Babydoll
He thought it was what he wanted, he really did. Ever since Christian was little, he enjoyed playing with dolls. Not so much because he liked to do what girls do–well, he did–but more that he wanted to be the doll. They got to wear pretty dresses and have their long blonde hair put into bows, their cutesy shoes switched out, and they got to be pampered and adored by someone else.
Speaking of pampered, Christian seemed to always gravitate towards the dolls that needed diapers. The ones that would squirt fake wets and messes so he could change them. He remembered begging his Mother for those toys.
His Mother knew that Christian would most likely not grow up to be a very strong, masculine boy. She knew her son was not like the others, he’d taken far too much interest in all things feminine, but she also never saw anything wrong with that. She would oblige him if he asked her to paint his nails, or put make-up on him, or make his hair curly. She thought it would be a phase, something he’d grow out of when he got to high school.
But college came and went and Christian was still living in her basement. She could hear him at night, making loud, pathetic mewling sounds. Watching god knows what on the internet and doing god knows what to himself. She found countless diapers in the trashcan that Christian did a pisspoor job of hiding. When a bra or panty set went missing, she knew the first place to look was in Christian’s room tucked into the back of his closet. She never said anything, though. She let her boy partake in his little fantasies and work himself raw. She’d change his sheets that only had a hint of piss soaked into them, as if most of it ended up somewhere else and this was only what leaked out when a certain item had reached capacity.
Christian had spent most of his life jerking off to sissy and abdl and feminization porn. He’d watched countless hypnos that made his brain rot, he even put his own penis in a cage sometimes and learned to cum like a ‘gurl’. But all of that was only when he was in the throes of hornydom. He’d dream of being a pretty little doll for someone, to get put in diapers and dresses and makeup and be ‘forced’ to live life as a little sissy bimbo. This, obviously, didn’t do much for the ladies, so he never had a true girlfriend.
So one day, Christian decided after 5 days of depriving himself of orgasms, that he was finally going to come out to his Mom. He was going to tell her about how he’s a sissy, how he likes to wear diapers, and be treated like a baby. He was tired of keeping all of this shoved down and tucked away for so long.
It felt so freeing to finally tell her. To let her know everything about what her son was secretly doing. But, apparently, it wasn’t much of a surprise at all. She hardly blinked an eye, and instead just smiled like a mother patiently waiting for her child to correctly solve what 6+8 is, and congratulating him for finally getting it.
“So you want me to treat you like a little sissy baby?” she asked, clarifying.
“Well, no…” he said. Or, at least, that’s what he wanted to say. Instead, he was awestruck by the idea, by the possibilities. He could finally get what he wanted! He could have someone treat him like the sissy baby gurl he’d always wanted to be! “Yes!” He said for real, “Very much yes!!”
His mother only laughed. “Are you sure that’s what you want? I mean, when will it stop? How long do you want to do this?”
“Forever.” He said, a single word sealing his fate. If he knew what he knew now, he would have never uttered that word.
“You’re sure?”
“Yes.” Okay…maybe he shouldn’t have said that one either.
So started Christian’s journey into sissy depravity. His mother pulled out all the stops, showing no mercy. Like a stern parent raising her child once more, she kept him in line using discipline, time outs, and a new one most mothers can’t use: chastity denial.
She watched as her son slowly transformed into a babbling, drooly mess. She wasn’t sure if it was the hypnosis she’d been making him watch, or all the childish TV shows. He wasn’t allowed to play his video games any more, something he threw quite the little tantrum over. Instead, he was given blocks and rattles and (if he was good) some of his favorite dollies. She didn’t have to cook much, Gerber took care of all his meals. She’d shovel pureed prunes and peas into his mouth and wipe up the contents to shove back in. She didn’t think she’d ever be changing Christian’s poopy diapers again, yet here she was.
But after only a few short months, she started to notice even more of a change in him. He became more reclusive, more whiny, more tearful.
“What’s wrong, pumpkin?” she asked, drying Christian’s eyes with his food splattered bib.
“I on’t wanna be uh baby anymore!” he cried.
But his Mother showed no sympathy. “Awww!! Well that’s too bad, hunny! This is what you wanted! Remember? You wanted this to be forever.”
Christian looked up at her with his little doe eyes, like he knew he’d made a grave mistake.
“I guess this is as good a time as ever to tell you…” Mother said, clearing her throat, “I’ve arranged for you to have a little…procedure.”
“Puceedur?” Christian could hardly get the words out, his brain was so numb.
“Yes honey. You know those little princess parts between your legs?”
He looked confused.
“The ones inside your pampers.”
That seemed to make sense to him, anything involving diapers was easy to get his head around.
“Well you see honey, this procedure, this operation is going to take those away!”
His eyes went wide, but he still looked hazy. Like he could only slightly understand the gravity of the situation. It took several more seconds to finally sink in.
“B-b-but…I on’t wanna lose my princess parts!!”
His mother just shrugged, arms crossed. “I’m afraid it’s too late for that, dear. You wanted this, and I’m just supporting you.”
She pulled a bottle from the bag, shaking it with her finger over the nipple, then brought that nipple to Christian’s lips.
“Drink up, honey!” she said softly, “This has all the ingredients to help you become the wittle baby gurl you’ve always dreamed of being!!”
~~~~~~~~~~~~
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Mommy's Boyfriend
Mommy's Boyfriend
Brian sat in his playpen, feeling more and more fussy and frustrated by the moment.
His wife—or rather 'Mommy', as he was required to address her, was sitting across the living room on the couch, her laptop open, as she was setting up a Zoom meeting with her latest boyfriend. Brian seethed with jealousy but he simply couldn't take his eyes off his sexy spouse. She was wearing a short, snug pencil skirt, high heels, and a new silky blouse that hugged her tremendous, mouthwatering breasts in the most exciting way.
She had come home earlier from a productive day of shopping and had purchased a collection of lingerie and skimpy outfits and now she was eager to show them off to her boyfriend, Hank.
As the call went through, Brian could hear her hunky boyfriend's deep voice on the other end.
“Hi babe!” she greeted him enthusiastically, “How's my sexy lover doin'?”
Brian couldn't make out his response and he sulked as he slurped noisily on the fat rubber cock pacifier filling his mouth.
Today, his Mommy had dressed him in an adorable cute baby dress; white with pink accents, short puffy sleeves, a frilly hem and a Peter Pan collar. Knee high lace socks matched his outfit, going perfectly with the satin white rumba panties with pink lace over his big, bulging diapers. Alas, during the course of the day, he had managed to soak them, although that was hardly surprising, given his total lack of control over his bodily functions anymore. As humiliating as it was for him to wear them, diapers and plastic panties were very much a necessary part of his daily life now. What had started as an occasional bedwetting problem had gradually devolved into total incontinence for the frustrated sissy. And despite his earlier request to be changed, his Mommy was too excited to share her purchases with her boyfriend to take the time and change his sopping wet diapers.
So as usual, Brian just had to sit there in his playpen, the childish smell of pee surrounding him and the clammy wet cloth clinging to his bottom as he watched his wife talking animatedly with her boyfriend.
Unbuttoning her blouse, Mariana pulled it away to reveal the sexy pink satin bra she was wearing underneath.
“What do you think?” she asked Hank, who no doubt, had his eyes glued to the screen, “Wanna play with these?”
Her voice was flirty and playful, and Brian sucked harder on his pacifier. Normally, it provided some comfort to him, but today, it was taking the brunt of his sexual frustration and he slurped and drooled, rapturously staring at his ravishing Mommy, desperately wanting something he could never have.
His situation was certainly made worse by the fact that his tiny micro penis flexed impotently inside his steel chastity device, unable to grow beyond the half inch confines of the cage. And the flexible urethra insert that went two inches down the shaft of his little willie ensured there was zero chance of his achieving any sort of sexual gratification. It had been months since his last (brief) sponsored orgasm and Brian was beside himself with horny desire.
Mariana cupped her big boobs in her hands and hefted them to tease her boyfriend.
“I can't wait for you to come over and play with me,” she cooed with a naughty grin on her pretty face.
For his part, Brian lived in fear of her six-foot-four boyfriend, who was built like a running back for a professional football team. For one thing, he liked nothing better than to belittle Brian, boss him around, and when the mood took him, yank him over his sturdy lap to spank his bare bottom. It rarely took more than two swats before Brian was bawling like a baby, kicking his feet helplessly as Hank paddled him soundly. He firmly believed in establishing his authority over the weak, diapered sissy and putting him in his place whenever he happened to stop by.
And Mariana had little sympathy for the sniveling pantywaist, often watching with satisfaction as Brian got taken down several pegs.
After pulling his diapers back up, he would often be sent to the corner or his playpen to sob and cry as he rubbed his blazing bottom through the multiple layers of Birdseye cotton cloth.
Brian desperately hoped that wouldn't happen today, but of course, he had no control over what Hank
would or would not do. At Brian's diminutive 5' 6”, the man he was required to address as “Daddy” towered over the weakling in his prissy diapers.
Turning away so her hubbie couldn't see her nakedness, Mariana unhooked her bra and put her slim arms through a different one, this one a black push-up in a demi-cup style. Only when her nipples were covered did she turn so that Brian could see the new bra. It frustrated him to no end that she no longer showed certain parts of her body to him, deeming him too childish to be able to view them.
“These are all yours, sweetie,” she cooed to the screen.
Softly stroking the pillowy soft skin of her breasts, she winked at her boyfriend on the laptop screen.
Brian was forced to watch and listen as she flirted with Hank for another ten minutes before finally ending the session and shutting her computer off. With a sigh of anticipation, her beautiful face glowed with excitement.
“Hank is so excited to come over and have sex with me,” she said triumphantly.
With a look of defeat and dismay on his face, Brian rose to his knees, clutching the padded rail of his playpen desperately.
“Mommy—my diapers are wet,” he whined miserably.
“I know sissy, but you'll have to wait a little longer,” she said as she passed by him, her high heels clicking as she went down the hallway to his nursery. Coming back out and carrying his red rubber enema bag, he heard water running after she had stepped into the bathroom. Brian bit his lip as he belatedly realized he was about to get another long, emasculating enema over Mariana's lap. These were a daily occurrence for the diapered sissy but they usually happened in the morning—indeed, he had gotten one right after Mommy has taken him out of his crib earlier this morning. He dreaded getting a second one, especially since she had begun using her new nozzle, something called the Sissy Splitter. It was a massive dildo with a fat, rubbery girth that made him squeal like a little girl when she forced it into his shy, pouting rectum.
More troubling was the fact that getting an enema in the afternoon often hinted at what he might expect when Hank came over later. The bully enjoyed bending Brian over the nearest piece of furniture or his crib mattress to take him from behind, using his gargantuan cock to punish the diapered bedwetter.
Finally, Mariana came down the hall and helped Brian out of his playpen.
“Time for another nice, soapy enema, sissy,” she told him sweetly.
“No,” he said petulantly, but as usual, she ignored him and led him waddling down the hallway to his nursery. The nearly bursting enema bag was hanging from its tall stand, soapy suds dripping down the glistening sides. Taking a seat on the spanking stool, Mariana patiently led Brian over to her side, where she grasped the elastic waistband of his snug plastic panties.
“This will make my little sissy all squeaky clean,” she said enthusiastically.
Brian hated it when she called him little but more concerning was the fat latex nozzle awaiting him.
With his damp panties now around his ankles, Mariana pulled him over her lap, his soggy diapers squishing against her bare, toned thighs. He whimpered and mewled, even as he gazed up at the full length mirrors on the wall, seeing the look of satisfaction and superiority on his Mommy's face. Unpinning the wet cotton cloth, she pulled his diapers back to expose his quivering pink hole.
“We better start you off with your medium dildo,” she remarked as she twirled one of his “smaller” dildos in the nursery jelly before positioning it at his back hole.
“Spread your legs, sissy,” she commanded him firmly.
“Oh—please—no, Mommy,” he squealed but he nevertheless spread his legs submissively as she began applying pressure with the dildo. It slipped in surprisingly quickly, even though it was also quite large.
“OH!” Brian exclaimed as he felt the thick, greasy invader sliding into his backside.
His Mommy pumped it slowly, allowing him to get accustomed to the rubbery phallus as Brian soon settled down and began panting.
“Baby likes this, doesn't he?” she asked coyly as she smiled down on her impaled hubbie.
Brian was blushing but he nodded his head guiltily. Having been deprived of any sexual release for so long, he was desperate to get anything he could and the slippery cock was teasing his boi pussy tortuously.
After several minutes pumping him in and out, she finally pulled it out and set it aside.
“Okay, that's enough of that—I think you're ready for the Sissy Splitter now,” she announced.
“No-no-no!” he cried, squirming fearfully on her lap.
The Sissy Splitter was a true leviathan, and although he had experienced its tremendous girth already today, he wasn't sure he could handle it again.
Positioning the fat, blunt mushroom head of the cock at his hole, Mariana pushed forcefully even as Brian shrieked and tried to pull away. He kicked his feet and wailed just as the monster head slipped past his weakened sphincter.
“OHHHH!!” he cried, his eyes wide open in panic.
Pushing slowly, his Mommy eased it into his aching passage until it finally bottomed out.
“Theeere,” she said with a grin, “I'll bet that feels just like Hank's big cock, doesn't it sweetie?”
Brian gasped and screwed his eyes shut, his hole stuffed beyond capacity.
“Little sissies need their enemas,” she told him cheerfully as she opened up the clip on the hose, allowing a strong surge of warm water to flow unimpeded into his bowels.
“Ohhhhh,” he moaned helplessly.
Brian squirmed and whimpered, unable to do anything about the torrent filling him up through the gigantic, rubbery shaft lodged into his back passage.
“Aren't you glad Mommy has a real man in her life again?” she taunted him.
He nodded his head as he tried to grapple with the growing pressure in his bowels but she wasn't satisfied.
“Answer me, Brian—aren't you glad I finally have a real man in my life again?”
“Y-yes, M-Mommy,” he bleated.
“And Hank is so much more of a man than you ever were,” she remarked as she closed the clip, giving him a brief respite, “After all, he's not a bedwetter that wears diapers and baby panties like you do.”
Brian blushed shamefully, but before he could think too much about it, his Mommy opened up the clip again and another strong surge flowed deep into his rectum. He gasped and was breathing heavy, feeling the cramps beginning to take hold.
“N-no more, Mommy,” he wailed desperately.
Ignoring his pleas, she patted him gently on his curvy rump.
“There, there, baby,” she said shushing him, “this is just what you need.”
Brian tried flexing his butt muscles to staunch the flow but it was a completely useless gesture. The warm, soapy water flowed on at the pace of his Mommy's choosing, making him struggle and moan.
“And aren't you glad that mommy decided to put you into diapers full time?” she taunted him.
A bead of sweat had formed on his brow and it trickled down the side of his face.
“Y-yes, Mommy,” he bleated.
“You really do need them just like a toddler, don't you?”
“Ye-yes, Mommy,” he replied.
“Say it, sissy,” she commanded him.
“I-I need diapers just l-like a t-toddler,” he stammered weakly.
Finally, at long last, the remaining water flowed into the whimpering sissy and when she was satisfied he'd taken every last punishing drop, she began easing the fat, imposing nozzle out of his sore, aching hole.
Brian wheezed with relief as he clamped his hole shut, lest he allow any of the enema to leak. He knew too, that that would earn him a trip over Mommy's knee.
As she carefully lifted him back up to stand on his feet, she scrutinized his flushed face.
“Do you need a buttplug to get you to the bathroom?” she asked.
He shook his head with humiliation and limped out of the room, his wet diapers still hanging awkwardly over his plastic panties.
Fifteen minutes later, a chastened sissy came back into his nursery, his head hung shamefully. Mariana was eagerly texting her boyfriend, looking forward to a night filled with fantastic, satisfying sex and lovemaking. For Brian, it meant an early beddie-bye time in his crib and as usual, no chance whatsoever of an orgasm.
“Alright sissy,” she said in her strict, maternal voice, “Let's get you back into your diapers where you belong.”
Leading him to his vinyl covered changing table, she set him down upon a fluffy stack of fresh, soft diapers that she had arranged for him. Laying down in the all too familiar position, Brian prepared for this most humiliating of rituals. It was bad enough being openly cuckolded by his hot wife but to be dressed like a little girl and put into diapers was beyond mortifying. And yet, the weak-willed sissy submitted mutely, afraid to stand up to his strong, domineering wife.
With her left hand, Mariana grasped his lacy anklet-attired feet and raised them over his head, examining his hole to make sure he had cleaned himself properly. A small, oval shaped paddle lay nearby, in case he failed to meet her standards for hygiene. Taking a glob of Desitin with her right, she began smearing the sticky substance across his bottom and between his legs, giving him a nice, white coating overall.
“There—that's a bedwetter's best friend, isn't it?” she said brightly.
Brian was ashamed that such measures were necessary but then, this was a ritual that he had endured repeatedly for years, his real mom having done the exact same thing to protect his bedding all throughout his Middle and High school years.
Lowering his legs, Mariana began applying baby powder to his front, between his legs and over the tiny steel cage holding his toddler-sized penis captive.
“Don't worry sissy—as soon as I get you changed I'll put a bottle in the warmer for you,” she told him as she brought the thick, bulky layers of cotton up and slipped a large safety pin through the ends to keep his diapers snugly in place. Pink duckies adorned the head of the pins, giving them a very babyish look.
And Brian wasn't looking forward to his bottle either. While Mariana and her boyfriend would soon be sipping chilled champagne, he would be nursing from his jumbo baby bottle of warm milk.
Stacks of plastic panties were arranged behind the changing table, requiring Mariana to reach over the top of Brian to choose one.
He gazed hungrily up at her pendulous breasts, swaying before his eyes and barely contained within her lacy push-up bra, wishing desperately he could just reach up and touch them. Alas, that too was strictly forbidden, and he knew it would only result in a blistering spanking over her lap.
“Lets see...how about these?” she said brightly.
They were a milky white pair of waterproof panties with a playful polka dot design. With dainty, pink lace around the leg holes, they screamed infant, but then, not really any more than his other plastic panties which were all in similarly childish pastels and nursery prints. All his old underwear had long since been thrown away so these babyish panties were all he had.
“Here you go, sweetie, she said as she fed them over his feet and up his smooth, girlish legs. It took a bit of effort to wrestle them over his big, bulging diapers but eventually, she was running her finely manicured fingers around the elastic waistband of his panties, making sure all the absorbent cotton cloth was contained.
“There—just look at you!” she exclaimed, “Mommy's big baby is all ready for his evening!”
Brian blushed with shame, her condescending words washing over him.
Choosing his glossy black Mary Janes, she buckled them on his feet and brought him to a standing position before the mirrored closet doors.
“What a cutie you are,” she gushed as she patted his fat, diapered bottom affectionately, “Mommy's little bedwetter is as prissy as can be!”
Brian bushed a bright red as he gazed at his sissyish reflection, looking just like a diapered little baby girl.
Suddenly, the doorbell rang and Brian nearly jumped.
“Looks like Daddy's here,” Mariana swooned eagerly.
Giving him another playful swat on his bottom, she took his hand and led him out of the nursery, down the hallway and over to the front door. Opening it wide, she grinned excitedly as her boyfriend Hank stood on the porch, a bottle of champagne in his hand.
“Hi baby!!” Mariana squealed as she rushed out to kiss him deeply and enthusiastically.
Brian had to stand there awkwardly while his wife passionately made out with the hunky man on their doorstep. He cringed as he thought of what his neighbors must be thinking as they saw a stranger having his way with Mariana. A trickle of warm pee began to flow out of his cage and into his voluminous diapers although Brian remained oblivious. He sometimes wondered if Mariana had purposely decided to marry him with the intention of later cuckolding him.
Filled with helpless jealousy and anger, he watched as Hank's hand made its way down the small of her back to squeeze Mariana's perfect derriere through her thin skirt.
Just then, a young woman walking her dog happen to go by on the sidewalk just ten feet away. Her mouth dropped open in shock as she took in the scene of passion and then made eye contact with a quaking Brian.
Blushing a bright red, he quickly turned away, sobbing tears of humiliation as he struggled to deal with his crushing shame. This time, a strong stream of urgent pee flowed uncontrollably into his diapers, as Brian let out a squeal of panic.
Finally, the two broke apart, Mariana breathing heavily with lust as they came inside and left the still staring woman on the sidewalk. For the first time, Hank took in the sissy baby standing red-faced before him. With a deep, dismissive laugh, he grasped Brian's wrist, yanked him around and landed a hard swat on his fat, diapered bottom. Although he was so thickly padded that it didn't hurt, the shame of being treated with such inferiority was deeply humiliating for the blushing pantywaist.
“Have you been thinking about my cock?” he asked with a crooked, lascivious grin.
“N-no, Daddy,” he peeped quietly.
“I'll bet you have,” he countered, “I'll bet you can't wait to wrap your sissy lips around my man meat again.”
Brian's cheeks flushed all over again as he recalled the last time Hank had forced his massive beast down his throat, gagging him and gripping his head to make sure he couldn't get away. But even worse was to come when he finally blasted his salty load down the diapered sissy's throat, making sure he swallowed every creamy drop of his semen.
“In fact, I think it's time you show me just how grateful you are now that Mariana is finally getting the sex she deserves,” he said as he pushed the weak sissy to his knees.
“No-no-no!” he cried, seeing what Daddy had in mind.
Unzipping his jeans, Hank reached into his boxers and pulled out his enormous cock, which was already starting to grow with anticipation. Brian gulped fearfully, even as his mouth unconsciously began to water at the prospect of sucking Daddy's big tool again.
“Please don't,” he pleaded plaintively.
Maneuvering himself before the quivering bedwetter, Hank positioned his massive cock in front of his trembling lips before shoving it forcefully into his mouth.
“MMMGRFF!!” Brian cried as his mouth was suddenly filled to capacity with Hank's gigantic member. The latter pushed it in and out to a rhythm of his own choosing, gagging the poor diapered sissy every time he jammed it down his larynx.
Brian slurped and slobbered over the fat pole, struggling to breath as Mariana bent down and giggled at his predicament.
“That's my little sissy cocksucker,” she said proudly, “This is right where you belong.”
Brian's cheeks flushed red and they bulged as he tried to accommodate the titanic piston forcefully sliding in and out of his mouth. Squealing and whimpering, he struggled as Hank face-fucked him roughly, showing the sissy exactly who wore the pants in this house.
Finally he pulled out, leaving Brian's mouth open as he gasped for air. A string of saliva hung between his lips and the fat, shiny head of Hank's cock.
“Okay, that's enough for now,” he told him, “Come along, little boy, let's go check on your progress with your bedwetting chart.”
Brian gulped hard as Hank grabbed him by the wrist, yanking him to his feet as he headed down the hallway, the whimpering sissy in tow. He knew there were at least ten big red 'W's in a row on his chart and just seven were enough to warrant a spanking. He tried to resist Hank but the bigger man was far too strong. He stumbled behind him, dreading his discovery and the spanking that was almost certain to follow.
As the three of them entered his nursery, their senses were assaulted by the smell of stale pee that permeated the room.
“Whew!” Hank remarked, “I don't know how you can sleep in here.”
“Sissies bedwetters just get used it it, I guess,” Mariana explained casually.
Going over to the large chart on the wall, Hank examined it closely, his features darkening as he counted the consecutive red 'W's over each day of the most recent week, signifying wet night after wet night.
“You really have no more control than a toddler, do you?” he snapped.
Brian quailed before him, but he nodded his head slowly, hoping it might possibly buy him some mercy from his Mommy's intimidating boyfriend.
“I think you need to be taught a lesson,” he said as he walked over and picked up the Spencer paddle with air holes hanging from its peg, “Maybe a good, hard spanking will motivate you to try harder.”
Brian's eyes misted with tears and he began begging Hank piteously to reconsider.
“No—please—please, Daddy,” he whined, “Please don't spank me.”
Mariana walked over and opened the window wide to make sure the neighbors could hear and be witness to Brian's punishment.
As Hank took a seat on the spanking stool, Brian trembled before him, a strong, panic-induced stream of pee suddenly flooding his diapers.
Glaring into Brian's tear-filled eyes, Hank scolded him like a father would his errant child.
“Do you know why you're being spanked today, sissy?”
Brian nodded his head sadly as a tear tumbled down his face.
“Answer me, boy,” he barked.
“Yes Sir—I'm being spanked for my bedwetting,” he sobbed.
“That's right, sissy. And you know you deserve it, don't you?”
“Y-yes, Daddy,” he blubbered.
“Then ask Daddy nicely, if he'll give you a good, hard spanking,” Hank said huskily. His cock was starting to grow hard in his pants again.
“Please Daddy—please spank me hard,” Brian wailed.
“I'd be delighted,” he said with a smirk.
Grasping the sides of his plastic panties, Hank jerked his entire diaper down around his ankles and threw him over his big lap. Brian let out a yelp as he struggled to get his balance, his damp bare bottom waving in the air as if to tease Hank. Without a moment's hesitation, his Daddy brought the wooden paddle down hard, searing a rectangular imprint across both of Brian's tender cheeks.
“YEOWWW!!!” he cried out at the top of his lungs.
Mariana smiled, seeing her sissy hubbie finally getting the overdue punishment he justly deserved.
Gripping Brian firmly, Hank brought the paddle down again and again, swatting his baby-soft cheeks fiercely as Brian kicked wildly and bawled like a child. Unfortunately, his wet diapers were tangled around his ankles, preventing his free movement.
Hank really meant business when he administered a spanking and today was no different. The bedwetting sissy's bottom quickly went from pink to a rosy, red apple shade, welts quickly rising from his stinging hot skin. The hard wood scalded his lily white bottom cruelly, bring tears in profusion as Brian wailed miserably. He tried desperately again and again to escape but Hank held him firmly in place, making sure he received every blistering swat of the paddle.
After what seemed an eternity, Hank finally stopped.
“Have you learned your lesson, bedwetter boi?” he said as he led the paddle poised over Brian's dark red bottom.
The bawling sissy barely manage to utter something that sounded like an affirmative answer and Hank rewarded him with one last bitingly harsh swat of the paddle.
With surprising gentleness, Hank lifted the crying pantywaist up and carried him over to his crib, placing him face down on the mattress with his crimson bottom on display. Brian grabbed his teddy bear and sobbed uncontrollably.
“I think we need to reinforce this lesson,” he said with an evil smirk as he unzipped his jeans and let them fall around his ankles.
Brian was too busy crying to see what was going on as Hank took his nursery jelly and smeared a liberal amount over his hardened cock. It was thick and veiny, rising from his crotch proudly like a mighty, fleshy sword.
Kneeling between Brian's legs, he forced them apart and positioned his massive pole at the sissy's hole. Just as Brian turned to see what was going on, Hank thrust his cock hard against the crying sissy's sphincter. With a slippery pop, he rammed it home, driving the fat shaft deep into Brian's bowels.
“OHHHH!!” he wailed as Hank's big, heavy balls smacked against the sissy's tiny locked package.
Hank let out a sigh of satisfaction as he gripped Brian's hips firmly and began a series of long languid strokes.
“Oh yes,” he said with immense satisfaction, “You have a nice, tight sissy pussy.”
Perhaps the earlier experience with the Sissy Splitter helped because while it was still painful having his back passage stretched wide, Mariana's dildo had prepared the way to some degree.
Still, Brian wailed and moaned like a little girl, feeling like he was being split in two. Hank's warm, slippery cock really stretched him to the limit, and Brian cried out every time he bottomed out inside his tortured boi pussy.
Mariana had moved around the end of the crib to gaze down at her hubbie being so thoroughly impaled.
“Feel that, sissy? That's a what a real man's cock feels like.”
Clutching his pink teddy bear for comfort, Brian was sure his hole would never be the same again. Sobbing like a child, he was completely helpless to prevent being forcefully raped by the larger man. He squealed and cried, and occasionally, Hank would slap the right side of his red bottom for good measure.
Finally, Hank gripped his hips with renewed vigor and rammed his cock deep into Brian's rectum.
“UGHHH!” he bellowed as he blew his warm, creamy load deep inside the squirming sissy.
With a shudder, Hank's eyes screwed shut as he relieved a week's pent up tension and semen into the captive bedwetter.
The next few minutes were a haze to Brian as Hank pulled out and Mariana led him over to the changing table for a fresh set of diapers. He was giving his baby bottle as Mariana gently applied cool Desitin to his stinging, fiery cheeks and pinned him into a soft, fluffy set of diapers. After pulling on some pink rubber panties, she swapped out his baby dress for his cropped fleece jammies, a bunny motif decorating the chest.
Gently tucking him into his crib, Mariana brought his fuzzy baby blankies up around him, setting his teddy bear underneath his arm.
“There, there,” she cooed softly, “You've had a big day, time for an early beddie-bye for Mommy's little baby.”
Brian was exhausted from the evening's events and his long lashes grew heavy as he nursed from his bottle of warm milk. Before long, his Mommy was turning out the light, although she left his door open so that he'd be able to hear their lovemaking if he woke up later.
Despite the intense, painful throbbing of his bottom and back hole, within minutes, Brian slipped off to sissy slumber, his half full bottle coming to rest against his pillow.
As the pantywaist entered into the dream world where all sissies are happiest, the floodgates opened up and warm pee spread throughout his diapers. In moments, they were completely soaked, meaning Brian could look forward to yet another red 'W' on his chart tomorrow.
THE END
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He thought it was what he wanted, he really did. Ever since Christian was little, he enjoyed playing with dolls. Not so much because he liked to do what girls do–well, he did–but more that he wanted to be the doll. They got to wear pretty dresses and have their long blonde hair put into bows, their cutesy shoes switched out, and they got to be pampered and adored by someone else.
Speaking of pampered, Christian seemed to always gravitate towards the dolls that needed diapers. The ones that would squirt fake wets and messes so he could change them. He remembered begging his Mother for those toys.
His Mother knew that Christian would most likely not grow up to be a very strong, masculine boy. She knew her son was not like the others, he’d taken far too much interest in all things feminine, but she also never saw anything wrong with that. She would oblige him if he asked her to paint his nails, or put make-up on him, or make his hair curly. She thought it would be a phase, something he’d grow out of when he got to high school.
But college came and went and Christian was still living in her basement. She could hear him at night, making loud, pathetic mewling sounds. Watching god knows what on the internet and doing god knows what to himself. She found countless diapers in the trash can that Christian did a pisspoor job of hiding. When a bra or panty set went missing, she knew the first place to look was in Christian’s room tucked into the back of his closet. She never said anything, though. She let her boy partake in his little fantasies and work himself raw. She’d change his sheets that only had a hint of piss soaked into them, as if most of it ended up somewhere and this was only what leaked out when a certain item had reached capacity.
Christian had spent most of his life jerking off to sissy and abdl and feminization porn. He’d watched countless hypnos that made his brain rot, he even put his own penis in a cage sometimes and learned to cum like a ‘gurl’. But all of that was only when he was in the throes of hornydom. He’d dream of being a pretty little doll for someone, to get put in diapers and dresses and makeup and be ‘forced’ to live life as a little sissy bimbo. This, obviously, didn’t do much for the ladies, so he never had a true girlfriend.
So one day, Christian decided after 5 days of depriving himself of orgasms, that he was finally going to come out to his Mom. He was going to tell her about how he’s a sissy, how he likes to wear diapers, and be treated like a baby. He was tired of keeping all of this shoved down and tucked away for so long.
It felt so freeing to finally tell her. To let her know everything about what her son was secretly doing. But, apparently, it wasn’t much of a surprise at all. She hardly blinked an eye, and instead just smiled like a mother patiently waiting for her child to correctly solve what 6+8 is, and congratulating him for finally getting it.
“So you want me to treat you like a little sissy baby?” she asked, clarifying.
“Well, no…” he said. Or, at least, that’s what he wanted to say. Instead, he was awestruck by the idea, by the possibilities. He could finally get what he wanted! He could have someone treat him like the sissy baby gurl he’d always wanted to be! “Yes!” He said for real, “Very much yes!!”
His mother only laughed. “Are you sure that’s what you want? I mean, when will it stop? How long do you want to do this?”
“Forever.” He said, a single word sealing his fate. If he knew what he knew now, he would have never uttered that word.
“You’re sure?”
“Yes.” Okay…maybe he shouldn’t have said that one either.
So started Christian’s journey into sissy depravity. His mother pulled out all the stops, showing no mercy. Like a stern parent raising her child once more, she kept him in line using discipline, time outs, and a new one most mothers can’t use: chastity denial.
She watched as her son slowly transformed into a babbling, drooly mess. She wasn’t sure if it was the hypnosis she’d been making him watch, or all the toddlerish TV shows. He wasn’t allowed to play his video games any more, something he threw quite the little tantrum over. Instead, he was given blocks and rattles and (if he was good) some of his favorite dollies. She didn’t have to cook much, Gerber took care of all his meals. She’d shovel pureed prunes and peas into his mouth and wipe up the contents to shove back in. She didn’t think she’d ever be changing Christian’s poopy diapers again, yet here she was.
But after only a few short months, she started to notice even more of a change in him. He became more reclusive, more whiny, more tearful.
“What’s wrong, pumpkin?” she asked, drying Christian’s eyes with his food splattered bib.
“I on’t wanna be uh baby anymore!” he cried.
But his Mother showed no sympathy. “Awww!! Well that’s too bad, hunny! This is what you wanted! Remember? You wanted this to be forever.”
Christian looked up at her with his little doe eyes, like he knew he’d made a grave mistake.
“I guess this is as good a time as ever to tell you…” Mother said, clearing her throat, “I’ve arranged for you to have a little…procedure.”
“Puceedur?” Christian could hardly get the words out, his brain was so numb.\
“Yes honey. You know those little princess parts between your legs?”
He looked confused.
“The ones inside your pampers.”
That seemed to make sense to him, anything involving diapers was easy to get his head around.
“Well you see honey, this procedure, this operation is going to take those away!”
His eyes went wide, but he still looked hazy. Like he could only slightly understand the gravity of the situation. It took several more seconds to finally sink in.
“B-b-but…I on’t wanna lose my princess parts!!”
His mother just shrugged, arms crossed. “I’m afraid it’s too late for that, dear. You wanted this, and I’m just supporting you.”
She pulled a bottle from the bag, shaking it with her finger over the nipple, then brought that nipple to Christian’s lips.
“Drink up, honey!” she said softly, “This has all the ingredients to help you become the wittle baby gurl you’ve always dreamed of being!!”
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Image is from @littlepinkss
Text written as a commission by wittlesissybab3 on Twitter.
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