The Perverse Revenge of Miss Hazel

[Baby Bobby]

"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 suc-kle 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 pen-is 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 pen-is throbbed urgently inside his chastity tube.
He tried to satiate his gnawing sexual need by suc-king 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 suc-ked 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 coc-k 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 pen-is 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 dil-do 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 coc-k jutting obscenely out 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-fuc-king, 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 dil-do, 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 dil-do 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 dil-do 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 dil-do 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 coc-k 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 pen-is 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 dil-do 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.

[Baby Bobby]

                                CHAPTER SEVEN
                       

It was Saturday morning, and Gina carried the warmed baby bottle of milk in her hands as she slipped quietly into Timmy's nursery. Gazing down upon the angelic boy, she sighed with happiness as she watched him peacefully suc-king 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 circ-umstances 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?"

[Baby Bobby]

"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 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.

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 circ-umstances 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 circ-umstances 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.

[Baby Bobby]

                                      CHAPTER EIGHT                       


Lunch time was always a wet, squishy affair for Timmy.

By noon, it would have been several hours since his last diaper change and by the time Hazel lifted him up and strapped him into his highchair, the soggy cotton cloth inside his plastic panties was almost always completely saturated.
His lunch was inevitably accompanied by the distinctive smell of pee wafting up around him as Hazel spoon-fed him his baby food.

But today, Timmy was feeling edgy and anxious. It had been five days now, since he'd had his unexpected, albeit very welcome orgasm, and as a result, he was hornier than ever. Indeed, having experienced it once, he wanted some sexual relief now, more than ever. He felt like a shark that had tasted blood--he had to have more!

Hazel certainly wasn't making things easier for him. Sometimes, he felt she dressed provocatively just to torture him. This morning, she had chosen to wear a sheer white top that did nothing whatsoever to hide her lacy pink push-up bra underneath. Timmy had swallowed hard when he got his first good look at his stunning babysitter. Her big, beautiful breasts pushed defiantly against the thin, filmy fabric of her top and the poor befuddled sissy couldn't think straight.

He was further confused by the volatile cauldron of mixed emotions swirling around inside of him. Was it his budding love, that made him feel certain that there was something significant going on between them? Hadn't her kiss on Friday said as much? Oh, how he longed for another chance to touch her full, succulent lips again.

However, right now, his libido was winning out between his two polarizing desires. He wanted to touch Hazel's big sexy breasts like there was no tomorrow! Just one touch--one chance to feel how big and soft they were, to feel their weight in his hands.

After lunch, she had taken him down the hallway to his nursery, making cheerful small talk with him. She seemed to be in good spirits, and her breathtaking smiles melted whatever paltry resistance Timmy might still have harbored.

Climbing onto his low, vinyl covered changing table, Timmy arranged himself on his back for her, as Hazel began peeling his cute ruffled plastic panties down off his sopping wet diapers.
Timmy bit his lip as he gazed longingly at his babysitter's incredible bosom, blatantly and openly displayed before him.
She looked so sexy today, with her silver hoops dangling from her delicate ears and her eyes looking playfully down upon him.

Watching as her heavy breasts swung within her top, Timmy could feel his little pen-is 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 moment's his small hand cupped the massive cup containing her magnificent bosom.

In an instant, the smile vanished from Hazel's pretty face and she drew back angrily. Her eyes flashed darkly and her features hardened with furious indignation.

"You-do-NOT-touch-my-breasts!! Do you understand me?!?" she snapped.

Timmy's mouth opened in shock and he began stammering incoherently, fumbling for some way to placate the gorgeous teen.  In an instant, Hazel reached down and grabbed the wooden paddle that was laying next to the crib. With her left hand, she gripped Timmy's flailing ankles together and in a flash, swung them high over his head. At the same moment, she brought the paddle down viciously, swatting his exposed baby bottom hard enough to make his whole body buck.

Timmy shrieked in agony as the wooden instrument of correction came down again and again in a blurry arc, slapping his soft, tender cheeks and leaving them a scalding color of crimson. His loud, piteous wails filled the nursery as he struggled wildly against Hazel's iron grip of his ankles. He felt utterly helpless, and all he could do was to desperately grip the sides of the changing table as she vengefully smacked his bare bottom repeatedly.

How could he have miscalculated so terribly wrong? He had been dreaming of her all weekend, pining for her, and now that Monday had arrived, she had seemed to confirm his feelings of affection.
And yet, now she was holding his ankles up high and blistering his bottom with her paddle again.

Timmy's hot tears flowing like a river and he repeatedly slapped the surface of the changing table in bitter, angry frustration.

Although Hazel looked to all outward appearances to be boiling with rage, inside, she gloated with immense satisfaction. She had purposely dressed as scantily as possible, hoping to goad Timmy into making an inappropriate move that would cross the line. Her kind-hearted friendliness this morning had only fed into the deception, lulling the sissy boy into thinking he could have his way with her.

And now, he had given her the perfect excuse to paddle him hard--something she hadn't done in at least a week. Gripping his ankles tightly, she looked down into his red face and crying eyes as he sobbed loudly and wriggled in her hand, unable to escape her cruel, avenging punishment. The sight made her loins wet, and her focus went back and forth from his distraught face to his blazing red bottom. She loved the sight of his pink butt plug, the rubbery base visible just between his scalded red cheeks. With renewed vengeance, she smacked him again and again.

She paused only long enough to angrily scold him.

"You--"

SMACKK!!

"Are never--"

SMACKK!!

"To touch--"

SMACKK!!

"My breasts--EVER!!"

SMACKK!! SMACKK!!

She emphasized each word with a blistering swat of the paddle.

Hazel could feel her juices dripping down the inside of her thighs and she knew she couldn't wait any longer.

With an abruptness that left Timmy gasping, Hazel simultaneously dropped his ankles and the paddle and picking up her strap-on harness, deftly stepping into it, and raising it up around her firm legs. Timmy had barely any time to register what was happening as he sobbed uncontrollably and his hands instantly shot down to rub his stinging hot, swollen cheeks.

There was an armless stool in the room, the same one Hazel used to sit on when she administered Timmy's enemas, and after securing the various straps of her dil-do 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 dil-do 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 dil-do 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 dil-do 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 dil-do), 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 dil-do 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 dil-do 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 pen-is 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 dil-do, 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.

[Baby Bobby]

                         CHAPTER NINE


Michelle set her Starbucks cup down on the kitchen table along with her purse as Hazel was picking up her car keys.

"Thanks so much for coming over, I'm not sure how long I'll be gone, and Timmy just can't be left alone--like any toddler still in diapers, he really needs to be supervised at all times," Hazel explained to her well-endowed, older friend.

"Oh--its my pleasure. I think he's adorable and I know we'll have all kinds of fun today," Michelle told her with a gracious smile, "And besides, since my little girl at home is no longer breastfeeding, my poor boobs are aching and full."

She emphasized her point by hefting her big breasts in her small hands.

The two laughed together although they purposely kept their voices low, so as not to wake Timmy.

"What time do I get him up?" Michelle asked.

"Anytime is good," she replied, looking over at the clock on the wall, "Now is when I usually do it."

"So where are you off to today?"

"Remember that nerdy guy from our science class...Francis Kendall?" Hazel asked her.

"Mmm, vaguely...he was someone I pretty much ignored throughout High School."

"Well, I'm going over to his place to see him today. He thinks he has a date with me...little does he know, he's got an appointment with my Spencer paddle," Hazel emphasized her remark by pulling the familiar wooden paddle out of her purse and gesturing with it.

Michelle giggled uncontrollably.

"Hazel, I swear," she chuckled.

Her haughty friend smirked, "He thinks I'm coming over to make out with him but when I'm through with him, his ass will be sore inside and out. I love taking weak sissies down a few notches."

Michelle laughed again. She could easily imagine the frail, shy boy she remembered from High School, forcefully bent over a sofa, his red, spanked cheeks on display, as Hazel pounded him mercilessly with her fat strap-on dil-do.

"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-suc-king 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 suc-king 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 pen-is 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.

[Baby Bobby]

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 dil-do 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 pen-is 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 dil-do nozzle in to the hilt.

"Ohh!!! Y-yes, ma'am," Timmy agreed submissively. He just wanted this emasculating enema to end.

"Is it hard being a chaste sissy boy in diapers?" she asked, "Aren't you horny all the time?"

"Uhh--ohh, y-yes, m-miss Michelle," Timmy stammered, "Its-its very hard."

She chuckled as she toyed with the clip in her hand, debating just when to open it again.

"But then--I guess you can't very well get hard--can you?" she laughed light heartedly as she reopened the clip.

Timmy wanted to say something, but his response was cut off as he suddenly moaned again from the urgent flow of soapy water surging deep into his bowels.

"I know--I have a great idea!" Michelle said as if she'd suddenly had an epiphany, "I think it would be a great idea if you were to write your mommy a little thank you note. You know--you could explain to her how smart and thoughtful it was for her to lock up your little pee-pee into a chastity device and prevent you from being able to play with yourself.
"After all, we both know when little sissies are left to their own devices--these bunny soft, fluffy diapers prove to be too much for a pretty boy like you to resist, don't they?"

Timmy blushed furiously--how could she have known him so well? It was like she could read his mind!

"N-no..." he moaned weakly, but unconvincingly.

"Big boys deserve to have orgasms, but we both know you aren't a big boy, are you? You're just a big sissy in diapers. And bedwetting sissies don't have any need for erections, do they, Timmy?"

"Ohh---no, m-miss Michelle," Timmy moaned as the cramps hit him full force.

"No...we both know you're a cute little baby bedwetter that can't keep his pampers dry," Michelle said as she slowly slide the slippery enema nozzle out.
Thinking he was finally free to release his punishing load, Timmy tried to rise up, only to find himself still being held in place by his beautiful, busty babysitter.

"Oh no, Timmy...not yet..." she said as she slowly pushed his pink rubber butt plug back into his protesting hole, "I think you need to write your mommy a nice little note right now, thanking her for all she's done and putting you into chastity where you belong."

Timmy winced and swallowed hard. He really had to go!!

"Please!" he begged her pleadingly, "Please let me go to the bathroom."

Michelle helped him up, but only to gently place him down onto his changing table.

"No baby--it's diaper time now, little Timmy, and then you can write your mommy a nice note thanking her for her thoughtfulness."

Timmy moaned weakly as she set him down on a thick stack of diapers, pulling them up between his prissy legs and pinning them snugly together with some yellow baby pins. Taking a nearby set of pink rubber panties, she swiftly pulled them up over his feet and legs, carefully positioning them around his fat, bulging diaper.

"Come on, Timmy," she said as she led him over to a low table with crayons, "The sooner you write this--the sooner I'll let you release your enema."

The teenaged sissy sobbed a little as he weakly made his way over, waddling awkwardly, the soapy suds churning achingly inside his belly. At the same time, his pink butt plug was buried deep into his back hole, stubbornly preventing any of his enema from escaping.
Michelle found a blank sheet of pretty pink drawing paper and set it before him, selecting the crayons she wanted him to use.

"Okay, I'll dictate it, and you just write, okay?" she told him.

Timmy groaned again as another cramp hit him.

Michelle stroked her delicate chin thoughtfully as she slowly paced the room.

"Let's see...okay--write this;

'Hi Mommy,

I know this is overdue, but I just wanted to thank you so much for finally putting me into a secure, tamper-proof chastity device. You see, I was finding that the older I got, the more my soft, fluffy diapers were proving to be a dangerous temptation for me. I was playing with myself every chance I got and I couldn't stop myself!

Thank you so, so much, for making the decision to lock up my naughty little wee-wee. I had become a chronic masturbator and I needed a chastity device to make me be a good little girl again. Sissies like me don't have any use for erections, so a secure chastity device was the perfect solution.
Now I stay nice and soft--just like a little baby girl should!  :)

I know that you did it out of true, maternal love, just like I love you mommy.

Your prissy baby girl,

Tammy

XOXOXXO' "
 
Timmy was writing furiously to keep up with Michelle's dictation and the end result was a sloppy, childish mess, barely legible to read. The use of crayons only added to it's infantile appearance but Michelle was clearly very happy with it.

"What a good little girl you are," she exclaimed as she patted him on the head patronizingly, "Okay, you can go release your enema now."

Timmy half waddled--half limped out of the nursery, going as fast as he could to get to the bathroom.

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

Michelle heard the bathroom door open and Timmy coming back down the hallway.

"Come along Timmy, its time to get you dressed. Your diapers are waiting for you," she told him.

Timmy walked into the room, his eyes downcast and shyly covering his little pink chastity device as he regretted the note Michelle had forced him to write.

"What a good little girl you are," she commended him again patronizingly, "Did you make poo-poos like a good girl?"

Timmy blushed and nodded his head.

She patted him on his soft bare bottom and took his hand, leading him back over to his changing table.

"Okay sweetie, now we're going to have some fun. We're going to play dress up--doesn't that sound fun?"

Timmy nodded again--now that he was done with the trying experience of holding his enema in--anything else seemed trivial by comparison.

"But first--we need to get you back into your baby diapers before you wet yourself," she said as she lifted his legs to make sure he had done good job of cleaning himself. There was something about her nature that made Timmy feel more embarrassed than usual, and as she wiped his crack with a baby wipe, shaking her head with obvious disappointment, he blushed with shame.

Michelle gave his bottom a thorough coating of sticky Desitin before sliding a thick, fluffy stack of diapers under his bashful rump. Baby powder followed and soon, his diapers were being tightly pinned around his narrow hips.

"I don't know where your mommy gets such soft diapers but it's no wonder that you were constantly playing with yourself," she said as she began working his pink rubber panties up his hairless legs. Unlike his usual vinyl panties, these tended to cling to his skin and required more effort to get in place around his fat, bulky diapers.

"Tell me, Timmy--which do you like better--your plastic or your rubber baby panties?" she asked him.

Timmy had never really thought about it but he knew his mommy liked the rubber panties for the better way they sealed against his thighs. He tended to leak less in his crib when she dressed him in rubber panties and for his part, he liked the buttery softness of them.

Timmy was about to offer his opinion on the subject when Michelle suddenly pushed the nipple of a baby bottle between his lips, cutting off whatever remark he had planned.

"Drink up, baby boy. Big sissies need their milk," she giggled as she winked playfully at him.

Timmy did as he was told while Michelle went over to his closet to pick out a pretty dress for him to wear. It was a difficult task to choose one, given that he had so many wonderful baby dresses and outfits to pick from.
After much deliberation, Michelle finally settled on a pink and yellow 'peek-a-boo' dress that openly displayed his fat, diapered bottom to good effect. After lowering it over his torso and securing the locking zipper in back, Michelle went over to his dresser to find a pair of matching rumba panties.

"What a lucky little sissy you are to be able to dress up in such cute, babyish toddler fashions everyday," she gushed with wonder.
One of his drawers was packed with frilly and lacy panties, all nicely full cut to accommodate his big, bulging diapers.

"Come here, little Miss Priss," she said cheerfully as she held out a pair of delicate white nylon panties, the seat decorated by rows of sassy pink ruffles.

"Just what mommy's little baby needs," she smiled enthusiastically as she held them lower and let him step into them. Timmy whimpered a little as she tugged them up his soft, girly legs and fitted them over his snug rubber panties.

"Perfect!" she declared, "Aren't you a special little girl!"

Timmy blushed again. He wasn't used to getting such attention and being unable to look his busty babysitter in the eye, his gaze kept returning to the long line of cleavage between Michelle's big breasts that were pressing against each other in a dazzling, mouthwatering display. Now that his stomach was feeling better, his horniness had returned with a vengeance and he could feel his little pen-is 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 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 blushing 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..."

 

[Baby Bobby]

                                                   CHAPTER TEN                           

Hazel was feeling antsy.

As she blew dry her long, luxurious chestnut hair in Gina's bathroom, she felt a growing sense of disquietude. 
When she reflected on the strap-on sex she'd been having with Timmy, it occurred to her that things were growing a bit stale. It's true that when she had first raped him, she had been thrilled by his plaintive cries and the look of absolute fear in his eyes. But after two weeks of humping his cute bottom in every imaginable position, the youth had come to appear to enjoy his sessions with her. Indeed, it looked like he was actually looking forward now, to having his tight little hole stuffed with her monster coc-k; 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 coc-k 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-fuc-ked 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 dil-do inside him.

Timmy was biting his lip anxiously, squirming in place as he tried in vain to escape the big, fat, probing coc-k 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 dil-do 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 coc-k 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 coc-k. She slapped his bottom and held his hips tightly, making sure he got every rubbery millimeter of her dil-do.

"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 coc-k," 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 coc-k 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 coc-k filling his mouth. His lips could only barely wrap around the tremendous girth of Kayla's dil-do and his cheeks bulged to capacity.

Hazel had her first orgasm but she knew a much bigger one was on its way.


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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.

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