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

A Proper Fitting For A Sissy

A Proper Fitting for a Sissy

My name is Tiffany Johnson.
I’m 29 years old and I work at Chastity Services, along with my best friend, Ariel. Primarily what we do, is to fit males for chastity devices, sometimes willingly, other times…not so much. But either way, any male coming into my shop will leave with his little penis imprisoned and secured under lock and key.

I deal with a lot of sissies in my profession. I find that they tend to have a fascination with panties, or dressing up like women, or some other such perverted fetish. We get geeky guys coming in on their own and they’re curious about the concept of chastity and I’m only too happy to help them out. They’re often shy and easily intimidated so that’s just what I do. Its fun to watch them blush and squirm in my office, especially since I’ve always had a thing for dressing provocatively, wearing low cut tops that display my big breasts and snug skirts to show off plenty of leg.
I like to question them bluntly about their masturbating habits, how often they do it, as well as what they masturbate to. They always blush furiously when I question them but they’re too weak-willed to actually get up and leave.

The fact is, I can spot a sissy from a mile away and I love nothing more than to humiliate them in any way I can. I’ve been that way for as long as I can remember, all through out my junior and high schools, but truth be told, I started even before that, in grade school.

Of course, a proper fitting for a chastity device means having them drop their drawers so I can measure their pathetic little penises. They probably come in thinking I’ll be very clinical and dry like a professional nurse but in fact, I’m just the opposite. It’s inevitably a mortifying experience for the guy, and I take every opportunity to embarrass him, making disparaging comments about his size and telling him just what a pansy he is. I also make sure to tell all of them that I assume they’re virgins and that they’ve never been with a girl before.

With regards to the devices themselves, its surprising, but what a lot of women don’t realize is just how small of one you can stuff a guy’s penis into. I don’t want these sissies to have so much as a millimeter to be able to grow in, so I always make a point of fitting them in the smallest chastity device I can get them into. Fortunately, we have lots of the smaller, harder to find sizes than you can’t get online, so the sissy boy is usually both shocked and ashamed at what we can fit him for.

We also talk to a lot of our manufacturers, giving them constant feedback and as a consequence, almost all of them now offer pink versions of their devices. And we make a point of pushing that color as a choice for most of our males, browbeating the wimps until they finally cave in. Believe me–nothing looks more pathetic than a male wearing a pink chastity cage around his tiny package and shaved crotch. No woman will ever take him seriously after they see that.

One of my favorite tricks is to fit them for a device, lock them into it, and at the end of the sale, I appear to hand over the keys.
Little do they realize that the keys I gave them aren’t the real ones, since I always keep those in a safe, secret location, but they don’t find that out until they get home, and sometimes, not even for several days. After that, I screen my calls, just to ensure the little sissies will squirm with panic and fear. I want them to experience at least a full week of real chastity, outside of their control–not knowing if they’ll ever be able to touch their pathetic wee-wees again.

It never ceases to amaze me what you can make a locked, desperate sissy do, just to get access to the real keys. And I make sure that whatever I demand of them will be extremely humiliating for him to endure.

In high school, I was something of a bully to the weaker guys and I’ve only become more determined to put these wimps in their place in my professional life. At 5′ 10″, I am on the tall side, and in my 5″ heels, I tower over most guys, especially sissies. My haughty, imperious nature is more than enough to make them tremble but being tall also helps.

Growing up, I was an early bloomer and I was already sporting a generous C cup by my 14th birthday. By 18, I was outgrowing my DD bras from Victoria’s Secret. Nowadays, I have to order my bras online from specialty stores to get ones that will fit. A 34EE size cup just isn’t to be found at Nordstrom’s.

All too often, these pervs coming into our shop try to steal glances down my low cut tops when they think I’m not looking, but I always catch them and scold them mercilessly, making the little creep blush bright red with shame.

The other day, I had an interesting visit from a couple that I think is worth relating.

A husband and wife came into our office last week and right away, I could tell the guy was a sissy. He seemed really nervous, and had difficulty making eye contact with me. Instead, his gaze would dart anxiously around the room, as if he were trying to find some way of an escape.
By contrast, the woman was cool and collected, confident and self assured–everything her husband wasn’t. She looked to be in her mid-thirties, with jet black hair and a slim, yet curvy figure. She dressed smartly, with a close-fitted blouse and a skirt that showcased her long legs.

I have an eye for detail, and looking at her fidgeting husband, I felt certain that he was wearing diapers underneath his trousers. He seemed very self conscious, and he shifted in his seat, as if desperately trying to hide his childish underwear.
Definitely a sissy.

After sitting them down in my office, I offered her coffee (purposely ignoring him) and took a seat before them, crossing my legs in a deliberate manner to test her sissy husband’s reaction. Sure enough, although he tried to hide it, his eyes couldn’t avoid staring as my short skirt rode up my thighs.

“Tell me how I can be of assistance,” I said, smiling pleasantly as I looked the wife in the eyes.

“My name is Leanne and this is my husband, Conrad,” she said, referring to her spouse with a dismissive thrust of her extended thumb.
“He has a chronic masturbating habit and I want to put a stop to it.”

“That’s disgusting,” I said firmly as I looked him up and down with disdain.

His face went bright red and he looked away, tugging at his collar anxiously.

“How often do you play with yourself, Conrad?” I asked him point blank.

His mouth opened, but it seemed there was no dignified way to answer the question, especially with his domineering wife right next to him.

“Every chance he gets,” she immediately replied without hesitation, “I make him wear diapers because of his nightly bedwetting, and Cassie simply can’t resist the soft cotton Birdseye I pin him into.”

I shook my head and stared hard at her wilting husband.

“I thought as much…am I right that he’s wearing his diapers now?”

“Yes he is–he made a fuss about coming down here today so after a trip over my knee, he got to wear his nighttime diapers instead of his regular underwear.
“Cassie–why don’t you show Ms. Johnson here your pampers?”

Her hubby shot a panicked look back at her and he shook his head pleadingly, silently beseeching her for mercy.

“Cassie? Do you need another dose of the hairbrush? Because I’ll do it right here and now if you want to push me.”

The color drained out of her hubby’s face and with a sob of shame, he slowly stood up. Fumbling with his zipper and clasp, he clumsily managed to undo them and his trousers slid down his slim, hairless thighs, revealing his prissy, embarrassing diapers. Obviously designed to ensure maximum humiliation for the wearer, Leanne had chosen a pair of pink nursery print plastic panties with babyish white ruffles around the legs and waistband.

“Well–I see who wears the pants in this relationship,” I snickered, “Are you wet, sissy boy?”

Conrad shook his head miserably but didn’t look up at me.

“Answer her when you are spoken to,” his wife barked.

“N-no Ma’am,” he whispered meekly.

“Good, let’s try to keep it that way,” I told him, “You might as well take those pants all the way off, you won’t be needing them for a while anyway.”

Conrad bit his lip and slowly removed his pants, folding them neatly and putting them on my desk. He looked absolutely ridiculous in his polo and bulky pink diapers and I noticed he took his seat gingerly, presumably because his bottom was still smarting from his earlier spanking.

Returning my attention to Leanne, I gave her my usual sales pitch.
“Now–I have a number of chastity devices for you to choose from for your little sissy here,” I explained to her, “Depending on his size and your preferences, we have steel, plastic, and a number of colors, although I think pink would suit Cassie here the best.”

“I agree,” she replied, “More than anything, I want it to be super secure so that’s there’s no chance he can escape from it or have access to his little penis.”

“Oh–absolutely. Trust me when I tell you that after today, your sissy’s masturbating days are over for good,” I assured her.

Out of the corner of my eye, I could see her hubby cringe with fear.

“Now–we have two kinds of devices–those with spikes and those without.”

“Spikes?” she asked in confusion.

“Oh yes, some of our devices have spikes inside, to discourage any sort of arousal from the wearer. They’re very good at making him focus on other things–like his chores around the house, for instance,” I explained.
“They’re usually not a problem for everyday wear, until he starts getting turned on, that is. At that point, the head of his penis will begin pushing against the spikes, quickly discouraging any further thoughts of naughty behavior,” I said, eyeing her fidgeting sissy with a knowing grin.

“Oh–that would be perfect,” Leanne agreed, “That way, when my boyfriend is over, Cassie will be less interested in what’s happening to me and more focused on his mopping duties.”

“Oh–you have a boyfriend?” I asked intrigued.

“Absolutely. This sissy here is completely incapable of satisfying me so I did what any sane woman would do–I went out and got myself a real man to take care of my needs.”

I smiled broadly at her.

“Good for you! Although I’m hardly surprised. I’m finding that most women in your place are doing the exact same thing. Why be stuck with a bedwetting sissy in diapers who can’t perform–when you can have a real man in your bed every night who knows just how to satisfy you?”

“Exactly. I leave Cassie to enjoy the wet diapers and crib sheets while I get to enjoy a nice big cock every night, reaching places that he never could. I can’t tell you the kind of mind-blowing orgasms I enjoy nowadays. Its so night and day from when I used to let Cassie into my bed,” she explained with another thumb pointed at her blushing, diapered hubby.

Cassie was fidgeting uncomfortably with all this humiliating talk about his shortcomings and it was clear he wished he could be anywhere but in this room.

“Well, I think its time now that we introduced your sissy to a life without orgasms of any kind, don’t you? Should we take some measurements?” I offered.

“Absolutely. Cassie–Pull your diapers down. I know its not much, but it’s time to show Ms. Johnson just how pathetic you are.”

With a sob of shame, her husband reluctantly began lowering his shameful diapers down his thighs.
And even though I’ve seen a hundred little peckers like his, I swear–every time its still a bit shocking.
Cassie’s penis looked like a little nub, no more than an inch, protruding from a small set of balls the size of marbles.

I couldn’t help it.
I burst out laughing, covering my mouth as I looked from his ridiculous “manhood”, up to his beet red face and then back down at his crotch.

Oh-my-god,” I said astounded, “You weren’t kidding–that thing is absolutely pathetic. And you’ve definitely made the right decision in locking it up–such a tiny little thing like that has no business being free. It needs to be locked up tight, where he can’t get at it or play with it.”

“I’m glad you agree with me,” Leanne concurred, nodding her head.

“Oh yes, believe me–I’ll make sure this little bedwetter can never play with himself again,” I said, filled with determination.

“You hear that, Cassie?” Leanne said, “I hope your last orgasm in your sissy diapers was a good one because it’ll be your last.”

Cassie winced and bit his lip, squirming in place while I began taking measurements of his tiny nub. It still had a slight coating of baby powder and in fact, if I hadn’t known better, I could have easily believed I was measuring a three year-old, diaper-dependant toddler, instead of a grown man.

“Its good you came here,” I told his wife, “Getting devices that will fit for a penis of his size are really hard to find. Fortunately, we deal with a lot of sissies so I know I’ll have something that will work.”

“That’s a relief,” Leanne confessed.

Going over to the wall behind my desk, I opened several drawers until I found what I was looking for. It was a small pink device, much like a CB6000S, but smaller and with short spikes on the inside of the tube near its tip.
I held it up for her inspection.

Leanne took it in her hands and a big smile crossed her attractive face.

“Yes…yes, this is just what my little sissy needs,” she said nodding her head in agreement, “This should keep you focused on your work instead of rubbing your diapers all the time.”

After handing it back to me, I disassembled it, and then knelt before her nervous hubby to begin fitting him for his permanent chastity. Quickly, I removed all the spacers and taking the cuff ring, I slipped it behind his little sack.

“This is the part I like,” I said winking over at Leanne.

“Say hello to your new best friend, Cassie,” I smirked as I held the short pink tube positioned before his penis and spat on his pathetic nub. With a quick, non-sexual stroke, I covered his shaft with the saliva and pushed it forcefully into the pink tube, quickly mating the holes in the base with the pins on the cuff ring. Taking the small brass lock, I deftly slipped it through the central pin and snapped it shut with a crisp flourish.

“There you are–another helpless sissy boy made chaste,” I said brushing my hands in a gesture of finality.

“Perfect!” Leanne exclaimed, clapping her hands with glee, “That looks wonderful. And the pink is so appropriate for him.”

“I couldn’t agree more. And its good you keep him shaved down there–he doesn’t have any need of pubic hair anyway,” I told her.

“Yes, I had it laser removed years ago when I first started putting him in diapers. It makes it so much more hygienic.”

Cassie was staring down at his little caged package, still trying to come to terms with what a future without sexual gratification would be like.

“What’s it like knowing you can’t play with your pathetic pecker any more?” I asked the squirming sissy.

“I don’t like it,” he bleated weakly, his cheeks blazing with shame.
“The only one having orgasms in your house from now on will be your wife and her lover. Your little sissy stick will stay soft and caged, just as it should be.”

Reaching over, Leanne grasped the device and gave it a solid shake, causing Cassie to whimper with anguish. It was obvious the device was on for good, until such time as she decided to unlock it.

“How does it feel, baby?” she asked her cowering hubby.

He shifted his feet and grasped the device gingerly, twisting it a bit in a futile attempt to remove it.

“Can you feel the spikes?” Leanne asked.

With his lower lip trembling in a pout, he shook his head.

“N-not yet,” he quivered fearfully.

“I think you can put his diapers back on,” I told her, “If you like, I can give you a quick demonstration of the power of the spikes.”

While a look of abject fear crossed Cassie’s face, his wife smiled wickedly and nodded her head.

“Oh yes–please do.”

After his prissy pink diapers were back in place, I sat him down in the chair and spread his legs slightly, bending over him and smiling warmly into his face. With my left hand, I began casually but sensually stroking the silky skin on the tops of my exposed breasts, right where the plump, curvy mounds pushed against each other.

“Do you like big breasts, Cassie?” I whispered in his ear seductively as my other hand reached down and lightly rubbed the front of his diapers. It was soft and cushiony and I could understand why he would be tempted to rub them so much.
Cassie was obviously feeling overwhelmed and he shifted nervously in his seat. Nevertheless, his gaze unerringly fell upon my cleavage and his breathing became heavy and labored. I stroked the shiny plastic front of his diapers lightly–after all, it only takes a little effort to get the right effect.
Sure enough, in just a few moments, he began shifting uncomfortably and a groan of pain escaped his lips.

“Owww!!” he suddenly cried, hastily shoving his hand down the front his diaper to wrestle with his package.
I stood back and watched him, looking down at him with satisfaction as he struggled to extricate his captured wiener from the device. Of course it was quite hopeless and no matter how he pulled or tugged, his penis continued to push urgently against the sharp spikes, making him writhe with pain and discomfort.

Leanne and I laughed and she clapped her hands again, immensely pleased with the results.

“Sold!!” she exclaimed happily.

I nodded and smiled, handing over the keys to her as Cassie bunched his fists in mute frustration.

“Be very careful where you put these,” I warned her, “I would recommend taking them to your work, or some other inaccessible location. If you hide them in the house, eventually, he’ll turn it upside down in order to find them.”

“You know what?–I think I’ll give them to my boyfriend. He can decide when or if the little sissy ever gets any satisfaction.”

“Excellent choice,” I commended her.

“Tell me–what’s the best way to relieve the built up pressure in his balls?” she asked, “I assume he needs to be ‘milked’, or something like that.”

“Yes, there are a number of ways you can do it. Some people use a device called an Aneros tool to massage his prostate gland. It can be a tedious process but eventually, you can completely empty his balls of any fluid that has built up over the course of a month.
“Some women use a strap-on and they have a once per month session with their sissy to drain him that way. And that’s also a memorable way to re-assert your dominance over him.
“Then again, other women just let their boyfriends bend him over a couch and have their way with him–it’s totally up to you.”

Leanne nodded in understanding.

“Most sissies are very resistant to getting their asses fucked by another man, but after a while, when they realize its the only kind of sex they’re ever going to get, they begin looking forward to having a nice big cock filling them up inside.
“In any case, there’s usually no need to remove his chastity device, it will all come out anyway.”

“Well,” Leanne said as she stood up, “I can’t say how happy I am that I found you. Your business is an absolute godsend!”

I smiled proudly, extending my hand to shake hers.
“I’m only too happy to provide a valuable service, locking up the pathetic dicks of sissies like Cassie here.”

As she took out her credit card for payment, she nodded absently to her hubby.

“Cassie–thank Ms. Johnson here for giving you the chastity device you so obviously needed.”

By now, his little penis had subsided, and he was no longer feeling the sharp spikes within his device.

Clearing his throat, he blushed and shuffled his feet, staring at the floor.

“Th-thank you, Ms. Johnson,” he mumbled, his cheeks burning with humiliation.

“Thank you for what?” Leanne prompted him.

“Th-thank you for fitting me for the ch-chastity device I needed,” he stumbled submissively.

“You’re quite welcome, sissy boy,” I said as condescendingly as I could.

Leanne and I shared another laugh at his expense and after ringing her up, I said my goodbyes.

Just another day’s job, well done, here at Chastity Services.

THE END

Surprise!

Chapter One
Loud, booming music filled the darkened room of the nightclub, making conversation difficult for anyone but the person in one’s immediate vicinity. Unfortunately, there was no one in my immediate vicinity as I nursed my drink, alone at the bar, as usual.

The company I worked for, a well established bank in town, had rented the club for the evening to celebrate a merger with a rival financial institution. But as I tended to be something of an introvert, I found myself secluded in a room full of people. It wasn’t that I was ugly, but I was considered somewhat of a geek by my co-workers and the fact was, my friends were few and far between.

It didn’t help that I was still a virgin at 22. Of course, I hotly denied it to everyone around me but I don’t think anyone believed me. The fact was, my list of achievements with girls could be counted on one hand. There was Sylvia, from the comic book club, who I briefly shared an evening making out in the back of her car. That night had ended ignominiously when I had prematurely ejaculated in my pants while kissing her.
And then there was Wendy, who upon discovering my minuscule, pre-pubescent sized boner, broke into gales of laughter and abandoned me in our high school parking lot, horny and ashamed of myself.

So my record with women was hardly something to be proud of. I had resigned myself to a life of solitary exclusion, masturbating at home in my pathetic studio apartment.

My sad self reflection was interrupted by the sudden presence of a person coming up to the bar next to me.

“I’ll get a glass of the Cab,” she said in a cool, commanding voice.

I shivered with instant recognition and my heart skipped a beat. Without turning my head, I knew without a doubt it was my supervisor, Denise.
She had started several months ago and quickly rose through the ranks while I still remained a lowly clerk. She had an authoritative air about her and she was used to getting her way. At 5′ 10″, she towered over me and with her ubiquitous high heels, she was, in fact, a full head taller. I always felt like a fumbling child in her presence, and even though she’d barely said more than a couple words to me during the few months she’d worked at the bank, I was completely intimidated by her.

It wasn’t just the force of her personality. She was stunningly beautiful too, with long, jet black hair that cascaded over her shoulders and down the middle of her back. She had steely blue eyes that took my breath away and made me unable to hold her gaze. But everyone agreed that she was the prettiest woman that had ever worked at the bank and with her cute nose and full, sensuous lips, she could have easily been a model.
Besides being tall and statuesque, she also had a narrow waist and big, impossible-to-ignore breasts. Her full, generous cups seemed to overflow from the restrictive confines of her sheer blouses and there was many a night I had spent, diddling myself as I fantasizing about her and her fabulous body.

As she waiting for her wine, I stared ahead, afraid to look over at her, my heart pounding in my chest and my mouth suddenly dry. Out of my peripheral vision, I could see the slinky black cocktail dress she was wearing, so low cut and revealing that our doddering old fool of a bank manager, Mr. Jenkins, had blushed when he first saw it this evening. At the same time, the female bank workers were looking at her with knives while the males were practically drooling over themselves. The latter group had done everything in their power to get her out on a date but so far, she had rejected them all. I could only speculate what sort of man could live up to her standards but I knew he would have to be incredible.
For my own part, I was content just to stay out of her way and not have her dislike me, at least not overtly.

“What are you drinking?” Denise asked casually.
My heart skipped a beat. Hastily, I looked around, certain she was talking to someone else.
When I could see no other person within shouting distance, I gulped hard and briefly looked up into her crystalline sapphire-blue eyes.
“Um–uh, j-just beer,” I replied lamely.
I instantly hated myself for my abysmal social skills. She must have thought I was the lowliest turd in the room.
And yet, instead of rolling her eyes (as I’d seen her do before), she flashed me an impish smile which only made her look more radiant, if that was even possible.

“You’re name’s Chris, right?” she asked.
I blushed with pride that she actually knew my name, despite the fact we had worked in the same small building for four months together.
“Uh, y-yes,” I stammered, “Hi Denise,” I croaked.
I felt so utterly unworthy of having a conversation with her. My palms were sweating and I felt the eyes of every guy in the room upon us.

Her glass of wine appeared but she ignored it.
“Want to dance?” she asked simply.
I swallowed hard in disbelief.
“M-me?” I stammered as I pointed to myself incredulously.
“I’m not talking to anyone else, am I?” she replied dryly.
I cleared my throat nervously. What was I going to say? No? I would have walked home naked if she had asked me.
“Um, s-sure,” I said uncertainly.

We made our way out to the dance floor and I followed behind like her little puppy. Just watching her walk was an intensely arousing experience, with her perfect buns and the feminine sway of her curvy hips. Gazing at her long, sexy legs, I felt myself getting hard in my pants.

It seemed like I was panting before we even began to dance and I was seeing a side of her I hadn’t seen before. Whereas at the bank, she carried herself with a cool, professional demeanor–here, she was like an exotic dancer, so completely exciting and delicious in every way.
She slid up against me and I shivered with delight. Her dance was tortuously erotic and once again, I could feel the eyes of everyone watching us. I smiled foolishly with pride at being the one that Denise chose to dance with–this was the single most amazing point of my entire life!

As the beat grew slower, she moved up close to me and deliberately ground herself against my thigh. It was all too much for me. I shuddered and abruptly climaxed in my pants.

She immediately sensed a change and she looked at me strangely.
“What’s wrong?”
I shook my head and blushed hotly.

“N-nothing, I’m okay,” I lied.
Suddenly, her slim hand reached down and cupped my crotch, feeling the damp spot forming in front. I jerked away like her hand was a red hot poker, ashamed of my pathetic lack of control.

“Chris, did you just cum in your pants?” she asked pointedly, her left eyebrow rising in a show of incredulity.
“No–I-I….” I stammered at a loss for words.

“I better take you home, I think you’ve had more than you can handle for one night.”
I blushed fire engine red and looked down at the floor in shame. Taking me by the hand, she led me past the groups of staring employees who were fortunately ignorant of my shameful deed.
We walked out to the parking lot, Denise leading the way and holding my hand like I was child. I felt so humiliated, having her think I had no more control than a pimply-faced 13 year-old boy.

Opening the door to her Lexus, she pushed me in without giving me a chance to explain myself.
“Really, I-I can drive myself home,” I tried to tell her.
“Oh no, you’re coming home with me,” she said firmly, “I have something you need at my house.”
I couldn’t imagine what she was talking about, but I was relieved that she at least wasn’t laughing at me or scorning me openly in front of our other co-workers.
As she drove us through the darkened city streets, her delicate, manicured hand came to rest on my thigh, which she began to rub softly.

“So…do you find me sexy?” she asked, her voice taking on a sensuous timbre.
“Oh my god–yes,” I replied without equivocation.
“Well, I think you’re kind of cute too, Chrissey,” she said with that impish smile again.
Even though she had used a more feminine form of my name, I could hardly protest because her hand was making it’s way over to my crotch.
“What have you got hiding down in there?” she asked playfully.
I froze with nervousness, afraid of what she would discover. Even when I was fully erect, my penis was no more than two inches–on my best day. Limp, it could barely be referred to as my “manhood”.

“Hmm…” she said as she reached further down, “I’m not finding anything…are you sure you have a cock?” she teased.
I felt the sides of my cheeks burning with shame and my neck getting red as well.
“Y-yes,” I stammered, “it’s-it’s just not, um, very big.”
“Well, I’ll have to take your word for it, cause I’m not finding anything.”
This was mortifying to have to go through again, with her, of all people.

At last, we pulled into her driveway and the humiliating inquiry was interrupted. We got out and went into her house where she gave me a beer from out of her refrigerator. Pouring herself a glass of red wine she instructed me to follow her down the hallway.

“Chrissey, if you’re going to be with me, we’re going to have to take some steps to take care of your little problem.”
I wasn’t sure if she was referring to the size of my penis or my tendency to prematurely ejaculate, neither of which I was very proud of.
Turning to face me, she reached down and began unbuttoning my pants.
“Wha-what are you doing?” I squeaked, suddenly nervous again.
“Look. Let’s get something straight–in this relationship, I make the rules. If you can’t deal with that, you can walk out the door right now and I’ll never speak to you again,” she said defiantly.
The color drained from my face. How could I tell this incredibly gorgeous woman no? How could I deny her anything?

“I…I’m okay with that,” I said meekly.
“Good. I’m glad to hear it,” she said, her voice taking on a bossy tone, “because I have something here that will help your little problem.”

I still didn’t know what she had in mind but I stood there like a child as she unzipped my pants and dropped them to the floor. I shivered as her smooth hands slipped inside my underwear and pulled them down, ignoring the gooey wet spot on the front. She looked at my shriveled member and shook her head, making me blush all over again. I groaned with embarrassment as she reached into her dresser drawer and took out a clear plastic device of some sort.

“I only hope this is small enough,” she said as she took it apart and then put the pieces aside.
Despite my humiliation, I felt myself getting aroused all over again. As she was bending over, I couldn’t help but gaze down the scoop neck of her cocktail dress and stare at the two big twins spilling out of her top. They were truly massive and they pushed up against each other, creating an unbelievably sexy cleavage. As I felt her handling my sack, I started to get erect once more.

“That’s good, keep staring at my breasts, Chrissey,” she said as if reading my mind, “it’ll help me to get your little penis into this device.”
I whimpered as she placed a clear ring around the base of my genitals and with a little lube, began pushing my semi-erect member into a short, cock-shaped tube with a slit at the end.

“Wait–wha-what are you doing?” I asked suddenly apprehensive.
“Something your mommy should have done a long time ago,” she said as she pushed the tube up against the ring to mate it with the pins facing forward. In no time, she took a small lock and slipped it through the hole in front, clicking it closed with an air of finality. My penis, small as it was, felt stuffed into the device and it was now forced into a downward facing angle.

“There, that should take care of that little problem,” she said with a smug look on her face.
“But…but how am I going to get any satisfaction now?” I asked dumbly.
“You’ve already had your satisfaction, and I hope it was good for you because it will be the last orgasm you have for quite a while.”
Before I could protest, she continued without pausing.
“And now, we need to take care of a little unpleasant business. Well…unpleasant for you, that is,” she said with a smirk as she reached into her dresser drawer and pulled out a long rectangular wooden paddle with air holes in it.

“Wait–what are you gonna do?” I quaked nervously as I tried to back away from her.
“This will help you understand who makes the rules in this relationship,” she snapped as she snatched my wrist and yanked me over her sexy lap.
“Wait! Stop!” I cried desperately.
I hadn’t been spanked since my mom caught me masturbating at the age of sixteen. She had quickly reduced me to tears (as she always did) in short order and I didn’t want a repeat here. With the floor only inches from my face, I tried to get up off her lap but she held me in place with steel-like strength.
Denise gripped my shirt firmly with her left hand as her right arm swung up in an avenging arc with the paddle.
“Stop it! Stop it!” I wailed as I kicked my feet frantically.

The paddle swooped down and landed squarely across both my bare cheeks, searing them like a hundred wasp stings.

“OWW-WOW-OWW!!!”

SMACKKKK!!!

Another harsh swat landed right where the first one did and I gasped in shock, my eyes bugging out of my head. I struggled mightily against her but nothing I did could extricate myself from her grasp.

SMACKKK!! SMACKKKK!!

A few moments ago, I had been worried about the chastity device but that was the last thing on my mind right now. My eyes filled with tears and I looked down at her high heels, spread a little apart to give her support as she spanked me hard like a naughty little boy.
Her paddle rained down on my defenseless bottom again and again, scalding it and turning it into a flaming sea of crimson welts. I tried to hold back but I couldn’t take it anymore. As her harsh paddle swatted my tender cheeks over and over, I burst into tears and sobbed like a baby.

She kept up her punitive rhythm and I slapped my hands in the floor in frustration and impotence. How could I ever have imagined this is how I would be spending my evening? Why was she punishing me so thoroughly? This was certainly no sensual play spanking, but a blistering paddling that would leave me unable to sit for some time.
Every time I tried to position one of my cheeks away from her attentions, she’d smack it especially hard several times.

Tears were streaming down my face and my nose was running when she finally stopped and let me up. Standing me on my shaky legs, I stamped my feet and rubbed my throbbing, blazing cheeks. For several moments, I just bawled unashamedly in front of her, knowing I looked like nothing more than a defeated, punished child.
She gazed back at me with a look of tremendous satisfaction, a pleased, superior smile on her pretty face.

“Why did you spank me so hard?” I sobbed in bitter frustration.

“So you’d know who wears the pants around here,” she said as she stood up. Reaching her hands out, she took me into her arms and held me close, burying my face into the soft, pillowy cushions of her big breasts. I cried and cried, my chest heaving as she softly stroked my swollen, flaming bottom.

“There, there, baby, get it all out,” she whispered softly in my ear.
Despite the intense, searing pain on my cheeks, it was wonderful to have my nose deep between her beautiful boobs. They smelled fantastic and felt even better against my wet, sobbing face.
For so long, since the first day Denise started working at the bank, I had fantasized about doing just this, although, certainly not under these circumstances.

“And now, it’s time my little sugarplum took care of mommy,” she said with a coy smile.

Chapter Two
“And now, it’s time my little sugarplum took care of Mommy,” she said with a coy smile.

Holding my face gently in her slim hands, Denise bent down and gave me a long, slow, sensuous kiss.
I closed my eyes and relaxed, feeling myself helplessly melting in her soft hands. She tasted fabulous and it was obvious she was in no hurry to end our embrace.

I felt so confused! The same beautiful woman that had just paddled my bottom to a five alarm fire and made me cry like a baby was giving me the most passionate kiss of my life!
Although my mind may have been confused, my penis certainly wasn’t. It expanded within the chastity device until it was straining like a Pit Bull against it’s leash. Without thinking, I reached down to alleviate the constriction but could do little other than helplessly grasp my imprisoned wiener in futility. It throbbed with frustration and angst.

Denise reached down and tweaked my nipple, making me groan with desire.

“I have a surprise for you,” she said finally as she ended the kiss and whispered in my ear.
“You-you do?” I asked breathlessly.
I was so worked up and aroused–I wanted her desperately!
“I have a very big surprise for you,” she said, and even though I thought I heard a trace of mirth in her voice, I was so excited, I dismissed it.
“I want you on your knees, Chrissey,” she told me with a provocative smile on her pretty face.

Maybe she wanted me to lick her pussy? If so, I certainly didn’t have any objections. I had never been that close to a woman’s sex before but I figured it couldn’t be that difficult. Presumably, she’d tell me what she wanted if I wasn’t doing it right.
“Um, will you teach me how to do it?” I asked her timidly.
“Oh yes,” she grinned, “I’ll train you to be the very best.”

As I knelt before her on my knees, she took a small object in her hands and pressed a button. I thought I heard some mechanical device being turned on but I couldn’t be sure and as I glanced around the room, I couldn’t see anything apparent.
“What was that?” I asked innocently.
“Don’t you worry your little head about it, Chrissey, you just need to focus on the job ahead of you,” she said, still grinning.
Part of me suspected she had something up her sleeve but I couldn’t imagine what it was, and in any case, I wanted to prove to her I could satisfy her like a man.

“Close your eyes, Chrissey, it’s time for your big surprise,” she instructed me.
Doing as I was told, I knelt in place, not understanding why such a thing would be necessary. I heard her moving a bit and thought I could discern her pulling her panties down her legs. My breathing quickened as I imagined her sex–was it shaved down there? That would be super sexy, I mused.

“Open your mouth, sissy,” she told me, “Nice and wide…wider, Chrissey…that’s it…nice and wide…good boy.”
I heard her giggling and couldn’t imagine what she found so amusing.
“Here you go…just what every sissy boy needs,” she said.

Suddenly, I felt a warm, massive object being pushed into my mouth, quickly filling it to capacity. My eyes shot open and I squealed with shock.

Denise had a fat, gargantuan cock and she had just thrust it deep into my mouth!

I felt her hands firmly holding the back of my head, preventing me from escaping but I struggled anyway.

“Surprise!” she said with a throaty chuckle.

“AWFGH!!!!” I gagged as she pushed her cock all the way in, all the way to my larynx, nearly choking me.
She smiled down on me wickedly, keeping her hands on the back of my head as she pulled her member out a little and then shoved it back in. Each time, I gagged and struggled to breathe through my nose.

“Don’t worry sissy, you’ll be getting plenty of practice. Just use your tongue…that’s it…thaaaat’s it…suck that big lollipop,” she said in a husky voice.
I didn’t want to accommodate her but there was little I could do as she thrust it in and out of my mouth, forcing me to suck her titanic phallus.

“This is right where you belong, on your knees with a big hard cock in your mouth…”
She paused only long enough to moan deliriously.
“Oh yessss…That’s it…show mommy what a good little cocksucker you are…”
I couldn’t believe what I was doing. Was I really sucking my supervisor’s cock right now? On my knees, giving my hot boss a sloppy blowjob?
My lips were wrapped around the slippery shaft of her big, thick cock and she slid it in and out of my warm, wet mouth at a pace of her own choosing.
“More tongue…that’s it…that’s my little sissy…Mommy’s going to teach you to be the best little cocksucker there is…”

Her words were so humiliating to hear, and yet, I felt like I had no choice. I could only hope and pray that if she decided to cum, she’d pull it out of my mouth first.
One time, I had experimented with my own, tasting the strange semen while masturbating and I hadn’t liked it at all.

“Maybe I’ll have you do this to me in the break room at work…would you like that, Chrissey?”

Needless to say, with eight inches of hard cock meat stuffed into my mouth, I was in no position to respond.
Some of her precum was leaking as I sucked on her and the salty taste mixed with my saliva like a lubricant. Her fat shaft was pistoning in and out and a steady stream of drool was dribbling down my chin.

“Get ready sissy…oh…oh…oh-my-god, I’m…I’m about to…” Her voice trailed off.
Her thrusts into my willing mouth were becoming more urgent and I sensed her orgasm was not far off. It felt like she was practically raping my mouth, battering her big pole in and choking me, only to pull it out and thrust it back in again. My head was getting dizzy from all the pounding until she stopped abruptly and held my head tightly in place with both of her hands. The head of her cock was positioned just inside my mouth, with my lips wrapped around the big, bulbous head.

“OHHHHH!!! OH MY GODDD!!!” she shrieked.

I felt her cock swell in my mouth, followed by a huge explosion as she came like a tidal wave. Instantly, my mouth was filled to capacity with hot, creamy semen and I gagged as I struggled to swallow it. No sooner did I gulp it down, when she blew a fresh batch into my mouth, filling it to overflowing. I squealed and shook my hands in the air, desperate to get relief from the mighty cannon my lips were wrapped around. Semen spilled out of the corners of my mouth and dripped down my chin. I tried to back off and get away but she continued to hold my head firmly in her hands, forcing me to take all her cum as she thrust her hard cock all the way in and shot a third load, right down my throat.

All the time, she was gasping for air as she roiled in the throes of her multiple orgasm.
I could hardly breathe and I swallowed again and again, trying to keep up with what seemed like a fire hydrant.
At last, the spasms lessened, and she leaned back against her bed, exhausted, her beautiful blue eyes rolling into the back of her head.

“Oh my god, that felt good…I’ve wanted to cum in your mouth for months now,” she confessed between gasps for breath.

I blushed with humiliation at having willingly sucked a cock and swallowed her massive load of semen, to say nothing of being the object of her pervy desires. My lips and chin were sticky with cum and the inside of my mouth was slick with her semen. Blushing furiously, I swiped my arm across my face even as I subconsciously licked the cum from around the corners of my mouth.

“But it’s true,” she said still trying to catch her breath, “ever since I first saw you in the bank, I’ve pictured you on your knees, with my cock in your mouth–and we both know that’s where you really belong.
“With that tiny little penis of yours, you’re useless as a man, but as a cocksucking sissy, I think you have a very bright future,” she giggled.

Reaching down, she grasped my locked up genitals and gave them a shake.
“And fortunately, we’ve taken care of that little problem,” she smirked, “with emphasis on little.”
I stood up, shaken and upset, my cheeks burning with shame.

“Honestly, you didn’t really think you were ever going to satisfy a woman with that tiny thing, did you?”
Her scorn washed over me and made me want to cry again.
Craning my neck to look up into her pretty and confident face, I felt so completely inferior to her while she stood there, her hands on her hips and looking down at me with that smug, superior expression of hers.

“Aww, come here baby,” she said, taking me in her arms again and using a voice reserved for toddlers. Once more, she pushed my nose into her deep cleavage and held me there, stroking the back of my head tenderly.
“I’m sorry baby, I didn’t mean to hurt your feelings,” she said soothingly, “don’t be upset, okay?”
She reached down and kissed my ear to comfort me.
I was so confused! My emotions were all over the place! In one moment, Denise could be as cruel as my worst enemy, and in the next, loving and warm.
Meanwhile, I breathed in deeply of her feminine scent and savored the wonderful feeling of her big, soft breasts against my face.

“Okay Chrissey, you’ve been through a lot today, I think it’s time you got a little reward,” she said in a seductive voice.
Wondering what she had in mind, I pulled my face away as she took one of her long nailed fingers and pulled the spaghetti strap of her dress aside, letting it fall past her shoulder. As the dress fell away, it revealed the cup of her sexy satin black push-up bra. I licked my lips as she reached between the cups to undo the clasp holding them together.

“Is this what baby wants?” she cooed to me.
I nodded hungrily and she peeled back the cup from her right breast to reveal a big pink aureole and a perky nipple.

“Here sissy, suck from Mommy’s breast,” she urged me.
Since she was so tall, I hardly needed to bend over to accommodate her. I happily wrapped my lips around her warm nipple and suckled, feeling waves of bliss washing over me.
“That’s just what Mommy’s baby needs, hm, sugarplum?” she asked me in a sweet voice.
I nodded and savored the taste of her nipple, reaching up with my right hand to fondle her left breast.

“Nope, hands off sissy, that’s not for you to touch,” she scolded me lightly.
I whimpered but continued enjoying the wonderful nipple in my mouth.

“Hmm…I’m starting to think Mommy needs to get some clothing more appropriate for her baby…like maybe some diapers and plastic pants? What do you think, baby Chrissey? Is that what my little sugarplum needs?”

I shook my head and mumbled no, although it was considerably muffled with her gigantic breast filling my mouth.
“Well…I don’t know Chrissey, I think you’re more of a sissy baby than you’ve led us to believe…I might just have to get some baby clothing for you and dress you up properly.
“One thing’s for sure…I’m taking you off the market so I can have you all to myself,” she said as she beamed down on my blushing face, “I have big plans for you, Chrissey.”
Chapter Three

For the next three days at work, Denise practically ignored me. Once, when I tried to talk with her alone in the hallway, she simply brushed me aside and said she was “busy”. I couldn’t understand it. What had I done wrong? Had I not submitted to her completely that first night?

Despite my shock at discovering her anatomy, I still found her incredibly sexy. She still had that gorgeous model-esque face and the big boobs to die for. Every time I thought of suckling from her hard nipples, I swooned.

All week after the night at her house, my heart was doing somersaults–that a woman so totally out of my league would be interested in me, just blew me away. But then, I also couldn’t understand why was she so cool with me at work. It hurt my feelings that she made no acknowledgement of what had happened between us and yet, I couldn’t get her off my mind. I worked at my counter, constantly daydreaming about her. Every time she walked into the room, my heart stopped beating and my eyes followed her every move.

The other issue was, I was beside myself with horniness. I had never gone more than a couple days without being able to masturbate freely and this chastity device of hers was killing me! I had tried everything I could to remove it but it’s design was devilishly made to prevent any kind of escape.

I found myself waking up in the middle of the night, my nighttime erections becoming a source of pain I never thought possible. I found that if I got up and walked around, the budding erection and the associated discomfort would subside, but it was still tremendously frustrating.

I made a vow to demand Denise remove the device the very next time we were alone.

On the other hand, my social standing at the bank had gone up considerably since the party. All the guys thought I was some kind of stud and even the cool ones who never talked to me looked at me in a whole new light. If only they knew I had been on my knees that night, swallowing load after creamy load of Denise’s semen!

I tried to block out that experience but the fact was, I was so horny all the time now, I was willing to put that aspect of her aside. In the big scheme of things, I rationalized that it just wasn’t that important.
But regardless, I didn’t think it was fair for her to ignore me and leave me locked up like this.

Finally, on Friday, I found a brief note left at my counter station along with a stack of checks. It said; ‘Be at my place 9 pm sharp–Denise‘.

I sighed and held the note to my chest, smiling to myself. She did care about me after all.

That night, after a fresh shower and a change into my best shirt and slacks, I showed up Denise’s door with a bouquet of flowers, precisely at 9 pm on the dot. When the door opened, my heart stopped and I was momentarily breathless. She looking absolutely ravishing with her long black hair falling in curls over her bare shoulders and a dark red lipstick on her sensuous lips.
Once again, I was struck by the difference between her attire at work and how she looked when outside of it. She was wearing a black Lycra bustier with a matching skirt and of course, her usual sexy high heels. Around her neck, she wore a thin gold necklace with the key to my chastity device on it, as if taunting me with my freedom.

She gave me a coy smile and then reached down, gently holding my face and planting a long, erotic kiss on my lips that left me panting.

“Hi Chrissey, glad you could make it,” she said with a playful wink, “The flowers are lovely.”
An electric rush rippled through me. I gulped as I drank in her beauty and all the demands and frustrations of the week seemed to evaporate. I had intended to make her remove my device and complain about her ignoring me but now that I was actually face to face with her, my heart was doing cartwheels and I couldn’t find the words. I was just happy to see her smiling at me again–everything else seemed trivial by comparison.

As we went inside, she turned and took me into her arms, pushing my nose into that source of nirvana, her deep cleavage. I sighed and nuzzled, happier than I could ever remember being in my life.

“Did you like nursing from my boobs last time, Chrissey?” she asked softly in my ear.
“Oh yes, that was awesome!” I exclaimed.
“I liked it too,” she replied, “I think you’re just the sweetest little sissy I’ve ever known and for some reason, you bring out the mommy in me.
“How would my baby like to go into my bedroom and nurse again?” she asked.
“Oh yes–for sure!” I replied enthusiastically.
Even though I didn’t like the reference to being a baby, the thought that she saw me as “hers” made my heart swell with pride and joy.
Taking my hand, she led me down the hallway into her large bedroom with it’s four poster king bed. However, as walked through the threshold, I was quick to discover that she had placed several items on the bed, none of which I found welcome.

A thick set of cloth diapers, baby powder, plastic pants and pins lay next to a frilly pink top of some sort. And next to that, was Denise’s fearsome Spencer paddle, ready for immediate use. My heart skipped a beat and I stopped in my tracks.

“Chrissey, I want to dress you up in a cute little outfit I picked out just for you–I know you’ll just love it.”
She beamed at me like she was presenting me with a new car.
“B-but, I’m not a baby,” I protested in a whining voice.
“Oh, I think you’re very babyish,” she immediately replied, “You have a little baby penis, you have an obvious fetish for breastfeeding, and let’s face it, you’re hardly much of a man.”

Once again, her words stung me to the core. It seemed like Denise could go from one extreme to the other in the blink of an eye, from loving to cruel without a second thought.
“But I don’t want to wear diapers!” I complained bitterly.

The fact was, the sight of those diapers and plastic pants brought strong, unpleasant memories of my early teens flooding back, from a time when I had been a habitual bedwetter. My mom had responded by putting me in diapers and plastic pants every night and the practice continued for several years–in fact, pretty much up to the point at which I moved out. I still had the occasional accident in bed but since I had few, if any visitors over to my apartment, I never gave the problem or the associated smell much thought.
And now, Denise wanted to put me back in diapers just like my mom!

“I won’t do it,” I said, but my voice lacked conviction.
The warm smile on Denise’s face vanished, to be replaced by an angry scowl.
“What did I tell you about obeying my instructions?” she snapped as she went over and picked up the paddle, “Do I need to put you over Mommy’s lap again?”
Her voice had taken on a stern edge to it, and the hair went up on the back of my neck.
I gulped nervously and looked around the room in a panic. I didn’t want to blow my relationship with this beautiful babe but I didn’t want to be dressed up like a baby, or be thought of in that way.
And yet, the steely determination in her pretty blue eyes as she held that hard wooden paddle in her hands made my knees weak. I held an instinctive fear of being spanked from my experiences growing up under my strict mother.
And it had taken days for the bruising to go down on my bottom after my last session over Denise’s lap—I wasn’t about to do that again.

“What’s it going to be, Chrissey? A hard spanking–followed by diapers…or just the diapers? It’s up to you,” she said crossing her arms across her impressive chest, her voice as hard as iron.
I felt like I was being scolded by my mom all over again and my will, never very strong, crumbled before this tower of female authority.
“Just-just the diapers, please,” I squeaked.

“That’s better,” she said, sounding smug and superior once again.
Putting the paddle down on the top of her dresser (to my vast relief), she scooped up a large pink pacifier and held it before my mouth.
“Suck on this baby, while Mommy puts you into your diapers.”

I whimpered weakly and reluctantly parted my lips as she pushed it in, the fat rubber nipple filling my mouth and making any kind of coherent speech impossible.
“You are not to remove that under any circumstances, got it?” she demanded.
I nodded my head mutely as she began undoing my pants and taking my shoes off.
What had I gotten myself into? It seemed that every encounter with Denise took me deeper and deeper down the rabbit hole.

Her demeanor changed when my chastised penis came into view and she suddenly giggled to herself.
“And how’s Chrissey’s little pee-pee doing today?” she asked in an amused, condescending tone, “Having difficulty dealing without playing with yourself everyday?”
Even though it was humiliating to admit to her charge, I nodded my head, hoping the admission would grant me some leniency from her.
“Better get used to it, Sissy, your days of masturbating are long gone.”
I winced and gritted my teeth in frustration.

As she pulled my freshly ironed shirt off of me, I wanted to ask when she planned to unlock my plastic prison but the pacifier stuffed into my mouth only garbled my words. I tried again but she just dismissed my babbling by shushing me and guiding me over to the bed.
Laying me down on top of the thick stack of diapers, she squeezed some Desitin in the palm of her hand and after raising me by my ankles, began smearing it across my bottom.

“The last time I saw these cute little buns, they were sporting a nice, deep shade of red,” she smirked as she set my legs down.
I blushed and sucked harder on the pacifier, the entire experience bringing back waves of humiliation from my bedtime routines with my mom.
Denise sprinkled my entire area with baby powder and even up on my chest, softly rubbing it in as she looked down on me and winking playfully. The fragrant scent brought back memories of weakness and inferiority in me, making me recall my childish lack of control.
Drawing up the bulky, but very soft cloth, she slipped a pair of safety pins through to secure it around my hips, first one side, and then the other.
“There!” she said with a flourish as she patted the fat front of my padded crotch, “All set and ready for your baby panties!”

I cringed with embarrassment as she took the pink pair of waterproof pants next to me and positioned them over my feet, drawing them up my legs in a tortuously slow fashion, no doubt intended to draw out the humiliating procedure as long as possible.
“How does it feel to be wearing baby pampers again, sissy?” she asked me.
My face glowed red with embarrassment and I looked away.
Using her perfectly manicured fingers, she slowly ran them around the elastic waistband, pulling them up and over the thick cloth surrounding me until the fluffy diapers were fully contained inside the plastic pants. With another dusting of baby powder between my legs, she put the diapering supplies away and came over to put my top on.

“I don’t have much for you to wear just yet, but don’t worry, sugarplum, I’ll get you all fixed up in no time,” she assured me.
The top she was putting on me was made of pink fleece, with short white puffy sleeves and a teddy bear playing with blocks decorating the chest. The hem, which was so short it barely went down to my navel, ended in a soft row of white ruffles.

I felt extremely babyish and I couldn’t put my legs together due to the thickness of the diapers between my thighs. Looking up at Denise’s pretty smiling face brought on sensations of helplessness in me. And I felt that whatever control I might have had in this relationship was rapidly disappearing.

Climbing onto the bed, she slowly unzipped her bustier, tantalizing me as she allowed her tremendous breasts to gradually be revealed in her sexy push-up bra. With a seductive look, she crawled over and straddled me, her magnificent bosom only inches from my face. Looking up into her stunning eyes, I felt powerless before her.
Taking out the pacifier from my mouth, she put it aside and positioned her cleavage right in front of my nose.

“Does baby want to nurse from Mommy’s boobs?” she asked in a musical voice.
“Uh-huh,” I said weakly. My penis had expanded in it’s tube and was pushing against the end as hard as it could. If only she would let it out!

“Um…D-Denise?” I ventured carefully.
“Shushhh, baby,” she said as she put a finger to her lips. She undid the clasp at the front of her bra and her gigantic melons fell free like two watermelons falling out of a basket. Reaching on either side of me, she held my arms down, pinning me in place. Before I could say another word, she mashed her big left breast into my face, forcing her enormous pink nipple into my eager mouth. I wasted no time in sucking it, and it quickly became hard in my mouth.

“Thaaaat’s Mommy’s baby,” she cooed.
Reaching back, she began softly stroking the smooth front of my diapers, which only aggravated my arousal level, making my little imprisoned penis throb with frustration and impotence. It was maddening, not being able to do something as simple as have a normal erection!

After about ten minutes, she switched over to her other breast and the sexual torment continued. I had never been so turned on in my entire life!

Once again, I tried to reach up and cup her free breast but she slapped my hand away.
“Sorry sissy, that’s not for you,” she told me.
I mewled in frustration but continued to enjoy the engorged nipple in my mouth.

After another five minutes or so, she pulled away from me without warning, bringing my breastfeeding session to an abrupt end.
“Okay, that’s enough of that for today–now baby needs his ba-ba before beddie-bye,” she said.
I furrowed my brow with disappointment–I didn’t want to be treated like a baby anymore, I wanted to be treated like an adult and her peer.
Reaching behind her, she picked up a baby bottle with a pink top that was on her night stand and brought it over to me.
“Open up, baby,” she said with that heart stopping smile.
I whimpered and shook my head no.
“Come on–open up, baby,” she repeated, pushing the dripping rubber nipple to my lips.
When I refused to open my mouth, she slapped my bare thigh which elicited a yelp from me. As my mouth opened, I was rewarded with a fat nipple and the big bottle of warm milk.

I had always detested milk, especially warm, since I considered it to be a drink only for infants. I whined and shook my hand but Denise kept the bottle to my mouth and forced me to continue to drink from it.
“There, there,” she said, whispering down at me, “that’s a good baby, drink your milk like a good little boy.”
It was so humiliating having to nurse from the bottle and listen to her treat me like a toddler but I had to admit it was also wonderful to be in such close proximity to such a pretty woman, and to have her fawn over me. I decided if the price of that was playing her little game, for now, then so be it. I drank the milk which seemed to make her happy, although for my part, I started to feel myself getting unexpectedly drowsy.

“Tell you what, Chrissey,” she said as she beamed down at me, “If you can manage to keep your diapers dry tonight, maybe I’ll consider letting you graduate to some training panties, okay?”
I nodded my head in acknowledgement. I wasn’t used to drinking anything before bedtime but it wasn’t too late yet and I could always use the bathroom before I went to sleep.

The last thing I remembered as the lights faded around me was looking up over the top of the baby bottle at Denise’s smug, smiling features.

Chapter Four
When I woke up, I felt somewhat disorientated and it took me a moment to get my bearings. Looking around the dimly lit room, I realized I was in Denise’s bed and I was still wearing the thick diaper she had put me in last night.

And it was at that moment, that I suddenly realized I had thoroughly soaked it during the night!

Oh my god–what was she going to think of me now?
Of all nights to have an accident, why did it have to be the one night I spent with the hottest woman in town?
I was only too familiar with the feeling of cool, clammy Birdseye cloth clinging to my hips and bottom. I had felt it every morning during my early teen years as a result of my mom putting me in diapers and plastic pants every night. Her solution, while it kept my bed dry, ensured I felt the soggy effects of my incontinence until she decided to change me.
Somehow, I had to get rid of them before Denise discovered me.

Slowly rolling over to see if she was awake, I came to find her right next to me in bed, naked and lying on her side, her head propped on her hand as she lay there, smiling over at me.
“Did my baby sleep well?” she asked with a beautiful smile.

I blushed and swallowed hard.
“Um…yes, yes I did,” I replied uncertainly.
I glanced around the room, trying to think of some way to get out of bed to remove the diaper before she discovered it was wet.

“And was my little sugarplum able to keep her diapers dry?”
I bit my lip as my face turned a bright red.
“Um…ah, I um…” I stuttered.
Reaching down beneath the blankets, I felt Denise’s smooth hand slip inside my diaper, revealing my wetness to her all too clearly.

“Looks like Mommy has a little bedwetter on her hands,” she said with a knowing smile.
“I-it-it was j-just an accident,” I stammered, afraid she would kick me out and never speak to me again.
“I don’t think so, Chrissey. And I don’t think Mommy’s little baby can be trusted today without her diapers,” she told me.
I shook my head, my apprehension rising as to where this was going.

“Oh no–it was just an accident–I don’t know why it happened–it was just a fluke,” I tried to explain.
“Now Chrissey, you and I both know it was no accident. How do I know you won’t wet your pants today at work?”
I didn’t like where this was going at all.

“Mm-hm, I think my little baby’s going to have to wear some diapers to work today,” she told me with a disarming smile.

I shook my head and put my hands up.
“Now wait…I mean, I can’t–I mean, I’m not wearing–”
“–On the other hand…I can think of one way in which you could get out of it…”
She was smiling coyly at me and with those devastating blue eyes, it was all I could do to resist her charm.

“I’ll tell you what…all this talk of putting you in diapers is getting me hot…if you can make me cum in five minutes, I’ll let you go to work without your diapers.”
Before I could respond one way or another, Denise was already rising up and she pushed me onto my back, quickly straddled my torso.
“No–wait!” I squealed.
She inched her way up my chest, her big, hard cock quickly closing to within inches of my face.
“My phone says it’s 7:05–you have until 10 past the hour Chrissey–better get to it,” she smirked at me.
“No…please,” I pleaded, “I don’t like sucking cock–”
My words were interrupted as she shoved her meaty leviathan into my mouth. She was straddling me, supported by her knees as she steadied herself with her arms against the headboard of the bed. In this position, with my head backed against the pillow, I could do nothing as she face-fucked me, shoving her fat cock deep into my mouth and grinding her pelvis against my face.

“Use that tongue again, Chrissey…oh…that’s it…yes, that’s better…suck it good…ohhh…that’s my little sissy…thaaaat’s Mommy’s little boy…suck that sweet cock…mmm…yes…”

Her big balls were slapping my chin as the fat end of her cock pounded urgently against the back of my throat.

“Ohhhh…what a good little cocksucker you are, Chrissey,” she moaned.

Knowing I had an impending deadline, I tried my best to please her, despite my feelings to the contrary. I swirled my tongue along the warm, throbbing underside of her massive head, sucking and slurping as best I could.

But there was only so much I could do. The pillow kept my head from moving and Denise was the one controlling her thrusts into my slobbering mouth.

“Get ready, Chrissey…breakfast is coming,” she said breathlessly.

I hoped it was inside the five minute deadline but it seemed like she had been pounding my face for 8 or 9 minutes already.
Her cock swelled in my mouth, and she jammed it deep into my throat.
“OHHHHHHHHH GODDD!” she cried, as she loudly and forcefully emptied her balls.
I could feel warm globs of thick, sticky semen being blasted down my throat and I swallowed again and again. Finally, she pulled her cock out long enough to fill my mouth with one last good load before pulling it out entirely.

A white strand of cum followed the blunt tip of her cock from my mouth and I gasped for air.
“Oh, that felt so good,” she said as she held her still hard cock in her hand, moving it left and right and smearing the last bit of cum across my lips.
“Lick that up, Chrissey, it’s what all sissies love,” she said condescendingly.
Reluctantly, I did what I was told, hoping I could get my wet diaper off and get ready for work. I reached over and picked up her phone, but to my dismay, the face read 7:15 on it.

“That’s right baby…looks like someone is going to work in diapers and plastic panties today,” she said with a big smile.
“Noooo,” I moaned unhappily.
“Don’t worry sugarplum, I won’t make it as big as the one you’re wearing now,” she assured me.
“But–how am I going to hide it?” I whined miserably.
“Don’t worry, honey-bunch,” she said dismissively, “no one will see a thing, you can wear your jacket which will cover that cute bottom of yours.”

Reaching down, I felt the hard object inside my diapers that was my chastity device.
“Denise, when are you going to unlock my penis?” I asked her, “I haven’t been able to cum for a week now.”
“If I’m going to be changing your wet diapers, you better start calling me Mommy,” she corrected me.
“Okay, M-Mommy,” I said awkwardly, “When are you going to unlock my chastity device?”
“Tonight, if all goes well,” she assured me as she got of bed, “I promise I will unlock you.”

My spirits rose immediately. Finally, I would get some relief for my poor, aching balls! As Denise laid out a changing pad, I was already thinking of ways in which to cum. My imagination, deprived of an orgasm for so long, began working in overdrive, thinking of all the delicious ways I could cum…would she be returning the favor of oral sex for me? Maybe she would let me rub my penis between her big, beautiful boobs? Hell, even a handjob would be wonderful from this sexy babe.

Denise busied herself getting the diapering supplies out and arranging them on the bed; she put a fresh diaper, baby powder, wipes, and diaper rash creme next to me. I didn’t see any plastic pants so I assumed the diapers today would be more symbolic, than for real purposes.

She pulled my wet ones off and placed them in a plastic bag, using the baby wipes to clean me up.
“Wow, I’ve never seen so little hair on a boy before,” she said as she wiped my pubic area, “Are you sure you’ve been through puberty yet?”
I blushed and assured her vehemently that I had.
“Well, this looks suits you better anyway,” she replied as she took a palm full of diaper rash creme and smeared it across my bottom cheeks. A thorough dusting of powder followed and I grew apprehensive again.

“Not so much!” I complained, “Some one will smell it on me.”
“Oh no, they won’t,” she disagreed, “Besides, you’ll be more comfortable this way.”
In no time at all, she deftly pinned the new diaper on me which was thankfully, much thinner than last night’s, although I still had concerns that I would be able to conceal it.
Turning around briefly, I thought she was done until she revealed a pair of pink nursery print plastic pants in her hands.

“D-do I have to wear those too?” I asked crestfallen.
“Of course, baby–what if you wet yourself today?”
“I won’t do that–I promise–please don’t make me wear the pants too,” I protested.
“Sorry sissy,” she said ignoring me and feeding my feet through the leg holes, “We can’t take that chance.”
I felt like I was with my mom all over again, who did as she pleased, regardless of my objections. I shook my fists and whimpered with frustration.
Worse yet–these waterproof pants were made of a somewhat stiffer plastic and they crinkled loudly as she drew them up my legs.

“I still don’t see why I have to wear diapers during the day,” I complained bitterly.
“Because I can’t trust you to keep your pants dry, sissy. Now if I hear one more word out of you, I’ll put you over my knee and warm your little bottom with my paddle.”
I pouted but remained silent as she positioned the humiliating pink panties over my diaper.

“Okay, stand up, Chrissey,” she instructed me.
I stood up next to her and she physically turned me around, fiddling around with something at the back of the waistband of the plastic pants.
“What are you doing?” I asked suspiciously.
I felt the waistband getting cinched snug and a lock clicking shut.
“Just making sure you don’t get any ideas about removing these during the day,” she said with a smug tone in her voice.
She emphasized her statement with a smack to my diapered bottom.

I gasped and craned my neck around to look. I hadn’t realized it before, but the waistband contained a small chain and Denise had just locked it closed, permanently securing the plastic pants, and therefore the diapers around me until she chose to remove them.

I balled my fists and stamped my feet in frustration.

I wanted to protest loudly and demand she take them off immediately but the memories of being over her lap were still fresh on my mind. She had already proven that she was physically stronger than me and I didn’t need a repeat demonstration of that fact over her lap.
Instead, I gritted my teeth, rationalizing that these were acceptable sacrifices to be made for having a relationship with such a drop-dead gorgeous woman as Denise.
I didn’t like it, but compared to what my love life had been a week ago, this was a thousand times better.

And tonight, I was going to get to cum with her. How many other guys would have willingly paid to be in my shoes?

 

 

Chapter Five
That morning at the bank, I was nervous as hell.
I had done everything I could do to conceal my diapers by keeping my jacket on but the plastic pants were infuriatingly loud. Every step I took threatened to reveal my shameful secret to everyone at work. I had to walk slowly and cough to try and cover the sound of the crinkling. Even still, some of the people were giving me strange looks and I saw some of the female clerks whispering amongst each other. Were they talking about me? I couldn’t be sure.

It didn’t help things that I smelled like baby powder. It was a distinct smell that would be hard to explain away, should someone ask me.

It also frustrated me that Denise seemed to be distant with me again; acting cool and treating me in a perfunctory fashion. She wouldn’t return my smiles at her and what little conversation we had, was strictly professional.
I sent her several text messages but she didn’t reply to any of them.

About midmorning, I signed for a small package from FedEx which was addressed to her. She seemed very pleased to get it but then when I tried to stick around, she dismissed me curtly.

It hurt my feelings that she could be so warm and intimate with me at her house but cold and indifferent during the time we spent at work together. I mean–I didn’t expect her to exactly throw her arms around me when I walked into the room, but why was she treating me like a total stranger?

In addition, even though I had done everything I could to limit my liquid intake today, I was still fighting a strong urge to pee all morning. I was crossing my legs and fidgeting, practically dancing at my station as I dealt with bank customers.

Lunch was coming up and I had been told that the management was taking everyone out, on account of the new merger. I was determined to ask Denise to unlock my plastic pants at that point and relieve some of the built up pressure.

I was only an hour away from lunchtime when it all became too much to bear. All the dancing in place wasn’t going to make my urge go away and I reasoned if I just let a little out, I could hold the rest back.
And maybe Denise wouldn’t even detect such a small amount of dampness anyway?

Finally there was a break in the line to the tellers and I relaxed ever so slightly. I felt a stronger than expected surge suddenly empty into my diapers and I tried to cut off the flow. I stifled a sob as I realized the futility of holding back the dam. My little penis flexed weakly inside my chastity device and more and more hot pee flooded my diapers as wave after wave saturated the soft cotton cloth surrounding me. In no time at all–I felt like I was swimming in pee!

My mouth was hanging open and I looked over to see Ashley, my co-worker staring at me.
“Are you okay?” she asked pointedly.
I blushed furiously and looked down at my checks.
“Y-yes, I’m–I mean, uh, I was just daydreaming,” I stammered foolishly.

Ashley’s eyebrows went up as if to say ‘whatever‘ and she shook her head.
Did she realize I had just soaked my diapers?
My face wouldn’t stop burning as I felt the pee seeping between my legs, absorbing into the seat. I felt so babyish! I tried to stand with my feet apart but I could feel the warm wetness already upon my buns. For the moment, it appeared that I was the only one that was aware of my catastrophe, but I couldn’t stop blushing–I was so humiliated!

For the next half hour, it was impossible to concentrate on my work, and I kept making mistakes with customers.

“Mr. Jones!”

I heard my name being called from across the room behind me and I froze in position. Turning my head around carefully, I saw Denise standing at her doorway, a serious look on her pretty face. She was wearing a silky white blouse that clung deliciously to her big breasts, a short, snug grey skirt and her stiletto heels.
She looked like a goddess of justice, about to pass sentence on a weak mortal.

“Come to my office,” she ordered me in a demanding voice.
Out of the corner of my eye, I saw Ashley smirk as I walked slowly away and into my supervisor’s office.
Moving past Denise, I was filled with trepidation, and she closed the door behind me.

I saw my underwear laying on the top of her desk and she looked down on me, her hands on her curvy hips.
“Did Mommy’s little baby wet his diapers, or is he ready for his big boy underwear again?”
I felt so weak and inferior before her, unable to look up into her eyes. It was like I was five years old, all over again, being scolded by my mommy.

I shuffled my feet and stared at the floor, knowing she would discover my soggy diapers, all too soon.

Without waiting, she reached down the front of my pants, slid her slim fingers inside my diapers and a smile crossed her face.
“Well…looks like someone isn’t quite ready to graduate to his big boy underpants, is he?”
I blushed hotly and stared at the ground.
“What do you say, Chrissey?” she pushed me.
“I-I couldn’t hold it anymore,” I whined.
“Mm-hm,” she nodded, “Just as I thought. Well, sissy boy–looks like you’ll just be wearing your wet diapers the rest of the day.”

“C-can’t I get a fresh change, please?” I whined pathetically.
“Nope, I didn’t bring a diaper bag with me–I didn’t realize what a big baby you were,” she countered emphatically.

With that, she spun me around and slapped my diapered bottom hard, essentially dismissing me. I walked out, thoroughly ashamed and returned to my counter, my plastic pants crinkling audibly.

Everyone was closing their drawers for lunch and I put my stuff away and locked up.

We all met at a restaurant across the street and the employees sat among three tables. I had never felt like I was a part of their crowd but on this occasion, the guys made room for me at their table.
I sat down with a humiliating squish and I prayed no one would detect the smell of pee coming from my general vicinity. It was hard to concentrate, with the saturated cloth clinging to my bottom and hugging my tiny, caged genitals. I prayed it wouldn’t leak out past my plastic pants and reveal my secret to everyone around me when I stood up.

The guys were having an animated discussion amongst themselves until Denise entered the restaurant. As always, she was the center of attention whenever she entered a room. And as always, she ignored them as she sauntered over to the table where the women were seated. All eyes followed her, admiring her sexy, voluptuous body in her short pencil skirt and revealing white blouse.
Her table was close enough that I could hear snatches of conversation between her and her friends but not much else.

A few moments later, Jordan showed up, and Denise’s face lit up in a display of obvious joy.

Jordan was a girl that had been working at the bank since before I started there. She was in her mid-twenties, slim, with long straight blonde hair. With her toned physique, beautiful face, and what many of the guys said were fake boobs, she attracted almost as much attention as Denise. The difference was she wasn’t as stand off-ish as the latter and therefore, didn’t have a reputation as an “ice queen”.
Nevertheless, like all hot women, she barely knew I existed.

Jordan was perhaps the only true friend that Denise had at the bank, probably because from a social status perspective, they were two of a type, and the fact is, beautiful women tend to congregate with each other. I had known that simple fact since my high school years.

But the look on Denise’s face made me start to wonder if there was more to their relationship than they let on.
She stood up from her seat to hug Jordan, and I couldn’t help but suspect there was more affection being shown than one would think for just two friends greeting each other. I felt a strong pang of jealousy ripple through me that someone else had Denise’s attention and it gnawed at me all through lunch. They were chatting busily between each other and occasionally, I would see Denise’s hand linger on Jordan’s toned thigh.
Was there something going on between them? Was Denise attracted to Jordan sexually?
I couldn’t stand the thought that I wasn’t the only sexual interest in her life.

Lunch finally ended and we were the last group to get back to the bank. When I walked up to my counter, I saw our manager, Mr. Jenkins, at my station and he was facing my computer screen, although because he was blocking my view, I couldn’t see what it was he was looking at.
And as I got closer, I could see a very angry look on his face. Ashley was trying to act busy, but clearly, she wanted to see what was about to happen.

He saw me out of the corner of his eye and he turned to face me.

“Mr. Jones? Do you have an explanation for this?” he snarled at me.

Looking at the computer screen, I saw a web page for something called SpankedSissies.com and I froze in place.
I blushed a deep shade of red and began stammering nervously. A trickle of pee escaped into my already very wet diapers.

Chapter Six

I stood before Mr Jenkins, shocked and humiliated with his unexpected discovery. I had no idea how the website had been put on my screen or who was responsible.

“N-no, Sir, I don’t know who put that there.”
“This is–your station–is it not?” he demanded as his white eyebrows furrowed into a menacing V.
“Y-yes sir, b-but I’m just coming back from lunch–I don’t know who put that on my screen,” I tried to explain.
“I’ve been running this establishment for over thirty years…” he lectured me, “and our computers are not for the purposes of viewing porn–Do I make myself clear??”

“Y-yes, Sir,” I quaked.
“This will serve as a verbal warning to you, young man. If it happens again, it will be a write-up in your employee record,” he told me sternly, “Maybe you think the rules don’t apply to you around here but let me assure you that they do.”

I was so scared, I felt another warm stream of pee suddenly flow into my already soggy diapers. My face, burning red with shame, blushed even deeper.

I really needed this job. It was my first one out of high school and I could barely make ends meet as it was. One more late payment on my apartment and I would be out in the streets.

“Y-yes, Sir,” I repeated.
Ashley was staring at me and it was obvious she felt no sympathy for me at all.
Mr. Jenkins stormed off, muttering something about ‘sissies’ under his breath and I quickly changed the screen back to the default browser.

Glancing back at Ashley, I saw her shaking her head in disapproval before returning to her work.
I was at a loss to explain how the embarrassing webpage had been pulled up on my screen–obviously someone had to have put it on there as a prank.
But I was SO humiliated! It was bad enough to be treated like a sissy by Denise, but to advertise it like this was mortifying. I knew Ashley would be telling all her friends at her first opportunity. Now, everyone at the bank would be thinking I harbored secret, perverse fantasies of being a sissy and getting spanked. Nothing could have been farther from the truth!

The rest of the day was awkward, uncomfortable, and humiliating for me.
Finally, as I was walking out to my car, I got a text message from Denise. It said;

If you want to get changed out of your wet pampers, come over to my place.

That was first and foremost on my mind so I headed straight over.

After my degrading meeting with her in her office, I was afraid she would take back her promise to unlock my poor caged penis, but on the other hand, maybe she would have mercy on me after all that had happened to me today.

When I arrived, Denise ushered me in, smiling at me warmly. She was wearing a tight fitted top, and as low cut as it was, she had still unbuttoned the top two buttons. My eyes just about popped out of their sockets as I gazed lustfully at her sexy, yawning cleavage.

She guided me to her room and began undressing me, removing all my clothes except for the sodden diapers. Positioning me on the changing pad, she pulled down my clinging plastic pants and unpinned the soaking wet cloth.
“My my,” she commented, “My little baby really wet herself today, didn’t she?”
I nodded my head, even as I blushed at her remark.
“Don’t you worry, baby, I’ve got some new, thicker diapers that came in the mail today. They have nice, thick soaker pads down the center for heavy wetters like you.”
I wanted to argue with her contention but I didn’t want to do anything that was going to cause her to change her mind about my chastity. I had to get it removed today.

After she put the wet diapers aside, she produced a razor and some shaving cream.
“You hardly have any pubic hair as it is, but I want my baby to be girly smooth down there,” she said as she removed the few strands of light hair around my package.
When that was completed, she took the necklace from around her neck and unlocked the chastity device.
Never had I been so happy to see my penis again! After removing all the pieces of the chastity device, my little stub was finally free.
I immediately reached down to rub it but Denise slapped my hand away.

“No sissy boy, I’ll take care of that for you,” she assured me.
Putting some baby oil on her hands, she reached down and began gently massaging my tiny member.
I sighed and relaxed, or as much as one can relax when gazing at a woman as pretty as Denise, with the most spectacular boobs on the planet.
As I began breathing deeply, she paused long enough to retrieve the pacifier and she pushed it between my lips.
“There you are baby, you should have something filling your mouth at all times.”

I didn’t mind at all. I was willing to play baby games with her as long as I got to cum, and this one promised to be an earth shattering climax.

As she continued to fondle my diminutive penis, she began a childish banter with me in her sultry, sexy voice.
“Does mommy’s little baby like this? Hmm? Does my little sugarplum want mommy to keep rubbing her tiny baby pee-pee?”
I blushed even as I moaned and looked into her eyes, my lust and desire making my breathing labored.

“Mommy’s got a little present for her baby tonight…would you like to see it?” she asked me playfully.
I nodded my head deliriously, curious as to what she might have gotten me.
Taking my head in her hand, she guided it down and pushed my nose deep into her cleavage, momentarily blocking my view. I felt her slipping something around my scrotum, and pulling my balls and penis through.

Suddenly very concerned, I pulled my head back and looked down. A singular, solid pink plastic ring was behind my balls and Denise was holding the other half of a new pink chastity device in her hand.

“This one is a little different from the one you had on before,” she said as she held it up for my inspection, “See the spikes on the inside of the tube? Those will ensure my little baby stays nice and soft, all of the time.”

My mouth fell open and the pacifier dropped onto the bed.

“I-I’m n-not wearing that,” I gasped in horror.
“Oh yes you are, Chrissey–this is your new chastity device and your new best friend.
“You see, erections are for real men, and these spikes will make sure a sissy like you can never have one.”

“B-but, you-you said you were going to unlock me today!” I croaked.
“And I did,” she smiled at me, “And now you’re going to be locked back up.”

“No! I’ve had enough of this!” I shouted angrily, “I’ve gone along with your weird games but this is going too far.”
Denise dropped the chastity tube and quickly grasped my ankles together, abruptly swinging them upwards over my head and forcing me to put my hands out to steady myself. With her free hand, she snatched up the paddle and brought it down hard on my exposed bottom.

SMACKKKK!!!

I howled in pain and tried to wrest my legs free but she held me too strongly.

SMACKKKK!!! SMACKKKK!!!

I cried out at the top of my lungs as she continued to swat my damp, bare cheeks mercilessly.

SMACKKKK!!! SMACKKKK!!!

Her paddle scalded me with blistering slaps and I immediately burst into tears.
Each fiery swat from her paddle made her tremendous breasts shake and jiggle within her top. Any other time, I would have found the display highly erotic but right now, all I could think about was the stinging bite of the wooden instrument of punishment in her hand.

My vision became blurred as the tears filled my eyes and streamed down my face. I bunched my fists and shook them as I bawled like a baby. At this moment, I hated Denise completely. I hated her for her strength, her unflinching, domineering resolve, her smug, condescending treatment, and lastly, for her incredible beauty.
I wailed like a helpless toddler as she harshly paddled me with abandon.

Occasionally, Denise would pull my legs even higher so she could swat my seat more effectively. I couldn’t believe how strong she was! Just when I thought she was done, she would devote her attention to the sides of my cheeks, giving them slap after biting, vengeful slap.

When she was finally finished and she let my legs down, I was gasping for breath and crying hard. I couldn’t see the expression on her face clearly through the tears filling my eyes.

“Now–Is Mommy’s little baby ready for her chastity device?” she asked me sternly.

I nodded my head vigorously as I tried to wipe my wet face with my arm.
Denise dabbed a little baby oil on my shriveled penis, rubbing it softly until she produced a little rise and then she popped it into the short pink tube. Pushing it up against the base ring, she inserted a long key and locked it shut.

“There, that’s much better,” she said satisfied, “And now, it’s time I put my baby into her new bedwetter diapers.”

Chapter Seven
The next couple of weeks began to develop into a pattern of sorts.

I was spending the night more and more over at Denise’s house and she was making sure I was diapered for bed on a regular basis. I didn’t always spend weekend days with her but when I did, she was dressing me up in ever more humiliating ways, which would always include as part of my outfit, thick, babyish diapers and plastic pants. I don’t know where she found them, but the tops she would put me in were short and frilly, often in pastel colors with ruffled or lacy puff sleeves. They usually had infantile designs on them which made me look even more like an incontinent toddler.

I didn’t like it, any more than I liked having to suck her big, thick cock every morning and evening. It was a humiliating, degrading job, made more so, by her continuous litany of condescending comments and taunts. And it wasn’t made any easier by the fact I could barely stuff it into my mouth or the struggles to swallow her copious loads of warm, creamy semen, but she gave me no choice in the matter.

I had never had a lot of willpower, and it seemed this relationship was only emphasizing that fact. I sometimes mused that she had picked me for precisely that reason, but to be honest, I didn’t want to dwell on it too much. The important thing was, the guys at my bank thought I was cool because I was dating the most amazing woman in town, so that was reason enough to put up with Denise’s peculiar and eccentric preferences. I had never once been the object of anyone’s envy, so this was an entirely new sensation for me.

The only problem was, I hadn’t cum in two weeks and I was frantic for some kind of satisfaction. This was made worse by the fact that Denise made a point of dressing provocatively at home which had a predictable effect on my poor, caged little penis. One word from her, a button undone, or a soft caress from her hand caused my long deprived penis to grow in it’s short tube until the soft, tender head pushed into the hard, unyielding spikes inside the device. No amount of fidgeting or wrestling with my chastised package would alleviate the agony. The spikes were as cruel as they were unforgiving and I couldn’t make the pain go away unless I concentrated on mundane things like bills or taxes. But that technique only worked until the next time Denise bent down in front of me, and then the vicious cycle began all over again.

I think she took an evil delight in tempting me with her sexuality, just to watch me cringe and writhe from the sharp bite of the spikes. When I asked her when she was going to release me, she always answered in vague terms like, “soon”, or “you’ll just have to be patient”.
But the enforced chastity had the effect of making me so horny I was willing to do anything she asked, and no indignity was too much to bear in hopes of getting released from my penis prison.

So far, I had only been put over her lap for a spanking on one occasion since the dreaded paddling the night she introduced me to the new chastity device. Still, those experiences were enough to make me never question her absolute authority over me, and I was extremely hesitant to push her any more than I dared on a topic of disagreement.

There was one weekend that will stand out in my memory for it’s singular level of humiliation at her hands.

The morning had started out normally (for a visit to Denise’s house anyway), with her changing me out of my wet nighttime diapers and into an outfit she had chosen for me for the day.
In this case, it was a short white fleece top with a teddy bear design on the chest and short, puffy sleeves decorated in a pink nursery print. The hem, also very short, was lined with soft pink ruffles and barely extended past my navel. I wore pink ruffled anklets which matched the ruffles around the leg and waist bands of the white nursery print plastic panties covering my fat, bulging diapers.

She had put me on the floor of her living room with a Disney Princess coloring book and given me instructions to fill out several pages using some crayons. I guess I must have gotten distracted because I never heard the vehicle pulling up in her front driveway.

Before I knew it, Denise had walked over to the front door and opened it, allowing two workmen to stroll right into the house without any sort of warning. Looking up from my drawing, I gasped with shock as they walked in and stared down on me, the amusement plain on their gruff, unshaven faces.

Denise was all smiles as she came over, acting as sultry and charming as only she could, saying, “Can I get you boys something to drink?”

“Yeah, a beer would be great,” the bigger of the two grunted as he stared down on me in disdain and disbelief.

I blushed a hot shade of red, as I looked into their smirking faces, only barely managing to stem the flow of panic-induced pee into my thick, embarrassing diapers. It was obvious that they had been forewarned of my appearance and equally obvious that Denise had planned this encounter specifically to humiliate me.

“Oh, don’t mind Chrissey here, he just has a hard time keeping his pants dry so I had to put him back into diapers.”

The burning in my cheeks spread down to my neck and chest and I gulped in abject shame. She made it sound like I had no more control than a little boy still being potty-trained!

Denise sauntered out of the room, while both men’s eyes followed her every move, greedily drinking in her sexy curves. Today, she had chosen a short, bouncy skirt that barely covered her trim derrière and her strappy high heels lent her a sexy, impossible-to-ignore gait.

Once around the corner, the men returned to looking down at me and I squirmed with anxiety and embarrassment. I felt like such a total sissy, my big, thick diapers, plain to see with their shiny plastic pants and babyish print.

“Dude, I didn’t see a ring on her hand,” the big one told his friend, “I think I’m gonna make a move on her before we go.”

I felt successive waves of humiliation, resentment, and jealously wash over me as it became obvious that they didn’t consider me in the least, a contender or competition for their lustful ambitions with Denise. They hadn’t even bothered to ask–one look at my sissy baby outfit and they assumed a woman like her would have nothing to do with a prissy boy like me.

And yet, I was afraid to open my mouth and dispel their conclusion. They would only laugh and ridicule me with greater contempt.

Denise returned shortly with two cold beers and she handed them over with a ravishing smile on her pretty face.
“Let me know if there’s anything else I can get you boys,” she said in her most flirtatious voice.
The big one stood up a little straighter and grinned back at her lecherously.

Well, since you asked…here is my card–that number at the bottom is my personal cell phone. You feel free to call me anytime–anytime at all, you need a man’s help in this house.”
I knew the tone of his comment was a direct reference to my lack of the same and I bunched my fists in anger.

Denise giggled and led them back to the end of the hallway and into a spare room while I was left to pout on the floor in frustration.

To add insult to the situation, it was only then that I realized my diapers were wet–it had happened without me even realizing it!
I blushed anew at my childish lack of control, but I blamed Denise for being the ultimate architect of my humiliation. This would never have happened if I had hadn’t come over to her house in the first place.

When Denise came back into the living room, I angrily threw the coloring book at the wall and began shouting at her, accusing her of arranging this whole situation to deliberately humiliate me.

My tantrum brought about what was becoming a predictable response.

Inside of a minute, I found myself bent over her lap, diapers unpinned and pushed back, my plastic panties tangled around my ankles, as she soundly paddled me within easy earshot of the workers.

Through the tears filling my eyes, I could see their blurry forms as they came out to watch the weak, diapered sissy getting his soft, bare bottom spanked hard by the oh-so-hot woman that had employed them.

Chapter Eight
The line of bank customers finally began to grow shorter and I glanced up at the clock on the far wall, only to see I still had three hours left to go.
I sighed heavily and looked down at the pile of work next to my computer.
I was bored as hell and wanted to go home, not take checks and dispense cash to people who didn’t care if I lived or died.

Across the main room, I could see Denise talking with Mr. Jenkins, our manager. One couldn’t help but notice that her blouse was super snug as always, and I could clearly make out the outlines of her sexy white push-up bra underneath.
I sighed with admiration.

Just last night, she had allowed me to nurse from her big nipples for a half hour before bed. She had even mashed my face between her massive breasts, practically suffocating me in her glorious, feminine embrace.
My pleasant memory was interrupted by the biting sensation in my groin as my little penis grew with arousal and began pressing urgently against the sharp spikes in the tube of my chastity device.

I winced painfully and shifted in place, trying in vain to alleviate the torture to my tender head.
I had to stop looking at her–everything about her screamed sex and that was the one thing I couldn’t think about.

Ashley came over to drop off some checks and she looked at me strangely.

“Why does it always smell like baby powder over here?” she said accusingly.

“I dunno,” I replied lamely as I blushed with shame.

I had pleaded with Denise to use less of the fragrant smelling powder when she chose to diaper me in the mornings but she always ignored me or worse, put even more on. I always smelled like a baby’s nursery when I arrived at work and people were starting to get suspicious. I had bought some larger pants to wear but even those barely concealed the fact that I was wearing diapers and plastic pants underneath.

“Here,” she said thrusting a stack of checks at me, “Sort these and Heather’s before you go today.”
“Why can’t she sort her own checks?” I complained.
“Because I’m giving you that job,” she quipped.
Ever since Ashley had been promoted to lead teller last week, she had been lording her authority over me at every opportunity.

I bit back the remark on my lips and accepted the additional workload in sullen silence. I also resented that it seemed that the women here were getting all the lucky breaks and being given positions that I should have been considered for. It wasn’t fair, and I hated being ordered around all the time.

An hour later, I had to take some cash to the vault and I locked up my drawer before stepping away. I was required by our rules to notify Ashley but my ego prevented me from doing so and instead, I just walked away without saying anything.
Anyway, it was only for a few minutes and I figured the other tellers could handle the few people we had in line.

I went to the vault and sorted the cash, placing the notes in their appropriate sections.
Taking a moment to reach down into my diapers, I reflected that they weren’t too wet and I knew from past experience I wouldn’t have any difficulty getting through the last couple of hours of work.

My feelings of good nature were rudely shattered as I came back to see Ashley and Denise standing at my station, engaged in what sounded like a very serious discussion.

“Wha-what’s going on?” I asked nervously.

“Didn’t Mr. Jenkins tell you you weren’t allowed to look at porn on these computers?” Ashley said bluntly.
I gasped as I looked down at the screen between them. Splashed across the face of the monitor was a picture of a feminine looking guy bent over and being forcibly humped from behind by some dominant, leather clad woman. The website’s name was in big pink letters across the top which read PunishedSissies.com.
I blushed red and my mouth went dry.

“What do you have to say for yourself, Mr. Jones?” Denise said, her tone both accusing and overly formal with me.

“I-I didn’t put that there!” I cried, “Somebody else must have put it on my screen.”
The other tellers were starting to look at us and I felt a bead of sweat trickle down my temple.

“No one’s been at your station since you left it,” Ashley said pointedly, “which, by the way–you failed to inform me.
“This isn’t the first time, Denise.”

I felt the blood rushing to my head from indignant frustration.

“Is that true?” Denise asked.

While I knew I had nothing to do with the website on my computer, she did have me on the rule of notifying Ashley prior to leaving my station.

“Um…yes,” I muttered.

“I think we are going to need to finish this discussion in my office,” Denise said gravely.
My heart sank as the two of them turned and led the way, leaving me to face the stares of the rest of the staff who appeared anything but sympathetic.
It was customary during disciplinary situations to have a witness present, for reasons of liability. That way, the employee couldn’t claim later that something was or wasn’t said.

When we got to her office, Ashley closed the door behind me, her expression dead serious. Despite my innocence, I felt a shiver of fear go down my spine. This was all I needed.
Predictably, a stream of hot pee surged into my damp diapers before I could stop it.

“Have a seat,” Denise told me curtly, indicating with her pen, a chair in front.
I slumped into the chair as the other two took their places across the desk from me.

“Viewing porn on company computers is a serious breach of the rules,” Denise began dryly, “And you were warned about it by Mr. Jenkins himself, just two weeks ago.”

“–But that wasn’t me either!” I protested bitterly.
“Don’t make this worse for you than it already is,” she replied.

I couldn’t believe the woman who had let me nurse from her boobs only 14 hours previous was lecturing me and putting my job in jeopardy.

“Who else could have put it there?” Ashley countered, her certainty apparent.

“I don’t know, but it wasn’t me,” I complained, desperate now.
Denise dismissed me with a wave of her meticulously manicured hand.
“I’m afraid I have no choice but to document this and put it in your written record,” she informed me.

My spirits sank and my shoulders sagged with defeat.
Now my job was really on the line.

Who was setting me up? And why? I knew I wasn’t that popular, especially with the women at the bank, who viewed me with disdain or a mild contempt.
Was it Ashley? She was a logical choice, from a motive perspective. But somehow, I couldn’t imagine her bothering with something like that. I doubted she even knew about kinky fetishes like sissies and spanking–she seemed too vanilla for that.
Still, she was the only one close enough to have had access to my computer…

“I’ll need you to sign here,” Denise indicated on the form with her long nailed finger.

It seemed so surreal and ironic–and not in a good way, that the woman of my dreams was being instrumental in the destruction of my job here at the bank.

With angry silence, I snatched up the pen and scribbled my signature on the document.

“You are being given your final warning, Mr. Jones,” Denise told me, “if you are found with porn sites on your computer again, you will be terminated.”
My face flushed with hot shame and anger.
“But I didn’t do anything!” I whined.

“And I better not hear again that you are leaving your station without informing Ashley,” she added, pouring more salt on the wound, “Do you understand me?”

“Yes, Ma’am,” I answered, my head hung low.

“That is all. You are dismissed,” she said as she signed below mine and handed the pen to Ashley.
I got up and looked over only long enough to see a look of smug satisfaction on the latter’s face.

Even if my job wasn’t ruined, I knew that by this time tomorrow, my reputation would be, thanks to Ashley. Everyone would be certain I was a closet sissy that couldn’t even wait to get home to surf for the humiliating porn.
I felt tears threatening to erupt and I quickly made my exit, rushing to the bathroom to hide my face from the others.

There had to be some solution to stop my downward spiral, but what?
Chapter Nine
For the next several days, I felt strong feelings of anger and resentment toward Denise and I went out of my way to avoid her, for what I saw was her role in betraying me at work.
And yet, she seemed oblivious to my change of attitude. She kept sending me crude, dirty messages via text, like ‘I want to cum in your mouth’, and ‘I miss your lips around my cock’.
In my anger, I simply ignored them and went about my day.

To make matters worse, I was wetting the bed at home almost every night. I didn’t want to wear diapers, because they were humiliating and reminded me of Denise, but my sheets were getting stained and my bedroom was starting to smell of stale pee. I couldn’t understand why I was having such difficulty controlling my wetting and my shameful pre-teen years came back with a vengeance to haunt me.

At work, I felt conflicted and confused. The first few days after my write-up, I was too angry to think about Denise but at the same time, it was also impossible to ignore her. She’d come over to my station, the key to my chastity device hanging on a small chain that dangled above the deep line of her cleavage, which, because I was so short, was nearly eye level for me.
And like every other male, I couldn’t resist gazing lustfully at her big, proud breasts, barely contained within her silky white blouse. It was absolute torture!
From every angle, she was magnificent to behold.

And beyond my unrequited arousal, I felt, despite all my misgivings, that I was starting to fall in love with her. I knew my lack of previous relationships with women was a big weakness, because now that I had being shown some attention by someone as desirable as Denise, I was totally helpless to resist her.
Every time she winked at me or smiled when no one was looking, my heart skipped a beat and I was wracked by an intense longing for her.

I remained conflicted and in doubt until fate conspired to force my hand.

I was working at my station during the midmorning rush when, totally unexpectedly, I suddenly felt the front of my pants getting warm and wet. I gasped in horror as I looked down to see a big wet spot forming in my slacks. I was able to stop the flow, but to my dismay, the damage was done. There was no way I was going to be able to hide the accident–I was going to have to leave and go home to take care of it. And I knew the only person that was able to approve something like that, was Denise.

For the next ten minutes, I stood as close to the counter as I could to hide the evidence, cursing my lack of control and hating the fact that I was going to have to go crawling back to Denise and beg to be allowed to leave in the middle of my shift. Not only that, it was going to be tricky just to cover the distance to her office without anyone seeing the dark spot on the front of my pants.

Finally, marshaling my courage, I grabbed some papers, putting them in front of my groin, and asked Ashley if I could be excused to see Denise about a matter of importance. Did I mention that I hated sucking up to her? Fortunately, she was busy with another customer, and she dismissed me curtly with hardly a glance.

I strode briskly over to Denise’s office, relieved to see that her door was open and she wasn’t with someone. I ducked inside and closed the door behind me.

“Denise–I had an accident!” I blurted out in a panic.

She looked up from her work and her gaze fell upon the dark patch in the front of my pants. Immediately, she burst out laughing, showing her perfect white teeth and I blushed hot red with shame.

“Aww, did Mommy’s little baby wet his pants?” she asked in a syrupy voice reserved for children.
I fumed and shuffled my feet, unable to reply with anything dignified.

“I don’t know what happened–I just…I mean…this has never happened before,” I tried to explain.
Denise looked unconvinced and she smiled back at me.

“This is what happens when little sissies like you don’t wear their diapers like they’re supposed to,” she told me.
I bite my lip and stared at the floor as my cheeks burned with humiliation. The last time this had happened, was when I was in the third grade, and I still cringed with shame when I recalled Ms. Taylor’s condescending treatment of me.

“Um, do you think I could, um, leave to change my pants at home?” I asked tentatively.

Denise crossed her slim arms over her magnificent chest in a sign of doubt.
“I don’t know Chrissey…who will fill in for you while you’re gone? I can’t give special treatment to just anyone–the others might think I’m showing favoritism towards you.”

“I’ll only be 20 minutes,” I pleaded desperately, “and then I’ll be right back.”

Denise stood up from behind her desk and she slowly came around to stand before me. For some reason, the crisp click of her high heels on the hardwood floor seemed particularly loud in the quiet room.
I looked up into her pretty blue eyes, aware that I was totally at her mercy. I felt like I were standing before Ms. Taylor again, asking to be excused from class.
But there was no way I could go back out and work with my pants so obviously wet.

“Well…” she began, appearing to consider an option, “I think there might be a way we can come to an understanding…”

She smiled down on me coyly, as she reached down and began snaking her lacy panties down her firm, silky thighs.

“On your knees, Chrissey, I think we can make some sort of arrangement.”
I felt her slim hand on my shoulder pushing me down to that all-too-familiar position of subservience and I looked around me in a panic.

“B-but, shouldn’t we lo-lock the door or something?”

“I’ve always wanted you to suck my cock in my office,” she replied with a chuckle as she began stroking herself, “and the excitement of possibly getting caught only adds spice to the situation.”

“I don’t think–I mean–” I stammered nervously.
“Better work quickly, Chrissey,” she smirked as she looked down at me, her semi-hard cock in her hand, “before someone comes in for something.”

In a frantic panic, I wrapped my lips around her massive tool, swirling my tongue over her warm, thick head as visions of one of our co-workers discovering us swam through my head. My cheeks flushed with shame as I imagined the look on their faces, were they to find me on my knees, slobbering on a big thick cock in my mouth. I would never live that down in a million years! I’d have to move out of town if that were to happen!

Like a demon possessed, I went to work on her cock, using my hands to stroke her big, meaty shaft while my mouth sucked and slurped on the fat head. Denise moaned deeply and I knew I was having an effect on her. If only I could get her to cum quickly, I might avoid the catastrophe that she had so carelessly risked for us.

My head was bobbing up and down, my saliva working overtime as my heart beat wildly within my chest. At any moment, someone could come barging in!

Denise had moved her hands down to guide my head, and she slowed my frantic pace to a rhythm of her own choosing. I was impatient to get the job done, but on the other hand, experience dictated that she would cum sooner if she, rather than I, controlled the way things went.

I heard voices outside the door and I nearly choked in panic. Was someone about to come in??
My cheeks blazed with flaming humiliation.

Denise heard it too, and she grasped my head firmly.

“Keep going cocksucker…that’s my little sissy…I’m going to make sure you get a big mouthful of cum…show me what a good little cocksucker you are…”

Her humiliating remarks made me blush with shame even deeper but I had little choice but to finish the job at hand.

Finally, I felt the familiar sensation of her mighty cock swelling in my mouth and she soon erupted with a barely muffled moan, choking it back so as not to let everyone outside know what was happening. She filled my mouth with warm, creamy semen which I gulped down, only to be dwarfed with a second, even bigger load. That too, I swallowed but she pulled her cock out and proceeded to spray my face with the last of her milky ejaculation.

Reflexively, I moved my hands up to wipe it off but she pushed my hands away, and using her still hard cock head, she smeared her cum across my lips and face.
“Lick that up, sissy boy,” she told me breathlessly.
Obediently, I did as I was told and quickly rose to my feet, extremely humiliated, yet relieved we had gotten away without getting caught.

“Okay, I think we can allow you to leave for a quick break to take care of your pants,” she said with a superior wink.

My cheeks still burning, I hastily cleaned my face up before heading out the door.

Chapter Ten
The next couple of days, I managed to keep from peeing my pants at work, although to my frustration, I was still wetting the bed at home every night. Being somewhat stubborn by nature, I refused to admit I had a problem and I simply ignored the growing smell of stale pee that greeted me every time I walked into the door of my apartment.

At work, my reputation, which at one point, had risen me to the enviable status of a rock star, had now plummeted to below what it had been before I started going out with Denise. Whereas before, I had just been considered a geeky loner, now I was considered a diaper dependent sissy with a fetish for bizarre porn.

What few friends I had acquired now shunned me, and all the girls looked at me like I was some sort of freak.

I was still going over to Denise’s house about three times a week but she never explained what the builders had been doing there, what they were working on, or the many packages that I saw arriving in the mail when I came over. The room they had been in remained locked whenever I was around and when I asked about it, Denise merely shrugged and replied with something vague, like “it’s storage”.

I was working at my teller station, anxious for the hours to pass so I could flee my humiliating work conditions when unexpectedly, I received a short and simple text message from Denise;

How would Mommy’s little baby like to cum tonight?

My heart skipped a beat and I snatched up my phone, punching the letters so frantically, I had to re-type it three times. After telling her of my enthusiastic agreement, she instructed me to show up at her place at 8.

For the rest of the afternoon, I willingly endured the pain of the spikes in my chastity device whenever Denise came by my station teasing me with her fabulous body. I reasoned that soon enough, my little penis would be free and I would finally, at last, get the relief I needed so badly. In the back of my mind, I hoped that Denise didn’t have some trick up her sleeve but I could only hope for the best.

That night, I showed up at her place, dressed in my best clothes, a suit jacket, pressed slacks and crisp collared shirt. After giving me a long and affectionate kiss, she led me through the door and took me to her bedroom.

“Take off all of your clothes and fold them up neatly,” she instructed me.

I was a little surprised, hoping that after having endured everything I had, that I could assume more of a conventional role with her tonight, but then, anything that got that accursed device off me sooner was fine by me.
In moments, I stood before her nude from head to toe, except for the emasculating pink chastity device securely locked around my genitals.

With great ceremony, Denise removed the small silver necklace she regularly wore and brought the key over to where I was waiting. I was giddy with anticipation as she bent down and undid the small titanium lock securing the device.

I exhaled with relief as she removed the spiked tube and worked the cuff ring out from around my sack. Looking down, I saw that my shriveled penis had numerous red indentations from where my head would repeatedly push up against the spikes.
Taking my tiny member between her fingers, she pinched it somewhat hard and giggled aloud.

“Do you ever wonder if the girls at the bank know just how small you are?” she asked with amusement.
I shifted my feet nervously, wondering in the back of my mind if she was subtly implying that she had already told them. I blushed crimson, the very notion that Denise would share such a humiliating and private detail of my life with them.

“You-you didn’t tell them, did you?” I bleated.

Denise giggled, but didn’t reply as she led me over to the bed and sat me on a waiting stack of soft but very thick diapers.
“It’s time I got my little baby dressed for this evening,” she said with a devastating smile that washed over me like a tidal wave, “I have a few items that came in the mail I’ve been just dying to dress you in.”

This wasn’t really what I had in mind but as always when I was in her presence, I was helpless to deny her anything.

Taking some baby oil, she began slowly massaging my little member, which quickly responded to her ministrations by becoming stiff and erect. It was embarrassing to see just how small it was, even throbbing and hard, and her running commentary only served to dampen my arousal.

“Look at this tiny little baby stick,” she giggled, “Its just exactly like a little toddler’s… It’s no wonder you’re still a virgin…Did your girlfriends laugh at you when you pulled your pants down?”

I tried to fight the intense blushing of my cheeks as I listened to her humiliating comments. And yet, at the same time, her soft, steady caress of my pee-pee kept it rock hard and stiff. I was at once, extremely mortified and aroused all at the same time!
Dipping her middle finger into a nearby jar of Vaseline, she slowly pushed it up inside my anus, making me squeal like a little girl with surprise.

“Ever had a man take you here?” she asked with a knowing smirk as she plunged it in and swirled it around.

“No!” I replied hotly, angry and humiliated that she would imply such a thing.

“Hmm, well, we’ll have to see about that,” she said as she pulled her finger out. I fumed in silence and looked away as she wiped her hands on a baby wipe.
Taking the container of baby powder, she lifted me up by my ankles and powdered my bottom generously before lowering my legs and getting the front.
“I’m going to let my little baby girl cum in her diapers tonight,” she said with a playful wink, “which is entirely appropriate, given what a big sissy you are, don’t you think?”

It was so humiliating to be treated by her like this, but I didn’t want to give away my one good chance for relief by saying something that would anger her. I just had to do my best and go along with it, and besides, no one else was ever going to find out about how I had achieved my orgasm.
I nodded my head in shameful silence, wishing I had the backbone to stand up to her bossy personality.

Pulling the big, soft fluffy diaper up between my legs, she pinned it securely on either side of my hips.
“That’s mommy’s little baby,” she praised me, “Such a good little baby girl you are.”
My cheeks reddened all over again as she pulled out some nursery print, snap-on plastic pants, positioning them at my feet.

“Aren’t these cute?” she asked in her syrupy voice, “They’re perfect for when baby is taking his nap and mommy needs to check his diapers. I’m sure a chronic bedwetter like you can totally appreciate that feature.”

I whimpered weakly as she snuck them up my ankles and over my smooth, hairless thighs.
Even though this had come to be something of a ritual for us, it was still mortifying as an adult to have her treat me like a helpless, incontinent little infant.
I bit my lip with embarrassment as she fitted them up over the fat, bulky diapers, working her long nails around the waistband to make sure all the soft cotton cloth was contained inside.

“What a good little girl you are,” she said again as she beeped my nose and began putting some pink lacy anklets over my feet.

“Look what came in the mail for you today,” she exclaimed as she held forth a pair of white glossy Mary Janes with buckles, “These will go perfectly with the cute little Sunday school dress I’ve been waiting to put on you.”

I cringed and pouted fussily as she easily put the sissy style shoes on my feet and buckled them in place. I looked down at my babyish lower half, knowing my child-like penis was buried between layers of bunny soft cotton Birdseye.
Denise turned around and then brought over a pink gingham little girl’s dress, with a built in petticoat that flared out the very short hem.

“Isn’t this the cutest little thing you’ve ever seen?” she gushed proudly, “It’s like it was made just for you.”
I whined with protest as she forced my arms up and dropped the frilly confection down over my torso.
“It even smells wonderful,” she beamed down at me, “I got that baby powder scent from a company called Eternal Essence–it’s like the perfect perfume for diapered sissies like you.”

My cheeks flushed as they attained an even deeper shade of red. True to her word, the powerful scent of a baby’s nursery surrounded me and I squirmed in place with embarrassment.
As she zipped up the back, she slipped a small lock into the very top, snapping it shut.

“The seamstress was very thoughtful to have put a pair of eyes up here on the neckline so that it could be locked in place–that will make sure mommy’s little sissy doesn’t get any ideas about removing her dress until I say it’s time,” she said with another wink.

I bunched my fists in mute frustration, helpless to prevent her from dressing me up like a little baby girl.

“And last but not least,” she said grinning as she held up a pair of lacy pink panties before me, “this little ensemble wouldn’t be complete without the piece-de-resistance.”

I whimpered impotently as she held them in place for me and brought them slowly up my legs, teasing me again as she did so.

“If only Ashley could see you now,” she said with a chuckle, “Just think what she’d say!”

I felt the blood in my cheeks expand to my ears and chest as I imagined myself standing before my co-worker, dressed in all my little girly, babyish finery.
After easily slipping the stretchy panties over my fat, bulging diapers, Denise stood me up and led me over to the full length mirror against the far wall.

“Take a look at yourself,” she insisted with a big smile of satisfaction on her beautiful face, “Aren’t you the most precious little baby girl that ever lived!”
She stood behind me and reaching down, she squeezed the thick seat of my diapers making me squeal in my high pitched voice.

“This is the real you, Chrissey…not the boy that came over tonight masquerading as a man, but a diaper wetting sissy who belongs in baby dresses and lacy panties.
“We both know that’s where you belong.”

My blood felt hot on my face and chest and I bunched my fists in anger and frustration, petulantly stamping my foot on the ground.
“No!” I snapped, “I do not!”
Denise laughed but reached down and planted a big wet kiss on my cheek, leaving a red lipstick imprint.

“This is how you’ll be dressed whenever you’re at my house, so you better get used to it.”
Giggling with amusement, she turned me around and swatted my bottom, sending me back like an errant little child to a seat next to her bed.

“Okay Babykins, here’s your big chance,” she said as she took a seat opposite me, “You have three minutes to cum in your diapers before I pull them down and lock your little penis back up in your chastity device.”
I gasped and looked around the room, as if expecting some other solution to inexplicably present itself.

“Ju-just like this?” I stammered uncertainly.
“Mm-hm, just like that–just imagine you’re back at home and looking at sissy porn–do what comes natural,” she told me.
“Bu-but I can’t…not with you…you know…watching,” I whined.
“Better make it quick, Chrissey–the clock’s ticking,” she smirked as she gazed down at her watch.

With a gulp of despair, I spread my legs and reached down and began tentatively rubbing the front of my thick diapers over the plastic panties. Secretly, I had to admit that the fluffy soft cloth felt wonderful against my newly freed penis, but it was still tremendously humiliating to fondle myself in front of Denise, who was not only my girlfriend but also my boss at work.
As I began rubbing myself, powerful sensations of arousal filled my being and my breathing soon became labored.

“Oh wait!” Denise said as she stood up and came over to me.
Taking my pink lace panties, she yanked them down around my ankles.
“There. Now you look just like the little sissy masturbator that I always knew you were.”

My cheeks flushed with shame and I momentarily stopped playing myself.
“Better not stop now,” she warned me, “you’ve only got two minutes left.”
I gulped and renewed my efforts, rubbing the front of my plastic covered diapers with abandon. In no time, my heart was pounding in my chest and I was breathing heavily again. The soft, pillowy Birdseye material felt so incredibly wonderful against my little pencil, it was an entirely new sensation for me.

Denise giggled as she crossed her legs and sat back, enjoying the view of her diapered sissy baby, frantically masturbating like a horny adolescent school girl.

I looked down at the fat diapers I was rubbing, reveling in how deliciously erotic they felt, only to look up and receive the shock of my life.
Denise was sitting there, snapping pictures of me with her cell phone as she chuckled with glee!

“Stop that!” I cried as I rose to my feet and stormed over to her.

Denise tossed her long hair out of her face with a shake of her head while holding her cell phone out of arm’s reach from me.

“Is my baby saying she’s ready to be put back into her chastity device?” she asked.

I shook my fists with frustration, my little boner having shrunk back down from the fear of my being exposed with such incriminating pictures.

“Go ahead baby,” she taunted me, “You can sit back down and play with yourself for another minute or I can pull your diapers down and put your chastity device back on–it’s up to you.”

Her smug, superior smile made me burn with resentment–I hated being so completely helpless to her will. But on the other hand, I had been so close to cumming, I was desperate to finish the deal.
Sighing with defeat, I walked back over and sat down on the chair, my thick diapers forcing me to waddle.

“Go ahead sissy, show mommy how her little baby likes to play with herself.”
No sooner did I begin fondling my diapers again when she pulled her phone out and began taking more pictures of me. And once more, my weak will prevented me from doing anything to stop her. Instead, I rubbed myself furiously, hoping to achieve that elusive orgasm before my minute was up.

I blushed with utter shame as I imagined the images she was taking of me, my panties tangled around my ankles as I spread my legs and rubbed the front of my diapers. At that moment, nothing was more important to me in the world than spraying my creamy load into the soft, welcome embrace of my babyish underwear.

I was panting like a dog, my head swimming with erotic abandon. My orgasm was bubbling up, ready to explode gloriously in a shattering climax like I had never experienced in my life. My eyelids became heavy and I felt filled with euphoria–this would make all the humiliation I had suffered and endured worth it.

Suddenly, Denise’s voice cut through the air, abruptly derailing the freight train of my impending orgasm.

“Time’s up!” she announced, “Looks like my little sissy didn’t have to cum that bad after all.”

“NOOO!” I cried, “Please De-I mean, Mommy–please just give me thirty more seconds,” I begged her piteously.

She stood towering over me, her hands on her curvy hips as she looked down at me, an unsympathetic look on her pretty face.

“Chrissey, I gave you more than a fair chance, and you blew it,” she said firmly, “Now we’re going to do things my way.”

Chapter Eleven

Before I could respond, she grabbed a tuft of my hair and forcefully pushed me to my knees.

“Time to do what you do best,” she ordered me roughly.
I whimpered and protested as she yanked her panties down and pulled her skirt up to reveal a big, thick hard-on staring me in the face.

Without hesitation, she shoved the fat head of her cock deep into my mouth, practically choking me.

“Suck it, sissy,” she hissed.

My cheeks bulged as I struggled with her titanic member filling my mouth and it muffled the panicked, girlish squeal I made.
Adjusting quickly to breathing through my nose, I began moving my head up and down her meaty shaft, caressing the underside with my tongue.

The tip of her head had a bead of pre-cum on it, which served to awaken my saliva glands. In no time at all, I was bobbing up and down like a cheap whore, her massive piston slick and wet with my juices.

“Ohhh…that’s it…that’s my little cocksucker,” Denise moaned, “This is right where you belong…on your knees with a big cock in your mouth…”
She emphasized her point by grabbing my head and slamming her fat hard-on all the way into my throat, gagging me on purpose.

“MFGHHHHH!!!” I squealed, before she relaxed her grip and let me resume my rhythm.

“Okay sissy,” she said throatily, “Stand up, come on–stand up,” she ordered me.
Momentarily confused, my mouth was still in the shape of a big ‘O’ as she popped her big cock out of my mouth and helped me back to my feet. My chin and lips were wet with saliva and I could still taste her pre-cum coating my mouth. Leading me over to the bed, she turned me around and pushed me over it, none too gently.

“Stay right there,” she commanded as she yanked my plastic pants open with a flurry of snaps.

“Wha-what are you gonna do?” I quivered.

Without answering me, Denise unpinned my diapers and let the back fall down between my legs, although bent over as I was, my little penis was still pressed up against the thick, soft, cotton cloth in front.
With her high heeled legs, she forcefully kicked my feet apart and my bare bottom was exposed and ready for punishment.

“Please don’t spank me, Mommy!” I wailed pitifully, “I’ll do better next time, just give me another chance.”

“Don’t worry baby, you’re getting another chance, just not the kind you were hoping for.”
I watched in horror as she dipped her tremendous cock into the jar of Vaseline and then took up a position behind me. Shaking my head violently, I pleaded with her to reconsider as she flipped up the back of my dress and using her hands, spread my cheeks wide.

“Oh no–oh no Mommy!” I squealed.

She pushed a big dollop of Vaseline into my hole, followed by another.

“Your virgin days are over, Chrissey–I’m going to pop your cherry tonight,” she said with a wicked grin.

“NOO! No–please!” I wailed, “Please Mommy!”

I felt the fat, warm tip of her organ pressing urgently against my small sphincter and I pinched my cheeks shut in a desperate bid to prevent her entry.

“Noooo!” I cried.

Reaching over, Denise picked up the oval shaped paddle on her night stand and she brought it down hard, swatting the right side of my bare bottom harshly.

“OWWW!!” I howled.

Using my distraction as my bottom momentarily relaxed, she pushed with determination, hard against my hole and I felt her gigantic head push past and plunge deep inside me. My eyes went wide and I gasped again in shock. Gripping the bed sheets frantically in my hands, I sobbed with defeat.

Denise moved slower now, pushing her big monster deep up inside me, stretching my hole tightly like it had never been stretched in my life. It felt like she was shoving a baseball bat into my pouting rectum.

“OHHHHHH!!!!” I moaned.

“There…” she whispered breathlessly in my ear, “Mommy’s little baby is getting just what she needs.”

I struggled to try and get away but between being bent over the bed and having her weight upon me, I was completely helpless. I moaned weakly as she ground her giant cock against me, pushing it in as far as it would go until it bottomed out.

Looking up, I saw our reflection in the big mirror covering the opposite wall of her bedroom. I looked so weak and pathetic, whereas she looked powerful and strong, the very picture of feminine superiority. Here I was, wearing a little girl’s frilly Sunday dress, holding onto the bed sheets for dear life as Denise stood imperious and proud, a smug smile on her face as she slowly pumped my aching hole.

“You see who’s in charge in this relationship? Not you sissy boy–I am,” she said firmly.

She emphasized her point by smacking my stinging bottom cheek again with the paddle and making me cry out in pain.

“OOUCHH!!”

A tear trickled down my face and I groaned as I felt her plunge deep inside again.

“Your job is to take my cock–however and whenever I want you to.”

I let out a weak moan of defeat and acknowledgment. I couldn’t believe I was a 22 year-old virgin who’s first real sexual experience was being helplessly raped from behind.
I squirmed again with all my might but she slapped my bottom and forcefully rammed her phallus deep inside me again.

“UUUGHHH!” I sobbed.

“So if I snap my fingers at you at work, you better make haste to my office and get on your knees. You’ll be my little bitch and suck my cock whenever it suits me.”

My cheeks reddened as I pictured myself being at her beck and call, constantly at risk of being discovered I was a sissy cocksucker.

Grasping my hips, she began humping me purposefully, in and out, the long thrusts of her gargantuan shaft making me whimper and moan like a weak little school girl.
Looking up at our reflection in the mirror, I saw the disparity of power between us. I would never be her equal, in or out of the bedroom. She would always be the one calling the shots while I was forced to do her bidding. She held all the cards and I held…nothing.

“This is what happens to weak sissies like you, Chrissey–they get bent over and ass fucked like emasculated little boys. And you’ll take it because it’s the only sex you’ll ever get,” she explained in her bossy voice.
She slapped my right cheek again hard with the paddle.

I howled out and struggled against her but it was hopeless. As usual, Denise had complete control over the situation, like she did with everything in her life, and she was going to make sure I got what was coming to me.

Her paced changed and began to get more urgent as she dug her long nails into my bare hips and thrust her huge member harder and harder into me. I was moaning and crying, alternately slapping the bed mattress and gripping the sheets for comfort.

“Does baby Chrissey need his teddy bear?” she taunted me.
Her pretty face held a dark fire I’d never seen before–one of absolute power, like a lion that had cornered her prey and was about to lunge for the kill.

My poor hole was being stretched so wide from the battering ram of her cock and it ached like nobody’s business. And yet, somehow, I was getting a sensation of fulfillment like I’d never had before. My own little penis was rubbing against the soft cotton cloth beneath me and the weeks of deprivation meant the stimulation in my punished anus was translating to stimulation for my penis. I was deeply ashamed to admit I was getting turned on but I couldn’t help myself.

Denise pounded me relentlessly and I felt my own orgasm starting to become imminent too. I felt her big balls slapping my own as she fucked me hard and relentlessly. Looking up at her in the mirror, she looked so powerful and beautiful, a patina of fine sweat on her brow which was creased with concentration.

At some point, the aching in my hole became transformed into pleasure and my head was swimming deliriously as I felt myself teetering on the edge of my climax. I looked up to see Denise closing her eyes and I felt her big tool swell inside me.

Shrieking like a banshee, she plunged it all the way until it bottomed out, filling me with a warm, gooey enema. At the same time, I toppled over the edge myself, squirting my little load into the welcoming folds of my baby soft diapers.
As Denise spent herself, she collapsed on top of me, her fat, hard-on still buried inside me.

Both of us were breathing heavily, and she leaned into me, kissing me gently on my ear.

“Well Chrissey, you’re no longer a virgin,” she whispered with a chuckle, “And you have a nice tight, sissy ass that I’m going to enjoy taking on a regular basis.”

I blushed hotly and whimpered weakly in response.

Now that I had cum, I became acutely aware of her shaft stretching my hole to the limit and I mewled painfully. Sensing my discomfort, Denise pulled out and I let out a tremendous sigh of relief as her slippery tool slid out of me.

Turning me over, Denise lay down next to me, her finger reaching over to gently describe a line from my ear to my chin.
“How did my baby like her orgasm?” she asked me sweetly.

I blushed to think of how my orgasm had been achieved, not something I was ever going to be able to brag about. I also became aware or a warm river of semen oozing out of my hole, reminding me of my new status.
“It-it felt good,” I confessed ashamedly, my cheeks burning a hot shade of red.
It was true at least that I felt a strong sense of relief that I hadn’t had since I last masturbated some four weeks ago.

Pushing me over on my back, she knelt down and gave me the most sensuous kiss I’d ever experienced in my life. I sighed happily, my feelings of affection and love for her impossible to ignore.

Bending down, Denise gathered the pieces of my pink chastity device and began working the cuff ring over my genitals.

“Couldn’t we…you know…leave that off?” I asked timidly.

“I don’t think so, Chrissey,” she said firmly, “You’d be masturbating first thing tomorrow morning.”

I gritted my teeth with resignation as she fitted the tube onto my shriveled penis and mated the pins into the corresponding holes. Slipping the lock through the central pin, she clicked it shut and put the necklace with the key back around her neck.

“And now, it’s time to get my baby bedwetter dressed for beddie-bye.”
Chapter Twelve

Grabbing my car keys and closing the door of my apartment behind me, I was struck by the difference in the air outside. Or rather, how different it smelled from the pungent air inside my single room dwelling being affected by my thoroughly pee-soaked and stained mattress.
My wetting hadn’t abated and I was seriously thinking I would have to start wearing diapers full time for nights. I absolutely hated the idea that I had no control over something like that at the adult age of twenty-two but what was I to do?

I walked the far way around the building to my car, purposely avoiding my apartment manager’s room so as to avoid her seeing me. Once again, I was late on my rent, and I was running out of excuses.

Nevertheless, I was in good spirits. I had received a text message from Denise that morning that was still making me swoon with desire;

I can’t wait to have you nuzzling my cleavage again. ;o)

It was followed by two pink hearts.

I sighed with contentment. I think I was in love.
I knew Denise wasn’t perfect–she had her flaws just like anyone. But I reasoned that her good points more than made up for her down side. Yes, she had taken part in my write-up at work, and to be sure, our sexual relationship was anything but conventional. But no one else knew about that side of her and besides, where I was I ever going to find a perfect woman like her? It would never happened again as long as I lived.
She was so pretty, and sexy, and awesome in every way. And when she smiled at me my heart sang with joy. I could easily forget about the many humiliations she had made me suffer through, if only to get that sign of approval from her when we were alone.

I pulled into the parking lot at work and locked my car, bringing my small sack lunch along with me.
I was just turning the corner of the building when I received a rude shock that froze me in place like a statue.

There, against the wall, I saw Jordan and Denise, locked in a wildly passionate embrace with their mouths eagerly pressed against each other’s, French kissing amorously as if they were in a bedroom instead of a very public place.

I gasped and my mouth hung open as I stared at them in disbelief.

Jordan’s back was against the wall and Denise had her hands pinned against it, as if she was forcing herself on her beautiful blond friend. However, that seemed highly doubtful–Jordan’s hands soon began freely roaming over her boss’s sexy body, exploring her shapely ass and cupping her big, heavy breasts.

I staggered back and tried to grapple with the enormity of what I was seeing. Obviously, the relationship between the two of them was far more developed than I had ever imagined. And just as obviously, it put my own relationship with Denise in a whole new light.

My entire being was blazing with an all consuming fire of jealousy, competing with alternating emotions of anger and anxiety.

How could she do this to me? I wanted to burst into tears and it was only with great difficulty that I pulled myself together.
As I staggered drunkenly into the bank, I walked in a daze, my heart turning somersaults. I ignored the usual disdainful stares of my co-workers and went to my station, trying desperately to focus my mind on my job.

About ten minutes later, I saw Jordan coming in, fixing her hair and makeup, her face still flushed from whatever they were doing out in the parking lot. Needless to say, she was very late by now for her shift, but I thought it extremely unlikely that anyone was going to hold her accountable for her tardiness.

I glared at her with unremitting hatred and envy. She had never given me the time of day ever since she first started working here and now I had a whole new reason to resent her.

For the rest of the morning, I was tormented with the vision of those two making out and it gnawed at me like tiger on my leg. My emotions surged from despair to raging anger, back to despair again. It was just so unfair that finally, after finding someone that I thought was perfect, that I should discover that she had feelings for another person.

What was I to do? I wanted to break up with her, but deep down, I wasn’t sure if I had the necessary emotional fortitude to do it. I felt helpless in the grip of her attraction, unable to stand up to her or demand she treat me with respect. The fact was, I felt weak in her presence and even now, I found her very intimidating.

All morning I could think of nothing else and my work suffered for it. Four times, customers complained I had given them the wrong change and once it even came to Ashley’s attention. I knew I was on thin ice with her and I struggled with difficulty to concentrate on my job.

I was with an older lady and trying to deal with that transaction when I saw a previous customer come up to Ashley’s station. An exchange followed in which the lady accused me of mishandling her funds and after taking care of it, Ashley turned to face me.

“Chris, what in hell are you doing today? That’s the second mistake I’ve had to deal with just this morning alone. We don’t hire people to play willy-nilly with our client’s cash.”
She was scolding me and my face was getting red as people were turning to look at us. Ashley was never one to turn away from making a spectacle and this one was turning into a doozie. I feared Denise or Mr. Jenkins would overhear and feel compelled to get involved.

“Don’t you realize how important the funds are that we handle here? It’s not just babysitting money to them…”

Her voice trailed off as I saw her gaze look past my shoulder to the computer screen behind me. Her mouth hung open in midsentence, registering the shock that was apparent on her face. I had no idea what she was looking at but her features darkened even further and her mouth tightened in a grim line.
With mounting trepidation, I slowly turned around to look at my computer. Due to inactivity, it had gone into screensaver mode except that instead of displaying the usual moving picture of the bank logo, I was now watching a slideshow presentation of pictures of myself. My mouth dropped open as I stared in horror at my image, dressed in the pink Sunday school dress, lacy panties tangled around my ankles as I was frantically rubbing the front of my bulging, fluffy diapers.

I gasped in shock as the image was replaced with a close up of the side of my face, Denise’s monster cock buried to the hilt as my cheeks bulged to accommodate her.

“That-is-it!!” Ashley shrieked, “I am going to make sure you get your ass fired!”

My heart was in my throat and I was stammering out an incoherent response when Denise suddenly appeared behind Ashley.

“What’s going on here?” she asked suspiciously.

The rest of the tellers were looking now too and several of them could plainly see the incriminating images on my screen.

In an instant, it all became crystal clear to me.

Denise had been behind this from the very beginning. I still wasn’t sure how she’d accomplished it, but the first night I had been at her house and heard what I thought was a camera shutter, she had been secretly her taking pictures of me. And then the blatant cell phone photos she’d taken the other night of my masturbating had obviously been intended to supplement those.

I was so utterly mortified, I was on the verge of tears. My mouth was moving but I couldn’t say a thing. That was until I saw Ashley’s gaze drop down to focus on my pants. Looking down, I saw the dark wet patch increasing in size as I helplessly wet myself like an incontinent toddler.

Heather, one of the other tellers, had come over to see what all the commotion was about and she shook her head disdainfully.

“Looks like someone needs diapers,” she muttered.

My heart was pounding wildly and I blushed red hot with shame. I would never live this down for as long as I lived! Tears tumbled down my face as Denise looked down on me like a little boy who had failed his potty training for the umpteenth time.

However, her expression hardened and she crossed her arms over her big, proud bosom to address me.

“Mr. Jones, it is clear that you are unprepared to handle the adult responsibilities required by this establishment. You’ve been given ample warning about your filthy porn habits and you’ve chosen to disregard them.”

“–You put these on here, you bitch!” I shrieked bitterly as I wiped the tears streaming down my face.

Denise slowly shook her head patronizingly and Ashley angrily pointed her manicured finger at me.
“You are some kind of sick pervert and you should have been fired a long time ago!” she snapped.

I was tempted to argue that the cock shown in my mouth was actually Denise’s but I knew that would never fly, short of lifting her skirt up, which would probably get me arrested, on top of being fired. My shoulders sagged in defeat as she continued to dress me down.

“Effective immediately, you are terminated, Mr. Jones,” she said in her no-nonsense tone, “Please take your things and leave the building at once.”

Looking around me, I saw nothing but contempt and a total lack of sympathy for me on the faces of my co-workers. I snatched up my car keys and headed for the nearest door without bothering to gather up any of my other things.

The entire front of my pants were soaked and I tried to shut out the sniggering comments being made at me as I pushed through the crowd around my station. Everything was in a blur and I was going on instinct alone.

I ran to my car and started it, jamming the key in and mashing the gas pedal to the floor. Swerving wildly out of the parking lot, I only narrowly missed a soccer mom and her kids in a van that was heading down the street at that moment. I drove through the streets recklessly, not caring whether I ran through stop lights or crosswalks.

By some miracle, I got home without being arrested.

Getting out of my car, I violently slammed the door shut and strode across the parking lot to my apartment. My anger was soon replaced by grief and shame and I hung my head in despair as my pace slowed to walk up the steps.
Because I was looking at the ground, instead of where I was going, I failed to see my apartment manager waiting for me at my door.

“Well, looks like you’ve had quite a day,” she sneered.

Looking up, I saw her standing defiantly in front of me, a slip of paper in her hands.
I had never really known Tasha, the woman who ran our apartment complex, although we had had a few brief exchanges. I knew she didn’t think much of me and of course, I resented her for that.
She was about thirty-something, slim, with long brown hair and a very attractive face. In other circumstances, I might have tried flirting with her but putting aside her distaste for me, she was way out my league anyway. I was used to being treated like trash by beautiful women and Tasha was just one more example in a long line of females throughout my life.

“This is your written eviction notice to vacate the premises. You have five days to clear your stuff out before I call the sheriff,” she said sternly.
Walking past me, she shoved the paper in my hands and strode off without another a word.

Looking down, I sighed heavily as I gazed at the harsh notification, so impersonal and final.
I fumbled with my keys and opened my door. This day had gone from good, to bad, to worse and now to disastrous. I honestly couldn’t think of how things could possibly be any worse for me.
I had no job, no income, no savings, no girlfriend, and now, no place to live, with nowhere to go.

What in the world was I to do??

And that’s when it hit me…

Denise was still holding the key to my chastity device!!
Chapter Thirteen

To say I was between a rock and a hard place, was a woefully inadequate understatement.

Denise was utterly and irrevocably out of my life now, and I still had no more access to my penis than I had when she was my girlfriend. My little member was still locked up tighter than Fort Knox and my chastity cage was going nowhere without getting possession of her key.
The obvious thing, would have been to simply go over to her house and demand she give it back to me but I wasn’t so sure. What if she refused? Worse yet, what if she and Jordan met me at the door and simply laughed at me? I had already suffered more humiliation than a person should have to go through in one lifetime and I wasn’t prepared to endure some more.

But the fact was, I had much bigger problems to deal with than that. I had one day left before I became homeless and I was no closer to being employed than I was when I had gotten sacked. Yes, I had applied at numerous places but due to the nature of my termination and the small size of our town, I was quickly finding out that I was persona non grata everywhere I tried to get a job.

That, combined with the fact that I would soon be without a roof over my head, made my situation increasingly dire. I was wracking my head for a solution and I honestly had no idea whatsoever as to how to proceed. I had 24 hours in which to come up with a solid plan and every hour made me increasingly desperate.

During this time, I found myself pondering what Denise was thinking about me, why she had conspired to get me fired, and why she had shown such an apparent interest in me in the first place.
What was she thinking now? Did she despise me? Did she still like me? In my heart of hearts, I hoped for the latter. But I had no way of knowing without communicating with her. It wasn’t like I saw her any more on a regular basis and her texts had grown silent since I lost my job.

Then again, if I was ever going to cum again, I had to face the fact that she was the only person who had the key I needed. As much as I loathed the idea, it seemed increasingly that I was going to have to make the first move and reach out to her.

After considerable deliberation and much soul searching, I finally took up my phone and punched the thread that had her name on it, typing the following message;

Can I call you?

I must have waited a half hour before getting the courage up to send it and then I finally hit the button.

The phone remained silent for several minutes.
It was infuriating, sitting there waiting for an answer. I kept turning my phone on to see if maybe I’d missed a notification, only to see that nothing at all had transpired.

Finally, after 56 minutes, my phone did its familiar ‘bleep-ba-bleep’.

I scrambled to get it and I shakily scrolled the icon over to reveal the message.

Sure sissy

I wasn’t sure how to take that response exactly but at least it wasn’t a flat out rejection.
Nervously, I went over in my mind how I should conduct myself and what I should say. It wasn’t made any easier by the fact that she held all the cards and I had none.

Finally, I tapped the icon to call her and listened to it ring. She answered after the first ring but said nothing into the phone.

“H-hi, Denise,” I began uncertainly.

“Hi sissy Chrissey,” she greeted me cheerfully.

I breathed a small sigh of relief. That was a positive sign, albeit a humiliating one.

“Umm, how-how’s it going?” I asked, for lack of anything else to say.

“I’ve missed you, baby,” she told me.

Despite myself, my heart surged. In that instant, I forgot all about the many things Denise had done to ruin my life and humiliate me. All I could think about was the spectacularly beautiful woman on the other end of the phone that I had fallen in love with.

Before I could say something in reply, she took the initiative.

“Have you missed sucking my cock?” she asked with amusement in her voice. I thought I heard another woman’s giggle in the background. Was that Jordan?
My heart skipped a beat.

“Are-are you with Jordan?” I asked, my voice quivering.
“Mm-hm,” she replied. Although I couldn’t see her, I knew she was smiling.

Once again, a massive surge of jealousy swept through me unchecked, my anger not far behind it.

“How could you do this to me?” I angrily demanded, “You got me fired and now you’re cheating on me with that slut!”

Denise didn’t reply immediately but her voice took on a bored tone.

“Was there a point to this call?” She sounded ready to hang up.

I had thought I would be able to keep my emotions in check but the presence of Jordan had unexpectedly pushed me over the edge. Nevertheless, I still had to resolve my living situation and this was my only chance, slim as it was.

“I’m sorry, I just…um…I mean…” all of a sudden, I felt my emotions getting out of control and I choked up, unable to speak.
“I don’t have anywhere to go,” I sobbed miserably.

“What do you mean?” she asked, her interest returning.

“I’m about to get evicted from my apartment!” I blubbered, barely coherent.

“Awww,” she said in her honeyed voice, “You could stay with me, baby.”

I wiped the tears off my face as I straightened up.

“I-I could? I mean–you’d let me…live with you?” I could hardly believe my ears.

“Mm-hm,” she said pleasantly.

“As-as your b-boyfriend?” I stammered anxiously.

“Well…not exactly as my boyfriend,” she giggled.
Again, I thought I heard Jordan giggling in the background.

“Wha-what do you mean?” I asked suspiciously.

“If you live in my house, you’ll live by my rules,” she said firmly, “You’ll do as I say without question.”

I bit my lip nervously.

“Li-like what?” I asked timidly.

“We can discuss the details when you get here. But first, I have to know that you will agree without question. Otherwise, we’re through talking.”
Her voice had taken on that bossy character that I knew all too well. There was zero room for discussion when she had her mind made up like this.

“Do you agree or not?” she demanded.

I looked around my mostly empty apartment at my ratty furniture and pee-soaked mattress.

“I-I agree,” I replied. What choice did I have? Once again, she had me cornered and checkmated.

“Good. Then there’s something you will have to do to show that you agree that I’m the one in charge here.
“Remember that outfit I sent you home with a few weeks ago?”

I cringed as I looked over at my couch and saw the white and pink ruffled fleece top laying on it.

“Ye-yes,” I answered her.

“I want you to put that on, along with your anklets, Mary Janes, and the biggest, thickest diapers you have. That’s how you will come over here. If I don’t see you get out of your car and walk up the driveway in that outfit, I won’t even answer the door,” she explained to me.

I gulped hard as I tried to imagine how excruciatingly humiliating that would be.

“Bu-but couldn’t I…couldn’t I just put that on when I got there?” I whined.

“Those are my terms. Take it or leave it.”

I bit my finger in angst, knowing I had little choice. It was either that, or become a homeless beggar in the streets. My mind raced as I tried to think of a way out but I couldn’t see any. I was going to have to go crawling back to her on my hands and knees, and dressed in the most humiliating way possible.

I gulped in trepidation and then began trying to think of ways to justify doing it. After all, it would mean room and board, and an end to all my troubles, to say nothing of a life with a beautiful woman. The short ride over would be embarrassing, for sure, but on the other hand, I wouldn’t be seeing anyone here again anyway, I reasoned.

“Okay,” I agreed quietly.

“That’s ‘yes Mommy’,” she corrected me.

“Yes Mommy,” I quickly replied. I could hear Jordan giggling in the background.

“Good. Be here by 4, I want there to be plenty of light still outside.”

“Yes Mommy,” I responded submissively.

“See you then, sissy,” she said before she hung up the phone.

I looked down at the phone and sighed heavily. It seemed that ever since I had met Denise, humiliation and degradation had become a normal part of my life.

With little else to do, I decided I might as well get this over with. I could come back for the rest of my stuff later.
Walking over to the couch, I laid out three of the soft Birdseye diapers Denise had given me, along with some pins and baby powder. She had only given me one pair of plastic panties, a white nursery print with babyish characters on it. It was going to be mortifying to go out in broad daylight wearing them but if this was the price for free rent, I was going to have to do it.

After arranging the cloth diapers in a thick, rectangular stack, I sat down upon them and proceeded to powder myself as I had seen Denise do so many times before. These particular diapers had an absorbent soaker section sewn down the middle and I was amazed as I pulled them up between my legs to see just how bulky they were. They spread my legs apart just like a baby’s and I blushed with the familiar sensation.

Taking the pink headed diaper pins, I pushed them through the soft cloth awkwardly, unaccustomed to having to do this for myself. It took a few attempts before I got the right fit and then I was ready for the plastic panties. Holding them in my hands, I blushed again that I was willingly doing this to myself. What would people think if they were to see me? I tried not to think about it as I slid them up my legs like my usual underwear. I had to work them around the diapers which were so fat and bulky but eventually, all the fluffy, spongy cloth was contained inside the waterproof vinyl.

I put the top on next, a white and pink fleece garment with short, puffy sleeves and a frilly lace hem that came down to about my navel. A diapered teddy bear amongst some building blocks decorated the chest. Very mature indeed.

I went into my closet and found the white lacy anklets and glossy pink Mary Janes, idly wondering to myself where Denise found all this stuff. Sitting down, I slipped the socks and sissyish shoes on, standing up to look at myself in the mirror.

Of course, I had seen myself dressed like this at Denise’s house many times, but this was the first time I had seen myself in my apartment, and more importantly, having agreed to dress in it myself.
I blushed a hot red as I beheld the thickly diapered sissy looking back at me in the mirror, looking like he needed his mommy and a bottle.

I swallowed hard, grabbed my car keys and headed for the door. Was I really going to do this? How many people would see me? I could only hope I would be able to run to the car and once inside, people wouldn’t really be able to pick up on just how ridiculous I looked.

I was holding the doorknob in my hand, afraid to twist it open. With my heart pounding in my chest, I took a deep breath and opened the door. Looking down the second story balcony hallway, I didn’t see anyone in either direction.
With my heart feeling like it was about ready to jump out of my chest, I tried to walk briskly toward the stairwell going down to the parking lot, only to discover that the extreme thickness of the diapers forced me to waddle like a baby. I went as fast as I could, bolting down the steps but then when I turned the corner, who should I find standing there before me, but Tasha!

Her mouth dropped open (as did mine) and she stared incredulously at me, her gaze taking in my pink Mary Janes, baby smooth thighs devoid of hair, my thick, bulging diapers with the shiny nursery print plastic panties, and lastly, the white and pink sissy baby top.

I nearly dropped my car keys but then I felt a familiar and childish sensation happening in my diapers as I suddenly flooded them in panic.

Oh-my-god,” she said in awestruck shock.

Completely at a loss for words, I tried to move around her but she stepped in my way.

“Whoa there, baby boy,” she said with a smirk coming to her face, “I always suspected you were some kind of weird pervert but I had no idea…”

My face flushed a deep red and I felt another stream of hot pee saturate the cloth between my legs. I ducked around her and fled for my car, her raucous laughter ringing in my ears.

Once again, I was making a panic stricken escape, mindless of my surroundings. Driving like a maniac, I just wanted to get to Denise’s house as fast as I could.
I took the on ramp to the freeway and floored it, accelerating into the left lane as quickly as I could. Keeping my eyes forward, I ignored the cars that were slowing down or speeding up to keep pace with me and see the strange sissy in the driver’s seat.

I had almost reached the exit for Denise’s street when the flashing red and blue lights suddenly caught my attention in the rear view mirror.

With a sinking realization, I knew my day was just about to get a whole lot more interesting.

Chapter Fourteen

As I looked with disbelief into the rear view mirror at the red and blue flashing lights closing in, my entire being surged with panic. How was I going to explain my appearance? How could my situation be any worse?
I bit my lip so hard, I almost drew blood.

With my heart beating wildly, I slowed the car and started pulling over to the right lanes of the freeway. Maybe, just maybe, he was after someone else.

But no, he followed right behind me as I made my way over and I knew with sinking certainty that it was me he was after.

My breathing was coming in short gasps and I thought I was going to hyperventilate. What would he do when he saw my sissy top and diapers? I was already blushing a deep red and I hadn’t even stopped the car.

At last, I pulled off the active lane and onto the wide shoulder, shutting off the engine. The policeman had been driving a suburban and he kept the lights flashing as he got out, which had the effect of calling attention to every motorist who should happen to drive by us.

I swallowed hard as I watched him walking toward me, his dark sunglasses making him look all the more menacing. The big cop rested his hand on his gun as he approached and I squirmed in my seat, only to realize I had just let out another stream of pee into my thick, fluffy diapers.

Rolling down the side window, I tried to get my erratic breathing under control. The cop came alongside and looked down at me, his expression darkening as he beheld the ridiculous image of the sissy baby behind the wheel. I couldn’t read his eyes, but his look was that of contempt and displeasure.

Without a word, he put both his hands on his hips and his chiseled jaw hardened.

“What in god’s name are you wearing, boy?” he demanded.

I swallowed hard and tried to say something but my mouth was so dry I could only stammer foolishly.

“Never mind,” he cut me off in a curt tone, “Do you know why I pulled you over?”

I-I-I wa-was speeding?” I quaked, guessing the obvious.

“That’s right sissy boy. Give me your license and registration.”

My face flushed as I suddenly realized that in my haste to get over to Denise’s house, I had left my driver’s license in my pants pocket which was now lying on the floor of my apartment. With my hands visibly shaking, I fumbled for my car’s registration from the glovebox and almost dropped it on the ground as I gave it to the stern officer.

“Driver’s license,” he barked at me.

I felt another stream of pee surge into my already wet diapers.

“I-I-I seem to have, um, uh, forgot it,” I replied lamely.

He regarded me with a fierce expression that made me cringe in fear.

“Looks like your going to be taking a trip to jail today, young man,” he told me simply.

I gasped in horror. There was no way I could go to jail dressed as I was–no way.

“Please! Wait–please, isn’t there something–something we could do?” I was beside myself with panic. I tried to squeeze my thighs together to staunch yet another steam of terror-induced pee into my diapers.

The cop looked at me long and hard without saying a word as he appeared to consider the alternatives. At last, he put his ticket book into his breast pocket and stood back a step.

“Get out of the vehicle,” he ordered.

With my heart threatening to jump out of my chest, I fumbled with the door handle and stepped out, the cars passing by enthusiastically honking at me as they caught sight of my babyish outfit. Looking around nervously, I followed him as he led me to the opposite side of his suburban from the traffic. He then made me face the oncoming traffic while he stood behind me. I wanted to hide behind the vehicle but he pushed me forward so I was next to the rear view bumper, ensuring everyone in the near lanes would get an unobstructed view of me as they drove by us.

I blushed hotly as I stood there, every fifth or sixth car honking at me as they whizzed by. I heard him undoing his belt and unzipping his pants and wondered what exactly he had in mind.

Before long, I felt the waistband along with the back of my diapers being pulled back. I squealed with surprise but the worse was yet to come. I knew I had no choice but to submit to whatever he was going to do to me and in my naïveté, I thought maybe he’d just drop something down the back of my diapers.

It was with mortified shock that I felt a strong stream of hot pee suddenly splashing against my lower back and into the crack between my buns as began peeing into my diaper like it was his own personal urinal.
The cars passing us could probably see his head behind me but it was my full body that they saw as he slowly relieved himself into the thick, absorbent cloth inside my plastic panties.

My face went a bright shade of red and I bunched my fists, stamping my feet in frustration as I stood in place, letting him do his business without any sort of interference. He must have thought me a complete weakling to stand there and do nothing. Somehow, all my previous moments of spinelessness seemed to come back to haunt me, as if to say that all my cowardice in the past had led me to this ultimate of humiliating degradations. To be sure, I was showing absolutely no backbone now or doing anything to discourage this bully.

I could feel his hot pee accumulating in a deepening pool in my seat as the fluffy, soft cotton struggled to absorb it all as fast as it could. I felt the soggy warm wetness seeping in between my legs and up into the crotch of my diapers to surround my little balls and caged penis with his nasty urine.

The force behind his stream was very strong and as it splattered against my lower back, I pictured he must have had quite a big cock. He kept peeing freely, emptying what must have been a very full bladder until it trickled to a halt. And then, just when I thought he was finished, he started with another equally strong stream.

I sobbed with humiliation and felt my eyes filling with tears of shame. My diapers were sagging by now with the weight and I whimpered with helplessness. Who else was so totally lacking in dignity to let another man pee freely into the back of his diapers? But then, who else would have willingly put on diapers, plastic baby panties and a sissy outfit to drive around in public? Obviously, my shame had no bounds.

I waited until he was finally done, and then stood there submissively as he let go of my plastic panties and slapped my thickly diapered bottom roughly as a form of dismissal.

“Run along, sissy boy,” he commanded me.

“Yes sir,” I whimpered in defeat.

In my utter humiliation, I waddled back to my car, holding my diapers on either side to prevent them from sliding down my smooth thighs from the weight of all that pee. With a humiliating squish, I sat in my seat, the warm pee seeming to surround me completely as my snug plastic panties ensured I felt every soaking square inch of my diapers.

I sniffed away the sob threatening to engulf me as I pulled back onto the freeway and slowly took the exit to Denise’s house.
Needless to say, I could never tell anyone what just happened. If she asked–and I knew she would–Denise would have to be told I simply couldn’t hold it anymore and I’d peed my diapers like any other incontinent toddler.
Chapter Fifteen
After my humiliating encounter with the cop, I drove much slower, and with a heightened sense of apprehension as I made my way to Denise’s neighborhood. I rebuked myself for forgetting my driver’s license–I wouldn’t be swimming in another man’s pee now if I had just been more careful and less impulsive.

Earlier, I had been dreading my arrival at my former girlfriend’s house but by comparison to what I had just been through, walking up her driveway in my sissy top and exposed diapers was going to be easy.

I hadn’t wanted to move too much in my seat but regardless, I couldn’t escape the cop’s warm pee surrounding me everywhere. There wasn’t one section of my diapers that wasn’t fully saturated and I felt like a toddler who couldn’t be trusted with training pants yet. I was utterly ashamed and part of me even felt like I had gotten what I deserved for my total lack of backbone and my cowardly personality.

Getting out of the car, I closed the door behind me and waddled awkwardly up the paved driveway to Denise’s front door. My diapers were so heavy, they sagged under the weight and I was forced to use one hand to help support them. With my free hand, I knocked on the door and waited nervously, hoping my exposure outside would be as brief as possible.

Before long, I heard the sound of Denise’s high heels clicking on the hardwood floor as she approached. The door opened wide, and I beheld my former boss for the first time since she had fired me so ignominiously at the bank earlier in the week.

She was wearing a snug, form-fitting white skirt and matching crop top that clung deliciously to her big, mouthwatering breasts. In all my trauma lately, I had forgotten just how mesmerizing they were. No wonder I was willing to do anything and everything she had wanted!

Her lovely long black hair spilled over her mostly bare shoulders in big curls but it did nothing to hide the deep, sexy cleavage between her big, proud breasts. Now that I stood before her, I felt foolish and weak when confronted by her power and beauty and I found myself blushing all over again.

She stood well above me, her hands on her curvy hips as she looked down at me imperiously, as if I were an errant child.

“Well…Did my little baby manage to keep her diapers dry for the ride over?” she asked skeptically.

I squirmed and turned bright red with embarrassment. Without waiting for an answer, she stepped outside, physically turned me around to face the street, and squeezed the thick, spongy seat of my diapers.

I squealed with embarrassment.

“Oh my, you are absolutely soaked!” she exclaimed, “You really do need diapers, don’t you?”

My face burned with shame as a neighbor across the street came out to check her mail. The woman looked across to gaze at me and I could see her eyebrow rising quizzically.

“Um, can-can we go inside?” I whined.
Denise answered me by swatting my seat and I stumbled forward clumsily, showing anyone who was watching who wore the real pants in this relationship.

Just as I turned to go in, Jordan appeared next to Denise blocking the way, and she looked down on me, the disdain plain on her face.

“Oh–it’s you,” she said by way of greeting.

I squirmed awkwardly and shifted my feet, not knowing what to say.

“That outfit suits you perfectly,” she remarked, “Just what I’d expect from a big sissy like you who can’t keep his pants dry.”

My cheeks burned with shame as I stood before the two of them, thoroughly humiliated. And to be sure, things weren’t made any better by the fact that the thick diapers I was wearing were sopping wet, only confirming her dismal opinion of me.

“Chrissey, I think you need to tell Jordan what you did,” Denise told me.

Biting my lip, I looked down at the concrete walkway in front of us. I badly wanted to duck inside and hide but she was apparently going to drag this out and make me humiliate myself in front of everyone.

“I-I w-wet myself,” I admitted shamefully.

Jordan shook her head in disgust.

“What a surprise.”

“Don’t worry, Chrissey,” Denise said with a forgiving smile, “Your days of wearing pants are over. Why don’t you come inside and I’ll show you to your room.”

Feeling a mixture of relief and trepidation, I followed them inside but not before looking over my shoulder to see if their neighbor was still there. Sure enough, the woman was still standing by her mailbox, staring at me and trying to figure out what kind of weirdo I was.

I rushed inside, waddling awkwardly behind the two sexy women as they led me down the hall toward the mysterious room Denise had been having work done to previously. As the two of them went in and stepped aside, I entered and looked around in shocked amazement.

It has been re-designed as a nursery, and judging by the pink and white decor, it looked like it was intended for a baby girl, albeit, a rather large one.
An oversized pink crib dominated the room, with a teddy bear nestled cozily amongst it’s Disney Princess baby blankets. Next to it, a low vinyl-covered changing table sat nearby, stacks and stacks of thick cloth diapers and other supplies ready for use along with a short chest of drawers that were open to reveal many pairs of waterproof plastic panties. My stomach buzzed with nervous anticipation.

A shelf containing nursery books and baby toys was to one side and next to it, a folded playpen stood ready for use.

Three sides of the room were wallpapered with designs of baby bears and building blocks while the fourth wall was covered with a mirrored set of closet doors. A warm light shone in through gauzy pink curtains over the only window on the opposite side of the room.

In the far corner, stood a large pink dresser, with dolls lining the top, it’s sides decorated with more playful nursery characters.
Hanging above it on a peg, I suddenly shivered as I recognized Denise’s formidable Spencer paddle, an instrument of discipline I was all too familiar with.

I gasped as I took it all in.
I guess I hadn’t really given too much thought as to what the conditions of my living here would be but I never imagined this!

“This is where a sissy like you belongs and it’s where you’ll be spending the majority of your time, Chrissey,” Denise explained firmly, “Judging by how wet your diapers are, it’s obvious you need them 24/7 now.”

My face reddened and I wanted to blurt out that most of the pee in my diapers wasn’t my doing but somehow, I didn’t think that explanation was going to do me much good.

“Time to explain a few ground rules,” Denise said in her no-nonsense tone, “First, under no circumstances are you to touch your diapers. If either of us catch you doing that, you will immediately get a severe spanking. Your diapers will be changed at our discretion, either by one of us, or one of your babysitters–”

“–Ba-babysitters?” I spluttered, trying to take it all in.

“Yes, babysitters. We won’t always be here to watch over you so I have a number of girls in mind that will be babysitting you when we’re gone.”

She saw the shock and horror registering on my face and a sly smile appeared on hers.

“Oh yes, Chrissey, don’t think for one minute that when people are visiting that your diapers will remain a secret. These are your underwear from now on,” she said slapping my thickly padded bottom, “And we’ll change your wet diapers regardless of company, so you might as well get used to the idea.”

I bit my lip and balled my fists as I struggled with the intense frustration, humiliation, and fear rising within me.

“Second, your bedtime will be 7:30 sharp. Any bad behavior during the day and I’ll move it up to 7, or even earlier. That means you will be in your crib, diapered and locked in with the lights out by bedtime. Any whining or complaining will result in trip over my lap.”

My mouth hung open again and my lips quivered as I tried to deal with what she was telling me.

“Third, I’ve already told you that you are to do whatever I tell you without question. That goes for Jordan here too. She has equal authority over you and if she feels you need a spanking, she has every right to do it.”

As I stood there in shock, Jordan strode over to the dresser and reached over to pick up the Spencer paddle.

“And just to get things off on the right foot so you’ll see who’s boss around here, I’m going to give you a taste of how things are going to be from now on,” Jordan told me.

I couldn’t believe what was happening to me. The very woman I resented and hated and had stolen my girlfriend was about to pull my diapers down and spank me!

I gulped in panic and felt a fear-induced stream of pee flood into my already soggy diapers.

“No-p-please,” I begged her as I put my hands up in protest.

She snatched my wrist roughly and yanked me over as she took a seat on a sturdy stool that I assumed served one purpose only–one in which I was about to participate in. With grim determination, she tugged my plastic panties and heavy wet diapers down with one quick move, leaving my pink chastity device fully on display.

I blushed hot red with shame as the strong smell of pee surrounded us.

“Pathetic…absolutely pathetic,” she said shaking her pretty head, “And I can see why Denise locked up this tiny little thing. A sissy like you doesn’t deserve to be able to cum anyway.”

Looking back up into my fear-filled eyes, she fixed me with a stern gaze.

“I’ve been wanting to paddle you for a long time now, Chrissey,” she told me, “so you can be sure I’ll make this one count.”

“Please don’t spank me!” I begged her shamelessly, the panic rising uncontrollably and making my knees weak.

“Get over my lap,” she told me tersely.

I squealed like a little girl as she yanked me over her skirted thighs, causing me to fall face forward helplessly.

“Wait! Please–please don’t spank me,” I sobbed. I knew there was no escaping now and as usual, my weak nature had put me in a place where I was going to receive a painful, humiliating punishment at the hands of the very person who was my arch enemy.

“By the way…I just thought you should know…” Jordan said smugly as she rubbed the fearsome paddle against my damp bottom, “Everyone at work knew you were wearing diapers–you smelled like baby powder and pee all the time and the girls used to call you ‘Pamper Princess’.”

I groaned with crushing shame at the realization even as I squirmed feebly on Jordan’s lap.

I opened my mouth to say something but I was cut off by the harsh, biting impact of the hard wooden paddle being seared across both my tender cheeks. I gasped in pain and howled as the paddle came down again and again in quick, scalding succession. Jordan was letting loose with months of pent-up frustration and resentment and she spanked me with all her strength. I burst into tears immediately and kicked my feet as I bunched my fists and beat the floor.

My wet diapers had only served to make my bottom more sensitive and I bawled with bitter indignation as each hard slap of the paddle impacted my damp, pee-soaked buns.

With tears flooding my eyes, I could no longer see Denise clearly as she stood above me, but her hands were on her hips as she watched her lover soundly paddle me with impunity. It felt like a thousand wasps were stinging my blazing cheeks and I was crying like a baby, struggling to escape Jordan’s terrible retribution but her grip was like steel as she continued my excruciating punishment.

Denise must have taught her well because after bringing the center of my buns to a flaming hot, cherry red, she turned her attention to the virgin sides, slapping them harshly until they glowed equally to an angry, red crimson. I prayed that she was done but then she returned to the center of my seat, repeatedly bringing the paddle down hard, delivering deep, vengeful swats right at the soft curve of my bottom where it reached my thighs. I wailed at the top of my lungs, kicking wildly as the hot tears spilled off my face to splatter on the floor while I pounded it with my fists in bitter, impotent frustration.

Was this to be my fate? Being paddled like a naughty little boy whenever the mood struck them?
While I had some sort of relationship with Denise (the exact nature of which I was still unsure), I could tell Jordan wouldn’t think twice about putting me over her lap for the slightest infraction.

I had resented Jordan from day one and it was the worst possible fate for me to find myself under her harsh and unforgiving authority. And now–to be spanked by her! It was more than I could bear.

At last, the terrible spanking was over and Jordan dumped me unceremoniously on the floor. I immediately reached around and rubbed my flaming, swollen cheeks as I cried like a baby before them.

“That was only the first of many spankings you can expect from me, sissy boy,” she informed me.

Denise came over and bent down to my level, smiling warmly at me in sharp contrast to Jordan.
“Aww baby,” she said, her voice for once revealing her sympathy, “Come here, sugarplum.”

Scooping me into her arms, I sobbed miserably as she held me to her soft, pillowy bosom in a tender, motherly embrace.

“I’m sorry that was necessary but it was important for you to learn that Jordan means business when she tells you what to do,” she said in a voice for simple toddlers.

I wiped my arm across my wet face and looked over to Jordan who still had the paddle in her hand, her arms crossed over her chest defiantly and an unrelenting, smug look on her face. As much as I hated and begrudged her, she was my boss now and I was going to have to respect her rule over me.
Whereas before, I had been an insignificant worm to her–now, I was her bedwetting sissy baby for her to punish and humiliate as she pleased.

Denise was soothing me and rubbing my head in a maternal way as she pushed my wet nose between her mammoth breasts.

“Poor little sweetums,” she cooed, “Mommy needs to put her little baby back into her diapers.”

I wasn’t about to resist her. I had no strength left.

Choking back a sob, I let her take me over to the changing table where she laid out three thick cloth diapers. I certainly didn’t want to live the life of a little baby girl but these two gave me no choice.

I pouted and continued to cry as she sat me down on the diapers but I howled out as soon as my blazing bottom came into contact with them.

Denise smiled down on me again and she pushed a big, pink rubber pacifier between my quivering lips to quiet me. I found it oddly comforting and I tried not to look at Jordan who was still standing there looking superior, staring down at me with disapproval. I whimpered as Denise pinned me into my new, permanent underwear; thick, embarrassing diapers, and I tried not to think of how it would be like to be seen by everyone that came over.

“Time for your baby panties, Chrissey!” she said gleefully as she positioned a pair of pink nursery print waterproof panties at my Mary Jane-clad feet. I sniffled as she worked them up my smooth legs and worked them over the bulky cloth, running her fingers around the waistband to be sure all the cloth was contained inside.

Rising up, she went over to the closet and came back with a fluffy pink and white baby dress which she held before me proudly.

“Is this what my little girl wants, hm?” she asked in her syrupy voice.

With the fat pacifier stuffed in my mouth, I nodded submissively.

“Well, don’t you worry sugarplum, ’cause Mommy bought a whole wardrobe for you, and you’re going to be just the cutest little baby girl from now on,” she said enthusiastically as she removed my fleece top and replaced it with the frilly dress.

Standing me up, she stood behind me as she zipped up the back and adjusted the short hem of the girly ensemble which barely covered the top of my diapers. I cringed as I stared at our reflection in the mirror, looking like mother and baby daughter.
Even without her heels, Denise was much taller than I but with her stilettos on, she practically towered over me. She stood behind me proudly, beaming with pleasure at the final result of all her careful scheming and planning.

“From the first day I met you, I knew I had to make you my baby girl,” she said with her beautiful smile, “And we both know this is where you really belong, Chrissey–not trying to impersonate a man, but wearing dresses and diapers in your very own nursery like the big sissy we all know you are.”

I blushed hotly from behind the fat pacifier filling my mouth at her humiliating words.

Jordan stepped forward and stood next to Denise.

“I think we should invite the girls from the bank so they can see the diapered sissy that used to work with them.”

“Oh my god–what a great idea!” Denise agreed, clapping her hands with eagerness, “I can’t wait to tell Ashley and see the look on her face when she sees him.”

Turning around to face Jordan, Denise threw her arms around her neck and planted a big, passion-filled kiss on her lips.

As I watched the two of them groping each other lustfully, I seethed with mute jealousy and envy.

Breaking her kiss momentarily, Denise looked into Jordan’s willing eyes but kept her arms around her.
“I think we need to leave our baby to play with her toys while we have some fun of our own,” she suggested in a husky voice.

“I thought you’d never ask,” Jordan grinned.

The two left me standing there, locking the door behind them to prevent me from leaving or interfering with their lovemaking.
I sniffled and sighed heavily, sitting down to look at the dollies and toys that had been gotten for me.

Several minutes later, the rhythmic sounds of the two of them moaning could be distinctly heard from the adjoining room as I stacked my colorful building blocks.
I didn’t even notice as I began wetting my soft, fluffy diapers.
THE END

Epilogue
…six months later

Anxiously, and with rising concern, I sat on the padded, vinyl covered floor of my playpen, surrounded by a collection of my dollies and a number of big plastic building blocks.
Not surprisingly, my diapers were soaking wet, as they often were these days. I had long ago lost my ability to control my wetting, and it was rare that I even got any kind of a warning sensation beforehand. More often, I just found myself helplessly wetting my diapers like any completely incontinent toddler.

Denise had explained to me that during the first few days after I’d met her, she’d put a mild sedative and diuretic in my baby bottle, just to get the process started, but after that, it had all been me. I think all the pressure I had been under, both at the bank, and trying to deal with Denise during the early stages of our relationship had caused me to revert to bedwetting, which in turn, started my uncontrolled wetting during the day. In any event, my diapers were indispensable now and they normally only remained dry for the first hour or so. After that, it was only a matter of time before they grew heavy and began to sag with all the pee accumulated from several consecutive wettings.

I had certainly become used to the feeling of wet diapers on a regular basis and it no longer bothered me like it used to. And to be sure, I had gotten used to the smell of stale, pee-soaked diapers in my nursery which no amount of fragrance could cover. Any visitors that should happen to come in, quickly realized that my diapers weren’t just for show but we’re absolutely necessary to keep my childish wetting under control.

True to her word, Denise spared me no dignity around her friends.
By now, they all knew of the sissy baby in her house and I was regularly paraded in front of them wearing my short dresses, onesies, or diaper shirts. And if she felt it was time, my diaper changes would take place in front of any or all of them, with some of them even lending a hand during the process.

And even though this was happening on a regular basis, the intense humiliation I suffered was as if each one, was the first time. Some of her friends really enjoyed teasing me, especially Ashley who was a regular visitor, or her bossy but sexy friend, Ariel. The latter particularly enjoyed humiliating me and making me explain in great detail why I “wasn’t ready for big boy underpants”, and why diapers would be my constant companion.

I had hoped my spankings, which had become a regular event since I moved in, would be kept private but that too, was something I had to suffer in front of everyone. Here again, Ashley and Ariel were only too happy to lend a hand and it was to my utter shame whenever one of them would unpin my diapers and pull me over their lap to soundly paddle my bottom.

But overall, I couldn’t really complain. My room and board were provided for by Denise and Jordan and I had zero responsibilities. My main concerns centered around what kind of food I was served in my high chair, and how soon I could get my perpetually wet diapers changed. To my frustration, it wasn’t uncommon for Denise to squeeze the thick seat of my diapers and dismissively tell me “you can wait another hour”, which meant enduring the annoying, clammy wet embrace for who knew how long.

I spent most of my time in my nursery, which on the whole, was about as dull and boring as it could get. And even when I was let out, it was usually just to be strapped into my high chair for meals or be placed in the playpen so they could keep an eye on me.
I had traded the stress of living in a competitive world for my freedom.

Denise kept my schedule of orgasms rare so the spikes in my chastity device remained as a constant source of pain for me. I tried my best to avoid thinking about sex but it wasn’t easy with the two of them going around the house wearing little in the way of clothing. I was generally allowed but one orgasm a month, and that, only by being bent over the crib mattress, my diapers pulled down as Denise pounded me for an hour from behind with her big, hard cock. Jordan made a point of telling me I was lucky to get even that, and maybe she was right, although it always left my hole sore, aching, and leaking of her gooey semen.

My sex life could be varied, in that sometimes Denise allowed me to masturbate into my diapers instead of being humped for my monthly orgasm. However, those rare instances always occurred under the most humiliating circumstances, like when she made me do it front of all her friends. After removing my chastity device, I was re-diapered and made to sit in the middle of the living room floor, then given a set time limit in which to rub myself to orgasm.
Given the audience I was to perform in front of, I preferred being bent over the crib mattress to the mortifying humiliation of playing with myself in front of a bunch of jeering, mocking women.

It was Jordan’s idea that I should receive regular “maintenance spankings” once a week, just to make sure I remembered who was boss. I certainly didn’t need any reminding and I dreaded them terribly but like everything else, I had absolutely no say.
On Sundays, either Jordan or Denise would come into my nursery, take down the paddle and put me over their lap for a blistering spanking that left me kicking and crying like a baby.

The only plus out of that arrangement was when Denise was the one administering the punishment. She would often re-diaper me afterwards and place me on her lap, allowing me to nuzzle her big, beautiful breasts as she bottle fed me.

Another aspect of my new life that I soon discovered after moving in were regular, daily enemas. Denise had a big dildo nozzle she liked to use when she bent me over for my daily purging, and it made her giggle to watch me squirm and whimper as I took in the quart or more of hot, soapy water deep into my rectum. She said she loved nothing more than to see me weak and helpless, bent over her lap with my legs spread as she administered the enema and I moaned like a little girl.

As much as I hated that humiliating procedure, I was wishing now that I had gotten one earlier today. The weekend morning had been unusually busy for the two of them and Denise had simply forgotten all about it. While one would think that would be a good thing, two circumstances were now dictating otherwise.

The first, was that I was starting to feel warning cramps and an urgent need to go. The second, was that Jordan had put my big rubber pacifier in my mouth with strict instructions not to remove it.
I knew better than to disobey her when she had issued that kind of order. My bottom was still sore from last night’s severe paddling.

But at the moment, I was sitting in my playpen in the living room, while the two of them were on the couch opposite me, kissing and fondling each other. Even under the best of times, this was a tortuous situation for me. It was agony watching or listening as they became amorous with each other because my little penis couldn’t help but get aroused and it wasn’t long before I felt the cruel bite of the sharp spikes in my chastity device. No amount of thinking about mundane things would alleviate the pain and I was left to suffer in silence.

However, today I had a whole new set of concerns. My dinner last night had worked its way through my bowels and was now seeking escape in the only way it could. I was shifting my position in the playpen but I knew there was no escaping nature’s inevitable course.

Rising up on my knees, I gripped the softly padded sides of the playpen and looked over anxiously at Denise and Jordan. They were completely oblivious of the torture I was undergoing as they kissed and explored each other’s bodies freely.
As the urges became stronger and stronger, I chewed my pacifier and whimpered, trying to get their attention. I knew that neither of them were fans of messy diapers and I could only imagine the punishment that would await me if I were to go right now.
Nevertheless, I was getting closer and closer to surrendering and I fidgeted anxiously, trying to find a position that would take some of the pressure off.

I gripped the side of the playpen until my knuckles grew white, mewling and desperately trying to make them look my way.

Finally, I couldn’t take it anymore.

With a sob of defeat, I knelt down a bit and relaxed. A huge, solid load pushed out between my spreading cheeks into my waiting diapers, oozing slowly, only to be followed by another equally thick one. A tear of shame trickled down my cheek and I was shocked at how big the mess was as the big slippery log slid up my crack. It filled my entire seat and felt heavier than I expected. I groaned as a third, smaller load joined the first mess in a growing, nasty pile within my diaper.

My face was red already from my exertions but now the utter shame of my childish act hit me. Even though I was still positioned on my knees, there was no escaping the warm, sticky mess being held closely and intimately against my bottom cheeks. And worse yet, my knees were getting tired, with neither Denise or Jordan showed any signs of noticing my distress.

At last, my knees couldn’t take anymore. With a sob of humiliation, I slowly sat down, the gooey mess squishing against my seat and spreading all around. I had never felt more like a helpless baby in all my life and I sniffled with shame, fighting back the tears that threatened to burst from my eyes.
At that moment, I hated being Denise’s little sissy baby!

I was sitting there miserably, trying to think of how things could be any worse for me when the doorbell rang. I gasped in shock and felt a strong stream of warm pee join the big, babyish mess that was already in my diapers.

Jordan stopped kissing Denise momentarily and she gave me a wicked look.

“That must be Chrissey’s babysitter,” she explained.

The very last thing I wanted was to have my mess discovered, let alone, by an outsider.
Jordan scurried over and opened the front door, standing aside as she invited her guest in. I winced as a tall, good looking, muscle-bound man entered. He was wearing snug white shorts and a tank top which served to showcase his very impressive physique.

Jordan gave the tall man a quick hug and then brought him over to the playpen. I blushed hotly as I looked up in embarrassment at the big man that was towering over me.

“Chrissey, meet my friend Hank. He’s a personal trainer down at our gym and he’s been super anxious to come over and meet you. I told him you were just a big sissy who wears diapers and dresses but he didn’t seem to mind.”

His crotch was eye level to me and I couldn’t help but notice a growing bulge in his shorts. I squirmed nervously in my seat, which only spread the big, sticky mess in my diapers further.

“Hank said he’d gladly babysit you for free, although god only knows why,” Jordan said sourly.

He looked down at me with naked lust in his eyes and I swallowed hard, watching as he slowly stroked his big, growing boner idly through the thin fabric of his shorts.

“Oh–” Jordan said by way of an afterthought, “–Did I mention that he’s gay? I’m sure the two of you will have lots of fun together.”
THE END

Reunion With an Ex-girlfriend

“Come in, come in,” Stephanie said, keeping her voice purposely low, “He’s taking his nap now, so he has no idea you’re here.”

Tessa, tall, brunette, and very pretty, strode through the front door, being careful not to let her high heels click too loudly on the wooden parquet floor. Her figure-hugging skirt looked sexy, yet businesslike, and her fitted top revealed that she was a woman that men looked twice, and then three times at.

“Is he really wearing diapers?” she asked incredulously, still not quite prepared to believe what her new friend had told her.

Stephanie smiled, “You’ll see soon enough…come down the hallway, but don’t let him hear you–I want him to be completely surprised when he sees his ex-girlfriend in the flesh.”

The lighter haired woman stopped at a door and slowly, carefully and quietly pushed it open, her smile increasing as she spied her boyfriend sleeping across the room. Standing aside, she beamed at Tessa and allowed her to take in the unique decor of the room.

It looked exactly like a baby girl’s nursery, with a pink dresser, changing table, stuffed animals and dollies, and a bookshelf filled with childish coloring books. The afternoon sun shone strongly through the single window in the room, despite the gauzy pink and white curtains that were pulled closed. Nursery print wallpaper surrounded the room and a large pink crib dominated the corner.
It was in that piece of over-sized furniture, that Tessa’s shocked face beheld Conrad, her former boyfriend. Hardly able to believe her eyes, she quietly and tentatively stepped into the room, the subtle but distinct smell of stale pee making her cute nose crinkle distastefully.
The two of them moved over to the edge of the crib and looked down at the sleeping occupant, oblivious to the audience he now had standing above him.
Sometime during his nap, he had pushed the baby blankets aside, and he lay there now, peacefully sucking his thumb in slumber.

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Tessa stifled a giggle as she looked down on the prone form of her former boyfriend. He was wearing a fuzzy white and pink, short-sleeved, fleece top that came down just past his navel, but what really grabbed her attention were the bulging fat diapers and colorful nursery print plastic panties now fully exposed around his hips. He looked every part the innocent baby toddler, soundly asleep with his pretty pampers humiliatingly revealed.

Giggling to herself, Tessa quickly dug in her purse and eagerly took out her cell phone. With a few keystrokes, she brought up the camera function and immediately began snapping pictures of the big sissy sleeping blissfully beneath her, making sure she got his face in the shots.

Stephanie reached down and carefully slide a finger inside the leg holes of his plastic panties. Quickly withdrawing her finger, she rubbed them together, indicating the wetness she’d discovered.

“Soaking wet,” she whispered, a conspiratorial smile on her beautiful face.

Tessa shook her head in disbelief, taking two more pictures to satisfy herself. Then Stephanie silently motioned them out, closing the door quietly behind her.

“We’ll talk in the dining room,” she told her new friend quietly.

The two of them tip-toed down the hall and into the dining room, which was some distance from the nursery.

“I wouldn’t have believed it if I hadn’t seen it with my own eyes,” Tessa remarked with astonishment as she scrolled through the pictures on her phone she’d just taken, “How did you find me?”

“Oh–that wasn’t too difficult. I just went through Conrad’s contact list and I saw your number there.”

“Okay–you’ve gotta tell me how this whole thing started. I mean–I thought he was a perv and all, but I never figured he was some sort of big baby,” Tessa explained in a rush.

“Well as I’m sure you know, sex with him was never very good.”

“I’ll say,” Tessa quickly agreed, “Pathetic, would be a better description.”

“Thank you. Yes–I couldn’t have said it better. I can’t tell you how many times he came after only thirty seconds of thrusting inside me. It was bad enough I could barely feel him, but then to have him lose it after less than a minute…”

“–Believe me–I know,” Tessa interjected, “Thank god, I don’t have to deal with that anymore.”

“Well anyway…I think it was about six months ago that I found his secret baby stash; plastic pants, diapers, pins, baby powder, all kinds of weird stuff. Once I got over the initial shock–it all kinda started making sense to me. He didn’t want to be a man–he wanted to be a big baby, free of any responsibilities.”

Tessa was nodding her head slowly in understanding.

“That was when I decided to give him just what he wanted–a nursery fit for a big sissy baby–all of it being paid for with his credit cards, of course.
“He was overjoyed at the beginning, thinking he was in masturbation heaven–that is, until I decided to get him fitted for a nice, secure chastity device. Unfortunately for Conrad–that put an abrupt end to his ability to play with himself. Finally, he had all the soft, fluffy diapers and sissy outfits he ever wanted, but no way to satisfy himself,” Stephanie chuckled.
“Now I leave the keys at work so there’s no chance he can get out unless I decide.”

Tessa clapped her hands and giggled with glee.

“How often do you let him out?” she asked.

“Once a month, if he’s good. I unlock his device and let him cum in his baby diapers–he looks absolutely ridiculous, rubbing himself like a horny toddler. But after one orgasm, its right back into his chastity cage for another month.
“Last time, he got sassy with me so I added another month to his lock up time.”

Tessa smiled with admiration and satisfaction.

“But what about you?” she suddenly asked, the realization hitting her that the situation being described hardly sounded mutually satisfying.

“Oh, don’t worry. Once Conrad got his nursery–I immediately started dating other men. I mean–after pinning him into his diapers and pulling his plastic panties up, it was impossible to take him seriously as a man anymore, you know?
“He didn’t like it at first but I have a paddle I keep in his room that I use for occasions when he tries to stand up to me. I just yank his diapers down and put him over my lap. After ten swats–he’s bawling like a baby but I make sure he gets a full five minutes so he really learns his lesson.”

Tessa nodded her head in agreement with Stephanie’s methods.

“Serves the big sissy right.”

“I thought you’d approve,” her friend replied, “Of course…I don’t know what your relationship was like with him…he described you as a total bitch to me…but I’d bet you have some grievances of your own to settle with him.”

Tessa’s pretty features darkened as she imagined her pathetic former boyfriend making up all manner of stories to justify how their relationship had ended.
For Tessa, his ridiculous attempts to try and fulfill his manly duties in bed had been quite enough. With her looks and body, she had no difficulty whatsoever trying to attract men and she was far too young to let her life be wasted by a sissy like Conrad.

“Anyway, thanks for coming over to babysit him for me. I haven’t seen my boyfriend for a week now and I can’t wait get to his place, if you know what I mean,” she said with a mischievous wink, “I may not be home tonight.”

“No worries,” Tessa said, smiling pleasantly again, “I have an old score to settle with Conrad and I brought my stuff for an overnight just in case.”

“Great–I’ll let you know later on tonight what we plan to do,” Stephanie told her, “And now…should we wake up our little bedwetter?”

An evil smirk crossed Tessa’s face.

“Oh yes.”

Walking back down the hallway, the two of them entered Conrad’s nursery and Stephanie unlatched the side of his crib, lowering the rail. With a sharp slap on his thickly diapered bottom, Stephanie woke the sleeping sissy out of his dreams.

“Time to wake up, baby boy,” she announced.

Conrad’s naturally long eyelashes fluttered open and he slowly focused on his beautiful girlfriend, only to see her step aside and reveal the tall, pretty brunette standing behind her. His mouth dropped open in shock and recognition and he gasped with horror.

“Wha-what are y-you doing here?” he stammered in a panic.

Tessa stood over him, her hands on her curvy hips, a look of smug superiority on her face.

“Well hello, Conrad–or should I say baby Conrad,” she sneered derisively.

The diapered sissy’s face flushed beet red as his eyes darted from Tessa to Stephanie, and then back to Tessa again. He grabbed the blankets in a futile attempt to hide himself but Stephanie wasn’t having it. With a firm grip, she hauled him out of the crib and stood him before his tall, imposing ex-girlfriend. With her free hand, she smacked his thickly diapered seat which landed a dull thud.

Tessa suppressed a giggle. Stephanie looked just like an angry mother chastising her errant child.

“Is there something you want to tell Mommy?” she asked.
It was obvious from her tone of voice that this was a ritual of some sort that they practiced upon his waking up.

Conrad’s cheeks blazed with humiliation as he stared down at the floor, unable to look his pretty ex-girlfriend in the eye.

“Come on sissy–what do you say,” Stephanie prodded him.

Conrad let out a nervous breath, his shame overwhelming him.
“I-I can’t,” he whined.

“Say it. Or you’ll say it over my lap,” Stephanie warned him, her voice taking on a cutting edge.

Conrad shuffled his feet, the blushing making his ears and chest red.

“I…I wet my d-diapers,” he stammered under his breath.

“Speak up, sissy,” Stephanie said as she reached over to pick up a fierce looking wooden paddle hanging from a peg on the wall.

“I-wet-my-diapers,” he blurted out, the humiliation practically crushing him.

Tessa shook her head, both amazed and disgusted at his display of self degradation.

Setting down the paddle, Stephanie pushed him down onto the changing table, a large, vinyl covered surface with playful nursery characters decorating the surface.

“I’m going out on a date tonight, so Tessa here has graciously agreed to babysit you,” she said as he began peeling his clinging plastic panties off his sopping wet diaper.

“B-babysit??” Conrad stuttered nervously.

“That’s right, sissy boy,” Tessa interjected, “You see–just like me, your girlfriend here isn’t satisfied with a bedwetting pansy like you–she needs a real man tonight.”

Pulling his damp plastic panties off his feet, Stephanie tossed them into the nearby diaper pail.
“So this evening, while I’m in bed with my boyfriend, you’ll be taken care of by Tessa…if I were you, I wouldn’t do anything to piss her off.”

Conrad bit his lip so hard he almost drew blood.

Meanwhile, Stephanie removed his pee-soaked diapers and deposited them in his diaper pail as well, cleaning him up with some baby wipes.

Seeing his chastity device for the first time, Tessa bent down and grasped the small pink cage that was imprisoning his little penis, looking at it carefully.

“So this is a chastity device, I’ve never seen one before…Looks like money well spent,” she remarked.
The contraption was only about an inch in length and it bent his small shaft downwards at angle, guaranteeing against any erections.

“Definitely,” Stephanie agreed, squeezing a large glob of diaper rash cream in her hand, “A sissy like Conrad should never have free access to his pee-wee.”

Tessa shook her head at the man she used to date.

“Just look at you–your girlfriend is about to go out on a date with another guy and here you are, with your little shrimp dick locked up and getting your wet diapers changed like a baby.
“Could you be any more pathetic??”

The object of their scorn looked away, tears threatening to tumble down his cheeks.

Taking a firm grasp of his ankles, Stephanie unceremoniously swung them up over his head and smeared the cream across his bottom, leaving a sticky white layer across his cheeks. With her other hand, she positioned a fresh stack of fluffy white diapers underneath his rump.

“Here you are, Pamper Princess,” she said mockingly as she powdered his front area and pulled the thick cloth up between his legs, “A fresh set of diapers for mommy’s little bedwetter.”

Conrad felt crushed with shame, getting changed like a helpless infant before these two beautiful women.

“Tell me, Conrad–is being a big baby everything you thought it would be?” his ex-girlfriend asked scornfully.

The sissy bowed his head, too mortified to be able to reply. To be sure, he was certainly regretting now the day his girlfriend found his secret stash of baby items.

Stephanie shook out a pair of yellow nursery print plastic panties and positioned them before his anklet covered feet.

“Here you are baby–your favorite plastic panties–do you think Tessa will think they’re cute?”

Conrad blushed a deeper shade of red but said nothing.

“What do you think,” she asked Tessa as she snaked them up her sissy’s skinny legs, “Do any of your new boyfriends wear these?”

Tessa laughed contemptuously.

“Not hardly.”

“You see–Tessa only sleeps with real men–not big babies like you,” she explained as she tugged the plastic panties up and over his fat, bulky diapers.

Standing up, Stephanie dusted her hands together.

“Well–I think you can take over from here, I’m going to get going.”

“Oh yes, I’ve got everything I need,” Tessa said somewhat mysteriously.

Stephanie took a tube of lipstick from her pocket and unrolled it, sliding it across her full, luscious lips as she checked herself in the mirror over Conrad’s pink dresser.

“If you need anything, just give me a call,” she said as she smacked her lips together.
Turning to face her deeply humiliated boyfriend, she wagged her long nailed finger at him in warning.

“And you better be on your best behavior, Mister, or your bottom will pay the price,” she told him as she gathered her things and made ready to leave.

Conrad gulped with anxiety.

The two women exchanged hugs and then Stephanie left, leaving the two of them alone in his nursery.
As soon as they heard the front door close, Tessa stepped over to the wall where the paddle was hanging from the peg. Picking it up, she smacked it hard against the open palm of her hand.

Looking her diapered ex-boyfriend squarely in the eye, she stood up straight and proud, her legs slightly apart in a commanding stance.

“I think you and I have a little unfinished business to settle.”

THE END

A Comprehensive List of my Work

Note, This is a complete listing of all of my work, including some stories I have never posted. I have put them into two categories; the first are stories that stand on their own, while the second are groupings in which one or more characters reappear in the same set of stories as a series.

Most can be found at Betty Pearl’s Stories Pub while the newer and shorter ones always get posted first on my home page at Fetlife. Readers can find me there, along with pics and stories under the user name of Bobby1111.

Over time, I will endeavor to upload all of my stories here, so that there will be one repository for all my work, available to anyone who enjoys it, and without charge.

 

 
A Sissy Gets Punished
A Sissy Learns His Lesson
A Sissy Tastes his First Cock
A Wife Takes Control
Be Careful Who You Steal Panties From (pics)
Bedtime For Bobby
Billy’s Dilemma
Defeated With a Kiss
Denna’s Babysitter
Ethan’s Slide into Sissihood
Getting Sissy Ready for Bed
Instructions For the Babysitter
Leanne’s Night Out
Melissa’s Solution
One Summer Day
Putting a Sissy in his Place
Reunion with an Ex-girlfriend
Seven Wet Nights
Stephen’s Rude Awakening (unfinished)
Substitute For Mommy
Surprise!
The Babysitter’s Surprise
The Date
The Dominant Wife
A Visit to my Sister’s House
Babysitting for my Sister

Barbara’s New Baby Girl
Barbara’s Baby Girl–3 Years Later

A Change for Danny
Danielle’s Birthday Party

Chrissey Series
A Sissy Gets More Than he Bargains For
Chrissey’s Wild Adventure
Chrissey’s Summer in Diapers

Tiffany Series
Tiffany’s Date
Tiffany’s Date–A Sissy’s Perspective
A Proper Fitting for a Sissy

Josh Series
Josh’s New Home
Back to School For Josh

Francis Series
Confession of a Bedwetting Sissy
Francis Meets His New Babysitter
Waiting for Mommy
An Afternoon With Francis
My Nephew–Still a Baby at 16

Ariel Series (Chastity Services)
A Surprise of Chastity
The High Cost of Playing with Panties
A Babysitter for Marcus

Baby Bobby Series
Bobby’s Babysitter
The Continuing Adventures of Baby Bobby
The Further Adventures of Baby Bobby–the Strict Nanny
A Sissy Gets Milked

Jimmy Series
Jimmy’s Return to Diapers
Jimmy’s Day at School
Jimmy’s Day of Shopping
Jimmy and his new Babysitter
Jimmy’s Potty Training Fiasco
Once a Sissy, Always a Sissy
Jimmy Gets A Mouthful

One Summer Day

It was a day I will never forget for as long as I live.
It had all started so routinely, a warm summer afternoon in which my mom had to go run some errands. Normally she would drop me off with my usual babysitter, old Mrs. Snagworth, but for some reason, she was unavailable today. So instead, she was going to leave me with another woman named Barbara.

I hadn’t seen Barbara for years, but I remembered her being very pretty. If I had to guess, I would’ve said she was from Norway or Sweden, maybe one of those Scandinavian countries. The last time I saw her, she had had long blonde hair, mostly straight, and it framed her gorgeous face and high cheekbones. In addition, Barbara had a very feminine air about her and there was something indefinably magnetic that set her worlds apart from other women.
Having said all that, I think it was her stunning blue eyes that made me unable to hold her gaze.

I had always been a very shy individual, and I found women like Barbara incredibly intimidating. The way she carried herself just gave me the shivers.
As for myself, I was unremarkable, being somewhat skinny and plain looking. Inevitably, I found when I received attention from people like Barbara that it was simply overwhelming to my youthful sensibilities.

Pulling into the driveway of the suburban home, my mom shut off the engine and we got out of the car. It was a nice neighborhood and somewhere down the street, a dog barked and then was silent.
Wordlessly, I followed my mom up the sidewalk to the front door, my heart beating nervously. I knew I was being silly, for Barbara had always been nothing but kind to me. And to be sure, she was a huge improvement on my usual babysitter, Mrs. Snagworth.

The door opened and Barbara smiled broadly as she greeted my mom. Quite frankly, I was completely astounded–she was even prettier than I remembered. As she bent down to say hi to me, I blushed hotly and looked away. I just couldn’t keep my eyes on her gorgeous face! My mom thought I was being rude and she slapped my arm, telling me to acknowledge Barbara’s greeting.

“H-hi, Miss B-Barbara,” I stuttered nervously.

She was wearing short shorts that revealed her long silky legs and a white top so thin that I could see right through it. I swallowed hard as I gaped at the gold swim suit bikini top underneath but it was the way that her big breasts were pushing her top out that had me so flustered.

At the tender age of ten, I was still in the midst of a sexual awakening of sorts, and I was starting to experience feelings I didn’t fully understand. Looking at the incredible form of Barbara standing before me, I felt a mixture of nervousness, excitement, intimidation, and arousal, all at once.

My heart was beating a million miles an hour as we stepped inside the comfortable house and my mom made small talk with her. I don’t recall a word of what they said as I looked around the living room anxiously, wondering what it was going to be like to be alone with this stunning, sexy woman.

All too soon, my mom said her goodbyes and made ready to leave, causing me to grab her wrist in a panic.

“Mommy,” I cried, “Can I go with you today?”

“Now Francis, there’s absolutely nothing for you to worry about. Barbara here is going to take very good care of you. I have a lot of stuff I have to do today and you’ll only get in the way,” she explained patiently.
I hung my head and shuffled my feet, knowing I was being difficult and immature.

“Francis,” Barbara said sweetly, “I have a really big back yard and a swing set that you can play on. I think you’ll have all kinds of fun while you’re here.”

“You see? You have nothing to worry about,” my mom added, “I’ll see you before long and I know you’ll have a good time.”

With that, she headed out the door and a moment later her car was pulling out of the driveway.

“Francis, make yourself at home,” Barbara told me, “is there anything I can get for you?”

I shook my head, still unable to look up at her beautiful but intimidating features.

“Okay sweetie,” she said cheerfully as she picked up a bottle of suntan lotion, “I’m going to head out to the back yard and work on my tan.”

I watched as she sauntered over and opened the sliding glass door, going out onto the stone patio that surrounded her pool. There were a number of lawn chairs and she sat down on one, peeling her top off in an incredibly delicious display that had me staring dumbfounded at her. At my age, I have never spent a lot of time looking at the adult female form, but hers seemed to be the epitome of perfection. With a super slim waist, it only seemed to emphasize her wonderful, big round breasts, and her shiny gold bikini top seemed unequal to the task of containing them.

Staring at her, I felt an electric buzz ripple through me and I licked my dry lips as I gaped hungrily at this incredible woman.

“Francis!” she suddenly called to me, “Can you bring me my cell phone, please?”

I swallowed hard and looked around the room before seeing the phone on the table. Scooping it up, I went out, opening the sliding glass door and handing it over to her.
I felt so incredibly awed by her, and as my eyes glanced over her flawless body, my heart was beating wildly.

“Thank you, sweetie,” she said as she accepted the phone from me with a smile.

I didn’t want her to catch me staring at her, so I hastily withdrew to the inside of the house, but once there, I turned back around to gaze at her again. With her back turned obliquely to me, I knew she couldn’t see me, and unconsciously, I reached down and began fondling the front of my pants as I took in the sexy scene.

She was doing something with her phone and looked oblivious to her surroundings so I knew I was free to indulge myself.

Masturbation was an entirely new sensation for me, as was my exposure to such a fantastic woman, and I wasn’t about to let this opportunity be missed.
She was talking on her phone now, and with the other hand applying suntan lotion to her smooth, perfect skin. I shook my head in amazement as the sun reflected off of her shiny curves, the lotion giving her a sensually erotic sheen.
I bit my lip and stroked myself, my eyes glued to this beautiful babe. All I could think was, what an incredible woman!

After several minutes of self indulgence, I began to get nervous, afraid she might suddenly turn around and see me playing with myself. Reluctantly, I turned and walked down the hallway, figuring I would explore her house a little bit.

Walking past the bathroom which didn’t interest me, I came to what I assumed was her bedroom. Everything about it was oh-so feminine and just breathing in the faint scent of her perfume filled me with contentment. A four poster bed with pink and lavender sheets was neatly made up and her large dresser had numerous pictures of her and her girl friends, all of who seemed similarly attractive. I picked up a few to admire before putting them back, trying carefully to return them to their original positions.
Next, I began opening drawers until I found the one containing her lingerie. Oh, the sights and sensations that were overwhelming to a youthful boy like me! Picking up one of her big-cupped bras like it was the Holy Grail, I gazed at it in wonder. Each cup was the size of my head!
God, she was incredible.

Finally, I sighed and walked out of the room.

The next room seem to be devoted to storage, which I walked past, but the next one instantly piqued my interest.
Surprised and intrigued, I stepped into what looked like a baby’s nursery. In one corner stood a crib with pink baby blankets, a mobile, and a teddy bear waiting patiently alongside the pillow. A vinyl floored playpen stood across from the crib, and a low chest of drawers was nearby it.
My heart quickly began beating faster.

The room smelled gloriously, like baby powder, and something else, maybe plastic, but it had that distinctively unique scent that brought me instantly back to my early childhood. Unfortunately for my mom, it had taken her forever to potty train me, and it wasn’t until kindergarten that I finally graduated to trainers. But even then, it was still a couple years before I could go to bed without wearing thick diapers and plastic pants every night.

Dropping to my knees, I knelt before a low changing table covered in waterproof plastic. My hands slowly stroked the playful nursery print characters decorating the surface before settling on a tall stack of cloth diapers. They were incredibly soft and thick, and without thinking, I quickly picked one up and held it to my face. My heartbeat quickened as I deeply inhaled the special, babyish scent. I blushed at the thought of being pinned into them.

I couldn’t explain or understand my feelings, but I felt like I was a cauldron of swirling sensations; excitement, arousal, and shame, all inextricably mixed together. What would Barbara think if she were to catch me here? The idea filled me with both trepidation and a certain naughty excitement, but I was sure that she wasn’t due to come back in for quite some time.

On a whim, I opened one of the drawers nearby and sure enough, a large selection of colorful plastic panties were to be found. They looked so cute and babyish, so much fancier than the plain white ones my mom used to dress me in.
I picked out a pink pair with nursery print and held it in my trembling hands. What would it feel like to wear waterproof panties again? For some strange reason, these excited me like nothing else. My little wiener had become stiff in my pants and a wet spot was forming in my underwear.

“So! You like to play with diapers, do you?” I suddenly heard from behind me.

In an instant, I tried to hide the panties behind me and I jerked around to face Barbara, who was standing in the doorway, still wearing her sexy gold swim suit. There was a mischievous smile on her pretty face and her slim hands were casually resting on her curvy hips as she looked down upon me. Her big breasts looked like two enormous melons, threatening to burst out of her much too small top.

“N-n-no, M-Miss Barbara,” I quaked in a panic, “I-I w-was just, um, looking.”
My cheeks burned with guilty shame.

Silently, Barbara crossed the threshold and came over to me, and as she bent down, her big, sexy bosom was only a foot from my gaping face.

I gulped hard and a trickle of sweat appeared on my forehead.

“It’s okay baby,” she smiled warmly at me, “some little boys still need to wear diapers and plastic panties, it’s perfectly all right.”

Totally at a loss for words, I swallowed hard and looked around the room nervously, my cheeks burning.

“I’ve been watching you for several minutes now, so there’s no point in trying to deny it,” she explained calmly, “I think you’d like me to pin you into some diapers of your own.”

The redness in my cheeks spread to my chest and ears and I felt my hands trembling.
Without another word, she began slowly untying my shoes and removing them but when she reached for the button of my jeans, I put my hands up in panicked protest.

“No–wait, I-I was just–just exploring,” I lamely whimpered, almost on the verge of tears.
As over-the-top sexy as she was, I was crushed with humiliation to be caught red-handed in here. If it had been Mrs. Snagworth, maybe it wouldn’t have been so bad, but being confronted by a gorgeous babe like Barbara made it ten times worse.

Ignoring my whining, she briskly and authoritatively undid my pants, unzipped them, and pulled them down off my skinny legs, making me squeal with angst.

“I’ve got just the thing for a little boy who likes to wear pampers,” she said in a soft, sultry voice, her gorgeous smile washing over me like a warm bath.

My heart was racing and my mouth was dry. What was I to do?

Taking three of the bunny soft diapers I had been fondling just moments before, Barbara put a thick soaker pad down the center and then slid the white cotton stack under my rump.

“You won’t be needing these anymore,” she said with a grin as she snaked my Batman underwear down my legs and off of my feet. I squealed again and blushed with embarrassment as my bald little pee-pee came into view. Other than myself, no one had seen it except for maybe my mom, and that was only during bath times. Being limp with fear, it was no larger than either of my two little balls on either side.

Squeezing a generous portion of diaper rash cream on her buttery smooth hands, Barbara smeared it gently across my youthful cheeks, covering the surface of my sensitive bottom with the cool, sticky substance. After lowering my legs back down, she began powdering me with Johnson’s, and unconsciously, I breathed it in deeply.

For so long, I had wondered what it would be like to wear diapers again. And now, here was this stunning woman lovingly pinning me into a set just like I was her own little baby. Gazing up at her, I felt our age difference very acutely, even though she was only in her mid-twenties.

“Looks like someone likes to wear diapers,” she grinned as she powdered over my now stiff, throbbing little member.

I blushed again and looked away but not for long. The view of her luscious bosom was getting me so hot, along with her wonderful ministrations that I was on the verge of having an explosive orgasm right here!

“I’ll bet my little baby likes the pink bunny pins,” she said as she held one of the safety pins before me. It looked like something an infant girl would have pinning her diapers together and shamelessly, I nodded my head.

“Mm-hm,” she said smiling as she slipped them through the corners of the soft cotton cloth, “I thought so…I think there’s a bit of a sissy in you, Francis.”

Biting my lip, my cheeks burned hotly with embarrassment but I was too worked up to argue with her.

Humming to herself, Barbara pulled the other side tightly and pinned it closed as well.

“And since you’ve already picked out your baby panties, I’ll just put them on for you,” she continued in her warm, yet teasing tone.

My head was swimming with the magnitude of feelings sweeping through me. Deep humiliation mixed with intense arousal–it was like nothing I’d ever experienced.

Gathering the delicate panties in her beautifully manicured hands, she guided my feet through them and began working them up my slender legs.

“Look at me, Francis,” she said sweetly as she slowly pulled them past my knees.
Blushing a deep red, I gingerly looked up at her dazzling blue eyes. They were glittering playfully and I swooned with emotion.

“I want you to remember this moment–the first time you were put back into diapers and plastic panties. It’s a moment little boys never forget.”

I didn’t doubt her for a moment. I would never forget this for as long as I lived!

Pulling the cute vinyl panties up over the huge diaper swaddled around my hips, Barbara used her fingers to work all the cloth inside until it was fully contained. Then she pulled my t-shirt off and over my head, setting it aside.

“I think I have something that will fit you here,” she said as she went over to the closet and rummaged around for a moment.
Looking down at the shiny pink plastic covering my diapers in its snug embrace, I breathed in the babyish scent around me, reveling in the powerful sensations.

“Here we are,” she said brightly, bringing over a frilly short top with puffy sleeves.

Raising my arms to her, she dropped the short top over my head and helped fit it around my torso. Kneeling down again, she removed my striped socks and replaced them with some shorter, fuzzy toddler socks, following them with a pair of pink Ked’s sneakers.

Taking my hand, she helped me to stand and she led me over to a full length mirror on the far wall.

“Take a look at yourself, Francis–or should I say, Baby Francis,” she giggled.

My cheeks were a bright, blazing red as I beheld my babyish reflection. I was deeply ashamed, having submitted to being dressed like a diapered toddler but then Barbara’s seeming acceptance of my appearance helped me to cope with my conflicted feelings.
Bending down slightly behind me, Barbara patted me gently on my fat, plastic covered bottom, beaming back at me in the mirror. Reaching over to the top of the dresser, she picked up a pink and white pacifier and eased it between my lips.

“There, you just suck on that for a bit–I’ll be back in a couple of minutes.”

After she strode out of the nursery, I continued to gaze at my reflection in the mirror. I couldn’t believe I was dressed as a baby! I looked just like a little diapered toddler girl.
Turning around, I twirled slightly to see my reflection in back. The diapers were so thick and round, so curvy and fat across my bottom, it made me feel very babyish.

When I had first entered the room a half hour ago, I’d felt like an outsider but now I felt like I belonged here.
My eyes gazed around, taking in all the sights when Barbara came back in, carrying a pair of baby bottles filled with milk.

“If you’re going to act like a baby–I might as well treat you like one,” she said with her pretty smile.
Taking my hand, she led me into the crib and then sat on the edge so she could cradle me in her lap. With her left arm, she supported my head and brought me up close to her mouthwatering breasts, putting my face mere inches from them. I mewled with intense feelings of intimidation, mixed with white-hot arousal. Her skin was so soft and velvety, and her cleavage close enough I could kiss it. My heart was pounding wildly in my chest.

Before I could ponder any further, she pulled the pacifier out of my mouth and pushed the warm rubber nipple of the bottle between my lips. I squealed helplessly but soon began nursing submissively.

“That’s my baby…” she cooed softly as she rocked my head in her arm, “That’s my little baby.”

I drank and drank, occasionally stealing glances up into her dancing blue eyes. God, she was beautiful.
I think I was falling in love.

Even though I didn’t particularly like milk, especially warm milk, I emptied the bottle fairly quickly and tried to get up, only to have her hold me in place. Removing the first bottle, she put it aside and quickly replaced it with the second full bottle. I squirmed and whimpered in protest but she held it firmly, forcing me to nurse like a helpless toddler.
I didn’t want to drink it but still–I couldn’t really complain. Her big breasts were so close to my face, I could smell her alluring skin and the view of her deep cleavage, inches in front of my nose, was fabulous.

Nevertheless, by the time I finished the second bottle, I was well and truly full.

“I know–why don’t we go outside and you can play on the swing set?” she asked enthusiastically.
The thought of going outside like this sent me into a wild panic–the last thing I wanted was to be seen by anyone else on this planet while dressed like a baby girl.

“B-but…won’t people be able to…you know…see me?” I asked uncertainly.

“Oh no–don’t worry, baby,” she reassured me, “The walls around my yard are high enough so no one can see in. It’s very private.”

Not entirely convinced, but not wanting to oppose her on anything, I gave my reluctant consent. Leading me by the hand back out of the house, I waddled awkwardly and soon felt the warm summer sunshine upon me as we stepped outside. The soft diapers felt wonderful between my thighs and the plastic vinyl panties swished pleasantly. Still, I felt extremely naked and exposed with these fat babyish underwear so humiliatingly displayed.
I glanced around the yard, my eyes everywhere, fearful of discovering a way that someone might see me.

Taking me over to the swing set, Barbara helped me get into the seat, which proved somewhat difficult, due to the bulky width around my hips. She had to practically wedge me in but once settled, she positioned herself behind me and began pulling me back to release me. I pulled on the chains and began swinging higher and higher, the wind tickling my bare legs. I couldn’t believe I was outside and dressed like a baby wearing diapers and pink plastic panties! I felt exhilarated and free!

She pushed me every time I swung back and I cried out with joy.

“WEEEEE!!!”

Sometimes, I would swing so high that I could catch a glimpse of the yard next door, and I blushed again to think that they might be able to see me too. Nevertheless, I continued swinging happily until I felt Barbara stop pushing me.

“You keep playing, Francis, I think I hear my phone ringing,” she said from behind me.

I didn’t mind at all and I kept swinging while she went inside.

It seemed like she hadn’t been gone for more then ten minutes when I started to feel a pressure building in my lower area. Slowing my pace, the swing went forwards and back, the momentum decreasing as I realized I hadn’t peed all morning and the milk was starting to take effect on my bladder.
Reluctant to stop playing, I held it in and continued swinging, until a particularly strong pang hit me.

With a sigh of resignation, I brought the swing to a halt and tried to stand up but the swing set was gripping the fat bulk of my diapers and wouldn’t let go. Wrestling with it, I finally managed to extricate myself and just in time. Another really strong wave of need rippled through me and I just barely managed to stop it. I had to go!

Waddling as quick as I could, I made my way to the sliding glass door and pulled on the handle only to find that it was stuck. Now in a panic, I jerked it wildly, trying to open the jammed door. I yanked it again and began pounding on the glass, trying to get Barbara’s attention. Where was she??

Suddenly–to my horror, the floodgates opened and an overpowering, strong surge of hot, urgent pee streamed into my waiting diapers.

Oh no!!!

The thick cloth between my legs quickly grew heavy and warm with pee and I sobbed with despair. If I didn’t feel like a complete baby before–I certainly did now!

Finally, I saw Barbara striding quickly across the room inside, as she hurried to open the door for me. Her cell phone was still in her hand as she yanked the door open and looked down at me with genuine concern across her pretty face.

“Oh baby–I’m sorry, sometimes that door locks itself when you close it–is everything okay?”

Tears spilled down my face as I stared at the ground between us.

“I-I-I w-wet my diapers,” I sobbed miserably. I felt so ashamed and incredibly childish.

“Aww baby,” she said as she gathered me in her arms, mashing my face against her big soft breasts, “That’s okay, sweetie. Don’t you worry about a thing–I’ll get you all fixed up in a jiffy.”

My cheeks were red with embarrassment and as I swallowed my tears, I let her take my hand and lead me inside. While it was mortifying, wetting my diapers like a little baby, I was relieved that she wasn’t angry with me. Grabbing another baby bottle out of the warmer in the kitchen, Barbara led me down the hallway and back into the nursery.

“I’ll just change your diapers and then it’ll be naptime for you,” she said cheerfully.

“N-naptime?” I quailed, “I don’t take naps anymore.”

“Little babies that wet their pampers need to take naps in the afternoon, Francis,” she explained patiently.

Although I didn’t like the idea, I was reluctant to argue with Barbara. I didn’t want to do or say anything to make her not like me.
Sitting me down on the changing table, I felt the warm, wet cloth squish humiliatingly against my bottom. I was about to launch into a spirited defense as to how it happened and why it wasn’t my fault when Barbara pushed the rubber nipple of the baby bottle between my lips.

“Drink that up, sweetie,” she said as she began peeling my clinging wet plastic panties down off my sodden diaper, “Babies need their milk.”

I blushed and did as I was told while she unpinned my diapers and removed the wet cloth beneath me. The air around me smelled like pee and I blushed again, sure that Barbara had determined that I was incapable of controlling my wetting.
Taking a pair of baby wipes, she began carefully cleaning my bottom and groin, paying close attention to my little penis. Looking up at her prominent bosom that was swaying slightly within her bikini top, I felt myself stiffening immediately.

“Well Francis, are you a big boy? Can you be trusted not to wet the bed or do I need to put you back in diapers again?” she asked as I lay there getting more worked up by the second.

I swallowed hard, my cheeks burning with embarrassment. Clearly, she thought I was still so immature that I very much needed diapers. And yet, I was so incredibly turned on, looking up into her pretty blue eyes that the thought of her pinning me back into diapers was overwhelming.

“Y-yes Miss Barbara,” I stammered nervously.
“Yes what?” she replied.
I swallowed hard as I gazed at her big pendulous breasts.
“I um…need d-diapers,” I admitted shamefully, my cheeks again burning hotly.

“Then ask me properly, baby boy,” she told me.
I cleared my throat, unable to look her in the eye.
“P-please…will you, um…p-put me back in d-diapers, Miss Barbara?”
I couldn’t believe I was saying those words–I was so humiliated! I was basically admitting that I wasn’t potty trained yet.
“–And plastic panties–say it all together,” she corrected me.
I gulped back my crushing humiliation.

“Um, will you please…um, p-put me back in diapers and p-plastic panties, Miss Barbara?”

“I’ll be happy to,” she said with a smile that could melt ice, “A baby bedwetter like you needs all the protection he can get.”
Her words stung me to the core but I was too turned on to care.

After another coating of Desitin, Barbara slid another tall stack of soft, fluffy white diapers beneath my bottom and powdered me generously. Pulling the pillowy bulk between my legs, Barbara beamed down at me.

“This will keep baby’s crib dry during naptime.”

Pinning the diapers around my slim hips snugly, she picked out a white pair of nursery print plastic panties and gathered them in her hands. Nursing from the bottle, I whimpered a little as I watched her slide the babyish panties up my hairless legs, taking her time to fit them around my voluminous diapers.
With that, I felt once more, like I had been returned to babyhood.

“There–all safe and secure again,” she said with satisfaction and she began removing my Ked’s sneakers.
I finished the milk and after taking back the bottle, Barbara guided me into the pink crib. I sighed as she pulled back the soft baby blankets and helped me in, tucking the diapered teddy bear under my arm.

“Here you are, baby Francis,” she said as she pushed a rubber pacifier in between my lips again.
I returned her smile as she lifted the side rail and clicked it in place, starting the mobile above my head.

“Sweet dreams, little one,” she said as she left the room, turning out the light as she went.

Lying on my back and listening to the nursery rhyme, my hands immediately went down beneath the blankets and I began aggressively rubbing the front of my diapers. It felt wonderful and I had never been so aroused in all my life. I masturbated furiously, rubbing the cushiony soft cloth of my diapers and enjoying the buttery feel of the plastic panties as I re-lived Barbara’s humiliating words to me;

“Well Francis, are you a big boy? Can you be trusted not to wet the bed or do I need to put you back in diapers again?”

I blushed again as I heard her words in my head and in moments, I exploded in the most powerful orgasm I’d ever experienced. My eyes crossed and a low moan escaped my lips.

Gasping for air, my head was spinning as I slowly came down from the intense rush of my climax. My chest was heaving and finally, I had been able to satiate the tremendous, consuming need that had had me in its grip since I first arrived at Barbara’s house.

With the release of all that tension, I was finally able to relax and in the peaceful quiet of the nursery, I slowly drifted off to sleep.

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

Slowly and gradually, I felt myself coming out of the clutches of slumber, as I hazily became aware of the sound of indistinct voices somewhere else in the house. Feeling groggy, I sleepily opened my eyes and was momentarily disoriented as to where I was. Surrounding me were the reassuring pink bars of the baby’s crib and looking through them, I could see the familiar infantile furnishings of Barbara’s nursery.

Yawning, I pleasantly recalled the wonderful orgasm I had enjoyed before falling asleep. My big diapers had felt so comforting, so bunny soft and wonderful.
It was only then that I felt the warm but clammy wet embrace of the Birdseye cloth surrounding me.
In a panic, my hand shot down to confirm my worst fears–my diapers were soaking wet!!

How had that happened? I remembered drifting off to sleep after playing with myself but nothing after that until now. I hadn’t wet the bed in years and I was at a total loss to understand what had happened–what would Barbara think?

Suddenly, I heard voices from down the hall and I realized belatedly someone else was in the house.

“He’s sleeping in this room?”
“Yes, it seemed more appropriate for him, since the mattress is protected by a waterproof sheet.”

I bit my lip in fear as I instantly recognized my mom’s voice and it filled me with utter panic. Before I could think of what to do, the door to the nursery opened abruptly.
Barbara strode into the room, now fully dressed, followed by my mom. Strong waves of shame washed over me and I blushed furiously as they came over to the crib and looked down over the rail at my cringing form.

“Well now…so it’s true–looks like someone wanted to play baby today,” my mom remarked sardonically.

Barbara smiled down on me warmly–she was wearing a pink, snug fitting button top that clung tightly to her mouthwatering breasts and she lowered the crib rail, taking my hand and helping me to sit up. Without thinking, I clutched the teddy bear in my arms for comfort as I struggled to think of some sort of explanation for my mom, who was crossing her arms over her chest, shaking her head in disapproval as she looked down on me.

Barbara took a seat on the edge of the crib mattress and she pulled me over her lap, cradling me in her arm again as she produced another baby bottle of milk.

“No-no!” I cried, putting my hands up in protest. Now that my mom was present, playing baby for her had lost all of its appeal.
Ignoring my pleas, Barbara pulled me down on my back and over her lap so I was once again facing her and her enormous bosom. Unfortunately, this had the effect of pulling me out of the cover of the blankets, fully exposing my baby outfit and fat, shiny diapers for my mom. I watched as her jaw dropped in shock and she beheld her sissy son, looking like an over-sized baby girl.

I tried to say something by way of explanation but Barbara pushed the bottle in between my lips and my words were muffled by the wet rubber nipple. Warm milk dribbled down my chin and dripped onto my chest. I squealed and whined, the panic causing a fresh stream of hot pee to flow into my already wet diapers.
As if reading my mind, Barbara reached down and slipped a finger inside the elastic leg hole of my plastic panties, feeling the soggy wetness inside.

“Looks like baby Francis wet his diapers during his nap,” she announced with a maternal smile.
My cheeks blazed with shame and I sucked desperately on the bottle, the humiliation crushing me.

“Francis–what has gotten into you?” my mom demanded angrily.
I gulped hard and struggled in Barbara’s arm, trying to get up but she held me in place.

“Not yet baby, finish your bottle first,” she chided me.

“Francis–I don’t know what’s gotten into you but when we get home, you can count on taking a trip over my lap. Remember what happens to bedwetters?” my mom scolded me.

I whimpered as my eyes brimmed with tears. I hadn’t been spanked in years but the last time, her paddle had left my crying like a baby.

“Would you like me to change his diapers before you go?” Barbara offered helpfully, “Its no trouble.”
She sounded so casual, she made it sound like it was my usual clothing.

“No,” my mom replied, her expression dark, “Since he wants to dress and act like a baby, he can just wear his wet diapers home. After that, he’s got an appointment with the paddle.”

Barbara giggled as she held the bottle to my lips.

“These plastic panties should be able to handle his wetting until then–and I can give you a fresh change to take with you for his beddie-bye if you like,” she suggested.

“Yes,” my mom said conspiratorially, “My little baby will be wearing his diapers to bed after his bottom’s been warmed.”

Finally, the bottle was empty and Barbara helped me up. She quickly gathered several thick, fluffy diapers, plastic panties and some baby powder, handing them over to my mom.

“Well Francis, it was fun having you over. I hope you had a good time,” Barbara said as she bent down and hugged me closely. I sniffled, wondering how things could have gone so wrong for me today. Seeing my sad face, Barbara popped the pink pacifier in my mouth and beamed down at me.

“You can keep that sweetie, I’m sure it will make you feel better on the ride home.”

I blushed hotly, wishing now that I’d never come over here.

“Come along, Francis, the paddle’s waiting for you,” my mom told me as she took my hand and led me to the door.

THE END