Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: Baby Bobby on March 07, 2023, 10:55:45 AM
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When I was twelve, going on thirteen, my parents got a divorce. As dictated by the terms of the final settlement, I was to move into my dad's new home along with his girlfriend, Desiree. I was not happy about the situation, to put it mildly, and I resented my new stepmom intensely, not the least of which was the fact that she was twelve years younger than my dad and tended to dress in a way I thought was overly provocative. Tight clothes and low cut tops were her common fare, showcasing her long legs and enormous breasts. Despite my misgivings about her, I have to say that in my heart of hearts, I could certainly see why my father had gone for her; physically, she was superior in every way to my mother—younger, in better shape, very pretty, and with a heart-stopping body she was obviously proud of. Nevertheless, I was determined never to give her a fair chance and there was no way that she was going to replace my mom.
Another addition to our family was Desiree's gorgeous daughter, Megan. At sixteen, she was four years older than me and a total babe, having inherited her mom's sexy curves. Initially, I tried everything I could do to ingratiate myself with her, but despite my efforts, she rebuffed me every time and was generally very dismissive of me. She was fond of telling me I was nothing but a little sissy, a nickname that stung me to the core and that I was particularly sensitive to. More and more, we argued all the time and I was desperate for her to respect me but all she saw in me was a wimpy little kid, unworthy of her consideration.
Conversely, she and her mother were very close and I often heard them whispering amongst themselves, making me suspicious and even more resentful. This situation was made more difficult by the fact that my dad was often out of town on business, so he left the running of our household to my stepmom.
I definitely felt like the odd man out and I think it was the stress of the divorce and the awkwardness of my new living arrangements that caused me to start wetting the bed. It wasn't every night, but about twice a week and Desiree was furious when she discovered it. I told her they were just random accidents but she had zero sympathy for me, threatening dire consequences if I didn't get it under control.
Which brings me to this morning.
I woke up once more to the feeling of very wet sheets and a soggy mattress below my waist, signaling yet another disaster that I was going to have to try and explain away to my new stepmom. I knew I was already on thin ice with her and as I heard her mounting the steps to come upstairs, I yanked off the sheets in a wild panic, stuffing them under the bed and pulling the covers back up. I had just swapped out my pajama bottoms when the bedroom door opened and she strode into the room, a haughty look of maternal superiority on her face.
Sniffing the room suspiciously, she wagged her finger at me in an accusing way.
“Brian? Did you wet the bed again?” she demanded sharply.
I bit my lip hard, almost breaking the skin.
“Umm, uh n-no,” I stammered nervously.
“I can smell the pee in here,” she said tersely, “If I find you're lying to me, you'll be taking a trip over my knee,” she warned me ominously.
My hair stood up on the back of my neck at the idea of a real spanking. Neither one of my parents had ever spanked me before and I couldn't believe she'd actually make good on her threat!
Going over to my bed, she yanked back the covers and saw the big wet stain on the mattress.
“It's ruined!” she shrieked, “My new mattress is ruined!”
My mouth had gone dry and I trembled in fear as she turned to face me.
“You are going to get your bare bottom paddled and then we are going shopping for diapers and plastic panties, bedwetter boy!” she barked.
Before I could stutter out some sort of reply, she grabbed me hard by the ear and frog-marched me down the hall, past Megan's room, who's door was currently open.
“Mom—what's going on?” she called out as we passed her room.
“Brian managed to wet his bed again and now he's going to get a spanking,” Desiree quipped.
Dragging me into the master bedroom, she grabbed an oval wooden paddle off the top of her dresser and took a seat on the bed.
“Y-y-you can't s-spank me!” I cried frantically, “I-I'll tell my dad!”
“He's already told me I have complete authority to discipline you in any way I see fit,” she snapped as she jerked my pajama bottoms down, revealing my tiny pen-is before her for the first time. The shocked look on her beautiful face clearly revealed that she'd never seen one that small but she quickly recovered and threw me over her lap.
“No-no-no!” I wailed as I looked up to see Megan framed by the bedroom doorway, smiling down at me in gleeful anticipation.
I felt my child-sized pen-is mash against Desiree's firm, bare thighs as she positioned me, making sure my feet didn't quite reach the floor. I squealed in helpless fear, waving my hands around as I felt the cool, smooth surface of the paddle slowly rubbing against my now defenseless cheeks.
“Brian, I've always thought you were very childish from the moment I met you. So I bought this paddle just for you and now you're going to get the childish punishment you've so rightly earned,” she growled.
I squealed again and struggled against her hold but she held me with a grip of steel as her other hand swooped up, bringing the paddle down with all her strength against my twitching, bare bottom.
SMACKK!!!
My mouth opened but my voice momentarily left me.
SMACKK!!!
This time, I howled at the top of my lungs in agony as the cruel paddle seared itself across both my tender cheeks, leaving another bright red oval pattern. Hot tears spilled down my face as I openly cried like a baby, my feet kicking wildly behind me. Desiree smacked my cheeks good and hard, over and over, delivering the strict, humiliating punishment she had promised. Slapping the ground desperately before me, I bawled like a toddler as she peppered my soft bottom with her hard, unforgiving paddle. Hot, swollen welts soon covered both cheeks and she moved her attention to the pink sides, using her seasoned wrist to slap them harshly.
Megan watched with immense satisfaction, obviously pleased that I was getting my just punishment for all the childish taunts I had made at her expense. This, without a doubt, was the most humiliating experience of my entire life as her mom spanked me like a naughty little boy. I knew it would be several days before I would be able to sit again.
Again and again, the hard paddle flattened my youthful bottom, each fierce swat like a salvo of buckshot.
Finally, Desiree stopped her assault on my derriere and she paused as I helplessly sobbed and cried, unable to control myself.
“Now, if you hadn't lied to me, your punishment would be over,” she said as she rubbed the smooth paddle across my scalded, flaming skin, “but since you were a dishonest little sissy with me, now you're going to get some additional swats.”
I stammered and blubbered out a protest just as her paddle came crashing down again, blistering my cherry red bottom and making it explode with fire. I kicked wildly even as she smacked my buns repeatedly with vicious retribution.
At long last, she stopped and put the paddle aside. I couldn't stop my crying and Megan looked down at me with neither sympathy or respect.
Standing me up, Desiree looked me hard in my eyes which were filled with fresh tears. Bawling like a baby, I grabbed my pajama bottoms and swiftly raised them to try and hide my tiny pen-is from the two of them.
“You and I are going shopping little boy,” she told me firmly as she waved the paddle at me, “We need to get you a supply of diapers and baby panties since you obviously can't be trusted with adult underwear.”
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I was so utterly humiliated. And it was made worse that I couldn't stop my crying. Megan looked down at me like I was just a errant child, unworthy of her respect, before shaking her head, turning and leaving the room.
I was about to put my pajama bottom back on when Desiree returned and held a flower-patterned pull-up before me.
“Uh-uh. This is what you will wear until we get some proper diapers for you,” she scolded me, “I don't want to take any chances of you wetting your pants while we're out.”
I burst into fresh tears as she pulled them up my slim, hairless legs, working her long fingernails around the stretchy waistband to make sure it fit correctly. After she finished, she turned me around and swatted me on my padded bottom.
“Run along now and get dressed,” she told me curtly.
Wiping the tears from my wet face, I stumbled back to my room, my bottom throbbing with pain. I managed to find some jeans that would otherwise have been loose on me—however, it was still going to be obvious I was wearing the pull-up when I zipped them up and buttoned the fly. Looking in the wall mirror at my bulging midsection, I stamped my feet in frustration.
Ten minutes later, we were driving downtown as I shifted in my seat, unable to get comfortable.
We pulled up in front of a big box store and Desiree came around to my side of the car, yanking me out and giving my thickly padded seat another swat.
“Come along little boy. Time to get my little baby some diapers and plastic panties.”
I whimpered with embarrassment as I stumbled after her, the soft bulk of the pull-up making me waddle slightly. Going through the sliding glass doors, we passed a customer holding a box of detergent in her hands and she looked me up and down out of the corner of her eye, her gaze fixed on my big bottom. I blushed and followed my stepmother down the aisles to the infant section where she stopped at the displays of plastic pants. Carefully selecting the largest size available, she held them up before my waist, stretching them between her fingers to estimate whether they would fit. My face was blazing red as I imagined what other customers were thinking.
There was another mother behind us who was deciding between which sippy cups to purchase and she began looking over at the two of us, obviously wondering about me being fitted for plastic panties.
“Your boy looks a little old to be wearing diapers, isn't he?” she asked.
I blushed hotly and looked away as Desiree gave her a wry smile.
“He certainly is. But he's ruined my new mattress with his constant bedwetting so it's pampers and rubber panties for him from now on,” she replied.
“Aww, you poor little thing,” she said, although she didn't sound overly sympathetic, “Well, you may have difficulty trying to find the right sizes for him here. I would suggest you go online...I think Rearz.com would be a good starting place—they have adult size diapers and all kinds of plastic and rubber panties that would fit him and give him room to grow.”
I was mortified to be a part of this conversation, or rather, to have this humiliating conversation about me. Worse yet, was the notion that I'd need diapers for long enough to grow into them!
Desiree turned to face her directly.
“Really? You seem to know a lot about this.”
“Well, I have a fifteen year-old bedwetter at home who is kept in diapers 24/7. Some little boys are just natural sissies and they seem to be more comfortable being babied than acting their age. I've had a sturdy crib and a highchair made for him and he enjoys playing with his toys in his playpen.
“Maybe that's what you need too, hmm?” the lady asked me as she smiled and bent down to look at me closer.
I gulped hard and shook my head as my cheeks blazed red with shame.
“You're definitely going to be wearing diapers and if you don't behave, I might just follow her suggestion and turn you into a full time toddler,” Desiree said as she wagged her long nailed finger at me.
“Please-please don't,” I winced.
“Thank you so much for the information. I'm going to stock up on a few items we'll be needing here like baby powder, diaper rash cream, pins...anything else you can think of?”
“Oh yes, your little sissy is going to need a waterproof mattress cover and I would also suggest a bedwetting chart to track his progress. That way, everyone can see how he's doing and encourage him when he's had a dry night.”
“I think that's a great idea,” Desiree agreed enthusiastically, “And that way--all your little friends can see how you're doing too.”
I was appalled at the idea that my friends might learn of my new shameful habit and I swallowed hard in abject fear.
“Please—I'll try harder,” I pleaded desperately.
“You'd better,” Desiree snapped, “Or you'll find yourself in diapers during the daytime too.”
We spent another twenty minutes shopping as my stepmom picked up the various things she thought I would need. When we reached the check out counter, I stared at the floor as the cute sales girl rang us up, giggling and looking me up and down. I could only imagine what she must have been thinking, seeing this pre-pubescent bedwetter in his pull-up before her and stocking up on all of the humiliating baby items I needed.
Holding up the bedwetting calendar as she scanned it, the sales girl smiled at me and gave me a wink.
“Good luck with your potty-training.”
Desiree spent the time while we were in line, shopping on her phone and showing me the various styles of plastic panties that were available, along with cloth and disposable diapers. I cringed at each view, knowing she was placing a big order for me. At last we finally left the store, but not before everyone in line a got a good look at the little boy who needed diapering supplies and a waterproof mattress cover for his bed.
That evening, Desiree put the cover on my bed (which already smelled strongly of pee) and arranged the diapering supplies on the top of my dresser. Since her order wasn't due to arrive any sooner than tomorrow, I was told to wear the pull-up to bed and we'd hope for the best.
Alas, maybe it was the stress of the day's events, but while I was asleep, I completely soaked them and even leaked onto the pajamas I was wearing.
After a hard swat with her paddle, Desiree took the red 'W' sticker and placed it on my new bedwetting calendar, alongside the one she had put for the night before, signifying two wet nights in a row.
Three days later, a large box arrived via FedEx from Rearz.com.
Desiree opened it in my room and she eagerly took out each item to show me. First, were two dozen cloth diapers, each very fluffy, with a prominently thicker section down the center of them. Next she pulled out pair after pair of plastic panties, all in various nursery prints and pastel colors.
“There...these will keep your bed dry,” she commented with a smile, “These are just what a little sissy needs.”
Under any other circ-umstances, I would have argued that I wasn't a sissy but my bottom was still sore from being paddled three days earlier. I certainly didn't want a repeat of that. Instead, I quietly and submissively accepted my new nightwear without a quibble, watching as she filled my dresser drawers with the babyish items.
Pulling out a package of disposable diapers decorated with clowns and bunnies, she looked over them skeptically.
“Hmm, I'm not sure these are going to be absorbent enough for how much you wet. I think we'll stick to cloth diapers for you.”
Lastly, she pulled out two short tops, each with a toddler-style motif across the chest. One was white and yellow and the other had baby-blue trim. With short, puffy sleeves and a lace lined hem, they looked just like something an infant would wear.
“Here are your new jammies, Brian,” she said, obviously proud of her selection, “Purposely cut short in case your diapers should leak.”
Looking into the box, I didn't see any matching pants to go with them.
“Where are the bottoms?” I asked nervously.
“Your diapers will be all the bottoms you need,” she said firmly as she removed my pajama bottoms from my drawer and took them out to the kitchen to throw them in the trash.
My heart sank as I looked at my new collection of diapers, panties and supplies, fearing my life was about to irrevocably change.
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Excellent story as always!
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Wonderful to see you back here, Baby Bobby! Equally wonderful to have you post another outstanding addition to your superb catalog of stories. Thank you!
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Wonderful to see you back here, Baby Bobby! Equally wonderful to have you post another outstanding addition to your superb catalog of stories. Thank you!
Nothing comes closer to my heart than a sissy bedwetter being disciplined by his strict Mommy. As a bedwetter myself, I can definitely relate to the scenes of waking up to a soaking wet diaper and fearing the cruel swats of mommy's wooden paddle.
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That evening after dinner, my stepmom led me to my room and told me to undress.
“B-but it's only 7:30,” I complained bitterly.
“Yes, I know, but I want to get you prepared for bed so we don't have to worry about it later,” she explained as she began arranging a thick stack of the cloth diapers one on top of each other.
I stamped my feet in frustration and anger, knowing there was nothing I could do to stop her.
Seeing me trying to stall the inevitable, she snapped her fingers in vexation.
“Come on—get those clothes off. And don't make me ask again or your bottom will pay the price.”
My lower lip trembled and my eyes misted with tears as I reluctantly began undressing before her.
“I-it's not fair,” I pouted miserably.
Ignoring my protest, she took hold of me by the wrist authoritatively and sat me down on the trio of fluffy white diapers.
“Brian, you have only yourself to blame for this. In this house—bedwetters get diapers, and that's just what you'll be wearing for the foreseeable future. Better get used to it,” she scolded me as she sprinkled baby powder over the tiny cap of my limp pen-is. Along with my minuscule sack, my entire package was about the size of three little grapes. As the infantile, fragrant cloud rose around me, she pulled the bulky but very soft cotton cloth up around my hips and pinned the corners securely in place.
Just then, Megan poked her head in the doorway, looking down at me with tremendous amusement written all over her pretty face.
“Well, looks like the little bedwetter is finally getting the treatment he deserves,” she said with a smirk.
I looked away as my cheeks and chest flushed a bright red. After the spanking, this had to be the most humiliating experience of my entire life!
Shaking out a pair of white nursery print plastic panties, Desiree fed them over my feet and worked them up my legs.
“Up,” she said tersely, as he pulled them up and over the bulging layers of cotton swaddled around my hips.
Looking down, I gazed at the shiny vinyl, the colorful Disney characters giving the panties a decidedly babyish look. Desiree selected the yellow and white diaper shirt and pulled it over my head, completing my ensemble.
“Oh wait—I have just the thing!” Megan said as she disappeared down the hall. She returned a moment later with a pair of short, lacy white anklet socks.
“This will go perfect with your outfit,” she said as she bent down and began putting them on my feet without waiting for approval from her mom. However, Desiree only looked down at me and smiled, happy her daughter had taken the initiative. Standing over me, she placed her hands on her curvy hips and regarded me with a look of maternal superiority.
“There. Now you're all ready for beddie-bye. Which by the way, I'm setting back to nine pm from now on. A sissy bedwetter doesn't get to stay up like the adults so that's your new bedtime.”
Crossing my arms angrily, I sulked in silence as Megan grinned down at me in victory.
The two strode out of my room, leaving me to contemplate my new status as the childish bedwetter of the house. Standing up, I looked at my humiliating reflection in the mirror. Between the fat, embarrassing diapers, nursery print plastic panties, sissy top and lacy anklets, I looked just like a diaper-dependent toddler who needed his mommy.
I was determined to keep my diapers dry and I made a point of not drinking anything further until bedtime. Sure enough, at 8:50, my stepmom came into my room and made sure I was ready for bed, turning out the lights as she left. I was left in my bed, listening to life going on normally in the rest of the house while I had been put to bed at a ridiculously early time. In my anger and frustration, I balled my fists and kicked off the covers. However, after several moments pouting in resentment, my hands gradually found their way to the thickly padded front of my diapers. I discovered that the prissy plastic panties felt wonderfully soft to the touch, along with the fluffy cotton diapers contained within them. Rubbing the pillowy front, I sighed with pleasure at this new and strange sensation. To be sure, it was beyond humiliating to be wearing the babyish underwear but my tiny pen-is twitched with excitement as I caressed the vinyl material. In no time, it had grown to it's rock hard length of nearly two inches and I closed my eyes in pleasure. Memories of Megan's tight, breast-hugging, fitted top swam into my consciousness and I came explosively in my diapers within thirty seconds.
In my post-orgasm bliss, I slowly drifted off to sleep.
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Yes i too was a bedwetter at that age, and if not nappied at night i would still wet my bed. I love shopping at Rearz got some more nappies and pins and another onsie coming on Tuesday. Hope the sissy ends up nappied 24/7 and has all the baby items he needs.
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I LOVE this story already, I already cannot wait for the next chapter and see how it will develop.
It's just what this form needs as I feel there has been a bit of a lull in stories/updates to my favourite ones
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Is this a rework of this story or am I imaging I have read this before? ?? your stories!!
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Is this a rework of this story or am I imaging I have read this before? ?? your stories!!
I think I may have posted this on my Tumblr site before it was taken down. It's not on my current site, so it's possible you may have come across it on the now deleted original site.
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I woke up to the lights being turned on and my stepmom barging into my bedroom without notice. Coming over to my bed, she pulled back the covers and slipped her finger under the elastic waistband of my plastic panties.
“Soaked again,” she announced, her voice filled with annoyance.
Sure enough, the pungent tang of my pee surrounded us, making me cringe with shame.
Stepping over to my bedwetting chart, she placed another red 'W' on it, indicating five consecutive wet nights.
“Seven in a row and you'll be taking another trip over my lap, sissy boy,” she warned me severely.
“You can keep your diapers on until after breakfast. Maybe sitting in your own pee will help motivate you.”
“Yes Ma'am,” I mumbled.
I trudged downstairs, my thick diapers heavy and starting to sag from so much pee. Megan was in the kitchen, texting someone on her phone, but I couldn't stop myself from admiring her busty profile.
“Let me guess—wet again?” she asked Desiree.
“Mm-hm, just like a two-year old,” she responded acerbically.
“Oh my god—I've babysat children that were more mature than you are,” Megan said disdainfully.
Sitting down, the thick, soggy cotton squished against my bottom and I kept my eyes downcast.
“I think I'll order a few more baby outfits for you,” Desiree stated.
“Good idea—can I help?” Megan asked eagerly.
“Sure thing. I found a few more sites online that specialize in adult babies—I had no idea there was such a huge market for such thing.”
“I guess there are more sissy bedwetters out there than we thought,” Megan remarked with a condescending chuckle.
The two of them rose from the kitchen table to go into the other room where the PC was while I was left to eat my cereal wearing my soaking wet diapers.
The morning after next, I woke up once more to my stepmom barging into my room and flipping on the lights. As I blinked away the night's drowsiness, I saw she had her oval paddle in her hand and a look of steely determination on her beautiful face.
“Well, it's time to see how my little bedwetter is doing. Am I going to have to give you another spanking?” she asked me.
Without waiting for me to answer, she pulled down my covers and slipped a finger down the front of my diapers. With a look of surprise, she stood up and put her hands on her hips.
“What a surprise,” she declared, “ You've managed to stay dry. Looks like I won't be needing to take you over my lap after all.”
I shuddered with relief at my good fortune, fleeting as it was.
“Nevertheless, I want you to keep them on until after breakfast,” she told me as she turned and walked out of the room.
Once she was gone, and I was sure she was going down the steps to the kitchen, my hands slipped under the covers to begin fondling the soft, cushiony front of my diapers again. This was quickly becoming a daily habit for me. They felt so soft and warm, and I began eagerly rubbing my little pen-is through the fluffy cotton with abandon. It didn't take long, the sensations being so wonderful against my stubby shaft and I quickly splashed my little load into the comforting folds surrounding my package. I sighed with pleasure and relief, although a part of me guiltily wondered what my stepmom would think if she ever caught me.
Leaving my bedroom, I padded down the stairs where Desiree was drinking coffee and texting on her phone.
I poured some cereal in a bowl and after adding milk, sat down at the table to eat my breakfast. I had my spoon halfway to my mouth when I suddenly heard Megan and another girl's voices coming in from the other room.
In a wild panic, I stood up, intending to bolt up the stairs but it was too late. The two girls rounded the corner and Megan's friend stared at me in shock as she took in my outfit; a short sissy top, thick, bulging diapers contained within shiny nursery print plastic panties and white lacy anklets.
“Oh—my god,” her friend blurted out as she broke into a big smile, clearly amused at her unexpected discovery.
Although not quite as pretty as Megan, this girl was still stunning and her low cut top revealed a sexy line of deep cleavage.
“And who is this little toddler?” she asked with a big smile.
I nearly wet myself with fear and only a lighting quick response prevented me from soaking my diapers right then and there.
Desiree had moved up behind me to block my escape.
“This little sissy's name is Brian,” she introduced me.
“Why are you wearing diapers, Brian?” she asked in a simple tone of voice that suggested I was mentally challenged.
Staring at the floor with a blushing face, I shuffled my feet, wishing the floor would open up and swallow me.
“Go ahead, Brian, tell Brittany here why you're wearing diapers,” my stepmom urged me.
I mumbled under my breath and looked away, too ashamed to say anything.
“Come on, Brian,” she said with a threatening undercurrent to her tone of voice, “Everyone's going to find out sooner or later, you might as well start with Brittany here.”
“No,” I whimpered weakly.
“Do I need to get the paddle?” Desiree asked, “I'm sure Brittany here would love to see you take a another trip over my lap.”
Megan's friend giggled at the revelation I got spanked like a child.
I gulped hard with fear.
“I-I, um, I s-sometimes w-wet the bed,” I stammered, blushing an even deeper shade of red.
“He even has a bedwetting chart hanging up in his room,” Megan added derisively.
Brittany giggled again and looked me up and down, focusing on my shiny diapers.
“There. You see?” Desiree beamed, “That wasn't so hard, was it?”
I wanted to cry with shame but I fought back the tears, knowing that would only make me look more like a sissy.
“Can I go now?” I bleated miserably.
“Go ahead, run along,” Desiree said with a dismissive swat to my padded bottom.
I waddled off and retreated to my bedroom to escape the humiliating encounter.
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Looking forward to the adult baby outfits and more people finding out he is a sissybaby
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Several days later, I was sitting on the edge of my bed, having gotten up before my stepmom checked on me. And as usual, I couldn't stop myself from rubbing the bunny-soft, pillowy front of my diapers. Even though they were soaked from last night's bedwetting, it still felt incredible to caress the plasticky front and my tiny stub responded immediately. I was imagining Megan in my mind's eye, her delightful curves filling up and practically overflowing her sexy smooth push-up bra. I felt my orgasm bubbling up and was just about to explode when suddenly Desiree strode into the room unexpectedly.
“WHAT IN HOLY HELL IS GOING ON HERE?” she demanded angrily.
My hands shot away from my diapers and I stuttered incomprehensibly.
“I-um-I just...um...”
“You little sissy masturbator!” she barked, “You are NOT to play with yourself in this house!”
She snatched up the paddle from the dresser top and quickly took a seat on the edge of the mattress, jerking my plastic panties down a in ring around my calves.
“No! N-no!” I squealed weakly.
Yanking me over her lap, she swiftly unpinned my wet diapers and pushed the soggy bulk between my legs.
Without warning, she smacked by damp bottom as hard as she could, eliciting a loud cry of anguish from my quivering mouth. I kicked as she brought down the paddle again and again, first against one soft cheek and then the other. I burst into tears and cried like a baby as she swatted by reddening bottom mercilessly, my feet scissoring helplessly behind me. The cruel wooden paddle scalded my tender skin viciously, filling the room with the loud, crisp swats and I wailed at the top of my lungs with each smack. Slapping the floor with the palms of my hands frantically, I squirmed like a fish out of water as she peppered my behind. With a crisp snap of her wrist, she began smacking the pink sides of my buns and I cried desperately. I knew from experience it was going to be three long days before I'd be able to sit down again without wincing.
Finally, at long last, the terrible spanking was over. I lay over her lap, too weak to stand, sobbing my eyes out as she rested the paddle against my blazing bottom.
“Young man—I am going to be checking your diapers from now on and if I find even the slightest trace of goo in them, you can count on another blistering spanking over my lap—do you understand me?”
I nodded my head quickly and blurted out a wailing 'yes' between my sobs.
“You're a disgusting little boy and I won't tolerate a masturbator in my house,” she emphasized her remark with another swift smack from the paddle, right across both bright red cheeks, making me howl in agony as a fresh set of tears tumbled down my wet face.
A week later, it was about eight in the evening and I was just stepping out of the shower, when I heard my name being called from downstairs. I couldn't be sure, but when I opened the door, it also sounded as if my stepmom has some guests over to visit. Wrapping the towel around my torso, I stepped over to the head of the stairs hesitantly.
“Brian; come downstairs, it's time to get you ready for bed,” I heard Desiree call to me.
My heart skipped a beat. Tentatively, I tip-toed slowly down the stairwell, afraid she intended to put me in my diapers in front of someone else. Putting aside Megan's friend, I certainly didn't want any other strangers to know about my bedwetting if I could help it.
“Um, but what about...you know?” I said, not wanting to come down any further.
“Brian—come down here this instant, I won't ask again,” I heard her say in a tone of voice with an edge to it.
I swallowed hard and descended the staircase, seeing three of my stepmom's friends comfortably sitting along with her around the living room on the couch and easy chairs. I bit my lip and my cheeks reddened as I suddenly spied the changing mat in the middle of the floor, along with a stack of fluffy cloth diapers, pins, baby powder and yellow nursery print plastic panties.
Blushing hotly with shame, my spirits sank as the women looked at me expectantly, clearly having been told that the diapers were waiting for me.
“Come along, we don't have all night,” Desiree said as she brusquely removed my towel and sat me down on the stack of diapers. My hands shot down to cover my embarrassing, tiny little package from everyone's intent gaze. The women giggled with amusement as my stepmom squeezed a glob of Desitin in the palm of her hand while her other one firmly grasped my ankles together and swung them up over my head. I squealed like a little girl and was forced to move my hands to maintain my balance as everyone was treated to a grand view of my bare bottom. My eyes misted with tears of humiliation as they all looked down on me both literally and figuratively. Here I was all of twelve years old, about to be pinned into my bedwetter's diapers in front of everyone. Could anything be worse for a budding teenager?
“Looks like this little boy got his booty spanked,” one of them commented with a chuckle.
My stepmom smeared the Desitin slowly across my bottom, leaving a thick, sticky coating across both cheeks.
“That's right. I walked into his room to find him playing with himself and rubbing the front of his diapers. That earned him an immediate trip over my lap.”
The women collectively giggled as one of them wagged her finger at me.
“Naughty little boy. Now you know what happens to little boys that misbehave.”
My cheeks blazed red as Desiree shook baby powder over my little genitals. As usual, all that one could see was the small, cap-shaped protuberance of my wee-wee above my toddler-sized sack.
“Would anyone care to guess Brian's age?” she asked the group.
“Judging by the size of his package, I'd say...three?” the blond one quipped.
Everyone burst out laughing and a tear of humiliation trickled down my cheek.
“Stop teasing me!” I whined in a pouty voice.
I knew I sounded like a total wimp but I had to stand up for myself.
“Aww,” the brunette said in a syrupy voice meant for toddlers, “I think the wittle one needs his bedtime bottle.”
Once again, the group erupted in laughter. It was clear that they had zero respect for me.
“Des—have you ever considered a chastity device for him?” the blonde asked, “I'll bet it would do him a world of good.”
I cringed, not quite sure what she was talking about but instinctively knowing it probably wasn't in my best interests.
My stepmom was halfway to pulling my diapers up between my legs when she stopped in mid movement.
“You know—that's not a bad idea,” she said, clearly interested in the notion, “But could I get one small enough to fit him?”
“These days, you can get them in any size. I would suggest the Sissy Tamer, by LockedUpPansies.com. It was specifically designed for determined sissy masturbators with maximum security in mind so there would be no chance whatsoever he can escape. Trust me—once he's locked in that device, his days of erections are over. No more orgasms and no more playing with himself.”
While it was mortifying to be getting pinned into my diapers like a baby in front of these women, it was even worse to be talked about by them in this way.
“Well, that sounds like just what our little bedwetter needs,” my stepmom said with a big grin as she pinned the sides of my diapers snugly around my hips.
I didn't like where this was headed at all! To have my orgasms taken away? Up until now, that had been the only source of pleasure I had enjoyed since being put back into diapers. And now this woman was giving my stepmom ideas that would put an end to my masturbating activities forever!
'I-I d-don't think that's a good idea,” I mumbled even as I blushed anew at the idea of defending my naughty behavior.
“No? Well that's too bad, young man,” my stepmom snapped as she positioned my plastic panties around my feet, “Because you clearly need a secure chastity device to prevent you from playing with yourself. And I'm going to order one for you right after I put you to bed.”
I bunched my fists in mute frustration as she slowly brought the yellow nursery print plastic panties up my legs and began working them over my fat diapers.
“Don't worry, sweetie,” the brunette said, a look of smug satisfaction on her face, “Before long, you won't even notice you're wearing one.”
I swallowed hard as the others giggled.
Pulling my sissy top over my head, Desiree stood me up to face the others.
“Say goodnight to our guests, Brian,” she said with a pat on my fat, diapered bottom.
Staring at the floor like a chastened toddler, I mumbled goodnight to them before my stepmom took my hand and led me waddling up to my room.
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Totally forgot the chastity. Every good sissy baby needs one. Love the story.
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I think I may have posted this on my Tumblr site before it was taken down. It's not on my current site, so it's possible you may have come across it on the now deleted original site.
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Please, what is your current site. Difficult to keep up.
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Please, what is your current site. Difficult to keep up.
Yes indeed. Here you go: https://babybobbysstories.tumblr.com/
It has lots of stories and captioned pics.
Enjoy!
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Three days and six desperate orgasms later, the dreaded device showed up at the house via a UPS delivery. Desiree led me to my room where she took my pants down and had me sit on the changing pad that was on my bed. I fidgeted and squirmed, trying to think of some way to convince her to delay this terrible development.
“Now Brian, I know you may think you don't need this but believe me, it's for your own good. I know your diapers are baby soft and they'll always be a constant temptation to you. But now you don't have to worry about that because your new chastity device will keep your little pen-is--sissy soft and safe. No more naughty erections and no more playing with yourself. Now you'll use your diapers for their intended purpose, and trust me--this will put a stop to your nasty behavior, once and for all.”
I gulped hard and my little wee-wee shriveled in fear.
She unlocked the strange looking contraption and holding the small steel ring in her hand, fed my little limp package through it, positioning it behind my sack. It was a snug fit, to be sure, but pushing one ball after the other, she eventually got it in place. My feet kicked in frustration as she took the remaining cap-shaped part which was no bigger than the tip of my thumb, and carefully fit it over the tiny stub of my shaft. Pins allowed it to mate snugly against the cuff ring, mashing my imprisoned pen-is inside the cap as she slid a long key into the side, locking the two pieces together.
“There!” she said, obviously very pleased, “It fits perfectly!”
She beamed down at it with a look of total satisfaction.
“No more erections and no more orgasms for you! Just soft diapers and plastic panties to keep your bed dry.”
I grasped the minuscule device in my hand and shook it but it was clear that it was there to stay.
“But how long am I gonna hafta wear it?” I whined bitterly.
“That stays on until you stop your childish bedwetting, sissy boy,” she said as she crossed her arms over her substantial chest.
“It's not fair!” I complained, slamming my fists against the mattress.
“No? Well I think maybe I'll just put you in your diapers early today,” she quipped, always ready to up the ante with me, “That way, you can feel what it's like without having to wait until tonight.”
Before I knew it, my stepmom was powdering me and pinning me into my humiliating diapers and plastic panties, this time, a lavender pair with lace around the legs and waistband. She swapped out my t-shirt for one of the newer cropped diaper shirts, one with a Barney applique across the chest she'd purchased online and finished with my lacy pink anklets.
“There. Now if you need to use the bathroom, you come to me and I'll take your diapers down—do you understand me??”
“Yes, Ma'am,” I muttered sullenly.
As she left my bedroom, I sat down on the edge of the bed feeling sorry for myself and wondering how my situation could possibly get any worse. As I struggled to come up with a solution out of this mess, I began gazing out the window on the street below. A truck pulled up and I could see Megan was just arriving, being dropped off by her boyfriend, some big jock on the football team. What a world of difference there was between the two of us. Here I was, wearing a big, bulging baby's diaper, a sissy top and lacy anklets while my tiny pen-is was permanently locked away inside. I'll bet I was the only one at school without free access to my own willie! And I'll bet Megan had already stroked that guy's big coc-k to orgasm many times. That was certainly never going to happen to me. Not with her or any other girl now that it was locked in steel. Besides that, what girl would ever want to be with a sissy bedwetter who wore diapers and prissy plastic panties?
Still sullen and pouting, I watched as she bent over to kiss him goodbye, her perfect shaped fanny pointed my way and framed by her skin-tight shorts. I sighed and unconsciously, began softly rubbing the front of my diapers. I was intensely jealous of her boyfriend, who no doubt got his way with her on a routine basis while she wouldn't even give me the time of day.
The two of them seemed so very adult to me while they made me feel like a bedwetting toddler in need of his diapers.
For a moment, she stood up and was saying something to him and my eyes wandered over her succulent curves. To be sure, she had the sexiest body of all her friends, which were without exception, very attractive themselves. But Megan liked to push the envelope of what was socially acceptable for a teenage girl to wear and today's clinging pink top certainly did not disappoint.
I rubbed my diapers furiously now, hungrily drinking in her busty profile from my voyeuristic vantage point as she continued her conversation with her boyfriend, oblivious to my lustful stares. Unfortunately, my tiny pen-is could only throb in frustrated angst as I rubbed the soft, pillowy front of my diapers, unable to get even the tiniest erection. I rubbed and rubbed, a bead of sweat trickling down my forehead but it was no use. All my efforts served to do was make me even hornier than I already was.
Bunching my fists, I slammed them on the bed again, wanting to scream with exasperation. I tried to distract myself and think of something else but the sun was shining brightly on my new stepsister, making her look like a golden angel. She was so beautiful and sexy and my little nub throbbed in desperation, struggling in futility against the tiny steel cage surrounding it.
Finally, she said her last goodbye, kissed him, and walked into the house out of sight. With a heavy sigh, I gave up and tried to think of something to get my mind off my raging libido.
As the days went on, I found my stepmom taking longer and longer to remove my wet diapers in the morning and she would put me into them earlier in the evening as well. And because I wore them for most of the first half of the day, I found myself just wetting them again since there was little point in asking Desiree to remove them. I guess I was starting to get lazy about controlling my wetting.
This came back to me one afternoon with terrible repercussions when I was walking down the hallway in my regular clothes and I could hear Megan doing something in my room with one of her friends. I could hear them giggling and I knew they were talking about my diapers and baby outfits. My ears and cheeks flushed a bright red with shame and in my panic I stood there and suddenly felt the front of my pants growing wet. My pee darkened the crotch area before flowing down my legs as I whimpered with fear and humiliation. Looking around wildly, I frantically tried to think where I could hide while I did something to conceal what I'd done.
Just then, Megan and her friend walked out of my room and they stopped in their tracks as the stared at me and saw the clear evidence of my wet pants.
“Mom?!” Megan called out loud enough that her voice carried throughout the house, making me wave my hands in a desperate panic to try and dissuade her.
“No-no-no!” I cried hysterically.
“Brian wet his pants!” she called out, looking me firmly in the eyes with an evil smirk on her face.
Soon, my stepmom was determinedly stomping up the stairs to see what was going on, her beautiful features darkened with anger.
The three of them surrounded me while Desiree clutched me by my ear.
“Brian-you little sissy-you've just earned yourself a good, hard spanking!” she snapped.
I started crying as she led me into my room with the other two following close behind.
All too soon, I found myself in the very familiar position with my wet pants and underwear down around my ankles as my stepmom delivered another painful and humiliating punishment, blistering my bare bottom with her paddle as I howled and bawled like a baby.
Megan and her friend watched the entire thing with gleeful delight and afterwards, I was put straight into my diapers.
The next morning, I woke up to a dull pain as my little pen-is struggled and failed miserably to become erect inside the tiny confines of its steel cage. I groaned in misery, reaching inside the front of my soggy wet diapers to try and relieve the pain but nothing I did helped. To be sure, the dream I had just woken up from didn't help; nursing from Megan's big breasts like a baby and caressing her flawless skin. It seemed that now that I was wearing and wetting diapers every night, it was causing me to have dreams that were increasingly babyish.
In any event, having woken from that intensely erotic scene, I was beside myself with horniness but there wasn't a single thing I could do about it.
Just then, my stepmom came into the room, carrying a bulging red rubber bag with a long white hose that extended from it. Soapy suds were dripping from its sides and I could see it was bursting to capacity. Not sure what it was, I watched as she hung it up on a tall stand she pulled from the closet before pulling me out of bed and standing me up.
“Wha-what are you gonna do?” I quaked, “Am I g-gonna get sp-spanked?”
“No, sissy boy, that is—unless you decide to put up a fuss,” she said as she held a huge dil-do nozzle in her hand, smiling as she looked me firmly in the eyes, “I'm going to give you a nice, soapy enema, Brian,” she said firmly, “It's just what every little sissy boy needs.”
My lower lip quivered and I sniffled helplessly as she tugged my clinging plastic panties down off my sopping wet diapers and pulled them down around my ankles.
“B-but—wait!” I cried as she pulled me across her lap, “I-I don't want this!”
“Brian--it's obvious that you're not making any effort to stop your bedwetting, so I've decided from now on, you're going to wear your diapers full time,” she said as she unpinned the soggy Birdseye cotton from around my hips.
“N-no, no!” I wailed as my eyes filled with tears of shame.
Pulling away the clammy wet cotton, I felt cool air upon my backside and I shivered a little. Suddenly, I felt her slippery finger at my rosebud and a dollop of Vaseline being pushed inside. I squealed like a little girl at this invasion but she continued, making sure my snug passage was very well lubed.
“This nozzle was specifically designed for sissies like you and you may find it a little big to begin with. However, the soft, pliable material ensures eventually it will all fit inside you, even if it stretches you a bit so my suggestion is that you just relax.
“This is what you've been asking for and you're going to get this whether you like it or not,” she explained.
I kicked my feet and whined miserably. I didn't ask for this at all!
“No—I don't want that!”
“Brian, I may tolerate your wet diapers but this will make sure you won't do any number twos in them. Now spread your legs and relax—it will go in much easier if you just submit.”
Feeling the fat, blunt tip of the dil-do nozzle pushing insistently at my hole, I squealed loudly again, flailing my arms in panic.
“No-no! It's too big!” I cried.
Suddenly, the big rubbery head popped through and past my sphincter making me moan helplessly.
Looking up at the wall mirror opposite us, I could see my stepmom smiling with immense satisfaction.
“Theeere,” she said soothingly, allowing my hole to get accustomed to the leviathan stretching me wide, “Just relax and take it. This is exactly what you need.”
I was breathing hard as she slowly began pushing it in deeper, and I moaned again like a little girl. Never in my life had I had anything so big back there and I felt deeply emasculated.
Soon, it was all the way in and I squealed loudly as she pushed on it, making sure I got every inch of the fat, rubbery invader.
Without warning, I heard her undo the clip, and a raging torrent of soapy water suddenly surged into my bowels.
“OOHHH!” I moaned helplessly.
She left the valve open for about twenty seconds before finally clipping it shut.
“Brian, you're going to get a nice, soapy enema every morning so I can be sure you won't be messing your diapers,” she told me simply.
She squeezed and patted my right bottom cheek as she laid out my future.
“It's obvious you enjoy wearing and wetting baby's diapers so I'm going to give you what every sissy truly wants deep down; to be treated like a little toddler.”
Before I could grasp the significance of what she was saying, she opened the clip, releasing another soapy torrent deep into my bowels.
“OOHHH!” I cried.
“From now on, you'll be dressed like a the little baby you've been acting like; diaper shirts, onesies, short, cute little dresses—everything an aspiring sissy bedwetter could ever want.”
The water churned inside me, giving me cramps and making me moan again.
“I thought we could keep your diapers for just bed times but after seeing you wet your pants yesterday, it's obvious you're just too immature for big boy underwear.”
I moaned softly, trying to adjust to the quart of warm, soapy water flowing into me.
“No, you're much better off with thick, thirsty diapers and rubber panties, so that's just what you'll wear.”
My back hole ached from the mammoth dil-do stretching it wide but my efforts to clench down on it did nothing and I was forced to take the enema at the pace of her choosing.
“I want you to say after me; 'I'm a bedwetting sissy',” she instructed me.
Releasing the clip, more water flowed into me, forcing a moan I was holding back.
“I-I'm a b-bedwetting sissy,” I bleated.
“That's right—you are. And bedwetting sissies need diapers and rubber panties don't they?” she taunted me.
“Y-yes ma'am,” I admitted.
“Say it, sissy,” she prompted me with a gentle squeeze of my right cheek.
“B-bedwetting sissies need d-diapers and rubber p-panties,” I confessed.
Desiree smiled with smug satisfaction at me in the wall mirror opposite us.
“I think you're going to enjoy being my little toddler,” she said as the last of the water gurgled into my backside.
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Nasty i don't like enemas either. Step Mummy really turning him into a sissy baby. Love it.
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From that day on, Desiree kept me in diapers and plastic panties around the clock, and I became the defacto baby of the house. As time went on, my stepmom and Megan began slowly converting my room into a true nursery, with colorful Disney Princess stickers covering the walls, and a pink carpet covering the floor as my collection of infantile outfits gradually grew. Eventually, I found out she'd thrown my sneakers away, to be replaced with glossy black or pink Mary Janes.
The crowning achievement occurred when she had a contractor come in and convert my bed into a pink and white crib, complete with a mobile overhead. This is where I took my afternoon naps and after a while, my tenuous bladder control vanished. Although it had been my stepmom's intention that I notify her whenever I had to go, I was finding that even during the day when I was fully awake, I'd find myself just peeing freely, the warm urine soaking the thick cotton between my legs before seeping up into the thirsty seat. Eventually, after several wettings, they would start to sag and I would be forced to go find my stepmom and ask her to change my diapers.
Her friends all enjoyed having a baby to play with and often, one of them would bottle feed me before my afternoon nap. It was so utterly humiliating, laying on the couch in the living room with my head in their lap, wearing a bright lemon yellow party dress, Mary Janes, and my exposed sissy diapers. Everyone loved to check me to see if I was wet and if I was, my diapers would be changed before everyone present. This often happened in front of Megan and her friends and eventually, they all began to see me as nothing but a diaper-dependent baby.
Although I gradually came to accept my circ-umstances, the enforced chastity was much more difficult to deal with. Every morning I would wake up in my crib, wet and ravenously horny, rubbing the front of my soggy but fluffy diapers but never able to satiate my needs. And since Megan had lost whatever respect she may have ever had for me, she also lost any inhibitions she might have had about going around the house in just her underwear. While she would never have done it with a male teenager under the same roof, now she saw me as little more than an impotent, harmless, diaper-dependent infant. Nevertheless, watching her saunter down the hall in nothing but her bra and panties would make my tiny pen-is ache painfully in its steel cage. It left me edgy and cranky, chewing in frustration on the fat rubber pacifier that was now a permanent part of my wardrobe.
Sometimes, when her mom was busy, she would relegate the task of my daily enema to Megan, who took to it with eager enthusiasm. She loved to see me helplessly squirm and squeal across her lap, as she slowly fed two quarts of warm, soapy water into my bottom. I became intimately familiar with that huge dil-do nozzle and a secret part of me even began to savor the feeling as the fat, slippery shaft slid deep into my rectum every morning. Perhaps it was the absence of any sort of sexual relief or orgasms that I began to crave the feeling of being filled by that titanic instrument.
Another aspect of having my erections and orgasms taken away is that I became increasingly submissive to both Desiree and Megan (and of course, their friends). I no longer fought with the latter—instead, I obediently did her bidding, like cleaning her room and hand washing her lingerie. By now, she had complete authority from my stepmom to discipline me as she saw fit, and if she found my work unsatisfactory, I could count on taking a trip over her lap to have my bottom soundly paddled.
Having said that, as time went on and I slipped comfortably into the role of their sissy baby, the two of them began to soften their attitudes toward me. I found that the more I embraced the lifestyle of an helplessly incontinent, diaper-wetting sissy, and gave them my unquestioning obedience, the more they warmed to me and treated me like part of the family.
They say a sissy is always the last to recognize what he truly is and I guess I'm no exception. After a while, I came to love the ritual of having my soaking wet diapers changed, to be replaced with a fluffy soft new set of pampers. Or being dressed in the morning by my doting stepmom into a frilly new sissy dress complete with glittery tights. I secretly loved the sassy ruffles of my pink rumba panties as she pulled them over my fat, bulging diapers. And I could see the pride in her beautiful face as she combed my now longish hair into pigtails, securing them with two shiny pink bows.
Leading me downstairs to the living room, I'd happily take my place in my playpen, watching my favorite children's channel as I played with my plush toys while my new Mommy would visit with her friends.
All in all, life was pretty darn good for this bedwetting sissy.
THE END
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:)
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Would have liked more description of the baby dresses and the feelings he had wearing them. However, all in all another fun Baby Bobby story. TY.