CHAPTER THREE
Later that night, Timmy tossed and turned in his crib, horny, frustrated, and unable to sleep.
After having struggled for hours in his attempt to defeat the chastity device, he finally gave up and fell into a fitful sleep from his exhaustive efforts.
His first attempts had focused on trying to everything he could to extricate his pen-is 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 circ-umstances, 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 dil-do.
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 suc-ked 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 pen-is 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 pen-is 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 suspicions.
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 suc-ked 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.