As I sat on the bus making it’s way across town, I fidgeted nervously, pondering the events that had led me to this point. Last week, my first and only serious girlfriend had kicked me out of her apartment after she had caught me masturbating again.
Things had not gone too well for me with Jenny, starting with her discovery of my penis, or rather, the lack of one, in her eyes. I suppose I had been in denial about my diminutive weiner, which had never really grown much since I was in the second grade. It still was little more than a stub, even when it was erect, and it’s diameter was about that of my pinky finger. Of course, it didn’t help things that I was a premature ejaculator as well. These things all conspired to bring a my relationship with Jenny into a downward spiral and she immediately stopped giving me any sexual attention of any kind. At the same time, she started treating me more and more like a little boy but I guess I was so used to being dominated by strong women all my life that I just went along with it.
Two weeks ago, she informed me of her intention to start dating other men. When I protested, she responded by pulling me over her lap and spanking me with her hairbrush until I was sobbing like a baby. I should have left right then and there but I couldn’t. I guess I’ve always been weak willed and I kept rationalizing why I should stay with her so I just learned to accept the situation.
However, since I wasn’t getting any sexual gratification from her, I became increasingly horny and masturbation was the only relief I could get. One day while I thought she’d be away for a while, I found one of her Victoria’s Secret catalogs lying around. No sooner were my underwear in a circle around my ankles and I was readying myself for some badly needed relief, when Jenny barged in with one of her new boyfriends. To make a short story even shorter, she lost no time in yanking me over her lap and spanking the daylights out of me with her hairbrush again–in front of her boyfriend no less! After that, she kicked me out permanently and I was forced to walk all the way back to my mom’s house.
The masturbation episode was the last straw for Jenny and immediately after had she kicked me out, she called my mom up and told her everything, telling her I was nothing more than an immature sissy who needed his mommy. Needless to say, my mom was anything but pleased when I got home. I knew that for sure when she met me at the door with the paddle in her hands. She dragged me inside and after tearing my pants down, proceeded to give me my second blistering spanking of the day.
After a good cry and a ‘time out’, with my nose pressed into the corner and my trousers gathered around my ankles, my mom returned to the living room with a suitcase in her hand.
“Jimmy,” she said with great deliberation, “I’ve tried to do my best to raise you to be a decent young man. Apparently, I’ve failed in my task so it’s time for someone else to have a crack at the job.
“I’m sending you to live with my friend Vanessa who lives on the other side of town,” she informed me stonily.
“V-Vanessa?” I asked shakily as I rubbed my stinging bottom that was still bared and red as an apple.
“That’s right Jimmy, Vanessa. I trust her completely and I know she can handle a grown up sissy like you.”
Now, as I sat on the bus, still shifting uncomfortably in my seat because of the duel spankings, I pondered my new living arrangement.
I hadn’t seen Vanessa for years, not since I was kid, although I still remembered her with a strange mixture of arousal and humiliation. She had treated me to my first and only sexual experience when she had allowed me to nurse from her wonderful, massive breasts. Everytime I thought about it, my tiny pecker stirred and my heartbeat quickened. Back then, Vanessa had been a total babe, with an unbelievable body. I had been ten and she was in her mid-twenties which would make her mid-thirties now.
What did she look like now, I wondered. Maybe she’d let herself go and gained a million pounds, I thought absently. Maybe she was wrinkled and ugly, or just plain dumpy looking…
I would know very soon, I realized as the bus took me steadily closer to her home. If she was good looking, I was determined to show her the new me. Now that I was twenty and all grown up, I was in a position to be able to talk with her as an equal. This time, she wouldn’t be changing my diapers, and this time, maybe we could even go out on dates! I knew I was getting ahead of myself but I couldn’t help fantasizing with my memories of her. I pictured myself taking her to an elegant restaurant, and then back to her house, where I’d ravish her and kiss her wonderful bosom. Ah, if only I could make that happen!
The bus finally lurched to a stop outside a wealthy gated community and I took my suitcase and got out, introducing myself at the guard shack. The sentry let me in and gave me directions for the short walk to Vanessa’s house. Evidently, she had done very well for herself since I had known her, as was quickly becoming apparent by the expensive homes I was walking by. Holding the paper in my hands with her address written on it, I came at last to her house. It was quite impressive, with a Mercedes parked out front in the driveway and a fancy hedge surrounding the large yard.
Walking up the stone pathway, I rang the doorbell, with butterflies in my stomach. In the silence of the neighborhood, I could hear the clicking of high heels as they approached the door on the other side. My heart immediately began beating harder when the door suddenly opened.
A young woman of about eighteen, dressed in a french maid’s outfit stood framed in the doorway and she took my breath away. She wore 5″ high heel black patent leather pumps, dark silky hose that showed off her fabulous, long legs, a very, very short black skirt that flared out over a white ruffled petticoat and a low cut white blouse, revealing a pair of beautiful breasts that were pushed up into a mouth watering cleavage. She had a dark choker around her neck and her long brown hair was pulled back from her gorgeous face. As I stared up at her green, piercing eyes, my mouth opened and I tried to stammer out some sort of greeting.
She was the kind of girl who was quite aware of her beauty and despite her veneer of politeness, she looked down on me with obvious superiority and confidence, making me wilt in return.
“I’m-uh, ah, I’m…my name is, ah,-” I babbled incoherently.
“Jimmy,” she said sweetly as she broke into a smile that just about knocked me over.
“Er, Jim…is my name,” I said, trying to correct her.
“Come in, we’ve been expecting you,” she said as she stood back to let me in.
I stepped up into the house and was led into a fancy living room, lavishly appointed with furniture and art that looked like it cost a lot of money. Out of the corner of my eye, I watched the maid walking in behind me, her long sexy legs competing for my attention as well as her exciting breasts.
“My name is Barbie,” she said softly, making me want to melt, “I’ll inform Vanessa you’re here.”
I was totally captivated by this young, sexy beauty and I nearly drooled as she turned around and stode into the other room, her high heels clicking on the hardwood floor.
This was going to be great! I thought to myself as I pondered the best method to flirt with this knockout. Somehow, I had to put my experiences with Jenny behind me and score with Barbie at the soonest possible opportunity.
My mind was still reeling from the possibilities when I heard two sets of high heels coming my way. Standing up, I saw the tall, familiar figure of Vanessa come around the corner and my jaw dropped for a second time. Far from having put on the pounds, my former babysitter was awesome in every way! She wore a semi-sheer white blouse that looked like it was about to burst open from her massive cups, held in check only by a lacy white demi bra that could plainly be seen underneath. She had unbuttoned the first three buttons of the blouse which gave me a view of the deep line of cleavage that disappeared down between her incredible breasts where they were pushing against each other.
Below that, she had on a beige skirt that came down to a few inches above her knees, which hugged her slim form very nicely. Her high heeled open toed sandals revealed her immaculately manicured toenails.
I had forgotten how tall she was and when she came over to hug me, she mashed her big bosom against my chin, smothering me in a wonderful, erotic embrace. I was ready to die and go to heaven!
“Jimmy!” she said cheerfully, “you’re all grown up now.”
“Uh-huh,” I said as I relaxed within her strong embrace.
“Last time I saw you, you were still in diapers,” she commented with a knowing smile.
I blushed deeply, hoping she wouldn’t elaborate any further in front of Barbie, who I hoped was still unaware of my long and drawn out childhood that had been filled with diapers up until the age of fourteen.
“Er, a lot of things have changed since then, Vanessa,” I said meakly.
“Well, we’ll see,” she said with a smile as she patted my bottom affectionately.
I wasn’t sure what to make of that comment but in my fog of arousal, I brushed it off without further thought.
“Come upstairs, I’ll show you your room,” she said to me.
Barbie wandered off elsewhere and we climbed the curving steps that led to her upper floor.
My eyes were glued to Vanessa’s saucy bottom and her smooth, slender legs atop her high heels as she slowly ascended the stairway.
“This sure is a nice place,” I said in wonderment, trying to ease my excited tension from being in such close contact with two total babes.
“Thank you, I’m an investment banker for a financial institution here in town,” she informed me.
She sure didn’t look like any banker I’d ever met, I thought to myself.
She led me into the first door on the right which was a softly lit room, appointed in a very feminine fashion, but which was very typical of Vanessa. It was more girly than I would have liked but who was I to complain about free room and board?
I sat on the four poster bed and recognized immediately the sound and feel of a vinyl mattress cover under my rump. Why would that be here? I wondered.
For my fifteenth birthday, my mom had given me several pairs of training panties, to replace my daily diapers although I was still having a problem at night. By the time I was sixteen, I finally stopped wetting the bed although my mom still insisted I wear diapers and plastic panties to bed for another year, just to be sure. Had she said something to Vanessa, I asked myself. Again, I decided not to say anything about it. Maybe it was from someone else who had stayed here.
“I’ll just let you unpack your things, Jimmy. I run a pretty informal place here and Barbie usually eats dinner with us. That’ll be about six o’clock,” she told me as she stood with her hands on her curvy hips.
“Okay, thanks Vanessa,” I said, trying studiously to avoid staring at her boobs.
“It’s good to see you again, Jimmy,” she said smiling, as she bent down and kissed me on the cheek, leaving the impression from her lipstick there while I blushed furiously.
“Me too,” I stammered, feeling foolish and inadequate all over again.
After Vanessa left, I struggled to get my runaway libido under conrol and settle down, even though I wanted badly to sit down and diddle myself with the images of Vanessa and Barbie swimming through my head.
I began opening drawers to put my stuff away. I froze when I opened the top drawer which revealed a stout, oval shaped wooden paddle, with a double line of holes going down it’s length. I looked at like it was a cobra and my stomach tightened into a knot, my mind imagining it slapping my bottom while I was made to bend over Vanessa’s lovely lap. I shuddered involuntarily and closed the drawer.
I filled the second and third drawers with my clothes but then got another shock when I opened the bottom drawer. It was the tallest of the group and it was filled with stacks of soft, cloth diapers. On the right side of the drawer were stacks of plastic panties, in various pastel colors of pink, yellow, peach and lilac. With my heart pounding in my chest, I picked up one of the panties to check it’s size. Maybe they were for a kid, I hoped. My hope dwindled when I saw they were right in my size. Frantically, I threw it back and closed the drawer quickly. I could only hope and pray those weren’t intended for me although I had a nagging suspicion they were.
Dinner went well and I forgot about the diapers as Barbie showed that she was as good a cook as I’d ever experienced. We sat around talking until about nine when Vanessa drew me a bath and invited me to make use of whatever I needed. I relaxed in her tub and it seemed all my troubles had gone away as I soaked in comfort. Finally, when I was finished, I dried off and went back into my room, my towel wrapped around me. Vanessa was waiting for me there, with her back to me, and when she stood back up to face me, my mouth dropped open in shock. There, laid on the bed, was a changing pad, three diapers in a stack, pins, baby powder, and pink plastic panties.
“I thought I’d help you get ready for bed,” she offered very matter-of-factly, as if it were nothing in the world.
“Huh?” I exclaimed, “but I don’t wear diapers anymore!”
“Now Jimmy, it’s been a long day and I think we both know this is better for both of us. This mattress was twenty five hundred dollars and I don’t want to take any chances,” she explained patiently.
My heart sank as I realized that Vanessa’s perception of me hadn’t changed at all in the last ten years. To her, I was still a bedwetting child who needed to be fastened up into his diapers every night.
“But-but, I really don’t need them,” I tried to tell her.
“I’m sure you don’t,” she said, although her tone of voice clearly said otherwise, “but I think for tonight, we’ll just be sure, okay Honey?”
I hated being talked to like I was four year old, especially now that I was an adult.
“But-I-I,” I tried to protest as she removed my towel.
“Hush, Baby,” she said soothingly as she lowered my nude form over the stack of diapers.
I blushed beet red as my bottom came into contact with the bunny soft cloth underneath me. All the more so since she could now see my tiny penis plainly sticking up like a tan crayon. Looking down at it, she giggled and put her hand to her mouth to try and hide her amusement. I blushed even redder and Vanessa bent forward, her huge breasts swinging before me, mesmerizing me like a form of hypnosis.
“It’ll be our little secret,” she assured me as she took a handful of diaper rash creme and began smoothing it across my bottom. I bit my lip in embarrassment as she looked into my eyes while she did this most intimate procedure. When she had coated it with a thick, sticky layer, she rubbed her creamy fingers down my slippery crack, sending erotic shivers coursing through me. Baby powder followed and she wasn’t stingy with it as she covered my crotch and between my thighs with the softly scented powder, making a cloud rise up around me. Humming to herself, she drew up the thick cloth between my legs and pulled the ends together at my side.
“This is just like old times, isn’t it, Honey?” she said as she smiled down at me while she pinned the diapers shut with pink duckie pins.
“Uh-hm,” I said, too embarrassed to return her look. I felt like I was ten years old all over again, having my diapers changed by my beautiful babysitter.
Shaking out the shiny pink plastic panties, she gathered the leg holes and then began snaking them up my legs. When she reached the base of my diaper, I lifted up my bottom obediantly as she tugged the panties up and over the fat diapers, circling around my hips several times with her manicured finger nails as she worked the panties over the big, bulging diaper.
“This should hold you ’til morning,” she said, obviously satisfied as she snapped the elastic waistband with a flourish.
I blushed again while she held me close to her and hugged me, bringing my face into close contact once more with the softness of her big breasts. I breathed in the intoxicating scent of her skin and perfume and my head swam with desire, despite the intense feelings of humiliation that were washing over me.
After a moment, she stood up and pulled the sheets back, beckoning me to get in bed.
“Nighty-nite, Jimmy,” she said, “sleep tight, Baby.”
I waddled over to the bed and got in, the all too familiar feeling of thick padding between my legs and embracing my hips. As I moved around, the noisy vinyl sheets reminded me of their presence and I felt so childish that Vanessa couldn’t trust me in her bed without diapers and waterproof sheets.
With another kiss on the cheek, she turned and left the room, shutting out the lights as she went.
I sat there, staring up at the ceiling, wondering if I’d ever be treated like an adult.
That night, I had troubled sleep.
My dreams were filled with humiliation and visions of when I was ten. I was wandering around Vanessa’s house in a pink party dress and diapers, desperately trying to find my babysitter. I looked in every room but I couldn’t find her anywhere. All of a sudden, Brittany showed up from out of nowhere and she had a mean look on her face. I was terrified of her after all she had subjected me to, and my only response was to flood my diapers in a wild panic. She laughed mockingly at me and then she dragged me out into the living room where everyone had gathered. They all laughed at my appearance and made humiliating comments to me which only made me pee my diapers worse and that’s when I started crying like a baby. Suddenly, Brittany was approaching me with the paddle in her hands, a determined look on her face.
“Now I’m really going to give you something to cry about,” she said as she grabbed me roughly by the wrist.
“Nooooooo!!!” I cried.
Suddenly I awoke with a start.
Warm sunshine was streaming in through the lace curtains and I realized it was morning already. With a shock, I also became instantly aware of the soggy wet mass within my plastic panties–the all too familiar feel of soaked diapers.
I glanced up at the door and saw it was slightly ajar. I could hear voices nearby in the hall and I recognized them as Vanessa and Barbie. What was I to do? I looked around the room thinking maybe I could stash the diapers somewhere but then what? My mind raced as I tried to concoct a plan but I just couldn’t think straight.
Then, suddenly without notice, Vanessa came into the room. She was wearing a short, white halter top that hugged her big, bountiful breasts showing every curve in the most delightful manner. They seemed to be spilling out of the top and her spaghetti straps looked strained to hold her bosom in. A smile was on her face as she came in and stood next to the bed, bending over to greet me.
“How’s my little baby?” she asked as she started pulling the covers back, “did you have a dry night?”
Despite the fact that I was being treated to the most fantastic view known to Man, my mouth went dry and I clutched at the blankets with an iron grip, panic overwhelming me.
“Come on, Jimmy,” she said as she pulled downwards against my efforts, “I just want to check your diapers, Honey.”
“Uh-uh,” I pleaded but she tricked me. Instead of pulling downwards, she switched her grip and simply lifted up from the side, exposing my bare legs and diapers competely. Dropping the blankets, I threw my hands down in a futile attempt to hide the wet diapers from her.
Vanessa looked at them and then shook her head at me.
“Looks to me like you haven’t quite outgrown the need for your diapers, have you, Jimmy?” she said as she crossed her arms over her ample chest. This time, she was no longer smiling.
“I-I don’t know what happened,” I said haltingly, “I think I-I had an accident.”
Vanessa turned away and without a word, started pulling diapering supplies out of the dresser. In silence, she began arranging the items on the changing pad she’d laid out and It was becoming obvious that she was going to put me back into another pair of diapers for the day. That was something I just couldn’t tolerate. I was twenty years old, for crying out loud! I didn’t need diapers, and I sure as hell wasn’t going to let Barbie see me wearing them.
Pulling me out of the bed by my wrist, Vanessa stood me up so she could pull my plastic panties down.
“No way!” I shouted defiantly and I pushed her away belligerently.
All of a sudden, the room swam before my eyes and I found myself on the floor, facing up at Vanessa while stars rang around me. My head was pounding where it had hit the floor.
“Try that again and you’ll really be sorry,” she said, as she towered over me with her hands on her hips and her legs spread slightly apart. I don’t know where she learned karate but I wasn’t going to give up without a fight. I launched myself at her, only to go crashing against the far wall where she had deftly flung me like a ragdoll.
“Okay…okay…I give up,” I mumbled as I rubbed my aching head.
Vanessa grabbed my wrist again and she pulled me over to the bed, sitting down calmly as she hitched up her skirt.
“Vanessa? Is everything okay?”
My head jerked up to see Barbie, staring at me in my pink plastic panties and wet diapers, standing next to Vanessa, and my face turned three shades of purple.
“Can I get you anything?” she asked out of concern.
“Yes. Can you open that top drawer and get me the paddle? I have a naughty little boy here who’s wet his diapers and needs a spanking.” Vanessa told her firmly.
Barbie giggled and walked into the room. She was wearing a similar french maid outfit again with another pair of black stilletto heels and short mini-skirt. Reaching into the drawer, she took the wooden paddle and handed it over to Vanessa.
“This situation should be very familiar,” she said as she peeled my clinging pink plastic panties down my legs. I whimpered in fear as I held her gaze for a moment, the look of a little boy who knows he’s about to get a blistering spanking from a strong woman. My knees went suddenly weak and I felt unsteady on my feet. I glanced down at her two massive boobs jiggling within her top, then at the wooden paddle in her hand, and finally, into her dark, determined eyes. Once again, Vanessa had defeated me with diapers and now she was going to reduce me to a bawling crybaby in front of this beautiful girl.
With an abruptness that I wasn’t expecting, she yanked me across her lap and I landed with a wet squish. Looking over my right shoulder at Barbie, I whimpered meekly as Vanessa unpinned my saturated diapers, pulling them back between my legs. Drops of pee were dewed upon my bottom cheeks and the room filled with the humiliating smell of urine. I could feel the blood going all the way to my ears as I was overcome with shame.
“Well, well, Jimmy. I guess once a sissy, always a sissy, hmm?” she said as she readied her spanking arm.
I stared down at her high heels and sexy calves but before I could utter a response, the paddle seared itself onto my damp bottom.
“OW-WOW-WOW-WAHH!!!!” my eyes shot open and I cried at the top of my voice.
SMACKK!! SMACKK!!! SLAPPP!!
I immediately started bawling like a baby, kicking my feet frantically within the confines of my damp plastic panties.
The paddle landed three times in quick, stinging succession. I screwed my eyes shut and gasped for air as I beat the floor with my fists. This woman could spank!
WHAPP! SMACKK!! CRACKK!!
“WAHHHH!! WAAAAHHHHH!!” I cried, my voice sounding high pitched and girlish.
Tears streamed down my face and I sobbed uncontrollably. I didn’t make any attempt to get off Vanessa’s lap because she was far too strong for me anyway. I knew this spanking would end only when she was ready for it to end.
SMACKK!! THWACK!! SMACKKK!!!
“AH-HA-WAHH!!” I blubbered.
My legs kicked and kicked while the hard wooden paddle rained down again and again on my dampened rump, always right on target. She delivered each stinging slap with the impact of a squash player, causing me to buck wildly across her silky thighs. I felt so pathetic, bent over this beautiful woman’s lap, my wet diapers now exposed to both of them, while she slapped my sissy bottom repeatedly with her paddle. I had wanted so badly to impress my pretty babysitter from ten years ago and now, I was right back where I started, getting a good hard spanking while I cried like a baby girl.
WHAPP!! SMACKK!! THWAPPP!!
Each angry slap from the paddle landed crisply, delivering more stinging pain to my already punished cheeks. When the face of each had been spanked a shiny, ruby red, she turned her attention to the sides, whapping and slapping them mercilessly while I wriggled helpessly beneath her. My soft, tender bottom was paddled to a glowing, fiery blaze, which prickled like a panty full of red coals.
After what seemed was an eternity, she finally stopped and handed the paddle back to Barbie.
I was too weak to get up, and I sobbed and cried, my chest heaving as she helped me to my feet. I hid my face in my hands in shame while I shifted my weight from one foot to the other. The heat emenating off my bottom could’ve cooked an egg and I howled miserably. I could only imagine what Barbie was thinking of me as she discovered what a miniscule pee-wee I had, which was mostly hidden within my modest bush.
Vanessa took several baby wipes and cleaned her thighs of the pee that had touched her legs until she was satisfied it was clean again. Standing up, she re-arranged my fresh diapers, a stack of three that had a soaker pad sewn down the middle. Taking my hand, she gently shifted me over and sat me down on the diapers, which caused me to erupt into a fresh torrent of tears. From out of my field of view, she brought a big pink pacifier over and pushed it between my quivering lips. I sobbed loudly as I accepted it meekly, feeling like a baby all over again.
Vanessa shook her head as she went about her business, smearing my bright red bottom with more diaper rash ointment while I cried shamelessly. Several good shakes of the powder followed, after which she pulled up my diapers and secured them closed with pink bunny diaper pins. I looked away in humiliated misery as she snaked a pair of pink nursery print waterproof panties up my shaking legs, tugging them over the fat diaper without regard to my feelings of shame.
Barbie stood silently watching all this, her hands on her hips, no doubt amazed at what a big baby I was.
When Vanessa was done, she stood up and looked down at me, an immensely satisfied look on her beautiful face.
“Okay, Jimmy. It’s time we got a few things straight,” she started.
She looked so strong and powerful, with her dark penetrating eyes, the firm look on her face, her big breasts thrusting out proudly, and her tall, imposing stature. I knew I would never cross her again. She was right–nothing had changed between us–she was still the all-powerful figure that would hold sway over my life, changing my diapers when needed and spanking my bottom when that was what I needed.
“First off, your mommy sent you over to me because she was fed up with you. She said you were an immature little sissy and I’m in complete agreement with her.”
I hung my head in shame as she revealed her true feelings about me.
“It is apparent that you need a firm hand to give you the discipline you so obviously lack. I will be that firm hand,” she said, her voice like bands of steel.
“You will wear diapers from now on, since you can’t be trusted without them. If you need to be changed, either I or Barbie will do it for you. You are not to touch your diapers by yourself, under any circumstances, do you understand me?” she said pointedly.
I nodded my head sadly and was rewarded with a hard slap to my face.
“OWWW!!” I cried out.
“You will address me as ‘Ma’am’ from now on, do you understand??” she demanded.
“Y-y-yes M-Ma’am,” I whimpered fearfully as I rubbed my stinging cheek.
“You will also address Barbie as Ma’am. Is that understood?”
“Yes Ma’am,” I responded quickly.
Barbie was smiling wickedly at me but there wasn’t a thing I could do about it.
“Good. Then gather your wet diapers and put them in the washing machine. Barbie will show you how to do laundry around here. We have a clothesline in the backyard where you can hang your plastic panties up to dry.
“I will have a further list of chores for you but for now, you can start with the laundry,” she said as she turned to go.
“Oh, by the way,” she said as she turned back to face me, “my lingerie needs to be hand washed. And don’t get any ideas about wearing the panties–they won’t fit over your diapers and I don’t want you stretching them out trying.”
I blushed from the humiliation of her insinuation while Barbie smiled back at me.
After Vanessa left the room, Barbie crossed over and slapped my thickly padded bottom.
“C’mon Diaper boy. I’ll show you where to get started.”
During the next several weeks, I began getting accustomed to my new status under Vanessa’s rules. I found her to be a lot more strict than I remembered and she, along with Barbie, enforced her domain with an iron hand (and a hard wooden paddle). I was made to go to bed at 9 pm sharp, my tv time and usage were severly restricted, I was required to take afternoon naps, I had to ask for my diapers to be taken down so I could use the toilet, and my list of chores seemed to grow daily.
Barbie, while being the official maid of the house, was only too happy to have me assume her duties, with her watching and supervising my efforts. She barely talked to me except to tell me something wasn’t clean enough or that it wasn’t up to her standards.
I, on the other hand, couldn’t keep my eyes off her. I never missed an opportunity to watch her walk and it didn’t matter if she was coming or going, she looked fabulous either way. Her short, poofy mini-skirt tended to bounce and sway with her saucy bottom as she strode around and I noticed that when she walked, she put one high heeled foot in front of the other, sashaying like a model down a runway. Of course, she was certainly good looking enough to be a model although I don’t know if she was or not. She had shapely, sexy legs that never failed to stimulate whether she was wearing black hose or fishnets, as was sometimes the case. I don’t know why Vanessa required her to dress so sexily, I only knew I loved it.
Of course, I would have loved it more if she felt the same way about me, but that was hardly the case. She was all business with me and never spared me a glance, unless she thought I was staring at her too much. She had slapped me several times when she had caught me ogling her fantastic legs or her luscious breasts and she had threatened worse if I didn’t stop. Nonetheless, that didn’t prevent me from watching her secretly as she moved about the house and just seeing her move was enough to make me become aroused. She liked to recline on the sofa and put her feet up on the coffee table while she made me vaccum the house. I would steal glances at her sexily crossed legs, admiring her stilletto heels from whatever vantage point I was at.
Even when she changed my diapers, she was strictly business with me. I suspect she’d never have touched me if she hadn’t been specifically required by Vanessa to do so while she was at work. She did a rather rushed job of it, making me pull my wet diapers off and deposit them in the hamper while she hurried me through the rest of my changing. In her haste, she sometimes stuck me with the diaper pins and she never apologized for it. More often, she chided me for being such a big baby and she scolded me telling me that if I were a real man, I wouldn’t be wearing diapers anyway. Of course, it was one of the few times where I could stare at her breasts without being slapped since they hung right in front of my face as she was changing me. I figured she was about a 36D by the look of them and she never failed to dress in such a way that they were displayed in the most erotic way. With her sexy push-up bras, the upper halves of her breasts were lifted up into two glorious mounds of smooth, youthful flesh, tempting me daily with their perky splendor. Her tops were always low cut so that when she bent over to powder me and pull up my diapers, I was treated to a fabulous view down the front of her blouse, allowing me to see the center of her bra and sometimes the lace of her cups when I was lucky. My little weiner often rose to the occasion although the sight of it only brought laughter and disdain from Barbie. She’d often pinch it painfully and laugh, showing me her perfect set of teeth between her delectable, full lips as she told me such a tiny penis belonged wrapped in a thick baby’s diaper, rather than be free for adult use.
Being in such close proximity to two such sexy babes kept me in a perpetual state of arousal. It didn’t help matters that Vanessa bought the softest possible diapers to keep me in and they conspired to caress my wee-wee all day and night in a torturously erotic embrace. The trouble was that I was rarely left alone so my opportunities for relieving myself were few and far between. Vanessa had made it quite clear that there would be serious consequences if she caught me touching myself and I didn’t doubt her for a second. However, working in the same house with the young and sexy Barbie day after day kept me constantly horny and frustrated.
Once, while I was dusting in Vanessa’s bedroom, I came across a framed picture of her in a bikini. Even at first glance, it set my heart beating wildly and my pee wee twitched inside its baby soft prison. Picking it up, I gazed longingly at her incredible curves, the sensual shape of her hips and thighs, her smooth, supple skin, the way the strings of her bikini bottom tied at the side, but more than anything, her big, beautiful boobs that were straining at her top. Words cannot begin to describe the glorious shape of her full, round breasts, barely contained in the small stretched triangles of the thin fabric of her bikini top. I marvelled at the perfection of her bosom and as I did, my little weiner began to grow, quickly attaining its full length of (almost) two inches.
By reflex, my free hand went down to stroke it over the cushiony padding of my diaper. Along with super fluffy, triple thick cloth diapers, Vanessa also bought the softest plastic panties and my efforts brought about an immediate reaction. My breathing quickened as I stroked the bunny soft, thick cotton padding and let my eyes linger over the bikini bound image of my governess. Darting my eyes at the door, I saw no sign of Barbie and I sat down on the bed to provide myself with some badly needed relief. In no time at all, I was swimming in ecstasy, my eyes mesmerized by Vanessa’s angelic body.
I knew I was taking a tremendous risk, but I couldn’t help myself. My diapers felt so caressingly soft and Vanessa’s picture was so sexy. Looking at her pretty face, I could easily imagine what she’d do if she caught me in here but I was quickly rising to a blinding climax.
Being a premature ejaculator, I came quickly and I splashed my little load of jizz into my waiting diapers. I panted deliriously from the orgasm and gulped at the intensity of it, my head spinning wildly. No sooner did I set the picture back down on the table when Barbie came around the corner.
“What are you doing sitting around?” she demanded, “get to work! When you’ve finished in here, I’ve got another list for you to start.”
With my face a bright red, I bolted up and murmured a quick ‘yes ma’am’, as I grabbed the pink feather duster and finished the table, hoping she hadn’t seen me in my brief moment of pleasure. As she strode back out of the room, I breathed a sigh of relief at my victory, giggling as I felt the warm sticky mess in my diaper that would remind me for the rest of the day of my secret success.
It was also during these first couple of weeks that I noticed other changes.
I was in the kitchen, hand washing Vanessa’s lingerie with Barbie close by, supervising my efforts. With my hands deep in a sink full of sudsy water, all of a sudden I felt a stream of warm pee escape into my diaper without warning.
“Oh!” I cried out, crossing my legs quickly to try and stop the flow.
“What’s the matter?” Barbie said suspiciously, looking me up and down.
“Nothing,” I said meakly as I blushed a deep shade of red.
That was the first time I’d wet myself and not even felt anything beforehand. While it was true that I was wetting my diaper occasionally at night, usually during the daytime, I’d have enough notice that I could ask Barbie to take me to the toilet to allow me to do my business. She’d watch while I made my tinkle and then she’d swat me on my bottom as I scurried past her so she could pin me back into my diapers. But this was a disturbing trend, not having any indication or inkling of what was about to happen, before it happened.
Two days later, it occured again, while I was hanging my plastic panties up on the clothesline out back. Suddenly, without any prior indication, I felt the front of my diaper growing wet and warm and by the time I was able to shut off the flow, the front of my diaper was well soaked. I ran inside, my eyes brimming with tears, while I struggled with what was happening. Had I completely lost all control over my functions? Would I need diapers the rest of my life? I paced back and forth in anxious concern as I pondered this latest event.
The next question was what to do about it. I knew Barbie would be furious if she found out I’d wet my diapers during the day. Two days ago, she’d slapped my bottom with the paddle when she found my first accident and I could already hear the disparaging remarks she’d have ready as she changed me in the bedroom. I could try and hide it all day but then Vanessa would find out when she changed me before bedtime. Odds are, she’d probably spank me for being such a sissy and I didn’t want to chance that. The way I saw it, Barbie would probably just yell at me but then that’d be it. That sure beat a stinging spanking from Vanessa so I figured that was the way I’d go.
However, during the tension filled hour in which I debated the issue back and forth, I couldn’t help but leak a little more and my frazzled nerves made it impossible to hold it back. It was also made more difficult by the fact that my diapers were already wet–my first reaction was to just let it go and pee some more. Pacing back and forth in the kitchen, I wet a little, bit by bit, until the pee began to seep back into the seat of my diapers. Several times, I started to go and find Barbie, only to stop myself out of childish fear. As the minutes ticked by, the pressure on my bladder only increased. I tried to relieve the pressure by letting out just a little but my diapers were getting wetter and wetter as the afternoon progressed.
Finally, I decided I couldn’t wait any longer.
Walking upstairs, I found Barbie in her room, bending over at the waist to get something off the floor. In her tall, black patent leather pumps, her legs were spread slightly apart and my eyes immediately went to her sheer, black panties that framed and hugged her perfect derriere in the most delicious way. I swallowed hard as I gaped at the fantastic image before me, trying to summon up the bravery necessary to tell her of my accident.
“Uhm…Barbie?” I inquired timidly.
She spun around in surprise, a look of anger on her pretty face.
“What are you doing there, you little panty pervert–spying on me?” she said accusingly.
“Oh no! No Ma’am!” I was quick to say, “I just walked in.”
“Well? What do you want?” she snapped impatiently.
“Um, well, you see-“
“I haven’t got all day, Diaper boy, what do you want?” she interrupted me brusquely.
My face reddened at this rude assault by such a sexy babe.
“I wet my diapers!” I blurted out. Tears started to fill my eyes again and she looked at me with a mixture of pity and disgust.
“You’re nothing but a big sissy, aren’t you?” she said, shaking her head.
I nodded, hoping it would get some sympathy from her. Whether it did or not, I wasn’t sure because she walked past me and out into the hall.
“Well, come on, Sissy-boy, looks like it’s time to change your diapers again,” she told me.
I blushed hotly, ashamed at myself for my infantile behaviour but I followed her into my room where the changing pad was still set up on my bed from this morning. Sheepishly, I clambered onto it while Barbie retrieved a fresh stack of diapers from the dresser. Coming back over to me, she began yanking down my plastic panties, shaking her head as she did so.
“Please don’t tell Vanessa, okay?” I pleaded desperately, hoping against all hope she’d agree.
Without a word, she unpinned the sopping wet diaper and pulled it out from under me as she held my legs high up in the air by my ankles. I saw her bend down to pick something up and then she hoisted my ankles back up into the air abruptly. Suddenly, I saw the paddle come swooping down, landing on my upturned bottom with a loud SMACKK!! I cried out in shock but she smacked me again even harder. I tried to kick my feet but she held them like a vice and she brought the paddle down again and then again. Gripping the vinyl changing pad for support, I burst into tears and howled in pain, struggling in her grasp but this time, she only slid the stack of diapers under my damp and stinging bottom. I whimpered childishly, while she smiled down at me wickedly.
“Oh, I’ll tell her alright,” she said as she sprinkled powder over my shriveled pee-wee, “I’ll tell her what a big sissy baby you are and how she should dress you up like a little baby girl.”
“Please, please don’t tell her that,” I begged her as hot tears trickled down my cheeks, “I couldn’t help it.”
Barbie ignored me as she pinned up both sides snugly and retrieved a pair of pink, ruffle lined plastic panties from the drawer.
“See these?” she said as she held them up for me to see, “they’re perfect for a big, diaper wetting sissy like you.”
I sobbed tears of shame as she snaked them up my skinny legs and over my fat, bulky diaper.
“Here you are, a nice wittle pacifier to make you feel better,” she said as she stuffed my pink rubber pacifier between my lips. I cried softly as I sucked on it, knowing deep down inside that what she was saying about me might be true.
That night, I didn’t get a spanking from Vanessa as I was sure I would. Instead, she merely sent me to bed early and predictably, I woke up the next morning with my diapers soaked again. Without a word, Vanessa changed me and left for work, leaving me alone with Barbie again.
Barbie seemed to relish humiliating me and she never passed up an opportunity to do so. Last week, she had made a point of making sure I was hanging up my plastic panties out on the clothesline, right at the time when the school kids were getting out of school. They walked by, seeing me in my t-shirt, sneakers and bulging diapers, and they laughed non-stop, taunting me and calling me childish names. In my state of panic, it was all I could do to keep from flooding my diapers.
Barbie also liked to make me go outside to get the mail. This meant walking a good distance out in front, in plain view from the street, where people would see me and my shameful diapers. Often, she would purposely wait until she saw someone coming by and then she’d send me out, locking the door behind me. It made me want to cry from the humiliation of it!
Today when I got the mail, I was fortunate that no one was around but when I ran back to the house, I noticed one of the packages was from a place called Babyland. The package felt kind of squishy like clothing and I wondered nervously what it might contain. Opening the door, I was glad to be back in the house when Barbie snatched the mail from me and handed me the feather duster.
“Get to work,” she ordered me, “you can start with the study.”
Wordlessly, I took the duster and walked away but I was aware of the angry stare at my back from Barbie. Over the last week, I had noticed a tension building between us which stemmed from my resentment at being bossed around by this girl who was both younger and physically smaller than myself. She lorded over me like I were her personal slave and she demanded absolute obediance. I knew it infuriated her when I didn’t say ‘yes ma’am’ to everything she said and I did it on purpose as my only means of getting back at her.
When I reached the study, I allowed myself a smug look of satisfaction for my small victory, and I plotted more ways of defying her whenever the opportunity should present itself.
I was so absorbed in my plans that I failed to hear the front door open. I also failed to hear Barbie’s friends as they walked in. It wasn’t until I heard numerous giggles behind me, that I finally broke out of my reverie.
At the moment, I was bent over, my ruffle covered plastic panties sticking up in the air when I heard them behind me. I shot up like a jack-in-the-box to see three girls standing next to Barbie, staring at my diapers and laughing in open amusement. I blushed hot red in embarrassment and tugged my t-shirt down in a desperate attempt to hide my frilly diapers.
“Stop it!” I squeaked in a shrill tone of voice.
Barbie had joined in the laughter and in my state of panic, I felt a hot stream of pee surge into the front of my diaper.
“Stop it!” I repeated frantically, sounding more girlish than ever.
“Stop it!” one of the girls said mockingly, imitating my wimpy tone of voice.
The other girls laughed all over again and my face turned a deep shade of red.
Barbie stopped laughing and she suddenly became serious.
“Jimmy. I want you to pull up your shirt and show the girls what it is you’re wearing there,” she ordered me.
“No!” I said hotly. I was angry and humiliated and I wasn’t going to let her get away with anymore of this.
Suddenly, the room fell silent.
“What did you say?”‘ she said slowly and menacingly.
I swallowed hard and wondered if I had made the right desicion.
“No!” I repeated, trying as hard as possible to sound firm and manly but my voice faltered and cracked with uncertainty.
The girls all looked at each other realizing they were in the midst of a showdown where only one of us could win.
“You will address me as Ma’am, little boy,” she said icily, her beautiful steely eyes drilling into me, “now get over here this instant.”
Her words hit me like a bucket of icewater and now real fear set in. Already I was questioning the wisdom of standing up to her in front of her friends but now it was too late. Unable to move, I stared back at her as I bit my lip in angst, holding the hem of my t-shirt down trying to hide my diapers. Deep inside of me, I carried a fimly ingrained and well placed fear of strong, determined women. I was on the verge of buckling in this contest of wills.
With slow, deliberate moves, Barbie reached over and retrieved a stalk of very thin bamboo that was in a decorative vase. It was about the thickness of a pencil and roughly three feet long.
“Get over here–right now,” she ordered me. Her voice was low and it made me shiver with fright.
Another surge of pee escaped and I let out a cry of despair as I crossed my legs.
“Now!” she barked, emphasizing her command with an abrupt slash of the bamboo stick. It hit the wall next to her with a sharp snap, causing even the girls to jump.
By now, I realized I had pushed her too hard. I was in big trouble and there was no way out of it. Whimpering in fear, I inched forward, afraid to do anything that might make her angrier.
“Pull your t-shirt up,” she commanded me.
“Yes, Ma’am,” I said, now completely subservient. I lifted up my t-shirt, allowing her girlfriends to easily see my frilly pink plastic panties, covering the thick, bulging diaper underneath.
“Now, put your hands on the arms of that chair,” she said, pointing to an ornate wooden chair next to her.
With great trepidation, I moved over to the chair and bent over it, placing my hands on the arms as I was instructed. My heart was beating frantically now in my chest and my mouth was parched from fear. Now, my diapered bubble butt stuck out for everyone to see and make fun of. Barbie came up behind me and began slowly pulling my panties down, drawing out the agony of my punishment and increasing my level of anxiety. When they were mid-thigh, she unpinned my diapers and pulled them back, exposing my bare bottom before the girls.
“Well, well, well,” she said as she discovered the wet cloth below my crotch, “looks like our little sissy-boy has wet his diapers again.”
Her voice was heavily condescending and I blushed hotly, my neck and ears growing red with shame.
“This is what happens when you disobey me,” she said evenly.
As I faced downwards, I heard the swish of the bamboo through the air and then it landed on my tender upraised bottom with a crisp wwwhoop!!
“OOWWWWW!!” I cried loudly, jumping up from my position.
“Get back down!” she ordered me, “if your hands move once more, I’ll make sure Vanessa gives you a good paddling when she gets home.”
That put the fear of god in me and I quickly put my hands back down on the arms of the chair, leaving my bare bottom in the most inviting position for her once again.
I yelped in pain and kicked my feet up individually as I struggled with the fierce stinging on my fanny. I couldn’t believe the intensity of the pain caused by the narrow strip of bamboo.
I quickly burst into tears and began sobbing as my bottom now sported four angry red stripes across it’s round, youthful surface.
Swish-whap! Swattt! Swwwatt!
I held onto the chair while hot tears streamed down my face and I bawled like a baby. Barbie was a good aim and she never missed her target, no matter how much I thrashed around. The cruel strip of bamboo landed unerringly on my cheeks, raising crimson stripes with each searing impact. She took her time, waiting for me to move back into the best position before she let me have it again, slashing at my poor striped bottom mercilessly. One of the girls had moved around to see the look on my face and I clutched the arms of the chair miserably, wailing like a little girl, as Barbie whipped away at my fanny. I knew I looked like a big sissy crybaby but I just couldn’t help myself. My bottom was on fire!
At last, she stopped and put the bamboo back into the vase.
I sobbed and moaned while she pulled up the back of my diaper and pinned it tightly on either side. I felt her pulling up my plastic panties as I looked up to make eye contact with the pretty blonde in front of me. With tears streaming down my face, I flooded my diapers with streams of hot, urgent pee. The tension of the ordeal must have done it because I couldn’t stop myself this time. I remained bent over in my humiliating position as my diapers grew wet and warm, the pee saturating the front very quickly and then collecting between my legs, where the other girls could see it. One of them pointed it out to the others and they giggled at my humiliating display of babyishness. I just kept crying, half from the stinging pain that was throbbing on my bottom and half from the shame of what was happening.
I didn’t dare get up from my servile position, now that Barbie had clearly shown everyone who was in charge here.
“Stand up and face me,” Barbie commanded me.
With my face red and wet with tears, I stood up but was unable to look her in the eyes. My brief, foolish stand of defiance had ended disastrously, and my shame knew no bounds.
“Maybe that will teach you a lesson,” she said smugly, as she put her hands on her hips.
“Yes, Ma’am,” I said abjectly as the last stream of pee filled my soaking wet diapers.
“Good. Maybe from now on, you’ll show me the proper respect that has so far, been lacking,” she scolded me.
“Yes, Ma’am,” I sniffled.
“Now go to your room and get into bed. It’s your naptime, Diaper boy,” she ordered me like a four year old.
“B-but…my diapers are wet now,” I complained timidly.
“Too bad Sissy, you’ll just have to get used to it,” she declared.
“Yes, Ma’am,” I sobbed as I shuffled out of the room, completely defeated again.
As I walked by, she swatted me on my ruffle pantied bottom, causing me to yelp like a little girl.
Her girlfriends erupted in laughter.
More and more often, I found myself discovering strange packages that were arriving from places like ABWorld, LLmedico, Babyland and BigBabies.com which made me very nervous. Some were small packages and I assumed they were clothing but others were large, heavy boxes, and I could only wonder at what they contained. Worse than that was having to sign for the packages when UPS dropped them off. Barbie insisted that I greet the UPS lady at the door, saying I was the “baby of the house” and could sign for any packages. She would giggle and hand me the clipboard, often adding a humiliating comment on her way out.
At about the same time, workmen started arriving, doing some kind of remodeling to a room at the end of the hallway. Neither Vanessa or Barbie would tell me what it was but they made a point of locking the door when the workmen went home for the evening.
At about the same time, what little control over my bladder seemed to gradually disappear and it was impossible to hide the problem from Vanessa. All too frequently, I would soak my diapers during the day and of course, I rarely woke up anymore without my diaper sopping wet. Vanessa was fond of saying ‘once a sissy, always a sissy’ but there was nothing I could do to reverse the trend. It just happened suddenly and without warning, and before I realized what was going on, my diaper would be wet and warm and I was helpless to stop it. It really made me feel like a feeble baby to be dependant on diapers again and it left me angry and frustrated. Worse than that was having to wear my wet diapers for long periods of time before one of them felt like changing me. I came to looking forward to getting to wear a fresh diaper and being dry for however brief that might last.
Part of me wondered if these were the secret hopes of all sissies–simply to be able to wear dry diapers.
One night, I overheard Vanessa talking to Barbie about a double date that they were clearly excited about. Apparently they were planning on meeting two hunky men and they were determined to dress as sexily as possible for them. I did everything I could not to think about it but inside, I was burning with jealousy. Here they were going to go out and have a fun time, and I was going to be stuck at home, sent to bed early after being pinned into my sissy diapers. It was all so unfair! Not to mention that I was frantically horny. Well, I was going to show them!
I conspired and made plans to take advantage of their absence. I fantasized all day about going into Vanessa’s room, laying her bras on the bed and slowly stroking myself to orgasm as I looked at her bikini picture. It was the perfect plan! They would be gone all night and I would be free to do whatever I pleased. I couldn’t wait! Yes, I was frustrated with their freedom and the lack of mine, but at least I would get a dizzying orgasm out of it.
That evening, I did everything I could to make them believe I had nothing up my sleeve, although it hardly seemed necessary. Clearly, they had their manly dates on their mind and they barely paid me any attention at all while they got ready for their night out.
If I was horny before, these two succeeded in making me even hornier. I was frantic with lust as I serrepticiously watched them fastening their dark stockings up to their garter belts, hitch up their silky panties, and fitting their push-up bras to get the maximum cleavage. I nearly came in my diapers as I watched them dressing and they picked out their sexiest dresses to wear. Snug, form fitting little things that revealed the most skin and showed their luscious curves to maximum effect. Both of them did their make up so that they looked even more ravishing than usual, if that were even possible. In a way, I couldn’t wait until they left, so that I could finally masturbate myself to my heart’s delight. I was so excited!
My plan was to wait until they left the house. I’d pretend to fall asleep and then, after they’d left, I’d jump out of bed to begin a night of forbidden, wanton pleasures! It was all falling into place.
Vanessa, just like clockwork, came in to change me just like usual before bed. Even my soaking wet diapers couldn’t spoil her mood and she hummed merrily as she pinned me into another triple thick set of bunny soft diapers for the night. There was only one small difference. While she was waiting for Barbie to get ready, she insisted on making me drink a large baby bottle of warm milk. I tried to tell her I wasn’t thirsty but she only ignored me, and she held the bottle to my lips, forcing me to drink it while she waited. I never liked milk, especially warm milk, but even this drink tasted a bit strange to me. No matter. I’d do what she wanted because in ten minutes, she’d be gone, along with Barbie and I’d be free to enjoy my masturbatory adventures.
Vanessa was wearing a very low cut dress with a scoop neck and my little pecker was at full attention. She was so pretty and strong, and as she held the baby bottle to my mouth, her big breasts pressed against my face. I gazed impatiently at the deep crevice between her boobs, watching them rise and fall with each breath she took. I wanted so badly to stroke the soft surface of my plastic panties but I held back, knowing I had just another few minutes to wait before they were gone.
After I’d drank half the bottle, I tried to turn away but Vanessa kept the bottle positioned in such a way that I couldn’t escape it. I was forced to nurse from it like a baby and it was obvious I was going to have to drink it all before she’d remove the bottle. I felt a strange sense of euphoria as I sucked on the rubber nipple. I felt like such a baby, wearing my thick diapers that would soon be wet, and nursing from a bottle forced upon me by my beautiful governess.
At last, I finally finished the milk. A line of drool remained attached as Vanessa slowly lifted the bottle from my lips. Glancing at her watch, she smiled down at me.
“Sweet dreams, little Sissy,” she said in her most sexy voice.
For some reason, my limbs felt heavy and I could hardly keep my eyes open. The room went hazy as I watched Vanessa saunter out of my room, her sumptous derriere fantastically encased in the thin fabric of her short mini dress.
I seemed to be spinning downwards, into a pool of warm darkness and I was only vaguely aware that my plans had been defeated–there would be no masturbating and no orgasm for me tonight.
My last thoughts as I fell asleep were that I had once again, I had been outsmarted by Vanessa.
Several days later, I was still horny and frustrated, with no outlet for my sexual desires. I was so horny, I was ready to cry! I was desperate to get into Vanessa’s bedroom so I could masturbate to her picture and finally, on Saturday, I got my chance. I knew my window of opportunity would be limited so I wasted no time in doing my deed. In less than a minute, I had stroked myself to an earth shattering climax, only to have Barbie walk in on me just after I’d finished. I was still breathing a little hard but vastly relieved she hadn’t caught me.
However, she looked at me strangely and then walked out again. Consumed with guilt, I went out after her, only to find her whispering in her bedroom to Vanessa. When I walked in, the latter told me to come over to her. Today, she was wearing a short skirt with a slit up the sides, her chrome high heeled sandals, and a strapless top that pushed her huge bosom up into two wonderful globes.
Once again, my heart rate shot up wildly and I hoped there was no sign on my face as to what I’d just done.
“I want to check your diapers,” Vanessa told me straight out.
I racked my mind for some reason to stall her but I couldn’t think of anything. In my panic, I tried to force myself to pee and cover up the evidence of my misdeeds but of all times, nothing would come!
“But why?” I asked innocently, “I’m not wet or anything.”
“Come here, Jimmy,” she commanded me, her voice taking hold of me with its iron grip.
“B-but, why?” I stammered, even as I edged closer to her.
Without explaining herself, she reached forward and yanked me closer to her, making me cry out in fear.
“Oh!” I exclaimed.
With her long, manicured nails, Vanessa tugged down on my lilac colored plastic panties, lowering them to the level of my calves. My knees suddenly went weak as I looked up to see Barbie staring hard at me, her ravishing green eyes drilling into me accusingly.
Vanessa unpinned one side of my diapers and folded it down, revealing the gooey, sticky cum from my masturbatory misadventures. She took one disgusted look at it before looking up at me, fixing me with her withering stare.
“Barbie, would you be so kind as to fetch the paddle from Jimmy’s room?”
I immediately began fidgeting in front of Vanessa, the threat of a spanking weighing heavily on me.
“I-I didn’t mean it,” I offered lamely, hoping somehow that would make it better.
“You are going to get a good, hard spanking, Jimmy,” she said as she looked me in the eye, “and then, there are going to be some changes around here for you.”
My heart skipped a beat as I imagined what those would be.
“You are a naughty little boy who needs to have his bottom paddled. And after that, I’m going to give you a nice, hot, soapy enema,” she said as she looked deep into my eyes.
I quivered with fear and my little sphincter puckered in anticipation of it’s upcoming punishment.
“Oh no! I promise I’ll be good!” I squealed.
At that moment, Barbie returned with the wooden paddle in her hand and a big smile on her face.
“I’m going to enjoy watching you cry like a baby,”she said smugly.
I whimpered in terror as Vanessa pulled me over her lap, the gooey cum in my diaper pressing against me as if to mock my recent orgasm.
“No-no-please no!” I whimpered, “please don’t spank me, please!”
Vanessa ignored me as she rubbed my bottom with the face of the paddle.
“Aww…are you going to give us a big sissy cry now, Jimmy?” she asked demeaningly.
As if to confirm what she was saying, crocodile tears spilled out of my eyes and I squirmed as she removed the other pin from my diapers, revealing my bottom for the spanking it so badly needed.
“Mommy,” I whimpered weakly.
The spanking that followed was long, painful, and humiliating, and it left me bawling like a three year old girl who’d had her doll taken away from her and ripped apart. Vanessa paddled my bottom into a flaming hot, cherry red and every square inch stung like bees were attacking me.
As I lay over her lap, sobbing and trying to regain my breath, Barbie brought over a big, red rubber enema bag that she’d filled to bursting with hot, soapy water. I could see the suds and bubbles where the cap sealed the container and beads of water glistened from its bulging sides. She hung it from a hook on the wall and uncoiled the long white tube that was connected to the bag. At the opposite end, was a large rubber dildo that had a hole in the end where the water would soon be flowing out of. I gulped in fear as she swirled the thick phallus in a jar of nursery scented vasoline, coating it with a thick layer of the lubricant.
“No…no…no,” I begged weakly, as I tried to wipe the tears from my eyes.
Vanessa ignored me as she stuck her fingers in the vasoline and then brought them up to my anus, coating it well and pushing inside the rest as she pulled my reddened cheeks apart.
“I want my mommy,” I whined as I squirmed over her lap.
Taking the fat dildo in her right hand, Vanessa brought it up to my hole while the other hand kept my cheeks spread. With resolute determination, she began pressing it firmly against my sphincter, refusing to let me squirm away from it.
“Relax, Jimmy,” she said softly, “it’ll go in a lot easier if you just relax.”
“Oh!” I squealed, “it’s too big! I can’t take it!”
Vanessa kept up the pressure, bearing the fat, slippery dildo against my hole while she worked with my stinging cheeks to open them up wider.
“No! Please…it’s…it’s too…big…oh!…I can’t–“
All of a sudden, that fat head of the dildo slipped past my rim and Vanessa smiled with satisfaction as she pushed the rest of it slowly inside me.
“Ohhhhh!” I moaned.
“That’s a good little boy,” she commended me, “that’s my little sissy.”
She twirled it around slowly and began pumping it in and out as I moaned helplessly. I knew I sounded like a little girl but I couldn’t stop myself.
“This is just what a sissy needs,” she assured me as she continued to pump me with the slippery dildo, “and it’s something you can look forward to from now on, every morning.”
“Ohh…” I moaned in distress.
I felt the pumping motion stop and Vanessa’s hand went to release the clip. With a suddenness I wasn’t prepared for, the hot soapy water surged into my rectum and I cried out in surprise.
“Oh! Oh! OHH!!”
“There, there, Sissy. We’re going to get you all squeaky clean today,” Vanessa told me.
The water flowed into me with great force and I soon found myself in the throes of strong cramps. I tried desperately to pinch my stinging cheeks together in the hopes of cutting off the flow but it was hopeless. The fat rubber dildo was buried deep into my rear and the soapy water continued unabated.
I was panting heavily when she finally snapped the clip closed, allowing the first flow to work it’s way deep into my bowels. While she waited, she teased me with the slippery dildo, twisting it around and pushing it further in.
“I hope you enjoyed yourself today, Jimmy. Because that was the last time you’ll ever come in this house,” she informed me.
I bit my lip anxiously as I wondered exactly what she meant by that although at the moment, I was pretty well occupied with the water churning around inside me.
“How many times have you masturbated since you got here, Jimmy?” she asked as she pushed the dildo in deeply, making me moan in reponse.
“Um-uh…just f-four times,” I admitted.
“And did you always use that picture of me in the swimsuit?”
How had she known about that? And I thought I had been so sly!
With a thick dildo buried in my bottom and more soapy water waiting to fill me up, I couldn’t hold back the truth.
“Y-yes, Ma’am,” I replied meakly.
Vanessa smiled as she released the clip and the water flowed once again into my pouting bottom.
“Ohhhh!” I moaned.
“Well, I’m going to put a stop to that from now on,” she told me.
Beads of sweat appeared on my brow but tears filled my eyes as I saw my one chance for relief being taken away. I wasn’t sure how she would do it but I was certain she’d find a way.
Meanwhile the pressure continued to build inside of me and I felt like I was ready to explode. Vanessa squeezed the clip shut again and I lay there, panting over her lap, the cramps painful as the soapy water filled me up. I squirmed helplessly for several moments until she released it again. I cried softly until the last of the water flowed into me, gurgling with finality. I heard the bubbles disappearing into my rectum announcing the end of the enema and, after waiting an infuriatingly long time, she slowly removed the fat, imposing dildo from my anus.
“Ohh!” I exclaimed as it slid out of me.
“Go into the bathroom now and release that. And I better not find one drop on the floor or you’ll be going right back over my lap again. Do you understand?”
“Yes, Ma’am,” I replied obediently.
I limped weakly to the bathroom and practically fell on the toilet as I released all the pent up liquid. My cheeks stung bitterly where they contacted the seat but the relief from releasing the enema made up for it. Several times during the next ten minutes, I stood up thinking I was finished, only to feel another wave of liquid waiting to get out.
At last, I had completely expelled the enema, and slowly I made my way back to my room.
Barbie saw me out in the hallway, and she called me down to her.
“In here, Jimmy. This is your new room,” she said with a smile.
Butterflies filled my stomach as I walked slowly and hesitantly toward the room that had remained locked up and hidden from me for the last couple of weeks. When I turned the corner, Vanessa was waiting inside, a cool smile upon her pretty face. The room was made up like a little girl’s nursery, with the walls decorated with cartoon characters and frilly pink curtains on the windows. A big wooden baby crib dominated the room, painted in pink and I could see the waterproof sheet on its mattress, all ready for me. To its right was a raised changing table with more nursery print vinyl stretching over its shiny surface. Underneath lay stacks of diapers and in a shelf beside it were a wide selection of plastic and rubber panties. A pink dresser with bunnies on it was to the right of that and in the open closet, I could see dresses and baby clothes of every type imaginable. Lastly, a mesh walled playpen was off to the left side, its floor containing numerous baby toys.
My mouth dropped open in shock as I took all this in.
“From now on, this is where you’ll live,” Vanessa said firmly, “you’ll start each day with a hot, soapy enema and then we’ll dress you for the day like the sissy that you’ve been acting like.”
As I stood in silence, listening to her lay down the law, I held my hands over my privates since by now, I was only wearing my sneakers and a t-shirt.
“It’s obvious that you can’t be trusted wth adult privelages so I’m taking those away. From now on, you’ll be treated like a helpless little baby girl, who has no control and wets her diapers like any infant.”
Vanessa took me by the wrist and sat me down on the changing table as she began gathering a stack of diapers for me. Tears were trickling down my face as I looked around my new surroundings and then back at her.
“I don’t wanna be a baby!” I sobbed as I bunched my hands into fists.
Vanessa took a big pink pacifier that hung from a loop and stuffed it in between my quivering lips, passing the loop over my head.
“There. That will be your constant companion from now on. If I ever catch you without it, I’ll paddle your little bottom–do you understand?”
I nodded tearfully as I nursed on the fat rubber nipple in my mouth.
She tucked my diapers underneath me and proceeded to coat my crimson bottom with diaper rash ointment as she continued to scold me.
“Jimmy. Just look at you. You’re an immature little sissy who simply refuses to grow up. You belong in diapers so that’s exactly where you’ll stay.”
A cloud of baby powder rose around me as she sprinkled the front of me with it.
“And I want everyone who comes over, to see you as you really are, a diaper wetting panty-waist, trapped in the body of a man.”
She pinned my diapers closed securely and I sobbed in shame. Reached over, she picked out a pair of pink, nursery print plastic panties and quickly snaked them up my legs, fitting them over my bulky diaper with a bit of a struggle. With my bottom sealed up again within my waterproof panties, the stinging on my cheeks was increased measurably and I squirmed on the changing table in discomfort.
Standing up, Vanessa went to the closet where she returned with a pair of glossy black mary janes, their buckles, a shiny silver chrome. Untying my sneakers, she removed them along with my socks and threw both sets in the trash.
“What are you doing with my shoes?” I cried incredulously as the pacifier fell out of my mouth.
“These, are your new shoes,” she said as she held up the childish mary janes to me. I pouted as she stuffed the pacifier back in my mouth and pulled a pair of pink and white lace anklets over my feet. After that, she put the shiny black shoes over my feet and buckled them in place. I felt so sissyish as I looked down at the babyish shoes, with the lacey edges of my socks encircling my ankles.
Returning to the closet, she picked out a puffy petticoat with multiple white layers, each, softly ruffled so that it formed a flared out hem at the bottom. Taking my t-shirt off, she threw it in the trash as well and I squealed in protest through my pacifier. Ignoring me, she lowered the frilly confection over my head and adjusted the thin shoulder straps, making sure the layers of the petticoat fell evenly. Standing up again, she browsed the well stocked closet until she pulled out a lacey pink party dress, with short, puffy sleeves and white lace highlights all over it. I shuddered as I noted the short ruffled hem. Pulling it over my head she turned me around to button it up in back. All the while, I was whimpering through my pacifier while Barbie smiled down on me, smugly satisified with how things were progressing.
“Stand up, Sissy,” Vanessa ordered me curtly.
Sniffling to myself, I stood up on my babyish shoes and looked for the first time at the huge mirror that was covering the opposite wall. Looking back at me was an insecure little girl, pacifier in her mouth, her diapers and pink plastic panties plainly visible under the multiple ruffles of her party dress. Except that the little girl was me! Turning slightly, I noticed that the thick diapers gave my bottom a fat, round profile that only enhanced my infant look. I blushed deeply as I gazed at the reflection and it occured to me that I made a very natural looking baby girl, especially with my soft, feminine legs.
“Since you obviously still need your mommy, I will fulfill that role,” Vanessa explained, “from now on, you will address me as ‘mommy’. Do you understand?”
“Yes Mommy,” I replied submissively.
“The bathroom is now off limits to you. Since you can’t seem to control your peeing anyway, you can just use your diapers like every other little baby.”
“Yes Mommy,” I repeated.
Barbie led me over to a vanity and she began methodically putting small curlers in my hair, adding a foul smelling permenant solution before sealing each curl in place. I was angry and frustrated about the process but there was nothing I could do about it. It was still painful to sit down, even on the padded seat, and I sure didn’t want another session with Vanessa’s paddle.
While Barbie was attending to my hair, Vanessa busied herself by painting my nails a glossy, bubble gum pink, which gave my hands a distinctively sissyish look. I could only chew on my pacifier and pout as these two beautiful women transformed me into a prissy, sassy, sissy baby girl.
A half hour later, they were done, and they had me go out of the room and wait for the solution in my hair to take effect. Two boring hours later, they took out the curlers and fluffed my hair out. Peals of laughter ensued as the women snickered at me and my new Shirley Temple hair-do.
Barbie practically dragged me back into my new nursery so I could see the whole effect in the full length wall mirror. I blushed a deep shade of red as I witnessed in total, the full effect of my sissy transformation. I held the ruffled hem of my satiny party dress daintily with my pink tipped fingers as I realized my nursery print plastic panties were in full view below. My glossy mary janes gave me a childish look but the pacifier still in my mouth, along with my thick diapers, verified what I really was–nothing but a big baby.
Tears filled my eyes as Barbie led me over to my new playpen, sitting me inside with strict instructions not to get out unless I wanted another spanking. As I stared over the padded rail, I gazed at my babyish reflection and softly cried to myself. I stopped only momentarily as I felt the front of my diapers growing wet and warm. I was wetting myself without control again and I burst into sobs befitting my appearance.
The next day, Vanessa strode into my nursery with Barbie, a ravishing smile on her face. In her hand was a small plastic bag with something I couldn’t identify within it.
“It’s finally arrived!” she exclaimed as she dug her long nailed fingers into the clear manufacturer’s bag, “and just in time for your birthday.”
She pulled out a strange looking item that I didn’t recognize, a series of loops made from a type of soft braided cord.
“Barbie, be a dear and take his diapers down will you?” she asked her maid.
Barbie strode forward and pulled me out of my playpen, leading me toward the changing table where she sat me down, smiling wickedly at me as she did so. I had no idea what was up so I lay back and let her pull my plastic panties down, revealing my semi-wet diapers underneath. When she unpinned the cloth, Vanessa bent over and began positioning the loops of cord around my scrotum and penis. I looked down naively, not knowing what it was she was doing, as her smooth hands fiddled and adjusted the loops, securing them and cinching up them snugly.
“I had to get the smallest one they made, but even that was too big,” she explained to Barbie who watched with great fascination, “the man even asked me if this was for a little boy but I told him, no, just an immature little man.”
Barbie giggled and asked, “so how did you find one small enough?”
The nice man said he’d custom make one for me,” Vanessa told her, “he said anyone with such a tiny penis probably didn’t have any use for it anyway.”
On closer examination, I saw that one loop encircled my sack, another went around the base of my wee-wee, while another encircled it just a bit higher. They were all interconnected by a section of the cord.
Vanessa continued to adjust the device while I stood in helpless apprehension. I felt her cinching the loops tighter until they were snug, but not uncomfortably so. I wanted to stop her and stand up for myself but how? She’d just yank me over her lap and spank the daylights out of me.
Finally, she stood up and looked down on me to observe the results of her work.
”There,” she said, clearly satisfied, ”now for the true test.”
I stared down at my tiny pecker, now securely bound within the three loops of this device and I was seized with panic. The cord wrapped around my balls made it stick out slightly, now that it was encircled like a tie around a bag of candy and the ones around my shaft looked snug and secure.
“Okay Jimmy, let’s see you take it off,” Vanessa challenged me.
With the desperation brought on by the realization that I might never be able to play with myself, ever again, I clawed frantically at the corded loops, trying to tear the contraption off me. The material didn’t stretch in the slightest and despite its smooth feel, it had the strength of steel. Pulling mightily, the loops dug painfully into my balls and weiner as I tried to rip the thing off me. I gasped in pain and was forced to let go because of the agony I was inflicting on myself. Stamping my feet in frustration, I stormed about my nursery in a tantrum more like a five year old, than the adult I thought I was.
Barbie clapped her hands together and laughed with glee at my predicament. Vanessa smiled down at me with smug satisfaction while I made repeated attempts to prize even a part of my organ out of the device. At last, I gave up and slumped onto the edge of my crib in defeat.
“It’s not fair!” I sobbed, ”it’s not fair!”
“Jimmy,” Vanessa said suddenly in a very provacative voice.
I looked up from my misery to see her gazing at me with a seductive look I’d only seen once before.
Stepping over to me, she bent over slightly, hands pressed against the tops of her thighs, her immense breasts displayed in front of me within the confines of her tight, low cut top.
“Remember a long time ago when you were a little boy and I invited you for a closer look at my breasts?”
Her voice was soft and sultry with a timbre that was electrifying and as she spoke, her smooth, creamy hands began to caress her big, round cups sensuously. My eyes dropped to stare at what she was doing and I was hypnotized as I watched her stroking her bosom, alternately squeezing and lifting her boobs in a manner that drove me wild with desire. Vanessa was a living goddess with a heavenly body and her sexy game left me panting with excitement.
My little pee-wee responded immediately but no sooner had it begun to harden, than the restrictive diameter of the loops began to cut into my skin, preventing it from growing any larger. My sensation of sexual arousal quickly turned to unrelenting pain and I jumped up, trying once again to tear the restrictive device off me.
“Owwww!” I cried as my weiner battled in futility against its bonds.
“Take it off,” I begged her, ”please!”
Vanessa grinned down at me broadly, like a scientist who’d finally solved a vexing problem.
“Welcome to the sweet bonds of chastity. That should put an end to your masturbating nonsense, once and for all,” Vanessa proclaimed firmly as she stood back up straight, her hands on her hips in the classic posture of female authority, “happy birthday, Jimmy!”
“Serves you right, you big sissy,” Barbie said, still giggling.
“And now, it’s diaper time, Jimmy!” Vanessa announced cheerfully.
My lower lip quivered as I sat there, helpless and frustrated. I was desperately horny with absolutely no means of getting relief, and now entirely subject to the whims of this beautiful, but implacable disciplinarian.
I sniffed in resignation as Vanessa went about her usual thorough job of putting me in my diapers, the thick sticky layer of diaper rash ointment, baby powder, and soon she was pinning me up for my nap in my triple thick cotton diapers. A glittery pair of pink plastic panties followed and she finished by powdering between my thighs and the vinyl material of my panties.
“Beddie-bye, Baby,” Vanessa cooed as she slipped a full bottle of warm formula between my lips and began removing my mary janes. I drank the foul, tepid liquid submissively, still trying to grasp the enormity of the catastrophe that had befallen me. As Vanessa tucked my feet under the pink blankets of my crib, I think she sensed my misery.
Bending over me, she shifted my plastic pantied bottom across the crinkly waterproof sheet covering my mattress which in only a week’s time, had taken on the smell of stale pee.
“Don’t you worry, Honey,” Vanessa said soothingly as she held the big bottle to my lips, ”I’ll take care of those little balls of yours before they get too blue.”
Barbie giggled as if she were sharing a secret joke with Vanessa.
I wondered just what that might be as I drifted off to a troubled sissy sleep.
A week later, I had the opportunity to find out what she had in mind.
It was a Saturday afternoon and I lay awake in to my crib, still trying to get used to my freshly wet diapers from my afternoon nap. By now they were cool and clammy and they hugged my damp skin within the confines of my snug plastic panties.
It was also my birthday, and Vanessa had promised me we’d celebrate it in style. I was eager and hopeful that maybe today, of all days, she’d release me from my chastity for a brief, if fleeting, moment of pleasure.
My heart quickened as I heard the high pitched clicking of her high heels coming down the hall toward my room. I could tell by now who it was by the sound they made since both women had a distinctive stride. In this case, it proved to be both, and my suspicions were confirmed by the whispering I heard as they approached my door.
Vanessa came into the nursery, followed by Barbie, and she came across the room, unlatching the side bars of my baby crib. She was wearing a light green halter top, whose thin material stretched across her tremendous breasts tightly, leaving the entire curvy surface wrinkle free. I noticed her nipples poking out slightly and I could make out clearly, the outlines of her demi cup push-up bra. I prayed silently that she’d let me suckle once more from those magnificent, mouth watering mammaries.
Her small top left her firm, flat tummy exposed and below that, she wore a small pair of bun hugging white shorts.
Barbie, of course, was dressed in her obligatory french maid uniform, which was no less exciting.
I had to make a conscious effort now to restrain my penis which wanted desperately to react to this display of unbridled sexuality. To do otherwise was to invite a quick and painful reaction from my chastity device, which knew no mercy for my needs. I found the best thing to do was to think of other, non-sexual thoughts to try and distract myself and submissively bow to the reality that there was absolutely no way for me to relieve myself.
Vanessa pulled down my baby blankets, exposing my bare legs and bulging diapers. My pink nighty had worked its way up around my waist, leaving the colorful nursery print on my plastic panties exposed.
Instead of moving me to my changing pad as she usually did, Vanessa began peeling down my clinging vinyl panties there on the mattress, tossing them into the large diaper pail I had next to the bed. Even though it was emptied daily, my diaper pail added considerably, its pungent aroma of wet diapers to those of vinyl, rubber, and baby powder that normally permeated the nursery.
As usual, my diapers were soaked from my nap and Vanessa surprised me by humming an agreeable tune as she unpinned them. As she began cleaning my bottom and crotch, she didn’t immediately get another stack of diapers for me. Instead, she began the detailed proceedure for removing my chastity device, and after several minutes of work, my weiner was at last free. I sighed with relief and my excitement increased exponentially as she cleaned it with baby wipes and then put it aside.
Vanessa pulled back the baby blankets, exposing my nursery print mattress cover and instructed me get on my knees, facing away from her as I braced myself against the opposite side of the crib rail. I could only speculate what she had in mind for me but I knew it wasn’t a spanking or an enema. I was also made hopeful by her obvious good mood and I was sure she had something pleasant in store for my birthday.
“Now, I want you to be a good little boy and keep your hands on the crib rail. Can you do that for mommy?” she asked sweetly.
“Yes, Mommy,” I replied, trying to reign in my excitement.
“It’s very important Jimmy. I’m afraid if I catch you taking them off, I’ll have to give you a spanking,” she warned me.
“I’ll be good, Mommy” I said hopefully.
Looking over my shoulder, my bare bottom sticking out behind me, I craned my head to see what she was doing.
She appeared to be dipping something into the jar of nursery jelly but I couldn’t see clearly.
A moment later, I felt her prying my bottom cheeks apart with her fingers while she began coaxing something smooth and plyable into my anus.
“Ohh!” I squealed in surprise as I wiggled my fanny around.
“Stay still, or mommy spanks,” Vanessa warned me again, but her voice didn’t carry its usual threatening edge.
I settled down and the object slide in without too much difficulty. It was much smaller than the dildo nozzle she used with my morning enemas and didn’t stretch my sphincter to the limits.
As she moved it slowly in and out to find the right position, I moaned deliriously, the waves of pleasure washing over me. In a matter of seconds, I was panting hard and Vanessa stopped for a minute to allow me to cool down. My little weiner was rigid and begging for relief as it pointed downwards like the udder of a cow. Breathing heavily, I wanted so badly to reach down and give myself the relief I desperately needed but I kept my hands where they were, clutching the pink upper rail of the crib until my knuckles turned white.
When my wee-wee finally went soft again, a drop of pre-cum had appeared at its head and it slowly began to drool down towards the vinyl crib sheet.
“Okay, get ready with the cup,” Vanessa told Barbie, who was standing by with a shallow glass in her hands. I had no idea what her purpose was in all this but I quickly forgot about it as Vanessa began her ministrations in back again. I moaned deeply and pushed my bottom against her, trying to take the soft dildo as far in as it would go. She teased me mercilessly, never allowing me the satisfaction of feeling it deep inside my rectum, where I craved the sense of fullness. My penis was rock hard again and my breathing came in short gasps when Vanessa abruptly stopped again.
Sticking straight down, my pee pee twitched and flexed, frantically seeking release. Vanessa was patient however, and she stopped and waited for the inevitable to happen. Without further stimulation to sustain it, eventually my weiner began to shrink back to its usual limp length of an inch.
“Try it now,” Vanessa said to Barbie.
With a devious smile on her pretty face, Barbie bent forward and grasped my penis, pulling downward like she was milking a cow.
“Oh!” I squealed as I felt her handling it as if it were a tube of toothpaste she was trying to extract the last bit out of.
Her efforts were rewarded by a small, gooey string of cum that dribbled out of the tip, to collect in the small cup she held underneath.
I cried out in dismay as she not only deprived me of my joy juices, but also the explosive orgasm that would have accompanied it.
When no more semen could be extracted, Barbie stopped milking me and Vanessa resumed her slow, deliberate pumping of my anus. Tears of frustration filled my eyes as my weiner responded without regard to my wishes, growing hard again according to the will of Vanessa. Before long, I found myself once more at the brink of a mind shattering orgasm, struggling to bring it about on my own by grinding my hips against Vanessa’s hand that controlled the plyable dildo. She succeeed brilliantly in foiling my efforts, by simply relaxing the pressure whenever I tried to push against her. When I finally gave up in defeat, she’d resume her maddeningly slow massage of my prostrate, prolonging my erection in an unbearable torture of unrequitted pleasure.
When she finally stopped, my breathing was coming in ragged gasps and my face and neck were flushed.
“Please Mommy, please!” I sobbed as the tears of frustration rolled down my cheeks.
Vanessa smiled sweetly and stroked my bottom gently with her silky soft hands.
“There, there, Baby,” she cooed, ”we’ll get all that icky cum out of you, don’t you worry.”
Barbie giggled and bent forward, waiting for my tiny pecker to shrink back down.
In a frantic attempt to frustrate her efforts, I flexed my pee pee wildly, trying to reach orgasm on my own but it was like trying to catch the moon with a butterfly net. Clutching the crib rail with a death grip, I sobbed as my willy slowly softened and became limp again.
“Come on, Sissy,” Barbie said coaxing me with a mocking tone, ”cum like a big boy.”
I remained in my position, bent over and helpless as Barbie slowly squeezed more of my seed from my tormented penis. She managed to extract another big spoonful until at last, it went dry.
“My, that was a good one, Jimmy,” she said like she were commending a three year old on a successful potty attempt.
“I think that’s about as much as you’re going to get,” Vanessa advised sagely.
Barbie held the small cup in her delicate hands and gazed at the milky colored semen filling the bottom.
“What a good boy you are, Jimmy,” she said with feigned sincerity.
“You see, what we’ve done here is to remove all that pent up sexual tension, while still denying him any sort of release,” Vanessa explained as she grasped me by the hips and sat me down on the edge of the crib mattress.
“Now, as an experiment, to see how effective we were, we’ll just see if our little baby has any more get-up-and-go left in him.”
Vanessa took a bottle of Johnson’s baby lotion and squeezed out a small quantity in the palm of her hand. As I sat there whimpering and rubbing the tears from my eyes, she reached down and began slowly rubbing the lotion into my groin. My pee wee was so small, her hand dwarfed its limp form and she softly stoked it, but to no effect.
“There, you see,” she said as she pulled her hand away, revealing a well lotioned but nonetheless limp penis, ”no effect whatsoever. This sissy has been effectively milked.”
Barbie burst out laughing, her disdain and lack of sympathy washing over me like icewater.
It was all too much for me to handle and I burst into tears, crying like a two year old.
“Awww, there, there, Baby,” she said as she dipped the pacifier hanging around my neck into the cup containing the spent semen. She coated the big rubber nipple generously and coaxed it between my lips. Like the submissive sissy that I was, I willingly opened my mouth and accepted the creamy covered pacifier.
“Awww, poor wittle baby,” she said as she held it in my mouth, forcing me to suck and swallow my own cum.
“Oh,” Vanessa said as an afterthought, “this, is the best way to complete his milking.”
Taking hold of my arm, she pulled me up to an almost standing position and turned me slightly, so that my bottom was exposed to her side. Before I knew what was happening, I felt the searing impact of the paddle on my rear as she swatted me fiercely.
The pacifier shot out of my mouth as I shot up straight.
“OWWW!!” I cried in bewildered surprise.
Barbie burst out laughing and she took the paddle from Vanessa.
“You mean like this?” she said, her hand swooping down to deliver another stinging swat on my poor tender fanny.
“OWWW!! Stop it!” I wailed.
Barely surpressing a giggle, Vanessa took back the paddle.
“No. Like this,” she said as she yanked me over my my left arm and smacking me equally, if not harder than Barbie had.
“OW-HOW-WOW!!!” I shouted, dancing from one foot to another as my free hand went down to rub my reddening cheeks.
Barbie was laughing hysterically and she retrieved the paddle back from Vanessa.
“Oh,” she said between fits of laughter, “I thought you meant like this.”
Pulling my hand away that was trying to protect my defenseless bottom, she brought the paddle down hard, right in the center of my cheeks, leaving a bright red oval impression there.
I howled in pain and stomped my feet as the tears spilled down my face. By now, Vanessa was laughing too hard to continue the game so she sat me back down on the crib mattress as she tried to regain her composure.
“Sorry, Jimmy,” she said still chuckling, “but you have such a cute, spankable ass, sometimes I can’t resist it.”
I looked away and wiped the tears out of my eyes, trying desperately to keep a stiff lip through it all.
“Aw, cheer up Jimmy,” Vanessa exclaimed still giggling, “now it’s time to get you dressed up for your birthday party!”
She spent the next several minutes getting me secured in my chastity device and when she was satisfied that I was locked in and trussed up, she prepared my diapers for the day. I sucked my cum coated pacifier and sniffled while she slid the stack of soft, thick diapers underneath my rump, humming again to herself.
Normally, it would have brought about a painful reaction to look down at her big, swaying breasts, as she busied herself applying my diaper rash ointment and baby powder, but not now. Now that I had been relieved of my sissy juices, I could stare at her perfectly shaped boobs and not get hard or feel the accompanying pain. I could also allow my eyes to wander over Barbie’s immaculate body, savoring her glossy black stilletto heels and her long, sensuous legs. Her thighs were firm and trim and her skirt was oh, so short, threatening to reveal her silky sheer black panties if she bent over. And that’s just what she did as went over to get my socks and shoes for today’s outfit.
Even through my anger at her, I looked with longing admiration as she bent over and I saw her cute little bottom, nicely framed by the see-thru black panties stretching over her youthful cheeks. When she came back, she caught me staring at her and she came alongside the crib, the cup still in her hand.
“Ready for some more?” she asked, as she popped the pacifier out of my mouth and coated it again with the remaining semen. I twisted my face into a grimace of disgust but I obediently opened my mouth to take it back in again, my tongue once more tasting the creamy, somewhat salty sperm and the rubber of the pacifier nipple.
“How does that taste?” she asked as she bent over, revealing her wonderful cleavage as she did.
I said nothing but looked away as Vanessa was pulling the thick cloth up and pinning the sides of my diapers securely. She retrieved a pair of white, nursery print, plastic snap-on panties and she guided my feet thru as she pulled them up my legs. Getting to my thighs, she paused for a moment.
“Up, Sissy,” she commanded me.
I lifted up my rump in compliance as she worked the panties up and around the thick cloth of my diapers.
Bending over, she once again put her hands on the front of her smooth thighs to talk to me closer.
“Don’t worry Jimmy. Since you’ve got guests coming over to see you, I won’t make you wear a baby dress.”
I mumbled a sound of surprise through my pacifier, somewhat relieved by this unexpected turn of events.
“Nope. Instead, today you can be mommy’s little sailor boy. Doesn’t that sound like fun?” she said as if she were addressing a four year old.
I frowned in disapproval and she brought over a sissyish, baby blue colored satin top, lined with white lace and ruffled at the hem. The chest had a lace lined bib and puffy short sleeves with more lace around the edges. She raised my hands and lowered the softly lined top over my head and arms. In frustration, I tugged at the short hem of the top, hoping against hope it would cover my embarrassing diapers but that was not going to happen.
“Aww…you’re concerned someone’s gonna see your big poofy pampers, aren’t you,” Vanessa said in the most condescending tone of voice as she saw me tugging at the top.
I nodded my head numbly, unable to look her in the eye.
“Well I’ve got just the thing,” she said cheerfully.
Going over to the dresser she dug around until she found what she was looking for. Coming back to the crib, she held a frothy pair of white lacey satin rhumba panties before me, the lace on the seat edged with baby blue.
“Aren’t these just scrumptious?” she exclaimed with a ravishing smile.
I pouted miserably as she snaked the silky confection up my legs and over the smooth plastic of my waterproof panties. This was followed by a wide brimmed straw hat with a baby blue ribbon around its crown. At the same time, Barbie was rolling knee high socks up my calves and my glossy black mary janes over that. I noted that the socks had a satiny blue ribbon tied into a bow at the top of each sock. I couldn’t remember ever feeling like more of a sissy.
“Stand up Jimmy, so you can see your new outfit,” Vanessa said enthusiastically.
Pulling me up, they stood aside from me so I could see myself clearly in the wall mirror. Gazing at my reflection, I blushed deeply as I imagined what people would say when they saw me in this childish ensemble.
As if to confirm my fears, the doorbell suddenly rang.
“Oh!” I cried out in panic as a small stream of pee accidentally leaked into my fresh diapers.
Barbie giggled at my appearance without making ready to answer the door as she normally would have.
“Jimmy?” Vanessa asked sweetly, “wouldn’t you like to answer the doorbell? It’s probably one of your party guests.”
I blushed again and bit my lip in angst, then shook my head violently.
“Now, Jimmy,” Vanessa said, her voice taking on an edge, “don’t be rude. These nice people have come from a long way and they’ve brought presents for you. You wouldn’t want to leave them waiting would you?”
I looked up at her helplessly, praying she wouldn’t make me go through with this.
The doorbell rang again, its tone somehow seeming more urgent now.
Without a word, Vanessa picked up the oval wooden paddle and looked me in the eye.
“Maybe we need to have a little lesson in manners, hm?” she said, her voice cutting through me like a knife.
“No Mommy!” I cried frantically as the pacifier fell out my mouth again.
I bolted out of the room quickly, or at least, as quickly as I could, considering I had to waddle with the thick diapers I was wearing. I tried to shut out the giggling coming from my nursery as I went downstairs and to the front door. My heart was pounding in my chest as my hand went to the door knob. I could see the vague shape of two, slim young women through the glazed side window next to the door but I was frozen in fear. One of them rang the doorbell again and I heard Vanessa’s voice behind me at the top of the landing.
“Open the door, Jimmy,” she ordered me in her commanding voice that made my bottom tingle with fear.
As another small stream of pee leaked into my diaper, I opened the door and stood aside.
The two women burst into uncontrolled laughter as they took in my sissy outfit and as I stood there blushing, I recognized Brittany from my childhood grade school. After a moment, I realized the other one was Tammy, although both had changed quite a bit. I remembered them as two small girls, at the time, no more than ten, like myself. Now, they were about twenty and I was shocked at how they appeared. Brittany looked like a model, and she wore a fashionable silky dress that showed off her long, sexy legs. Tammy was now a beautiful blonde and she wore a black leather bustier that pushed her considerable bosom up into two fabulous mounds of femininity. As she laughed at me, I almost thought they’d spill out of her top as they jiggled from her mirth.
“Jimmy!” Brittany finally said when she could stop laughing, “you haven’t changed a bit! Still dressing up like a sissy and wearing your big, thick diapers!”
That comment made them burst into peals of laughter again.
“Couldn’t your mommy ever potty train you?” Tammy asked incredulously.
I glared at them angrily but remained mute as my face and chest reddened.
Vanessa came alongside and invited them in, thanking them politely for coming. Evidently, they were old friends and for a moment, I was forgotten as they chatted busily amongst themselves. She took them into the spacious living room and sat them down while Barbie brought them drinks. I endured more of their humiliating comments as Brittany related the numerous times she’d tricked me and gotten me spanked. Vanessa thought it was all a riot and she laughed along with everyone while I sat in silence, chewing my pacifier in frustration. Before long, the doorbell rang again and I was prompted to answer it.
Going to the door, I opened it up for another shocker. It was Ms. Taylor, my school teacher from the fifth grade! She was ten years older now but still a total knockout, and a classy one at that. She wore a sleek beige skirt and a white sweater that hugged her big bosom in a very form fitting way. As she saw me, she cocked her head little to the side in the cutest way and beamed in recognition of me.
“Jimmy!” she said as she came in and hugged me close, her large breasts pushing against me, “don’t you look darling!”
She didn’t seem to be surprised that I was still in diapers, at the age of twenty, and I was a bit put off by the fact that she obviously hadn’t had too much faith that I’d ever grown up. I guess she knew me pretty well, after all. As she hugged me, her hand went down to squeeze the ruffled seat of my diapers, checking to see if I was wet like she were my mother.
“It’s good to see you,” she said kindly and she planted a wet kiss on my cheek, leaving her dark red lipstick print for everyone to see.
In her hands, she carried a box gift wrapped in baby wrapping, with frollicking bears and lambs on its pink paper.
“I’ve bought you something very special that I’m sure you’ll love,” she whispered in my ear.
I blushed at the thought of that, fearing it was probably a sissy dress of some sort.
Ms. Taylor came inside and I noticed she was still quite a bit taller than me, particularly in her high heeled sandals. She took a seat on the sofa and Vanessa introduced herself and the others.
As they were making their aquaintances, the doorbell rang again. Vanessa snapped her fingers at me and I hopped up to go answer it.
This time it was my old adversary, Melissa and her equally tough friend, Tara. Both looked fantastic and as I stood aside, Melissa swatted my padded bottom with her gift, which was long and rectangular shaped.
“Ha!” she smirked, “looks like it works.”
I rubbed my bottom as they came into the living room to join the others. On the coffee table, the guests had stacked my presents, all wrapped in nursery print gift wrap, making it look more like a baby shower instead of my birthday. I wanted to run away and hide but Vanessa instructed me to turn around to model my pretty rhumba panties for everyone. Just when I thought I was going to die of embarassment, the doorbell rang once more.
I went to answer it and I was surprised to see my aunt Suzie standing before me. She wore a tight wrap around that hugged her delicious bosom, and a pair of short, Daisy Duke cut off shorts.
“My, my, Jimmy, I guess some little boys just never grow up, do they?” she said as she shook her head at my general appearance.
“It’s not my fault,” I tried to explain but she wouldn’t have any of it and she dismissed my excuse with the wave of her hand.
“Jimmy, you might be able to convince someone else that, but I know what a sissy you really are,” she told me in no uncertain terms, “I’ve always known you were a sissy and I’m glad Vanessa decided to put you back into diapers. That’s right where you belong.”
I was taken aback by my aunt’s blunt appraisal and I stood aside as she walked in with a gift under her arm. When she had taken a seat in the living room, everyone’s attention turned to Barbie, who was bringing in a birthday cake with pink and white frosting. I noted there were only two candles on it and everyone began singing happy birthday to me. I blushed as Vanessa came up behind me to tie a pink baby bib around my neck that said ‘Bedwetter’s Anonymous’ on it. They all laughed at that and she told me to blow out the candles.
“Jimmy’s twenty…going on two,” she announced to everyone’s amusement.
After serving everyone a piece, Vanessa spoon fed me my cake, while Barbie brought out a big bottle of warm milk for me to nurse from.
When all the ladies had finished their cake, Vanessa prompted me to begin opening my presents. Reluctantly, I did as I was told, and the first present turned out to be a pink patent leather sissy purse, with the words ‘Little Missy’ written on both sides in silver glitter.
“That’ll be perfect for when you’re out on the town,” Tara said with a disparaging laugh.
I blushed and put it aside, hoping that little adventure would never come to pass.
Pushing another big box before me, I felt Vanessa’s big breasts pressing against my back as she told me to open the next present. With much encouragement and giggles from my guests, I opened the childishly giftwraped covered box and found a frothy white baby dress, generously adorned with pink accents and lace throughout. It had a fancy layered petticoat sewn into it and it looked like it was made for a three year old girl except that it was obviously in my size.
Tara, who was sitting to my right, impatiently shoved her gift in my hands, a lewd smile on her face.
“This is one you’ll always have with you,” she said.
It had a strange feel to it, being about the size of my hand but a little bigger. When I tore off the wrapping, I discovered what looked like a short, fat dildo displayed in a plastic package, except that the base of it had a large plastic ring, exactly like a baby pacifier. The label on the package said ‘Dr. Cock’s Baby Pacifier’ and it showed a young woman wearing a bonnet and sucking on the product with an innocent look on her cute face.
I blushed as I imagined myself using such a thing but Tara wasted no time in grabbing it out of my hands and tearing open the package. She brought the big fat dildo up to my lips, pressing it against my face forcibly but I kept my mouth petulantly shut. Seeing my resistance, she slapped my bare thigh painfully which caused me to yelp out in distress and she responded by jamming the dildo in my mouth.
Everyone burst into laughter at her cleverness and she took the pink plastic loop and dropped it around my neck.
“There,” she said smugly, “guess you know who’s boss around here now.”
I sucked on the cock pacifier in mute humiliation, my cheeks buzzing with shame as I avoided the stares of all the beautiful women present who were witness to my defeat.
“That is so perfect for you,” Melissa said who was sitting to my left, “I always knew you were a cocksucker and now everyone else does too.”
I whimpered in embarassment as Ms. Taylor set her gift down before me. She offered me a sympathetic smile and I hoped her present might bring some measure of joy to this otherwise dreadful affair.
It was lightweight to hold and when I’d removed the giftwrap, I found a white box with tissue inside. Pulling back the tissue, I found three pairs of fancy ruffled rhumba panties, in pink, white, and lilac. They featured soft ruffles around the leg holes and big sassy layers of lace across the seat. I looked down at them in disappointment and then up at Ms. Taylor.
“I thought you might like to wear those for special occasions,” she offered sweetly.
The next present was from Tammy, Brittany’s childhood friend and willing accomplice. It was the smallest of all the presents there and it actually felt like two small cyclinders. Opening it up, I found one was a stick of Bonny Bell bubble gum pink lipstick and the other, a small sprayer of perfume labeled ‘Nursery Nights’.
Tara wasted no time in pulling out my pacifier and apply several thick coats of the bright glossy lipstick to my lips, before pushing the pacifier back in.
“Oh. That’s definately you,” she said, nodding her head.
The perfume, she took the liberty of opening and spraying me throughly with. It smelled like baby powder and something else I couldn’t quite put my finger on but it reminded me of my nursery and diapers. Even though I was already dressed like a baby, wearing a wet diaper, somehow this scent really brought it home to me and my face went bright red all over again.
“Now you smell like the sissy that you’re dressed up as,” she smirked.
“I know!” Brittany suddenly exclaimed, “why don’t we have Jimmy model his new dress and purse for us?”
“I think that’s a wonderful idea,” Vanessa said and she reached over and began unbuttoning my sailor suit top.
I squirmed in protest but soon she was replacing my sissy sailor suit with the frothy white baby dress, lowering it over my head despite my reservations. She buttoned it up securely in back and I noted in frustration that they were purposely put out of my reach. Lowering my silky rhumba panties down my skinny legs, she sifted through the box that Ms. Taylor had given me and selected a pink pair. They were a soft pink color with three large white ruffles crossing the seat and around the legs. At the top, in the front of the panties was a tiny white bow but stitched across the front, in fancy script, it said ‘Sissy Jimmy’. I wanted to cry when I read that and Vanessa happily snaked them up my legs, telling me, “you know Jimmy, people in life will judge you by the panties you wear. And these should make it clear just how much of a sissy you are.”
Lastly, she handed me my purse after putting my lipstick in it.
“There. You’re all set. This would be a wonderfull outfit for you to wear out in the park. I’m sure all the little girls would be green with envy,” she told me.
Everyone laughed at that and Vanessa made me parade around in front them. When I went by Tammy, she insisted on applying some blush to my cheeks, even though I was already several colors of red as it was. Several times, I felt my diapers growing wet and warm, no doubt caused by the trauma I was enduring at these women’s hands. I felt like such a babyish sissy, with my swishy white and pink dress, my bulging diapers covered by the pink lacey rhumba panties, my purse and my mary janes. I felt even more infantile due to the fact that my rhumba panties were helping to keep the wet cloth of my diapers pressed snugly against my skin. My shame knew no bounds as the girls took turns patting me on my ruffled bottom and making humiliating comments.
“There’s still one present to open,” Melissa said to the crowd, making my heart jump in fear.
She handed me the present she had been holding on to since she walked in. It was rectangular, about a foot and a half long, by four inches, and about 3/8″ thick. I sucked on my pacifier nervously as I held this particular gift in my hand, knowing instinctively what it was.
“Come on, open it,” Melissa dared me, a dark smile crossing her face.
Reluctantly, I ever so slowly tore off the paper and I revealed a polished wooden paddle, with two rows of half inch holes running down the length of it.
“Well! Jimmy already has one of those that gets a lot of use around this house but now we’ll have a choice of styles!” Vanessa stated happily.
“I say we give the baby his birthday spanking,” Melissa suggested impulsively to the group of women.
“Yes!” Tammy agreed,
“Excellent!” Brittany seconded.
“It’ll be fun,” Ms. Taylor suggested.
The girls all chorused their agreement until aunt Suzie raised her hand.
“But wait. I suggest we have Jimmy thank everyone individually and then they can give him his birthday spanks,” she offered to everyone’s enthusiastic approval, “let’s see, he’s twenty now and there are one, two, three, four, five, six…seven of us here. That means three spanks apiece.”
Brittany clapped her hands together in glee at the opportunity to spank me again and in a panic, I felt another stream of warm, wet pee go into my diaper.
Vanessa came over and stood me up, taking the paddle and handing it to aunt Suzie.
“Now, Jimmy. Thank your aunt Suzie for the pretty white baby dress,” she said as she pushed my reluctant form in the direction of my aunt.
I stumbled forward and pulled the fat pacifier out of my mouth as I stood before my sexy aunt, my pink sissy purse still in my hands. I tried not to be obvious as I gaped at her deep cleavage created by the tight wrap she was wearing but I think she saw me looking.
“Um, thanks, um, thank you for the, um, d-dress, aunt Suzie,” I stammered uncertainly.
“Well you’re most welcome, Sugarplum,” she said politely as she pulled my rhumba panties down to reveal my nursery print plastic panties.
“Jimmy? Have you wet your diapers?” she suddenly said accusingly.
I bit my lip nervously and looked away at the floor, slowly nodding my head.
“Looks like your birthday boy’s going to need to have his diapers changed,” she said to Vanessa as she took me over her lap, “thank god for side snap plastic panties.”
Everyone laughed at that remark except me who was quivering nervously as I clutched my purse, awaiting the first three slaps of the paddle.
I didn’t have long to wait. After pushing up the fluffy hem of my dress, she unsnapped the back of my plastic panties, pushed them back and unpinned my wet diapers. This kept the vinyl of my panties between her thighs and the wet cloth of my diapers.
SMACKK!! WHAPP!!! SMACKK!!
Three times, the paddle swooped down, landing squarely on my damp and tender bottom. I gritted my teeth and fought to retain my composure, even as the tears began to fill my eyes. The last thing I wanted to do was to cry like a baby in front of all these women.
Lifting me back up, she instructed me to hold the front of my diapers and plastic panties in place so that I wouldn’t get pee on the next person’s lap.
I waddled nervously over to Tammy, who had taken the paddle from aunt Suzie.
“Thank you for the lipstick,” I mumbled barely audibly as I stood before her.
With a speed I didn’t think possible, Tammy swung the paddle and landed it on my bared fanny with a stinging ferocity.
“OOWWW!!!” I cried out, jumping up in shock and pain.
“What did you say? I couldn’t hear you,” she said with an evil smile.
“Tha-thank you for the lipstick and perfume,” I said obediently, in a much louder voice, my cheeks smarting badly now.
“You’re welcome, Sissy,” she said smugly.
I took my place over her lap fearfully, slowly getting myself situated with my diaper.
THWACKK!! SMACKK!! WHAPP!!
Despite my best intentions, I burst into tears and cried out like a baby, shaking my purse in a sissyish fury.
I jumped off her lap and carried my wet diapers and panties over to Brittany who quickly took the paddle and yanked me abruptly over her lap.
My required thanks were cut off by Brittany’s impatience to spank me.
I bawled openly now, my bottom on fire and I jumped up as the tears rolled down my face.
“Oops,” she said with mock sincerity, “I think I miscounted.”
Giggles filled the room.
Next was Ms. Taylor and she looked up at me with kindness and compassion.
“Thank you for the pretty panties, Ms. Taylor,” I said between sobs, hoping she’d be easier than the others.
Gently, she took me over her lap and waited until I had gotten myself and my diaper situated.
“It’s been quite awhile since I’ve seen your bottom from this perspective, Jimmy,” she said as she rubbed my red fanny appreciatively with the long wooden paddle.
SMACKK!! THWACK!!! WHAPPP!!! SMACKKK!!! CRACKKK!!
I kicked wildly with my mary janes in pain and frustration as she slapped my already stinging cheeks harshly. Still gripping my purse, I jumped up and looked down at my former teacher who hadn’t given me any sympathy at all.
“Sorry Jimmy. But I didn’t want to show you any favoritism,” she said in her sweet, innocent voice.
I wiped the tears away and stumbled over to Vanessa who was waiting patiently for me.
“Well, little birthday boy. You probably didn’t realize it, but you’re already wearing my present to you. It’s your penis prison,” she told me.
The other girls laughed as she took me over her lap and I kicked even before she began spanking me.
“Settle down, Jimmy. Or mommy will really give you something to cry about.”
On and on it went, my poor botttom being smacked by everyone present until finally, I reached Melissa. I think I dreaded her most of all because she’d never shown me anything of her personality besides her bullying nature.
Now as I stood before her, my face wet with tears and my bottom a blazing red, I felt a last surge of fear-induced pee flow into my diapers. It was warm behind my hand and I blushed anew at such a humiliating sensation.
“Is there something you want to tell me?” she said, coaxing me provacatively in a syrupy tone of voice.
“Tha-thank you-for-for-giving me, the-the new p-paddle,” I said haltingly between sobs.
“It’s my pleasure,” she said wickedly taking me over her lap.
“Please don’t spank me hard!” I pleaded to her desperately.
SMACKKK!!! CRACKKK!!! THWACKK!!
I squirmed around on her lap desperately as the harsh wooden paddle landed on my punished bottom with a blistering sting. Thinking I was done, I tried to get up but Melissa held me down.
WHAPP!! SMACKKK!! SLAPPP!!! THWACKK!!
I cried like a baby, slinging my purse and pounding the floor as she kept spanking me, slapping my glowing globes with ever greater ferocity. I wanted to cry out that she was only supposed to spank me three times but I could barely catch my breath and when I did, I howled with pain, squalling like a little child.
SMACKK!! CRACKK!!! SMACKKK!!!!
I thought she was going to break the paddle on that last whack and my mary janes danced frantically on the floor as I kicked and cried. Bawling like a baby, I struggled to my feet, holding my wet diapers, plastic panties and purse before me like a sissy shield.
Vanessa held her arms out and I ran to her embrace, sobbing against her big, soft bosom as she held me close and stroked my head soothingly. I held her tightly, my new mommy, beautiful and powerful and so very strong. I looked up into her pretty dark eyes and I knew she would always know what was best for me. I sniffled loudly and cried, watching her chest slowly rising and falling as she reached down and took hold of my cock pacifier. Still whimpering softly, I watched as she brought it up to my lips and gently pushed it into my mouth.
“There, there,” she said soothingly, “hush, little baby.”
I had to open wide to fit the big dildo in my mouth and I blushed as I sucked on the big rubber cock head.
Slowly, she sat me down on the floor in front of everyone and re-arranged my wet diapers, pinning the squishy, saturated cloth back into place. I squealed in protest but she ignored me and re-snapped my plastic panties back into place, sealing in both the wetness and the fire on my bottom.
“Come here, Jimmy,” Ms. Taylor beckoned to me, “here’s your panties.”
Holding the panties up that went with my white baby dress, I went over and stepped into them. I must have lost them sometime while I was getting my spankings. Ms. Taylor pulled the stretchy pink panties up my legs and then over my plastic panties, adding to the effect that Vanessa had already started.
One by one, my guests said goodbye and Vanessa made me stand on the front porch and wave at them as they walked out to their cars. At one point, I noticed Melissa whispering to Vanessa and I cringed at what she might be discussing. It was early evening by the time everyone had left, with the exception of Melissa and Tara. At last, my former nemesis took me by the hand and led me upstairs where I was terrified as to what was going to happen.
“Melissa says she wants to see your nursery,” Vanessa had explained, but for some reason I didn’t believe her.
Opening the door, Melissa slapped me on my pantied bottom to get me in quicker. I stumbled in with my wet diapers clinging to my seat and crotch while Tara moved to close the door.
“It’s just like old times, ain’t it?” her trouble making, but attractive friend said threateningly.
I looked from her to Melissa hoping for some reprieve but none was coming.
I watched as Melissa tore off her mini-skirt with a haste that took my breath away, revealing a pair of high cut, black leather panties. For some reason, the dark, shiny look of them against her smooth, supple skin filled me with fearful anticipation.
Opening her purse, she produced a large, imposing strap-on dildo, at least ten inches in length and big enough that her fingertips couldn’t completely wrap around its massive circumference. It was extremely realistic in appearance with multiple veins running back from the big, shiny head. With a wicked look in her eyes that I’d seen before, Melissa stepped into the intimidating device and secured it around her sexy, curvy hips, making me gulp and suck feverishly on the fat rubber dildo pacifier in my mouth.
I watched her with a mixture of familiar fear and secret admiration. I had always felt a confused, yet deep seated envy for this strong, confident woman, despite her bossy and demeaning nature. With her long, powerful legs and big breasts, my will crumbled and I was easily intimidated. Just being in her presence brought about strong feelings of submissiveness and inferiority in me and I felt like a weak, little boy in his diapers.
She went over to my crib and swung the side downwards, opening it up for me. With her long, red tipped nails, she snaked my satiny rhumba panties down my legs and gathered them around my ankles. Leading me over to the crib, she bent me over and made me grasp the far bars, forcing my knees to the floor.
“Spread your legs, Sissy,” she ordered me tersely, “you’ve had this coming for a long time.”
I whimpered fearfully with my mouth full of rubber cock as she grasped the back of my plastic panties and yanked them down forcefully, unsnapping the double rows of snaps on either side of my panties with one quick pull and exposing my wet cloth diapers. Unpinning them impatiently, she pushed them down just far enough to give her an unobstructed access to my anus. I heard her coating the massive dildo with vasoline and my heart was beating wildly with nervous anxiety. My mouth went dry and my rear end puckered with anticipation as I waited for the inevitable, forceful invasion of my rump.
With my cheeks still hot and stinging, I felt her prying them apart and the blunt, sticky end of her dildo pressing urgently against my hole. I squealed like a little girl as Melissa applied steady, but firm pressure against my rosebud, trying to fit an impossibly big cock into my teeny passage. I tried to squirm away from her determined entry to try and prevent the gargantuan dildo from coming in and I was rewarded with several harsh slaps against my already smarting bottom. I cried loudly but the big dildo filling my mouth made my protests sound girlish and insignificant.
Finally, after several minutes of earnest, but unsuccessful attempts, I felt her halt her anal attack and she delivered an angry smack of frustration against my bottom cheek.
I howled in pain but was relieved in my belief that she had at last given up.
“Tar,” she said to her friend, “can you pull his cheeks apart so I can get this in?”
I quailed in fear at her implacable determination and I whimpered in terror around my pacifier.
Tara was only too happy to help and I felt her grasping both bright red cheeks in her hands, spreading them wide for Melissa’s big rubber cock. With another layer of vasoline quickly applied to its massive rubber head, she pushed it up against my defenseless back door, refusing to give up.
I tried to squirm away from the determined invader prodding impatiently against my anus but Tara easily held me in place, preventing any hope of escape.
Suddenly and inexorably, I felt the huge phallus slowly push past the ring of my sphincter and I moaned loudly.
“OOOOMMPHHH!!” I wailed helplessly.
I knew the skin around my hole had been stretched to the very limit, struggling mightily to accomodate such a monstrous dildo, and I gasped as it slowly slid into me. I felt like I were being impaled by a baseball bat and my toes curled as I put my head against the vinyl plastic of my crib mattress and lay in place, submissively taking my punishment. Rather than fight it, I lay obediently motionless, and let her push the monster deep into my rectum. With my face against the waterproof plastic, I breathed deeply the smells of vinyl and stale pee as Melissa slowly pumped my tender bottom. Gazing backward at the mirror covering the wall, I watched as she grasped my hips and forced herself deep inside me, making me moan like a little girl.
I looked like such a weak, effeminate sissy in my white fluffy baby dress and knee socks while she looked infinitely powerful, her strong, firm thighs flexing as she drove the fat dildo deep, in and out of my backside. Her big breasts hung down within her top, swinging back and forth with each punishing thrust of her pelvis. I grabbed my pink teddy bear and sucked frantically on the big rubber cock in my mouth trying to take comfort while Melissa proceeded to pound me from behind. I watched in the mirror as she thrust her strap-on in again and again, reaming my poor sissy hole with her tool. Tears of frustration trickled down my face as she buried her faux cock deep into my rear end, driving it in until it bottomed out and then she’d hold it there, forcing me to feel every inch and refusing to let go of my hips while I squirmed and moaned. At the same time, my little trussed up penis was receiving it’s own share of torment. With by backdoor being filled to capacity and pumped like never before, I wanted nothing better than to obtain sexual release, if only briefly.
My chastity device seemed to mock me without mercy and its bonds cut into my little package as Melissa rammed me again and again.
“OOOMPHH! OOMPHH!!!” I cried as Melissa smiled down on my sissified pose.
I sobbed with humiliation and groaned as my little pecker strained against its bonds, trying to get hard but completely unable to do so. It was so incredibly frustrating, being humped without mercy by stern, strong Melissa, and unable to get any kind of relief for myself. I gripped the crib bars and sucked harder on the the fat dildo pacifier filling my mouth, gasping to take in air.
Stepping up her pace, Melissa forcibly pounded my fanny remorselessly. I watched her clenching her teeth in intense determination as she hammered my bottom with deep, powerful thrusts. My body bucked while my bottom quivered and I had to grip the crib bars just to hold on while she drove the massive dildo in and out. I squealed and moaned at the top of my lungs, my poor rear getting the reaming of its life. A fine patina of sweat had appeared on Melissa’s forehead but she kept driving away in earnest, her boobs shaking mightily and threatening to spill out of her top.
It was then, that I caught movement out of the corner of my eye. I saw the nursery room door open and framed in the doorway was Vanessa. At last! My new mommy had come to save me, save me from this punishing ordeal! My hole was sore and it ached from being stretched so mercilessly. I was desperate for her to be my saviour and save me.
Melissa saw her too but she never missed a beat and she just kept pounding away at me, driving the dildo like a jack hammer into my back hole. I saw Vanessa smiling and nodding in satisfaction, apparently pleased by the fact that I was getting humped good and hard.
Finally, after I thought my hole couldn’t take any more, Melissa cried out in orgasm, and she plunged the dildo in as far as it would go, holding it there while she spent herself. I struggled to get out and away but she held me in place, forcing me to savor the big rubber cock buried deep inside me. At last, after she’d caught her breath again, she eased it out and I sighed with relief. My poor butthole was throbbing and my penis was in pain from the constrictive chastity loops. Vanessa walked in and rolled me over, checking my little weiner closely.
“Works like a charm!” she beamed at the others who broke out into giggles.
Melissa undid the strong harness straps of her strap-on with the practiced ease of someone who used it regularly.
“All done?” Vanessa asked her.
“Yeah,” she said, still breathing hard, as she looked down at me with a leering smile, “for now, I am.”
“Well, I’m sure Jimmy would love to thank you personally but unfortunately he’s got his mouth full of cock right now,” Vanessa told her jokingly.
Tara and Melissa burst out laughing and then Vanessa moved me over to the changing table to take care of my diapers. Melissa was cleaning her tool like a professional, wiping down the long, thick shaft with baby wipes until all the vasoline had been removed.
“Thanks for calling me,” she said to Vanessa, who was busy smearing diaper rash ointment across my red, spanked bottom.
“Don’t mention it,” she replied as she slid a stack of fat diapers under me, “anytime you want to come over and do it again, just holler. I’m sure it will do him a world of good.”
My heart sank as I contemplated further sessions with Melissa and her strap-on. It was going to be a week before I could walk normally again!
The three hugged and exchanged kisses while I sat on my arranged diapers, waiting for Vanessa to finish. When they left, Vanessa returned to getting me ready for bed.
“Well, you certainly did have a wonderful birthday, didn’t you?” she said with a big smile on her beautiful face.
With my lips wrapped around the rubber cock filling my mouth, I wasn’t in a position to contradict her and soon, my diapers were being pinned into place and a pair of plastic panties drawn up my legs. My satin rhumba panties had been put away for the night but she found a babyish pink nightey that was soft and comfy and she helped me into it. Putting me back into my crib, she pulled up the baby blankets around me and raised the crib bars, latching the side shut with a secure ‘click’.
“Nightey-nite, Sissykins,” she said softly as she walked out of the room, turning off the lights as she went. It was only seven o’clock and I was left in the quiet of the room, my only companion, the Barney nightlight on the far wall.
As I pondered the events of the day, I saw the nursery door open once more and an unfamiliar figure was backlit by the hallway. Pulling down my blankets, I sat up to see who it was that was walking in and staring at me.
“Jimmy? Is that really you?”
I froze in place, as I realized the voice belonged to my mother.
Whereas she was silhouetted by the light behind her, I was fully illuminated and she stared down at me in shock with my baby clothes and sissyish appearance. When she’d last seen me, I had had the look of an adult man but now, with my girlish Shirley Temple hairdo, frilly nightey and thick diapers, I looked like a three year old toddler girl. I gulped in fear and apprehension at her seeing me like this.
Pulling down my blankets the rest of the way, she exposed the shiny nursery print plastic panties I was wearing over the super thick diapers clearly visible through the filmy fabric of my nightey. Gripped by panic, I proceeded to flood my fresh diapers. My eyes began to tear up as I felt the spreading wet warmth that I was helpless to stop.
Putting her hands on her hips, she stared down at me angrily.
“Well. I guess I always knew that you were a sissy but I never realized the extent until now.
“Still wearing diapers, I see,” she said in disgust, “and wetting them like a baby, from the sounds of it.”
I hung my head in shame as the pee saturated my crotch and began to seep back between my legs.
“And what on earth is that in your mouth?” she suddenly asked incredulously.
I blushed three shades of red as she popped the cock pacifier out of my mouth roughly. I had been sucking on it for so long, I had simply forgot it was in my mouth.
“Mommy!” I cried out, suddenly bursting into tears as I continued to soak my diapers in a display befitting my infantile appearance.
“Don’t mommy me, you big sissy baby!” she snapped angrily, “it’s obvious you still need diapers and the kind of discipline that only Vanessa can provide for you.”
I pouted in silence as my mom scolded me like a child.
“I guess it’s true what they say,” she continued, “once a sissy, always a sissy.”