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.
SMACK! CRACKKKK!!! WHACKKK!! SMMACKKK!!
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.
SMACKK!! SMACKK!! CRACKK!! THWACKK!!
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.
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.
SMACKK!! CRACKK!! SMACK–SMACKKKK!!!
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.
WHACKKK!!! SMACKKK!!! SMACKKK!!!
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.