My Nephew, Still a Baby at 16
Posted on October 28, 2016
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
Posted in My other stories... | 3 Comments
The Perverse Revenge of Miss Hazel
Posted on August 18, 2016
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
Posted in My other stories... | 3 Comments
Surprise!
Posted on February 7, 2016
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
Posted in Bobby's Stories, My other stories... | 3 Comments
Reunion With an Ex-girlfriend
Posted on February 1, 2016
“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
Posted in Bobby's Stories, My other stories... | 6 Comments
One Summer Day
Posted on February 1, 2016
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
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Barbara’s Baby Girl–Three Years Later
Posted on March 31, 2013
Chapter One
The last flush of the toilet signaled to Barbara–my de facto mommy, that I was finished in the bathroom, having finally spent the warm, soapy two-quart enema she’d administered twenty minutes earlier.
This was all the more obvious, since the door was wide open as it was required to be on those rare occasions when I was allowed into the bathroom.
Stepping out sheepishly, I looked up into the lovely blue eyes of Barbara.
“All done, Sweety?” she asked pleasantly.
“Yes Mommy,” I replied.
Daily enemas were Barbara’s way of avoiding messy diapers with me and the truth was, I couldn’t remember the last time I’d had a normal bowel movement. I was afraid to imagine how weak my muscles might have become should I ever go a morning without an enema. After living three years in Barbara’s house, I was now hopelessly incontinent and diapers were an absolute necessity.
Having pulled off the pair that I had soaked last night to give me my enema, I was now naked except for my fuzzy Strawberry Shortcake diaper shirt and frilly pink anklets.
Barbara reached down and grasped my hand, leading me firmly back to my nursery.
“How’s mommy’s little girl today?” she asked brightly.
“Good, Mommy,” I replied, gripping her warm hand tightly.
I felt not only naked but somewhat vulnerable outside of my nursery and I was anxious to get back to where my toys and stuffed animals awaited me.
Padding down the hall, we entered the bright and warmly lit room that was home for me 95% of the time. The morning sunlight streamed into the room through soft, gauzy pink curtains, filling the nursery with the makings of a new, happy day.
My room was decorated much like any little toddler’s, with soft pastel colors and a wonderful Disney Princess theme throughout. A large pink and white baby’s crib dominated the room, now open and revealing the nursery print waterproof mattress cover that helped guard against leaks during the night. To the right was my changing table, a slightly raised surface also covered with a practical vinyl plastic for my frequent diaper changes. On the other side stood my pink dresser with my extensive doll collection arranged across the top. Inside the drawers were a vast collection of diaper shirts, onesies, frilly anklets, and bonnets.
On the opposite side was my playpen with its soft padded rails and plastic lined floor where I spent most of my afternoons when Barbara was busy. A large diaper pail sat nearby and even though the lid was tightly sealed, a distinctive aroma of stale pee nevertheless pervaded into the room, serving as a constant reminder of my childish incontinence. Nobody visiting could fail to notice that this was the room of a bedwetter.
Stepping over to the changing table, Barbara helped me to take my place upon its shiny plastic surface, gathering a fresh set of diapers for my morning use.
“Looks like your diaper rash is much better this morning, Chrissey,” Barbara observed happily.
“Yes, Mommy,” I replied, relieved that the generous slathering of ointment she had applied to my bottom the last few days had done it’s trick.
Lifting my legs by my ankles, she slid a thick trio of bunny soft cloth diapers under my upturned rump.
“Say hello to your diapers, Babygirl,” she said with her beautiful smile.
I giggled merrily as she powdered me generously, filling the air around me with that all too familiar but wonderfully babyish scent. Breathing deeply, I sighed with pleasure as I watched Barbara select a pair of Duckie headed diaper pins.
Today she was wearing a short skirt that showed much of her fabulous thighs–firm thighs that I was frequently bent over, either for my morning enema or more rarely, for a sound spanking. Fortunately, the latter had become much more infrequent although there were still occasions in which she felt my behavior warranted a session with her hard, unforgiving oak paddle. Not one to tolerate any nonsense, Barbara wouldn’t hesitate to punish me, whether alone or in front of company if she felt I deserved it. Her spankings never failed to leave me sobbing like a baby with tears streaming down my face and incoherent apologies tumbling out of my mouth.
But today she was happy and I was happy to be her baby. I couldn’t imagine a life without her.
As she bent forward to pin the side of my diapers, I gazed in admiration down the front of her nearly see-thru blouse. This morning, she was wearing a snow white top that her big, round, milk-laden breasts filled to capacity, straining mightily against the buttons. I smiled as I noted the smooth edge of her bra, plainly visible from my vantage point.
Barbara was a goddess by any standards. Although she was in her late thirties, she was in far better shape than many girls in their teens. Tall in stature, with a skinny waist and massive, jaw-dropping breasts, she inevitably turned heads wherever she went. All that and a face that stopped traffic with her pretty brown eyes had me head-over-heels in love with her years ago.
But as she bent forward to pin the other side of my diapers closed, I couldn’t help but be entranced by the heavy sway of her beautiful bosom. Any other guy of 17 would be rock hard at the sight but that was quite impossible for me. Years ago, when Barbara had first taken me in to become her baby girl, she had immediately taken the measure of placing my little penis into a foolproof chastity device which has remained forever locked since that first fateful day. Since then, I haven’t been able to get hard, play with myself, or have an orgasm of any kind, regardless of the circumstances. So despite the fantastic view that was before me, my insignificant noodle remained imprisoned and controlled, just as every other aspect of my life was controlled by Barbara.
With both pins now in place, the thick cloth of the triple diapers forced my legs apart which I knew from experience would cause me to waddle as I toddled around the nursery. This was not really much of an issue, since there was virtually no place for me to walk to. Confined to the inside of Barbara’s house, I spent most of my time crawling around from one side of my nursery to the other. Even some parts of the house were off limits to me, like the garage, the spare bathroom, and of course, Barbara’s master bedroom. And with the sole exception of my nursery, Barbara never let me out of her sight for one minute. Even when I was allowed out into the living room, more often than not, I was restricted to the playpen she kept there so she could keep an eye on me.
She was humming to herself now as she sifted through the overflowing drawer of plastic panties.
“Let’s see…what does mommy have for her precious little babykin’s…” she mused aloud, “How about these?”
Stretching a pair of semi-translucent pink panties with bunnies on it between her fingers, she beamed down at me expectantly.
“Uh-huh,” I nodded breathlessly.
I loved the super soft vinyl of these cute panties which were heaven to wear.
Gathering them at the legholes, she worked them over my feet and slid them up my calves. I mewled babyishly as she raised them up my skinny thighs and began tugging them up and over the thick, yet comforting bulk of my diapers. Once it was enclosed, she worked her manicured fingers around the elastic waistband making sure all the cloth was on the inside and then did the same with the leg holes. I shivered with delight as her silky fingers touched the sensitive skin of my inner thighs.
As a finishing touch, she powdered between my legs, leaving a whitish layer between my skin and the vinyl of the panties.
“Well–just look at you, Miss Prissy Pants!” she exclaimed eagerly, “All diapered and ready for the day.”
I blushed slightly and looked away, even though my sense of safety and security felt palpable now that I had been changed.
“Now we just have to find a sweet baby dress for mommy’s little sissy,” she said as she patted the fat front of my diaper playfully.
Standing up, she went over to my open closet and began carefully looking through the vast selection. There were countless dresses and rompers, most in pink, yellow, white, or baby blue.
After moving through the first third, she selected a white sailor suit with soft pink satin lace and a big pink floppy bow over the traditional bodice.
“How about this, sailor sissy?” she asked enthusiastically, “Are you ready for the high seas?”
Despite the beguiling smile on her pretty face, her tone was one reserved for toddlers and children and I couldn’t help but hear what sounded like sarcasm.
“Yes Mommy!” I replied immediately. Even though it was still humiliating after all this time, I still enjoyed playing her game if only to bask in her intoxicating beauty.
Dropping the light frilly garment over my head, she turned me slightly and as my arms went through the short, puffy sleeves, she zipped up the back behind my neck. I felt so girly as I felt the delicate pink lace around the short hem and admired the big floppy pink bow underneath the Peter Pan collar.
Kneeling down, Barbara took my Mary Janes and buckled them over my feet which were still wearing the frilly white anklets. Taking my hand, she gently stood me up and had me look at the large, full length mirror permanently mounted to the opposite wall.
As I gazed at my sissyish reflection, I was amazed at how babyish I looked. My hair was short and curly, with a Shirley Temple style Barbara had permed years ago. The sailor dress was so short it barely covered the waistband of my plastic panties, leaving my babyish thick diapers fully on display. And my soft, smooth legs seem to compliment my girlish appearance, lacking any muscle tone or hair at all. If they had ever looked boyish before (and I couldn’t remember them being so), they certainly weren’t now.
Turning around, I admired the perfect round curve of my thickly padded and pantied bottom. I sighed with satisfaction as Barbara bent down to softly pat my seat.
“Aren’t you just the CUTEST little girl on the block?” she whispered with a proud smile.
I blushed again, embarrassed at my own sissyishness.
Still looking at our mutual reflection in the mirror, Barbara bent down slightly to speak closer at my level.
“Do you want to wear some rumba panties with your dress or leave your plastic panties on display?” she asked with interest.
“Umm, I think I’ll go with just these,” I said shyly, casting my eyes at the floor.
“Can you tell mommy why you don’t want some rumba panties? ” she asked softly.
“Ummm,” I said hesitantly, “cause I um…like the bunnies,” I said barely audibly as I pointed at the colorful yellow bunnies decorating the shiny pink vinyl panties.
“Okay Chrissey,” she said with a giggle that made me blush crimson, “you can wear these pretty panties by themselves.”
As she gently stroked the soft, thick seat of my diapers, her beautiful bosom jiggled and I shivered with delight.
“I love you Mommy!” I suddenly blurted out, throwing my arms around her slim waist. Because she was so much taller than I was, I found my face mashed against her big, pillowy breasts.
“Mommy loves you too, Sweety,” she said with amusement, hugging me in return.
“And mommy has a special surprise in store for her baby girl,” she said as she led me over to the side of my crib. Sitting down on the edge of the plastic lined mattress, she guided me next to her and produced a slim catalog with a sexy woman on the cover dressed like a baby.
“My little sweety’s birthday is coming up and I thought you’d like to pick out some new baby outfits,” she explained as she put her arm around me. It always gave me an electric thrill to have her touching me, partly because I’d never been touched by a female except for my real mom, but also because she was so incredibly sexy. Sitting next to her on the edge of the crib mattress, I had the opportunity to gaze surreptitiously at her tremendous breasts that were threatening to burst out of her snug top. Barbara didn’t like me staring at them, and in fact, she’d spanked me in the past for doing it blatantly but at the moment, there was no way to avoid it.
“Oh yes, Mommy!” I exclaimed, “That would be wonderful!”
I was used to Barbara making every conceivable decision for me, whether it was what I was to wear, eat, or when my bedtimes were, so this was an extraordinary privilege.
Flipping past the first few pages to a section on dresses, she smoothed the catalogue out over our laps.
“Here’s a lovely play dress,” she pointed out, indicating a cute little dress with designs of ducks and bunnies on the bodice.
“How do you like that, Chrissey?” she asked.
“I like it very much, Mommy,” I admitted shyly.
“And here’s one in pretty pastel yellow–just look at all that lace, Honey!” she exclaimed.
“Uh-huh,” I acknowledged.
Between the cute, babyish clothes and the warm proximity of Barbara’s sexy body, I was starting to become very aroused. My tiny penis was starting to throb anxiously and I tried hard not look at the luscious curves of her breasts that were each, nearly the size of my head.
Flipping the page, she pointed out a diaper shirt and chuckled with amusement.
“Oh–here’s one that’s just right for you, Chrissey–see what it says on the chest? ‘Still a bedwetter’.”
I blushed with embarrassment.
“Yes Mommy,” I whispered.
“Would you like that top, Baby?” she asked in a seductive voice.
“No Mommy,” I shook my head.
“Who’s the little baby bedwetter in this room?” she nudged me.
“I am, Mommy,” I mumbled as my cheeks reddened.
“You certainly are–I think we’ll get it anyway–its so perfect for my little sissy.”
Sometimes Barbara asked me questions for which I knew she’d already decided the answer beforehand. This was apparently one of those times.
“I just love these tops with the cute phrases,” she continued, “here’s another one…read what it says, Chrissey…” she prompted me.
I cleared my throat and paused awkwardly.
“Sissies wear diapers,” I squeaked.
“Wouldn’t that be a perfect shirt for you, Chrissey?” she asked eagerly.
“Umm…I guess so,” I replied uncertainly.
“Chrissey–you’re mommy’s special little sissy and you’ll always be in diapers,” she assured me confidently.
Looking up into her gorgeous, smiling face, I felt her love for me and I sighed happily.
“Yes, Mommy.”
I’m so glad we could share this mother-daughter moment,” she said as she hugged me closely. I savored the feel of her plump breasts pressing against my cheek.
“Me too, Mommy,” I agreed.
Flipping the page, we got to my favorite section, the page with the panties.
“Baby likes her pretty panties, doesn’t she?” Barbara cooed.
“Yes Mommy,” I admitted.
Truth was, I’d always had a secret fetish for girl’s panties and though it was unlikely I’d ever get to wear them, my preference had shifted to baby panties and diaper covers.
“Ohh, now look what they have here,” she said, “It looks like you can get lace around the legs and waistband of any of these plastic panties. Wouldn’t that be cute?”
“Uh-huh,” I agreed.
Suddenly, and without any warning at all, I felt the cloth between my thighs growing warm and wet. I was peeing freely with a strong surge and I only barely managed to stop the flow. Even so, a few good squirts still managed to add to the already saturated cloth, before I could bring it to a halt.
“M-Mommy!” I squealed, “I just wet my diapers!”
Barbara looked up from the page and casually placed her hand on the warm, cushiony front of my vinyl panties.
“That’s okay, Honey,” she said calmly, “It can still take quite a bit more–I’ll just change you after breakfast, okay?”
I sniffled and nodded, knowing she was right. Even my daytime diapers were extra thick, enabling multiple wettings before a change was necessary. The down side of that was that I was often wearing a wet diaper more often than not.
“Now–tell me which panties you’d like to get for your birthday,” she urged me.
“Umm…I kinda like these,” I said, pointing to a pair of nursery print plastic panties with clowns and blocks.
“Oh yes, those are very cute, aren’t they,” she concurred, “would you like lace around the legs too?”
“Uh-huh,” I said, too embarrassed to look her in the eye.
“How about some satin rumba panties? Do you like the pink ruffles on this one?” she asked.
My little penis was starting to throb inside the chastity tube although at this point, it wasn’t too painful, just a growing ache that was making me conscious of my ever present need to cum.
“Mm-hm,” I nodded.
“These would look super special with the pink party dress Pamela got you, don’t you think?”
I blushed beet red at the mention of my real mom. Years ago, before she sent me to live with Barbara, I used to manipulate her at my whim. Now the roles were reversed and she never hesitated to humiliate me whenever she came to visit.
“Yes Mommy,” I mumbled as I looked away.
“You know, I’ve got another surprise for you Chrissey,” she said excitedly, “Today I’m going to take you to the park and let you play in the kiddie’s sandbox–won’t that be fun?”
My mouth hung open in shock as I turned to look up into her beaming smile. Suddenly, I felt another strong flow of pee soaking the cloth between my legs again and I cried out in angst.
“Oh!” I whimpered in my high-pitched girlish voice.
Barbara’s face took on a look of confusion.
“What’s the matter Sweety? Don’t you want to play outside? I thought you’d be dying to get back out again after all this time.”
It was true that I hadn’t been outside for nearly three years. Barbara had kept me cooped up inside here for so long I had forgotten what it was like in the outside world. At first, I’d been deeply resentful and thrown numerous temper tantrums to force her to my will. Without fail, these always resulted in my being pulled over her lap for a blistering spanking. After becoming intimately familiar with her unforgiving wooden paddle, and after countless tears had been shed, I learned not to question her rules.
Some time later, after I got settled into a lifestyle befitting a toddler, I tended to forget about my previous life and in fact, after my initial bout of resistance, I actually came to enjoy being babied.
Now she was talking about taking me not only outside, but out in public where others would see me.
“Am…am I gonna go out d-dressed like this?” I asked with a shaking voice.
“Oh course, Honey, what else would you wear?”
“B-but–everyone will see me–you know…dressed as a b-baby.”
“That’s because you ARE a baby, Chrissey. How else would you be dressed?”
She seemed honestly perplexed at my question.
Looking down at my bare legs, my bulging diaper and the lacey hem of my sissy pink sailor suit, I was terrified to think what people would say if they saw me in the park.
“No Mommy–I can’t!” I squealed.
Barbara reached forward and calmly grasped the large pink rubber pacifier that was permanently kept on a loop around my neck.
“Open up Chrissey,” she said with her classic, confident smile.
In my rising panic, I felt another strong surge of pee soaking my already soaking wet diapers.
“No Mommy–no!” I cried just as Barbara pushed the familiar object between my pouting, quivering lips, stifling any further argument from me.
“There,” she grinned triumphantly as she patted me on the head condescendingly, “I just know you’ll have a wonderful time.”
Chapter Two
About an hour later, I found myself strapped into a carseat in the back of Barbara’s minivan, making our way across town. Every stoplight we came to brought fresh stares at the oversize baby sitting in back wearing a white and pink sailor suit and diapers. At a distance of three feet, it was plainly obvious that I was a 17 year-old guy dressed as a toddler, rather than a bonafide baby.
I blushed vividly as a pair of high school girls rolled down their window and made sneering comments at me, asking me humiliating questions that made me squirm with discomfort. I tried to look the opposite way but there was little escaping their laughing and condescending remarks until our van finally turned down a different street.
Although it had been three years since I’d been outside, I was now more than ever filled with apprehension about the day and Barbara’s plans for me.
“Mommy, I wanna go home,” I whimpered miserably, but the words were completely unintelligible with the fat rubber pacifier filling my mouth.
“Now Chrissey,” Barbara chided me as she guessed my fears, “you’ll feel much better when we get to the park. Aren’t you looking forward to playing in the sandbox?”
“Uh-uh,” I whined, shaking my head.
“Don’t worry, Sweety, you’ll have a great time today–you just wait.”
I slumped down in the raised carseat, although that did little to hide my appearance from the people in the cars that kept coming by all around us. Looking down at my colorful, shiny plastic panties, bulging from the fresh diapers Barbara had recently changed me into, I now regretted my earlier choice of panties. Not that the rumba panties she had in mind for me would have made me look any more adult. But there was certainly no mistaking the look of nursery print plastic panties and it spoke volumes about what I’d become. I was foolishly trying to hang on to the fantasy that I was a still a regular guy. The fact was, I was a big sissy who couldn’t keep his pants dry for more than an hour and I needed diapers just like the baby I was dressed up as.
As we pulled into the parking lot, I was still hoping against hope that nobody would be there but as Barbara started driving slowly down the rows of cars, I realized to my dismay that the place was packed. We were driving slow enough, occasionally stopping, that everyone walking alongside could take a good, long look at me. My breathing increased and my hands grew clammy as mothers stared in at me, not knowing what to make of the teenager sucking feverishly on his pink pacifier.
Loud, urgent sucking noises could be heard from the backseat as I whimpered and whined, fidgeting nervously against the harness that held me in so securely.
Up ahead, a car was pulling out and Barbara had stopped while waiting to take the vacating car’s spot. An attractive girl in her twenties passed by our van and as she looked at me oddly, I felt my bladder’s floodgates suddenly bursting open without warning.
Hot, urgent pee flooded into my diapers uncontrollably, soaking them in moments as I squirmed and shook my fists in frustration. Not again! I was really hoping to get through this outing without a humiliating diaper change. My hopes were dashed as the pooling wetness seeped thoroughly into my seat and upwards into my crotch. Suddenly, I couldn’t take it anymore. As my pacifier tumbled out of my mouth, I burst into tears, wailing an incomprehensible deluge of regrets.
Barbara had just parked and shut down the car when she turned to face me, motherly concern all over her pretty face.
“What’s the matter, Baby?” she blurted out in surprise.
Without waiting for an answer, she jumped out of the driver’s seat and ran around the front of the van, yanking the sliding side door open as if I were choking to death.
With her maternal instincts spot on, she bent over me, her soft hand going down between my legs and cupping the fat bulk of my diapers.
“Aww, mommy’s little baby just wet herself, that’s all,” she cooed as she scooped up my pacifier and pushed it back between my trembling lips. With her gorgeous face just inches from my own, she leaned forward and kissed me tenderly on the cheek.
“Don’t you worry, little sugarplum–mommy’s going to change you into a nice fresh set of diapers in no time!”
I was mortified at the thought of her changing me here where so many people were walking by and I stomped my feet in frustration and anger.
“No! No! No!” I wailed but of course, it sounded more like ‘wo-wo-wo’ instead.
Barbara beamed at me with what looked like pride as she unbuckled the harness holding me in. Pulling me out of the seat, I could feel the familiar wet, sticky feeling of a soaked diaper clinging to my backside.
In between the front seat and the bench seat I was on, the floor was at least three feet wide and after laying a vinyl changing blanket down over the carpet, Barbara set me down upon it.
I was still whimpering loudly, waiting impatiently for Barbara to close the door but she made no move to do so. Before I knew it, she was tugging my clinging plastic panties over and off my diaper and down my skinny thighs. Knowing there was absolutely nothing I could do to stop her, I cried tears of shame as my pee soaked diaper came into view.
Without a second thought, Barbara shook the vinyl panties out over the edge of the van and folded them up before putting them in a plastic bag. Humming to herself, she busied herself with unpinning the diapers themselves and pulling them back. Until now, this had all seemed like a bad dream but as I felt the cool air against my smooth, hairless crotch, the reality of it all hit me like a stack of bricks.
“No Mommy–no!!
My pacifier fell once more from my mouth.
Without a moment’s hesitation, Barbara grasped my ankles and lifted them up high, abruptly exposing my bare bottom to the entire outside world. I squealed in dismay as her other hand came swooping down to deliver a sharp, punishing swat to my bare, dampened cheeks.
“OWWW!!!” I wailed, loud enough to attract the attention of another mother and her kids. I tried to kick my feet but her grip holding my ankles was like steel and she delivered another stinging swat right on top of the first reddening handprint.
“Time for you to settle down, young lady!” she scolded me as she wagged her long finger in my tear-stained face.
I sobbed in shame as she pushed my pacifier back into my pouting mouth, muffling my whimpering protestations. Then, as if nothing had happened, she began her usual task of wiping my diaper area clean with some baby wipes when a voice of greeting was heard behind her.
“Barb? Is that you?”
Barbara popped the baby wipe in the plastic bag and turned to face the young woman coming up behind her. There was only a brief pause before Barbara recognized her friend.
“Hello, Norah!” she exclaimed eagerly, “How have you been?”
An attractive woman about 30ish strode up and threw her lithe arms around Barbara. My eyes just about bugged out as I observed her giant breasts mashing against Barbara’s own huge melons. The scene made me stop crying and I gaped in amazement at the voluptuous woman.
“Its been what–two years? Since I last saw you?” her friend inquired.
“Yes–yes. How have you been?” she asked excitedly.
It was apparent that I was immediately forgotten in the course of Barbara getting re-acquainted with her sexy friend. At home, I would have hardly minded but here in the middle of a parking lot with my hairless and locked genitals displayed for everyone to see, I was aghast with embarrassment. Trying desperately to cover my shame, my hands flew down to cover my crotch.
“Simmer down, Missy,” Barbara said as she absently slapped my hands away, “If I have to tell you again, I’ll be putting you over my knee.”
In mute frustration, I was forced to keep my hands by my side, although Barbara didn’t appear to be in any particular hurry to finish changing me. On the contrary, other than an occasional glance in my direction to make sure I was behaving, she completely ignored me.
Her friend was nothing short of incredible, with a big, beautiful bosom barely contained by the tight lemon colored top she was wearing. Her long brunette hair spilled over soft shoulders, fortuitously leaving an unobstructed view of her fabulous curves. I momentarily forgot my exposed circumstances as my penis struggled to become hard.
“So this must the little sissy you’re taking care of,” Norah said as she finally took notice of me with a broad smile upon her beautiful face.
“Yes, Norah–this is Chrissey–Chrissey, meet my good friend Norah.”
Without removing my pacifier, it was quite impossible to articulate any sort of greeting. Instead, my muffled response sounded like more babyish gibberish.
“Aww, he’s so cute,” she said as she beamed down on me.
I blushed at the unwanted attention and tried to will her to go away so Barbara would finally finish changing me.
“Well, and what do we have here?” she asked excitedly as she caught sight of the small, clear device encasing my penis. Bending down, she held the hard plastic chastity tube in between her slim fingers.
“That’s just a little something I had custom made for Chrissey when I first started taking care of her. She was a chronic masturbator when she arrived and that little gem solved the problem once and for all,” Barbara replied proudly.
Norah’s pretty features furrowed slightly as she looked closer at my diminutive, captive penis.
“Oh my–I’ve never seen such a tiny wee-wee except on real babies. Did it shrink after you locked it up?”
Obviously, she had a hard time believing a 17 year-old guy could have such a small wiener.
“Just a little, but it was half sized even when I met her. That’s why I had to get the device custom made–she would have fallen out of the normal ones.”
Norah kept handling my package as she examined it with obvious fascination from all angles. She was gentle in her handling but it was mortifying to be examined in such an impersonal manner.
“What’s the relief schedule you have him on, Barb? Once a month? Every other month?”
For a second, a look of confusion crossed Barbara’s face but she quickly recovered.
“Oh no, silly,” she giggled, “Chrissey here hasn’t had an orgasm in three years–babies don’t have orgasms–that kind of pleasure is only for adults and as you can see, Chrissey is certainly no adult,” she said emphatically.
Norah smiled and nodded in complete understanding.
“But isn’t it harmful to keep all that um…fluid, trapped inside him?”
“That’s true,” Barbara acknowledged, “which is why she gets milked once a month. As a matter of fact, Chrissey here is due to be milked this very afternoon.” I sucked anxiously on the fat piece of rubber filling my mouth.
“Do you have to remove his chastity device for that?”
“No, not at all. I have a slim rubber tool that I slide into her bottom to massage the prostate gland with. In about three minutes, she starts dripping like a faucet. It takes about ten minutes to drain her completely but you’d be surprised at the quantity,” Barbara remarked.
“I see,” Norah nodded with interest, “I can’t imagine a real man letting someone take control of his orgasms like that–my husband certainly wouldn’t tolerate it for one second.”
“No, of course not. No real man would ever let that happen but Chrissey here isn’t a real man–not by a long shot. She’s the prissiest little sissy I’ve ever come across. She just loves dressing up in her frilly dresses and panties and being a sassy toddler girl–don’t you, Sugarplum?”
I blushed a deep shade of bright red and looked the other way as I chewed on my pacifier anxiously.
“No…Chrissey here knows that she’ll always be my precious little baby girl and that means she’ll never have another orgasm again. Of course, that’s the way it should be for all sissies, don’t you agree?”
“Oh, without a doubt,” Norah nodded, “I think this was the best thing you could do for him. By locking up his little nub, he won’t be tempted to play with it as so many sissies are,” she reasoned.
“Exactly. And sissies don’t need to cum anyway–they get enough satisfaction just from dressing the part.”
Norah nodded again as she looked down and saw the object of my distracted gaze.
“You know, your little baby here seems very interested in my breasts,” she said as she dangled her slim, manicured hand over her bosom and giggled with amusement, “His little package has been twitching and he can’t seem to take his eyes off my cleavage.”
Barbara chuckled.
“Oh, don’t be concerned about that, Chrissey is breastfeeding everyday and she’s naturally entranced by well-endowed women.”
Norah stood back, placing her hands on her hips which only caused her big, plump breasts to thrust out even more prominently.
“Ha ha! Sorry to disappoint you Chrissey, but only real men get to touch these. I’m afraid this is as close as you’ll ever get to them.”
Her haughty, superior attitude hurt my feelings and I choked back a tear of shame and envy. Despite her rejection of me, I still found her incredibly sexy and appealing and her denial of me only made me want her more.
“Well, I better get back to putting Chrissey’s diapers on–she really has no control and I’m afraid she might wet herself as we speak,” Barbara explained.
“Of course,” Norah agreed, “No sisssy should be without his diapers.”
Taking a thick stack of fresh ‘Bedwetters’ from my Minnie Mouse diaper bag, Barbara slid them under my upraised bottom and then set my legs back down.
“He must be a heavy wetter, hm?” Norah remarked as she gazed down at the soft, bulky Birdseye cloth that Barbara was pulling between my widely spread legs.
“Oh my–yes,” Barbara exclaimed, “these are Bedwetters brand–they have a nice thick soaker pad sewn in down the middle and as you can see, each individual diaper is very thick on its own.”
“So soft too,” Norah said appreciatively, “I’ll bet you’re little baby just LOVES wearing these.”
“Oh yes,” she agreed, “She certainly does. Chrissey loves anything that makes her look and feel more babyish, but truth be told, she’s wearing these diapers out of necessity, not preference. The little sissy wets so much that anything less than three diapers and she risks leaking. So all her plastic panties are nice and snug to make sure her wetting stays right where it belongs.”
My cheeks blazed crimson with shame as I lay there, helpless to deny her remarks.
Barbara was snaking up a pair of see-thru polka dot plastic panties over my diaper as an older lady happened to walk by.
“Excuse me, but…isn’t he a little old to still be wearing diapers?” she asked skeptically.
“Oh no–some boys never outgrow the need for diapers and plastic panties,” Barbara replied without a moment’s hesitation.
The lady didn’t seem entirely convinced and she shook her head as she strode off without any further comment.
Barbara giggled to herself but I whimpered with embarrassment at all the exposure I was getting. She proceeded to powder between my legs and then she announced me ready to go.
“There you are Sweety, all safe and secure again.”
I blushed as Norah giggled at my appearance.
“Well, I better be getting on,” she told Barbara.
“It was great to see you. Stop by the house sometime, I’ll show you Chrissey’s nursery.”
“I’d love that,” Norah replied eagerly, “See you next time, Chrissey.”
I waved feebly, still laying on my back with the bulk of my diapers forcing my legs apart.
After Norah left, Barbara helped me climb into the oversize stroller she had brought in the back of the minivan. I still didn’t know how I was going to cope with people seeing me dressed the way I was. I could only hope the canopy top would provide some measure of anonymity to me as she pushed me along the path. Nervously, I suckled from my pacifier as she pushed me along.
About five minutes down the mostly deserted path, Barbara got a call on her cell phone and she halted our movement long enough to take it. I sat in place, completely incapable of going anywhere due to the construction of the stroller. Not only was it awkward to get in and out of, but Barbara had taken the extra precaution of having a seatbelt installed so that I wouldn’t be able to climb out on my own. It secured to a locking clip located on the back of the stroller and was totally out of my reach. Like it or not, I was staying put until she decided to release me.
With little else to do, I sat and watched the only thing of interest in my field of view, a young couple sitting on a park bench, their attention completely devoted to each other. The girl looked to be about my age or slightly older, a pretty blonde wearing a clinging pink crop top which revealed a firm and tanned tummy. My penis twitched with interest as I took in the perfect round curves of her breasts and her narrow waist that complimented her perfect body. How I envied the guy that was stroking her bare thigh! What I would have given to be in his place!
I watched in vicarious angst, as his hand slid slowly up, caressing her curvy hips and then moving on to her sexy waist. My wiener was throbbing now, my libido raging as I watched and wished it were me doing the touching. His hand moved up from her waist now, cupping those full, perfect breasts one by one. I chewed my pacifier anxiously and whimpered as she sighed with pleasure and kissed him passionately in return.
By now, Barbara had finished her phone call and she appeared before me with a large baby bottle in her hand, partially blocking my limited view.
“I’ll bet mommy’s baby is thirsty now, hmm?” she asked as she bent down before me. I had just been able to discern the cute blonde’s perky nipples poking through the thin material of her snug top as a result of her boyfriend’s attentions when Barbara proceeded to completely obstruct the love fest taking place a short distance away.
I squirmed and whimpered, trying to crane my head to see the sexy girl but Barbara was holding the bottle poised before my mouth.
“Open up Sweety, time for num-nums,” she said with an accomodating smile.
Apparently oblivious of my distraction, Barbara removed my pacifier and as a string of saliva followed the rubber soother, she pushed the warm and dripping rubber nipple of my baby bottle into my open mouth.
“Owmmph,” I squealed as I pulled away trying to avoid her ministrations. Unfortunately there was nowhere to go and as my head found the back of the canopy, Barbara held the bottle in place making sure I nursed from the warm breastmilk milk she’d pumped earlier.
“That’s my baby,” she cooed.
I squirmed in my seat, frustrated that I couldn’t see the sexy girl not twenty feet away. My little penis was still throbbing from the image burned into my memory of her incredible body and I pouted helplessly.
It was times like this that I hated my life as a baby. Yes, I had lots of fun normally, wearing my sissy dresses and wetting myself without a care in the world but this was the reverse side of that coin. I was so horny I couldn’t stand it and there was absolutely nothing I could do about it.
The guy that was fondling that girl would be getting his rocks off in no time, probably within the hour, if he played his cards right. And I’d still be here, horny and frustrated, wishing I could do something as simple as rub myself to an orgasm. Full time chastity was one facet of my life I could never quite get used to. If it wasn’t Barbara herself that was constantly arousing me, it was someone else, like this girl on the park bench. And it wasn’t like I could get some quick relief and then be done with it. I was forced to endure my frustration, day after day, without any hope of respite. It was so cruel!
Chapter Three
I was still thinking about the amorous couple at the park when we came back home an hour later. With all the visual stimulation I’d received, I was desperate to try and alleviate my horniness but I was completely at Barbara’s mercy and in the last three years, she’d shown me none at all in that department. Strapped into my carseat, I was re-living in my mind for the thousandth time, the scene of the couple making out when I saw my mom’s car pull up behind us in the street.
That was all I needed. It used to be that I had the upper hand with my mom, manipulating her with my whining and complaining but now the tables had been irrevocably turned. Barbara had seen to that. And now my mom reveled in her ability to make me do her bidding, ordering me around and using her new authority to emphasize my subservience.
Anxiously, I wondered what it was that had prompted her visit today. Barbara closed the driver’s door and came around to open the sliding side door, just as a cool breeze blew the short, frilly hem of my sailor suit up.
I squealed loudly, although the fat rubber pacifier filling my mouth muffled my cries considerably. I struggled to push the hem back into place but it really made little difference. With the cross straps of the childseat buckled in place, my bulging diapers were on full display no matter what I did. And needless to say, I didn’t dare touch them. The last time I had unbuckled myself, Barbara had pulled me over her lap, taking only enough time to pull down my diapers before she blistered my bottom. I could still remember her lecture on ‘safety’ as she gave me swat after stinging swat of her paddle…
Just then, Barbara caught sight of my Mom.
“Hello Pamela, great to see you again!”
They said their hellos while I squirmed uncomfortably, knowing there was nothing I could do that was going to get me inside any faster.
After an interminable conversation, Barbara finally unbuckled me and led me inside.
“You’re just in time, Pam,” Barbara told her as she put her purse and keys away, “Chrissey’s due for her milking today–you’d asked to watch next time I did it.”
“Yes! Well, what a wonderful coincidence!” my mom exclaimed.
Barbara was still holding my hand, afraid to let me be free even for one moment until she’d put me in my highchair, playpen, or the nursery. So despite the fact that we were home, I had to stand there, a virtual prisoner, to wait until Barbara decided what she wanted to do with me.
Knowing what was in store for me, I shifted my feet and visibly pouted. I really resented getting milked and as I stood in place, I stamped my feet in bitter frustration. It meant that all the built up cum that was driving my libido would be drained from me, while I’d get no satisfaction whatsoever. It had to be one of the most emasculating experiences to have my balls drained by a woman determined to prevent me from cumming.
Barbara ignored my fussiness as she led me into the nursery and placed me into my playpen. It was a net sided box of sorts, very much like a real toddler’s except that the sides were about three and a half feet tall. I could just barely climb into it and Barbara had placed bells around the edges as a precaution so she’d hear me if I tried to get out by myself.
Sitting on the soft, cushioned vinyl surface of the playpen, I watched sullenly through the mesh netting as Barbara got a few things together.
“So as I recall, you said that this is the only time his chastity device ever comes off right?” my mom inquired.
“Yes, it’s also a good time to make sure she’s nice and clean down there–and after we’re done, I’ll be sure to lock her little thing right back up again,” Barbara replied.
“I think you were so smart to do that–he really shouldn’t have free access to his willie,” my mom praised her.
“You’re very kind, Pam. It’s always been my rule with sissies to put them under strict chastity at the very first opportunity. We were only delayed in Chrissey’s case because she was so small, I had to have her device custom made.”
“Those are worth their weight in gold. And you just need to milk him every month for health reasons then?” she asked.
“Yes, I’ve found once a month is more than adequate. She gets edgy and fussy if I go longer than that,” Barbara explained.
It was bad enough that I had to endure this humiliating routine but it was rubbing salt in the wound to have my mom here to watch the whole thing. I took one of my dolls and slammed it down on the padded floor but it went unnoticed by the other two.
“Okay Chrissey, let’s get started,” Barbara finally told me.
Reaching down, she pulled me out of the playpen and stood me up.
“Did you wet your pampers, Chrissey?’ she asked me pointedly.
Blushing with embarrassment, my pacificer still in my mouth, I shook my head no. Sometimes it seemed like every word out of her mouth was specifically intended to humiliate me.
I felt her cool fingertips slip inside the elastic waistband of my plastic panties and pull them down, working them off the bulging cloth and then down my smooth, hairless legs. I whimpered in protest, knowing the fuel for an explosive orgasm would all too soon be taken from me against my will.
With little effort, she pushed my thick diapers down around my ankles and helped me to step out of them. I knew very well the procedure and without being told, I stood in place while Barbara recovered the small key. Bending over me, I gazed idly down the front of her blouse, marvelling at her yawning cleavage and her big, beautiful breasts. Her skin was so smooth and creamy…it was impossible to not be distracted by her.
“Didn’t you glue that lock shut some time ago?” my mom asked.
“Yes, but I found I really couldn’t keep her as clean as I wanted–and we want our baby girl to always be squeaky clean–don’t we sissy?” Barbara asked as she looked directly into my eyes.
I nodded my head obediently in response.
“So I had the lock removed and I got a custom titanium one made. As you can see, it’s super small and it can’t be picked–not like Chrissey would ever have the opportunity to do it anyway.”
My mom chuckled as she came closer to look down at my miniscule caged penis.
Slipping the narrow, uniquely shaped key into the bottom of the lock, Barbara twisted it and freed the hasp after which she removed it and placed it on the dresser top. Gently, she grasped the clear plastic tube of my chastity device and pulled it away from the pins that kept it in position. My penis was already in an excited state from earlier and staring at Barbara’s big, round breasts made it spring to life as she pulled the tube away from the rest of the device. She chuckled as she held my little wiener in her hand, watching as it grew to its full length of about an inch.
“Looks like you’ve lost another quarter inch since the start of the year, Chrissey,” she said smiling eagerly.
I gasped in angst and bunched my fists in mute frustration. When I first met Barbara, my penis was already undersized, for reasons I never knew–it just seemed to stop growing when I got into grade school. But since it had been kept under lock and key within the restrictive confines of my chastity device, it had begun to gradually shrink over the course of time. Now, it truly looked ridiculous as I gaped at the twitching pencil stub in her warm hand.
“Is that as big as it gets?” my mom asked incredulously. Her wide eyed expression showed that she was clearly having difficulty believing what she was seeing.
“That’s it,” Barbara laughed, “Honestly, I think Chrissey really was born the wrong gender, but as you can see, we’re making steady progress towards correcting that mistake.”
The two laughed together and my cheeks blazed with shame.
Her demeaning comments were also having a negative impact on my erection, despite my horny state, and it gradually began to wilt before the two of them. I squirmed uncomfortably, blushing with embarrassment as it shrivelled even smaller, to half its size, looking like no more than a small nub in between Barbara’s larger thumb and forefinger. I bit my lip anxiously as I was made to stand there while they examined my diminutive organ.
“Okay, Sweety, let’s get down to business,” Barbara said as she led me over to the crib and had me kneel down before the open side. A vinyl changing pad had been placed on the floor between my legs to catch the eventual discharge. Placing my hands on the nursery print waterproof mattress cover, I breathed deeply from the smell of stale pee that had gradually permeated the plastic surface over time. I soon felt Barbara’s soft hands guiding me and positioning my rump so that it faced outward to them at the proper angle. In my embarrassed state, I clutched my big pink teddy bear for comfort.
My mom watched closely as Barbara slipped a rubber glove on and dipped her finger into a jar of Vasoline to get a good dollop of lube.
“Spread your legs, Baby girl,” Barbara instructed me as she knelt down behind me.
I complied with reluctance and felt her other hand on the side of my hip to steady me.
No matter how much she gave me advance warning, I still winced when I felt the cold gooey tip of her finger invade my backhole.
“Ohh!” I squealed as my pacifier tumbled out of my mouth.
My sphincter puckered as she slid her slippery finger deep into my rectum, twirling it around to give me a good coating. My little penis twitched nervously in anticipation and then when she was satisfied, I felt her withdrawing her finger.
Out of the corner of my eye, I saw Barbara reach down to pick up the milking tool she always used.
“This little item is called an Aneros,” Barbara told my mom, holding the smooth, thumb-shaped dildo in her hand. It was about three and a half inches long with two tabs that extended 90 degrees off the end and formed a handle of sorts. Rolling it into the jar of Vasoline, she coated it liberally before positioning it back at my bashful, quivering hole.
“Sit still and take it like a good girl,” my mom commanded me unneccessarily.
“Here it comes, Baby,” Barbara sang gleefully.
I knew better than to resist her but I didn’t want to entirely submit without a fight.
I felt the first indication of pressure against my anus by the slippery tool.
“No…mommy…unh…wait–” I whimpered weakly.
Barbara ignored me and she gently pushed the greasy rubber phallus deeply into my back passage.
“OHHH!!!” I cried and I gripped teddy tightly as I felt my hole suddenly being filled by the soft, pliable invader.
Within seconds she established a consistent rhythm and as she found my prostate, I slowly relaxed and began to breathe heavier. Her ministrations were soon bringing waves of pleasure to me and her other hand gently patted the buns of my spread cheeks.
For once, my tiny penis was free, and now that it was no longer restrained by my chastity device, it grew to a full erection (or as full as mine ever got). Oh, how I longed to reach back and give it several satisfying strokes! I even leaned back out of instinct, my right hand surrepticiously slipping ever lower but Barbara saw the movement right away.
“Hands back in front, Chrissey,” she commanded me firmly.
In utter frustration, I fussily complied and knelt there captive as she pumped me rhythmically and steadily, massaging my prostate and causing my penis to harden even further. For her, it was a completely non-sexual activity, like kneading bread, and just a routine that needed to be done once a month for my own good.
In my excitable state, I knew it would only take a few quick rubs against the waterproof mattress cover to blow my accumlated load of a month but with Barbara’s paddle in such close proximity, I didn’t dare to try it.
“You know what to do, Chrissey,” she said with calm confidence.
My mom looked at her quizzically until Barbara explained.
“As I massage his prostate gland, Chrissey here gets very close to ejaculating…but she knows she has to tell me before it happens so I can stop the massage and let her cool down.”
My mom giggled at her control over me.
“Ohhhhh….” I moaned weakly, the waves of pleasure washing over me. A drop of precum appeared at the tip of my tiny tool and I clutched my teddy bear close for security.
My penis throbbed urgently and the vision of the blond girl from this afternoon floating back into my consciousness. God, she had a fantastic body, I reflected and as I felt an explosive orgasm bubbling up from deep within me, I moaned helplessly again.
“Oh–ohhhhhh,” I cried, “M-Mommy…I…I…”
Barbara stopped her rhythm and my penis, without anything to further sustain it, throbbed and flexed, unable to reach climax.
It was maddening and I grit my teeth, anger replacing my frantically horny feeling as I waited impatiently for Barbara to resume. As usual, she was in no hurry and instead, she slowly rubbed and squeezed my bottom, holding the Aneros in place, buried to the hilt with her free hand.
At long last, she began slowly pumping me again and my eyes rolled into the back of my head.
“Ohhh…,” I moaned.
I felt drunk from the sensations she was making and I couldn’t keep my eyes open. My penis was once again rock hard and throbbing and I wanted to cum more than I’d ever wanted anything in my life.
“M-Mommy…I-I-I have to…to…I have to cum,” I mumbled deliriousily.
Barbara stopped immediately and she gently rubbed my buns again, my penis twitching miserably with impotence.
One yank and I’d blast a shot of cum like nobody’s business but I knew Barbara would never let it happen.
I pouted and quivered with anger–it was so unfair!! Every other guy was free to cum and cum and cum til he couldn’t cum any more. But not me! I was to be denied that most basic of human functions, for the rest of my life!
In frustrated anger, I slapped the smooth surface of my crib mattress, making a loud ‘whap!’ against the vinyl covering.
“Its not fair!” I whined miserably, trying to grind my hips against the stationary dildo buried deep inside me, hoping for just enough stimulation to bring about an orgasm.
“Chrissey!” my mom snapped, shocked at my display of disrespect.
“It’s okay Pam,” Barbara assured her, “we’re about halfway done here and then Chrissey will be going over my lap for a much deserved spanking.”
I winced at her casual statement and a tear of frustration trickled down my cheek. Not only was my orgasm to be taken from me but now I was going to get paddled on top of it!
“We’re just about there…” Barbara said as she carefully reached between my legs and grasped my tiny twitching penis. She could read my erection like a book and she knew I’d already gone past the point of imminent climax. Putting her thumb and index finger together to form a ring, she slowly pulled it down the inch length of my shaft towards the jelly bean-sized tip. At first nothing happened but by her second attempt, a long string of semi-clear fluid began to dribble down from the end.
I gasped in dismay as I felt my orgasm being inexorably extracted from me while I knelt there, docile with lamb-like compliance as I whimpered and clutched my stuffed bear. When the first stream of semen petered out, she resumed her rhythmic ministrations with the dildo; in and out and around in a circle…
I moaned helplessly and this time, my penis didn’t grow nearly as hard.
“See that?” Barbara smiled, “I should be able to get at least two more squirts out of her and then she’ll be done.”
After a couple of minutes, she once more ran the ring of her fingers down, tugging on my organ and being rewarded with another thicker stream of gooey cum.
“So he’s not feeling any sort of climax during this?” my mom asked skeptically.
“Oh no–not at all,” Barbara said as she carefully pulled another stream of sticky gunk from my penis, “Its almost as if she’s just peeing, and there’s not the sort of pleasureable reaction that would normally happen during ejaculation.”
“Oh…oh…nooo…” I protested weakly as I felt the last bit of cum gradually being milked from my softening penis.
“There, that should do it,” Barbara said satisfied as she gave my noodle one last tug to be sure. A large pool of goo had accumulated on the pad between my legs and I looked down at it filled with regret and an acute sense of loss.
Setting the Aneros down, Barbara helped me to my feet and then led me over to the spanking stool which was kept in the corner. Pulling it out away from the wall, Barbara casually picked up the paddle and took a seat, smoothing her skirt down with her usual meticulous care.
“Chrissey, do you know why you’re getting a spanking today?” she asked.
I nodded my head sadly, my heartbeat increasing rapidly.
“Tell Pamela why you’re going to get your bottom spanked,” she instructed me in her usual condescending manner.
I blushed hotly and stared at Barbara’s smooth, silky thighs, unable to face my mom.
“Be-because I complained during my milking,” I mumbled.
“That’s right Sissy, and you know what happens to babies who complain about getting milked, don’t you?” she said as more of a statement than a question.
“They-they get spanked,” I said bitterly.
“Yes, they do–they get spanked hard,” she told me firmly as she looked me hard in the face.
I began whimpering and fidgeting as she carefully pulled me over her lap, moving me into a helpess position where my feet and outstretched hands could barely touch the ground. Tears were filling my eyes and I sniffled in anguish about my imminent punishment.
“Say you’re sorry to your mommy,” Barbara told me as she gently rubbed the hard wooden paddle across my soft, bare buns.
“I-I-I’m s-sorry Mommy,” I babbled nervously, dreading that first, terrible swat.
It came before my mom could respond, smacking both my tender cheeks with a harsh, blistering impact.
“OOOWWWW!!!” I wailed, just as a steady succession of hard, crisp swats came raining down after the first.
I kicked and sobbed, flailing my hands in the air as Barbara paddled me soundly and without pause. Tears streamed down my face in endless profusion and I cried unashamedly like a baby. Despite the fact that I was seventeen now, I felt as childish as a toddler, lying passively over Barbara’s lap as she spanked me vigorously, taking little effort to hold me in place. I knew better than to try to get up, which would have been futile in any case. In the three years since I had come to live with her, my physical strength hadn’t increased measurably–in fact, I was probably weaker and more delicate, due to my inactive and sedentary lifestyle. To be sure, I was no match for Barbara who was both taller, stronger, and in perfect physical shape.
As she continued to thoroughly pepper the entire surface of my bottom with her hard paddle, I slapped my hands on the floor, helplessly bawling as I received my just punishment. Five minutes ago, I was angry about being deprived of an orgasm but now that paled in comparision to my urgent desire to have this terrible spanking end. Of course, that wasn’t going to happen until Barbara was sure I’d learned my lesson and been thoroughly punished.
Finally, after what seemed like forever, her paddle seared itself one last time upon my flaming red bottom. I was hoarse from crying and my breath came in ragged gasps. Setting the paddle down, she helped me to my shaky feet and led me over to the changing table. I was loathe to sit down on anything, even the padded vinyl surface of my changing table but Barbara didn’t offer me any choice.
Picking up the tube of my chastity device she’d set aside earlier, she knelt down to mate it with the cuff ring that was still in place around the base of my genitals. My shriveled penis easily slipped back into the familiar tube and Barbara threaded the lock into the front pin, pushing it closed with a crisp click. My chest was still heaving from my crying as she pushed a thick stack of soft diapers beneath my cherry red rump and then powdered me with a thick coating of baby powder. The infantile scent surrounded me once more as she pulled a pair of white nursery print plastic panties over my feet and up my skinny legs. Still sobbing, I leaned back on my elbows as she worked them over the fat, bulky cloth and fitted the snug elastic wasitband to ensure everything was fully encased.
With a look of maternal concern, my mom came over and took my hand, gently lifting me up and leading me over to the loveseat that was used exclusively for my breastfeeding sessions.
Wiping my arm across my wet, tear-stained face, I tried to say some words of protest but it all sounded incoherent with my uncontrollable, childish sobbing. With nothing but love for me, she sat down and laid me across her lap on my back, so that her big, swollen breasts were mere inches from my face.
“Don’t cry little baby,” she cooed softly as she unbuttoned her blouse, “Mommy’s got a nice warm surprise for her little sissy.”
I shook my head trying to dissuade her–unlike being breastfed by Barbara which happened on a daily basis, nursing from my biological mother did nothing for me. I hated being forced to do it and it reinforced not only my submissiveness, but the transformed relationship between us in which I was at her mercy.
With her buttons undone, she pulled her top aside, exposing her plump, milk-laden breasts within the silk cups of her nursing bra. I mewled and shook my head but she undid the flap in front and revealed her damp nipple, hard and pink as if impatient to be suckled from. With tears still trickling down my face, she brought my cradled head up and forced me to accept her breast. With a sob of defeat, I opened my mouth and wrapped my lips around her warm areola.
Almost immediately, I was rewarded with a steady stream of her mammary milk, filling my mouth as I swallowed gulp after gulp. I continued to fidget and fuss until she gave my bare thigh a stinging slap.
“That should quiet her right down,” Barbara said with an approving smile.
Helpless to resist her, I settled down and began nursing without protest. I still whimpered weakly but my mom smiled down on me with obvious pleasure.
“It’s such a wonderful transformation you’ve made with Chrissey,” she marveled, “And these hormones you recommended have kept my breasts practically bursting–its quite a relief to finally have him taking some of the strain off them.”
“I know exactly how you feel,” Barbara concurred, “And don’t let her fussiness deceive you–she loves suckling from the real thing much more than any bottle.”
“Oh yes, I’m sure of it,” my mom agreed.
“Please feel free to stop by anytime when she’s not in her crib–Chrissey’s naptime is from 2 to 5 and her bedtime is 7:30.”
“Thank you, I think every three days or so, I’ll need to stop by so he can nurse from me, given all the milk I’m producing now,” my mom told her.
“It’s just what a pampered sissy needs,” Barbara assured her.
Pulling her right breast from my puckering mouth, she positioned the left one which was still straining from the milk inside.
I shook my head no and closed my mouth but my mom looked down on me disapprovingly.
“You’re not done yet, baby–you still have a ways to go,” she said with a smile as she rubbed the dripping nipple across my pursed lips. I squealed timidly but did nothing as she pushed her bursting nipple past my lips. In moments, I obediently resumed my nursing as she dried my face of spent tears.
“That’s mommy’s baby…” she whispered, “that’s it…get your fill of mommy’s milk. Diaper wetting sissies need to breastfeed just like little babies, don’t they?”
I blushed but kept up a steady pace until I felt my belly growing full.
“I think we’ll put Chrissey down for her nap early today,” Barbara announced, “that way, we can have a chance to catch up over coffee.”
“Uh-uh,” I moaned, although it was completely muffled by the nipple filling my mouth, sounding more like ‘muh-muh’.
“That would be great,” my mom said eagerly, ignoring my disgruntled face.
Ever so gently, she pulled her big breast out of my mouth and pulled the flap back over her nipple. Barbara helped me up and I stood fussily, pouting that my day was being cut short so soon. Normally, I would have an hour or two to play with my toys but now Barbara was sending me to my crib early. I wanted to say something in protest but my bottom was still blazing from the five alarm fire of my recent paddling.
With businesslike efficiency, Barbara removed my sailor suit top and pulled a fuzzy pink fleece diaper shirt over my outstretched arms.
“What does that say?” my mom asked as she looked closer at the script on the top of my shirt.
” ‘Bedwetter in Training’ ,” she read for herself and let out a delighted giggle.
I blushed again as my lower lip trembled with frustration. This day had started out so good!
Without any further delay, she turned to my crib and pulled the Disney Princess blankets down, revealing the crinkly nursery print waterproof sheet underneath.
“Beddie-bye time, Chrissey,” she sang merrily, guiding me firmly into the crib.
Sniffling in defeat, I crawled into bed as Barbara pulled the baby blankets back over me.
“Here’s your teddy bear, Sweety,” she said warmly as she tucked my stuffed bear under my arm.
I accepted it passively, not looking forward to another long afternoon in my crib. The only break I could expect in the tedious boredom would be when I inevitably wet myself and I stared miserably up at Barbara as she eased my pink rubber pacifier between my lips.
“Sweet dreams, Chrissey,” Barbara said as she brought the side of the crib up and closed it with a click.
I sniffled with resentment as the two walked out of the nursery, closing the door behind them. The light went out and I was left to ponder my life, not as a 17 year-old guy, but a baby toddler girl who couldn’t keep his diapers dry for one hour.
Posted in My other stories... | Tagged Chastity, Diapers, Femdom, Humilation, Spanking | Leave a comment
Barbara’s New Baby Girl
Posted on March 31, 2013
Chapter One The Store
My mom’s 20 year-old Honda Accord made its way, wheezing tiredly but steadily across town with myself as its reluctant passenger. Sitting in the back seat, I sulked in silence, unhappy with my situation in which I was being forced to accompany my dumb sister to get some girly clothes. My mom had insisted I come along because she didn’t want me home by myself, despite the fact that I was all of 13 years old now, going on fourteen. It was mortifying to still be treated like a snot-nosed kid at my age.
To show my general disapproval of my mom’s plans, I let out a loud and dreary sigh. This went unnoticed so I did it again until I saw my mom look up at me in the rear view mirror.
“Why do I hafta spend all day at this lame store?” I whined miserably.
“It’s not all day, Chris, she said tiredly, “It’s just long enough to get Lindsey a dress and then we’re done.”
“But I don’t wannnna go,” I complained bitterly, not for the first time.
My mom sighed in resignation.
“Tell you what Chris, once we finish at the store, I’ll take you to get some ice cream. How about that?” she offered, hoping desperately to placate me.
Fact was, my mom was easily pushed around. And truth be told, I knew just how to do it, through pleading, whining, and complaining until she eventually capitulated.
“Okay,” I replied sullenly, although I was secretly pleased to have wrung a concession out of her.
We pulled into the parking lot of the store a short time later and as I craned my neck, I could read the pink cursive writing on the neon sign. It said Missy’s Dresses and Apparel and I cringed at the thought of spending more than five minutes as a captive within it’s walls.
On the way over, we’d stopped for lunch at Chuck-E-Cheese and my sister and I still carried our disposable soda cups with our leftover drinks. Personally, I hated Chuck-E-Cheese because it catered to such a juvenile crowd but that was one contest I had decided to let my mom win.
As I got out of the car, I was crunching some of the ice from my cup, having discarded the lid somewhere in the back of the car.
“Chris, put the lid back on,” my mom told me, “I don’t want you to spill anything in the store.”
“Aww Mom,” I started, “I’m not gonna spill anything,” I said as I kicked a stray rock in the parking lot.
“Chris, just do it this time, okay? Just once I’d like to have you do something without a major ordeal,” she muttered in exasperation.
“I’m not gonna spill anything–I promise,” I said, my voice approaching it’s maximum tone of whininess.
My mom sighed heavily, finally giving up and I strode behind her, noisily crunching my ice as I chocked up yet another victory.
My sister Lindsey was eight and very excited to be able to pick out a dress of her own. Apparently, this store was known for it’s fancy, frilly dresses, the kind like you’d see at an Easter party or something. Personally, I couldn’t care less so the sooner I could get them out of there, the better.
Walking in through the main doors, I stopped my crunching of ice and suddenly swallowed hard. Standing before us, was an absolutely breathtaking woman who smiled down upon us, greeting us into her establishment.
“Well hello!” she beamed enthusiastically at us, “Welcome to Missy’s Dresses!”
My sister was grinning ear to ear and bubbling with excitement but I was finding my mouth going dry as I stared openly at this stunning angel from heaven. Immediately capturing my full attention and right at eye level, I gaped in awe and amazement at this gorgeous woman’s deep, plunging line of cleavage, disappearing down into the V cut of her silk top that was stretching mightly to contain her massive breasts. They were round, perfectly shaped, and in all honesty, huge! I had never seen boobs so big in all my life, especially on a woman so slim. My heart thumped within my chest and I felt a familiar stirring in my groin as I stood there mesmerized.
She had a snug pencil skirt that wrapped around her curvy hips and seemed to accent her narrow waist and hourglass figure. Her long, silky blonde hair was pulled back, not severely, but in a very feminine way that emphasized her very pretty face. Full, luscious lips and delicate, yet commanding eyes that held me in their gaze, prevented me from evaluating her further. I felt instinctively that here was a woman of presence, so completely night and day from my own weary mother.
“And what’s your name, Young Man,” she said as she bent down slightly to speak to me.
Her cleavage yawned before me and I licked my dry lips as I stared at her soft twin mounds of feminine glory.
“C-C-Chris,” I stuttered uncertainly. I felt my cheeks glowing red at being the center of attention of this goddess and I was forced to look down at the floor.
“Hello Chris–Let’s see…I’m guessing you’re about ten, right?”
My face flushed with embarrassment at her gross underestimation of me. It’s true that I was short with somewhat effeminate features but I always thought of myself as a guy’s guy.
“I-I’m thirteen!” I protested.
“Oh!” she exclaimed, putting her slim, manicured hand in front of her mouth, “I’m sorry, I had no idea!”
“And are you here to get something pretty?” she asked in her syrupy voice.
I had no idea why she’d draw that kind of conclusion about me but it was enough to allow me to finally regain my composure.
“No way!” I snapped, “We’re here for my dumb sister.”
I pointed at Lindsey who was staring with star struck eyes at the vast selection of frilly, girly clothes all around us.
“Well I know we’ll find just what it is you’re looking for,” the lady said, focusing in on my sister, “My name is Barbara, and this is my store.”
She gave us all eye contact and when her gaze fell upon me, I practically shivered. I think I was in love! What a total babe!
My mom explained the type of dress they were looking for and Barbara led them to a different section of the store where they might find it.
All the while, I took the opportunity to drink in her sexy, adult curves. What a woman! From every angle, she was incredible. She wore high heeled pumps that matched the silky top she was wearing and her snug skirt went no further than the top of her knees, allowing me to admire her smooth, shapely legs.
Following behind her, I was looking her up and down, when she suddenly turned around to make sure I hadn’t become lost. Unprepared for her about face, I stumbled forward and ran right into her, my face mashing against her soft pillowy breast.
“Oh! I’m so sorry!” she exclaimed, although she was wearing a knowing smile as I blushed furiously from my clumsiness. Despite my embarrassment, my penis was rock hard and I was already thinking of ways to relieve it the second I got home. To be sure, this woman would feature prominently in my fantasies for quite some time.
My sister began picking out dresses, far more than I knew we could afford, or would have time to try on and when Barbara went to help out another customer, I quickly began to get bored.
“Mom? How long is this gonna take?” I whined pitifully.
“Just a little bit longer Chris, try to be patient,” she chided me.
“But this is soooo boring,” I complained, making myself a complete nuisance.
“Chris, why don’t you go amuse yourself somewhere in the store–we’ll find you when we’re done,” she told me tiredly.
Muttering to myself, I shuffled off, knowing I was going to be bored to tears no matter where I was in the store.
I spied Barbara about twenty feet away, talking to what I assumed was her assistant, a real knockout from what I could see. While not as curvy as her boss, this woman looked to be about 19 or 20, with long, straight blonde hair and a body that looked like had been sculpted in a gym. She looked like a real hottie!
Totally distracted, I set my drink down on one of the store’s fixtures, not even paying attention to what I was doing. I just wanted to spy on these two while they were unaware of my attention.
All of a sudden, I heard the contents of my drink spill noisily as the cup fell about a foot off the ledge I’d set it on. Looking down, I gasped in shock as the red liquid splattered all over several fancy white dresses that had been laid out on the next shelf down.
Oh my god! What a huge mess!
Looking around, I saw that no one had yet witnessed my blunder and taking in the scene of disaster, panic filled me and rendered me incapable of rational thought. The only thing that occurred to me was to flee and right away! If only I could get my mom to leave before it was discovered, I might escape punishment.
Barbara and her assistant were still occupied with their conversation so I scurried back to where my mom was evaluating my sister’s latest choice.
“Oh that’s lovely, Dear,” she remarked, “What do you think?”
“I think I like the pink one better, Mommy,” she replied.
“Do you?” she asked.
It was obvious they were in no hurry to get going and I fidgeted nervously, shifting my weight from one foot to another as I bit my lip in angst.
“Are you guys about done?” I asked anxiously.
Oblivious to my state of panic, my mom hardly looked my way.
“Chris I thought you were going to occupy yourself until we came and got you.”
“How much longer is this gonna take?” I pleaded with her.
“For heaven’s sakes, Chris, you’re really becoming a trial,” she replied with annoyance. Of course, she always said that but what grated at me now was that she used to it delay whatever it was I wanted at the moment and what I wanted right now was to get out of there fast!
From behind me, I heard the distinctive sound of approaching high heels; a ‘click-click-click’ that announced my moment of retribution was at hand.
“Excuse me, Ma’am,” the commanding voice spoke from behind me and I knew with sinking certainty it belonged to Barbara.
It was only with great effort I was able to turn around to face her and I saw she was holding my empty Chuck-E-Cheese cup in her lovely slim hand.
The blood drained from my face and my palms felt suddenly clammy.
“Does this cup belong to one of your children?”
I resented being classified as a child but that was the least of my worries as my mom looked from the cup and over to me.
“Why yes it is, did Chris neglect to throw it away when he was done?” she asked, innocently unaware of what I’d done.
“Will you come with me a moment?” Barbara asked. Her voice was friendly but firm and it filled me with dread.
As we followed along behind her, my mind raced with any possible excuses as to how I could talk my way out of this. The problem was, I simply couldn’t think straight. Somehow, I knew this woman wouldn’t tolerate being manipulated like I was used to with my mom–she’d see right through me.
When we got to the scene of my spill, my mom’s face showed both horror and dismay. This was exactly what she had warned me about before coming in and my blithe dismissal was still ringing in my ears.
“I found this mess just now and I recognized the cup from the ones your children were drinking from,” Barbara explained, “Would anyone like to own up to what happened here?”
My sister was still holding her cup with it’s lid still on and there could be absolutely no doubt as to who the culprit was. Still, I kept my silence with my eyes downcast, hoping somehow, by some miracle, this would all be forgotten. Barbara stood towering over me, her hands on her curvy hips as she waited for an answer with growing impatience.
“Young Man,” she addressed me sternly, “Is there something you want to tell me?”
A bead of sweat trickled down the side of my forehead and I absently wiped it away.
“It wasn’t me,” I bleated weakly, but it was quite obvious no one believed me.
“Chris, I am very disappointed in you,” my mom said with uncharacteristic authority.
“But it wasn’t my fault,” I began to whine. This tactic had always served me well and I hoped it would serve me again or maybe at least lessen my punishment.
“I’m sorry, but these were very expensive dresses,” Barbara informed my mom, “Something will have to be done.”
My heartbeat was thumping in my chest as I glanced anxiously up at the store manager. Despite the fact that she was incredibly sexy, I feared her on a level I didn’t fully understand and she looked capable of just about anything.
“I’m so sorry,” my mom said, a look of anxiety and worry creasing her face, “He’s just more than I can handle these days. I honestly don’t know what to do with him anymore.”
“If you will allow me, I will see to it that he is properly punished, and then we can make arrangements for him afterwards.”
My mom appeared immensely relieved, probably because she had no means of paying for the damaged goods. She was also glad, I think, to have someone who would finally be able to give me the discipline she was incapable of providing.
“Yes, by all means,” she quickly agreed.
“But Mom,” I whimpered piteously, “it wasn’t my fault!”
“Come along Young Man,” Barbara said as she snatched my wrist with surprising strength, “You’re going to be taking a trip over my lap.”
“Huh?” I gasped.
I gulped in fear and tried to wrench my hand from her grip but her hold was like steel.
“No!” I squealed, “You can’t spank me! Mom!”
I was sure my mom would intercede on my behalf, after all, I hadn’t been spanked since kindergarten and that was by my teacher. My mom would never allow me to be given such a childish punishment by a total stranger! Not at my age!
To my surprise and chagrin, my mom not only didn’t stop her but she added a few words of her own.
“Chris, you’ve had this coming for a long time now. I think this is exactly what you need and deserve.”
I pouted and whimpered as Barbara dragged me into her spacious back room, opening a drawer from a tidy desk against the wall. She deftly retrieved a stout, oval shaped wooden paddle with nickel sized holes in it’s face.
Panic seized me and I stomped my feet frantically.
“No…no….please–please, I didn’t mean to–I–I was just…” I pleaded.
Barbara took a seat in a straight backed chair and faced me as she began unbuttoning my shorts.
“I don’t like liars, Young Man,” she told me in no uncertain terms, “I’m going to give you a good, hard spanking and teach you a lesson you won’t soon forget.”
By now, tears had formed in my eyes and I tried to stop her hands from pulling down my shorts.
“Oh–oh–no! Wait! P-please–please don’t spank me!” I wailed.
This woman was implacable and she was completely ignoring my whining pleas for her to stop.
Her beautiful features were set firmly as she went about her serious business, slapping my hands away and as she yanked my shorts down, her tremendous breasts defiantly teased me as they jiggled within her tight silk top. Without the slightest pause, she yanked my Superman underpants down and jerked me over her toned lap.
“No–no–please–please don’t!” I wailed as the first tear spilled down my trembling, panicky face.
With her high heeled pumps, I found myself lifted completely off the ground, off balance and all too helpless in her steely grasp.
SMACKKK!!!
The hard oak paddle seared itself across both my soft, youthful buns and I howled out in angst and surprise at the ferocity of her first swat.
Tears poured down my face now as I began bawling like a child instead of the teenager that I was.
Looking up, I could see Barbara in a nearby mirror as she paused long enough to look back into my eyes.
“You really are a sissy, aren’t you?” she said as she shook her head disapprovingly.
Desperate to make her believe I was tougher than I really was, I shook my head vigorously.
“No–no Ma’am!” I cried between sobs.
“Well, I know a sissy when I see one and you have sissy written all over you. You’re not the first little boy who’s felt the sting of my paddle but you can be sure you’ll get what’s coming to you,” she said tersely, finishing her sentence with another pair of hard, angry swats to my defenseless buns.
SMACKKK!!! SMACKKK!!!
I kicked and swung my hands wildly in the air, gasping for breath as her vengeful paddle came down again and again. Looking up briefly in the mirror, I saw a blurry image through the tears flooding my eyes and streaming down my face. I looked like a naughty little boy being punished by his babysitter as her fierce paddle swatted me repeatedly with impunity.
I kept waiting for her to stop, after all–she’d taught me a lesson and then some–but she just kept up an even rhythm, slapping one tender cheek, then the other, then the side of one rosy cheek that had escaped her attentions. My pliant, stinging buns danced under her ferocious assault, flattening briefly under the impact and then jumping back up to receive another dose of her unyielding wood.
I cried like I’d never cried in my life, snot dribbling down my face and tears spilling down my cheeks as I shook my fists in helpless futility.
At last, she stopped and pulled me to my feet, staring down suspiciously at my damp, limp genitals.
“Did you wet yourself on my lap?!” she asked incredulously.
I was so distraught all I could do was bawl incoherently and dance in place as she held my wrist captive.
Taking my lack of denial for a confession, she wrenched me around and landed another harsh, stinging swat on my bright red bottom.
I howled again and bucked forward but could go no more than a few inches due to her iron grip on my arm.
“You belong in diapers, you little sissy,” she informed me as she looked down on me coldly, “But I have something here that will do temporarily.”
I could do little but focus on the blistering inferno blazing across my bottom and I hopped from one foot to another as the tears poured down my ashen face.
“I want you to place your hands on the desk here,” she commanded me, “And if I see you move either one, I’m going to pull you right back over my lap–understood?”
“Y-y-yes M-Ma’am,” I bawled.
Doing as I was told, I sobbed and felt sorry for myself as I stared at the near wall. In my present position, bent over slightly as I was, my bright red bottom stuck out like a beacon of shame for everyone to witness. As if to heap further humiliation on my situation, the backroom door opened up and Barbara’s stunning blonde assistant came in. Her gaze fell from my tear-stained face, down to my candy-apple cheeks before she smirked knowingly.
“Looks like you found the one who made that mess,” she remarked.
“Yes I did, and as you can see, he’s one sorry little boy now for causing all the trouble,” Barbara replied.
The cute blonde chuckled, her lack of sympathy obvious.
“I’ll say, maybe that’ll teach you a lesson,” she said to me before going back out onto the salesfloor.
I was mortified, having to stand there, nude from the waist down, and so obviously punished, although at least I’d managed to keep my privates hidden from Barbara’s assistant.
Offering my mom a place to sit, Barbara turned to face her directly.
“So, tell me Mrs…”
“–Schaaf,” my mom replied, “but please just call me Pamela.”
She seemed eager to work with this stern woman which made me all the more nervous.
“Thank you Pamela, I’m very pleased to meet you,” Barbara said cordially as she extended her hand.
“I’m wondering if you might tell me a little about your son,” she began “I have my own ideas from what little I’ve observed on my own, but I’d like to get your own impressions of him.”
“Of course, I’m only too happy to help,” she answered.
“Has he always been this bratty? He seems inclined to try and get his way by whining and being a general pest.”
“Oh yes–very much so,” my mom replied quickly, “And it’s only gotten worse over the last couple of years–its gotten so he’s constantly fighting me on every little point, doing anything to avoid being responsible.”
“Mm hm, I thought so. And would you say he tends to stay indoors a lot? I’m guessing he doesn’t have many friends and he’s disinclined towards sports.”
“Yes…yes, now that I think about it, that’s exactly right.”
“Mm-hm, now tell me, when I first saw him, he looked more like a little girl in boy’s clothing than a young man of thirteen. I know that any girl would die for his smooth hairless legs and soft features. Does he get pushed around a lot at school because of his looks?”
“Mm, I’m afraid so,” my mom answered, “I guess they don’t see him as much of a guy’s guy. In fact, some even call him a sissy.”
“I can certainly see why,” Barbara responded.
“I’m not a sissy!” I interrupted them as I sobbed in desperation.
Barbara tried valiantly to hide the smirk on her face before pressing on.
“Let’s see…I imagine that he spends a lot of time masturbating too…am I right?”
My face blazed scarlet and even my mom’s face showed a little color as she nodded her head in dismay.
“Yes, its really become quite a problem,” she explained, “He’s constantly in his room with his underwear around his ankles, stroking himself to god-only-knows what. I’ve tried everything I can but I’m just not having any effect on his behavior.”
“That’s a lie!” I hollered angrily, my face still wet with tears.
“Young man,” Barbara said firmly, “I’m this close to pulling you over my lap again for another spanking—is that what you want?”
“No!” I sobbed petulantly.
Barbara and the others went back to ignoring me and she crossed her arms over her big, curvy chest.
“It’s clear I have a lot of work to do,” she announced authoratively.
“I have a proposal to suggest which will take care of the damage your son has caused and erase any financial obligations for you.”
“Oh–anything,” my mom quickly agreed. It was clear she was only too happy to have someone else deal with me.
“I suggest you drop off Chrissie here after school and he can work for me until he’s paid off his debt for the damage that he’s done.”
“It’s very kind of you to offer that–of course we’ll do that. Just tell me when.”
I groaned inwardly. As if her spanking wasn’t punishment enough, I was going to be under this terrible woman’s thumb for who knows how long! And who knew what further humiliations she had in store for me…
“How about a week from Monday?” Barbara asked, “There are a few things I’d like to have ready for him when he arrives for his first day of work.”
I could only imagine what those were but I held my tongue in silence.
“Oh yes–certainly,” my mom hastened to agree.
“Good–then it’s settled,” Barbara announced with pleasure,
“Chrissie? Since you seem to have trouble keeping your pants dry, I’ve got a little something that might help in the short term.”
Barbara went to a set of drawers and brought forth a white and pink set of underwear. Wiping the tears away from my face, I saw that they were actually thickly padded training pants, with a Barbie motif on the front and seat. Normally, I would never have submitted to such an indignity but there was no way I was going to stand up to this woman.
“Come here, Chrissie,” she ordered me, “That’s a good boy. Now step into your new panties.”
I whimpered and continued to sob as I gingerly lifted my legs one at a time into the childish trainers she was holding open for me. Wavering uncertainly before her, I had to reach up to her shoulders to help steady me. All too slowly, she pulled them up my smooth, skinny legs and pulled them around my hips. Her big, sexy round breasts were mere inches from my face but now I was regretting having ever set eyes on them.
The trainers were soft and comforting, at least upon my genitals, but the seat felt like sandpaper as soon as it made contact with my hot, stinging buns. I let out fresh sobs of defeat as she pulled them snugly into place but I also managed to breathe in the scent of her perfume as I stared down the front of her silky top at her incredible cleavage.
Scooping up my shorts, I thought she was going to put them on me but instead, she handed them to my mom.
“I suggest you leave these off until later,” she told her matter-of-factly to which my mom nodded.
I was going to make some sort of protest, but then I thought better of it–I certainly didn’t want to go over this stern woman’s lap again!
Towering over me in her heels, Barbara turned to face me once more.
“Can you do your best to keep those training panties dry until next Monday?”
My cheeks burned with shame as I stared at the floor and nodded reluctantly.
“Okay Sweety?” she repeated, as if she hadn’t seen my first response.
“I will,” I sobbed anew as I blushed again.
“That’s a good boy,” she replied as she smiled down at me, “I have the feeling we’re going to get along, just fine…”
Chapter Two Chris’ New Home
For the next two weeks, I could think of little else, other than Barbara. And my situation was made worse by the fact that I was helplessly caught between two diametrically opposed emotions–shame and lust.
On one hand, every time I thought of the buxom store manager, I blushed furiously as I re-lived my painful and humiliating punishment at her hands. Never had I met such a powerful, strong woman, so stern and strict, who insisted on dealing with me like I were nothing but a small child. I hated her total confidence and absolute authority, not to mention the fact that she was a lot stronger than me.
On the other hand, when I saw her in my mind’s eye, I couldn’t help getting intensely aroused, despite my burning anger towards her. That voluptuous body and pretty face; her long, shapely legs and silky brunette hair. She was sooo sexy! Putting aside my smoldering resentment toward her, I found myself masturbating shamelessly several times a day as I hungrily fantasized about her. I hated myself for giving in to the temptation when she’d shown me nothing but humiliation and a blazing bottom but I couldn’t stop no matter how hard I tried. After dreaming about her delicious curves, my mind focused on her incredible bosom. Imagining being able to touch those soft, fabulous breasts sent me over the edge of orgasmic ecstasy every time…
But today, I was sitting in class, trying to scheme some ploy in which I could foil my mom’s plans to take me back to that woman’s store. I had in mind my usual whining and complaining, hoping to wear her down until she finally gave up. I was fairly certain I could put a wrench in her plans when suddenly, I heard a very distinctive sound coming up from behind me.
Click, click, click, click…
“Who’s that?” I heard someone nearby whisper in awe.
My hair stood up on end as I slowly turned around, dread filled certainty washing over me like an icy bath.
“Hello Chrissie,” Barbara said in her melodious, yet commanding voice.
I felt myself wilting as my heart began beating wildly in panic. I hadn’t anticipated this turn of events at all!
Standing tall over me in her high heels, I stared up at the object of my anger and lust, my mouth hanging open stupidly. She was wearing a very short skirt and a snug, form-fitting button top that clung tightly to her proud, eye-popping breasts. It took my breath away and my mouth was suddenly parched.
“Your mommy has given me permission to pick you up myself, Chrissie,” she told me with a knowing smile, “And your teacher has graciously decided to let you out of class early.”
“B-b-but…I-I-I don’t–” I stuttered.
“Come along Chrissie,” she said in a friendly, yet firm tone, using her name for me that I detested, “I’m your babysitter now and it’s time for us to go.”
Without waiting for an answer, she reached down and took hold of my hand, standing me up like I were a toddler. With every one of my classmates now staring at us, her other meticulously manicured hand reached down and squeezed my bottom inquiringly.
“Not wearing your training panties today?” she asked, loud enough to make sure that everyone could hear.
“She-she’s just kidding, fellas,” I croaked with a nervous laugh, hoping to defuse her comment and minimize the intense humiliation she was causing me.
“Well I just hope you can keep from wetting your pants long enough before I can get you over to the store and put you into some diapers and plastic panties,” she announced merrily.
I felt the blood rushing to my face as the word ‘diapers’ got repeated by everyone around me. Blushing furiously, I couldn’t help but hear a chorus of giggles erupt from around the class.
“Wa-wait!” I squealed anxiously, “Y-you can’t take me with you.”
I struggled to free myself from her grip but only succeeded in making myself look weak and foolish.
“Perhaps I should tell your classmates of our last meeting, Chrissie,” she smiled with mischievious sweetness.
Abruptly, I stopped all resistance. I couldn’t risk her telling everyone how she’d spanked me like a child and then left me to stand there, my bright red bottom on display for all to see.
“Mmm-hm. I thought so,” she said smugly, “Come along now.”
Defeated and shamed, my world was a blur as I hung my head low and walked along behind her. Taking me by the hand, she led me out of the classroom as everyone openly stared at me. My face burned with shame at being treated like a child in front of all my peers–I’d never live this down!
As we went out into the parking lot, Barbara led me to a white, late model minivan. I was about to take a seat in the front when she held me back and opened the sliding rear door instead.
“No, sissies sit in the back,” she instructed me and before I knew it, she was pushing me into an oversized child’s seat that was secured to the bench seat.
“Wha-what are you doing?” I protested.
Out of the corner of my eye, I could see a group of sophmore cheerleaders stopping to take in this strange scene–a 13 year-old being strapped into a child’s seat by what looked like his mommy. I blushed again heatedly as Barbara quickly secured the seatbelts and straps holding me in place, all while I whined desperately for her to leave me be. Once she finished, she stepped inside and closed the door, at least providing us with a welcome sense of anonymity as she took a seat next to me.
Barbara was all smiles as she cozied up close to me, her big breasts jiggling within her thin top. I felt a little nervous, alone with this incredibly sexy woman who was much older than me and trapped in her car as I was, I felt like her captive. As I gazed over her enticing, bountiful curves, my hands felt clammy and I became aware of a nervous buzz in my stomach.
“Chrissie, I think we may have gotten off on the wrong foot,” she said in a warm, friendly way. Her voice was soft now, soothing and pleasant to my ears.
“We-we did?” I said, my voice breaking. It suddenly felt very warm in the van.
“Yes, but I can’t tell you how excited I am that you’re going to be spending time with me. We’re going to have so much fun together! I even bought you a special present.”
I was completely taken aback. I was expecting more of the same stern, disciplinarian that I’d encountered at her store. This side of her made me feel at ease, although her smoothering sexy presence so close to me continued to make me nervous.
Slowly, I watched as she undid the upper button of her snug, straining top, revealing the lacey clasp of her bra underneath. My heart was pounding in my chest wildly now as I stared at her big soft breasts, pushed together and displayed before me in a way I couldn’t ignore. Her scoop necked top was plungingly low as it was and this exposed yet another inch of her smooth, plump bosom. My little penis reacted instantly and it strained urgently within my underwear. She was even more incredible than my imagination remembered her!
I licked my dry lips and tried to breathe normally as I saw her produce a small box, wrapped with babyish gift wrap. Placing it in my hand, she beamed down at me, as if this was some wonderful present that I had been waiting all my life for.
“Go ahead, Chrissie, open it up–it’s especially for you,” she told me encouragingly, her beautiful smile overwhelming me.
I was at a loss for words as I slowly undid the pink silk ribbon and tore away the childish nursery print wrapping paper. I couldn’t imagine what it was she could have gotten me, nor why she chose to wrap it like something for a baby shower.
Inside was an oversized rubber pacifier, still in its orginal see-thru plastic packaging and the label that identified it as a ‘Sissy-Paci’.
With a confused look on my face, I held it in my hand while Barbara suddenly drew closer to me. Taking her slim hand, she held my face gently as she slowly and deliberately planted a big wet kiss right on my quivering lips!
If I was breathing hard before, now I was ready to hyperventilate!
I’d never kissed a girl in my whole life and now this stunning babe had just kissed me in the most erotic way!
With her rose colored lipstick still upon my lips, I stared dumbfounded at her, although my throbbing erection didn’t have to be told that I was the luckiest teenager in the world.
“You see?” she said sweetly, “You and I are going to get along just fine.”
I still didn’t know what to say but her smile was infectious and it made me swoon with desire.
“Now…this baby pacifier is very special–it’s made specifically for big sissies like you that are going to be nursing soon,” she said cryptically as she opened the package and took the pacifier in her creamy hand.
“Open up Chrissie,” she said softly as she positioned it before my lips.
I didn’t know what she was doing and I was completely confused. What did she mean by “nursing soon”?
“No–no…” I squirmed but the straps holding me in made it difficult to struggle.
“Open up Sissy,” she smiled as she gently rubbed the big rubber nipple against my trembling lips. Just as I managed to bleat out another protest, she pushed it past my parted lips and into my mouth, stifling my words.
“Mmrphh,” I whimpered as the pliable rubber object filled my mouth completely. Sucking on a soft, flexible rubber nipple suddenly brought back long forgotten memories, making me feel very babyish.
“There you are,” she said happily, “It’s perfect for you.”
I shook my head in protest, the large pink plastic ring in front jiggling, but Barbara continued to smile broadly at me.
“Now I know today is going to be a lot for you to take in Chrissie,” she said as she passed the plastic loop over my head and around my neck, “I know right now, you’re feeling confused and a little unsure. But first, I want you to understand that this is your very own pacifier and you must never take it out. Ever. Okay? Do you understand? Because if I see you take it out, I’ll have to pull down your pants and give you another spanking, except this time, it’ll make your last trip over my lap seem like love taps.”
I felt a shiver of fear ripple through me as I stared back into her pretty piercing eyes while she explained all this to me. Her voice was still warm and friendly but it carried a firmness that left no doubt about her willingness to enforce her rules.
“I don’t want to have to spank you again but I will if you make me…and you don’t want to cry like a little baby again, now do you, Sweety?” She asked tenderly.
I shook my head slowly feeling numb all over.
“That’s good,” she said reassuringly. I felt her soft hand on my thigh now and she gently began stroking me as she talked. I was so confounded and bewildered I was paralyzed with indecision but there was no mistaking the incredible hard-on that was tenting my trousers.
“You see, I recognized right off that you were a big sissy. You’re actually a little baby girl in a big boy’s body, desperately trying to get out, but no one will let you,” she said in cutesy voice designed for talking to toddlers, “But now that’s all going to change.”
I shook my head no but she just ignored me and plowed on like she couldn’t see me.
“Oh yes, because from now on, you’re going to be my precious little baby girl–I have so many plans for you–I can’t tell you how excited I am to show you everything that’s waiting for you back at my place,” she gushed, “You’re just going to love the cute, prissy outfits I’ve got for you–you’ll have a wonderful time!”
I was aghast at the picture she was painting for me but it was obvious she was truly thrilled about her plans and it was equally apparent she expected me to feel the same.
“And I know a big sissy like you must feel truly naked without a thick pair of diapers and plastic baby panties–but don’t you worry–we’ll soon take care of that problem,” she giggled.
I shook my head and whimpered pleadingly.
“Now–you just keep that pacifier in your little mouth–okay Sweety? Don’t even think of taking it out–all little babies need their pacis and you’ll come to love yours–I just know it!”
Rising up, Barbara moved past me and opened up the door–just in time for a pair of high school girls who were walking past at that moment to look in and see me, sucking my pacifier with its big pink plastic ring on the mouthguard. I blushed in shame as they giggled and walked past, too late for me to take it out, even if I’d had the courage to do so.
Barbara closed the sliding door and went around to get in the driver’s seat, buckling herself in as she looked back at my panicky face.
“Don’t worry Chrissie, everything’s going to be just fine from now on.”
The thought occurred to me to spit out the pacifier, undo the seatbelts and bolt out of the car. And I almost did, but the van was already moving and my window of opportunity was gone.
It didn’t take long to reach her store, and once again, she insisted on holding my hand like a child all the way in. To be honest, I wasn’t sure how I was going to deal with her once we got there but now that we had arrived, I still didn’t have a good plan. I felt like a fool as I walked through the store, a fat pink pacifier stuffed in my mouth, as shoppers stared at me openly. I did my best to look the other way but their whispers followed me relentlessly.
“I’m sure you must be feeling very insecure without some diapers and plastic panties on but don’t worry, Chrissie–I’ll get you changed in no time,” she assured me.
Butterflies buzzed in my stomach as I searched around for some sort of escape. This was all happening too fast!
Taking me through a back door, we walked down a short, well tended pathway that led to the front door of her house. Without pausing to tell me what was going on, she ushered me into her home, a modest but immaculately clean single story house. Passing a large living room area, she wasted no time taking me down a brightly lit hallway.
“And down here is going to be your new bedroom Chrissie, or should I say, your nursery. I know you’ll just be thrilled when you see it,” she waxed enthusiastically.
Opening the door, Barbara practically pushed me inside but as she stood behind me, she brought her head down to my level to speak closer to my ear.
“You see, Chrissie?” she said softly, “there ‘s everything a little sissy could ever hope for–over there is your dresser, which I’ve stocked with lots and lots of plastic panties, rumba panties, diaper shirts and sissy tops. And you have your very own crib to sleep in, with a nice waterproof vinyl mattress cover in case your diapers ever leak. I’ve collected a big assortment of baby dresses that I know you’ll just love–see all the colors and styles? All in pretty pastel colors, although as you can see, pink has always been my favorite, just as I’m sure it’s yours too.”
My head was swimming as she extolled the many wonderful items of this babyish room, which looked to all intentions to be that for a two or three year-old toddler, rather than a young man of thirteen. The walls were papered with a nursery print design of giraffes and bunnies over a pink and lilac background. There were dollies arranged next to a box of plastic building blocks and next to the crib was a vinyl covered changing table, large enough to accomodate my semi-adult frame.
Sucking nervously on my pacifier as I tried to take all this in, I suddenly felt Barbara’s hands on my waist as she began pulling my shirt up and off of my torso without warning. I squealed in protest which was dutifully muffled by the pacifier filling my mouth but nevertheless, in seconds, I was shirtless. No doubt, any other young man would have spit out the pacifier at that point but I obediently kept it in my mouth which made me look like a petulant toddler.
“Its time to get you changed, Chrissie,” she announced happily, “I’m sure you must be very anxious to be pinned into your new diapers.”
I shook my head and tried to stop her but she was both quick and deft and despite my efforts to stop her, she got my pants unbuttoned and was bringing them down quicker than I thought possible. My struggling caused me to stumble and I fell over, landing with an unceremonious thud on the carpeted floor.
“Careful Chrissie, you don’t want to hurt yourself do you?” she said as she succeeded in removing my shoes and pants.
All the time I was whimpering and protesting, trying to communicate my desire to keep my clothes on but she only ignored my muffled jabbering.
“I have a lovely top that I just know you’ll think is the cutest thing,” she said as she picked up a white and pink t-shirt sort of garment.
“And after we’ve got you all dressed and diapered for beddie-bye, we can do some coloring in your Barbie coloring books–would you like that?” she asked hopefully.
I shook my head but she was already pulling the soft fuzzy top over my arms. It had short, puffy, elasticized pink sleeves and birdseye lace around the cropped hem. But what really made me cringe was the cartoon applique on the front and word ‘Princess’ in childish writing on the chest.
“Oh, that looks just wonderful on you,” she enthused, “but these ugly underwear simply won’t do.”
“Come look at your new underwear, Chrissie,” she said as she had me step over to the changing table, “Stacks and stacks of bunny soft diapers, for you to wear and wet from now on. No more pretending to be a big boy anymore. And there’re all kinds of plastic panties in the cutest designs so no need to worry about leaking either.”
That was it. I had reached as far as I could go with this crazy woman. There was no way she was going to dress me up like a baby, put me in diapers and do whatever it was she wanted with me. I had no plan in mind, only that I was going to get out of here and run as fast as my legs could carry me. I was reasonably sure I could outrun her in those heels of hers, I just needed to get a head start.
“Stop it!!” I shouted angrily as I finally spit out that accursed pacifier, “I’m not wearing any damn diapers and you can go to hell!” I shouted indignantly.
Barbara’s face registered genuine shock, but she quickly recovered and steeled herself for a confrontation. It was only then that I noticed she was blocking my way to the door, to say nothing of the fact that my pants were still on the ground.
“Chrissie, you’ll learn that I do not tolerate misbehavior or any cursing of any kind in my house.
“I was hoping we could get through a day without you going over my lap but I guess I was wrong,” she told me sternly. Standing before me authoritatively with her slim hands on her hips, her big breasts seemed to thrust out defiantly.
With a swiftness I was unprepared for, she suddenly clenched my wrist in her hand and jerked me over to the crib which had one side already open. Taking a seat on the edge of the plastic covered mattress, she flung me over her lap and yanked my Batman underwear down.
“NOOOOO!!!” I cried as I saw her reach in front of me to snatch her wooden paddle.
“Chrissie, I hope your little tantrum was worth the tears you’re about to shed,” she said tersely, “I’m going to give you the spanking you so richly deserve.”
Before I could think how to respond, I felt her paddle slap my bottom with the scorching wallop of buckshot.
CRACKKKK!!!
I howled out and kicked instinctively just as she swatted me again even harder.
SMACK!!! WHACKKK!!
Unable to maintain my composure a second longer, I burst into tears just as her paddle rained down on my defenseless cheeks again and again. With crisp, angry swats, she spanked me with a vengence, turning my pale cheeks from pink to a bright fire-engine red in a matter of seconds. She peppered my bottom, swinging her wooden paddle in a punishing rhythm as I wailed helplessly and shook my fists in frustration. I saw now how foolish I had been, thinking I could stand up to her. Her sexy nature automatically made one inclined to underestimate her but I wasn’t underestimating her now!
Bawling like a baby, my legs scissored in the air as I my underwear went flying into another corner of the room. Through eyes brimming with tears, I gazed back at her high heeled sandals, spread slightly apart to support my weight as she held me securely with one hand and spanked me mercilessly with the other. Every cruel slap of her paddle on my soft, tender cheeks reduced my will to resist her until I was willing to do anything–anything in the world, just to make the terrible spanking stop.
SMACK! CRACKKKK!!! WHACKKK!! SMMACKKK!!
Her fearsome paddle seared itself across my cheeks like a swarm of hornets as I sobbed and cried helpessly against her superior will and strength.
At long last, she stopped my painful punishment.
I lay over her lap, too weak to get up, my face wet with tears as I bawled like a naughty toddler.
“Are you ready to behave yourself now?” she asked patiently.
Howling miserably, I did my best to respond in the affirmative.
“That’s a good little boy,” she said, all traces of anger suddenly gone.
Helping me to my wobbly feet, she hugged me to her big cushiony bosom, rubbing my back and speaking softly into my ear.
“There there, Baby, its all over now, everything’s going to be okay….”
I shifted my feet from one to another as I practically danced in her arms but my buns stung so much I couldn’t stop crying. My tears splashed down onto the exposed buttery skin of her soft breasts, trickling down the deep crevice of her cleavage.
“There there, little sissy,” she cooed as she kissed my ear, “Go ahead and cry, it’ll do you good.”
I hated the fact she had such complete control over me and I bawled in frustration, even as I felt her big, warm, soft breasts pressing against my chest.
She continued to stroke my back and comfort me, occasionally kissing a tear from my cheek tenderly.
“Thaaat’s it, Chrissey,” she whispered, “Get it all out….cry like the little sissy you are…”
She talked to me warmly and without anger, although I found her words extremely humiliating to have to hear.
With the loving care of a mother, she started gently rocking me as she began softly singing a lullabye in my ear; “Mommy’s going to put her little baby in diapers…diapers…diapers to keep her dry…”
I certainly didn’t want to wear diapers but I wasn’t about to try and stand up to her again.
Stepping back from her, I wiped the tears from my face with a swipe of my arm as I gazed at her pretty face. Still sobbing uncontrollably, with my breath heaving in my chest, I looked into her deep, captivating eyes. I saw nothing but love and affection, motherly love that I hadn’t felt for many years but the pain that was raging across my backside still filled me with anger and resentment towards her.
“Come along Chrissie, it’s time for us to get you changed into your diapers and plastic panties now.”
Gently, she led me over to the wide vinyl covered changing table and set me down where I winced in pain as my hot bottom came into contact with it. A fresh set of tears burst from my eyes and Barbara responded by smiling understandingly and pushing my pacifier gently back into my mouth.
“Now, I know you want to act like you don’t like this but we both know you do,” she told me in no uncertain terms, “All sissies love their diapers and in no time–you’ll feel naked without them.
“But don’t worry–I want you to know that from now on, you’ll never be without them. And you are never to touch them either–understand? The only ones who have permission to change you or touch your diapers in any way are adults–okay, Chrissie?”
I nodded miserably as she smiled with satisfaction down on me.
“That’s mommy’s good little girl,” she said to me.
She took a trio of cloth diapers that were stacked neatly next to the table and positioned them below me. Lifting me up easily by the ankles, she slide them under and began working them around beneath me for a proper fit.
I protested weakly and incoherently as she smeared diaper rash creme across my hot, stinging buns, then set me down on the soft, pillowy mass of cotton.
“You don’t have to worry about wetting anymore Chrissie,” she said cheerfully as if it were a big problem for me, “See the extra soaker pads that are sewn into these? They’ll be sure to hold all your pee, even after a long night of wetting. They’re even called Bedwetters, and they were specifically designed for big sissies like you that wet a lot.”
I felt so childish as she sprinkled fragrant baby powder all over my loins and even up onto my chest. The infantile scent assailed my nostrils and breathing deeply of it, I felt transported back to my childhood.
“Here’s one pink bunny pin,” she announced merrily as she held the bulky sides together and pushed the safety pin into the cloth to secure it.
“And here’s the other,” she said, doing the same with the other side.
“There! Look at you!” she exclaimed as her long-nailed creamy hand gently patted the front of my now thickly diapered crotch, “Your very first diaper since your mommy potty trained you. Now, all you need is a pretty pair of plastic baby panties!”
Sucking anxiously on my pacifier, I squirmed nervously as she leaned over and began sifting through my new dresser for a covering.
What would my friends say if they were to see me now?
“Here we are!” she said brightly, “Perfect for a sissy’s first day in diapers!”
Holding them before me, I gazed in dismay at the white translucent plastic panties decorated with blocks and rattles. Pink birdseye lace lined the legs and waist and without delay, she began working them over my feet and down my legs towards my hips.
“See how these are partially clear?” she asked, “That way, Mommy can tell when her little baby girl has wet herself.”
I shuddered at the thought even as I noticed her subtle change of pronouns when she referred to me.
Bending over me as she went about her business, I gazed absently at her big sexy breasts within her tight top as they swung ponderously before me.
Tugging the soft waterproof panties up my legs, she worked them over the thick, bulging diaper until the elastic waistband was hugging my skin. Taking the baby powder, she powdered between my legs and then softly rubbed it into my tender skin.
“Oh my, you look soo cute,” she gushed happily, “So completely natural in diapers, just like a perfect little sissy girl.”
I blushed hotly and whimpered around my pacifier as she helped me to stand up. The thick bulk between my legs felt awkward and I was forced to stand with my legs slightly apart.
“Come take a look at yourself in the mirror, Chrissie,” she said as she led me over to a full length mirror in the corner of the room, “You’re so cute I just want to eat you up!”
She emphasized her point by squeezing the thick seat of my diapers, making me squeal with surprise like a girl.
Looking at my childish reflection, I blushed fiercely as I beheld myself for the first time. My legs, which had always been smooth and free of any hair, only added to my babyish appearance and with my pink sissy top and bulging diapers, I truly looked like a toddler. And the fact that I was still sniffling around the big rubber pacifier stuffed in my mouth served to complete my humiliating look.
“Now I’m afraid since you acted up earlier, Mommy’s going to have to put you down for your naptime now,” Barbara said, a trace of disappointment in her voice.
Leading me over to the crib, she helped me in and tucked me in tenderly, pulling the baby blankets up and putting a teddy bear under one of my arms. She raised the side bars and then to my surprise, lowered a closing top which made the crib a veritable cage! Taking a stout lock, she fed it through a hasp at the edge and locked it shut.
“That should keep baby in her place,” she said, “Now you just hold still, and Mommy will get you your bottle, Honey.”
Instinctively, I reached out and felt the wooden bars that surrounded my new prison–they were strong and quite secure.
Before long, Barbara returned with an extra large baby bottle in her hand.
“Here you are, Chrissie, a nice big bottle of warm milk. Now I want you to make sure you completely finish that before I come in again for you,” she warned me with a wag of her long nailed finger, “Little sissies that do what they’re told get treats but those that disobey get spanked. Okay Sweety?”
I nodded my head sullenly as I took the bottle from her.
Reaching between the bars, she pulled my pacifier out and pushed the big rubber nipple of the bottle between my lips.
“That’s a good baby,” she cooed musically, “Nurse on your ba-ba.”
She stood there to watch me for a bit, just to make sure I was going to do as I was told and then she turned to go, making sure the Care Bears nightlight was on.
“Sweet sissy dreams, Chrissie,” she sang out as she softly closed the door.
Quickly removing the bottle from my mouth, I set it down next to me, pouting miserably in frustration. Never in my entire life had I been so completely humiliated! Oh, how I hated this woman! She’d punished me far worse than anyone had ever come close, and yet, I was so helpess before her! My cheeks burned with shame over my babyish outfit, even as my bottom cheeks burned from the recent paddling. To think I was wearing diapers and plastic pants! How had this even happened to me?
One thing was for sure–as soon as my mom found out, there would be hell to pay. I intended to explain everything to her–well, maybe not everything. I’d do my best to down play certain things. I had no intention of describing the diapers I was forced to wear for instance. But I’d be sure to tell her this crazy woman had done everything humanly possible to humiliate me. She’d be as indignant as I was and then I’d never have to see Barbara again.
Lying back in the semi darkness, I sighed in frustration.
On the other hand, who was I kidding? My mom would probably applaude Barbara for so thoroughly punishing me. Maybe she’d even agree to some long term arrangement for me to stay here. God, how terrible would that be?
Pouting to myself in misery, my mind began wandering and I found myself once again thinking about Barbara’s tremendous curvy breasts. Man oh man, they were huge, I thought to myself. Her skin was so soft and her round boobs so plump and sexy. Without warning, my penis sprang to attention and I reached down to it without thinking. Unfortunately, my hand was seperated by the snug plastic panties I was wearing and several thick layers of cushiony cotton diaper.
Impatient to stroke myself, I began rubbing the soft pliable front of my diapers, which resulted in a wonderful, pleasurable massage of my aching penis. Waves of ecstasy washed over me as I used the other hand to join in. Much as I hated my humiliating new underwear, I had to admit they felt fantastic between my hands and my hard on. Spreading my legs, it only took a moment before I had one of the most powerful orgasms of my entire young life, making me shudder with joy in the crib. It left me gasping for air and it was several seconds before my eyes finally uncrossed.
As I lay there, coming down from the high of my climax, the full weight of my shame hit me like a stack of bricks. Here I was, dressed like a little baby girl and I had just used my diapers to masturbate into. Worse yet–it had felt better than anything I’d ever experienced. As hard as I tried to, I couldn’t stop Barbara’s words from ringing in my head: “All sissies love their diapers and in no time–you’ll feel naked without them…All sissies love their diapers and in no time–you’ll feel naked without them…”
Was I really a sissy? I despised myself for proving her right. Looking down in the soft light at the shiny plastic of my bulging diapers, a new wave of humiliation swept through me. Only a complete sissy would be caught wearing these! And yet, they felt cozy and wonderful. I was so confused! In my angst, I cried myself to sleep.
Chapter Three A Visit From Melissa
I slept the better part of the afternoon, despite the unfamiliar, awkward bulk between my legs and the crinkly vinyl waterproof mattress cover I was lying against.
In my dreams, Barbara was letting me kiss her wonderful big breasts, unbuttoning her tight top to reveal more and more of her soft, silky smooth skin. She smelled lovely and I luxuriated in her intoxicating closeness.
I woke up slowly and as I did, I found myself rubbing the front of my diapers with eager abandon. Once again, I found the combination of soft, comforting cotton to be more than I could stand, and in no time, I came explosively as visions of Barbara swam before my blurred, half closed eyes.
Like deja vu, once the rush of the orgasm had faded, I was crushed by shame. Here I was, fantasizing about my arch foe–a woman who had reduced me into a simpering, sissy baby girl! How low had I sunk? Yet, I was a helpless slave to my lustful desires. There was no denying Barbara’s beauty and incredible sex appeal. How could anyone resist such a woman? Subconsciously, I realized it was just one more weapon in her arsenal that she used against weak willed guys like me. And I was completely defenseless against her!
Out of the corner of my eye, I saw the nursery room door open and recognized the hourglass silhouette of Barbara coming in.
“Hello Chrissie,” she called out softly, “Is my little baby awake?”
“Uh-huh,” I answered.
She turned on the light and came over to the crib, bending over to look in on me. I took the opportunity to stare down the front of her low cut top and I gaped at her magnificent boobs. Even having cum so recently, I felt my little penis beginning to stiffen within my diapers.
“Chrissie? Did you finish your milk like I told you?” she asked suspiciously.
I had completely forgotten about it and bleated out a nervous ‘oops’ as she picked it up.
“You’re a naughty little sissy!” she scolded me but I sensed she wasn’t really angry, “I’m going to re-warm this and then you are to finish it immediately. I’ll let you get away with this on this occasion but the next time is going to cost you a spanking.”
I gulped hard as she strode out of the room, determined to avoid another blistering session with her paddle.
It wasn’t long before she returned and after handing me the bottle, she unlocked my crib top and lowered the side rail. I wasted no time in nursing from the bottle and as she helped me up, she squeezed the thick seat of my diapers.
“Did mommy’s baby wet her pampers?” she asked in a syrupy voice.
“Un-uh,” I mumbled and I blushed nervously, hoping she wouldn’t put her hand down the front and discover the big gooey wet spot from where I had cum twice. That would be a sure way to end up taking another trip over her lap.
“Okay, well, we can wait on changing your diapers, let’s find a pretty outfit for you to wear,” she said eagerly as she took my hand and led me over to the closet.
I was amazed at all the frilly dresses and rompers she had, and I suspected some of them must have come from her store. Her hands stopped at a silky lilac colored dress and she pulled it out, putting up before me to see how it would look.
“Oh, that will be just darling, she exclaimed with great enthusiasm, “the purple in this dress goes just perfect with your baby blue eyes–you’ll be just the prettiest little thing!”
I blushed in embarassment and she helped me out of the sissy top I had worn for my nap. Holding my arms up dutifully, she brought the dress over my head and fitted it into place. It was made of soft, purplish-lilac silk material with a Peter Pan style collar and a white frilly bodice. Short puffy sleeves ended with elasticized delicate lace, causing them to billow out on either side of my shoulders and masking my boyish torso. The hem, which I soon discovered was extremely short, barely came down past the waistband of my diapers.
“These are all cut very short, so that diaper changes are much easier,” she explained as she buttoned it up in back, “And they all have a secure tie string in back, which prevents any unauthorized removal–this dress will stay on until I decide to take it off.”
I had to stand patiently while she fastened it up carefully, tying the back in a knot I knew I’d never be able to reach, never mind undo. Taking me back over to the crib, she sat me on the edge of the mattress while she went back to the dresser and retrieved some socks.
“Aren’t these special?” she asked, “Look at the cute purple lace around the ankles and the little plastic pacifiers–they jingle like bells when you walk around.”
I groaned inwardly, even as I did my best to finish the big bottle of warm milk. I hated milk, especially warm, but I knew better than to make an issue of it. Unfortunately, between having already drank quite a bit and cumming twice, I was starting to feel a real need to pee. I wasn’t about to use my diapers and I figured I could just wait until my mom came by for me. It shouldn’t be long now, I reasoned.
After putting the frilly, purple trimmed anklets on me, Barbara knelt down to buckle a pair of glossy black Mary Janes onto my feet.
“You’re going to be the cutest little baby girl ever!” she gushed proudly.
“I think the next item I need to get for you is a little purse,” she said as she looked me over critically.
“Okay, I’m sure you’re getting hungry–let’s get you ready for dinner,” she remarked as she stood me up.
Taking my hand, she led me down the hall and into her spacious kitchen. The fat diaper forced me to waddle and I was unacustomed to feeling the slippery plastic bulk brushing against my inner thighs. The dress swished noisily and it made it impossible for me to forget I was dressed like a little baby girl.
Once we got into the kitchen, Barbara helped me up into a sturdy pink highchair, much bigger than a normal one and apparently made for someone of my size. As soon as I was seated, she removed the step I had used to get into the chair which left my feet swinging uselessly. There was a matching tray that she brought over and slid into the sides of the chair where it clicked with a locking sound. If I didn’t already feel helpess with that, she began securing my wrists with two pink velcro straps.
“That’s just so baby doesn’t interfere with her feeding,” she told me as she beeped my nose playfully.
With the tray against my abdomen and my wrists restrained against the sides, I was completely at her mercy.
“Now, we certainly don’t want to mess up your pretty dress so here’s a nice baby bib for you.”
She came around behind me and tied a big plastic Dumbo bib around my neck, carefully smoothing it down over my chest.
“That’s a good baby,” she said, “now you’re all ready for num-nums!”
She wasted no time in emptying several jars of baby food onto a green plastic divided plate and with a large spoon in hand, she brought it over and set it on the tray in front of me.
I started to squirm uncomfortably because my need to pee was getting more urgent and I wasn’t sure how much longer I could hold it. At the same time, none of the slop she was about to feed me looked in the least bit appetizing and I wasn’t looking forward to this meal.
“Here we go, Chrissie, din-din time!” she sang merrily.
Scooping up a big spoonful of something yellow, she brought it up to my lips but I blanched at the smell.
“Un-uh,” I balked weakly.
“Open up Sissy, baby needs her veggies,” she urged me.
I turned my head but she followed my lips with the heaping spoon of slop. I was keeping my lips pursed shut but then she pinched my nose with her free hand and held it closed, smiling down on me as she waited patiently. In no time at all, I gasped for breath and she rewarded me with the entire spoonful of pureed corn. Most of it got in, although some slopped on the side of my mouth. I nearly choked on the foul tasting glop but I managed to gulp it down nonetheless.
I wanted to wipe the food off the side of my mouth but I couldn’t move my hands and Barbara was already bringing another heaping spoonful up to my face.
“Here comes the train…into the tunnel!” she sang in some sort of nursery song.
“Nooo–” I whimpered but she shoved it into my mouth anyway.
“MMRPHH,” I gurgled and it was all I could do not to spit it out.
Barbara was ready with another spoonful, this time of a green colored food. I shook my head no but once again, she held my nose and forced it into my mouth. Half of it spilled down my chin and plopped onto the front of my bib.
“Oh, you’re a messy eater,” Barbara chided me.
Scooping up the slop from my bib, she combined it with another spoonful of something else and brought it up to my face.
“Open up Chrissie, this is good for you,” she assured me confidently.
I was squirming in my seat, struggling to get away but the velcro straps kept me securely in place. On top of that, my bladder was aching and ready to burst. It was all I could do to fight Barbara’s frenetic feeding pace but the need to pee was becoming even more critical. And everytime I opened my mouth enough to cry out, she filled it with more slop. By now, my chin and mouth were covered with different colors of baby food, yet she still kept bringing more to my lips. My stomach was turning somersaults and I felt queezy from the nasty food I was forced to gulp down.
I shook my head no but once again, she held my nose closed until I was forced to gasp for breath.
“Here you go!” she sang with a big smile as she poured another heaping spoonful of mashed peas into my open mouth.
Struggling helplessly against my bonds, I suddenly felt the dam burst. With a plaintive cry, I felt a strong surge of hot pee flooding into my diapers. I wriggled in place and cried out, only to have Barbara shove another spoonful of slop into my mouth, muffling my wail of desperation. Another strong surge followed the first, and the warm wetness spread rapidly across the front of my diaper. I sobbed in despair and gave up in defeat, capitulating to nature’s call as millions of babies had done before me. My bladder had been holding a day’s worth of pee and there was no stopping it now. After soaking the front of the thick cotton cloth of my diaper, the warm pee seeped back between my legs, quickly saturating my seat. More pee followed the beginning surge, creating a warm yellow puddle between my legs. In helpless frustration, I burst into tears, the food in my mouth spilling over my jaw and down my chin.
Barbara stopped momentarily to look down at me in sympathy.
“Awww, what’s da matter Sweety?” she said in her cutsey baby’s voice, “Is Cwissie having a bad day?”
The tears streaked down my cheeks and into the slop that was caked all over my face. My pee was still running strong and I feared it would leak out the sides and onto the seat of my highchair. Shifting in my chair, I felt the warm wet cloth squishing and clinging stubbornly to my bottom. I felt so babyish, having been forced to wet my diapers like an infant and I bawled uncontrollably.
Barbara lowered her head sideways and gazed at the darkened front of my diapers.
“Ahhh, I see,” she beamed at me with a look of pride, “Mommy’s little girl just wet her diapers!”
I shook my wrists in frustration but the velcro straps held me all too well.
With the palm of her hand, she placed it against the warm front of my diapers to feel my wetness.
“Oh my, you are quite the little wetter, aren’t you?” she giggled, “I’m glad I triple diapered you, but don’t worry Honey, those plastic panties will keep it all in.
“Tell you what,” she suggested, “We’ll finish up dinner and then I’ll get you into a nice, fresh set of pampers, okay?”
Without reponding, I just sat there and cried like a toddler. Ever since I had seen her, Barbara had been forcing me to her will and I was sick of it. I was so angry I wanted to scream and I hated myself for crying but I couldn’t seem to stop. Once started, I could no more stop my crying than I could my wetting.
Just then, the doorbell rang and I froze in position.
“You just stay right there,” she said unnecessarily as she set the spoon and plate down on the tray, “I’ll be right back.”
I watched with trepidation as she sauntered off, her sexy bottom sashaying and her high heels clicking across the hardwood floor as she went to the front door. I was terrified of being seen like this and I kicked my feet helplessly as I struggled in futility to free myself. What was I going to do if someone saw me in this position? With my soaking wet diapers, baby food caked face, and the fact that I’d obviously been crying, I looked no better than a crabby two year-old.
Opening the door, Barbara stood aside as she greeted her caller in a friendly voice.
“Hello Melissa!” she exclaimed as she gave her friend a big hug, “Come in, come in!”
I watched in horrified panic as a tall, raven haired woman stepped into the entranceway. She was quite a looker and she was dressed smartly as well. Black leather high heeled boots accented her skin tight pants showing off her fabulous physique. She had a white blouse, unbuttoned to the waist and underneath, what looked like a black corset that pushed her sexy breasts into two exciting mounds of feminine glory.
But right now, I sat cringing as she turned to face me, the look of disapproval plain to see on her pretty face. I had never felt more like a complete loser in all my life.
“I hope I haven’t come by at a bad time,” she said cautiously to Barbara.
“No, not at all! In fact, you’re timing couldn’t be better. Chrissie was just finishing up his dinner and he’s already wet himself so I was just going to change him. I’ll get him cleaned up before you start so it’s a perfect time to get his measurements,” she explained.
My face, already covered with colorful baby food, just turned another shade of deep red.
Melissa came over to get a better look at me and I sat there sniffling, puffy eyed, with slop caked all over my face. She shook her head at what she saw–a teenaged guy wearing a dress and wet diaper who looked helpless without his mommy.
“What a sissy,” was all she said as she shook her head.
“He certainly is,” Barbara confirmed, “I knew right off when I first saw him he was either a panty thief or momma’s boy. I was able to get some information from his mother and when I brought him over, I put him straight into diapers and baby clothes. I think this stage suits his immature, whiny personality the best–dressed like a two-year old toddler. No bras and panties for him–it’ll be diapers and onesies from now on,” she chuckled smugly.
I felt myself blushing all the way to my ears at her humiliating appraisal of me.
Melissa had crossed her slim, toned arms over her prominent bosom as she watched Barbara take a warm washcloth and wipe my face of food and the tears I’d cried. I was devastated to be seen like this and I kept my eyes on the floor, unable to look this tall, strong woman in the face.
When Barbara was finished and my bib had been removed, she undid the velcro straps around my arms and pulled out the locking tray in front of me.
“Come on Chrissie,” she said brightly, “Let’s go get those wet diapers changed.”
She emphasized her point by giving my thickly diapered seat a slap which landed with a dull thud.
I trudged along behind her as she held my hand and led me back to the nursery, Melissa coming along behind us.
“D-does she hafta watch?” I whimpered in my pleading voice.
Barbara turned to look at me in surprise.
“Don’t you worry your pretty little head about that, Sweety, you’ll be seen by all my friends sooner or later so this is something you’ll just have to get used to.”
I pouted and stamped my feet in frustration over the unfairness of it all.
“There’s no point in getting fussy, Chrissie–you can bet some of them will want to change you themselves, once they see you what a big baby you really are.”
Sitting me down on the changing table, Barbara pushed the short lacey hem of my dress up my chest, further exposing my sopping wet diapers. I blushed hotly with shame as Melissa stared down at me hard, not a trace of sympathy to be found on her stern face.
With Barbara’s long glossy fingernails, she reached into the clinging elastic waistband of my plastic panties and began tugging them down over the wet cotton cloth.
“As you can see, a big sissy wets quite a lot; I’m using triple thick diapers with a soaker pad for him which is just what he needs–that, and a good snug pair of plastic panties.”
Melissa started fishing in her purse and she got out a pen and paper, along with a small measuring tape. I hadn’t the slightest idea what she had in mind but to be honest, that was the last thing on my mind. Not only was this strange woman seeing me with wet diapers, she was also about to discover just how small my weiner was.
My penis had always been an acute source of embarrassment for me. It seemed that after about the second grade, it had just stopped growing and it was by any standards, tiny. While the rest of my body had grown more or less normally, my penis remained stunted and disproportionately small. I had always hoped that puberty would spur the growth somehow but so far, I hadn’t seen any evidence of that.
I squirmed in embarrassment as Barbara unpinned the sides of my diaper and peeled the soaking wet cloth back.
“OH-MY-GOD,” Melissa exclaimed in shock, “Is that thing real?”
Barbara stopped my changing as she burst into laughter, her hand coming to rest on her friend’s shoulder as she shook with amusement.
“Yes, that’s all there is,” she said as soon as she could talk again, “Do you see what I meant about needing a custom device?”
“Oh my god–yes,” Melissa nodded her head, “I’ve never seen a penis that small! It must be an inch or so!”
Without waiting, she held her tape measure down next to my wilted, humiliated member, scrutinizing the size carefully.
“Yes, that’ll be a total custom order for sure,” she affirmed.
“Can you do it?” Barbara asked hopefully, “Even the Birdlocked Mini will be way too big for him.”
“Oh yes, way too big,” she agreed, “No, this one will be completely hand made to fit him.”
I had no clue what they were talking about but I wished Barbara would finish and cover me back up. It was mortifying laying here while these two made fun of my diminutive weiner.
“What are you measuring for?” I asked uncertainly in a small, feeble voice.
Barbara just smiled down at me before taking my pacifier and pushing back it into my protesting mouth.
“There you are Sweety, this is just grown-up talk that doesn’t concern you. You just suck on your paci.”
I pouted in frustration and did as I was told, but I wished I knew what they were talking about.
“Do you shave his legs and crotch?” Melissa asked in wonder.
“No, not at all,” Barbara laughed, “Amazing, isn’t it? This is how he came to me, bald as a baby, even around his little package here.”
I blushed hotly at her keen observation.
“His legs are so girlish,” Melissa remarked disparagingly, “I thought maybe you’d waxed them or something.”
Barbara giggled and shook her head as she removed the heavy wet diaper from underneath me, plopping it into a sturdy plastic bin.
Melissa took her tape and ran it around the base of my genitals, noting the figure on her pad.
“I’ll have to get a measurement of him erect–can you do that?” she asked.
“Sure thing,” Barbara replied and she picked up a bottle of baby lotion that was next to the changing table. Squeezing some in her hand, she began rubbing it gently around my shrivelled, embarrassed penis.
“Do you like big breasts, Chrissie?” she said as she undid the uppermost button on her top.
I was extremely humiliated with what was taking place but as I stared at the perfectly round shapes of her sexy bosom, my weiner responded all too predictably. In no time, it was stiff and hard, throbbing within her soft, sensuous grip as she smiled down upon me.
I groaned with desire and yearning for a third orgasm even though a part of me was saying I should show some dignity to resist her.
“There you are,” she said as she released my slick penis, “I think that’s as big as it’s going to get.”
Melissa just shook her head in amazement.
“Unbelievable, it looks like a stubby crayon.”
Afraid it would collapse without further stimulation, Melissa hurried to measure it with her tape, jotting down the last figure on her pad.
“Got it,” she said with finality, “So, does he masturbate quite a lot then?”
I shook my head no and bleated out a muffled protest but they both ignored me as if I didn’t exist.
“His mother told me he’s a chronic masturbator, that’s why I wanted to get this as soon as possible,” Barbara informed her.
“Yes, he looks like a little masturbator, I’ll bet he does it several times a day.”
It was clear she thought of me as a nasty little perv and I blushed, shaking my head vigorously in disagreement.
“I’m sure of it,” Barbara agreed, “Is there any way you can put a rush on that?”
“How about a week?” she responded, “This one is going to take longer than usual due to how tiny he is.”
“I understand, do what you can,” Barbara told her.
If only I knew what they were talking about!
Barbara had slid another tall stack of fresh diapers beneath me and she pinned them around my hips as they made small talk between themselves. I was totally forgotten as they laughed and talked about the men in their life–real men, they emphasized, and it made me jealous as hell to have to sit there getting my diapers changed like a toddler and act like I couldn’t hear them.
Barbara finished my changing as she pulled a pair of soft pink plastic panties up my legs.
“Here you are, Chrissie, all diapered and ready for bed. I’ll just get you some jammies to wear.”
I whimpered around my pacifier and made it obvious my disapproval.
“No, it’s 7:30, Chrissie. That’s bedtime for sissies who wear diapers,” she told me firmly.
Moving behind me, she began untying the knot she’d made earlier at the back of my dress and she pulled it over my head. After she hung it back up, she brought over a fuzzy white onesie with bunny designs decorating it. I fussed crankily as she worked it over my head and pulled it down over my chest and waist. It had a big row of pink ruffles around the elasticized waist with smaller matching ruffles around the leg openings. Reaching between my legs, she snapped closed the four metal snaps between the legs, making the soft fuzzy fabric cling snugly to my bulging diapers. Somehow, I found this babyish garment even more humiliating to be dressed in–maybe because it also signified my early bedtime and the crib I’d soon be sleeping in.
Catching sight of myself in the full length mirror, I couldn’t believe how sissyish I looked. My fat diapers gave me a distinctive bell shape with the big ruffles looking like a sissy belt. My glossy Mary Janes only added further to the effect although Barbara soon removed them and put them away.
“I’m going to get you your bedtime bottle and then it’s off to the crib for you, Missy,” she said as she rose to her feet.
I chewed the fat rubber nipple that filled my mouth in acute frustration as Melissa ignored me and made a call on her cell phone, telling someone about the measurements she’d just taken. I was impatiently waiting for my mom who should have come over by now and I didn’t understand what was taking her so long. If she didn’t come over soon, I’d be in bed already and I was afraid she’d leave me here.
Melissa left without so much as a goodbye and while I thought she had a sexy body, I was very intimidated by her and was relieved to see her go.
Barbara soon returned with the bottle of warm milk and she guided me to my crib with stern admonitions to drink it all or I’d start off tomorrow with another sore bottom. As soon as the pacifier was out of my mouth, I began squealing for an end to this.
“When’s my mom gonna come get me?” I whined, “I don’t wanna play baby anymore.”
Barbara was very patient and she sat me down on the edge of the crib mattress while she picked up the teddy bear that was lying there.
“Chrissie, it’s time for you to face a few facts. Your mommy isn’t coming to get you…not tonight, and not anytime in the future. We’ve talked about your behavior and it’s been decided that you’ll be staying with me from now on.”
My jaw dropped open in shock as I tried to digest this devastating news.
“I know this must seem like a lot to take in one day, Chrissie, but believe me, it’s all for the best,” she continued.
I shook my head in disbelief as I struggled for words to say.
“I can see you’re upset but there’s nothing to worry about, Honey. Nothing at all. Because I’m going to make sure you’re the cutest, best behaved little baby girl any mother could hope for.
“Don’t you see how this is what you really need? We both know that deep inside, you’re just a little sissy that’s dying to get out. And I’m going to make that happen for you. You don’t have to worry about being a tough little guy anymore, trying to act like something you’re not and you don’t have to be responsible anymore…I’m you’re new mommy and I’m taking away all your responsibilites from now on.
“I’ve got lots of fun toys for you to play with, some cute dollies and coloring books, some big plastic building blocks and tommorrow, I’m getting a big playpen so you can play in the living room while I’m entertaining my girlfriends.”
She told this to me like it was something I really wanted but it was all horrifying news to me. All this time, I had been waiting and counting on my mom to come rescue me from this domineering, controlling woman. I still couldn’t believe she wasn’t coming.
“But I don’t want any of that!” I whined strenuously, “I’m not a baby and I don’t wanna wear diapers anymore.”
Despite my best efforts to give the appearance of being strong, hot tears, brought on by panic, began brimming in my eyes.
“You poor little sissy,” Barbara said soothingly, “I know this must seem rather unfair and a bit overwhelming…after all, just this morning you were a big teengage boy in class and now you’re a diaper wetting baby being put to bed in your crib.
“But it’s really all for the best, Honey, believe me,” she repeated, “Your mom and I talked it over and we agreed this is just what you need. You don’t belong in school, wearing your jeans and trying to fit in with the other guys. Where you belong is in a nursery, wearing diapers and dresses and that’s just what I’m going to do for you. You won’t have to figure out what to wear anymore because I’ll do that for you. I’ll dress you in the morning–after I’ve changed your wet diapers that is–and I’ll decide what to feed you. I’ll decide where you can play with your toys and I’ll decide when your naptime is.”
I was shaking my head silently as the tears spilled down my face. My shoulders began to shake as the finality of my situation came crashing down on my like an iron portcullis. Barbara was too strong for me to face physically and she’d already shown that I was no match for her mentally either.
Taking the bottle out of my hand, Barbara gently stood me up and led me over to a plush love seat situated in the corner of the room.
“There, there, Baby,” she said in her soothing voice, “Don’t cry now…tell you what–I know just what baby needs, you come right over here.”
I didn’t want anything to do with her but I didn’t fight her as she sat down and guided me into a lying position over her lap. As I looked up into her pretty eyes, her massive bosom was just inches from my face and I sucked my breath in as I gaped at it’s fabulous shape. Barbara smiled down on me as she saw I was momentarily distracted and I watched as she slowly undid the first button on her top. I knew she was manipulating me–it was only too obvious, and I hated her for it. Yet, there was no way I could resist her either. Even as the tears trickled down my cheeks, my penis was hardening and becoming erect within the soft, comforting folds of my diaper. I was angry with her for what she was doing to me but I was completely powerless to hold back my libido.
I watched in captive fascination as she undid the next straining button, and then the next, until her clinging top was pulled aside and the front of her white lacy bra was exposed before me. I had never seen a bra this close, not even my mom’s, since she made a point of hiding them from me. Of course, I’d masturbated to pictures in magazines before but this was the real deal!
I found my breath becoming labored as I greedily took in the unbelievable sight before me. The smooth, satiny cups of her bra were so sexy, and my eyes were riveted, taking in every feminine detail for the first time.
My lips were dry and I licked them nervously as Barbara used her lovely manicured fingers to undo the clasp that held her two huge cups together.
“Don’t cry, Chrissie…Mommy’s going to give you something all little babies need.”
Having been shy all my life and having never kissed a girl prior to this morning, I was quite overwhelmed with my present circumstances. My face was flushed and my heart was pounding in my chest as I squirmed uncomfortably on her lap. As she eased her right cup away, I stared dumbfounded as she pulled it back, revealing more and more of her incredible plump breast. It was as big as my head!
“These are just bursting with milk, Chrissie,” she beamed down at me, “And I’m going to make sure you get your fill everyday.”
I whimpered weakly, pleading with her that I wasn’t ready for this. She smiled warmly and cupped her big round mammary in her small hand, positioning her large pink areola in front of my face.
“This is what you need, little sissy, a nice warm nipple and mommy’s milk to sooth you.”
I shook my head and closed my eyes in panic but I felt the damp tip brush against my lips.
“No…no…please…” I whimpered as I blinked back more tears.
“There, there, little baby, open up for mommy now…” she urged me softly, “Take mommy’s pink nipple….time to suckle….open up my little sissy.”
I felt her gently pressing it against my lips as her other hand reached around to cradle my head, effectively trapping me. I squirmed and squealed but I couldn’t escape. I felt her firm, urgent nipple between my lips and as I struggled and pleaded with her, she gently pushed it into my mouth, filling it and muffling any further complaints. A sob was stifled as I tasted her warm nipple on my tongue. Still trying to speak, the movements of my jaws flexing around her breast brought forth a stream of strange tasting liquid to my mouth and my eyes popped open in surprise.
“That’s right baby,” she said as she smiled down on me knowingly, “Mommy’s got her own milk for you.”
I whimpered weakly as she gently stroked the back of my head and without thinking, I began nursing like an infant.
“Thaaat’s a good baby,” she whispered softly to me, “That’s mommy’s little baby.”
My face was red with embarassment at this uniquely infantile act but despite that, my penis was rock hard in my diapers.
“This is what you’re going to get everyday from now on, because all babies need their milk,” she cooed gently in my ear, “And guess what? Some of my friends are lactating too so you’ll get the chance to nurse from them as well.”
I sucked feverishly now and was rewarded with a steady stream of her maternal nectar. I swallowed it and hungrily sucked harder, my head spinning at what was taking place. Never in my wildest imaginings would I have pictured what I was doing. It was humiliating in the extreme, yet my heart was pounding with excitement. Barbara’s big breast tasted wonderful in my mouth and the scent of her skin was like ambrosia. As I nursed like a baby from her bountiful bosom, I felt a sexual wave swelling within me and my penis throbbed mightily. I could feel my blood coursing through me like electricity and I was breathing heavily through my nose. At the same time, my cum was bubbling up, closer and closer and there was nothing I could do to stop it.
With an inevitablity I knew I couldn’t resist, I climaxed with an explosive force in my diapers. Howling noisily, Barbara kept my mouth firmly in place with her big nipple filling my mouth like a gag as I moaned deliriously. My eyes crossed and my head swam as I tried to cope with the magnitude of my incredible orgasm while my body convulsed and shuddered in ecstasy. I could feel a big gooey wet spot forming in the front of my diaper and I marveled at the fact I hadn’t even touched myself.
Barbara smiled down on me with what looked like pride on her beautiful face. Or maybe it was the smug look of her knowing she’d bent me to her will but either way, I didn’t care. Right now, I was riding the delightful wave of post-orgasmic bliss, feeling my hard-on gradually beginning to soften slowly as it began shrinking down to it’s usual limp form.
For a moment, Barbara pulled her breast out of my mouth as I lay there, gasping for breath. My face was flushed and I looked up at her through half closed eyelids, suddenly feeling very sleepy.
“Well, I think that took all of thirty seconds,” she told me, “You really don’t have much control do you?”
I swallowed and looked away, extremely embarrassed with myself. It was true I had very little staying power but I’d never really given it much thought.
“But that’s okay because with aunt Melissa’s help, we’re going to take care of that little problem next week.”
“Wha-what do you mean?” I croaked as my breathing began to become normal again.
“No need to worry about that, Chrissie, Mommy’s got everything under control. And very soon, you will be too,” she giggled.
I sensed danger in her vague statement and felt I should press her further.
“What do you mean? What’s going to be under control?” I asked again.
Without answering, Barbara reached over and brought the baby bottle to my mouth, easing it between my lips as she shushed me.
“Hushhh little baby,” she whispered, “It’s beddie bye time for mommy’s sissy girl.”
I hated being denied anything, and her ignoring my questions left me frustrated and resentful.
Standing me up, she led me back over to the crib and tucked me in, placing the teddy bear under my free arm as she pulled the soft fuzzy blankets up around my chest.
“There, there, Chrissie, Baby’s had a big day but it’s time to go to sleep now.”
Closing the top of my crib, she slipped the lock in the hasp and clicked it shut, sealing my prison for the night. The Barbie clock on the dresser read 7:32 pm.
Chapter Four A Baby Shower For Chrissie
Barbara peeled the soaking wet diaper off my bottom and plopped it into the big rubber bin behind her. Even though she made a point of washing my soiled diapers on a daily basis, the nursery had begun to take on that distinctive smell of a toddler’s room who frequently wets–it was the pungent calling card that let everyone know the diapers I were wearing weren’t just for looks.
After the first day, I resolved to hold off my urge to go until the very last minute–that was–when I knew Barbara would be changing me anyway. It was my only means of rebelling, however small, against her implacable rule. Of course, sometimes it didn’t work and I was forced to wear a wet diaper for some time before she eventually changed me. And there were times when she’d just changed me and only minutes later, I’d have an urgent need to pee that I couldn’t hold. That was the worst and often, even when I told her about it, she’d still make me wear them until my usual changing time. her usual response being to tell me that “all babies need to get used to wearing wet diapers” and that it would “do me good”. Nevertheless, I resented having to wear a wet diaper around for several hours at a time, especially when they were trapped inside a snug pair of plastic pants.
Fortunately for me, I had been thus far, completely successful in hiding my frequent masturbatory activities from her. As far as I could tell–she was none the wiser that I was playing myself three to four and sometimes five times a day. And in my defense, there was little else of interest to do–it was either that, or play with her baby toys she had all over the house. But I was also convinced that it was a physical necessity as well. Barbara never wore anything that didn’t show her big luscious boobs in the most flattering way possible and even after I’d cum, the sight of her in a tight, clinging top never failed to make my penis begin to harden all over again.
And during the afternoon, she’d sit down on the couch and let me breastfeed from her which inevitably resulted in another orgasm for me. Truth be told, my sex life had never been so active, although it was still entirely one-sided.
I watched Barbara carefully now as she wiped my damp buns with a baby wipe. Her side to side movements made her big round breasts sway and jiggle in the most erotic way and my penis stiffened immediately. I had stopped trying to hide my sexual attraction towards her, despite what she’d reduced me to. Of course, it would have been impossible in any event, because she saw my physical reactions every time she changed my diapers. For her part, she often ignored my hard-on or giggled to herself as she powdered it and pulled my diapers back up to pin them closed. And I knew I’d be masturbating furiously without fail, the moment her back was turned so I had learned to be patient.
We seemed to have arrived at a sort of understanding between each other. Or rather more accurately, I’d learned to obey her without question. In any case, it had been two days since she’d taken me over her lap to give me one of her blistering spankings. I certainly wasn’t anxious for another.
“Let’s see…” she mused as she sifted through my bulging drawer of plastic panties, “We want something extra special for my little baby today, and do you know why?”
I shook my head as my pacifer was in its usual place, filling my mouth with soft, pliable rubber.
“It’s your very own baby shower, Sweety!” she said merrily as she playfully beeped my nose, “Your going to have so much fun!”
I gulped hard and squirmed uncomfortably as I pondered the implications of what she had in mind.
“After I get you all dressed up, we’re going over to my good friend Emily’s house where we’re throwing a baby shower, just for you!” she gushed, “Everyone’s bringing presents and I know you’ll have the most wonderful time.”
She told me this as if she expected that it was the best possible news for me to hear.
I shook my head desperately in protest. So far, my humiliating babyish treatment had been seen by only one other person, Barbara’s friend Melissa, and I didn’t want it going beyond those two.
“I’ve got a very special baby outfit for you today–your very own sissy sailor suit–what do you think of that?”
She pulled out my pacifier just long enough to get a response.
“Noo!” I squealed, “P-please don’t take me over there!”
Barbara smiled down at me and pushed the warm nipple of a big bottle of milk in between my trembling lips, stifling any further argument from me.
“Don’t worry Babykins,” she assured me, “I know you’re very shy but my friends just can’t wait to see how much of a sissy you really are.”
I whimpered in vain as I nursed from the big bottle she was holding in place before me. It was my second today and unconsciously, I knew I was going to have a tough time holding all this liquid back for long.
“Let’s see…” she said, returning to the drawer of baby pants after making me hold the bottle for myself, “…Here we are–aren’t these scrumptious?”
She held a pair of white nursery print plastic panties with colorful bunnies and flowers on it before me.
I swallowed weakly, knowing there was little point of fighting her.
She worked the soft, shiny panties over my feet and down my legs, surrounding the big, bulging cloth of my diapers as she carefully fitted them around my hips.
“Oh yes, these will be just perfect with the see-thru rumba panties I have in mind,” she commented.
I nursed from my bottle as she went over to the closet and began poking around until she produced a white, frilly lace top. Bringing it over, she held it before me as if expecting me to show my unbridled enthusiasm for it. It was mostly white, with pink and baby blue accents around the short, puffy sleeves and hem. A big pink satin sash was tied in a bow across the bodice in sailor fashion and I cringed at the layered pink rows of lace along the short hem. Raising it over my head, she pulled my arms through and down over my torso. There were a pair of matching frilly panties on the hanger and she took them off to hold them open for me.
“Here you are, Baby,” she said encouragingly as she fed my feet through and worked them up my skinny legs. They were made of a soft, stretchy, see-thru material that glittered and I noted the fuzzy pink ruffles around the leg and waist. I’d never seen anything so babyish in my entire life but as she pulled them over my diapers, I realized the nursery print of my plastic panties could easily be seen through the material.
“Oh–that is just the cutest thing,” Barbara remarked glowingly.
“Do you know you have the smoothest legs of any boy I’ve ever met? Just like a baby’s,” she remarked as she stroked my bare thigh.
I shook my head but I don’t think she was really expecting a response.
Before long, she was pulling some pink lacey anklets over my feet and buckling my shiny black Mary Janes. I squirmed and whimpered as I contemplated being seen dressed like this. My stomach was turning somersaults and I was tense with nervousness.
“And now, we’ll do your nails in a pretty matching pink–won’t that be fun?” she asked cheerfully.
Sitting me down on the edge of my crib, she took a bottle of pink glossy nail polish and began carefully painting my fingernails, humming to herself as she worked.
“I wish your hair was longer so we could put in curls, Chrissie,” she remarked, “But don’t worry, it won’t be long before that happens.”
I nursed my bottle, switching hands when she’d finished the first one. Then she applied some light blusher to my cheeks and some glossy pink lipstick as I pouted for her. Finally, she sprayed me with a small bottle that said Nursery Nights on it. It smelled like a combination of things; baby powder, soft nursery scents, and somethng else indefinable. In any event, I smelled so babyish, it seemed to eradicate any trace of boyishness I’d ever possesed.
“Take a look at yourself now, Chrissie,” she said in an almost taunting manner as she held my hand and stood me before the full length mirror.
I stared in awestruck silence as I gazed at the sissyish reflection in the mirror. With my slick glossy lips and light make-up, I actually looked quite attractive, albeit in a prissy kind of way. My bare legs and lacey panties and top made me look like an overgrown toddler and there was no mistaking my big, bulging diapers that announced I wasn’t ready for regular underwear yet. I blushed hotly as I quivered in anticipation of someone else seeing me like this.
“You see?” Barbara said as she bent over next to me and we looked at my reflection together, “This is the real you. This is how you should be dressed all the time. Not in some nasty boy’s clothes where you don’t belong. A cute little sissy like you should be dressed prettily, in prissy clothes that allows him to show the world who he really is.
“Of course, you’re more than just a sissy–you’re really just a big baby who isn’t ready to grow up. And believe me, I’ll make sure you don’t. You’re going to be my little baby girl from now on, wearing your diapers and dresses, just like a little toddler girl should.”
I gulped nervously at the picture she was painting. While I could grudgingly admit my features lent themselves well to a sort of prissier side, I didn’t want to dress like this all the time.
“Come along now Sissy,” she said taking my hand, “Here’s your purse with a few things I put in there just in case you need them later. But we have to be going–your new friends are all waiting for you.”
Before I could say another word, she was dragging me out the door and into her minivan, securing me in that oversized carseat in back. By now, I’d finished my bottle and she’d pushed my pacifier back into my mouth before closing the door. I squirmed helplessly, knowing there wasn’t a damn thing I could do about her plans for me.
It didn’t take long before we reached our destination. Her friend Emily’s house was just over in the adjacent neighborhood. As we pulled into the spacious driveway, I noted the large number of cars parked nearby, obviously from the other people who were here to see me. Looking down at my fat, frilly diapers and bare, hairless legs, I whimpered loudly to Barbara.
Opening the sliding side door, she began unbuckling me which also provided me with another opportunity to stare down her top at her big, beautiful breasts. But unfortunately, that was the last thing on mind at the moment. The full force of what was about to happen struck me with all it’s gravity and I struggled to stay where I was. There was no way I was going to let her drag me into this stranger’s house so they could look at me dressed like a baby girl!
As Barbara reached in to pull me out of the seat, I resisted her efforts, my muffled protests sounding babyish, just like my appearance. My pacifier fell out of my mouth and I tried to push her hands away to prevent her from getting me out of the van.
“Noo!” I whined, “I don’t wanna go!”
Barbara slapped my bare thigh with her immaculately manicured hand.
“Oww!” I cried.
“Chrissie–it’s time to mind your mommy and do as you’re told.”
“But I don’t wannnna!” I whimpered piteously.
She slapped my thigh again sharply and although it wasn’t that hard, I cried out in pain, tears brimming my eyes.
“Come along now, Sissykins,” she said firmly, “There are a lot of nice people waiting for you and you’re being rude to make them wait.”
Stuffing my pacifier back into my mouth, Barbara pulled me out of the seat and as I exited the van, I saw several women peering out through the living room window at me and smiling. I whimpered and balled my fists in frustration when all of a sudden, I felt a stream of wetness escape into the front of my diaper. I squealed in panic, my free hand going down to cover my humiliating accident, although it was doubtful that it could actually be seen. Still, the fact that I’d already wet myself would only show these women what a sissy I was and that I really did need diapers. On the way over, it occurred to me that the best plan would be to hold it until we were leaving but now that was clearly going to be pointless. Sooner or later, my accident would be discovered and Barbara would have an opportunity to heap yet further shame on me.
The front door opened before us and a gorgeous woman in her late thirties stood framed in the threshold, a big smile on her face as she looked down on me.
“Hello little Chrissie!” she beamed warmly, “My name is Aunt Emily–welcome to my home.”
Sweeping my up into her arms, she hugged me closely, mashing my face against her incredibly bountiful bosom. I could barely breath but for the moment, I wasn’t complaining. Her hand reached back and gently patted the ruffled seat of my diapers as she kissed me on the cheek.
Releasing me from her wonderful embrace, Barbara and her were soon hugging and chatting eagerly between each other. They ushered me in and I was taken into her large living room, now filled with a handful of beautiful women. They were dressed in various styles, from casual to what looked like business attire although they were all very attractive and sexy, most wearing heels and enticing clothes.
“Come in, come in,” Aunt Emily said as she gently but firmly beckoned me into the middle of the room. My face went three shades of red as these hotties stared at me and giggled, one feeling the lace on the hem of my sailor suit top, another rubbing my smooth thighs while another brazenly squeezed the thick seat of my diapers. I squealed in fright that she’d discover my accident and my pacifier dropped out of my mouth.
“Awww, the little sissy lost his paci,” one of the women said with mock sincerity as she patted me consolingly on my shoulder.
“Ladies,” Barbara said in a louder voice, “This is my new sissy baby, Chrissie–Chrissie, say hi to these nice ladies.”
My mouth was parched as I looked around in panic and my heart was racing as I barely prevented another stream of pee from escaping. I couldn’t speak a word!
Aunt Emily could see the terror in my eyes and she bent down before me, looking into my eyes with maternal warmth as she took my hands into hers.
“Hello there, Chrissie,” she said softly, “Did you know you’re the prettiest little sissy I’ve ever seen?” Her voice was musical, sexual, and filled with kindness all at the same time. In addition, I couldn’t help but stare at her wonderful, plump breasts, barely contained within a tight form-fitting top
I’d never been called pretty before and it gave me a strange sensation–I wasn’t sure whether to be proud or angry.
Still holding my hands in hers, she looked deep into my eyes, her attractive face just inches from my own.
“Chrissie? Are your diapers wet?” she asked full of concern, “Do you need me to take you into my nursery to be changed?”
“Uh-uh,” I croaked hoarsely. My face blushed an even deeper red as I feared she could read my mind and already knew the truth.
“Are you sure?’ she asked, a growing smile on her face.
I shook my head vigorously as the heat went all the way down my neck to my chest. I had never been so humiliated in all my life!
The women continued to giggle at my discomfort and I was unable to even raise my head to return their stares.
One of the women spread out a baby blanket on the floor and she beckoned me to sit down upon it. Awkwardly, I sat down, unsure of how best to position myself, keenly aware of how obvious my fat diapers were to everyone present. All around me, the comfortably seated women looked down on me and I could see them holding gifts that were wrapped in pastel paper with nursery designs. Looking up at their crossed legs, their high heels dangling before me while I sat on the ground, gave me a feeling of inferiority that I couldn’t shake.
“Here Chrissie, here’s a little present I know you’ll enjoy, ” a cute younger woman said, “–My name is Sarah,” she added as an afterthought.
Nervously, I licked my lips as I tore open the small, odd shaped package in a wrapping paper with building blocks on it. I saw a pink plastic ring about the size of a silver dollar and it was attached to a large rubber pacifier. Except the pacifier was shaped like a big, fat penis, not the usual elongated nipple. I blushed anew as everyone burst into laughter, obviously greatly amused with Sarah’s gift for me.
“I’ll bet you’d much rather have that in your mouth than your old pacifier,” she chuckled in a condescending manner. My face reddening, I tried to put it aside but Sarah stood up and came over to retreive it, picking it up and removing the plastic packaging. Tossing it aside, she forcefully pushed it between my quivering lips, forcing it deep into the back of my mouth. I gagged and threw my hands up, squealing like a little girl as everyone laughed at my emasculating predicament. This woman had a cruel look in her eyes, totally unlike Aunt Emily’s and I feared her instantly even as my lips submissively wrapped themselves around the big rubber cock filling my mouth.
Sucking noisily on the fat rubber phallus, I squirmed helplessly as she smirked down on me with a smug look on her face.
“I’ll bet that feels natural in your mouth–hm, Chrissie?” she asked.
Afraid to oppose her, I nodded and hung my head low.
“Awww you poor little thing,” Aunt Emily said sypathetically as she quickly came over and pulled the pacifier out of my mouth. She didn’t however, remove it entirely and instead, she looped the strap around my neck for later use, “Here Honey, now here’s something I know you’ll just adore.”
She presented her own gift that was delicately wrapped, and it too was in nursery print wrapping paper. I gritted my teeth as I ripped it open, to discover an elaborate pink and white dress, with yards of frilly lace and bows decorating it. It was obviously expensive and Barbara knelt down to feel it herself.
“Oh my!” she exclaimed, “Isn’t it beautiful, Chrissie?”
I nodded numbly, wondering how I’d ever come to be in this place, dressed like a baby and opening gifts made for a sissy.
“Now thank Aunt Emily for your wonderful dress, Chrissie,” she prodded me.
I was anything but grateful but I didn’t want to make Barbara angry either.
Clearing my throat, I coughed nervously.
“Thank you,” I practically whispered.
“Thank you–Aunt Emily,” Barbara corrected me.
“Thank you Aunt Emily,” I mumbled.
“Thank you for…” Barbara pressed.
“Thank you Aunt Emily for the pretty pink dress,” I finally blurted out, much to my embarrassment and everyone’s giggles.
“Well you’re quite welcome, Sugarplum,” she cooed, “And I’m very much looking forward to seeing you in it.”
Just then, a tall, dark haired woman with her hair pulled back in a severe bun stepped forward and thrust her own flat shaped package into my hands. It was long and narrow and looked suspiciously familiar.
“My name is Mrs. Sterne,” she said with an authoritative voice that could have cut through hardened steel, “And I run the Francis Merrimont Boys School.”
If Sarah had put me on edge–this woman was terrifying. Her dark eyes drilled through me like I were butter and I squirmed under her intense stare. She was quite attractive, but the firm set of her delicate jaw and the steely look in her eyes told me she meant business.
Swallowing hard, I slowly unwrapped the gift. It was a black oak Spencer paddle with a custom leather-wrapped handle and dime sized holes cut throughout it’s length. My heart pounded anxiously in my chest as I chewed my lower lip.
Everyone else oohed and ahhed but I was afraid to look the woman in the eye.
“I think we should give that one a try right now,” she stated firmly.
So certain was I that this forceful woman would get her way that I turned to Barbara, my eyes pleading with her for mercy.
“Don’t worry Chrissie,” she chuckled, “There will be plenty of opportunities for using that later.”
While not the answer I was exactly looking for, I was nonetheless relieved that she wouldn’t be using it right now.
Looking up, I noticed a younger female that had so far, said very little. She was devastatingly pretty, like Megan Fox, with bewitching eyes and round, perfectly shaped breasts. Her long, raven colored hair spilled over her soft bare shoulders and framed her toned, athletic body. The low cut halter top she wore was achingly taut against her perky bosom and below the cropped hem, I noted her washboard flat tummy.
I was in awe of her beauty and a little disappointed she’d been practically ignoring me thus far.
“I know,” aunt Emily suddenly suggested, “Why don’t we have Chrissie sit on Victoria’s lap while he opens the rest of his presents?”
I could tell from the young woman’s general demeanor that she had no interest in our proceedings and in all likelihood, she probably thought I was creepy. As if to confirm my suspicions, the dark haired beauty rolled her eyes and shook her head at aunt Emily.
“Look, I just came along ’cause I’m friends with Barbara,” she stated as she held her long nailed finger up in protest, “I don’t get what you guys are into with this sissy kid and his weird party.”
The way she said ‘sissy kid’ so dismissively was almost worse than Sarah’s overt condescending attitude towards me, maybe because she was the youngest one there and closest to my age, although she looked to be in her twenties. But to be so callously disregarded by such a pretty woman really hurt my feelings.
“Now Victoria,” Barbara interjected, “You’ll be having your own baby soon. You really should try to nurture your maternal instincts with Chrissie here. He may be a lot older than most boys who wear diapers but he’s really just a big baby deep inside.”
I tried to contradict the impression she was giving but the fat rubber pacifier only muffled my words and she talked right over me.
“Why don’t you just let him sit on your lap for a moment?”
While they were engaged in this discussion, I felt a strong surge in my bladder, signaling that Mother Nature was ready to make a call in a big way. The last thing I wanted was for this hottie to discover my wet diapers, but how could I avoid it?
“Naah, you hold him on your lap,” Victoria countered, “I’m not into sissies–I have a real man waiting for me at home.”
“Now Victoria…” aunt Emily said persuasively, “Just humor us this one time…he won’t bite–I promise you.”
“Yes, he’s really the best behaved little baby you could ever ask for,” Barbara added, “You haven’t even given the little sweety a chance…”
Victoria rolled her eyes again in apparent resignation.
“I know that Chrissie would just be thrilled to sit on the lap of a pretty young woman like you,” aunt Emily said with flattery, “Won’t you grant his wish this one time?”
Victoria exhaled audibly as Barbara took my hand and lifted me up. I shook my head and tried to tell her under my breath not to do it but she only ignored me, patting my diapered bottom and ushering me over. This was incredibly awkward and even though Victoria was stunningly beautiful, her obvious lack of interest in me made me loathe to be so near to her. But worse than that was my growing need to pee–I was flexing my fists and clamping my legs together just to keep it in but I knew I couldn’t hold out for much longer. How would I hide it if I were sitting on her lap?
Barbara sat me down and my bare thighs crossed Victoria’s which were exposed from the short shorts she was wearing. The touch of skin to skin made me feel prickly all over and as I looked into her pretty face, her drop-dead gorgeous eyes regarded me with indifference.
Another attractive young woman–also in her twenties–approached with a gift in her hands and she handed it over to me sweetly.
Still tense from struggling to keep from peeing, I took the package with trembling hands and opened it anxiously. Inside were a pair of frilly rumba panties, with multiple rows of fancy ruffles across the seat and leg openings. One was pink with white lace while other was baby blue with white accents.
As I fumbled uncertainly with the panties, the woman came over and put a comforting hand on my shoulder.
“Don’t worry Sissy–they’re cut full enough to fit comfortably over diapers even as big as yours,” she assured me.
Before I could think of some sort of response, a powerful urge gripped me to pee and I barely managed to resist it. However, I sensed that some had manged to leak out just as I relaxed my muscles. I squirmed on Victoria’s lap and whimpered helplessly but her only response seemed to be annoyance with me. Aunt Emily came over with another package and I knew I wasn’t going to make it. With a gasp and a sob, the floodgates opened with a vengeance. A strong, hot stream of pee surged unstoppable into my diapers, saturating the front instantly. Without thinking, my hand dropped to my crotch in a futile attempt to halt the flow but my actions only served to bring attention to what was happening. Another powerful surge came on the heels of the first and Victoria was starting to realize what was taking place. My pee was already soaking into the section between my legs and seeping back into my seat, giving direct evidence to Victoria as she felt the growing heat against her legs.
“Oh my god!! Are you peeing your diapers?!” she demanded.
My lip trembled in fear as I beheld her angry expression but before I could respond, she dumped me unceremoniously on the floor.
“Eww!! That is so gross!” she exclaimed.
Looking at her tall, strappy heels, up the length of her long, toned legs, the look on her face made me afraid she was going to reach down and slap me.
Without batting an eye, aunt Emily reached down and squeezed the thick seat of my diapers, even as I released another powerful stream. At this point, there was really no stopping it and I didn’t even try.
“It’s okay,” she said assuringly, “It’s just a wet diaper…He can’t help it–he really has no control.”
Despite myself, I felt hot tears of shame filling my eyes and one trickled down my cheek as Victoria stared down at me in disgust. Aunt Emily was running her finger around the leg holes of my rumba panties, checking for wetness as the last bit of pee flowed freely out of my bladder.
“You see? No leaks at all,” she proclaimed proudly, “His snug plastic panties kept it all in.”
“Aww, you poor thing,” Sarah said with her mock sympathy.
She was sitting closest to us and she reached down and grasped my new pacifier, stuffing the big rubber cock back into my mouth.
Victoria was shaking her head as she stared down at me coldly.
“That is so gross,” she repeated.
“Aww, come here,” Aunt Emily said, genuine concern in her voice, she bent down and wrapped her arms around me, hugging me close as she consoled me in her motherly way. She buried my head into her soft, cushiony bosom and my cheeks were surrounded by her big round breasts. Her hand patted my back and then reached down, patting my well padded posterior.
“Shushhh Baby,” she cooed, “Mommy’s going to change her baby’s diapers–don’t you worry.”
I sniffled and felt another tear tumble down my face as waves of shame washed over me. Any kind of speech was quite impossible with Sarah’s penis pacifier filling my mouth but inexplicably, I made no move to take it out. Sarah stood up and came to my side and together, they lifted me to my feet, checking once again to make sure I wasn’t leaking.
“Come on Chrissie, let’s get those wet diapers changed,”aunt Emily said as she took me by the hand and led me out of the room. I waddled between them, feeling very helpless and childish as the warm, soaked cloth clung stubbornly to my seat and between my thighs.
They took me back to another room, one made up very much like my own nursery at Barbara’s house. At first, I assumed aunt Emily had a baby of her own but then I noticed that everything was oversized in the same manner mine was; the crib, changing table, even the playpen looked like it were made for a small adult. I also recognized the faint but ever present odor of stale diapers, which made me wonder who else was being treated like me. Could there really be another teenager that was being dressed like a baby day after day?
Aunt Emily sat me down on the changing table, a low fixture that was padded and had nursery print vinyl stretched over the surface. But as she reached for the waistband of my rumba panties, I squirmed in resistance, whimpering as I vigorously shook my head. I didn’t want this pretty stranger to discover how small my little wee-wee was!
“Don’t worry Chrissie, I’ve changed plenty of sissy’s diapers in my time, there’s nothing you have that will surprise me, believe me,” she said as she tugged the flimsy rumba panties down off my diaper. I kicked and fidgeted, whining through my pacifier and wishing Barbara had come back to change me, maybe she would have interceded but now there was nothing to prevent aunt Emily from pulling my rumbas down my legs, revealing the big wet spot visible through my waterproof panties.
“My, you’re quite a wetter, aren’t you,” she commented as she reached under the elastic waistband of my vinyl panties and began working them down over the wet cloth.
My muffled protests did nothing to dissuade her or make her think I was anything other than an incontinent sissy. She snaked the panties down and proceeded to unpin my heavy wet diapers.
“Sarah–can you grab a pair of plastic panties for me? Joshy’s should fit him just fine–they look about the same size.”
Who was Joshy, I wondered. It felt doubly odd to be wearing baby pants from someone else my own age. And the thought I’d be wearing plastic pants that had been wet in by someone else bothered me too.
After sliding the soiled diapers from beneath me, Emily began wiping my groin and bottom with baby wipes. I blushed a hot red as she held my little penis like a crayon and began rubbing my tiny sack clean with the wipe. There was nothing the least bit sexual about her actions–it was simply a mother carefully cleaning her friend’s baby.
“Well,” she said as she slide one of the cool cloths down the length of my stiffening willie, “Looks like this sissy is still roaming free.”
“Not for long, I heard,” Sarah interjected as she handed aunt Emily a pair of pink polka dot vinyl pants, “That’ll be taken care of on Monday, I think Barbara said.”
What did she mean by that, I wondered. Once again, these enigmatic references to my penis caused me to be nervous about what she had in store for me.
“All I can say is enjoy it for now, Sissy,” aunt Emily said as she slid a thick stack of soft diapers under my rump.
“How long has it been for Joshy now,” Sarah inquired as she held the diaper pins for Emily.
“Oh…six, maybe seven months now, but I think he’s come to terms with it,” she responded.
Did she mean being treated like a baby or was there something else to her remark, I wondered.
Taking a big container of baby powder, aunt Emily began shaking it generously over my crotch and stomach. I kept waiting for her to stop but she just kept going, shaking more on me and rubbing it all the way up to my chest. The babyish scent assaulted my nostrils and I whimpered and fussed but she just smiled down on me and continued as before.
After pinning both sides of my diapers snugly into place, aunt Emily slid the soft but noisy plastic pants up my legs and worked them over the thick, bulging cloth.
“A big baby needs a big diaper–hm, Sugarplum?” she asked as she patted the shiny front of my fat diapers.
“And you know what?” Sarah asked as she beamed down on my prone form, “Its feeding time for my little baby–but today’s a special day for sissykins, you know why?”
I shook my head wordlessly.
“Because today, you get to pick which of these ladies you’d like to breastfeed from, won’t that be fun?” she said without waiting for an answer.
I sucked desperately on the fat penis pacifier in my mouth as I blushed anew and looked in panic from Sarah to aunt Emily. Why did Barbara have to tell them about that?
I whimpered in muffled futility but Emily wasn’t even paying attention.
“I know who he’ll want…” she said conspiratorily, “This little sissy here has a crush on Victoria.”
Sarah looked down at me as if she’d just been made privy to a naughty secret.
“You think so?” she asked intrigued.
“Oh yes–I saw the look in his eyes when he first saw her–the pretty young thing. I could tell he was hoping to make a good impression on her before he had his little accident…but I guess its a little late for that now.”
Sarah giggled with glee at the picture her friend was painting.
“Well we certainly can’t deny our little sweety her wish, now can we?” she replied.
Standing me up, Sarah held my hands in hers as she bent over to look me in the face.
“Chrissie, now that you’re wearing fresh diapers, I want you to go back out into the living room and ask Victoria if she’ll let you breastfeed from her.”
She finished her command by popping the pacifier from out of my mouth.
“N-no way,” I rmumbled, “I d-don’t wanna do that.”
She had to be deaf and dumb to think Victoria would give me the time of day–never mind let me suckle from her sexy boobs.
“Now Chrissie–this is for your own good. You march yourself right out there and do as I tell you,” she said firmly.
As if that were the end of the conversation, she turned me around and swatted my thickly padded rump, causing me to stumble forward in the direction of the hallway.
“No!” I argued, balling my fists in defiant fury.
No possible good could come from my asking Victoria what Sarah was suggesting and I knew my only chance to stop her was here and now. Holding my ground, I placed my feet apart in a stance of rebellious obstinacy. I knew I must look silly, standing there in my Mary Janes, fat diapers and a pink sailor suit and expecting to be taken seriously.
“Chrissie…you will go out there, and you will ask Victoria in a polite manner to please give you your feeding–do you understand me?” Sarah said, her voice taking on a menacing new edge.
“Uh-uh,” I replied stubbornly. I wasn’t willing to budge an inch.
“Chrissie, I’m going to give you three seconds to walk out that door or so help me, I’m going to pull you over my lap and blister your bottom–its that simple.”
I bit my lip anxiously as I considered my position. This woman looked determined to do what she was threatening and I didn’t doubt her ability in the least. Like everyone else here, she was taller, even without her high heels, and I knew she would be stronger than me as well, even without aunt Emily’s help.
“One…two…”
“–Okay, I’ll do it!” I suddenly blurted out in panic.
“–Three.”
Sarah reached into her purse and produced a hard, oval shaped wooden paddle with the words ‘For sissy bottoms only’ in red across its face.
“Do you need a hand?” aunt Emily asked casually, her face showing amusement at my impending punishment.
“Oh no, this little sissy looks as weak as a lamb,” she said calmly, “But he’s about to find out what happens when he doesn’t do as he’s told.”
“No–no wait!” I pleaded as she snatched my wrist in her iron grip, “I said I’d do it!”
Without paying me any heed, Sarah dragged me over to a straight backed chair in the room and took a seat.
“Time for a little lesson in manners, Sissy-boy,” she told me.
“No…no….no,” I pouted as I stamped my feet in frustration.
Sarah tugged my pink polka dot plastic pants back down and then forcibly jerked me over her lap as a new set of tears spilled down my cheeks.
“Wait! Please–please don’t spank me!” I cried.
“If you had done as I’d asked of you, you could’ve been nursing from pretty Victoria by now but instead, you’re going to get your little sissy bottom paddled,” Sarah said as she unpinned either side of my diapers.
I kicked and fidgeted, pleading with her to give me one more chance.
“B-b-but you didn’t even get to three!” I wailed in consternation.
As if in answer, her paddle swooped down and landed with a loud crisp SMACK! on my raised bottom. My argument ended in a burst of tears that immediately began streaming down my face.
SMACKK!! SMACKK!! CRACKK!! THWACKK!!
Swat after punishing swat landed on my defenseless fanny. The nursery door was wide open and I knew my crying and sobbing would be clearly heard by everyone still in the living room. Not only that, the loud, angry slaps of Sarah’s paddle reverberated in the room as it impacted my soft, youthful buns and I knew the women could hear every stinging swat, each time it landed with impunity. Everyone would know the childish punishment I was receiving and there was nothing I could do about it!
My Mary Janes were drumming a frantic rhythm on the floor as Sarah methodically ensured that every square inch of my rear received it’s scorching, blistering reward. Bawling loudly, I beat my fists on the floor as I lay there, helplessly enduring each swat of the paddle as it seared itself into my skin.
When she at last finished, she put the paddle back in her purse and pulled the back of my diaper up into position. I looked down through tear filled eyes upon aunt Emily’s high heeled sandals as she handed my diaper pins to Sarah.
“There…I don’t think we’ll be getting any more arguments from Chrissie today,” Sarah stated smugly.
“Are you ready to be a good sissy now?” she asked me.
I howled out and nodded my head emphatically as she helped me to stand. The inferno on my rump caused me to dance in place and I stamped my feet in pain and frustrated anger.
“Stand still Chrissie, so I can pull up your baby panties,” she chided me.
As I fidgeted in place, Sarah snaked the cheerful polka dot panties up my quivering, skinny legs and worked them over the bulky cotton cloth. Once again, I felt the temperature rise about twenty degrees as she sealed the smoldering heat inside my diaper.
“Maybe that’ll teach you a lesson, next time you get sassy with me,” she scolded me firmly, “When I tell you to do something, you’ll do it without question, and without any backtalk–you got that?”
I cried even harder as I nodded me head, keeping my eyes submissivley downcast so as not to anger her any further. This woman was strict!
While I cried unashamedly, aunt Emily looked down and smiled at me. Oh, how I hated her now! She’d done nothing to stop my humiliating punishment and if anything, seemed happy to have taken part!
Standing up, Sarah took my hand and led me out of the room, looking like a punished toddler as I sniffled and wiped my hands across my wet face. To make matters worse, she wasn’t even giving me the chance to get my crying under control before everyone saw me, looking like a naughty little crybaby.
“Come along Sweety, there’s something I know you want to ask Victoria.”
I realized there was no getting out of this and the only thing to do was play along and be humiliated in front of everyone. How could things possibly get any worse for me?
Waddling into the living room, everyone grew silent and their eyes were upon me as I sniffed and did my best to act brave. It was obvious that everyone could see my puffy eyes, wet cheeks, and it was certainly no secret as to what just happened.
“Looks like a certain sissy just got his bottom spanked,” Mrs. Sterne remarked in her smug, superior tone.
“If you’re trying to potty train him–I fully agree with your methods,” she told aunt Emily, “A good hard spanking always does a sissy a world of good. Maybe next time, he’ll tell you before he decides to wet himself.”
“Oh no, it wasn’t that,” Sarah smiled, “We just had to settle a little disagreement but its all resolved now.”
With her hands on my shoulders, Sarah walked me over to Victoria, who was still sitting on the couch, filing her long, French manicured nails. Her long, sexy legs were crossed again and her high heel dangled over the floor.
“Um…” I began uncertainly.
I was used to being ignored by the hot girls at my school and this only brought that feeling of inferiority back with a vengeance. Victoria barely looked up from her nails to acknowledge my presence.
I was hesistant to say anything further but Sarah nudged me in the shoulder blades.
Clearing my throat, I began again.
“Um…Miss Victoria?” I began in a small voice, “…Um, do you think I could-um…kinda..um, n-nurse from you t-today?”
For the first time, she peered up from what she was doing to look me in the eye.
“You want to do what?” she asked incredulously.
My face reddened hotly at her blunt reply.
“Um…I mean…can I…I mean…do you think…” I stammered as I looked into her cold, piercing eyes, my face burning with shame, “Could I b-b-breastfeed from you?”
“Are you freakin’ kidding??” she demanded, “Get away from me you little twerp.”
Hot tears of shame filled my eyes as the other women giggled merrily with amusement. This was far worse than any dismissal I’d received from any schoolgirl, anywhere.
“You poor little sissy,” aunt Emily said as she came over to my side.
Taking me by the hand, she plopped me over her lap so abruptly, I landed face up, my legs sprawled across the love seat she had taken a seat on.
“Don’t you worry Babykins,” she said in a voice designed for addressing toddlers, “Aunt Emily’s going to make sure you get your fill and then some.”
I gasped in shock as she unbuttoned her snug top and revealed two giant globes of femininity, straining desperately within a smooth, satin white bra. I began fidgeting and whimpering, shaking my head as she undid the clasp in front and releasing her heavy breasts from their cups. Her pink nipple was staring me straight in the face and I gaped at it and then up into aunt Emily’s beautiful grinning face.
“Its milk time, Chrissie,” she said cheerily and without waiting for a reaction she mashed my face against her giant breast.
I squealed loudly but in opening my mouth, her firm nipple slipped in and my cries were soon completely muffled. Whining and fussing, I struggled in her lap but soon settled down, to nurse from the steady stream of milk flowing into my mouth.
Flush with victory, aunt Emily beamed down on me as she stroked my cheek softly.
“Thaaat’s it Baby….take all you want…there’s plenty for a thirsty sissy here…”
Looking over at her other plump breast, I had no doubt she was correct. The one in my mouth seemed to have an endless supply and I suckled away for some time until my jaw began to get sore. By now, the other women had begun talking amongst themselves, having completely forgotten about me. In their minds, I was just another baby getting breastfed by his aunt who was in no danger of running out of milk. After getting my fill of her right breast, aunt Emily switched me over to the other one, working her leaking nipple across my pursed lips until I finally capitulated and surrendured to her will. It was another long fifteen minutes before she finally eased her nipple from my sore mouth and helped me to sit up.
My stomach was full and I could feel the liquid sloshing around in my belly. I felt both dizzy and a bit queazy as I fought back a burp and looked up at Barbara through half closed eyes.
“Well, its Chrissie’s naptime, girls,” she said as she took my hand, “Tell everyone thank you for a wonderful afternoon, Chrissie.”
Unaware of the milk that had dribbled down my chin and dried during the course of my breastfeeding, I mumbled out my thanks to everyone under my breath.
“Nighty-nite, Chrissie,” one of them said and I waddled along as Barbara took my back to the nursery.
Taking only enough time to remove my Mary Janes, she lowered the crib side and helped me in, pulling the baby blankets back up as I settled in. I had to admit I was rather tired from everything that had happened although I still resented having to take a nap like a little baby. And the waterproof vinyl sheet I was laying on smelled slightly of stale pee which only humiliated me more. After all, I wasn’t a bedwetter so why did I have to sleep in a bedwetter’s bed?
After Barbara had gone, and the crib top was locked in place, I began feeling the first stirrings that all that milk was having on my system. I fought it, squirming and fidgeting as long as I could until nature finally won the battle. Lying on my back and staring up at baby’s mobile above the crib, I relaxed and wet my diapers heavily, hoping my plastic pants would be able to hold it all in again. Sobbing in defeat, I hugged my teddy bear closely as I softly cried myself to sleep knowing I’d probably only wet some more while I slept.
Chapter Five Chrissie’s Present
Monday morning, I woke up with a very wet diaper. This was a disturbing trend that had started a few days ago with just some dampness in the morning that at the time, I’d dismissed as an accident. But then the next night, the cloth between my legs had been wet and cool when I woke up and today, my diapers were completely soaked. I hadn’t wet the bed for years and I had no idea why it was happening now. Could wearing diapers 24/7 have had some subliminal effect on my system?
This was normally the time in which I’d masturbate at a nice, relaxed pace before Barbara came in to get me. I always woke up horny, and the cushiony soft, comforting cotton of my diapers was simply too tempting to ignore. Truth be told, I was beginning to develop a secret appreciation for them. The male side of me told me that I should despise the babyish underwear and realize they were part of Barbara’s cruel design to sissify me. But the physical side of me was growing to love their soft comfy hug around my loins and bottom. When I walked, or rather, waddled, the plastic panties slid pleasantly between my inner thighs which I had come to enjoy. But more than anything else, the pillowy folds of bunny soft cotton made for a perfect means to massage my perpetually horny penis, so I could indirectly stroke it to orgasm after shattering orgasm.
Fact was, I’d never played with myself so much in my life. Part of that was because of the diapers but another part was being in such close proximity to a sexy woman like Barbara. Yes, I resented the hell out of her for turning me into her baby girl, but my penis didn’t care that I was wearing a dress most of the time. All it knew was that Barbara had the sexiest boobs I’d ever laid eyes on and they were all the inspiration I needed to stroke myself to a eye crossing climax, day after day.
This morning however, the fact that I’d wet myself so thoroughly was distracting me from my usual activity. I rubbed the front of my diapers but all that pee it was holding had taken away some of the cushiony feel I had taken for granted. And it was still nagging me as to why and how it’d happened. Waves of guilt washed over me as I lay there, staring through the pink bars of my crib. My body was punishing me for accepting my babyish status–that had to be it. I’d come to accept and even secretly enjoy my diapers and now my body was telling my brain it didn’t have to give me any notice if I needed to pee. Was I destined to wet the bed from now on? And what about during the day? Would I just find myself wetting my diapers without any prior indication?
Even as I rubbed the soft, smooth vinyl covering of my diaper, trying to get some relief, these thoughts kept intruding on my conscience.
Suddenly, the nursery door opened and in walked Barbara which forced me to stop masturbating as well as distract me from my line of guilty reservations.
“How’s mommy’s little baby?” Barbara asked sweetly.
She was wearing tight white shorts and a breathtaking button up top that displayed her plump, sexy breasts to great effect.
I was ashamed to admit I’d wet my diapers but at the same time, I wanted her to change me because they were getting cool and clammy.
“Um…I um…” I stammered uncertainly.
“Yes, Sweety?” she said as she unlocked the top of the crib and pulled it back. Looking down on me, her big, mouthwatering breasts hung before my eyes and my penis began to harden all over again. It was a sight I never tired of gazing upon and I felt an electric wave of horniness ripple through me. I was going to enjoy my morning stroke when she finished changing me.
With her infallible instincts, she put her hand down against the front of my diaper and gently squeezed it. I wasn’t concerned about her detecting my hard on because my penis was far too small to be felt or seen in my thick diapers.
“Aww, did mommy’s little baby wet her diapers?” she asked in her honey voice.
“Uh huh,” I mumbled as I blushed a little.
“Don’t you worry Sugarplum, because we’re going to get you changed right away. Today’s a big day for you because aunt Melissa dropped off her special present. I just can’t wait to show you–its just what you need,” she gushed.
“Wha-what is it?” I asked, somewhat apprehensively. I had become increasingly skeptical of Barbara’s special presents.
“You’ll see very soon, don’t you worry Sissikins,” she told me as she reached down and grasped the pacifier that was looped around my neck. Holding it before my lips, she began rubbing it against them until I reluctantly submitted and let her push it into my mouth.
“That’s a good girl,” she commended me, “Now, its very important that your pacifier stays in this morning, okay Chrissie?”
I nodded my head in ackowledgement; it wasn’t a big deal with me. Hopefully, in less than an hour, she’d be done with whatever she had in mind and I’d be able to stroke myself to another dizzying orgasm. I don’t know why, but looking at the smooth skin on the round curves of her beautiful bosom was making me especially horny this morning.
“Its very important that you don’t take it out because if you do, I’m afraid I’ll have to give you a nice hard spanking and you don’t want that, do you, Baby?”
I shook my head slowly in silence, idly wondering why it was so important to keep my pacifier in.
Taking my hand, she raised me up in the crib so I was on my knees and my hands were resting on the side rail.
“And just to make today even more special, you have two visitors that are here to see you,” she said as she patted my arm in a motherly way. The last thing I wanted was to be seen by anyone new but I was hardly in a position to argue with her about it.
Stepping back, Barbara put her head outside the nursery and beckoned to someone out in the hallway.
“Come on in Pamela, your baby son’s awake and eager to see you.”
My eyes grew as big as saucers as my mom and sister strode into the room. My mouth dropped open in utter shock but Barbara was quick to hold my pacifier in place. In a fit of panic, a strong, hot stream of pee surged into my diaper, making me whimper around the rubbery nipple filling my mouth.
“Well!” my mom exclaimed happily, “What a change you’ve made in so little time!”
“You’ll find Chrissie is just the best behaved little baby anyone could ask for,” Barbara boasted.
My mom came over and looked me up and down, obviously very pleased with my infantile attire. This morning I was wearing a fuzzy soft Strawberry Shortcake top in pink and white with short, puffy shoulders. The hem came down just past my navel leaving my babyish pink plastic panties fully on display.
“Has he been using his diapers, or are they just for looks?” she asked curiously.
“Oh–he uses them alright, every day–several times a day. As a matter of fact, Chrissie’s wetting the bed regularly now so there’s really no going back now for him. Feel for yourself.”
My mom reached over and felt my diapers, immediately sensing the wet warmth beneath my plastic pants.
“My little baby boy!” she cried wistfully. It was if she were happy to have me back as a baby again.
I sucked desperately on my pacifier, blushing fiercely and making panicky slurping sounds as she looked me over. I wanted to say something, but I didn’t dare risk Barbara’s wrath with her paddle. Out of the corner of my eye, I saw my little sister approach and stare up at me in wonderment.
“Mommy? Why is Chris wearing diapers?” she asked innocently.
“Because he has no self control,” Barbara quickly replied, “And because he’s a sissy and all sissies need diapers or they’ll pee their pants.”
That seemed to satisfy her for the moment and she smiled up at me, not a little surprised at what she saw.
“You look like a baby girl,” she said in her little childish voice.
I hung my head in shame at being the center of attention. Trapped in my crib, with no where to go–this was absolutely mortifying!
Barbara unlatched the crib rail and lowered it to help me out.
“You’re right on time Pamela, because I was just about to change Chrissie’s diapers, would you like to lend a hand?”
My mom sighed with maternal contentment.
“I haven’t changed Chris’ diapers for…”
“–Mommy–can I help too?” Lindsey interrupted impatiently.
“I don’t see why not,” she replied, “Why don’t you pick out his plastic panties, Dear.”
“Okay!” she cried with glee.
Barbara led me over to my changing table as Lindsey began excitedly thumbing through the drawer that contained my waterproof pants.
“Is it hard to find baby clothes for a boy of his size?” my mom inquired with interest.
“Oh no–not at all,” Barbara told her emphatically, “And Chrissie has taken to them like a fish to water. As a matter of fact, he wet himself the very first day and hasn’t had a dry night since. I know he was glad to finally be rid of his boy clothing and he just loves the feel and comfort of wearing soft diapers and his other baby things. He’s so much happier getting to dress up every day and he looks forward to seeing which outfits I’m going to pick out for him. His favorites are always the most babyish, frilliest ones, usually in pink or other girly colors.”
“Oh my,” my mom murmured in wonder.
I shook my head trying to deny what was being said but she wasn’t paying attention.
“So I guess all this time, he’s just been acting like he enjoyed boy’s activities, but in reality, he probably just wanted to be a little girl again,” my mom reasoned.
“Yes…but in Chrissie’s case, the fact is, he’s not yet ready for dresses and panties–he still very much needs his diapers and plastic panties–as you can see for yourself.”
As I lay on the vinyl covered table, Barbara pulled down my clinging baby pants to reveal the sopping wet diaper underneath.
“Basically, your son here is a little sissy that just refuses to grow up. I think if he had it his way, he’d stay a baby girl for the rest of his life.”
I whimpered around my pacifer in mute protest.
“Well, the change has certainly done him a world of good,” my mom agreed wholeheartedly, “I think this is the best thing that’s ever happened to him.”
I winced in frustration at this humiliating discussion concerning me.
“And if I may, I think you should stop thinking of him as your son. Chrissie wants nothing more than to be a good little baby girl and I’m going to give him–or should I say her–that chance.”
“Yes…I guess I always knew he’d never amount to much of a man, if and when he ever grew up. With his soft, smooth legs, lack of pubic hair and his sissyish ways, it looks like he was always meant to be a toddler girl.”
“That’s what I thought, the first time I saw him. It really is the best for him.”
“Seeing him now in his baby clothes and wet diapers–I’m certain of it,” my mom concurred, “Lindsey, you may have lost a brother but you gained a baby sister.”
My sister giggled merrily in response.
Barbara had removed my diaper and was cleaning my bottom and genitals as Lindsey brought over a pair of plastic pants. Just as I feared, they were the most girliest ones that were there; pink with white bunnies and frilly eyelet lace around the legs.
“Mommy? Are these panties okay?” she inquired earnestly.
“Yes Honey, thank you,” my mom said accepting them.
“Chrissie, I want you to hold these while we’re getting your diapers ready,” my mom told me.
I was crushed with humiliation, having my mom treat me like a child again and a tear of shame trickled down my cheek as I sucked miserably on my pacifier. In helpless frustration, I took the panties and held them to my chest while Barbara slid another fresh stack of diapers beneath my rump.
“He really does need thick diapers, doesn’t he?” my mom asked.
“She certainly does, and there’s really no reason to try and hide them or be discreet about it–everyone knows she needs them and I don’t want there to be any doubt about what she’s wearing. In addition, I’ve made sure her outfits are all cut short so her sissy diapers can be seen by everyone and actually, it makes changing her that much easier too.”
“And now we’re ready for Chrissie’s special present,” Barbara announced dramatically.
Lindsey’s brow creased slightly as it seemed like I was getting all the attention and she wasn’t getting any. That was the last thing I wanted!
Barbara turned briefly and when she came back around, she was holding a small white box in her hand. From inside it, she produced a strange semi-clear looking device that was shaped more or less like a penis except that it had a wide collar of some sort near the base and I could tell it was made of a slightly flexible material.
“Is that what you were telling me about before?” my mom asked with interest.
“Yes, Pam. This little gem will put an end to your son’s masturbating habit–once and for all.”
Barbara unwound a circular plastic strap that went around the thicker silicone collar and put it down next to me. I tried to pick it up to get a closer look but she slapped my hand away brusquely.
“That’s not for you to play with, Chrissie” she chided me, “Only grown-ups can touch this.”
“How does it work?” my mom questioned her.
“Chrissie’s little sack and penis go through this collar and then her willie goes into this tube. As you can see, this extension piece draws her little penis down and between her balls which prevents her from getting an erection. Also, the size of the tube limits how much her wiener can grow so that she won’t be able to get hard anymore. She won’t be able to touch or stimulate it, which means she won’t be able to stroke herself and masturbation will now be a thing of the past.”
“Does it really work effectively?” my mom asked in amazement.
“Oh yes–it’s quite foolproof. Once this collar is locked in place, there’s absolutely no way she can pull her pee-wee through or get access to it,” she said simply.
“But will it hurt him?’ she asked concerned.
“Oh no–not in the least. It’s comfortable enough to stay on 24 hours a day, seven days a week–after a while, she won’t even know she’s wearing it. And sissies really don’t need to cum, so she’s not losing anything there, either.
“You see, one problem with sissies who wear diapers is that the diapers themselves can be a tremendous temptation. The soft, cushiony cloth feels wonderful on their little penises and they can’t seem to control themselves. Chrissie here has been no exception–she’s been playing with herself nonstop since she arrived.”
I gasped in shock–how could she have known??
Looking back down on me, Barbara smiled with a smug grin.
“Oh yes, baby girl–I’ve known all about your little masturbating activities from your first night here. You thought you were keeping it a secret but I’ve known all along. And now I’m putting a stop to it. I hope you had a good orgasm last night while rubbing your diapers because its going to be your last one.”
A shiver of fear and trepidation raced through me as I contemplated the terrifying magnitude of her words.
“This will keep her from being naughty, and make her the best possible sissy any mommy could ask for,” she said as she turned back to face my mom.
“If only I’d had this a year ago,” my mom lamented.
“Better late than never,” Barbara replied, “Now Chrissie, I want you to ask your mommy if she’ll be so kind as to put your chastity device on for you.”
Hearing all this, I was completely aghast. How could such a diabolical device exist? How was I going to go without cumming–ever again?
When Barbara pulled the pacifier out of my mouth, the panic induced words tumbled out of me like apples from a barrel.
“Mom! You’ve got to get me out of here! I don’t wanna dress like a baby–I don’t wanna wear that thing! Pleeaasse–please Mom–don’t let her do this to me!”
My pleading turned into a whining, babbling cascade of noise that was quickly becoming unintelligable.
They both looked down on me but neither showed the least signs of sympathy.
“Mom!–She made me wet my diapers!–This wasn’t my idea–please take me home–I don’t wanna stay here anymore,” I pleaded desperately.
“Hmmph,” she sniffed, “It’s just like you said he’d be–acting like he doesn’t like his diapers and baby treatment.
“I don’t believe you for a second. The amount of time you’ve spent masturbating in them proves beyond a shadow of doubt how much you like them, Chrissie.”
I blushed red with shame, realizing that at least on some level, there was a kernel of truth to her accusation. If only I’d had more restraint! But what could I say now?
“Oh no, ever since you were a little boy, I’ve suspected you were nothing but a sissy. And remember that time aunt Holly caught you playing dress up with her daughter? You tried to tell me it was her idea than as well.
“Oh no Mister–you’re staying right where you are. I knew when I first walked in and saw you in your wet diaper and sissy top that Barbara had pegged you exactly right. You are a sissy and you do need diapers. Not only that, you need a secure chastity device to put an end to your constant masturbating. Its a disgusting habit and I won’t put up with it another minute.”
I’d never seen my mom so full of conviction and authority in all my life and I was temporarily at a loss for words. Barbara, on the other hand, was smiling with cool, smug satisfaction. Everything had gone exactly as she’d planned.
Taking a bottle of baby oil, she squeezed some out onto my small, hairless genitals, rubbing it all over my little sack. Despite my shock and confusion, her gentle, soft touch felt wonderful and as I gazed numbly at her big beautiful breasts, jiggling sexily within her snug top, my wiener automatically stiffened to attention.
Grasping the silicone device in one hand, Barbara began working each of my balls carefully through the collar until both were on the other side together. With the container of baby oil, she dribbled a little more and stroked my wiener with it.
“We want to get you all nice and slippery for your new home, Chrissie,” she said sweetly as she smiled down on me.
I began whimpering helplessly as she pushed my wiener down through the collar so that my whole package was now on the one side of the device and the collar ran around the base of my genitals.
“No…no…please…mommy!” I protested weakly.
Grasping my slippery wiener between her thumb and index finger, Barbara poised it before the opening in the penis shaped tube.
“Say hello to your new friend, Chrissie, you two are going to become very well aquainted,” she gloated.
I squirmed and whimpered, too much in a daze to interfere as she pushed my hard-on into the snug, restrictive tube.
“Need this?” my mom asked as she held a bag of frozen peas in her hand. I had seen them earlier but didn’t understand why she had brought them in.
“Yes, thank you,” she replied as she took the bag and held them up firmly against my scrotum.
“AGGHH!!” I cried as the frozen bag hugged my balls.
Barbara smiled down on me with satisfaction as she held them in place.
“It’s okay, Sissy, just a little coldness to take away your last erection so we can get you all locked up properly.”
I squirmed and thrashed on the table, trying to get away from the bag but she followed my movements and held it cruelly in place. I could feel my hard-on inexorably losing the battle and shrinking down; in just a moment, my little penis was once again, limp as a noodle.
“There you are,” she beamed down at me, obviously happy with the results.
Now that my wiener was no longer stiff, Barbara tucked it, now trapped inside the tube, down and between my balls where the locking strap came up and around the collar. My willie was now positioned straight down and unable to move.
“No…please Mommy, don’t let her do this to me,” I begged her piteously as I stared down at this evil, devilish device.
Ignoring my protests, Barbara wrapped the locking strap around the collar and joined both ends, pushing the locking pin into the holes on either end. From somewhere below me, she produced a small lock and I watched in horror as she slipped it through the pin, and snapped it shut with a crisp click.
“There,” she said with tremendous satisfaction, “That’s put an end to your masturbating, once and for all.”
I looked up at her with horror and shock on my face.
“Chrissie. I told your mom I’d stop your masturbating and now I have, permanently. This will stay locked in place under your diapers from now on except for periodic cleaning and a milking once a month. Now you’ll be using your diapers for their intended purpose, just like a sissy should,” she told me.
Looking down at my caged penis, I watched it wriggling like a trapped fish as I flexed my muscles, unable to get hard within the snug confines of this dreaded silicone chastity device.
“Its not fair!” I wailed as I brought my fists down on the table in sissyish frustration. A tear trickled down my cheek and I angrily swiped it away.
Barbara giggled merrily, obviously quite pleased to see me so thoroughly controlled.
More tears tumbled down my face as I grabbed the device and struggled to get it off. The design of it was ingenious however and I couldn’t even get to a part of my penis to extract it from its rubbery prison. Nor was it possible to slip my balls back out now that the collar was locked in place.
Waves of panic swept over me as I saw my last avenue of pleasure closing like an iron door.
“Okay Chrissie, finished playing with it? Because now its diaper time for you,” Barbara said nonchalantly as she began positioning the stack of fresh diapers beneath my rear.
“Noooo! Noooo!” I wept bitterly as she lifted my kicking legs and powdered my rump generously.
“Chrissie? Do you need your bottom spanked before I put your diapers on?” she asked as she paused her ministrations.
“No!!” I snapped angrily, knowing she held all the cards now and I was helpess to do whatever she demanded.
“Good, because you’re going to do as I say or I’ll pull you over my lap for a good hard paddling.”
My mom grinned with a smug look I wasn’t used to seeing as I pouted in frustrated silence, my lower lip thrust out like a petulant toddler. She knew I was beaten and completely at this strict woman’s mercy.
“That’s right, Sissy, better hold that tongue if you know what’s good for you,” she taunted me as she pinned the diapers up snugly. I sniffled impotently as she took the plastic panties I was holding and began snaking them up my legs.
My mom reached over and grasped my pacifier, holding it before my face.
“Open up, Chrissie, here’s your paci,” she said.
I burned with frustration over this complete reversal of power but I knew I had no choice but to submit. Choking back a sob, I opened my mouth and was rewarded with a large rubber nipple.
Looking down, I watched as Barbara shook baby powder between my inner thighs.
“And now, I think we’ll give your new friend it’s first test,” Barbara announced, “You see, in addition to being a chronic masturbator, Chrissie here is also a premature ejaculator. I’ve been nursing her like the big baby she is but she can hardly stand it for more than two minutes before she cums in her soft, fluffy diapers. She really has no control at all. But now that her little penis is locked down, we’ll see if she can’t stay for her entire fill.”
“I didn’t know you were lactating,” my mom exclaimed with amazement.
“Oh yes, I was helping out a friend who just had her own baby but then I met Chrissie here, and I realized a sissy like her should be weaned at least once a day, as part of her discipline program. She enjoys it immensely, until she cums that is, and then she starts to fuss like a whiny baby with a wet diaper.”
“I can imagine that all too easily,” my mom concurred.
“Come along, Chrissie, it’s time for your breakfast…come to mommy,” Barbara said as she took my hand and led me over to the loveseat she used expressly for that purpose.
Reluctantly, I took my place across her lap, face up, as she made herself comfortable, unbuttoning her low cut top. I was angry as hell with her but my horniness had suddenly reasserted itself and the sight of her big, succulent melons being further exposed somehow managed to push my resentment onto a back burner. She cradled my head gently and with her free hand, gently undid the clasp holding her two giant mammaries in the cups of her satin bra.
“Here you are Sissy, time for yum-yums…”
I was ashamed to be such a willing participant in her childish game and I pursed my lips in a pathetic show of defiance.
“Open up Baby, mommy’s got her milk for her sweet little sissy,” she sang.
With her usual patience, Barbara simply pinched my nose as I stared at the large, dripping pink nipple poised before my lips. I squirmed and whined, shaking my head but she only smiled down at me and waited. At last, I gasped for breath and was quickly rewarded with her warm, milky nipple. I tried not to think about it, but my entire field of vision was filled with Barbara’s soft, sexy boobs, one in which I had my mouth clamped onto and the other, still partially contained by the silky cup of her bra. My penis had a mind of it’s own and it throbbed wildly now in it’s new prison, struggling frantically to become erect and hard. I fought the urge to nurse but then Barbara slapped my bare thigh with her hand. Dutifully, I began suckling, the firm nipple filling my mouth as streams of milk started to flow.
“Thaaat’s my good girl,” she cooed, “That’s a good baby.”
My horniness was building inside and I felt my heart pounding within my chest. My wiener was flexing and doing everything it could to break through the silicone tube it was trapped inside but it was quite impossible. I whimpered weakly as I tried to get some satisfaction but my penis couldn’t feel a thing. Normally, just a little friction inside my diaper was enough to make me explode but the chastity device was preventing any kind of contact. Meanwhile, Barbara was giving me encouragement, softly stroking my head and telling me what a good job I was doing. I felt so babyish but I was also so horny I could cry!
My mom had taken a seat next to us and while I couldn’t see her directly (all I could see were breasts!), I sensed she was watching me with intrigue.
“So does he nurse everyday?” she asked Barbara.
“Oh yes, without fail. The problem before was her premature ejaculating but now, we seem to have that all under control–don’t we Sugarplum?” she said in her syrupy voice reserved for toddlers.
She seemed eager to explain her methods for dealing with me as she continued;
“I produce enough milk of my own that–now that we’re not having to stop early–I know she’ll be able to get a full meal from each nursing session,” Barbara said with a trace of pride.
“Yes, I can well imagine,” my mom said appreciatively. It certainly wasn’t hard to believe, given the tremendous size of her breasts.
“But I also have a couple friends who happen to be lactating–I’m planning on bringing them over so she can get some extra breastfeeding from them,” she explained, “I want her diet to have a large liquid intake which will also help break down years of trained continence. It’s already having quite an effect.”
I felt completely excluded from the conversation, just as a baby would who’s mommy was breastfeeding it.
“A sissy needs breastmilk, and it helps to reinforce her position mentally that she’s still just a baby. Making the adjustment from a grown boy to a helpess baby girl can be somewhat stressful and this helps to keep her calm and mold her into her new role. I’ve also found that regular breastfeeding makes a sissy more docile and easy to control. They fuss less, and naptimes are less of a trauma. They really become quite submissive.
“Another side effect seems to be incontinence. I’m not sure why, but when a sissy begins breastfeeding again, they tend to lose control of their wetting. I’ve found many become bedwetters in just a couple days and they begin wetting their diapers during the day, shortly thereafter.”
I cringed and whimpered at the thought of what she was saying. Could it really be true? It sure seemed like it in my case.
Barbara gently pulled my suckling lips from around her nipple.
“Okay Sweety, time for the other breast now.”
I whined some more as the wet nipple was pulled away from me but in moments, she had positioned her other one before my still mewling mouth. It was huge, like the other, pink and glistening with milk.
“Open up Chrissie,” she whispered, “Breakfast time.”
My wiener was aching with desire and I felt dizzy from my futile efforts to achieve an orgasm. Hungrily, I gobbled at her nipple, sucking it hard in my desperation. Subconsciously, I think I believed that if I could just get a little more milk, I’d be able to get that elusive orgasm.
“Gently Honey…gently,” Barbara chided me.
I fought to control myself and I tried surrepticiously to reach down with my hand to rub the front of my fat diapers, oblivious to the fact my mother and sister was watching me closely. Ordinarily, I would never have done something so blatant but my sex drive was making me crazy to get satisfaction.
“Now, now, Chrissie, keep those naughty hands where they belong, they can’t do anything for you now.”
I whimpered as I swallowed another warm mouthful of milk. I wanted so badly to cum–it was so unfair! I would have killed to be able to climax in my cozy diapers at that moment but she had made it totally impossible!
As I nursed from her giant right breast, I was feeling my tummy getting full from all that milk. Much as I hoped to be able to achieve an orgasm from my continued efforts at her breast, it was becoming increasingly clear that I was no closer to cumming than when I started.
“How’s that, Sweety? Did mommy’s baby girl get her fill today?” she beamed down on me.
I nodded weakly, my penis still throbbing in frustration.
“Don’t you worry Honey, mommy’s going to make sure you get as much as you can take from now on.”
Gently, she pulled her swollen nipple out of my mouth and I squealed in angst. My heart was still beating wildly and I very badly wanted to cum.
Seeming to sense this, Barbara turned to my mom.
“You see, Chrissie’s little device is working just fine, no more sticky messes in her diapers and no more naughty behavior when mommy’s back is turned.
“I’m very impressed,” my mom marveled, “That chastity device is really a godsend–perfect for masturbating sissies like Chrissie.”
Carefully lifting me up, Barbara took me over to my playpen where she put me inside.
“Now you stay right there and play with your dollies, Chrissie. If you need me for anything you just call. Your mommy and I are going to be in the kitchen having grown-up talk but I’ll be able to hear you with the baby monitor when you wet yourself.”
“And don’t even think of getting out–I don’t want you hurting yourself or getting into any trouble. Everything you need is right here in your playpen.”
I resented both the fact that she took as a given I was going to wet my diapers and also for some reason, being excluded from her “adult” conversation.
Pushing my fat rubber pacifier in my mouth, Barbara led my mom into the other room. I watched her go, my eyes riveted to her sexy, pert bottom, but the moment they were out of the room, I began rubbing my diapers furiously, trying to relieve my pent up sexual need.
Although outwardly, my actions felt the same as always, my penis was only getting about five percent of the physical contact it was used to. My diapers felt soft and comfy as they always did but now, none of that was being transmitted to my needy wiener. I rubbed and rubbed, trying to make it work but all I succeeded in doing was getting myself even more worked up.
I slammed my fists onto the soft, padded rail of the playpen in bitter frustration.
Again, I rubbed frantically, hoping to somehow defeat the device my penis was trapped in but it was no use. I fought back tears of resentment and anger–there had to be a way!
I found I was breathing hard and a fine patina of sweat had appeared on my forehead but that was all I had to show for my efforts. At last, I gave up and sat back against the netted sides of the playpen to pout, my anger focused on Barbara. I had been willing to play along with her weird game of babying me but with this new, evil twist–she’d gone too far. It wasn’t fair! And the tantalizing softness of my prissy diapers seemed to mock me–letting me touch and stroke them but denying me anything further.
In a fit of rage, I threw one of the dolls at the far wall. I barely managed to bite back the curse upon my lips, knowing Barbara would hear me and probably paddle me for it. Her control over me was now complete and absolute.
I wanted to destroy everything here; rip off my diapers, flip the playpen upside down and make my escape but where would I go? More immediately, what would I wear? There were no clothes anywhere in the house that were made for a guy and I couldn’t very well go out nude.
I sighed heavily and sat back down in a huff. Who was I kidding? At the first sign of a tantrum, Barbara would be in here and I’d find myself over her lap, getting the daylights spanked out of me.
I hated the fact that she was stronger than me, both physically and mentally but worse than that was that I still lusted after her–despite everything she’d done to me. It was infuriating! Even now, I could see the soft, smooth skin of her curvy breasts, as she gazed down on me with her smothery, maternal love. She did love me and as much as I hated to admit it–I was starting to love her, although I had to admit my emotions were still in a chaotic, confused state.
All of a sudden, and without warning, I felt a strong, warm stream of pee surge into the front of my diaper.
“Oh!!” I squealed, just as I caught it in time to stop it.
Feeling gingerly, I placed my hand on the front of my diaper. I could feel the warmth spread over most of my crotch and a surprising amount of wetness had saturated the cloth.
I choked back a sob as I wondered what was happening to me. Was Barbara right? Was my urgent need to breastfeed from her causing me to lose control over my bladder? I was becoming more of a baby with every passing day.
Just as I was contemplating that terrible thought, another stream of pee flooded into my diaper. I was able to stop it, just barely, but now I could feel there was plenty more behind it. Gripping the side of the playpen, I felt like I was holding back the Mississippi. With a sob of shame, I let go and let it flow uninhibited. Hot pee splashed into my diapers, soaking back between my legs and deep into my seat. I was kneeling on my knees, afraid to sit down for fear it would leak out the sides. On and on it went, seemingly without end as I soaked my thick diapers completely and thoroughly. I felt so helpless, unable to prevent wetting myself and I felt the heat in my cheeks as I imagined what my friends would say if they could see me now.
As I knelt there, gripping the rail with one hand, my other went back curiously to feel the warm pee-soaked seat of my diaper over my plastic pants. I caught a sight of myself in the wall mirror and I blushed with shame. I’d never felt so babyish before, my pacifier still in my mouth as I looked at myself, a big sissy baby who’d just wet his diapers like an infant.
A tear trickled down my face as I stared back at my reflection. Barbara had been right about everything–she had been right and I had been wrong. Looking at myself, I knew I could never be a real guy. It just wasn’t in me. What I wanted and what I needed was a mommy, a mommy like Barbara that was willing to care for me and love me for what I was–a whiny, weak-willed sissy who belonged in diapers and baby clothes. I was beginning to understand why she had paddled me over the last week. In my heart of hearts I knew I deserved it and needed it.
But what I needed right now was a change. My diapers were completely soaked and they were sticking stubbornly to my rump and hips.
My voice quavered as I gripped the side rail weakly.
“Mo-Mommmmy!!”
Chapter Six Back to School for Chrissie
Strapped into the carseat in the back of Barbara’s minivan, I sucked nervously on the fat pink pacifier filling my mouth to capacity. Today I was headed back to school, although what kind of school–I wasn’t exactly sure. I was dressed no differently than a three year-old baby girl so I dreaded the prospect of being seen by anyone, regardless of the type of school. Barbara had picked out a delicate white baby dress, generously trimmed with pink eyelet lace and a big decorative pink bow on it’s Peter Pan bodice. She had me in glittery white tights and my fat, embarrassing diapers were covered with a set of fancy pink rumba panties which had three sassy white ruffles crossing the seat. My stockinged feet had pink anklets and my ever present glossy black Mary Janes. Lastly, Barbara had pulled my growing hair into two pigtails and secured them with pink satin bows. She’d also applied a light coating of blush to my cheeks but I was already blushing at the thought of others seeing me like this.
On top of that, my enforced chastity certainly wasn’t making my situation any easier. I’d woken up several times during the night with painful attempted erections that my body still hadn’t learned were now forbidden. But worse than that was my time during the day when I was fully awake and aware of my surroundings. Maybe it was just me, but it seemed like Barbara was dressing even more provocatively than before. She constantly teased me with her form-fitting clothes and plunging, low cut tops. I had been on edge all week as I gazed hungrily at her jaw-dropping body, my little penis throbbing desperately in it’s device but unable to get any relief. At times, I felt light headed and physically weak with desire, at other times, I felt ready to explode with frustration. It was so unfair!! I found that after a day of constant stimulation, the precum would begin to ooze uselessly from the end of my chastity device, partially draining me but still leaving me horny and completely unsatisfied.
I was starting to suspect that it had been Barbara’s plan all along to get me to first accept, and then even want to wear diapers, because of their soft, comforting embrace. I’d never known such an exciting, pleasurable outlet for sexual relief and I was sure she known from the start I’d come to find them irresistible. She’d given me a taste of how wonderful they felt for a chronic masturbator, only to cruelly take that pleasure away.
And every day, Barbara would smile sweetly at me, her touch gentle and loving, as she let me nurse like a baby from her big bountiful breasts. Sometimes I’d literally cry with pent-up desire as she forced me to suckle from her firm, milky nipple but she’d only giggle at my predicament and softly pat the front of my sissy diapers as if to mock my desperation. She knew without question that she had me completely under her control and there was nothing I could do about it.
All this receded into unimportance as we pulled into a parking spot in front of the Francis Merrimont Boy’s School. I could see normal guys my age, milling about as they talked amongst themselves while they got ready to go inside. I whimpered nervously as I frantically sucked on my pacifier, terrified at having to walk past them in my prissy baby outfit.
Barbara came around to my side of the van and after opening the sliding door, unbuckled my carseat straps.
I shook my head and looked at her pleadingly but she only smiled down on me with her usual warm, yet dismissive look.
“I know this is going to be hard at first, Chrissie, but it’s important for you to completely accept what you are and be seen as the sissy baby we both know you are deep inside. You see, you’re still clinging to an image of yourself as a boy but the fact is, you know and I know that’s not the real you. You’re just a little baby that needs his diapers and his mommy–and the sooner you accept that, the easier it’ll be for you.”
I shook my head, even as a tear of shame tumbled down my cheek. And as if to verify what she said, as she helped me out of the seat and onto the sidewalk, I felt a sudden, strong, hot stream of pee escape into my diapers. Squealing helplessly, I dropped my hands down as if that might be able to prevent it but the damage was already done. Of course, between the rumba panties, tights, and my usual plastic panties, there was no visible evidence of my accident but the warm wetness inside only added to my feelings of babyishness.
No sooner was I standing in the open sunlight when several guys looked my way and began pointing at me. Their jeers and laughter washed over me and my cheeks burned hotly. Barbara responded by taking my hand and forcing me to wave back at them, even as I stared at the ground in utter shame.
“Say hi to those big strong boys, Chrissie,” she said encouragingly.
I think she sensed I was about to burst into tears because she closed the van door behind me and took my hand, leading me into the big main doors of the building. The guys continued to make mocking comments although as we got closer, Barbara’s sexy body tended to have it’s usual distracting effect on them. She smiled coyly back at them, her high heels clicking confidently and crisply on the concrete steps before we went inside.
I was looking around feverishly, only to find more guys staring at me in disbelief as Barbara led me through another door and into a separate room. I was vastly relieved to be away from their staring, contemptuous faces and alone for the moment but for how long? Barbara removed my pacifier and just then, the other door in the room opened and a drop-dead gorgeous woman in her late twenties sauntered in.
She was a smoldering blonde with unbelievable pretty green eyes, a cute button nose and full, luscious lips. She wore a tight wrap around top that hugged her full sexy bosom and showed off a deep line of cleavage that was impossible to ignore. Her short, summery skirt left much of her smooth, firm thighs exposed which was emphasized by her strappy high heels.
“So this is the pretty little sissy girl you were telling me about!” she exclaimed excitedly.
My face went a deep shade of crimson as she bent down to look closer at me. I’d always been intimidated by beautiful women and as usual, I couldn’t hold her gaze. I was staring at the floor, too shy to look up when her long nail reached down and lifted my chin to look up into her gorgeous eyes.
“My, you certainly are a pretty one, aren’t you Little Miss Priss?” she asked sweetly.
I felt a mixture of emotions, mostly shame at being called pretty but I also guiltily felt some small measure of pride by the compliment being paid to me by this incredibly stunning female. I really didn’t like being thought of as pretty but if that was what made this babe like me, how could I complain?
“Chrissie, say hello to your new teacher–her name is Ms. Taylor,” Barbara said as she patted me on the thick, ruffled seat of my diapered bottom.
Forced to look at the arresting features of her face, my cheeks burned brightly.
“H-h-hi,” I croaked nervously and I swallowed hard.
She smiled a devastating smile that washed over me like a warm bath and made my toes tingle. What a hottie she was!
“Hello Chrissie, welcome to my nursery,” she said in a light, sexy feminine voice, “My, my…I think you’re going to make all the other sissies jealous with your cute, girly looks–you’re not really a boy under all those frills are you?”
Still blushing three shades of red, I nodded in confusion.
“Uh-huh,” I squeaked weakly.
Ms. Taylor laughed musically.
“I don’t believe it! You’re the prettiest little girl I’ve ever seen, but I better keep my eyes on you–some big strong boy is going to want to kiss you!”
I blushed furiously at her words as Barbara laughed with Ms. Taylor delightedly.
“Now that I could see all too easily!” Barbara added, “Do you think you would you like it if one of those boys outside gave you a nice big kiss?”
“No!” I snapped petulantly but I couldn’t stop blushing.
I felt so sissyish that it was easy to imagine one of them forcing his will upon me.
“And it looks like your mommy’s got you very well diapered–is she a big wetter?” Ms. Taylor asked Barbara.
“Oh my–yes,” she replied, “But her next change isn’t due until lunchtime and her diapers can hold any accidents she may have for awhile yet.”
“Don’t you worry Sugarplum,” Ms. Taylor smiled down at me, “I’ve got plenty of diapers and plastic panties for sissies like you who have no control. I’ll take very good care of you.”
I hated being thought of as having no control but I guess it was to be expected in my present outfit.
“Well, since that’s all set then…I better be going, I have to be heading back to work now,” Barbara said as she pulled her keys out of her purse, “You be a good little girl for Ms. Taylor–she has my permission to spank you if you misbehave, you know.”
Between the two of them, I was crushed with humiliation, but I was even more distraught at being left alone in this strange place, with a bunch of strange people. Even though Ms. Taylor was a major knockout, I was terrified of the unknown humiliations that were almost certainly awaiting me here.
“Mommy–don’t go,” I pleaded anxiously with her.
“I’m sorry Sweety, but mommy has to go to work–you’ll be just fine here,” she assured me, “Don’t you worry about a thing.”
In my rising panic, I felt a hot stream of pee suddenly released from my bladder. Stamping my Mary Jane-clad feet in frustration, I stood helplessly as yet another, even stronger surge quickly soaked the front of my diapers in a humiliating display of my lack of control. My lower lip trembled and I looked up in panic at Barbara as I felt my diapers being flooded uncontrollably.
The combination of everything was too much for my fragile temperament and I abruptly burst into tears.
“Nooo!” I wailed as even more warm pee flowed freely into my diaper.
“Mommmmy!”
I threw my arms around Barbara’s neck and hugged her tightly as the pee quickly saturated my seat and began soaking the surrounding cloth. My tights and rumba panties conspired to make sure the drenched cloth hugged my buns and inner thighs in a sopping wet embrace.
“Don’t leave me Mommy!” I wailed as tears streamed down my face.
My shoulders heaved and my breathing was labored as I sobbed like a baby on her shoulder.
Barbara sighed and helped me over to a seat behind a desk, sitting down and then taking me upon her lap. In moments, her blouse was undone, her delicate bra unclasped and her big, plump breast was put before me. Easing her firm, milky nipple in between my trembling lips, she pulled me gently to her as she wiped a tear away from my cheek.
“There, there now Baby….everything’s going to be okay…Mommy’s only going to be gone for a little while today…you’ll be just fine with Ms. Taylor here.”
I sobbed helplessly and nursed feverishly on the big nipple filling my mouth, quickly being rewarded with a steady stream of warm milk.
“Aww…you poor little thing,” she said soothingly, “Mommy’s little baby girl is just having a terrible first day already, hmm?”
I sobbed again and sucked even harder on her nipple, trying to regain my composure.
“Oh my…Chrissie’s already wet herself, I’m afraid,” Barbara informed Ms. Taylor as the warmth of my bottom gradually made itself felt on her thighs.
“That’s no problem,” Ms. Taylor replied, “I’ll be happy to give her an early change in the nursery, it’ll give us a chance to do a little bonding.”
“I’m afraid when she gets this upset, the only thing that will soothe her is a nipple…I’m sorry to make such a fuss,” Barbara said as she gently patted my head and encouraged my nursing from her breast.
“Oh, don’t even mention it, perhaps I can be of help here.”
Ms. Taylor pulled up another chair and undid the knot holding her wrap around top in place.
“Are–are you…?” Barbara queried.
“Yes,” Ms. Taylor giggled, “I’m lactating too so I can take over any time you’re ready.”
“Oh, that’s wonderful,” Barbara said, much relieved, “I usually let her nurse until she stops crying–you should be fine with her pacifier after that.”
Barbara helped shift me over to Ms. Taylor’s lap and I whimpered as her firm nipple was taken from my mouth. Whining miserably, I watched in captivation as Ms. Taylor opened the front clasp of her silky smooth satin bra to reveal a perfect, flawless breast; full and heavy with milk.
“Come here Chrissie, I’ve got a nice warm nipple for you to suckle from.”
I whimpered in embarrassment but soon began nursing from her breast.
Using her long, slim finger, she brushed away another of my tears and beamed down on me with satisfaction.
“That’s a good baby,” she cooed, “You take all you need my pretty little sissy.”
There she said it again. Was I really pretty, I wondered? I’d always known I had rather feminine features…could it be that with my baby dress, tights, sissy shoes, and a little make-up that I actually looked pretty? It gave me a strange feeling inside. It also gave me a familiar feeling inside my chastity device. My poor little penis was starting to strain mightily against it’s silicone prison in angst. Was it because a beautiful woman was letting me nurse from her awe-inspiring breast? Or was it something more?
Assured that I had finally settled down, Ms. Taylor returned her attention to Barbara.
“Does she need an enema today?”
“No, thanks though–she had one this morning during her diaper change,” Barbara replied.
She remained a little longer but when it was apparent I had stopped my crying, she made her goodbyes and left us alone. I continued to nurse until I’d had my fill from Ms. Taylor’s succulent breast.
Easing her nipple out of my mouth, Ms. Taylor gently pushed my pacifier in between my lips.
“There you are Chrissie. Are you ready to have your pampers changed?”
I sniffed and nodded weakly as she helped me up and took my hand in hers. Leading me through the door she came in, we entered a large room, that looked like a cross between a kindergarten classroom and a baby’s nursery. The walls were decorated with cartoon characters and several cribs were in a group at the far corner. I recognized a changing table with stacks of cloth diapers and a dresser nearby containing plastic panties and other supplies. On one side of the room were several desks at which two boys my age were sitting. One was an obvious sissy, dressed much like myself and it was strangely gratifying to see someone in the same predicament as I was. The other was another guy, dressed in a little boy’s romper with a white t-shirt and baby blue shorts and suspenders. At first glance, he didn’t appear to be diapered, although it was hard to tell and I thought I discerned a bulge around his hips.
As for the other sissy, he was very clearly diapered, wearing nursery print plastic panties over a fat, bulky diaper, much like mine. His short party dress was lilac and patterned with flowers and lace and I could see his legs were smooth to the touch. Upon seeing my arrival, he beamed happily, and skipped over to see me.
“Hi there–my name’s Joshy–what’s your name?” he asked enthusiastically in a high pitched, feminine voice.
I was still a bit taken aback by my circumstances and the appearance of another sissy but Ms. Taylor answered for me.
“Joshy, this is your new sissy playmate, Chrissie, although I rather think ‘Little Miss Priss’ is a better name–don’t you, Chrissie?” she asked me as she bent down to look me in the eye.
I wasn’t used to this kind of attention from such a gorgeous woman and I blushed shyly, unable to speak.
“I just know you two are going to have all kinds of fun together,” Ms. Taylor gushed.
Before I could respond, Joshy came over and hugged me close, nuzzling my neck with his nose in an all too friendly way.
“Wow–you sure are pretty!” he exclaimed cheerfully, as she stood back to look me over, “Do you want me to show you how to do your make-up?”
My face went red at the compliment and offer, as I tried to reconcile my confused feelings inside. Growing up as a boy, I had always wanted to be considered handsome and now that I was being thought of as pretty, I felt sort of indignant and humiliated, yet at the same time, my craving to be accepted made me inclined to be receptive. I was so befuddled and mixed up–I didn’t know what to think!
“Matty, come over and say hi to your new playmate,” Ms. Taylor told the other boy.
“Hey,” he said without rising, and none too eagerly. He was playing with some blocks and seemed altogether disinterested in my arrival.
Oddly enough, I felt a strange compulsion to want to know him, unlike the overly enthusiastic sissy Joshy, who from all appearances, seemed to have an immediate crush on me. There were other differences as well between the two–whereas Joshy had an obvious femmy nature about him, Matty seemed rather out of place here–he looked like a boy’s boy, with muscular legs and an undefinable rough edge to him. I could easily picture him tearing down a transmission in the auto shop or playing football on the school team.
I felt strangely disappointed that he was openly dismissive toward me. Why did it matter? I didn’t know. But for some reason, I wanted to be accepted by him and more than that, I wanted him to like me.
“Come along girls,” Ms. Taylor said as she took Joshy’s and my hands, Chrissie needs her diapers changed and then you two sissies can get to know each other better.”
I felt a little frustration at being lumped together as a “girl” but then I had to admit it wasn’t an unreasonable expectation either. And despite myself, Joshy’s enthusiasm was becoming infectious. As he skipped along gaily, I felt a lighthearted sashay start to enter into my own gait. Deep down–something felt tremendously liberating to be girlish and carefree and I still enjoyed the bulky feeling of my diapers between my thighs, despite my frustrating chastity device.
We entered another room, this one even more nursery-ish than the other, larger room and I saw more baby supplies and furniture arranged within it. Ms. Taylor guided me to a low, vinyl covered changing table and sat me down gently, while motioning Joshy to sit on the floor next to us.
“Joshy, why don’t you help me get Little Miss Priss here undressed so I can change her diapers?” she asked sweetly.
Like mommy’s little helper, Joshy enthusiastically agreed and they began unbuckling my Mary Janes and removing my lacey anklet socks. Soon, my ruffled rumba panties and glittery tights were being peeled down my legs and Ms. Taylor asked Joshy to get the baby bottle she had in the warmer.
“Oh my–look at these smooth legs of yours,” Ms. Taylor exclaimed as she stroked my bare thigh with her soft, slim hand. It send an electric thrill through me to have her touch me and I couldn’t prevent a shy smile from breaking across my face. I was used to being self conscious of my lack of hair but now, it was actually gaining me attention unexpectedly from this pretty teacher.
Joshy came back and–far from being jealous of the attention I was receiving–he bent down to stroke my thigh himself.
“Oh my gosh!” he gasped, “So soft and smooth! You are sooo lucky!”
For some reason, my penis was once again throbbing in it’s prison and I blushed with pride and excitement.
Joshy handed over the bottle and Ms. Taylor eased it between my lips.
“There you are Sweety–all my babies get a bottle when they get their diapers changed.”
My embarrassment returned and I watched closely as Ms. Taylor unpeeled the clinging plastic panties off of my sodden diaper and brought them down my legs. She tossed them into a large bin behind her and then unpinned either side of my diaper, pulling it down to expose my hairless crotch and tiny captive penis.
Both of them beamed cheerfully at me as they gazed down at my restrained, childish genitals.
“Aww, looks like someone’s been a naughty little girl,” Ms. Taylor said in a voice meant for a toddler, “Did my wittle Miss Pwiss get in trouble for pwaying wiff hersewf?”
My face burned with shame and I looked the other way as I sucked desperately on my bottle. Ms. Taylor giggled and pulled my heavy, wet diapers out from beneath me and then began wiping my buns and crotch with cool baby wipes.
“Don’t you worry Babykins, Joshy’s little pee-pee is locked up too,” she assured me as she sprinkled baby powder over my chest and tummy, “Little sissies like you two just can’t be trusted not to play with their wiennies.”
I was mortified to have her talking to me like this but there was zero I could do about it.
“Tell you what–I have something that I’m sure will make you feel better. You won’t be able to cum but it might give you a little relief, okay?”
I whimpered with anticipation at anything she might be able to do to relieve my poor aching penis. This had to be my lucky day!
Reaching behind me, Ms. Taylor brought forth a strange looking object that looked like a streamlined dildo. Looking prettily like an angel from heaven, she smiled down at me enigmatically as she carefully coated it with KY. Her smile alone was enough to make me hard but there was also something indefinable in her feminine demeanor–so subtly sexy it made my heart beat wildly within my chest. Her finger probed my hole and I gasped again, even as my cheeks burned with desire and shame. Very gently, she began pushing the dildo object into my puckered hole, never forcefully, but with loving care as she slowly eased it past my bashful sphincter. I whimpered weakly, my breathing labored as I watched her through half closed eyes while she alternately twirled and slide the dildo inside me. I moaned like a little girl and she began a tortuously erotic rhythm, smiling down at me knowingly as she slowly plunged it in deeply and made me gasp like the virgin I was. I let out a small sigh of pleasure as she eased it out, only to push it in again.
Joshy was captivated with watching me but my eyes were closing again as I moaned weakly. Waves of pleasure were washing over me–I’d never felt anything so wonderful in my life and my hole craved the slippery pliable rubber of her dildo, yet at the same time, my penis ached painfully as it surged and throbbed frantically within my chastity device.
With my eyes still closed, I suddenly felt warm lips kissing my own.
Opening my eyes in surprise, I was shocked to see Joshy amorously and eagerly locking his lips to mine while he held my wrists to the changing table. I squealed loudly and squirmed beneath him, my shock competing in confusion with the erotic bliss I was receiving from Ms. Taylor. Joshy’s eyes opened and he smiled at me, even as he kissed me hard again.
I wriggled like an imprisoned fish and he finally let go of my arms, sitting back with a happy, contented smile on his cherubic face.
“I’m sorry Chrissie–you’re so pretty, I just had to kiss you!” he giggled.
My face flushed even redder than it already was as I stammered incoherently. Whatever reply I was attempting to make was cut off as Ms. Taylor plunged the slippery dildo deep once more inside of me. I moaned deliriously and gazed weakly up at her pretty face. As my eyes wandered down, I drank in the soft, silky smooth skin of her breasts, full and round like two honeydew melons. I helplessly straddled the line of being tortuously close to cumming as she continued her erotic ministrations. I moaned again, unable to speak, and I shuddered with ecstasy everytime she pushed the dildo back inside me. I felt wonderfully emasculated and feminine, savoring the feeling of having my own hole so deliciously filled. Yet at the same time, I also craved that orgasm that felt so tantalizingly close. I was desperate to cum!
Looking down at my penis, I could see a fair sized pool of cum dribbling out from the tip. It was dribbling down between my legs in a steady drip, and Ms. Taylor used her free hand to coat my pacifier with it before easing it between my lips. I whimpered weakly as I tasted my first semen, blushing with guilt as I passively and submissively humiliated myself before her.
A random thought entered my mind; could this be what Matty’s cum tasted like? I blushed hotly at the thought, even as other, even more forbidden fantasies swam into my imagination. What would it be like to have Matty’s cock in my mouth, I wondered. I pictured myself, reverently on my knees before him as he drove his manly tool deep into my mouth while I did my best to please him. Would I be able to satisfy him? Would he like me then, I wondered.
Finally, Ms. Taylor slid the dildo out and she put it aside. My own penis throbbed weakly within it’s prison, deprived of a mighty, earth-shaking orgasm, yet fully drained of my joy juices. It was so frustrating, I felt on the verge of crying!
Still breathing heavily, I whimpered impotently as Ms. Taylor lifted my ankles and slid a thick stack of bunny soft diapers beneath me. Sprinkling baby powder on me, she smiled down on me sweetly as she pulled the cloth around my hips.
“These are extra thick down the center, Chrissie, for heavy wetters like you.”
I fought back the urge to cry, even as the tears filled my eyes. It was all so unfair! Why couldn’t I be allowed to cum??
Looking down, my imprisoned penis was soon buried in the soft, thick folds of her triple layered diaper as she pinned either side with pink headed safety pins. Taking a pair of clear plastic panties with colorful polka dots in her hands, Ms. Taylor shook them out in front me.
“Aren’t these cute, Chrissie?” she asked brightly, “I think they’ll look just perfect with your frilly baby dress.”
As I sucked on my semen coated pacifier, she gathered the leg holes and began working them up my hairless legs.
“You know, I can’t really blame Joshy here for kissing you,” she chuckled as she began working them over the bulging cloth of my diaper, “With girly smooth legs like yours, all the boys here are going to be hot to try and make a pass at you.”
I wasn’t so sure, but then, I wasn’t sure about anything anymore.
“There you are, my Little Miss Priss,” she declared cheerfully as she gently patted the fat front of my diaper, “All diapered and ready for the day!”
I blushed again at being called her little nickname. It was bad enough having to dress like this without her heaping even more shame upon me.
Ms. Taylor lifted me to my feet just as her phone rang from the other room.
“Now, you two girls be good while I go get that,” she said as she winked mischievously at me. I watched her saunter out of the room, my eyes lingering on her perfectly shaped rear and long, sexy legs but once she was gone, my attention returned to Joshy.
Without another thought, I reached out and slapped him on the face. I meant to hit him hard but somehow, it came across weak and ineffectual.
“How dare you kiss me!” I cried indignantly.
Joshy’s smile evaporated and he looked back at me in shock as tears brimmed in his eyes.
“I-I’m sorry Chrissie…please don’t be mad at me,” he whined in his little voice. A tear trickled down his cheek as he held it tenderly, obviously hurt by my attack, although it was probably more emotionally than physically.
I was still feeling humiliated by the whole experience and I crossed my skinny arms over my chest petulantly. I knew I must look like a fussy little girl in my prissy white and pink baby dress and bulging diapers but I did my best to appear macho.
“I don’t even know you!” I continued, although no sooner were the words out than I regretted them. It wasn’t because of my lack of familiarity with this sissy–I was trying to show him I was still a guy’s guy!
My words obviously had the wrong effect because Joshy came over to put his hands on my shoulders in a gesture of warmth and caring.
“I know that Chrissie–but I want to get to know you and be your friend,” he emphasized strenuously, “Will you please forgive me?”
Still feeling huffy, I brushed off his hands warily.
“I don’t know…”
“Please?” he begged me.
I sighed wearily. Today had already been so trying for me and I had no fight left in me.
“…Okay…” I finally replied without returning his anxious gaze.
“Oh–thank you!” he exclaimed as he threw his arms around me and hugged me tightly, “I’m going to be your very best friend!”
Ms. Taylor strode back into the room, only to find us hugging like lovers as Joshy fondled the thickly padded seat of my diapers.
“Well…I see I can’t leave you two girls alone for a minute,” she giggled, “But I guess sissies will be sissies.”
I blushed and pushed my way out of Joshy’s clingy embrace, unsure how best to respond to her implied accusation.
“Oh my gosh–I almost forgot your shoes, Sweety!” Ms. Taylor exclaimed, “You just sit your pretty little bottom down and I’ll get you all fixed up.”
Sitting back down on the changing table, Ms. Taylor helped put my lacey anklets back on, followed by my Mary Janes.
“I thought your pink tights were really cute but it seems a shame to cover such silky smooth legs like yours–don’t you think, Chrissie?” she asked me.
“I guess so,” I mumbled, although Joshy seemed to be in complete agreement with her.
“Joshy, why don’t you show Chrissie here your collection of dollies–And I’m sure she’d just love to see your dollhouse.”
“Okay!” Joshy replied happily.
Taking my hand, he tugged at me eagerly to guide me into the adjoining room. Ms. Taylor took a moment to go and check on Matty before taking a seat at her desk. Her workspace was nothing special, except that it was open to view from the front and I watched in fascination as she slowly crossed her lovely legs, letting her high heel dangle over the floor. I sighed in admiration at her incredible beauty and sexiness. She was such a total babe!
Joshy continued to blabber on, oblivious to my lack of interest, telling me all about his doll collection, wearing make-up, styling hair and games of hopscotch and cat’s cradle. My attention varied between making noncomittal grunts to Joshy and dividing my gaze between Ms. Taylor and Matty. The latter had short hair, beautiful blue eyes and a boyish, pug nose. I felt strong feelings of envy for him as another guy, although our shared gender was where our similiarities ended. Clearly, he was everything I was not, nor would ever be. I sighed in resignation at the thought.
I hoped he would come over and talk to me but that seemed highly unlikely. Other than staring at Ms. Taylor’s fabulous body, he rarely looked up from what he was doing and seemed hardly aware we were in the same room.
I was distracted by the sound of Ms. Taylor’s cell phone ringing and she answered it with a musical greeting that made my heart skip a beat. I tried not to be obvious and stare at her but it was impossible to ignore the happy expression on her pretty face as she talked to whomever it was on the other end. A closer listen revealed that it was a man, and most likely a boyfriend.
Given her incredible beauty, it shouldn’t have come as a shock that she had a lover but for some reason, it did. I seethed with irrational jealousy that someone else would be enjoying her considerable charms and I hated myself for giving in to the emotion.
Before long, the conversation ended and she hung up, a happy smile lingering on her gorgeous face. Leaning forward on her desk, she pressed a button on the school wide intercom.
“Sarah?”
“Yeah?” came the casual reply.
“Would you mind covering me for my lunchbreak?” Ms. Taylor asked.
“Sure thing Hon–I’ll be right there.”
“Girls–I’m going to be gone for about an hour–maybe more,” she giggled, as if she were privy to some private joke, “But Sarah will be here to take care of you, okay?”
The others answered, although none too enthusiastically, and I felt a shiver of anxiousness based on their reactions. Of course, it was easy to imagine that whoever Sarah was–she was not Ms. Taylor. That alone would make me regret her departure, but I sensed an uneasiness that went beyond our being deprived of our smoldering hot teacher.
When the far door opened, I began to understand why they had been less than receptive to our substitute. I recognized Sarah from my baby shower all too well–she was the one who had paddled me so fiercely after my diaper change. Not only that, the only side I had ever seen of her was her cruelty. Her arrival certainly boded ill, for me at least.
Ms. Taylor grabbed her purse and car keys and was out the door in a flash, leaving us alone with this vengeful vixen.
“Well, well, well…” she said as she came over to look down on me, “If it isn’t Barbara’s little sissy…Chrissie, isn’t it?”
“Uh-huh,” I mumbled nervously, my heartbeat quickening perceptibly.
Her slim hand was out like lightning and she slapped my cheek harshly before I could so much as blink.
“Yes Ma’am,” she corrected me, as she towered over me with her hands on her curvy hips, “You will answer me with a ‘yes ma’am’ or ‘no ma’am’–understood?”
“Yes Ma’am,” I quickly replied as a tear tumbled down my reddening cheek. It stung painfully and I realized belatedly that I had woefully underestimated her despite my initial assessment.
“Well, since you’re here now, it’s time you understood a few things. First, we don’t tolerate any backsass or horseplay–got it?”
“Yes Ma’am,” I immediately replied in a whimper.
“Second off, we don’t allow any hanky-panky between any of the students–or by themselves. You got that one?”
“Yes Ma’am,” I answered her, even as my cheeks reddened. Was she somehow aware that I used to be a chronic masturbator?
“The school principal at Francis Merrimont Boys School is Mrs. Sterne. The boys all fear her, and for good reason, but she especially puts the fear of god in prissy little sissies like you.”
“Yes Ma’am,” I responded, even though she hadn’t actually asked me a question.
“But rather than give you a speech about who she is, I think we should introduce you to her, personally.”
The way she said ‘personally’, made me doubly nervous but I was afraid to try and stand up to her. And to be sure, the days of whining my way out of a situation I didn’t find agreeable were long gone–Barbara had seen to that.
“Come along, Chrissie,” she instructed me, “It’s time you met Mrs. Sterne.”
Snatching my hand in hers, she dragged me into a different room where she knocked on a closed door with a small plaque saying ‘Principal Mrs. Sterne’ on it. Ordinarily, I would have wet my diapers in fear at this point but I had just gone a little while previously and didn’t need to go.
“Enter,” a firm, yet feminine voice replied.
Sarah opened the door to a spartan office, minimally furnished, with a large mahogany desk set off to one side. Behind the desk, sat the imposing figure of Mrs. Sterne, the severe looking brunette lady who’d given me the Spencer paddle as a gift at the baby shower. I just about choked with fear as she looked up at me, her eyes registering both recognition and contempt on her beautiful face.
“Barbara has enrolled Chrissie here in Ms. Taylor’s class,” Sarah said by way of introduction.
Without a word and without taking her eyes off me, Mrs. Sterne slowly rose and smoothed the tiniest of wrinkles from her immaculate grey pencil skirt. I felt as small and insignificant as a lowly bug as she gracefully came around the desk to look down on me, her gaze cold and steely.
“Yes indeed,” she said simply, although my stomach was doing somersaults as I tried to return her attention.
Given how close she was to me, I was forced to look up into her darkly beautiful countenance, although I couldn’t help but notice her wonderfully big breasts thrusting proudly against the pristine white fabric of her businesslike satin blouse.
For a moment, nobody spoke (I was too terrified) and my eyes drifted down to her rising chest, which expanded outward magnificently with every breath she took. I licked my lips anxiously as my eyes took in the delicate lace on the huge cups of her bra, clearly visible beneath the thin, silky top it was trying so hard to burst out of.
Suddenly and without warning, I felt the scalding sting of her steel-like hand as she slapped my cheek hard enough to make me see stars.
“Don’t you ever let me catch you staring at my breasts–do you understand me?” she barked viciously.
I burst into tears and gripped the sore side of my face tenderly.
“Y-y-yes Ma’am!” I bleated repentfully.
She most definately lived up to her namesake–of that, there was no doubt! I’d never met someone so hot, yet so intimidating!
Like her assistant, she placed her slim, perfectly manicured hands on her broad, curvy hips and stared down at me remorselessly, daring me to challenge her.
“When you enter my office, it will only be for one thing,” she informed me in clipped tones, “And that is to receive the painful and humiliating punishment you have so richly earned for yourself.”
I quailed at the thought of facing her under those circumstances.
“When that happens, you will have the opportunity to become better acquainted with the paddle I call the ‘Sissy Tamer’,” she said as if describing a sacred and noble sword.
Reaching over, she picked up a long, black wooden Spencer paddle, much like the one she’d given me as a present, and hefted it in her hands. It looked light as balsa wood, given the ease in which she handled it but when she slapped it against the palm of her free hand, I nearly gasped with the impact.
“I apply this to bare bottoms, especially sissy bare bottoms, who badly need to feel the harsh slap of oak from time to time.”
“I-I-I p-promise I’ll b-be good,” I stuttered in terror.
An evil glint appeared in her dark eyes and she smiled the briefest smile before it vanished like a winter wind.
“Yes you will,” she replied, “And you’ll be one sorry little sissy after you’ve been over my lap.”
I gulped hard, desperate to escape such a fate.
“But I promise!” I bleated, “I promise to be good!”
“You know,” she said ignoring my response, “I’ve paddled more sissies than I can count and watched them all cry like babies…but you have to be the prissiest, most frou-frou sissy I’ve ever laid eyes upon.”
“Y-yes Ma’am,” I said, afraid to disagree with her.
“Some of the sissies here “graduate”, if you can call it that–and are sent to live with strict women who have their own purposes for them, although what someone would do with a limp-wristed, pansy such as yourself, I have no idea.”
I wilted miserably under her scolding lecture.
“You should be very grateful you’re under the care of someone like Barbara who is willing to mollycoddle you…if you were living under my roof, you’d receive nothing but the strictest discipline, and you’d learn what real obedience means.”
I had no doubt in my mind she meant every word of what she was telling me.
“Y-yes Ma’am,” I responded reflexively.
Turning around, she retraced her steps back around her desk to take her seat, with the poise and grace of a panther.
“That will be all for now,” she said dismissing me, “I’ll look forward to giving you your first taste of the Sissy Tamer.”
Sarah reached down and snatched my hand, jerking me around as she led me out through the door we had come in. My head was still spinning after my perilous encounter with Mrs. Sterne. I made a mental note to seek out Joshy’s advice later on and find out how to avoid her terrible wrath.
Once back in the Nursery, Sarah called Joshy over, almost as if she had been reading my mind.
“Joshy, I want you to do Chrissie’s make-up for her, just like you’ve done your own,” Sarah ordered him.
I could sense his nervousness and as he began applying pink glossy lipstick to my lips, we shared a look of mutual fear. What did she have in mind, I wondered. It couldn’t be good.
I could tell by the care and skill that Joshy did my make-up that he obviously had a lot of experience with it. At least that was something I could take pride in–only a true sissy would have developed such girlish skills.
“Make sure you give her plenty of lipstick,” Sarah instructed him, although she didn’t elaborate as to what her reasons were.
Joshy dutifully twisted the cylinder of glossy pink lipstick to expose more of the rose scented material. With careful precision, he ran it across my puckered lips and then back again, ensuring a thick, slick coating.
Just then, a large man wearing a yellow polo shirt and khaki shorts entered the room, his presence exuding male confidence from every pore on his ripped, imposing body. Sarah’s eyes lit up immediately at his handsome appearance and she grinned amorously at him, moving over and taking his big, muscular arm in hers. He eyed us strangely, looking us over carefully as if looking for some special attribute, although I couldn’t imagine what a man like that would want with either Joshy or I.
“Okay everyone, line up here. Coach Saunders wants to get a better look at you,” Sarah instructed us.
It was easy to believe this guy was a coach, and I suspected he was actively involved with the school’s football team. His physique was without peer, and his ice blue eyes drilled into us from his manly, rugged face. His square jaw and close cropped sandy hair made me think that even Sarah–who was no slouch in the looks department–must have felt lucky to have this guy as her boyfriend.
I saw Matty come over but Coach Saunders quickly put up his meaty hand to stop him.
“Not you son–just the sissies.” he said in a gruff voice.
Matty complied and Joshy and I stood in place, nervous and fearful about what they wanted of us. I squirmed in my frilly short baby dress and diapers, acutely aware of how sissyish and feminine I looked. My hairless legs felt painfully exposed and unconsciously, I pulled the hem of my short dress down in a futile attempt to hide my embarrassing sissy diapers.
Why would a coach for the school possibly have any interest in us? Could it be they wanted to parade us before the rest of the school to humiliate us? After meeting Mrs. Sterne firsthand, I was willing to do anything to avoid a return trip to her office.
“Hmm,” the coach said, “This one must be new here,” he said, thrusting a huge calloused thumb in my general direction.
“Yes, the prissy thing just started today,” Sarah informed him.
Stepping closer to me, he gave Joshy a rude push, who fell backwards awkwardly.
“That one’s no where near as girly as this one,” he said to Sarah as he inspected me closely.
I felt hurt by his appraisal but my instinctive fear for this rough man overrode my wounded pride.
Looking up into his steely cobalt eyes, I saw what I thought was lust beginning to glaze them over.
“Oh yes, this one will be just fine for what I have in mind…” he said ambiguously.
My eyes fell to the growing bulge in his pants and my heartbeat quickened in fear.
“Ever sucked a cock, Sissy?” he asked me bluntly.
I blushed bright red with embarrassment.
“N-no Sir,” I replied meekly, although I felt sure he didn’t believe me.
“Well today’s your big day,” he chortled, ” ‘Cause you’re gonna suck my cock and swallow my load–whaddya think about that?”
I couldn’t believe my ears. Was this guy really talking about making me suck him off?
“B-but I’m n-not even g-gay,” I stammered uncertainly.
“You’re a sissy and all sissies suck cock,” he informed me in no uncertain terms, “You should consider yourself lucky I’m allowing you to wrap those pink lips of yours around my tool.”
I felt anything but lucky–I was terrified of this brute!
“B-b-b-but–”
Unbuttoning his shorts, he rested his hands on his waist and looked down upon me brazenly.
“Get down on your knees,” he commanded me.
“Y-yes Sir,” I quivered.
“Unzip my shorts.”
With trembling hands, I did as I was told, trying desperately to think of a way out of this. Obviously, I couldn’t confront him physically–he looked like he could snap me in two!
“Now, pull them down.”
I reached around his solidly built hips and worked his shorts down the tree trunks of his legs. His underwear were already tented in front and I stared with awe and trepidation at the massive bulge growing like some giant beast.
“Now pull my underwear down, sissy-boy.”
“Y-yes Sir,” I replied squeamishly.
As the elasticized waistband of his boxers came down, I gasped in shock at the leviathan it had been covering. His cock was truly massive, eight or nine inches in length and unbelievably fat. I had no idea they could be so big. I gulped hard as I stared at the huge pink head, a dribble of precum already oozing out of it’s tip and the scent of his cologne filled my nostrils heavily. I found myself breathing harder in anticipation of what was about to happen. Was I really going to have to put this throbbing monster into my mouth?
“Take it in your hands and kiss the head,” he ordered me.
“P-please don’t, I-I don’t think I–”
His big hand reached forward and pulled my head toward his cock brusquely.
“Kiss it, you sniveling sissy,” he demanded gruffly.
“But I-I-I–”
He grabbed my head and pulled it forward until my shiny wet lips touched the tip of his warm tool. It left a glossy pink imprint against his hard, firm flesh.
Whimpering weakly, I gave it a little frightened kiss.
“Ha ha!” he bellowed, “You even kiss like a sissy.
“Now I want you to ask me politely if you can suck my cock…go ahead sissy–ask me.”
I looked around the room as if expecting someone to intervene on my behalf but nobody was moving. Joshy was watching in horror and Sarah was looking down on me with an evil smirk on her face.
“Um…I um…” I stuttered haltingly.
His hand reached down and he swatted the top of my head roughly.
“Look up at your betters when you ask them a question,” he barked.
I certainly didn’t want to make this brute angry!
I sniffled and cleared my throat nervously.
“Um…Sir? May I um…please suck your, um, penis, please?” I said hesitantly.
“Its a cock, you little faggot,” he sneered, “now open wide.”
Fearfully, I did as I was told but I was too afraid to keep my eyes open. No sooner had my pink glossy lips parted when I was rewarded with his meaty battering ram. He shoved it deep into my mouth, ramming it all the way in until it bottomed out at the back of my throat. My eyes flew open and I gagged reflexively, my hands waving the air in front of me as I tried to put a stop to his abuse. He pulled it out, just enough to give me a good taste of his firm, throbbing head, before plunging it back in again. I felt like I was choking on a baseball bat! I’d never had anything this big in my mouth in my entire life and my jaws hurt just trying to take it all in.
I squealed like a girl as he gripped the sides of my head firmly and began pumping me forcefully. I could already taste his copious precum and it coated my mouth with salty slickness as his fat head slipped in and out between my wide open jaws. My cheeks were stretched to the limit as I struggled to accommodate his mighty thrusting pole. I squealed helplessly, waving my hands again for him to stop but he showed no signs of hesitating.
“Suck on it good, sissygirl,” he said in a husky voice as he energetically plunged it deep into my mouth again.
My gagging only made him chuckle with glee at my plight and he widened his stance to give himself a better balance. I was forced to take a hold of the base of his cock but my small hands only went halfway around it’s massive girth.
“Look up at your Master when you have his boner in your mouth,” he demanded.
My eyes fluttered upwards to gaze upon his handsome, mocking features.
“That’s better,” he said smugly, “I want you to see who it is that’s gonna fill your mouth full of cum.”
I was terrified at the thought of having his semen in my mouth. It was only a week ago that I kissed my first girl and now I was being forced to give this brute a sloppy blowjob! I prayed he wouldn’t really cum in my mouth but instead pull it out. Maybe he was just trying to frighten me.
Would there be much, I wondered. I certainly hoped not.
“You know, I recognized right off that your sissy faggot friend was just a guy wearing a dress and diapers but I really thought you were a girl,” he admitted to me.
My face went red with shame as he pumped his hard cock in and out of my slick mouth.
“But with pouty, dick-sucking lips like yours, you better count on some guy wanting to ram his cock down your throat everyday. I’m gonna teach you the fine art of sucking a real man dry if it’s the last thing I do.”
He laughed heartily as he looked down on me, slamming his big fat member deep into my throat and making me gag on it again.
I squealed weakly in protest, unable to defend myself verbally.
Already, my jaw was hurting and my muscles were sore as I silently prayed for him to stop his brutalizing of me. Nevertheless, the sooner I could get him to cum, the sooner I would be finished here, or at least, that’s how I rationalized it to myself. Unconsciously, I sucked and slobbered with determination and diligence, trying to manipulate his mighty shaft into releasing it’s liquid treasure.
Suddenly, I felt him grab my ears so hard I thought I’d cry out with pain. Inexplicably, he paused his rhythm for a moment before jamming his shaft as far in as it would go.
With a heavy guttural grunt, he exploded in orgasm, blasting a huge creamy load right down my throat. I was forced to swallow it in one gulp and as he eased his cock out slightly, I thought he was done but then he quickly flooded my mouth with another warm, creamy batch of his thick semen. With my mouth still crammed full of cock, I squealed loudly and shook my fists in frustration, struggling to swallow the latest salty load he’d given me. No sooner did it get past my larynx when he blew a third and equally large load, filling my mouth again completely with more sticky cum. I felt like I was drinking from a fire hose–was there no end to this man’s semen?
At last, he eased it out of my aching mouth and I gasped for breath, even as his cum dribbled past my lips and down my chin. Halfway down the shaft of his gigantic member, I could see a pink ring left by my lipstick.
Coach Saunders was breathing heavily and he used my head to steady himself as he swayed uncertainly. A large pearl of cum appeared at the tip of his throbbing cock and grasping his tool in his hand, he shoved it back in my warm, wet mouth.
“There’s still more to come,” he said breathlessly.
Sure enough, one last bit of ejaculate spilled onto my tongue and I dutifully swallowed it, desperate for this terrible ordeal to be over with.
“Now, kiss it and say thank you sir,” he ordered me as his chest heaved from his exertions.
Blushing hotly, I reached forward and kissed his reddened and pulsing head tenderly before looking up into his leering face.
“Thank you Sir,” I said, almost in a whisper, “for letting me suck your cock.”
“Not bad for your first try,” he said ruefully, “You’ve got a long ways to go, but I’ll make sure you get plenty of chances to practice.”
I blushed hot red as he openly humiliated me before the others and I felt I had to say something.
“But I..I don’t want to do it again,” I stammered.
“Yes you do. And you better not breathe a word of this to anyone, if you ever want to kiss my cock again–got it?”
I was both shocked and ashamed that he would make such assumptions about me but I was too afraid to contradict him. Looking up at his manly, confident face, I felt powerless to defy him.
After pulling up his underwear, he zipped up his shorts and tucked his polo shirt back in.
“If you’re good, maybe I’ll let you have some more cock tomorrow,” he snorted as he turned to go.
I wiped the cum off my chin resentfully and licked my lips to get the last of it. Was this what it was going to be like for me at this school? I felt so used and the shame I felt was crushing me like a boulder. My face burned hotly even as I licked my lips of the last bit of his salty cum and swallowed it as Joshy watched me closely.
I wanted to shout at him that I wasn’t a cocksucker and that I’d been forced to do this against my will. But somehow, I felt my explanation would fall on deaf ears.
The coach gave Sarah a peck on the cheek and he left us without a further word.
I still couldn’t believe what just happened. I could still taste his slick cum coating the inside of my mouth and I felt so violated and humiliated. Why had he picked me over Joshy, I wondered?
“Now that you’ve had your lunch, it’s naptime for you sissies,” Sarah announced as the door closed.
The other two were still looking at me and I blushed in embarrassment, wondering what they must think of me, a prissy sissy who had willingly swallowed so much cum.
Sarah escorted us to our cribs and helped us in, before shutting out the lights and leaving us alone.
Clutching my soft teddy bear to my chest, I looked out the short distance between my own crib and Joshy’s. He was still watching me and I sensed he wanted to talk to me badly.
“Gosh Chrissie, that coach sure has a big wiener, huh?” he said breathlessly. “I’ve never seen anything so big!”
I sighed heavily as I lay against my pillow, still ashamed at what just happened.
“Have you ever seen a penis that big? I can’t believe you even got it in your mouth.”
Was that a trace of envy I was discerning in his voice?
“I didn’t want to, you know,” I snapped angrily.
“Yeah, but still…I can’t believe you swallowed all his cum. What was that like?” he asked earnestly.
“Huh? What do you mean?”
“I mean, I’ve never done–you know–had a man’s penis in my mouth…what was it like to use your tongue to please him?”
I blushed furiously at his line of questioning. He seemed to take for granted that I was a cocksucker and that I did this sort of thing all the time.
“Well it wasn’t like I was trying or anything,” I retorted defensively, “Anyway–he made me do it–I didn’t want to do it.”
“Was it hard to swallow all that cum? It looked like he really came a lot,” he said excitedly.
For a moment, I just stared at him, wondering if he could see how red my face was.
“You don’t mind me asking do you Chrissie? We’re best friends–remember?” he entreated.
“I thought I was going to drown,” I replied honestly, “I was swallowing as fast as I could.”
“I wish he would have picked me,” Joshy sighed longingly, “I would have taken longer, just so I could savor the feeling of having his big wiener filling my mouth….Do you think he’ll let you suck him again?”
“I don’t want to suck him again!” I tried to explain, “I’m not gay or anything!”
“Yeah but still,” he repeated, ignoring my response, “I would love just to kiss his tool…” he sighed again like a star-crossed lover, “And you had it all in your mouth! I’m sooo jealous!”
I shook my head in consternation.
“What did his cum taste like?” he pressed.
“I don’t know,” I said in exasperation, “I can’t describe it.”
“I wish he would have picked me,” he said, his voice heavy with desire and regret, “but I know why he picked you–it’s cause you look like a real girl.”
The way he said it sounded so petulant and accusing, a surge of anger burned inside me.
“No I don’t!–You do,” I replied in a snotty fashion.
“Oh no, did you see how quickly he picked you? It was because you have those girly legs and pouty lips…any guy would want to have you.”
I sensed jealousy and resentment from him but also genuine admiration and it made me stop and think for a moment. Did guys really look at me like that? Was I desirable and sexy to some of them? The idea of having sex appeal made me feel strangely excited and to my surprise, I felt my own penis starting to harden.
“Do you mean that?” I asked tentatively in a whisper.
“Oh yes Chrissie–you’re so lucky. Guys like me have to really try hard to be prissy and femmy but you’re a natural. That’s why I couldn’t resist kissing you when I first saw you.”
He sighed again and leaned back in his crib.
“I guess I have a sissy crush on you, Chrissey,” he admitted.
I was lost in thought as I contemplated being the focus of lust and desire for a segment of the male population….what would that be like, I wondered to myself.
Suddenly, the door opened and Sarah thrust her head in, a shaft of bright light shining upon our cribs.
“Do I hear talking in here?” she demanded accusingly, “Because if I hear one more peep out of you, you’ll both be taking a visit to Mrs. Sterne’s office.”
We cowered in our cribs and tried to act like we were sleeping, fearful she might not wait for any further provocation.
At last, without another word, she stalked out of the room.
I closed my eyes and thought further about the notion of being pretty and desirable, an unfamiliar feeling to be sure.
I woke up some time later to find the lights were still turned out in the Nursery. Everything was quiet, although I could hear faint, indistinct sounds from one of the classrooms nearby.
I became instantly aware of the cool, clammy embrace of my diapers pressing against my hips and buns. With my hands, I made a furtive investigation which quickly revealed, to my utter dismay, that somewhere in the course of my nap, I’d completely soaked my diapers. Why hadn’t I woken up??
Worse than that, the clinging rumba panties Ms. Taylor had dressed me in combined with my plastic panties to ensure the sopping wet cloth remained annoyingly and persistently pressed against my skin. I tried rolling over and assuming several different positions but it made no difference–these wet diapers were going to continue to remind me of my incontinence no matter what I did.
Just then, the door opened and Ms. Taylor strolled in airily, a pleasant smile on her pretty face. Clicking on the light, she came over and reached into Joshy’s crib, squeezing the thick seat of his diapers.
“I don’t know why I even check you anymore,” she said, smiling with mock irritation, “Your diapers are always soaking wet after naptime.”
Joshy giggled merrily as he looked up at her shyly.
Rising out from under the baby blankets, I gripped the wooden rail of my own crib as I waited impatiently for her to come over to see me. I felt so childish, my own pee-soaked diapers clinging stubbornly to me–a clear example of my own lack of self control. I had wanted so badly to make a good impression on Ms. Taylor but it was clear she saw me as nothing more than a big baby and I knew this would only confirm it.
The day’s humiliations came rushing back at me as I re-lived the shame of having Coach Saunder’s big cock rammed in my mouth, and along with my unexpected accident, it was all too much for my fragile ego.
A sob quivered up through my throat and my lip trembled as I fought back a flood of confused emotions.
“I-I wet m-my diaper!” I wailed miserably.
Tears tumbled down my cheeks as Ms. Taylor’s gorgeous face transformed into one of heartfelt sympathy.
“Ohh, my poor little sissy girl!” she exclaimed as she came over and swept me up in her arms. Resting my head on her soft, bare shoulder, her slim hand reached back and squeezed the saturated thick seat of my diapers.
“Oh my yes–you’ve really soaked yourself haven’t you?”
Unable to speak, I could only sob incoherently as I buried my nose into the fragrant softness of her hair and neck, luxuriating in the wonderful scent of her perfume.
“Don’t you worry, little Sugarplum, I’ll get you all changed and into a nice dry diaper in no time.”
I felt a little relieved, albeit embarrassed but I was happy to have her focusing her attention on me as she opened my crib and let me out. I sniffled and and waited helplessly as she turned to Joshy’s crib and opened the side rail as well. I watched in indignation as she led the simpering sissy over to the changing table and sat him down with the obvious intention of changing him first. My impatience getting the better of me, I stamped my feet and shook my fists in frustration.
“But I need my diapers changed!” I whined urgently.
Ms. Taylor turned to me and she bent over slightly to grasp my pink rubber pacifier in her elegantly manicured hand. Momentarily transfixed by her sexy adult cleavage, inches in front of my face, I gazed foolishly as she positioned the pacifier before my lips.
“Open up, Chrissie,” she urged me with her million dollar smile.
“Uh-uh,” I whined, turning my head away.
I didn’t want to suck on my pacifier–I wanted her to change my wet diaper!
“Open up, Chrissie,” she said, ignoring my protestations, “time for your paci…”
I didn’t like being ignored and frankly, I was tired of being treated like a two-year old.
“I don’t wanna,” I replied stubbornly and I crossed my skinny arms over the pink ruffles on my chest.
“You didn’t mind it when you had some of your gooey-goo on it–is that what you’re trying to get me to do again?” she asked with a coy smile.
I blushed hotly as I recalled what she had done to me earlier and she took advantage of my shock to push the pacifier into my gaping mouth.
“Now, its good experience for sissies like you to learn certain girl skills, like caring for babies. So today, you’re going to be my teacher’s pet and help my change Joshy’s diapers.”
I sucked my pacifier in defeat as Ms. Taylor went about her duty, first peeling off Joshy’s plastic panties and then unpinning his heavy wet diaper.
“Okay Honey, why don’t you put these in the diaper pail, okay?” she asked sweetly.
I felt a certain revulsion about touching something Joshy had peed in but my distaste vied for the frustration I felt with being taught “girl skills”.
Gingerly, I took the wet diaper and panties and carried them over to the big rubber diaper bin, holding my breath as I opened the lid. My efforts notwithstanding, I was assailed by the pungent smell of stale diapers until the lid fell back into place. I was ashamed to be a contributor to that smell and I knew it only added to Ms. Taylor’s infantile assessment of me.
She was already positioning a new stack of diapers beneath Joshy and I took a moment to stare down at his hairless crotch. His minuscule penis was caged in a similiar chastity device to mine, although his was made of clear acrylic. Still, it was obvious that it rendered his wiener just as useless and inaccessable as mine and I felt a twinge of sympathy for the smiling sissy. Joshy giggled, oblivious of my concern as he stared up at Ms. Taylor and her beautiful big breasts.
“Chrissie? Be a good little girl and go and pick out a nice pair of plastic panties for Joshy. Oh, and you might as well pick out a pair for yourself too. But if it’s not feminine enough, I’ll have to spank your bottom,” she chuckled with amusement.
I caught my breath until I realized she was just joking. Yet despite her sweet nature, I could nonetheless visualize her paddling one of us all too easily over her firm, sexy thighs.
I went over to the panty drawer and began thumbing through them carefully. To my surprise, I felt a strange tingle in my groin, and an electric buzz of excitement as I sorted through the colorful plastic panties. There were all kinds of panties, in every pastel color one could imagine although most were pink, lilac, lemon yellow, or baby blue. Several were white with pink accents and a large number were nursery print. I gazed in interest at a pink pair with designs of bunnies and blocks and three rows of playful ruffles across the seat. For some reason, as I held them in my hands, my penis throbbed in my chastity device and I felt my heart rate quicken. Selecting the pink pair for myself, I picked out a plain pair of yellow ones for Joshy and brought them over to Ms. Taylor.
“That’s mommy’s little girl,” she said brightly as she accepted them, “And now you get to put them on your little baby friend here.”
“M-me?” I stammered uncertainly. It felt weird to be getting so intimate with another boy.
“Yes Chrissie, someday you may have your own baby to take care of–pull Joshy’s panties up for him,” she instructed me patiently.
Feeling timid, I awkwardly pulled the soft panties over his feet and up his skinny legs. It took some effort, but I was able to work them over his fat, bulging diaper and then the elastic waistband was circling his waist.
Joshy hugged me gratefully as I circled his waist with my fingers to make sure all the cloth got inside the panties.
“Thank you, Chrissie,” he said tenderly in my ear and he kissed me on the cheek with affection.
“What a good little girl you are,” Ms. Taylor beamed proudly at me.
I glowed with pride at being the object of her praise and I blushed shyly, very pleased with myself.
“And now it’s time to get my Little Miss Priss changed–don’t you think?” she inquired.
“Yes, Ms. Taylor,” I said blushing.
Joshy and I traded places and Ms. Taylor began taking my rumba panties down. I was very glad to at last see my own damp plastic panties being peeled off my diaper and tugged down my legs. With a few deft movements, she unpinned my diapers and slid them out from under me. I drank in her delicious curves and pretty smile as she gently and lovingly wiped my bottom and hips with baby wipes.
“I see the cute panties you pick out,” she said with a playful wink that made my heart stop, “I’ll bet you picked them because of the ruffles and lace.”
Reluctant to say anything in opposition to this beauty, I nodded in agreement.
“Uh-huh.”
“It’s important for a prissy little girl to have cute panties–isn’t it?” she said accomodatingly.
“Uh-huh,” I said, even as I blushed.
With a new stack of fluffy, soft diapers beneath my rump, Ms. Taylor powdered and pinned them into place, her movements practiced and graceful. After pulling the plastic panties over my feet, I stood up and let her pull them up my smooth thighs. I felt a certain giddy helplessness as she tugged them up around my bulky diaper and I hugged her to maintain my balance. Every moment spent close to her was like a slice of heaven and I sighed happily as I looked up into her gorgeous green eyes.
“There you are Sugarplum,” she said as she beeped my nose, “All ready for your mommy.”
Reaching down to buckle my Mary Janes back on, the far door opened and Barbara came walking in wearing her jacket and purse. She opened her arms wide and called to me with maternal love written all over her attractive face.
“Chrissie!” she called out to me.
My heart leaped with joy and I waddled briskly over and let her swoop me up in her arms. She kissed my cheek affectionately and reached down to squeeze my thickly diapered seat.
“You’re still dry?” she asked in amazement.
I blushed hotly at her assumption that I couldn’t keep my diapers dry for any length of time.
“Uh-huh,” I admitted shyly.
“I just changed him,” Ms. Taylor clarified, deflating my balloon, “I only woke Joshy and Chrissie from their naps about ten minutes ago and she was completely soaked.”
Barbara looked down at me, with a look of knowing as she nodded in understanding. I could only blush as Ms. Taylor explained how I’d wet my diapers during my nap and was on the verge of tears just minutes before.
“But now you’re all pinned back into a nice fresh set of diapers, aren’t you, Chrissie?” she said as if that was the only thing standing between me and a happy life.
“Yes Ma’am,” I replied meekly.
“Did you have a good time today in your first day at school?” Barbara asked eagerly.
I thought back and re-lived the memory of coach Saunders thrusting his monstrous cock into my mouth and my struggle as he exploded his incredible quantity of cum down my throat. I wanted to tell her about how I was abused and at the mercy of cruel women like Sarah and Mrs. Sterne but for some reason, the words wouldn’t come. For some reason, some small part of me looked upon the coach with admiration and envy–he was the epitome of a man I would never be in a million years. Our differences were so great that I guess it didn’t surprise me that he’d treat me like his plaything. It would be absurd to think he’d look at me with respect. Perhaps a part of me felt that what he did to me was what I should expect from a man who was my polar opposite.
Still, I knew that I was avoiding the 800 lb. gorilla in the room. In some deep recess of my mind, I knew there was some secret part of me that had enjoyed pleasing him, even if I wasn’t ready to admit it, even to myself.
In any event, I merely shuffled my Mary Jane clad feet and said little about the day’s activities.
“Uh-huh,” I said without much conviction.
“And it looks like you’ve made a new sissy friend too,” she said brightly as she looked over at Joshy.
The object of her attention beamed back at her and came over to drape his skinny arm over my shoulder.
“That’s right, Ma’am,” he said enthusiastically, ” Chrissie’s my new best friend!”
“Well give your little sissy friend a hug Chrissie, it’s time to go home.”
I sighed and did as I was told. Joshy held me close and nuzzled his cheek against mine.
“Bye-bye, Chrissie,” he bade me tenderly.
“Bye Joshy,” I said in return.
At least I had one friend that I’d made today, even if he was as big a sissy as I was.
“Goodbye, Babykins,” Ms. Taylor said as she waved her hand at me like I were a toddler.
“Bye, Ms. Taylor,” I said as my cheeks reddened again bashfully.
“I’m sure you’ll have even more fun tomorrow,” she said with a wink in her eye.
That thought lingered in my mind as Barbara took my hand and led me out to her minivan for the ride home.
Chapter Seven A Birthday to Remember
Sitting in the center of the playpen in my nursery, I looked out through the mesh that made up the sides of the enclosure at the TV located on the far wall. A Barney DVD was on continuous loop and the dialogue had already become well memorized by me earlier this morning. It was Barbara’s way of keeping me “entertained” although it was starting to get annoying.
I was sitting cross legged, Indian style as I fumbled with one of baby dolls that comprised my immediate selection of toys. I was forbidden by Barbara from getting out of the playpen and what aggravated me was the ease in which I could do it, if I so chose. It would be a simple matter of stepping over the side but I didn’t dare risk it. My new mommy had an uncanny ability to know when I’d done something I wasn’t supposed to and she’d often burst into my nursery without notice. Being a woman of her word, it was rare that I didn’t find myself face down over her lap getting my bottom paddled for some infraction she’d warned me against. I knew she kept my baby monitor on continuously and if I didn’t know better, I would have believed she had a hidden cam somewhere in the room to spy on me when she wasn’t around.
It was a level of precaution that was completely consistent with the way she treated me. She didn’t trust me to even walk to the living room without her holding my hand and anytime she wasn’t doing anything specific with me, I was either placed in my playpen (I had three) or my crib. These were the places I spent the vast majority of my time and it was only broken up by events like mealtimes in the highchair and diaper changes. It was routines like these that made me resent my life under Barbara’s rule.
On the other hand, my new regime definitely had it’s advantages.
Unlike when I used to live with my mom, everything was done for me now. I didn’t have to make any decisions and there was zero stress in my life. It had always been tough at school for me, trying to live up to people’s expectations. I was never tough enough to hang out with the guys and the girls all thought I was just a big sissy. I guess in retrospect, they hadn’t been too far from the truth. Looking down at my present outfit, it was certainly hard to deny it. Barbara had dressed me today in a frilly pink and white Alice in Wonderland baby dress with a girlish gingham print and scalloped lace around the short hem. I was wearing knee socks with pink satin bows adorning the tops and my glossy black Mary Janes. She intended for me to wear the matching set of lace rhumba panties for this dress but I had slopped baby food on them at breakfast so now my pink nursery print plastic panties were on display instead.
And as I shifted my weight on the padded surface inside the playpen, I realized I’d wet myself at some time during the morning without knowing it. The triple thick layers of my diapers were warm, wet, and spongy against my buns, giving me a constant reminder why I couldn’t be trusted without them.
This seemed to happen more often than not these days–I just peed without even thinking about it and I didn’t really notice when my diapers had become wet, unless they got heavy or had had the chance to cool down. Whining came naturally to me and I found Barbara was usually pretty quick to change me unless she had something important occupying her attention. In those cases, I just had to sit there in my wet clammy diapers, waiting for when she could make time for me.
The last two weeks at school had followed closely the routine of my first day at the Francis Merrimont Boy’s School. Most days, Sarah brought Coach Saunders by who inevitably wanted me to service him like I did the first day. He was determined to give me an education, although what he wanted to teach me had nothing to do with P.E. Through his usual method of slapping, grunting, and explaining, he taught me how to take as much of his monster cock into my mouth and how to cope with swallowing his huge loads of cum which signaled the end of my lessons. It was still quite a challenge but I was getting better and more confident every day. I think even he was amazed at how much I could swallow without gagging. Secretly, that had become a small source of pride for my shattered ego.
By all rights, I should have despised him for what he was doing to me but for some reason, I just didn’t. I guess I felt oddly flattered that he picked me out over all the other sissies and in any case, it was easy to admire him for his physical looks and natural charisma. I never told Barbara about my daily oral duties but I often found myself looking forward to the opportunity to bring about the coach’s next orgasm. Being deprived of any sexual relief meant I looked for in it other ways–in this case, giving the coach the best blowjob I could.
As far as my own orgasms, I had nearly forgotten what they felt like. And perhaps it was that same lack of relief that made me so eager to please the coach. To be sure, I wasn’t getting any myself, even though I’d since discovered that the pre-cum I generated from being sexually stimulated tended to dribble uselessly into my diapers. But an hour never passed in which I thought about what it would be like to be able to masturbate like I used to.
With little else to do, I amused myself with trying different outfits on my dollie which I had secretly given the name of Priscilla. I had laid out a number of them on the floor of the playpen and I was having my own private fashion show when Barbara walked into the nursery.
“Hello Chrissie, how’s mommy’s little baby girl?” she asked sweetly.
“Hi Mommy!” I cried out, happy to have her attention. Truth was, I felt starved for attention, or at least companionship. Certainly, I couldn’t consider Barbara any kind of peer, but I did enjoy her company, if for no other reason than the fact that she was both beautiful and sexy and she seemed to genuinely love me for who I was.
As usual, her hand slipped down to squeeze the seat of my fat diapers where she discovered my wetness.
“Hmm,” she mused as she flipped up the short hem of my baby dress and pulled back the waistband of my nursery print plastic panties, “Not too wet, looks like…I think we’ll wait to change you.”
“Yes Mommy,” I replied obediently as I stared down her low cut top. Her delicious bosom was displayed in the most alluring fashion for me and I took advantage of her position to drink it all in. She was wearing a tight white tank top under a loosely fitted blouse and I reveled in her fabulous curves.
“I have a special surprise for you Chrissie,” she announced as she straightened up, “Today, you have a special playmate to keep you company.”
“I do?” I asked with amazement.
“That’s right, Honey, this afternoon, you’re little friend Matty from school is going to be spending some time with you. Maybe you can show him your dollies and show him your collection of sissy outfits. Won’t that be wonderful?”
Obviously, Barbara had never met Matty or she’d know that he had zero interest in such things. For that matter, he’d never shown any interest in me either and I felt a growing sense of apprehension at the thought of him being forced to spend time with me.
“Oh,” was all I said.
Barbara’s smile vanished as she perceived my apparent lack of interest in her proposal.
“What’s the matter, Baby–don’t you like Matty?”
“Oh yes, Mommy, but I don’t think he likes me,” I replied honestly.
“Aw, Sweety…well that’s just because he doesn’t know you yet,” she blithely assured me, “I’m sure once you two have had the opportunity to get to know each other, he’ll want to be your best little friend in the whole wide world.”
I wasn’t so sure but I didn’t say so and right at that moment, the doorbell rang.
“That must be them now,” she said, her initial excitement having returned.
Turning on her heel, she strode out of the nursery and I heard her go to answer the door. A moment later, I heard her greeting what must be Matty’s mother and then the three of them coming down the hall.
Even though Matty had seen me in my most sissyish outfits and acting like nothing more than a big priss, I still found myself blushing at the thought of him seeing me in my “bedroom” which reflected who I really was–a diaper dependent sissy baby. Here, he would be seeing “the real me” and I cringed at how he’d respond. What would he think of me when he saw how I really lived?
As the three of them entered the open doorway, I tried to hide the little dresses and baby clothes of Priscilla hoping maybe he wouldn’t see them.
“Matty–you remember Chrissie from school don’t you?” Barbara asked as she swept her manicured hand in my direction.
“Yeah,” he said sullenly. It was obvious he had been coerced into coming over here and I couldn’t help but wonder if maybe he’d even been spanked to make him more amenable.
“Chrissie? Say hi to your little playmate,” Barbara beamed down at me.
“Hi Matty!” I said, trying to put the best face on the situation. Even though I’d tried and failed to get him to like me at school, perhaps in these circumstances I could hope to influence his opinion of me for the better.
“Chrissie, maybe you can show Matty here the lovely outfits you were dressing your dollie in,” Barbara suggested cheerfully.
I groaned inwardly and wilted under her ignorance of our true relationship.
“Oh, um…it’s nothing really…” I mumbled trying to minimize my willingness to play with dolls.
Matty rolled his eyes as Barbara reached down and picked up a few frilly dresses that belonged to Priscilla.
“Aren’t these lovely?” she said as she showed them to Matty.
I blushed hotly as his brow furrowed and his opinion of me visibly sank even further.
“So tell me, Sharon,” Barbara said as she turned to his mom, “How often do you normally change Matty? Has he already wet today?”
Stifling a giggle, she shook her head.
“Oh no, Matty here is just in trainers. I’ve been threatening him with diapers if his behavior doesn’t improve but for now he’s just in trainers. He should be fine for the afternoon and if he needs to use the bathroom, he knows to ask you.”
Matty’s face showed his look of smug superiority that he wasn’t required to be diapered like me.
Barbara had a look of surprise, but she smiled down at him in admiration and nodded with understanding.
“So I’ll be back at Chrissie’s naptime to pick Matty up–he’s got soccer practice later on,” Sharon explained.
“That sounds great,” she said, “I normally change Chrissie’s diapers around two and then put her down for her nap, unless she’s been otherwise naughty.”
I blushed at her explanations of my babyish treatment which contrasted so greatly with Matty’s own routine.
Sharon said her goodbyes and then Barbara left the two of us to be alone in the nursery. I felt very awkward, having never been with Matty by myself and it was made worse by the fact that I knew he wanted nothing to do with me. Nevertheless, I admired him for being the guy I could never hope to be and I tried to think of some way to make him accept me as his friend.
“I…I didn’t know you played soccer…I’ll bet you’re really good, huh?” I asked timidly.
Matty only grunted in response. It was clear he had no intention of making idle conversation with me so I decided on a different tactic.
“Um…I don’t get why you’re wearing trainers…do you wet your pants sometimes?” I asked hopefully. If he had bladder issues, at least we’d have that in common.
“Are you kidding? I’m not a sissy like you,” he snapped defensively.
I winced inwardly but continued in my obtuse way.
“Yeah, but your wearing trainers…do the other guys on your team wear them too?”
This seemed to strike sensitive nerve with him and his cheeks reddened noticeably.
“No–of course not. I’m only wearing them because I made problems for my mom at home.”
“Ahh…” I said in new found understanding, and with a trace of pride, “Sounds just like me…my mom sent me here because I was always getting in trouble.”
I hoped he wouldn’t see through my boasting and would instead see a kindred spirit in me but he only snickered at my attempt to compare myself to him.
“I’m nothing like you. You’re a sissy and always have been. I’m not and never will be,” he replied curtly.
Even though I couldn’t help but acknowledge the truth of his words, it stung nonetheless and I felt a vast gulf between us. Yet, how I wished I could be more like him!
For a while, I remained silent, my feelings hurt as Matty trudged around my nursery, amazed and at the same time disgusted at my living arrangements.
“Man, you really are a baby aren’t you?” he sneered, “lookit all these baby toys.”
I blushed in embarrassment and stepped out of my playpen, even though I knew I wasn’t supposed to.
“Aw, that’s just stuff Barbara got me–but I don’t actually play with it,” I lied unconvincingly.
Matty’s silence told me he didn’t believe me but he didn’t even care enough to bother trying to contradict me.
“But you’re the only baby I’ve ever seen that sucks cocks,” he goaded me in a challenging tone as he turned abruptly to face me.
My face was beet red as I tried desperately to think of a way of explaining that one.
“Well…it’s not like I want to…” I replied feebly, “Coach Saunders makes me suck him off.”
Matty crossed his arms over his chest and looked at me with his superior air.
“Doesn’t look to me like you put up too much of a fight. And it looks to me like he’s got you pretty well trained,” he said smugly, “Hmm…Maybe you should try out those skills on me?”
For a moment I was speechless as I stared back at Matty, wondering what to say. Should I keep up the charade about my unwillingness to blow the coach? I didn’t think he believed any of my attempts to diminish what a sissy I was and it might even make him more hostile towards me.
On the other hand, a part of me thought this might be the one and only way I might win him over to actually start liking me.
I really wanted Matty as a friend. He had obvious charisma and I knew even under different circumstances he’d wouldn’t normally associate with me.
Taking a deep breath, I summoned what little courage I had.
“I-if you’d like…” I offered meekly.
Standing with his chest thrust out, he put his hands on his hips in a defiant and confident pose.
“Come over and unzip my jeans,” he ordered me in a cocky manner.
My heart skipped a beat and nervously, I stepped over and hesitantly reached down to unbutton his pants. I sure hoped Barbara wouldn’t decide to walk in right about now. I could only imagine how furious she’d be!
Matty pushed me down on my knees forcefully as he grinned deviously at me.
“That’s where you belong, Sissy-boy,” he told me.
My cheeks reddened again and I unzipped his jeans, pushing them down past his trainers. Seeing the Transformers design on his training pants, I stifled a giggle as I looked back up at him. He seemed embarrassed about them and he hurriedly pushed them down himself to avoid any further discussion of them. Grabbing his limp willie in his hand, he wiggled it in front of my face like a piece of sausage.
“You know know what to do with this,” he said gruffly.
His cock was not the beast that coach Saunders possessed but it was impressive nonetheless. Even though it wasn’t erect at the moment, I could see it was thick and about five inches long.
Knowing that time wasn’t on my side, I quickly stuffed the head of his cock into my mouth, swirling my tongue around the underside of it. To my relief, he responded immediately and I felt it becoming firmer as his tool began to lengthen.
I heard him exhale as he made his pleasure apparent and I began working more of it deeper into my mouth, teasing the sensitive underside with my tongue as my lips wrapped around the widening girth. In no time at all, he was fully erect and my hands went to grip the base of his tool, helping to steady my efforts.
“I can see why the coach picks you all the time,” he said breathlessly.
Judging by the difficulty he had in speaking, it seemed apparent that he was enjoying my blowjob immensely.
My head was bobbing up and down now and his hands went to the top of my scalp to adjust me to his own particular rhythm.
“I’m gonna blow my load in your mouth, Chrissie,” he said in a husky voice, “M-make sure you swallow it all.”
This was going quicker than I expected and I could sense his cock growing more firm in my mouth, like a cat ready to pounce on it’s prey.
Matty’s breath was coming in short heaves and although I couldn’t see his face, I knew it must be taunt and flushed, ready for a big climax. Certainly, this had to be making a good impression on him.
Somehow, it felt so natural to have his thick, throbbing tool slipping in and out of my mouth. I loved the taste and feel of his hard, masculine erection stretching my cheeks to capacity and I longed for him to reward me with his gooey seed.
“I…I…” he was trying to say something but was he was lost in ecstasy and I knew his moment was at hand. I prepared my throat to receive a massive load of warm, creamy cum.
Just then, at the most inconvenient moment, Barbara barged into the nursery, followed by both Matty’s and my mom, their mouths dropping open in collective shock. Matty was too far gone to put the genie back in it’s bottle and he came with a loud groan, laced with grief and dismay as he took in their stern demeanors. His cock flew out of my mouth even as he sprayed my face with a rope of his pearly semen. I gasped in panic as I gaped wide-eyed up at Barbara standing before me, her face a picture of fury.
“WHAT IS GOING ON IN HERE?!?” she demanded in a voice that set my every hair on end.
“I-I-I-um-” I babbled incoherently as my mom came around to get a better look at me.
“I can’t believe it,” she said in utter shock and disapproval, “My son is a cocksucker.”
“I leave you alone for five minutes and this is what you do?!?” Barbara screeched.
“B-b-but, I-I-um,” I stammered, trying to find words to extricate me from this terrible predicament.
A sticky glob of semen dribbled down from my upper lip and unconsciously, my tongue reached out to lick it up.
“Young lady–this is totally unacceptable behavior,” Barbara said tersely, her raging anger barely under control.
“B-bu-but…I was so, you know…I was so horny, Mommy,” I whined in desperation. I knew she didn’t like to hear that word but it was the absolute truth–I was going crazy not being allowed to cum.
“I don’t care what you were, you little sissy, that is an adult activity that you have no business engaging in. You are in so much trouble, you are going to be one sorry little baby when I’m through with you.”
A shiver of real fear rippled through me and I felt a strong stream of pee flooding into my already damp diaper. I stamped my Mary Jane clad feet in anxious trepidation.
Barbara took the few shorts steps over to my pink dresser and snatched the dreaded wooden paddle hanging up on the peg. How many times had I felt it’s painful sting on my bare bottom?
“No-no-no-Mommy!” I wailed miserably.
Waving my hands in front of me, she grabbed my left wrist harshly and yanked me over to her as she took a seat on the edge of the vinyl covered crib mattress. At the same time, Matty’s mother was hauling him over to the only chair in the room, my “spanking chair” that Barbara used expressly for that purpose. She flipped him over her lap before he could even say anything in defense and he landed unceremoniously, only a couple of feet away from me.
Even though my diapers were pretty wet, Barbara was so worked up, she didn’t even take the time pull her skirt out of the way. Instead, she jerked my plastic panties down in three quick movements and threw me over her lap.
“Pu-please Mommy!” I sobbed, “Please don’t spank me!”
“I’m going to blister your little sissy bottom–and that’s only going to be the beginning for you,” she snapped as she unpinned my diapers and pulled them back between my legs to expose my terrified, twitching buns. Looking up in panic, I saw Matty’s face with an expression I’d never seen–genuine fright. His mom had produced a large flat-backed hairbrush and I watched as she ripped his trainers off with a vengeance and threw them aside contemptuously.
“Mama! No!” he cried.
This was a side of him I’d never seen and I could tell his mom was no pushover. He was about to get spanked, and spanked hard!
I whimpered and squirmed but it did me no good.
Barbara’s paddle seared both my bare cheeks with a fiery impact and I gasped in shock, my breath momentarily taken away. She followed her first swat with another, equally harsh one right in the same exact place.
At last, I found my breath and I wailed at the top of my lungs.
“WAA-HA-HAAAA!!!”
Barbara didn’t pause and her angry paddle rained down over and over like the holy sword of vengeance, first one defenseless cheek, then the other, and then back to the first one. I never knew which one she was going to swat and I kicked and sobbed as she spanked me with a severity I’d never seen. My soft, youthful bottom jiggled and shook under the constant battering it was getting from her oaken paddle. I beat my fists on the ground, even as I saw Matty bawling directly in front of me. I struggled and squirmed trying to escape her terrible wrath but she grabbed a fistful of the back of my Alice in Wonderland dress and effectively prevented me from wriggling off.
SMACKK!! CRACKK!! SMACK–SMACKKKK!!!
My face was wet with tears and I sobbed like a baby. Not only was I upset about being caught and punished by Barbara, but I could hear Matty’s mom telling him between the harsh slaps of her hairbrush that she’d be taking him out of our school and enlisting in some boot camp, far away from me and my “bad” influence. So much for my hopes of having him as my boyfriend!
It was no consolation for me to witness his being punished and brought down to my level–my own bottom was blazing and Barbara’s paddle felt like a red hot frypan against my burning, crimson cheeks. I still squirmed over her lap but nothing prevented her paddle from scalding my soft, helpless buns.
WHACKKK!!! SMACKKK!!! SMACKKK!!!
As the tears streamed endlessly down my wet face, I knew I wouldn’t be able to sit for several days.
Finally, Barbara stopped and she held the paddle firmly as she scolded me further.
“You are NOT to play with other boy’s pee-pees!” she snapped angrily, emphasizing her point with a savage, blistering swat on my red, stinging bottom.
SMACKKK!!!
I tried to articulate my willingness to comply but I couldn’t verbalize anything through my uncontrolled, ragged sobbing.
“And I’d better NEVER find out you’ve had one in your mouth again–do you understand me?” she growled.
I nodded my head, even as more tears spilled down my cheeks. All I wanted was to get off her lap and away from that paddle!
With quick, haphazard movements, Barbara pinned my cool, wet diapers back in place although not with the usual care. With an abruptness I wasn’t used to, she stood me up and placed the paddle on my mattress. Just as quickly, she laid me down in my crib on my back and I assumed she was going to change me, although she almost always used my changing table for that.
“Don’t you move so much as an inch!” she warned me as she shook her long nailed finger at me.
Without another word, she stalked out of the nursery and into the nearby bathroom where I soon heard running water. Meanwhile, Matty was having his trainers and pants pulled back up by his mom as he stood there, crying unashamedly before me. They walked out of the room, saying a few brief words to Barbara before letting themselves out the front door.
Barbara returned with an big red enema bag bursting with hot, soapy water, except that it wasn’t my usual enema bag but a larger one.
I gulped in fear as I looked at the volume of it–and all of it destined for my rear end!
“You’ve got some very naughty ideas that someone put into your head and I’m going to flush them right out of you,” she explained as she positioned the heavy bag on a hook put into the nearby wall. I was still crying as I watched her attach a thick, penis shaped nozzle to the end and briefly test the flow. A strong squirt of water and bubbles burst out of the end and dribbled down the shaft, reminding me of coach Saunder’s semen. Then she leaned forward and unpinned my diapers, pulling the soaking wet front down and exposing my tiny caged penis in it’s chastity prison. Normally, I would have enjoyed seeing the view down her snug top but I was too frightened by what was about to happen to appreciate her big breasts.
“Since you seem to like boy’s penises, I’m going to see that you get one with your daily enema, Chrissie–starting right now,” she explained as she pushed my knees apart.
“No…no…please, Mommy,” I begged her between sobs.
Dipping the fat dildo nozzle into my Vasoline jar, she brought it down and poised it at my shy back hole.
“Spread your legs and open up Chrissie–you’re getting this whether you like it or not.”
I moaned and whined as she pushed the thick, blunt tip determinedly against my anus, using ever greater pressure as I gripped the sidebars of my crib and squirmed on the vinyl crib sheet.
“No…no Mommy,” I quailed as I felt the greasy nozzle end prodding my quivering hole looking for entry.
“OHH!!” I squealed as I lost the battle and the big warm tip suddenly slid past my sphincter.
Barbara smiled grimly as she gently pushed it further in, twisting it and easing it in as I gasped from the fullness of it.
“How does that feel, Sissykins?” she asked with a smug look, “Do you like having a nice big cock filling up your pussy?”
My face burned with shame as she slowly pushed it in and pulled it out slightly, only to push it back again until it bottomed out. Looking up at my real mom, I saw a look of immense satisfaction on her face as she watched me being impaled by this rubber leviathan.
I moaned like a little girl as I looked back at Barbara, knowing I was helpless to do anything about what was happening. She was so powerful and I was so weak, a true baby by comparison to her.
“One thing is for sure–I’m pulling you out of that school before the day’s over. It’s obvious that you’re not ready to enter a world with other boys–never mind grown-ups. I can see that I need to keep a very close eye on you. You are going to stay in this house, except for occasional, short, supervised trips outside when I need you to go somewhere. And you can bet your sweet little sissy bottom that the number of babysitters I’ll approve of is very short indeed.”
I could see my world closing in to these four walls, rarely to step outside, with my nursery becoming the center of my universe.
“Baby girls have no business playing with boys and I’ll make sure you’re never exposed to them again,” she continued.
Reaching up, she undid the clip and I felt a strong force of hot, soapy water invade my bowels.
“Uhhngg,” I wailed.
“Let that be a lesson to you,” Barbara said as she looked down into my tear-stained face.
My mom gazed down at me with a look of disapproval clearly written on her face.
“And here I thought you were behaving yourself under Barbara’s care. To think you’ve just been scheming for ways to suck other boy’s cocks…You barely made it through potty training the first time–what made you think you were mature enough to handle sex at your age now?”
Barbara pinched the clip shut and waited for the water to settle before resuming my enema.
“You are not an adult who plays with guy’s penises–you are a little baby girl–do you understand me?” she said as she glared down at me.
“Ye-yes, Mommy,” I squealed miserably.
“You are a little sissy baby who wets her diapers and likes to wear baby girl clothes,” she continued relentlessly.
“Yes-yes, Mommy,” I agreed.
I squealed and whimpered with each new surge of water, trying in vain to pinch my scalded cheeks together to try and stop the endless flow. Barbara towered over me like an all-powerful goddess, deciding when I should receive more of the enema and when I should get a break. My complaints fell on deaf ears and she continued to drain the enema bag into my puckering, protesting hole.
“My tummy’s cramping, Mommy,” I moaned as I felt the water filling me heavily.
“Good. You’re going to take every drop or we’ll just start right back over again,” she told me firmly.
“Ohhhhh,” I moaned again.
“Tell me what you are, Chrissie,” she said as she released the clip again.
“Ohhhh—I-I…(gulp) I’m a sissy baby g-girl,” I admitted.
“Are you ever going to put another boy’s penis in your mouth again?”
“N-no-no, Mommy,” I whimpered, “ohhhhhh.”
Taking her time, Barbara manipulated the clip, allowing more of the water to flow into my helpless back passage as my sphincter gripped the massive rubber nozzle tightly.
I had never taken this much water before and I felt ready to explode.
“Well now,” Barbara said with a wicked smile, “When I take this out, you’re going to go back over my lap and I’m going to finish your spanking. Are you ready Little Miss Priss?”
“No–no…” I whimpered weakly.
“Okay, I can see you need some more soapy water,” she said as she released the clip again.
“Noo!” I cried as I squirmed helplessly, “I’m ready–I’m ready!”
Barbara snapped the clip shut and gripped the fat base of the rubber nozzle.
“Alright Sissy, I’m going to pull this out and if you spill one drop, just one drop, I’m going to push it back in and we’ll resume where we left off.”
I cried softly as she gently pulled the mammoth dildo from my anus and set it aside. I wheezed and moaned as the large rubber head slid past my sore, protesting hole but I pinched my cheeks together, desperate to prevent any loss of liquid. Pulling my wet diapers back up, she pinned the clammy cloth together which made for an unwelcome embrace of my hips and burning cheeks.
Looking around, she located my plastic panties that had been kicked aside when she was spanking me earlier. Gathering the leg holes together, she worked them over my Mary Janes and up my slim, hairless legs.
Pl-please–please don’t spank me,” I begged her weakly but she ignored me as she worked the clinging nursery print plastic panties over my soggy diaper.
Helping me to my feet, I swayed uncertainly and sniffled, the heavy liquid cramping uncomfortably inside my bowels.
“Chrissie, you were a very, very naughty little girl today. This is what happens when you disobey your mommy,” she said in a calm, rational voice.
“Please…” I whimpered as she lowered me over her lap.
Taking the paddle in her hand, she rubbed it against the smooth plastic of the baby panties covering my bottom.
“Let this be a lesson to you next time you try and act like an adult,” she said evenly.
The paddle swooped up and then came down again with a loud splat against my diapered rump. The thick cloth did much to alleviate the stinging impact although the conditioning she’d already done pretty much cancelled any advantage I had there.
Again and again, she swatted me harshly and once more, I burst into fresh tears. Not only did the slaps of her paddle really hurt, I was losing control of all that water trapped in me. Slowly at first, I felt it leaking inexorably out of my hole but what started as a trickle soon turned into a messy deluge. It gushed out even as Barbara’s hard paddle slapped my spongy, expanding diaper. I wailed miserably as the sludgy fluid emptied in a flood against my punished cheeks and was quickly slapped hard and flat against my skin. Eventually it seeped down my front and I cringed against the disgusting mess.
Beating my fists on the floor, I wailed and cried in helpless frustration.
Finally, the humiliating spanking was over and Barbara set my paddle down on the mattress in front of me. Helping me to my feet, she stood me up and wrapped her arms around me, hugging me close. Hot tears of pain and remorse spilled down my cheeks and onto the soft skin of her bosom where they disappeared down the front of her blouse.
She began shushing my crying and kissing me gently, telling me my punishment was finally at an end.
I felt completely defeated by this buxom, authoritarian woman but at the same time, strangely, I felt a closeness I’d never felt with anyone else. I knew that as strict as her punishments were, she really cared for me and wanted what was best. As she pushed my fat pink pacifier into my mouth, I looked up into her beautiful eyes and I knew she was right. I hugged her tightly and she kissed my forehead lightly.
“It’s all over, Chrissie,” she assured me, “Mommy loves her little baby girl.”
I felt like a very messy baby and my buns twitched as the warm, sticky material of my diapers clung tenaciously to my scalded rump.
“Okay, it’s time to get you cleaned up and into a fresh set of diapers, Sweetie-pie,” she said as she guided me to my changing table.
Much as I enjoyed having Matty’s cock in my mouth, I knew I’d never risk it again while under Barbara’s roof. However it was that she did it, there was no escaping her constant, omniscient attention.
For the better part of the next fifteen minutes, Barbara cleaned the nasty mess of my diaper area before declaring me ready for my change. Taking a thick stack of soft, fresh diapers, Barbara positioned them under my still stinging buns.
“This is what all sissies want, don’t they Chrissie,” Barbara asked of me.
“Yes, Mommy, I just want to be back in my diapers again,” I admitted weakly but truthfully.
“It’s what you need, isn’t it?” she prodded as she sprinkled fragrant baby powder all over my caged loins and chest.
“Yes, Mommy,” I replied deferentially as I breathed deeply of the baby powder. And in fact, I knew all too well I couldn’t last an hour anymore without helplessly wetting myself. Like it or not, I was going to need diapers and plastic pants for the forseeable future, if not forever. Barbara gently pulled the pillowy soft cloth of my diaper and as I continued to sniffle, I reflected on how much I’d come to love this ritual of ours. Barbara was always so tender with me, making sure she never pricked me with the diaper pins and as she lovingly pulled the cloth snug around my hips, I adored the soft, comforting embrace. I felt so secure, not only because it protected me from accidents but also because the whole process made me feel safe and sheltered from harm. No bullies would ever taunt me again so long as I lived under Barbara’s roof and in her care. All I wanted was to be her little toddler.
After pinning my comfy diapers closed, Barbara took a pair of cute polka dot side snap baby panties and pulled them over my feet, working them up my smooth legs to enclose the bulging cloth within. While Barbara was cleaning and diapering me, she was also discussing some related matters with my mom.
“So Pamela, how have those hormones been working out for you?”
“Oh, faster than I expected,” she said excitedly, “As a matter of fact, I think I’m ready to give Chrissie his first wet nursing in ten years.”
“Ten years?” Barbara asked quizzically, “How long were you breastfeeding Chrissie the first time?”
“Oh, until he was four years old, at least,” she admitted, “He’d cry and fuss whenever I tried to give him a bottle and it took forever to get him weaned.”
“I can so easily imagine that,” Barbara nodded.
She picked me up and gently led me over to the love seat where my mom was already sitting.
“Now there’s just one thing, Pamela,” Barbara hedged, “You really shouldn’t think of Chrissie in those masculine terms anymore.”
“Ah yes,” she remembered.
“There’s really nothing left of “his” boyhood to justify terms like ‘his’ or ‘him’. And it’ll only become more so as time goes on. When I locked up her little penis, she soon learned that she wouldn’t be able to act sexually as a boy anymore. And as you’ve unfortunately already observed, Chrissie feels naturally compelled to please other boys with her mouth. I’m sorry you had to see that, but I guess I should have seen it coming. As time goes on, she relates more and more to her feminine side and I’m doing everything I can to encourage it–With the exception of letting her have sexual relations, of course,” she added quickly.
“Of course,” my mom repeated, “I’m in complete agreement.”
Pouting in frustration, my lower lip puffed out a typical sissy display of displeasure.
“You see these things so clearly,” my mom gushed in admiration for Barbara, “Looking back in retrospect, I don’t know why I didn’t see it myself. I almost feel guilty for trying to raise him–I mean her, as a boy. It’s obvious to me now that she always wanted to be a little sissy girl and the diapers and baby treatment are the crowning touch. You were right all along.”
“Thank you,” Barbara replied gracefully, “My little buttercup here knows that she just wants to be mommy’s little baby girl now–don’t you Chrissie?”
I nodded in acceptance of her truth.
“I’m just so impressed by the transformation you’ve made–and it’s such a relief to be free of her whiny, pestering tantrums.”
“The only tantrums our little baby has anymore is whether she has creamed corn or spinach for dinner,” Barbara chuckled with amusement.
My mom giggled, even as she marvelled at Barbara’s complete authority over me.
“How about we have Chrissie take her lunch directly from her former mommy now?” Barbara suggested.
My mom smiled down on me happily as she opened her blouse to reveal her swollen breasts. They had obviously grown quite a bit since I last saw her and now I understood the reference to the hormone treatment. The wet spot on her bra confirmed my suspicions. My mom was actually lactating again!
“Come on now, Chrissie, show Mommy what aunt Barbara has taught you,” she said as she brought my head up to her dribbling nipple.
I was distinctly uncomfortable with the notion of breastfeeding from my real mom–after all, my previous desire with Barbara had been borne out of my lust for her fabulous bosom. I harbored no such feelings for my mom.
“Uh-uh,” I whimpered as I pulled my face away.
“Chrissie,” Barbara admonished me in a sharper tone, “You know better than to act like that.”
“But I don’t wanna,” I whined pitifully.
“In situations like this, it’s better just to take the intitiative with her–just push your nipple into her mouth and she’ll begin nursing,” Barbara coached her.
My mom complied willingly and brought my face up until her dripping nipple was brushing between my lips.
“Open up, Chrissie,” she instructed me.
With a small slap on my bare thigh, Barbara caused me to yelp and open my mouth which my mom quickly filled with her engorged nipple. My mouth clamped down and I accepted her breast, albeit unwillingly.
“That’s better,” Barbara commended her, “she needs to understand that the choice isn’t hers and that this isn’t sexual in any way–it’s simply a mother giving her the nursing she needs.”
“Mmm…yes,” my mom concurred as she looked down at me with happiness written all over her face.
“This is right where you belong, Sweetie,” she told me, “Now you’re the baby I always knew you were.”
I whimpered helplessly as I drank in the slightly different taste of my own mother’s milk.
Although she wasn’t as endowed as Barbara was, she still had a considerable quantity of milk to provide. I was nearly full when she switched me over to her left breast which I took with less resistance than previously.
“Thaaat’s mommy’s baby,” she cooed down at me.
I blushed and realized that perhaps more than anything else, my mom’s acceptance and encouragement of my new baby status was perhaps the final nail on the coffin of my boyhood. But somehow, it no longer distressed me. Two months ago, I would have agonized over being called a sissy by the girls at school. Now, I realized it was the truth–not only that–but I enjoyed being a sissy baby. Deep down, under the thin, fragile veneer of my maleness, I knew a prissy, feminine sissy had always been there, waiting to come out. And Barbara had known right from the beginning. I felt a fresh surge of affection for that woman, who even now was looking down on me with her overwhelming maternal love.
I had finished my mom’s other breast and was now full and ready for my nap but Barbara slipped in next to my mom on the loveseat and she began moving me into position over her lap.
“No…no, Mommy,” I whimpered weakly as I saw belatedly what she had in mind.
With her lovely, creamy fingers, she deftly unbuttoned her straining top to expose her big, beautiful breasts.
“Here you are Chrissie, time for more nursing,” she smiled down on me.
“Uh-uh,” I shook my head, “I’m full,” I whimpered.
She shushed my pleading with her gorgeous smile even as she guided my face towards her left breast.
“Baby girls need looots of milk, Chrissie,” she told me as she unclasped the front of her lace bra, “And I’m going to make sure you get it.”
“Uh-uh,” I squealed but as usual, Barbara only ignored my protests and pushed her big, firm nipple past my lips. Even though my stomach was sloshing uncomfortably with milk, I began nursing by instinct, using my lips and tongue to suck the warm, familiar milk from Barbara’s bursting breast.
“That’s it, Sissy,” she smiled, “Baby doesn’t decide when to nurse–Mommy does.”
Looking up over the soft upper curve of her tremendous bosom, I looked into her pretty green eyes which glittered with firm, motherly love. And now that I was suckling from Barbara’s breast again, I felt my sexual desire starting to rise, if not my penis.
Barbara’s hand had shifted to the soft, cushiony front of my diaper and she was softly rubbing it now. I could hear the plastic crinkling under her touch and feel the wonderful sensations reaching me, even though my wiener was completely enclosed in it’s silicone cage. Closing my eyes, I drifted off into a world of pleasure as I luxuriated in Barbara’s delightful ministrations. As I continued to slowly nurse from her plump breast, she reached down and began unsnapping the side snaps one by one on my plastic panties. My heart skipped several beats as my mind began racing at the possibilities of what she had in mind, her beautiful smile washing over me like a warm bath and before long, I felt her unpinning the front of my diapers.
“Baby Chrissie needs her mommy, doesn’t she?” she whispered in her voice reserved for infants.
“Mm-hm,” I mewled as I sucked on her sweet, firm nipple.
She slowly pushed the front of my diaper down between my legs and began softly stroking my hairless balls in the most electrifying fashion imaginable.
“You know you’re always going to be my baby, don’t you Sugarplum?” she asked.
My heart was pounding in my chest as I looked up into those twin pools of emerald comfort. I nodded fervently back at her in reply.
“Now…real babies don’t get to have orgasms, you know that right, Chrissie?”
Huh? My head was swimming with desire and confusion. On one hand, her soft, slow caressing of my balls was driving me wild with sexual excitement. And as usual, the sight of her luscious, big breasts against my face had me already up against the edge of what would otherwise be a powerful orgasm. Her skin smelled wonderful and the silky smoothness of her bosom only added to her powerful attraction. But I felt a strong desire to be agreeable with her, in what I only now realized was a deep seated streak of submissiveness. Worse than that, my pounding, sexual excitement was pushing me against my will to agree with her terrifying premise.
Slowly, and contrary to my better judgement, I found myself nodding in agreement.
From behind her, I saw her reach over and when her hand came back into view, it was holding a small tube of superglue. She looked down at me with that warm, loving smile that said she’d never do anything to harm me.
“Now you know that I know what’s best for you, right Sweetie?” she murmured in her syrupy, sexy voice.
I paused, my heart thudding loudly in my chest, before slowly nodding.
Barbara bent down and kissed me tenderly on the forehead as her hand softly and sensuously stroked my excited balls. Inside my tube, my little penis throbbed violently against it’s implacable prison, fighting frantically for release.
“Sooo…” she began breathlessly, “I think it’s only for the best that I fill the keyhole of your chastity lock with this glue…what do you think, Chrissie?”
I could feel the cum building in my balls, waiting impatiently to explode in a massive ejaculation of climax. But by some perverse twist of biology, my own burning libido was encouraging me to go along with her. How could I say no to this beautiful woman I was in love with? My submissiveness was warring with my desire to achieve sexual release. I couldn’t think straight! And her sensuous massage of my balls wasn’t making it any easier!
Slowly and deliberately, Barbara pulled my puckering lips from her milky breast.
“Say ‘yes mommy’,” she smiled down at me.
“Oh–oh–bu–but,” I whimpered.
“Say ‘yes mommy’,” she repeated as she unscrewed the cap of the dreaded superglue.
“M–m–mommy,” I mewled weakly.
“Say ‘yes mommy’,” she said again as she leaned forward to bring her beautiful face closer to mine. Her rose colored lipstick shimmered in the soft light of my nursery and I felt my resolve crumbling.
I looked from the long line of her sexy cleavage, to the delicate lace cups of her bra, and then lastly, into her firm, pretty green eyes that were imploring me to agree to something that went against everything I knew.
“M–m–m…y-yes, Mommy,” I croaked in barely a whisper.
She smiled broadly and placed the thin nozzle of the tube of glue to the keyhole on the lock securing my chastity device. With a small squeeze, I watched in mute horror as the glue seeped into the lock effortlessly, quickly filling the tumblers and rendering them unable to open ever again. In seconds, I saw the glue glaze over the hole as it inexorably began to harden.
What had I done???
“Now you’ll be my baby girl forever, Chrissie,” she said as she gave me a warm, wet kiss right on the mouth.
The End
Posted in My other stories... | Tagged Chastity, Diapers, Femdom, Humilation, Spanking | Leave a comment