Note to the reader: this is the sequel to Babyhood for Billie
Billie’s mommy clutched his hand as she awkwardly lifted him out from the oversized car seat she’d recently installed in the passenger side of her Camry. Billie waddled uncertainly, his fat, imposing diapers forcing his exposed, girlish legs apart. With her usual patience, his Mommy led him up the short path to her good friend, Mrs. Johnson’s house.
Although Billie very much liked the woman—who had always been loving and kind to him, he still found her to be very intimidating. It wasn’t just that she was stunningly beautiful, with deep brown eyes, full, luscious lips and long dark hair, but she also had an unbelievable body that she was not inclined to hide behind loose, unflattering clothing. On the contrary, Mrs. Johnson tended to wear snug, form-fitting outfits that showcased her big, mouthwatering breasts in the most enticing way. Billie often found that his tiny, one-inch pen-is would twitch excitedly in his diapers whenever she happened to be his babysitter.
After ringing the doorbell, Mrs. Johnson answered the door, her infectious smile washing over Billie and his mommy. Unfortunately, this attention had the predictable effect on Billie, who promptly flooded his diapers like the incontinent sissy that he had become. The fact was, after his mommy had decided to turn him into her little baby girl, whatever tenuous bladder control he might have possessed before, had by now, completely vanished. He wet freely now, without any kind of notice beforehand, making his thick, embarrassing diapers a very essential part of his wardrobe.
As Mrs. Johnson led the two inside, Billie could feel the warm wetness pooling between his legs before seeping back into the bulky, absorbent seat of his diapers. Fortunately, the colorful pink plastic panties he was wearing did a wonderful job of keeping it all contained.
Mrs. Johnson and his mommy talked for a while before saying their goodbyes, finally leaving Billie alone with the sexy woman. Today, she was wearing a snug pair of shorts and a white halter top that clung deliciously to her massive, round breasts. Billie gasped as he stared up at her deep line of cleavage until he felt her finger under his chin, gently redirecting his attention to her smiling face.
“Up here, Billie,” she chuckled with amusement.
Billie’s face blushed crimson, having been caught red-handed, once again, staring at her magnificent bosom.
“What a cute little top your mommy dressed you in today,” she exclaimed as she fingered the delicate lace on his short, puffy sleeve. The pink and white garment had a motif of Disney Princess with a hemline that barely went to his navel, leaving his fat, sissy diapers fully exposed. Billie blushed at her attention and a second stream of hot pee soaked the bunny soft cotton between his legs.
Turning him around slightly, Mrs. Johnson squeezed his amply padded bottom, confirming her suspicions.
“Looks like mommy’s little baby wet his diapers again,” she said as if she were talking to a child instead of a thirteen year-old boy, “Come on, let’s go get you changed.”
Feeling embarrassed at her condescending assessment of him, he sheepishly followed her down the hall and into the nursery. In one corner of the room, a padded changing pad was bordered by stacks of thick cloth diapers and plastic panties and in the other, a pink baby’s crib stood waiting for him.
Billie had become very familiar with this room, as he often spent his afternoons here, either restricted inside the mesh-sided playpen, or taking his daily nap in the crib. The room smelled strongly of stale pee and soiled diapers, bringing home Billie’s childish lifestyle. Leading him over to the changing pad, Mrs. Johnson sat him down and began peeling his damp, clinging plastic panties off his sopping wet diapers.
“Don’t worry sissy, I’ve got some nice, soft pampers for you to wear—just what baby needs for his afternoon nap,” she remarked cheerfully.
Billie whimpered in embarrassment although by now, he realized just how much he really needed the protection.
Unpinning the soggy, pee-soaked cloth, Mrs. Johnson deposited them in the diaper pail before pulling three more from the stack next to them. These had soft, cotton soaker pads sewn down the center which made the middle section quite a bit bulkier. She positioned them one on top of each other and slid them under Billie’s raised rump.
“Before we get you pinned up, sweetie, I’ve got something very special for you—something your mommy and I feel is just what you need.”
Billie was both intrigued and anxious, curious as to what she had in mind for him.
Turning away from him for a moment, Mrs. Johnson picked up something out of his view and came back with a strange pink contraption in her hand.
“Wha-what is that?” Billie quaked nervously.
Taking the device apart, she took one of the parts, a small, pink ring, and carefully fed his tiny, quivering package through it. Mrs. Johnson smiled down at the squirming boy as he started to grasp what she was doing.
“It’s your very own chastity device, sweetie,” she told him with her heart-stopping smile, “It’s perfect for little boys like you who still need diapers. Don’t worry--it won’t hurt a bit.”
Mrs. Johnson’s cute wink notwithstanding, Billie wasn’t entirely convinced and he watched with nervous apprehension as she placed the tiny pink cap over the head of his baby-sized pen-is and compressed it against the ring, slipping a long key into the internal lock and twisting it closed.
“There you are baby,” she said, obviously very pleased, “Soft, safe, and secure—just the way it should be for a diaper-wetting sissy. No more erections, no more orgasms—just a soft little pen-is locked in its cage where it will stay from now on.”
Billie flexed his little nub but could feel it was stuffed inside this implacable plastic prison, only now realizing it spelled an abrupt end to his chronic masturbating habit.
“B-b-but...” he stammered uncertainly. He didn’t want to admit to his perverse behavior but at the same time, he recognized this was one of those critical moments in his life where it was imperative to stand up for himself.
With her loving smile, Mrs. Johnson took a nearby pacifier and worked it between his trembling lips, holding it in place until Billie began submissively nursing on it. He blushed with shame, realizing that once more, in a battle of wills with his sexy babysitter, Billie was hopelessly outmatched.
“Spread your legs baby,” she instructed him as she took a big, pink, jelly butt plug, swirled it in a jar of nursery jelly and positioned it at his puckering back hole.
“Just relax and open wide, baby boy,” she said sweetly as he began applying pressure with the fat plug.
Billie squealed helplessly and tried to back up but before he could really respond, the slippery plug was forcibly pushed past his defeated sphincter.
“MMMPH!” he squealed in shock.
“There you go baby,” she giggled as Billie chewed the pacifier in angst, “that should hold you until your enema.”
Lifting him by his ankles, she swung his glossy pink Mary Janes over his head as she smeared diaper rash cream all over his bottom. After she was satisfied with the sticky white layer on his cheeks, she lowered his legs and began powdering over his new chastity device. Despite all the other distractions going on, Billie gazed up, staring at Mrs. Johnson’s big, pendulous breasts swinging within her thin top. He felt so utterly helpless as she hummed to herself and pulled the bunny-soft cotton cloth up and pinned either side snugly around his hips.
“Since it’s almost baby’s naptime, I think we’ll use a pair of rubber panties over your pampers,” she said as she selected a ruffled pink pair.
Billie kicked his feet in a childish attempt to forestall her but she quickly thread his shiny Mary Janes through the leg holes of the stretchy latex panties, working them up his smooth, hairless legs. He whimpered as she pulled them over his soft, bulky diapers, working her long nails around the rubbery waistband to make sure all the cotton cloth was contained inside.
“There you go baby,” she exclaimed, “all safe and protected again.”
Billie looked around, feeling embarrassed and emasculated. He certainly didn’t feel like a mature, budding teenager, but instead, like a bedwetting toddler having just been pinned into his naptime diapers.
“And now it’s nursing time,” she said enthusiastically as she stood up and led him over to the crib. Taking a seat on the edge of the mattress, she positioned the abashed boy on his back, so that his head was now in her lap. He looked up at her pretty face, suc-king desperately on his pacifier as she slowly and seductively, began unbuttoning her tight halter top. Her heavy, milk-laden breasts jiggled temptingly as more of her silky skin became exposed. Billie mewled anxiously, knowing exactly what was coming. Mrs. Johnson was still lactating and Billie’s mommy was only too happy to have her available to breastfeed her little sissy boy.
As Mrs. Johnson unclipped the clasp in the front of her sexy bra, Billie chewed anxiously as his little pen-is began throbbing desperately inside the hard, plastic cage it was held captive in. The last time he had nursed from his babysitter’s fabulous boobs, he had c-um hard, his stiff little one-inch member exploding with uncontrollable excitement as he splashed a couple drops of gooey, useless sissy sperm into his baby soft diapers. Now however, instead of being caressed by the pillowy folds of his diapers, his tiny wee-wee was stuffed into an even tinier cage, unable to get even the slightest bit hard. And he certainly wouldn’t be stroking it later for any kind of satisfaction.
His eyes roamed hungrily over his babysitter’s voluptuous curves, the diapered pantywaist horny beyond words. As she pulled back the big, lacy cup of her bra, Billie whimpered helplessly and she removed the pacifier he was chewing on.
“Here you are sissy baby, nurse from Mommy,” she said sweetly.
As her firm, warm nipple entered his mouth, Billie sighed and he suc-ked frantically, his child-sized pen-is aching miserably inside its petite, plastic prison. With his legs spread apart by the soft bulk of his diapers, he felt extremely babyish and helpless. He wished desperately that she would unlock his chastity device but deep down, he knew in his heart of hearts it would never happen. Like everything else in his life, this too would now be controlled by someone else, since he had proven that he couldn’t be trusted to have that control himself.
His horniness made him suc-k frantically and Mrs. Johnson had to chide him to go slower.
“Easy there, baby boy, there’s plenty of milk for you today, take it nice and slow,” she cooed at him.
While her right arm supported his head, her left hand went down to gently caress the soft, pillow front of his diapers, covered by the thin, stretchy rubber panties.
“After baby gets his fill here, I’ll prepare your enema and then it will be naptime for babykins,” she smiled down at him.
Billie hated his enemas, which were always a long, drawn out affair, both humiliating and uncomfortable, as she slowly fed two quarts of warm, soapy water into his bowels. Nevertheless, it was the last thing on his mind at the moment as his babysitter continued to teasingly stroke the front of his soft diapers. His tiny pen-is pulsated frantically in unrequited angst, desperate to grow hard but irrevocably trapped in this terrible new chastity device which would now be his permanent companion. He moaned in helpless anguish, suc-king like a newborn while he flexed his little nub uselessly. Finally, he couldn’t take it anymore.
“Please, Mrs. Johnson,” he pleaded in his whining voice, “Please unlock my wee-wee just this once.”
Looking down at him, she grinned broadly, showing her perfect white teeth, “Sorry baby boy, that’s here to stay. Sissy bedwetters don’t need orgasms—they need diapers and discipline.”
With that, she pulled him closer, forcing her hard, wet nipple back into his mouth and stifling whatever else he had to say.
“Don’t give that another thought—you just nurse from mommy’s breasts and get your fill, sweetie pie.”
Feeling more frustrated than he had in his entire life, Billie did just that, suc-king and nursing like a baby, first from her right breast, and then from her left. Finally, when she had decided he was finished, she tucked her big bosom back into her lacy bra and re-buttoned her top.
“That’s a good boy,” she said, condescendingly patting him on the head as she stuffed his pink pacifier back into his mouth, “you just sit tight and I’ll prepare your enema.”
Billie pouted but the second his babysitter left the room, he began furiously rubbing the front of his diapers, desperate to defeat his chastity device. He quickly found that while the sensation against his hands was the same—his soft, cushiony diapers felt wonderful as he fondled them, his captive pen-is could neither respond or grow within the devilish device it had been locked into. As he heard the sound of Mrs. Johnson’s footsteps coming back down the hall, he finally gave up in anger and frustration.
“This is just what all sissy boys need,” she exclaimed brightly as she hung the glistening red rubber bag on a tall stand near the crib. Soapy suds were dripping down off the sides and Billie could see the bag was nearly bursting with warm water, soon to be fed into him!
Taking a seat on the edge of the crib, Mrs. Johnson maneuvered Billie to the side of her lap, where she began peeling the stretchy rubber panties down and off his diaper. Once the pink latex material was ringing his calves, she gently pulled him over her lap, positioning him so that his feet were off the ground and putting him off balance, making it harder for him to get up. Unpinning the thick cotton cloth of his diapers, she smiled as she gazed down on the pink butt plug, still firmly lodged in his hole. Grasping it firmly, she pulled until it popped out, making Billie gasp with relief. However, all too soon, the thick, lubricated tip of the rubbery enema nozzle was pressing against his little pink hole as Mrs. Johnson began pushing with greater effort. The nozzle was about the size of a long, fat cuc-umber, and although Billie’s hole had already been previously conditioned by the butt plug he’d been made to endure, he still felt like there was no way this monster was going to fit inside him.
Squealing like a little girl, the sissy kicked his Mary Janes and shook his bunched fists in protest.
“NOOO!!” he wailed desperately, “P-please-please don’t!”
With a final push, his babysitter slid the massive shaft past Billie’s puckering sphincter and he moaned loudly.
“OOOHHHH!” he wailed.
“There you are, sissy,” she assured him as she gently patted his cheek, “That’s a good little baby.”
Looking down at his hole, she could see it was stretched to the very limit, stuffed with eight inches of fat, rubbery coc-k. Billie was breathing hard, still trying to deal with this imposing invader of his back passage.
Bunching his fists, he was gasping and whimpering as Mrs. Johnson opened up the clip, sending a strong, irresistible torrent of soapy water surging deep into his insides.
“This will keep your diapers from getting messy—isn’t that wonderful?” she asked.
Billie could only moan helplessly, trying to cope as best he could with the rapid feeling of growing fullness in his bowels. To be sure, his chastity device was the last thing on his mind now—all he could focus on, were the cramps setting in and his inability to do anything about it. He frantically tried to close his back passage but the gargantuan nozzle kept a wide, clear channel, allowing the unobstructed passage of soapy water to fill him up.
Mrs. Johnson regulated the clip judiciously, patiently ensuring Billie got every last drop in the bulging two quart enema bag. At long last, she finally allowed the gasping sissy to stand up on his shaking feet, leading him down the hallway to the bathroom. There, she stood over him as he released all that soapy liquid into the toilet.
Fifteen minutes later, she led the defeated sissy back into the nursery, pinned his diapers back in place, and pulled his prissy rubber panties back up. Giving him a baby bottle with warm milk, she lovingly tucked him into the crib and gave him his dollie to cuddle with as she pulled the baby blankets up around his chin.
“Sweet dreams, baby Billie,” she told him as she left the room.
Betty Pearl's Sissy Stories 20.1
Topic: Babyhood For Billie – Babysat by Mrs. Johnson (Read 10467 times)
