diaperpantysissy - Tumblr blog

diaperpantysissy · 1 year

Text

Sissies Get Spanked!

Nearly six months to the day after I received a very generous pay raise from the law firm I work for, I completed an important goal of mine; the conversion of one of my spare rooms to a baby’s nursery. No, I wasn’t planning on getting pregnant, this was intended for something else entirely. Although at first glance, it looked very much like that of any typical toddler girl’s room, a closer look revealed the distinctive differences; the pink and white crib, as well as the playpen were large enough to contain a small adult, and all the clothing was similarly sized larger. From the stacks of fluffy diapers, to the many sets of plastic panties and the dresses filling the closet, these were big enough to fit an incontinent sissy of larger proportions.

All it needed, was an occupant, and for that, I already had someone very specific in mind.

Tim Johnson (I called him Timmy) worked at the local Frederick’s of Hollywood, about a mile from my house. He was short, about 5’ 5”, with a frail body, and he looked like all it would take, would be for a strong wind that could blow him down. Although he was of average looks, he had baby blue eyes that I found quite endearing and his mop of blonde hair gave him a certain feminine air.

The first time I met him, he couldn’t look me in the eye and he stammered helplessly to my demanding questions. I caught him staring at my deep cleavage and he blushed furiously when I smirked and asked him if he liked what he saw. I flirted with him but he was clearly overwhelmed with a woman of my caliber. To be fair, even a modest appraisal of my capabilities put me far outside of his social class, with my model looks and statuesque frame. At 5'10” and in my heels, I easily towered over the poor wimp and he was forced to crane his head to look up at me. I particularly enjoyed seeing him stare dumbfounded at my impressive bosom which was at his eye level.

It was Timmy who first inspired me to build the nursery. And although for years I had always had a vague idea formulating in my mind to dominate a sissy, it wasn’t until I saw the panty lines under his slacks that I realized he would be the perfect candidate to turn into my very own baby girl. Sometimes, when he would stutter and blush before me on one of my many shopping trips to the store, I would imagine him bent over my lap while I paddled his bare bottom to a cherry red. The idea of making Timmy cry like a baby made me wet with arousal and I knew it was only a matter of time before I made my dreams come true. I chuckled to myself as I pondered ensnaring the unsuspecting weakling and making him submit to me.

And though I knew he had a thing for wearing women’s panties, little did he know that he would be trading those for plastic or rubber panties, pulled up over a nice, thick set of diapers…

I went back to Frederick’s on a slow weekday, knowing I’d have the store and Timmy all to myself. Going to the bra section, I started opening drawers when I saw Timmy standing nearby and trying hard to act like he wasn’t leering at my busty profile. Turning to face him, I snapped my fingers crisply.

“Timmy—I want some help here,” I told him in my commanding voice.

The sissy nearly jumped, and I could see he was blushing a bright red as he came closer.

“Y-yes ma'am?” he quivered nervously.

I regarded him with a smile like a kid with a magnifying glass looks at an ant he’s about to fry.

“I need a size 34HH—do you have any in that size?”

The sissy swallowed hard and his face got even redder.

“Um-I, um, I think…” his voice trailed off as he averted his gaze to rifle through the drawers, his hands trembling in search of the size I wanted. Clearly, he was extremely intimidated by my presence and I leaned down closer to watch him squirm uncomfortably. The cream colored silk blouse I was wearing was unbuttoned about halfway down, revealed the deep chasm of my cleavage to further befuddle the wimp.

Finally, he pulled a large red bra out of the drawer and held it before me in his shaking hands.

“H-here y-you go,” he stammered.

Taking the silky lingerie from him, each of the cups the size of his head, I held it against my chest.

“What do you think? Suppose it’ll fit?” I asked him with a haughty, superior tone.

His cheeks flushed a bright crimson as he gulped and stared dumbfounded at my enormous, proud bosom.

“Um, I-I think so,” he squeaked.

Turning on my heel, I went into the nearby changing room and stripped off my blouse and bra to try it on. I could only imagine the emotional trauma Timmy was going through as his imagination ran wild. The bra cupped my heavy breasts very sexily, the underwire lifting them into two big, bountiful mountains.

Drawing the curtain open, I stepped out of the changing room and walked over to where Timmy was standing nearby, fidgeting nervously with a display.

“What do you think?” I said as I placed my hands on my hips and thrust my breasts out before his face, “Do you think a real man would find this sexy?”

Timmy gasped and it looked like his eyes were about to pop out of his head as his cheeks reddened again. And no doubt, he was ashamed at the implication that he obviously wasn’t a real man in my eyes.

“I-uh…I-um, well…” he babbled.

“Timmy–are you wearing panties!?” I said suddenly, my voice taking on a stern, accusitory edge.

Completely caught off guard and unprepared for my question, the pansy could only blush and look around, unsure how to respond.

“N-no, No, I’m not,” he stuttered although I could easily see he was lying.

“Timmy—are you telling the truth? Because I put liars over my knee and spank them.”

His eyes went even wider and I thought he might wet his pants in fear.

“I’m going to ask you once more and you’d better tell the truth. Are you wearing women’s panties?” I snapped.

His cheeks and chest were the color of an apple but he shook his head vigorously as his lips trembled uncertainly.

“N-no-no!” he quaked and he backed up slightly as if looking to escape.

With a swiftness he wasn’t prepared for, I reached down and rapidly unbuttoned his slacks, even as he tried desperately to stop me. We struggled briefly but it was obvious he was no match for my superior strength. Dropping his pants in a curtain around his calves, I stared at the frilly pink see-thru panties he was wearing and trying so hard to hide from me as he squealed in anguish. Whereas any other guy would have had a pronounced bulge in his underwear, Timmy’s ‘package’ looked like a tiny cap, about the size of a thimble, protruding straight out in a pathetic wet pool of pre-cum.

“Well, well, well,” I said gravely, “Looks like we have a pantywaist here.”

Before he could respond, I grabbed him by the wrist and yanked him over to a nearby stool. With his pants around his ankles, he stumbled clumsily and I threw him over my lap like a child.

“Timmy—you’re nothing but a big sissy and I’m going to give you a good, hard spanking,” I growled.

Timmy wailed and struggled against my grip but he was completely helpless.

“No! Stop it!” he cried, “Let me go!!”

Whimpering like a little girl, he kicked and thrashed over my lap as I swiftly removed a wooden paddle from my purse. Protesting wildly, he begged me to let him up but I responded by bringing the paddle down as hard as I could, searing a pink oval pattern across his bottom.

“YEOWWW!!” he cried, just as I swatted him again.

The thin, filmy panties provided absolutely zero protection and my paddle rained down over and over against his defenseless cheeks. He immediately burst into tears and began bawling like a toddler. With each scalding swat against his red bottom, Timmy elicited another piteous wail of agony and I felt my womanhood becoming wetter by the minute. He renewed his desperate effort to escape from off my lap but I held him like a vice and smacked him even harder.

Fortunately for Timmy, the mall was closing down soon and few people were around outside to take notice of his humiliating punishment. Still, as mortifying as that was, it was doubtful he could think of anything else beyond my avenging instrument of discipline. The sheer material of his panties revealed his dark red, blotchy cheeks where angry welts soon covered the entire surface. Moving my attention to the sides of his rear, I blistered it until it matched the fiery color of his seat. His cheeks danced miserably beneath the punishing assault of my paddle and I returned my attention back to the center to make absolutely sure he wouldn’t be able to sit down for the better part of a week.

Finally, I stopped spanking him and I slipped the paddle back into my purse. He was bawling unashamedly and I easily lifted the sobbing sissy off my lap and stood him before me, looking hard down into his wet, crying eyes.

“Timmy—you are to come over to my house this evening. Be there at seven sharp,” I ordered him as I gave him a slip of paper with my address.

He held it in his shaking hands but couldn’t get his crying under control so I slowly lifted his slacks back up for him.

With that, I put my blouse back on, grabbed my old bra, and strode out of the store like a victorious, conquering queen. Needless to say, I didn’t pay for the new bra.

I waited anxiously at my house as the afternoon slowly rolled into evening. Would Timmy actually come over? I couldn’t be sure. Any other guy with a modicum of dignity would have outright refused after having his bottom soundly paddled but Timmy? My gut feeling was that he was so weak and submissive that he would acquiesce, even if it meant enduring further humiliations and degradations. After all, this was his one and only opportunity to spend time with a woman of my social standing—and I was sure he would be unable to pass up the opportunity. He probably thought he’d be able to brag later on to all his sissy friends about how he’d been invited over to the stunning knockout’s house. Little did he know what I had in mind for him…

And then sure enough, at 6:58, I heard my doorbell ring.

Walking slowly down the hallway, my five inch heels clicked loudly on the wooden floor, announcing my commanding presence to the timid sissy. Opening the door, I looked down at the nervous little pantywaist, my hands on my curvy hips. I had slipped into a fitted halter top that hugged my massive breasts like a second skin and left a plunging cleavage to make Timmy salivate.

“Come in, Timmy,” I said graciously, allowing him to walk past me into the foyer.

“P-please—y-you can call me Tim,” he squeaked.

“Come in, Timmy,” I repeated, deliberately ignoring his preference, “Is your bottom sore?” I asked with a chuckle.

“Yes ma'am,” he answered meekly, “Please don’t spank me again.”

“You’ll get a spanking anytime I feel you need one, and regardless of the company present,” I told him firmly, in my superior, maternal tone of voice.

He gulped hard and shivered anxiously but he was too intimidated to actually argue with me.

“Come along, Timmy,” I said taking his hand, “I’m going to show you your new room.”

“M-my new room?” he asked uncertainly.

“Yes, I’ve created a baby’s nursery that will be your new home, complete with everything a little sissy boy like you could ever want.”

Timmy didn’t know what to make of that but when he entered the room, his jaw dropped open in shock. Looking around the room, his gaze took in the pink and white baby’s crib, large enough to fit his semi-adult frame, a playpen with stuffed animals just waiting for his company, a pink horsey rocking chair, and a glossy pink dresser packed with onesies, diaper tops, anklet socks, tights, and plastic panties. A row of Mary Janes were lined up in front of the dresser in black, pink, yellow and white. More ominously, a pair of Spencer paddles were hanging up on the wall behind the dresser, making Timmy quake with fear.

As Timmy took all this in, I picked up a large rubber pacifier and brought it over to him. The business end was taken from a fat jelly dildo, that was wider in the middle and slightly tapered near the mouth guard. I positioned it before Timmy’s mouth and began gently pushed the cock head between his trembling lips. He was so weak-willed and submissive, he simply whimpered and opened wide to accept the pacifier as he looked up at me fearfully with his baby blue doe eyes.

“This should come as natural to a pantywaist like you,” I told him as the faux cock completely filled his mouth, eliciting a muffled squeal of panic from him.

“Now that pacifier stays in until I remove it. Under no circumstances are you allowed to take it out unless I tell you—do you understand?”

He nodded in fear, clearly afraid to stand up to me.

“Now I know you have a thing for women’s panties but that just doesn’t work for me. A sissy like you belongs in diapers and plastic panties and that’s just what I’ve got waiting for you.”

Timmy balled his fists and adamantly shook his head, his fervent protests effectively muted by the fat rubber cock filling his mouth.

“But first, there’s a little something we need to take of,” I said as I began undressing him. He squealed again and tried to resist but the skinny weakling was no match for me and soon, he was stripped down to his sheer, pink panties and sitting on the raised changing table looking helpless and vulnerable.

Walking over to the dresser, I picked up a small steel device and brought it over to Timmy. It was a special chastity restrainer called the Sissy Tamer and was renowned for its foolproof security. Pulling his panties down, Timmy squealed as I took in his tiny little package critically. It really was incredibly small, only the head of which protruded from his groin like a mushroom head. Fortunately, the Sissy Tamer had a 3” flexible urethra insert that would make sure after it was locked in place, Timmy would have no way to be able to remove the chastity device.

I unlocked the cap-shaped cage from the cuff ring, taking the latter part and pulling Timmy’s shy little sack and head through it.

“I hope your last orgasm was a good one when you were jerking off in your panties because it was the last one you’ll ever get. Sissies like you need strict chastity control and that’s exactly what I’m going to give you,” I beamed down at him, “Whereas before, we both knew you were a pussy-free pantywaist, now I’ll make sure you’re orgasm-free too.”

Timmy’s blue eyes were filled with fear and he whimpered helplessly around his cock pacifier as I prepared the other part for insertion. Dabbing some Surgilube on the rounded tip of the urethra insert, I positioned it before Timmy’s quivering little head.

“Say goodbye to erections, Timmy, however pathetic they must have been. This will keep you soft, safe, and secure,” I said eagerly as I began slowly pushing the small insert into the tip of his tiny dick. He squealed in panic and flailed his hands as the tube gradually began to disappear into his stubby little shaft.

“This is just what a sissy masturbator like you needs. You’ll probably be frustrated and horny for the first month or two but eventually, you’ll get used to doing without cumming and living a chaste lifestyle. This will teach you that orgasms are for real men and not sissies who wear panties and like to play with themselves.”

Timmy sucked desperately on the fat rubber pacifier filling his mouth and his eyes darted about anxiously.

“I’m told that this chastity device was specifically designed for determined pantywaists who will do anything to free their little dicks, but short of a metal saw, your tiny penis is staying right where it belongs—locked up where you can’t play with it anymore,” I explained.

At last, all three inches of the flexible insert tube were inside of Timmy and the steel cage was capturing his tiny head, compressing it against the cuff ring. I slipped a long key in the back and locked the device securely in place.

“There!” I said enthusiastically, “Perfect. And now—it’s diaper time!”

Timmy shook his head bitterly and protested his disapproval but the imposing rubber cock stuffed in his mouth kept it all unintelligible.

Arranging a thick stack of diapers one on top of the other, I unceremoniously raised Timmy’s feet over his head and slid them under his red, still-stinging rump. Squeezing out a big glob of Desitin in the palm of my hand, I smeared it across his swollen cheeks, making sure the sissy got a nice, sticky coating of diaper rash cream.

Timmy’s cheeks reddened with shame as he experienced this very babyish ritual, helpless to oppose me.

Sprinkling baby powder generously over the front of his groin, the babyish scent surrounded us and I smiled down at him as I brought the fluffy soft cotton up to secure the sides with two pink, duckie-headed safety pins.

“Doesn’t that feel nice, sissy boy? Most pantywaists never forget their first diapering. And before long, they’ll feel as natural as your frilly panties used to feel. And don’t worry—I’ve got plenty of diapers for my little pantywaist to wear and wet every single day!”

Timmy gulped hard at the prospect.

Shaking out a pink pair of nursery print plastic panties, I worked them over his feet and began pulling them up his hairless, skinny legs.

“Timmy, just imagine if your mommy could see you now,” I said with an enthusiastic smile, “I’ll bet she’d wholeheartedly agree with you being put back into diapers–they really do suit your weak, prissy personality, don’t they?” I asked him rhetorically as I pulled the stretchy elastic waistband up and over the fat bulk of his fluffy diapers.

Timmy looked away in abject humiliation, unable to respond with anything other than babyish gurgling.

Standing back up, I went over to the closet and carefully selected a pink and white gingham dress, purposely cut short to make sure Timmy’s diapers would be left clearly on display.

“Raise your arms, sissy,” I said tersely and Timmy lifted them up so I could drop the lacy confection over his head. It had short, puffy sleeves that accented his frail, effeminate body and a Peter Pan bodice.

“Isn’t this the cutest little thing, Timmy? And I’ve got tons of other pretty, frilly outfits for you too,” I told him as I slipped some lacy white anklet socks over his feet and followed them by buckling on a pair of glossy black Mary Janes.

Pulling him to up to stand, I brought him over to the mirrored closet doors to face his reflection. Patting the thick, bulky seat of his diapers, I smiled as I stood over him, proud of my transformation of the timid little sissy boy.

As he took in his babyish reflection for the first time, tears of humiliation filled his eyes and for a moment, I feared I had gone too far. Turning him to face me, I hugged him tightly, mashing his face against my big, soft bosom.

“Oh, you look absolutely adorable!” I exclaimed, hoping my words would help comfort him. Failing that, having his nose buried between my big breasts had to have been some consolation for the trembling, defeated pantywaist.

Taking him by the hand, I led him out to the kitchen and physically lifted him into a stout highchair. It was hard to imagine he weighed much over a hundred pounds and it must have been particularly humiliating for him to be lifted up so easily like a small child.

After securing him with a waist belt, I locked the serving tray in place, effectively trapping the confused sissy. Taking a baby bottle from the warmer, I removed his pacifier and pushed the wet rubber nipple between his lips.

“Drink this all up, Timmy—it’ll make you grow up big and strong,” I told him with a sarcastic chuckle.

Actually, the warm milk was loaded with powerful diuretics I had mixed in which would soon have him helplessly wetting his diapers like a baby before long.

Timmy mewled submissively as he nursed from the bottle. I smiled down on him and caught him staring hungrily at my deep cleavage.

“You like Mommy’s boobs, don’t you?” I asked him coyly.

Timmy nodded his head enthusiastically.

“You can look all you want but you don’t get to touch,” I warned him, “These are for a real man, not a diapered sissy like you.”

Timmy frowned, looking like puppy who had been swatted with a rolled up newspaper.

After tying a plastic baby bib around his neck, I proceeded to spoon feed him some canned spaghetti which soon became a sloppy mess around his face, due to my frenetic pace. Some ended around his mouth, some on his nose, and some got smeared on his chin. By the time he was finished, he was an absolute mess.

After dinner, I cleaned him up and let him out of the highchair, taking him to my sofa where I made him nurse from another full baby bottle of warm milk. The poor sissy was beside himself with arousal as I cradled his head with my free arm, positioned his head mere inches from my bountiful bosom. His eyes wandered desperately over my soft curves and he shifted uncomfortably on my lap as his chastity device effectively restrained his tiny, throbbing penis.

“Well, it’s about 8:30. Looks like it’s baby’s bedtime. Let’s get you changed into your jammies and ready for beddie-bye,” I said as I lifted him up.

Timmy pouted, but he seemed to know better than to argue with me—I’m sure his bottom was still sore and tender from his earlier spanking this afternoon. Leading him to the nursery, I removed his dress and exchanged it for a fleece Disney Princess-themed top. It had short sleeves and an even shorter hem, which would come in handy in case Timmy’s diapers leaked. Which made me think to inquire.

“Timmy? Are your diapers wet?” I asked him sweetly.

He blushed with shame and looked at the floor.

“N-no, Ma'am,” he squeaked.

Taking his chin, I turned him up to face me.

“Timmy—from now on, I want you to address me as ‘Mommy’. Understand?”

“Yes Mommy,” he replied dutifully.

“Good boy,” I said with a smile and I took off his Mary Janes and tucked him into the crib, arranging his baby blankets around him but not before giving him a comforting teddy bear to snuggle with. Turning on the mobile over his head, childish music softly filled the room and with one last look at my cherubic sissy captive, I turned the lights out and quietly closed the door.

The next morning, my friends Anna and Gina came over at 8:00, to join me for coffee and croissants, as well as making for a nice little surprise for Timmy. We crept into his room as sunlight was filtering through the pink, gauzy curtains and I quickly became aware of the the pungent smell of pee that surrounded his crib. The girls burst out laughing as they took in the sleeping sissy and Timmy woke with a start, looking both confused and frightened.

“Good morning, Timmy!” I beamed down at him, “How did Mommy’s little baby sleep?”

He gasped audibly and clutching his teddy bear tightly to his chest, looked about the nursery in a panic, both unsure of where he was and clearly mortified to be exposed under these humiliating circumstances.

“Come on Timmy, let’s check my baby’s diapers. Did Mommy’s little boy have a dry night?” I cooed.

Timmy’s face went bright red as my fingers slipped inside the elastic waistband of his plastic panties and I felt the warm, wet diapers underneath.

“Well, well, well,” I said with a smug smile, “Looks like I’ve got a little sissy bedwetter on my hands.”

“I-I-I don’t know how it happened,” Timmy quaked, looking like he was close to tears.

“That’s okay, sweetie,” I said as I guided him out of the crib, “Most sissies have little or no control which is just one reason why they need diapers and plastic panties. We’ll get you changed after breakfast.”

Timmy was deeply ashamed as my beautiful friends took in his infantile diapers, with their pink nursery-print theme and the equally childish Disney Princess top. It seemed like the contrast of their very adult clothing only served to intimidate the trembling sissy further and his cheeks and chest blushed furiously.

I introduced him to my friends, who treated him with the same respect one would for any incontinent toddler.

“Aren’t you a cute little sissy boy!” Anna exclaimed.

“Those diapers sure came in handy, didn’t they, baby Timmy?” Gina giggled.

Timmy’s eyes misted with tears of humiliation as he sat before three beautiful, sophisticated women, looking like a prissy toddler in his soaking wet diapers.

Once more, I led him to the kitchen and lifted him into the highchair, giving him a nice, full bottle of warm milk to start his day with. My friends enjoyed teasing the poor sissy until he appeared to be on the verge of tears again.

“You’re so short—you look more like a little boy than an adult,” Gina commented.

“You must be a real sissy if you’re still wetting the bed,” Anna added, “I had a little brother that wet the bed all throughout his teens. He didn’t graduate from his diapers until he was 18.”

After another messy feeding, I left him trapped in his highchair while I prepared a nice, soapy, two quart enema to properly start his day with. Having given this a lot of thought beforehand, I had previously discarded the standard enema nozzle and replaced it with a much bigger dildo type. It was very fat, and at eight inches long, I was certain it was going to make Timmy squeal like a little girl.

Leading him back to his nursery, I lowered his plastic panties and took him over my lap as the other two watched closely.

“Now Timmy, part of being my little baby means getting a nice, soapy enema every day,” I explained patiently as I unpinned his sopping wet diapers and pulled the soggy cloth back, “Not only will this keep my little sissy squeaky clean, but it will also drain out a lot of your useless, built up semen. Your little balls will tend to get full from never cumming and they need to be drained from time to time.”

The red faced sissy whimpered and pleaded desperately to be spared this humiliating indignity but I simply ignored him and stuffed a dollop of Vaseline into his quivering pink hole.

“This dildo nozzle is really thick. So thick that I think I’m going to need to prep your little pussy with a medium sized dildo to get you properly relaxed,” I explained as I pushed the medium-sized rubber cock in my hand against his puckering sphincter.

“No! No!” he squealed as his hand jerked back to try and stop me.

“Gina—do me favor and hold his wrists for me?” I asked as I pushed harder against his hole.

With a slippery pop, I buried the greasy dildo deeply into his rectum, twisting it and sliding it back and forth. Meanwhile, Gina was firmly holding Timmy’s arms, preventing him from interfering with me and I took my time, teasing his tight virgin passage with the jelly dildo.

“There…doesn’t that feel wonderful?” I asked him sweetly, “Tell me, sissy; how many nights have you laid awake in your bed, rubbing your tiny dick through your panties and wishing a big stud would do this to you?”

Timmy’s face flushed red and I suspected I had hit a shameful secret of his.

“Mm-hm. And I’ll bet in the school locker room, you would stall and try to sneak peeks at the more well-endowed boys, didn’t you?”

“No!” he bleated weakly and unconvincingly.

He struggled against Gina’s grip, looking away and unable to escape her leering grin.

After several minutes, he seemed to relax a bit and his eyelids grew heavy as a low moan escaped from his lips.

“Mm-hm. I think baby’s ready for his enema nozzle now,” I said with a big smile.

Slowly removing the medium sized dildo, I put it aside and grasped the heavier enema nozzle. This was one was truly titanic and I could barely get my hand around its circumference. After liberally greasing the fat cock head, I positioned it against his quivering hole.

“Take a deep breath, Timmy, this one is really going to stretch you,” I told him as I began pushing against his gaping pussy hole.

He squirmed on my lap and squealed as he tried to resist the massive phallus pressing urgently and insistently against his back hole.

“Just relax and submit, it’ll go in much easier,” I told him, “But like it or not—you’re going to be getting this everyday.”

He struggled mightily against Gina’s grip and squealed loudly as the mammoth dildo bulldozed into his tight but slippery passage.

“OHHHHH!!!” he wailed.

Fortunately, the dildo nozzle was made from another jelly dildo and was therefore, very flexible. Still, I could see his little hole was being stretched to capacity and the mighty rubber cock was filling him like he’d never been filled.

“How does that feel, my little sissy bedwetter?” I asked him, “I’ll bet you’ve dreamed of this for a long time.”

Gina grinned broadly as she stared Timmy in the face, watching as I slowly pushed the monster cock deeper and deeper into his bowels. He could do nothing to stop me and the feeling of fullness must have been overwhelming. Once more, I twisted it a bit, then pushed it in, pulling it out a few inches, before pushing it back in as far as it would go. Timmy moaned helplessly, his ass being stretched wide as far as it could go. I kept up a slow, tortuous rhythm, pulling the massive nozzle out and then slowly sliding it in. Every time it bottomed out, I pushed harder just to make sure Timmy got every punishing millimeter of the fat, rubbery cock.

Soon, the pantywaist was breathing hard and moaning helplessly and appeared to enjoy having his sissy pussy filled. By now, his cum was undoubtedly dribbling uselessly out of his chastity device, adding another mess to his soggy wet diapers.

Without warning, I released the clip on the hose, and a mighty torrent of warm water surged strongly into his bowels. Timmy’s eyes went wide and he squealed again as Gina gripped his wrists tightly and grinned broadly in his face.

He moaned as the water flowed unimpeded, helpless to stop his purging. Bunching his fists and gritting his teeth, he breathed heavily while Gina and Anna smiled down on the captive weakling.

“Theeere, my little sissy boy, “ I smiled as I patted his damp bottom, “This is just what you need. Two full quarts for my little bedwetter boy.”

Timmy gasped and struggled weakly against Gina’s grip.

“Now Timmy…I think you and I both know, deep down, just how much you really need diapers…” I said as I patiently manipulated the enema clip.

He bit his lip as he felt the warm soapy water churning uncomfortably inside him.

“Tell me, have you ever wet your pants?”

Timmy let out a low moan as he struggled to deal with the volume of warm water filling him up but after several moments, he nevertheless slowly nodded his head.

“I can’t hear you, sweetie,” I said as I released the clip again, forcing the squirming sissy to gasp and struggle against Gina’s grip.

“Y-yes, Mommy,” he whimpered weakly.

“Mm-hm, just as I expected,” I said as Gina and I smiled knowingly at each other.

“Well, a sissy like you belongs in diapers and baby panties and you can count on that from now on,” I told him.

“Y-yes, Mommy,” he replied submissively.

Finally, the last of the enema flowed into his stuffed rectum and he lay across my lap, gasping helplessly.

“Okay little pantywaist—go release that and then I’ll get you dressed for the day,” I said as I helped him struggle to his feet.

He quickly tried to hide his locked up penis from everyone’s view with his hands and I chuckled as he fled the room. After he’d left, I plopped his wet diapers in the diaper pail and turned to my friends.

“Well what do you think, guys? Isn’t he just the perfect sissy?”

“Without a doubt,” Anna agreed, “And he’s so cute!”

“Looks like his bottom got quite a spanking,” Gina remarked thoughtfully.

“Yes—I did it right in the store where he works at–right out on the sales floor where anyone could see,” I winked at them.

They both burst out laughing.

“Did he cry?” Anna asked.

“Oh yes—right with the very first swat, he started bawling like a baby,” I explained, “So after that, I really paddled him hard.”

The others giggled again.

“You know, this boy seems like such a simpering pantywaist, I’ll bet we could have some fun with bringing Jeff over,” Anna said, referring to her kinky boyfriend.

A smile grew on my face as I looked back at the others.

“Oh yes, I can think of a few things that would be fun,” I said mischievously.

About five minutes later, Timmy came back into the nursery, his hand still shyly covering his crotch and he couldn’t bear to look us in the eyes.

“All done, sweetie?” I asked him.

“Y-yes, Mommy,” he whispered.

“Okay baby—let’s get you back into your diapers before you have another accident,” I said as I sat him down on a thick stack of fluffy diapers that I had already arranged on the changing pad. He whimpered and weakly tried to stop me from moving his hand away as my friends looked down and giggled at their first sight of his little locked penis.

“Oh my god—that is one tiny little shrimp dick!” Anna exclaimed in shock.

I quickly pushed a bottle of warm milk between Timmy’s sputtering lips before he could mount any sort of defense.

“It’s the smallest I’ve ever seen in my life,” I admitted as the two others bent down to take a closer look.

“Wow—you really do belong in diapers,” Gina marveled.

Timmy immediately flushed a deep red in shame.

“Yes, he really is just a baby in many ways,” I told them, “And now his tiny nub is locked away for good. No more orgasms for this pantywaist—just secure, permanent chastity.”

The girls laughed and I began powdering his hairless crotch as Timmy frowned in frustration, his cheeks blazing with humiliation. The distinctively babyish scent of the Johnson’s baby powder surrounded us, further reminding everyone of the gulf of maturity between ourselves and Timmy.

“There baby, some nice, soft diapers for you,” I cooed as I brought the thick, bulky cotton up between his legs and pinned the sides together, “Right where a sissy bedwetter belongs.”

Timmy’s cheeks went an even deeper red at the mention of his earlier act of shame.

“Now let’s find some fun plastic panties for you to wear. The girls know just how much you like your sissy panties so let’s see what we can find…

“Oh—how about these?” I said, holding a white pair with colorful polka dots before him, “These will look wonderful with the baby dress I have in mind for you.”

I snaked them over his feet and then drew the soft vinyl panties up his hairless thighs, silently reveling on just how smooth and girly his legs were.

“Here you are, sissy boy, these will keep your peeing right where it belongs and prevent any leaks,” I told the blushing wimp as I wrestled them over the fat but soft bulk of his diapers, running my fingers around the elastic waistband to ensure all the cotton was inside.

Standing up, I went over to the closet and brought back a short, virginal white dress with pink satin accents and lace. It looked like something a three year-old girl would wear to communion. Unbuttoning the back, I dropped it over his head as he gazed away, unable to look any of us in the face. Helping him to stand, I turned him around and efficiently buttoned the double row in back as the others beamed at him, which only embarrassed him further. Lastly, I helped him into his glossy black Mary Janes which I dutifully buckled in place, before standing back to look at my handiwork. Timmy shifted his feet anxiously, tugging in futility at the short, ruffled hem of the dress, hoping in vain to hide his fat sissy diapers.

“I know—I’ve got just the thing!” I said as I went over to the pink dresser and returned with a some pink lip gloss.

“Pucker up, Timmy,” I giggled as I applied a glossy coating to his pouting lips.

As he unconsciously batted his long lashes shyly before us and blushed, I had to admit he made a very pretty sissy.

“My my,” Gina said impressed, “You are the cutest little thing.”

Even though Timmy was deeply humiliated to be dressed up like a toddler girl, never in his life had he been given this sort of positive attention from a trio of stunning females. He reddened bashfully and aimlessly shuffled his feet.

“Okay, Babykins, why don’t you play in your playpen while the adults have some coffee,” I said as I led him over and had him step into the mesh sided enclosure. He sat down submissively and I gave him another bottle to nurse from.

Anna smiled as she bent over the padded rail of the playpen, looking down on the diapered pantywaist, “Such a sweet little sissy.”

I started the mobile over Timmy’s crib and childish music again filled the nursery that I hoped would sooth him. The three of us left the room, leaving him to play with his dollies and nurse from his bottle.

Timmy had his first daytime accident later the very next day (this following another bedwetting incident when he woke up in his crib that morning having helplessly wet his diapers again for the forth night in a row). In a routine that would become the pattern for him, I fed him breakfast in his highchair, administered his morning two-quart enema, changed his wet diapers, and dressed him for the day. Today, I had chosen a sissy sailor suit dress in pink and white with matching ruffled rhumba panties over his thick pampers.

I had put him in his playpen out in the living room when the UPS delivery woman happened to come by and she rang the doorbell, startling the poor sissy. Opening the door wide to sign for the package, she got a grand view of Timmy in his shiny fat diapers and sailor suit. We both looked over at him with a smile as he blushed a cherry red and desperately looked away, his eyes brimming with tears of shame.

“What a cute paci you have there,” the woman said gaily as she waved at Timmy like he were an infant.

He squealed as I pulled it out of his mouth to show her the fat rubber cock he’d been anxiously sucking on which only made her giggle harder.

After she’d left, I checked his diapers and found he had (without even realizing it), managed to soak himself in the trauma of the encounter and I led him back to the nursery for a change.

The second time it happened, was not long after his afternoon nap. Of course, he’d flooded his diapers again while he was sleeping, and the timid pansy was nearly in tears as to why it kept happening for no apparent reason. I chuckled to myself as I slathered his bottom with more diaper rash cream and changed him into some fresh pampers.

Later that afternoon, as Timmy was in his playpen, I was teasing him to finish his bottle of milk before I’d let him out. He whimpered and pleaded and then gamely tried to finish his bottle but it was too much for the weakling. With a sudden gasp of surprise, his face went beet red and I instantly knew what was happening. With a sob of defeat, tears began to fill his eyes.

“Mommy—I wet my diapers,” he wailed piteously.

I tried without success to suppress a giggle.

“You really are becoming a big baby, aren’t you?”

The third time it happened was completely random.

I decided it was time to take Timmy out, not anywhere ambitious, but just to a local park nearby which was infrequently visited. I dressed him in a striped t-shirt and put some stretchy short shorts over his big, thick diapers, to give him a modicum of dignity. Not that it wasn’t totally obvious what he had on underneath. But I browbeat the submissive wimp and convinced him that nobody would notice. Still, the glossy black Mary Janes lent him a distinctively sissy look, even without the frilly anklets he normally wore.

After the short drive to the park, we walked along the path and I’m sure Timmy was vastly relieved that we hadn’t run into anyone. And then, by total chance, we came across my good friend Amber, who was out for a run. She is a gorgeous woman of 28, very fit, and her jogging outfit displayed her many curves to great effect.

She stopped and hugged me briefly before looking Timmy up and down.

“Aren’t you the guy that works at Frederick’s in the mall?” she asked, her eyes fixating on the big bulge around Timmy’s hips.

“Uh-huh,” he blushed, instantly realizing that his diapers were just as obvious as he feared, despite my earlier insistence that they wouldn’t be.

Taking his pacifier out from my purse, I positioned it before his trembling lips.

“Open up, Timmy.”

He squealed with embarrassment and tried to pull away but I just pushed the fat cock into his mouth as Amber giggled with amusement.

“Are those diapers he’s wearing?” she asked incredulously.

“Mm-hm,” I replied, “Timmy’s a chronic bedwetter and he can hardly stay dry for more than a couple hours.”

Reaching down, I summarily tugged his thin, slippery shorts down his legs to reveal his shiny pink diapers as he gasped with shame from the humiliating exposure.

Amber laughed and laughed, obviously very amused by the adult sissy baby.

Bunching his fists in frustration and looking very much like an overgrown toddler, Timmy could do little but quake with mortification before her. Suddenly, a low moan escaped from him as the sissy’s cheeks flushed a bright red. He looked around wildly and then at me in a frightened panic as I smiled down at him knowingly. The diuretics he had been consuming for the last week were inexorably weakening his bladder muscles and the poor wimp simply couldn’t hold it anymore.

Towering over him, I placed my hands on my hips and smiled.

“Did mommy’s little baby wet his pampers again?”

The blushing pantywaist nodded his head sadly and I scooped him up in my arms, mashing his face against the cushiony comfort of my soft, pillowy breasts.

“You poor little thing,” I said consolingly, “It’s a good thing I brought your diaper bag. But don’t worry sissy. I’ve got some nice, fluffy pampers waiting for you. C'mon, Timmy, let’s go get you changed.”

Fortunately, we were already close to the parking lot and after lowering the back gate of my Range Rover, I pulled his shorts completely off and stuffed them into my purse.

Reaching into the diaper bag, I produced a baby bottle of milk and gave it to Timmy after positioning him on the changing pad. He continued to whimper and whine at this humiliating public indignity being done to him but I simply ignored him and continued my conversation with Amber.

“Some little sissies just aren’t ready to handle the responsibilities of big boy underwear,” I explained as I peeled his clinging, damp plastic panties down his smooth legs, “Timmy thought he was mature enough and he even had a big collection of women’s panties he liked to wear. But I decided that the only panties he’ll be wearing from now on will be plastic or rubber.”

“Looks like that’s just as well,” Amber commented as she looked down on the cringing sissy.

“Sorry little sissy boy,” she said condescendingly as she smiled down at him, “You just aren’t ready for big girl panties yet.”

Timmy blushed furiously and looked away.

Unpinning his soggy wet diapers, I pulled them out from under him and dropped them into a large plastic bag, revealing his tiny, caged penis for the first time.

“Oh—my god,” Amber exclaimed, covering her beautiful smile with her hand, “That is unbelievable! It’s so tiny!!”

She burst out laughing as Timmy sucked harder in frustration on the rubber nipple filling his mouth.

“No wonder you wear diapers,” she added, “You’ve got a toddler’s dick!”

I nodded in agreement.

“Timmy was an absolute failure as a man, but as a sissy baby in diapers, he’s finally found his niche in life,” I said as I arranged a thick stack of fluffy diapers and slid them under his rump.

“I’ll say,” Amber replied as she shook her head in disbelief.

“And now his tiny little penis is safe and secure, locked away permanently so he can’t play with himself anymore,” I explained.

I was shaking soft scented baby powder over his front when a stranger happened to be walking past the back of my vehicle and she stopped in curiosity.

“Is that–? Is he–?” she stuttered, unsure of what she was witnessing.

Timmy’s legs were dangling over the back of the gate and he swung his Mary Janes in bitter frustration. Clearly, this was utterly mortifying for the squirming wimp but I also knew it was just what he needed.

“Timmy wet his diapers in the park today so I’m just changing him before I take him home to his nap time,” I explained patiently.

“Aren’t you a little old to be wearing diapers, young man?” she asked in a stern, judgmental voice.

“I think it’s very appropriate for a big sissy,” Amber offered, “I think your mommy has you right where you belong.”

It was clear she felt zero sympathy for the abashed pantywaist.

“Is that a chastity device you have him in?” the stranger asked as she drew closer.

“Yes it is. Made from hardened steel, this little masturbator’s days of erections and orgasms are over for good,” I said proudly.

The woman shook her head as she looked down at Timmy.

“Disgusting little perv,” she muttered.

Pulling up the thick cotton cloth, I slipped some pink, duckie-headed safety pins in either side, at last hiding Timmy’s shameful little package.

“Sissy bedwetters like Timmy here don’t deserve the adult privileges of an erection, and they certainly shouldn’t be allowed an orgasm,” I stated emphatically.

“No, instead, they need strict, permanent chastity and diapers to keep their childish messes contained.”

A tear of shame trickled down Timmy’s cheek as his ears burned from this deeply humiliating situation. Nevertheless, he was too weak-willed to take the baby bottle out of his mouth to try and defend himself. Not that there was anything he could say—he looked just like any incontinent toddler having his diapers changed by his mommy.

“Amber, would you like to put Timmy’s rubber panties on for him?”

“Sure thing,” she replied eagerly as she fished in the diaper bag and pulled out a pink pair of semi-transparent latex panties. They had three playful rows of ruffles across the top of the seat and she held them open as the stranger continued to watch.

“Here you are, Timmy,” she said with her beautiful smile, “These will keep your crib sheets dry.”

The diapered weakling slid off the tailgate, studiously avoiding the eyes of those watching him as he poked his Mary Janes through the leg openings. Standing up, Amber slowly working the thin, rubbery panties up his girly legs as Timmy held onto her shoulders for support.

The stranger watched and shook her head with distaste.

“Pathetic,” she said as Timmy whimpered helplessly, his cheeks a scarlet red as he nursed from his bottle.

Just as Amber was working the clingy panties up and around his voluminous diapers, a lady and her small child happened to be walking by. The park was suddenly getting busier.

“Mommy, why is that man wearing diapers?” she asked in her little voice.

The woman’s brow furrowed and she pulled on her daughter’s hand.

“Come along, Cindy,” she urged her.

Timmy finally took the bottle out of his mouth, a string of warm milk extending between the rubber nipple and his lips.

“C-can I put my shorts back on now, Mommy?” he pleaded, looking up at me desperately with his baby blue doe eyes.

“No,” I replied firmly, “I think what you’re wearing will be just fine,” I said as I patted his thick, padded seat in a maternal fashion.

Timmy bit his lip in frustration at yet another disagreement he’d lost, revealing his weak, inferior position in this relationship.

“It’s time to say goodbye now to our friends and then I’ll take you home for naptime in your crib, Timmy,” I said eagerly.

Completely defeated, Timmy said his goodbyes and then I strapped him into the over-sized car seat I’d gotten for the back seat of my Range Rover.

“See you soon, little Timmy,” Amber called out, waving at him like he were a child.

It was not many days later that I began reducing the amount of diuretics I was mixing into Timmy’s milk, but by this time, his control was already rapidly slipping away. By the end of the next week, he was hopelessly incontinent, wetting his diapers freely and I had achieved all I had set out to. Whenever my friends visited, I made a point of making him admit he needed diapers and plastic panties because he couldn’t control his peeing and they all found it quite amusing.

On Sunday, I decided to give Timmy his first maintenance spanking.

Truth be told, I had been waiting for an excuse to paddle him again, ever since I’d spanked him at the store he worked at, and this was the perfect solution. And although he’d been a very good, submissive sissy throughout the week and had hardly complained about any of his humiliating baby treatment, nevertheless, I still felt a weekly spanking would do him a world of good.

Gina happened to be visiting that day and I always felt the extra female company makes for a memorable occasion to a sissy.

Walking into his nursery, I found him sitting on the floor, happily playing with his doll set. Today, I had dressed him in a brightly colorful Disney Princess-themed dress, with short, puffy sleeves and a lacy hem that extended just to the waistband of his pampers. His fat, shiny diapers with their babyish white nursery print panties were plainly visible and his Mary Janes completed his toddler look.

Amber’s nose crinkled as she smelled the pungent, sour tang of stale urine so typical of a bedwetter’s room.

Standing over Timmy, I looked down on him and regarded him sternly. I was wearing a snug white satin blouse, a curve-hugging mini skirt and tall stiletto pumps just to intimidate him further.

“Timmy,” I announced, “there is going to be new rule in this house. Every Sunday, we will review your behavior and address any rules you’ve broken or any misdeeds that you may have gotten away with during the week, and we will settle it with a trip over my lap.”

Timmy’s mouth dropped open and he gazed up at me fearfully.

“However, you should know that even if you’ve been a perfect little boy—you’ll still get your bottom paddled. I believe very firmly in the adage that sissies should get spanked, so your rump will be feeling the bite of my paddle–without fail, every Sunday,” I explained.

Timmy’s eyes began to fill with tears and his lower lip trembled anxiously.

“Further, anytime I want to institute a new rule, you will also be given a spanking, just to make sure you remember and obey what I tell you,” I said as I took him by the wrist and hauled him to his feet.

“B-but, I-I haven’t done anything wrong,” he whined piteously.

He really did look and act like a child which only made me want to spank him harder.

“Yes, generally speaking, you’ve been a very well behaved boy this week. However, you’re still going to be paddled whether you like it or not,” I told him sternly.

The tears began tumbling down his cheeks freely now and he stamped his feet in frustration as I took the two paddles down from where they hung above his dresser.

“Fortunately, you get a choice today, Timmy. I can use either the wooden paddle, or the lexan one. Which would you prefer?”

“I don’t want either one!!” he wailed as he continued to cry.

“The wooden one has a deep seated wallop that will make it difficult for you to sit for several days,” I explained cheerfully, “However, the lexan paddle has a particularly nasty bite which is especially effective against soft bottoms like your own.

“So which should we use today?” I asked him brightly.

Timmy shifted his feet, wiping the tears from his face as he whimpered unintelligibly.

“It’s not fair!” he sobbed.

“Now Timmy—you need to choose which paddle or I’ll have to assume you want me to use both,” I warned him.

With shaking hands, he pointed at the lexan paddle.

“Is that what you want? Would you like today’s spanking with the lexan paddle?”

Timmy nervously shook his head, his hands trembling with fear.

“Okay sissy. I need you to ask me nicely now. Ask me to please use the lexan paddle to give you a good, hard spanking with,” I told him.

Timmy was openly crying now.

“P-please, M-Mommy. W-would you use the lexan paddle to-today?” he blubbered.

“Well, since you asked so nicely—I’d be delighted to, Timmy,” I replied as I put the wooden one down.

“Okay Princess, can you help mommy out and lift the hem of your dress for me?” I asked him sweetly.

With shaking hands, Timmy lifted the lacy layers of his dress and petticoats up and I reached underneath, tugging his babyish plastic panties down off of his big, bulky diapers. Not surprisingly, Timmy was wet, and after pulling his plastic panties down around his ankles, I gently took him over my lap as he continued crying softly.

With maternal patience, I recounted the various times during the week previous when he’d been fussy or he’d complained about his baby food, scolding him like a good, strict mother and telling him that this spanking was exactly what he needed.

“Sometimes, a sissy just needs a good cry, and I think we’re already well on the way there,” I chuckled.

By the time I had pulled his plastic panties down around his ankles, he was openly sobbing and Gina smiled down at him, explaining that this was what all sissies need to be good little boys.

Pushing the soggy, pee-soaked cotton between his thighs, I bared his bottom for the paddle. I knew he was scared, because I could feel my lap getting warmer and wetter as the poor sissy wet himself in fear.

Rubbing the paddle across his damp cheeks, I caressed them just to put even greater fear before the big event.

“You really are just a big baby, aren’t you, Timmy,” I teased him.

“Yes Mommy,” he sobbed plaintively.

“And now, everyone is going to know you’re a big crybaby too,” I said as I watched Gina filming the whole thing with her cell phone.

With a growl of sexual arousal, I raised the paddle up and swung it down good and hard, searing it across both his soft, tender cheeks. Timmy’s eyes went as wide as saucers and he howled out in pain and anguish. I brought the hard wooden paddle down again and again, fiercely swatting each cheek on its own before blistering both at the same time. I flattened his cheeks with the unforgiving lexan paddle, watching as they jiggled and danced, eager and ready for another agonizing, stinging swat. Timmy’s palms slapped the floor madly and made a staccato rhythm as he was forced to take his punishment while his Mary Janes kicked wildly behind him. Hot, salty tears streamed down his face and he cried openly like the big baby he’d become. I kept at it, delivering a blistering punishment that he wouldn’t soon forget.

The lexan paddle really scalded Timmy’s damp cheeks, the added moisture making his spanking all the more painful. Red, stinging welts covered his bottom and I made sure to swat the sides with equal ferocity until every square inch was an angry, crimson shade.

In a move of futile desperation, Timmy frantically reached back with his right hand to try and block my paddle. I grabbed his wrist with my free hand, which forced his head lower to floor, giving each of his cherry red buns a blistering swat as a reward. He kicked in pain and frustration, his bitter tears streaming down his face in an endless procession.

I wanted to drive home the lesson that while Timmy’s new life would now be full of soft, fluffy diapers, fuzzy plush toys and blissful nights in his crib, it was also going to be one of harsh, painful spankings, to give him the strict discipline he and every pantywaist needs so badly.

I was going to make damn sure that he knew that in this house–sissies get spanked!

THE END

338 notes · View notes

diaperpantysissy · 2 years

Text

New Year Pt 1 (nsfw 18+ only)

Alex whimpered as she pulled the soft padding up between his legs. “Do I really need to wear this?” he whined, laying his head back on the pillow and covering his eyes.

“Of course you do, silly,” tutted Claire as she pulled the tapes snugly around his waist, giving him a wonderful view of her breasts. “We had a bet and you’re going to keep your end of the bargain, unless of course you’d like to go double or nothing.” She grinned.

Alex cringed and flushed bright red at the reminder of that damn bet. Three weeks ago when he and his girlfriend had been fooling around in the bed watching porn, they had stumbled across a video where a man had been tied down by his wife and anally toyed with until he came, without ever touching his cock. Naturally being dominant, Claire had immediately taken interest and had eagerly asked Alex if she could try it on him. It had taken ten minutes of playful coercing and the condition that if she failed to finish him within an hour (he hadn’t been able to talk her down to less) that she had to do whatever he said for a day, a complete reversal of their normal dynamic. He’d been tempted by the prospect of having complete control over his tall, curvaceous lover for an entire 24 hours, making her service him and dress in the sluttiest outfits for his pleasure. Unfortunately, Claire had also insisted that the condition apply to him as well. Alex had shrugged it off at the time, confident in his victory. After all, they hadn’t tried anything like that before, and there was no way it could feel good enough for an anal virgin like him to reach orgasm. He had given her an hour. Unfortunately for him, it only took eight minutes of gentle caressing before he had a steady stream of cum dripping down his shaft. At ten minutes, Claire wore a devilish grin as he moaned and shuddered his way to his first anal orgasm.

Alex groaned at the memory, keeping his face covered as Claire turned away from her freshly diapered boyfriend.

“Oh come on, its not that bad, its just one night you can deal with it,” she admonished, rummaging through her dresser.

“But I didn’t think it would be… like this… and in front of all your friends…” he whined. For her prize, Claire was making him go with her to her best friend’s New Year’s Eve party. To his mortification, she had also decided he should go dressed as Baby New Year.

“You’re the one who made the bet. The only reason you’re in this mess is because you couldn’t hold in your little stickies,” she chided him. “Plus, think about how cute you’re going to look in this!” She turned to him, proudly displaying a frilly pastel blue dress with lace lining.

Alex’s eyes widened as he beheld it, his padded cock giving a strange throb as he began to shake his head. “I can’t wear that!” he blurted out. “I’ll look like a three-year old!”

Claire raised an eyebrow and placed her hand on her hip. “Really? That’s your argument?”

The padding between Alex’s legs rustled slightly as he shifted and looked away in embarrassment. Claire sighed and pulled him to his feet, easily lifting his slight frame as she roughly pulled the dress onto him. Alex mumbled in protest and resisted her rough treatment, though there was nothing he could really do against her.

Claire stepped back as she finished, admiring her work. “There, all done! Awww, don’t you look precious,” she teased, turning him towards the mirror in their bedroom.

Alex couldn’t believe what he saw. In the mirror stood Claire, dressed in heels and a sheer black dress that perfectly accentuated her body, pressing her breasts together and tightly hugging her hips to outline the curve of her ass. Every inch of her screamed mature, erotic confidence. Next to her was the starkly contrasting image of Alex: effeminate, petite, and dressed in girlish toddler’s clothes. The dress barely reached to his upper thigh and did nothing to hide the bulk of his diaper. If anything, the dress made it more obvious as it lifted when he moved, clearly revealing the shameful garment beneath.

“Claire, I…” He didn’t get any further, as she produced a matching blue pacifier out of nowhere and plopped it between his lips. Where the did she even find something like this?! Alex thought.

“You hush now. I don’t want to hear anything out of you until I take that out. Naughty diaper babies get spanked in front of Mommy’s friends, got it?”

She was calling herself ‘mommy’ now? Alex felt his cock harden slightly as he nodded meekly. Does she know? No there’s no way…

“Come on now, let’s go,” she said, grabbing his wrist and pulling him behind her like the toddler he looked like.

The walk to the car felt like it took forever as he turned bright red and kept his eyes focused on the ground, taking quick glances to either side and sucking on the pacifier nervously. Luckily, it was 10 pm and most of the neighborhood was on vacation or busy partying in their houses, too busy to take notice of the bizarre sight of a gorgeous woman pulling along her emasculated and padded boyfriend.

Adding further humiliation, Claire had him sit in the back seat, stating that babies need to stay in the back where it’s safe. “I just couldn’t BEAR to think what would happen if my precious little angel got hurt,” she gushed while buckling him in, enjoying his discomfort.

Sigh, at least it’s just Julie and a few other girls, Alex thought, thankful that at least his shame would be limited to a few people.

After a tense twenty minutes of praying no one would catch a glimpse of his pacified visage, they finally pulled up to the front of the house of Claire’s friend, Julie.

“Hold still, sweetie, I’ll come get you,” she said, hopping out of the car.

I’m just going to get smashed and get this night over as fast as possible. Hopefully I won’t remember it when I wake up, Alex thought dejectedly.

Claire opened the car door and helped him up, the bulk of the diaper making it harder for him to maneuver. She giggled to herself as they walked towards the front door, noticing a distinct waddle in Alex’s step. Alex shot her a quizzical look, pausing his nervous suckling.

“Oh, it’s nothing you need to worry about. Just thinking about a joke I heard earlier,” she said, giving his bottom a light smack. Alex cringed at the muffled sound. Claire rang the doorbell, grabbing his hand and giving it a reassuring squeeze. “Don’t worry baby, I won’t let the pretty girls be mean to you,” she reassured him. “Well, at least not too mean.” She flashed him a grin while he felt himself shrink inwards.

“Claire! How are yo— Oh my god is that Alex?!” Julie said as she opened the front door, her dark brown hair pulled back to reveal a lascivious view of her cleavage. Alex squirmed and felt himself begin to grow hard. “Holy shit, you actually did it! I can’t believe he went along with it,” Julie said, her hand to her mouth. Small giggles escaped as she took in the sight, a (mostly) grown man, in thick white diapers sucking a pacifier holding the hand of a woman who could clearly have anyone she wanted. “Oh my God, I can’t wait to tell everyone else!” she said excitedly. “Hang on a second.” She turned away and rushed down the hallway, calling out between her laughs, “Hey girls! Claire just got here! You gotta come see this!…”

Alone for a moment, Claire lightly pushed Alex into the house, closing the door behind them. “Well, it looks like auntie Julie likes your outfit. Doesn’t that make you happy, hmm?” she purred, bending slightly to give the front of his diaper a squeeze.

Shit, Alex thought as he felt her groping him.

“Oh! What’s this?” Claire sounded genuinely surprised as she felt the hard outline of his dick tenting through the diaper. “Awww, did somebody get a little stiffy when he saw Auntie Julie’s boobies?” she cooed.

Of course I did, what guy wouldn’t get hard looking at that? Alex thought, though in response he only meekly suckled on the pacifier.

“I seriously didn’t think you’d be able to get a boner dressed like that. I mean, what kind of man gets hard in a diaper after seeing a little cleavage?”

Alex shuffled in indignance and grumpily mumbled through his pacifier, “Who cares if I got hard, plus you’re the one who put me in this stupid diaper in the first place…” He looked up at her defiantly and spat out his pacifier, gaining confidence as he spoke. “Plus, we haven’t had sex in like two weeks, so I don’t really think its fair for you to…” He didn’t get any further as Claire swiftly pulled him forward, bending him towards the wall.

“—it’s crazy, you’re going to love this.” Julie’s voice reached them, accompanied by the voices of several other girls.

“Oh good, they arrived just in time to see how I deal with little boys who throw tantrums,” Claire said coldly.

Alex trembled. “Claire, I’m sorry, please—”

“What’s going on here?” Julie asked quizzically as she arrived with the others in tow.

“I’m glad you showed up,” Claire said lightly. “I was just about to punish little Alex here.”

The two other girls accompanying Julie, Stephanie and Paige, burst out into laughter.

“What the fuck is he wearing?” Paige said, holding her sides.

“Well,” Claire explained, “We had this little bet where if I could make the little boy here cum without touching his cock then he would have to do whatever I said for an entire day.”

“But why the diaper?” Stephanie inquired, finally getting a hold on her mirth.

“Actually, that’s a funny story.” Claire glanced at Alex and gave his padded bottom a pat. “Two months ago, I was on the computer trying to find this site for exercise equipment I used before when I noticed somebody forgot to clear their internet history.”

Alex gave a start and tried to stand up. “Wait, what? Claire, I can explain!”

Claire roughly pushed him back into position, giving his thigh a stinging slap, making him wince. “Shush, sissy, grown-ups are talking. As I was saying, it turns out little Alex here was looking up ALL kinds of dirty porn with men and women being forced to wear and use diapers by more mature, dominant people.”

Alex couldn’t believe he had been found out. He had tried so hard to cover his tracks.

Claire continued, “Of course I was a little disturbed at first. I mean, who wouldn’t be when they find something like that out of the blue about someone they’ve been dating for years?”

The girls nodded in agreement, and Alex wished he could just fade away.

“But, after giving it some thought—" she nodded towards Julie, who grinned devilishly, “I thought it might be pretty fun to have my own sissy baby girl.” She smiled. “After all, I could do what I want… who I want—"

Alex gasped and his cock began to leak.

“—and I think I’m owed a little reward after having a secret kept from me for so long. Plus, I mean, a girl can only get so much pleasure out of him. He just doesn’t measure up to the competition,” Claire said with a little laugh.

Alex cringed.

“Oh, speaking of things that don’t measure up…” she grabbed his crotch tightly, causing him to jump and let out a little squeak. “That actually brings me back to the point.” Claire began to lightly run her nails over his bottom, causing Alex’s skin to goosebump and drawing little shivers out of the humiliated sissy. “It seems like some wittle baby got a widdle stiffy when he saw Auntie Julie’s boobies. Isn’t that right, baby?” she crooned.

Alex shook and remained silent until Claire stopped running her nails over his skin to deliver a hard swap to his ass.

“I said, isn’t that right?” she demanded.

Alex nodded fervently, scrunching up his face in humiliation.

Julie walked towards them with an entertained expression. “Is that right, little boy? Did someone get excited by the pretty lady?”

Tongue-tied, Alex merely nodded, head bent in shame and suckling fiercely on his pacifier. Steph and Paige had their phones out at this point, clicking noises interspersed with their giggles. Julie smacked his ass, harder than Claire’s previous swats. Alex yelped as tears began to form in his eyes.

Julie continued raining blows on the sissy’s bottom. “It’s too bad for you I’m not into little diaper boys with little pee pees that won’t stay hard. Claire told me all about how your sex life has gotten worse over the past year and now we finally know why! You weren’t that big to begin with, but when you couldn’t stay hard Claire was fed up. Apologize now!” Julie demanded, continuing to punish Alex’s continually reddening ass.

Alex sobbed and squirmed as Julie continued to berate him. “I’m sorry, Claire. Please tell her to stop!”

Claire stood to the side, smirking at the pathetic display. “What are you sorry for?” she asked sweetly.

“I’m sorry for not being able to please you!” Alex squealed and kicked his legs.

“And why weren’t you able to do that?” Claire continued, drawing forth his confession one bottom-blistering slap at a time.

“Be- be- because—" Alex sobbed as he drew in a breath of air. “Because I was masturbating too much!” he cried out.

Claire held up a hand to Julie, halting the onslaught. Alex sobbed and his legs wobbled, completely spent. Claire bent to eye level with Alex and tipped his chin towards her. “And why were you masturbating too much?” she pressed.

Alex struggled to speak. He didn’t know what else he could possibly say to appease her. “Because… because… I umm…” Claire raised her hand in warning. “Because it made me horny thinking about being your sissy!” he blurted, eyes closed in preparation for the blow.

Claire let him suffer in anticipation for a moment before gently kissing his lips and brushing away his tears. Alex’s shoulders slumped in relief, glad he had guessed correctly. “I know, sweetie. I’m just upset you didn’t tell me before.” She gave him a soft smile as he sniffled and tried to return it through a veil of tears. “If you had told me before, we could have had so much fun…. And I wouldn’t have to do this.” Claire’s hand came down with startling speed, the meaty THWACK sound resounding throughout the room.

For Alex, it was the final straw, and he felt his bladder release in response to the surprise and pain. A soft hissing sound ensued as his diaper began to gain bulk and color. The girls stood in shocked silence for a moment before bursting out into laughter.

“No fucking way!” Paige exclaimed.

“Oh my God, I’m never going to forget this!” Stephanie blurted, shaking with laughter.

Claire gently rubbed Alex’s back. “It’s ok, sweetie, just let it all out; that’s what the diaper is there for.”

Alex felt numb. The warmth in his crotch continued to expand as his diaper gained weight. He had just pissed himself in front of four hot girls after getting spanked for getting an erection in his diapers. He wished he hadn’t made that stupid bet. He wished he was home right now. He wished the girls would stop laughing. He wished Claire would stop rubbing his back and soothing him like he was five and had an accident. Mostly though, he wished he wasn’t so hard.

Claire stood up and faced Julie. “I thought something like this might happen. Sorry to ask this of you, Jules. Could you go to my car and get the bag out of the trunk? It’s the pink one with the strawberries on it.” Alex couldn’t hear anything being said at this point, too caught up in the storm of conflicting sensations coming from his crotch and brain. “Paige, Steph, would you mind helping me move my sissy to the bathroom?”

“Of course!” they exclaimed, not wanting to miss a second of the entertainment.

The cold tile of Julie’s bathroom distracted Alex from his embarrassment enough to again take notice of his surroundings. With a start, he tried to sit up but was gently held down by Claire’s strong hand. “Hang on a second, sweetie, we’re almost done.”

He and Claire were the only ones in the bathroom, though he could hear voices from outside the door. A large pink bag stood on the toilet, its surface covered with cartoonish depictions of strawberries. His dress hung from a hook on the door. He’d been vaguely aware of Claire removing it, but he’d been too focused on his chagrin to wonder why. He glanced down at what Claire was doing and was shocked to see his crotch completely devoid of hair. “Claire what are you doing!?” he exclaimed.

“Just making it easier to change my baby’s diapers in the future,” she said calmly. “Sissy babies don’t need any hair down there, do they?”

“But I don’t want to be a—”

She interrupted him by plopping the rubber nipple back into his mouth. “Of course you do. Don’t think I didn’t see that little baby boner in your wet diaper.”

Alex flushed and opened his mouth to respond but thought better of it as Claire shot him a warning glance.

“There, all done!” Claire scooted back to admire her work. Alex’s splayed legs revealed a completely hairless crotch. She smiled at the sight of his limp cock hanging weakly above his balls. While it was true his cock was smaller than average, she had still enjoyed sex with Alex until his habit had gotten out of control. It had always excited her to see how hard her little boyfriend tried to make up for his lack of size. She gently ran her hand over his thigh and enjoyed the shudder her touch elicited. Oh well, I guess I don’t have to worry about that for a while. He made his crib, now he gets to lie in it, she thought with a chuckle. Claire grabbed a new diaper and spread it out. “Up,” she commanded, smirking as Alex eagerly complied, not wanting to be on her bad side a second time that night. Grabbing a bottle of baby lotion, she gently rubbed it into the skin around his crotch.

“Mmm,” Alex groaned as she caressed his skin.

“Do you like that baby?” she said softly, gently gripping his shaft between two fingers.

Alex nodded vigorously as he arched his hips upwards towards her.

She slowly began to stroke him between her index finger and thumb as she felt the heat begin to build between her legs. “Such a sweet little sissy. Do you like when Mommy plays with your cock?”

Alex continued to thrust, trying to get more contact than her two fingers allowed.

Claire leaned over and with one finger slipped a strap of her dress down her shoulder, almost, but not quite, exposing her breasts. “Do you want to play with Mommy?” she said breathily, her hand working his shaft faster.

Alex had his eyes riveted on her chest as he nodded and reached for her.

Claire playfully batted his searching hand away as she began to gently rub the head of his penis, making small swirling motions with the stream of precum dripping from her desperate sissy. “Ah, ah,” she chided. “Only big boys and girls get to touch Mommy. Are you one of those?”

Alex mewled pathetically through his pacifier as his need grew. Oh god… Mommy please…

“Hmmm, no. I don’t think you are…” She slipped a lotioned finger into his hole. Alex writhed and gasped as she penetrated him, continuing to thrust between her fingers. “No… you look more like a little sissy than anything to me…” She began to stroke harder as her finger found his button. “In fact, I don’t think we should even call this a cock anymore. Cocks are what men have, and you’re clearly not a man, right?”

Alex nodded in agreement, willing to accept anything as long as the sensations would continue. Oh my God… I’m so close. Please don’t stop.

Claire was working herself into a frenzy at this point. Her breasts rose and fell with lust as she toyed with her submissive boyfriend. “A pee pee this small doesn’t deserve to be called a cock. From now on, we’re going to call it your little clitty, understand?”

“Yes!” Alex squeaked through his pacifier, feeling himself begin to clench and shudder in response to his mommy’s administrations.

Claire shifted slightly, revealing her soaking panties and causing Alex to suckle ever more vigorously. Her breaths came in labored gasps and she looked like she was actively restraining herself from leaving off Alex to rub herself sore. “I guess that settles it, sissy. No man would ever agree to calling their cock a clitty.”

“Mommyyyy…. I’m going to… I—” Alex didn’t get any further as his entire body shook with the thunderous explosion of possibly the best orgasm of his life. His cock pulsed and his fingers dug at the tile as his cum shot into the air, splattering across his chest and face. His hole convulsed and shuddered around Claire’s finger as she continued to fuck him, determined to wring every last drop of cum out of her new slut. After a few seconds of spastic pleasure, Claire began to slow her administrations. Alex gasped as her finger slid out of him, his head empty and buzzing as his cock dribbled the remains of his orgasm into his new, now not so dry, diaper.

Claire stood up slowly, Alex’s cum dribbling down the side of her face and shoulder where it had splashed during his convulsions. She tsked, mentally adding another tally to the list of reasons to punish him later. She reached a finger up to scoop it off her face and wiped it on the dry padding of his diaper. Working quickly, she taped him back up and patted his crotch, satisfied his sissyhood was back where it belonged. “I hope you enjoyed that, because it’s the last time you’re going to be cumming outside of diapers for a loooonnng time. Happy New Year, sissy.”

1K notes · View notes