The screen door clattered with a bang behind me as I entered the house and saw my babysitter, Stacey, sitting at the table. I deeply resented that my mom still felt it was necessary for me to have one, since I was, after all, thirteen, going on fourteen. Not only that, Stacey was only a mere two years my senior, hardly the matronly adult one would expect to oversee my wellbeing.
Still, much as I hated being perceived as a child, there were few people in this world I admired more than Stacey Plum. She was head of the cheerleading squad and probably the most popular girl at our school. Standing a few inches taller than I (certainly much more in her heels), she had an unbelievable body, sculpted by hours doing workouts on and off the field. Mother Nature had generously blessed her with an impressive bosom and I could hardly stop myself from staring hungrily at the deep line of cleavage she often proudly displayed.
The truth was, with my skinny, frail body and average looks, the two of us were in totally different social worlds and wouldn’t otherwise have had any association with each other, were it not for the fact that my mom was friends with her mom.
Today, Stacey was sitting at the dining room table, texting on her phone, and still wearing her school uniform. I was certain that no other female could make such an ordinary set of clothes look so sexy; she had somehow—without attracting the ire of the school authorities, contrived to raise the hem of her plaid skirt an inch or two, which showcased her fabulously toned thighs to great effect. And once she was out of class, she untucked the bottom of her white blouse and tied it together in a knot beneath her succulent big breasts, while undoing the top buttons to show off her incredible curves.
I felt my little pen-is stirring as I drank in her profile.
“Hi Stacey!” I greeted her cheerfully.
Looking up at me for the first time, her mesmerizing auburn eyes gazed me up and down until I saw her staring disapprovingly at the front of my pants.
“Brian—you wet your pants at school again,” she announced with annoyance.
Looking down myself, I gasped as I took in the silver dollar-sized wet patch at my crotch—I hadn’t even realized I had had an accident!
Stacey sighed with resignation as she stood up from the table.
“Come along, you know the drill,” she told me.
“B-but...it-it was just an accident,” I whined desperately.
“Come along little boy,” she said condescendingly, “you know the drill,” she repeated.
I certainly did ‘know the drill’, as she put it. My mom insisted on making me wear diapers and plastic panties, not just for my nightly bedwetting, but also increasingly, as a punishment for anytime during the day that I happen to wet myself. It was absolutely mortifying that Stacey not only knew all about this but also happened to be a part of my discipline program. And although I already felt a tremendous social gulf between us as it was, having her undress me and pin me into my babyish diapers made me feel even more childish before her.
Taking me by the hand, she led me down the hallway and into my bedroom, which anymore, smelled strongly of stale pee, the classic hallmark of a chronic bedwetter. I was so ashamed to have my idol wrinkle her cute, button nose in distaste every time she entered the room but of course, there was no getting around it.
Telling me to remove my shoes, she bent down to unzip my pants, slipping her long nails inside the waistband of my damp undies and pushing them down together. I stared dumbfounded down the front of her blouse, gaping at her mouthwatering boobs—she was SO adult and sexy!
Although I tried my best to cover my tiny little pen-is with my hand, Stacey’s dismissive look said it all—clearly, she thought I had the equipment of a toddler, despite the proud half inch of growth I’d achieved during puberty. To be sure, even semi-erect as it was now, my diminutive, inch long stub was not likely to impress anyone, and certainly not Stacey Plum.
Although there was already a stack of bunny soft diapers awaiting me on my changing table, Stacey took another one and after folding it in thirds, she placed it lengthwise between the layers of the other three to create a soaker pad down the center and make for an even thicker diaper.
I trembled with shame and anxiousness as she guided me down onto the fluffy stack.
“Honestly, you must be the only one in the eighth grade still wearing diapers and baby panties,” she said as she grasped my ankles and abruptly swung them over my head.
My cheeks flushed a bright red and I looked away, too embarrassed to reply.
A moment later, I felt her soft hands, smearing cool diaper rash cream across my bashful bottom, leaving a thick, sticky layer of protection that I felt was completely unnecessary, but which she did, almost certainly, just to humiliate me further.
Lowering my legs, she shook fragrant baby powder across my child-sized package, shaking her pretty head in silent disapproval as she did so. It was crushing to see the look on her face that said she saw me, not as some sort of peer, but just a diaper-wetting toddler.
Pulling the thick, absorbent cotton cloth up between my thighs, she pinned the sides together snugly around my hips. The bulk was so thick, it spread my legs apart in an embarrassing, babyish display.
Stacey was well familiar with all my diapering supplies and unlike my mom, who tended to use the plain white plastic panties on me, she deliberately selected a lilac pair with a nursery print on it. Nevertheless, I felt I had to put my foot down at this assault on my dignity.
“No!” I protested bitterly, “I don’t want to wear those.”
Gathering them in her creamy hands, she regarded me sternly.
“I’m your babysitter and I will determine what you wear. Do I need to put you over my knee for a spanking?”
My mouth dropped open in shock and my face flushed hotly. I couldn’t believe she was threatening to punish me like a naughty little boy! She was only two years older than me!
I wanted to shout out and defy her but she was both bigger and stronger than I. The fact is, I was hardly confident in a physical confrontation that I would come out on top. Much more likely, I’d find myself over her lap, getting my bare bottom severely paddled in a repeat of my mom’s punishment sessions.
I bunched my fists in angry frustration and my mouth clamped shut in defeat.
“No? Alright then.
“Maybe if you didn’t wet your pants like a child, you wouldn’t have to wear diapers and baby panties, hm?”
I blushed crimson with shame as she tugged the humiliating plastic panties up my legs, working them over the fat diaper. After dusting between my inner thighs with baby powder, she put my shoes back on and tied them for me.
“Wha-what about my pants?” I complained, my eyes moist with tears of shame.
“These are the only pants you’ll need today,” she said with a smug smile as she gently patted the bulging, bulky front of my diapers.
I knew then and there that as soon as my mom walked in the door, she would know immediately I had wet my pants at school and these were my punishment clothes. This would be the third time this month it had happened and I swallowed hard with trepidation, terrified at the thought of how she’d react.
Maybe I’d be able to convince Stacey to take my diapers off later, and my mom would never find out, I tried to convince myself.
I sniffled as Stacey helped me to my feet and I stood before her, feeling more childish than ever as I looked up at her pretty, superior face.
Taking me by the arm, she turned me around and swatted my thickly padded bottom.
“Run along and play,” she told me dismissively.
Pouting miserably, I waddled out of the room, anxious to be as far away from her as possible.
For the next hour or so, I amused myself in the back yard, which fortunately was heavily wooded and fenced off from our neighbors. Still, every step I took, further reminded me of my babyish existence, the embarrassing plastic panties crinkling loudly and the soft cloth swishing between my legs. Looking down, the ambient sunshine reflected brightly off my pretty panties which only reinforced my infantile status. I could only imagine what my friends would say if they were to see me now.
It was true, most people regarded me as a sissy, a nickname I had never been able to fully shake. I suppose I might not be the most macho guy at school but I’d lost track of how many times I’ve been called a ‘pantywaist’, ‘pansy’, or ‘sissyboi’. And the fact that I’m a chronic bedwetter who wears diapers certainly doesn’t help my self-image.
Waddling back inside the house, I entered the living room, only to discover that Stacey had apparently invited some of her cheerleader friends over without telling me. As they turned as one to gape at me and take in my childish diapers, I gasped aloud in shock and panicked. Before I could think or try and stop it, I suddenly felt an urgent stream of hot pee flooding the front of my pampers, quickly soaking them as my cheeks blazed red.
Her friends burst out laughing as a second strong stream followed the first.
“Who’s the sissy baby in his diapers?” Wendy Johnson asked as she continued to laugh uproariously.
Rachel shook her head in disbelief as Stacey smiled with amusement.
“Brian wet his pants at school today so I put him back in his diapers as soon as he got home,” Stacey replied.
“Oh, my-god,” Rachel exclaimed.
“Come over here, sissy boi,” Stacey beckoned me.
I wanted nothing more than to run and hide in my room but deep down, I knew they would only chase me down and subject me to some humiliating punishment for my defiance. Perhaps better just to get it over with, I thought as I slowly waddled over to them.
Wendy whistled as she ran her fingers down my exposed thigh.
“Such smooth, girly legs,” she remarked mockingly, “They really compliment your sissy diapers.”
“You should get him some Mary Janes and a dress to go with his pampers,” Rachel suggested.
“I just babysit the little pantywaist—that’s his mommy’s job,” Stacey sneered with a dismissive wave of her hand.
Rachel’s reached over and abruptly yanked me closer, her other hand squeezing my thick, vinyl covered bottom.
“Eww! He wet his diapers!” she exclaimed, slapping my fat seat with derision.
My cheeks flushed deep red with humiliation as everyone looked at me like I was a helpless toddler.
“Oh my god,” Stacey rolled her eyes in exasperation, “Already?—I just changed your diapers an hour ago.”
My lower lip quivered uncertainty, even as another warm stream of pee added to my already soggy wet diapers before I could stop it.
“Come along, sissy boi,” she said with obvious annoyance.
This was a disaster! It was bad enough that Stacey was privy to my bedwetting secret—but now, two of her hot friends were about to find out about it too!
I dragged my feet but there was no preventing the inevitable. All too soon, the three of them filed into my bedroom, where my changing table with its stacks of cloth diapers and baby panties awaited me.
“Eww, it stinks!” Rachel complained loudly.
Wendy shook her head in dismay as Stacey began peeling my plastic panties down off my wet, sagging diaper.
“Normally, Brian is able to keep his wetting under control during the day but come bedtime—the floodgates open up and he soaks himself like a helpless toddler,” she explained, “You’ve always been a bedwetter, haven’t you?”
My chest and ears burned with humiliation as I kept my eyes downcast and nodded in shame.
“Yep, and that’s why you’ll always be in diapers,” she continued as she sat me down on the changing table.
I whimpered in fear, knowing in mere moments, the other girls were about to see my tiny little package and there was nothing I could do to prevent it.
“Looks like I’m going to have to have a talk with your mommy,” she said as she pulled my wet diapers out from beneath me, “I seriously think she needs to start keeping you in diapers during the daytimes too.”
I gulped with fear, aware of my already precarious position with my mom—the fact was, she had already threatened me with daytime diapers several times. One word from Stacey was sure to push her over the edge.
“Please don’t!” I begged her, “Please don’t tell her.”
“You need diapers like a baby,” she said with a harsh slap of my exposed, damp bottom, “And I’m going to make sure she knows it.”
My lip quivered again and I felt like I was on the verge of tears.
“Aww, is the wittle baby gonna cry?” Rachel said mockingly, “Maybe you should get him a pacifier.”
“Wow,” Wendy said as she stared at my tiny shriveled pen-is, “You really do belong in diapers. My toddler cousin has a bigger package than that.”
I looked the other way in a futile attempt to avoid her attention.
After smearing Desitin across my exposed cheeks, Stacey slid another fat stack of diapers beneath me and began powdering me. Rachel had removed her cell phone and was busy snapping pictures of my humiliating ritual.
“Oh my god, wait til the girls see this,” she remarked.
“I’ll bet you’re a chronic masturbator too,” she said, looking up from her phone.
“Eww,” Stacy answered as Wendy laughed out loud, “I don’t even want to think about that.”
“Maybe you should get the little sissy a chastity device,” the latter suggested with an evil smirk.
The girls all laughed collectively at my expense.
“But do they make them small enough to fit that?” Rachel asked, the disdain plain in her voice.
“Hmm,” Stacey paused to consider it, “We should look and see what we can find online.”
“I’m sure his mom won’t mind,” Rachel urged her.
“Oh no—she’d totally be onboard,” Stacey said as she pulled the soft, bulky cotton cloth up and pinned the sides firmly around my hips.
“Looks like your masturbating days will soon be over, sissy,” Wendy told me, as she looked down at me from the bed.
My heart skipped a beat and I gulped hard at the thought of losing access to my little wee-wee. It was true that I was an inveterate masturbator and there were some days when I did it two or three times. The notion of having my little nub permanently locked into a steel cage was terrifying!
“I think it’s a fantastic idea,” Stacey announced, “Sissies who wear diapers don’t deserve to have erections like a real man and they definitely shouldn’t be having orgasms.”
The other two nodded in agreement as Stacey pulled a stretchy pink pair of rubber panties up my legs.
“Here’s one that looks like it would fit. It’s called the Sissy Restrainer and it fits dic-ks as short as one inch. What do you think?” Rachel asked excitedly.
This was all happening too fast! I couldn’t believe I was about to have an actual chastity device ordered for me.
“I’ll gladly pay for it,” Stacey said as she wrestled the rubber panties up and over my fat, bulky diapers, “As long as we can be sure he won’t be able to remove it.”
“This one is stainless steel and it gets a rating of ten for security,” Rachel replied eagerly, “Once it gets locked on—it’s there to stay.”
“Perfect!” Wendy grinned, “Better play with yourself as much as possible tonight, bedwetter boy—your new chastity device is on its way.”
Stacey stood over me with her perfectly manicured hands on her curvy hips, looking down at me over the twin mounds of her big, round breasts.
“Right where a sissy bedwetter belongs—in diapers with his little baby stick about to be locked away in a secure chastity device.”
I bit my lip anxiously, looking from one smug, smiling female face to the next. How was I going to get myself out of this? And what would my mom say? Unfortunately, I knew only too well that she would enthusiastically embrace the idea of my baby-sized pen-is being locked away so that I couldn’t play with it anymore. And when would she ever unlock it? Most likely never, I reflected glumly. That meant my secret stash of masturbating material would be completely useless to me from now on. My heart skipped a beat at the thought of never having another orgasm again. This was something I was totally unprepared for!
Just then, I heard the front door close and a moment later, my mom’s footsteps coming down the hallway toward my room. I waited in dread, fearful of her reaction to this latest episode of me wetting my pants.
As she was about to step into my room, she stopped in her tracks, framed by the doorway. Looking first at the three cheerleaders surrounding me, her gaze fell upon me, where I was still sitting on my changing table like a helpless toddler, my legs splayed outward, due to the fat bulk of my diapers.
“Brian—did you wet your pants at school again?” she demanded sternly.
I gulped hard, trying desperately to think of an excuse that might yet save me and my defenseless, bare bottom.
“Yes, he did,” Stacey volunteered, “And then he wet his sissy diapers I put him into after he got home. I’ve just finished changing him for the second time today.”
My cheeks and ears burned hot with shame as I saw my mother’s smoldering anger steadily rising.
“Is that true?” she snapped.
“I-I-I—” I stammered in terror.
“Well, you’ve just earned yourself a trip over my knee, young man,” she said in her cutting voice as she wagged her finger at me threateningly.
“N-no Mommy!” I quailed as she swiftly stepped over to my dresser and scooped up the oval shaped wooden paddle on it.
Rachel and Wendy smirked, clearly delighted that they were about to witness my humiliating punishment.
Taking a seat on the spanking stool, she yanked me to my feet as I whimpered in fear before her.
“P-please!” I pleaded with her, my lips trembling, “I-it was only an accident!”
Jerking my pink rubber panties down off my bulging diapers, she pulled them down past my knees and then threw me over her firm, skirted lap.
“No-no! Stop! Stop!” I wailed, my hands waving in the air as I kicked my feet in a helpless, futile struggle.
With practiced movements, she quickly unpinned my diapers and pulled them back, exposing my white, Desitin-coated bottom once more to everyone present.
Glancing up at Stacey, she stood over me, her slim arms crossed over her big breasts as she shook her head at my pathetic display.
The first swat of the paddle landed across the center of my rump, searing an angry red imprint and making me howl in agony. The next swat landed squarely on my right cheek, followed right after by a blistering swat to my left. I immediately burst into tears as she continued to soundly paddle me, giving me the humiliating, painful punishment I so richly deserved. I kicked miserably, struggling across her lap but of course, she easily held me in place and continued her assault on my soft, tender bottom. My cheeks quickly went from pink, to a deep shade of scorched red as she peppered every inch of it with the cruel oak paddle. My mom is very thorough and after turning the center of my bottom into two stinging, crimson globes, she smacked and swatted the sides, making sure they received an equal amount of punishment.
I bawled like a baby and slapped my hands on the floor as the others watched with obvious approval. Each hard, scalding swat brought fresh tears that streamed down my face as I wailed and cried like a little girl.
At long last, she finally stopped spanking me. I lay over her lap, sobbing uncontrollably as she carefully pulled my thick cotton diapers back up and pinned them tightly around my hips. The temperature inside rose appreciably, trapping the heat of my paddled bottom with the multiple layers of fluffy soft Birdseye.
Standing me up on my quivering, unsteady feet, she pulled the stretchy pink rubber panties up my legs and positioned them over my fat diapers.
“Brian--it’s become clear that you can’t be trusted without your pampers anymore,” she said firmly as she waved the paddle at me and scolded me before the girls, “Therefore, I’m throwing away all your underwear. Since you’re determined to act like a baby--I’m going to treat you like one. From now on, it’s diapers and plastic panties for you, daytime and nighttime. And if your classmates ask you why you’re wearing them, you’ll just have to explain that you aren’t mature enough yet to wear big boy underpants.”
I cried like the baby she was describing, stamping my feet in place as I rubbed my stinging and throbbing hot bottom.
“Maybe I tried to raise you too quickly…maybe I’m to blame…but it’s looking to me like we need to start your childhood all over again—right from the start.
“You obviously can’t handle the responsibilities of being a teenager, so perhaps you’d be more comfortable with those of a toddler.
“What do you think, girls?” she asked the others, “Would Brian make a better baby than a teenager?”
“Oh—absolutely,” Stacey answered enthusiastically with the other two voicing their complete agreement, “In fact, I think you should convert his bedroom into a baby’s nursery. A bedwetting sissy in diapers needs a crib to sleep in and a playpen to spend his afternoons in.”
The other two giggled at her suggestion.
“Stacey—you’re both smart and resourceful. I’ll start putting it together today,” my mom told her.
“Oh—and I think he should start wearing outfits more befitting his childish status. Might I suggest a sissy sailor suit and perhaps several onesies? Something to go with his diapers. I think it’s only limited by your imagination.”
“I couldn’t agree more,” my mom said as she looked me up and down, “Yes, there are definitely going to be some changes around here.”
THE END
� Betty Pearl's Sissy Stories 20.1
Topic: Wet Diapers and a Hot Bottom (Read 10291 times)
