Jimmy's Return to Diapers
This is the prequel to the "Jimmy" Series I had written previously, several years ago. If you are not familiar with the titles, they are "Jimmy's Day at School", "Jimmy's Day of Shopping", and "Jimmy's New Babysitter". This story takes place before those three and gives you some idea how our poor little hero started his way down the inevitable path of sissyhood. I'm posting it now because I think the original was lost on the website here.
When I was ten, I was still small for my age and frail, by most standards. My mom wouldn't have dreamed of leaving me alone in the house, so whenever she needed to go somewhere, she'd drop me off at a friend of hers who lived in the neighborhood. This woman, who was twenty five or so, did most of the babysitting for the kids on our street. I remember her as being a total knockout, dark haired, and very curvy, if you know what I mean.
It was an average morning that I was introduced to her...
"Come in Jimmy, it's nice to make your acquaintance," she said to me cheerfully.
I was, by nature, very shy and I was unable to hold the gaze of this extremely pretty woman. I mumbled something but kept my eyes downcast.
"Don't worry about him," my mom assured her, "he'll warm up to you once you've had a chance to get to know him."
"Well he certainly is a little cutey," she remarked as she ruffled my hair.
We went inside and my mom made small talk with her until it was time for her to go. I was a little nervous about being alone with a stranger, especially one so beautiful and sexy as this woman but it sure beat old Mrs. Snagworth, down the street. She was a crotchety old kiester my mom once made me stay with and all I ever got out of that arrangement was a hard spanking.
This woman, who's name I learned was Vanessa, was certainly different, with her snug shorts and tight crop top. I had never seen a woman who was made like her and I found it impossible to take my eyes off her big, bountiful breasts. I didn't know at the time what cleavage was but instinctively, I realized I liked it.
Closing the door behind her, she bent down, offering me a breathtaking view, and taking my hand very sweetly.
"Jimmy, I want you to come into the other room with me so I can get you changed," she told me.
"Cha-changed?" I asked dumbly, " but...I'm already dressed."
"Jimmy, in this house, we have a rule. All little boys have to wear diapers and plastic panties until they can prove that they don't need them."
My mouth hung open as she led me down the hall and into another room.
"B-but I don't need d-diapers," I insisted shakily. My heart starting beating much faster and I hoped she hadn't heard the uncertainty in my voice.
"Well, we'll see Jimmy. Last week I had a little boy over here who ended up wetting his pants and I don't want to take any more chances."
She lifted me up onto the bed and began untying my shoelaces.
I felt my eyes begin to moisten and my cheeks redden with embarrassment.
"But I don't wet my pants!" I protested.
"That's good," she said as she pulled my shoes and pants off, "then you'll only have to wear diapers for this afternoon. After that, you can go back to wearing your regular clothes."
My lower lip quivered and I pouted helplessly as she slipped her beautifully manicured nails inside the waistband of my underwear and slid them down my legs. I gasped as my privates were exposed and my hands shot down to cover them. Vanessa smiled at me and took several cloth diapers from a stack and arranged them on the bed next to me. I gulped as I saw how thick they were and my heart beat even faster as I imagined having to wear them.
Taking my feet in her left hand, she raised my legs and slid the stack of diapers underneath my rump, laying me down on them gently. They felt bunny soft on my fanny and she held my hands aside as she shook baby powder over my groin and between my legs. From a flat jar, she produced two large diaper pins, with a duckie design and she put them between her full lips. Pulling the thick cloth up between my legs, she held the corners together snugly as she snicked the pins closed.
I bit my lip in embarrassment as she went over to a drawer to get something else. Thinking I was done, I sat up and got ready to get off the bed.
"Not yet Jimmy, you still need some plastic panties," she said cheerfully.
I winced as she brought over a pair of white nursery print waterproof pants and held them up to me.
"These should be just your size," she said with a big smile.
I whimpered in humiliation as she gathered the leg holes and began snaking them up my legs. I felt so babyish as she pulled them up my skinny thighs and then over the very thick diaper that was pinned on me.
"There!" she said as she ran her fingers around the elastic waistband, "a perfect fit. It's as if they were made just for you!"
She shook some more powder between my legs where the plastic might rub and then began putting my shoes on.
"B-b-but, can't I wear my pants please?" I quailed.
"These will be just fine," she said as she patted the now thick crotch of my waterproof panties, "besides, you'd never be able to get your pants over these diapers anyway."
I bunched my fists in mute helplessness and fought back tears of humiliation.
"It's not fair!" I pouted.
"Now don't you worry about a thing. In half an hour, you will have forgotten all about your diapers," she assured me as finished tying my shoes, "but if you have to go potty, you be sure to tell me, okay Honey?"
I nodded my head but my cheeks buzzed with shame. I hadn't worn diapers for five years now and it was utterly humiliating to have to wear them now.
As I got off of the bed, I felt the slippery plastic between my legs as they rubbed against the thick material. With only a t-shirt on, the fat diaper made me look like a two year old toddler and that's exactly what I felt like as I waddled out of the room. I passed by the bathroom and I couldn't help but look at myself in the full view mirror there. The colorful nursery characters decorating my plastic pants seemed to be shouting what a big baby I was and my bottom bulged roundly. I hurried away from the humiliating reflection as fast as I could.
Going out into the living room, I turned on the tv to see what was on.
"Why don't you go outside and play?" Vanessa suggested.
"No thanks," I mumbled. The last thing I needed was for anyone else to see me dressed up like this. I was determined to do whatever was necessary to keep my diapers dry and get out of them as soon as possible.
Before long, I was absorbed in a show on tv and I tuned out the rest of the world. So much so, that I didn't see or hear the people coming up the front sidewalk that went along the front window. I was lying down on my stomach, my head propped on my hands watching the tv when the group opened the door unannounced.
"Vanessa! We're here!" an older woman's voice said.
Behind her were two young girls about my age or a little older, and when they walked in and caught sight of me, they broke into gales of laughter.
I gasped and blushed beet red, jumping to my feet in horror. This was the worst possible thing that could happen! I recognized the girls from my school. I had always thought they were really cute but they had never deigned to talk to me and now here they were, staring at me and laughing out loud. In a state of panic, I tried to bolt out of the room but instead, I ran headlong into Vanessa. She blocked my way and prevented me from escaping as she took hold of my wrist and turned me around to face her guests.
"Jimmy, don't be so rude. Say hi to our friends," she insisted.
I struggled weakly as my face turned a bright shade of red.
"Well, it looks like someone has been very well diapered," their mom said approvingly.
"Yes, I didn't want a repeat of last week's little incident," Vanessa told her.
"Well, these should take care of that, shouldn't they, Young Man?" she said as she reached down and patted me on the thick seat of my diaper.
I was speechless as I stood there, helpless to get away from them.
"Jimmy, I think you know Tammy and Brittany from school?" Vanessa asked sweetly.
I nodded my head in shame.
"Girls, this is Jimmy. Now I want you all to get along while your mother's out shopping, okay?" she said.
"Yes Ma'am," they said in unison as they stifled some more giggles.
"That's it girls," their mom said pleased, "And don't you worry Jimmy," she said as she held my chin up to look me in the eyes, "some little boys take longer than others to grow out of diapers. And some boys just never seem to outgrow them.
"I'm sure you three will have a wonderful afternoon together."
I fidgeted nervously as they said their goodbyes and the mother departed. Almost immediately, Tammy and Brittany began whispering to each other and I knew it could only be about me.
"Come on Baby, you can play house with us," the latter said with a snicker.
"My name's Jim!" I said hotly, "And I don't wanna play any dumb house with you."
"Temper, temper, Baby," Tammy said, wagging a finger at me, “better not get snotty with us or we'll tell everyone at school what you're wearing now."
A new shiver of fear ran through me as I imagined what my friends would say if they heard I was wearing diapers again.
I had had a long and difficult time getting potty trained, much to my mom's chagrin and frustration. I was four by the time I graduated to training panties and another long year before I was finally able to go to bed without being pinned into a thick diapers and plastic pants to protect my bed at night. I still had the occasional dribble or accident before I reached the bathroom but nothing too often or too much for my mom to put me back into diapers.
"Please don't!" I begged suddenly, my earlier bluster gone, "please don't tell anyone."
"Then you better do as we tell you...Baby," Brittany said ominously.
We went into the back yard which thankfully, was fenced off from the rest of the neighborhood. However, that didn't prevent me from looking around every five minutes just to make sure no one was looking over the edges.
I played along with the girls reluctantly and hoped by cooperating that they'd keep my diapers a secret. They teased me mercilessly, calling me a little sissy baby and a potty pants but I had no choice but to tolerate their treatment.
At one point, we got into a bit of a tussle and I found myself wrestling with the two girls. I had to admit, I felt pretty lucky to be in such close contact with these cuties that otherwise never would have given me the time of day back at school. But things took a turn for the worse when they held me down and started tickling me. I begged them to let me up but they were much too strong for me. I giggled hysterically until the inevitable happened. Kicking my feet into the air as I struggled, I proceeded to pee uncontrollably into my diapers. I think they sensed what was happening because they kept on tickling me until I had thoroughly soaked myself.
When they let me up, I looked down at the huge wet spot in the front of my diaper and my laughter turned into tears.
Just then, Vanessa appeared at the back door to investigate.
"What's going on out here?" she inquired.
The girls just looked at each other and smiled while I sobbed in shame.
Vanessa came over and looked down at my diapers, instantly realizing what had happened.
"Shhh...don't you worry Jimmy, we'll get you into some fresh dry diapers right away," she said as she hugged me to her big, soft bosom.
"B-but, they made me do it," I cried in despair.
"Shhh," she said shushing me, "it's okay Jimmy. It's like Mrs. Turner said, some little boys just need their diapers a little longer than others. Come on inside and we'll get you all fixed up."
Everyone went inside and we went back into the bedroom where I was first diapered.
"What about them?" I protested as I saw Vanessa wasn't making any attempt to exclude them from watching.
"Hush Baby," she said without answering me.
She unfolded a changing pad and placed it on the bed, sitting me on top of it. If I was embarrassed before, this was twice as bad as Vanessa peeled the clinging plastic pants off of my diaper and down my legs. The girls watched with amusement as she unpinned my wet diaper and pulled it out from under me, dropping it into a nearby diaper pail. I turned my head away from the girls as she began meticulously wiping my crotch and bottom with cool baby wipes. After powdering me and smoothing it onto my bottom and tiny pen-is, she began gathering a new stack of diapers to put on me.
"Please, please can't I go without diapers Ma'am?" I pleaded strenuously.
"I'm afraid not Jimmy. You've shown me very plainly that you can't be trusted without them," she explained, "and after this it'll be naptime and I don't want you wetting my bed.
"Just in case, I think I better add a soaker pad since you seem to be a heavy wetter."
I cried softly as she lifted up my bottom and slid the thick diapers underneath me. More powder followed and she re-pinned the sides, locking me securely into my baby soft prison once again.
"Here's some plastic panties for him," Tammy offered, a little too helpfully, as she held out a pair of pink nursery print vinyl panties.
"Thank you Tammy," Vanessa told her, as she took them and began sliding them up my legs.
I resisted her efforts, thrashing my legs in protest.
"But those are for girls!" I complained.
"Now Jimmy. I don't have a lot of plastic panties for you to choose from. You'll just have to wear what I have available," she said tugging them up and into place.
"It's not fair," I pouted, "it's not fair."
"Shu-shush, Little Baby," she said trying to sooth me.
These diapers were even bulkier than the last set I was wearing and they billowed out from my skinny body in the most humiliating way.
"There you go. All safe and secure!" Vanessa enthused as she snapped the elastic waistband of my panties.
Tammy and Brittany giggled at my predicament and I felt my eyes filling with tears.
"And now it's naptime for my little one," she said as she put the diapering supplies away.
"But I never take naps!" I whined bitterly.
"Well you do in this house," she said firmly, "and I've had just about enough of that attitude Young Man. You'd better work on your manners or you'll find yourself over my lap in no time."
I gulped in fear but said nothing as she led me down the hallway to another room. It looked like a little girl's room with frilly curtains and pink furniture and she closed the curtains before sitting me on the bed. My thick diapers caused me to sit a little higher than I would normally and Vanessa untied my shoes while I gazed down the front of her top. I could easily see the soft, smooth skin of her breasts where they curved together and formed a deep cleavage, her lacey bra peeking out from the low cut of her top.
She pulled back the covers and tucked me in, handing me a teddy bear to console me.
"That'll make you feel better, Honey," she said as she draped my arm over it.
Walking out of the room, I watched the light play on her long, silky legs as she went out the doorway.
For the first time since my traumatic morning began, I was alone.
My hands went down to touch the soft vinyl of my plastic panties. My diaper felt very cushiony and it occurred to me that they were far more pleasing against my skin than my normal underwear. I had forgotten how soft cloth diapers were and I blushed at the realization of it.
Somehow, I drifted off to sleep, hearing voices down the hall and wondering why the girls didn't have to take a nap like me...
I woke up to the feeling of my bottom being squeezed by Vanessa's hand. For a moment, I forgot where I was and in a panic, I jerked away and sat up.
"Mommy!" I cried.
In the darkness of the room, I heard the unmistakable sound of Tammy and Brittany's giggling and I remembered where I was.
"Jimmy. Have you wet your diapers again?" Vanessa asked incredulously.
"Uh-uh!" I denied emphatically but as I sat here on the bed, I knew with certainty that I was soaking wet. How did THAT happen? I almost never wet the bed, I thought frantically. I blushed in shame as the girls whispered amongst each other and giggled some more.
Vanessa stood there with her hands on her curvy hips, framed in the light from the door staring down at me.
"You really ARE a big baby, aren't you?" she said, her voice filled with disbelief and disappointment.
"I don't know what happened!" I cried, "honest!"
She shook her head and frowned down at me but said nothing.
"Come along, Jimmy," she said with a heavy sigh, "time to change your diapers...again!"
I followed her out, accompanied by the whispers and snickering of the other two girls. Somehow, I wondered if they had done something to me while I was asleep.
"Honestly, I don't know how your mother ever graduated you out of diapers," Vanessa said as she placed me back on the changing pad.
"But I never pee my pants at home!" I said defensively.
"Oh, and you only do it when you're being babysat then?" she asked pointedly.
"No!" I cried, but she was already peeling my plastic panties down again.
"Well I'm going to tell her you belong back in diapers, full time. I've never seen someone with a wetting problem like yours and I've babysat a lot of little boys. You should be ashamed!" she scolded me as she gave my bottom a stinging slap.
I cried tears of humiliation as she pinned me back into another set of thick, thirsty diapers, covering them again with a frilly pair of pink plastic panties with snaps on the sides.
Just then, the doorbell rang and I held my breath in nervous anticipation.
"You come along where I can keep an eye on you," she said firmly.
Vanessa took a firm hold of my wrist, pulling me along behind her and I waddled as best I could. The thickness of these diapers made normal walking impossible but I also found that the soft ruffles around the panty legs kind of tickled my inner thighs.
Doing everything I could to hide behind Vanessa, I swallowed hard as she answered the door.
"Hello!'' she said as she greeted my mom.
My face turned a bright shade of red as she spied me fidgeting behind my sexy babysitter.
"Jimmy? What happened to your pants?'' she demanded suddenly.
"I think you'd better come inside,'' Vanessa told her.
My mom fixed me with a hard look and I bit on my lip nervously. This was not going to look good for me and I racked my mind for a suitable explanation that would help me avoid the inevitable punishment.
"Lately, I been having to take 'precautions' for some of the little boys who stay over here,'' Vanessa began, ''there have been some wetting incidents from some of them that I had been led to understand were already potty trained.''
My mom listened in silence while I looked at the ground, praying it would open up and swallow me. I was for sure going to be in serious trouble when my mom found out what I'd done today and my bottom twitched nervously.
"Apparently little Jimmy here has a wetting problem because I've already had to change him twice today.
"If I were you, I would strongly consider putting him back into diapers full time,'' she finished.
My mom regarded me darkly with a mixture of anger and disgust.
"Jimmy? You are in big trouble Young Man. What do you have to say for yourself?'' she demanded.
As I stood there, quivering in fear, dressed only in my sneakers, t-shirt, and a thick diaper and frilly plastic panties, Tammy and Brittany showed up to witness what was happening.
"I-I-um, I just...um...'' I stammered foolishly. I couldn't think of anything to get me out of this situation.
"Jimmy--you should be ashamed of yourself!'' she snapped, cutting me off sharply.
I fidgeted in front of everyone, shifting from one foot to another as I kept my crimson face downcast. I could feel the heat all the way to my ears and I knew my neck was flushed as well.
My only hope was to stall until we got home, maybe then I could hope to explain my way out of a spanking.
"So help me, if I had a paddle here...'' she said menacingly.
"Maybe I can help you,'' Vanessa offered brightly.
Stepping out of the living room, she disappeared down the hall, only to return a moment later. In her hand, she was carrying an oval wooden paddle, with a double row of small holes in its face. My heart skipped a beat and my eyes went wide as she handed it to my grateful mother. I licked my dry lips as she fixed me with her determined stare.
"No mommy-please!'' I begged her abjectly.
Ignoring my plea, she reached down and snatched my wrist, yanking me over to the couch. My legs felt like rubber and I whimpered in fear as she took a seat. In my heightened state of anxiety, I felt a trickle of pee escape into my diapers before I could prevent it.
"Oh!'' I squealed.
My hands shot down to the front of my diapers and I crossed my legs in futility. Crocodile tears filled my eyes and I tried weakly to stop her from pulling my diapers down.
"Nooo! Please Mommy! It was an accident!'' I cried.
"What did I tell you was going to happen if you wet your pants again?'' she said as she brusquely slapped my hands out of the way.
"I-I-I'd g-get a sp-spanking,'' I sobbed pitifully.
"Thats right Jimmy. A spanking, And now I'm going to blister your bottom.''
Throwing me across her lap, she surprised me by leaving my diapers in place. Maybe she intended to just give me a demonstration of her anger by spanking me on my well padded fanny. If that were the case, all I'd have to do was to cry some more fake tears for show, and then it'd be all over.
My short lived sense of reprieve was not to be however--instead, as I lay face downwards with my diapered bottom up in the air, she gripped the elastic waistband of my plastic panties and yanked downward, unsnapping the side snaps in one swift move. Pushing the back of my panties out of the way, she proceeded to unpin the thick cloth of my diapers and push that back as well.
Now my tender bottom lay exposed to everyone and I saw Brittany smiling at me wickedly.
"Mommy nooo!'' I wailed but I was cut short by the stinging slap of the paddle.
"OWWW-WAA!!!" I cried.
The paddle rained down on my youthful cheeks harshly, searing them in a merciless rhythm of retribution. I kicked and sobbed, banging the floor with my hands and wriggling over her lap in a futile attempt to escape. My mom was quite strong however and I was no match for her. She easily held me in place while she paddled my bottom determinedly.
I cried for all I was worth as the assault on my fanny continued. My mom delivered harsh, angry swats with the paddle, starting first with the center of my rump, and then steadily working her way outward, so that the sides of my cheeks received equal punishment. They went from a bright, candy apple red, to a flaming, deep crimson, hot and stinging over every square inch.
At long last, the spanking was over.
I lay over her lap, too weak to move, bawling like a baby. I knew I was making a spectacle of myself in front of all these people but I couldn't help myself. As I cried, I felt my mom pulling the sides of my diaper together and pin them closed. Apparently I was going to have to wear them home, although at this moment, I no longer cared.
Taking the back of my plastic panties, she pulled them up and began snapping the individual side snaps. This effectively sealed in the blazing heat on my bottom, causing me to burst into a fresh set of tears.
With little sympathy, my mom raised me up into a standing position and I rubbed the soft, ruffled seat of my diapers desperately, trying to assuage the pain. At the same time, my legs were wobbly and unsteady and my sobbing went unabated.
''Jimmy, since you've demonstrated that you can't be trusted without wearing diapers, you can just wear these home,'' my mom instructed me.
"Y-yes Mommy,'' I cried through my tears.
"But on the way, we're going to stop by the store and get your own supply. From now on, you are going to be wearing diapers full time, until you can prove to me that you've grown up enough to go without them. Do I make myself clear?''
"Yes M-mommy,'' I responded abjectly.
"Now I want you to thank Miss Vanessa for taking care of you while I was gone,'' she ordered me.
"Tha-thank you, Miss Vanessa,'' I sniffled between my sobs.
"And thank her for having the foresight to put you back into diapers where you belong.''
I had never been so humiliated in my entire life but after that spanking, I was completely defeated.
"Th-thank you for...for putting me in...d-diapers,'' I mumbled.
"I don't think she heard you Jimmy,'' my mom said as she crossed her arms over her chest.
I cleared my throat nervously, blushing again.
"Thank you for putting me back in d-diapers, Miss Vanessa,'' I repeated, my face turning a fresh shade of red.
"You're quite welcome, Sweety,'' she said pleasantly, ''you can be my little baby anytime you want. Maybe next time, we can find a cute little outfit for you to wear."
That last comment brought a round of giggles from Tammy and Brittany which caused me to lower my gaze in embarrassment.
"Well come along, Jimmy. It's time to go now. Say goodbye to your little friends here,'' my mom instructed me.
''Bye,'' I said, barely audible.
"Bye Jimmy,'' they sang in unison with big smiles on their faces.
My mom returned the paddle back to Vanessa on our way out in exchange for my folded pair of jeans.
"Thank you again for everything,'' she said to her.
"No problem at all,'' she replied, ''good luck with your potty training, Jimmy.''
I waddled out to the car miserably and sat down, wincing as my fanny came into contact with the seat. My mom got in behind the steering wheel and started the car.
"When you get home, the first thing I want you to do is to go to your room and box up all your old underwear. Do you understand me?'' she asked.
"Yes Mommy,'' I said meekly. I knew better than to argue with her now since I didn't want another session with the paddle she kept at home.
"From now on, these will be all the underwear you require,'' she said as she patted the plastic covered front of my diapers.
I sniffled abjectly as I shifted in my seat, trying to find a position that wasn't so painful for my punished bottom.
We drove down to a store nearby our house that until now, I'd never paid any attention to as it was devoted to babies. When we pulled up, I looked with feelings of dread and fear at the displays of baby furniture in the windows.
As my mom shut off the engine, she got out and waited for me to follow but I was frozen in my seat.
"Mom...can't I just stay in the car?'' I pleaded.
"Young Man, you get out of that car this instant. If you didn't want people to see you in diapers, you should have thought about that before you started wetting them like a little baby,'' she told me in her no nonsense tone.
With great reluctance, I stepped gingerly out of the car, moving towards her hesitantly.
"Come on Jimmy, we haven't got all day,'' she snapped impatiently.
Pouting helplessly, I trudged behind her and we entered the store.
It was like a giant department store for babies and toddlers and I felt very subconscious at my advanced age of ten. She pulled me along like a small child behind her and we went down the aisles toward the diaper section. We passed several mothers and their children and without exception, they looked me up and down thoroughly, some of them shaking their heads before moving on.
When we reached the diaper section, my mom began sifting through the various types trying to find the ones she wanted. From behind me, I heard a woman's voice and it caught me by surprise.
"Is there anything I can help you with?'' she asked.
Turning to face her, I saw she was a pretty woman in her late twenties, with long curly blond hair, and a generous bosom. I blushed deeply as she bent down to take a closer look at me and her beautiful smile only made me more uncomfortable. Her tight yellow halter clung deliciously to her big breasts and I stared at their perfect curves with my mouth open.
"Yes, maybe you can,'' my mom replied, ''My little Jimmy here has a wetting problem and has to wear diapers. Can you recommend any that would fit him?''
For a brief nanosecond, I held out the hope that she'd say no but then once again, my hopes were summarily dashed.
"Oh yes!'' she exclaimed, ''we have all kinds of diapers to fit your little boy.''
My heart sank upon hearing that and I reluctantly followed them down the aisle about ten feet. Once there, the pretty saleswoman showed my mom several different types of cloth and disposable diapers, all cut generously to fit bigger boys like me. My mom held up a thick disposable that were made by Pampers, noting how crinkly they were.
"Do you think these will be heard under his regular pants?'' she inquired.
"I'm afraid so,'' the woman admitted, her smooth brow creasing slightly.
"Well, you'll just have to get used to it Jimmy,'' my mom told me.
After getting several armloads of both types of diapers, we went over to the plastic panty section. I was starting to feel the beginnings of the need to pee and I hoped this wouldn't take much longer. My bladder control had never been very strong and I worried how long I'd be able to hold out.
My mom and the lady talked for what seemed like forever on the benefits of the various types of rubber and plastic panties, which of them were most comfortable for long term wearing, which were the most leak proof, how best to wash them, and so on. All this talk about wetting made me have to go all the more and I became impatient to leave. I danced around next to them counting the seconds and straining my pee-pee to hold back the tide. I also tried to distract myself by watching the saleslady before me. I noticed that every time she breathed, the smooth, exposed tops of her breasts would rise and fall erotically and they jiggled as she moved about. They reminded me of two big grapefruits, perfectly round and barely contained within her top. At one point, she accidentally bumped into me and my heart skipped a beat as her big soft breast mashed against my face.
I blushed again but she smiled down at me knowingly.
After my mom had picked up numerous pairs of plastic panties, we finally headed to the checkout counter. I had to stand in line with a number of other people, all of whom stared at my exposed diapers and bare legs. I bit my lip in frustration as a woman in front of us was conducting a return transaction, bringing our progress to a crawl.
By now, the pressure on my bladder was growing ever greater and I shifted back and forth trying to hold it in. It didn't help things that there was a damp spot already in the front of my diapers and I began to seriously doubt whether I'd be able to hold it until I got home.
"Mommy,'' I said urgently tugging on her sleeve, ''I gotta go pee!''
My mom gave me an annoyed look and she frowned down at me.
"You'll just have to wait until we get home,'' she said curtly, ''try to control yourself.''
I bit my lip again as I strained against the growing urge. Suddenly, from behind me, I felt the thick seat of my diapers being squeezed. Turning around, I blushed red as I saw an older woman smiling broadly down at me.
"You remind me of my own grandson,'' she said warmly, ''he wore baby diapers until he was seven.''
My face burned from embarrassment but I said nothing.
"How old are you, little boy?" she asked nicely.
"Ten and a half,'' I mumbled, instantly regretting the latter embellishment.
"My, you're a little old to still be wearing diapers, aren't you?'' she asked surprised.
"Yes Ma'am,'' I murmured, my ears starting to warm as well. By now, the ladies behind her had taken an interest in our conversation and they listened and watched me closely.
Hoping to put an end to this humiliation as quickly as possible, I spun around and faced forward, trying to block them out and concentrate on not wetting myself any further.
The lady behind me patted my ruffled bottom gently and bent down to whisper in my ear.
"Don't worry Honey, some little boys never outgrow their diapers. But you look very cute in yours.''
My eyes filled with tears as I endured the intense humiliation. Worse yet, my bladder felt ready to explode. As we finally got to the checkout stand and my mom was placing the diapers and plastic panties on the counter, I shook her sleeve frantically.
"Mommy, I gotta go!'' I pleaded piteously.
"Jimmy! Control yourself!'' she replied angrily.
I let out a whimper and the floodgates opened. With a sob of despair, I proceeded to flood my diapers, the warm streams of pee coming one right after another. I balled my hands into fists and shook them impotently while I stood, helplessly wetting myself like a two year old toddler in front of everyone. Soaking them thoroughly, my diapers grew heavy and began to sag. The warm wetness seeped back, saturating my crotch and then between my legs as the last stream finally reduced to a trickle.
The lady behind me bent down and patted my warm bottom tenderly.
"It's okay Baby, let it all out.''
The humiliation was too much for me and I burst into tears. My mom looked down at me and sighed heavily. The lady behind me dug in her purse and produced a large pink pacifier, holding it in front of my quivering mouth.
"Aww, poor thing, would you like a paci to sooth you?'' she asked sweetly.
I shook my head no but my mom took the pacifier and coaxed it into my mouth where I was forced to suc-k on it. A couple of younger women behind us giggled at the sight of my infantile appearance which did nothing to help my disposition. In a fit of sissyish frustration, I stamped my feet and threw a tantrum.
My mom ignored me but thanked the lady behind us and then, noticing my diapers sagging lower, she reached down and tugged them upwards by the waistband. The wet, pee soaked cloth embraced me closely, hugging my bottom and groin areas in a constant reminder of my babyishness.
After paying for our items, we finally left the store but not before the lady behind me gave my seat a playful slap. It landed with a distinctive sound of a firm maternal hand striking thickly padded vinyl panties.
"Bye-bye Sweetie-pie," she called out to me.
I was vastly relieved to escape that store - I had never experienced anything so humiliating in my entire life.
The ride home was silent and I knew my mom was still upset with me. My bottom remained sore from my earlier spanking but by now the wetness had seeped back and was covering my tender cheeks. With my snug plastic panties, there was no escaping the warm wetness that clung stubbornly to my skin.
When I got home, we both went to my bedroom together. As my mom began making space for the stacks of cloth diapers she'd purchased, I stood in such a way as to minimize my skin contact with the wet cloth I was wearing.
"Mom? Can I please get changed now?'' I begged her.
"Not yet Jimmy. I want you to go out to the garage and get a box for your old underwear,'' she told me.
"But how long am I gonna have to wear diapers?'' I complained.
"As long as you insist on acting like a baby, that's how long,'' she retorted.
Glumly, I trudged out and got the box, still unaccustomed to the feeling of wearing a warm, wet diaper that I couldn't ignore.
When I returned to the bedroom, I was surprised to see that my mom had set up an extensive diapering area. On my dresser, she had cleared away all my model airplanes and pictures. In their place were baby powder, diaper pins, baby wipes, and diaper rash creme.
Wordlessly, I began gathering my underwear and dumping it in the cardboard box as my mom filled the drawer with various plastic panties. She had chosen several different types, both pull up and sidesnap and all in childish pastel colors of white, yellow and baby blue. Removing a pair of the yellow ones, she laid them next to a vinyl changing pad that was spread across the bed. I grimaced as I looked at the nursery characters decorating the pad and taking my hand, she sat me down on it where I landed with a wet squish. Putting her fingers inside the elastic waistband of my plastic panties, she peeled them down off the sopping wet cloth and pulled them down my legs. Unpinning my diapers, she tugged them out from under me and dropped them into a plastic pail.
After getting several baby wipes, she cleaned my bottom and private area thoroughly, before getting the jar of diaper rash creme. With three fingers, she took a good sized glob of the creme and as she lifted me up by my feet, she proceeded to slather my still pink bottom with a thick coating of the substance. I blushed anew at this distinctively babyish procedure which was further enhanced by the nursery print that surrounded me on my new changing pad and the smell of the nearby vinyl. However, for the first time since we'd left Vanessa's house, my bottom was finally getting some relief and the cool diaper rash creme soothed the residual stinging on my tender fanny.
"I'm sorry I had to spank you Jimmy," my mom said, as her hand gently spread the creme over the surface of my buns, ''but you really disappointed me today.''
"Yes Mommy,'' I said, happy to see her change of demeanor.
"I thought we were all done with your potty training when you got into kindergarten, but now it seems like we're right back where we started.''
"I'm sorry Mommy. I promise to do better from now on,'' I told her hopefully.
"Hmmph. I doubt that,'' she said skeptically, '' I think you'll be wearing diapers and plastic panties for a long time to come.''
If only I had known how true her words would turn out to be...
Taking three of the pre-formed diapers, she slide them under my now shimmering rump, situating them until they were even on both sides. Then she shook baby powder over my privates and between my legs, even lifting up my tiny pee-pee to powder there. When she was done, a cloud had risen around me and the unmistakable infantile scent filled the room.
She pulled the diapers up between my legs and pinned each side closed securely while I looked away in embarrassment. Taking the yellow pair of plastic panties, she removed the cardboard label and shook them out, gathering the leg holes together in her hands.
"Feet up,'' she ordered me tersely.
I did as I was told and she pulled the soft plastic panties down my legs to the base of my thighs. It took a little effort to maneuver the panties up and over my bulging diapers but by running her fingers back and forth around the waistband, she worked them up and over until the cloth was completely encased. My mom was nothing if not thorough and she ran her fingers around the leg and waistbands, making sure the diapers were completely contained. That done, she pushed my legs apart and powdered between them generously to prevent chafe.
"There you are Jimmy. That should last you until bedtime.''
I blushed again at her appraisal which showed how little confidence she had that I'd be able to stay dry anymore.
Sliding off the bed, I waddled out of the room, extremely conscious of the soft, but bulky diapers I was now permanently imprisoned in. It was a feeling I would come to be intimately familiar with.
A week and a half later, I was no closer to getting out of diapers and back into my regular underwear. Even though I hadn't had any major accidents or anything, I occasionally would have "dribbles'' or wet spots, where I didn't quite get to the bathroom on time. And my mom never made any mention of letting me wear regular underwear, despite what I thought had been a pretty good record.
On one day, she had to go in town for a long meeting and she dropped me off once again at Vanessa's house. When I arrived, my earlier nemesis, Brittany, was already there and my heart sank. I was wearing my usual outfit for these days, a t-shirt, sneakers, and by now, the mandatory exposed diapers and plastic panties.
Vanessa looked as stunning as she was the first time I met her, even though she was only wearing a very simple outfit. She had on a short pink skirt which showed off her fabulous legs and thighs to great effect. However, it was the top she was wearing that I couldn't take my eyes off of. It was a thin, tight white material that wrapped across her unbelievable bosom diagonally from either side, resulting in a plunging V that displayed her deep cleavage that couldn't be ignored.
"Well, it looks like your mommy decided to keep you in diapers after all, Jimmy,'' she said brightly.
I nodded in embarrassment and she patted my thick seat appreciatively.
"I guess I better make sure I've got plenty of spares if you plan on wetting them like you did last time you were here,'' she said, bending down to speak to me.
I remained mute as I gaped openly at her mouth watering breasts, hanging before my face with perfect form and roundness.
As soon as we were alone, Brittany wasted no time in teasing me mercilessly. She compared me to her little brother, a toddler of four who was just graduating to training pants.
"Maybe someday YOU can wear training pants, Sissy,'' she derided me.
I was forced to endure her insults as best I could since she still held the power over me of revealing my secret to everyone else. The problem was, she seemed to be using that power to greater and greater effect to dominate me. She decided we were going to play house again but this time, I was going to be her baby girl. I resisted strenuously until we got in a scuffle. I had never been known for my fighting prowess and as it turned out, despite the fact that I was larger in size, she had me down on the ground with my arm twisted behind my back in a matter of seconds. She made me say all kinds of humiliating things but the worst was having to beg to wear a dress. She made me promise to repeat myself to Vanessa or else she'd really make me sorry.
Being rather meek by nature, I reluctantly agreed and we went inside to find Vanessa. Brittany instructed me to let her do most of the talking and we found Vanessa filing her nails.
"Aunt Vanessa? We wanted to play house outside and Jimmy wants to be my little girl. Do you think you might have anything that he could wear?'' she asked.
"Well,'' Vanessa said, clearly interested, ''I'm sure I can find something cute for him to try on. My niece stays here from time to time and I think I have one of her Sunday school dresses in the other room.''
I followed them down the hall with leaden feet as Vanessa went to retrieve the clothes. Sorting through a closet, she produced a pink and white taffeta dress, very fancy, with miles of frills and lace. As Brittany giggled with delight, I groaned in helpless frustration as this instrument of my humiliation was held in front of me.
"Well, it looks like it may be a bit short but you don't mind that, do you Jimmy?" she asked me.
I was about to blurt out that I very much did mind but I felt Brittany step on my toe painfully.
"Ouch! ...No Ma'am...i-it's okay," I mumbled, cursing myself for my weakness and lack of will.
Removing my t-shirt, she threw it on the bed and then instructed me to lift my arms up. She lowered the lacey confection over my head and adjusted the puffy short sleeves and hem which only just covered the elastic waistband of my plastic panties. I tugged at it myself to help but it was obvious that no effort was going to make it cover any more of my bulging diapers than the top inch or so. Under the dress was a petticoat of sorts, that flared the dress outwards with row upon row of white, pretty ruffled lace. Turning me around, she buttoned up the dress in back all the way to the neckline, effectively securing me into the babyish outfit.
Vanessa smiled down at me and saw me tugging at the hem in frustration.
"Aww...you'd like something else to cover your diapers wouldn't you?" she asked me gently.
"Yes Ma'am," I quickly agreed. Maybe she'd forget about this dumb dress and let me go back to wearing my t-shirt. Instead, she dug in a drawer until she found a silky pair of pink rhumba panties, with three rows of big ruffles gracing the seat.
"Here you are Sweety!" she said, obviously very pleased.
I stamped my feet and gritted my teeth as she snaked the stretchy panties up my legs and over my thick diaper. Afterwards, she fluffed the hem of my dress all around, making sure it wasn't tucked in anywhere.
"Oh, don't you look darling," she said admiringly.
I blushed as I looked down at my sissyish appearance. The thing is, the dress had a strange effect on me, making me feel even more effeminate and babyish. It was like Vanessa was reading my mind because she snapped her fingers and turned around, getting something from behind her.
"I know! I have just the thing!" she said as she popped a big pink pacifier in my mouth.
I suc-ked helplessly as my eyes brimmed with tears of shame. Vanessa must have noticed because her smile briefly disappeared.
"What's the matter Honey? Have you wet yourself?" she asked, immediately checking at the legbands of my diapers.
I shook my head no and pouted in front of her like a toddler.
"Well if you do, you just tell Brittany and we'll make sure to get you changed you right away...okay Honey?" she said ever so sweetly.
I nodded my head and sniffed as I looked down at the floor.
"Come on Baby," Brittany said with a broad grin, as she took my hand and pulled me out of the room.
A moment later, we were outside again in Vanessa's sunny backyard. Brittany sat me at her tea table and made me talk like a baby with her, after which she filled a bottle with warm milk and instructed me finish it. In my diapers and frilly dress, I couldn't help but feel like a little baby and I found myself thinking less and less like a big boy of ten and a half. Without thinking, I nearly wet myself and I only caught it, just in the nick of time. My mom only needed the slightest excuse to extend my diaper treatment and if she found out I'd wet another pair, she'd be sure to forget any plans for potty training me.
After about an hour, we heard the voice of Brittany's mother calling her from inside the house. I would of course, have preferred to stay where I was but Brittany insisted on forcibly pulling me by my wrist back inside.
When her mom spied me in my sissyish outfit, she giggled and smiled down at me, looking me up and down in an appraising manner.
"Yes...oh yes. That definitely suits you," she said enthusiastically. Walking around to where she could see my behind, she nodded her head up and down agreeably, "oh yes, you should have been born a girl, Jimmy. That dress looks just right on you."
I blushed hotly under her examination and comments, unable to form a reply.
"Where did you find it?" she asked Vanessa who was also smiling down at me.
"I was fortunate to have a few outfits left over from when Janie was here last month," she explained happily.
"Well, it seems so appropriate for someone like him, an obvious sissy who still needs his diapers."
I tried desperately to fight back the tears from this humiliating assault but I didn't want to appear more like a baby than I already was.
"Now all you need are some lacey anklets and mary jane shoes, Jimmy," she said as she adjusted the short puff sleeves of my dress.
They finally said their goodbyes, much to my relief, and I was left alone to amuse myself as I saw fit. Even though Brittany was gone and I was no longer obligated to "play house", Vanessa left me as I was dressed, and she went back to whatever she was doing previously.
At one point, I wandered into the bathroom where a full length mirror stood on the wall. A strange part of me was curious to look at the way I appeared and after making sure Vanessa wasn't around, I gazed at my reflection in the mirror. My sneakers gave me a boyish look but that was where it ended. When I looked at the white ruffled edges of my pink rhumba panties, my face reddened and grew redder as I twirled around to see the bouncy rows of ruffles across my big, round, diapered bottom. The frilly dress I was wearing made me feel girlish and I felt an odd sensation inside that I couldn't quite explain. Part of me wanted to admit that secretly, maybe I was just a big sissy, who needed to be dressed in diapers and little girl's clothes. I shuddered to myself at the realization but quickly rejected it.
Suddenly, I heard Vanessa call my name from down the hall and I wondered to myself what further torments she had in mind. Waddling down the hall, I made my way into her bedroom, which was softly lit and very feminine. She had an ornate four poster bed with frilly curtains that adorned the corners and the rest of the room's appointments reflected her sexy personality.
I saw her sitting on the bed, looking relaxed with a couple of fluffy pillows propped up behind her back. I couldn't help but notice that the warm lighting only enhanced her fabulous figure, creating deep shadows between her fabulous breasts.
"Come over here and sit next to me, Jimmy,'' she said, beckoning me as she patted the bed. I found it difficult to hold the gaze of her beguiling eyes because of my shyness, but I moved closer and worked my way onto the bed.
Vanessa had a devastating smile and when she graced me with it, I nearly fainted. Taking me by the hand, she pulled me up between her long, smooth thighs and fixed me with a seductive look that made me quiver.
"You know, in my house, naughty little boys get spanked...'' she said, her voice silky and disarming.
"Um...uh-huh,'' I said uncertainly, suddenly becoming very nervous.
"But good little boys get treats,'' she continued, her beautiful smile washing over me like a warm wave.
Her perfectly manicured hands moved to her immense bosom, stroking and cupping her breasts in a very inviting manner.
"I've noticed you staring at my boobs, Jimmy, maybe you'd like to take a closer look, hmm?''
My heart was beating wildly now in this intimate setting and I felt a strange but pleasant sensation in my groin as I stared openly at my sexy babysitter fondling her massive breasts. Each one looked about the size of my head and I found my breath coming in short gasps as I tried to come to grips with what was happening.
Slowly and teasingly, she slid back the thin material of one side of her top, exposing the white lacey bra that barely held her tremendous breast. I licked my dry lips, unable to take my eyes off her smooth, curvacious skin. I watched her long french nails as she pinched the firm nipple through the fabric of her bra, causing it to protrude even more enticingly.
Vanessa put her other hand on my head and gently pulled me toward her chest. At the same time, she pulled her big breast out of the cup of her bra and offered it before my quivering lips. Like a starving boy, I closed my mouth over her nipple, the flesh warm and delightful in my mouth. My nostrils were filled with the wonderful scent of her skin as well as a slight trace of her perfume and my head swam with ectasy.
"That's it, Little Baby,'' she said softly as she caressed the top of my head, ''nurse from mommy's boobs.''
Within the warm folds of my thick diaper, I felt my tiny pee-wee straining against it's bunny soft confines and I suc-ked greedily on the hard nipple filling my mouth. I was in state of unbridled pleasure as I felt Vanessa's hand move down to the front of my diaper and begin stroking it softly. My breath was coming in gasps as I suc-ked like an infant. My forward vision was filled with her incredible breast and out of the corner of my eye, I could see across her deep cleavage, where her other boob was still confined within the cup of her lacey bra. The combination of sensations and sights was too much for my juvenile composure and I suddenly experienced my first orgasm, blinding in it's power and scope. I whimpered and gasped as my head spun and my vision swam. I had never experienced ANYTHING like this in my entire ten years of existence.
I sat back, breathing hard as my heart raced and my vision began to return, my mind still trying to understand what just happened.
"Did my little baby like that?'' Vanessa whispered softly in my ear.
I nodded enthusiastically, still unable to speak as I tried to catch my breath.
Vanessa gazed down at me with that devastating smile as she placed her breast back within the cup of her bra and returned her top to its original position.
"And now I want you to do me a favor,'' she said sweetly.
At that moment, I would have chopped my arm off for this heavenly goddess if that was what she required.
"Aunt Vanessa wants you to just relax and do your little tinkle in your diapers. Can you do that for me?''
Strangely enough, as my orgasm subsided and my tiny wee-wee began to shrink back to it's not-so-impressive one inch size, I felt a growing need to urinate. I thought her request was a bit odd but in my state of lingering bliss, I didn't give it a second thought. Closing my eyes, I just relaxed and let my muscles do what came naturally. In moments, the distinct sound of pee streaming into my diaper could be clearly heard.
"That's my baby,'' Vanessa coaxed me softly as she squeezed my hand. Looking up into her beautiful dark eyes, I couldn't help but blush as the the front of my diapers became saturated and the wetness began to seep back between my legs. After about a minute, I had released everything I had been holding inside and my diapers were completely soaked. Vanessa put her hand down and felt the warm front of my panties, patting them gently.
Suddenly, her eyes focused on the wall clock and she looked back at me abruptly.
"Oh my, will you look at the time!'' she exclaimed, ''your mommy will be here any minute.''
I thought I caught the faintest hint of a smile on her face and I wondered...
My mouth dropped back open and my heart began beating hard again as I realized what I had just done.
As she rose from the bed, she smoothed out the wrinkles on her short skirt and went to get a brush from her nightstand. I snapped out of my pleasant reverie and started thinking hard about what I should do about my now soaking wet diapers.
"Um, Aunt Vanessa?'' I asked tentatively.
"Yes Honey?'' she replied without looking away from the mirror as she brushed her luxuriant, long brown hair.
"Um...do you think you could, um, change me, before my mom shows up?'' I asked hopefully.
"Hmm....'' she said, taking longer to consider my question than I really thought was necessary.
Before either of us could say anything further, the doorbell rang.
Uh-oh, I thought as I felt the warm wet cloth of my diapers pressing against my skin. What was my mom going to say when she discovered them, I asked myself frantically. Why did I do it, I demanded of myself. Now I'd never get out of diapers, no matter what excuse I thought of! Except I couldn't think of even the lamest excuse at the moment!
Vanessa left me to my panicky thoughts as she went to answer the door. Sure enough, it was my mom and Vanessa went on to explain to her that I had wanted to play dress-up with Brittany and they had found a "cute" dress for me to wear. She made it sound like it was all my idea and my mom simply shook her head at her sissyish son standing before her. I was only half listening as I was still trying to figure out how I'd explain my wet diapers to her. Wouldn't you know it, the next thing she did was to slip one of her fingers underneath the legband of my plastic panties. The wetness inside was plain to see as she rubbed her fingers together in front of me.
"Soaked again,'' she said, obviously fed up, "and to think I thought you'd reached the maturity level to move on to training pants,'' she said shaking her head.
"Well? What have you got to say for yourself?'' she demanded.
"Um, I-um, ah...I dunno,'' I stammered.
My sense of well being from the orgasm evaporated like drops of water hitting a hot stove as she reached down and swatted me on the thick seat of my diapers. Her firm hand landed with a dull thud but I squealed like a little girl anyway.
"Vanessa, you were quite right. I'm going to make sure Jimmy stays in diapers from now on...day and night."
Crossing her arms, she looked down at me, her disappointment obvious.
"Jimmy, I don't know what's gotten into you but you can just forget about those training pants you wanted. You'll be in diapers for as long as you're under my roof. Now get out to the car, you little sissy!" she punctuated her last remark with another sharp smack to my diapered bottom.
I began crying softly as we went out the door and as Vanessa said goodbye to us, it seemed to me that her smile was filled with satisfaction.
So began my long and humiliating path down the road to complete sissyhood.
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The following morning, I awoke to my dismay to discover that I had soaked my diapers sometime during the night. I could feel the wetness all the way back through my seat and even around where the diapers were pinned. The cool, wet cloth clung to my clammy skin, forcing me to face my infantile lack of control. I was at a loss to understand why it had happened and I couldn't believe that I hadn't been awakened by the sensation. I knew my mom wouldn't be happy about it--I just hoped and prayed I wouldn't earn another trip over her lap. By now, there was no hope whatsoever of convincing her to let me wear training panties, never mind, my big boy underwear. That was definitely a thing of the past. Part of me even considered that maybe I did need diapers and plastic pants. My control seemed to be slipping away before my very eyes.
I considered trying to change my own diapers before my mom found out but no sooner did I get out of bed and stand up when my mom barged into my bedroom.
"How's mommy's little baby?" she asked as she strolled through the door.
My heart skipped a beat and I instinctively jerked away when her hand went down to check my diapers.
"Jimmy! Did you wet yourself again?" she asked angrily.
"Ummm...I um," I said as I bit my lip in angst.
Without hesitating, she simply reached down and squeezed the seat of my thoroughly soaked diapers.
"Mm-hm. Just as I suspected," she said as she crossed her arms over her chest, "wet, as usual."
I stared at the floor, crestfallen.
My mom sighed heavily.
"Come along Baby Boy, it's time for your bath, then we'll get you changed right back into your diapers" she said as she led me out of my room.
Down the hall, she took me into the bathroom where a hot bath was waiting. I couldn't help but notice that bubbles filled the tub and I smelled the scent of baby shampoo filling the room. Pulling down my clinging plastic panties, she allowed my sopping wet diapers to fall on the bathroom floor but as I stepped out of them, she slapped my bottom sharply.
"Oh!" I squealed in surprise, sounding more girlish than ever.
My mom frowned at me and just shook her head.
Putting me into the tub, she washed me thoroughly as she would a baby, scrubbing my private regions with great familiarity which left me blushing. Afterwards, she left me to dry myself off while she went into my bedroom to prepare my diapers.
I tried to stall as long as possible but my mom wouldn't have any of it.
"Jimmy!" she barked from the other room, "get your sissy bottom in here."
I blushed again at that reference and walked in with the towel wrapped around my waist in a pathetic attempt at modesty. My mom simply yanked it off me and guided me down onto the stack of thick cloth diapers waiting on my changing pad. I
Betty Pearl's Sissy Stories 20.1
Topic: Jimmy's Return to Diapers (Read 41050 times)
