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…
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.
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.
…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.
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.”
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…
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.
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.
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.
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.
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;
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,
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…”
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.”