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Jordan stood at her living room windows, watching with growing consternation at the neighborhood bully across the street, Trevor Osteroff.
At thirteen years old, he was the terror of the neighborhood, constantly picking on younger and smaller boys as well as every one of the girls on the street. It was common knowledge that his mother was at her wits end and was clearly incapable of reining in the bratty teenager.
Jordan gritted her teeth in anger as she watched Trevor deliberately splashing a mud puddle and drenching Susie Parker from two doors down.
Finally, her temper snapped and she marched out the front door, striding purposely straight for Trevor, who at the moment, had his back to her. Snatching him by the ear with one hand, her other swung down and swatted him hard on the seat of his pants.
Caught completely by surprise, Trevor cried out in surprise.
“Come along, young man, you’ve had this coming for a long time now,” she said as she frog-marched him back into her house.
Trevor stammered protest after protest, a string of foul-mouthed curses streaming out in rapid succession as he stumbled along, unable to wrest his skinny arm from Jordan’s steely grasp.
He nearly tripped over the step as she hauled him in through the front door, pausing just long enough to grab a stout, wooden paddle waiting nearby. Without wasting a moment, Jordan swiftly undid his jeans and tugged them down past his knees even as Trevor’s voice raised in pitch and defiance.
“What are you doing, you fuc-king bitch!! I’m gonna call the cops on you!” he screamed.
Taking a seat on an armless chair, Jordan yanked the bratty youth over her lap even as his arms flailed wildly. He continued to shout hysterically, using every nasty word and epithet he’d ever heard and then some.
Using her long nailed finger, Jordan reached under the waistband of Trevor’s Spider-Man underwear and angrily jerked them down.
The cursing youth kicked and tried to get up from his compromising position but Jordan used her left hand to force him to remain in place. Her other hand gripped the paddle firmly and she raised it high, bringing it down as hard as she could against his bare bottom. The crack of hard, unforgiving wood against soft, bare flesh filled the room.
Trevor wailed in anguish and pain as Jordan brought the oak paddle down again and again. Bright red patterns quickly formed across his cheeks as the punishing wood impacted his defenseless bottom in a withering rhythm of retribution. He kicked wildly and beat his fists against the floor as Jordan paddled him hard, the holes in the wood causing a vicious, biting sting.
Both front windows were wide open, and a number of neighborhood girls had started to gather outside, watching with deep satisfaction as they saw their nemesis finally getting the punishment he so richly deserved. Trevor was crying unashamedly, the hot tears tumbling down his face and his feet scissoring behind him, helpless to stop the humiliating spanking.
His bottom was now a deep crimson and Jordan began fiercely slapping and swatting the sides to ensure they received equal attention. Trevor’s buns jiggled miserably under her punitive assault, the tender skin scalded to a blistering five-alarm fire.
After searing the sides to the same swollen shade of red, Jordan returned to the center, that curvy point of his bottom where the thighs met his cheeks.
The harsh crack of wood on bare flesh was only broken by Trevor’s high-pitched wailing as he cried like a baby.
At last, Jordan stopped long enough to push a stray wisp of her long chestnut colored hair from her pretty face.
“Trevor—you’ve been acting like a child ever since you moved into this neighborhood. I don’t know how they handled it where you came from, but I simply won’t take it any longer.”
The sobbing teenager was having difficulty catching his breath and it came in ragged sobs.
“You are going to do exactly as a I say—without question—do you understand me?”
He nodded his head, the tears still streaming down his red face.
The paddle swooped down and landed with a deafening impact, making him howl out at the top of his lungs and wildly kick his feet again in frustrated helplessness.
“I asked you a question, little boy,” she snapped.
“Y-yes-yes!!” he blubbered. At this point, he was willing to do or say anything to end this mortifying and painful punishment. It wasn’t lost upon him that four or five girls had gathered at the front window and were eagerly watching his comeuppance.
“Your days of terrorizing the neighborhood are over. And before the day is done, you’re going to apologize to every one of the girls that you’ve been bullying,” she told him as she lifted him off her firm lap.
The boy sobbed miserably and rubbed his scorched and stinging backside, turning away from the audience at the front window.
Leading him over to a corner of the room, Jordan instructed him to put his nose into it, leaving his pants and underwear in place around his ankles. Trevor could only imagine the smirks and conversations taking place amongst his former targets as they avidly watched him take his place in the corner of the room like a naughty school boy.
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Like any naughty boy should he got the spanking he deserved. Surprised he didn't piss himself with the spanking.
I love to see what is coming for the next chapter and how he has to apologize the the girls.
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I love this approach, Baby Bobby! Most of your protagonists are total pushovers, so it's cool to see a bully dominated in one of your stories.
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Ha ha! That's true, although Trevor has met more than his match in the form of Jordan who is hellbent on instituting strict maternal disciple over this obnoxious bully.
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Oh thank you Bobby! My Daddy has unlocked me for one day and I'm allowed to make stickies in my nappies and you post a new story!
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He could only wonder what further punishment Jordan had in mind as he heard water running in the other room. It was coming from what he supposed was her kitchen, so he knew she wasn’t going to bath him.
Maybe she’d give him another stern lecture and then let him go? If so, he would lay low for a little while but he had every intention of returning to his old ways and getting his revenge on the girls and smaller boys so they’d still think of him as the tough guy his image merited.
Because of his position in the corner, he couldn’t see what was in Jordan’s hand as she walked past him and down the hallway with whatever she was preparing. A moment later, she came back and took his wrist like a child, leading him down the hall and into a brightly lit room that looked much like a baby’s nursery. A larger than usual sized crib occupied one corner of the room and pink, gauzy curtains diffused the bright daylight streaming into the feminine-decorated room.
Taking a seat on the edge of the crib mattress, Jordan bent him over her lap again even as the still sobbing youth began with more protesting, although this time, without the cursing.
“Please-please don’t spank me anymore,” he pleaded desperately.
His bottom was hot, burning, and throbbing in agony and he knew he couldn’t take any more of her paddle.
He squealed with surprise as he felt her finger pushing a dollop of cool, greasy Vaseline into his virgin hole.
“Wha-what are you doing?” he whimpered anxiously.
“Giving you just what you need—a nice, soapy enema,” she said with smug satisfaction, “spread your legs now little boy—this nozzle is much bigger than the usual ones,” she instructed him.
Trevor had no idea what a “usual” enema nozzle was but before he could think too much about that, he felt the big, blunt tip pushing insistently against his little hole.
“N-no-no!” he squealed frantically. He didn’t like where this was headed and it was a new and entirely unwelcome sensation.
“Trevor—do I need to get the paddle? Because I’m only too happy to re-light the fire on your bottom.”
The sniveling youth shook his head.
“No please, please don’t spank me,” he whined.
“Just relax and this will go in a lot easier,” she told him firmly as she renewed her efforts.
“OHHH!” he squealed loudly as he felt the fat, slippery rubber nozzle invading his snug back passage. It was a strange, unfamiliar, and unwelcome feeling as Jordan slowly pushed the thick phallic tool deeply into his rectum.
“Ohhhh,” he moaned weakly.
“In my experience, bullies that pick on girls that are smaller than you are in fact, nothing but big sissies and a good, filling enema will set you straight.”
Trevor could feel her cool fingers on his hot, stinging cheeks as she held the nozzle in place while he trembled nervously.
With the long white hose in her other hand, Jordan released the clip, allowing a strong, steady torrent of warm, soapy water to flow uninterrupted into the squirming boy’s bowels.
Trevor moaned deeply as he felt the liquid gurgling into him. He squeezed his cheeks together but it made no difference—the water continued to flow without any discernible slowing. After about thirty seconds, Jordan shut the clip closed and waited patiently.
“As I said, after we’re done here, you are going to apologize to the neighborhood girls for your misbehavior. But first, I’m going to dress you up like the big sissy I know you really are,” she told him.
With her right hand, Jordan pulled off his jeans and underwear and tossed them aside.
“Most sissies deny their true nature so its important that you admit it now, so that we can move on. Go ahead Trevor, tell me you’re a sissy,” she instructed him.
With his hole stuffed with a fat rubber enema nozzle, Trevor felt helpless and emasculated. Already, the water was churning uncomfortably inside him.
“Ohh,” he whimpered weakly.
“Go ahead little boy,” she said condescendingly, “tell me what you are,” she said as she released the clip again.
Trevor moaned again as he tried to contend with the growing fullness inside.
“I-I’m a sissy,” he said weakly.
“That’s right, sissy boy. And sissies need diapers and plastic panties...see that changing table in front of you? I’m going to pin you into your very own fluffy diapers and some cute plastic baby panties,” she explained as she closed the enema clip.
Trevor was now truly regretting all of his misdeeds and the suffering he had inflicted on the neighborhood kids. No one had ever brought him to task for his behavior and now it had finally caught up to him.
“I-I don’t wanna wear diapers,” he whined miserably.
“That’s too bad, sissykins,” she said as she opened the clip again, sending another strong stream of soapy water into the squirming youth’s rectum, “Because that’s exactly what you’re going to wear, in addition to a frilly, prissy baby dress.”
Trevor could only moan weakly, flexing his hot, stinging cheeks in vain as more and more soapy water flowed deep inside of him.
At long last, the residual bubbles passed through the hose, filling Trevor to absolute capacity. He was squirming and morning weakly on her lap, struggling with the cramps of a very full enema.
Jordan slowly and carefully slid the slippery nozzle out and placed it aside. Taking his right hand, she positioned it against his back hole, instructing him to make sure none leaked out as she led him down the hallway to the bathroom. Keeping the door open, she watched as Trevor limped over to the toilet where his bowels exploded in a rushing torrent of water. Deeply ashamed, his cheeks flushed as he sat there under the humiliating supervision of his stern neighbor.
Finally, after about ten minutes, Jordan stood him up, turned him around and wiped his messy bottom as if he were still a toddler. By now, Trevor was so defeated, he submitted to every indignity she was prepared to subject him to.
In no time, she was taking him back down the hallway to the nursery where she sat him down on the vinyl covered changing table.
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Love it baby bobby nothing like a nice enema for a sissy baby who has to come to the realization it is a sissy baby.
Looking forward to the sissy being diapered.
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Agreed with PervScenes11, love the setup here with the bully. Waiting for the scenes with his impending public apologies has me on the edge of my seat.
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“Oww!” he wailed as fresh tears threatened to erupt when his tender, stinging bottom made contact with the waterproof padded surface.
Raising his ankles above him, Jordan took three rectangles of thick cotton cloth and placed it under his red and swollen rump. With her free hand, she dipped it into an open jar of Desitin and smeared it across the warm, swollen skin of his bottom. Trevor squealed and wriggled his feet but Jordan held his ankles firmly while she did her job.
Soon, his bright red bottom had a nice, sticky white coating of diaper rash cream covering it.
Letting his legs down, Jordan shook baby powder all over his tiny pen-is and between his legs, making sure the infantile scent surrounded him.
“Sissies needs their diapers and now everyone is going to see you for what you really are—nothing but a weak little pantywaist,” she explained as she pulled the thick, fluffy cloth up and pinned it securely around his waist. The extra soaker pads down the center ensured he would be wearing a very thick, puffy diaper, and one that would be impossible to hide.
“No...please don’t,” he pleaded with her.
“You should have thought about before you started picking on little girls, sissy boy,” she said as she chose a pair of pink, nursery print plastic panties and positioned them over his feet.
“All sissies need plastic panties and you’re certainly no exception,” she told him as she drew the babyish panties up his trembling legs.
Trevor blushed hotly as familiar memories flooded back of his mom diapering him in the evening for protection against his nightly bedwetting. To think that another woman has arrived at the same solution was utterly shameful for the boy.
After dusting between his inner thighs with more baby powder, Jordan went to the closet and came back with a white and pink frilly baby dress that flared out widely at the hem.
“I think this will be perfect for sissy’s first day in the neighborhood—won’t you be a big hit?” she smirked.
“I’m gonna tell my mom!” he sniveled petulantly.
“Well—maybe we can tell her together, hm?” Jordan replied with a smug smile, “I’ll just bet that she’ll be delighted to see her sissy son dressed up properly for once, not to mention well protected,” she said as she patted the fat, plastic covered front of his diapers and winked at him.
Trevor’s bluster evaporated at the thought of being marched over to confront his mother, dressed like an overgrown toddler in diapers. He was only too afraid that she would approve, given that all her efforts to discipline him had failed so miserably.
Pulling off his t-shirt, Jordan positioned the dress over his head and curtly ordered him to raise his arms. The soft, ruffled garment fell down around him and Trevor discerned a slight perfumed scent that smelled like something a little girl would wear. It only served to reinforce his feelings of childishness.
Turning him around, Jordan fastened up the small row of buttons and then adjusted the short puffy sleeves and the prissy elasticized lace that hugged his skinny upper arms.
Next, Jordan removed his socks and replaced them with white, ruffled anklets and a shiny, glossy pair of pink Mary Janes.
“Don’t you look special!” she beamed as she stood him up and led him over to the full length mirror so he could see his new outfit.
Trevor blushed hotly as he tried in vain, pulling down the short, lacy hem of the dress to try and cover his embarrassing, bulging diapers.
Taking him by the hand, Jordan led him out of the nursery, down the hall and into the kitchen, where she placed a large baby bottle of milk into the microwave. Thirty seconds later, it dinged and she took it out, checking the temperature on her wrist.
“Perfect, baby boy,” she announced as she pushed the rubber nipple into his gaping mouth.
Trevor hated milk, especially warm milk, but his bottom was still sore and stinging inside his sissy diapers and he was reluctant to say or do anything to make his gorgeous neighbor angry.
Sitting him down on the couch next to her, Jordan supervised his bottle feeding, sometimes tipping it up to force him to drink more.
As he reluctantly drank in silence, Trevor couldn’t help but to grudgingly admire the curves on this attractive, albeit stern woman. She was wearing a snug, fitted yellow top, that not only showed her toned arms but clung deliciously to her big, round breasts. In any other circ-umstances, Trevor would be lusting over her but under his present humiliating situation, he hated her for her strength and absolute power over him.
At last, the bottle was finished, and a string of milk followed him as Jordan took the bottle and re-filled it, popping it back into the microwave.
Trevor’s eyebrows furrowed in frustration—he was full and could already feel the milk sloshing around inside his belly. Surely, she didn’t intend to make him drink more??
Once the microwave dinged agin, Jordan removed the bottle and brought it over to Trevor.
“Alright sissy—it’s time for your apology tour,” she told him firmly.
Taking his hand, she stood him up and pulled him toward the front door.
“B-b-but—wait! Please-please don’t make me go outside,” he wailed as tears threatened to overwhelm him.
“After terrorizing all the kids in this neighborhood, it’s high time for you to say you are sorry,” she told him sternly.
“Please!” he sobbed, “I’m sorry—I promise never to do it again.”
“I know you won’t,” she said as she placed her hands on her hips in the ultimate stance of superior female authority, thrusting her big breasts out proudly, “Now you can either march your sissy butt out that door, or I can put you over my knee. What’s it going to be, prissy boy?”
Trevor’s shoulders sagged with defeat as he trudged slowly out the door, the fat diapers forcing him into a babyish waddle. Right now, he hated his beautiful neighbor for her strength and control over him. He also realized that all his bratty behavior was now coming to pay him back in spades.
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LOVE IT! Looking forward to the reaction from all the girls i am sure they will have fun as well as his mommy.
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Love your stories Bobby Thank you, can't wait to see where this one goes..
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As they went out the front door, a pair of younger girls were right next door, and they immediately skipped over to see the babyish looking boy in his fat diapers and sissy dress.
Peals of laughter erupted from the pair as they looked over their previous tormentor. Trevor blushed hotly as he stared at the ground, hoping somehow lightning would strike him dead and end this mortifying experience.
After enduring all manner of condescending remarks from the two about his appearance, Jordan told him to apologize to the girls for his previous bullying.
“I-I’m sorry,” he bleated, his cheeks flushed a deep shade of crimson.
Bending over, Jordan whispered into his ear.
“Tell them that from now on, you’ll be dressing like the true sissy that you are, wearing your diapers so you don’t wet your pants.”
Trevor could feel his ears and chest burning but with Jordan’s hand patting him on his fat, diapered bottom, he didn’t want another trip over her lap.
“This is m-my new outfit,” he stammered, “s-so I won’t wet my pants.”
The girls broke into gales of laughter as they looked him up and down. It certainly was a pleasant change from his previous threatening demeanor.
“We better check you right now, baby,” one of them stated as she reached over and slipped her little finger inside the elastic leg band of his pink nursery print plastic panties.
“Still dry—good baby!” she announced.
They both laughed uproariously, happy to see the bratty youth finally put in his place.
“Alright sissy,” Jordan told him, “Let’s go find some of your other victims.”
Taking his hand like a child, Jordan led him down the street, the mocking taunts of the girls ringing in his ears. Besides the humiliation of suffering his exposure in public, Trevor was also starting to feel the pressure of a very full bladder. Although he hadn’t drank any more of the bottle, just having it slosh in his hands made him hyper conscious of his growing need.
They soon came across a twelve year-old girl and her younger brother, neighbors from three doors down.
Once again, Trevor was made to apologize profusely and let them laugh at his compromising situation. All the time, he found himself starting to shift from foot to foot, trying to stave off the building pressure he could no longer ignore.
Just then, Trevor caught sight of Samantha Pierce, the hottest cheerleader at his school, approaching them from down the sidewalk. He felt a strong, nearly overwhelming panic seize him and he tried unsuccessfully to wrest his hand from Jordan’s.
Samantha was a tall, leggy blonde that every male at school lusted over, with Trevor being no exception. She had spotted the odd sight of the diapered teenager and she quickened her pace, squinting in the sunlight to see who it was.
Jordan made sure to hold his hand tightly, ensuring this pretty young woman got to see Trevor in all his babyish glory.
Stopping in front of the two of them, Samantha laughed freely, showing her perfect, white teeth, her mocking, dismissive tone only too obvious.
Trevor’s knees buckled as the dam finally burst and a strong stream of hot pee began flooding his diapers. He tried to stop it, but quickly realized the hopelessness of the situation and he whimpered as his bladder gradually emptied itself into his big, thirsty diapers.
“Well, well, well,” Samantha smirked as soon as she could control her laughter, “Looks like Mommy’s little baby is out for a walk...or is that a ‘waddle’, diaper boy?”
“Trevor is visiting all the people he bullied over the last six months,” Jordan explained.
Samantha sneered in derision. Obviously, she had a hard time believing this prissy diapered pantywaist could bully anyone. His legs were girly smooth and free of hair and his arms looked skinny and weak. He was also shorter than the statuesque cheerleader and she looked down on him, both literately and figuratively.
“Does the sissy wet his diapers like a baby too?” she asked, the disdain in her voice plain.
Without warning, Jordan bent down and squeezed the fat seat of Trevor’s diapers, making him squeal with shock. Instantly, she felt the warmth of the soft Birdseye cloth through his plastic panties, clearly indicating his wet condition.
“Yep, just like a baby,” she replied.
Samantha shook her pretty head, at a loss for words over the pathetic sight before her.
“What a total loser,” she said as she moved past them and continued on her way.
Trevor hung his head in shame, the misery painted across his red, blushing face. To think that he had just stood before his idol, wearing a baby dress and wet diapers was too much to bear.
“We better take you home to your mommy,” Jordan told him, “I’m sure she’ll want to see about getting you stocked up on your own diapers and plastic panties.”
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Nice to see some of his victims tormenting him. Really looking forward to his mommy's reaction
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whee perhaps some baby bonnets too and matching mittens and booties :)
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Trevor shuffled down the street, the humiliating, soggy wet feeling of his thick diapers squishing between his legs and surrounding his little package.
In moments, the two of them were standing on his front porch, ringing the doorbell, as they waited for his mom to answer. It didn’t take long, and as she pulled the door back, her mouth dropped open in shock as she beheld her sissy son for the first time in his adorable baby outfit.
“Trevor was bullying the girls next door—again—and I decided to take matters into my own hand. Looks like all that was needed was a fluffy set of pampers and a baby dress to get him under control.
“And sissy Trevor’s been enjoying his outfit so much, he’s already managed to wet his diapers.”
His mom shook her head in disbelief as she looked down on her prissy son, now so thoroughly pacified.
“Trevor, I’ve always thought you belonged in diapers—and the fact you’ve wet them only proves it. It’s obvious that you enjoy wearing them so it looks like it’s time for some changes around here.
“Your bullying days are over but your potty-training days are just beginning,” his mom told him, her arms crossed over her chest.
“I’ll be happy to help out until you get the stuff you need,” Jordan offered, “I’ve got plenty of diapers, plastic and rubber panties, a crib for afternoon naps and a hard oak paddle for those times when Trevor gets fussy or sassy.”
Trevor gulped with fear to think that he could expect to be getting spanked on a regular basis now.
“Excellent. That’s just what he needs,” his mom readily agreed, “Trevor, I’m going to box up all your big boy clothes today and put them in the attic.
“It’s time everyone sees you for the bedwetter you are.”
The flustered teenager’s cheeks flushed hotly at her blunt, humiliating announcement.
“I’m not a bedwetter!” Trevor protested vehemently.
While it’s true that Trevor’s bedwetting days were (mostly) behind him, he was mortified to have that history revealed to Jordan here on their porch.
“If you’d like, I can take sissy Trevor back over to my house, change his wet diapers and put him down for his nap,” Jordan offered helpfully.
“Thank you so much—that would give me time to get online and order up a big supply of the diapers and panties he’ll be needing now,” his mom replied gratefully.
Trevor stamped his feet in frustration. Now that Jordan had inserted herself into his life, he was helpless to prevent the strict, maternal discipline she had planned for him.
Reaching down, Jordan squeezed the fat seat of his wet diapers.
“Come along sissy, lets get those soggy pampers changed,” she told him.
Trevor’s lower lip thrust out, and he pouted in helplessness as Jordan took his hand and led him waddling across the street.
“I don’t wanna be a baby!” he complained bitterly.
“Well that’s too bad, sissy boy, because that’s exactly what you’re going to be from now on. You can count on diapers and baby outfits, bottle feedings and early bedtimes—oh, and a nice, long, soapy enema every morning.”
Trevor shook his fists as she led him inside and down the hallway towards the nursery. Just as she was reaching under the frilly lace hem of his baby dress to pull his plastic panties down, the doorbell rang unexpectedly.
“You stay right here,” she ordered him as she left the room to find out who was at the door. Trevor felt foolish standing around in his wet diapers and a quick glance at the full length mirror made him blush all over again—he looked just like a little toddler girl!
Several minutes later, Jordan returned with another woman behind her. Trevor recognized her as Leanne, one of the parents in the neighborhood who’s child he had routinely bullied.
“Well. I had to see it to believe it,” the woman said, “Looks like Jordan has finally put you right where you belong—in diapers and dresses.”
Trevor blushed even redder as he looked away in shame.
“Sissy Trevor wet himself and needs a diaper change before his nap,” Jordan explained, “but now that you’re here, maybe I should give him another enema for all the trouble he’s caused your children.”
“I think that’s a wonderful idea,” Leanne agreed wholeheartedly.
“He already got his bottom paddled this morning for terrorizing another girl but a second enema will do him a world of good,” Jordan said as she took the red rubber bag and went into the bathroom with it.
Trevor could only fret and wait in angst as Leanne glared down at him, eager to see him get his long, overdue punishment.
A few minutes later, Jordan returned, the bag straining to contain two quarts of warm, soapy water. Trevor began softly crying as she pulled his wet diapers down and took him over her lap for the third time today. He was so utterly humiliated to be shamed like this and he squealed anew when he felt Jordan pushing more Vaseline into his quivering little hole.
Before long, Trevor was receiving his just reward as a strong torrent of sudsy water was again flowing deep into his rectum.
“Just what a big sissy needs,” Jordan said with obvious satisfaction as she patted his bruised, red bottom.
Trevor moaned weakly, trying to contend with both the growing cramps and Leanne’s superior gaze—she was clearly very happy to see this incorrigible brat punished and humiliated.To be sure, whatever tough-guy image he might have held before, had completely evaporated now and his reputation in the neighborhood would forever be in tatters.
Ten minutes later, the last soapy suds disappeared into the squirming sissy’s bottom as he whimpered helplessly.
Helping him to his feet, Jordan led him to the bathroom where she stood by and supervised his shameful release. Trevor’s cheeks burned with humiliation as she again wiped his messy bottom like a child and led him back to the nursery where a fresh set of diapers awaited him.
Setting him onto the fluffy stack of bunny-soft cloth, Jordan paused long enough to pick up a strange looking device next to the drawer of plastic panties. With practiced movements, she separated the device into two pieces, one which was tube-like and the other which was an irregular plastic ring. Pulling his shy little package through the ring, she positioned it behind his sack and then applied a dab of baby lotion to his tiny little shaft.
“Wha-what are you doing?” he quailed in fear.
“This will ensure you are all safe and secure inside your diapers,” Jordan replied.
Leanne instantly understood the restrictive chastity device that her friend was fitting him for and she grinned down on him broadly with smug satisfaction.
Trevor fidgeted and kicked as Jordan mated the two pieces together, compressing his tiny little shaft inside the even tinier tube (which was more of a cap really, than a tube) and locking them together with a unique, narrow key.
“Sissies that wear diapers shouldn’t be experiencing erections and this will make sure you can no longer masturbate, either.”
Trevor gasped and bit his lip with embarrassment.
If only they knew just how often he played with himself!
“No!” he wailed miserably.
Grasping his ankles together, Jordan swung them up and over his head as her right hand snatched up the paddle and brought it down harshly, swatting his bare bottom with a terrific crack that filled the room.
Trevor howled with pain and desperately tried to kick his feet free from her grip as the paddle slapped each of his defenseless cheeks hard once more.
Sobbing like a baby, hot tears tumbled down his face as she set his legs down and began powdering his diaper area.
“Serves you right, you little brat,” Leanne told him unsympathetically.
Trevor cried softly as Jordan brought the thick cloth up and pinned it snugly around his hips.
“Don’t cry, little sissy,” Jordan said in a syrupy voice meant for toddlers, “these are a bedwetter’s best friend.”
Pulling a frilly pink pair of rubber panties up his skinny legs, Jordan ran her fingers around the waistband to make sure all the soft cotton cloth was contained inside.
Removing the prissy baby dress he was wearing, she replaced it with a fuzzy fleece top with baby bears playing on it. After removing his Mary Janes, she helped him into the crib, tucking a stuffed animal under his arm and pushing another bottle of milk against his pouting lips.
“Make sure you drink that all up, baby boy,” she instructed him as the two of them left the room.
Trevor did as he was told, reflecting on just how far he’d fallen in the space of a few hours. Was he doomed to live the life of a toddler in diapers from now on?
A half hour later, the exhausted youth was sound asleep, clinging to the soft, fuzzy Koala bear in his arms and dreaming blissfully as his bladder relaxed and slowly but surely, released all the milk he’d been given during the day into his thick, fluffy diapers.
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Poor Trevor !!!
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Finally Trevor getting what he deserves. Being a bedwetter he should have already been in diapers. Now he is and love the sissy dresses and plastic panties.
Being a sissy baby myself i know what it is like to be caged and diapered.
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Hi Bobby,
Just love your stories, one of if not the best writer of ABDL fiction ever, have you ever considered putting them all together in a book and self publishing ?? I would willingly purchase a copy .. Thank you again Kindest regards Dave xx PS I thought that these little illustrations would be something your stories relate too ..
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I love that image of Sissy standing on a kitchen chair in his jim-jams Dave.
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Nicely done, Dave. I love the thick[er] diapers and the paddle awaiting the sissy. ;)
It's been suggested that I sell my material and I know there's a market for it out there (I know, because others have already stolen my work and sold it on Amazon), but it's always been my policy that my stories should be available for everyone, free of charge.
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Hi Bobby,
OK, I get your point, likewise my artwork is never copywrited (Is that the right word) ??
Like you my pleasure comes from the pleasure that others get from my work.. If you ever fancy a joint, no profit project then let me know, would be great to illustrate some of your fantastic stories for all to see..
Thanks Bobby..Kindest reagrdas D x
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Hi Baby Bobby and davelo thanks for your great gifts over the years, I have been an avid fan of both of you from the start, that is why I would like to make a suggestion, how about you work together on a one-off piece to be used to help donations to Betty's, because we all know she deserves it and more for providing such a wonderful website for all these years.
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I would LOVE to see an illustrated “David’s fateful day” story. That story changed my life. I first at it at 14 and I’m now in my mid 30’s. Does anyone remember the old sissy site “Sarah Sissy World”? It was something like that. Maybe “Sarah Jane”. That’s where I first read David Fateful Day.
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Hi Baby Bobby and davelo thanks for your great gifts over the years, I have been an avid fan of both of you from the start, that is why I would like to make a suggestion, how about you work together on a one-off piece to be used to help donations to Betty's, because we all know she deserves it and more for providing such a wonderful website for all these years.
Well first off thank you for your kind words, and a great idea, if Bobby has the time and is willing then so am I Thank you xxx
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Dave, would you be keen to provide an illustration for each chapter of a future story? In that way, we could collaborate and present the combined work together here.
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Hi Bobby, yes I would, but I struggle to get my work on here without shrinking it to the size of a postage stamp before I can upload it, it would be easier if I could mail you the finished piece and you upload it as I am not the sharpest knife in the box when it comes to dealing with stuff like that ..
Kindest Regards and Thank you again D..
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Six months later...
Sissy Trevor sat crosslegged in his playpen, musing over which set of plastic blocks looked best as he arranged them in a wall of sorts. His fluffy cotton baby diapers swaddled him generously, and he welcomed their safe, protecting embrace around his hips and loins.
About four months ago, Trevor was starting to have accidents in his diapers, usually just a little bit of wetting, but then the incidents became more and more frequent. Perhaps it was his growing used to the feel of wearing the the bulky underwear everyday that made him more comfortable, but what started as an occasional accident soon became a daily occurrence.
Similarly, Trevor’s previous bedwetting habit came back with a vengeance— it might have been due to the daily humiliations he suffered, but it was a rare morning when his diapers were not completely soaked.
His mom was not overly bothered by these developments, feeling that it was a far preferable situation than to his previous bratty persona. She was much happier taking care of a childish bedwetter in diapers than being the pariah of the neighborhood.
Over the course of the next couple of months, Trevor began wetting his diapers more frequently during the day. It happened anytime he was surprised by someone or something, but also just randomly, like when he’d be playing with his trucks and he would sit back, only to discover to his surprise that his sissy pampers were soaked.
Later on, when his mom would call him in to check on him, he would blush and stammer out some absurd excuse but she usually just ignored him, pushing his fat pink pacifier into his mouth and changing his diapers like she would any incontinent toddler.
By now, the entire neighborhood knew him as ‘Baby Trevor’, the sissy who couldn’t keep his diapers dry and long gone, was the fear he used to invoke in his younger peers.
Over time, his mom had gradually transformed his bedroom into a proper baby’s nursery, decorating it with soft pastel colors of pink and yellow. His closet was now filled with short, frilly dresses that always left his fat, childish diapers humiliatingly displayed. He had whined and protested with her for something that would at least cover up his embarrassing underwear but she would only shake her head and say ‘Mommy knows best’.
With only a little effort, his bed had been converted into a proper crib, with solid pink bars now surrounding it, a waterproof mattress cover and soft baby blankets.
A large, red rubber enema bag stood hanging from a stand next to his crib, ready at a moment’s use, although she was now making a point of administering a long, soapy purge of her wayward son every morning without fail. It had been months now since he had had a regular bowel movement.
The daily enemas also helped to drain some his of built-up semen, although despite that, Trevor was still left constantly horny and frustrated by his inability to masturbate.
Oh, how he missed that favorite of his previous activities!
The chastity device was his constant humiliating companion, compressing his short little nub and keeping it nice and sissy soft inside his comfy baby diapers.
No matter how he begged and pleaded with his mom, she insisted that it was there to stay, and he would just have to get used to a life without erections.
Now as he sat in his playpen, he tried not to think about his hot, stinging bottom, still throbbing from the sound paddling he’d received earlier for throwing his food. His mom had certainly taken a page from Jordan’s book, realizing the solid benefits of taking her errant child over her lap for a good, hard spanking whenever he acted up.
Now, it was rare for a week to go by in which Trevor did not find himself bent over her knee, his diapers unpinned as she smacked his bare bottom to a bright, fiery shade of red. What made it worse, was that she always made a point of opening the windows and drapes so all the neighbors would know he was getting paddled.
More often than not, the neighborhood girls would come over and watch as the sobbing teenager stamped his feet and stood in place as his diapers and plastic panties were pulled back up over a red hot bottom.
Today had been no exception, and afterwards, his mom had put him in his playpen to keep an eye on him before his afternoon nap.
Trevor fidgeted as he sat on the padded waterproof floor of his playpen, his bottom still hot and stinging from his childish punishment.
A knock at the door distracted him and his mom crossed the room to answer it. Trevor was always nervous whenever someone came by, as it almost always meant some further humiliation for him. As he anxiously raised himself up to a kneeling position, he could see out the front window, the busty profile of their sexy neighbor, Jordan. Suddenly, to his surprise, the floodgates opened unexpectedly and without even realizing it, Trevor began helplessly flooding his diapers like a baby.
His mom opened the door and greeted her friend, cheerfully inviting her in. At the same time, Trevor whimpered as he felt his diapers growing warm and heavy with urgent pee. It flowed unchecked, collecting in a pool around his little locked package and then seeping into the thick, thirsty seat of his diapers.
As Jordan came into the living room, she saw him and beamed down upon the blushing youth.
“Well hello, babykins!” she exclaimed, “Look what I brought over you.”
She held forth a baby doll wearing a short dress and diapers with blonde hair tied into pigtails.
“She looks just like you, don’t you think?”
Trevor blushed furiously just as another strong stream of pee flooded into his already very wet pampers.
“Aw, what’s da matter, babykins?” she asked in her voice for toddlers, “Does baby Trevor need his ba-ba?”
Today, Jordan was wearing a snug, plunging pink halter top that hugged her glorious big breasts in the sexiest possible way. Trevor bit his lip and tried unsuccessfully not to stare at them.
He was so horny!
Although he resented Jordan for putting him in his present situation, he couldn’t help but be infatuated with her, lusting after her voluptuous, curvy body, especially when she dressed the way she was today.
Jordan reached down and lifted the squirming boy out of the playpen, ignoring his whimpers of embarrassment. Taking a seat on an armless chair, she placed him to sit across her firm lap. It was when his fat, diapered seat squished warmly against her thighs that she smiled knowingly to him.
“Is there something you want to tell your mommy?” she asked the brightly blushing sissy.
While having his bedwetting habit explained to Jordan had been embarrassing enough, his recent daytime wetting incidents were even more humiliating. To think that he was starting to wet himself during the day, with no more control than an incontinent toddler was mortifying for the little pantywaist.
With his cheeks blushing bright red with shame, he looked around the room nervously, desperately wishing he could avoid this uncomfortable conversation. Nevertheless, the childish smell of pee could easily be discerned wafting up around him, even if the warm, soggy Birdseye cloth against her thighs didn’t give him away.
“Come on babykins, tell mommy what you did,” she prodded him.
“I w-wet my diapers,” he mumbled under his breath.
“Sorry, we can’t hear you,” she told him.
“I w-wet my diapers,” he stammered louder. Trevor’s ears burned hotly, along with his chest and neck.
His mom brought over a large baby bottle filled with warm milk, handing it over to a Jordan who promptly pushed it between his trembling lips.
“Hush baby,” she comforted him, “you just drink your ba-ba.”
The two women giggled as Trevor did as he was told, his cheeks blazing with humiliation.
Although it was mortifying for the prissy teen to have to nurse from the bottle like an infant, he couldn’t help but gaze hungrily at Jordan’s very impressive bosom, just inches before him. For one, her tight halter top couldn’t quite hide the sexy smooth bra she had on underneath and a portion of the shiny pink silk of her huge cups was peeking out in a most exciting way.
And every time she breathed, her tantalizing chest would rise and fall.
With his post-puberty hormones now raging like a forest fire, Trevor’s tiny little pen-is throbbed and strained urgently inside his chastity device as it struggled in futility to get hard.
His heart rate shot through the roof as his eyes wandered over her big, beautiful breasts, so round and perfect. The babyish notion of nursing from them made him both blush and grow agitated with shameful excitement.
He squirmed and whimpered on her lap in frustration, wishing so badly he could just touch them. Of course, such a move was out of the question—he knew without a shadow of doubt that he’d find himself bent over her lap in seconds, his bottom bared as she paddled him to tears.
“After you finish this, we’ll change those wet diapers and then it will be naptime for you in your crib,” she explained as she smiled at him with her usual look of adult superiority.
Trevor gulped down the tepid milk, even as his caged, child-sized pen-is continued to throb eagerly.
Jordan slipped a long-nailed finger inside his elastic waistband and down the back of his diapers before withdrawing it.
“My, you’ve really managed to soak yourself, sissykins. You’re becoming more babylike all the time.”
“He really doesn’t have very much control anymore,” his mom confessed, “Most often, he simply wets himself without even realizing it.”
Trevor blushed anew. This was SO humiliating!
It’s true he had had a number of accidents lately during the daytime but he was pretty sure he could still get it under control. And anyway, it was all his mom’s fault in the first place for making him wear diapers during the daytime. If she’d just trust him to keep his pants dry, he would prove to everyone that he was still a big boy...
“Poor little sissy,” Jordan lamented as she pursed her sexy lips into a mocking pout, “You really do need your baby pampers, don’t you?”
“No!” Trevor suddenly blurted out in his high-pitched voice.
“That’s enough of that,” his mom warned him sternly, “Come along—it’s naptime for you.”
Trevor pouted angrily as she took him by the hand and led him waddling down to his nursery which more and more, smelled strongly of stale pee and unwashed diapers.
“Hold still, baby bedwetter,” she chided him as she began pulling his soggy wet pampers down.
Once again, Trevor was forced to endure this humiliating, childish ritual, witnessed by Jordan who looked down upon him with smug amusement.
“I’m not a baby!” he wailed miserably as he stamped his feet.
Unfortunately, with his soaking wet diapers around his ankles and the half empty bottle of milk in his hands, he looked very babyish indeed.
“Looks like our little pantywaist got his bottom spanked,” Jordan remarked with a wry smile as she took in his pink, bruised cheeks.
“Yes, the little sissy was throwing his food today in a classic toddler temper tantrum,” his mom explained with a barely concealed chuckle as she set him down on a fresh set of fluffy diapers, “So he earned himself a trip over my lap and a session with the paddle.”
Jordan chuckled as she shook her head.
Trevor wanted to say something in his defense but his mom was already pushing his big rubber pacifier past his lips, stifling his protests before he could start them.
Soon, his Mary Jane-clad feet were swung up over his head as his mom smeared more Desitin across his bottom. She made sure it was sticky and well coated before lowering his legs and generously powdering his diaper area.
Trevor breathed deeply of the babyish scent, feeling helpless and infantile. Pulling the thick, soft cotton up between his legs, she slipped a pink headed pin in one side and secured it snugly around his hips. This was followed by the other side and Jordan had already selected a dainty pair of yellow rubber side-snap panties that she fed his feet into.
“Here you are babykins,” she said cheerfully, “these are the only kind of pants you’ll ever need.”
Trevor blushed hotly as she worked the rubbery, stretchy panties over the fat bulk of his diapers although secretly, he wondered if she wasn’t right. He was upset and ashamed at his growing lack of control which he knew rightfully pegged him as a sissy.
With a soft pat on his shiny diapered bottom, his mom led him into his crib after which she raised the side and latched it in place.
“Sweet dreams, baby Trevor,” Jordan said with a cutesy wave.
Trevor felt so childish at moments like this. The infantile smells of baby powder and wet diapers surrounded him and he pouted in frustration, his feelings of helplessness overwhelming him. As he lay there in his crib, staring at the ceiling and suc-king his pacifier, he reflected that by now, everyone at school knew of him as nothing more than a diaper-wetting pantywaist, dressed like a little toddler girl by his mommy.
He blushed with shame at the notion.
And now Jordan knew he was wetting during the day! Just like a baby!
He slammed his bunched fists on the crib mattress.
Aggravating his feelings of humiliation and frustration, were the gnawing sexual desires that swirled about him.
He suc-ked feverishly on the latex teat in his mouth, wishing more than anything he could relieve his needs just this one time. With visions of Jordan’s picture-perfect bosom still swimming through his head, he was beside himself with both shame and arousal. He tried, for the millionth time, rubbing the front of his soft, prissy diapers but it only made things worse. His tiny little member was held captive inside its secure plastic prison, unable to grow longer than an inch.
He blushed to think it was Jordan herself that had put him in enforced chastity.
He suspected she deliberately wore her tight, sexy tops, just to mercilessly tease him with!
It was so cruel!
But like it or not, Trevor was just going to have to resign himself to a frustrating life without orgasms, or any kind of sexual relief. It was to be a life filled with wet diapers, daily enemas, humiliating, bare bottom spankings, and early bedtimes in his crib.
But it was the perfect lifestyle for a bedwetting sissy brat like Trevor.
THE END
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Thank you for another wonderful story Baby Bobby. I absolutely loved it.
Please keep writing as you are a very gifted writer. Once again thanks.
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your stories are excellent, thank you for them. When reading them i sometimes picture myself as the sissy baby in diapers and a crib...oops i am.
Thank you.
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Hi Bobby,
Again a FAB story, I really love your writing, you have a real talent the way you draw the reader in, I have been a fan for years, and, would indeed love to work a together project, I just struggle with tech, and just need to figure a way to link my work with your own.. anyway, keep writing Bobby, love it THANK YOU ...!