A Sissy Becomes a Baby Cuckold - Chapter Four
These are the chapters that make up the entire series;
Chapter one - A Bedwetter's Beginning
Chapter Three - Training a Sissy
Chapter Four- A Sissy Becomes a Baby Cuckold
Chapter Five - Penis Reduction Therapy for Sissies
Chapter Six - Milking my Sissy on Date Night
Chapter Seven - Taking Control From a Sissy
Chapter Eight - Nana Comes to babysit
Chapter Nine - Two Sissies--One Babysitter
Chapter Ten - A Playdate for Two Sissies
Chapter Eleven - Nana's Retribution
Mikey slowly stirred out of his state of slumber, not sure where he was.
As he slowly became adjusted to the dark lighting of Kendra's bedroom, he became aware of hushed voices from somewhere, possibly outside the house.
For some reason that Kendra hadn't shared with him, she'd decided to send him to bed early, and now that he'd drifted back into consciousness, he soon became aware that he'd wet his diapers, and the warm, clammy cotton clung to his bottom within his snug plastic panties. The smell of pee wafted up from under the covers and Mikey blushed that Kendra would smell it when she came into the room to go to bed.
Then he heard it again, what sounded like whispered voices, from the general direction of the driveway.
Slipping out of Kendra's king size bed, he padded over to the window. By now, Mikey had a several sets of jammies to sleep in―fuzzy, soft “diaper shirts”, that were purposely cut short, so as not to risk getting wet from the incontinent sissy's pampers while he slept. On his feet were frilly anklets, which were usually matched with his top and plastic panties, and hanging from a loop around his neck was his now ubiquitous pacifier, in babyish pink latex.
Gazing out the window, he spied Kendra wearing a slinky dress that fit her like a second skin, and a large man, with who she was speaking to in a seductive tone. Suddenly, she reached forward and began kissing him, as the man's hands roamed freely over her curvy body. Mikey was shocked beyond belief, and before he knew what was happening, he felt a strong torrent of hot pee flowing into his already wet diapers. Whereas a real man would have been filled with rage, Mikey's response was to wet himself like a toddler. A plaintive cry escaped his lips as his hands grasped at his diapers, the shame of his lack of control washing over him.
Looking back up at Kendra, Mikey bit his lip anxiously as he watched the man hold the door of his sports car open as she slid into the seat, her sexy high heels the last part of her he saw before her date closed the door.
Mikey let out a sob of anguish―she was never going to see him as anything remotely equal, or some sort of peer. No, at best, Mikey knew he was nothing but her sissy plaything, a toy to do with as she pleased.
As the car drove down the street, Mikey's gaze was drawn to the full length mirrors on the wall that covered Kendra's closet. By now, his eyes had adjusted to the dim, ambient light, and he gazed at his reflection, with his babyish top, pacifier and anklets, and his warm, soggy diapers starting to sag from around his hips.
Some man I turned out to be, he reflected glumly.
Tugging at the elastic waistband of his plastic panties to pull his heavy, wet diapers up, Mikey sighed as he looked at the cute, sissy bedwetter gazing back at him in the mirror.
As he slowly slipped back under the covers, he held his soft teddy bear close to his chest, slipping his comforting pacifier back between his lips. Between the two of them, it helped to take away some of the sting of seeing his “girlfriend” going off on a date with another man.
Over the next several weeks, Kendra never mentioned her late night liaisons and Mikey never admitted that he knew what she was doing behind his back. She was just so beautiful and sexy and he was deathly afraid of losing her, even under the unusual circumstances of their relationship. He didn't dare to confront her.
On the weekends, Kendra began dressing up Mikey more and more as her own baby girl, with pretty satin dresses in pastel colors, frilly onesies, and short, cropped tops with babyish designs on them. These were stored in the spare room next to Kendra's bedroom where she bought a large pink dresser to accommodate them.
On the weekend of Mikey's birthday, Kendra treated him to a marathon session with her strap-on dildo, milking his poor, swollen balls of a copious amount of semen, while stretching his sissy pussy to new, tormented limits. After recovering from her incredible orgasm, she dressed Mikey for the day, putting him into a delightful high-waisted, frilly pink baby dress with a bunny motif across chest below the Peter Pan bodice. In addition to his glossy black Mary Janes, Kendra had made him wear her favorite white nursery print plastic panties with his diapers, over which she pulled on some glittery, see-thru tights. Between the absurdly short hemline of the dress and the thin fabric of his tights, the playful pattern of his waterproof panties could be plainly seen, giving him a decidedly little-girl, toddler look.
Mikey pouted as he gazed at his babyish reflection in the mirrors on the wall.
Kendra was looping his pacifier around his neck when the doorbell suddenly rang.
Mikey froze in place as his eyes widened with panic. At the same time, a strong, uncontrollable squirt of pee flooded into his fluffy diapers.
“Go ahead sissy,” she said brightly, “Go answer the door.”
“Dr-dressed like this?” he quaked.
“Don't worry―it's just my mom,” Kendra replied, as if that would assuage his concerns.
“B-b-but...” he stammered anxiously.
“Don't worry sweetie―I've told her all about you. In fact, mom is the one who bought the cute dress you're wearing today,” she said with a giggle.
Mikey blushed hotly, from his cheeks down to his chest, unaware that Kendra had told someone else about his diapers and childish outfits.
“Run along, sissy,” she said, pulling him to his feet and patting the rounded, fat seat of his diapers.
Mikey stumbled uncertainly toward the door, absolutely dreading the moment when he'd be exposed to this new stranger. He held his hand on the doorknob for several moments before the doorbell rang again urgently, making him jump.
Finally, with great reluctance, Mikey opened the door and pulled it back.
Standing before him on the porch, was a tall, attractive woman in her late forties, closely resembling Kendra in many ways. Although she was a little thicker in the middle, one could easily see where Kendra had inherited her mother's big breasts and long legs. But whereas Mikey's boss tended to wear her long hair down, spilling over her shoulders, her mom wore hers in a severe bun that suggested she was accustomed to giving orders.
Despite her strict looking demeanor, her first reaction upon seeing Mikey in all his sissy glory was to burst out laughing. Standing before her feeling completely foolish, Mikey felt another surge of pee flow into his already wet diapers. It was a childish reaction, but the sissy simply couldn't help himself.
Still laughing, Kendra's mother pushed her way past Mikey. It was only then, that he saw she was carrying a rectangular shaped, gift wrapped package in her arm. Walking in, she set it down on the coffee table and turned to face Mikey.
“You're every bit as pathetic as I thought you'd be, except more,” she told him derisively.
Mikey blushed hotly as he shuffled his feet before her. It was absolutely mortifying standing before this older woman, dressed as a baby girl and feeling the warm, soggy cloth of his humiliating diapers clinging stubbornly to his bottom. He felt just as pathetic as she was describing him.
Mother and daughter greeted each other warmly, momentarily forgetting the spectacle standing before them.
Finally, after making a little small talk, Kendra's mother, Helen, turned to face Mikey.
“On the floor,” she ordered him in her firm, commanding voice, pointing to a place before the coffee table.
Having become used to being told what to do, Mikey immediately sat on the rug, the soggy wet cloth of his diapers squishing against his bottom cheeks.
“Look what mom got you for your birthday, Mikey!” Kendra said brightly as she handed the gift over to the cowering sissy.
Mikey accepted it with trembling hands, still trying to come to grips with the fact he was dressed like a toddler girl in front of this stranger. It certainly didn't help that he'd helplessly wet his diapers, either.
Ripping the pretty nursery style wrapping paper off the package, Mikey's mouth dropped open when he discovered the box contained a two quart enema kit.
Reaching down, Kendra's mother snatched the box from Mikey, opening it and revealing the custom nozzle that came with the kit―a very large, imposing, lifelike dildo.
“This is called the Sissy Tamer,” she declared with a smug grin, “And it's especially recommended for bedwetting sissies like Mikey here.”
Mikey's face was a beet red as she walked into the kitchen and started running water in the sink.
“Kendra, I like to add a squirt of dish washing soap to the mix, just to make sure he gets squeaky clean,” she called from over her shoulder.
“This is going to do you a world of good,” her daughter chuckled as she looked down on the cringing sissy.
Going to the coat closet, she retrieved a tall hat stand and set it alongside an armless chair. Taking an apprehensive Mikey by the hand, she stood him up and brought him over to her side as she took a seat and pulled her skirt back.
Her mother brought the enema bag back into the living room and Mikey could see it was nearly bursting with soapy water.
“N-n-no! P-please, Kendra,” Mikey stammered with fear.
“First―you are to address me as 'Mommy' from now on,” Kendra said firmly, “Second--this is exactly what you need, whether you like it or not.”
Mikey recognized by the tone of her voice that he was perilously close to risking a spanking so he hung his head in defeat.
“What do you say, Mikey?” she demanded.
“Y-yes, Mommy,” he bleated submissively.
Reaching up under the frilly hem of his baby dress, she pulled his tights and plastic panties down off of his saturated diapers.
“Mikey―did you wet yourself??” she snapped.
“I-I had an accident,” he sobbed piteously.
“Over my lap, you big baby,” she told him, clearly annoyed, “Time for a nice, soapy enema.”
Mikey felt like he was five years old all over again as she pulled him over her firm lap, his smelly wet diapers squishing against her bare thighs. He whimpered as he felt them being unpinned and pushed back to expose his back hole, cool air against his damp cheeks.
Mikey let out a squeal of panic as he felt a cool blob of nursery jelly being pushed into his puckering hole. Before he could stop it, a squirt of warm pee escaped, further soaking into his diapers.
Having so much experience with her strap-on, Kendra easily positioned the fat dildo nozzle for the proper angle and she pushed it firmly past his little pink anus.
Kendra's mother stood over Mikey, hands on her hips and grinning with satisfaction as her daughter slowly pushed the thick, rubbery shaft deeper and deeper into his rectum. Mikey waved his hands in the air helplessly, feeling extremely emasculated and completely at the mercy of his boss.
No sooner was the dildo rammed in to the hilt, than Kendra released the clip, sending a strong torrent of soapy water into Mikey's bowels.
“Ohhhh,” he moaned, kicking his Mary Jane-clad feet.
Kendra squeezed his right cheek as her other hand kept the dildo pushed in as far as it would go.
“There you go,” she said in a soft, soothing voice, “Just what Mommy's little bedwetter needs.”
Mikey gasped and moaned, helpless to stop his punishing purge. It brought back memories of when his real mom had given him enemas, claiming they were for his good health, although Mikey had always had his doubts. They had been particularly humiliating when administered in front of his aunt, who soon adopted his mother's methods herself.
Kendra regulated the clip judiciously, allowing Mikey to get adjusted to the volume, before opening it back up to send another strong flow into his insides. Mikey shook his fists in frustration, idly wondering how he had ever gotten into this position.
“N-no more, Mommy,” he bleated weakly.
Kendra stopped the flow and gently patted his cheek.
“There sissy―you're doing just fine,” she smiled, “Now be a big boy for mommy and take your enema. And when you're done, mommy will change your soggy, wet diapers―won't that be wonderful?”
Mikey was breathing heavily but he squealed as he felt another strong surge of warm water flowing into him. He tried clenching his anal muscles around the thick shaft of the dildo but it did no good―the water continued to flow strongly, uninhibited by his weak efforts.
At long last, the bag was finally empty, hanging flattened from the top of the hat stand.
Mikey was wheezing and moaning, his face a deep shade of red.
With a gentle pat on his bottom, Kendra slowly began easing the big dildo out of his rump, Mikey whimpering from the cramps inside.
“Careful Sissy,” she warned him, “Don't let any of that leak or you'll be going back over my lap for a different kind of session.”
As Mikey slowly rose to his feet, his hand moved to cover his caged genitals in a belated attempt to hid them from Kendra's mother. Limping down the hallway, Mikey barely made it to the bathroom without releasing the enema all over the floor.
Fifteen minutes and numerous flushings later, he emerged from the bathroom, feeling defeated and deeply emasculated.
“Mikey―come into the spare room, mommy has a surprise for you,” Kendra called to him eagerly.
Unsure of what awaited him, he walked toward the open door of the room next to Kendra's with trepidation in his heart.
“Happy birthday!” they both exclaimed as Mikey took in the transformed room.
A large pink and white crib stood in the corner, with soft pink blankets and Mikey's teddy bear laying next to the pillow. In the other corner of the room was a pastel colored, mesh-sided playpen, containing a variety of toys fit for a toddler. Nursery characters covered the pink and white walls and Mikey's changing pad lay on the floor, a fresh set of diapers waiting for him.
He bit his lip nervously as she spied Kendra's fearsome Spencer paddle hanging from a peg on the wall.
“Welcome to your very own nursery!” his boss gushed excitedly.
“It's perfect for a little pantywaist like you,” her mother added in her disparaging tone.
Mikey stood in shock, momentarily dropping his hands from his tiny, caged package as he took it all in.
“This bed will be so much better for you, sweetie,” Kendra explained eagerly, “It's got a nice, waterproof mattress cover for those times when your diapers leak.”
“--An important feature for a bedwetting sissy,” her mother added with a smirk, “But I think you'd better get your little pantywaist back into his diapers before he has another 'accident'.”
“Come along, Mikey, let's get mommy's little bedwetter onto the changing pad, I've got your diapers all ready for you,” Kendra told him as she grasped his hand and sat him down on the waiting stack of soft, fluffy cotton.
Mikey felt incredibly childish and her humiliating words washed over him in waves of shame.
Helen reached down and pushed his pacifier in between his trembling lips and Mikey accepted it gratefully.
Kendra applied a nice, sticky white coating to his rump, before powdering him over his tiny chastity device. Now that he had become somewhat used to Helen's presence, and despite the mortifying ritual taking place, Mikey's eyes began to wander over Kendra's curves and his little penis throbbed with need inside his cage. Her big, luscious boobs were impossible to ignore, especially when she was bent over him changing his diapers.
“Those aren't for you, little boy,” Helen admonished him, having seen what he was staring at, “Those are for a real man―not a bedwetting sissy in diapers.”
Mikey pouted as he sucked his pacifier in frustration. It was maddening, being in such close proximity to a sexy babe like Kendra and his child-sized penis couldn't even get hard.
Sensing his angst, Helen decided to goad Kendra's sissy boyfriend.
“I think you should thank Kendra for locking up your pathetic little wiener,” she said, a smug grin on her face, “You certainly weren't going to please a woman with it.”
Kendra stopped for a moment after securing the sides of his thick diapers around his hips to look down at her sissy boy.
“She's right, you know,” she said, placing her finely manicured hands upon her hips, “I've done you a big favor, locking your little nub in steel.”
“Please, Mommy,” Mikey whimpered with his pacifier muffling his words, “I'm soo horny all the time. Please―please unlock it, just this once,” he begged her piteously.
Wagging her finger before her, she smiled down at the helpless pansy, “Sorry sweetie. Bedwetters get diapers―not orgasms.”
Helen smirked again and she shook her head disdainfully.
“You leave the orgasms to real men and they'll leave the wet diapers and plastic panties to you,” she told him as she sifted through his growing selection of waterproof panties.
Kendra handed Mikey his teddy bear as Helen began feeding a pair of white nursery print vinyl panties over his Mary Janes.
“Here you go, sissy boi,” she said, her voice heavy with condescension, “Some cute baby panties for mommy's little bedwetter.”
Sliding them up his smooth, hairless legs, she worked them over his bulging diapers, running her fingers around the elastic waistband to ensure that all the cotton cloth was properly contained.
“Just look at you, Mikey,” Kendra said brightly, “All safe and protected again.”
“Let's get you into your playpen so you can play with your new baby toys,” Kendra said as she helped the befuddled sissy into his new enclosure.
“Aww, aren't you just the cutest thing,” she gushed eagerly as she clasped her hands together in appreciation.
Helen looked down at him as she shook her head with disdain.
“You're right where a bedwetter belongs―diapered, denied, and controlled.”
Mikey woke up to see the late afternoon sunshine dimly streaming through his nursery windows.
Reaching down between his legs, he discovered his diapers were soaking wet, as they always were after his nap. The shameful smell of pee permeated the room, although Mikey was so used to it that the diapered sissy hardly noticed any more.
Just then, Kendra breezed into the room and she crossed over to the window, pulling aside the gauzy pink curtains.
“Hello sweetie,” she greeted him cheerfully, “How did you sleep?”
Mikey yawned, “Good, Mommy,” he replied.
He watched as Kendra prepared a fresh set of diapers for him and she lowered the side of his crib railing to help him out. Today, she was dressed in a thin, low cut halter top that showcased her magnificent breasts in the most mouthwatering way. Mikey stared at her hungrily, wishing for the millionth time, he could nurse from her beautiful bosom.
As she came over to the side of the crib to help him out, Mikey always felt somewhat vulnerable in these moments. It was the the time when she saw him for what he really was―a sissy bedwetter with no more control than a diapered toddler. And it still made him blush as she gazed down upon him in his fleece jammies and pampers, no longer an adult, but just a simpering little pantywaist.
Kendra helped him out of his crib and onto the changing pad where she began pulling his rubber panties and soggy, wet diapers down.
Gazing longingly up into her pretty face and dancing eyes, Mikey realized he was hopelessly in love with her.
“Mommy's got a little something for babykins,” she said sweetly as she set a tube of something behind her and produced Mikey's chastity key from her pocket. With excited abandon, Mikey watched as Kendra inserted the key into the side of his device and twisted it, unlocking the device for the first time in 10 weeks. As the cage was removed, Mikey's tiny little member quickly began to grow with anticipation.
“Now don't get too excited, Mikey,” she giggled, “You don't get to cum today―Mommy's just going to give it some cream that's supposed to help you with your size.”
Even though he was crushed to learn that he wouldn't be cumming today, Mikey felt a surge of gratitude that she was thinking of new ways to make his little penis grow into something more of a real man's proportions.
Slipping a thin rubber glove on her hand, Kendra was careful to hide the name on the tube which said Penis Away along its side as she squeezed a generous portion onto her open palm.
“Theeere...is this what baby likes?” she grinned down upon him.
Mikey sighed and his eyes closed with ecstasy, reveling in the pleasureful feelings coursing through his body.
Kendra was very careful, shrewdly reading his body signs to judge how far she could take him before he exploded in her hand. Mikey's face was flushed and she had to stop her stroking several times to allow him to cool down, before resuming the rubbing in of the penis reducing cream.
“Don't worry, baby,” she said with her ravishing smile, “We're going to make this part of our daily routine from now on.”
Mikey could feel a monumental orgasm rising and just as he was clenching his teeth in anticipation, Kendra abruptly stopped stroking him and she removed the latex glove from her hand.
“Aww, Mommy!” Mikey cried.
“Sorry, sissy,” Kendra giggled, “But don't worry―Nana is coming over later to give you a nice, soapy enema. That should help clear out those swollen little balls of yours.”
Mikey bunched his fists in bitter frustration. He had never been so close to an orgasm before, only to be denied!
Ignoring his angst, Kendra slipped the metal cage back over his wilting erection, mashing his tiny penis into the device and mating the metal pins against the cuff ring.
“What do you say, babykins?” she asked sweetly.
Mikey shook his head petulantly.
“Come on―if you want some more of this tomorrow, you need to say your little line for mommy,” she told him firmly.
Mikey's brow furrowed and his lower lip jutted out in a full blown pout.
“Th-thank you, Mommy, for my chastity device―I really need one,” he said grudgingly.
“Yes you do, you little sissy masturbator,” she said with smug superiority as she locked the device together, rendering him once more frustrated, desperately horny, and sexless.
Several minutes later, Mikey was freshly diapered again, smelling like baby powder, and back in his crib, his head laying upon Kendra's lap as she held a 16 ounce baby bottle of warm milk to his lips.
“That's mommy's baby,” she cooed as Mikey nursed from the bottle. Nearly his entire vision was taken up by Kendra's enormous breasts in front of his face.
“Now Mikey, it's time we had a little discussion,” she began, “As you might imagine, Mommies like me have needs. Needs that a sissy in diapers just can't meet.”
Mikey mewled in protest but the big rubber nipple filling his mouth prevented him from being able to articulate a reply.
“Mommy needs a real man from time to time. A man with a real cock, not a tiny little nub like you have. So that means from time to time, say, once or twice a week, I'm going to be dating other guys and having hot, mind-blowing sex with them. Sometimes it will be at their place, but sometimes it will be here.
“Now, you can either deal with that, or we can end our relationship now―it's up to you.”
Mikey was dumbfounded―of course, he knew all about Kendra's dating but now that it was out in the open, it forced him to give her his full approval, which would only show how weak and spineless he really was.
With a little squeak, he suddenly felt the seat of his diapers growing wet and warm as a steady stream of pee began flowing helplessly between his legs.
At the same time, as he looked up into the firm but beautiful features of Kendra, he knew deep down that he would willingly play any price she demanded to remain with her.
“What do you say, sissy? Are you going to stay as mommy's little baby or do we call it quits?”
Mikey shook his head desperately.
“Please don't leave me, mommy!” he cried, the nipple suddenly slipping out of his mouth.
Kendra smiled victoriously down at her prissy toddler boyfriend.
“That's my little baby bedwetter,” she said with a smug smile, “Mommy's very happy to hear it.
“Now I know I promised you I would allow you to have an orgasm after three months, but I've decided to add another month, just for good measure. What do you think of that?”
Mikey frowned with dismay but he nevertheless knuckled under.
“Th-thank you, M-Mommy,” he said, the bottle nipple muffling his practiced line, “for my--my chastity device―I really need one.”