Be Careful What You Wish For

Note to the reader; This story was inspired by one of the very first pieces of erotica I ever read, some 37 years ago, when I was just a shy youth with an over active imagination and a raging libido.

It was a letter written to a magazine called Variations about a boy who was intrigued with the notion of being spanked, and it sparked a kinky interest in me that I have carried ever since. I combined the plot from what I remembered, with my own personal experiences as a child, when I would sometimes wet my pants at school.

Enjoy.  ;o)

 

 

 

 

Timmy sat at his classroom desk, his history book open before him, but unlike the students around him, he simply couldn’t concentrate on what he was supposed to be reading. Class was due to end in five minutes, and he was wracked with both nervous and excited anticipation.

Glancing up at the head of the class, Timmy gazed with longing at his smoldering hot, sixth grade teacher, Ms. Taylor. As usual, she looked absolutely amazing, the long locks of her soft brown hair spilling over her bare shoulders as she idly toyed with a strand in her free hand. Her pretty features were cast downwards to the desk before her as she graded papers in the silence of the classroom.

Timmy had always been completely infatuated with her, with her long legs, dazzling eyes, and full, sensuous lips. And it was a rare day that she didn’t wear a top or dress with a plunging neckline, displaying a breathtaking view of her big, beautiful breasts.

Physically, Ms. Taylor was all a male could want or hope for.

But there was another element that inexplicably drew Timmy to her like a moth to a flame.

Over the course of the last school year, Timmy had had the opportunity to observe a number of his classmates being punished for various things they had done wrong. The punishment was almost always the same; a trip over Ms. Taylor’s lap for a hand spanking. Sometimes this was done after class, but if the infraction were severe enough, she wouldn’t hesitate to call them up before the rest of the students, scold the guilty party and take the person over her lap for the punishment.

Timmy had watched these sessions with a rapt, voyeuristic fascination. He would tremble with excitement as he watched his stunning teacher unbuttoning the poor boy’s pants, pulling them down, and then tugging his underwear down past his knees. From the perspective at his desk, Timmy was unable to see the student’s frightened face but he could well imagine it as she took him over her skirted lap and began spanking his bare bottom.

Before long, the child’s buns would go from pink to a bright red as he helplessly kicked and cried, shouting promises of contrition and better obedience.

It was always a sobbing and subdued boy that would shuffle his way tearfully back to his desk, taking his seat again only with great difficulty.

Timmy watched each of these punishments take place with his heart beating excitedly in his chest. Despite her delicate, pretty features, Ms. Taylor was the epitome of strength and authority in the classroom and for reasons he couldn’t explain, the whole process made him frantically horny.

By and large, Timmy was a model student.

He never got into trouble and his grades were at the top of his class. He had done everything he could to ingratiate himself with Ms. Taylor and even achieved the lofty position of teacher’s pet.

But as the end of the school year was quickly approaching, Timmy felt as if he were going to miss out on this strangely unique and exhilarating experience. He had never once done anything to merit one of Ms. Taylor’s spankings but for some reason, the idea thrilled him to the core. He knew that they had to hurt and for those that had to experience them in front of the rest of the class, they had to be incredibly humiliating as well.

Although in his fantasies, he often dreamed of her spanking him before the other students, he knew in his heart of hearts he could never bring himself to make that happen.

Nevertheless, today, he intended to make at least a part of his fantasy come true.

Having thought about this many times, Timmy felt certain that he was not likely to have Ms. Taylor as his teacher next year, so it was imperative that he implement his plan and soon. There were only a few days left in the school year and today he had managed to summoned every ounce of courage in order to make it happen.

The bell rang clamorously, and Timmy just about jumped out of his seat. All the other students quickly scooped up their books and ran out of the classroom as if it were on fire but Timmy hesitated. In less than a minute, the room was empty except for himself and Ms. Taylor, who was still sitting at her desk watching with amusement as the scurrying students departing her classroom.

Timmy rose to his feet on shaky legs, cobbling up his jittery nerves to confront his sexy teacher. As he approached her desk, she sat back and smiled up at the nervous child. She looked utterly ravishing today, with large silver hoop earrings dangling from her petite ears, partially hidden by the gorgeous curls of her luxuriant brown hair. Her rose colored lipstick reflected the sunlight in the room and Timmy ached to be able to kiss her, that being the highest, most supreme act of sexuality to the innocent 11 year-old boy.

“Timmy, is there something I can help you with?” she asked politely as she looked up from her work.

Timmy cleared his throat nervously.

“Um, I…” he began haltingly, his cheeks steadily growing redder.

“What is it, sweetie?” she asked, her pretty eyes sparkling up at him, “Is everything okay?”

Timmy swallowed hard, struggling to make eye contact with his beautiful teacher.

“Um, well you see… I, um, was thinking…that… you know, I had never gotten a sp-spanking…from you,” he said, his stammering voice practically a hoarse whisper.

Ms. Taylor beamed back at him, her beauty washing over him like a warm wave.

“That’s right, honey,” she nodded, “you’ve been a very good boy this year, and unlike some of the naughtier kids here, I’ve never had to punish you for anything.”

Timmy swallowed again and shuffled his feet as he stood before her, his palms suddenly clammy with sweat.

“But you see–I–I…I want one,” he suddenly blurted out, his cheeks blushing bright red.

Ms. Taylor’s delicate eyebrow raised in surprise as the side of her sensuous mouth curled in a mischievous smile.

“You want a spanking?” she asked incredulously.

Timmy couldn’t look her in the eyes and he nodded his head in embarrassed silence as he licked his dry lips. His heart was pounding in his chest that he had finally uttered aloud, his long cherished, secret fantasy.

Ms. Taylor rolled her office chair over to the side of her desk, reaching for Timmy’s sweating hand and gently pulled him over to her side.

“Well Timmy,” she smiled, “maybe you should tell me about all the things you did this year that you didn’t get caught for, hmm? And then we could take care of them right now with a trip over my lap.”

A small, scared part of him deep down inside had hoped she’d refuse him and he’d be saved the pain and humiliation of a trip over her lap but her tone of voice practically sounded eager and hopeful.

Timmy’s pulse was racing and he was so excited he could hardly breathe. Here he was, standing before his beautiful, sexy idol and about to get spanked like all the naughty schoolboys he had seen during the year. Her firm thighs looked fabulous today and she was wearing a strappy set of high heels that he found particularly exciting.

“Um…Well,” he began, as he struggled to control his breathing, “there was this one time when I, um…jammed a…a pencil lead into another guy’s lock on his locker…”

Ms. Taylor nodded patiently.

“Go on.”

“Umm, and…um…well, last week, I um…I accidentally wet my pants right before the um, end of class,” he confessed shamefully.

“I see,” she said thoughtfully, “do you wet your pants very often?”

Timmy’s cheeks, already a blushing red, flushed brightly with humiliation and he nodded his head, unable to verbally admit to his childish lack of control.

“Timmy, how often do you wet your pants?” she pressed the trembling boy. Her voice had subtly taken on a more authoritative edge.

He stared at the floor and shuffled his feet, looking away from Ms. Taylor as he swallowed back his embarrassment and agitation.

“Timmy?”

“Um, I don’t know…maybe…twice a week?” he replied uncertainly

“I’m afraid this is more serious than I thought,” Ms. Taylor said gravely as she opened a drawer in her desk and purposefully took an oval wooden paddle from it. Timmy gasped when he saw it and his heart lurched as it suddenly skipped a beat.

“No–I–I…I didn’t want to be paddled…Ju-just a hand sp-spanking,” he quivered.

Ignoring his protest, Ms. Taylor calmly began unbuttoning his slacks and she let them fall in a ring around his ankles. Gazing down at the crotch of his snug white underwear, she noted the pee stains in front before slipping her long nailed thumbs inside the waistband.

“P-please, please don’t use the paddle, Ms. Taylor,” he begged her more urgently.

This wasn’t what he had in mind at all

Ms. Taylor tugged his underwear down past his shaking knees and smiled as she laid eyes on his tiny, bald little package. It wasn’t particularly cold in the room, but his baby-sized penis was no bigger than a grape, quivering and protruding from his small, hairless sack.

He squealed with real fear and distress as she took him over her lap, rubbing the paddle softly on his bare bottom. What had he gotten himself into?

“I-I-I ch-changed my mind–I don’t wanna spanking now!” he blurted out, his voice choked with fear.

“Timmy, I’m glad you came to me about this,” she said as she held him in place with her free hand and continued to stroke his defenseless cheeks with the paddle, “A big boy like you shouldn’t be wetting his pants like a baby. In fact, if you can’t handle the responsibilities of being a big boy, you should probably be wearing diapers and plastic panties.”

Timmy had never felt so humiliated in all his life, but before the blushing boy could respond, Ms. Taylor raised the wooden paddle and brought it down with a hard, scalding swat across his bottom. A searing band of fire ignited across his cheeks and he howled at the top of his lungs, kicking his feet wildly.

SMACKK!! SMACKK!! SMACKK!!

Again and again, Ms. Taylor swatted his jiggling little bottom harshly, making the boy cry out and struggle frantically over her lap. Hot, bitter tears spilled down his flushed face and he now sincerely regretted his ill-advised scheme.

It had been one thing to watch his peers being given a hand spanking, but it was quite another thing altogether, now that it was him on the receiving end of her hard wooden paddle, his own cheeks stinging and blazing like hot coals.

Besides the shameful humiliation that he would never live down for the rest of his life, the searing pain was much more intense than he had imagined. Each blistering swat of her paddle against his soft, tender cheeks brought fresh tears to his eyes as he slapped the floor with the palms of his hands in helpless frustration. Timmy had imagined she would give him a modest spanking, not the excruciating paddling of retribution he was now receiving.

Ms. Taylor kept up an even pace, harshly slapping one of his soft, tender cheeks, then the other, then both at once, right where the delightful curve of his cute bottom connected with his upper thighs. Occasionally, she would smack the same cheek twice, just to throw him off, so he never knew where her avenging paddle would land next.

Timmy had never experienced anything like this in his entire life, and he bawled like a baby, kicking his feet wildly and sobbing uncontrollably. This was definitely no fantasy spanking–it was the real deal, and each time the hard paddle painfully flattened his cute, round little cheeks, he howled out anew.

Abruptly and without warning, Ms. Taylor suddenly stopped and he lay there sobbing and struggling to catch his breath.

“Timmy? Tell me the truth–are you a bedwetter too?” she asked him.

Normally, Timmy would never have revealed such an intimate, humiliating secret to anyone, but being that he was in such a vulnerable position with her paddle raised over her shoulder, the boy was completely at her mercy.

“Y-yes, Ms. Taylor,” he sobbed shamefully.

“Just as I thought,” she said as she delivered a blistering hard swat to each of his punished, red cheeks. Scalding pain exploded as his bottom danced miserably to the blows of the hard wooden instrument of punishment she was wielding.

Timmy howled in agony, kicking his feet again as she at last stopped spanking him and began softly stroking his blazing, swollen bottom with her paddle.

“And how does your mommy handle your bedwetting, Timmy?” she asked evenly.

Timmy choked back his sobbing, struggling to make a coherent response as hot, salty tears dripped into his mouth.

“Sh-she m-makes me wear diapers to bed,” he cried bitterly.

“Well, sounds as if you should be wearing diapers during the daytime too,” she said as she set the paddle down on her desk and helped him to rise to his shaking feet.

Clearing a few items off of the top of her desk, Ms. Taylor pulled open a large drawer and placed three fluffy cloth diapers one on top of each other.

“Don’t you move a muscle,” she warned him even as his hands shot back to rub his inflamed bottom.

Stamping his feet in frustration, he cried like an errant toddler as he watched her prepare for his humiliating diapering like he was still a helpless baby. Backing him up against the end of the desk, she lifted him up and placed him on the stack of diapers, causing Timmy to wail in pain again as his hot, blazing bottom made contact with the soft cloth. Squeezing a large glob of diaper rash cream into her creamy hand, Ms. Taylor used her free hand to raise his ankles up over his head and began applying the cool substance to his roasting, swollen cheeks. Timmy choked back another sob, although the cool cream brought some small relief to his punished bottom.

Shaking a generous amount of baby powder all over his front, Ms. Taylor smiled down upon the distraught boy as she pulled the thick layers of Birdseye cloth up between his legs to pull the corners snug around his hips. A large, pink, bunny-headed safety pin was pushed through the cloth and clicked closed on either side, securing the diaper snugly around his waist.

“There Timmy…” she said with her ravishing smile, “This is how your mommy should have been dressing you for school every morning.”

Timmy’s feet were dangling over the side and Ms. Taylor tugged his trousers and underwear over and off his feet, folding them up neatly and placing them on her desk behind him. Reaching back into the open drawer, she pulled out a pair of baby blue nursery print plastic panties lined with playful white ruffles around the elasticized legs and waistline.

“Come on, Timmy,” she told him as she gathered the leg holes before his feet, “these will keep your wetting confined to your diapers where it belongs.”

Timmy sobbed with defeat as she threaded the shiny, infantile panties up over his ankles and knees, working them over the fat, bulky diaper pinned around his hips.

In ten short minutes, he had managed to completely destroy his reputation with her–the same one that he had worked so hard to build up with his pretty teacher, the woman he had idolized and fantasized about the entire year. Now she saw him as nothing but a childish bedwetter and one that belonged in diapers no less.

Powdering between his inner thighs, she grasped his hand and gently pulled him to his feet.

“Okay, Timmy, let’s take you home, I think you’ve had quite a day already.”

Taking him by the hand, Ms. Taylor led the sniffling, blushing boy from the room and guided him outside to where her car was parked. He knew that each waddling, humiliating step was taking him closer to his stern mother that would be expecting and waiting for him at home.

He could only imagine what she would say when she saw him, having been brought home by his teacher and wearing diapers and babyish plastic panties…he knew only too well, what to expect and what she’d say…

‘Timmy–you can plan on spending the entire summer in diapers.’

 

 

THE END

 

 

 

 

 

 

 

 

 

The Last Straw

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 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 he 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, with 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,” 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 warned 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 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

Trading Panties for Diapers

 

 

 

 

Making sure the address matched the note his mother had written for him earlier, Jimmy set his suitcase down on the front porch of the suburban home and rang the doorbell with some trepidation.

His mom was leaving the state for the summer and she had left the care of her prissy, innocent 12 year-old son to her younger sister, Tess. Jimmy was familiar with his aunt, although not that familiar, as he’d only visited her a few times during the last several years. Still, she had seemed nice enough, and from a physical standpoint, she was beyond reproach. Jimmy could still recall the many times he had been caught red handed, leering at her busty profile when he thought she wasn’t looking.

As he was waiting at the door for her to answer, he thumbed the sealed envelope once more in his hand that he had been instructed to give to his aunt.

What had his mother written about him? he wondered anxiously, not for the first time.

After a moment, he heard footsteps approaching and the door swung open to reveal his pretty aunt smiling down upon him.

“Well hello there, Jimmy!” she exclaimed.

She stepped out onto the porch and bent down to hug her slight and diminutive nephew.

“Come on inside!” she invited him warmly, “How was the bus ride over? Any troubles?”

Jimmy was very shy by nature, and suddenly he felt rather overwhelmed by his gorgeous, voluptuous, and much taller aunt. By and large, he was unaccustomed to getting a lot of attention, particularly by attractive females, and he found himself at a loss for words.

Jimmy’s cheeks reddened and after mumbling something incoherent, he thrust out the envelope to aunt Tess.

“M-my mom said to give this to you,” he said, trying without success to avoid staring at the long line of deep, sexy cleavage disappearing down the front of her snug top.

“Okay, sweetie,” she said as she took the envelope and ran her long, glossy nail under the flap to open it.

Taking out the single hand written page inside, she unfolded it and read it over;

Hello Tess,

Thank you so much for taking in Jimmy for the summer months. He really is a well behaved boy and I’m sure he won’t give you any cause for concern.

As you know, Jimmy sometimes wets his bed, so I’ve taken the precaution of packing his waterproof mattress cover in his things. I’m sure it’s just a phase that he’s going through and will soon be over. Please put the cover over his mattress tonight and I’m sure everything will be fine.

Also, and I know this may sound strange, but over the last couple of years, Jimmy has become particularly interested in, of all things…panties.

I’ve been allowing him to wear them under his regular pants, but I will leave it to you as to how you’d like to handle this new desire for women’s clothing. It seems harmless enough and so long as it doesn’t go any further–I’m okay with it.

 

Aunt Tess looked up from the letter to see her nephew fidgeting nervously. To be sure, she intended to continue having him wear panties, although undoubtedly, not in quite the way he was expecting…

Two more things; I’ve packed his favorite teddy bear in his suitcase. I know he is rather old to still be clinging to such a silly thing but he becomes very upset if he doesn’t get it at bedtime.

 Lastly, while sleeping, Jimmy sometimes sucks his thumb.

I’d really like to break him of that habit, for a number of reasons, but so far, I’ve been unsuccessful. Hopefully, you will have better luck…

 Love, your sister,

 

Samantha

 

Aunt Tess folded the paper carefully and she eyed her anxious nephew, silently imagining him sucking his thumb like a infant.

I can think of the perfect remedy to solve that little problem, she reflected.

Taking him down the hallway, she led him into a warmly lit room that looked more like a baby’s nursery than a spare room. A large pink and white crib stood in the corner and nursery print designs decorated the walls. A lemon yellow rocking horse stood waiting for it’s next rider and a number of childish dolls sat atop a brightly pink colored dresser.

Jimmy quailed at the thought that this was where he would be sleeping but he was simply too shy to speak up about it.

Inwardly, he cursed his lack of backbone.

He was also acutely aware of the distinctive smell of stale pee, like wet diapers and vinyl panties that had been used so often, they forever retained the odor. He was deeply ashamed that his aunt might think he needed such precautions and for the first time, he found his voice.

“A-aunt Tess?…I-I won’t be sleeping here, will I?” he asked timidly.

His beautiful aunt bent down to look him in the face, holding his trembling hands in hers. “Yes sweetie, this is where I keep all the little bedwetters that come to stay with me. But don’t you worry–I have just the thing to take care of your problem.”

Jimmy’s cheeks flushed a bright red and he almost choked.

“I-I’m not a-a bedwetter,” he squeaked, the anxiety rising in him. The lie came automatically to him but instinctively, he feared she knew his shameful secret. Could that be what the note said? he wondered.

“Honey, we both know you are and I have some very special ways to help you with it.”

As Jimmy gazed down at the thick stacks of soft, fluffy cloth diapers nearby a changing table, he gulped with fear but he was afraid to ask further.

He certainly didn’t want to give her any ideas!

“Now–don’t you worry your little head about any of that,” she said as she playfully mussed up his hair, “I’ve got dinner all ready for you and you can tell me all about your school year and the TV shows you’ve been watching.”

Without waiting for an answer, she led him out of the room, back down the hallway and sat him down at the kitchen table.

Jimmy was still feeling flustered as his aunt placed a plate of steaming lasagna before him, along with a bowl of salad. It had been a long day, and the scent of wonderful food distracted him from his immediate concerns. He dove into his dinner with abandon and soon, the two of them were engaged in an upbeat and light hearted discussion about all manner of things.

After they’d finished and aunt Tess had cleared away the dishes, she came over and took Jimmy by the hand.

“Okay sweetie, let’s get you ready for bed now.”

“A-already?” the effeminate boy whined. It wasn’t even 8:00 yet.

“Yes, you can stay up a little longer but I want to have you all ready ahead of time,” she explained patiently.

Jimmy couldn’t think of why it was so important that he get into his jammies so soon, but he didn’t argue as she led him back down the hallway to the nursery.

He expected her to open his suitcase to retrieve his Power Rangers pajamas but instead, she sat him on the edge of a raised diaper changing table and began untying his shoes. After removing those and his socks, he watched with growing concern as she began undoing the snap on the front of his pants.

“I-I can do it,” he whimpered uncertainly, not used to having someone else taking his pants off for him.

“That will be quite enough of that, young man,” she warned him sternly as she slapped his hands away.

Jimmy wasn’t used to strong authority figures outside of school but he sensed that he probably shouldn’t do anything to anger his aunt.

She continued her ministrations, tugging his jeans down his legs and exposing the lacy pink panties he was wearing underneath.

He blushed hotly and was worried for her reaction but she only smiled at him saying; “Don’t worry, sweetie, your mommy told me all about your interest in panties, and I’ll make sure you’re wearing some the whole time you’re here.”

She chuckled to herself at her private joke as she folded his pants, putting them aside.

Jimmy was somewhat relieved to hear that but he also had a creeping suspicion that his aunt had something else up her sleeve.

Tucking a long nailed finger into the delicate waistband of his panties, Tess suddenly yanked them down as Jimmy let out a gasp of surprise.

“Wha-what are you doing?” he quaked.

“In this house, bedwetters wear diapers and plastic panties,” she told him firmly as she looked him in the eye with steely resolve. Her stern look seemed to be goading him to defy her and out of the corner of his eye, Jimmy spied for the first time, a wooden paddle lying next to the crib.

Jimmy blushed furiously as his hands shot down to cover his still hairless genitals.

“B-but I don’t need diapers,” he cried piteously.

Taking a thick stack of three fluffy diapers in her hand, Tess lifted the poor abashed boy’s ankles up together and slid the baby soft cloth under his curvy rump.

“I’ve found that the best way to deal with bedwetters is to keep them in diapers and plastic panties,” she repeated as if his claim was meaningless.

Jimmy bunched his fists in mute frustration. His mom had never used diapers for his problem! Did his aunt think he was nothing but a big baby?

While keeping the whimpering boy’s ankles aloft, she dipped her free hand in a large jar of Desitin and smeared it across his quivering bottom. Between being exposed to the cool air and the even cooler diaper rash cream, Jimmy shivered a little until she set him down and began powdering his front.

His eyes misted with tears as he realized with humiliating finality that he was going to be diapered like a toddler by this strong-willed woman no matter what he said. As the crushing realization washed over him, he cried softly but lay there submissively, resigned to his fate.

Taking a pink pair of clown safety pins, aunt Tess pulled the bulky ends of cotton together tightly around his slim hips and pinned them closed. Jimmy was amazed at how thick the cloth was and he could barely bring his legs together.

Selecting a lilac pair of translucent plastic panties, Tess gathered the leg openings and began working them up Jimmy’s trembling legs. He whimpered in defeat as he watched his humiliating new panties being pulled up his legs and then worked around the fat diaper swaddling him.

“There…” she said slowly with satisfaction, “These will keep my little sugarplum’s bed dry.”

Jimmy blushed again, feeling very babyish. His nose was assailed by the twin infantile scents of baby powder and stale pee and he was mortified having just been pinned into pampers like a helpless baby. Worse yet, was the virtual certainty that some of these items must have been previously worn and wet by someone else. He felt totally ashamed.

After running her fingers around the elastic waistband of the shiny panties to tuck his diapers in, Tess sat back and smiled down with satisfaction at her blushing, embarrassed nephew.

“There you are–all set for beddie-bye. Why don’t you go brush your teeth and then you can watch the TV for another half hour.”

Jimmy’s heart sank at the thought of having to go to bed at such an absurdly early hour–he was used to 11:00 pm at home and yet, it was barely 8:00 here!

Standing up, he almost lost his balance as the imposing diapers conspired to keep his legs apart. The closet doors on the opposite wall were mirrored and as the sissy boy gazed at his babyish reflection, he nearly burst into tears. What would his friends say if they could see him now??

He fled out of the room as quickly as he could waddle, the fat cloth feeling slippery between his legs but inhibiting his stride nevertheless.

After brushing is teeth, Jimmy went into the living room to watch a show that was playing on the TV, but he found it hard to concentrate on what was happening on the screen. He was extremely conscious of the strong scent of baby powder surrounding him and he couldn’t get used to the feeling of his hips being wrapped in bunny soft cotton. He felt so immature and babyish that his aunt had decided to put him back in diapers as a solution and waves of humiliation swept over him, one after another. Obviously, all these years, she had thought of him as nothing more than a sissy bedwetter.

Fidgeting in place while lying on the floor, the plastic panties crinkled with his every move, constantly reminding him of his shameful, infantile underwear.

Before he knew it, the half hour had passed and his aunt came into the room to retrieve him.

“Okay Jimmy, it’s beddie-bye time,” she said as she reached over and unceremoniously shut off the TV.

Jimmy’s heart sank and reluctantly, he rose to his feet. Patting his fat, diapered bottom affectionately, aunt Tess guided him back to the nursery. After sitting him on the edge of the crib, she removed his t-shirt but instead of opening his suitcase, she went to the pink dresser instead, sifting through a drawer until he held up a white and pink top.

“Here, I think this will do just fine,” she proclaimed happily.

Bringing it over, Jimmy could see it was a fuzzy fleece top, with short, puffy sleeves and a baby bear motif across the chest. It looked just like something a  toddler would wear.

Shaking his head, Jimmy held his hands out in protest.

“No!” he said fussily, “I want to wear my own jammies.”

He was humiliated and angry and he was going to stand up to her right now.

“Young man–in this house–I determine what you will wear. If you have a problem with that, I have no problem with putting you over my knee where we can continue this discussion,” she said firmly.

Jimmy’s mouth dropped open in shock–he had never been spanked by his mother and the prospect terrified him! Thrusting his lower lip out in an epic pout, he dropped his hands in defeat, accepting the top, as she fitted the soft garment over his head, pulling the short hem down until it almost reached his waist.

“It’s not fair,” he whined petulantly under his breath.

Ignoring his comment, aunt Tess grabbed a large pink rubber pacifier and bending down to his level, she slowly began pushing it between his trembling lips.

“That’s it…that’s my baby,” she smiled as he submissively accepted it.

He could smell her perfume surrounding him and as he gazed down her top at her big, round breasts, he felt very intimidated.

Helping him under the soft baby blankets, Tess tucked the squirming boy in and then remembered his teddy bear. Going over to his suitcase, she reached inside and took it out, putting it between his arms before raising the side rail of the crib.

“There you are sweetie,” she smiled down at him, “Have a good night.”

Jimmy hugged his teddy bear like his life depended on it as he sucked the rubber pacifier filling his mouth. Aunt Tess turned on her heel and walked out of the nursery, turning the lights out as she went. Filled with anxiety and uncertainty, Jimmy tossed and turned in the crib until he finally gave way to slumber.

 

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

 

The next morning, Jimmy awoke to the window curtains in his room being pulled back. Bright sunlight streamed into the nursery and he looked up to see his beautiful aunt smiling beatifically down upon him. She was happy to see the pacifier still in his mouth, and she smiled at his innocent, baby-like countenance.

“Good morning, sweetie!” she said brightly, “How did you sleep?”

Jimmy had to admit that he’d slept very well–the bed was soft and comfortable, with the slight exception that every movement was followed with the crackling of the waterproof mattress cover beneath him.

Lowering the side of the railing, aunt Tess took his hand and led him out of the crib, sitting him gently down on the changing table. It was only then, as the thick, soggy Birdseye cloth of his diapers squished against his rump that Jimmy realized to his horror, he’d helplessly soaked them during the course of the night. He blushed hotly as he anticipated her discovering the shameful fact any moment.

Putting a finger on either side of the elastic waistband of his plastic panties, Tess tugged them down, exposing the sopping wet cotton pinned around his hips. The humiliating smell of pee surrounded them and Tess gave him a knowing smile.

“Just as I expected,” she stated with conviction.

Jimmy looked away in mortified embarrassment as she unpinned the wet cloth and dumped it with a heavy thud into a nearby diaper pail. She used some moist towelettes to clean his damp bottom and front before raising his ankles to slather his cheeks with another sticky coating of Desitin.

As the realization struck him that she fully intended to pin him into another set of diapers, the embarrassed boy suddenly spit out his pacifier.

“Wa-wait! Wha-what are you doing??” he cried frantically.

“Jimmy–we’ve already had this discussion,” she explained patiently, “As I said last night, when I have bedwetters staying with me, I keep them in diapers and plastic panties,” she told him as she slid a fresh trio of thick diapers beneath his upraised bottom, “That’s where you belong, and that’s what you’ll wear while you’re here.”

“B-but–I-I don’t wet during the day!” he wailed desperately, trying in vain to kick his ankles free of her grasp.

“Jimmy–these will be your underwear from now on. Until you stop wetting the bed, you can depend on wearing diapers and plastic panties indefinitely,” she told him firmly.

Jimmy burst into tears but his aunt only continued her ritual of changing him, powdering him generously before pinning the soft, bulky cloth around his hips. After pushing the pacifier back between his squalling lips, she chose a cute pair of white nursery print plastic panties and pulled them over his feet. With practiced movements, she tugged them up his hairless thighs and worked them over the fat cotton cloth surrounding his hips.

Jimmy cried to himself as she put some short socks on his feet and tied his sneakers in place.

“I’ll let you get yourself together while I make your breakfast, sweetie,” she said kindly. Bending down, she kissed him on the forehead, granting him a heart stopping view down her top.

Gazing at his humiliating reflection in the mirrored closet doors, Jimmy burst into fresh tears of self pity. What was he to do now? To think that he’d have to spend his entire summer, dressed like a baby in diapers and plastic panties! It was too much to bear!

 

 

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

 

To be sure, it was a big adjustment for Jimmy, getting used to wearing his embarrassing diapers not only at night but also during the day. And it wasn’t like wearing a watch, that one quickly gets acclimatized to. He was constantly aware of the slippery squish of soft, bulky cotton between his thighs as he waddled about and the extra padding every time he took a seat.

The whole experience made him feel not just childish, but very babyish and he cringed every time he passed a mirror and saw his shameful reflection.

He also felt like Tess treated more like a four or five year-old boy, instead of the 12 year-old that he really was.

However, other than the somewhat draconian measure of being diapered and sleeping in a baby’s nursery, Jimmy found living under aunt Tess’ roof to be, all in all, very enjoyable. She gave him lots of attention and it was obvious she was happy to have him around. She was eager to spend time with him and they often played games around the house together.

 

 

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

 

When aunt Tess walked into the house, she found her sissy nephew lying on the floor, a box of crayons arrayed before him as he intently drew in his Trucks-For-Tots coloring book. His legs were spread apart and his feet were crossed behind him, while his snug, shiny plastic panties stretched over the very fat diaper he was wearing.

Sitting patiently next to him was his familiar teddy bear, happy to be included in his activities.

As soon as Tess came in the door, Jimmy scrabbled to his feet and waddled over to her, eager for his daily hug.

“Aww, that’s my little baby,” she commended him happily, as she held him to her soft, cushiony chest.

Without thinking, she reached down and slipped her fingers inside of his waistband to check his diaper for wetness but as usual, he was dry.

Jimmy had settled into his new home comfortably and over the few weeks since his arrival–and like all true sissies, he’d gradually becoming accustomed to wearing diapers 24 hours a day.

His claims to the contrary not withstanding, Jimmy managed to wet his bed every single night in his crib; waking up sheepishly to pee-soaked diapers in the mornings and his aunt, who clearly expected nothing less from him.

During the day, Jimmy was allowed to use the restroom for his needs, but he was required to summon his aunt whenever he felt the need to go. She would stop what she was doing, take him to the bathroom, and pull his diapers down long enough so he could do his business. After that, she pulled them back up and with a friendly slap of dismissal on his well padded bottom, Jimmy was free to go about his day.

Nevertheless, regardless of whatever he was wearing, aunt Tess made sure his fat, embarrassing diapers were always clearly on display. She felt it was important that they be seen at all times and she refused to let him cover them with any other kind of clothing. This was to make sure there was no doubt to anyone that saw him that her little nephew was a well-diapered sissy.

And every Sunday, Tess had a routine set where she would come into his nursery, undo his diapers, and give him what she called a “cleansing enema”; a quart and a half of warm, soapy water she patiently administered into the squirming sissy’s bottom before releasing him to go to the bathroom.

Jimmy didn’t like these enemas, which were always conducted over her lap as she admonished him to try harder in controlling his bedwetting. They were uncomfortable and extremely humiliating for the effeminate boy but he knew better than to put up a fuss. He had seen aunt Tess’ wooden paddle, and he didn’t want to find out what it felt like, firsthand.

Indeed, Jimmy had accepted everything about his life with hardly a quibble. Perhaps it was his weak, sissy nature that he fell so easily into a regime that was not that much different from a toddler’s.

And so it was that Tess was so pleased with his docility and willingness that she went out and purchased a gift for her bedwetting nephew.

“You’ve been such a good little boy these last few weeks that today I got you something I hope you will like,” she explained to him as she briefly turned her back on him to reach into her purse. Turning back around, she held forth a light, pink pair of rumba panties, decorated with three flouncy rows of ruffles across the seat.

“Here you are sweetie–your very own rumba panties–aren’t they darling?”

Jimmy blushed deeply but inside, he was secretly pleased. He missed wearing his girly panties and these were likely to be as close as he was going to get to his former fetish.

“And they’re cut nice and full, to fit over your big diapers–isn’t that neat?” she asked enthusiastically. Tess was nothing if not pragmatic.

Jimmy felt a strange mix of both shame and arousal. He was humiliated that the only way he’d be able to enjoy his fetish was over his embarrassing “protection”, but he nevertheless nodded silently as he stood before her.

They were made of a thin, stretchy nylon and aunt Tess held them low so he could climb into them. Once his feet were inside the leg holes, she began slowly drawing them up his baby smooth legs. He held onto her shoulders for balance as she tugged them lightly, pulling them up over the fat, bulging diapers pinned around his hips.

“There you are…oh, they’re a perfect fit too! Let’s go look in the mirror,” she said eagerly.

Taking him by the hand, she led him down the hallway to his nursery where the two of them stood before the mirrored closet doors. Jimmy was still blushing brightly and Tess took the opportunity to grab his pacifier and push it into his mouth, completing his babyish look.

“What a good little sissy you are,” she told him proudly as she patted him on his fat, ruffled bottom, “I think I need to get a nice, cute little baby dress for you. How would you like that?”

Jimmy’s cheeks blazed and he shook his head but Tess only chuckled and beeped his nose playfully.

 

 

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

 

 

Things went smoothly for a month until one day in late June, when Jimmy happened to be out in the back yard, playing with his Tonka trucks. The yard was surrounded by a tall wooden fence, so there was very little chance of him being seen by the neighbors.

His aunt had dressed him in a short top with bunnies on it, his usual diapers, and his sneakers.

Tess was in the kitchen, re-arranging some canned goods when she saw Jimmy suddenly come in through the sliding glass door, sobbing loudly, his face wet with tears, and an obvious scuff on his right knee.

Aunt Tess dropped what she was doing and came over to hug her diapered and distraught nephew, pressing his wet face against her pillowy, soft bosom.

“Aww, what’s the matter baby? Did you skin your knee?” she asked, full of maternal concern.

Jimmy nodded, his crying unabated.

Taking a seat next to her, Tess carefully guided the prissy boy onto her lap to comfort him. It was then, as she felt him settle his weight upon her lap, that she suddenly felt the distinctive warmth through the thick seat of his diapers and plastic baby panties upon her thighs. Obviously, he had managed to wet himself during the traumatic incident.
Reaching over to the near counter, aunt Tess picked up a baby bottle of milk and slowly pressed it against Jimmy’s trembling lips.

“Here you are baby,” she said soothingly, “This will make you feel better.”

Jimmy nursed from the bottle, looking much like any diapered toddler in his mother’s arms as his crying was gradually reduced to sniffles.

With her free hand, Tess slipped a couple of fingers down the back of Jimmy’s baby panties, feeling the warm, pee-soaked cloth inside.

“Looks like my little boy wet his diapers,” she told him sympathetically.

Jimmy hadn’t even realized he’d done it and he blushed red with shame and whimpered a bit as he kept his eyes downcast.

“That’s okay baby, you just finish your bottle and then we’ll get you changed into some fresh pampers.”

Leaning forward, she kissed his forehead lightly in a show of comfort and affection. At the same time, her action served to fill his entire forward view with her big, round breasts and cleavage, displayed inches before him in her clinging, white halter top. He whimpered again, this time with sexual angst, staring at the soft curves of her bountiful chest, wishing he could somehow have her.

As the last milky bubbles drained from his bottle, Tess eased it from his lips and stood him up.

“Okay baby, let’s go change those wet diapers and then it will be naptime for you,” she told him as she squeezed the sissy’s thickly padded seat.

Jimmy squealed a little but he clutched her hand as she led him down the hallway to his nursery.

 

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

 

 

Two weeks later, another event happened that made for a big impact, both figurative and literally on young Jimmy.

It was late in the afternoon and aunt Tess was just coming into his nursery to wake her charge up from his daily nap. Looking down on the still sleeping sissy, she smiled to herself as she watched him for a moment, contentedly nursing from the pacifier still lodged in his mouth and his teddy bear tucked under his skinny arm. To be sure, since she’d begun training him with a pacifier, he hadn’t once gone back to sucking his thumb.

Lowering the crib rail, she gently pulled back the soft, fuzzy Disney Princess blankets as Jimmy’s sleepy eyes fluttered open.

“Good afternoon, baby,” she greeted him cheerfully, “Did you have a nice nap?”

Jimmy nodded, his eyelids still sticking a bit.

With practiced ease, aunt Tess helped him out of his crib and gently set him down on the changing table. Removing his pacifier, Tess replaced it with a baby bottle filled with warm milk, which she let Jimmy hold for himself. Tugging his clinging rubber panties down off his soggy diaper, Tess tossed them in his diaper pail before unpinning the wet Birdseye cloth.

Jimmy was still blinking sleepily as she pulled the pee-soaked cloth from under him and put it aside.

In just a few minutes, Jimmy was powdered and pinned into a fresh set of diapers and a new pair of plastic panties pulled up around his hips. After tying his sneakers on, aunt Tess beeped his nose and left him to his own devices in the nursery.

After he’d finished his bottle, Jimmy waddled out of the room to return it to the kitchen. It was only then, that he realized aunt Tess was entertaining one of her friends.

He froze in his tracks and nearly dropped the baby bottle in his hands. In his half awake state, he must have missed their conversation from down the hall.

All eyes turned to him as his mouth opened in shock.

Unfortunately, the surprise of being seen dressed like a toddler in pampers was too much for the young sissy and he promptly flooded his diapers in a helpless torrent.

Feeling the hot, urgent pee suddenly warming the front of his diapers, Jimmy cried out in panic.

“Oh!” he exclaimed in his high pitched voice.

“Hi Jimmy–I forgot to mention, this is my friend Katie,” Tess said as if it was the most ordinary thing in the world, “Come over and say hi.”

Jimmy blushed hotly, feeling very childish, not only for being seen in his sissy diapers but also for having just wet them like an incontinent baby. Tears of shame filled his eyes and he was on the verge of a full blown cry when aunt Tess stood up and quickly embraced the poor child.

“There, there, baby,” she comforted him as she hugged him closely, pressing his cheek against her mammoth bosom, “Don’t be shy.”

Jimmy choked back a sob. Ordinarily, he might have confessed his wet condition to his aunt but he certainly wasn’t going to say anything now.

“Don’t worry honey, Katie knows all about your bedwetting,” Tess explained  as she patted his fat, diapered bottom to sooth him.

That’s right, Jimmy,” her friend chimed in, “Some little boys just aren’t ready for big boy underwear and they need to stay in diapers longer.”

Jimmy blushed hotly, feeling the heat all the way to his ears.

How many people has she told about my bedwetting? a voice was screaming in his head.

And he didn’t like being called a little boy. He was almost thirteen years old already!

Of course, his appearance wasn’t helping the situation, given that he was wearing a fuzzy fleece diaper shirt adorned with a motif of building blocks and a short, ruffled hem that barely extended to his navel. The pacifier hanging from his top and the baby bottle in his hand only added to the impression of being an overgrown, diaper-dependant toddler.

Of course, Katie’s humiliating appraisal of him was spot on but it was nevertheless devastating to the fragile boy’s ego to hear it put in such frank, condescending terms.

Just then, the kitchen sliding glass door to the back yard opened and a cute girl who looked to be 10 or 11 came through. She looked about ready to say something to her mom, when she suddenly came face to face with Jimmy.

Apparently completely unprepared for this unusual sight, she abruptly burst into giggles as she looked him up and down.

“You’re wearing diapers!” she squealed in her little voice.

This unexpected arrival to the scene only caused another strong burst of warm pee to flood unchecked into Jimmy’s already wet diapers.

His mouth trembled as his cheeks and chest burned with hot, flushed intensity while he struggled to find words to say.

“Now Mikayla,” her mother chided her, who also happened to be trying to suppress her own smile, “Jimmy has a little bedwetting problem. You are not to tease him about it.”

Although theoretically said on his behalf, Jimmy was mortified by the entire situation. He wanted more than anything to run away, or at least waddle, as fast as he could go–to anywhere else.

Aunt Tess seemed to sense it, and she bent down to his level to speak sweetly in his ear.

“Honey? Why don’t you and Mikayla go and play in the living room? I know she’d love to have someone to help her with her dollhouse.”

Gazing across the room in a daze, Jimmy spied a large dollhouse on the floor, with numerous dolls awaiting a collection of outfits.

“I don’t want to play with any stupid dolls!” he suddenly burst out angrily.

He just wanted these two to leave, and he didn’t want to do anything to condone or contribute to the situation.

At that moment, aunt Tess summarily yanked him around to face her and she wagged her long nailed finger at him.

“Now you listen to me, young man,” she said sternly, “I know you’re upset at being seen in your diapers and plastic panties but you’re just going to have to get used to it. Until you stop your silly bedwetting–this is how everyone is going to see you.”

Hot tears of shame tumbled down Jimmy’s face as his aunt continued to scold him before the others.

“These two people are my good friends and you had better learn to get along unless you’d like to spend the rest of the afternoon with a hot, stinging bottom.”

As Jimmy choked on the ominous threat, Tess emphasized her point by roughly turning him around and delivering a hard swat to his diapered bottom.

“Oh!’ he cried.

He blushed furiously as everyone looked at him.

Mikayla stood up a little straighter and smiled at seeing this older sissy boy being humiliated and castigated before her. She was an attractive young girl and one could tell that someday, she would be a real beauty.

With a sob of resignation, Jimmy trudged over to the dollhouse and sat down with a warm, wet squish in his seat. Mikayla followed and in no time at all, she was bossing him around, confident of her own superior social position.

However, this soon devolved with Jimmy becoming more resentful and angry by the minute. Mikayla was teasing him and calling him a ‘diaper boy’ which only heaped further shame on the poor sissy.

At last, Jimmy could take it no longer. Taking one of the dolls, he brought it down violently on the edge of the roof of the doll douse, snapping it’s little plastic head off.

Mikayla reacted with shock and disbelief as she burst into tears.

Jimmy was yelling at her and oblivious to his surroundings when he suddenly felt himself being physically yanked to his feet by his wrist.

“You’ve just earned yourself a good, hard spanking,” aunt Tess snarled as she jerked him over to an armless chair nearby.

Jimmy shuddered and his eyes widened as he saw she was now holding the stout wooden paddle in her hand, ready to bring swift retribution to the diapered pantywaist. As Tess angrily tugged his plastic panties down, he let out a squeal and let loose with another hot stream of pee into his diapers.

“No-no-no!!” he cried, flailing his arms before him in a futile gesture to make her stop. With his waterproof panties below his knees, Tess threw him over her lap, quickly unpinning his warm, sopping wet diapers and pushing them back between his thighs to give her an unobstructed access to his youthful bottom.

A string of incoherent statements piled out of his mouth in a tumble as he tried to defend himself.

“Y-you can’t do this–sh-she started it–she was the one–“

–SMACKKK!!!

The paddle landed flat across his damp cheeks and Jimmy wailed like a little girl at the top of his lungs. Two more harsh, crisp swats scalded his tender rump, searing a bright red oval pattern across both his curvy little cheeks.

Jimmy kicked his feet wildly, slapping his hands against the floor as he tried in vain to get up off her lap. However, aunt Tess was obviously not one to be trifled with. She used her free hand to hold him securely in place while her paddle viciously struck it’s target again and again with harsh, blistering slaps. It stung terribly and Jimmy was bawling his eyes out, now regretting the day he’d ever arrived at his aunt’s house.

Katie and her daughter sat silently, watching his punishment with obvious approval and satisfaction. To be sure, Jimmy was at the very bottom of this totem pole in social standing.

Tears of bitter frustration at the unfairness of his spanking poured down his face–why was it he was the one being punished while Mikayla got away scott-free?

Every time he thought the spanking couldn’t get any worse, another hard, angry swat landed on his bright red bottom, making him howl in agony and bringing forth fresh tears. They spilled down his cheeks and dripped on the floor as he kicked his feet frantically. He’d never been spanked like this in his life and he wailed helplessly as the hard wooden paddle continued to slap his stinging, blazing cheeks.

At last, the terrible punishment was over and Jimmy lay across her lap, too weak to move.

With surprising gentleness, aunt Tess lifted the crying sissy to his feet and hugged him closely as his wet diaper fell away, leaving him nude from the waist down.

“There, there baby,” she consoled him as she pressed his face against her big, soft breasts, “Don’t cry sweetie.”

However, her words had little effect on the spanked youth as he only sobbed louder, desperately rubbing his red, blotchy, swollen bottom with his hands.

“Katie–can you get me his baby bottle from the warmer there?” she asked her friend, “Yes, that one…thank you.”

Taking the bottle filled with milk, Tess eased it into Jimmy’s crying mouth which was salty from his tears.

Feeling both defeated and very babyish in front of them, Jimmy accepted the wet nipple and began nursing from it. He realized all too well, that in a battle of wills, he stood no chance whatsoever against his aunt.

As before, the rubber in his mouth had a calming effect and his crying abated somewhat, becoming ragged sniffles.

“We’d better get this little sissy back into his diapers,” Tess said sagely, “There’s no telling when he might have another accident.”

Leading him by the hand, with Jimmy doing his best to shuffle while his damp plastic panties were still around his calves, the four of them went down the hallway and into his nursery. Once there, the pungent smell of Jimmy’s diaper pail advertised to one and all that an incontinent bedwetter lived in the room.

“This is a lovely room you have for Jimmy,” Katie exclaimed glowingly, “Everything a little boy still in diapers could ever want.”

Aunt Tess smiled proudly.

“His mommy told me about his desire to wear little girl’s panties but as you can see–he’s much too immature to handle that responsibility yet.”

“Oh yes,” Katie laughed, as she bent down to face the boy nursing from his baby bottle, “I’m afraid you’re going to need diapers and rubber panties for quite some time, baby boy.”

Jimmy didn’t like Katie and his cheeks blazed red with shame under her condescending remarks.

“Can I help change him?” Mikayla offered, not wanting to be left out.

“Absolutely!” aunt Tess told her, “Go and pick out a pair of plastic panties for Jimmy. They’re in that stack over there.”

Jimmy was mortified to be the center of everyone’s attention, especially during this most humiliating of rituals. He squirmed and fidgeted on the changing table, his embarrassing, tiny little bald genitals and red, stinging bottom on display for everyone to see.

Nonetheless, the blistering spanking had taken all of the fight from him and Jimmy was now more than willing to cooperate with whatever aunt Tess deemed necessary.

Seeming to know that she had him right where she wanted him, Tess undid his shoes and removed them along with his socks. She soon replaced them with lacy pink anklets and a glossy white Mary Janes.

Grasping him by his ankles, aunt Tess swung his girly-smooth, sissy legs up over his head and began applying a nice, sticking coating of Desitin to his bright red bottom.

“I’m afraid that’s going to hurt for several days, sweetie,” she told him as she slid a new, thick stack of fluffy fresh diapers under his white and red cheeks, “But sometimes little boys need to be taught a lesson.”

Jimmy whimpered and drained the last of his bottle.

“All finished?” Tess asked, “That’s a good baby–here’s your paci now,” she said as she pushed the rubber nipple into his mouth.

Jimmy dutifully accepted the pacifier as Tess powdered him all over his front and between his legs.

“Jimmy really wets a lot, so I use thick soaker pads between the layers of his diapers,” she explained to her friend, “It means his diapers are too thick to be able to put regular clothes over but that’s okay–I want to make sure everyone sees them anyway.”

“I couldn’t agree more. A sissy boy like he is should always have his diapers visible.

“Jimmy–you’re very lucky to have such a loving aunt like Tess here who knows just how to handle bedwetters,” Katie told the blushing boy.

“How about these?” Mikayla said brightly as he held forth a cute pair of pink polka dot plastic panties. Delicate white lace edged the leg holes giving it a  look of girlish, toddler fanciness.

“Wonderful!” Tess praised the beaming child.

Gathering them in her hands, Tess worked them up the prissy boy’s hairless legs and then over his big, imposing diapers.

“There! All safe and secure now, babykins!” she said, hugging the befuddled sissy.

In his heart of hearts, Jimmy was beginning to realize that he could no longer be entirely trusted not to wet himself, even during the day, and as humiliating as these were, they were also very necessary. Of course, even if he had felt otherwise, the large rubber pacifier filling his mouth made any kind of coherent speech impossible.

“I think I’ll take my highchair out of storage so I can have a place to keep Jimmy while I’m preparing his dinner,” Tess told her friend as she led her babified nephew out of the nursery and back into the kitchen.

Ten minutes later, Jimmy found himself strapped into a baby’s highchair, with a plastic tray snapped in front of him. Aunt Tess poured several jars of baby food onto a plate and after tying a colorful bib around his neck, proceeded to start feeding him.

“You know,” Katie offered as she watched the sloppy process taking place, with baby food spilling over his chin and bib, “I still have a playpen I can let you have–it would be a great place to put Jimmy where you can also keep an eye on him.”

“Oh thank you! That would be wonderful!” Tess exclaimed enthusiastically.

“You hear that?–” his mommy asked excitedly, “Now you’ll have your very own playpen–and it’ll be a really big help to me so I’ll know where you’re at and know you won’t be getting into any trouble.”

Jimmy felt like he was sliding inexorably down a slippery path to complete babyhood but his bottom was still blazing like a five alarm fire. The last thing he wanted to do was defy her again.

Instead, Jimmy swung his legs uselessly as she continued to shovel large portions of creamed corn into his mouth with a large, plastic spoon. It slopped on his chin, around his mouth, and down onto his plastic Barney bib which Tess would then scoop up and re-feed him.

This babyish and unappealing meal was followed up with a large bottle of warm milk which Jimmy nursed as the women talked amongst themselves.

Some time later, when he had finished, he was feeling quite ignored and bored, and he tried unsuccessfully to stifle a yawn.

“Is baby tired?” aunt Tess suddenly asked him, “I think an early bedtime is just what you need.”

Jimmy shook his head vehemently.

“No! I don’t wanna go to bed,” he whined petulantly.

Indeed, it was only just after seven.

“Come along baby, let’s get you ready for beddie-bye,” she told him as she unlocked the tray and led him down the hallway to his nursery.

Once there, Jimmy pouted angrily, stamping his feet in place as his aunt removed his diaper shirt and replaced it with a soft, fuzzy yellow onesie. It had a delightful bunny appliqué on the chest and even a poofy ball on the seat.

“But I don’t wanna go to bed,” the fussy pantywaist repeated.

Tess pushed his pacifier into his quivering mouth and patted him on the head with a smile. Checking his diapers, she pronounced him dry and tucked him into his crib, along with another baby bottle and his teddy bear. Turning the lights out and closing the door to his nursery, Jimmy was left with his Tinkerbelle nightlight.

Down the hallway, he could hear Mikayla’s high pitched giggles and he bitterly resented that he had been sent to bed much earlier than the younger girl.

Jimmy tossed and turned in the crib, the crackly waterproof mattress cover and the ever present smell of the nearby diaper pail reminding of his childish status as he stared up at the ceiling.

At last, the bedwetting sissy finally fell asleep.

 

 

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

 

 

As the days progressed, and Jimmy became accustomed to an increasingly more babyish lifestyle, he found himself wetting his diapers with greater frequency during the day. Perhaps it was the constant wearing of his infantile underwear or his aunt’s childish treatment of him but he found his already tenuous control over his bladder gradually slipping away.

Meanwhile, aunt Tess was, bit by bit, transforming his wardrobe to a more feminine style, albeit, that of a little toddler girl. Frilly baby dresses and tops became his daily wear and it was supplemented by occasional gifts from her friends like Katie, who reveled in seeing the sissy boy treated like a baby.

Being the true sissy that he was, Jimmy put up only token resistance, although even if he’d been inclined to stand up to his aunt–in a war of wills–Jimmy was hopelessly outmatched.

And although Jimmy rarely defied her anymore, there were times when she felt the need to pull down his diapers and give him a hard spanking, and these humiliating punishments occurred whether or not there were guests present. Soon, the whole neighborhood thought of Jimmy as nothing more than a diaper-dependant toddler, who’s sissyish personality befitted his prissy appearance. They all treated him with the same general lack of respect one would a three year-old.

At the same time, Jimmy’s weekly enemas soon became a daily affair, with Tess pulling his wet diapers down every morning to administer a thorough, warm, soapy purge before his usual diaper change. Before long, Jimmy no longer needed to summon his aunt for #2, and more often than not, he was simply wetting himself during the day without even thinking anymore.

One day. Katie was over visiting with Tess when she brought out a small box from her purse and presented it to her friend. Jimmy was across the room, busy in his playpen and occupied with his plastic blocks, not paying any attention to their conversation.

“What is this?” Tess asked curiously.

Katie giggled and lowered her voice.

“It’s a chastity device for little Jimmy,” she said conspiratorially.

“A what?” Tess asked, not sure of what her friend was talking about.

“It’s a chastity device,” she repeated, “It will prevent Jimmy from being able to get any erections, which, I’m sure at his age, are starting to become more frequent.”

It quickly dawned on Tess what she was looking at and a smile appeared on her face.

“Oh yes…” she exclaimed enthusiastically, “This is exactly what he needs.”

“Is it secure?” Tess asked, suddenly concerned.

“Oh yes–very. It comes with a lock so that only you will be able to remove it. And I managed to find this version in pink,” she giggled again.

Both of them chuckled as their heads turned to the sissy boy in his playpen, quite oblivious to their plans.

“Oh, that’s perfect,” Tess exclaimed, “Can you show me how it works?”

Katie opened the small box and spilled the pieces on the table, going over how it fit and the proper sizing of the cuff rings.

“I’m sure he’s wet now–we can change his diapers and put this on him right away,” Tess said eagerly.

She stepped over to his playpen, bent over and lifted the back of his dress up to slip her fingers down his diaper.

“Mm-hm,” she nodded, “Somebody’s in a very soggy diaper. C’mon little boy–let’s go get you changed.”

Jimmy blushed a little as she took him by the hand and helped him out of the playpen, guiding him back to his nursery down the hall. As usual, the two were greeted with the sour, pungent smell of stale wet diapers as they entered his room and Tess quickly set about removing his soaked pampers, depositing them in his diaper pail next to his changing table. After cleaning him up and arranging a fluffy new set of thick diapers under his rump, Katie bent down and pulled Jimmy’s tiny little package through the small pink cuff ring of the chastity device.

“Wha-what’s that?” he quaked uncertainly.

“Nothing to worry yourself about,” Tess said as she pushed a baby bottle of warm milk into his protesting mouth. This effectively blocked his view and allowed Katie to work without his interference.

Jimmy’s penis was little more than an inch in length but the pink cage that she slipped over the head captured it effectively and she mated the two parts together, further compressing his toddler-sized nub.

“Would you like the honors?” she asked Tess as she held forth a small bronze lock.

Tess smiled broadly as she looked down on her quivering nephew, the obvious concern written on his cherubic face.

“This is just what he needs,” she said as she slipped the shank though and snapped the padlock shut with an audible click.

Jimmy kicked a little in helpless frustration as he felt his tiny little penis now effectively trapped in it’s new home.

“There you are, sissy boy–no erections for you anymore,” Katie announced smugly.

Although he wasn’t presently aroused, Jimmy could feel the close confined restriction around his wee-wee and his agitation only increased. It was apparent that this very last vestige of control in his life was being irrevocably taken away and he felt helpless to stop it.

Tess dusted his tiny package with fragrant baby powder and quickly covered it up with his soft, fluffy diaper, pinning the sides snugly around his hips.

“Don’t worry, Jimmy–you’ll get used to that in no time at all and before long, you won’t even know it’s there,” she assured him as she swiftly tugged his pink baby panties up his legs and fitted them over his bulging diapers with crisp, maternal efficiency.

“There,” she said with obvious satisfaction, “That’s where my baby belongs–right back in his diapers and plastic panties.”

Jimmy blushed and looked the other way–too ashamed and intimidated to return their collective gaze.

He knew he should have stood up to his smothering, domineering aunt a long time ago but now it was far too late. From now on, it would be a baby’s life for him–a life filled with wet diapers, early bedtimes, enemas and bare bottomed spankings, highchairs and playpens, and from now on–one without orgasms of any kind.

But it was also the lifestyle perfectly suited for a bedwetting sissy like Jimmy.

 

 

 

THE END

Frustrated Again

*Note to the reader: this story takes places 12 years after Babyhood for Billie.

 

 

 

Billie waddled tentatively into his wife’s bedroom, his thick, embarrassing diapers spreading his legs apart and preventing him from being able to walk normally as an adult.

One had to admit he looked rather cute; his wife had dressed him in his short, cropped fleece top, the pink and white one that said “Mommy’s Little Bedwetter” on it, matching anklets, and a flouncy pair of stretchy nylon rumba panties over the waterproof rubber panties covering his bulky nighttime diapers.

As usual, he felt emasculated and very babyish.

“Mommy?” he inquired timidly.

Jenna, his wife of five years, was lounging on her bed, filing her perfectly manicured nails and occasionally sipping a glass of wine. She looked absolutely fabulous. Dressed only in her sexy push-up bra and panties, her long, curly brown hair flowed down over her soft, bare shoulders like a waterfall, spilling down across her lithe arms but not covering the two spectacular mounds of her big breasts.

Billie stared at them now with unconcealed lust and unconsciously, his hand drifted down to gently rub the bunny soft front of his cushiony diapers.

“Yes, sissy?” she replied without looking up.

“Umm, I was wondering…” he began, “Do you think it would be alright if I slept with you tonight?”

Jenna chuckled dismissively and smiled as she looked up at her diapered husband for the first time.

“No sissy, that’s why I got a nice cozy crib for you to sleep in, so when you wet your bed, your mattress would be protected by a waterproof sheet. You know as well as I do that sometimes your plastic panties leak,” she explained patiently.

She looked so desirable right now, the soft light only enhancing her fabulous curves and Billie could see she’d done her make-up meticulously. His tiny little penis throbbed urgently with need inside his restrictive metal chastity device.

“But I’m so horny,” he whined pathetically.

Jenna smiled sweetly and got up out of the bed. Gently, she took his hand and led him out of her bedroom and back into his baby nursery next door.

“It’s only another month, and then Mommy will let you out of your chastity device so you can play with yourself in your diapers. Won’t that be fun?” she asked him in a condescending tone meant for toddlers.

Billie blushed at the humiliating “treat” she was describing. But he also knew it would be his only chance for an orgasm, however brief.

“But I’m horny now,” he bleated.

Jenna patted his fat, ruffled bottom and guided him into his pink crib.

“Aww, poor little thing. Is my pampered princess feeling frustrated again?”

She stood over him and cupped her big, sexy breasts with her hands–the latter of which looked small by comparison, presenting him with a maddeningly sexual display of femininity. The sight made Billie’s mouth water and he licked his dry lips. His little nub, so long ignored, was throbbing and aching painfully with desire and need.

Please let me cum, Mommy,” he pleaded desperately.

“Sorry sissy, it’s your bedtime–Mommy’s boyfriend is coming over and I want to look as pretty as possible for him.”

Billie’s entire being seethed with jealousy. He knew he was incapable of satisfying his sexy young wife but he boiled with frustration and envy that she openly cuckolded him, while at the same time, denying him any sort of sexual relief.

Every night was the same–after completing his list of chores, it was an early bedtime, pinned into his humiliating diapers and plastic panties. And every morning, he’d wake up soaking wet, desperately horny, and more frustrated than before.

Taking the bottle of milk that was on his pink dresser, Jenna pushed the big rubber nipple into her sissy hubbie’s trembling mouth, effectively ending the conversation, and then tucked his teddy bear under his arm.

“It’s nite-nite time, my little bedwetter,” she said as she raised the side of his crib and latched it shut, “You leave the sex and orgasms to a real man and he’ll leave the wet diapers and plastic panties to you.”

Billie frowned and pouted as he nursed his baby bottle submissively.

It was so unfair!

With that, she turned and walked out of the nursery, turning the light out and closing the door behind her as she went. Billie could hear her high heels clicking down the hall and he inhaled the infantile scent of baby powder that surrounded him. He felt so childish–being given an early bedtime and confined to his nursery while his hot wife had sex with her boyfriend. It was like he was four years old all over again!

To be sure, he knew his diapers would be soaked by morning, just as they always were. Indeed, that was the reason Jenna had started diapering him in the first place.

But she had found that the more she treated him like the bedwetting toddler he acted like, the less she saw him as a man. The constant smell of stale pee and baby powder started turning her off and she just couldn’t get aroused at the thought of a grown man who helplessly wet his diapers every night like a baby. That was when she realized she was going to have to find a real man to satisfy her needs.

And then later, when Billie’s skills in bed were revealed to be nonexistent, she decided it was time, once and for all, to take away his ability to masturbate and she put him under a strict chastity regime. Erections and orgasms were to be completely off limits to the incontinent sissy.

While initially, his opportunity for relief had started out as a bi-weekly affair, it had now become a memorable event only once every two months; Jenna would unlock his steel chastity device and let him play with himself before her in his diapers. She never once considered the idea of letting him inside her anymore.

During these short-lived occasions for relief, he was allowed to gaze at her sexy body and she usually dressed in something exciting and provocative for him to enhance his brief and humiliating experience.

Alas, it was often over within a minute or so.

After that, Jenna would pull his diapers back down and swiftly lock his little penis back into his chastity device where it would stay for another two months. She reasoned that a bedwetting pantywaist didn’t have any need for more than that.

Of course, just because she had put an end to Billie’s sexual activities, didn’t mean she was going to be left high and dry herself. Quite the contrary. Jenna immediately started dating again, and it wasn’t long before she’d found a steady boyfriend–one that was only too happy to give her all the breathtaking sex she could handle.

She smiled to herself when she imagined Brad’s massive cock filling her so completely and deliciously. It was so different from her sissy hubbie’s pathetic little stub.

He really did belong in diapers and chastity, she mused, and not for the first time.

And that was exactly where he was going to stay–denied, horny, and frustrated, like the sissy bedwetter he was, while she got all the eye-crossing orgasms she could ever want.

Jenna had come to enjoy humiliating Billie and she was always pushing the envelope to see how far she could take her dominance over him. She liked dressing him up in a short, frilly baby dress and parading him in front of Brad who would often condescend to slap his fat, diapered bottom and make him blush beet red with shame.

And she was always thinking of new and inventive ways to increase his humiliation further.

Recently, the idea of having him on his knees, dressed in all his toddler finery and sucking her lover’s big cock was tremendously arousing to her and she knew it was only a matter of when, not if, it would happen.

The knock at the front door interrupted her daydreaming.

Striding down the hall past Billie’s nursery, her stilettos echoed loudly on the hardwood floor as she went and opened the door.

Her boyfriend Brad grinned broadly as he drank in the sexy woman framed in the doorway.

“You look amazing tonight,” he gushed.

Smiling back at him prettily, Jenna quickly hugged him tightly and they kissed passionately.

Although Billie could no longer hear her, he could well visualize the scene, as he knew Jenna would be locking lips with Brad while the latter ran his hands all over her curvy, voluptuous body. It was a privilege he had long been denied.

He tossed and turned in his crib, the vinyl waterproof mattress cover crackling loudly beneath him. He was frustrated and angry, and the baby soft diapers swaddling his hips seemed to mock him with their comforting, teasing caress. Before Jenna had put him in chastity, he had secretly enjoyed masturbating nightly in them to an explosive orgasm just before nodding off to sleep. As a bedwetting teenager, he had done that every night under his mommy’s roof and then again, in the current nursery created by his wife. But now, such pleasures were forbidden to him but the buttery, pillowy cotton of his diapers remained–reminding him every night of the enjoyment he could no longer partake in. It was so frustrating!

As he lay in the semi-darkness of his nursery, he heard Jenna giggle and her high heels clicking as she walked past his door, followed by Brad’s heavy footsteps. They were headed for her bedroom.

He wanted to jump out of his crib and run shouting into his former bedroom, to tell her he was through being treated like a sissy baby.

But the idea died as soon as it was born.

Putting aside the fact that he was terrified of Brad, who could probably flatten him with one punch, Billie was also completely intimidated by Jenna. She was taller than he was–even without her heels, and she had a will of iron. She was used to getting her way and the force of her personality always made Billie back down.

She enforced her rule over him by routinely pulling him over her lap and spanking him like a child. This was almost always followed up with him being put into diapers and a sissy dress of some sort, regardless of the hour or company present.

The sight of his sexy wife with her paddle in hand filled him with a dreadful fear. Too many times, he’d been reduced to tears as she painfully meted out her retribution on his tender bare bottom. But as bad as that was–it was made even worse when she spanked him in front of her friends.

They knew all about her cuckolding him, and they delighted in watching as she pulled his pink lacy panties down, yanked him over her lap, and proceeded to paddle him like he were an errant child. If it were early evening, he would be led back to his nursery, to be pinned into his diapers and a short baby top. Then he would be taken back out, to play with some blocks or other such infantile toys while the girls commented on his humiliating outfit and diapers. They loved to rub it in–telling him how much of a pathetic pantywaist he was, and how much he deserved his permanent chastity. Billie would sniffle, and feel sorry for himself, but they would only laugh at how weak he was.

Of course, it never occurred to him to stand up to their jeers and mockery–after all–they were all authorized to paddle him as well if he were to displease them. And he could still recall as if it were yesterday, the time when Jenna’s friend Amber had blistered his bottom when she’d caught him looking up her short tennis mini-skirt from his position on the floor.

No, Billie knew his place, and he knew better than to talk back to Jenna’s friends or make them angry. A humiliating and painful spanking administered by one of them was to be avoided at all costs.

Soon, Billie could hear his wife’s amorous moans from the other room. She sounded so sexy, and despite himself, Billie felt his little penis growing hard again. It strained inside the tiny steel cage, struggling to get an erection that was quite impossible.

Before long, Billie could hear his wife’s mattress creaking and the headboard striking the near wall as Brad pounded her with his mighty cock. Her screams of pleasure and joy filled the house as she called out his name over and over and demanded more.

Billie rubbed the front of his diapers frantically, wishing somehow he could defeat his chastity device and achieve an orgasm but alas, it was hopeless. It only made him hornier and as he always did at times like these, he silently cursed his lack of manhood which had ultimately led to this situation.

Eventually, after the last shrieks of his wife’s orgasms died away and the house fell silent again, Billie fell into a troubled, frustrated sleep.

 

 

 

 

 

Billie was awakened the next morning as his nursery door was opened and Jenna strode in, followed by Brad.

“Well–how did my sissy hubbie sleep?” she asked pleasantly.

Billie had been sucking his thumb, and he jerked it out of his mouth as he blushed deeply in shame. He hated being caught doing that, but for some reason, it sometimes just happened unconsciously.

Jenna unlatched the rail of his crib and swung it aside, pulling her diapered hubbie up to a sitting position. She knew without checking that he was wet but she wanted to humiliate him in front of Brad.

This morning Jenna was wearing a loose fitted robe over her push-up bra and panties (she never appeared before Billie without a bra anymore), and she crossed her slim arms over her big beautiful breasts as she looked down on Billie with a smug look of satisfaction. Indeed–she was satisfied to the point of being sore after last night’s marathon sex, and it offered the perfect opportunity for her to put her plan into place.

“Billie–tell Brad why you have to wear diapers,” she told him.

Billie blushed and it was only then that he realized the thick cotton cloth was soaking wet inside his snug rubber panties.

Swallowing hard, he looked away in embarrassment as he stalled for time.

“Come on,” she snapped impatiently, “Tell him what you are.”

Billie cleared his throat as he stared at the floor.

“I-I’m a b-bedwetter,” he confessed shamefully.

“And how long have you been a bedwetter, sissy?” she pushed him.

“Umm, a-all my life,” he admitted as his cheeks burned hotly before them.

“Needless to say,” Jenna said as she turned slightly towards Brad, “This was a secret the little pantywaist kept from me while we were dating. If I had known he’d never been potty trained…”

She didn’t finish the thought.

“Okay sissy, climb out of your crib–it’s time you learned your proper place in this house. We both know you can’t satisfy a woman but maybe you’ll have better luck with a man…”

“Wha-what do you mean?” he stammered, suddenly filled with apprehension.

Forcing him into a kneeling position before her imposing boyfriend, she began fondling Brad’s big member through his boxers.

“I’ve seen the way you look at Brad’s cock when he’s around–I’ll bet you’ve always wondered what it would feel like inside your mouth, hmm?”

Billie blushed bright red and abruptly shook his head, deeply ashamed at what she was implying.

“Haven’t you always wondered what it would be like to have his big, thick cock jammed down your throat as he blasts his huge, creamy load into your tonsils?”

“No!” he squeaked, too embarrassed to put up a proper defense.

“Well, today’s your big chance,” she said ignoring him, “Brad wants another orgasm and frankly–I’m too sore from last night.”

By now, her boyfriend’s massive cock was tenting his underwear and it looked like he was concealing an oversized cucumber. Billie licked his dry lips nervously as he gaped at the intimidating monster his wife was stroking.

Pulling down his boxers, Brad slowly lowered them past his muscular hips and let them drop in a ring around his ankles. His cock was truly enormous, with prominent veins running down the engorged shaft and a smooth but fat, mushroom shaped head–a bead of precum now oozing from the tip.

Billie swallowed hard as he stared at it, throbbing with eagerness, inches before his face. It was so completely different from his own, tiny little penis; it was like comparing a baseball bat to a crayon.

Without warning, Brad suddenly grasped the base of his cock and pushed it into Billie’s gaping mouth. The latter squealed loudly, his cheeks expanding widely as she struggled to take the gargantuan piece of warm meat thrust into his mouth. Brad pushed it in until it bottomed out against the back of Billie’s throat, causing the sissy to gag frantically.

“Suck it, pantywaist,” Brad ordered him gruffly.

Billie wasted no time and immediately did as he was told, running his tongue under and around the fat, slippery shaft filling his mouth. He whimpered and tried to maintain his balance as Brad grasped his head tightly and established the rhythm of his choosing. Soon, his big hairy balls were slapping Billie on his chin and Jenna laughed out loud.

“Look what a good cocksucker I’ve got here,” she exclaimed enthusiastically, “If only your mommy could see you now.”

Billie blushed furiously at the thought. His own mother had always proclaimed to him and anyone who would listen that he was nothing but a big sissy–a bedwetting pansy who belonged in diapers and dresses.

He could almost visualize her now, standing over him, her arms crossed over her chest as she shook her head in obvious disappointment and dismay. Some man he had turned out to be!

Meanwhile, Brad was hammering his mouth with deep, hard thrusts, making Billie’s jaws sore from being stretched too far. At the same time, his precum had awakened Billie’s saliva glands and the monster hard cock was sliding in and out of the sissy’s warm, wet mouth like it were an eager pussy.

Just as Billie was staring to get dizzy, Brad stopped his pace and the diapered sissy felt his massive cock expand even bigger in his mouth.

“UUUUUGGHH!!!” he bellowed loudly, his mighty cry shaking the walls.

Billie felt a huge load of warm, creamy goo fill his mouth and without thinking, he swallowed it obediently. However, it was quickly followed by another one which was forcefully blasted into his mouth behind the first one. Billie squealed as every taste bud in his mouth was treated to his first encounter with fresh, sticky semen, straight from the source. He gulped hard and gulped again, only to have Brad shove his rigid tool right into the back of his throat and explode with another overwhelming shot.

Jenna was laughing and snapping pictures with her cell phone, delighted to finally see her sissy hubbie being put into his rightful place. This made up for all his deceitful denials during their early dating, when she’d confronted him about his pee-stained sheets and sissy ways.

Now, she watched with glee as his cheeks were stretched to the limits and he gagged on this last load of cum being forced down his throat.

As Brad finally eased his still hard member from Billie’s trembling mouth, a string of semen ran from his lips to the fat head of Brad’s shiny cock.

“Billie, you can count on a lot more of that in the future–I think I’ve finally found something you’re good at, besides wetting your diapers,” Jenna told him.

“Kiss it, you little pantywaist,” Brad ordered him roughly.

Deeply ashamed, Billie did as he was told, tenderly kissing the big purple head while keeping his eyes submissively downcast.

“I think I’ll invite my friend Charles over–he’s as queer as a three-dollar bill, but I know he’d love jamming his big cock between your lips.”

Billie blushed as he tried to use his tongue to remove the slick coating of semen lining his mouth. He was sure he’d be tasting it all morning.

 

 

THE END

Babyhood for Billie


 

Billie was nervous.
And as the 13 year-old boy trailed behind his mother, he grew increasingly nervous as he eyed the numerous cars parked in the driveway of his aunt’s house. Clearly, she had company visiting her.

For anyone else, this wouldn’t be an issue, but Billie had an troubling tendency to occasionally pee his pants, and his pragmatic mom had responded by putting him in diapers and plastic panties, particularly when he was going somewhere where he might embarrass himself with an accident.
Often, when Billie got excited, or was suddenly surprised, or scared by something, he would wet himself. Not a lot, but enough to cause an obvious dark spot in the front that would be noticeable to anyone around him.

His aunt Wendy knew of his mom’s methods and she fully approved–in fact, she kept a good supply of diapers at her house just for the occasions when Billie came over to be babysat by her.

She loved her nephew, but she wanted to make sure he was safe and protected whenever he was in her care.

Billie bit his lip and fidgeted as he imagined the difficulty he was going to have, hiding his crinkly diapers under his jeans from the various women visiting his aunt.
Knocking at the door, his mom held his hand securely as they listened to his aunt’s footsteps approaching from the other side. Billie tightened his own grip on his mom’s hand as the door opened, revealing a number of women sitting around the living room behind his aunt Wendy.
Seized with anxiety, Billie suddenly felt a hot stream of pee soaking the front of his diapers. He winced as his smiling aunt gazed down upon his cringing visage.

“Well hello Billie, how have you been?” she asked warmly.
Billy was both short in stature and slight in frame so he had to crane his neck upwards to look at his aunt.
He shifted his feet and his eyes darted about as he mumbled something under his breath.

Without waiting, aunt Wendy bent down and undid the snap on the front of his jeans, shamefully revealing the shiny waterproof panties covering his diaper. He squealed as she slipped her hand down the front to feel the warm wetness humiliatingly surrounding him.

“Did Mommy’s little boy wet his diapers?” she asked, louder than necessary.

Billie blushed furiously, his cheeks a bright red as he looked away in embarrassment.

“Don’t you worry, honey-bunches, I’ll get you fixed up right away,” she assured him.

Billie was acutely shy and having the backbone of a jellyfish, he was used to being pushed around by others. In fact, his inability to maintain eye contact with people meant that they often took advantage of him–he was unable or unwilling to stand up for himself, and he was often the target of bullies, both male and female at school.

After saying their goodbyes, aunt Wendy led the blushing boy past the group of her girlfriends and down the hallway to her bedroom. He kept his eyes straight forward, studiously avoiding making eye contact with the curious women who’s eyes were closely following him.

As they entered aunt Wendy’s bedroom, he saw to his dismay that she already had a fresh change of diapers laid out on a changing pad she’d arranged on the bed–three fluffy white rectangles of cotton alongside a colorful pair of yellow, nursery print plastic panties.
Seeing what was in store for him, Billie sniffed a little, feeling sorry for himself as his aunt busied herself untying his sneakers and removing his pants. After folding them neatly and setting them aside, she tugged his clinging white waterproof panties down off his wet diaper, putting them in a bag, before reaching down to undo the pins.

“Poor Billie,” she said sympathetically, “you must have gotten excited again, hm?”

The boy was too humiliated to answer properly, and he only managed to mutter something incoherent as she took his soggy diapers down and put them in the same bag as his plastic panties.

Reaching under his arms, aunt Wendy easily lifted the abashed boy up and onto the bed, depositing him onto the fluffy, thick stack of fresh diapers.

“I’ll get you all fixed up in a two shakes,” she said with a big smile.
Billie cringed as he looked about the room nervously–these were much thicker diapers than he was used to wearing, with a noticeably more prominent center section–they were going to be all but impossible to hide from those around him.
Taking some baby wipes, aunt Wendy cleaned him up before rolling him over to thoroughly coat his bottom with diaper rash cream. Billie wondered nervously if she’d let him stay in her bedroom until her guests left so they wouldn’t see the massive bulge under his pants but he was too shy and nervous to actually suggest it.

Rolling him back onto the diapers, aunt Wendy powdered him with lots of babyishly fragrant powder, surrounding him in the infantile scent as she pulled the bunny soft, thick cloth up between his slim legs, forcing them apart as she pinned either side snugly around his narrow hips. Billie whimpered weakly as his aunt performed this profoundly childish ritual and not for the first time, did he find it mortifying that he still needed diapers like a baby.
Shaking out the nursery print plastic panties, she fed them over his feet and then had him stand so she could pull them up his legs.

“I just thought these were so cute,” she gushed proudly as she pulled them up past his trembling knees, “I love the playful pattern of the bunnies and rattles.”

Billie blushed with shame as he held onto her for balance and gazed at his reflection in the mirror covering the opposite wall. He looked just like a helpless toddler having his waterproof panties pulled up for him by his mommy. He knew he was the only one of his peers still being put in diapers, that was for sure.

He resented that she was using such thick ones for him, when a much thinner diaper would have sufficed, but of course, he said nothing.

Biting his lip, he whimpered again as she tugged the plastic panties up and over the fat diapers, working them around until the elastic waistband was above the top of the bulging cotton cloth.

Sitting him back on the bed, aunt Wendy began tying his sneakers but Billie finally found his voice.

“Wa-wait!” he squealed, “Wh-what about my jeans?”

Aunt Wendy finished tying his shoes and patted the bulky front of his shiny yellow panties, “I think these will be just fine,” she grinned, “Plus, it will make changing you much easier for when you wet again.”

Billie’s cheeks flushed an even deeper red that she had so little confidence in his ability to control himself.

Taking his hand, she stood the nervous boy up on his feet. With just his Superman t-shirt, sneakers, and bright yellow bulging diaper, he looked like any three year-old toddler ready for an afternoon of play.

“Come along, Billie,” she said as she playfully swatted his fat bottom, “let’s go out to the living room where I can keep an eye on you.”

“N-no!” he protested, but it only made him sound weak and petulant.

Using one hand under his bulging, plastic covered rump, Wendy easily pushed the trembling boy out of the room and down the hallway. He stumbled headlong down the hall, unable to stop his inevitable and humiliating exposure. Needless to say, his entrance caused everyone to stop dead in their conversations and stare openly at the freshly diapered teenager.

“Say hi to my friends,” aunt Wendy told him.

Billie swallowed hard as a strong, powerful steam of warm pee suddenly surged unbidden into his waiting diapers. He gaped at the women looking back at him with amusement, feeling helpless and very babyish.

“Billie wets his pants occasionally so his mommy has started putting him back into diapers and baby panties,” Wendy cheerfully announced by way of an introduction.
She reached down and gave his thickly diapered bottom a playful squeeze which made Billie squeal with surprise. Everyone laughed and giggled as a second stream of hot pee followed the first.

To think that only moments ago, he had walked past these same women and only been concerned about hiding the sound of his diapers under his pants!

“Why don’t you sit down and play with your Legos,” Wendy suggested as she gently pushed him down onto the floor.

Billie’s legs folded under him and he landed with a soggy wet, humiliating squish. Looking up around him, the other women smiled down at him, one of them unable to resist reaching over to pat his cute baby bottom but soon, their conversation returned to their earlier discussions, and they more or less ignored Billie.

It was excruciating for the budding teenager to sit there, with the eyes of these women gazing down at him from time to time at his shameful, babyish circumstances. He could only imagine what they must think of him and he was lost in thought when one of them, a very pretty brunette, suddenly reached down without notice and gave the fat seat of his diapers a squeeze.

“Wendy, I think Billie wet himself,” she declared.

Billie’s cheeks flushed crimson in shame as his childish condition was suddenly announced to all. And as if in confirmation of her words, as everyone turned to stare at him, he felt another strong stream of hot pee re-warm his already wet diapers.

Wendy rose to her feet and went over to Billie who was cowering on the floor, biting his lip as his cheeks blazed hotly. He looked the other way as she bent down and slipped a finger down the back of his diapers.

“Mm-hm, I think I’ll change you and then it’ll be naptime for you, Billie,” she told him.

As if wearing baby’s diapers at the semi-adult age of thirteen wasn’t bad enough, now everyone knew he’d be taking a nap just like any other toddler. Billie hung his head low as Wendy took his hand and stood him up, squeezing his diapered seat one more time, as if she wanted to confirm what she already knew. Billie whimpered and made ready to leave but Wendy unexpectedly turned him around to face the gathered women.

“Billie–say goodbye to everyone before you go and then we’ll change those wet pampers of yours.”

With his cheeks blazing hotly, Billie mumbled something to the smiling females before glumly turning around to return to her bedroom.

“If you’d like, I’d be happy to lend a helping hand,” the pretty brunette offered.

“Well thank you,” Wendy replied, “that would be wonderful, Gina.”

Together, the three of them made their way down the hallway, with Billie waddling awkwardly and his heavy wet diapers swishing between his legs.

Once they reached Wendy’s bedroom, she tugged his damp plastic panties down off from the soggy cotton layers underneath. The childish smell of pee surrounded them and Billie felt completely humiliated.

“How old are you Billie…ten?” the stunning brunette asked.

“I-I’m thirteen,” he replied in embarrassment.

Both of the women giggled and Wendy pulled Billie’s wet diapers off him, exposing his shriveled little penis before sitting him down on a fresh stack of fluffy Birdseye cloth. The sissy teen quickly covering his unimpressive privates with his hands as he squirmed and whimpered, unhappy having this most humiliating ritual exposed to his aunt’s attractive friend.

He was already extremely shy and being exposed before this stunning woman was more than he could stand.

“Can you pick out a pair of baby panties for him?” Wendy asked her.

“Sure thing,” Gina said as she began sifting through a pile of waterproof underwear on the floor. After selecting a pink pair of rubber panties, she held them up for Wendy to see.

“How about these?”

“Perfect,” she said with a smile, “Billie is a chronic bedwetter and he never fails to soak his diapers during naptime–the rubber panties seem to make for a better seal against his thighs.”

Seeing his discomfort, the brunette bent over and smiled down warmly at Billie.

“Don’t worry, sugarplum–I think you look really cute in your pampers.”

Unfortunately, her words provided little solace as Wendy moved his hands away, began powdering his front area, and efficiently pinning his fat, fluffy diapers around his hips.

Seeing a pacifier on Wendy’s dresser top, Gina scooped it up and popped it into Billie’s quivering mouth. He kicked his feet a little in embarrassed, helpless frustration, but did nothing to remove the pacifier.

“Maybe that will help you sleep easier,” Wendy said, beaming down at the fussy, diapered teen.

Gathering the stretchy pink panties in her hands, Wendy fed them over Billie’s kicking feet, pulling them up his slim, hairless legs and tugging them over the fluffy bulk around his hips.

“There,” she said smiling as she ran her fingers around the soft, stretchy elasticized waistband, tucking in the top of his diaper, “Now you’re all safe and protected again.”

Billie was crushed with shame as the two of them gazed down on him with amusement, his fat, bulky diapers forcing his legs apart.

“Does he have a nursery at home?” Gina asked.

“No,” Wendy giggled, “But he should.”

“Well it looks to me like you failed potty training 101,” Gina said as she placed her hands on her hips, “If I were your mommy, I’d make you my little baby and start all over again.”

Billie’s cheeks blazed crimson and he looked away, deeply ashamed at the humiliating picture she was painting. Wendy pulled the covers back and the mattress crinkled under him audibly as he shifted his weight, due to the waterproof cover designed for bedwetters she had put down for him.

Turning the light out, the two of them left the room, leaving Billie to re-live over and over in his mind, the afternoon’s traumatic events.

At last, he fell into a fitful sleep.

Billie woke to the sight of his aunt and her pretty friend leaning over him. Wendy pulled the blankets down, and slipped her finger inside the soft waistband of his rubber baby panties.

“I see that mommy’s little baby wet himself again,” she remarked pointedly.

Billie cheeks reddened and he bit his lip. He was acutely aware of the strong smell of pee surrounding them and Wendy slid his feet out so she could change his diapers.

“Gina here has agreed to babysit you tonight since your mommy won’t be home until late,” she told him as she began peeling the stretchy pink latex panties down and off his soggy diaper. Soon, his wet diapers followed the damp rubber panties and his aunt began cleaning his bottom and crotch with some baby wipes.

Billie blushed down to his chest–he was mortified to have his aunt’s pretty friend see him like this again, looking like nothing more than an incontinent toddler but he was even more troubled by the thought that he’d be all alone with her this evening.

“Don’t you worry, Billie,” the gorgeous brunette told him as she looked down upon his bare and bald diaper area, “we’re going to have so much fun tonight!”

Billie found the generously endowed woman very intimidating, and her incredible beauty only increased his feelings of anxiety. He wanted nothing more than to run away but Wendy was firmly holding his ankles over his head as she smeared sticky diaper rash cream across his bashful bottom.

“Gina–do you have some diapers at home for Billie? I can let you borrow some if you don’t,” Wendy offered.

“Oh–don’t worry at all–I have a fully stocked nursery that I’m sure Billie here will just love to play in. It’s got stuffed animals, dollies, and plenty of diapers for our little bedwetter.”

Billie blushed furiously and Wendy giggled, making no attempt to correct her friend’s childish appraisal of him as she slid a thick stack of soft, fluffy diapers under his little, upraised rear. He felt utterly helpless as she powdered him thoroughly, surrounding him with the babyish scent, and then pulled the ends of the diaper around his hips, pinning them snugly together. Once again, the bulky cotton cloth forced his legs apart and he whimpered with humiliation.

“I think these plastic panties are just what the doctor ordered,” Gina giggled as she held forth a white and pink pair of rumba panties. The seat had playful ruffles covering the upper half, and with practiced movements, she slid them up Billie’s smooth, hairless legs.

“I think you’re a bit of a sissy, aren’t you?” Gina asked, but with a tone of certainty.

Billie’s face flushed hotly. He wanted to argue with her but at the moment, he felt like such a baby getting pinned into his big, bulky diapers like an incontinent toddler.

As her fingers circled around his waist, fitting the stretchy panties over his diaper, the distraught teen struggled to speak up for himself.

“I-I’m not a s-sissy,” he said in a shaky voice, even as he gazed down on the prissy, babyish panties now covering his fat diapers.

“I think we both know that you are,” Gina countered firmly as she began tying his shoes on his feet.

Billie was aghast as he watched her helplessly.

“B-but what about my p-pants?” he squealed frantically, for the second time that day.

It was one thing to be dressed this way indoors but a trip to Gina’s house like this?

“We wouldn’t want to hide these special rumba panties your aunt bought for you, now would we?” she giggled as she patted the shiny, bulging front of his diapers.

Before Billie could respond, Gina pushed the rubber pacifier she was holding between his quivering lips, putting an abrupt end to his protest before he could reply.

He had never felt so deeply emasculated and defeated.

As the two of them helped Billie to his feet, he noticed he had to stand with his feet apart, so wide was the bulk between his legs.

“That should last you for the ride over,” Gina beamed happily at him as she took his hand and led him waddling out of the bedroom. He wanted to spit the pacifier out and jerk his hand from her grasp but she was already firmly leading him out and into the living room. Gina had a strong, forceful character and she was exactly the kind of person Billie always felt unable to stand up to. Like it or not–he was going to get his full dose of humiliation and then some.

Everyone stopped what they were doing to smile as the blushing sissy in his cute diapers and rumba panties appeared before them.

His cheeks immediately flushed an even brighter red as everyone cheerfully waved him goodbye. At the same time, he felt himself helplessly flooding his diapers again, the warm pee quickly soaking the front and gradually seeping back up into his thickly padded seat. With the big rubber pacifier filling his mouth, his squeal of distress only sounded as babyish as he looked, anxiously waving his free hand frantically in the air while the women giggled back at him.

Everything became a blur and before he knew it, he was being whisked outside to Gina’s waiting car. The cool air breezed over his bare thighs and he whimpered with shame at being so utterly exposed. He cursed his lack of backbone and he did nothing as Gina sat him in the passenger seat and buckled his seatbelt for him. This forced him to look down the front of her top and he gasped as he stared dumbfounded at her big breasts mashing together. The sight only seemed to further emphasize the vast gulf between their two levels of maturity.

Absently, he wondered if she could smell the pee wafting up from within his diapers.

“Don’t worry, sissy,” she said as she kissed him affectionately on the cheek, “I live just around the block.”

Although he didn’t like being called a sissy, his cheeks reddened again at being kissed by such a pretty woman. Up until now, the only other female that had ever kissed him, had been his mom.

Hopping into the driver’s seat, Gina started the engine and pulled out into the street.

“I have some really cute outfits for you to try out,” she told him excitedly, “Do you like to play dress up?”

Billie shook his head and tried to say no, but the pacifier only made him sound childish.

“All sissies love to play dress up,” she continued, answering her own question, “And I have the perfect baby dress for those panties.”

She patted his exposed, bare thigh and he felt an electric thrill at her touch.

Billie’s breathing increased rapidly and he squirmed nervously in his seat. This was all happening too fast! Who was this strange woman, anyway?

In no time at all, they pulled in front of a modest house and Gina came around to undo his seat belt. He was in the process of doing it himself when she lightly slapped his hands away.

“No baby boy–that’s your babysitter’s job.”

Once more, he felt horribly exposed as she pulled him out of the car, his fat, ruffled diapers fully on display for anyone who happened to be looking. Another stream of warm pee flooded into his diapers and he whimpered in muffled frustration.

Sweeping him into her home, she led him down the hallway into what was obviously a girl’s nursery, decorated in colorful pinks and whites. A somewhat large baby’s crib stood in the corner and a pink dresser, adorned with cheerful nursery characters was nearby. Billie’s tummy buzzed with nervous anticipation as he looked around the feminine, babyish room. He didn’t want any part of this and he grew anxious for what she had in mind. He wanted to stand up from himself, but he seemed totally unable to confront this beautiful, intimidating woman.

Gina went over to the closet and picked out a fancy white and pink baby dress, with lemon yellow accents, generously ruffled along the flared hem. It looked just like something a three year-old girl would happily wear on a Sunday picnic.

“Isn’t this pretty?” she gushed proudly as she held it up before him.

He shook his head in protest but Gina was already removing his Superman t-shirt. She dropped the frilly confection over his head and then turned him around to fasten the buttons up the back. Billie sucked feverishly on the rubber pacifier filling his mouth and before he knew it, Gina was sitting him down on the edge of the crib mattress.

Before he could stop her, Gina removed his shoes and socks, swiftly replacing them with lacy anklets and a pair of glossy pink Mary Janes.

“That looks so much more appropriate,” she told him.

Grasping him by his puffy, short-sleeved shoulders, Gina stood him up before her to look at her handiwork.

“Aren’t you just the cutest little thing!” she exclaimed as she hugged him tightly. The emasculated sissy squealed as he felt her big, soft breasts pressing against him.

Billie felt overwhelmed as Gina ushered him over to a full length mirror. He blushed hotly as he beheld his babyish reflection staring doe-eyed back at him. The ruffled hem of the baby dress only came down just past the waistband of his rumba panties, leaving his shiny fat diapers shamefully exposed.

Shaking his fists in frustration, the poor diapered sissy suddenly burst into tears, his pacifier tumbling out of his mouth.

Gina’s delicate brows furrowed in surprise.

“Awww, don’t cry little baby,” she said, her voice filled with warmth and compassion.

From somewhere, she produced a baby bottle full of milk and sitting him back down on the edge of the crib, she carefully pushed the nipple between his squalling lips.

“Here you are my wittle babykins,” she said in a syrupy voice for toddlers, “Just what a sissy needs.”

Billie sniffled as he nursed from the bottle, feeling very infantile next to this very adult, pretty woman. He wanted to stop her somehow but his mind was spinning in circles.

As she held the bottle for him, he couldn’t help but gaze down Gina’s top again, feeling overwhelmed to be in such close proximity to such a voluptuous, sexy woman. His tiny little penis, surrounded by warm, soggy wet cotton, twitched anxiously as he stared at the curvy twin mounds of her glorious breasts.

He felt completely incapable of resisting her and her manner made him feel like nothing more than an weak little boy. Gina smiled down upon him, patiently holding his bottle until Billie had finished nursing from it.

“Come along, baby Billie,” she said as she stood up and led him out of the nursery.

Taking him by the hand, she took him into the kitchen, his plastic panties crinkling noisily and she helped him climb into a large highchair that was off to one side. His warm, soggy diapers squished beneath him and once again, he breathed in the shameful smell of his own pee.

Gina slid the front tray into place and it locked with an audible set of clicks, effectively trapping the diapered boy in place. Squirming in his seat, Billie could do nothing but swing his feet idly as she carefully tied a colorful plastic bib around his neck.

Taking a multi-partitioned serving plate, she emptied several jars of baby food into each space and began serving him with a large plastic spoon.

“I’ll bet my little baby is hungry,” she said with exaggerated gravity.

Billie’s stomach churned at the smell and sight of the glop but before he knew it, she was pushing a heaping spoonful of creamed corn to his pursed lips.

“Uh-uh!” he whimpered weakly but she pushed determinedly against his mouth.

Looking up into her big brown eyes, he opened his mouth in submission and was promptly rewarded with a big spoonful of the slop.

“AWGFF!!” he cried as he struggled to swallow it all. She pulled the spoon upwards, spilling some on his nose and chin before scooping up another huge portion of something green.

“Open up, baby!” she grinned as Billie struggled to keep up with her.

In no time, his face was caked with semi-dried baby food and his stomach groaned uncomfortably.

“And now let’s wash that down with a nice bottle of warm milk!” she said enthusiastically.

Billie shook his head and swung his feet, wishing he could escape but Gina was already pushing the wet nipple between his lips. Holding it in place, she forced him to nurse from it as she smiled down upon him. Billie gazed from her deep cleavage, up into her bright, dancing eyes while he slowly drained the baby bottle.

With her free hand, Gina slipped a finger under Billie’s baby dress and inside the waistband of his plastic rumba panties.

“Baby Billie really soaked his diapers again, didn’t he?” she said in the third person.

His cheeks blazed with embarrassment as his eyes darted around, desperately trying to avoid her gaze.

“Its a good thing that your aunt put you in such thick diapers, isn’t it sweetie,” she observed, “You certainly need them.”

Gina seemed to go easily from condescending, to sweet, and back to condescending again.

Billie whimpered in humiliation as she wiped his face with a wet washcloth and removed the serving tray from in front of him.

“I better change those soggy pampers of yours before your mommy gets here,” she told him as she led the blushing boy back to the nursery. The saturated cotton of his diapers clung stubbornly to his bottom and embraced his hips as he waddled down the hall behind his sexy babysitter.

He felt some measure of relief that his humiliating ordeal would at last, be coming to an end. His mom would put a stop to this, that was for sure.

Standing him before a raised changing table, Gina reached under the ruffled hem of his baby dress and she grasped the waistband of his plastic panties. Working them down and off his diapers, Gina looked the nervous boy in the eye.

“I think I’ll add some soaker pads to your diapers–you wet so much you need all the protection you can get,” she told the embarrassed, blushing teen.

Unpinning his heavy diapers, she let them fall around his ankles before gently setting him down on the changing table. Billie looked away anxiously as she cleaned his bottom and tiny little package with some wipes, giggling to herself at just how small he was.

He squealed as Gina grasped his ankles and swung them up over his head so she could coat his cute bottom with Desitin. The ruffled hem of his baby dress gathered around his chest as he grasped the sides of the changing table for support.

“This is a bedwetter’s best friend,” she remarked with a pretty smile as she applied some cream between his legs and around his diminutive sack. This was followed by a thorough dusting of baby powder, which she shook up even up onto his chest, to make sure he’d be surrounded by the babyish scent all evening.

“Here we are baby,” she said as he pulled the bulky thick diapers up between his legs.

“These baby pins are perfect for a little sissy like you,” she said as she showed him the pink duckie safety pins. She carefully inserted them into the corners and snugly pinned his fat diapers together around his hips.

Sifting through her substantial collection of waterproof panties, she finally selected a pink rubber pair with white lace.

“Since you’re going to bed soon, I think I’ll use these rubber panties–your aunt says you’ll leak less when you’re in your crib.”

Billie was too ashamed to tell her he didn’t sleep in a crib and he bit his lip in humiliated angst.

The panties were light and stretchy and Gina slowly pulled them up his quivering legs, taking her time to work them over his big, fluffy diapers.

Just then, the doorbell rang and Billie froze in fear.

“I’ll bet that’s your mommy,” she said brightly, “Perfect timing!”

Billie’s heart skipped a beat and he felt a warm squirt of panic-induced pee escape into his fresh diapers.

Gina stood up and left the room to answer the door, leaving Billie to squirm nervously on the changing table. Biting his lip, he gazed apprehensively at his reflection in the mirror–he looked to all appearances to be a cute toddler girl in diapers.

Just as he was desperately trying to think of how he’d explain his attire to his mother, she walked into the room behind Gina.

“I hope you don’t mind–I thought I’d dress Billie in some clothes that were more befitting his childish behavior.”

His mom gasped in shock–she barely recognized her sissy son in the frilly ruffled dress and Mary Janes he was wearing.

“Oh my…” she exclaimed.

A big smile came over her and she bent down to touch the delicate lace on the elasticized puffy shoulder sleeves of his baby dress.

“Oh Billie, I think this suits you just so perfectly,” she gushed as she beamed down at her squirming and blushing diapered son, “I’ve always wanted a little girl and now I have one!”

“If you’d like, you’re more than welcome to take him home in his dress–it can be my gift to your little baby bedwetter,” Gina said with a gracious smile.

Billie’s mom clapped her hands together and she thanked Gina profusely.

“I’m going to get a whole new wardrobe for you, Billie–you’re going to be mommy’s cute little baby girl from now on.”

Billie probably should have taken this opportunity to argue the point but he was so weak-willed and spineless that all he could do was look around uncertainly, his cheeks blazing with embarrassment.

Taking him by the hand, his mom lifted him to his feet and with her free hand, she squeezed the thick, baby soft seat of his fat diapers.

“My, these are certainly well suited for my little water fountain. Make sure you thank Miss Gina for your diapers and baby dress, Billie,” she told him.

Billie shifted his feet, unable to look up into the beguiling brown eyes of his babysitter.

“Come on, Billie, don’t be rude,” she said as she gently patted his soft, rubber pantied bottom.

Blushing furiously, Billie cleared his throat but he was unable to look directly up at Gina.

“Um–I, um…tha-thank you, M-Miss Gina,” he stammered.

“What are you thanking her for, Billie?” his mom prompted the blushing boy.

“Th-thank you for my d-dress,” he stuttered.

“And your diapers and pink rubber panties,” she added.

“A-and for my d-diapers and pink rubber p-panties,” his voice croaked as a strong torrent of warm pee flooded unstoppable into his diapers. All that milk was coming back to haunt him.

“You’re certainly welcome, sissy boy,” Gina beamed as she bent over and gave him a kiss on the cheek, “And now you’ll get to be the little baby girl that I know you’ve been trying to hide inside of you. It’s just what you deserve.”

Billie’s cheeks flushed a deep red.

“I can’t thank you enough,” his mom said as she held Gina’s hands in hers, “You need to give me all your sources for baby clothes. I want him to have the cutest, frilliest dresses and panties from now on.”

“I’ll be delighted to.

“Sometimes, a sissy is the last one to recognize what he truly is. Fortunately–I realized immediately Billie for what he is–a prissy pantywaist who needs to be treated like a little baby.”

“Truer words were never spoken,” his mom agreed.

Reaching down, she took Billie’s hand in hers.

“Come along, Billie, it’s past your bedtime which I’m moving up to 7:30 from now on.

“Tomorrow, we’ll start converting your bedroom into a proper nursery.”

Billie pouted but followed his mom as he waddled down the hallway behind her.

Gina was the last one out of the doorway as she smiled to herself and took one more look around the nursery.

Three bedwetters reverted to sissy babies in as many months, she thought to herself…this was money well spent, she reflected.

She smiled again as her gaze fell upon Billie’s fat, rubber pantied bottom, waddling down the hallway in tow behind his mother.

And now, it was time to focus her attentions on the sissy’s bedwetting friend Francis…

THE END

My Nephew, Still a Baby at 16

The hard, unremitting slaps of the paddle rained down without respite on Francis’ tender, bare bottom as I spanked the 16 year-old sissy relentlessly. It was already a deep shade of pink and rapidly turning to a fiery, angry red. He was sobbing and desperately kicking his feet, even as he beat the floor with his bunched up fists. After the center of each of his round, youthful buns had reached the proper color of punishment, I turned my attention to the sides, swatting them with equal ferocity as my nephew bucked and howled in pain.
He was getting his just reward, for a day of misbehavior and a snotty attitude.
It had all started out this morning, when he had put up a fuss over the frilly pink Sunday dress I had picked out for him. He didn’t like it because the ruffled hem was so short, and his thick, embarrassing diapers would be on display the rest of the day. Normally, that wouldn’t have been such a big deal, except for the fact a couple of my friends would be coming over and he was mortified to be seen by them dressed like that.
The second infraction occurred when he started pouting when Mrs. Johnson wanted to give him his baby bottle. Again, while this is a common, daily event for him, the added humiliation of having our striking next door neighbor administer the ritual was more than he could stand.
Lastly, he threw a tantrum when I put him down for his nap a half an hour early this afternoon. That was the final straw.
So now his humiliating diapers were down, his plastic panties tangled around his calves as I blistered his sissy bottom with my stout oak paddle. And it was made all the more embarrassing by the fact that his punishment was being witnessed by the same Mrs. Johnson. I think his first tears were more due to utter shame than from the slap of the paddle but since he almost always begins crying right from the beginning, it’s hard to tell.
At last, the spanking was over and I helped lift the sobbing boy off my skirted lap to stand him before me. He was bawling his eyes out, and his hands immediately shot back to begin trying to sooth the blazing inferno on his stinging, cherry red bottom. I gathered him in my arms and held him close, soothing him and stroking his hair as he buried his face in my ample bosom.
“There, there, Sweety…” I cooed softly, “it’s all over now. Mommy forgives you.”
Even though I was technically his aunt, ever since his mom had died in a car accident in his early years, I had become his defacto mother and he had been calling me mommy since right after his arrival.
“Let’s get baby’s diapers back on and then it’s beddie-bye time for you,” I told him as I consoled the crying child.
Mrs. Johnson smiled knowingly at me and she helped to arrange the stack of diapers on the changing pad that was a staple part of his nursery.
By now, Francis had lost all of his earlier bluster and was now quite compliant, ready to be pinned back into his bulky diapers for his daily nap.
It may seem strange to the reader that a 16 year-old boy is still wearing diapers, living in a nursery, and sleeping in a crib, much like any other incontinent toddler. So perhaps I should explain by starting at the beginning…

 

Even when Francis was still living with his mother, he had been a bedwetter up to the age of five. She had coped with it by putting him in diapers and plastic pants at night which at least kept his bedding dry, if not him. But when she died and he moved in with me, he started having daytime accidents as well. Not a lot, but often enough that I just decided to keep him in diapers during the day after changing him out of his wet ones in the morning. This turned out to be a wise precaution, as his daytime wetting only increased during his first year with me. At first, it was enough just to change him once, maybe twice, but as his wetting increased, I found it necessary to change him before his nap, afterwards, and sometimes when we were out in public or even during the evening too.
As Francis grew older, I noticed he really wasn’t interested in the things most boys are, and truth be told, most people thought of him as a sissy. Strangely, this didn’t bother me, and because I had always wanted a baby daughter of my own, Francis’ ways dovetailed nicely with some ideas I had in mind.
At first, I enjoyed dressing him in clothes that were a little feminine; flowered tops and thin, stretchy shorts that only emphasized the thick diapers he was wearing underneath. But as time went on, I decided to take things a step further, buying him clothes that were decidedly babyish or something a much younger girl might wear. He didn’t like it, but he was so passive and weak-willed that I easily bent him to my own, even if it was extremely embarrassing for him.
Most, if not all of my friends knew of Francis’ situation and they delighted in checking to see if he was wet, or playfully teasing him with his pacifier. But if anything, instead of trying to assert his masculinity, Francis became more and more of a sissy as time went on. I responded by regressing him even further and converting his bedroom into a baby’s nursery, complete with a pink crib, changing pad, frilly curtains, and nursery print wall paper. A pink dresser and netted playpen soon followed.
Nowadays, Francis dresses in much the same clothing one might expect to see a four year-old toddler girl wear; short, frilly tops that go to about his navel, party dresses full of frills, ruffles and lace, and fleece diaper shirts that make changing him much easier. Many of his outfits have babyish designs on them, whether it be building blocks, duckies or bunnies. He also has a small collection of Mary Janes, white, pink, and glossy black.
For the most part, Francis is a perfect little angel but it sometimes happens that I feel the need to take him over my lap for a hard spanking. He dreads these occasions and he begs and pleads not to have his diapers taken down, particularly if there are others present. Nevertheless, such attempts always fall on deaf ears and the sissy soon finds himself draped over my lap, his plastic panties pulled down past his knees and diapers unpinned, as I scold him for his latest childish infraction. Although I spank him until his face is wet with tears and his buns are a flaming, deep red, I always make sure to hold him afterwards and console him so that he realizes all is forgiven.
On his thirteenth birthday, Francis received as a special gift, a very secure chastity device which was promptly locked into place without delay or ceremony. It had been difficult trying to find one that would fit his diminutive size, and eventually, I had to get it custom made, based on an existing design. You see, he had never really developed down there and his genitals still pretty much resembled the equipment of six year-old child. However, as he reached puberty, he was starting to take advantage of his soft, fluffy diapers by playing with himself when he thought no one was looking at him. I found this to be disgusting and I simply wouldn’t tolerate it in my house.
Much to his chagrin, the chastity device put an abrupt and permanent end to both his budding erections and his nasty masturbating habits, which is just how it should be.
Francis was cranky and edgy for the next several weeks as he adjusted with difficulty to a life without self-pleasuring or orgasms. And there were times when I felt a spanking or a hot, soapy enema were warranted when his attitude became unacceptable. But in the end, the chastity device won the day. If anything, Francis became even more compliant and passive although he could still be fussy on occasion, much like any toddler who complains when his diapers are clammy and wet.
Francis has a babysitter named Kaitlin who is a senior at the local high school. She takes care of him when I’m unavailable to supervise him. This is particularly useful when I have a date and can’t be around to put him in his crib for his 8:00 bedtime. Kaitlin is a wonderful girl and she has my full approval to discipline him whenever she sees fit. It must be terribly embarrassing to be given a spanking by such a pretty girl as her, but that is just one of Francis’ many ordeals that he must contend with.
One of the things that I like about Kaitlin is that she is so strict–a very no nonsense kind of young woman that doesn’t tolerate any backsass from Francis. While sitting in his high chair, she often holds his hands in place with one of hers while she pushes the rubber nipple of a bottle of warm milk into his pouting mouth, forcing him to bow to her powerful will. One can see the expression of frustration and angst as he gazes helplessly down her low cut tops, gaping at her big breasts and wishing he could do more than just look.
Such experiences have a profound effect on him and it leaves him desperately horny and totally unable to do anything about it. The truth is, I think Kaitlin deliberately dresses provocatively just to tease the poor sissy but I really don’t mind. She usually just giggles and plants a big wet kiss on his cheek, leaving a red lipstick print for everyone to see, while forbidding him to remove it.
I’m not sure if it is the effect of being kept in a restrictive chastity device or if its just Francis’ lack of development but his little penis hasn’t grown significantly since I locked it up three years ago–it still measures about an inch and half when limp. One time recently, just out of curiosity, while I had the device temporarily removed for routine cleaning, I used some baby oil on his little guy to see how long it would get when fully erect. I’m sorry to say, it wasn’t very impressive, just rising to a little over two inches when hard. He shamefully begged me to rub it some more with the slippery oil but I simply pushed it back into its tube and locked it in place, leaving him denied and frustrated for the rest of the day.
It’s hard to say what lies in store for sissy Francis but for the foreseeable future, he will continue to be my precious little baby girl, dependent on his diapers and mommy for all his daily needs.

 

 

THE END

The Perverse Revenge of Miss Hazel

 

 

CHAPTER ONE

 

Ever since she had been little, Gina Carver had wanted a baby girl of her o

As a child, she had always had a very realistic (and expensive) baby doll she had cared for as her own, and in her later years, she was perpetually busy babysitting the neighborhood’s youngest children.

Growing into her teens, her goal of having a family and a baby girl of her own began taking clearer shape–first, to find a man who wanted a family as much as she did, and then to settle down and get married.

Although some might have called her obsessive, and her goals, perhaps a bit short sighted, she was fortunate to be blessed with good looks and a body that attracted men like bears to honey. Unfortunately, many of the guys she  went out with, really only wanted to get the curvy brunette into the sack, before moving on to greener pastures. Very few, if any, expressed any interest in settling down and raising a family.

That was, until she met Daniel. They hit it off immediately, and their courtship soon blossomed into love. He appeared to be the perfect man for her–her soul mate that shared her desire to have kids and raise a loving family.

Six months after they first dated, the two were married in a simple ceremony and a fabulous whirlwind of a honeymoon followed, with three weeks in sun-drenched Tuscany.

And then, a bit over a year later, Gina joyfully gave birth to her first child, a cherubic boy they named Timmy.

Although inwardly, Gina was disappointed that he wasn’t a girl, she was buoyed by his delicate features and attractive, almost pretty looks. Many people thought he had the makings of a child model and Gina smothered him with her love and affection.

Nevertheless, her desire to achieve her lifelong goal of having a baby girl hadn’t receded with the arrival of Timmy, if anything, it had only gotten stronger. However, despite her early success in bearing a child, the second one stubbornly eluded her. Daniel and Gina tried everything they could, but every month, brought no further good news from her pregnancy tests.

As the months rolled by, and slowly turned to years, Daniel began thinking there was something wrong with his wife. His strict religious upbringing made him inclined to believe that god had turned his back on her, and by extension, him–making him cast doubt on their relationship. As time went by, he became resentful and suspicious of his attractive wife.

In addition, the two of them began having differences in how Timmy was being raised. From Daniel’s perspective, Gina seemed to be making little or no effort to potty train Timmy, and to all outward appearances, she seemed content to keep him as a baby in perpetuity. She coddled and cuddled him, treating his daytime wetting as if it were perfectly normal

And then one day, on Timmy’s fourth birthday, the entire house of cards came tumbling down when Daniel abruptly announced he was having an affair with one of the parishioners at their church. This was a devastating blow for Gina, who had invested everything, both emotionally and career-wise into their relationship.

During the subsequent contentious argument, the shouting back and forth devolved until Daniel revealed his anger over Gina’s methods of parenting their only child. He thought she had kept him diapers for far too long and he questioned why a four year-old should still be treated like a toddler and still be breastfeeding from his mother.

Shocked and stung by his angry words, Gina vociferously defended Timmy, saying not all children could be expected to be potty trained at such a tender age, and that she had wanted her breast milk to be as ready as possible for their next child.

Poor Timmy burst into tears at the sight of his parents fighting so heatedly and he cried himself to sleep that night after his father stormed out.

And so began a very difficult phase of their lives, as Gina struggled to cope with raising her child alone. Timmy was fortunate, in that his beautiful mother had a deep and vast reserve of unquenchable love for him. To be sure, some outside observers might have found her techniques strange, noting that Timmy continued to sleep in his crib, and his diapers remained a daily fact of life, even going into his fifth year.

As time passed, some of her friends even began to shun her, which only caused to her to become more reclusive, and obsessed with her Timmy. She no longer had any legitimate reason to continue breastfeeding her son, but she found he became upset when he was denied nursing from her and the act had a profound calming effect on the distraught child.

While she never actually acknowledged it verbally–subconsciously, Gina wanted to keep Timmy as her precious little baby forever. She abandoned her plans to potty train him, and Timmy’s vast collection of infant clothes only continued to expand as time went on. The fact was, Gina loved to dress him in soft, innocent colors of pink, lilac, and cheerful yellows. His outfits grew more and more girlish and Gina delighted in buying him babyish, colorful plastic panties for his diapers in nursery prints, polka dots, and playful patterns.

Now unhindered and left to her own devices, Gina scoured the internet for baby clothing in larger sizes, dressing him each day in short diaper tops, onesies, and cute, ruffled rompers.

For Timmy’s part, he loved all the attention and love she showered upon him, and he never questioned what others thought was an increasingly bizarre treatment of him by his mother. Having only rarely been exposed to other kids his age, he didn’t think it was unusual to be treated as a baby, even as he blew out six candles from his highchair on his most recent birthday.

He loved the smell of baby powder and adored all the soft, fuzzy outfits he got to wear on a daily basis. He giggled happily when his mother tickled his tummy while changing his soaking wet diapers and treasured the moments when she read childish, bedtime stories to him in his crib.

And on those occasions when Timmy woke up crying from a bad dream, his mommy was always close at hand to let him nurse from her big, soft breasts. On such nights, he would fall asleep in her arms, to be cuddled by her as she gave him soft, comforting kisses, watching happily as he drifted off to untroubled slumber…

 

 

CHAPTER TWO

 

Seven years later…

Steadying himself on the soft, padded rails of his playpen, Timmy looked wistfully out the front windows of the living room, his soggy wet diapers sagging heavily from under his short, ruffled baby dress. It was still early in the afternoon, but Timmy’s diapers were already completely soaked, the warm milk he had been served at lunch having gone right through him. Every time he shifted in his kneeling position, he was reminded of his incontinence as the distinct smell of pee wafted around him, surrounding him in its childish embrace. Nevertheless, Timmy was oblivious to it and today, as usual, he was barely even aware that he had wet himself

The rain had finished hours ago, and a warm summer sun was now shining down cheerfully upon his neighborhood street. Puffy cumulus clouds scudded busily across the sky, as if in some hurry to get somewhere.

Today, like many days, Timmy was filled with boredom, idly looking out on the sidewalk, and wishing he could leave the confines of his house to play outside. Unfortunately, not only was the front yard forbidden to him, but today, his mommy had restricted him to the 4 x 4 netted enclosure of his playpen and he had to content himself with the few plastic toys he had available to him.

A lone, slim figure came walking down the sidewalk, and Timmy’s interest was suddenly piqued as he watched with intrigue, an attractive teenager approaching.

She was wearing glossy black, high heeled pumps and some super snug jeans that served to enhance her trim, curvy physique. Although she was still at least 50 feet away, as she drew closer, Timmy could easily tell that she was both good looking and in great shape. She wore a fitted white halter top with a low scoop neck, and when she stopped unexpectedly in front of his house to do something with her cell phone, her profile caught Timmy’s breath.

At the age of 13, Timmy was coming into something of a sexual awakening, and increasingly, he was discovering things around him that he found extremely arousing. This sexy, older teen in front of his house was just the most recent example.

The blond girl was busy manipulating her phone, completely unaware of the undivided interest Timmy was paying her from inside his house on the other side of his narrow yard. Staring hungrily at the delicious curves of both her derrière and generous bosom, Timmy’s little baby-sized penis quickly stiffened within the soggy, warm, wet confines of his diapers.

As he openly gaped at the female not twenty feet away, his rubber pacifier fell out of his mouth to hang from the pink strap that was clipped to his chest.

From behind him, he could hear his mommy working in the kitchen, cleaning up the dishes from their earlier lunch and he knew he could count on her being distracted for little while longer.

Without a moment’s hesitation, he reached down and quickly began rubbing the soft, cushiony front of his thick diapers, reveling in the wonderful sensations as he eagerly fed his need. Even though the cloth was completely saturated, it still felt marvelous against his throbbing little nub.

Drinking in her curves, Timmy rubbed himself feverishly, his nursery print plastic panties crinkling audibly. He had to be careful and make sure his mommy didn’t hear him–so far, he had been successful at hiding his budding obsession with the joys of masturbation but he didn’t want to risk her finding out. Nevertheless, he was so turned on and horny, he was willing to take a few chances as he gave his complete attention to the pretty girl outside. Under normal circumstances, it took Timmy no more than 30 seconds to achieve an orgasm. It wasn’t much really–hardly more than a dribble in his diapers when he was done. But he knew the girl might decide to start walking away at any time so it was important for him to reach his climax before that happened.

However, much to his dismay, he suddenly heard Gina’s footsteps coming out of the kitchen, signaling an unexpected and unwelcome end to his pleasurable activity. She came in, smiling down at him and wiping her hands on her apron as she approached his playpen.

“Well baby, looks like it’s time for your nap,” she said cheerfully, “I’ll just get you changed out of those wet diapers and then it will be beddie-bye time.”

Timmy felt a strong pang of resentment and frustration as his penis throbbed impotently and unsatisfied. Not that Gina would’ve noticed–unfortunately for Timmy, the poor boy had hardly developed much down there in the last five years and he was still essentially as small as a young toddler. Because he had never been exposed to, or had seen an adult male’s genitals, he lived in a state of blissful ignorance and he simply assumed that all young males were as under-endowed as he was.

Gina, for her part, couldn’t have been happier about his lack of development, since in her mind (which in the intervening years had become somewhat divorced from reality), she still saw Timmy as her precious little baby girl. To be sure, she had made sure that his clothing had evolved over time, and he now wore short toddler dresses during the day, while his nightwear had become both babyish and decidedly feminine.

In fact, at some point, Gina had unconsciously stopped calling him by his given name of Timmy, and now addressed him as Tammy all the time. She had always felt that deep down, her son had been born to be a girl, and it was only his diminutive genitalia that stood in the way of that goal.

Gently lifting her delicate, diapered boy out of his playpen, she helped him waddle down the hallway to his nursery, a comforting place filled with soft toys and all the baby furniture one would expect for a little toddler girl. There was nothing here to suggest that a boy lived in the room–quite the contrary. From the pink, fuzzy curtains, to the nursery print patterns of playful giraffes, baby bottles, and diaper pins covering the wall–from the frilly canopied pink and white crib in the corner, to the row of baby dolls on top of his pink dresser, no one could confuse this room for anything other than that of an infant girl.

As Gina prepared a fresh set of soft, fluffy diapers for him, Timmy stamped his feet in frustration, bunching his fists as he stood defiantly before his mother.

“But I want to go outside and play,” he whined petulantly, “I don’t wanna take a nap.”

Taking the baby bottle of warm milk, Gina patiently positioned it before his pouting lips, pushing the warm, wet rubber nipple into his protesting mouth and putting an abrupt end to their dialogue.

“Now, now,” she shushed him, “Mommy’s little baby needs to take her nap, you know that.”

Indeed, Timmy did know it all too well. There wasn’t a day that went by in which they hadn’t followed this familiar routine; after he was spoon-fed his lunch in his highchair, he normally had about an hour to play before his mommy came in to put him down for his afternoon nap.

During Timmy’s early years, he had actually enjoyed being treated as a baby by his mother–after the traumatic breakup between her and his father, Timmy had found a comforting safeness in her infantile treatment of him. And given his lack of social interactions with those of his own age, he hadn’t really given too much thought as to whether it was normal or not. But now, as he grew older, and was going through puberty, it was becoming increasingly obvious that his childhood was anything but routine.

And to add to all that, his growing feelings of sexuality had now become the catalyst for his changing attitude.

From his perspective looking out the window of his living room, Timmy saw the world going by and he wanted to become a part of it. With each passing day, he began to grow resentful of his mommy’s smothering baby treatment and quite simply, he wanted to grow up. He wanted to exchange his diapers and plastic panties for regular boy’s underwear, and his baby dresses for shirts.

And after his missed opportunity for a satisfying orgasm just moments ago, it only seemed to rub salt into his wounds.

“Why can’t I go out and play like the other boys?” he complained bitterly.

Gina pushed the big, wet nipple of the bottle back into his mouth, and then began peeling his clinging plastic panties down off his soggy diaper.

“Because you’re not like the other boys,” she explained patiently, “You’re mommy’s little baby, and you need your pampers and waterproof panties for when you wet yourself. Mommy needs to keep you safe and protected, and I can’t do that if you’re outside where you don’t belong.”

Without thinking, she unconsciously held her breath as she opened the enormous diaper pail next to his crib and tossed the damp vinyl panties into the bin. The sour, pungent smell of pee-soaked diapers surrounded the two of them, although Timmy didn’t take notice of it.

Holding him by the hand, Gina gently laid him down on his sturdy vinyl covered changing table as he fidgeted and whimpered, kicking his Mary Jane-clad feet in the air in helpless frustration. Pushing the multiple layers of his frothy Sunday school dress up, Gina swiftly unpinned the sopping wet cloth of his diapers, depositing them in the rubber pail as well.

“But maybe I could start wearing trainers some of the time?” he pleaded in an attempt at compromise as he paused from nursing his bottle.

“No Tammy,” she countered patiently as she firmly grasped both of his ankles and swung them high over his head to expose his soft, curvy little bottom, “Remember that time I took you over to your aunt’s house in just your trainers? Even with your plastic panties on, you still completely soaked them and leaked all over everything…

Timmy blushed at the embarrassing memory.

“No…You’re still just a big baby, and mommy’s going to keep you in your diapers where you belong for a long time to come.”

Timmy frowned and pouted miserably, helpless to defy his overbearing mother.

Squeezing out a generous amount of Desitin in her hand, Gina began smearing it lovingly all over Timmy’s bottom cheeks, giving them a nice, sticky coating of the cream to prevent diaper rash. With her middle finger, she ran it teasingly up and down the cleft between his buns, noting that he had suddenly stopped struggling against her.

In fact, as she looked below the frilly lace hem of his dress, she observed a decidedly unfeminine reaction in response to her maternal ministrations.

Timmy’s little penis, unrequited from his earlier efforts, was now standing stiffly to attention, as if to mock her attempts to baby him. Gina gasped, for this one involuntary act destroyed her carefully manufactured façade that her precious little child was a baby girl.

This had happened twice before, and much as she had hoped it had only been a fluke, Gina was forced to confront the reality of what was before her. Fortunately, she had had the foresight to take steps to it address this, just in case it should happen again.

Gently lowering his legs onto the changing table, she stepped away for a moment and retrieved a small box from inside the drawer that contained his baby panties. Emptying the multiple pieces of pink plastic out next to his prone body, she quickly but carefully fed his tiny package through the smallest ring available. With her fingers still slippery from the Desitin, she ran them along his hard little shaft to lubricate it before pushing it into a very short, restrictive tube that was no more than an inch long. It was barely bigger than a thimble and shaped much like the end of a penis but it contained a slit at the end so that Timmy’s peeing would not be inhibited.

Although Gina was by no means a large woman, her hands dwarfed Timmy’s tiny little genitals as she forcefully pushed the pink tube up to meet with the rounded ring behind his sack. This had the effect of compressing his miniscule shaft even more as it filled the tube to capacity and squashed his erection.

Now filled with concern, Timmy squealed anxiously, not comprehending what was taking place as his mommy inserted a key and twisted it, locking the two pieces irrevocably together.

Now his naughty little package was locked away, safe and secure, and totally unable to achieve another orgasm.

Sitting back, she looked down on his captive little penis and sighed with satisfaction. Never again would she have to gaze upon her precious, innocent baby and see a nasty erection. No, now those manly pleasures would be forever denied him, and by extension, so would masturbation.

Just as it should be for a baby still in diapers, she thought to herself.

“There,” she smiled, “that’s so much better. That will make you mommy’s perfect little girl again.

Taking up the baby powder, she sprinkled it all over him and began humming a happy tune as he anxiously kicked his feet, whimpering with angst and frustration.

Taking the multiple layers of the thick cloth diaper underneath his bottom, she pulled it up between his legs and tugged each corner snug, slipping a pink, duckie-headed safety pin through it to tightly secure the sides. Timmy reached down to try to make sense of the strange object imprisoning his penis but his mommy slapped his hand away and deftly fed some pink plastic panties over his feet.

“What is that you put on me, mommy?” he asked desperately.

“Nothing for you to worry about, sweetie-pie junior. Just a way to make sure my sweet little baby girl stays good, ” she grinned down upon him reassuringly.

Slipping the soft plastic panties up over his smooth, feminine legs, she worked them up and around the bulky mass of his fluffy diapers, running her fingers around his waist until she was sure of a good fit.

“We wouldn’t want our little girl to leak in her crib during naptime, would we?” she asked rhetorically in her syrupy, motherly tone as she smiled at her freshly pampered sissy boy.

 

 

CHAPTER THREE

 

Later that night, Timmy tossed and turned in his crib, horny, frustrated, and unable to sleep.

After having struggled for hours in his attempt to defeat the chastity device, he finally gave up and fell into a fitful sleep from his exhaustive efforts.

His first attempts had focused on trying to everything he could to extricate his penis from the contraption and when that failed, he tried rubbing the front of his diapers in a desperate attempt to climax without an erection.

Both efforts failed miserably and he only succeeded in getting himself more worked up and horny than when he had begun.

He was extremely frustrated, and filled with anxiety about contemplating a life without masturbation, to say nothing of ever having another orgasm.

 

Meanwhile, in the other room, Gina was spending some time on her computer, eagerly looking over a recent reply to an ad that she had posted last month for a babysitter. Recently, she had accepted a consulting job in another town that would require that she would be away Monday through Friday. It was hardly an ideal arrangement, but the money was generous and she was in dire need of replacing her depleted funds.

It almost seemed as if finding babysitter for her little Tammy was going to be as time consuming as that of getting a job.

To say it had been a difficult process, was putting it mildly. It was like looking for a needle in a haystack–trying to find someone suitable, trustworthy, and discrete, and a person that would understand Timmy’s…unique situation.

It was almost a month ago that she had posted the following;

Seeking a babysitter for my 13 year-old baby girl. She’s still in diapers and lives very much as any other toddler would.

Those applying must be between the ages of 18 and 35, responsible, and used to being very firm with children. Duties will include dressing, feeding, nursing, and changing my baby’s frequently wet diapers.

Generous salary offered for the right person.

 

Most of the replies she’d received expressed surprise and reservations about Timmy’s age–that is, until tonight.

It was with eager anticipation that Gina read a response and resume from one Hazel Marwood, 19, who lived in a nearby town. With her professional demeanor and strict, no-nonsense attitude, Gina was sure the girl would be a perfect choice to watch over her precious baby.

 

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

 

Hazel Marwood was a beautiful, but nevertheless troubled girl.

Like most people, she was the product of her background, and her background was checkered, to say the least.

Puberty had come early for her–and her body had developed spectacularly, far ahead of her peers. By 12, she was already sporting a full C cup and by 15, her mom was hard pressed to find bras for her in 34EE.

Her body was not the only thing that attracted every male in her school; with long, curly locks of dark chestnut hair framing a stunning face, beguiling brown eyes and full, luscious lips, Hazel was every man’s dream.

As she progressed into her teenage years, she found herself inundated with requests for dates and other, less honorable propositions.

Unfortunately for Hazel, her violent stepfather was not immune to her considerable charms, and after divorcing her mother under dubious circumstances, he began sexually assaulting the pretty teen on a regular basis. This continued for several years in which he physically forced himself upon her nightly, until one day when she finally ran away for good.

Her stepfather’s depredations had had a profound effect on her psyche as she grew up and as time went on, she began looking more and more at the opposite sex as the enemy. A deep-seated need for revenge began to form, first as a dark, flickering spark, only to grow inexorably within her until the flames of anger had reached a raging inferno.

She needed an outlet for her fury and some of the unwitting males who happen to be ‘fortunate’ enough to get dates with her, soon became the focus of her frustrations and inner demons.

Perhaps due to the perverse nature of her stepfather’s abuse, Hazel developed a fetish for anal play, particularly the use of strap-ons, which she used to dominate the few males that had the temerity to ask her out on a second date. If they had any doubts when they started, they soon learned just who would be wearing the pants in that relationship.

She began preying on shy, introverted males, who often lacked confidence and suffered from feelings of insecurity. To their dismay, they often found themselves bent over a pair of pillows or the end of a bed, their legs forcefully spread, as Hazel delivered a humiliating lesson in role reversals with her fat, rubbery strap-on dildo.

They would beg for mercy but their plaintive, pathetic cries simply fell on deaf ears.

Hazel’s interest in domination spread to other facets of the fetish, including enforced male chastity and spankings. She could recall only too well, her cruel stepfather’s method of obedience–namely, the use of a stout wooden paddle harshly applied to her perfectly shaped bottom whenever and however she defied him.

After searching online, Hazel selected several that were just like the ones he had used on her, except that she intended to use them on the weak males foolish enough to find themselves behind closed doors with her. Even those that willingly cowered submissively before her, soon found themselves bent over her lap, their pants pulled down, as she remorselessly blistered their bottoms.

Hazel’s life, like her relationships, was anything but stable, and she often went from job to job, unable to stay focused with the requirements that were needed. She was unique, in that she could land any job she wanted, but could never keep it.

It was late one night when she was well into her second bottle of cheap Chardonnay, when she came across an advertisement on Craigslist that caught her eye.

Seeking a babysitter for my 13 year-old baby girl. She’s still in diapers and lives very much as any other toddler would.

Those applying must be between the ages of 18 and 35, responsible, and used to being very firm with children. Duties will include dressing, feeding, nursing, and changing my baby’s frequently wet diapers.

Generous salary offered for the right person.

 

Something inexplicable about it appealed to her, and although Hazel had no real babysitting experience, that didn’t stop her from whipping up a resume that claimed otherwise. This was money that she badly needed and despite her lack of appropriate skills, she knew she could rely on her looks and charm to get her way. Both males and females were little more than putty in her hands, to be molded as she saw fit. She had always been quick-witted, and her ability to think on her feet gave her all the confidence she needed.

Over the next week or so, Hazel and Gina exchanged several emails before the latter set up a date for her to come over and meet Timmy in person.

The busty teen dressed professionally but provocatively, as was her nature when trying to win someone over. Besides her physical presence, she had a forceful personality that many found intimidating and she used it to her advantage, sometimes browbeating the people around her until she got what she wanted.

On the day of her visit, Hazel wore a hip hugging pencil skirt that did little to hide the tantalizing curves of her fit, sexy figure. Her top was a crisp, snow white blouse, the first three buttons purposely undone to reveal the deep, yawning cleavage between her spectacular, big breasts.

Her tall heels clicked crisply on the sidewalk leading up to the front door as she held her head up high, her stride revealing her confidence and self-assuredness. Ringing the doorbell, she waited patiently until she heard the approaching footsteps of Gina coming to the door. As it swung open, Hazel found herself somewhat surprised at the striking older woman before her. It wasn’t that she was unaccustomed to attractive females, but for whatever reason, it just wasn’t what she had imagined for the single mom requiring a babysitter.

“Come in–come in,” Gina greeted her cheerfully, “I’m so pleased you could make it.”

“I’m happy we were able to make this meeting happen on such short notice,” Hazel replied graciously.

Leading her inside, Gina stopped for a moment to look Hazel up and down.

“My, I have to tell you that you look fabulous,” Gina gushed, “You must have to fight the boys away with a stick.”

Hazel smiled to herself, recalling the wooden Spencer paddle she had just used to such good effect last night on the timid boy who had thought he had gotten “lucky” with her. It was an experience he wouldn’t soon forget.

“Thank you, ma’am,” she said pleasantly, treating Gina to her breathtaking smile, “I think appearances are very important.”

“Oh–no need to call me ma’am–I’m Gina, and this is my very special baby girl, Tammy.”

As she stepped aside, Hazel was able to get her first good look at the person she would be caring for.

Gina had dressed him very meticulously today in a fluffy, multilayered baby dress, it’s ruffled hem so short, that Timmy’s white nursery print plastic panties were fully on display. The perfectly smooth skin of his soft, girlish legs was complimented sweetly by the delicate lace anklets and his ubiquitous glossy white Mary Janes. Although the hem of his white and pink baby dress flared out in a cute, infantile style, his big, thick diapers were very much prominent–the shiny vinyl of his plastic panties giving them a precocious, distinctively toddler look.

Gina had combed his long, silky blonde hair into two pigtails and placed a big, pink satin bow at the base of each of them.

Timmy stood demurely, nervously batting his long eyelashes, his pretty baby blue eyes darting around the room as he sucked feverishly on the big rubber pacifier filling his mouth.

To be sure, he was overwhelmed by the presence of this tall, extremely gorgeous woman, six years his senior. She was the most stunning thing he had ever laid eyes upon, and her fabulous, overtly sexy body left him swooning with desire. It was only with great difficulty that he was able to stop staring at the two mammoth melons straining her bra and the semi-sheer fabric of her filmy white blouse.

A weak whimper of awe escaped his throat but was muffled by the fat pacifier in his mouth. As his heart beat rapidly in his chest, he could feel his tiny little penis throbbing and straining frantically within the short, stubby confines of his still new chastity device.

At first, Hazel was momentarily taken in by Timmy’s apparent sex–he really did make a convincing prepubescent girl in diapers. His pretty doe eyes lent him the look of innocence, and his cute, babyish attire only made him look all the more effeminate and prissy.

But Hazel was a shrewd judge of things and she could see through the monumental effort that Gina had made to give Timmy the look of a girl.

The diapered boy was quivering with admiration and wonderment as he made furtive efforts to look up into the beautiful woman’s dazzling eyes and unconsciously, a strong, hot stream of pee flooded into his diapers.

Knowing instinctively when to seize the moment, Hazel strode over, her high heels clicking on the hardwood floor as she flung her welcoming arms around the fidgeting boy, smothering him in her warm, bosomy embrace.

“Aren’t you just the cutest little thing!” she exclaimed enthusiastically, “And I’ll bet that you just love to play dress up.

Although Timmy knew full well that his mommy had a babysitter coming over to meet him, this was not at all what he had been expecting. Beside the fact that he’d assumed she’d be average looking, secretly, he had really hoped to win the person over and convince her to let him start being the young teenage boy that he really was.

What he didn’t want–was another female authority figure in his life that was only going to continue his mommy’s relentless policy of babying him.

Nevertheless, as Hazel mashed his face against the soft, forgiving pillows of her enormous breasts, he felt himself breathing heavily with white-hot desire and arousal. His short little penis was throbbing urgently and painfully in his device and he shifted his weight from foot to foot, fighting back the uncomfortable and slightly painful sensation emanating from within his diapers.

Paradoxically, Hazel was feeling sensations of arousal herself, but for completely different reasons.

There were certain facial characteristics of Timmy’s, that reminded her, in a somewhat distant way, of her hated stepfather, and the cruel, sadistic streak deep inside of her saw in Timmy, the perfect object of her twisted ambitions of revenge.

Without waiting for a response from her diapered charge, Hazel knelt down to Timmy’s eye level, brazenly reaching between his baby soft legs and slipping a finger inside the elastic leg hole of his plastic panties. Withdrawing her hand, she rubbed her fingers together and smiled knowingly, looking confidently and directly into Timmy’s eyes.

“Looks like mommy’s little baby wet her diapers, didn’t she?” Hazel giggled, “Maybe you should take me back to your nursery so I can give you a change.”

As Timmy’s cheeks buzzed with shame, Gina smiled with relief. She had been reluctant to get her hopes up, but this girl seemed to be the perfect fit for her little sissy.

“Come along Tammy,” Gina said as she took his hand, “let’s show your new babysitter your nursery.”

Timmy had little choice but to follow his mommy as she led him waddling sheepishly down the hallway, Hazel following closely behind.

“It’s almost Tammy’s bedtime, so we might as well change her wet diapers and get her ready for beddie-bye,” Gina explained.

As they walked into the room together, Hazel couldn’t help but be amazed at the attention to detail that had gone into creating Timmy’s nursery. In their conversations, she had been left with the impression that he had a certain minimum of furniture and clothing befitting a 13-year-old baby, but as she looked around the room, she was astounded by every little thing she saw. Clearly, this boy had been brought up as a diaper-dependent baby for years and the ever present smell of stale pee permeating the room only confirmed her suspicion.

Walking over to his pink dresser, Gina pulled open the second drawer to reveal an extensive collection of fuzzy fleece tops and colorful onesies.

“This is where I keep her nightwear for when she’s sleeping in her crib.”

It took some effort for Hazel to wrap her mind around Gina’s odd use of female pronouns for her son but she was careful not to let it show.

Without waiting to be asked, the busty teen took charge right away and stood Timmy before her, reaching under the multiple layers of his soft, frilly petticoats to grasp the damp elastic waistband of his plastic panties. With several sharp tugs, she peeled it off from his wet diapers and down his smooth, hairless legs.

Timmy stood blushing in place, shuffling his feet but he was acutely aware of an overwhelming sense of shame as this gorgeous girl treated him with no more respect than a helpless, incontinent toddler. His mommy was standing behind him, unzipping his baby dress and pulling it off of him. With a glance over his shoulder, Timmy spied the yellow pastel onesie decorated with elephants and bunnies that was awaiting him, draped over the rail of the crib.

The inevitability of it all made him feel more childish than ever; in a few moments he would be getting pinned into his nighttime diapers and dressed for bed–even though his bedtime wasn’t for another 45 minutes–while these two stayed up as long as they liked and discussed their plans for him. Plans he knew that as usual, he would have no say in.

Just as his onesie was waiting for him, so were three thick cloth diapers with a generous soaker pad sewn down the center of each of them. Unpinning the wet cotton around his hips, Hazel dumped it into his diaper pail and then sat him firmly down on his changing table.

It was then that she spied his pink little chastity device for the first time. She smiled broadly with approval but inwardly, her heart skipped a beat. Few things in life made her happier than knowing another male had been permanently deprived of orgasms. To think this sissy’s mom had already thought of it, filled her with respect and admiration.

Still, she directed her feelings elsewhere, acting as if his chastity device, like his diapers, were perfectly normal.

“You’ve really done a fabulous job here,” she remarked, clearly impressed, “Tammy has everything a little diapered toddler could ever hope for.”

“Thank you,” Gina answered with a proud smile, “Its taken some time, but I really think it was worth it.”

Seeing the tube of Desitin nearby, Hazel squeezed out a big glob and began slowly and sensuously coating Timmy’s cute bottom with it. As she reached his puckering pink hole, she suddenly slipped a well coated finger inside, making the poor abashed boy squeal with surprise.

Hazel smiled down on him knowingly, slowly easing it in and out and watching him blush a bright red as his breathing became labored. Kneeling the way she was, her back partially blocked Gina’s view, so Timmy’s mommy was unaware of the unexpected stimulation he was receiving.

Oh yes, I know were going to have all kinds of fun, she thought to herself as she picked up the baby powder next to him.

“Is this what mommy’s little baby wants?” she asked in a cheerful but patronizing voice.

Timmy swallowed hard, feeling overwhelmed by her sexy, intimidating presence. He was still groping with the pleasurable, yet shameful sensation of being so intimately invaded by this pretty stranger–and in front of his mommy no less!

Nevertheless, Hazel began powdering him generously, noting his pink chastity device was now throbbing anxiously with need.

Gina knelt down next to them and eased Timmy’s baby bottle between his quivering lips, giving him something to focus on as Hazel arranged the thick layers of his soft diapers beneath him.

Timmy couldn’t help but stare fixedly at Hazel’s big, beautiful breasts that swung heavily in her blouse before him. He gaped openly as they jiggled every time she tugged on his diapers and he whimpered in unrequited frustration.

Pulling the sides of his diapers snugly together, Hazel slipped a pink safety pin through the cloth and snicked it closed. After doing the same on the other side, she began sifting through Timmy’s panty drawer, marveling at the myriad of choices available.

“Wow, just look at all these cute plastic panties…so many to choose from…which one should we pick for you tonight, honey bunch?”

Timmy blushed and sucked harder on his bottle, consumed with arousal and frustration

“How about these?” she asked as she held forth a pair of pink vinyl panties with a Disney Princess theme, “I think they’re super cute.”

Without waiting for an answer, Hazel threaded them over Timmy’s Mary Janes and up past his calves, stopping momentarily to stroke the baby soft skin of his thighs.

“Oh my, you have just the most girly legs I’ve ever seen, and your skin is like butter,” she remarked with amazement, “How do you do it, Gina?”

“Lots of baby lotion, every day without fail,” she replied, the pride obvious in her voice.

“Well, you should be very grateful to have such a loving mommy as you do, Tammy,” she said as she began working his prissy plastic panties over the fat bulk of his fluffy diapers.

Hazel had beautifully manicured nails, and she used them to run around the stretchy elastic waistband of Timmy’s panties until all the soft Birdseye cloth was contained inside.

“There,” she said as she playfully patted the bulging crotch of his prissy diapers, “Mommy’s little baby is all ready for beddie-bye.”

Gina pulled the cute onesie she had been holding over Timmy’s head and tugged the stretchy material down and over his fat diapers, snapping the line of metal snaps one by one between his thighs. After removing his Mary Janes, she stood him before Hazel who was looking down with warmth and admiration at his bell shaped figure.

“Say goodnight to Miss Hazel,” Gina instructed her diapered son.

“Goo-goodnight, M-Miss Hazel,” he stammered, still completely awestruck and feeling overwhelmed by this stunning, sexy woman.

Bending down to his level, Hazel wrapped her lithe arms around the highly stimulated, trembling boy, using her bountiful bosom to further get him worked up. A shudder of pleasure rippled through him as he desperately hugged her back, not wanting to let go.

At last, Hazel released him, eliciting a wince of disappointment from Timmy.

Gina lifted the baby blankets back and guided her reluctant son into his crib, tucking his teddy bear under his arm.

“Nighty-nite, sweetie,” she said as she gently pushed his pacifier into Timmy’s quivering mouth, raising the side of the crib and latching it in place.

He squirmed anxiously under his covers as he watched the two women leave his nursery, turning the light out as they went.

After they were gone, and he could hear their footsteps receding, his hands immediately shot under the covers, seeking out the oh-so-soft, cushiony front of his diapers. Even though he knew his efforts were completely futile, he couldn’t stop from furiously rubbing himself as he re-pictured the breathtaking beauty that had just changed his diapers minutes before.

God, she was amazing, he thought to himself.

As he rubbed and fondled the front of his pillowy padded crotch, his feelings of arousal reached a fever pitch. His heart was pounding in his chest, and his breathing was coming in gasps.

Finally, with beads of sweat on his temples, he gave up in despair, utterly exhausted from his efforts.

Other than his ragged breathing, the room was silent, and Timmy lay there, wide awake, straining to listen to the muffled voices in the other room down the hall. Occasionally, he heard them laughing, but he was unable to discern anything of substance being said.

Finally, the frustrated youth fell asleep, his dreams filled with visions of Miss Hazel.

 

 

CHAPTER FOUR

 

…One week later…

The warm morning sun shone softly through the frilly pink curtains of Timmy’s nursery, happily illuminating the room, and giving it a warm, comforting aura. Just outside, a collection of birds sang cheerfully, their songs mixing in a clamorous cacophony of summer.

Inside the nursery, all was quiet, and its single occupant slept peacefully, clutching his fuzzy teddy bear in his arms, his usual pink pacifier still filling his mouth contentedly. Sometime during the course of the night, Timmy had kicked away his baby blankets and his round, diapered bottom now lay exposed, his shiny plastic panties reflecting the morning light.

Unbeknownst to the incontinent sissy, a two quart rubber enema bag, bulging to capacity with hot, soapy water, had just been hung from a hook over his crib, a long slender white hose running down from it to somewhere below the edge of his crib mattress, out of view.

The door of his nursery swung open unheard, and Hazel stepped quietly and gracefully inside.

It was Monday morning, and Gina had left town for her consulting job, leaving the care of Timmy in the buxom teen’s hands.

Walking over to the side of his crib, she gazed down at her charge silently, observing the petite, pretty boy in his diapers and clinging to his teddy bear as if his life depended on it. Bending down, she reached in between the bars of his crib and surreptitiously slipped a finger inside the waistband of his plastic panties. A smile crossed her beautiful face as she rubbed her fingers together, confirming her suspicions.

Not surprisingly, Timmy was soaking wet. But he wasn’t the only thing that was wet in the room.

As Hazel looked down on the innocently sleeping sissy and reflected on her elaborate, devious plans for him, she felt a shiver of arousal run through her body and she gently bit her lower lip. She had brought a large suitcase over for the week, and when she reflected on it’s unusual contents, it created a familiar wetness in her loins. To think that she had a whole week by herself, left to her own devices, filled her with eager anticipation.

Unlatching the side rail of the crib, she bent down to gently rub Timmy’s fat, diapered bottom, stopping to give it a playful squeeze before reaching up and stroking his silky blond hair.

Sleepily, he opened his eyes, looking up with surprise at his drop dead gorgeous babysitter. Nursing on his pacifier reflexively, he let out a mewl in surprise at this unexpected, yet sexy intruder and he blinked his baby blue eyes several times.

“Good morning, sleepy baby,” she said cheerfully as she gently grasped his pacifier and pulled it out. A long string of saliva followed it, but she was quick to push a bottle of warm milk she had brought along into his still open mouth.

Timmy accepted it and began nursing as Hazel helped him out of his crib and onto the changing table that was alongside. Humming to herself, she began peeling his clinging plastic panties down off his soggy diaper, the familiar, humiliating smell of a bedwetter suddenly surrounding them.

Timmy nursed feverishly as he stared up at his beautiful babysitter. She was wearing an impossibly tight pink crop top that hugged her stupendous breasts deliciously, and a pair of equally snug white short-shorts. Her curly brown hair spilled over her shoulders in a cascade of stunning femininity.

Gaping at his unexpected babysitter made Timmy suck harder on his bottle, as if he were trying to quench some insatiable, imagined thirst.

After unpinning his wet diapers and depositing them in his diaper pail, Hazel took a bottle of baby lotion and squeezed some into her hand.

She began by first applying a bit to his little sack, gently fondling each of his balls and smiling down at him. It only took a few moments before his penis stiffened in his cage, and he was forced to stop nursing from his bottle as his breathing became labored.

“You have such a cute little chastity device, Timmy,” she remarked as she held his diminutive package in her soft, feminine hands, “Does mommy’s little baby ever get horny?”

Timmy winced and nodded his head vigorously.

As if ignoring her own question, she put his throbbing genitals down, and began applying the creamy lotion to his sensitive bare bottom, sending shivers down the sissy’s spine.

“But you’re still a little baby who wears diapers…And babies don’t have orgasms, do they?” she reflected with a ravishing smile.

Although he could follow her logic, Timmy couldn’t bring himself to agree with her. She was running her slippery fingers up and down his crack and it was getting him frantically excited. A girlish moan escaped his lips and he looked up into her pretty brown eyes pleadingly.

“But I know something a little sissy like you needs,” she said assuredly.

Before Timmy could guess what she had in mind, she suddenly slipped a lotion covered finger up into his quivering pink rosebud.

“Ohh!” he squealed helplessly.

Smiling knowingly, she pulled it out, then plunged it back inside, reveling as Timmy squirmed and blushed deeply.

“Mm-hm, I think our little baby likes this,” she grinned as she began a tortuous rhythm in and out.

Timmy was panting, and his gaze fell to the long line of cleavage disappearing down Hazel’s snug top. He couldn’t remember being so horny in all his young life!

“But that’s just the warm up…” she said cryptically as she reached down and retrieved the enema nozzle that had been lying waiting in a jar of Vaseline. It was long, about eight inches, and shaped like a slender dildo, the white hose coming out of the base that led up to the enema bag.

She positioned it at Timmy’s hole, putting her left hand gently on his inner thigh.

“Spread your legs, baby, this one’s much bigger than my finger,” she told him.

Seeing the nozzle now for the first time, Timmy squirmed in fear, kicking his lacy, anklet covered feet in the air.

“No–please, I can’t take that!” he quailed.

“Hush, Timmy,” she replied as she began pushing the thick, rubbery tip into his quivering pink hole, “I know you’ll really enjoy this once it’s inside.”

Timmy tried to shift his weight on the table back away from Hazel but she was quicker and she thrust the greasy nozzle tip inside his pouting hole.

He squealed plaintively, bunching his fist and shaking his baby bottle as the slippery nozzle invaded his defeated back passage for the first time.

Hazel smiled knowingly, pausing for just a moment for him to get used to it before slowly pushing the nozzle all the way up inside him.

“Ohhh!” he moaned, gasping as he adjusted to the feeling of fullness.

Just as before, Hazel began slowly sliding it in and out, humping the hapless boy with the well-lubricated dildo until Timmy’s cries of shock soon turned to pleasure and then naked lust. He was breathing hard again, and his focus had returned once more to Hazel’s tight pink top, admiring her swelling curves and wishing he could touch them.

“We’re going to start this week off with a nice, soapy enema,” she announced merrily, “And I’m going to get you all squeaky clean, inside and out.”

Timmy bit his lip in angst. Although his mommy had given him enemas all through his childhood, he’d never had it done with a fat dildo nozzle, nor with the worrisome quantity of liquid contained in Hazel’s enema bag.

As she continued to slowly tease him with her rubbery invader, Timmy’s gaze wandered up to look at the bulging red bag, soapy suds still gathered around the opening.

“B-but…not a-all that w-water, right?” he stammered nervously.

“Mm-hm,” Hazel replied confidently, “Don’t worry, sissy–I’ll go nice and slow. I’m going to make sure you take every soapy drop.”

She gave him a playful wink but Timmy swallowed hard.

He wanted to protest further but between her sensual manipulation of the dildo nozzle and the breathtaking view down her top, Timmy’s voice failed him and he continued to pant with arousal.

“Here we go, Timmy,” she said as she plunged the nozzle all the way to it’s base and undid the clip.

The look on Timmy’s face said everything, as warm soapy water suddenly invaded him in a strong torrent, flowing deep inside of him.

“Ohhh!” he moaned desperately, clenching his sphincter muscles in desperate futility around the dildo to try and stop the flow. Hazel smiled prettily, enjoying the look of concern on Timmy’s innocent, cherubic face.

Closing the clip shut, she waited patiently for a minute to let the liquid settle inside of him, allowing it to flow through his bowels before undoing the clip again.

Timmy moaned helplessly, gritting his teeth and bunching his fists as he struggled to contend with the cramps forming in his abdomen.

“There…that’s mommy’s good girl,” Hazel said to comfort him, pulling the nozzle out just an inch and then pushing it back in, all the way.

She closed the clip again and waited, occasionally swirling the dildo just to tease her captive sissy.

Timmy was breathing hard now, but he moaned weakly as another warm, soapy torrent was released into him.

“Ohhh…I wa-want…I want my mommy,” he whined.

“Now, now,” Hazel smiled, “You’re doing just fine…you still have about half to go and this is going to make you all nice and clean inside.”

While Timmy was struggling with the fullness of his enema, Hazel could feel the wetness in her loins and she shifted slightly, wishing she could satisfy her own urges.

Patience, she chided herself, that will come soon enough.

Open and closed, Hazel carefully operated the enema clip, ensuring that Timmy took every last drop of the punishing liquid. He was moaning and whimpering when she finally began easing the slippery dildo back out of his hole. Timmy was desperate to get up, but his pretty babysitter had other plans. After setting aside the nozzle, she took a Vaseline coated butt plug and stuffed it unceremoniously inside his hole.

“That will help you hold it on your way to the bathroom,” she explained.

She helped the bloated and cramping sissy to his feet and giggled to herself as he limped weakly out of the nursery and down the hallway to the bathroom. While he was away, she took the enema bag into the kitchen, squeezed three portions of dishwashing detergent into it, and filled it once more to bursting with warm, soapy water.

Where one enema was good, two was twice as good, she chuckled to herself. This little bedwetter was in for quite a surprise when he should return from the bathroom, expecting to have his daytime diapers pinned onto him.

Hanging the heavy enema bag back onto its hook, Hazel took a seat on the edge of the crib mattress, and pulled her cell phone out of her purse to wait for Timmy’s return.

Ten minutes later, the sissy teen came back into the nursery, his baby blue eyes cast shyly downwards.

“Come over here, Timmy,” Hazel instructed the youth, “Get over my lap.”

Confused by her curt demand, he stood in place momentarily, still holding the pink butt plug in his hands.

“Come on, sissy–come over here,” she said, beckoning him over with her beautifully manicured hand, “over your babysitter’s lap.”

“Wha-what are you going to do to me?” he quaked nervously, as he took a few tentative steps towards her.

Without answering him, she grasped his hand, and pulled the wriggling pantywaist over her firm lap, situating his hips so that he was off-balance and vulnerable.

“Time for your second enema,” she said, her voice taking on an authoritative edge, “I want my little boy as clean as a whistle.”

Timmy began struggling for real, trying to rise up even as she easily held him down.

“Timmy, take a look in that full-length mirror,” she instructed, her finger pointed to the angled glass across the room. She had purposely set it up in such a way that Timmy would be able to see both of their reflections as he was bent over her lap.

He suddenly froze with fear as he looked and saw the stout wooden Spencer paddle she now had poised in her hand.

“Yes, my little baby bedwetter,” she smiled as she rubbed the paddle across both his bare cheeks in a manner that was both soothing and threatening at the same time, “this is what happens to little boys who disobey me.”

Timmy choked back a gasp of terror. He had never been spanked in his entire life, but he knew the little boy next door was occasionally paddled, as he could hear his wailing and sobbing coming from the open window of their house. During those traumatic times, he had cringed in fear as he sat in his nursery, playing with the simple toys in his playpen and listening, as each blistering swat of the paddle and the boy’s answering cries made him flinch.

He very rarely saw the little boy next door, but when he did, he appeared to be a very well behaved child. Timmy simply couldn’t understand why his parents felt the need to spank him.

And now, to his shock and surprise, he was facing the prospect of being paddled himself.

“Is this what you want, Timmy?” Hazel asked him as she continued to gently rub his soft, tender bottom.

“N-no, miss Hazel. I-I’ll be a good boy–I promise,” he pleaded desperately.

His babysitter set the paddle down next to her and smiled back at him, her pretty eyes twinkling.

“That’s good, sissy, because you’ve got a nice, warm soapy enema waiting for you,” she said gleefully as she picked up the lubricated dildo nozzle and stuffed it right back into his puckering pink hole.

“Ohhh!!” he cried, his feet kicking a little.

Hazel undid the clip and once more, an unstoppable flood flowed unhindered into his bowels. Timmy squealed and bunched his fists, wishing there was something he could do but knowing he was totally helpless against this beautiful and determined woman.

He certainly didn’t want to risk a spanking. Timmy had a very low threshold for pain and he knew he would begin crying even after the first swat.

No, as unpleasant as this was, he was just going to have to endure it.

The enema continued much as the first one, and it was mid-morning by the time he came back into the nursery, a chastened sissy boy with a newfound respect for his gorgeous babysitter.

“Okay Timmy, let’s get you into your diapers and plastic panties,” she told him as she led him back over to the changing table.

Timmy was much relieved and for the first time in as long as he could think, was looking forward to having his childish diapers pinned around his hips. Hazel had arranged three rectangles of the soft, fluffy cotton cloth in a stack, and she guided him down on top of it, acutely aware of the fact he was staring at her breasts again. Squeezing a large portion of Desitin onto her creamy hand, she grasped his ankles with the other and raised them up over his head, smearing the sticky substance onto his cute, youthful bottom to protect against his perpetually wet diapers.

As she lowered his legs back down, she looked into his eyes, a thoughtful expression on her face.

“You know,” she pondered, “I know your mommy has been diapering you all your life, but I’m inclined to think you’re a bigger boy than all that. Have you ever wanted to wear regular underwear like the other teenagers?”

A flicker of hope flashed through Timmy. Never before had anyone considered that he would be mature enough to go without diapers. And as his own mom had rightfully pointed out, his last attempt at wearing trainers had ended disastrously.

Still, he was reasonably sure that he had the wherewithal to control his wetting, now that he was the respectable age of 13.

“Oh yes–I’ve been telling my mommy that for years,” he replied quickly, with no small amount of exaggeration.

Without interrupting the task of diapering him, Hazel shook baby powder all over his frontal area and pulled the thick, bulky cloth up between his legs and pinned it on either side of his hips.

“Well, if you’d like, I’m prepared to give you the opportunity to show how truly mature you are. How does that sound?”

“Oh yes! Thank you miss Hazel,” he gushed enthusiastically. He still hadn’t lost hope that he might somehow gain her respect.

“Okay Timmy, here’s how it’s going to be,” she explained as she looked down on him with a look of firm resolution on her face, “If you can make it until lunch time without wetting your diapers, I’ll change you into your trainers, which you can wear until bedtime. If you have to go potty, just come and tell me, and I will take you into the bathroom, okay?”

Timmy was nodding his head, the excitement building inside him. Finally, someone was going to give him the chance that his mother would never consider.

“However…I should point out, that if you are willing to try this, there will be consequences if you let me down,” she said warily, as she positioned a yellow pair of plastic panties around his feet.

Timmy gulped–he had assumed that this was a risk-free proposition.

“If I find that you’ve wet your diapers and didn’t tell me beforehand, you’re going to get a very hard spanking.”

Timmy froze with anxiety as his beautiful babysitter tugged the babyish plastic panties up his silky smooth legs and began working them over his bulging diapers. He was terrified at the prospect of going over her lap to be spanked, but then, when would he ever get a chance like this again? She might never offer it again, or she might not become his permanent babysitter, or his mom could just veto the idea…the possibilities were endless.

No, despite the huge risk, he was going to have to try it. Nothing ventured, nothing gained, he reflected ruefully.

“O-okay, miss Hazel. I-I promise to get you if I have to go pee,” he told her nervously, praying and hoping that he wouldn’t mess it up

His babysitter looked back at him carefully, wanting to give him every opportunity to take back his bold stance if he so chose.

“All right Timmy, if that’s what you want, let’s see if you can prove to me what a big boy you really are,” she told him as she lifted him up off the changing table, “Let’s go get you some breakfast then.”

With a swat on his thickly diapered bottom, she took him by the hand and led him into the kitchen, helping him up into his highchair. Hazel wasn’t prepared to radically alter his daily routine, but instead of feeding him as Gina would have, she allowed him to use his spoon himself, albeit only after she had tied his baby bib around his neck.

In addition, she made sure he finished two full bottles of milk, since, to her way of thinking, all sissies needed to stay hydrated.

After breakfast, Hazel took him back into his nursery and the two laid on the pink carpeted floor together, happily coloring in his Disney Princess coloring books as the morning wore on.

Timmy soon became engrossed in creating a masterpiece with his crayons, and he hoped his sexy new companion would be equally impressed with his artistic skills. Carefully staying within the lines, and choosing his colors with care, Timmy was bursting with pride at his accomplishment.

He was nearly finished with the picture, and filled with eagerness to show off his work when Hazel unexpectedly reached across the space between them and slipped a finger inside the elastic leg band of his plastic panties.

Timmy froze in fear–he had totally forgotten about trying to be careful with his wetting! A dark expression clouded Hazel’s pretty features as her fingers felt the soggy wet cotton inside his waterproof panties.

Simultaneously, they both rose to their feet, Hazel shaking her head with disappointment.

“Looks like you’ve just earned yourself a trip over my lap,” she told the shaking boy.

“Y-you–you c-can’t spank me,” he quailed, “M-my mommy never spanks me.”

He licked his dry lips as a short squirt of panic-induced pee added to his already wet diaper.

Hazel reached for his hand and then took a seat on the edge of the crib mattress, bringing him stumbling over to her right side.

“Your mommy and I have different ideas on how we discipline naughty little boys,” she told him severely, “And now you’re going to get your sissy bottom spanked.”

Feeling the panic rising in him, Timmy’s eyes filled with tears and he stamped his feet in place.

“No!” he cried desperately, the tears tumbling down his cheeks, “I want my mommy!”

Hazel patiently reached over and sharply tugged his lemon yellow plastic panties down past his knees, even as Timmy made weak, futile attempts to stop her.

“I told you to let me know when you were going to wet your diapers and you disobeyed me,” she snapped.

Please miss Hazel!” he pleaded with the busty teen, “Can’t I just have one more chance?”

“It’s time for you to get a good, hard paddling, Timmy. Maybe then, you’ll try harder the next time.”

Yanking him over her lap, she felt his warm, pee-soaked diapers squish against her bare thighs and she swiftly removed the pins from either side. Pulling the thick Birdseye cloth back, she exposed his soft, quivering pale bottom.

“No! Please–please, miss Hazel!” he sobbed bitterly.

Timmy had been dominated for so long and so thoroughly by his mother, that it never even occurred to him to try to resist Hazel physically. Although given that she was a full foot taller than he was, even without her heels, it would have been pointless anyway.

Grasping the paddle, Hazel rubbed it against Timmy’s damp cheeks, just to fill him with fearful anticipation. By now, he was sobbing incoherently, begging her not to do it even as another stream of warm pee flowed helplessly into the diaper beneath him.

Hazel felt it too, and gripping the paddle with firm determination, she raised it over her shoulder and brought it down with a tremendous thunderclap on his bottom.

A band of fire seared itself across both his tender cheeks and Timmy howled out at the top of his lungs. He kicked wildly, his Mary Janes scissoring in the air but they were restrained by his damp plastic panties.

SMACKKK!!!

A second broad red stripe overlaid the first one, bringing a whole new color to Timmy’s cute little bottom. He beat his fists on the floor, the tears pouring down his cheeks to drip onto the carpet beneath him. This hurt far more than even he had expected, and he fought desperately to get up, only to be held in place by hazel’s firm grip.

From somewhere deep inside of her, a deep reservoir of anger and resentment rose to the surface, fueling Hazel’s pace and giving her the strength to wield the paddle like a holy instrument of retribution. Here was another sissy that she was going to teach a long lasting, and well deserved lesson to. It was obvious that Gina had been lax with the boy, and had neglected to give him the proper discipline that he should have received growing up.

I’m only too happy to correct that oversight, Hazel reflected with an evil smile as she viciously swatted his soft bottom again and again.

As Timmy cried uncontrollably, his cheeks soon took on the color of a glowing red furnace, and his skin became blotchy and swollen.

Somewhere, detached in the back of his mind, it occurred to him that the boy next door must now be realizing it was finally his turn for a spanking.

Hazel kept up that pace, smacking and swatting his bottom harshly, as Timmy bawled like a baby.

At last, the buxom babysitter was satisfied with his punishment, and she laid the paddle aside on his crib mattress. She smiled and briefly closed her eyes as a mini orgasm rippled through her body.

As she listened to the boy crying uncontrollably, she gently stroked his inflamed bottom, squeezing one cheek and then the other, as she evaluated her handiwork. The skin was hot to the touch, and she continued to caress it with admiration.

Reaching her two middle fingers into the open jar of Vaseline, she spread Timmy’s legs and pushed a dollop into his little pink hole. Next to the bed, Hazel had kept his butt plug handy, and she picked it up now after swirling it again in the Vaseline. Poising it at Timmy’s rosebud, she gently but firmly pushed it inside him, evoking a squeal of surprise and angst from the distraught, crying boy.

Helping him to his wobbly feet, Hazel smiled to herself as she looked down once more upon his little pink chastity device, thinking how perfect it was that he was plugged in back and caged in front.

This is what all sissies deserve, she reflected.

Kneeling down, Hazel took a few of the thick, soft diapers stacked up alongside Timmy’s changing table, and arranged them one on top of each other.

“Come along baby, we need to get you back in your pampers where you belong,” she told him.

Still crying as he frantically rubbed his blazing bottom, Timmy knew just how right she was.

As she sat him down on the diapers, he cried out bitterly as his scorched, candy apple cheeks made contact with the fluffy, soft cotton. In no time, Hazel had his feet over his head while she smeared another layer of cool Desitin across his punished behind. Bringing his legs back down, she powdered all over his chastity device and up to his navel, the babyish scent filling the air.

“I’m going to give you another chance, Timmy,” she told him as she drew the thick cloth up between his legs and pinned it around his hips.

“This time, you are going to come to me when you feel the need to wet yourself. Do I make myself clear?” she said sternly as she looked him in the eye, “Or you’ll be taking another trip over my lap.”

“I-I-I can’t,” he sobbingly admitted, the tears still spilling down his cheeks, “I can’t help it when I wet myself…It just, happens.”

“Timmy, you’re 13 years old now and a teenager. Your mommy might think it’s okay for you to spend the rest of your life in diapers and plastic panties, but it’s high time you grew up,” she said as she clipped the pink duckie-headed safety pin closed on the other side, “You are going to tell me when you have to wet, or you are going to get your bottom spanked. It’s that simple.”

 

 

CHAPTER FIVE

 

Timmy sat strapped into his highchair, his face a mess from the baby food Hazel had been spoonfeeding him, and his plastic Dumbo bib was splattered with numerous colors of the pureed slop. The butt plug she had forced into him earlier had ached a bit at first, and even now, he could hardly ignore the sense of rubbery fullness stuffed into his virgin back passage. Every time he shifted in his seat, the fat plug seemed to burrow deeper into his pouting rectum.

One of Hazel’s many male admirers had called her and now Timmy sat bored and very much trapped in his highchair, idly swinging his legs as she ignored him, chatting and giggling on her cell phone.

Finally, after what seemed like forever, she hung up and went over to the sink to retrieve a wet wash cloth. Bringing it over to the sissy waiting for her, she wiped it across his messy face. Hazel removed the bib, and she looked his short baby dress over carefully, to make sure none of his lunch had slopped onto the delicate, frilly confection.

Before she unlatched the tray that was keeping him captive, she reached down and lifted the multiple layers of his dress to expose his yellow nursery print plastic panties. Her unexpected movement caused Timmy to bite his lip nervously, fearing her imminent discovery of his soggy wet diapers.

Wordlessly, she held his dress out of the way while her other hand went down behind the elastic waistband, feeling the soft cotton cloth, now fully saturated with warm pee. For a brief moment, Timmy was treated to a fabulous view down her snug pink top but he cringed in fear when he felt her fingers against his skin.

Hazel stood back and made no effort to release the serving tray–instead, she placed her hands on her curvy hips, and a look of resigned disappointment darkened her pretty face.

“Well…once again, you’ve went and wet your diapers just like a baby without telling me,” she stated as she addressed him sternly, “Looks like I didn’t paddle you hard enough the first time.”

Timmy, who was already whimpering and fidgeting in his seat, suddenly burst into tears–his poor bottom was still painful and stinging from his earlier spanking.

“Please–please, miss Hazel,” he begged her pathetically, “Please don’t spank me again.”

“You have two choices, Timmy,” the tall brunette said as she crossed her slim arms over her bountiful chest, “I can put you over my lap and give you another sound paddling–or…I can punish your bottom in a different way. It’s your choice.”

“I-I’ll take the different way,” he blurted out between sobs.

“Very well,” she said as she unlatched the serving tray from his highchair, undid the buckle from around his waist, and helped him to step down. Timmy’s crying had abated somewhat and he was sniffling now as she took him by the hand down the hallway and into his nursery. Once they were there, she stood him in place and tugged his plastic panties down off his wet diaper, placing them on his changing table for later use.

“You won’t be needing those for a while,” she told him as she suppressed a smirk.

“I want you to climb into your crib and lay face down over these two pillows,” she explained as she patted a pair of pillows arranged in the middle of the bed.

Timmy didn’t know what to make of her instructions and he wondered anxiously what further terrible punishment she had in store for him. Climbing into his crib, he looked over his shoulder and watched as Hazel began pulling an elaborate leather harness up her shapely thighs, tugging the straps snug and tight around her hips. Timmy gulped hard when she turned around and he saw the massive rubber dildo with realistic looking veins running down it’s shaft that was now protruding from Hazel’s pelvis.

“Wha-what are you going to do with that?” he quaked nervously, his voice cracking.

“This is what happens to sissies who can’t control their wetting and pee their diapers during the day,” she scolded him as she grabbed the jar of Vaseline and climbed into the crib behind him.

Timmy began whimpering and his eyes filled with tears.

“No–please–please don’t do it to me, miss Hazel–I promise I’ll be good,” he pleaded with her.

Hazel could feel herself getting wet again and her heartbeat increasing as she slowly unpinned Timmy’s wet diapers and pulled them back, exposing his pink, bruised bottom. It looked so cute and girlish, and she couldn’t wait to bury her dildo deep into his sissy hole.

His butt plug was still firmly lodged between his punished cheeks as she began generously coating her dildo with the Vaseline. As she pulled the plug out, Timmy squealed and kicked his feet a bit but Hazel had already straddled the back of his thighs and her weight was preventing him from escaping.

Bending over slightly, she used one hand to pry his stinging cheeks apart and the other to position the fat, blunt tip of her dildo against his quivering anus.

“I’m going to pop your cherry, Timmy–I hope you’re ready for it,” she growled.

Timmy was sobbing uncontrollably but otherwise making no real attempt to try to escape. He fully recognized the complete superiority of his new babysitter and he knew he was going to get violated whether he liked it or not.

Having a vast amount of experience using strap-on dildos, Hazel knew just where to position it and what angle to use. In no time at all, she was pressing firmly with her pelvis against his puckering little pink hole, and the wide, rubbery head finally pushed past his defeated sphincter.

“OHHHHH!!!” Timmy squealed, his Mary Janes kicking ineffectively behind her.

Slowly, Hazel pushed the massive shaft in deeper, inch by inch, taking her time with the helpless, squirming sissy. His little hole had never been stretched like this before, and he beat his fists on the bed as he cried out plaintively.

“Thaaat’s mommy’s little girl,” Hazel said throatily, her voice having become consumed with lust. Her clitoris ached from having been aroused for so long and not having had any satisfaction and his cries of vulnerability only excited her more.

Timmy’s girlish squeals filled the room and Hazel plunged it in until the big, fat dildo bottomed out.

“Take my big cock, sissy boy,” she grunted from above him.

Gripping his narrow hips tightly, Hazel pushed even harder, reveling in the wonderful sensation being transmitted to her dripping wet pussy. At the same time, Timmy wriggled and squirmed beneath her like a fish trying to escape. Except there was no escape for Timmy today!

The fact was–the more he struggled, the more turned on Hazel became and a moan of pleasurable satisfaction escaped her lips.

Pulling it out until only the fat, bulbous head remained, she paused and then slowly plunged it back in again, forcing Timmy to take every inch of the slippery silicone cock. The poor boy thought for sure he was being split in two, and he moaned piteously. Hazel’s clit throbbed with the sound of his squealing, and she began a slow, teasing rhythm, in and out, stretching his tight, aching hole to it’s very limit.

Every time she thrust inwards, she used her hands to stretch Timmy’s pink cheeks outward, as she plunged the 9″ shaft deep inside of his virgin rectum.

Desperately gripping the baby blankets of his crib, Timmy sobbed, grimacing with the dull pain of his back passage being so thoroughly violated. Occasionally, Hazel would bury her cock in to the hilt, grinding the rubbery invader hard into his very bowels which would elicit load squeals and moans from the trapped little sissy.

Picking up the pace, she gradually went faster and faster, plunging the massive shaft in and out as Timmy kicked and wailed. At last, she rammed it in hard, grinding all her weight against his backside and holding it there.

Timmy cried with defeat just as Hazel shrieked with ecstasy, her eye-crossing orgasm washing over her in a tidal wave of delicious, all-consuming pleasure.

With her heart pounding and her head swimming, she gasped for breath, gulping in great draughts of air as she struggled to recover from her climax. Her body felt weak, and she didn’t have the strength yet to move.

Timmy lay whimpering, squirming beneath her and desperately wanting to be free of her gargantuan, emasculating cock that was still buried deep in his throbbing back passage.

Finally, once her head had cleared, Hazel slowly eased the slippery battering ram out of his aching pink hole. Stumbling out of the crib, Hazel drew her arm across the patina of sweat upon her forehead, amazed at the force of her own orgasm. Drunkenly, she undid the snug straps around her hips and let the heavy rubber dildo and harness fall to the floor with a thump.

“Oh my God, that was so amazing,” she exclaimed, her head still spinning, “Trust me,” she said breathlessly, “you’re going to be taking my cock every day from now on.”

Timmy was still laying over the pillows, his pink bottom pointed skyward and his legs spread apart, whimpering and crying softly.

“Come on baby,” Hazel beckoned him gently, “let’s get you into a fresh set of diapers and plastic panties, it’s my sissy boy’s naptime.”

Pushing Timmy’s pacifier into his pouting mouth, Hazel went through the familiar routine of powdering and pampering the young teen, tucking him into his crib when she had finished.

After leaving the nursery briefly, she returned with a baby bottle of warm milk in her hand. Bending down, she gently wrapped her right arm around Timmy’s head and after removing his pacifier, she eased the dripping rubber nipple of the bottle between his lips.

“There, there,” she said soothingly, “here’s some nice warm milk for mommy’s little baby. And don’t you worry your pretty little head about wetting yourself while you’re asleep–I know how much you need your pampers–everyone knows you’re a hopeless bedwetter who just doesn’t have any control.”

Timmy sobbed uncontrollably and nodded, overwhelmed with this afternoon’s traumatizing events.

“Please don’t punish me, miss Hazel,” he whimpered around the big rubbery nipple filling his mouth, “I can’t help it.”

“Shhh…I know baby,” she said softly as she caressed his tousled blonde hair, “that’s all over now,” she assured him as she kissed his forehead tenderly.

“You won’t have to try to prove that you’re a big boy anymore, you’re mommy’s little sissy toddler. Let’s not have any more talk about you wearing regular underwear–you belong in nice, thick diapers and plastic panties and I’m going to make sure that’s where you stay.”

Timmy hugged his teddy bear tight and nursed from his bottle, both relieved and ashamed to hear her announcement. He had really hoped to enlist Hazel as an advocate for his plans but to his dismay, he realized he had only succeeded in giving his mommy another determined enforcer of his humiliating baby regime.

Hazel stayed by his side, giving him tender kisses as he finished his bottle, his long lashes fluttering sleepily.

 

Later that afternoon, as Timmy lay in his crib with his diapers wet again and clinging to his bottom, his dreams were filled once more with Hazel. Sucking feverishly on his pacifier, Timmy occasionally whimpered in his sleep and his angelic face appeared troubled.

As he tossed and turned in his crib, unconsciously, his hands had slipped beneath the blankets, to anxiously rub the front of his fat, cushiony diapers while he dreamed of pretty Hazel plunging her big dildo into him, again and again…

 

 

CHAPTER SIX

 

Timmy sat in his playpen, feeling dirty and thoroughly humiliated.

Just like the two mornings previous, Hazel had administered two, long soapy enemas to the boy, but today, instead of letting him up to release it, she had instead, swiftly re-diapered him and told him to let nature take its course. It wasn’t long before all that soapy water came rushing back out, to fill up his diapers in a sequence of gushing hot, liquid torrents.

Timmy had burst into tears, overcome with feelings of shame and helplessness. Now he felt like he was practically swimming in his diapers. Eventually, the multiple layers of thick, absorbent Birdseye cotton and his plastic panties did an admirable job of containing it all, but it only made Timmy feel more babyish than ever.

Hazel left him in his playpen to keep him out of her hair while she relaxed with her cell phone, texting her friends. Two of them had expressed an interest in checking out her teenaged baby, in part because they found it impossible to believe, but also because with Hazel–anything was possible. To be sure, their busty friend had acquired a reputation at school for having defeated and humiliated a number of geeky nerds and sissies, but nothing like this.

As she read the messages indicating they would be over shortly, Hazel smiled knowingly at Timmy sitting across the room in his playpen. Humiliation was always better when it was shared amongst friends.

Timmy was stacking his big plastic blocks, the seat of his thick diapers sticking tenaciously to his rump. On the plus side (if there was one), he felt fortunate to be free of his usual morning butt plug, which had become an emasculating, daily routine for him.

He paused momentarily in his activity to wet himself, the pee re-warming the soggy cloth between his legs in a way that was both familiar and welcome.

Happily, Hazel was no longer spanking him when he wet his diapers. But instead, she had made good use of her strap-on, raping his tight little hole for an hour last night before bed while he squealed and moaned. It had left him sore with his rosebud aching as he fell asleep in his crib.

Timmy was just thinking it was going to be another quiet morning, when they suddenly heard a knock at the door. Frozen in place, Timmy looked over to Hazel, who smiled and walked casually across the room to answer the caller.

As soon as the door opened, mutual, exuberant greetings were heard as Hazel hugged her friend and brought her inside.

Timmy blushed deeply as he beheld the young, attractive woman standing before him.

She was about 5’8″, with long, shimmery blond hair cascading over her soft shoulders. She had a modest bustline, but her narrow waist gave her a decidedly womanly figure, accentuated by her choice of a tight lace-up top that left her flat tummy exposed. Because it was summer, she wore equally snug shorts that hugged her perfect bottom and showcased her fabulous toned legs.

It was very apparent that this girl spent regular time in the gym.

Her pretty blue eyes seemed to contain a glint of cruelty and instinctively, Timmy feared this woman.

Looking down at Timmy who was cringing in his playpen, she shook her head in obvious disapproval.

“You know, I really didn’t believe you,” she said to Hazel without taking her gaze off the diapered teen, “But everything you said was exactly right.”

Timmy could only wonder what sort of things his babysitter had said about him and he bit his lip as his eyes darted around the room nervously.

“I can’t believe you’re thirteen years old and still in diapers–Didn’t your mommy ever potty train you?” she asked pointedly.

Timmy blushed hotly. For years, he’d never given any serious thought to the bizarre way in which his mommy had raised him. But now that he was going through puberty and being exposed to more and more people, he felt his shameful status most acutely.

Without waiting for an answer, the girl continued on in her acerbic tone of voice;

“Are you sure he’s a guy?–With those pigtails and long lashes, I would have sworn he was a little girl when I first saw him. And look at those soft, girly legs–not a trace of hair anywhere.”

As she stood over the padded rail of his playpen looking down at him, he felt very small indeed. It didn’t help that his fat diapers were absolutely soaking wet–her scorn made him feel like he was no more mature than an incontinent toddler.

Hazel was enjoying watching her friend humiliate Timmy. To be sure–it was nothing he didn’t truly deserve.

“Timmy, this is my good friend, Kayla,” Hazel introduced her.

With his cheeks burning red, Timmy was too overwhelmed and intimidated to speak. Instead, he looked away, licking his dry lips and wishing he could be anywhere else, rather than under the demeaning glare of this beautiful blonde.

Just then, another knock was heard at the door.

“Oh, that’s got to be Michelle,” Hazel announced.

As she answered the door, Timmy was shocked to see another good looking girl coming into the room and greeting his babysitter warmly. She looked to be older than the other two, probably in her mid-20s, but what caught Timmy’s eye was her very generous bosom, barely contained within her fitted white top. As she strode into the room and caught sight of the diapered boy in his playpen, a big smile appeared upon her gorgeous face.

“Oh my God! He’s sooo cute!” she exclaimed as she came over to take a closer look at him.

Timmy gulped hard as he gazed up at the twin mounds of femininity stuffed into her top and then up into her twinkling green eyes. Whereas Kayla felt nothing but disdain for him, this girl seemed to embrace the idea of a young teenager still in diapers. While it was humiliating in the extreme to be shown off like this, he was happy to receive her approval, however he could get it.

“Wow, he really looks like a pretty little girl,” Kayla gushed, “Hiya cutie!”

She reached down and pinched his blushing cheek playfully.

The move caused her swelling breasts to heave forward, threatening to leap out of her struggling top and Timmy gasped with amazement.

“I have a baby girl at home, too, Timmy. I’ll bet you two would love to play with her dollies together,” she added.

“How is your little one, Michelle?” Hazel asked her solicitously.

“She’s strong and healthy,” her auburn haired friend replied proudly, “and she’s drinking so much milk, I think I’m producing extra,” she smiled.

She emphasized her remark by cupping her tremendous bosom in both her hands and hefting them like melons at the market.

Timmy swallowed hard at the gesture, and unconsciously, he licked his lips hungrily. Although it had been many years since he had actually nursed from the breast, well-endowed women such as Michelle and Hazel were a constant source of arousal for the childish boy. However, this was due less to an adult sexual desire, than it was to an infantile need to nurse from them.

“So does your little baby here wet her diapers like a real one?” Michelle asked with a giggle.

“All the time,” Hazel quipped, “As a matter fact, I was just about to change him when you two came over.”

Michelle seemed thrilled at the prospect, although Timmy was filled with anxiety.

“No, miss Hazel,” he whined pathetically in a small voice, “Can’t we do it later?”

“I know you’re past overdue,” she replied firmly as she lifted him out of his playpen, squeezing the soggy seat of his round, diapered bottom, “Come on sissy boy, let’s get you changed.”

Timmy whined miserably as he waddled down the hall after her, his wrist held securely in her hand.

As the three of them entered his brightly lit nursery, Kayla’s brow furrowed.

“Ewww, what is that smell?” she demanded.

“Oh, sorry,” Hazel said as she tugged the boy’s cute plastic panties down off his diaper, “that’s Timmy’s diaper pail. I’m afraid a bedwetting sissy creates a lot of laundry and the smell just goes along with the territory.”

Kayla shook her head as Timmy avoided her disapproving glare.

The reality was–wet diapers were a fact of life for him. He could no more stop his wetting than for the earth to stop turning, and he just wanted to get through his day with a minimum of humiliation.

“Well I think you’re nursery is absolutely scrumptious,” Michelle said, exuding enthusiasm as her eyes surveyed the pink room, “There’s everything here and more that a big baby could ever want.”

Hazel had placed Timmy on his changing table and his sopping wet diapers were now unpinned, revealing his pink chastity cage to the other girls for the first time.

“No way! Is that what I think it is?” Kayla asked, her voice revealing both scorn and interest in equal measures.

She had bent down and was looking closer at the tiny device imprisoning Timmy’s little penis.

“Wow! That is really small! It’s the size of my pinky!” she laughed contemptuously.

Timmy felt completely humiliated. It was bad enough having his baby lifestyle revealed to these beautiful, adult women but for them to see his chastity tube was absolutely mortifying. His cheeks blazed and his blushing went all the way down to his chest.

“Well, I guess we know he’s not playing with himself,” Kayla smirked derisively.

“Nope. His mommy thinks of him as a little girl and she decided that erections don’t have any place in his life. So his chastity device keeps him sissy soft down there, 24/7. I’m afraid that also leaves the little masturbator high and dry in the orgasm department,” Hazel chuckled.

“Just as it should be,” Kayla remarked caustically.

“Awww, you poor thing,” Michelle said sympathetically as she looked down upon the squirming sissy.

Hazel grasped his ankles and swung them unceremoniously up over his head, putting him in the most humiliating position possible and revealing his pink rosebud to the three of them.

“Kayla, can you hand me that butt plug over there?…Yes, the one in the Vaseline,” Hazel asked as she pointed behind her.

Rather than actually picking up the silicone object, Kayla handed her the entire jar of Vaseline instead, a disagreeable look on her face.

“Thanks,” she acknowledged as she swirled the butt plug in the jar, coating it generously and then positioned it at Timmy’s sissy hole.

“Open wide, baby, it’s time again for your butt plug.”

Timmy moaned piteously as she slowly but forcefully pushed the fat, rubbery plug deep inside of him. His reluctant sphincter soon gave up and embraced the emasculating invader, quickly closing up around the narrow base and leaving him unable to expel it.

“There, just what a little sissy needs,” she grinned as she began smearing diaper rash cream across his bottom.

While she held his ankles over his head, with her free hand, she pushed three fluffy white diapers under his rump and then let his legs down. The pungent smell of urine surrounding them was briefly exceeded by that of the fragrant baby powder, as Hazel applied it generously to Timmy’s diaper area.

Pinning the sides snug around his hips, Hazel picked up some white nursery print plastic panties and pulled them over his feet. Timmy whimpered weakly as she pulled the crinkly panties up his legs and worked them over the fat bulk of his diapers.

“Hey, so I was wondering,” Hazel began tentatively, “Do you guys mind taking things outside while I wash my car? It’s such a beautiful day, and I figured we could talk out there.”

“Oh sure,” Kayla agreed, “my car needs it too.”

“What about Timmy?” Michelle asked.

“Let’s take him outside with us,” Kayla suggested, “We can take his playpen out to the front yard–that way you can keep an eye on him, Hazel.”

“Yeah, why not?” she said in agreement as she sat back and gazed at the freshly diapered youth.

Timmy was aghast at the idea, and his lacy anklet covered feet kicked nervously.

“I-I-I can’t go outside, n-not to the front yard, my mommy never makes me do that,” he quailed.

“Oh yes you will,” Kayla said sternly, “You’ll do as I say, you little pantywaist.”

“No! You’re not my mommy!” Timmy snapped petulantly.

Unfortunately, with his fat diapers and sissy top, his tantrum only served to make him look more childish and befitting of his baby status.

Without warning, Kayla reached into her purse and swiftly retrieved a wide backed hairbrush. She grabbed Timmy by his twig-like arms, yanking him to his feet and quickly delivered three hard swats to his fat, diapered bottom. Even though he was well padded, he nevertheless burst into tears, stamping his feet in frustration as Kayla’s hairbrush landed with a dull thud, three times in quick succession.

Taking a seat on the edge of his crib mattress, Kayla jerked him awkwardly over to her side and quickly tugged his plastic panties back down past his knees. In seconds, she had pulled him over her lap and was undoing the pins that Hazel had just clipped shut. Timmy howled and kicked, struggling to get up and off from her lap but she grabbed his arm and twisted it behind his back, forcing him towards the floor again.

Hazel watched with avid interest, feeling no particular desire or need to intercede. On the contrary, as she watched the diapered sissy being roughly handled and about to get his cute bottom spanked, she felt her loins tingling and becoming wet again.

With Timmy’s tender cheeks now fully exposed, Kayla wasted no time and immediately began spanking him hard with her hairbrush. He kicked and howled miserably every time the unforgiving wood impacted his defenseless bottom, turning it a bright shade of red in no time.

Tears streamed down his cheeks, dripping onto the floor as he cried like a baby, helpless to prevent this humiliating punishment.

Hazel wanted badly to slip her hand down the front of her shorts and rub her aching clitoris. It throbbed in angst as she watched the boy flailing and kicking frantically, his buns looking like two red candy apples.

Finally, she couldn’t take anymore.

“Okay–my turn,” Hazel said, her voice thick with desire.

Somewhat taken by surprise, Kayla paused, holding her hairbrush at the ready as she looked up to her friend.

Hazel pulled Timmy to his feet briefly, and then took Kayla’s place on the edge of the crib mattress. Before the punished sissy could figure out what was going on, he was being pulled back over Hazel’s lap, where he landed with a loud squeal.

Reaching for the paddle lying next to the crib, Hazel grasped it firmly and immediately swatted his crimson bottom as hard as she could. The air holes in the face of the paddle produced a tremendous sting and Timmy howled at the top of his lungs with grief.

It felt good to hurt him, and she spanked him harshly, his sobbing being sweet music to her ears. Looking down on the pink rubbery handle of the butt plug seated between the cleft of his scorched cheeks, it gave her a special satisfaction knowing that his bottom was being punished inside and out at the same time.

Not until his bottom was blistering red and swollen did she stop and set the paddle down.

Helping him to his feet, Hazel stood up and wrapped her arms around the youth who was crying uncontrollably. He buried his face into the plunging deep cleavage between her mammoth breasts, his sobs coming hard and ragged.

“There baby…its all over now…” she soothed him, “shushhh…there, there…don’t cry, baby.”

The punished youth rubbed his blazing bottom frantically as he bawled, his face pressed into her bosom.

“Timmy, sweetie?” Hazel asked him softly, “I hope you’ve learned your lesson…You know that you don’t question my friends, right?”

The sobbing sissy nodded his head in defeat, acknowledging her absolute superiority once again.

With that, Hazel sat him down on his changing table and re-diapered him in her efficient, businesslike manner. After that, she and Kayla went out to the living room to move his playpen to the front yard.

Michelle took a seat on the changing table next to Timmy, who was still sobbing and wiping the tears from his face.

“Hey there, little Timmy…Don’t cry, baby…” she said in a caring, motherly voice, “Hey–I know something that will make you feel better…”

Unbuttoning the first four buttons of her top, Michelle’s big breasts seemed to burst out of her halter and her soft skin was soon revealed as Timmy looked up at her in disbelief. She smiled down at him, and undid the clip between the two satiny cups of her bra, releasing her impressive, milk-laden mammaries before him.

“Come here baby,” she said as she took his head in her arms and carefully guided his mouth to her big, dripping nipple.

Still traumatized, Timmy swallowed the salty tears in his mouth and greedily wrapped his lips around the big, pink aureole. He was rewarded with a steady stream of mother’s milk flowing into his mouth that he eagerly gulped down.

“There…that’s a good baby…yes…Just like momma’s little baby,” she cooed softly, stroking his long blonde hair maternally.

During times of stress, breast-feeding had been a steady and reliable source of comfort for Timmy during his childhood. Although Gina stopped producing milk by the time he was five, she still allowed him to suckle at her breasts up until the age of 10, wanting nothing more than to ease the burdens from her troubled child.

Now, as Timmy nursed from the warm nipple in his mouth, the shame and humiliation he had felt at Kayla’s hands slipped away and he began to relax. Although it still felt like a red hot skillet was being held against his abused bottom, his little baby penis nevertheless twitched anxiously within his chastity device. Michelle continued to speak softly to him and give him comfort as he took his fill from her big, plump breasts.

There was however, a fundamental difference between Timmy’s earlier nursing with Gina and his current situation. Whereas before, he had looked to breastfeeding as a source of comfort and love, he was realizing now, there was a new and significant sexual component.

Breathing in the intoxicating scent of Michelle’s skin, he watched with growing arousal, the rise and fall of her fabulous chest as his eyes wandered over her magnificent curves. Timmy’s breathing grew heavier and his little penis throbbed urgently inside his chastity tube.

He tried to satiate his gnawing sexual need by sucking harder on Michelle’s nipples until she softly winced in pain.

“Careful, baby boy,” she giggled as she playfully beeped his nose.

Her warm, comforting nature only served to heighten his sexual tension and his little nub ached desperately with arousal.

Just then, Hazel stepped into the room from behind him.

“Well–I see my baby is getting his proper feeding–I’m going to have to get you over here more often, Michelle,” she teased her friend.

Timmy blushed and as Michelle pulled her big breast away from his pursed lips, Hazel pushed his pink pacifier into his mouth.

“Come along sissy boy, its time to go outside.”

Timmy whined but let himself be led out of the nursery, down the hall and out the front door. Put simply, his bottom was stinging far too much to do otherwise.

As they went outside, the warm summer sun shone down brightly on the embarrassed sissy and he felt painfully exposed. Their yard was not big, nor was it fenced, and the other two women had placed his playpen in the middle, nearby the driveway where Kayla was washing her car.

Timmy’s head spun around in every direction, anxiously scanning the street for passer-byes. To be sure, the diapered sissy had lived a sheltered life and he was completely unaccustomed to being seen freely in public.

Hazel led him over and helped him to step awkwardly over the soft, padded rail of his playpen. Sitting down, he sucked his pacifier nervously but his attention was soon distracted by Kayla, who was washing her car. The sun shone off her toned legs and every time she bent over, Timmy could hardly fail to gaze longingly at her trim figure.

He was watching her closely and getting turned on, when he suddenly heard giggling from behind him.

Spinning around, he saw a pair of young girls, around aged ten or eleven, standing on the sidewalk, pointing at him and laughing together.

“Why are you dressed like a baby?” one of them asked bluntly.

Timmy’s mouth dropped open and his cheeks blazed hotly.

Stranding up from her job of washing the bumper of her car, Hazel smiled pleasantly at the girls.

“He can’t control his wetting, so his mommy makes him wear diapers,” she told them, happy to explain.

The girls looked at each other and giggled again.

“Why is he dressed like a girl?” the other one asked.

“Timmy’s mommy feels it’s more appropriate for his prissy personality. He’s always been very girly, and dresses just seem like they suit him better than wearing pants,” Hazel said, the soapy sponge dripping in her hand, “And I have to tell you…as his babysitter, it certainly makes changing his wet diapers easier.”

Timmy’s cheeks burned with shame and he regretted being trapped out here in plain sight.

The girls laughed and walked up closer to the blushing sissy who was cringing in his playpen. Unconsciously, a strong stream of pee flooded into his diapers.

“I think you look silly,” the first girl said.

“Me too,” chimed in the other one.

“I’m gonna tell my sister about you, she takes care of babies too. Maybe she’ll want to come over and babysit a sissy like you,” the first one said.

Together, they laughed and continued their way down the street.

 

An hour later, both cars were clean and Timmy had been exposed to more of his neighbors than he had in the last four years previously. Most found it amusing, although one particular older lady thought it was perverse and disgusting. After getting Hazel’s flippant explanation, she had stormed off in a huff.

The girls left soon after, with Michelle giving Timmy a big hug and informing Hazel he needed to be changed once again.

Once the door was closed, Hazel turned to Timmy, who was back in his playpen in the living room.

“I can’t wait to get my cock inside of you,” Hazel told him eagerly.

Timmy’s heart skipped a beat and instinctively, his sphincter tightened around the big rubbery butt plug stuffed inside of him. Taking him by the hand, Hazel led the whimpering sissy down the hall to his nursery, his soggy wet diapers drooping noticeably.

Once inside, she peeled his plastic panties off, followed by his wet diapers which she let plop onto the changing table. Leading him into his crib, she had him lie down on his back, with a pillow under his head and another under his bottom to raise it up and make his sissy hole easier to access. She smiled as she gazed at the pink butt plug lodged firmly inside of him, now exposed for her intentions.

Meanwhile, she took off her snug jeans, allowing Timmy to see the pretty pink thong she was wearing. It wasn’t necessary for what she wanted to do, but she wanted to keep him sexually frustrated. Timmy watched with rapt attention as she slowly unbuttoned her fitted top, revealing her big breasts in a lacy black push-up bra. His little penis began throbbing wildly in his chastity device and his heart rate shot up dramatically.

Timmy was both excited and nervous. Excited, because he was seeing a whole new sexy side of his intoxicating babysitter, but nervous because her fat strap-on dildo always stretched his hole painfully to it’s limits. He licked his dry lips as she stepped into the harness and methodically pulled it up her shapely thighs. There were several straps the she buckled tight, but Timmy couldn’t take his eyes off the huge, ungainly rubber cock jutting out obscenely from her pelvis. When she was satisfied that it was secure, she climbed into the crib with Timmy, a smug, evil smile on her pretty face.

“Time for a nice hard, ass-fucking, sissy,” she grinned.

Timmy whimpered weakly and Hazel stuffed his pacifier in between his quivering lips.

Grasping the base of his butt plug firmly, Hazel pulled it out, which caused a yelp to escape from Timmy. Reaching into the jar of Vaseline, she scooped out a handful of lubricant and fed it into his small but gaping hole. With a quick coating applied to the meaty dildo, Hazel positioned it between his pink cheeks. The blunt tip contacted his hole and Timmy squealed with fear.

“Just relax, sissy, it will go in a lot easier,” she said breathlessly.

Timmy fidgeted nervously as he felt himself being invaded once again. The monster head of the dildo pressed hard against his hole and he moaned loudly as he felt it push forcefully past his sphincter and burrow deep into his tight rectum.

“OHHHH!” he cried, the pacifier falling out of his mouth.

Hazel’s pussy was wet with anticipation and she nearly came as she looked down on the bleating boy’s face, his eyes wide and his fists shaking impotently. Slowly, she pushed the massive dildo in deeper and deeper, until it bottomed out and Timmy squealed helplessly.

Grasping his soft hips in her hands, Hazel used her weight and held the dildo inside of him as she watched him breathing heavily, struggling to come to terms with what was happening. Then she began a slow, tortuous and tantalizing rhythm, in and out, always leaving the fat, mushroom shaped head inside the rim of his back passage.

Timmy moaned weakly, looking up at his beautiful babysitter who was determined to rape him. Her big, sexy breasts swung in her satiny bra before him and Timmy moaned both from the pain but also from sexual angst. She was SO desirable, so exciting to behold, and Timmy felt overwhelmed with raging, pent-up arousal. Without thinking, he locked his Mary Jane-clad feet around her waist as she forcefully plunged her big rubbery cock in and out.

To Timmy, Hazel seemed all-powerful, exuding a combination of strength and devastating beauty. As he looked up into her dark, commanding eyes, the pain below had faded and he was slowly getting accustomed to the stretching girth of her mighty strap-on.

On the other hand, his trapped little penis was straining at his tube, aching for release.

Looking into her determined, lust-filled eyes, he couldn’t take anymore.

“OHHHHH!!!” he cried as he felt a heart-stopping orgasm erupt from his caged member.

Hazel misunderstood the distraught look on his face and she came too, shrieking loudly as she buried the dildo in as far as it would go. Throwing her beautiful head back, her wild hair in a spray, she cried out in sexual ecstasy, her taut body shaking violently.

With her eyes closed in bliss and her disheveled hair strewn across her face, Hazel gasped for breath.

Timmy too, was in another world. He hadn’t experienced an orgasm in almost a year, and the mighty climax left him exhausted, spent, and weak. Looking up at his stunning babysitter through half closed eyes, he experienced a mixture of feelings; admiration, desire, longing, and a wish to be forever in Hazel’s life.

 

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

 

 

Two nights later, Hazel was putting Timmy to bed in his crib for what would be the last time until after the weekend. He had brushed his teeth, had his diapers changed, and been put into his jammies. Gently, she helped him under the baby blankets and tucked his teddy bear under his arm.

Softly pushing his silky blond hair out of his precocious face, she bent over, her gorgeous face inches from Timmy’s.

His long lashes fluttered and he felt a tremendous yearning for her as he gazed longingly into her pretty eyes. Hazel smiled, came closer and gave him a tender, sexy kiss on the lips, filled with promise.

 

After the eventful week and everything he had been through, Timmy’s emotions suddenly swept up and overwhelmed him. As Hazel ended her kiss and she sat up, Timmy suddenly burst into tears.

“Miss Hazel–please don’t leave me!” he cried miserably.

“Aww,” she said as she stroked his hair softly, “Don’t worry Timmy. I’ll be back on Monday–I promise.”

Sad tears tumbled down the boy’s cheeks and Hazel pushed the wet rubber nipple of his baby bottle into his mouth.

“Shhhhh,” she cooed, her ravishing face smiling warmly at him, “Your mommy’s anxious to see you–I’m sure she’s missed you terribly.”

For Timmy, the weekend seemed like a insurmountable period of time to have to wait to see Hazel again. His throat swelled with sadness and he had difficulty swallowing the warm milk.

“Now you be a good little boy while I’m gone and I’ll see you Monday morning, bright and early.”

She gave him a playful wink and stood up, turning the lights out as she left his nursery.

Timmy sobbed a little and nursed his bottle, replaying the memory of Hazel’s sweet kiss over and over.

 

 

CHAPTER SEVEN

 

It was Saturday morning, and Gina carried the warmed baby bottle of milk in her hands as she slipped quietly into Timmy’s nursery. Gazing down upon the angelic boy, she sighed with happiness as she watched him peacefully sucking his thumb like an infant. Apparently, his pacifier had fallen out of his mouth some time during the night and the diapered boy was resorting to an old habit.

He was sleeping blissfully, and his teddy bear was snuggled against his cheek, his arm wrapped tightly around it.
Gina imagined he was probably innocently dreaming of bunnies and kittens.

Unlatching the side rail of his crib and lowering it, Gina took a seat on the edge of the mattress. For a moment, she stroked the soft blonde hair of her babified son, not wishing to disturb him.

Sleepily, the long lashes of his eyelids fluttered open and he slowly recognized his mommy.

“Hi, my little sweetie-pie junior,” she said happily as she pushed the wet rubber nipple of his bottle between his lips. Without thinking, Timmy began nursing on the bottle and he made soft, babyish mewling sounds as he gazed up at his mommy.

“I’ve missed you so much, Tammy,” she exclaimed, a big smile on her face, “How have you been?”

Without waiting for his answer, she bent down and hugged the infantile sissy tightly, giving him a big wet kiss on his cheek. Timmy squealed, but he smiled back at his loving mother.

“Hi mommy,” He said as he removed the bottle from his mouth, “I had so much fun with my new babysitter. Miss Hazel is really nice to me and I really like her.”

Gina bent down and rubbed her nose across Timmy’s several times in a sign of warm affection, “I’m so glad–I was really worried while I was gone. Has she been doing a good job of taking care of you?”

“Oh yes, mommy,” he gushed, “–she’s so pretty, and she’s always nice to me.”

Timmy decided not to tell her about the two blistering spankings he had received at her hands, as well as the daily punitive sessions with her strap-on. He was pretty sure she wouldn’t approve of those things. Instead, he emphasized all of her kinder points, exaggerating the warmth of her apparent friendship with him.

The fact was, Timmy had begun to construct an artificial relationship in his own mind between the two of them. Between the orgasm he had experienced, and last night’s tender kiss, he was building up the bond between them, one which really didn’t exist.

“I brought you two presents while I was away,” Gina announced, “I hope you like them.”

She brought over two large boxes, gift wrapped with white and pink nursery print paper and a matching satin bow.

For the life of him, Timmy couldn’t think of what his mother might have brought back for him, but he always loved presents so he climbed out of the crib and sat down on the floor next to them. The thick, pee-soaked Birdseye cloth inside his plastic panties squished wetly against his buns as he eagerly began unwrapping the first package.

Lifting off the lid, he gazed down to see a stack of white, fluffy diapers filling the box. Somewhat surprised, he looked up to his mommy.

“These are a new brand of diapers,” she said excitedly, “They’re extra, extra soft and have a unique material in them that makes them spongy and springy–here, feel them, Tammy.”

Tentatively, Timmy reached out and touched the material. He was amazed at just how soft they really were–they were like feathers to the touch.

“I can’t wait to try these on you, I just know that you’ll love them!” she exclaimed as she led him over to the changing table and began peeling his clinging plastic panties down off his soaking wet diaper. Timmy whimpered a bit, as he always did when someone made decisions for him and forced their will upon him. He felt helpless against her overwhelming force of personality as she sat him down and unpinned the soggy wet cotton from underneath him, putting it into his diaper pail.

Taking some baby wipes, Gina cleaned him up and then applied a thick, sticky coat of Desitin to his bashful bottom. Choosing three of the new diapers from the box, she slid them under his white-coated rump and powdered him in front all over his pink chastity device.

“I just know my little baby girl is eager to try out these wonderful new diapers,” she grinned, “Doesn’t it feel absolutely fabulous against my baby’s tender skin?”

Timmy had to admit that they did feel great. It was like having the softest fleece embracing his most sensitive areas, wrapping him in thick, babyish layers of comfort.

Taking one of his thinner pairs of pink plastic panties, Gina pulled them up his smooth, girlish legs and worked them over the big, bulky diapers. After making sure all the soft, fluffy cotton was contained inside, she rubbed her hands across the shiny surface of his waterproof panties and felt just how cushiony they were–like he was surrounded by down pillows.

“Feel it, Tammy,” his mommy encouraged him, “Doesn’t that feel amazing?”

Timmy softly stroked the front of his diapers which were fatter and rounder than usual. The soaker pad down the middle seemed spongier to him, and yet incredibly soft. He could easily imagine what it would feel like to masturbate in such diapers. Not for the first time, did he bitterly resent his chastity device, which prevented him from being able to play with himself as he used to.

“Here you are, Tammy,” Gina said as she brought the other present over to him, “open this one.

Timmy tore at the infantile wrapping and opened it, revealing a very fancy and delicate baby dress. It was white, decorated with orange, yellow, and pink flowers, a Peter Pan bodice and elasticized, short puffy sleeves. It contained a built-in petticoat of white ruffled lace that would keep the hem flared out in the style of a little girl’s dress.

“This one is cut really short to show off your pretty rumba panties,” Gina told him excitedly, “Here…see?”

She held the frothy white panties up for him, turning them around so that he could see for himself, the three rainbow colored ruffles crossing the top of the seat.

“Won’t you be the most special baby girl on the block?” she asked him eagerly.

In her excitement, Gina nearly ripped Timmy’s fuzzy yellow top as she hurriedly removed it and cast it on the floor. Dutifully, he raised his hands and Gina lowered the frilly confection over his head. The double row of buttons in back were made purposely small to prevent him from being able to remove it himself, and it took the better part of a minute to do them all up.

As she turned him around, she held his new rumba panties out for him to step into.

“These are just the cutest panties in the world,” Gina said glowingly, “I think you’re a very lucky little baby girl.

She pulled the soft panties up his legs and fitted them over his fat, bulging diapers. Just as she promised, the elaborately ruffled hem of his dress kept his diapers clearly visible, despite Timmy’s strenuous efforts to tug it down and try to hide them.

Gina quickly put on his glossy white Mary Janes and stood him up before the full length mirror in his nursery. It was obvious from the proud smile on her face that she was very happy with the final effect and she beamed down on her diapered son eagerly.

“You are the prettiest little baby girl any mommy could ever want,” she said as she hugged him tightly, pressing his head against her soft, generous bosom.

In all truthfulness, Timmy didn’t share his mom’s enthusiasm for her gift, although he could tell it meant a great deal to her. He smiled back and put his arms around her, hugging her closely.

“Thank you mommy,” he told her, “it’s a very pretty dress.”

He blushed a little because the dress seemed designed to showcase his fat diapers and cute rumba panties.

Gina opened her mouth and was just about to say something else when suddenly they heard the doorbell ring. Her brow furrowed and she looked down at Timmy in confusion.

“Who could that be?” she asked him.

It was rare for her to get callers and there were very few people in her life that she was close to that she felt comfortable sharing Timmy’s circumstances with them.

Pushing his pacifier into his mouth, Gina left her sissified son in the nursery and strode out to the living room to open the door.

A smartly dressed woman in her 40s stood at the entrance, wearing a grey pantsuit and slacks, with sensible shoes. She carried a valise and her eyeglasses lent her an intellectual air. The aura she gave off, came across as both stiff and formal, and instinctively, Gina’s defenses came up.

“Yes? Can I help you?” Gina asked her from inside her open door.

“Mrs. Gina Carver? My name is Harriet Richardson, from Human and Social Services. I’m wondering if I might come in and have a few words with you about your son?”

An electric ripple of fear passed through Gina and she swallowed hard. While her vast love for Timmy was unquestioned and she felt no guilt for raising him the way she had–in her heart of hearts, she knew by the standards of society that other people would judge her harshly. It was just this sort of visit that she had feared for the last 10 years.

Stepping back, she held the door open wide, looking at the social worker gravely as she beckoned her in.

“Come in,” she said as she invited her inside, although her voice lacked its characteristic warmth to it.

Taking her into the dining room, she bade her to sit while she went into the kitchen, nervously stalling for time.

“W-would you like some coffee?”

“No thank you, but I have some questions for you,” she said stiffly.

When Harriet had received the call from an elderly lady two days ago, about a teenaged boy that had been dressed like a baby girl and put in a playpen in the front yard, she had been hard pressed to believe it. But as she looked around the living room and spied the baby toys, oversized highchair, and large, meshed playpen only a few feet away, she concluded that this situation required further investigation. To be sure, it was her job to look into all the reports that she received, regardless of how far-fetched they might seem at first.

“A couple of days ago, our office received a call from a certain Mrs. Bentworth, who claims she saw your son outside in the front yard, dressed as a baby girl,” the woman said evenly.

The color drained from Gina’s face.

“That can’t be true–Tammy is never allowed in the front yard,” she blurted out.

“I’m sorry…You say Tammy? I was told your son’s name is Timmy,” the older woman said, a confused look on her face. Bending down, she pulled a small sheaf of papers from her valise, trying to find her specific notes.

Gina swallowed hard, her mind racing to find the right answers that would shut this woman down, and quickly.

What if she were to disapprove of Gina’s methods? Did she have the power to take Tammy away from her? It was too terrifying a prospect to even consider!

“I-I’m sorry…Yes, my son’s name is Timmy.”

The words tumbled out of her mouth clumsily and she felt as if someone else were speaking them.

“Can you ask him to come out here please?” Harriet asked as she eyed the nervous mother before her.

“Oh, well–he’s–he’s taking his nap now,” Gina stuttered anxiously, stalling for time.

The social worker looked skeptically at Gina as she smoothed a nonexistent wrinkle from her pressed slacks.

Just then, the sounds of Timmy’s crying could suddenly be heard as he waddled quickly down the hallway and entered the dining room unannounced. Gina’s face flushed and her heart stopped, her mouth dropping open like a drawbridge.

Harriet too, turned to stare at the teenaged boy, his pretty face wet with tears as he held his teddy bear in one hand and his baby bottle in the other.

“M-Mommy–Mommy!” he wailed miserably, “I-I wet my diapers!”

Timmy ran to his mommy as quickly as he could, given the thick, bulky mass of cloth between his thighs that slowed his pace to a waddle. He threw his arms around Gina and hugged her tightly, crying softly as she soothed her baby boy without thinking.

Without a shadow of a doubt, here was all the proof that Harriet needed.

Shocking and bizarre to behold, she stared incredulously at the boy toddler, his big, bulging diapers and playful rumba panties clearly in evidence. With Gina’s arms wrapped around his back, it tended to pull his dress up even higher, and Harriet was astonished at how fat his diapered bottom was.

Even from across the table, she could hardly miss the smell of baby powder and pee that surrounded him.

Looking at the effeminate boy now, she had to admit, deep down inside, she found him bursting with cuteness. It made her feel guilty to acknowledge it, and she knew she wasn’t supposed to condone this sort of treatment towards children but there it was. Perhaps it was because he looked so utterly convincing as a baby girl. His exposed legs looked soft, like those of a little girl’s and his long blonde hair with the sassy pigtails made him look cute and precocious. A secret part of Harriet wanted to scoop him up herself and bottle feed the upset, crying child.

Gina knew Timmy better than anyone and she pulled him onto her lap to face Harriet.

“Did mommy’s little baby wet her pampers?” she asked solicitously.

Timmy nodded his head sadly but vigorously.

Although it was mortifying, willingly exposing himself like this, he was old enough now to understand that his mom was under some very unexpected, dire circumstances and for once, needed his help.

“Yes mommy, I couldn’t help it,” he sobbed pathetically.

Gina pushed the nipple of his bottle between his pouting lips and his whimpering soon subsided. Looking across the table at the strange woman dressed formally, Timmy’s long lashes batted fearfully.

“Mommy–please don’t let her take me away,” Timmy wailed, his eyes filled with tears, although the nipple in his mouth muffled his words very babyishly.

“Oh sweetie–don’t say such a thing!” Gina exclaimed as she choked back a sob of her own. She kissed Timmy’s forehead repeatedly and hugged him tightly, perhaps thinking that her love alone could save the situation. Her sissy son was almost crushed in her embrace and he squealed in angst.

“Oww, mommy–that’s too tight!” he cried.

Gina relaxed her grip somewhat and she kissed the tears rolling down his flushed cheeks.

Harriet made eye contact with the diapered boy and her heart went out to him. It was obvious that these two loved one another very greatly and although his circumstances were a bit bizarre, there was no denying the caring affection between them.

When Harriet thought of all the broken families that she had interceded with, with the abuse, conflict and strife that were her job to put an end to, she just couldn’t bring herself to call this one of those situations. Rightly or wrongly, this prissy little teenaged boy obviously needed his diapers just like any incontinent toddler. While she had no way of knowing the years of history that preceded this moment, Harriet believed this was a family best left to their own devices.

As she rose to her feet, she watched as Timmy continued to nurse from his bottle, his mommy holding it patiently for him and whispering soothing words of comfort in his ear. Shuffling her papers, she dropped them into her valise and closed it up.

“I’m sorry to have bothered you, Mrs. Carver,” she said, “You have an adorable little boy here and I would never dream of separating him from his mommy.”

Timmy looked up at her with his sad, puppy dog eyes, which only made Harriet want to reach down and hug him herself.

“Don’t you worry, Timmy,” she assured him, “Your mommy loves you very much and I wouldn’t think of taking you away from her.”

Gina tried to swallow but she couldn’t. The lump in her throat ached painfully and she could hardly believe her ears.

Timmy smiled weakly as he continued to nurse from the warm milk

“Fank you,” he replied, his pink Mary Janes swinging back and forth happily.

 

CHAPTER EIGHT

 

 

Lunch time was always a wet, squishy affair for Timmy.

By noon, it would have been several hours since his last diaper change and by the time Hazel lifted him up and strapped him into his highchair, the soggy cotton cloth inside his plastic panties was almost always completely saturated.

His lunch was inevitably accompanied by the distinctive smell of pee wafting up around him as Hazel spoon-fed him his baby food.

But today, Timmy was feeling edgy and anxious. It had been five days now, since he’d had his unexpected, albeit very welcome orgasm, and as a result, he was hornier than ever. Indeed, having experienced it once, he wanted some sexual relief now, more than ever. He felt like a shark that had tasted blood–he had to have more!

Hazel certainly wasn’t making things easier for him. Sometimes, he felt she dressed provocatively just to torture him. This morning, she had chosen to wear a sheer white top that did nothing whatsoever to hide her lacy pink push-up bra underneath. Timmy had swallowed hard when he got his first good look at his stunning babysitter. Her big, beautiful breasts pushed defiantly against the thin, filmy fabric of her top and the poor befuddled sissy couldn’t think straight.

He was further confused by the volatile cauldron of mixed emotions swirling around inside of him. Was it his budding love, that made him feel certain that there was something significant going on between them? Hadn’t her kiss on Friday said as much? Oh, how he longed for another chance to touch her full, succulent lips again.
However, right now, his libido was winning out between his two polarizing desires. He wanted to touch Hazel’s big sexy breasts like there was no tomorrow! Just one touch–one chance to feel how big and soft they were, to feel their weight in his hands.

After lunch, she had taken him down the hallway to his nursery, making cheerful small talk with him. She seemed to be in good spirits, and her breathtaking smiles melted whatever paltry resistance Timmy might still have harbored.

Climbing onto his low, vinyl covered changing table, Timmy arranged himself on his back for her, as Hazel began peeling his cute ruffled plastic panties down off his sopping wet diapers.

Timmy bit his lip as he gazed longingly at his babysitter’s incredible bosom, blatantly and openly displayed before him.

She looked so sexy today, with her silver hoops dangling from her delicate ears and her eyes looking playfully down upon him.
Watching as her heavy breasts swung within her top, Timmy could feel his little penis struggling mightily in his chastity device, pushing and fighting against it like his life depended on it. It was so incredibly frustrating–being completely unable to get even a partial erection.

She unpinned his diapers and pulled them out from under him, depositing them into his big rubber diaper pail.

Looking down, she winked at him and beeped his nose playfully. As she reached over his head to select a pair of plastic panties, Timmy stared up at her big lace cups, mere inches from his face.

Although Timmy was by nature, an extremely shy boy, his intensely heightened arousal had emboldened him, and he couldn’t stop himself. Without another moment’s hesitation, he did the unthinkable, reaching up and touching her big bosom. For the briefest of moments, his small hand cupped the massive cup containing her magnificent bosom.

In an instant, the smile vanished from Hazel’s pretty face and she drew back angrily. Her eyes flashed darkly and her features hardened with furious indignation.

“You-do-NOT-touch-my-breasts!! Do you understand me?!?” she snapped.

Timmy’s mouth opened in shock and he began stammering incoherently, fumbling for some way to placate the gorgeous teen. In an instant, Hazel reached down and grabbed the wooden paddle that was laying next to the crib. With her left hand, she gripped Timmy’s flailing ankles together and in a flash, swung them high over his head. At the same moment, she brought the paddle down viciously, swatting his exposed baby bottom hard enough to make his whole body buck.

Timmy shrieked in agony as the wooden instrument of correction came down again and again in a blurry arc, slapping his soft, tender cheeks and leaving them a scalding color of crimson. His loud, piteous wails filled the nursery as he struggled wildly against Hazel’s iron grip of his ankles. He felt utterly helpless, and all he could do was to desperately grip the sides of the changing table as she vengefully smacked his bare bottom repeatedly.

How could he have miscalculated so terribly wrong? He had been dreaming of her all weekend, pining for her, and now that Monday had arrived, she had seemed to confirm his feelings of affection.

And yet, now she was holding his ankles up high and blistering his bottom with her paddle again.

Timmy’s hot tears flowing like a river and he repeatedly slapped the surface of the changing table in bitter, angry frustration.

Although Hazel looked to all outward appearances to be boiling with rage, inside, she gloated with immense satisfaction. She had purposely dressed as scantily as possible, hoping to goad Timmy into making an inappropriate move that would cross the line. Her kind-hearted friendliness this morning had only fed into the deception, lulling the sissy boy into thinking he could have his way with her.

And now, he had given her the perfect excuse to paddle him hard–something she hadn’t done in at least a week. Gripping his ankles tightly, she looked down into his red face and crying eyes as he sobbed loudly and wriggled in her hand, unable to escape her cruel, avenging punishment. The sight made her loins wet, and her focus went back and forth from his distraught face to his blazing red bottom. She loved the sight of his pink butt plug, the rubbery base visible just between his scalded red cheeks. With renewed vengeance, she smacked him again and again.

She paused only long enough to angrily scold him.

“You–“

SMACKK!!

“Are never–“

SMACKK!!

“To touch–“

SMACKK!!

“My breasts–EVER!!”

SMACKK!! SMACKK!!

She emphasized each word with a blistering swat of the paddle.

Hazel could feel her juices dripping down the inside of her thighs and she knew she couldn’t wait any longer.

With an abruptness that left Timmy gasping, Hazel simultaneously dropped his ankles and the paddle and picking up her strap-on harness, deftly stepping into it, and raising it up around her firm legs. Timmy had barely any time to register what was happening as he sobbed uncontrollably and his hands instantly shot down to rub his stinging hot, swollen cheeks.

There was an armless stool in the room, the same one Hazel used to sit on when she administered Timmy’s enemas, and after securing the various straps of her dildo harness around her hips, she took a seat on it. Spanking Timmy had made Hazel incredibly horny and she had to satiate her need now, rather than later.

She was, after all, from the generation of immediate gratification.

Grasping the base of Timmy’s butt plug firmly, she yanked it out, eliciting a loud squeal from the sobbing sissy. Fueled by her impatience, Hazel scooped up a handful of Vaseline and while Timmy’s hole was still agape, she stuffed it up inside him. Taking the jar, she coated the huge imposing shaft of her dildo as she smiled wickedly at Timmy.

Looking up through eyes filled with tears into her lust-filled, determined face–he knew exactly what was coming.

Taking his hand, she lifted him to his feet, guiding the crying boy over to her lap. With tears streaming down his red face, he was at first confused by what she wanted until she made him face her knees and straddle her firm thighs.

Timmy was very petite for a thirteen year-old and Hazel easily lifted him up, positioning his puckering sissy hole above her tool. At the same time, she arched her back, bringing the head of her fat dildo lower for him to step over. When he was in the proper position, Hazel slowly pushed upwards, seeking out his vulnerable back passage as Timmy whimpered helplessly. He was teetering on his tip toes, his legs spread wide as he faced his sexy babysitter before him. Once she had the blunt mushroom-shaped head in place, she lowered Timmy down over the shaft, watching his flushed cheeks closely as he gasped with surprise.

With his girlish voice, Timmy moaned loudly, and Hazel savored the look on his defeated face as inch after massive inch, slowly filled his tight little passage. Lower and lower, she brought his frame down until she could feel his hot, spanked cheeks quivering against her cool thighs.

Timmy gasped with the feeling of fullness. His sphincter ached from being stretched so wide but with Hazel’s hands holding him in place, he was forced to sit and take the entire gargantuan dildo deeply into his rectum.

Hazel’s hands circled around his waist and she drew him closer, hugging the distraught, panting boy.

“There, sissy baby…” she said slowly, her voice thick with desire, “This is just what my little pantywaist needs.”

Timmy moaned weakly, but with his head on Hazel’s shoulder, he breathed deeply the wonderful scent of her long brunette hair.

After letting him get used to the feeling (as much as one can get used to sitting on and being impaled by an impossibly big dildo), Hazel gripped Timmy around the waist and gently lifted him up, looking into his eyes as they widened with the emasculating sensations he was experiencing. Once she could see six or seven inches of the shaft of her dildo exposed below him, Hazel lowered him back down, burying the massive invader deep inside of him. Timmy moaned again, as he struggled to deal with the feeling of rubbery fullness stretching him wide.

Hazel loved this position, for it allowed her to closely look at every delicious expression of fear, panic, angst, and defeated resignation on Timmy’s pretty, angelic face.

It just didn’t get any better than this.

Up and down, she guided him on her huge, slippery shaft, his feet on either side of her legs, trying to support his weight but in fact, he was her captive, forced to take the punishing dildo at the pace of her choosing. With each rise and fall of his body onto the fixed position of her strap-on, Hazel felt her orgasm boiling to a simmer within her. Her eyelids grew heavy and she struggled to stay focused on Timmy’s face.

For his part, Timmy was whimpering and moaning, having been coerced to be a part of her perverse sexual conquest once again. He was holding onto Hazel’s shoulders as he went up and down, riding her fat, slick shaft and feeling it bottom out deep inside of his bowels every time she brought his torso back down.

Hazel was moaning too now, and her seductive, erotic voice was having a predictable effect on Timmy. With her hair disheveled and her plump breasts jiggling within her sexy sheer top, Timmy felt his own arousal return, front and center. She looked so utterly ravishing, with her eyes sensually half closed, biting her lower lip as she savored the pleasures of raping him. His tiny little penis was throbbing wildly inside his chastity device and his heart was beating like a jackhammer.

Finally, Hazel’s grip weakened and Timmy plunged down on the dildo, watching in awe as his babysitter shrieked in the throes of an earth-shaking climax. It was all too much for him, and he squealed with childish pleasure as he exploded inside his chastity device.

The two of them panted heavily, Hazel wiping the sweat from her brow as she gazed into Timmy’s exhausted features. Holding his face gently in her hands, Hazel Kissed Timmy, softly at first, but then with greater passion.

Timmy threw his arms around her and kissed her back hard, his head reeling with an overwhelming love and desire for this strong, beautiful woman. With her massive shaft still buried deep inside him, he felt utterly and completely possessed by her. With a clarity of vision, Timmy wanted more than anything he’d ever wanted in his life, to be her little sissy baby forever and ever.

 

 

CHAPTER NINE

 

 

Michelle set her Starbucks cup down on the kitchen table along with her purse as Hazel was picking up her car keys.

“Thanks so much for coming over, I’m not sure how long I’ll be gone, and Timmy just can’t be left alone–like any toddler still in diapers, he really needs to be supervised at all times,” Hazel explained to her well-endowed, older friend.

“Oh–its my pleasure. I think he’s adorable and I know we’ll have all kinds of fun today,” Michelle told her with a gracious smile, “And besides, since my little girl at home is no longer breastfeeding, my poor boobs are aching and full.”

She emphasized her point by hefting her big breasts in her small hands.

The two laughed together although they purposely kept their voices low, so as not to wake Timmy.

“What time do I get him up?” Michelle asked.

“Anytime is good,” she replied, looking over at the clock on the wall, “Now is when I usually do it.”

“So where are you off to today?”

“Remember that nerdy guy from our science class…Francis Kendall?” Hazel asked her.

“Mmm, vaguely…he was someone I pretty much ignored throughout High School.”

“Well, I’m going over to his place to see him today. He thinks he has a date with me…little does he know, he’s got an appointment with my Spencer paddle,” Hazel emphasized her remark by pulling the familiar wooden paddle out of her purse and gesturing with it.

Michelle giggled uncontrollably.

“Hazel, I swear,” she chuckled.

Her haughty friend smirked, “He thinks I’m coming over to make out with him but when I’m through with him, his ass will be sore inside and out. I love taking weak sissies down a few notches.”

Michelle laughed again. She could easily imagine the frail, shy boy she remembered from High School, forcefully bent over a sofa, his red, spanked cheeks on display, as Hazel pounded him mercilessly with her fat strap-on dildo.

“Well, I’ll take good care of your baby boy while you’re gone,” she told her.

“Thanks Hon,” she said, giving her a quick hug before heading out the front door.

After she was gone, Michelle strode down the hallway to Timmy’s nursery. Ever since she had met the shy, effeminate pantywaist last week, she had been intrigued with the idea of dressing him up and making him into her own little baby girl. He was just so cute! She loved the idea of controlling the little sissy and forcing him to be her precocious toddler plaything for the day.

Easing the door open wide, she entered the room, lowered the side of his crib and took a seat down next to Timmy’s slumbering form.

“Good morning, sugarplum,” she announced cheerfully.

Timmy’s eyes opened slowly and he gradually focused on the unfamiliar woman smiling down at him. Suddenly, a look of uncertainty and panic abruptly came over his face.

“Y-you’re not miss Hazel–where–where’s miss Hazel??” he choked, his eyes darting around the room, “I want my mommy!”

No one had told him anything about being babysat by someone else, and by a person who was nearly a complete stranger at that. He felt betrayed–it was too sudden and overwhelming for the traumatized, teenaged toddler and without warning, the tears started to spill down his innocent face.

“Aww, you poor baby,” Michelle said immediately as she reached forward and stroked his cheek soothingly, “There, there sweetie…don’t cry, little Timmy.”

But once the floodgates had opened, it was always hard for him to stop the flow. He sobbed and cried just like any other thumb-sucking baby in his crib, desperately clutching his teddy bear with anxious frustration.

Michelle knew there was only one thing to do.

Swiftly unbuttoning her snug, peach colored blouse, she exposed her stupendous, milk-laden breasts before the squalling sissy. There was a clip located just between the two massive satiny cups of her bra, and without hesitation, she undid it, allowing her big, pendulous mammaries to swing free.

Her wet nipples were already hard, and she bent forward, positioning her left one before the upset child.

“Come here, baby girl,” she said encouragingly as she put a hand behind his head and gently guided his face towards her succulent breast. The big pink nipple dripped with milk and some spilled over his lip and down his chin. Seeing how panicked Timmy looked, Michelle seized the initiate and quickly pushed it into his trembling mouth.

The poor sissy squealed helplessly–his entire field of vision was filled with this stranger’s bountiful, curvy breasts. Nevertheless, the warm, wet nipple filling his mouth had an immediate effect on him, and he soon quieted down, nursing contentedly as she softly stroked his head and wiped the streaming tears from his cheeks.

“That’s momma’s little baby…that’s a good girl…drink your num-nums,” she whispered down at him.

As Timmy nursed eagerly, Michelle gazed idly around his room, acutely aware of the pungent, childish smell of pee surrounding her. To be sure, this little sissy needed his diapers, just like any other toddler who hadn’t been properly potty trained.

Hazel had been kind enough to prepare Timmy’s morning enema, and the heavy, red rubber bag hung from the hook over his crib, patiently awaiting it’s use. Warm, soapy suds clung from the neck of the nearly bursting container and Michelle marveled that this petite little boy could take it all. She was glad she had been instructed on how important it was to take it slow and patiently, because she wanted to make sure he took every last soapy drop.

Looking it up and down, a germ of an idea began to take form in her head.

Timmy had stopped whimpering, and as Michelle looked down at the serene child, she smiled with happiness that she had been able to calm him down so easily. He was busily nursing, drinking his fill, his tongue roaming over her firm aureole and sucking her big, milky nipple.

“What a good little girl you are,” she commended him.

It felt wonderful to finally ease the strain on her aching breasts and she made a mental note to make sure he drank fully from her other one as well.

With her free hand, she reached down under the baby blankets and slipped a set of fingers inside the damp waistband of Timmy’s ruffled plastic panties.

Not surprisingly, he was soaking wet.

“After your enema, I’ll change you into a nice, fresh set of fluffy diapers, okay, honey-bunch?” she asked with a glowing smile.

Timmy nodded his head, but his eyes were closed as he continued to drink from her plentiful supply of mother’s milk.

“I just love that your mommy decided to keep you as her little baby girl…” Michelle mused eagerly, “I think you’re the cutest little thing.

“Later on, we’ll dress you all up and play some baby games and then I’ll read you a bedtime story before your nap–doesn’t that sound fun?”

Timmy nodded his head as he looked up shyly into her glittering green eyes. Although not as drop-dead gorgeous as Hazel, Michelle was still extremely attractive and her warm, maternal personality eased any concerns Timmy might have felt about spending the day with her.

Not only that, being in such close and intimate contact with her exciting big breasts was making him ravenously horny and his little sissy penis was struggling to become erect inside his chastity tube. He groaned as his childish member pushed insistently, however futile, against the implacable device but the big wet nipple filling his mouth effectively stifled his cries.

Finally, after making him take all he could from the other breast, Michelle eased her nipple from his protesting mouth and gently placed her big boobs back into her sexy satin bra. This time, however, she only re-buttoned two of the buttons of her blouse, leaving a long, tantalizing line of cleavage for Timmy to gaze at throughout the day and be tempted by.

Looking down at the contented boy with milk dribbling down his chin, she used her finger to gently push aside a strand of his long blonde hair.

“And now, its time for a nice warm, soapy enema for my baby Timmy,” she announced cheerfully.

The diapered teen winced, but he made no real effort to protest as she helped him out of his crib, stood him before her and pulled his yellow, pee-stained plastic panties down his legs.

“You really are a sissy, aren’t you?” she asked glowingly, almost like it was something he should be proud of, “Most little boys don’t need enemas but for a sissy bedwetter like you–they’re absolutely necessary,” she explained cheerfully as she gently bent him over her lap and unpinned his soggy wet diapers, pulling them back to expose his damp, curvy little bottom. His cheeks were still a little pink from the blistering spanking he’d received two days previously and Michelle stroked them tenderly.

“My…looks like you’ve been a naughty little boy–did miss Hazel have to use her paddle on you?”

Timmy nodded as he blushed and mumbled something incoherent. Without a doubt, he’d learned that sissies aren’t allowed to touch a woman’s breasts without dire consequences. It was why he had made sure he kept his hands to himself while breastfeeding from Michelle.

Taking a handful of Vaseline, she pushed it into his cute little hole as she gently spread his soft, girly legs and tender cheeks.

“That’s it…nice and wide for mommy’s big enema nozzle,” she commended him.

Timmy squealed helplessly as Michelle slowly but insistently pushed the blunt end of the rubber enema dildo into his puckering, reluctant hole.

“Ohhh!!” the defeated sissy cried as it slipped past his sphincter.

“There….what a good little girl you are,” Michelle complimented him pleasantly.

She smiled as she pushed it in further, slowly burying the long, slippery rubber nozzle deeply into Timmy’s innocent sissy hole. After playing with it briefly, Michelle opened the clip, releasing a strong torrent of warm, soapy water surging into Timmy’s bowels.

“M-Mommy!” he cried helplessly as the liquid flowed unimpeded into his rectum.

Michelle sighed with satisfaction as she watched him squirming in a fruitless effort to resist the enema. Once again, it was astounding to her that such a slight, unimpressive boy could take a full two quarts of the soapy water but she was determined to show he could do that and more.

Unconsciously, she pushed the slippery enema nozzle in deeper, making Timmy squeal once more.

“I have to tell you Timmy…I just think the world of your mommy,” she said as she patiently manipulated the clip on his enema hose, “She loves you so much–you really are lucky to have her…”

Timmy squirmed on her lap, his hands waving weakly in the air to protest this inevitable morning ritual.

“And I’ll bet she knew when she was putting you into such soft, fluffy diapers, just how tempted you would be to play with yourself…

“All little boys get tempted and they just can’t help themselves–can they Timmy?”

Timmy certainly knew the truth of that but he groaned helplessly as he felt his insides slowly expanding to accept the insistent soapy water surging into him.

“…Which is why she locked your little baby penis into a nice, secure, chastity device, preventing you from getting any more erections or playing with it again. Wasn’t that simply wonderful of her?” Michelle asked, her voice filled with admiration.

Much as Timmy would have liked to argue the point, the soapy suds churning inside his belly made him moan weakly instead.

“Trust me…there are big boys who were made to have their way with women…” she paused to sigh longingly when she thought of her man at home, “And then, there are cute little sissy boys like you, who don’t need to have orgasms. All you need are soft, prissy pampers and cute plastic panties.”

At that moment, Timmy gasped with the cramps that were forcefully setting in. His tummy was full and distended, now that the enema bag was almost empty.

“Isn’t that right, Timmy?” Michelle asked as she pushed the fat dildo nozzle in to the hilt.

“Ohh!!! Y-yes, ma’am,” Timmy agreed submissively. He just wanted this emasculating enema to end.

“Is it hard being a chaste sissy boy in diapers?” she asked, “Aren’t you horny all the time?”

“Uhh–ohh, y-yes, m-miss Michelle,” Timmy stammered, “Its-its very hard.”

She chuckled as she toyed with the clip in her hand, debating just when to open it again.

“But then–I guess you can’t very well get hard–can you?” she laughed light heartedly as she reopened the clip.

Timmy wanted to say something, but his response was cut off as he suddenly moaned again from the urgent flow of soapy water surging deep into his bowels.

“I know–I have a great idea!” Michelle said as if she’d suddenly had an epiphany, “I think it would be a great idea if you were to write your mommy a little thank you note. You know–you could explain to her how smart and thoughtful it was for her to lock up your little pee-pee into a chastity device and prevent you from being able to play with yourself.

“After all, we both know when little sissies are left to their own devices–these bunny soft, fluffy diapers prove to be too much for a pretty boy like you to resist, don’t they?”

Timmy blushed furiously–how could she have known him so well? It was like she could read his mind!

“N-no…” he moaned weakly, but unconvincingly.

“Big boys deserve to have orgasms, but we both know you aren’t a big boy, are you? You’re just a big sissy in diapers. And bedwetting sissies don’t have any need for erections, do they, Timmy?”

“Ohh—no, m-miss Michelle,” Timmy moaned as the cramps hit him full force.

“No…we both know you’re a cute little baby bedwetter that can’t keep his pampers dry,” Michelle said as she slowly slide the slippery enema nozzle out.

Thinking he was finally free to release his punishing load, Timmy tried to rise up, only to find himself still being held in place by his beautiful, busty babysitter.

“Oh no, Timmy…not yet…” she said as she slowly pushed his pink rubber butt plug back into his protesting hole, “I think you need to write your mommy a nice little note right now, thanking her for all she’s done and putting you into chastity where you belong.”

Timmy winced and swallowed hard. He really had to go!!

“Please!” he begged her pleadingly, “Please let me go to the bathroom.”

Michelle helped him up, but only to gently place him down onto his changing table.

“No baby–it’s diaper time now, little Timmy, and then you can write your mommy a nice note thanking her for her thoughtfulness.”

Timmy moaned weakly as she set him down on a thick stack of diapers, pulling them up between his prissy legs and pinning them snugly together with some yellow baby pins. Taking a nearby set of pink rubber panties, she swiftly pulled them up over his feet and legs, carefully positioning them around his fat, bulging diaper.

“Come on, Timmy,” she said as she led him over to a low table with crayons, “The sooner you write this–the sooner I’ll let you release your enema.”

The teenaged sissy sobbed a little as he weakly made his way over, waddling awkwardly, the soapy suds churning achingly inside his belly. At the same time, his pink butt plug was buried deep into his back hole, stubbornly preventing any of his enema from escaping.

Michelle found a blank sheet of pretty pink drawing paper and set it before him, selecting the crayons she wanted him to use.

“Okay, I’ll dictate it, and you just write, okay?” she told him.

Timmy groaned again as another cramp hit him.

Michelle stroked her delicate chin thoughtfully as she slowly paced the room.

“Let’s see…okay–write this;

‘Hi Mommy,

I know this is overdue, but I just wanted to thank you so much for finally putting me into a secure, tamper-proof chastity device. You see, I was finding that the older I got, the more my soft, fluffy diapers were proving to be a dangerous temptation for me. I was playing with myself every chance I got and I couldn’t stop myself!

Thank you so, so much, for making the decision to lock up my naughty little wee-wee. I had become a chronic masturbator and I needed a chastity device to make me be a good little girl again. Sissies like me don’t have any use for erections, so a secure chastity device was the perfect solution.

Now I stay nice and soft–just like a little baby girl should! :o)

I know that you did it out of true, maternal love, just like I love you mommy.

Your prissy baby girl,

Tammy

XOXOXXO‘ “

 

Timmy was writing furiously to keep up with Michelle’s dictation and the end result was a sloppy, childish mess, barely legible to read. The use of crayons only added to it’s infantile appearance but Michelle was clearly very happy with it.

“What a good little girl you are,” she exclaimed as she patted him on the head patronizingly, “Okay, you can go release your enema now.”

Timmy half waddled–half limped out of the nursery, going as fast as he could to get to the bathroom.

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

 

Michelle heard the bathroom door open and Timmy coming back down the hallway.

“Come along Timmy, its time to get you dressed. Your diapers are waiting for you,” she told him.

Timmy walked into the room, his eyes downcast and shyly covering his little pink chastity device as he regretted the note Michelle had forced him to write.

“What a good little girl you are,” she commended him again patronizingly, “Did you make poo-poos like a good girl?”

Timmy blushed and nodded his head.

She patted him on his soft bare bottom and took his hand, leading him back over to his changing table.

“Okay sweetie, now we’re going to have some fun. We’re going to play dress up–doesn’t that sound fun?”

Timmy nodded again–now that he was done with the trying experience of holding his enema in–anything else seemed trivial by comparison.

“But first–we need to get you back into your baby diapers before you wet yourself,” she said as she lifted his legs to make sure he had done good job of cleaning himself. There was something about her nature that made Timmy feel more embarrassed than usual, and as she wiped his crack with a baby wipe, shaking her head with obvious disappointment, he blushed with shame.

Michelle gave his bottom a thorough coating of sticky Desitin before sliding a thick, fluffy stack of diapers under his bashful rump. Baby powder followed and soon, his diapers were being tightly pinned around his narrow hips.

“I don’t know where your mommy gets such soft diapers but it’s no wonder that you were constantly playing with yourself,” she said as she began working his pink rubber panties up his hairless legs. Unlike his usual vinyl panties, these tended to cling to his skin and required more effort to get in place around his fat, bulky diapers.

“Tell me, Timmy–which do you like better–your plastic or your rubber baby panties?” she asked him.

Timmy had never really thought about it but he knew his mommy liked the rubber panties for the better way they sealed against his thighs. He tended to leak less in his crib when she dressed him in rubber panties and for his part, he liked the buttery softness of them.

Timmy was about to offer his opinion on the subject when Michelle suddenly pushed the nipple of a baby bottle between his lips, cutting off whatever remark he had planned.

“Drink up, baby boy. Big sissies need their milk,” she giggled as she winked playfully at him.

Timmy did as he was told while Michelle went over to his closet to pick out a pretty dress for him to wear. It was a difficult task to choose one, given that he had so many wonderful baby dresses and outfits to pick from.

After much deliberation, Michelle finally settled on a pink and yellow ‘peek-a-boo’ dress that openly displayed his fat, diapered bottom to good effect. After lowering it over his torso and securing the locking zipper in back, Michelle went over to his dresser to find a pair of matching rumba panties.

“What a lucky little sissy you are to be able to dress up in such cute, babyish toddler fashions everyday,” she gushed with wonder.

One of his drawers was packed with frilly and lacy panties, all nicely full cut to accommodate his big, bulging diapers.

“Come here, little Miss Priss,” she said cheerfully as she held out a pair of delicate white nylon panties, the seat decorated by rows of sassy pink ruffles.

“Just what mommy’s little baby needs,” she smiled enthusiastically as she held them lower and let him step into them. Timmy whimpered a little as she tugged them up his soft, girly legs and fitted them over his snug rubber panties.

“Perfect!” she declared, “Aren’t you a special little girl!”

Timmy blushed again. He wasn’t used to getting such attention and being unable to look his busty babysitter in the eye, his gaze kept returning to the long line of cleavage between Michelle’s big breasts that were pressing against each other in a dazzling, mouthwatering display. Now that his stomach was feeling better, his horniness had returned with a vengeance and he could feel his little penis throbbing impotently within his chastity device.

He wondered if she would let him nurse from her breasts again before she left.

“Okay little cutie, let’s work on your hair now.”

Taking him by the hand, she sat him on the edge of his crib mattress and began brushing his long blonde hair, parting it on one side and putting pink flowered clips in it.

Once that was done, Michelle produced some pink nail polish and she began painting his nails, giving them several glossy coats.

All the while, Timmy stared fixedly at Michelle’s breasts, watching their hypnotizing rise and fall within her tight, mostly unbuttoned blouse. He wanted badly to reach out and touch them, but with his tender bottom still sporting the painful marks from his last session with the paddle, he wisely chose not to.

Sometime while Michelle was busy painting his nails, Timmy wet his diapers thoroughly and heavily, although he hardly took notice of it. The warm pee quickly surrounded his crotch before gradually seeping back into the spongy thick, absorbent seat of his diapers. It was an act as natural as breathing, and it didn’t end until Timmy’s weak bladder was finally empty. Fortunately, the sissy’s big bulging diapers could withstand numerous wettings before they got anywhere near capacity.

“Hold still, baby girl,” Michelle said as she carefully applied a coating of bright, glossy pink lipstick across his pouting lips. This was followed by some blusher and then several sprays of his baby perfume, something called Nursery Nights. It smelled strongly of baby powder, and something indefinable but very infantile.

Michelle had eradicated every last vestige of his maleness, and now the pretty little boy sat before her, a thoroughly feminized, diapered toddler.

Taking him by the hands, Michelle led him over to the full length mirror on the wall to show off her efforts.

“Look Timmy, aren’t you just the cutest little thing?” she asked eagerly.

She was so pleased and taken with his prissy, precocious appearance, that she reached down and gave him a big kiss on the cheek, followed by an affectionate hug. As a sudden afterthought, she bent down and impulsively squeezed the ruffled seat of his fat diapers, making Timmy squeal with surprise as she sensed the soggy wetness contained inside.

“Looks like mommy’s little baby has already wet himself,” she grinned at the blushing, sissified boy.

Timmy’s cheeks burned with humiliation and he nodded, only just now realizing what he’d done.

With a light giggle, Michelle took her cell phone out of her purse and took several shots of the red faced sissy, just to mark the occasion.

“Come on baby, let’s get you some breakfast,” she said, apparently having decided there was no immediate need to change him.

The rest of the morning went wonderfully for Timmy; Michelle fed him his favorite baby foods, after which they colored for a while together in his nursery until it was his time for his nap.

Michelle changed his soaking wet diapers, put him into a babyish onesie with a ruffled elastic waist that emphasized his bulging, diapered hips.

Getting him arranged in his crib with another baby bottle of warm milk, Michelle pulled out her cell phone and began scrolling through her Kindle library.

“I have a special little bedtime story for you, Timmy, one that I’m sure you’ll love,” she said as she patted him on his thick, ruffled seat, “It’s my all-time favorite and its about a little sissy boy just like you.”

“Ah–here it is,” she said, pleased with herself.

As Timmy nursed on his bottle, he gazed up in rapt admiration at the velvety soft skin of Michelle’s big, sexy bosom as she began reading her story to him;

“It was a cold, grey day and the rain was coming down in sheets, heaping only further misery upon me as I trudged slowly and alone through the downpour.

          “Three weeks ago, I had been recently orphaned, due to a tragic car wreck involving both of my parents, and my arranged social worker recently set up living accommodations at my aunt’s house, some 80 miles from where I’d lived for the last twelve years of my life. It had been a trying ordeal for me and after the last horrific month of trying to cope with being without them, I was beginning to think that I could not possibly be more alone in the world.

          “Unfortunately, I had only spotty memories of my mom’s younger sister, Aunt Emily. The last time I had been there, I had only been five at the time and it had ended on a bad note for everyone involved. She seemed nice enough, and as I recalled, and she was quite pretty, or at least, she was at the time…”

 

CHAPTER TEN

 

Hazel was feeling antsy.

As she blew dry her long, luxurious chestnut hair in Gina’s bathroom, she felt a growing sense of disquietude.

When she reflected on the strap-on sex she’d been having with Timmy, it occurred to her that things were growing a bit stale. It’s true that when she had first raped him, she had been thrilled by his plaintive cries and the look of absolute fear in his eyes. But after two weeks of humping his cute bottom in every imaginable position, the youth had come to appear to enjoy his sessions with her. Indeed, it looked like he was actually looking forward now, to having his tight little hole stuffed with her monster cock; he no longer squirmed in terror but instead, lay there submissively and passively.

While it was true that she was still dominating the intimidated boy, it had started to lose its excitement with his growing lack of fear. It was time for her to step up her game and she knew just who to call.

Setting down the hair dryer, she picked up her cell phone and dialed Kayla’s number. They talked for several minutes, working out the details until Hazel was satisfied with their plan.

“Okay, great. Be here at one exactly,” she told her friend.

Hanging up the phone, she smiled broadly–this was going to be fun!

A little bit later, Hazel woke up Timmy and administered his usual pair of back-to-back enemas, followed by breakfast while strapped into his highchair.

She had purposely chosen a skimpy black top that clung deliciously to her big, beautiful breasts and tied in front; an effect that wasn’t lost on Timmy. He stared at her hungrily all morning, wishing he could rub the front of his diapers and get some sort of satisfaction out of the act.

She decided to wait until midmorning to change him, because she had purposely made him release his second enema into his diapers and she wanted to make sure he felt the full effect for a couple of hours at least.

By 11:00, she determined that he’d had enough and she ran a soapy bubble bath, scented with Johnson’s baby scent, to get the sissy squeaky clean. After thoroughly washing his every crack and crevice, she dried him off and pinned him back into a fresh set of soft, fluffy diapers, but not before pushing his pink butt plug back into his protesting hole.

Hazel let him play in his nursery for while, using his crayons in his coloring book while she spent some time on Facebook. At noon, she led him into the kitchen and put him back into his highchair, strapping him in and serving a three course meal of mashed peas, something vaguely chicken, and applesauce.

All the time, she was getting more and more excited. She giggled to herself when she pictured what she had in mind for Timmy in less than an hour.

Finally at 12:45, she took him into his nursery and took his diapers down to prepare him for his afternoon session with her strap-on.

“I want you on your hands and knees today, Timmy,” she said as she began tightening the sturdy straps of her harness.

“Yes, miss Hazel,” he replied quietly as he climbed into his crib, docile as a lamb.

Getting into his crib behind him, Hazel popped out his butt plug, positioned herself on her knees and then slapped his curvy little bottom.

“Spread those legs,” she ordered him tersely.

Timmy squealed but did as he was told, soon feeling the familiar cool, blunt tip of her greasy rubber phallus pressing urgently against his defenseless anus.

“Oh–oh–oh–” he quaked nervously, never fully prepared to take the massive cock into his small, puckering hole.

“Look into the mirror, Timmy,” she instructed him.

Hazel had purposely positioned the full length mirror again so that the two of them could see each other’s face as she ass-fucked him. It was of critical importance to her, and she loved nothing better than to see his frightened, panicked expression the moment she plunged her gigantic dildo inside him.

Timmy was biting his lip anxiously, squirming in place as he tried in vain to escape the big, fat, probing cock pressing determinedly against his sissy hole.

As Hazel gazed into the mirror, Timmy looked like a scared, trapped animal, about to be sacrificed by a strong, beautiful and confident Amazon. Hazel loved the feeling of absolute power, the ability to do anything she wanted with this weak, effeminate boy.

She knew she looked amazing–her big, prominent breasts were thrusting out proudly, in a display of superior femininity, and threatening once again to burst out of her much-too-small top.

With a determined thrust of her pelvis, Hazel grasped Timmy’s hips firmly and rammed the massive dildo into his quivering rectum.

“OHHHHHH!!!!” his eyes went wide and he squealed loudly as he flailed his hand in the air.

Hazel grinned broadly and savored the look of total defeat on the distraught, pretty boy’s face. His panicked look was making her wet and she forced her cock deep into his pink sissy hole, grinding it in as he squealed and moaned like a little girl.

The two pink satin bows holding his pigtails in place only added to his prissy, girly image and Hazel sighed with satisfaction as she began pumping him languorously.
The initial pain of penetration had eventually begun to subside, and Timmy was moaning weakly but helplessly now, in response to her firm, driving thrusts.

If he had known to listen for it, he might have heard the front door open and close, but as it was, Timmy was caught up in a multitude of sensations and he didn’t realize Kayla was in the house until she suddenly and unexpectedly strode into the nursery unannounced.

Timmy gasped with shock, and his face immediately went beet red.

Kayla was dressed for a typical summer day, wearing snug shorts and a low cut, fitted t-shirt. On anyone else, it wouldn’t have elicited a reaction but Kayla’s toned figure looked fabulous in the simple outfit.

However, Timmy only had a second to register her clothing as his eyes fell to the big pink strap-on she was carrying in her hands.
The look of panic returned as he moaned in fear and struggled to get away from Hazel’s pounding cock. She slapped his bottom and held his hips tightly, making sure he got every rubbery millimeter of her dildo.

“Looks like you’ve got him right where I want him,” Kayla announced with an evil smirk on her lovely face.

“He just needs another cock,” Hazel quipped as she continued pumping him, easily holding the sissy boy in place.

As Kayla stepped into the harness and began pulling it up, Timmy became more agitated and he squirmed in the crib trying to escape his babysitter. More harsh slaps followed on his pink bottom making him cry out anew.

Kayla climbed into the crib on her knees facing Timmy, her big silicone cock now firmly strapped around her hips. She held it forth like she was serving it for the boy’s dinner as she grinned lasciviously. Hazel too, was beaming, but her beautiful brown eyes were filled with lust and her loins were dripping wet.

“No–please–please–” Timmy begged her as he gaped at the gargantuan phallus staring him in the face.

“Open up, sissy boy,” Kayla ordered him as she pushed it roughly against his trembling lips.

Once again, Timmy cried out in protest and it was all the opportunity she needed. Thrusting with her pelvis, Kayla rammed the rubber leviathan into his open mouth, holding the back of his head in place so he couldn’t escape. Not that he was going anywhere. Hazel was applying equal pressure from behind so the poor sissy was being forcefully impaled on both ends.

He squealed for all his worth but his cries were now muffled by eight inches of fat rubber cock filling his mouth. His lips could only barely wrap around the tremendous girth of Kayla’s dildo and his cheeks bulged to capacity.

Hazel had her first orgasm but she knew a much bigger one was on its way.

 

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

 

 

Gina was feeling on top of the world.

Her conference had ended a day early, and she was now free from work for the next three days. She was happy and eager to get home, where her precious, innocent little baby girl awaited her. She wanted to rush home as fast as she could, scoop him up in her loving arms and kiss him all over.

Traffic was light in the middle of the day and having started right before noon, she soon found herself entering her neighborhood an hour later. Gina could picture her sweet little baby…Hazel would probably be putting him down for his afternoon nap about now, after a nice, fresh change of diapers.

Maybe she’d even be in time to give him his naptime bottle of milk?

She had really come to like and trust her new babysitter. After the first week, she had been nervous and anxious about leaving her tender little girl into the hands of a stranger for the first time, but Tammy seemed perfectly happy and content with the young woman. If anything, he seemed impatient for the weekend to be over so he could see his babysitter once again. Gina was a little hurt by that, although she buried her minor feelings of jealousy deep inside, not letting on that she envied the pretty teen for her stunning looks and perfect body. It wasn’t surprising that Tammy had taken such a shine to her–Hazel was the kind of woman that attracted both sexes.

While Gina, who was now in her mid-thirties, still turned heads wherever she went, she knew she couldn’t compare to Hazel in terms of raw sex appeal.

At last, she spied her house down at the end of the block, and she eased her car into the driveway, shutting off the motor and exiting the vehicle.

Just in case Tammy was already asleep, Gina thought it prudent to enter quietly–she didn’t want to disturb her little baby.

Coming through the front entrance, Gina closed the door quietly behind her and made her way down the hallway.

 

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

Timmy squealed again as Kayla rammed her dildo deep down his throat, causing him to gag and wave his hand in futile protest. The sissy bedwetter was really getting a workout today, and both of his holes were getting pounded and stretched to the limit. Never in a million years could he have imagined this turn of events and never had he felt so totally violated as now.

“You’re going to make a nice little cuckold bitch some day,” Kayla sneered as she plunged her cock into his mouth, holding his head tightly with her hands to prevent him from escaping.

“MMMRPHH!!” Timmy cried desperately.

Hazel could feel the blood rushing in her head. Her heart was beating wildly and her pussy dripped like a faucet. She grit her teeth and closed her eyes as she felt the mother of all orgasms coming.

Unfortunately, the mother that arrived first, was Timmy’s.

She came through the open doorway of the nursery and stopped dead in her tracks, staring in dumbfounded shock at the three of them.

“WHAT IN HOLY HELL IS GOING ON HERE?!” she shrieked.

Hazel’s eyelids flipped open like a broken shutter and she gasped as she saw Gina for the first time. Kayla too, froze in place, as she turned in surprise to meet their unexpected intruder.

Timmy would have liked to have said something, but since his mouth was filled with a fat, rubbery cock, all he could do is look up at his mommy and whimper.

Kayla was first to yank her dildo out, and Timmy gasped for breath, his mouth still gaping open foolishly.

“You’re home early,” Hazel said, stating the obvious.

Even she was momentarily taken aback and unprepared for this possibility.

“How dare you–how DARE you do such a thing to my baby!!” Gina shouted angrily

To be sure, Hazel was surprised by Gina’s sudden appearance, but she was quick to recover. Yanking her slippery tool out of Timmy’s aching hole, she stepped out of the crib and calmly stood up before Gina. In her heels, she was quite a bit taller than the older woman, and she placed her hands on her hips as she gazed down at Gina, looking her square in the eyes.

“I’ll do anything I damn well please with the boy,” she said defiantly, thrusting her big breasts out proudly in a challenging stance.

Gina’s cheeks were flushed with rage and she charged Hazel, irregardless of her physical disadvantage. The latter sidestepped, deftly grabbing her arm and twisting it behind her back. Gina cried out, and in one swift motion, Hazel sat on the edge of the crib mattress and brought Gina face down across her lap. Timmy’s mother struggled and howled in protest, but Hazel was clearly the stronger of the two.

“Hold her hands,” Hazel instructed her friend breathlessly.

Although this was certainly unexpected, Kayla was quick to respond and she took hold of Gina’s flailing hands, pulling them in front and preventing her from being able to rise up again. Hazel flipped up Gina’s skirt, exposing the pretty, innocent white panties she was wearing. They were sheer and full cut, framing her perky bottom beautifully.

“Stop it! Let me go!!” she cried out as she kicked her sexy heels in the air.

“This is something you should have been doing while Timmy was growing up. Looks to me like you’re going to need a firsthand demonstration,” she snarled as he reached for her wooden paddle.

Gina struggled furiously but with Kayla gripping her hands like a vice, she was helpless to stop the strong, determined teen.

“Goddamn it! You let me go!!” she shrieked furiously.

Gina had a perfect set of buns that curved deliciously within her cute lace panties.

Hazel brought the paddle down with all her might, mercilessly searing it across her employer’s bottom with a harsh slap that filled the room. Gina howled in pain and kicked her feet frantically as Hazel smacked her again and again.

Unfortunately, her delicate panties provided little in the way of protection and her buns soon went from pink to an angry shade of bright red. Hazel wasn’t showing any leniency and she slapped each cheek viciously and hard, going from one to the other and then both at once.

Gina couldn’t take anymore and she burst into tears, crying in pain as she looked through blurry eyes into Kayla’s youthful, smirking face.

The paddle rained down in punishing succession, delivering stinging swat after swat to her tender, scalded bottom.

Gina had never been so humiliated in her life, and she sobbed loudly, kicking her heels wildly as the tears streamed down her face.

SMACK!! CRACKK!! SMACKKK!!!

Swat after painful swat landed on the same spot, turning Gina’s pretty little bottom into a stinging hot, blazing inferno.

At last, Hazel stopped, and she held the paddle poised over the defeated woman across her lap.

All her resistance had been spanked out of Gina, and she was left to cry ashamedly.

Hazel set the paddle down as the other two looked at them, unsure of what just took place.

Gently helping her to stand on her wobbly heels, Hazel gazed down at Gina’s tear-stained face, her hair a mess and matted against her cheeks. Tenderly, she used her finely manicured long nailed finger to move the strands of hair back and wipe her wet cheeks.

Weakly, Gina looked up at the gorgeous, busty teen, deeply envying her youth and strength. She was so beautiful, and she epitomized everything a woman could aspire to be.

Hazel bent down slowly, her face coming intimately closer to Gina’s. Her anger was gone now, and her expression held nothing but warmth and compassion. A mere two inches separated their faces.

Slowly putting her comforting arms around Gina, she reached down and ever so gently, pressed her lips against the older woman’s. She could taste the salt from her tears, and she pressed firmer, closing her eyes as she kissed her slowly and deliberately.

Gina hadn’t been kissed like this for years, and her emotions swept over her in a flood, melting her heart and opening her soul for this dominant, statuesque beauty.

She kissed her back, tentatively at first, and then with desperate, passionate abandon. They locked lips and Gina threw her arms around Hazel, holding her tightly as her lips parted and Hazel’s tongue entered her mouth. The younger woman swirled her tongue inside, tasting the salt again from Gina’s tears as her hands tenderly stroked and soothed the punished woman’s blazing bottom.

At last, their lips parted, and, still holding each other in their arms, Gina gazed submissively up into the dark, pretty eyes of her babysitter.

“Well,” Hazel said finally, with a seductive smile on her beautiful face, “looks like you’ve met the new boss around here.”

 

THE END