Pink Penguin Club
Brian could not stop looking at the clock. Wednesday was the longest day of the week for Brian as the hours and minutes dragged until 5pm. Sitting in a wet spot that developed over the work day didn't help the situation. But wearing panties to work got him so excited for his Wednesday evenings. On Wednesday nights Brian didn't have to pretend, he got to embrace his true self: Brianna.
Every Wednesday the local strip club closes normal operations and hosts an alternative night called the Pink Penguin Club. Brian found it on a night of depression induced bar hopping. What followed was the most intoxicating night of his life, and it wasn't from the 6 cocktails he had before walking in the door of the Pink Penguin Club.
That first night still gave him chills when he recalled it. Through hazy eyes he saw beautiful women in lingerie that he didn't normally see in strip clubs: Maids in frills, the pinkest and laciest corsets and stockings, and full latex catsuits.
This wasn't Brian's first time experiencing kink. He grew up on the internet and had a healthy appetite when it came to porn, gooning away his teen years to increasingly kinky genres. While he swore up and down to all of his friends, family, and potential lovers that he was straight his pornography consumption painted a different picture. It started with anal, went to femdom and cucking, then trans women, finally settling on wearing a groove in his brain with sissy porn. Hypno, feminization, chastity and denial. He shot countless ropes to these videos, stories, and pictures. But it was all fantasy until he wandered into the pink penguin club.
5pm. Brian gathered up his work bag and went to his car. The wet spot in his panties had grown all day and he could feel the cold precum against his skin. He made the fifteen minute drive from his parking garage to the club, unconsciously biting his lower lip from excitement. He parked and grabbed his other work bag from his trunk.
The Pink Penguin Club was an older building. The front vestibule was unmanned as Brian walked in. The main stage was in a sunken floor, ringed by chairs with small low top tables on the edges. On either side of the mains stage were steps leading half a floor up to the bar and another smaller stage. A completely dolled up woman dressed in the frilliest made outfit imaginable flitted up and down, back and forth, trying to ready the bar for the evening.
"Looking good, Christie!", Brian complimented the bartender as she clinked glasses.
"Wait! Before you go change try this, it's tonight's drink," she poured a short rocks glass with a yellowish liquid, "I call it an egg cracker." Christie giggled as she slid the liguid to Brian who immediately slugged it back. It was minty with a heavy alcohol burn. "You know what they say, 'the stronger the liquor the stronger the tipper'."
They both laughed as Brian thanked her and went back stage to the locker room. Christie was right, Brian had noticed that the more relaxed the patrons were the more generous they became. They also became much more aggressive and touchy; which was Brian's favorite part.
He went to his station and dropped his bag. Growing up as a boy scout taught him to be prepared so he packed everything he imagined he could need:
For the first dance: a full white lace set including high heels, stockings, garter, thong, and corset all underneath a thrifted short wedding dress and a long brunette wig.
For drink service: a blonde wig for a black sequined one piece leotard paired with pink leggings, black heels, pink bunny ears and a cute bunny tail plug that sticks out the small access hole that he installed in the back of the leotard.
For the second dance: the cowgirl themed dance with cow print chaps and thong bikini, daisy dukes cut high, high heeled leather boots, a yellow checkered blouse tied up front, and a cowgirl hat and red wig.
The rest of the bag was filled with loose makeup, some towels and wipes, a 7" realistic silicone dildo, a flat cage and a pink silicone cage, an assortment of plugs, and plenty of lube.
Brian grabbed some towels, a razor, the flat cage , a jeweled princess plug, and hit the showers. Two dancers beat Brian in to the club so he took the last stall and turned on the shower and removed a weeks worth of stubble from his body until he was smooth all over. During the final rinse and moisturizing he slipped the plug in place.
Alana, a dancer in a towel with sandy blonde hair already tucked under a wig cap, was at the sink as Brian left the shower. Alana capped the bottle she was holding, squat down, moving her towel and inserted the bottles nozzle. Brian moved to the sink next to her as she stood and refilled the bottle.
"What is your first song tonight?" Alana asked.
"Marry you", Brian replied, putting on his wig cap. Alana capped her bottle again and began slowly shaking her hips side to side. "I couldn't resist this wedding dress I saw at the thrift store last week."
Alana squat again, emptied the bottle and moved to the toilet stall. The other shower curtain opened revealing the shortest dancer at the Pink Penguin Club, Carmel.
"Eyes up here, Brianna," Carmel said as she sauntered up to the sink. Brian barely registered it as he couldn't take his eyes off the baseball bat between Carmel's thighs. Carmel had one of the biggest cocks he had ever seen outside of pornography. Her short stature almost made the contrast between her sizeable pole almost comical.
"Sorry, Carmel, but it's hard to not gawk at one of the natural wonders of the world." The dancers all laughed over the sound of water pouring into the toilet Alana occupied. Brian felt the blood begin to flow between his legs and grabbed his cage.
Brian wasn't what people called well endowed but he also didn't have a micro penis. Shorter than average he had always had a bit of a complex about his size. Sissy porn and erotica had allowed him to accept his size and even embrace it rather than constantly worry about not being able to please a partner. Plus, he had to admit, it looked great in a flat cage. He slipped the cage on, securing it over the base and locking himself into flaccidity.
Carmel bent over the sink and looked into the mirror cupping her budding A cups, pressing them together, "what do you think, Bri? They are so sensitive now."
Brian was jealous of Carmel. Her massive rod, cute face, and fat ass made her very popular at the Pink Penguin Club. So popular, in fact, that costumers showered her with gifts. Clothes, toys, makeup, party supplies, and even estrogen showed up weekly as gifts for Carmel from the patrons she enchanted.
"They look great." He replied, "I think your regulars are going have a good night." She kept playing with them in the mirror as Brian went back to the dressing room back stage.
With the application of makeup and the curly brunette wig Brian became Brianna in under an hour. Lipstick, eyeliner, and concealer hid his boyish features and highlighted her more feminine cheeks. More dancers arrived. Alana came out of the bathrooms in a full latex dress.
"Show time girls!" A thickly muscled bald man burst into the dressing room. Ernie, and Italian man in his 60s, ran the Pink Penguin Club promotion.
"Your regulars are lined up outside, hopefully you girls are ready to show them a good time!" Ernie walked through the room looking the girls up and down giving brief compliments as he passed. His trousers clearly showed his excitement as brushed by Brianna.
Brian recalled his tryout for Ernie. After his first experience at the pink penguin club he came back regularly. After a month, and several hundred dollars spent on drinks and tips, Ernie invited him into the champagne room, plying him with a bottle of Tito's. When the door clicked behind Brian he realized there weren't any dancers.
"I think you would look beautiful in this," Ernie went into a duffle bag and retrieved a sheer pink chemise. Brian choked on his drink as Ernie continued, "some of our regular guests have latent talent that needs to be fostered. That's why I started the Pink Penguin Club promotion." He moved closer to Brian and took his drink from his hand to replace it with the lingerie. "Indulge me, I have an eye for talent," his eyes met Brian's.
Before Brian knew what he was doing he had taken off his clothes and slid the chemise on. He felt drunk but had only just finished his first drink of the evening. The chemise fit wonderfully and felt soft against his skin. His little prick tented the sewn in g string. Ernie smiled big and that made Brian even more turned on.
"Gorgeous! Wasn't I right? Now, dance for me." He sat back and gestured as the house music bumped on the speakers installed in the ceiling.
This was Brian's first time doing anything like this so he faked it. He thought about the girls he had been watching and decided to copy their moves. Shaking his hips and moving his arms he made his way to Ernie's seat. Brian ran his hands down Ernie's body from his shoulders to his knees as he bent down on his own knees. A wet spot began to develop in the g string.
Brian spun around and sat on Ernie's lap. As he pushed down he could feel Ernie's hard cock through his pants pressed against his ass. Ernie was hung. This information almost made Brian pass out from excitement. He had never touched another man, let alone a man that was two to three times bigger than him. Plus, the attention he was being shown by Ernie was intoxicating. The women Brian had dated were mostly lifeless in the bedroom, Brian would pump a few times and they would leave unsatisfied. Ernie caressed Brian's curves and cupped his flat chest as he kept grinding on his lap.
Brian couldn't take it anymore. His chemise was soaked and the feeling of Ernie's massive shaft between his cheeks was driving him insane. He spun around and knelt on his knees before Ernie. Ernie gave him an approving look and gave Brian access to his pants fly. Brian's fingers trembled as he wrestled the thick mast from ernies slacks. At least 8 inches of gnarled meat stood in front of Brian's open mouth. Ernie had clearly injured it at one point in his life as it sported a heavy curve half way up the shaft.
Brian's mouth watered and his little dick dripped into his panties as his mouth enveloped Ernie's thick purple head. His salty precum filled Brian's mouth as Brian moved both hands to work the shaft.
"Mmmm you are a natural, Brianna" Ernie groaned. Brian tried to take more of him into his mouth but gagged a little. He tried to withdraw but felt Ernie's hands grab the back of his head.
"I want you to join my sissy harem, Brianna. I want you to be the best sissy you can be." Brian's head was pushed further down the thick member and he could feel the head touch the back of his throat. "The tips are generous," he laughed, "and you get to live the life you were made for." Brian reached under his g string and began to furiously stroke. Ernie noticed this and became more aggressive with his hands, pushing further down Brian's throat forcing him to put both of his hands at the base of Ernie's cock.
"My sissies don't stroke, Brianna. You will be in a chastity cage from now on, do you understand?" Brian could only choke out an affirmative grunt as Ernie's pubic bone hit is nose. After the acknowledgement Ernie let up and Brian was able to back off a little and breathe. His drool covered Ernie's short pubic hair.
"Look at me, Brianna" Ernie commanded. They made eye contact as the thick dick rested on Brian's tongue, "you are beautiful and I want to share you with the world. I want to make your dreams come true." Brian began moving both hands to work the shaft as his tongue flicked Ernie's pulsing head. When he finally felt him release in his mouth a wave of warmth took over Brian's body. The semen was hot and salty but moved down Brian's throat like a white light of pleasure. Ernie groaned as he emptied his balls into Brian's stomach.
"Good girl. Clean up and head back out to the floor. Drinks are on me for the rest of the night but I expect you to bring those back, clean." He pointed to Brian's precum soaked chemise and turned to fumble in the duffle bag where he got the chemise from, "and when that subsides I expect you to wear this in from now on." He handed over a pink silicone cage. "You are going to love being one of my girls, Brianna."
Ernie was right. Brian, or Brianna as she became more confident in herself, loved the Pink Penguin Club. She loved the customers and the attention they showered on her. She also loved the money. She was making more at the Pink Penguin club in a night than her take home pay at her office job.
Thinking about her first time with Ernie made her strain against her flat cage under the wedding dress she was wearing. The cage redirected her energy back into her body and away from her throbbing, useless sissy clit.
"You're up," Alana said, jostling Brianna out of her memories. Alana was only wearing a vinyl bra and panties after her first dance finished. Her tuck job was immaculate, completely flat where her thighs met. "And your favorite couple is here, Bri!"
Brianna's heart fluttered. A married couple in their late 40s had started coming in a few weeks prior and had been showering her with tips and attention. The wife, Erin, loved to watch her husband get lapdances from the girls but she honed in on Brianna quickly.
Bruno Mars bumper on the speaker system, the queue for Brianna to start her performance. She parted the curtains to the stage as the announcer said, "please welcome to the stage, Brianna!"
The stage was brightly lit and surrounded by patrons only illuminated by black lights and the reflection of the performance space. Bri went for the pole and began her routine. She was an athlete in high school and found that a lot of her skills translated to the pole. She spun and twirled, slowly lowering herself to the floor in her wedding gown. Dollar bills began to fly as she leaned back on the pole.
A man she recognized from past performances gestured to her with a fat wad of rolled bills from a stage side seat. She crawled to him on the floor and spun around sitting to show him the zipper to her dress which he gladly unzipped. He slid a bill into her lacey white bra as she shrugged off the dress and got on her knees, still facing away from him. The dress remained on the stage as she stood up and out of it. The crowd cheered as she bent over to reveal her virginal bridal lingerie. Her jeweled plug glittered in the stage light, bisected by her thong. She somersaulted forward landing in her back, putting her white heels in the air and spreading her legs, which gave a full view of her cage and plug to Erin and her husband seated across the stage. She heard Erin let out a cheer.
"Time for the hard part," Brianna said under her breath as she rolled back onto her shoulders, she balanced on the tips of her toes presenting her ass to the ceiling. She began to push and clench. She had been working on her kegels and now the benefits were apparent. She pushed the plug out and moved her thong fabric with it. Just when she felt the taper change she pulled it back in. Her muscle control was on full display for her audience and they loved it.
Two gym buddies sporting grey sweat pants hooted for her so she got back on all fours in a quick flip and crawled to them. They started raining bills on her but she only focused how hard their dicks were through their sweat pants. She came up in a cobra pose at the edge of the stage where they stood throwing bills on her and bumped one of their strained erections with her face. Coming up further she dragged her flat cage against the stage, bringing her legs around, and sat in front of the two men, spread eagle with her plug touching the floor.
The darker skinned gym bro reached down and fondled Brianna's cage as he began to stroke his hard cock through his sweat pants. She saw her silver threads of precum drip from his fingers when he pulled away from her wet white panties.
"I think she likes you," his friend laughed as he slid a $50 into her garters.
Brianna, still spread eagle on her back with her heels in the air, scooted closer to the edge of the stage where the men stood. Her ass nearly off the side she clasped the dark skinned gym bro with her legs and pulled his body close to hers, she reached down between her legs and began to massage him, sandwiching his sweatpants clad cock between her hands and her cage. His eyes lit up as she gave him short strokes.
"Girl, you gotta come back to our place," the friend said while tweaking Brianna's nipple through her bra. This wasn't the first time Brianna had been propositioned at the pink penguin club. She made a mental note to come back to these men during drink service.
The song began to wrap up so she pivoted away from the gym bros and made her way over to Erin and her husband. Erin had a shot of tequila ready for Brianna and she took it without using her hands much to Erin and her husbands delight. She placed the shot glass back down on the stage with her mouth and blew Erin's husband a kiss. Erin bit her lip.
Brianna stood up in her heels as the song came to a close and began to gather her tips and discarded dress, "let's hear it for Brianna!" the DJ announced over the loudspeakers. The crowd applauded and Brianna returned to the dressing room.
"Those muscle guys are hot," Alana said, "did you get their names?"
"No, but they want to take me home."
"Ugh, lucky." Alana grunted.
"I'll see if they are serious if they take me in back after drink service." Brianna laughed. The private room had been a room of experiences for Brianna. From her first blowjob with Ernie to losing her virginity her second night working to a very handsome man around her age, to servicing 5 men on her knees last month.
Brianna started to change into her drink service outfit when Ernie came into the dressing room. "Brianna, you've been requested in the private room." Her heart fluttered. Those guys work quick, she thought. She stopped dressing and changed outfits: the pink chemise that started it all was her favorite thing to wear in the private room.
She finished changing and grabbed a hand bag from her duffle. In it she put a bottle of lube and her dildo. She made her way out of the dressing room through the main room towards the private rooms. Carmel was on stage twerking as the crowd went wild. She turned around to face the audience and her massive member popped out of her panties. Not missing a beat she began to spin it like a helicopter blade. Money covered the stage.
When Brianna opened the door to the private room she was surprised to not see the gym bros. Instead, Erin and her husband sat on the couch drinking champagne from an iced bucket. They were nicely dressed for a night on the town.
"I wanted to get Hank something special for his birthday," Erin stood up and walked to Brianna, "and I can't think of a better gift than you." Erin brushed hair back from Brianna's forehead and closed in giving her a deep kiss. Their tongues danced and twisted around each other. Erin's hands moved down Brianna's body as they stayed locked in a kiss.
Hank stood up and joined the two. He leaned in, breaking the kiss to apply his lips to his wifes then to Brianna. Hank was much larger in stature than the girls. His large hands gripped Brianna by her waste, as he pushed his tongue into her mouth. Erin giggled and dropped to her knees to remove Hank's engorged cock from his pants. She gave it a few quick strokes to take him to full mast. He was big. Erin began to suck as he continued to fondle Brianna's ass.
"What do you think, honey?" Erin asked Hank, "is she what you want?"
His short, greying goatee pulled away from Brianna lips, "she's perfect." Brianna felt her legs turn to jelly with the exchange and, thinking of safety dropped to her knees next to Erin. Erin pulled her husband out of her mouth and offered it to Brianna. She joyfully accepted.
As Brianna worked Hanks large erect cock Erin went back to the couch to drink champagne and reached down to rub her beneath her dress.
"We used to swing but found that a lot of them are too conservative up for the gender bending fun we like to have." She hiked up her dress to expose her shaved vagina. It was slick and engorged as she began to bury her fingers in it. "Ernie told us you were interested in this type of thing."
"Mmhmm" Brianna grunted around a mouthful of Hank. Her pink chemise began to show her wetness. Hank picked her up off the floor in a dead lift. His cock fell out of her mouth and he embraced her with a kiss, tasting his precum on her tongue. He was a bear of a man, easily 6'5" with a strong, hard body. She rested in his arms, feeling her sissy clit strain against the flat cage.
"I want to share my gift with my wife" he said as he spun Brianna around putting her in front of Erin's spread legs. Erin spread her sopping wet cunt with two fingers, the lips parted for Brianna like a flower blooming. Hank pushed her forward and Brianna began to lap at her wetness, covering Brianna's face with her sweet fragrance. Brianna felt Hanks fingers begin to probe her back side.
"My hand bag," Brianna came up from licking Erin's pussy, "check my hand-" her voice was cut off by Erin pushing her face back into her pelvis. Erin moaned as Hank walked over to retrieve the bag.
"What do we have here," Hank chuckled as he withdrew the dildo.
"Looks like it's the opening act to me," Erin purred with pleasure.
The cold lube dripped down Brianna's ass crack as Hank slid her g string to the side. He withdrew the princess plug that Brianna had put in earlier and she felt a single digit replace it. His hands were big and she could feel his knuckles as they popped inside of her. Her body instinctually pushed back against his hand, burying his finger all the way in. She pulled back and felt him add another finger which her hole immediately swallowed.
"Can I fuck her first, honey?" Erin grabbed Brianna's hair and pulled her head up. They kissed deeply, spreading Erin's sweetness to her lips. Hank lifted Brianna off the floor, again and put her on her knees on the couch facing the back rest. He went around back and forced his precum leaking cock into Brianna's mouth. Erin moved behind her and Brianna felt her tongue flick around her hole. It was bliss.
"Mmm you know how to suck a mean cock," Hank told Brianna in a sultry tone. Brianna felt Erin withdraw her tongue and the lube bottle squirt a little more onto her hungry hole. Brianna stroked Hank while continuing to suck.
Erin used one hand to spread Brianna's cheeks as she fed her her dildo. The pressure on her prostate pushed a thick gob drool-like precum out of her cage and onto the leather couch. Erin began to work the silicone dong in and out with an increasing tempo.
"Am I hitting the spot?" Erin asked, fiendishly. Brianna could only reply with a moan. Erin used the hand not working Brianna's hole to grab the base of her sissy bulge below the cage. She gave it a squeeze and Brianna felt that white hot light eminate through her body again. Erin began to squeeze and release as she pushed the dildo in and out. Hank began to match the thrusts as he pushed deeper into Brianna's mouth.
"This is the best birthday present I've ever gotten," Hank said caressing Brianna's hair as he continued to face fuck her. "Maybe we should move her in to the empty room and keep her as our fuck toy," he looked down at Brianna, "do you want to be our sissy sex doll? I need to cum at least three times a day and Erin gets sore after an hour or two..." He stopped mid sentence as Brianna increased the intensity of her suction. Being a kept sex pet was a major kink of Brianna's. Were they serious?
Hank pulled his spit soaked cock out of Brianna's mouth and she smiled at him, her mascaras ran down her face and drool ran down her flat chest. He stepped over the back of the couch and joined his wife behind Brianna. Both of their hands caressed her as Erin kept working the dildo in and out.
Brianna's body was trembling with pleasure as Erin gave one final thrust down to the dildo's silicone balls. With a quick yank she removed the fake dick and Brianna could feel her backside gape for a short moment. Her hole closed again and Hank stood her up on her heels still facing the couch. Erin sat in front of them, spreading her legs to work her clit and cupped a breath. She looked on as Hank bent Brianna over and grabbed her hips.
Brianna felt him push into her. He was thick and hard as steel. Erin's eyes lit up as she watched her husband begin to pound Brianna from behind. It took everything in Brianna not to let out a gutteral scream of pleasure. She wasn't sure if it was his is thickness or the position that was causing the sensation but she had never been fucked like this.
"Keep going, babe, she loves it," Erin cooed as she pushed her juiced stained fingers into Brianna's mouth, sitting up on the couch to get a better look into Brianna's eyes. "Let's take her home with us and use her every day."
Brianna felt a sensation welling up deep inside her. Hank increased the pace of his long, deep strokes. He pulled all the way out until Brianna could only feel his head only to drive deep in again and again. His balls slapped against the back of Brianna's cage every time he thrusted. She began to feel weak.
Erin picked up Brianna's dildo, still slick with lube and replaced her fingers with it. Brianna's choked a little as she felt the skin like material in her esophagus. Erin removed it causing spit and lube ran down Brianna's face.
"Such a pretty girl," Erin ran her hands down Brianna's body as Hank held her in place, "we could have so much more fun together."
Brianna could feel Hank's hands wrap around her waist to keep her standing as he began to grunt like a wild animal. Erin traced the dildo down Brianna's chemise stopping in front of her soaking wet panties. The tip of the dildo met Brianna's cage with a soft thud. Then another. Erin plapped the dildo against Brianna's cage as Hank's balls continued to slap her from behind. Something was building deep inside Brianna, something she had never felt before.
"Ummm," she tried to speak, "I think, fuck, I think I need to...ughnn, I think I need to pee." She managed to get her thought out, unsure if they understood her. The plapping and fucking continued, seemingly uninterrupted by her declaration.
That's when it happened. Brianna felt an orgasm build out of nowhere. Hank furiously pounded her from behind, his cock ramming deep. She opened her eyes and looked down to see a huge rope of cum squirt out of her cage, and on to her dildo still plapping against the underside of her cage.
Then another spurt.
Then another.
She was cumming in her chastity cage with a limp dick and couldn't stop.
"You made her squirt!" Erin squealed in delight. Brianna could hardly focus as the pleasure washed over her body. Every time Hank pushed into her another volley of cum was forced out onto her dildo or Erin's waiting hands. Erin gripped her cage at the base and Brianna felt another uncontrolled spurt fill her shoot out covering Erin's hands up to her elbow. Her cum leaked down to her thighs as she began to pant from exhaustion.
Hank made an animalistic grunt and Brianna felt his cock pulse inside of her. He filled her with his seed as Erin pushed her sissy squirt covered hands into Brianna's mouth. Hank's thrusts began to shorten in frequency as he bottomed out each time, pushing his cum deeper inside of Brianna. With his final push she felt his grip loosen, she wobbled and collapsed on the couch next to Erin.
"Happy birthday, baby," Erin stood up and kissed her husband, his thick cock, still dripping, began to lose its rigidity. Covered in lube, semen, sweat, and pussy juice, Brianna tried to catch her breath on the couch as the married couple embraced. It was actually quite a touching moment, Brianna thought.
Erin leaned down and kissed Brianna on the forehead, "you should come over some time. I'll leave our card in your bag."
And with that the couple put their discarded clothes back on and went back to the main floor holding hands. Brianna tried to regain her composure. She would need a shower before doing any drink service. She looked down at her cum soaked chemise and winced at the thought of having to wash it again.
"Every damn week" she muttered.
To be continued.