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The Last Straw
#1
Elizabeth was fuming.
She stared at her cell phone, her ears growing hot with the anger that was building within her as she read a text sent to her from her son’s home room teacher, Mrs. Rossi. 
Shaking her head with a mixture of disbelief and disgust, she re-read the short message;

Hello Mrs. Bell. It’s Mrs. Rossi, Robby’s teacher. I’m sorry to inform you that during an apparent altercation between your son and Melissa Chambers, one of the more popular cheerleaders here, it seems he managed to wet his pants. He may try and hide the fact from you when he gets home, but I just wanted you to know what really happened.

Elizabeth sighed in frustration and set her phone down, turning to her good friend, Julie who was sitting next to her. 
“I’ve just been told that Robby wet his pants at school,” she explained, her voice showing its hard edge, “That’s it–this is the last straw.”
Julie nodded gravely, knowing full well, her friend’s long standing disappointment with her prissy, effeminate son.
They were sitting amongst their other friends, attending a meeting of the Strong Matriarch’s Society, a group of women whose goals were manifold but included shaping their sons to become strong, successful men as adults. 
Clearly, Robby was anything but that.
At 17, he had long ago shown his true colors, favoring clothing and toys that were more suited to girls than boys. In school, he studiously avoided more typical male activities and physical sports, or any sports for that matter, which soon acquired him a reputation as a sissy.
Elizabeth watched all this with dismay, wanting her Robby to be a role model for other boys and paragon of male virtues. As the years went on, she attempted several things to try and change the course of his life; she’d enrolled him in several sports teams (all of which he’d failed miserably at), put him in auto shop classes (something he showed zero aptitude for), and even hired a personal trainer to turn the frail weakling into a man of steel. 
The trainer quit after the first week.
She had also blustered, brow beat him, and threatened him to try and coerce the boy to be more manly but ultimately, all of her efforts had failed.
She had come to her wit’s end.
Her friend Julie had watched this process over the last ten years and she shared Elizabeth’s disappointment with her sissy son. This was made all the more awkward by Robby’s silly crush on Julie. He had long lusted over his mom’s buxom friend, fantasizing about her whenever she happened to come over to visit.
“Extreme situations require extreme measures,” Julie told her older friend, “Have you got everything you need?”
“Yes, the last item were the Mary Janes and they came in last week,” Elizabeth explained, “I better get going–I want to make sure I’m there when he gets home.”
“Okay, I’ll see you tomorrow then,” Julie replied, “And we’ll put that device to good use.”
“Thank you so much,” Elizabeth smiled briefly as she hugged her before grabbing her keys and making her goodbyes to the rest of the group.
 
                         ************************************************
 
Elizabeth was in the master bedroom, sitting patiently on the edge of the bed, her familiar, well-seasoned wooden paddle in her hand and ready for use. She had arranged all the items she needed to transform her sissy son on the bed beside her; a very short, white and pink party dress, Mary Janes, lacy white anklets, a thick set of cloth diapers, pins, and pink plastic panties. 
She was smiling to herself as she gazed at the items when she heard the front door gently close. She could easily imagine her sneaky little boy, hoping he could escape his rightful justice.
Using her authoritarian voice that easily carried throughout the house, she beckoned her newly arrived son.
“Robby! Come here this instant!”
Elizabeth listened to the soft footfalls of the sissy as he came down the hallway, no doubt filled with dread. A moment later, he appeared in the doorway, looking reluctant to cross the threshold but when he saw the paddle in his mother’s hand and the steely look of determination on her face, he turned white as a sheet. 
All his life, Robby had lived in fear of his strict, overbearing mother, and over the years, he had been the focus of both her sharp tongue and the fearsome wooden paddle she wielded. 
Standing before her now, his hands were trembling and trying in a futile attempt to cover the wet spot on the front of his pants but Elizabeth wasn’t having it.
“Did you wet your pants?” she demanded bluntly.
“Um, I…um…” he stammered, his eyes downcast as his cheeks reddened with shame.
Without another word, Elizabeth stood up, towering over her cowering son. Snatching his thin arm in her hand, she abruptly swung him around and brought the paddle down with a terrific impact across his seat.
“OOWW-WOWW!” he cried, jumping a bit as his hands immediately went back to sooth his stinging bottom. Unfortunately, his move only revealed the wet spot in front and his mother glared down at the humiliating evidence before her.
“Robby–you are a sissy and a pantywaist! You’ve just earned yourself a good, hard spanking,” she told him as she resumed her seat on the bed and yanked him over to her side.
Tears were already trickling down his cheeks as she swiftly unbuttoned his pants and jerked them down his legs.
“Please…d-don’t…” he begged her uncertainly.
“You should be ashamed of yourself–wetting your pants like a little baby!” she scolded him as she peeled his pee-stained underwear down his thighs.
“You won’t be needing these anymore,” she said tersely as she situated the nervous youth across her lap and pushed his wet underwear out of the way.
“P-please, please don’t spank me, mama,” he began pleading.
“You’re a sissy and sissies need to be spanked,” she told him firmly, as she had said so many times before.
Without any further delay, she raised the paddle over her shoulder and began spanking her errant boy in earnest, slapping each tender cheek with blistering harshness. Her wooden paddle had air holes in it’s face and the sting was terrible on the sissy’s soft, unprotected bottom. Robby howled and kicked his feet, as hot, bitter tears streamed down his face.
Elizabeth kept up a steady rhythm, viciously slapping his buns that were quickly going from pale white, to rosy pink, and now an angry, deep shade of red.
She paused for a moment to scold the crying boy;
“You just couldn’t manage to be a man could you? Instead, you had to be a childish little sissy–one who wets his pants.”
She emphasized her last word with a particularly hard swat across both his blazing cheeks. Robby howled in agony and his feet scissored wildly behind him.
“I am done trying to make you into a man. Since you want to be a sissy so bad–that’s exactly what you’re going to get. From now on, as soon as you get home from school–you are going to change into this outfit I’ve arranged for you. And since you’ve demonstrated you can’t control your wetting, your new underwear from now on will be diapers and plastic panties.”
Elizabeth finished with a flurry of fierce, scalding slaps to his swollen, stinging red bottom.
Standing the crying youth up on his shaky feet, she angrily ordered him to take his clothes off. Robby quickly complied and he sobbed miserably, wiping his arm across his face to try clear away his still flowing tears.
Elizabeth patted the thick, fluffy set of cloth diapers waiting for him as she gave him an evil smile.
“See these? These are your new underwear, my little sissy boy. They were specifically designed for pantywaists like you that can’t control their wetting. Three layers of absorbent Birdseye cloth, with soaker pads down the center, along with these adorable pink plastic panties will make sure my little baby’s wetting is all contained. 
“Now, when you get excited or scared, or have another run-in with a big, scary girl, you can wet yourself and you won’t have to worry,” she told him, her voice heavy with condescension.
“B-but, I don’t want to wear d-diapers,” Robby sobbed weakly.
Grasping his arm again, she jerked him around and swatted his crimson bottom hard with the paddle.
“WAHHHHH!!” he cried loudly as fresh tears spilled down his face.
“Too bad sissy. I’ve bought two dozen diapers and plastic panties and you will wear them–everyday, from now on.
“Now, you can either sit your prissy butt down on these, or I’ll put you back over my lap and we can continue this discussion,” she replied, her lips a tight line on her determined face as she continued to grip the paddle.
Robby knew he was defeated and he quickly assumed his proper position upon the diapers, although he howled in pain as his scalded, stinging cheeks touched the baby soft cloth.
Elizabeth proceeded to powder him generously, even upon his hairless chest so that the infantile scent would remain with him for some time. Briefly, she grasped his baby sized penis–which was really no bigger than a AA battery–as she shook her head with dismay. It was obvious her sissy son was never going to be able to please a woman with such a thing. For years, she had been hoping it would start to grow but even after puberty, it had stubbornly refused to do so and it had remained the size of a small child’s genitals.
She powdered the pathetic stub and tucked it back between his legs before drawing the fluffy layers of cotton up and swaddling her sissy son in his first diapers since he was a toddler. She quickly pinned the sides snugly together and then took the waiting plastic panties and gathered them in her hands. 
“Here are your baby panties–aren’t they pretty?” she asked as she fed them over his shaking ankles, slowly drawing them up his nearly hairless legs. Robby whimpered as this ultimate symbol of babyhood was pulled up around his fat diapers, the ambient light reflecting off the shiny vinyl plastic.
“There…” she said with obvious satisfaction, “Now my little sissy boy is all safe and protected.”
That done, Elizabeth put some white lacy anklets over his feet, followed by a pair of glossy pink Mary Janes. Sitting him up, she lowered the fluffy white and pink baby dress over his head, turning him around so the she could button up the back. There was a double row that ran up the middle of the back, specifically made small and difficult to reach so as to make it impossible to get the dress off without her help.
The dress had multiple layers of delicate lace under its short, frilly hem, with a Peter Pan bodice and equally short, puffy, elasticized sleeves. It looked like something a three year-old girl would wear to Sunday school.
Standing him up, she moved him to stand in front of her full length mirror. Robby blushed a deep red, hot with abject shame as he took his first look at the cute sissy baby staring back at him with blue, doe eyes in his reflection. He tugged frantically at the short hem of the dress, in a hopeless attempt to cover his big, embarrassing diapers. Unfortunately, it only came down to just past the elastic waistband of his panties, leaving his childish pampers clearly on display.
“Now…whenever someone sees you in your diapers, you are to say the following line; ‘I have to wear diapers because I’m a sissy’,” Elizabeth instructed him firmly.
“Yes, mama,” he replied, keeping his eyes downcast.
 Secretly, he couldn’t help but wonder who he would have to recite such a humiliating line to but he said nothing.
“Say it.”
Robby cleared his throat nervously.
“I-I have to wear diapers be-because I’m a-a sissy.”
“Again,” she ordered him.
“I have to wear diapers because I’m a sissy.”
“Look at yourself in the mirror, sissy. Now say it again because you know it’s true.”
Robby’s face flushed red again. He could barely look at his humiliating reflection and his chest and ears were crimson with shame.
“I have to wear diapers because I’m a sissy.”
“Better get used to that line, because you’ll be saying it a lot,” she told him, emphasizing her statement with a slap on his fat, diapered bottom.

  ***********************************************************
 
All that afternoon, Robby struggled to get used to his new outfit, and in particular, the fat diapers swaddling his hips. They swished between his inner thighs somewhat pleasantly but also prevented him from walking normally. The short baby dress meant his childish diapers were constantly in view, and he blushed hotly every time he passed by a mirror.
He prayed that he would be able to convince his stern mother to allow him to go back to wearing his regular clothes, but the stacks of diapers and plastic panties in his room suggested otherwise.
That evening, Elizabeth informed her sissified son that she was moving his bedtime up from 11 to 9 pm.
“I want you to have your teeth brushed and ready for beddie-bye, no later than 8:45 every night, do you understand me?” she told him.
“Yes mama,” he replied submissively.
She removed his dress and replaced it with a fuzzy fleece diaper shirt and then sent him to bed.
Unfortunately, the day’s traumatic events haunted the poor, defeated sissy and he tossed and turned that night in his bed. Worse yet, at sometime while he was sleeping, the floodgates opened and Robby managed to soak his diapers. Thankfully, the snug plastic panties he was wearing kept the wetness contained but it was a red-faced sissy that greeted his mother the next morning. She was none too pleased and after pulling the soggy wet cloth down his legs, she took the opportunity to give his still pink bottom a good, hard swat with her paddle.
It was a tearful sissy that made his way to the bathroom for his morning shower.
After he finished, he found his mother back in his room, boxing up all his underwear, which she said was going straight to the trash.
Elizabeth proceeded to dress him in a some pink, nursery print trainers and a transparent pair of pink plastic panties before letting him finish dressing.
Choosing the loosest pair of jeans he could find, Robby decided that his childish underwear wasn’t too noticeable, except it was going to be difficult to hide both the infantile scent of baby powder and also the distinctive crinkling sound whenever he walked. He prayed desperately that no one would question it and he knew the challenge would occupy his thoughts, every moment he was at school.

***********************************************************

That afternoon, as soon as Robby got home from a fretful day of school, his mommy dressed him right back into his outfit, with a fresh set of fat, fluffy diapers replacing his trainers. Elizabeth brought forth another baby dress, similar in style to the one from the day previous, but this one was lemon yellow with white accents.
After getting his Mary Janes on, they heard the doorbell ring.
Robby froze in place, a look of panic on his face.
“Don’t worry sissy, it’s just Julie. She’s been looking forward to seeing your new look–lets go out to the living room so you can greet her.”
Robby shook his head frantically.
“No mama–please don’t!” he squealed. 
Elizabeth yanked him to his feet and swatted his diapered bottom to compel him to get moving. He whimpered and made paltry efforts to resist her but there was never any doubt that he was going to do exactly what she told him. In a battle of wills, the spineless sissy was simply no match for his stern, domineering mother.
Holding his wrist tightly in her hand, Elizabeth used her free hand to open the door wide, revealing her stunning friend Julie standing on the porch.
“Come in–come in!” she greeted her warmly.
Julie, a strong, confident woman of 36, coolly walked into the house, her high heels clicking on the hardwood floor. Robby hung his head low, his idol seeing him for the first time dressed like an overgrown toddler girl. Suddenly, a squirt of warm pee escaped into his diapers before he could stop it and he gasped audibly, even as Julie looked him up and down.
“Tell Julie why you’re wearing diapers, honey,” Elizabeth prodded him.
Robby swallowed hard, deeply ashamed to be seen like this.
“Umm…I…um,” he stammered.
“You can do it, come on baby,” she told him, gripping his wrist tightly.
Robby nervously licked his dry lips.
“I…I have to wear d-diapers, b-because I-I’m a sissy,” he admitted as he stared at the floor. He could feel the warm, damp cotton surrounding his tiny little package inside his pampers and he prayed his mommy wouldn’t check him.
“You certainly are,” Julie quipped as she looked him hard in the eyes, “You’re the biggest sissy I’ve ever known.”
This was absolutely mortifying for the weak pantywaist to hear and her words washed over him like a tsunami of humiliation. For as long as he could remember, he’d always pined and fantasized about his mom’s beautiful, sexy friend, and to stand before her now and hear her shameful appraisal of him stung him to the core.
“Shall we?” Elizabeth asked her friend cryptically. 
Julie smiled broadly.
“Yes, I have everything we need,” she replied.
The three of them made their way to Robby’s bedroom where his mommy stood him in place. The confused youth stood before them, shifting his feet and wondering what she had in mind for him.
All of a sudden, Elizabeth suddenly grasped the sides of his diapers and abruptly yanked them down his thighs.
Robby gasped and his hands immediately went to try and cover his baby-sized, twitching penis. At the same time, Elizabeth’s nose wrinkled as she caught a waft of pee and she reached down into the front of Robby’s diapers to confront her suspicions.
Did you wet your diapers?” she said accusatorily. 
Robby bit his lip hard and looked away, his cheeks blazing red with embarrassment.
“I-it was an accident, mama,” he wailed.
As Julie shook her head with disappointment, Elizabeth stood back up and placed her hands on her hips.
“Now you see why my little sissy has to wear diapers like a baby,” she explained.
Julie nodded her head as she dug in purse for something.
“Well, it’s high time you put this on then.”
Taking her hand out, she revealed a small, pink metallic object, looking like a small cage and connected to a larger ring. She quickly disassembled it and she knelt before the quivering sissy youth. 
“Wha-what’s that?” Robby quaked nervously. 
He was only vaguely familiar with the concept of chastity devices and this threatened to take away his freedom and imprison his tiny little penis.
“Something all sissies need,” Julie replied firmly, “Especially, sissy masturbators like you.”
Robby’s cheeks were burning as she grasped his little sack in her smooth hand, pulled it outward, and fit the larger ring behind his genitals. With that in place, she took the pink, thimble sized cage and stuffed Robby’s defenseless penis into it. This was quickly mated with the cuff ring, compressing his tiny noodle, and Julie efficiently slipped a small lock through the eye at the top.
With a firm snap, she closed the lock, irrevocably trapping Robby’s little nub forever in it’s new, restrictively short prison. It was over before he even understood what had just taken place.
“There,” she said rubbing her hands together in a sign of both completion and satisfaction, “No more erections and no more masturbation for you. From now on, your little penis is off limits,” she said with finality.
His package looked like three little grapes, except that the middle one was now trapped in a secure pink metal cage.
Robby couldn’t believe what had just happened. He grasped at the device and tugged at it, hoping against all odds to get it off. Quickly seeing the futility in that, he tried everything he could to pull his little nub out from the cage but it’s devilish design prevented that as well.
“Sorry, my little pantywaist. This device is guaranteed to defeat even the most determined sissy masturbator. Your days of being able to play with yourself are over,” she said emphatically.
“No!” Robby pouted with frustration, even as his cheeks reddened with shame.
Robby was used to playing with himself every opportunity he got and this fearsome device threatened to end all of that forever.
But beyond that, it was absolutely mortifying to be called out as a chronic masturbator by, of all people–Julie.
The beautiful woman laughed as she looked down on the frowning pantywaist; “Little babies that wear diapers don’t get erections and neither should you.
“Only real men deserve those and you’re not a real man, are you?” she goaded him.
Robby sniffed and his lower lip trembled.
“Answer her,” Elizabeth snapped.
“No Ma’am,” he replied, “I-I’m just a s-sissy.” 
“Without a doubt–you sure are,” Julie agreed as she reached down and pulled his childish diapers back up and around his hips.
“Looks like you’ll just have to wear your wet pampers for a while, sissy boy,” she said as she aggressively tugged the waistband upwards, making sure the warm, pee-soaked cloth was once again embracing his little, caged genitals.
“Run along and play,” his mommy said, dismissing the visibly upset youth with a slap on his fat, diapered bottom. He waddled off, not sure where to go or what to do as his mind struggled to grapple with the concept of permanent chastity.
 
          **********************************************
 
Robby sat in class, fidgeting and trying hard not to stare at his teacher, Mrs. Rossi.
She was sitting behind her desk at the head of the class, bent over slightly as she graded some papers and oblivious of his lecherous attentions. The rest of the students were studying quietly but Robby was far too distracted to be able to do that.
The object of his focus was wearing a snug, low cut tank top of pale pink, and it hugged her delicious breasts like a second skin. Robby licked his dry lips anxiously as he stared down her top, gazing at the deep cleavage between her two mammoth globes that were pressed together and creating a pair of sexy, soft mounds.
It had been over a week since Julie had locked Robby’s tiny penis into it’s implacable steel cage and he was frantic with arousal. In fact–he had never been so horny in all his life. He wanted nothing more than to tear the device off and wank himself silly but to his dismay, he had discovered that was quite impossible. Every day had become an exercise in sexual frustration–it seemed like everything around him was designed to tease and torment him.
And now his pretty teacher was making his life a living hell, causing his little nub to flex and strain painfully in it’s tiny, restrictive cage. Robby squirmed in his seat uncomfortably, wishing he could just reach down into his trainers and at least adjust the position of his package to alleviate the pain.
He had to be careful, he reminded himself. Mrs. Rossi had already warned him once to stop leering at her and she’d even threatened him with vague “consequences”, but Robby simply couldn’t stop himself. She was so over-the-top sexy, and Robby was deeply infatuated with her. He could only imagine what it would be like to suckle from her big breasts like a baby.
He blushed as he thought of how his mom would be getting him dressed in just a short time at home; baby diapers, plastic panties, a short dress, and prissy Mary Janes.
He shuddered to think of what his stunning teacher would think if she knew. He could see her so easily in his mind’s eye, laughing at him with her perfect teeth as she mocked his babified look.
He was in mid-daydream when she looked up without warning and caught him red-handed staring at her. He turned his head away in a flash but not before seeing the frosty look of anger cross her gorgeous features. He cursed himself for his lack of self control as his cheeks flushed red with embarrassment.
Just then, the class bell sounded, jarring everyone in the room. In a mass exodus, the students grabbed their books and rushed out of the room.
“Robby–I want you to stay after class,” he heard his teacher say in a stern, cutting voice above the commotion.
Robby froze in place, a sudden wave of fear washing over him.
Was he in trouble? he wondered as he bit his lip nervously.
After everyone had exited the room, Robby remained in place, still some distance from Mrs. Rossi.
“Come over here,” she commanded him as she opened a drawer and pulled out an oval wooden paddle, placing it carefully on the desk next to her.
Robby gulped in terror and he suddenly felt a warm wetness spreading in his trainers. This was a disaster!!
“Wha-what did I d-do?” he quaked fearfully.
Without answering him directly, Mrs. Rossi moved her chair clear of the desk and beckoned him over with an impatient gesture.
He stumbled forward, utterly terrified at the prospect of getting a humiliating, painful spanking by his sexy teacher.
“What did I tell you about staring at my breasts?” she demanded angrily.
Ironically, the mention of her fantastic bosom caused Robby’s gaze to immediately fall upon her big, bountiful chest and even as his heart thumped with dread, he couldn’t help but admire her perfect, round mammaries, stretching her thin, pink top in a staggering display of feminine sexuality.
“I-I, um, I mean…you said…” his voice trailed off uncertainly.
He was trying frantically to buy himself some time but Mrs. Rossi was as determined as she was beautiful. She quickly reached over and undid the snap on his jeans, jerking them down his thighs. Her mouth dropped open with shock as she saw his trainers and colorful pink plastic panties.
For a moment, she stopped what she was doing and stared up at Robby’s brightly blushing face.
“You wear training panties?” she asked, clearly astounded.
Robby choked back a sob of shame and nodded silently.
“Well, I’m afraid they’re going to have to come down,” she told him unsympathetically.
Hooking her thumbs inside the stretchy elastic waistband, she lowered the prissy, pink vinyl panties down until she made her next discovery.
“Did you wet yourself??” she asked with a mixture of disgust and astonishment.
Robby’s cheeks burned and he shifted from one foot to the other.
“Umm, yes, Ma’am,” he mumbled, barely audible.
“Well clearly–you belong in diapers–do you know that?” she said emphatically as he lowered the thick, wet underwear down past his knees.
Robby didn’t answer her but tears were already filling his eyes as he quickly covered his caged genitals.
“I’m going to paddle your bottom and paddle it hard–do you understand me?”
Robby’s lip trembled and he nodded his head as a hot tear trickled down his cheek.
Not wanting to soil her skirt with his pee-soaked trainers, Mrs. Rossi pulled the hem back, exposing her firm, smooth thighs to the scared, trembling sissy boy before hauling him over her lap.
Robby whimpered and squirmed, deeply afraid of what was about to happen. It was then, that he realized the door to the hallway was still wide open and anyone still in school, would be able to hear him getting spanked.
He waved frantically at it and was just about to say something when the paddle came down, slapping his bare bottom viciously.
Robby kicked his feet wildly and howled with pain.
“You are NOT–“
–SMACKKK!!
“NOT–“
–SMACKKK!!!
“NOT–to stare at my breasts,” she snarled as she swatted his blazing cheeks with all her might.
Robby cried like a baby, but out of the corner of his eye, he suddenly caught a blurry vision of someone standing in the doorway, who had heard the loud swats and was apparently now using their cell phone to snap pictures of his humiliating punishment. He could barely focus with the tears filling his eyes, but it looked like the bullying cheerleader, Melissa Chambers.
Robby kicked miserably and slapped the floor with his hands as Mrs. Rossi’s hard wooden paddle slapped his soft bottom again and again.
As bad as the sexual torment had been earlier–this was far worse. Beyond the fiery inferno on his rump, now, everyone would know he had gotten spanked like a child and maybe even know about his training panties too! He would never live it down!
Mrs. Rossi paddled the helpless sissy until his cheeks were thoroughly red, swollen, and well punished. She finally let him up and as his hands shot back to rub his blazing bottom, she caught sight of his tiny, pink cage for the first time.
Holding his diminutive jewels in her hands, she smiled a little as she shook her head.
“Your mommy certainly made the wise choice here,” she said dismissively as she looked up into his crying eyes.
Robby wiped his face and sobbed, using his other hand to sooth his stinging, scalded cheeks.
With several short tugs, Mrs. Rossi yanked his wet trainers and panties back up before helping him with his pants.
“I think I better take you home,” she told the distraught sissy boy.
Robby was too upset to argue with her and he let himself be led out to the parking lot where Mrs. Rossi had her car.
She gave him some tissues to blow his nose and they drove the short, ten minute drive to his house but the closer they got, the more agitated Robby became. He knew only too well what his mother’s reaction would be when she found out he’d wet his trainers, to say nothing of what she might do if Mrs. Rossi told her about why she spanked him in the first place.
“Y-you can l-let me out here,” he pointed anxiously out the window.
“Oh no, I better take you home–your mommy might be getting worried about you,” Mrs. Rossi said firmly.
As Robby bit his lip nervously, another stream of warm pee surged into his clammy wet trainers, and he whimpered in angst. He was going to be in SO much trouble!
They arrived all too soon and Mrs. Rossi came around to his side, taking his hand and leading him up the sidewalk to the front door. Robby could have walked straight in, but instead, he fidgeted and stalled for time, waiting foolishly on the porch as his teacher rang the doorbell.
His mother was not long in coming, and when she saw her sissy son’s teacher holding his hand like she was his babysitter, her eyebrow went up in suspicion.
“Hello, Mrs. Bell. I’m afraid little Robby had an another accident in class and he wet his trainers,” his pretty teacher explained.
Robby hated being called ‘little’, especially when he was nearly 18 years old, but at the moment, that was the least of his worries.
Elizabeth’s features darkened and she crossed her arms over her chest as she looked down on her wilting boy.
“And I’m afraid he also earned himself a spanking today. I’ve warned him about staring at my chest and I caught him today doing it several times.
“I’m sorry, but I had to take matters into my own hands,” Mrs. Rossi explained.
Elizabeth immediately stepped out onto the porch, grabbing Robby’s twig-like arm and spinning him around, she landed a hard, angry swat on his padded bottom.
“You disgusting little boy!” she reprimanded him, “You are in big trouble!”
Mrs. Rossi smiled with satisfaction and she looked ready to leave when Elizabeth stopped her.
“Oh–please stay. I’d like for you to see how this little sissy gets punished for his misbehavior,” she told her, as she bade her to come in.
Robby felt utterly childish and mortified that his gorgeous teacher was going to see everything he’d hoped to keep secret.
The three of them entered the house and Elizabeth led them to Robby’s room, which was looking more and more every day like a baby’s nursery. Infantile designs now covered the walls and his short, ruffled dresses could be seen, hanging up and ready for him to wear. A diaper changing station lay alongside his bed with stacks of soft, fluffy diapers and numerous plastic panties next to them.
“It’s only appropriate that you should see how Robby dresses when he’s at home,” Elizabeth said as she began removing her boy’s clothes in front of Mrs. Rossi. He squirmed and whimpered, fidgeting in place as he tried to prepare himself for the humiliation that was about to take place. Before long, the embarrassed sissy stood wearing nothing but his sagging wet trainers and plastic panties. Pulling them down past his bottom, she turned him around and gazed down at the pink and red marks still covering his curvy cheeks.
“Well–looks like you got yourself a good spanking,” Elizabeth remarked with some satisfaction, “Unfortunately for you–you’re about to get another one.”
Robby stamped his feet in frustration, whimpering as the tears filled his eyes and his mom laid him down on the changing pad to begin her daily ritual of diapering him.
“Don’t worry–these won’t be on for long,” she told him firmly.
With her perfectly manicured hands on her hips and a smug look on her beautiful face, Mrs. Rossi looked down on the nervous sissy boy.
“Looks like I didn’t give your mommy sufficient credit–I’m glad to see she’s putting you in diapers where you belong.”
“Oh yes, mommy’s little bedwetter is getting his just reward,” Elizabeth assured her as she powdered his little caged package, “And I think we’ll dispense with putting you in trainers anymore. You’ve proven that you can’t keep yourself dry so it’s diapers and plastic panties from now on.”
Robby’s cheeks blazed with shame and he burst into tears as she tugged his nursery print plastic panties up his legs and over his fat, fluffy diapers. In no time at all, his mommy was busy lowering a baby dress over his upraised arms as he timidly submitted to being dressed as a toddler. His shoes were quickly removed and replaced with lacy anklets and glossy Mary Janes as Mrs. Rossi marveled to herself how smooth and hairless his girlish legs were.
His teacher shook her head at the transformation, both for how docile he was while he was submitting but also for how perfectly appropriate his new outfit looked on him. Having observed the youth in class, Mrs. Rossi had watched him being pushed around daily, not just by the boys but also by the girls. Although she’d never voiced her opinion aloud, she’d always thought of him as nothing but a big sissy. This childish outfit he was being dressed in seemed so much better suited to his prissy personality than the jeans he usually wore.
She felt absolutely no sympathy for the pantywaist standing before him now, looking just like an overgrown toddler girl. In fact, she felt compelled to congratulate Elizabeth for her work.
“I have to tell you–I think you’ve finally started dealing with him in a way that a lot of people feel he really deserves,” she said.
“I’m so glad you agree,” his mom said as she handed his teacher a red rubber enema bag, “Would you be so kind as to fill this with as much warm soapy water as it will hold?”
Mrs. Rossi chuckled and nodded, “Sure thing.”
By the time she returned to Robby’s bedroom, his mom had him draped over her lap, his diapers and plastic panties were pulled back down and the ruffled hem of his dress pulled up the small of his back. Elizabeth was slowly rubbing her wooden paddle across his bare, bruised bottom, scolding him as she did.
Robby was already openly crying, fearing the spanking that was about to come.
“A little sissy like you has NO business looking at a woman like Mrs. Rossi in that way. And to think you wet your training panties–again! I hope you like your diapers because from now on–that’s all you’ll be wearing.”
With that, the paddle swooped up and came swiftly back down, landing with a deafening swat that filled the room. Robby’s soft, tender bottom flattened helplessly under the harsh impact and he howled in agony. More cruel slaps followed the first as the trapped sissy kicked wildly and cried like a baby, unable to stop the painful, humiliating punishment.
After bringing his cheeks to a bright, angry shade of red, Elizabeth stopped the spanking and set her paddle aside. Taking the bulging enema bag from Mrs. Rossi, she attached a long white hose that ended in a fat, dildo-like nozzle.
“That’s sure to make him squirm,” she remarked with a wry smile.
“I’m sure it will–I just got it last week and I haven’t had the chance to try it yet,” Elizabeth explained.
She handed the heavy, two quart bag dripping with suds back to Robby’s teacher and dipped the imposing rubber nozzle into a jar of KY.
“Robby–you’ve got a nice, long, soapy enema coming. Better spread your legs like a good girl because this nozzle is much bigger than your old one.”
Whimpering with anxiety, Robby did as he was told but he wailed in a panic when he felt the fat, greasy, blunt end of the nozzle pushing insistently at his back hole.
“N-no–M-Mommy–i-it-it’s too big!” he squealed as he waved his hands before him.
“Just relax and spread your legs–Mommy knows you can take it,” she replied as she continued to maneuver it determinedly against his puckering anus.
Robby cried out as the big, mushroom-shaped head abruptly slipped past his defeated sphincter without warning.
“OHHH!!” he cried.
Mrs. Rossi smiled with satisfaction as she watched the long, thick rubber shaft slowly disappear into the squirming, squealing youth’s rectum.
“Theeeere…that’s my little boy,” Elizabeth soothed him as she squeezed and rubbed his hot, stinging cheek.
Slowly pulling it part way out, she teased the confused sissy by twirling it, before plunging it back in, until all eight inches of the fat nozzle were buried inside him. Robby moaned helplessly, looking and sounding very much like a little girl.
Without warning, his mommy released the clip, sending a strong torrent of warm, soapy water flowing deep into his bowels. Robby moaned loudly again, gasping as he was forced to submit to the humiliating and emasculating punishment.
After a minute, Elizabeth closed the clip, allowing the liquid to settle within him before opening it up again. This went on for some time, with Elizabeth regulating the opening and closing of the clip and ensuring Robby got a very thorough purging.
Just as he thought he had managed to take in the entire enema, his mommy would surprise him by opening the clip again, rewarding him with yet another steady surge of the cleansing enema. The poor sissy moaned weakly, gasping helplessly as his back passage was stretched wide to be the conduit of his punishment. His virgin hole ached from the fat rubbery invader forcing it open but he was completely at his mommy’s mercy.
By judicious control of the flow, Elizabeth ensured that Robby took every last drop of the soapy water before at last, she slowly eased the slippery, massive dildo nozzle out of his rectum.
It was a defeated, whimpering sissy that finally limped off to the bathroom, his tummy cramped and his back hole, sore and stretched.
 
                             *********************
 
Twenty minutes later, Robby shuffled back into his room, his hands trying to maintain a ludicrous attempt at dignity by covering his tiny little caged penis.
“Have you learned your lesson, sissy?” his mommy asked sharply.
“Yes, Mama,” he replied submissively.
“Very well. It’s diaper time and then you can say goodbye to your teacher,” she told him as she led him over to his changing table.
Hanging his head in shame, Robby let his mommy smear diaper rash cream across his sore and stinging bottom, before pulling the multiple, thick layers of baby soft cotton up between his legs and pinning them snugly on either side of his hips. The cushiony bulk forced his legs apart and he whimpered as she pulled his nursery print plastic panties up his legs and fitted them over his fat, humiliating diapers. Fortunately, the ruffled hem of his dress was so short, Elizabeth had no difficulty making sure the elastic waistband of his panties covered all of the soft cloth inside.
Mrs. Rossi watched him with silent satisfaction. To be sure, this was a scene she would not soon forget. Finally, this prissy little pantywaist was getting exactly what he deserved. Seeing him dressed as a little toddler girl in diapers, Mrs. Rossi knew he was in good hands.
“Why don’t you tell your teacher why you have to wear diapers, Robby,” his mommy instructed him as she made a few last minute adjustments to his outfit.
“I-I have to wear diapers because I’m a sissy,” he replied obediently, using his memorized line.
“You know, if you ever need a babysitter for your little pantywaist, let me know,” Mrs. Rossi offered with a smug smile.
“That’s an excellent suggestion–Robby needs a firm, authority figure in his life that’s not afraid to spank first and ask questions later. You’re the perfect candidate for the job.”
The two shook hands and a new relationship was born.
 
THE END
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#2
Bobby, you are our shining star of stories for all of the naughty, tiny peepee, caged, plugged, diapered sissy boys.

I wonder how many are out there right now, rubbing away or humping as they read your stories, imagining themselves as Robby.
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#3
That's a delightful story, Bobby. Not often we get a story so believable (albeit clearly declared as fantasy) and so well written.

I wonder how much of this is your splendid imagination and how much is experience...!
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#4
That's a delightful story, Bobby and so well written.
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#5
I have always liked your writing. You've been an inspiration to me.
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#6
Smile 
(11-30-2019, 10:03 PM)Ali Wrote: That's a delightful story, Bobby. Not often we get a story so believable (albeit clearly declared as fantasy) and so well written.

I wonder how much of this is your splendid imagination and how much is experience...!

To be sure, this is an act of fiction. However, like so much of my work, many aspects are derived from my own personal experiences. Smile
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#7
thank you for your story. I like so much...my kind of stories
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