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.
“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.”