Amatuer Strip Night

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Shemale Sasha enters strip contest.
1.4k words
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Part 1 of the 2 part series

Updated 09/22/2022
Created 09/06/2007
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Sasha had just had her breasts done, and now fully healed wanted to show off her beautiful new C cups. She wandered around for a few days in low cut tops and certainly got a lot of attention, but she was aching for someone to really worship them.

Flipping through the paper, she saw an ad for an amateur striping contest at the local topless bar. "Do I, as a shemale, really want to enter this contest?" she asked herself. She knew that the girls weren't allowed to take off their bottoms, and after some experimenting with a moving and shaking dance routine determined that even in her sexy red thong, her penis would stayed tucked away, she thought why not.

After working out a cowgirl routine to "Wanted Dead or Alive" by Bon Jovi and "Cowboy" by Kid Rock, she went down to the club on the amateur strip contest night. She signed in with the manager, who explained that the 1st place girl gets $100, the second place girl gets $50 and the third place girl gets $25. Girls could keep all the tips they get during their stage show, and the winner would get invited up for one encore song.

The manager showed her to the dressing room, where five other girls were waiting. Sasha surveyed the competition, and decided that she was among the better looking of the bunch. Sasha changed into her outfit, already wearing her red g-string thong panties with her penis tucked away, she put on a pair of tight jean shorts, a pair of leather chaps with tassels, a black bra and a red and white checked shirt, which she left mostly unbuttoned and tied up to expose her stomach. She topped herself off with a cowboy hat and had one of those wooden sticks with a pony's head on the end as a prop.

A random order was selected for the girls to dance, and Sasha was selected to go fourth, with 3 girls ahead of her and 2 following her. The girls went out and watched the other girls perform. The 3 girls that went before Sasha were pretty, but they hadn't worked out any sort of dance routine, and mostly just strutted around on stage and tried (and mostly failed) to swing around the stripper pole.

Sasha was called up, and "Cowboy" by Kid Rock came blaring on the speaker. Sasha went into her routine, a very high energy, hip thrusting and tit shaking number that had the boys in the crowd going crazy. Sasha was so excited by the response that she skipped ahead in the routine just so she could get her breasts out for the excited boys to see. They loved it, and before the first song was over she already had boys lying on stage with dollar bills in their mouths. Sasha crawled around on the stage, mushing their faces into her breasts, and then lifting the dollar bills out between her tits. By the end of the first song, Sasha already had $15 in tips, much more than the first three girls had gotten for both their songs.

The second song, "Wanted Dead or Alive," slowed the tempo down a bit, but not the flow of men coming up to the stage. Sasha took some time to get out of her chaps and jean shorts, and did some slow, rhythmic dancing before collecting more tips. A few guys choose not to lay on the stage, instead standing with their tips in hand, and after enjoying a close up dance, slipping the tip into the elastic of her thong.

The song ended and the crowd erupted into applause. Sasha collected up her clothes and tips, and quickly counted them leaving the stage. $40 in just two songs! The Manager was standing at the side of the stage, and when Sasha told him the haul he whistled. "The last two girls are going to have to do something really special to beat you tonight, I think."

They didn't do anything really special, and without much surprise to the crowd, Sasha was crowned the winner of the strip contest. She was called up for her encore, and took the stage to "Wanted Dead or Alive" again. Sasha skipped the undressing part this time, entering the stage already with just her thong on. More men came to the stage with dollar bills, and soon she was collecting them from between in breast and in the string of her thong.

She approached one man, standing off to the side with a five dollar bill in his hand. "God, I love your ass!" he shouted at her, drunkenly slurring his words. Sasha obliged him by turning around, grabbing his face and rubbing his face on it. She released him, and he hooted his pleasure. Sasha, swept up in the moment forgot about the five dollar tip the man had, and started to walk away. At the same time, the man was reaching up and trying to put the five dollar bill in Sasha's g-string. Between Sasha already moving and the man's drunken lack of coordination, and accident happened, and the man soon found himself tugging Sasha's panties down around her knees. Sasha looked down, and saw her penis flop down from between her legs and be clearly visible for the whole crowd to see.

There was a moment of stunned silence, and Sasha remained frozen. Then, she heard noise from the crowd. Gasps, hoots, laughter. It sounded like the noises the crowd makes on "Jerry Springer" or "Montel" when they do a big reveal of a secret. Sasha, red faced, pulled up her thong, but without the time to re-adjust, the front of the thong had a bulge in it from her exposed cock. She looked around unsure, finally catching the manager's eye. He shugged, and made a sign for her to continue the dance. Sasha danced for another minute, acutely aware of her penis being visible through the fabric of her thong. Hoots and laughter continued, and Sasha was mortified.

Finally, she could take no more and ran off the stage, the song still only three-quarters done and ran into the change room. She sat down, more embarrassed than she had ever been, and started to cry.

The other girls filtered in to the dressing room to collect their things, and gave Sasha the coldest looks she had ever seen. Sasha's spirits sunk even lower. She got quickly dressed in a pair of jeans and a white t-shirt, and started to head for the exit. Walking out of the dressing room, she ran into the manager.

"Whoa, where you running off to? I haven't given you your first place prize yet," he said. "Come down to my office."

They went to the office, and Sasha could barely look up as the manager pulled out five 20 dollar bills and handed them to her. "It was really a good show, other than the wardrobe malfunction during the encore," he said, sympathetically. "You should be proud of yourself."

"I just want to go," Sasha said, still staring down at the ground. "Is there a back exit. I don't really want to walk through the front room."

"Yeah, if that's what you want, there's a back door. But I should tell you, after you left the stage I had 5 guys come up to me and ask if you'd be available for private dances this evening. Usually we don't allow the amateur girls to use the VIP room, but given the interest and the amount you made in tips on stage, I'd be willing to make an exception for you. The guys pay $20 a song back there. That's really where the girls make their money."

Sasha looked up. The manager didn't appear to be joking. "Five guys?" she asked. The manager nodded. "And it's not a problem that I'm... you know?"

The manager shrugged his shoulders. "Hey, not my cup of tea, but if the paying customers want it, I'm more than happy to provide it. If you want, I'd suggest changing back into your bra and thong and heading out on the floor. I'd be more than happy to point out the guys who were asking about you."

Sasha's mood suddenly improved greatly. Perhaps all those hoots and whistles hadn't been mocking her. Seems like that at least a few of the guys had liked what they saw. She smiled as she headed back to the dressing room to pull back on her costume. Now she only had one question to answer.

Should she tuck herself in, or leave herself untucked?

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