Simon gulped as the curtain opened. The bright lights bore into his eyes, the heat blazing into his cheeks, or was it just the blood rushing to them?
Miley Cyrus’ “BB Talk” started playing. The crowd went wild, but it did nothing to calm his nerves. If anything, it just emphasized how many people were seeing him in a pink dress and a diaper.
As he waddled further on stage, the people lining the edge became more clear.
At first he was caught in stage-fright. He just stood there trembling. The crowd was already a little restless from the previous ‘dancer’ that refused to move as well. Simon could see the Bouncers on the side ready to apply the cables again.
He snapped from his reverie, remembering he needed to dance to earn more cash and not be turned into a human puppet. He hesitantly started wiggling his hips.
Simon had never been a great dancer, he lacked rhythm and an ability to follow a beat, but he did his best. Anything to get out of that stupid chastity device.
He tried not to look at the onlookers’ mixed expressions.
“Is that a diaper?!” he heard one of them say when he grabbed the pole and bent over a bit.
Some were laughing hysterically, others turned up their nose, and even more were just in genuine shock. They’d probably never seen a grown man in a diaper before.
He self consciously tugged on his skirt, but that drew a raucous from the crowd.
“Show us your Pampers, Princess!”
“Highlight those Huggies!!”
“We love to see your Luvs!!”
Simon twirled nonchalantly so his skirt flew up and exposed his pink princess diapers.
“Awww!! Is he wet??”
“Looks soggy to me!” Simon heard from the side of the stage.
A girl flashed a $5 bill, using her other hand to crook her finger and call him over.
Simon hurriedly crawled to the group of girls.
“Check it, Kylie!”
“I’m not touching it! You do it, Kendall!”
“I’ll do it…” said another girl, bringing her hand forward and poking his pampered crotch. “Oh my god!! It’s warm and soggy!! He is wet!!”
Simon couldn’t believe it, but a quick clench of his legs confirmed it. He hadn’t been wet before he went on stage, which means he must have pissed himself sometime since he started dancing, and he didn’t even notice!
“Keep dancing, pamper pisser!!” Another girl said, fanning a stack of 1’s.
Simon turned over on his hands and knees, swaying his hips back and forth and trying—unsuccessfully—to look sexy. He felt ridiculous, but the girls hooted and hollered anyway and he felt a rain of bills shower over him.
That spurred him on. He twirled around the stage like a princess. Someone patted his padding and a cloud of the excessive powder exploded out the sides. This caused the crowd to whoo like it were a magic trick, and then everyone that could reach started smacking his ass to get the same effect.
He got back to the pole and hoisted himself up, trying to twerk and getting another round of cheers.
But suddenly, a huge cramp sent shockwaves through his gut. He dropped to his knees, keeled over, arms crossed as he convulsed, rocking back and forth.
“Awww!! Looks like somewon has to go poo poo!!” Someone cooed.
Simon was sweating. Groaning. His bowels felt like they were swirling. Whatever was in that bottle was hitting him at the worst time. He tried to stand, but he couldn’t. The cramps were too bad.
The crowd was under no misconceptions about what was happening. Everyone in the area knew he needed to go, it was plastered across his pasty face.
“Do it! Do it! Do it!” They started chanting. Money was flying again.
The enthusiasm from the onlookers helped encourage Simon to at least get up off the floor. He didn’t want to soil himself while sitting. Using the pole as an anchor, Simon pulled himself up onto his haunches, crouching like a catcher. There were giggles and guffaws around him.
“Awww!! He’s squatting like a baby!”
“Little guy needs to make a pushy!”
“Wook at the wittle baby making a boom boom!!”
Simon tried to block it all out and focus on his task at hand. It didn’t take much. He hardly even had to push, it was more like opening the floodgates and letting it all unload. He could feel the back of his diaper swelling as the warm mush filled what felt like every nook and cranny.
The crowd must have noticed too, because they all started pointing and laughing.
“Look! It’s inflating!”
“He’s doing it!”
“Oh my god!!”
“I didn’t think he actually would!”
“Look how droopy it is!!”
But then the smell hit them. There was an audible groan from the audience as the stench wafted across the room. People covered their noses, fanned their faces, and some even choked and gagged.
Simon actually felt relieved. Not only from being rid of the churning sensation from his insides, but also that his song had finally ended.
The crowd groaned again, sad to see him go. But others started chanting again:
“One more song! One more song! One more song!”
More started joining in. Crescendoing the chorus louder and louder. Waving their arm in rhythm with the syllables—the one that wasn’t plugging their noses, that is.
“One more song! One more song! One more song!”
Simon knelt there, stupified, until finally the announcer came over the microphone.
“Looks like ya’ll aren’t done with this one just yet!”
The crowd roared in agreement. They wanted to see him dance in the dirty diaper.
The DJ spun his turntables and dialed up another song. The chimes of “Down & Dirty” by Little Mix came in. The crowd started jumping and clapping, encouraging Simon to stand up and start dancing.
Simon was reluctant, but the sight of more money got him on his feet. His diaper sagged with the weight of the load, and swung as he swayed.
There were “whoo’s” from the girls and laughter from the males.
“Come here!” One girl called, fanning a wad of cash. When Simon started strutting over, she pulled it back, wagging her finger. “No no.” she said, “crawl!”
Simon flushed as he got down on his hands knees, crawling over to her at the edge of the stage like a pitiful puppy. Her nose crinkled as he got closer, but she shook it off and smiled, flashing the cash again.
“Say ‘goo goo ga ga’” she ordered, holding the bills tauntingly. The other girls in her group laughed, except for one, who just seemed to be observing intently.
“Goo goo ga ga” Simon repeated.
The girl slipped a $1 into his cleavage. “Kneel.” She demanded again.
Simon brought his knees beneath him, being sure to keep his bottom raised off the floor so as to not squish his mess.
She gave him another dollar. “Now suck your thumb and cry like a baby”
Simon did as he was told. It’s amazing what the prospect of a whole dollar will make you do. The girl pulled out her phone and videoed him going “waahh wahhh wahhh” over the music. She brought up another bill. Then, with one sharp shove, she pushed him backwards.
Simon fell onto his bottom. The soiled diaper squelched beneath him. The mushy mess spreading everywhere inside.
“Now wriggle back and forth, baby bitch!”
Simon wanted to tell her to fuck off. But she was making it rain on top of him as he scooched and scooted on the dancefloor.
He kept bouncing on his bottom like a babbling baby until the song finally ended.
“Suck on this, loser!” The lady said over the applause from the crowd. She took the penis pacifier dangling from the string around his neck and put it in his mouth. Patting his pampered butt as he gathered his cash and rushed off stage.
******
“You only made $147” Samantha said while changing Simon’s dirty diaper on the floor of the green room.
Simon didn’t know what to say. All that effort and humiliation, and he wasn’t even halfway to his goal. Turns out all those $1’s can be deceiving. It made him feel trashy and used.
“You’re gonna have to get back out there.” She shrugged, letting him raise his hips so she could slide the fresh diaper underneath.
Simon cringed. He didn’t think he could bear going out on that stage again. But Samantha had another idea.
“You’re gonna have to do some lapdances if you want out of chastity.” She smiled, jiggling his cage to emphasize her point. “You might even have to take them back to the VIP room!”
He didn’t know which prospect was worse. After those options were laid out, he’d honestly rather get back out on stage.
She gave him another healthy dose of powder before taping him tightly into the new diaper. She pulled him to his feet, running her hands down his dress, straightening it, and fluffing out the creases.
“You looked adorable on the dance floor, especially when you were rocking back and forth on your dirty bottom” she chuckled, shaking her head, “I can’t believe you did that.”
******
“I can’t believe you did that!” Kendall said to Kim, “pushing him on his butt like that!”
Kim grinned and shrugged, “I dunno, I guess my dominant side comes out of me when I’m drunk.”
The girls all laughed, even Claire. She’d be lying if she said she didn’t enjoy the show. It felt good to be out of the apartment and having fun again. Something to take her mind off of Brad.
There were still sissies dancing on the stage, but now some of them were coming out into the lobby to mingle with the patrons.
One of the sissies from before, (the one with the buttplug if Claire remembered correctly), timidly made his way toward them.
“C-can I interest y-you in a l-lap dance?” He asked, shuffling his feet.
Claire opened her mouth to thankfully decline, but Kylie cut her off. “She would love one!”
******
Simon moved sheepishly through the crowd. Everyone seemed to stop what they were doing and look at him.
“That’s the one with the diaper!” People called. Not bothering to whisper, but instead shouting and pointing like he were a zoo animal.
If he was going to give someone a lap dance, he would first have to approach them and ask if they wanted one. There were plenty of girls and guys around, but he had never been great at initiating conversation with girls, and he didn’t particularly want to dance on a guy.
He found a small group of girls and mumbled something that resembled “can I interest you in a lap dance?”.
The girls scoffed and laughed “No chance, poopy pants!!”
Simon didn’t even bother telling them his diaper was clean, he was too embarrassed and moved on to another group.
He got various answers that all basically centered around “yea right, fuck off”. He saw the group of girls from earlier that pushed him down on stage, but one of them was already getting a dance from another sissy. Simon didn’t want to subject himself to their torment again anyway.
There was one last group he hadn’t tried yet.
“Would you like a lapdance?” He asked timidly.
The girl turned up her nose, sipping her drink. “Are you still in that dirty diaper?” She asked.
Simon shook his head, face flushed with shame. “N-no ma’am…I got changed…”
She eyed him skeptically, sniffing the air. “Turn around and lift your skirt,” she ordered.
Simon obeyed the stranger, pivoting and pulling up the hem of his dress.
He felt the waistband of his diaper pulled back, and could feel her lean in and check the inside like he were a toddler.
After a while she seemed satisfied, pulling her finger out and patting his bottom with a poof of powder.
“Okay, you’re clean, how much?” She asked, sitting back.
Simon didn’t even think about how much he’d charge. “Uh…$50?”
The girl tilted her head back and roared with laughter. “Yea right!! Get lost, loser!!”
Simon practically whimpered as he waddled away. He was so stupid, he should have started low.
There were no more girls left to approach, at least that he could see. It was a constantly moving sea of people. Finally, a woman he hadn’t seen before approached him.
“You can give my husband a lap dance” she told him, “he’s in diapers too!”
Without even waiting for Simon’s approval, she grabbed his hand and led him over to a chair where a rather defeated man was sitting. He sat with a curled up slouch, like a turtle trying to hide in his shell and hoping no one would see him. He was dressed in otherwise normal clothes, but Simon had enough expertise to know the bulge in his pants was from none other than a diaper.
“Look who I found for you, Percy!” She cooed, nudging Simon forward. She strolled around behind the chair and nodded for Simon to begin. Simon didn’t know what to do, or where to start. He tried to think back to one of the few times he even visited a stripclub and got a lapdance of his own.
He remembered the girl being very close to him in an almost intimate sort of way, rubbing her cleavage in his face. Simon didn’t have much cleavage to speak of, and he didn’t like the feeling of being up close and personal with this random stranger. But he knew this was his only chance of making money and earning his freedom, so he sighed and started faking it.
Simon brought the man’s legs down off the chair. Leaning forward, swaying his hips back and forth to the music. Percy avoided eye contact, trying to look away and appearing to be just as uncomfortable as Simon was.
Simon decided to turn around and avoid the awkwardness. Continuing to sway back and forth, pulling up his skirt daintily and exposing his pampered bum.
He felt a smack on his ass that he assumed came from Percy, but when he looked back it was actually Percy’s wife. “Do better or no tip for you!” she seethed.
Simon whimpered and turned back around, trying to be more seductive. He straddled Percy and brought his head into his ‘cleavage’, moving it around like he was motorboating. It was silly and ridiculous, but the wife laughed heartily at that.
Simon started grinding his diaper into Percy, and even through the music he could hear Percy inhale sharply. He seemed to like that. So Simon kept doing it. Leaning in close and moving his hips back and forth against Percy’s crotch.
Simon could feel something stiff in there now, even through both of their padding. He tried not to cringe that he was making this random man hard in his diaper, but he had to keep going.
Simon flipped around again, dragging the back of his diaper across Percy’s tent in his pants. Backing it up into him like he was a slut at the club.
Percy was squirming now. Simon was worried something might be wrong, but he felt Percy put his hands on Simon’s hips. Pulling him closer, harder. Until it was like they were fucking with invisible genitalia on the chair.
Percy bit his bottom lip, he was straining in the chair, spasming, and then he ceased.
“Awww! Percy!! Did you have a wittle accident?” his wife asked after Simon climbed off him.
She reached into his pants and took a peek into the front of his diaper, then gasped. “Ohh!! You sure did! That’s quite the sticky little mess in there! You little loser! You just came from getting grinded on by a pampered princess!!!”
Both Percy and Simon blushed. The wife, and the onlookers, cackled with laughter.
“Here,” the lady said, shoving some bills into Simon’s hand, “thanks for the ‘ride’, Candi!” she said with a wink, then sent him away.
******
“See? That wasn’t so bad!” Kim said to Claire after the sissy completed her lap dance.
“It was…awkward. Haha.” Claire chuckled sheepishly. “His panties were wet and sticky the whole time!”
The girls laughed, “What about your panties? Did it turn you on a little bit?”
“Not even close.” Claire cackled, taking a sip of her drink and eyeing the door. “That bouncer though…” she murmured before she could stop herself.
Kylie gasped, “That one? The big white guy??”
Claire flushed and turned away, embarrassed at having said anything, but the girls swarmed her.
“Oh my god! You should take him to the VIP room!”
“I’m sure he’ll say yes!”
“Go get you some, girl!”
“You need it!”
“Forget Brad!”
“Yea, fuck him!”
They shoved Claire forward. Converging behind her to keep her from backing out, cheering her on.
“Just go talk to him!”
“You can do it!”
“You need it!”
Claire sighed, tipping her drink back and finishing it in one gulp. She approached the big, burly bartender and tapped him on the shoulder.
“Hi,” she said.
******
“Hello” Simon said to another stranger.
He had given three lapdances, all to men. Turns out you have to flirt a little bit to get them wanting. The last man had an insanely creepy smile and was very gropey with his hands. But he tipped well, so Simon counted it as a win.
The man he was speaking to now was dressed in a purple fur coat. He had a long gold chain around his neck, was wearing sunglasses inside, and puffing on a sweet smelling cigar.
“Hello there,” the man replied, flashing a set of gold teeth.
Simon shivered in the man’s presence. “C-can I interest you in a lap dance, s-sir?”
The man smirked and exhaled another cloud of smoke, inclining his head and looking Simon over.
“That diaper full?” he asked.
Simon clenched his legs, “No sir,” he squeaked, “Still dry.”
He turned his nose up at that, almost in disappointment. Simon had been forcing himself to hold it. He didn’t think anyone would want a soggy diaper rubbing against their leg or crotch.
“Wet it.” the man said.
“I..I’m sorry?”
“Boy don’t make me repeat myself!” the man barked, waving his cigar at him threateningly. “I said ‘wet it’!”
But Simon had already begun to do so. The man’s sharp tone got him so scared he started leaking into his pampers. It didn’t take much more effort to release the rest.
The man smiled as he watched the front of the diaper swell and sag, obviously taking some sort of pleasure in having power over him. Simon squeezed his eyes closed as he pushed the rest out.
The man said nothing, just smiled with his gold grill again. Simon stood there awkwardly with his now warm, wet diaper. “So uh…about that lap dance?”
“You ain’t rubbin’ that shit on me,” he said, “But we can go back to the VIP room.”
Simon gulped, “what are we going to do back there, sir?”
“Whatever the fuck I want,” he replied. Standing up and strolling to the back rooms without bothering to check if Simon was following.
Simon ran through the amount of cash he had in his head. $250, he needed just $50 more. He was terrified of what was waiting for him, but whatever it was, he had to do it.
The back hallway was lined with several booths. They each had their own poles, benches, and curtains. Most of the curtains were closed, and there were a multitude of noises coming from each. One room left the curtain completely open, with a sissy getting bent against the wall and absolutely railed by a very big man.
Simon tried to swallow the lump forming in his throat. They went almost all the way to the end until they found a vacant room. The man pulled the curtain open, and gestured for Simon to enter. He traipsed in reluctantly.
The curtain snapped shut behind them. The man plopped down on the bench and grinned. “So…what that mouth do?”
******
Claire had been a little nervous when they entered the VIP room. But the alcohol had given her a bit of liquid courage, and it helped that the bouncer was very patient and considerate with her. She was used to Brad, who tended to be very forceful and self-centered.
He held her in his arms and they chatted for a bit, turns out his name was John.
Soon they were kissing. Slowly, softly, passionately. Claire didn’t think such a big man could be so tender. His arms were big and bulky, but they made her feel safe and secure.
She could feel a yearning for him between her legs, but she controlled herself. Instead, she reached her hands down to his pants.
“Oh my” she gasped between kisses. It was the biggest she’d ever felt. He tentatively brought his hand to her belly. She led it up to her chest, giving him the okay. He squeezed her breast gently, but it sent a shockwave through her. He kissed her neck, nibbled her ear, rubbed his hands all over her.
She brought his hand down to her waist, a signal to let him know it was okay to go further. He obliged, slipping a hand beneath her skirt and fiddling with her panties. She was almost embarrassed by how wet she was. But he didn’t seem to mind, he deftly moved her panties over, and slipped a finger between her labia. Bringing it carefully upwards until he found her clit. He found it much faster than Brad ever did. Brad tended to play with her left thigh—if he participated in foreplay at all–and if he did manage to find her clit, he would swirl his finger in a circular motion very vigorously. It did not feel good. She didn’t know why guys were so obsessed with that motion, and slapping it did nothing for her either.
But John did it softly, rhythmically. He listened to her breathing intensify and actually kept doing that motion, instead of switching the speed or doing something else.
She was swimming in pheromones and a drunken daze. She couldn’t remember being this turned on in a long time.
“You’re sure you’re not too drunk?” John asked.
Claire wanted to melt from how caring he was, but she was plenty sober enough to make her own decisions.
She got down on her knees and started fiddling with his belt, pulling out his large, throbbing cock, “Oh i’m just fine.”
******
Simon stared at the big, twitching dick staring him in the face. He had never sucked a real dick before. But Samantha often had him service her strapon before he received a pounding.
The man didn’t seem to care, though. He sat back, puffing his cigar and waited expectantly.
“Your tip is dropping by the second.” he said.
Simon anxiously grabbed the fleshy stiffness of the cock. His fingers could barely touch around the girthy member. He tried not to look revolted as he stared at the big, bulbous head in the face. The man wasn’t even looking, just stared off in the distance looking faded.
That helped. Simon felt a little less pressure. He closed his eyes and leaned forward, feeling the sweaty, salty head of the penis enter his mouth.
He told himself it was like sucking on a pacifier, a really really big pacifier. He sucked and slurped on the head, revolted at the taste and texture, but trying not to show it.
He figured he could just stay at the top, swirling his tongue around the head and stroking the base until the man came. But Simon felt a hand on the back of his head, and he was forced downward until the cock slid further down his throat.
******
Claire was used to Brad jamming her head down when she gave him a blowjob, but John didn’t do that. He gave her free reign, groaning appreciatively and moaning with pleasure. Claire hated being forced to deepthroat, but with John, she wanted to take it as far down her throat as she could.
Her eyes watered as she took him deep, looking up at him so she could see his eyes rolling in the back of his head.
******
Simon sputtered. Snot shooting out of his nose and stomach acid rising up in his throat. He managed to choke it back down, coming up for air just for a second before he was shoved back down.
This wasn’t how he expected his first blowjob to go. He didn’t think he’d be giving a blowjob at all. But here he was. Doing his best not to throw-up on this man’s crotch.
“Lick my balls and ass,” the man said, slapping Simon in the face with his slimy dick and holding it up for him. Simon whimpered as he licked the man’s salty ballsack. He tried to stay there as long as he could, dreading going down further. But the man was impatient. He gripped Simon by the wig and forced him down between his cheeks. Simon cringed as he buried his tongue between the man’s crack. The taste was even less pleasant than before.
The man wrapped his legs around Simon and kept him there, cleaning his asshole until Simon was struggling for air.
Finally, he released and Simon gasped. He hardly had time to breathe before the dick was shoved back into his mouth.
******
Claire was sucking out his soul. She had never given a blowjob for this long. She was swirling her tongue around the head and her fingers around the base.
She could feel his dick throbbing. She would have been content with him cumming in her mouth, but he stopped her, gently placing a hand on the side of her face.
“What?” Claire asked between breaths, “Was it not good?”
“It was excellent.” John smiled. “But I want to take care of you.”
She was surprised at that. Brad never went down on her. But she didn’t feel particularly clean, and was a little self-conscious.
“Just fuck me,” she said, cringing a bit at her crassness, “Do you have a condom?”
John nodded, reaching in his back pocket and pulling out a gold-colored packet.
Claire smiled. It was always a relief when guys didn’t complain about wearing condoms.
She stood up and hiked up her skirt. “How do you want me?”
******
“Turn around and pull that diaper down, you little bitch.” the man said.
Simon whimpered while he followed orders. Turning to face the black, grimy wall, and pulling his pampers down below his cheeks.
He knew what was coming, but he didn’t think he could handle it. “P-p-please be gentle, sir!” He whined pathetically.
The man laughed as he stood up. Stubbing out his cigar and reaching into his pocket. Simon breathed a sigh of relief when he saw the small bottle of lube.
The man squirted a generous amount into his hand, coating it over his cock and stroking it to its full potential.
“Spread ‘em.” He said.
Simon didn’t need to be told twice. He reached behind him, shouldering the wall, and pulled his cheeks as far apart as they would go. He felt the head of the man’s dick poking at his hole as he approached. Simon tried to mentally prepare, but he didn’t have time before he felt it pressing into him roughly. He let out a sharp squeal, which seemed to spur the man on. Forcing it in more and more and working it in and out.
Simon suddenly wished he had a lot more lube.
*****
Claire was so wet.
John was holding her legs as he held her up against the wall. Thrusting in and out of her, making her see stars with every stroke.
*****
The lights were going on and off in Simon’s head with every thrust. He’d never felt so full. The man’s hands were gripping his hips and guiding them back and forth on the man’s cock. Simon felt like such a slut in that moment. Such a whore.
*****
Claire had never felt so full. John’s hands gripped her firmly yet sensually on the hips. She felt so powerful in that moment, so happy, so free.
John started picking up the pace, thrusting in and out of her. Letting her fall down on his dick, only to lift her up with ease and do it again.
She could feel an orgasm building. A small part of her knew it would end in disappointment. It always had with Brad. It was like he was often in a race to finish first, with no concern about her pleasure at all.
“Are you close?” John asked. Claire, a bit taken aback, nodded fervently. “Do you need me to go faster or slower?” he asked.
“Just like that,” she moaned, “Don’t stop. PLEASE! Don’t stop!”
******
“Please stop!!” Simon begged. “More lube! I need more lube!!”
Tears were streaming down his face. His mascara was probably running. But the man continued to press in and out of him.
He forced Simon further into the wall, holding him still while he violated him. Simon breathed out the side of his mouth that wasn’t pressed against the velvet. The slimy python slithering around inside him.
All of a sudden something switched. What felt like searing pain soon turned to an odd sort of pleasure. The man’s cock started to feel good as it pressed against something in his rectum.
“Ohhh…” Simon sighed, and the man behind him chuckled, “Ohhhhh!!”
Simon’s groans turned to moans as the pressure inside him started to build. “Yea! There!” he grunted.
******
“There! Right there! Yesss!!”
Claire was in heaven. A gorgeous, generous man was pounding her into oblivion, and she couldn’t get enough.
“I’m going to cum!” She shouted, “I’m gonna cum!!”
It had been a long time since she’d said that. She expected John to stop at any moment and say he finished, leaving her hanging. But he didn’t, he kept going. That steady rhythmic stroke.
She could feel the pressure building. Finally, she was about to cum!”
******
Finally, he was about to cum!
It had been so long since Simon was able to say that. He could feel the pressure building as the man pounded him into oblivion.
He’d heard of sissies cumming from anal only, but he’d never thought he’d be able to do so. Now he believed it as he felt like his cock was about to explode through his cage.
“Don’t stop! PLEASE! Don’t stop!” he begged. It was a stark contrast from his mood before.
Simon was right there, on the precipice. He could feel it. He was close. FINALLY, he was going to get to….
The man stopped. Simon could feel the cock twitching inside his assole. There was grunting behind him, and soon, a different kind of warmth spread inside him. The man was cumming, but Simon didn’t get to.
******
Claire was still quaking from the after effects of her orgasm when John moaned into her ear. She could feel his dick twitching and pulsing inside her.
They collapsed together onto the bench.
“Did you go?” John asked between his heavy breathing.
“Oh yea,” Claire sighed, “I sure did!”
******
The man’s cum was still leaking out of Simon’s asshole and into his diaper as he counted the money man tossed him after Simon collapsed in a heap on the floor. It was only $47, apparently all the man had in his wallet.
Simon whimpered when he totalled up his earnings from the night: $297. He was $3 short.
He exited the VIP booth and went down the hallway, wincing with every step from his abused hole. There was a girl in front of him that gave a big burly bouncer a hug and a kiss.
“Thank you so much” he heard her say, “I needed that.”
They exchanged numbers and said their goodbyes while Simon slid past them.
“Hey!” the girl called after the two had parted ways.
******
“Hey…” the sissy said meekly, staring at the ground and sniffling.
“Something wrong?” Claire asked. She reached a finger beneath his chin and raised his head up to look at her. The sissy’s mascara was running down his face, his wig was disheveled, and his face was leaking several different fluids.
The sissy shrugged, tugging on his dress. “It’s…been a rough night.”
“Tell me about it…” Claire said in agreement. She’d had a rollercoaster of a day, though the last hour or so had been quite the climax.
******
“I’m supposed to earn $300 tonight and I’m $3 short…” Simon answered. He figured her statement was probably rhetorical. But he needed to vent somehow.
The girl looked at him sympathetically and reached around for her pocket book.
“Well…I happen to have three $1’s right here…” she said, holding up the crisp bills.
Simon’s eyes went wide, but then he realized it would probably involve another overwhelming ordeal.
He hesitated to ask. “Is there…anything I can do to earn it?”
*****
Claire smiled, he looked like such a desperate little puppy.
She shrugged sweetly. “You can kiss my feet and tell me I'm pretty.”
She’d never seen someone drop to their knees so fast. The sissy bent over and planted several kisses on the tops of her feet.
“You are so beautiful!” he whimpered in a high pitched voice. “Gorgeous! Radiant! Mesmerizing!”
As he leaned down, his skirt rode up, and Claire got a clear view of his diaper. Claire giggled, wiggling her feet to indicate he could stand.
“One more thing…” she said as he reached his hand out.
The sissy cringed, obviously dreading what she might want him to do next.
Claire couldn’t help but giggle a bit. “Can I check your diaper?”
He deflated at that. Like a huge weight was off his shoulders that it wasn’t something worse. He gratefully lifted his skirt and allowed her to peek inside.
There was a sticky glob leaking in both the front, and the back side. But it was otherwise clean of messes.
“Hmmm…I thought there would be poo poo in there.” She chortled. “Most guys I know are full of shit. They should probably wear diapers too.”
The sissy shrugged. “Yea…maybe.”
Claire handed him the money, and he looked as if he’d just won the lottery.
“Promise me you’ll be a better husband to your wife.” she said as sternly as she could.
The sissy nodded frivolously, “I will, ma’am! Thank you!”
******
“$300! You did it, hubby!” Samantha smiled, counting the bills. “Unfortunately though…the house takes a 50% cut…”
Simon’s stomach plummeted. “B-but you said…”
“I said I’d unlock you if you made me $300. But you only earned me half that.”
Simon could feel the tears welling up again. All that work, all that humiliation, all for nothing.
Samantha burst out laughing. “I’m kidding, sweetheart! I’m not that cruel! I’m actually quite proud of you. You looked like such a bimbo dancing up on that stage. And watching you desperately ask to give lap dances was pure entertainment gold! I’ll absolutely unlock you!”
Simon still shed tears, but this time they were tears of joy. “Oh thank you honey! Thank you!!”
Samantha smirked at her own joke. “Of course, baby!” she said, switching tones, “But don’t think for a second I’m letting you use my vibrator!”
“Of course not, Mommy” Simon said, switching his own tone as well, “I never want to come back here again….”
She shrugged at that, “Well…never say ‘never’...”
******
“So who was your favorite of the night?” Kim asked the girls on their drive home.
“Mine was Chantal!”
“Oh, see, I liked Daisy!”
“I think Candi was cute..” Claire said over the rest, smiling.
“The one in the diaper?!”
“Are you kidding??”
Claire shrugged. “He was adorable. In fact…I think I figured out the perfect way to get back at Brad…”
The End.