on the world!”
I blushed at her subtly condescending words but continued nursing from my bottle.
“Let’s see…what can we find for our little sissy today…how about something fun…
“Here you are,” she announced brightly, “These are cute, aren’t they Joshy?”
I nodded as I looked at the pink vinyl panties she was holding before me. They were decorated in a nursery print with giraffes and bunnies with soft lilac ruffles around the leg and waist openings. Gathering them in her hands, she beamed down at me as she put them over my feet and began snaking them up my legs. It took a moment to work them over the thick bulk of my diapers and she ran her long fingernails around the elastic waistband until the panties covered the entire diaper. With a quick dusting of powder between my legs, she brushed her hands together in satisfaction.
“Well look at you,” she said with pride, “You’re diapered just like a big sissy should be. That should hold you until at least lunch time.”
She removed my nightey and then replaced it with a short white diaper shirt with frilly pink short sleeves and a design of building blocks across the chest that spelled out ‘Bedwetter’.
“That’s appropriate, don’t you think, Joshy?” she said as she adjusted the short, Birdseye laced-hem below my navel.
“Uh-huh,” I said without enthusiasm.
“That’s why your crib mattress has a waterproof sheet covering it,” she explained as she removed my socks and replaced them with white lacey anklets, “It protects your mattress for when you wet the bed, Sissy.”
Taking a pair of glossy black Mary Janes, she buckled them over my feet and helped me to stand up.
“Take a look at yourself in the mirror, Joshy,” she said encouragingly.
I turned to face the mirror as Aunt Emily stood behind me, looking at my reflection proudly. As she bent over slightly to speak in my ear, I could feel her big, soft breasts pressing against my back.
“Aren’t you just the cutest little baby,” she remarked and she gave me a playful kiss on the cheek.
Looking in the mirror I was shocked by my infantile appearance. Unlike yesterday, when I had been wearing a onesie, today my diapers were totally exposed and the babyish pink nursery print of my shiny panties seemed to shout out loudly at what a baby I was. My ‘bedwetter’ top struck me as a badge of shame, announcing my new and humiliating status to the world. And as I shifted in my feet, I blushed at the sissyish look of my Mary Janes and anklets.
Aunt Emily picked up my pink pacifier from the dresser top and looped it over my head, after which she popped it in my mouth. Her hand dropped down and gently patted me on my thick, diapered seat.
“Welcome to babyhood, Joshy,” she said with a smug smile.
I winced helplessly as my buxom aunt led me out of the nursery and into the kitchen where she helped me up into an oversized highchair. There was a step to allow me to climb into the chair but once I was seated, Aunt Emily removed the step, leaving my feet without any support. It made me feel all the more helpless as my feet swung uselessly. She then secured a sturdy plastic tray in front of me, further immobilizing me.
I heard the microwave ding and Aunt Emily went over and retrieved another baby bottle which she brought over.
“Time for some more formula Baby,” she sang merrily.
“Uh-uh,” I protested fussily as I shook my head. I hated the taste of that stuff and I didn’t want to be forced to drink it again this morning.
“Here you go, Princess,” she said, totally ignoring my resistance.
“Uh-uh!” I repeated but she pushed the rubber nipple into my mouth against my will and tilted the bottle upwards. I kicked my feet helplessly and waved my mittened hands in the air but I could feel the formula flowing onto my tongue. Some of it trickled out of the corner of my mouth and it dribbled down my chin.
“Oh my, I almost forgot your baby bib!” Aunt Emily exclaimed.
She set the bottle down and reached over to the counter, taking a plastic bib and tying it around my neck.
“I don’t wanna drink that stuff!” I complained bitterly.
“Now Joshy,” Aunt Emily said as she picked up the bottle and pushed it back into my mouth, “All babies need their formula—you’re just going to have to get used to it.”
I whimpered in defeat as she held the bottle in place, forcing me to drink the hated liquid.
Just then, the doorbell rang and I nearly choked in panic.
Aunt Emily seemed unconcerned and she shouted for the person to come in as she continued to hold the bottle in place. I couldn’t believe she was going to let someone come in with me dressed like this. It could be anyone!
As the door opened, I nearly wet myself in angst and I recognized Aunt Emily’s cruel but busty friend, Lauren. She was wearing a pair of snug shorts and a tight yellow buttoned t-shirt that hugged her big, mouthwatering breasts in an erotic embrace that made me gulp. Her top said ‘milk maiden’ on it which struck me as appropriate.
After closing the door, she sauntered over and looked down at me disparagingly, shaking her pretty head at my predicament.
“What a sissy!” she stated emphatically.
“Hi Lauren,” Aunt Emily grinned at her friend, “How’re you today?”
“Great—my boyfriend’s taking me to a movie later on and then we’ll head back to my place for a little fun,” she said with a knowing wink.
I burned with jealousy at the thought of another guy getting to enjoy this babe in a way that was totally off limits for me. Wearing fat diapers and a ‘bedwetter’ top didn’t exactly increase my eligibility towards the opposite sex. She looked down at my with her smug look of superiority knowing I wasn’t worthy of the title ‘guy’ but instead, something more accurate like ‘sissy’.
“What’s new with you?” she asked my aunt casually.
“Well, Joshy here had his first wet night in the crib last night,” she explained matter of factly, “His diapers were soaked when I came in this morning to wake him up.”
“Sounds like he’s taken to babyhood like a fish to water,” Lauren remarked caustically.
I blushed, unable to defend myself with the rubber nipple still filling my mouth.
“He certainly has,” Aunt Emily agreed, “But I keep him well protected against any accidents, as you can see.”
Lauren leaned over, giving me an eye-popping view down her top as she looked at my fat, bulging diapers clearly in view.
“Yes, I can see that. Your little bedwetter looks like he’ll be able to pee all he wants now, and not have to worry about the consequences.”
“Ahh…the life of a baby…” my aunt said and they both broke out laughing at my expense.
I had finished the formula and Aunt Emily took it away, to bring over a bowl of pureed baby food.
“Can you start him off on this while I go to the bathroom,” Aunt Emily asked Lauren pleasantly.
“Sure thing,” she said with an evil gleam in her eye as she picked up the big spoon and shoveled a pile of the slop onto it. Aunt Emily disappeared down the hall and Lauren held the spoon up to my face, a mischievous grin telling me she had something in mind.
“Open up Pamper Princess,” she said evenly, “Time for breakfast.”
I opened my mouth but she shoved the spoon in too quickly and much of it slopped down on my chin.
“Mmmphh!” I squealed in protest.
Grinning like a Cheshire cat, Lauren scooped up another spoonful and brought it up to my lips.
I kept my mouth shut as I struggled to contend with what was already filling it.
“Open up Joshy, or I’ll tell your mommy you’re being disobedient again,” she warned me.
I shook my head even as I attempted to swallow the revolting slop in my mouth. Prying my mouth open, Lauren forced the spoon inside although once again, a great deal of it spilled down my chin, landing with a splat onto my bib.
“Uhmm!!” I cried desperately.
She slapped my bare thigh briskly and I cried out again in pain.
“Bad baby!” she snapped, “Do I need to pull you over my lap and paddle your sissy bottom?”
“No!” I cried with my mouth still full of the tasteless glop.
“Then you’d better start cooperating—right now,” she informed me icily as she brought another spoonful up to my lips.
A tear trickled down my face as I opened up obediently to accept another portion which she quickly shoveled into my pouting mouth.
“That’s better,” she said with stern satisfaction, “Your problem is that you need more discipline.”
I looked at her fearfully as she brought another spoonful up to my face. I gulped down the mouthful I had and opened up dutifully for the next one just as Aunt Emily came back into the kitchen.
“How’s my little girl doing?” she asked.
“She’s a very messy eater, as you can see,” Lauren remarked disdainfully.
By now, baby food was spilled all over my chin and bib and I looked like a total mess.
“Oh my—yes,” my aunt agreed, “Well, fortunately, his clothing is easily cleaned and with his baby pants, you can just wipe the food off with a sponge.”
“Mm-hm,” Lauren giggled, “that’s one advantage of wearing plastic panties, isn’t it Sugarplum?”
They both laughed and another tear trickled down as I endured her humiliating taunts, unable to do anything about it.
Just as she brought up the last spoonful, the doorbell rang again.
Not another person!
Aunt Emily went to answer the door and in came another one of her friends, one I didn’t recognize. This one was younger, maybe 18 or so, with long, straight silky blonde hair spilling over her soft, bare shoulders. She looked like an absolute stunner and I blushed hotly as she came in and looked at me for the first time. She was wearing a small white crop top that showed off her flat tummy and covered a plump set of breasts that were perfectly shaped like two cantaloupes.
“Oh—my god,” she said as she shook her head and stared at me in amazement.
With baby food all over my chin, I stared down at the plastic tray in front of me, a helpless captive of these hot babes before me.
“You are the biggest baby I’ve ever seen in my life!” she exclaimed.
Before anyone could say anything, she burst out laughing, showing me a perfect set of white teeth.
“What a total sissy!” she exclaimed emphatically once she’d stopped laughing at me.
I was struck by the vast gulf of difference between us. Her face was model perfect with her make-up tastefully done while mine was splattered with caked on baby food. She looked at me like I was a total loser.
Aunt Emily removed the tray which only seemed to expose me more, especially when she untied my bib and revealed the top I was wearing underneath.
“Ha ha!” her friend laughed mockingly, “’Bedwetter’! How appropriate.”
I was crushed with shame and I felt like I was on the verge of bursting into tears at this merciless assault on my dignity.
Aunt Emily seemed to take sympathy on me and after cleaning my face with a wet rag, she helped me out of the chair, standing me up in the middle of them.
“Go and play in your nursery, Joshy,” she said as she sent me off with a motherly slap to my diapered bottom.
Wearing a baby’s diaper and a sissy top, I felt so inferior to these sexy babes with their big bosoms and pretty faces.
I fled the scene of shame as fast as I could waddle out of there. Going into my nursery (was I already starting to think of it as mine?), I sniffled in misery at the humiliation that seemed like it would never end.
With my hands immobilized in the mittens, it was virtually impossible for me to do anything on my own. Sitting on the floor, I gazed at my reflection in the mirror and realized why Aunt Emily’s sexy friend had reacted like she had. I did look like a total sissy, if not an oversized baby. Turning around, I looked in dismay at my fat diapered bottom, the shiny plastic panties only emphasizing my babyishness.
I sat down with a sigh, resigned to my new life as a prissy infant.
As I got bored, I began playing around with some large blocks with single letters on them, stacking them up as best I could with my mittened hands. I could hear the sounds of Aunt Emily and her friends in the other room, giggling and chatting amongst each other.
Before too long, I began to feel the call of nature and all that liquid I had drank was now starting to make itself felt in my bladder. Frustrated at my aunt’s new sissification regime, I decided I’d outwit her and save my peeing for when she’d be forced to let me in the bathroom to do my #2 business. Maybe I couldn’t stop her from dressing me up like a baby but at least this way, she wouldn’t be able to make me wet my diapers like one. It shouldn’t be long before I had to go #2 and then I’d do all my day’s peeing at that time.
It seemed like a pretty foolproof plan, that is, until I started to really have to pee. I knew I didn’t have to do the other business for a while and if Aunt Emily took me in the bathroom to pull down my diapers and all I did was pee, she’d probably give me a spanking right then and there. With my bottom still pink and sore from yesterday, I couldn’t take the chance of that happening.
I shifted positions, trying not to think about it but the more I did, the worse it got. Finally, I stood up and paced the floor. That alleviated the need for a second but then it was back, worse than before. Looking at the mirror, I felt so helpless and babyish, my hands useless and wearing my childish outfit just as I was about to wet my diapers like an infant. A last, I couldn’t hold it anymore. I let go and like a dam breaking, I flooded my diaper. Hot streams of pee flowed freely, quickly soaking the front and seeping back between my legs. I whimpered helplessly as I looked at my pathetic image in the mirror, a picture of sissyish defeat as my diaper grew ever heavier.
Finally, I was finished and I stood there, not sure what to do. I didn’t want to wear the wet diaper any longer than I had to but at the same time, I didn’t want to go out into the living room and announce my need to be changed to everyone present. That would only confirm to them what a baby I truly was.
I sat down again and resumed playing with my blocks but my heart just wasn’t in it. After a while, my diaper had cooled down and its clammy embrace of my hips and loins was becoming uncomfortable. I wanted to get changed!
Standing up, I went to the doorway of the nursery. To my irritation, Aunt Emily’s friends were still there, talking to each other but I couldn’t tell what they were saying. Maybe if I listened in, I’d be able to hear if they were wrapping things up. If that were the case, I’d simply wait a few minutes and tell Aunt Emily after they left.
Walking quietly down the hallway, I stopped just outside the living room to listen some more but from what I could tell, they were making no indications of finishing their conversation. For all I knew, they might be there for hours!
With a heavy sigh, I somehow summoned up the courage to walk out and I shuffled into the middle of the living room, hoping I could whisper in Aunt Emily’s ear of what I wanted. I saw her, on the far side of the room, sitting sexily in the easy chair, her long, smooth leg draped over the other and dangling her high heel up and down. I had forgotten how perfect her legs were and for a fraction of a second, I admired her curvy calves and shapely thighs, exposed below her short skirt.
But she was some distance away and I had to waddle by Lauren and her friend first. When I had entered the room, Aunt Emily seemed to be in the middle of telling an important story to her friends and I realized I’d chosen a particularly bad moment to interrupt. I waved at her, trying to get her attention, but she totally ignored me as if I wasn’t even there. I was used to being ignored by pretty women but not by Aunt Emily, and this time, I really needed to get changed!
“Mommy?” I ventured hesitantly, but she kept talking without even looking in my direction.
On the other hand, Lauren was now watching me closely, and she wore a mischievous expression on her cute face that spelled trouble to me.
“M-Mommy?” I asked again, trying unsuccessfully to get her attention, “I wet my diapers.”
Aunt Emily’s stunning blonde friend shook her head in disgust and I blushed hotly, hating the fact that I’d been forced into this humiliating position. And since Aunt Emily was studiously avoiding my plea, I was also forced to raise my own voice louder.
“I wet my diapers, Mommy. Can I please get changed?”
For the first time, Aunt Emily turned to look at me and I could tell she was annoyed with having been interrupted. Just then, Lauren grabbed me forcibly and pulled me onto her lap, positioning me on my back so I was forced to look up at her. I squealed in surprise and I tried to get off but she held me firmly. Her huge breasts hung before me, inches away from my nose and I swallowed hard, anxious to prevent from being humiliated by her but also captivated by the fabulous view I was now being treated to. I was both mesmerized and paralyzed, her big, plump boobs hypnotizing me with their maternal allure.
With her free hand, she quickly popped open a few straining buttons from her top and the fabric sprang back, revealing her giant bosom barely held captive within her lacey bra. Using her manicured finger, she deftly unhooked the front clasp and her monstrous melons fell slightly with a wonderful jiggle, no longer constrained by the pretty cups. I struggled some more but in no time at all, Lauren had pulled her right breast out which was nearly as big as my head and she mashed it in my face, effectively muffling my cries.
“Nurse on that, Babykins,” she ordered me.
I squealed in protest but she slapped my bare thigh causing me to gasp in pain and surprise. When my mouth opened, she pushed her firm nipple into it and my squeals became muffled and quieted. My face went beet red with shame as she held me there, refusing to let me go.
Mocking laughter filled the room as the girls took in the easy way in which Lauren had defeated me with her breasts. I squirmed and fidgeted but already, I could taste her milk being released into my mouth.
“That’s it Baby…you know you need mommy’s milk…just like a little baby…that’s it….everyone knows you’re a breast feeder now…”
Her humiliating words made me want to cry but there was little I could do. I sniffled and squirmed but her warm nipple seemed to leak without any effort on my part and I was forced to swallow her breast milk.
“That’s a good little girl,” she said with condescending praise, “Nurse like a good baby.”
Without thinking, I began suckling away at the big nipple in my mouth, closing my eyes to the giggles filling my ears.
“Lauren…I have to say,” Aunt Emily remarked, “I think you’d make the perfect babysitter for Joshy.”
“You just have to know what a baby needs,” she replied with a wink.
“Would you be interested in helping me out from time to time? You seem like a natural choice for my little nephew and I’d prefer it was with someone he already knew and was comfortable with.”
“I’d say he’s pretty comfortable right now!” Lauren exclaimed as everyone laughed at me.
The stunning blonde looked at me and smirked.
“So….is it true that he’s got some perverted fetish for girly panties?” she inquired.
I blushed hotly at the disclosure of my intimate secret.
“Oh yes,” Aunt Emily assured her, “Even before Joshy was put back into diapers, he had a thing for prissy panties.”
The girl shook her head again as she stared at me nursing helplessly on Lauren’s swollen breast, my face red as an apple.
“One day I caught him looking at a catalogue of panties and I made him confess his little secret to me,” my aunt continued, “That was when I knew for sure he was a sissy.”
I mewled in shame as they looked at me but I was powerless to defend myself. Lauren made sure I was unable to take her big nipple from my mouth and her milk was flowing quite freely by now. I had no choice but to swallow mouthful after mouthful.
“The only problem was that he was getting so excited wearing his panties and prissy outfits that he was starting to make wet spots in them,” Aunt Emily continued.
“Ewww!!” the blonde remarked distastefully.
“Yes, poor Joshy couldn’t control himself so we had to put him under strict chastity. Now, he won’t be able to get an erection or—Lauren can you cover his ears?—or m-a-s-t-u-r-b-a-t-e,” she only mouthed the last word silently but I could read her lips well enough to know what she had said.
“The CB6000s he’s wearing took care of that problem once and for all,” she told them, “I’ll probably milk him once a month, just to keep his prostate healthy, but he won’t be allowed to ejaculate until he’s 18.”
“That’s good,” the blonde concurred, “A sissy boy like him shouldn’t be involved with that kind of adult pleasure until at least 18, and maybe not even then.
“What kind of discipline do you use when he acts up?” she asked.
“He gets taken over my lap for a good old fashioned spanking,” Aunt Emily eagerly explained, “I use the paddle you see hanging on the wall there.”
The women’s eyes followed where she was pointing and they nodded their approval.
“Have you ever tried using a cane?” Lauren asked curiously.
“Not yet, but then, I’ve only had to discipline Joshy twice.”
“Oh, you should really give it a try,” Lauren said enthusiastically, “You can really make him dance with just a couple swats of a decent cane.”
“Does he cry easily?” the blonde asked.
“I would have to say yes,” Aunt Emily told them, “I’d say by the third slap of the paddle, Joshy was bawling like a baby. He really doesn’t have any more tolerance for discipline than a little girl.”
The girls giggled at that and I squirmed in embarrassment, my cheeks burning with shame.
“I’ll bet I could do it with one stripe of the cane,” Lauren boasted, “I’d make him put his hands palm down on the table, pull his diapers down and give him a good session with the bamboo one I have—he’d learn real quick who’s the boss.”
“Well,” Aunt Emily laughed, “I think we straightened him out on that issue last night.”
“Enemas are good too,” the blonde offered helpfully, “If he’s fussy or cranky, a nice, long, soapy enema is the perfect cure. It really helps to take the wind out of his sails.”
“That’s a great suggestion Pam. How much would you recommend?”
“I’d start him off with two quarts. Take him over your lap and feed it to him slowly—you’d be surprised how much he can take if you do it gradually,” she explained, “He’ll squirm and complain and make all sorts of promises but just keep filling him up ‘til you can hear the last bubbles going through the nozzle.”
“Oh yes,” Lauren agreed with conviction, “that’s just what this little sissy needs.”
“I like that,” Aunt Emily said with more enthusiasm than I would have preferred, “you can be sure I’ll try it some time soon,” she said agreeably.
“It’s the perfect solution for males who are overly aggressive,” Pam added, “And for those who just need an attitude adjustment.”
Lauren reached down and squeezed the diaper between my legs.
“Looks like your baby has really wet herself this time,” she said sagely.
“Hon?–”Aunt Emily asked Lauren sweetly, “can you just keep her occupied for a moment while I get her a change of diapers?”
“Sure thing,” she replied.
My aunt was only gone a minute before she came back with an armload of supplies. She laid out a vinyl changing blanket and Lauren helped me to lie down on it. I was mortified at the prospect of having my wet diapers changed in front of Pam but after hearing their discussion of how best to discipline me, I wasn’t about to make trouble.
Lauren had already made herself presentable by putting her breast back in her bra although her top was still tantalizingly unbuttoned. She popped my pacifier in my mouth as Aunt Emily began peeling my wet, clinging plastic panties down.
“Since Aunt Lauren was kind enough to feed you lunch with her breast milk, we’ll just get you changed and then you’ll be all ready for naptime!” my aunt informed me happily.
I pouted fussily and let her pull my cool, but very wet diapers off of me and set them aside. Pam bent down to inspect my chastity device close up and I couldn’t help but gaze down her top at her perfect breasts.
“So this stays on while you milk him, right?” she inquired as she pointed at my CB.
“Yes, that way, there’s no risk of him being able to cum,” Aunt Emily explained as she smeared diaper rash ointment across my still pink bottom.
“I see how it works now…it’s only long enough to contain his penis when it’s soft.”
“Yes, so with this on, erections are a thing of the past for Joshy,” my aunt said as she slid my new diapers beneath me.
“Awww, poor little sissy,” Pam said with mock sympathy.
I turned my head and looked away as she took the powder from Aunt Emily.
“You poor little thing,” she said as she took a handful of powder and began softly stroking my swollen balls with it. Her hand was silky smooth and I felt electric shivers as she tenderly stroked my sensitive package. I chewed my pacifier in sexually denied angst as I turned back to look at this cruel, yet beautiful female.
She was so lovely with her pouting face and sexy round breasts, swaying slightly in her snug crop top. My penis quickly swelled within the tube and it strained mightily, but in utter futility against its prison.
I moaned in anguish but Pam kept tormenting me, gently fondling my sack as she shook some more powder on it.
“He has the pubic hair of a three year-old,” she observed with a giggle.
I shook my mittened fists in mute frustration until she finally bored of her game and removed her hand.
“That should give him something to remember me by,” she said with a cruel smile.
My aunt pulled up my diapers and pinned them closed on either side as I continued to shift uncomfortably. I knew it would take at least ten minutes for my penis to finally calm down but until then, my entire groin ached miserably. Oh, to be able to stroke my hard-on just once!
Taking my original plastic panties, Aunt Emily fed them back over my feet and began pulling them up my legs. I could feel the damp elastic of the leg holes and I protested bitterly.
“Mommy! Those are wet!” I cried as I spit out my pacifier.
Aunt Emily continued tugging them upwards as Lauren reached down and pushed my pacifier back into my mouth.
“I know Joshy—sometimes babies don’t get a complete change,” she told me, “and this will make it easier for you to wet the bed during your nap.”
I was cranky and upset, feeling the cool, damp elastic grip around my thighs as she drew the panties up and then over my bulging diapers. Worst of all was that I was afraid she was right; with part of my diapers already wet, I feared my subconscious wouldn’t try and prevent me from wetting as it normally would.
She shook the powder once more to coat between my legs and then she sat back to look at me.
“There. All diapered and ready for your nap.
“Now, give your aunt Lauren a big hug, Joshy—she’s going to be your new babysitter!” she told me cheerfully.
I can’t say I was too happy about those prospects but I got up anyway and went over to where she was kneeling. Once more, I was being forced to acknowledge the superiority of another female over me and I chafed against it bitterly.
Lauren opened her arms and hugged me, a smug look of victory on her cute face that held the promise of more humiliation and discipline at her hands.
“You’re a sweet little sissy,” she told me as she patted the thick seat of my diapers, “And I’ll make sure you get plenty of breast milk when I’m babysitting you.”
“Oh, that reminds me!” Aunt Emily said as she got up, “I like to make sure he gets a full bottle every time before he goes to bed.”
Within a few minutes, my aunt had warmed another bottle of milk and she led me into the nursery to tuck me in.
“This makes it virtually impossible for him to stay dry,” she explained as she lowered the warm nipple into my mouth, replacing my pacifier with the bottle.
“Sweet little sissy dreams,” she bade me as she closed the locking top.
I sighed as they left the room and I began nursing once again, feeling more helpless and babyish than ever.

Aunt Emily’s plans to reduce me to an incontinent sleeper worked much faster than I expected. It only took three days before I was hopelessly wetting my diapers in the crib, waking up to that cool, clammy embrace while I waited impatiently for Aunt Emily to come in and open the crib. Sometimes it would happen during my afternoon nap as well but at night times, it was now a regular occurrence. She was delighted with the change and she beamed at me with motherly pride every time she discovered I’d wet myself like a toddler. She liked to tell me that before long, I’d soon be wetting myself during the day without even noticing it.
For my part, I hotly denied it but she only smiled knowingly at me as if to say it was inevitable.
One thing I had to admit (at least privately to myself) was that my diapers were feeling more natural for me to wear with each passing day. Although the bulk of them prevented me from walking like I used to, I secretly enjoyed the soft swish of the vinyl as it brushed the inside of my thighs. And the bunny soft cotton felt wonderful against my skin—I just wished I had the freedom to masturbate freely into them and the constant temptation was maddening. But I had also started to develop a sense of security while wearing them—I was actually feeling safer knowing I didn’t have to worry about wetting the bed or my pants.
I found the loud crinkle my vinyl pants made to be very embarrassing as it announced to everyone in the room that I was present. Much to my chagrin, Aunt Emily enjoyed patting me on the plump, plastic covered seat of my diapers whenever I walked by and her subtle look of superiority only reinforced my feeling of defeat.
She loved my helplessness and I found it mortifying having to ask her to pull my diapers down so I could do my business in the bathroom. She kept the door open and tapped her toe watching me while I struggled to let nature run its course. Afterwards, she’d pull my diapers up and re-pin them, snugging my plastic panties back into place for the rest of the day. I soon found that my earlier plan to try and do all my peeing during this brief visit to the bathroom was destined to fail utterly because I was forced to drink so many fluids. With a full bottle at every diaper change and more at every meal, I rarely went more than a couple hours before I felt the strong need to pee again. I held off as long as I could but before long, the inevitable happened and I soaked my diapers. I then had to go and tell Aunt Emily about it and ask her to change me. Most of the time she’d lead me by the wrist to the nursery for a fresh set of soft, cozy diapers but occasionally, she’d squeeze my seat and inform me I could just wear what I had for the time being. I hated sitting around the house in a wet pair of diapers but there was nothing I could do about it. I certainly wasn’t going to argue with my aunt about it. In addition to using her paddle, she had taken Pam up on her suggestion and begun giving me warm, soapy enemas every other day. She told me that even if my behavior didn’t warrant it, the process would help to keep me “clean and regular”.

One day, after breakfast, Aunt Emily was changing my diapers in the nursery when she told me she had some business to take care of in town.
“But don’t worry Sissy, Aunt Lauren will be coming over to babysit you today,” she explained to me.
I took that news with misgivings, since my impression of Lauren was that she was cruel, or at best, indifferent toward me.
“When are you going to be home?” I asked her anxiously as she tugged my noisy plastic panties into place over my bulging diaper.
“After your nap Honey,” she replied, “and I just know you’ll have a wonderful time with Lauren–she’s such a sweet person.”
I didn’t share that view but I didn’t say anything, especially since Aunt Emily had pushed another bottle of warm milk into my mouth.
“Since you’ll just be toddling around the house today, I think I’ll just put you in one of your onesies,” she told me as she stood up. “That way, Lauren doesn’t have to change your outfit for your nap.”
My aunt was nothing, if not practical. She went over to my dresser and brought back a pink and white onesie with the word ‘Princess’ on the front and an appliqué of a little baby girl below it.
“You’re my little princess, you know that?” she said brightly as she beeped my nose playfully.
I nodded as she stretched the top and brought it over my upraised arms. It was soft and fuzzy and despite the humiliation I felt at having to wear such a childish garment, it was at least comfy. Shiny pink eyelet lace edged the leg holes and sleeves, giving it a very prissy look and three rows of ruffles went across the seat. Aunt Emily busied herself, pulling the front and back together between my legs and snapping the snaps closed securely.
I was already wearing some pink Strawberry Shortcake anklet socks so my aunt helped me by tying my Ked’s for me. I thought she was done with me until she reached over to the dresser and grabbed a small bottle I hadn’t noticed before. With three generous sprays, she doused me with a sweet smelling perfume, giggling as she did.
“That’s a little something called Nursery Nights, Joshy. It’ll keep you smelling fresh and sweet for your babysitter.”
The fragrance smelled like a pungent mixture of baby powder and something familiar, yet indefinable. True to its name, it reminded me strongly of my nursery, further reinforcing my babyish feelings. I pouted silently as I squirmed, too late to be able to do anything about the scent that would be following me around for the rest of the day.
I heard the doorbell ring and Aunt Emily left to answer it. A few moments later, I heard approaching footsteps in the hallway and my aunt returned with Lauren behind her.
“Your babysitter is here, Joshy!” Aunt Emily announced happily.
Lauren was wearing a short black skirt and matching patent leather high-heeled pumps. Her cream colored sweater was the button down type but it looked like the buttons were at the point of failing any minute. Her big, impressive chest was pushing the material to its limits, straining the overtaxed buttons beyond their intended design. Her long, luxuriant dark hair flowed freely over her shoulders and my heart skipped a beat as I looked up into her pretty, yet condescending eyes.
“How’s mommy’s little breast feeder?” she asked, feigning concern for me.
“I’m sure she’s looking forward to a nice long feed from you this afternoon,” Aunt Emily remarked, her admiration for her lactating friend obvious.
“Oh, I’ll make sure she gets her fill,” Lauren promised with a smirk, “I’ll bet you’re just dying to get one of my nipples back into your mouth, aren’t you?”
I blushed hotly and squirmed in place as the vinyl crib mattress covering crinkled under my thickly padded seat.
As she teased me, she gently hefted one of her large breasts in her small, exquisitely manicured hand, dwarfing it by comparison. Despite myself, I felt my little penis hardening painfully within my chastity device. I hadn’t been horny before but now I felt the incessant throbbing in my groin as I stared with barely concealed lust at her big, luscious bosom, barely contained by her fuzzy sweater.
“Yes, I can see you are,” Lauren answered for me, giggling at my desperate plight.
“Well, I was getting ready to go–can you handle her from here?” Aunt Emily asked Lauren.
“Oh sure, I’ve got everything under control—are you ready to take off?”
“Almost, I just need to get changed for my date,” she replied as she turned to go into her own bedroom.
Her mention of a date was like a knife being driven through my heart and I nearly gasped with pain. Up until now, I had had Aunt Emily’s attentions all to myself and while I knew realistically I could never expect anything sexual from her, it was still devastating to hear of her interest in another male. I burned with jealousy, which was fueled by my resentment of her successful efforts to transform me into a sissy baby girl. Obviously, in my present state, there was no way I could compete with her boyfriend, or any other male for that matter. Looking down at the soft, fuzzy bulge of my onesie that was stretching over the thick bulk of my diapers, I knew I was nothing but a big baby in her eyes.
For the moment, I sat there alone and ignored as the two of them went into Aunt Emily’s room to chat. I sighed heavily, my sadness casting a gloomy cloud over my head.
After a few moments, I grew bored so I went out of my nursery and into the hall. Off to my left, I heard the two women’s voices as they spoke in excited tones about Aunt Emily’s date. As much as it pained me to hear it, I felt compelled to listen in on what was being said and I couldn’t resist the urge to sneak up and eavesdrop outside her door.
Tip-toeing up to the door and peeping through the crack, I could clearly see Aunt Emily in a ravishing state of undress. She had slipped out of her casual clothes and changed into a black silky bra and matching thong panties. I gaped in awe at the two perfect globes of her pert fanny, framed by the loose straps of her garter belt. My heartbeat kicked into overdrive as I had never seen such exciting undergarments on a real woman. I gulped hard and watched in captivated silence as Lauren helped roll her seamed stockings up her fabulous legs.
Instantly my little penis hardened and filled the limits of my CB, causing me to wince with pain. In helpless frustration, I reached down to stroke the front of my diaper, realizing for the thousandth time, that there was absolutely nothing I could do to alleviate my raging sexual appetite. It was so maddening!
Lauren rolled up the delicate, silky material over Aunt Emily’s smooth, firm thighs and I let out a sigh of admiration. Such perfection!
She attached the little straps at the tops of the stockings and then adjusted the fit down the length of her legs to straighten the seams.
“What do you think of these heels?” Aunt Emily asked as she held a pair of glossy, black patent leather 5” high heels sandals.
“Oh my god, those are sexy,” Lauren exclaimed and she took them to help my aunt put them on.
My wiener was throbbing insanely as I watched Aunt Emily sit down on her bed, crossing her sexy legs to make it easier for Lauren to buckle the tiny straps.
Looking at her angelic appearance, I knew she was way, way out of my league but I couldn’t help burning with jealousy as I saw that she was dressing to the nines for some other guy. Worse than that, was the fact that I was desperately horny and frantic to get some relief and Aunt Emily had made sure I’d be prevented from doing so. I stomped my feet in frustration as I unconsciously rubbed the front of my soft diapers in mute helplessness. I bit my lip as I reflected on the incredible inequity of my situation. Some guy was going to have all kinds of fun with my sexy aunt and once again, I’d be spending another long afternoon, frustrated and horny in my sissy diapers.
Aunt Emily slipped on a slinky, snug top and I could just make out the enticing lines of her bra underneath, pushing against the tight material by her big breasts. I shook my head in amazement at how incredible she looked, standing in her high heels and stockings, wearing just her top above the waist. Difficult as it was, I tore myself away from her bedroom door, knowing she’d be coming out any second.
It took longer than I thought, but about ten minutes later, Aunt Emily emerged from her bedroom, sashaying with her usual sexy gait, purse in hand. My penis was still straining to be erect within my CB and my efforts to think about something else to distract me had failed utterly.
As she passed me, she bent over and kissed me on the cheek and I greedily breathed in wonderful scent.
“Bye-bye Joshy. You have a good day, Sweety,” she said as she stood back up and strode toward the door.
I pouted in jealous silence but she completely ignored me as she gave Lauren a hug.
“You go ahead and take off, I’ll see you later this afternoon,” her friend told her.
“Thanks Hon,” Aunt Emily said as she gave her a brief but erotic kiss on the lips. I gaped in lustful amazement as I watched their big breasts mash against each other for a moment.
“See ya, Joshy!” she called as she strode out the door.
As soon as the door closed, Lauren turned to me, placing her hands on her hips as she looked down at me, both literally and figuratively.
“You’ve got a busy day ahead of you, Sissy-boy,” she said evenly.
I gulped in fear at the sudden change in tone of her voice that suggested she had much more in mind for me than simply watching me here.
“But tell you what—I’m going to give you a little freedom by removing your mittens, and if you’re really good, maybe we can talk about removing something else you’ve been wearing.”
My heartbeat increased excitedly at this completely unexpected turn of events. Could Aunt Emily have left her the key to my chastity device?
“Are-are you going to unlock my CB?” I asked her, trembling with excitement.
Lauren smiled wickedly at me as she undid the buttons on my mittens.
“Maybe…if you’re a good little girl today,” she said tauntingly.
My pee-pee throbbed impatiently and painfully in its cage as I contemplated finally being released from Aunt Emily’s cruel and implacable chastity.
“That would be totally awesome!” I exclaimed as my hands came into view one by one.
“Well, we’ll see,” Lauren said noncommittally.
I was willing to do just about anything to be able to cum and the thought of it being possible, changed my outlook entirely.
“Just remember,” she said sternly, “If you misbehave or back sass me, I’ll pull you over my lap and give you a spanking—got it?”
“Oh, yes Ma-am!” I quickly agreed, trying to sound as cooperative as possible.
“Okay, let’s get your purse ‘cause we’re heading out,” she said as she led me down the hall to my nursery.
“Wha-what?” I stammered. I didn’t know we were going outside!
“That’s right Sissy, I’m taking you out for a little bit today—you can’t stay cooped up in here all summer,” she stated with a trace of annoyance.
“Bu-but, I can’t go out dressed like this,” I wailed, my voice rising in a panic.
“You can and will, you little sissy,” She said as she stared down at me sternly, “And if you have a problem with that, we can settle it over my lap.”
To emphasize her point, she reached over and picked up the wooden paddle hanging above the dresser. It had already been the cause of more tears than I could count as wielded by my Aunt Emily and I could only too easily imagine Lauren using it to good effect.
“N-no, pl-please-please don’t spank me, Aunt Lauren,” I stammered fearfully.
“Are you going to do as you’re told?” she demanded.
“Uh…uh-huh,” I answered uncertainly.
“Good, because I won’t hesitate to blister your little sissy bottom, if that’s what it takes to make you fly straight.”
I hated buckling under so readily but I didn’t see any alternative.
Swallowing hard, I rubbed my thick, diapered seat unconsciously.
“I-I’ll be good,” I whimpered weakly.
“That’s better. But just in case, I think I’ll be bringing this along,” she said as she dropped the paddle into her purse, “Come to think of it, I better pack a diaper bag too, for when you wet yourself,” she said as an afterthought.
Quickly, Lauren grabbed a fresh set of diapers, plastic panties, and the other necessary items which she tossed into my big pink and white Tinkerbelle diaper bag.
I sniffled in dismay, wiping away a tear of trepidation at what this terrible day would bring. As Lauren busied herself getting my stuff together, I was still trying to come to grips with the idea of going out in public in my baby outfit. How was I going to deal with that? Did I dare argue any further with Lauren? I’d discovered she had a certain mean streak in her and I knew she wouldn’t hesitate to carry out her threat of a paddling. Looking her buxom figure up and down, I asked myself who would win in a physical confrontation but the most likely answer was her.
And I knew defying her would only make her angrier, resulting in an even more severe spanking at her hands.
“Come along Sissy,” she said as she saw me weighing my options, “Quit dawdling and let’s go.”
I trudged out of the room but Lauren grabbed the lacey collar of my onesie and held me back.
“You forgot your sissy purse,” she said, thrusting the pink, glittery accessory at me.
I sighed and hung it over my arm in defeat.
“Now everyone you meet will know how much you like Hannah Montana,” she smirked.
We went out of the room and Lauren held the door open for me to go out before her but at the moment of truth, I balked again.
“I-I can’t!” I wailed piteously.
The breeze outside tickled my bare legs and I felt terribly exposed to the street and sidewalk before us.
“Come along Sissy,” she snapped impatiently.
Tugging me sharply by my wrist, her other hand swooped down and slapped my diapered bottom hard, sending me stumbling forward down the sidewalk towards her car. In my fear and panic, I felt a small stream of pee escape into my diaper and I squealed like a little girl.
“Oh!!” I exclaimed in my high voice.
Behind me, Lauren quickly locked the door, preventing any chance of my returning that way.
I cringed in fear as I shot angst-filled looks at the surrounding yards and streets. To my relief, the area was mostly empty, due to the neighbors being at work. However, across the street, an older woman stopped raking her yard and she stared hard at me, the confusion on her face obvious. I blushed furiously and turned around, hoping Lauren would hurry up and let me into the relative cover of her car. She winked at me and slowly unlocked her door, taking her time to make me endure the full humiliation of my exposure as much as possible. As the breeze increased slightly, I could feel the lace ruffles around my leg bands and across my bulging, diapered seat being lifted and fluttering merrily as if to call further attention to my babyish condition.
Finally, Lauren released the locks on my side and I slipped inside as quickly as I could. Looking down between my legs, I could see the shiny vinyl plastic of my baby panties peeking out from the sides between my thighs. And in the closed space of Lauren’s car, I could again easily smell the babyish scent of my own perfume surrounding me.
The fact that I had just wet myself without any conscious thought was disturbing although not nearly as much as my desire to leave this neighborhood and the inquiring stare of the lady across the street.
We pulled out and were soon on our way across town. I did my best to look the other way every time we pulled up alongside another car at a stop light but on at least one occasion, I swear I could hear giggles from an open window next to us. I kept my head turned even as my cheeks burned with shame.
Before long, we pulled up in front of a store called Missy’s Dresses and Apparel, with pink neon letters on the sign done in an elegant cursive style.
“Wha-what are we going to do here?” I asked uncertainly.
By way of answering me, Lauren reached over and took the rubber pacifier hanging from the loop around my neck and pushed it firmly and authoritatively into my mouth.
“Mmpph,” I whimpered in frustration.
Lauren opened the door and shortly after, came over and opened mine.
“Come along Missy,” she said, chuckling to herself.
My heart was beating a million miles an hour as I took my first tentative steps outside again. Pushing me forward, Lauren made me walk in front of her towards the double glass doors of the store. I trembled nervously, suddenly very aware of the thick bulk of my childish diapers that forced me to waddle awkwardly. How could I possibly explain my appearance to anyone we met?
When we reached the door, Lauren reached over me and opened it, pushing me inside against my will. No sooner did we get inside when I came face to face with an older, but strikingly beautiful woman. She looked to be in her mid-forties but she was in excellent shape and her piercing brown eyes looked me up and down as she smiled knowingly at me. I felt like wetting again and I only barely managed to prevent it from happening as my cheeks and neck grew hot with shame.
“Well…” she exclaimed, “And who is this little baby girl?”
I blushed crimson and stared at the floor, seeing only her high heels in my vision as I sucked nervously on my pacifier.
“His name is Joshy,” Lauren explained in an unflattering tone, “And his aunt indulges his sissy behavior. Joshy likes to wear little girl panties but unfortunately, he just can’t be trusted to keep them dry. So his aunt decided instead to put him in diapers and baby clothes—they seem much more suitable for his daily wear.”
“Is that so!” the saleslady remarked with obvious enthusiasm, “Well you certainly brought him to the right place—I have all kinds of prissy little dresses I’m sure he’d just love to try on.”
“Why don’t we start by getting his measurements?” Lauren asked her.
“Sounds great! By the way, my name is Barbara–why don’t you two come back into my fitting room,” she said as she led us back into the interior of the store, “Joshy, have you wet yourself that we need to change you?”
Her tone of voice suggested that I had no control whatsoever over my bodily functions.
I blushed again and hastily shook my head no, even though I could guiltily feel a little dampness from earlier in the driveway.
“Okay, well just let me know—you’re not the first little boy we’ve had who couldn’t keep his pants dry,” she explained.
My cheeks burned at being compared to toddlers who hadn’t been potty trained yet.
Going back to her fitting room, Barbara took out a tape measure and took a speculative look down at me.
“Tell you what—why don’t we remove this onesie so I can get a better measurement.”
I whimpered in embarrassment at the prospect of being so exposed but Lauren quickly agreed and she bent down to reach between my legs to undo the snaps. Her movement presented me with an opportunity and I couldn’t help but stare in amazement down the front of her top as she quickly released each snap one by one. Her breasts were so full and plump, I felt a strange mixture of unquenchable desire and deep humiliation all at once.
The springy material popped upwards as it was released from the snaps and my babyish plastic panties instantly came into view. Barbara the saleslady bent down and patted my thick bottom appreciatively.
“Look at who’s wearing baby’s diapers!” she exclaimed a little too loudly as she acknowledged the obvious.
I blushed hotly and chewed anxiously on my pacifier as she stared down from my infantile underwear and then at my crimson face.
“I don’t think I’ve ever had a little boy in here as old as you and still in his diapers,” she stated with amused astonishment.
I felt my eyes moistening with tears of shame as she ran her hands over the smooth vinyl of my stretched baby pants but I almost jumped when I felt her soft hand caress my bare thigh.
“Oh–I’m sorry! Don’t worry little sissikins, I won’t hurt you,” she assured me in a kind, yet condescending tone.
“Such smooth legs!” she beamed up at me in surprise, “And so soft! Just like a little girl’s!”
Despite my intense humiliation, I felt an electric sense of arousal at the touch of her feminine hand on my thighs.
Lauren was enjoying my shame immensely and she wore a smirk of satisfaction as she looked down upon my quivering form.
“He’s a natural born sissy, don’t you think?” she asked the lady.
“Oh my–yes,” the lady quickly agreed, “And he’ll look just perfect when we get him his own dress.”
I shook my head in protest and murmured my disagreement although the pacifier prevented anything coherent from being heard.
“Now you just stand still while I get these measurements Joshy,” Barbara said as she peeled my onesie up and over my head, “I know wearing dresses might seem like a big step for you but trust me, it’s all for the best.”
A tear trickled down my check as she reached around me and began taking meticulous measurements of my chest, waist, and shoulders. Jotting down the figures, she looked me over appraisingly.
“You know, I think I may have something here in the store that can be adjusted to fit you. Wouldn’t you like to go home with your very own girly dress Joshy?” she asked enthusiastically.
I shook my head no and sniffled but she merely grabbed my cheek affectionately and squeezed it.
“Nonsense,” she stated firmly, “I’ll fix you up with something just scrumptious!”
Standing up, she pressed a button on an inter-store intercom.
“Suzie? Can you come back to the fitting room please?”
I scanned the far door anxiously; afraid of the inevitable humiliation that I knew would soon be happening against my will. I felt so exposed, just standing there stupidly in my fat diapers, lacey anklets and Ked’s. In a moment, a young girl about 17 appeared, but before the older saleslady could explain the reason for calling her back, she broke out in open laughter as she stared at my babyish figure. It was obvious from her reaction that she was unaccustomed to seeing young guys dressed in diapers and sissy shoes.
Without thinking, I felt another quick stream of hot pee flow into the soft cloth around my crotch and I cringed in mortified silence. This girl was extremely cute, with long, bleach blonde hair pinned back in an attractive style that showed her high cheekbones and stunning eyes. As she walked closer into the room towards us, she looked me up and down in amazement, shaking her pretty head as if unable to believe what she was seeing.
All I could do was shift nervously in my feet and stare at the floor in pacified silence.
“Suzie, can you see if the pink gingham dress in the window can be adjusted to fit these measurements?” the older lady asked as she handed her employee the figures she’d made.
“And we’ll want to bring up the hem about three inches,” she added as an afterthought.
Still giggling, Suzie took the paper and, giving me one last look of incredulity, strode back out of the room. I felt so embarrassed standing there, the center of everyone’s attention and looking like a whimpering toddler who’d lost his mommy.
“You know, I’ve ordered some food for lunch, maybe you’d like to stay while the dress is being re-cut?” Barbara offered Lauren.
“That would be wonderful—thank you very much,” she replied.
Deciding to take a chance, I pulled my pacifier out and faced up to Lauren.
“A-aunt Lauren? Can I please put something on to wear–please?”
“You’re fine with what you have on,” she replied with callous dismissiveness, “All you need are your diapers and baby panties.”
I pouted in silence but the lady bent over and looked me in the face.
“Don’t worry Honey, you’ll have your new dress before long, try to be patient.”
That wasn’t what I wanted to hear but I didn’t dare say anything that might make Lauren angry.
The lady began setting up some prepared food on a table that was used by the employees until Lauren stopped her.
“Oh, it’ll be just the two of us,” she said pointing to herself and Barbara, “Joshy’s still breastfeeding.”
The lady couldn’t help but giggle at that and she patted me on the head warmly.
“Of course,” she chuckled merrily.
Taking me by the arm forcefully, Lauren led me over to a couch and sat me down in such a way that I had now become accustomed to with her; face up and staring at her big, round breasts that were inches away from my nose.
“Come along baby, it’s time for lunch,” she told me in no uncertain terms.
I whimpered helplessly as she slowly unbuttoned her straining sweater top, revealing more and more of her wonderful, deep cleavage as she went lower. Mesmerized by her fantastic bosom, I stared back in wonder as her magnificent breasts came into view before me.
“Remember, good little boys get treats,” she admonished me as she unhooked the clasp at the front of her smooth pink bra, allowing her fabulous mammary to be free. I swallowed hard as she pulled the soft cup away and revealed her large, perky nipple which was already damp. I mewed weakly as she pushed it into my yielding mouth, a sob of shame and defeat being muffled by her delicious, plump boob.
“Thaaat’s it,” she cooed down at me, “show everyone what a big sissy baby you are.”
I sniffled but sucked obediently, a warm stream of milk soon flowing into my mouth.
As Lauren watched me carefully, her hand slipped down and caressed the smooth, shiny front of my plastic panties.
“Looks like baby already wet himself, hmm?” she said tauntingly as she felt the warmth trapped beneath.
I nodded and blushed hotly, closing my eyes to her riveting gaze.
“Don’t worry Joshy—everyone knows you’re a big baby, why else would a big boy like you still be wearing diapers?”
I whimpered in embarrassment, unable to argue against what she was saying about me and another tear trickled down my cheek.
“I think you’ll like the dress I have picked out for him,” Barbara said between taking a sip of her drink, “It’s really more suited for a baby than a little girl; cute blocks and rattles below the pink gingham pattern.”
“Sounds perfect for little Joshy—doesn’t it Sugarplum,” she said in her kootchie-koo voice.
Her big breasts seemed have an inexhaustible supply of milk and even drinking at a steady pace, there didn’t seem to be any end to it. She and Barbara chatted between each other, ignoring me for the most part as if I were a part of the furniture. At one point, Lauren shifted my head over and offered her other breast to me. I was already feeling full but when saw me pouting with hesitation, she gave my bare thigh a swift slap and I was forced to resume nursing. I was starting to feel the urgent call of nature from all this liquid and I knew it wouldn’t be long before I had to wet myself completely.
At last, Lauren decided I was finished and she lifted me up off her lap and allowed me to sit next to her. Somewhat dizzy, I could feel the milk sloshing around in my tummy and I felt slightly queasy. Just then, Suzie came into the backroom holding a fluffy pink dress in her hands.
Lauren gasped in happy surprise as she took in the babyish garment.
“Will you look at that Joshy? It’s like it was made just for you!” she exclaimed eagerly.
As it was brought closer, I got a better look at it myself.
It was made of two distinct patterns, one a pink gingham design for the short puffy sleeves and the other, a colorful nursery pattern with playful ducks and bunnies on the bodice. It had a lacey Peter pan style bib and the hem flared out over multiple layers of soft white petticoat ruffles. It looked like it had been designed for a two year-old toddler girl.
I shook my head no but no one paid me any attention.
“Here you are Sugarplum,” Barbara said as she took it from Suzie and brought it over to put it on me.
“No…please-please don’t make me wear that,” I whined as I tried to back away.
Lauren seized me firmly and whispered in my ear.
“Joshy? Remember what we talked about before? You’re going to have to wear your CB for a very long time unless you start behaving.”
I whimpered in frustration but stopped fighting as Barbara came closer, holding the dress aloft.
“Raise your arms Sweety,” she beamed down at me.
Reluctantly, I did as I was told and I felt the soft, underlining of the dress descend over my defeated form. My vision was momentarily obscured as the dress was lowered over my head and adjusted into position. I was amazed at how well it fit, the shoulders were roomy but not loose and the chest was quite comfortable. Unconsciously, I ran my finger under the elastic bands at the end of the short sleeves; I wasn’t used to seeing the puffy, balloon shapes on either side of my head.
Looking down, I could see my bare thighs clearly exposed and I tugged at the hem to try and make it go lower.
The women giggled at my maneuver and Barbara moved me closer to the full length mirror in the room.
“Take a look at what a cute little girl you are!” she exclaimed excitedly.
For the first time today, I looked at my reflection in the mirror and I was aghast at what I saw. Not only were my hairless legs in view but my shiny fat diaper was also fully and humiliatingly exposed. I tugged again but neither the dress nor the petticoats would go any lower. I twirled around to look at my backside and all three of the vinyl ruffles on my plastic panties could be seen.
I groaned in humiliated dismay.
Blushing hotly, I felt my need to pee suddenly overwhelming me. Picking the worst possible moment, just then, Barbara bent down and began fluffing up the soft, diaphanous petticoat layers to make them lay even. I tried to hold back but it was too late. With a strong, irrepressible pressure behind it, I let go with a hot stream of pee into the front of my already damp diaper.
Biting my lip, I looked down to see Barbara returning my gaze with a big smile on her beautiful face.
“Well, well…” she announced before I could do anything about it, “Looks like our little baby girl is wetting her diapers.”
My face burned like coals as everyone held their breath to listen. It could be plainly heard as my bladder emptied itself freely into the soft, cushiony folds of my diaper, signaling all too clearly why I was wearing them in the first place. Suzie shook her head and stared at me like I was a helpless retard.
I could feel my diapers growing heavy and sagging as the liquid continued to soak into the cloth. The warm wetness surrounded my sensitive, swollen balls, surrounding me with that familiar childish sensation as it slowly seeped backward into the thick seat of my diaper.
“My, my, you’re quite a little wetter, aren’t you?” Barbara said as she bent down to look me in the face.
A pair of tears trickled down my face as I nodded in shameful silence. Barbara seemed to take pity on me and she hugged me closely to her bosom, patting me on the back even as my peeing continued unabated.
“There, there, baby,” she cooed in a sugary voice, “Mommy knows you can’t help it.”
I shook my head in frustration but she kept consoling me, her hand slipping down to squeeze the now warm, saturated seat of my diapers through the baby pants.
“It’s good you’re wearing a nice thick diaper and plastic panties Sweety,” she reflected as she patted my seat gently.
“Hon, did you happen to bring along a change of diapers for your baby?” she asked Lauren.
“I sure did, and if he’s sounds like he’s done, we can change him right here,” she explained.
I whimpered weakly as I felt the last squirt of pee finishing up, my diapers now very wet and heavy.
Barbara pulled away and then bent down to look me in the eye. Unfortunately, with all three of them watching me closely, I couldn’t keep eye contact with her and I stared at the floor miserably. Taking her long finger, she put it under my chin and lifted it up so I’d be forced to look her in the eye.
“All done Sweety?” She asked nicely.
“Uh-huh,” I mumbled.
“Don’t you worry Baby, ‘cause we’re going to change those wet diapers right away,” she assured me.
Lauren began laying out the supplies on the floor, starting with my vinyl changing pad and one by one, she took out all the other items I needed.
“Here Joshy, why don’t you hold onto these while I’m getting you changed,” she instructed me as she handed me a pair of white nursery print baby pants.
I bit my lip anxiously as I held the infantile panties in my hands. The gesture seemed to say to everyone that the vinyl panties were for me and me alone.
“Just think,” she said in a tone of voice deliberately designed to humiliate me, “while all the other guys your age are getting their first dates with teenage girls, you’re in here getting your wet diapers changed.”
Her biting words stung and I sobbed in shame as I choked back the urge to begin crying in earnest.
“Aww, it’s okay Sweety,” Barbara interjected, “Some little boys just have a hard time keeping their pants dry, but don’t worry—yours are made of sturdy, waterproof plastic!”
Her words were hardly comforting and Lauren sat me down in the center of the big pad where I landed with a wet, warm squish. My bottom felt the full effect as the soaking wet cloth was squeezed against my buns.
After pushing my voluminous dress and petticoats out of the way, I could feel her slim fingers slip under the snug waistband of my plastic panties and begin peeling them off my diaper. I fidgeted fussily as she pulled them down my legs and placed them into a large plastic bag for that purpose.
It was when she unpinned the wet cotton cloth that I realized that I was about to have my chastity device exposed yet again to a pair of curious strangers. I whimpered in shame as she pulled the thick, darkened cloth back and revealed my little surprise package to Barbara and her assistant.
The older woman gasped and immediately reached down to feel the clear plastic tube for herself.
“Oh my word!” she exclaimed, her face breaking into a big grin.
“Looks like wetting his pants isn’t your baby’s only problem-is it?” she asked in astonishment.
“Nope, this little sissy’s also a chronic masturbator as well,” Lauren replied as she cleaned my groin and buns with a baby wipe.
“Well, I’ll bet this little wonder probably puts a stop to that filthy habit,” Barbara opined as she lightly grasped my CB between her fingers.
“It sure does. Without this little gem, I wouldn’t trust Josh for five minutes in his diapers—he’d be playing with himself non-stop.”
I grunted in disagreement but Barbara shook her head as Suzie came over to get a closer look for herself.
“I can imagine that the soft cloth is a tremendous temptation for the little sissy,” Barbara mused, “but this should keep him from being naughty,” she said as she wiggled my captive penis in its tube.
I sniffled and felt another set of tears running down the side of my face.
“Oh—I almost forgot,” Lauren suddenly said, “Josh is supposed to get a bottle of milk with every changing….do you happen to have any here?”
A shadow crossed Barbara’s attractive face as she sadly returned Lauren’s look of inquiry.
“No…I’m terribly sorry, I don’t.”
Looking down at my moist eyes, Barbara actually appeared like she might be feeling sympathy for me.
“And I’m afraid it looks like your baby’s going to start crying.”
I looked away, determined not to humiliate myself further even as I fought back the tears.
“I know!” Lauren announced with a sly grin, “Can you finish changing him? I have just the thing!”
“No problem,” Barbara replied and she took Lauren’s place between my legs. As I watched here begin arranging the stack of soft diapers in front of me, Lauren moved up on all fours until she was sitting next to my shoulder. With an evil smirk on her pretty face, I watched her unbutton her sweater again and once again, her big, beautiful breasts came jiggling into view.
“Here you are Joshy—a niiice serving of mother’s milk while Aunt Barbara changes your di-dees.”
She unclasped her bra and her massive, pendulous breasts swung freely above my head.
“And this should make those wittle baby tears go away,” she chuckled in her condescending nursery voice.
Her big nipples pointed straight at me and she lowered herself downwards, positioning herself in such away that one of her erect nipples came down before my lips.
Without waiting for my acquiescence, she dropped her breast down and it mashed against my face. I squealed as I felt myself being smothered but I couldn’t budge with her holding me in place.
“MMMMPHH!! UMPH!!” I howled, but her breast muffled every syllable that came from my mouth.
“Come on Joshy, nurse from Aunt Lauren while you get put back into your diapers,” she ordered me.
Powerless to resist her, I mewled in defeat, opening my mouth to accept her warm milk. It flowed immediately and trickled down my throat freely as I felt fragrant baby powder being shaken over my loins. I felt so utterly babyish and helpless, nursing the firm, warm nipple in my mouth as Barbara pulled my thick diapers up and pinned them securely into place.
“That’s mommy’s baby,” Lauren cooed satisfied.
Pouting impotently, I moaned in true sissy fashion and squirmed as Barbara began snaking my noisy plastic panties up my legs. She giggled at my plight, and Lauren shared a look of victory with her as she once again, forced me to her feminine will.
Finally, the humiliating and emasculating process was over and Lauren lifted her breast up and away from me. I wiped my face from the spilled milk that had dribbled down my cheek and looked down to see Barbara beaming proudly at me. My shiny plastic baby pants were stretching over a fresh, fat diaper that pushed my smooth thighs apart with their bulk.
“There you are Baby girl!” she proclaimed, “All diapered and ready for your ride home.”
I sniffled and looked around at the smug look shared by Lauren and Barbara. They were clearly pleased with having humiliated me so completely and it was equally obvious there was nothing I could do about it.
Lauren handed me my pink Hannah Montana purse but I pouted in miserable silence.
“Aww, would baby Joshy like a dolly to take home with her?” Barbara asked in that syrupy voice.
“Uh-uh,” I muttered but it was too late.
She brought a female doll of a baby over that was wearing a pink dress and diapers not unlike my own.
“Isn’t that something Joshy? She looks just like you. I know you two will have all kinds of fun playing together.” Barbara said gleefully.
Taking the doll reluctantly, I turned to Lauren who was writing out a check to Barbara for the dress.
“Thank you for everything, Joshy’s dress is absolutely wonderful—isn’t it Joshy?” she asked me.
I shrugged sulkily as I held the doll by her arm, feeling totally defeated and resigned to looking and living the life of a baby girl.
Waddling out of the store, I kept my gaze on the floor until I heard a pair of teenage girls gasping in shock at my appearance. They broke into open laughter as we passed them at the door and I hurried outside to get in the car, my Mary Janes clicking with embarrassing loudness on the sidewalk. Lauren just chuckled and smiled at me with bemused indifference.
“Better get used to it Sissy, ‘cause what you have on is what you’ll be wearing from now on,” she said firmly.
I continued to pout silently on the way home, contemplating a life of endless humiliations but Lauren simply ignored me. Once we got there, I was changed out of my dress and put into a footed sleeper for my nap. It was a soft, fuzzy pink garment that covered me head to toe, and was admittedly, very comfortable to wear. As usual, Lauren insisted I finish a bottle of formula before going to sleep. She set up a baby monitor near the crib, just in case I needed anything or was in any trouble. And with that, she closed the top and locked me in for the afternoon.
I still hated having to take a nap in the middle of the day—it seemed like such a waste of time to me. I’d lie there, staring up through the crib bars at the ceiling, unable to sleep but wishing I could take advantage of the privacy to at least play with myself.
Rubbing the bulky front of my diapers, I could feel their cushiony softness and it caressed my cum-filled balls pleasingly. I could only imagine how wonderful they would feel if my little penis were free of its cage. Oh, how I fantasized about being able to stroke it while dressed in my diapers. To explode in earth-shattering ecstasy would be too delicious for words. But Aunt Emily had made sure I would live exactly like a baby—right down to the inability to masturbate. It was beyond infuriating!
In the silence of the nursery, I could hear the front door of the house close and then the sound of voices, as Lauren conversed with someone who’d just come in. I could tell from the lower timbre that it was a man’s voice and I cringed for a moment as I wondered whether she’d be bringing him in to look at me. However, I soon realized she had other plans since I could plainly hear them going into the bedroom down the hall.
I say I could hear them plainly because apparently, Lauren had made a mistake with the baby monitor. Instead of leaving the one that transmitted in my room, she had left the one that monitors the other unit. Thus, I could hear every word she was saying quite clearly, even though it was several doors away.
I listened in silence as she greeted what sounded like her boyfriend, a guy apparently named Adam. Occasionally, I could hear their conversation interrupted as the two of them kissed and became amorous with each other. I could only grit my teeth in silence as I listened, a prisoner of the baby monitor which was out of my reach from inside the crib. It soon became all too clear that Lauren had invited Adam over to have sex with her and I cringed with bitter resentment and jealousy.
Perhaps it was just my overwrought imagination, but it seemed like she was doing a fair amount of talking for what I always imagined would be a mostly quiet business. She asked Adam to unbutton her sweater—“not too fast”, and then she encouraged him to nuzzle between her big breasts. I could imagine the scene all too clearly, having had my nose there only an hour before. However, this was entirely different. Lauren’s boyfriend was being allowed to fondle and caress her bosom with his hands and face, in a purely adult manner that had been strictly denied to me. It was obvious that she’d made no restrictions whatsoever to his intentions.
I held my breath, listening for every detail as she moaned with pleasure at Adam’s attentions. I could hear him kissing her and I could imagine all too well where on her luscious body he was doing it. My penis was throbbing painfully again, desperate to get freed from it’s implacable prison and I found myself breathing heavily as I heard Lauren moaning once more. I pictured her sitting on the bed, her sweater unbuttoned and open, her head canted back as Adam kissed and caressed her big, beautiful breasts.
In my frustration, I gripped the side bars of the crib while my penis raged in unrequited desperation. It was bad enough that I couldn’t stroke my wiener but I couldn’t even get hard!
Soon, I could hear the bed squeaking and it didn’t take a rocket scientist to tell what was going on. Lauren kept up a steady dialogue of encouragement to Adam which only served to throw fuel on the fire of my imagination, painting a complete picture of what was happening.
“Oh Adam….yes…..yes…oh, your cock is so biiiiig…oh god…yes…drive it in….harder…oh yes…oh my god Baby…don’t stop…”
My penis throbbed so badly I thought it was going numb. And my heart was beating a hundred miles an hour as I listened helplessly to Lauren’s impassioned moaning, filling the nursery with her dripping sexiness. I pictured her boyfriend, plunging his big mighty cock deep into her eager feminine pussy, her slippery insides gripping him with luxurious ecstasy. How incredible would it be to be in his place right now, I asked myself. My own pathetic little member was sore and aching but it was as if I had swallowed a bottle of Viagra. I couldn’t close my ears to the audio torture that was filling the room, nor could I prevent myself from imagining what was taking place two doors down from my own. Lauren was being ravished and satisfied in a way I knew I’d never be capable of. I envied jocks like Adam who were so naturally well hung that babes like Lauren and Aunt Emily flocked to them. And much as I resented her for everything she’d done to me, I would have forgiven her in an instant if I would have been allowed to be in Adam’s place doing what he was doing to her.
For a half hour, they went at it like animals, Lauren crying out in delirium and passion as she came over and over again. Finally, Adam grunted loudly himself and except for their labored breathing, a relative quiet fell over the room.
For my part, I was still worked up in a frenzy and I was panting breathlessly myself as I lay on my back. A bead of sweat had even appeared on my brow and I wiped it away as I grimaced from the pain of my poor caged penis, frantically trying to gain release. I’d never been so frustrated in all my life!
Evidently, the two of them left the bedroom because I didn’t hear much for the next hour or so. When Lauren did finally come into the room, her hair was in ravishing disarray, tousled from her sexual escapade in the bedroom. Seeing her pretty face and hourglass silhouette in the dim light of my nightlight, I was anxiously desperate to cum. The topmost button of her sweater was still unbuttoned and I gazed hungrily at the deep line of cleavage disappearing into her top.
“It’s time for you to get up, Joshy,” she announced, a deeply satisfied element discernable in her tone of voice.
“Is mommy home?” I asked anxiously.
“Nope–she called and said she won’t be home for a few hours. But that’s okay, ‘cause I still have plans for you.”
My heart surged with hope as I remembered her promise to unlock my chastity cage.
“Are-are you gonna unlock my CB now?” I stammered nervously.
“Not yet Joshy, there’s no time for that now—you have an appointment with a friend of mine,” she said vaguely.
“But…when’re you gonna unlock my cage?” I whined pathetically.
“If you keep pestering me about it—never,” she snapped.
I clamped my jaws shut so as not to further annoy her.
Lauren removed my sleeper and then grasping my arm, made me bend over so my diapered bottom was sticking out. With her free hand, she squeezed the thick seat and then gave it a slap which landed with a dull thud.
“Not wet yet, I see,” she remarked as she put away my jammies.
Her haughty treatment of me made me feel very childish and inferior.
I sat on the edge of my crib mattress as she brought my baby dress over and put it back on me. Since I was still wearing my Strawberry Shortcake anklets, all Lauren needed to do was to buckle my shiny black Mary Janes on before she declared me ready to go.
“On second thought, since this dress is so short, we should probably get some rumba panties over those diapers of yours–after all, everyone will be able to see them at all times. And what kind of babysitter would I be if I were to let you go out without some proper rumba panties?”
I grimaced as I wondered who “everyone” was that she was referring to but Lauren was already busy sifting through my panty drawer looking for a suitable cover. She came back over with a glittery pair of pink ruffled panties, slipping them over my shoes and pulling them up my legs.
“Ordinarily, I’d expect a guy of your age to be a bit resistant to wearing frilly panties but Emily told me all about your little fetish so I’m sure you’re quite excited to get to wear them.”
With her scornful tone of voice, I reached down to pull the panties up just to get it over with but she slapped my hands away.
“Hold your dress up, Sissy,” she ordered me tersely.
I passively did as I was told and Lauren slowly snaked the silky panties up and over the fat bulkiness of my diapers, taking her time to fit them carefully.
“You are without a doubt, the biggest sissy I’ve ever met in my life,” she remarked as she shook her head in disgust.
She pulled me over to the full length mirror and forced me to face my reflection.
“Just look at yourself,” she said as she spun me around so I could see my ruffled seat, “Just like a little baby girl.”
I had to admit she was right but there was little I could do about it. I was desperate to gain release from my chastity device and I was willing to put up with anything to make it happen.
“Okay Sissy, get your purse–it’s time to go,” she quipped.
Grabbing her keys, Lauren led me once more outside and we took another short ride over to a salon where she had a friend working. We entered the building through a back entrance and went into a room that was separated from the public area. For a moment, we were alone but my relief was short lived as a pretty young teenage girl wearing white jeans and a tank top soon came in.
“Oh my god!!” she exclaimed in a much louder tone of voice than I would have preferred.
Eyes wide open in shock, she looked me over like I had just stepped out of a flying saucer. I cringed uncomfortably as she examined my dress, feeling the material in amazement and then looking me in the eye as if to see what kind of guy would allow himself to go out in public dressed as a baby girl. The worse moment was when I felt her lithe hand reach down and softly pat the ruffled seat of my diapers.
“Well, you certainly are well protected,” she giggled with amusement.
“He needs to be,” Lauren remarked, “he can’t keep his diapers dry for more than an hour.”
“Is that so?” the cute girl declared excitedly. She seemed genuinely fascinated that she had a teenage guy before her who needed to wear diapers.
“What’s you name, Honey?” she asked sweetly.
I was about to stammer out my name when Lauren beat me to it.
“His name is Joshy,” she said simply.
“Aww, I think that’s a cute name,” she replied, “My name is Hope.”
“Hi,” I said weakly, overwhelmed by the combination of her close attention and pretty face.
“Why don’t you come over here and make yourself comfy,” she said as she took my hand and led me over to a salon chair that had been placed near a counter with a lighted mirror facing it.
I did as I was told, uneasy about what the two of them had in mind.
“You just relax Joshy, I’m going to fix you right up here.”
She proceeded to place a pink smock over me and begin working on my hair, cutting here and there and then she started applying a set of curlers all over my head.
“Wha-what are you doing?” I asked as I tried to get up from the seat. I didn’t like where this was headed, not one bit.
“Sh-shushh,” Hope said soothingly as Lauren came around and held me in place, “I know you’ll just love how this will turn out–trust me.”
I struggled weakly against Lauren’s grip and realized there was little I could do.
“Joshy…” Lauren whispered softly in my ear.
Her sexy voice disarmed me unexpectedly and I relaxed in my seat.
“When we get home, I’m going to unlock your chastity device and then you know what?”
I gulped with anticipation.
“Huh-uh,” I said with nervous excitement.
“And then I’m going to put you into a fresh set of baby soft diapers and let you take your time as you play with yourself without restriction…and you can kiss my breasts anywhere you want…would you like that?”
I couldn’t believe my ears–what a wonderful treat that would be, to finally feel the blissfully soft cotton of my diapers directly on my engorged, neglected hard-on.
“Y-yes Ma’am,” I answered shakily.
Hope turned my chair so I was facing away from the mirror and it was easier for me to remain compliant now that I wasn’t seeing my hair being transformed. It took another twenty minutes and then Hope applied some foul smelling chemical to my curled hair. Deep down, I knew I should be doing something to resist her efforts but I was ruled by my absolute need to get sexual relief. It had been weeks now and my heart raced as I contemplated my soon to be orgasm.
Hope covered my head with a plastic cover and then pushed a dryer into position behind me.
“Okay Joshy, just relax here and I’ll take care of your nails,” she said warmly.
‘Huh?” I asked, not sure what she meant.
Clicking on the dryer, Hope ignored my question and then sat down before me, taking one of my hands in hers. She filed each nail carefully and then took a small bottle of pink nail polish and opened it up.
“Oh…oh,” I whimpered in protest but Lauren had moved in front of me and unbuttoned the top button of her sweater, revealed another tantalizing inch of her deep cleavage.
“Joshy…” she cooed temptingly.
I bit my lip and settled down as Hope began carefully painting my nails a glossy coat of pink.
“What do you think about this color, Lauren?” she asked.
“It’s perfect,” she replied nodding with satisfaction, “And I’m going to make sure his aunt makes him keep them up.”
I cringed at the thought of having to maintain the feminine appearance of my nails but somehow, I put that thought out of my mind. Instead, I gazed at Lauren’s wonderful bosom and fantasized about kissing the plump tops of her breasts as I stroked myself to the mind shattering climax that had for so long been denied me. I felt mischievous to think that I’d soon be circumventing Aunt Emily’s cruel chastity regime.
Before long, Hope had finished my nails and she sat back to look me over.
“Tell me Joshy, have you always been a little sissy?” she asked with genuine interest.
It was mortifying to be asked such a direct question, all the more by a very attractive girl not much older than me.
“N-no,” I replied hesitantly, realizing belatedly that my answer became a tacit admission that I was a sissy.
“Well, you certainly are one now,” she giggled quickly, “I can’t recall ever seeing a boy of your age still in diapers.”
Her air of superiority washed over me, making me feel all the more weak and effeminate. My cheeks burned with shame and I swallowed hard trying to think of something to say. I was about to launch into a spirited defense of myself but Lauren quickly interrupted me.
“Joshy has a fetish for wearing prissy, frilly girl’s clothing and fortunately for him–his aunt is very understanding,” she announced boldly.
“Really?” Hope asked interestedly.
“Oh yes, but Joshy wasn’t satisfied with just wearing little girl’s panties–he wanted to take it a step further and he asked his aunt if she would start putting him in diapers and plastic pants.”
Hope was clearly shocked by this revelation and she turned back to face me.
“Was that because you were wetting your pants and you knew you needed diapers?” she asked me bluntly.
“No-no,” I protested as I shook my head, not happy at all with how the conversation was headed.
“Actually, it’s because he likes to play with himself, and not only does he love the soft, babyish feel of diapers, but it also makes it easier for him to hide the inevitable wet spot,” Lauren answered for me.
My mouth opened as I tried to blurt out how I’d been forced into diapers against my will but Hope wasn’t paying any attention.
“Eww,” she said in disgust, “That’s gross.”
“–And no sooner did his aunt start putting him back in diapers than he began wetting them just like a baby. As a matter of fact, he’s become so comfortable wearing them now that he’s lost complete control over his bladder.”
I blushed hotly as Hope looked me over closely.
“I have not!” I denied vehemently but it was obvious that Hope didn’t believe me.
“It’s okay Joshy, most little sissies have a hard time controlling themselves and that’s why they need a strong mommy to take care of them,” Hope explained, “Most sissies are bedwetters too so it is only natural you should want to wear diapers.”
“But when it became apparent that Joshy couldn’t stop playing with himself, his aunt had to put him in a secure chastity device–she’s got him wearing one all the time now, underneath his diapers.”
“Really?” Hope asked again, “He’s wearing a chastity device right now?”
“Absolutely,” Lauren replied, “It’s a godsend for little boys like Joshy who can’t stop masturbating.”
Hope’s pretty eyes drilled into me as I cringed with embarrassment.
“Does it really work?” she asked as she stared at me.
“It’s a 100% effective,” Lauren assured Hope, “Joshy’s little penis is held captive in a clear tube which prevents him from being able to stroke it and he can’t even get hard. Of course, he still gets horny as hell but now there’s nothing he can do about it.”
“Is that so…” Hope said with a devilish smile.
Cupping her breasts, she pushed them up together and gently stroked them, deliberately tempting me with her sexiness. I quivered in helpless silence as I gaped at this stunning female sitting before me. With a lustful look in her eyes, she leaned forward and kissed me full on the mouth. My heart beat double time as electric shock waves swept through my entire body. My tiny wiener immediately reacted and it stiffened painfully within my chastity tube.
To my shock and delight, Hope’s eyes closed and I felt her lips gently parting. Her warm tongue suddenly entered my mouth and I squealed with sissyish surprise. I felt so helpless, my hands waved in the air as this bold, confident female French kissed me with impunity. I moaned and squirmed like the virgin I was, feeling powerless before her erotic onslaught.
Finally she stopped and sat back, smiling wickedly at me. I was breathing heavily, my blood surging through me as my penis fought in futility against it’s implacable prison.
“How was that, little sissy girl?” she asked sweetly.
I was still gasping for air as she reached down and fondled the cushiony front of my diapers over my filmy rumba panties.
“You’re right,” she said looking up at Lauren, “No boner…nothing, just the soft feel you’d expect from a little baby.”
I pouted with frustration at her smug look of superiority with the knowledge that she knew there was nothing I could do about it. I was as harmless as a baby and just as sexless as far as she was concerned. It stung my pride terribly and hurt my feelings to be thought of in that way, and my lower lip quivered in misery.
“Aww, you poor little thing,” Lauren said with mock empathy.
Stepping forward, she pushed my pink pacifier in my mouth and placed the vinyl loop behind my head.
“Now Hope knows just how much of a sissy you are,” she told me in no uncertain terms.
Utterly ashamed of myself, I hung my head as Hope giggled with delight.
“I think your hair’s about done, Sweety–would you like to see the new you?” Hope asked brightly.
I didn’t say anything but she stood up and went around to remove the hairdryer from behind me. It took another five minutes to remove all the tight curls from my head and I felt an immense relief to finally get them out of my hair.
Hope used her soft hands to run through my hair, getting my hair adjusted the way she liked, all the time giggling to herself. My heart sank at what I was afraid it would look like but all too soon, she removed my smock and spun my chair around to face the mirror.
I gasped in shock as I stared at the little toddler girl staring back at me from the mirror. Tight, blonde sausage curls covered my head, transforming me into a frightened little girl who looked like he’d lost his mommy. My short pink baby dress and visible diapers below, combined with the Shirley Temple hairdo gave me a distinctively prissy toddler look. Raising my hands up to feel my formerly boyish hair, I saw how much the glossy pink nails she’d painted added to my image–I looked every bit like a four year-old girl still in diapers. Lauren stood there, her slim arms crossed over her bountiful bosom, smirking with satisfaction down at me.
Somehow the shock was too much for me. Without realizing it, I released a strong stream of warm pee into my diapers. Only upon feeling the second stream did I finally come to my senses.
“Oh!” I whimpered, and my pacifier dropped out of my mouth as my hands dropped down in a belated attempt to staunch the flow. Only barely did I manage to bring it to a halt but not before the front of my diapers were thoroughly soaked. Tears started to tumble down my cheeks and my puffy, frill covered shoulders began to shake.
“Oh my, I think our little sissy just wet himself,” Lauren pointed out.
Hope bent down, a look of genuine concern on her cute face, as she gently set her hand against the front of my diapers.
“Mm-hm,” she agreed, “Mommy’s little baby just wet his diapers–poor little thing.”
Lauren took my pacifier and pushed it back into my mouth even as more tears trickled down my cheeks.
“Did you bring a change of diapers?” Hope asked hopefully.
“No…to be honest, I didn’t think he’d need them–I just changed him a couple hours ago,” she replied sheepishly.
“Sorry Sweety,” Hope said as she knelt down to look me in the face, “I’m afraid I don’t have any diapers for you here either.”
“It’s okay,” Lauren said dismissively, “he’s used to wearing wet diapers–he can wait until we get home.”
Hope used her index finger to pull my chin upwards to face her.
“Please don’t cry, Joshy,“ she said sympathetically, “Would you like another kiss, Honey? Would that make you feel better?”
I shook my head angrily but Hope wouldn’t leave me be. Reaching down, she kissed me on the cheek, leaving a pink lipstick mark on me.
“Well, I guess it’s time to go,” Lauren announced, ignoring my distress, “Joshy–thank Hope for doing such a wonderful job on your hair.”
I wasn’t about to thank this girl for contributing so generously to my future humiliation and as I crossed my skinny arms over my chest, I chewed my pacifier in fussy silence.
“Joshy? Don’t be rude to your betters–I want you to thank Miss Hope for making you pretty,” she said with more insistence.
I shook my head petulantly, not realizing the big pink pacifier still in my mouth made me look infantile.
Lauren leaned down and grasped my arm firmly as she whispered in my ear.
“Now you listen here Sissy-boy. You are going to thank Miss Hope or I’m going to turn you over my knee right here and blister your bottom–you got that?”
I shiver of fear rippled through me as I contemplated a public spanking in this room, just shouting distance from the rest of the salon.
Taking out my pacifier, I kept my head bowed as I tried to cobble together the humiliating words.
“Th-thank you,” I mumbled.
“You can do better than that, Joshy,” Lauren informed me firmly.
I cleared my throat, desperate to avoid a paddling.
“Th-thank you, Miss Hope,” I said in a louder voice.
“-Thank you for what…” Lauren insisted.
I swallowed hard, my face blushing red.
“Thank you for-for helping me look more like the sissy I am,” I blurted out.
Both of them looked immensely satisfied and they looked down on me with obvious superiority.
“I’m delighted you like it, Joshykins,” Hope beamed down at me, “And now everyone will know just how much of a sissy you really are.”
I nodded in humiliated silence as I stared at the floor.
“Now can we go home, Miss Lauren?” I pleaded miserably.
Lauren sighed and picked up her purse.
“Yes Joshy, let’s go so we can change your diapers. Hope–thank you for everything–you did a fantastic job and I just know that his aunt is going to be thrilled when she sees what he looks like.”
Hope giggled.
“Glad to be of help–he won’t be able to hide his sissiness now,” she promised.
“Nope. Fact is–most prissy little boys like Joshy here would like to dress up in their femmy clothes until they’ve tossed off. Then they like to go back to being macho boys again. This way, Joshy is forced to live the sissy life he should be living and everyone will see him for the way he really is–a prissy, babyish little sissy,” Lauren explained at length.
Taking my hand, she pulled me to my feet and we said goodbye to Hope as I considered how my life would be in the future–a never ending series of humiliations and embarrassing moments which I would be powerless to stop.
On the way home in the car, I was fussy and cranky so Lauren put my rubber pacifier back in my mouth to keep me quiet. I pouted in frustration, the cool, wet cloth of my diapers clinging clammily to my skin. Several times during the ride, I felt the need to pee and I just let it go, figuring there was no reason to hold back any longer. At least the additional pee had the benefit of re-warming my diaper which providing me with some small measure of solace.
At last, we reached Aunt Emily’s house and after Lauren parked the car, she took me inside and straight to my nursery.
“Okay, Joshy, let’s get those wet diapers of your changed,” she said as she sat me down on my changing table.
“Looks to me like you’ve lost all control of your wetting,” she observed dryly as she peeled my rumba and plastic panties down.
I was beginning to have doubts of my own so I remained silent as Lauren tossed my damp panties into the large diaper pail at the foot of my crib.
“You really are becoming more and more like a baby everyday, aren’t you?” she added as she unpinned my soaking wet diaper.
“I-I couldn’t help it,” I bleated shamefully.
“I think you can but you choose not to,” she asserted as she wiped the pee from my groin and buns, “Personally, I doubt your mommy ever fully potty trained you.”
My cheeks went bright red as I struggled to think of a plausible argument to deny her words.
“Huh-uh!” I disagreed.
‘I’ll bet you were a bedwetter all through grade school and wetting your pants on a regular basis too,” she opinioned.
“Tha-that’s not true!” I stammered, knowing she didn’t believe me.
Lauren slid three thick diapers under my upraised rump and she positioned them evenly underneath me.
“Well, you’re finally getting what you need and deserve, Joshy,” she said as she sprinkled baby powder all over me, “to be treated like the big baby you really are.”
She pulled up the sides of my diapers and pinned them snugly closed with my pink bunny-headed pins. Opening up my plastic panty drawer, she chose a pair of clear, side snap vinyl panties with pink and yellow polka dots on them.
“This is the way all sissies should be treated–instead of allowing them to be out in the world to masquerade as men, trying to fool women into thinking they’re something that they’re not.”
I looked up at my beautiful babysitter, resenting her humiliating words but wishing I could deny their truth.
Lauren carefully snaked the babyish plastic panties up my hairless legs, working them over the fat, bulky diapers until they completely covered the cloth.
“Fortunately, now no one will ever confuse you for anything but a simpering, prissy little sissy baby, who’d cry if someone took his dolls away,” she said as she sat back to look at me evenly.
Just then, the doorbell rang.
Lauren abandoned me in the nursery to answer the door and I soon recognized her boyfriend’s voice as he came inside.
Hushed discussion followed and I could make out Lauren giggling as she led Adam back down the hallway toward my room. I briefly considered trying to hide but there was nowhere to go. Looking around the nursery, the open closet with my baby outfits seemed to mock my predicament.
A moment later, Lauren came into the room towing her boyfriend Adam behind her by the hand.
“Here he is–my girlfriend’s nephew, Joshy,” Lauren said by way of introduction.
I blushed hotly as her tall, hunky boyfriend gaped at me in awestruck silence before he broke out with a hearty bellow of laughter.
I cringed even as I unconsciously evaluated this guy who I knew was enjoying every aspect of Lauren without restriction.
He had a craggy square jaw with a shadow of stubble that gave his handsome looks a certain ruggedness. His short, dark hair was curled in a tousled, boyishly disheveled way, yet stylish like he had just come off a movie set. With his broad shoulders and chiseled upper arms, it was no mystery why Lauren found him attractive. He was my exact polar opposite–the very picture of masculinity whereas I looked like a toddler girl still in need of diapers.
He put his big hands on his solid hips and looked down at me, shaking his head and he smiled with amusement.
“Laurie told me you were a sissy but I had no frickin’ idea,” he remarked bluntly.
Was there no end to the humiliations of this day? I just wanted to crawl under a rock and die.
Lauren was clearly enamored with him and she drew his hard body to hers to give him a long, deep kiss, filled with the promise of much more. I watched in impotent silence as her slim hand dropped down to slowly stroke the front of Adam’s worn jeans. My eyes couldn’t help but see the enormous bulge in his pants that was growing like a monster that had just been awakened. I was mesmerized by her long manicured nails as she softly rubbed his growing erection through his pants. It was as if she were stroking my own neglected member and I felt myself growing hard along with Adam.
The difference was that I couldn’t do more than grow an inch or so before I reached the limit of my infernal chastity tube. Adam on the other hand, had no such limits and his bulge grew increasingly larger as they kissed passionately and openly in front of me.
Suddenly, Lauren tore herself away from Adam and looked down at me, her eyes clouded with wicked lust.
“You wanna cum, Sissy?” she asked me pointedly.
While I was certainly feeling acutely self-conscious in front of her intimidating boyfriend, I still had the wherewithal to realize I should seize this opportunity while I had it. God only knew when I might get another chance, if ever.
“Uh huh!” I replied without a further thought.
“Okay, I’ll unlock your chastity tube but you have to do one thing for me…actually, you have to do it for Adam here,” she giggled as if suppressing some great secret.
I didn’t know what to make of that.
“What do I have to do?” I asked uncertainly.
Without answering me directly, Lauren unzipped Adam’s jeans and slowly pushed them down around his ankles, her hands wandering over his muscular legs in obvious admiration as she did so.
“Come here,” she beckoned me provocatively.
I inched forward, not knowing what she wanted but also anxious to do whatever was required to get her to unlock my chastity device.
“All you have to do is take his cock in your mouth,” she said in a husky voice.
I slowly shook my head as I looked from her up to Adam who was leering down at me with a strange look on his face.
“It’s up to you…” Lauren said, suddenly ambivalent, “You can go another year or two without cumming if you’d prefer…I know your aunt will never give you the chance…or…you can do a little suck right now and earn yourself a nice, long orgasm…”
I have to say she was painting a picture that looked assuredly bleak if I were to say no to her…and then again…who would ever know if I did as she asked? For that matter, how could my dignity possibly plumb any deeper depths than I’d already explored today?
“How long do I have to lick it?” I asked tentatively.
“Just take it in your mouth, that’s all,” she replied simply, “And then I’ll make sure you get your just reward.”
Once again she giggled and some part in the back of my brain told me not to trust her but my penis was sore from it’s constant flexing in the tube.
I was still waffling about doing what she suggested as she pulled his boxers down his solid built thighs. As his underwear dropped lower, I caught sight of the monster hiding in his pants. What a beast!
It still hadn’t become fully erect but even in it’s current state it was truly massive. I likened it to a cucumber, big and fat in circumference and growing longer with each passing moment.
Glancing up at Lauren, I gazed at her wonderful cleavage, her top most button undone, and I knew I had no choice. I had to do whatever it took to get some relief.
Inching forward on my knees, I drew closer until I was staring at Adam’s rising hard-on directly before my eyes. His head was a purplish, firm piece of meat that reminded me of a fireman’s hat, pulsing and throbbing with pent up energy. Tentatively, I reached over and took a hold of his warm shaft but I couldn’t get my small hand all the way around it, it was so big.
Swallowing hard, I reasoned that it was only one quick slurp and then it’d be over. With that small chimera of insurance tucked into the back of my mind, I opened wide and carefully lowered my mouth over his gargantuan tool.
It was surprisingly warm in my mouth but I was amazed at how much I had to stretch my jaws to get even his head inside my mouth. I tasted a slightly salty taste and then felt his big hands take a hold of the back of my head.
“Ahh…” he exhaled in satisfaction.
With my cheeks stretched wide and my mouth full of hard cock, I was more than ready to be done, having fulfilled my obligation but Adam had other ideas.
“That’s it Sissy boy, suck daddy’s lollipop,” he told me throatily.
I struggled to lift my head but he now had a firm grip on it and apparently had no intention of letting go.
Squealing mightily, I waved my hands in the air to try and escape but Adam easily held me in place. I involuntarily began drooling which only made my mouth all the more slippery. Sensing my willingness, Adam slowly raised my head up a little before plunging his thick shaft deep into my mouth.
“MMMPHHHGHH!!” I gasped but it was entirely muffled by the massive cock buried down my throat. Keeping his hands locked around the back of my head to prevent my escape, Adam began a tortuously slow rhythm, grinding his hips in concert as he thrust his monster as far as he could push it down my throat before I gagged. At that point, he’d pull back, but not enough to allow me a chance to remove myself from my compromising position.
Off to my side I heard a digital click and in my peripheral vision, I could see Lauren gleefully snapping pictures of me with her cell phone.
Adam was breathing heavily by now, plunging his thick tool in and out as he satisfied himself with my wet, willing mouth.
“That’s it Sissy boy,” he told me between draughts of air, “use that tongue of yours…I’ve got a nice creamy surprise coming for you.”
Once again I had been tricked and there was nothing I could do about it!
I squealed again and tried to escape but I was helpless against his strong, vice-like grip. If anything, my struggles seem to excite him all the more.
“Get ready Sissy, ‘cause daddy’s gonna fill your mouth with cum,” he promised with delirious enthusiasm.
I knew better than to bite down on his shaft so instead I slurped on his fat, hard shaft as he bobbed my head up and down in a frantic rhythm.
By now, he was hammering my mouth with powerful thrusts, making me dizzy as I struggled to keep up. I whimpered weakly as I my hands found his powerful thighs and used them for support.
Suddenly, he stopped thrusting for a moment, and foolishly, I thought he was going to pull out. Instead, he rammed his baseball bat deep into my mouth and exploded with a roar of ecstasy. Warm, sticky cum shot down my throat, forcing me to swallow it even as another convulsion blew more of it into the back of my mouth. My eyes went wide as I struggled to cope with the onslaught of creamy semen being blasted into my mouth.
“Swallow it Sissy,” I heard Lauren instruct me but I had little choice.
No sooner did I gulp down the batch in my throat when it was replaced by another load that threatened to drown me. I felt like I was drinking from a fire hose!
Adam was still moaning with great effect when he pulled out and I thought the end was in sight. Instead, he seemed to be making room for another stream of warm, sticky cum that quickly filled my mouth to overflowing. I gulped it down even as more leaked out from his fat head, replacing what I’d already swallowed.
Finally, Adam staggered back, his eyes rolling in the back of his head as he coped with his shattering climax. His cock came out of my mouth and was dragged across my lips and face, leaving a sticky coat of saliva and cum across my cheek.
“Oh…man, that was awesome!” he said between breaths, “That sissy really knows how to suck cock.”
I blushed even as I struggled to catch my own breath. My jaws were sore from being stretched for so long and my neck was a little stiff. In addition, the inside of my mouth was coated with semen and the sticky white stuff was smeared across my lips and cheek.
“I’m not surprised,” Lauren agreed, “I sure wouldn’t expect him to know how to please a woman.”
“You-you tricked me!” I sputtered angrily, even as cum dribbled down my chin.
Both of them laughed heartily, knowing there was nothing I could do about it.
“You might as well get used to sucking cocks, Joshy, ‘cause you’ll never be able to get a real woman,” Lauren warned me, “the sooner you get used to that fact–the better off you’ll be.”
I burned with anger and resentment at her humiliating words and I got to my feet to challenge her.
“Y-you said you were going to unlock my chastity tube,” I practically shouted, a bitter edge to my voice. My blood was boiling and I was ready to fight!
“HA HA HA!” Lauren laughed uproariously in my face.
“Wh-where’s the key?’ I demanded.
At last she stopped laughing and she looked me squarely in the eye.
“I don’t have it,” she said evenly, challenging me to defy her.
Something in me snapped and I threw myself at her but she easily deflected my charge and grabbed my arm with her left hand. Holding me steady, with her free hand, she delivered a stinging slap to my face that had me seeing stars.
“OWW!!” I cried out.
For a moment I was in shock but Lauren wasn’t waiting. She jerked me over to the crib which had the side rails down and sat on the mattress, pulling me over her lap with one quick motion.
I squealed in surprise and fear as I flailed my arms out in front of me trying to regain my balance. In an instant, I found myself face down over her firm thighs with my fat, diapered bottom raised high as I struggled to stop her. I felt her bat the hem of my frilly dress up my back and then her hand inside the waistband of my plastic panties. With a yank, she tugged them down, the sides snaps letting go on either side like zippers.
“No! N-no! Please Miss Lauren!” I begged her desperately.
“I’ve wanted to do this ever since I first saw you,” she said tersely as she deftly unpinned my diaper and jerked it back angrily between my legs.
I squirmed helplessly and whimpered in fear as I felt cool air upon my defenseless bottom.
“Adam, will you hand me his paddle?” she asked, her voice once more full of authority and strength.
“Please–please don’t spank me!” I wailed frantically. I kicked my Mary Jane clad feet and wrestled against her grip on the back of my dress but to no avail. My eyes filled with tears as I contemplated the childish punishment I was about to receive.
Suddenly I felt the cool, menacing smoothness of the paddle resting across my bare buns.
“I want my mommy!” I bleated tearfully.
The paddle rose up and came down with a resounding slap across both my cheeks.
I shouted out in pain and distress, kicking mightily.
Two crisp swats, one on each cheek followed, leaving angry, bright red patterns on my pale skin. I howled out at the top of my lungs and put my hand back to try and protect my defenseless rump but Lauren took the advantage and seized my wrist in her free hand.
Thus restrained, Lauren resumed spanking me, delivering punishing swats evenly across my tender bottom as I sobbed and banged my fist against the ground. With all my thrashing around, Lauren spread her high heeled pumps further apart to brace against me but her spanking never slowed.
Slap after stinging slap landed without pause as she peppered my fanny with the paddle. Each blistering swat seared my bottom and brought fresh torrents of tears streaming down my face. Looking down past Lauren’s sexy high heeled pumps, I saw my own babyish Mary Janes and anklets flailing around wildly as I kicked in futility trying to escape. Lauren, for her part, had no intention of allowing that to happen. She held my wrist with a grip of iron, while she swatted my cheeks with impunity.
My soft, tender buns were made scorching hot by the merciless slaps of Lauren’s fearsome wooden paddle and I wailed helplessly, sobbing like a baby. Wet streams of tears coursed down my cheeks, splattering on the nursery room floor beneath me. Looking at the mirror across me, I saw the reflection of a little toddler girl, her dress and diapers pulled up and out of the way as she received a well deserved paddling.
Finally, at last, the punishing spanking ended.
“Maybe that’ll teach you a lesson,” Lauren said breathlessly as she returned my gaze in the mirror, “Are you going to behave now?”
“Ye-yes Ma’am!” I wailed between ragged sobs.
Her paddle landed dead center across both my blazing, crimson cheeks with unerring accuracy, making me howl and kick my feet again.
“Are you going to do as your told without any of your sissy backtalk?” she demanded.
“Ye-yes M-Ma’am!” I sobbed piteously.
Setting the paddle down, Lauren pulled my diaper back up that had been between my legs, pinning either side up and around my hips snugly.
“That should teach you who’s boss around here, once and for all,” Lauren told me.
I sobbed loudly as she pulled the back of my plastic panties up and snapped the snaps closed one by one. I could feel the stinging heat on my cherry red buns rising in temperature as the vinyl panties effectively sealed in the heat.
Shaking visibly, I slowly stood up and faced my stern babysitter, who’s unwavering stare was drilling me in the face. Adam hadn’t so much as raised a finger to help her and Lauren had single-handedly defeated and spanked me, showing how vastly superior, physically and mentally she was to me. Never again would I try and stand up to her.
Just then, I heard the front door open, followed by the distinctive ‘click, click, click’ of aunt Emily’s approaching high heels on the hardwood floor of the hallway.
I swiped my arm across my tear stained face as she came into the nursery, looking absolutely ravishing as always. Seeing my new pink baby dress and Shirley Temple blonde curls, she beamed down at me happily, showing her perfect dimples and the bright twinkle in her eyes.
Rushing forward, I flung my arms around her slim waist, hugging her for dear life.


Chrissey’s Wild Adventure

Today was definitely not going well for me.
I had been playing hopscotch outside and I waited too long to go inside and go to the bathroom. Consequently, I made a slight tinkle in my pants before I reached the toilet, leaving a small wet spot in the front of my pants. This was not entirely unusual for me as I had rather weak control over my bladder and as usual, I tended to forget about it and just hope that my mom wouldn’t notice. She was in a big hurry today so I wasn’t overly concerned.
I had walked into my mom’s room while she was packing for a short business trip. However, when she looked up from what she was doing, she caught sight of the wet spot on my crotch.
”Chris! Come over here this instant,” she commanded me.
Warily, I did as I was told, realizing belatedly that she had discovered my accident after all. Standing before her, I tried to cover the spot with my hands but she refused to be put off. Pushing them aside, she glared down at my crotch with disgust.
“Chris, what is the matter with you? Are you going to start wetting your pants in the daytime too?” she asked accusingly.
She was referring to the fact that I still hadn’t been able to keep from wetting the bed and because of that, she’d begun putting me in diapers and plastic pants at night. While this solution kept my bed dry, it was mortifying to have to wear such infantile apparel at the age of twelve.
“You know, I don’t have time for this,” she stated impatiently, ”I’ve got to get going and I still have to drop you off.”
Taking me by the wrist, she roughly dragged me into my bedroom where she sat me uncerimoniously on the bed. From my dresser, she pulled open the top drawer and removed several diapers and a pair of white plastic panties.
“No Mommy,” I pleaded, “it was just an accident-please dont make me wear those.”
I was desperate to avoid going over to my new babysitter wearing a diaper.
“Chrissey,” she said, using the name she’d use whenever she thought I was acting childishly, ”if you’re going to act like a baby, I’m going to dress you like a baby.”
With annoyance and haste, she untied my shoes and pulled them off, along with my pants. I bit my lip as she yanked down my dampened underwear but I continued to protest.
“Please Mommy, I promise to do better,” I pleaded.
“I don’t have time to wait for you to do better. You’ll wear these diapers and Ms. Johnson can decide what she wants to do with you.”
“No!” I shouted petulantly, “I won’t!”
Without hesitating, my mom lifted me up by my ankles and her hand swooped down and swatted me harshly on my exposed bottom with a resounding slap. I yelped in anguish as she brought her hand down two more times to deliver a stinging lesson to my youthful fanny.
With tears forming in my eyes, I pouted while she slid the cloth diapers beneath my rump and shook baby powder over my crotch.
“When I get home, you and I are going to have a long talk, Young Man,” she promised as she pulled the thick cloth up between my legs and pinned it tightly with oversized duckie pins. While I still put up token resistance, my mom pulled the crackly pair of plastic panties over my feet and up my legs.
“It’s high time you grew up and started acting your age,” she scolded me, as she wrestled the waterproof pants over my bulging diapers. “And maybe if you didn’t act like such a baby all the time, the other school kids wouldn’t call you a sissy.”
I blushed at her reminding me of the name the kids at school referred to me as; ‘Sissy Chrissey.’
“Now get dressed while I finish packing, I don’t want to be late,” she said tersely as she strode out of the room.
I looked down at my fat diapers in despair, agonizing as to what I could find to wear over them.
After unsuccessfully going through every pair of pants I owned, I finally managed to find some old tan shorts that just barely would fit over the bulky diapers. With great difficulty I was only barely able to zip them up but they looked like they’d burst back open at any minute. Worse yet was the fact that their light color only seemed to accentuate my diapered condition and I couldn’t walk without a pronounced waddle. As I looked in the mirror, tears welled in my eyes as the reality of my predicament hit me full force.
Sniffling in misery, I tried to find a t-shirt that would cover my bulging bottom but couldn’t get anything that went lower than just below the top button on the shorts that was straining mightily to stay buttoned.
“Chris!” my mom called from down the hall, “Come on, let’s get going!’
She sounded impatient and I hastened to waddle out to where she was waiting for me by the landing. With one hand holding her bag, she used her free one to hold my hand like a toddler, something I hated. It was bad enough having to wear thick embarrassing diapers but I wouldn’t stand to be further treated like a baby. With a snotty jerk of my arm, I freed my hand from hers but as I did, I heard the unmistakable sound of my shorts ripping up the back. Wide eyed in shock, I reached back, only to feel a gaping hole going up the seam of my pants, allowing my plastic pants to be clearly visible. My hands felt the hole and the smooth vinyl of my diapers through them. To my horror, the shorts ripped even wider when I turned my head to investigate the catastrophe for myself.
“Mom!” I shreiked in distress.
“Hmmph. Serves you right for being such a brat,” she replied without sympathy.
“I can’t go out in public like this now,” I wailed piteously.
“You can and will. Now get in the car this instant Chrissey, before you REALLY make me mad,” she said in a tone of voice that brooked no argument.
Whimpering to myself I sat in the passenger side in a pout, the rest of the seam ripping all the way up as I settled down into the seat.
Filled with anxiety, I dreaded having to step back out when we reached our destination. As we drove across town in silence, I gazed down at a business card for the place we were going to.
The card read;

Ms. Julie Johnson
Babysitting special people with special needs

Below the inscription were two small drawings, the left showing a paddle with holes in its face and on the right side a diaper. I gulped hard as I wondered what the significance of that meant.
At last we arrived at a large, imposing house in a well to do neighborhood. My mom got out and began walking to the front door, only to realize I was cowering still in the front seat.
“Chrissey, you better get out of that car this minute or I’ll pull you out myself and give you a good spanking!”
Whimpering and muttering, I stepped outside tentatively, only to find that the fat seat of my diapers were actually pushing the sides of the ripped shorts outward at a ridiculous angle, displaying the plastic beneath blatantly. Frantically, I grabbed the sides and tried to pull them closed as my mom rang the elaborate doorbell.
A moment later, a beautiful young woman in a french maid uniform answered the door and invited us in after my mom informed her who we were. We were ushered into a foyer that served as a waiting room and asked to make ourselves comfortable. Ms. Johnson was finishing up with another client and would soon be out to meet us, we were told. Another woman, apparently a mother, was sitting and acknowledged us with a hello from her seat. I wasted no time in rushing to sit down in an empty chair but the other lady looked down at my balooning shorts with a penetrating gaze and then smiled at me knowingly. I blushed deeply and looked away.
For the moment, the house was quiet until I thought I heard another woman’s voice coming from in the adjoining room. Her tone seemed curt and it was followed by a boy’s whiny voice, saying something I couldn’t make out. Again the woman spoke, this time more forcefully, followed by another sound I wasn’t sure of. I heard the boy squeal no in protest and shortly thereafter, the unmistakable ‘slap-slap-slap’ of a bare bottomed spanking. My hair stood on end as I heard the boy’s cries, mixed with an uninterrupted series of swats, no doubt from the fiercesome paddle portrayed on the face of the lady’s business card.
My heart was beating a thousand miles an hour as I looked around the room, listening to the hapless youngster getting his bottom paddled. In my mind’s eye, I could easily visualize the boy’s youthful cheeks being spanked a bright shade of red, while he cried like a little baby. For a moment, the other lady caught my eye and she smiled back at me as if to say, ‘that’s what you’ll be getting soon.’
The spanking continued until it stopped suddenly, the only sound to be heard was the boy’s sobbing and obvious misery.
A minute later, a side door opened and a tall, commanding woman in high heels walked in carrying the hand of a boy about ten, his face red and wet with tears.
The mother stood up as the boy shuffled over and took her hand, wiping the tears from his face and sniffling pathetically. I noticed that his own pants bulged below his waist and realized to my shock that he was also wearing a fat diaper.
“Thank you for all your help, Ms. Johnson,” the mother gushed gratefully.
“It was my pleasure Mrs. Holms. He should be much better behaved after today,” she replied, ”so shall I expect you tomorrow?”
”Yes, we’ll be by tomorrow night at eight if that’s okay.”
“Excellent. I’ll see you then.”
It was only then that Ms. Johnson seemed to notice me and she came over to me filling me with dread. In my panic, a trickle of pee seeped out into the front of my diaper as I quivered in her stern presence.
“Stand up,” she commanded me. She wore a tight white blouse that did little to hide her voluptuous breasts and a short, black skirt that matched her dark hose.
Shakily, I rose to my feet, only to have another small stream of pee escape into my waiting diapers.
As if to read my mind, she looked down at my bulging shorts and then back into my eyes.
“You’re a little old to be wearing diapers aren’t you?” she asked pointedly.
I shuffled my feet but said nothing looking down at the floor in embarrassment.
“Answer me when I talk to you,” she said sharply, grasping my chin and forcing me to look up into her piercing eyes.
“Uh-huh,” I quivered. I only came up to her big bosom and I gulped in fear.
“Yes Ma’am,” she corrected me firmly, not releasing her vicelike grip from my jaw.
“Yes Ma’am,” I quickly added as a third trickle of pee flowed into the front of my already damp diapers.
“We’ll have to work on that,” she said evenly. Without warning, she unbuttoned my shorts and pulled them down past my knees, leaving my diapers fully exposed to everyone in the room, including the mother who was putting on her coat and getting ready to leave. I blushed hot red as she reached down and gave the seat of my plastic pants a good squeeze.
“Wet I see. But looks like you can wait a bit before I change you.”
My mom shook her head in disappointment mixed with anger. I hung my head in shame as the two discussed my arrangements before my mom left for her trip. I fought back tears while I said goodbye to her, dreading my stay here at this stern woman’s house. After she was gone, Ms. Johnson took me by the hand and then she led me into the other room.
“Chrissey, do you have to go poo poo?” she asked as we walked into a huge bathroom.
“No Ma’am,” I mumbled, still upset as to how the day was progressing.
“Well I don’t want to take any chances, your mother might tolerate changing your messy diapers but around here, we have a few rules and one of them is that sissies who are still in diapers get a nice soapy enema everyday. That keeps your diapers clean and seems to be better for both of us,” she explained.
“Wha-what’s an enema?” I asked shakily.
“You’ll see soon enough,” she replied as she began filling a large red rubber enema bag with warm water. She squeezed a good portion of dishwashing soap into the bag before sealing it up tight and attaching the tube. In a plastic box there were numerous nozzles and by habit she picked up a long, slender one but then put it down after looking at me.
“No, I think for you a special nozzle is in order.”
With that, she reached in a drawer and pulled out a fat rubber dildo like nozzle and attached it to the end of the tube. I definately didn’t like the look of that and in my hightened state of anxiety, I felt another stream of pee soaking into my diaper.
We walked out to an adjoining room where Ms. Johnson hung the glistening bag on a hook attached to the ceiling and then sat down on a straight backed chair.
“Come on Chrissey, you might as well get used to this because this is what you’re going to get every day while you’re here,” she told me.
I felt tears starting to form again and I glanced around trying to look for an escape. Taking advantage of my uncertainty, Ms. Johnson grabbed me by the wrist and yanked me over to her, tearing my ripped shorts down and throwing them in the wastebasket.
“You won’t be needing those anymore,” she said with finality.
I quaked in fear as to what was about to happen but she ignored my feelings and began tugging my plastic panties down to my ankles. Tears of shame and anxiety trickled down my cheeks as my soaking wet diapers were revealed before this beautiful stranger. She placed a towel over her lap and then pulled me over, unpinning the wet cloth and drawing it back between my legs. My damp bottom was now fully exposed and I felt her stuff a big dollop of nursery jelly into my virgin hole.
“Chrissey, this is going to be a little uncomfortable due to it’s size but it’s best if you just relax and take it in,” she explained, “besides, most sissies take to this sort of thing right away and then start to develop a craving for it.”
“I-I’m not a sissy,” I said unconvincingly.
“I can spot a sissy a mile away and believe me, YOU’RE a sissy if ever there was one.
“Now spread your legs for me…wider Chrissey…that’s better…Mr. Dildo’s going to fill you up and make you feel all better,” she said soothingly.
She rubbed the bulbous tip of the rubber phallus against my anus, searching for my hole. With her free hand, she pulled my cheeks apart and gently but firmly pushed the dildo into my pouting rectum. I squealed like a girl and kicked my feet in response to this rubber invasion but Ms. Johnson kept a steady pressure until the larger head had slid past my sphincter. I felt like I was being split in two and I sobbed in pain and shame.
“This is what all sissies need,” she assured me as she patted me on my rump while she allowed me to become accustomed to the fat dildo.
I moaned and shifted over my wet diaper, flexing and unflexing my cheeks to try and repel the rubber nozzle but my efforts were futile. After a moment, she pushed the dildo all the way in and then eased it part way out but just when I started to believe she was going to remove it, she slid it back in until it bottomed out. Another girlish moan escaped my lips and she started a slow and gentle rhythm, pumping the warm, slippery dildo in and out of my anus until I felt my little pee pee start to become erect. Quite unexpectantly, I found myself starting to relish the feeling of the fullness and the stimulation I was receiving. I relaxed and felt myself getting closer and closer to orgasm when she suddenly stopped abruptly.
“Okay sissy, that’s enough pleasure for you today. Time for us to get down to business.”
Before I could think what that meant, I heard her release the clip on the enema hose and felt a strong rush of warm water enter my bowels. I moaned again but this time it was from helplessness, not pleasure. The soapy water gurgled into my rectum and again I tried to squeeze my butt muscles to stop the flow and again it had no effect. At the first onset of cramps, Ms. Johnson shut off the valve and resumed slowly pumping me again with the dildo nozzle. My insides were churning too much by now to really appreciate it and before long, she released the clip again, allowing the water to flow freely. Bunching my fists, I shook them impotently, frustrated at my inabililty to stop what was being done to me.
After about a minute, she cut off the flow and again began sliding the dildo in and out of me. I felt sure that I couldn’t take any more water and I pleaded with her to release me.
“Ma’am, please, please may I get up now? I promise to be good…Please?” I begged her.
Instead of answering me, she brought a big pink pacifier down to my face, searching for my lips and then pushing it into my mouth, effectively ending the conversation.
“Oh, I know you’ll be good,” she said smugly, “but first you’re going to take all of this enema whether you like it or not.”
I sucked desperately on the pacifier as she released the clip again, the warm water surging into me without restraint. I had never felt so sissyish, or helpless, in my life. My insides felt like they were ready to burst and I couldn’t get comfortable. All I could think about was getting that big fat dildo out of my butthole and releasing the tremendous pressure. The enema continued without respite and eventually, beads of sweat appeared on my forehead. Gasping from the pressure, the pacifier dropped out of my mouth and I sobbed like a sissy.
“I want my mommy-I want my mommy,” I whimpered pathetically.
“Feeling a little full, baby?” she taunted me.
“Yes, Ms. Johnson, please let me up, PLEASE,” I blubbered.
“I like my babies to get a very thorough cleaning, it does them wonders,” she gushed, “don’t worry, you can still take some more.”
“Mommy, I want my mommy!” I repeated.
At long last, the sound of the last bubbles dissappearing into my bowels could be heard and after what seemed like an eternity, Ms. Johnson slowly extracted the dildo nozzle.
“I better not see one drop on the floor Chrissey or you’ll find out first hand, just how much my paddle stings,” she warned me.
I rose up with difficulty, my entire being focused on the huge volume of water forced into me. My tummy was distended and I felt like I was holding back Niagara Falls. Without waiting, I limped off to the bathroom to disgorge my enema.

Twenty minutes later, I came out of the bathroom, wearing just my tennis shoes and a towel around my waist for some measure of modesty.
“Chrissey, I’m in here,” I heard Ms. Johnson call to me from down the hallway.
Apprehensively, I made my way down looking in each room until I reached the last one. Soft light filled the room and I looked in to see a baby’s nursery lavishly appointed with pink curtains and wallpaper. A large crib was in one corner and a pink dresser stood near a plastic lined changing pad. Dresses and other little girl’s outfits filled the open closet but what caught my eye was a menacing looking oak paddle hanging on the wall, ready for use. Six holes were drilled in it’s face and I shuddered at the thought of being its victim.
Ms. Johnson beckoned me to come in and she patted the changing table for me to sit on it. It was at that moment, that I noticed another girl in the room. She looked to be a couple years older than me, pretty, and I could tell right off she wasn’t wearing a diaper. I hesitated before sitting down.
I couldn’t allow this woman to put me in a diaper, especially in front of this girl.
“Chrissey, this is Susan. I’m also taking care of her today,” Ms. Johnson said. I noticed she didn’t use the term “babysit,” which I was sure she wouldn’t hesitate to apply to me.
Nervously, I stalled as I shifted my feet, but Ms. Johnson reached over and snatched the towel from around me and threw it in the corner.
I gasped in shock and quickly covered my privates, looking at the door for escape.
“It’s diaper time, Chrissey, and you won’t be needing that towel anymore,” she said simply, making me blush profusely.
Susan giggled and Ms. Johnson pulled me down onto the table where a thick, fluffy white diaper lay.
“There are no secrets in this house,” she said as began powdering me generously, “and a big sissy like you should be in diapers around the clock, so don’t be surprised if some other people find out about your wetting habits.”
I turned beet red and whimpered in embarrassment.
She pulled the soft cloth between my legs and pinned them up on either side snugly. These were much bulkier than the ones my mom put me in and softer too. The fleecy folds caressed my pee pee and hugged my bottom pleasingly.
My briefly enjoyable discovery was cut short as she shook out a pair of pink, nursery print plastic panties before me.
“Oh no!” I cried, “don’t you have any white ones?”
“This is what you’ll wear,” she said brusequely as she held them open by the legs holes and forced them up my relcaltrant legs. I kicked defiantly but she pulled them up to my thighs anyway. The diapers were so thick that she had to struggle with them a bit to get the shiny plastic panties to fit around their tremendous bulk. After tucking in a few bits of cloth that were outside the panties, she sprinkled some baby powder on my inner thighs. All the while, Susan was watching intently and beaming at me, obviously enjoying my predicament. My cheeks were hot with shame as I sat up in my new underwear.
Going to the dresser, Ms. Johnson pulled out a Care Bears t-shirt that was decorated with pink flowers and removing my own shirt, replaced it with the new one. I felt like a total sissy baby as she plopped another big pink pacifier in my mouth and passed it’s loop behind my head. Glancing at the mirror on the far wall, I blushed at my appearance as a thickly diapered toddler girl.
“There,” she said as she slapped my padded and pantied bottom, “run along now and try to stay out of trouble.”
I sniffled in shame as I waddled out of the room. Because of the powder between my legs, the thick diapers swished smoothly as I moved but the bulk was still very much apparent.
I went into the den and started looking around at books and things, trying to get used to my babyish condition. I was lost in thought when I heard Susan’s voice behind me.
“What are you doing Chrissey?” she asked pleasantly enough.
“Don’t call me Chrissey, my name’s Chris,” I insisted petulantly.
“You look very cute in your baby clothes, Chrissey,” she said, deliberately ignoring my remark.
I wasn’t used to pretty girls giving me attention so I decided not to be too particular about the name. In addition, I welcomed her admiration, even if if was due to my sissy clothes.
“I don’t normally wear diapers,” I tried to tell her, “I just had a little accident today, that’s all.”
“Really? You could’ve fooled me. You look like you’ve been wearing diapers all your life,” she said to contradict me.
I didn’t like the way the conversation had turned and I couldn’t help blushing.
“Your face is getting red,” she said pointedly, “its because its true isn’t it?”
Despite my best efforts, my face only grew redder.
“No! I don’t wear diapers!” I lied, “she only made me!”
“I’ll bet you’re a sissy bedwetter and I’ll bet you’d wet your pants too if your mommy ever let you out of your diapers during the day,” she said taunting me further.
I was angry at her assumptions, partly becuase they were so close to the truth.
“I do not!” I denied hotly, “I don’t wear diapers during the day!”
“Well you are now, sissy baby. And looks like you’ll be wearing them from now on,” she said with a smug smile.
I realized it was difficult to argue while I was dressed in a Care Bears shirt and a thick diaper and plastic panties so obviously displayed.
“Have you wet your diapers yet? We don’t want our little baby to get diaper rash,” she teased me.
“Stop it! Leave me alone,” I pouted.
“I better check you to make sure,” she said as she reached over to put a finger down the front of my diaper.
I pushed her away roughly but she twisted my arm with surprising strength. All I could do was flail around and I managed to scratch her forearm enough to make her cry out.
“You little sissy, you’re gonna get it now,” she spat viciously.
Before I could make a reply, she had spun on her heel and left the room. I fidgeted nervously wondering what she had in mind and part of me feared a spanking from Ms. Johnson. I started formulating some kind of defensive argument in case that were to happen but I didn’t have long to wait.
Ms. Johnson came down the hall, her high heels clicking on the floor and the fearsome paddle in her hand. I gulped in fear, terrified of getting a spanking at her hands. Susan was close behind her and she stood next to her holding her arm as Ms. Johnson glared down at me.
“Chrissey, Susan tells me you scratched her on the arm, is that true?”
I bit my lip nervously as I eyed the paddle she held in her slender manicured hand.
“Um…she started it,” I blurted out defensively.
“I don’t care who started it young man, around here, you will learn to behave yourself,” she said as she pulled a straight backed chair out into the middle of the room. As she sat down, she pulled me over to her and started tugging my plastic panties down.
“Please…please don’t spank me Ms. Johnson,” I pleaded, “I promise to behave-honest!”
“Oh you’ll behave all right,” she said as she pulled my panties down below my knees, “but first you’re going to become better aquainted with my paddle.”
I quailed in fear at the determination in her beautiful, dark eyes and she yanked me over her skirted lap, removing the pins from my diapers in short order.
“No…please, please don’t spank me!” I wailed piteously. Tears started streaming down my cheeks while I felt my diaper being pulled back and the cool air hit my naked fanny. Susan had moved around to sit in front of me and I saw the smug smile return to her face in anticipation af what was about to happen.
“Chrissey, I want you to think about what you’ve done. Maybe this’ll teach you a lesson.”
The first impact of the paddle seared itself on my virgin bottom with a loud and crisp SMACKK!!
My eyes went wide and I bolted upright but Ms. Johnson held me firmly in place over her lap.
The oaken paddle rained down upon my poor defenseless bottom, with harsh, angry slaps. I immediately burst into real tears and began bawling like a baby, kicking my feet and shaking my bunched fists.
My bottom quickly turned a bright shade of red as Ms. Johnson spanked every inch of it. When she had turned the center of my buns into a blazing inferno, she smacked the sides, making them look like two glowing apples. I wailed and flailed as the tears streamed down my face, perched helplessly over her long, smooth legs and high heels. Each new slap of the wood paddle brought with it a blistering sting and fresh tears. Now that the sides of my fanny were on fire, she returned her attention to the center, applying fierce, punishing swats until my cheeks became a reddish-purple.
At last, the painful spanking was over. I lay over her lap, my pink plastic panties in a tangle about my ankles and my face wet with tears. I bawled uncontrollably but she refused to let me up.
“Chrissey, are you going to be good little boy around here now?” she asked, the paddle still raised over my punished bottom.
“Y-y-yes,” I wailed through my sobs.
Once again, her avenging paddle crashed down on my derriere.
I cried out anew, blubbering like a toddler.
“Are you ready to say you’re sorry to Susan?” she asked.
“Y-yes!” I bawled. I tried to catch my breath which was coming in heaving gasps. My buns felt like a red hot frypan was being pressed against them.
“I-I’m s-sorry I scratched you S-Susan,” I stammered ashamedly.
“Well,” she replied smugly, “looks like you know who’s boss around here now.”
I continued crying as Ms. Johnson pulled the thick cloth of my diaper back up between my legs and over my stinging fanny, pinning it securely in place. This only served to contain the heat on my bottom and I squirmed in discomfort. Ignoring my sissyish whimpering, Ms. Johnson stood me up and pulled my nursery print plastic panties up my legs, struggling to get it over my bulging diapers. I was granted a generous view of her magnificent breasts, stretching her sheer blouse tight and revealing a white lacey bra underneath. Seeing me crying like a baby, she plopped my pacifier back in my mouth and I sucked on it obediently. For some reason, it felt strangely comforting and natural but it was plain that she felt absolutely no sympathy for this little boy.
“I think it’s time for our baby’s naptime,” she said as she stood up and looked down at me with her hands on her hips.
At this point, I was hardly in a position to argue with her so I followed her into the kitchen where she put a baby bottle filled with milk into the microwave. I shuffled in my shoes and rubbed my still blazing bottom through the thick padding of my diapers and plastic panties. After the oven dinged that it was finished, Ms. Johnson led me down to the nursery while she discussed with Susan what they would do the rest of the afternoon. I was extremely frustrated that they were going to be having a good time while all I had to look forward to was a baby bottle and a boring nap in a crib.
Once in the nursery, I pouted while Ms. Johnson busied herself untying my shoes and lowering the rail so I could get in. When she pulled back the colorful pink and white baby blankets, I saw waiting for me, a vinyl waterproof sheet, decorated with nursery characters. Still sniffling, I got in while my pacifier was replaced with the baby bottle.
“Make sure you finish all that,” she admonished me as she pulled up the blankets to my chin. With a solid click, she raised the crib rails, warning me that if she caught me out of bed, I could count on another paddling. Susan smiled down at me as she handed me a stuffed dolly and made sure I accepted it.
“See you at your changing time,” she said tauntingly.
As they walked out, they left the door open, making sure I wouldn’t have any notice should they decide to come in unexpectantly.
As I slowly drained the milk, my eyes wandered over the furnishings in the nursery and I wondered about my new life here. I felt like I was four again, not twelve and about to become a teenager. It had taken me a lot longer than most kids to graduate from sleeping in a crib and wearing diapers during the daytime. Even after that big step, it was many years before I could go without wearing a thick set of diapers and plastic pants when I went to bed. Maybe I really was a baby and a sissy deep down like everyone said.
Suddenly and without warning, I felt my diaper growing wet and warm. I realized to my dismay, that I seemed to have lost my daytime control again as I wet myself like a toddler.
Oh well, looks like I better get used to wearing diapers during the day again, after all, I thought.
I grew a little tired and slowly drifted off to the soft slumber of sissy sleep.

I slept restlessly and finally awoke to the sounds of laughter from out in the living room. Obviously, Susan was having a good time with Ms. Johnson and was enjoying quite a different relationship than my own.
To my surprise and dismay, I felt a soggy mass of cotton embracing my loins, securely encased by my crinkly plastic panties. I must have thoroughly soaked my diapers during my nap and I could only imagine how Ms. Johnson would react. As I lay on the vinyl covered mattress, it crackled and creaked with each movement. I could feel that even the thick seat of my diapered bottom was completely saturated and it clung miserably to my cheeks, a constant reminder of my infantile lack of self control.
As I pondered my bleak situation, I heard more laughing outside the room, this time approaching the door. Ms. Johnson strode through with Susan behind her and without delay, she came in and unlatched the side of the crib. Wordlessly she pulled down the baby blankets and squeezed the front of my diapers.
“Did he wet his diapers?” Susan asked bluntly.
“They’re soaked,” Ms. Johnson replied, a look of stern disapproval darkening her features, “you really are nothing but a big baby, aren’t you?”
I squirmed uncomfortably and blushed in embarrassment.
“Looks like I’d better get you changed,” she said with resignation. Taking me by the hand, she guided me over to the changing table, where the diapering supplies were arranged. I sat down with a wet squish and Ms. Johnson proceeded to peel my plastic panties down that clung to the pee soaked cloth. I bit my lip anxiously as she unpinned my diapers and pulled them out from under me, leaving me damp and bare below the waist.
“You sure have a small wee-wee,” Susan remarked.
I blushed again and tried to look the other way while Ms. Johnson began wiping my diaper area with several baby wipes. Reaching under the table, she pulled out two very thick cotton diapers, with sewn in soaker pads in the middle. Lifting my ankles, she slid them under my rump that was still pink from my spanking earlier.
“Do you hafta make them so thick?” I complained.
“A big baby like you needs a big diaper,” she said simply, as she shook powder over my crotch, ”maybe if you’d act your age, I wouldn’t have to put you in diapers. Ever think about that?” she quipped.
I looked over at Susan who was nodding with a big smirk on her face.
I said nothing as Ms. Johnson pulled the bulky cloth up between my legs and began pinning the ends together.
“Susan, would you mind picking out a pair of plastic panties for Chrissey?”
“Sure thing,” she replied eagerly.
I was mortified to have Susan standing there staring at me as I got my diapers changed so I welcomed anything that would make her leave, even if only for a moment. I realized belatedly how misplaced my relief was when she came back, displaying the panties before her by as she stretched them by their elastic waistband. They were a pale pink color with yellow flowers and bunnies and soft white ruffles around the leg openings and waist.
I cringed as she held them up for Ms. Johnson to see. She looked at them, and then me, as if she were determining whether they were appropriate or not.
“I think those will be just fine,” she said as she gathered the leg openings together. Seeing that she was about to slip them over my feet, I kicked to try and resist her.
“I don’t want to wear those-they’re for girls!” I squealed in protest.
“These’re perfect for a big sissy like you,” Ms. Johnson insisted sternly, ”but maybe you need another session with the paddle.”
“No-no!” I hastened to say quickly.
Ms. Johnson proceeded to pull the gathered plastic panties over my feet and up my legs to the top of my thighs. I pouted helplessly as she tugged them effortlessly up and over the bulky cloth of my diapers. Running her long manicured nails around the elastic waistband, she pulled them all the way around to cover the diaper completely. I whimpered meekly as her big breasts swung provacatively before me, pressed tightly against her white, semi-transparent blouse. She shook the baby powder between my legs to make the contact between my thighs and the vinyl panties silky smooth.
“There you go Chrissey,” she said as she let me up, “all diapered and ready to go.”
As I rose to get up, I was acutely aware of the soft bulk between my legs that forced me to waddle out of the nursery like a toddler. How had I allowed myself to slip down to this level of sissyhood? I walked down the hall but I couldn’t escape my feelings of babyishness. Wearing a soft Care Bears shirt and a fat diaper that made me look like a toddler girl, I felt like a total sissy. Would I ever be able to wear regular underwear again?
My thoughts were interrupted by Susan who had come out to find me.
“Hey, why don’t you come down to my room and we’ll have some fun?” she offered in a friendly manner.
I was still attracted to her, even if she had been cruel and I was eager to get on her good side so I followed her to one of the house’s bedrooms down the hall.
“What are we going to do?” I asked curiously.
“You’ll see,” was all she would say.
We went into her room which was very feminine in its decor and she sat me down on her vanity stool, taking care to face me away from the mirror. Taking a large hairbrush, she began brushing my longish hair which I found very relaxing, the first time I’d felt that way since my arrival at this house. I couldn’t see what she was doing but I felt her pull my hair tightly on either side and secure it with something out of my view. She hummed as she dug through a box of something behind me until she came back to me with a small make up brush. Before I could do anything, she brushed some pink blush on my cheeks.
“Hey! What’re you doing?” I demanded.
“Don’t worry, Chrissey,” she said as she held my outstretched hands down, “you’ll look really cute when I’m finished.”
“I don’t want to wear makeup!” I protested.
“Didn’t you ever play house when you were little?” she asked, “That’s all we’re doing now. And don’t worry, no one’s going to see you. Besides, I think you look so cute like this.”
Something inside told me she wasn’t being honest with me but I really wanted her to like me so I reluctantly acquiesed. She unrolled a stick of bubble gum pink lipstick and carefully applied it to my lips, telling me I had such cute ‘kissy-lips.’ As a last touch, she gave me several sprays of perfume which made me cringe.
“Come on, I’ve got one more thing to make you complete,” she said as she tugged me off the stool by my wrist. As we went out the door, I caught a look at myself in her vanity mirror. My hair was now in two pigtails, held in place by two big pink floppy bows which matched my pouty lips. I blushed profusely as I staggered down the hall behind Susan. We went back into the nursery where she sat me down on the changing pad. Going to the dresser, she chose a pair of white and pink anklets, very lacey and babyish, and put them on my feet. In the closet, she found some black patent leather mary jane shoes that she wasted no time securing to my feet.
“There,” she said, “now let’s take a look at you.”
Helping me up off the changing pad, she stood me up and stepped back to look at me.
I felt completely sissyish, my hair in pigtails, bright pink lipstick on my lips, my sissy Care Bears shirt that snapped up the sides and barely reached down to the thick bulging diaper that was wrapped in my pink nursery print plastic panties. The final touch was the ruffled anklets and mary jane shoes.
“Well, well, well,” Ms. Johnson said as she stood in the doorway, “aren’t you the little sissy.”
I blushed red as I tried to come up with an excuse for my appearance.
Susan giggled as Ms. Johnson came over and took my hand.
“Why don’t you come out to the living room Sweety-pie, there’s someone here to see you,” she said craftily.
I cringed in fear as I wondered who it could be. It really didn’t matter because I was terrified at the prospect of anyone seeing me like this.
I waddled out behind her helplessly and into the living room with Susan behind me.
“Mrs. Brooks, your son is all ready for you now,” she said as she pulled me out in front of her.
I blushed a hot beet red as I looked to see my mother’s mouth drop in shock and then try to suppress a giggle. I was practically swooning with embarrassment and without warning, the front of my diapers suddenly grew wet and warm. I bit my lip and fidgeted but it was too late, now everyone would see why I needed diapers during the daytime.
“Chrissey! You look so darling in your little outfit. I had no idea about this side of you,” she exclaimed.
“Yes,” Ms. Johnson explained, “I just walked in on them, it looks like he was playing dress-up with Susan here.”
“And don’t let him tell you any different, Mrs. Brooks,” Susan chimed in, “he loves dressing up like a baby.”
I was about to burst out with a long and spirited defence but Ms. Johnson, sensing my aggitation, quickly stuffed a big pink pacifier into my mouth, holding it in place while I meakly whimpered.
“Well, I guess I always knew he was something of a sissy, I just never really faced up to it,” my Mom admitted.
“The fact is, your little boy is still just an overgrown baby. He hasn’t been able to keep his diapers dry since you dropped him off this morning,” Ms. Johnson informed her.
My Mom shook her head in dismay and she reached down to slip a finger into the front of my diapers to check me.
“You’re right about that, he’s wet again,” she remarked disappointedly.
“That was quick,” Ms. Johnson replied, “I just changed him not fifteen minutes ago.”
“Well it looks like I’ll be throwing out all his old underwear when we get home,” my mom said tiredly, “It’s diapers and plastic panties from now on, for you, Young Man,” she told me sternly.
I quivered and wilted under her penetrating gaze as I stood there helplessly.
“And if you like to play with girl’s make-up so much, we can just get you your own. I’ll just throw out your boy’s clothing that you obviously have no interest in and replace them with something a little more appropriate.”
I shook my head vehemently but my mom just ignored me.
“Come along you little sissy,” she said as she slapped the wet seat of my diapers, “we’ll stop by the mall on the way home. Hope you don’t mind going out in public like that because thats exactly how you’re going. And I don’t want to hear one word out of you about your wet diapers. I didn’t bring over a diaper bag so we can just change you when we get home. Looks like you’re going to become very familiar with the feeling of soggy pampers, won’t you?”
Tears of humiliation trickled down my cheek as she scolded me in front of the others.
“Did he give you any trouble today?” she asked Ms. Johnson.
“Yes, but we got it all sorted out with the paddle. I think you may find his bottom’s still a little pink when you go and change him,” she replied with a smile.
“Good, he was due for a hard spanking anyway,” my mom told her, “and I think you can count on that little sissy bottom being paddled a lot more frequently since you insist on acting like such a baby, Chrissie.”
“If you need to pick up any baby wear, I can give you the address a for a shop here in town that caters to ‘bigger’ babies,” Ms. Johnson offered, “and you’ll find they have a huge selection of diapers, plastic panties and other hard to find items that will fit his size perfectly.”
“That would be wonderful, you are so helpful, what would I do without your services? Yes, we’ll need to stock up on plenty of diapers, I’d like to pick up some cute baby panties too-I love the plastic panties you’ve got him in now-they’re so appropriate for a sissy who can’t keep his pants dry.”
“Thank you Mrs. Brooks, I picked those out for him,” Susan told her.
“Well you seem like a very smart young lady. Perhaps you wouldn’t mind coming over to babysit for me sometime?”
“That would be great!” she exclaimed, “I’ve taken care of lots of babies and this one’s such a weakling, it’d be a cinch.”
“Excellent. Here is my number and address, please call me tonight and we can set up a schedule.
“And now my little Pamper Princess, it’s time to go shopping,” she told me firmly.
I should have spit out my pacifier and ripped off the sissy Care Bears shirt I was wearing but instead, I just sucked away, knowing I was about to be humiliated like never before in my life. As I pouted and contemplated my imminent exposure, I felt another trickle of pee seeping into my diapers.
“Say goodbye to Ms. Johnson, Chrissie, and thank her for all her hospitality,” my mom ordered me.
I thought back on the long soapy enema and the harsh spanking she’d given me and I just stood there.
My mom’s arm swooped down and slapped my diapered bottom with a thud.
“Chrissey! Don’t be rude!” she admonished me as she popped my pacifier from my lips.
“Th-thank you, Ms.-Ms. Johnson,” I stammered.
“Say; ‘thank you for recognizing what a big sissy I am,'” she instructed me.
“No Mommy!” I pleaded piteously.
“Looks like I’ll be using the paddle a lot sooner than I anticipated,” she said as she crossed her arms and waited for me.
Biting my lip, I stared at the floor.
“Tha-thank you for recognizing what a big sissy I am,” I quivered.
“Don’t you worry my little one,” Ms. Johnson replied as she chucked my chin, “I’m sure you’ll be a lot happier in your diapers and dresses than those nasty boy clothes.”
A tear of embarrassment formed in my eye and I looked away.
“Well, we better get going, we’ve got a lot of shopping to do. Thank you both again. We’ll be seeing you soon, I’m sure,” my mom said as we walked out.
They said their goodbyes and we got back in the car where I sat in my seat with a wet squish. I silently prayed that my plastic panties wouldn’t leak. That would be all the excuse my mom would need to blister my bottom when we got home.
We drove for about a half an hour until we pulled up in front of a small shop titled, “Mommy’s Fashions.”
It was only with considerable persuasion that my mom convinced me to step out of the car and walk in. Upon entering, I could see little girl’s dresses hanging everywhere and a vast array of baby furniture and toys.
An attractive lady came up to greet us and after looking me up and down, and then up and down again, she beamed and bent over to greet me. I couldn’t help but notice the line of cleavage that disappeared down the front of her top which was generously filled with her breasts.
“Well hello there,” she said pleasantly, “and what’s your name?”
All I could do was blush and look away.
“He’s a little bashful but his name is Chrissey,” my mom said for me.
“Well Chrissey, don’t you look cute today,” the lady offered.
I looked back into her pretty eyes but I didn’t know what to say. In the brief interlude of silence, my bladder decided to let go and the distinct sound of my diapers being peed into was unmistakable. As both of them focused on me, I turned bright red with shame. The lady giggled and smiled down at me, “It’s good your mommy has you securely diapered Chrissey, it sounds to me like this little girl is going to need a change,” she observed in her syrupy voice.
“Yes, perhaps you can show us some diapers in his size,” my mom asked, “I’m afraid I’ll be needing to stock up.”
“Of course! Come right this way,” she said as she made her way down the aisle.
“Now we have several styles in his size, but these are my favorite,” she said as she held up a large thick rectangle of cloth, “these are called ‘Soakers’ by Bedwetters. They were designed for little boys who can’t keep their beds dry at night,” she chuckled, “very thick and absorbant so he can go all night without a change. I recommend using two to three, depending on how much of a wetter your little one is.”
“Oh he’s a regular fountain, aren’t you Chrissey,” she prodded me.
“Well then, you should probably triple diaper him. Notice the extra thick padding down the center and this cotton is so bunny soft, he’ll be comfortable wearing them 24 hours a day,” she assured my mom.
“That’s good because that’s exactly how long he’ll be wearing them. All his old underwear are going straight to the trash when we get home.”
“And you’ll need some plastic panties to go with those,” she said as my mom filled a shopping cart with stacks of the diapers, “we have plain white of course but from the looks of things, maybe you’d like something a little more… feminine?”
“Absolutely,” my mom replied firmly, “have you got any rhumba panties in his size?”
“Oh yes! Take a look at these,” she said holding up a pair of pink ruffled panties, “soft plastic inside, and silky fabric outside, with three rows of ruffles across the bottom. These will easily fit over the triple diapers he’ll be wearing.”
“Those are SO cute!” my mom exclaimed.
“And these are also nice,” the lady said as she held up a pair of white nursery print panties, their legs and waistband adorned with pink, fuzzy ruffles.
“Perfect for a big sissy in diapers,” my mom agreed.
Together, they picked out about twenty pairs of plastic panties in all colors and styles. When that had been moved up to the register, they returned to the dress section.
“Since I discovered my son wanted to be a sissy, I thought some babyish dresses would be more appropriate,” she explained to the lady.
“I have just the thing-now how low would you like the hemline? I have some that would go to about his knees or I have higher…” the lady said.
“”Do you have any that will show off his diapers? I want them on display for everyone to see,” my mom told her, “After all, we wouldn’t want to hide those pretty panties. now would we?”
“I couldn’t agree more,” the attractive lady concurred, “Now this dress has a very short hemline,” she said holding it up against me, “his diapers will be exposed at all times.”
“Isn’t that one cute,” my mom remarked admiringly.
“See the extra stitching that went into this one, plenty of lace and frills for even the most demanding sissy.”
“Oh can he try it on now?” my mom asked breathlessly.
“Of course! I’m sure he’ll look just darling in it.”
Putting it over my head, I reluctantly held my arms up and let her fasten it up behind me.
“Notice that all of our dresses button up the back-that’s to make sure that mommie’s little sugar plum can’t remove it himself.”
“Excellent. Yes that definately suits him,” my mom said as she took in the full effect on me, “turn around Chrissey, let’s see how you look in back.”
I pouted but twirled around and could tell that the flouncy lace hem was right at my waistline, showing off my fat diapers completely.
“Would you mind if he wore this home?” my mom asked, “it’s just the most precious thing I’ve ever seen.”
“Not at all, let me just remove the price tag,” she said as she snipped it off from the neckline.
My mom and the sales lady spent another half hour picking out dresses before they were finally finished and were ready to check out. By now, my diapers were completely soaked and I was anxious for a change so I tugged on my mom’s sleeve tentatively.
“Mom, my-”
“From now on, I want you to call me Mommie. Is that understood?” she informed me.
“Yes Mommie,” I corrected myself, “um…my um, diapers are um, kinda wet. Do you think I could get changed now?”
Without answering, she reached down and squeezed the now soggy seat of my diapers, realizing that they were soaked.
“Nope. You can just get used to the feeling of being wet. You wanted to act like a baby and now you’re going to get the chance to feel what it’s like to be one,” she said very matter of factly.
“Don’t worry little sissy,” the lady said as she pouted her lips at me in mock sympathy, “everything’s going to work out just fine.” With that, she popped my pacifier between my quivering lips as I started to cry.
Tears streamed down my cheeks and I sniffled at how unfair life was.
“You know,” she said as she looked down at me, “it looks like his diapers are starting to sag a bit. If you’d like, we can slip on a pair of these rhumba panties. They’ll help keep up his diapers and he’ll also get to feel the wet cloth, closer to his skin.”
“Excellent idea,” my mom agreed as she finished writing out the check.
The pretty sales lady came around with a pair of the pink ruffled rhumba panties and held them down and open for me to step into.
“Here you go Sissykins, pretty panties for a pretty little boy.”
I sniffed and wiped my hand across my tear stained face as I lifted my foot to put it through the leg hole she was holding open. After one mary jane and then the other, she slid the satiny panties up my thighs and then tugged them into place over my bulging diapers.
“Isn’t that just the cutest thing!” she remarked admiringly.
I wanted to crawl under a rock and die.
“Don’t cry little baby, every sissy loves to wear special panties,” she cooed to me. She seemed to take special pleasure in teasing me.
My mom reached down and tugged all around at the waistband, ensuring the panty covered the diaper completely which had the additional effect of pressing the soaked cloth up against my skin. By now, the pee had seeped up the seat and even around the sides but still there were no leaks in evidence. This was one thirsty diaper!
My mom thanked the lady for all her help and gave me two large bags to carry out to the car which were combined with the two she was carrying for a lot of baby supplies. I cringed at the thought of having to wear all these infant clothes, day after day, and being exposed to the neighborhood as a total sissy.
As I waited for my mom to open the door, a pair of teenage girls walked by and stopped to stare at me, their initial shock being replaced with barely concealed giggles. I blushed again and dove in the car as soon as the door was opened, facing down to try and ignore them while my mom got in on the other side. As we pulled out of the parking space, I looked up to see them waving bye-bye to me, like they would a little baby.
“Looks like you found some friends, Chrissey,” my mom remarked sarcastically.
With my pacifier in my mouth, I remained silent with the exception of my sniffling and whimpering.
“Well, it’s getting late and you’ve got an early bedtime now. I guess we’d better head home,” she told me.
It was getting dark by the time we pulled up into our driveway which was fine by me. I hoped the cover of darkness would hide my appearance from the neighbors while I went from the car into the house. I expected my mom to grab the bags of clothing she’d bought but instead, she took her luggage from earlier and left the door open.
“Chrissie, take those bags to your room and then come back out here and get the others as well.”
“Yes Mommy,” I replied sullenly.
I hurried to get inside where I put the bags in my bedroom and then went to the window to see if anyone was outside that might see me as I went back out to the car. It looked like the coast was clear so I rushed out and yanked the door open, grabbing the last two bags and then spinning around to go back inside. In my haste, I tripped and the bags fell out of my hand, spilling their contents all over the lawn. A young woman, who happened to be walking by at that moment saw me, and came over to try and help me.
“Let me help you, Honey,” she said as she bent down to gather the fallen items. I hadn’t seen her when I walked out and now I was crushed with shame as she picked up each of my plastic panties and with great care, stacked them neatly into a pile.
“You’re a little old to still be wearing diapers, aren’t you?” she asked.
“Y-yes,” I stammered as my face grew red and flushed.
She looked at me with an odd look on her face as she tried to understand why I was dressed the way I was.
“You don’t actually wet your diapers do you?” she asked pointedly.
With my soaking wet diapers clinging close to my loins, I was hard pressed to try to deny the truth.
“I-uh…um, well I-” I stuttered.
Without waiting for an answer, she reached over and squeezed my rhumba pantied bottom, quickly feeling the saturated cloth contained inside.
“Oh my! You ARE wet! You better have your mommy change you, Little Sissy-boy,” she insisted.
“Um…I will,” I stammered as I quickly grabbed the panties in front of her and stuffed them into the bag. With all haste, I stood up and ran inside leaving the shocked woman on the lawn.

When I got to my bedroom, my mom was filling a large garbage bag with my old clothes, clearing the dresser and closet to make room for my new wardrobe. As I saw my jeans and shirts disappearing into the trash bag, I burst into fresh tears, stamping my feet on the floor in frustration.
“Mom!” I cried, “do you really have to do that?” I pleaded, “can’t I just keep some of them?”
“Chrissie, YOU are the one who has been acting like a baby, wetting you pants and your bed like a little toddler. And then today I come over to pick you up and I catch you playing dress up like a little girl!” she said vehemently.
“B-but, those two made me dress like that!” I insisted.
“Hmph! That I doubt. Remember last year, when I caught you going through your cousin’s panty drawer? Who was forcing you then, hm?
“No, I think you’re just embarrassed that you got caught this time. Only this time, I’m going to indulge your little sissy desires. You’re going to carry these clothes straight out to the trash and I don’t want to hear another word out of you. Is that understood?” she said sternly.
“”But Mom!-”
“That’s it!” she barked, “I’ve already told you once you are to address me as Mommy but you’ve obviously forgotten,” she said as she sat down on the bed and reached for the paddle. “Maybe this will help reinforce your memory. And next time when I tell you to do something, you’d better do it without argument.”
She yanked me over to her by my wrist and began tugging my rhumba panties down my thighs and past my knees. I blubbered and stomped my feet as she angrily peeled my plastic panties down as well, lowering them down to my ankles.
“No Mommy!” I begged her belatedly, “please don’t spank me! Please!”
Ignoring my protests, she hauled me over her lap and began unpinning my wet diapers, the smell of urine filling the room.
Tears of shame spilled down my face as I saw her reach for the paddle, my damp bottom now fully exposed.
“Chrissey, this is what happens to diaper wetting sissies that don’t mind their mommies in this house,” she said tersely.
With a harsh slap of the paddle, she landed it squarely in the middle of my tender and still pink rump. I shrieked in pain and kicked mightily but my panties restricted my efforts.
In quick succession, the paddle rained down on my fanny with stinging ferocity. I bawled and wailed, the tears streaming down my face as she spanked my blushing cheeks into a hot, cherry red.
As I sobbed and cried, I knew my days as a budding teenage boy were over. Never again would I argue about having to wear diapers and sissy clothes. Besides that, deep down, I suspected that what she was saying was true. I really was a big sissy, I’d just never admitted it to myself. Maybe she was right, that diapers and plastic panties really were more appropriate for me to wear than my old pee-stained undies. I guess some boys were destined to grow up and some, like me, were destined to be sissies that never outgrow their diapers.
Of course, all these thoughts made little difference as my mom continued to paddle me for the next several minutes. When she finally stopped, I lay over her lap completely defeated, sobbing and ready to be compliant. She stood me up and then took me in her arms, giving me a loving hug to say that all was forgiven.
“There, there Chrissey, everything’s going to be okay,” she cooed to me as she stroked my back, “Shush little baby, Mommy loves you.”
She kissed me on my tear stained cheek and then laid me down on the bed where she began cleaning my diaper area with baby wipes. While I continued to cry, she eased my pacifier in between my quivering lips which provided some measure of solace for me. She also gave me my old teddy bear and put it under my arm, urging me to hold him close for comfort. With several good shakes of the baby powder, she smoothed the sweetly scented powder over my bright red bottom and wee-wee area lovingly, before taking three of the new diapers and sliding them under my stinging fanny.
“These are SO soft,” my mom commented, “I’m sure your just going to love wearing and wetting them.”
Pulling the bulky thick mass of cotton between my legs, she pulled the corners up against my waist where she snicked them closed with the oversized diaper pins. I had to admit that they were extremely soft and comfortable and they caressed my wee-wee gently even as they pushed my legs apart with their bulk.
“Let’s see, which baby panties to wear…” my mom mused as she sifted through the plastic panties, “How about these?”
She held up a white pair of satiny rhumba panties with a pink lamb stenciled on the front. On the back were three rows of sassy ruffles, edged with pink lace.
“This should keep my little sissy happy,” she said as she slid them up my legs. I lifted my bottom to help her as she pulled them over the triple thick diapers. When she had finished, she ran her fingers around the elastic leg and waistbands, making sure the diaper was completely sealed. Standing me up, she re-arranged my dress and patted me on the thick seat of my pantied fanny.
“There. That should take care of you until bedtime,” she said satisfied.
“Now I want you to hang up all your dresses and put away your new panties. The diapers you can stack here next to the bed-I’ll go out and buy you a changing table tomorrow.”
I was still sniffling as I went to do her bidding. The heat from my blazing bottom was sealed within the thick folds of my diapers and plastic panties and it stung painfully. I had to be especially careful when I bent over and as I rubbed the smooth, satiny surface of the back of my panties, I resolved never to question my mommy again.
I managed to fill the top two drawers of my dresser with the new panties and I put some of the other clothes, like the diaper shirts and rompers, into the two bottom drawers. My closet was soon filled with a vast assortment of party dresses, petticoats, sissy sailor suits and nighties. When I had finished, my mom called me into the kitchen for dinner which proceeded, more or less, normally. I was told do the dishes and my mom made me wear a frilly apron to protect my dress while I worked. Just as I was drying the last one, she came in to the kitchen and looked over my work.
“All done? Good, because it’s your bedtime now,” she stated simply.
I looked at the clock which said 7:15 and my mouth dropped open. I was about to utter a cry of protest when I saw the look of determination on my mom’s face that brooked no argument. My cheeks were still burning from the earlier spanking and I was anxious to avoid a repetition.
“Yes Mommie,” I sighed.
“Go brush your teeth and I’ll be in to tuck you in,” she told me.
I went and did as I was told and then returned to my bedroom where she was waiting with a big baby bottle of warm milk. She patted the vinyl covered mattress and had me sit down where she removed my dress and replaced it with a soft pink nighty. Tucking me into bed, she pulled up the blankets and pushed the bottle nipple between my lips.
“Here’s a widdle ba-ba for my little baby,” she said as she removed the bows from my hair.
Obediantly, I took the milk and began sucking from the nipple. It seemed strangely comforting and familiar to me as she stroked my hair soothingly. I drifted off to sleep and dreamed of my soft, thick diapers, keeping me safe and secure.

Tiffany’s Date–A Sissy’s Perspective

I was sitting in the lunchroom of our school with some of my Astronomy Club pals and trying hard not to stare at the object of all my fantasies, Tiffany Johnson. She was about two years older than me, a senior, and totally oblivious to my existence. She was everything I could ever want in a girl; tall, beautiful, long, dark hair, captivating green eyes, and a fantastic body. But today what I couldn’t peel my eyes off of were her two wonderful breasts. She was wearing a snug yellow halter top and I could make out every mouth watering curve of her bosom, not to mention the deep plunging cleavage exposed by the low scoop cut of her top. She seemed ready to burst out of her top at any moment!
She was so incredible and she carried herself in the same way that all hot girls who are aware of it do. She was confident, even cocky, and I knew I didn’t have a snowball’s chance in hell of getting her to return a greeting in the hall, not that I had the balls to try that, of course. No, I’d sooner lasso the moon than get any attention out of her.
Still, I could watch her and admire her from afar. She was too hot to ignore and I thought she was the sexiest babe in our school. No doubt she would someday be a top paid model but I could always brag that we went to the same school together.
I was glancing at her and trying to be surreptitious about it when I saw her make eye contact with me for a moment. Before I looked away, I thought I caught a flash of anger in her pretty eyes and I tried to concentrate on my lunch instead. I was in mid-sentence with one of my friends when I heard the unmistakable sound of high heels clicking on the tile floor of the cafeteria. To an ardent masturbator such as myself, I was instantly drawn to the sound like a dog to a high pitch whistle. Turning around, I was stunned to see Tiffany walking toward us. She had a very sensuous sway to her, placing one high heeled foot in front of the other like a model on a runway and her curvy hips moved up and down in a perfect harmony.
Nonetheless, I was filled with a dreadful foreboding. Tiffany was known for her dismissive manner towards guys she wasn’t interested in and I feared she was coming over to slap me or something. I just about came unglued when she stopped across the table from me and fixed me with her ravishing smile.
“I couldn’t help but notice you looking at me,” she said in a voice that could have melted lead.
“Oh no-I was-um-I was just-” I babbled nervously. I couldn’t believe this hottie was actually talking to me!
“If you like me, why don’t you come over after school,” she said sweetly, and she slid a piece of paper across the table to me.
Was I on planet Earth? This must be a dream because there was no way the hottest babe in school could be asking me to come over to her place!
I was reasonably sure this was some kind of joke concocted by her and her sexy cheerleader friends and I was hesitant to pick it up and read it. Nonetheless, my friends were looking at me expectantly and I had to do something.
Cautiously, I reached over like I were about to pick up a tarantula, and took the folded piece of paper, afraid to read what it said. But when I did, I could plainly see the address in her perfect feminine handwriting and my jaw dropped open in shock.
I didn’t know what to say! I blinked and stared at the note and then up into her gorgeous face.
“Three-thirty, sharp,” she said tersely, and I gulped with excitement.
Before I could blurt out a reply, she turned on her heel and sauntered off.
Man, she had a nice set of buns, I thought as I admired her firm derriere within her short, form-hugging gray skirt.
My friends were babbling at me a million miles a minute but I was in another world.
Tiffany Johnson wanted me over at her house!!

Unfortunately, the time Tiffany had specified didn’t allow me any leeway to prepare after I got out of school. I would’ve liked to have gotten her some flowers or something but I didn’t want to take a chance of being late. I had just enough time to rush over after getting off the school bus to make it by 3:30.
As I stood quaking with nervousness on her doorstep, I checked my watch and then checked it again. I was right on time so I was hoping to score some points already.
During the last couple of hours of school today, I had been puffed up with pride. I knew that Tiffany only dated college guys and real stud types. Of course, I was the total opposite of that. I was somewhat small, shorter than most guys my age, and kind of geeky, truth be told. My friends could not believe I had been invited over for a date and all of them were green with envy. All except Harold who was the only one to discourage me from going over to see her. He wouldn’t explain why but I sensed he knew something that I didn’t. Still, I was caught up in the intoxication of pride and puppy love, and wild horses couldn’t have prevent me from accepting her offer.
Now, as I stood on her porch, my finger shook as it went up to press her doorbell. The first time I missed and I had to mash it with the palm of my hand before I heard the chime inside.
When the door opened, my breath was taken away.
Tiffany towered over me, her big bosom ready to spill out of an unbelievably sexy black bustier. It was laced up the front and I could see the soft curves of her breasts pushing against each other where they were exposed. Above that, her voluptuous melons were displayed in an awe inspiring presentation, her cleavage splitting and curving away from each other. I could see the rise and fall of her chest with each breath she took and I was sure her top was being pushed to the limit.
I wanted to say something but what could I say? My voice was trapped in my throat and my tongue was tied in a knot. I swallowed hard and opened my mouth but I felt like I were choking.
With a disarming smile, Tiffany reached down and took my hand like I were a small child–which incidentally was exactly how I felt–and she led me inside.
“Did I surprise you?” she asked me when she could see I was at a loss for words.
“Uh, yes, er, I mean, it’s just that, well, I’m uh…” I stammered. I had never been with a girl alone and Tiffany was no girl. She was all woman and I had serious doubts as to my ability to be able to handle her. As I stared up at her, I blushed red with the intensity of the moment.
I watched as she took a large hairbrush and began running it through her long, silky brown hair. As if she weren’t fabulous enough as it was, I noticed that as she did so, her arms being behind her head caused her delicious boobs to be even more prominent than they already were–if that were even possible. I was helpless as I gaped at her, unable to take my eyes off her captivating form.
“You like watching me, don’t you,” she said in a sultry tone of voice.
I turned a beet red at being caught again.
“Well, I um, ya know…” I rambled. I just couldn’t manage to sound like anything but an idiot!
Her pretty eyes bored into me as she took a stick of lipstick and began applying another coat on her full, sensuous lips. She was so freakin’ sexy!
“Do you like my breasts?” she said after she’d smacked her lips together and capped the lipstick.
What was the best way to respond to that question? I found her directness and confidence overwhelming me and I swallowed hard to try and communicate.
“Uh-huh!” I blurt out suddenly. What a fool I was!
“You don’t think they’re too big, do you?” she said as she stroked the curvy mounds of her breasts that were exposed above the top of her bustier. I noted that she had immaculately manicured nails and my eyes were hypnotized by her erotic teasing movement. My little wiener was straining within my pants at this unbridled display of sexuality.
“Oh no! I think they’re just right!” I finally managed to croak.
She smiled sweetly at me and bent over, allowing me to gaze down her top as she softly stroked my imprisoned erection. My face was burning bright red with embarrassment but I was about to explode from her electric touch. Unexpectedly, she quickly unbuttoned my fly and pushed my pants down, exposing my underwear and the small damp spot of pre-cum on the front. I gasped in response and she smiled at me with a strange look while she took a seat on one of the dining room chairs behind her.
All of a sudden, she reached over and grabbed me by the wrist, yanking me over toward her. I lost my balance and fell on her lap face down, and she made a quick adjustment to my torso which left my bottom sticking up in the air. It was all happening too fast and I was suddenly filled with terror.
“Wha-what’s going on?” I quaked fearfully.
“I’m going to show you what happens to little sissies who think they can stare at my chest,” she snapped at me, her voice taking on an edge.
I bit my lip nervously and squirmed trying to get up but I felt the searing impact of her hairbrush as she brought it down painfully on my rump.
I bellowed out in surprise and instantly tried to get up off of her lap but she was too quick for me. I felt her grab my right arm and twist it behind my back, making me squeal with pain. She drove it up behind my shoulder blades and I was forced to go back down, leaving my fanny defenseless and at her mercy. I felt her long nail at the small of my back as she jerked my underwear off my bottom and down my legs. I tried to wrench my arm free but her grip was like steel.
My fanny twitched and she brought the hairbrush down again, delivering a blistering swat right in the center.
“OOOOWWW!!!” I wailed at the top of my lungs. Frantically, I kicked my legs desperately as my eyes brimmed with tears. This woman could really spank! She had only swatted me twice but I was already ready to start crying. And that’s just what I did as she began spanking me in earnest.
Slapping my bare bottom with harsh, penetrating swats, she wielded her hairbrush with devastating results. I sobbed and cried as she brought it down again and again, slapping my cheeks with her pent up anger and resentment. With tears spilling down my cheeks, I could see the solid stance of her glossy black high heeled sandals, supporting my skinny frame as I squirmed and kicked like a little baby.
Eventually, I gave up and I just lay there, hoping to end the terrible spanking sooner. However, rather than reward my submissiveness, she seemed to take it up a notch, smacking my bottom with even greater ferocity. Her attention shifted to the tender sides of my cheeks which she paddled to a blazing inferno before returning once more to the center of my bottom. I kicked desperately and bawled openly as this amazon spanked my punished fanny.
Finally, I heard the wooden hairbrush clatter on the tabletop.
I thought she was finished so I tried to get up but she held me firmly in place.
“Not so fast, Sissy-boy,” she warned me gravely.
I felt a sticky glob of vaseline being pushed into my back hole and I squirmed helplessly as I sobbed like a child.
“Spread your legs, or we’ll start all over,” she ordered me tersely.
What was she going to do now? I asked myself in a state of panic.
Obediently, I spread my legs and I felt her pushing a big rubber object against my reluctant back hole.
“Stop!” I wailed, “Stop! Please! It’s too biiiiggg!”
There was no way that monster was going to go up inside of me and I struggled to free myself. But Tiffany just kept pushing harder and I felt the fat, blunt end of the buttplug pushing it’s way inside me.
“Spread your legs wider you big sissy!” she barked, “This is for your own good!”
I whimpered in defeat as the wide rubber plug slid past my pouting sphincter to lodge itself firmly inside me. I gasped from the feeling of fullness and emasculation and I sobbed with defeat. This busty woman was calling the shots today and there was nothing I could do about it.
As she stood me back upon my wobbly feet, I tried to brush away the tears that were streaming down my cheeks. She grasped my chin in her firm hand like my mom used to when I had been naughty as a child.
“Take the rest of your clothes off. Right now!” she snapped in her demanding tone.
I shivered with fear at what more this knockout might do to me but I was helpless to do anything but submit. With all due haste, I tore my clothes off, still trying to come to grips with this terrible turn of events. When I pulled my undies off, I covered my little pecker with shame, embarrassed to reveal its tiny size. However, Tiffany took advantage of the fact my hands were both occupied and she smacked my bare bottom with the hairbrush in a blistering swat.
“Get into the living room, Sissy!” she ordered me even as I wailed out miserably and grasped my flaming bottom with my hands. Now completely uncovered, my little wiener wiggled foolishly as I practically hopped into the other room, a fresh torrent of tears bursting from my eyes. With blurred vision, I saw what looked like a baby’s layout waiting for me on the floor. Before I could guess the implications of that discovery, Tiffany rudely shoved me onto the ground, positioning my red, stinging bottom on a thick rectangle of white cotton.
As I wiped away the tears from my face, Tiffany bent down and began shaking baby powder all over me, using much more than was necessary. The scent brought back instant memories from when my first grade teacher used to change my diapers during recess. That had been humiliating enough but now that it was being done to me by this buxom babe was almost too much to bear!
“Why are you doing this to me?” I whined between sobs.
She didn’t answer immediately as she pulled the thick, but very soft cotton up between my legs, and inserted a big, bunny headed pin through the cloth to secure either side on my waist. I barely had time to register the faint locking sound they made as they were snicked closed.
“Because you’re a panty-waist sissy. And it’s time you were put in your place,” she quipped as she shook out a pair of pink plastic panties.
I quailed as I beheld the babyish looking vinyl panties being pulled up my skinny legs. They were decorated with blocks and rattles and I knew they were meant for a baby girls. Here I was, sixteen years old, being put back into diapers and plastic panties by the woman of my dreams and I was completely helpless to do anything about it! I whimpered with shame as she tugged them up past my knees, working them over the bulging, bulky diapers she’d pinned on me.
Roughly pushing me over my side, I felt her pulling something within the elastic waistband of the plastic panties tight, and then I heard the distinct sound of a lock being closed. With a smug look of satisfaction on her pretty face she stared down at me with a challenging demeanor as if to say ‘try and get those off now’. It made me want to cry!
But then she picked up a peach colored t-shirt that was lined on its edges with frilly ruffles, pulling it over my head while I sat there dumbfounded. It barely reached my waist and when my head poked through the top, I looked down and read with shock the inscription written in gaily childish letters across the front:

I love my diapers

And just then, the doorbell rang.

With my mouth hanging open, I turned to Tiffany, unable to move.
“Well, who could that be, Sissykins?” she said tauntingly.
I gulped hard in a compete state of panic, still trying to come to grips with what was happening.
“Better go answer it, unless you’d like to take another trip over my lap,” she said with her smug, confident look.
My bottom was still blazing from the fierce spanking she’d given me moments ago. I was terrified at the prospect of going across her skirted lap again.
“Please,” I pleaded desperately, “please don’t make me.”
Without another word, she suddenly stood up and walked over to where she’d left her hairbrush, picking it up and looking back at me evenly. Realizing she was deadly serious, I gulped hard and jumped to my feet, desperate to avoid that terrible instrument of punishment. As I did, I could feel the fat buttplug making its presence known and it forced me to waddle even more than I would have normally from the thickness of the bulk of the diapers between my legs.
Maybe it was just a solicitor, I reasoned to myself as I trundled toward the door. If I could just open the doorway enough to peek out and get rid of them, maybe I could still escape here with a shred of my pride.
Pulling open the large ornate door just a crack and keeping the shameful words on my toddler top hidden, I looked out to receive another shock. There on the doorstep were three hot cheerleaders from my school, still dressed in their sexy and very revealing outfits, staring back at me with knowing smiles on their beautiful faces.
Just then, I felt the door being pulled open from behind me and I gasped with terror as I stood in my sissyish state before them. They took one look at the fat diapers I was wearing, encased in babyish pink plastic nursery print panties and the girlish t-shirt I was wearing, and they burst into gales of laughter. I was so shocked and mortified that without even realizing it, a stream of pee burst out from me, soaking the front of my diapers.
Even Tiffany erupted in laughter and the girls pointed at my diapers, falling against each other as they rolled with amusement. I could only hang my head in shame as I drank full from my cup of humiliation. A tear rolled down my face and my shoulders shook miserably.
It was at that moment when I felt Tiffany reach down and squeeze the thick seat of my baby pants, confirming the fact that I’d wet myself.
She shook her pretty head and looked at me knowingly with obvious disgust.
“Ready to go home now?” she asked me.
I nodded abjectly, completely defeated and broken by this beautiful woman.
With a smirk on her face, she reached down and threw my socks and shoes out the still open front door onto the lawn. Looking up at her in surprise, my mouth opened as I tried to understand what she had in mind. With rude abruptness, she turned me in the direction facing outside and swatted my thickly padded bottom with her hairbrush, sending me headlong onto her lawn past her giggling friends. I fell on my hands and knees just as I heard the heavy wooden door slam shut behind me. Seized with panic, I bolted back up and began pounding on the door, frantic to get back inside.
“Have a nice walk home, Sissy!” I heard her called out to me through the closed door.
I pleaded for her to let me in or at least give me my clothes back but the only response I heard was their mocking laughter and teasing remarks.
“Better get lost Sissy,” she warned me from behind the locked door, “Or I’ll call your mommy and have her come over and pick you up. You’ll have an interesting time explaining your wet diapers to her when she gets here.”
I felt my eyes filling with tears as the full weight of my predicament crashed down upon me. I was dressed like a sissy baby girl in wet diapers and there was no way these women were going to give in to let me have my clothes back. I sobbed with defeat as I finally gave up and started the long, humiliating walk back home.

Tiffany’s Date

The following is an excerpt from the story, “The Further Adventures of Baby Bobby-the Strict Nanny”

My name is Tiffany Johnson and I guess I was meant for this job. As a teenager, I always loved to tease and dominate the guys who wanted badly to see what was under my tight, short tops and skirts. I developed early in my youth, quickly moving into a D cup before I was sixteen which hardly went unnoticed by the opposite sex. In addition, I quickly grew in stature from 5’7” to 6’0′ by the time I was a senior in high school. I started to notice a certain attention I was getting from the sissy boys in high school. I think they wanted me to be their mommy but they soon found out that this mommy had a very strong spanking arm.

I thought for those of you who read that paragraph and wondered about what really happened, I would tell a little about one particular time, a very ordinary date, if you will, in which a timid high school boy learned his proper place once and for all.

Tiffany’s Date

I don’t like it when people stare at my boobs.
I especially don’t like it when nerdy, sissy guys stare at them, as if I might deign to let them touch them, or something.
Of course, I understand why people do stare at them. They are large, perfectly round, and hard to miss, especially considering the way I dress. At 38EE, even the girls in school tend to stare at them. But I love wearing revealing clothes, skimpy outfits and snug fitting tops and skirts that showcase my spectacular body. And I don’t mind when the good looking, hunky guys look at me, but it annoys me to no end when I catch one of the skinny little wooseys with glasses staring at me. How dare they! Don’t they know I wouldn’t give them the time of day?
I do my best to make them aware of my feelings by pushing them around whenever they get in my way. I like to cut in front of them in line and watch them pout as I act like they don’t even exist. And as if my six feet in stature weren’t enough of an intimidation, I like to wear high heels to school to make me tower even more over the wimps who get in my way. I like to give them a rude shove so that they learn their place. And any who show even the slightest trace of backbone by complaining earn themselves a harsh slap in the face. That usually sends them running and I laugh whenever I see it happen.
However, there are some times when the naughty side of me feels the urge to take it a little further.
They other day, in the lunchroom, I was sitting with some of my friends, a group some people would call, “the popular crowd”, made up mostly of cheerleaders and burgeoning models.
I was sipping my drink, when I saw two tables over, a nerdy guy, probably a sophomore, trying hard to hide the fact that he was staring at me. Today, I was wearing a clinging halter top over one of my favorite demi-cup push-up bras. The overall effect was quite impressive, if I may say so myself, with every curve of my breasts clearly on display.
At first, I started to get angry. And then, an idea suddenly dawned on me. The thought of it made me giggle and I took a piece of paper from my purse and wrote down my address on a piece of paper. Standing up, I walked slowly over to the wimp’s table, my saucy hips swaying seductively. His geeky friends immediately began gibbering amongst themselves as they saw me approaching. With my high heeled sandals clicking audibly on the tiled cafeteria floor, it announced my presence like a loudspeaker to any male nearby.
I watched as the nerd’s face grew red–no doubt he was aware that he had been discovered and now he was fearing the embarrassment I was about to unleash on him. Nonetheless, as I came up to the table of these boys, I stood over them and smiled pleasantly.
“I couldn’t help but notice you looking at me,” I said in my sultry, very feminine voice.
“Oh no-I was-um-I was just-” the nerd stammered frantically.
“If you like me, why don’t you come over after school,” I said invitingly, as I slid the paper with my address across the table to him.
The nerd looked as if I’d hit him with a two by four. His mouth dropped open and he stared first at the paper and then up at me unbelievingly. For a second, he just stared dumbfounded and then he scrambled to snatch up the note, no doubt thinking it probably said something like ‘drop dead nerd’, or something similar.
Instead, when he realized it really was my address, he still found himself at a loss for words.
“Three-thirty, sharp,” I said crisply, and I turned around and walked away without a further word.
Hushed, urgent, and excited whispering broke out from behind me as his flabbergasted geeky friends tried to grasp at what had just taken place.
I smiled to myself as I saw once again, how easy it was to manipulate the opposite sex.

The sissy arrived at 3:30 on the dot, just as I expected. When I opened the door, he looked flushed and uncertain, and he licked his dry lips nervously.
I was wearing a sexy black bustier that had strings that cinched it up the front, producing a fantastic cleavage and two big mounds where my voluptuous breasts were spilling out of the top. I made sure he wouldn’t see my nipples because that is a privilege that I would never grant a sissy like him.
As I stood before him with my hands on my hips, I still had on my short gray skirt from earlier which had the slit up the side. With my four and a half inch heels, the sissy’s face was right at the level of my boobs. He gawked at them in awe and tried to articulate some sort of greeting but his voice cracked when he opened his mouth. Intuitively, I could tell he was still a virgin and I merely smiled agreeably down at him as I took his hand and led him inside the house. My parents wouldn’t be home until later and in any case, what I wanted to do wouldn’t take long.
“Did I surprise you?” I asked the quivering wimp.
“Uh, yes, er, I mean, it’s just that, well, I’m uh…” he could hardly string three words together that made any sense and his face was flushed.
I began brushing my long, curly brunette hair with my hairbrush, a large oval shaped instrument with a back made of hard, firm oak. As I did so, I arched my back slightly, pushing my impressive chest outwards to further fluster the overwhelmed sissy.
“You like watching me, don’t you,” I prompted him.
He blushed furiously and I could see that I’d hit a sensitive spot with that remark.
“Well, I um, ya know…” he stammered stupidly.
I looked him deep in the eye as I applied a coat of dark, wine colored lipstick to my full lips, purposely taking my time to tease him with it. He watched me hungrily like a starved dog eyeing a piece of succulent bacon.
“Do you like my breasts?” I suddenly asked him boldly as I smacked my lips together and put away the lipstick.
He swallowed hard as he tried to come up with an appropriate response.
“Uh-huh!” he said, sounding completely geeky in doing so. It was obvious he’d never been with a girl, sexually or otherwise.
“You don’t think they’re too big, do you?” I asked as I ran my immaculately manicured fingers softly over the curves exposed above my bustier. His eyes watched my hands closely as they stroked the smooth skin and I observed a small bulge forming in the front of his pants.
“Oh no! I think they’re just right!” he said, now filled with determination.
I smiled enigmatically and without saying anything further, I moved my hand down to his crotch and gently rubbed his little erection. Even as he blushed beet red, he closed his eyes in ecstasy and I unzipped his fly, lowering his pants to his ankles. He gasped and tried to cover up his underwear, suddenly embarrassed at being so exposed.
With an abruptness that caught him totally off guard, I took a seat on one of the dining room chairs and suddenly yanked him over my lap.
“Wha-what’s going on?” he quaked in terror as he found himself staring down at the floor in front of his face.
“I’m going to show you what happens to little sissies who think they can stare at my chest,” I snapped, revealing the anger I had been hiding until now.
Before he could say another word, I brought the flat side of my hair brush down on his little round bottom with all my might, delivering a harsh, stinging swat to his cheeks.
He howled in pain and tried to get up but I was already anticipating his move. I reached over and quickly grabbed his right arm, wrenching it around and pushing it up between his shoulder blades. He squealed with panic and it forced him to put his head back down to relieve the pressure. When he was back in position, I jerked his underwear down and off his butt, leaving his backside bare and ready to be spanked. Already, a bright red oval shape had formed that covered both his round, nubile cheeks and I was determined to add much more color than that.
Holding his arm with my left hand so he couldn’t escape, my right grasped the hairbrush firmly and I brought it down with a hard, punishing swat that filled the room with its impact.
“OOOOWWW!!!” he cried desperately, his legs kicking helplessly.
Despite the slimness of my arms, I’m quite strong and I used my strength to good effect, wielding the hairbrush with fierce, blistering swats. He gasped for breath as he tried to cope with the assault on his smooth, tender cheeks but his facade of manliness evaporated in an instant. By the third time my hairbrush had smacked his bottom, he was bawling like a two year old. I settled into a determined, calculated rhythm, slapping his quickly reddening fanny and watching as it turned a hot, angry shade of crimson. Before long, he stopped fighting me and he willingly submitted to his punishment although he was still flailing his legs desperately in response to the severe spanking he was receiving. I rewarded his submissiveness by increasing the tempo and severity of the sissy’s paddling, giving the little crybaby exactly what he deserved.
After blazing a red inferno on the center of each cheek, I moved outward, slapping the sides with crisp, deliberate blows that made him wail in agony. When the sides had achieved the same degree of color as the center, I returned my attention to the original target, the middle of his seat where his youthful, fleshy cheeks curved most delightfully. My hairbrush swung down again and again, and the poor sissy sobbed and cried like a little girl. Bunching the one fist that he had free, he beat it against the floor in frustration as the tears streamed down his face.
This was the image I wanted to forever sear into his mind: that of a helpless sissy being severely paddled by a superior woman who is in complete control. He would never look at the opposite sex in the same way again.
At last, I stopped spanking him and I set the hairbrush down next to me with an abrupt clatter.
The nerd tried to get up but I rudely forced him back down again with his bent arm.
“Not so fast, Sissy-boy,” I warned him and I reached around behind the chair where a jar of vaseline was hidden and waiting for me. Dipped inside, was a nice, thick buttplug that was coated liberally with the sticky lubricant. Taking a dollop in my hand, I pressed it up against his anus which made him struggle once more to get free.
“Spread your legs, or we’ll start all over,” I told him evenly.
Sobbing pitifully, he did as he was told and I pushed a glob of the vaseline into his hole. Taking the big rubber buttplug, I brought it up and rubbed it against his rosebud, looking for the right angle for penetration. He squirmed and squealed as I began slowly but firmly pushing it in.
“Stop!” he wailed, “Stop! Please! It’s too biiiiggg!”
I ignored his pleas and pushed harder.
“Spread your legs wider you big sissy! This is for your own good!” I commanded him.
He moaned as the buttplug finally eased past his sphincter and disappeared inside him, the rectangular handle the only thing left exposed. He was breathing heavily and still crying but I knew he needed still further humiliation. Standing him up, I looked down into his tear stained face and held his jaw firmly in my hand while he stood on shaking legs.
“Take the rest of your clothes off. Right now!” I ordered him in my authoritative voice.
He crumbled before me and I knew he was completely defeated. No doubt he was frantic to know what was going to happen next but I kept him in the dark. When he had finished and he was covering his pathetic little wiener with his hands, I took advantage of the fact that his bright red bottom was completely defenseless. Picking up the hairbrush, I brought it down with a blistering smack against his stinging rump.
“Get into the living room, Sissy!” I told him.
He howled in torment and practically ran into our spacious living room where I had a few things laid out for him. On the floor, I had arranged a thick set of baby diapers, big enough for him to wear, some safety pins, powder, and of course, plastic panties. I was going to dress this sissy in the most humiliating way possible, and show him what I thought of pansies like him at the same time. I pushed him down on the floor on top of the diapers and began situating him over them while he whimpered from the pain of his punished bottom.
With several good shakes of the baby powder I covered his crotch and up to his chest, giving him the infantile smell of a toddler.
“Why are you doing this to me?” he whined between sobs.
I pulled up first one side of the diapers, then the other, pinning him securely in place with the special locking pins. He’d have to find some way of cutting those off if he ever wanted to remove them again.
“Because you’re a panty-waist sissy. And it’s time you were put in your place,” I told him as I shook out the plastic panties. They were a pink translucent pair with patterns of blocks and rattles decorating it. He grimaced as I snaked them up his skinny nerd legs, brusquely pulling them up and over the thick, bulging diapers. He must have been surprised to find that they fit him so well and I snapped the waistband against him before making sure the diaper was completely tucked in. As a final touch, I snapped shut the tiny lock in back, making sure the panties would be staying right where they were. This sissy was going to be wearing his diapers home whether he liked it or not!
Next, I gathered a peach colored t-shirt with pink edging and feminine frills. He nearly burst into tears when he read the gaily written inscription on the front. It said “I love my diapers” on it, and I smirked as I pulled it down over his head.
With his fat, plastic covered diapers and sissy shirt, he looked every bit, the overgrown baby.
That was when the doorbell rang.

“Well, who could that be, Sissykins?” I taunted him.
I saw abject fear all over his face as he looked terrified at the door.
“Better go answer it, unless you’d like to take another trip over my lap,” I told him, leaving no doubt in his mind as to what would happen if he refused.
“Please,” he pleaded desperately, “please don’t make me.”
Without a word, I walked over and picked up the hairbrush, fixing him with a severe look.
He probably wet his diapers out of fear because he jumped to his feet in his hurry to get to the door. Between the thickness of his diapers and the fat buttplug stuffed in his ass, he stood with his legs spread apart in a distinctively babyish pose. Biting his lip in angst, he slowly pulled the door open, but only enough to peek through without exposing himself.
That wasn’t going to do it for me. I came up from behind him and yanked the door open the rest of the way, revealing his diapered state to my friends who were waiting on the front porch. They immediately burst into laughter as they came inside and took in the ridiculous image before them. The poor sissy reacted predictably enough–I heard a hissing sound and soon a darkened spot appeared in the front of his plastic panties. The pansy was actually wetting his diapers! I burst out laughing myself since I couldn’t contain myself anymore.
Tears of shame filled the sissy’s eyes as he struggled to take in the humiliation being dished out to him. I imagine nothing could possibly have been worse for the nerdy panty waist than to have four beautiful and sexy girls from his school laughing at him as he wet his diapers like a baby.
Coming up behind him, I squeezed the thick seat of his diapers and I could feel that he’d wet so much that his pee had soaked down between his legs and into the seat of his pampers.
I shook my head at his pathetic display but made no move to change him.
“Ready to go home now?” I asked him.
He nodded abjectly, totally subservient now.
Opening the door, I threw his socks and shoes out into the yard. Turning him in the direction of the open door, I swatted him soundly on his diapered butt with the hairbrush, causing him to stumble outside. Once he was through the threshold, I slammed the door shut, locking him outside while the others laughed themselves silly.
“Have a nice walk home, Sissy!” I called out to him through the door.
I could hear him beating on the door frantically, begging for his clothes and to be let back in.
“Better get lost Sissy, or I’ll call your mommy and have her come over and pick you up. You’ll have an interesting time explaining your wet diapers to her when she gets here,” I told him as I chuckled at his predicament.
The nerd stood for a moment considering his perilous choices before we heard his footsteps quickly retreating down the sidewalk.
I think we laughed until our sides hurt.
That was one sissy who had learned his lesson once and for all.