Trailer Trash Tranny Ch. 03

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Tranny hooker has rough sex in strip club parking lot.
1.7k words
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Part 3 of the 8 part series

Updated 11/02/2022
Created 04/17/2008
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Chapter 03: Strip Club

Jeannie, a blonde tranny living in a trailer park outside of Omaha, Nebraska, was working as a hooker to try and make enough money to get a boob job and move to New York City. She was working the parking lot of the truck stop just down the highway from her trailer. After an initial night where Jeannie made a good amount of money, things had been a lot tighter at the truck stop. The novelty of being the "new girl" working the lot had worn off and so the prices that the truckers were willing to pay for Jeannie's company was dropping. After paying for booze and cigarettes and giving some of her money to her mama, Jeannie wasn't saving much.

One night one of the genetic girls working the lot was chatting with Jeannie. "You know, you are much too pretty to be working here at the truck stop. This fuckers are real cheap. You should go work at the strip club."

Jeannie shook her head, lifting her skirt to show off her cock. "They ain't gonna want no tranny stripping on stage."

"No, dear. Not in the strip club. Out back in the parking lot. The guys coming out of the strip club are drunk, horny and got way more money and less brains than these truckers. They'll pay to fuck a pretty face like you. I used to work there, but I'm too old now. But young and pretty, you'd make lots of cash."

So in addition to working at the truck stop on weekday nights, Jeannie started hanging out in the back parking lot of the strip club on Thursdays, Fridays and Saturdays to get the drunk, weekend crowd. She would pay of the bouncers to leave her alone, and then sit in her car smoking. As guys would come out of the club, she would flash them a smile and a look up her skirt at her panty-less dick and ass. If the guys were interested, she would go back to their car and after shoving the money in her bra, give them blow jobs or fuck them.

The old whore at the truck stop was right, the guys there were so drunk they would often agree to prices that were double or triple what the truckers would pay, and sometimes the guys would pass out during the act, which allowed Jeannie to pocket a little extra cash from the wallets of the sleeping drunks.

One night, Jeannie was sitting in the parking lot of the strip club, dragging on her cigarette and taking swigs out of bottle of Jack Daniel's when three guys came out of the club. Usually Jeannie didn't try and solicit groups of guys, as most guys wouldn't want their friends to know they fucked a tranny, but these guys were loud and drunk and obviously checking Jeannie out. They were cute guys, probably in their early twenties, and dressed up nicely, like college boys. Jeannie liked college boys. It was a nice change from the toothless, high school drop outs in the trailer park that want to fuck her for a pack of smokes and a bottle of beer.

Jeannie opened up her legs and pushed her hips out of the car a bit to make sure the boys saw she was a tranny. The loudest of the guys smiled and walked over. "Look what we have here, boys. A real life shemale whore. What do you say, whore? You wanna fuck me and my friends?"

"How much you gonna pay?" Jeannie asked.

"$80 each," the main guy said. He then grabbed Jeannie's hair and dragged her out of the car. Jeannie was shocked, but trailed behind the guy, trying to keep up so he didn't rip her blonde hair right out of her head.

Instead of taking her to their car though, the guy dragged her behind the dumpster. His two friends followed them.

The main college boy undid his pants and dropped. "Start sucking, you dirty slut," he said.

"Money first," Jeannie said, but the boy grabbed her head and pushed her down. Jeannie fell to her knees into the sludge of dirt, grease and garbage that was surrounding the dumpster. The boy's hard cock was right in front of Jeannie's face. Jeannie knew that if she started sucking, she probably would get fucked over on the payment, but the boy was so cute and Jeannie was hungry for the cock, so she started sucking anyway.

One of the other boys walked up behind Jeannie, and put his foot up under Jeannie's skirt. He started pressing against Jeannie's ass, like he was trying to put his shoe in her asshole. There was no way the guy's foot was going to fit, but Jeannie stuck out her ass and started pressing against the guys shoe. It felt good to have the guy pressing up against her asshole and taint with his foot.

Jeannie heard a voice from behind her. "Holy fuck, this fucking tranny wants my foot in her ass! What a slut!" Jeannie wriggled her ass, letting the guy's foot run up and down her ass.

The guy she was sucking started fucking her face, pushing his cock deep and fast into Jeannie's mouth. With the one guy pushing her from behind with his foot, and the other guy pushing her by pounding her mouth, Jeannie started sliding around on the grimy pavement by the dumpster. She could feel her knees starting to scrap and hurt, but she was enjoying having the cock in her mouth.

The guy with his foot reached down and pulled Jeannie's ass up. He rammed four fingers into her and started fucking her ass furiously with his hand. Once her ass was wide open, the guy pulled his hand out and rammed his cock in her ass. Jeannie was loving the feeling of having a cock in her mouth and one in her ass.

The third guy walked up and put his cock in Jeannie's hand. She started jerking him off. Jeannie broke off from the blow job to scream out, "I love all these cocks." Then she went back to deep throating the cock in front of her face.

The guy she was blowing made a strange, gurgling sound, and then released his load into Jeannie's mouth. He stumbled backwards, spent from the blow job. The guy in Jeannie's ass took the opportunity to move Jeannie up against the dumpster so that they could both steady themselves. The guy started pushing fast and deep into Jeannie's ass. Jeannie's face was soon being rammed up against the dirty dumpster, but Jeannie was loving it. "Fuck me. Fuck me." she kept repeating.

The college boy fucking her pulled out and jerked himself off. "I'm going to spluge," he said. His cum shot all over, covering Jeannie's ass and also spewing against the dumpster.

The leader of the pack had recovered from his blow job and walked up to the dumpster. "Look at that, you filthy whore. Jack wanted to come all over your ass, but you couldn't stand still enough for him to hit his target. You'll have to pay for that, you dirty slut." With that, the guy pushed Jeannie's head down until it was in front of the cum running down the side of the dirty dumpster. "Lick it up, you filthy cunt."

Jeannie stuck out her tongue and licked the side of the dumpster, swallowing down the dirty cum. Jeannie was loving being dominated by these three assholes.

"What a fucking whore. I love it," said the third guy who hadn't come yet. "Let me at this bitch so I can show her what a real man feels like." The third guy grabbed Jeannie and pushed her down onto the pavement. Jeannie landed on all fours and felt the guy's cock push into her asshole.

Jeannie tried to stay on all fours, but the guys was fucking her so strongly and the pavement greasy and slippery that Jeannie soon found her face against the pavement. She turned her face to the side, but she felt the dirt start to cover the one side of her face. She could feel the burning of her knees being scrapped furiously against the pavement.

"Do you love this, you dirty slut? Being raped by the dumpster?" the guy in her ass called out.

"Yes, fuck me. Rape me," Jeannie answered. She was loving it. She could feel her cock rock hard bouncing up and down in rhythm with the pounding she was getting from behind.

The guy fucking her grabbed Jeannie's hair and pulled her head up out of the dirt. He put a hand around her throat and started lightly choking her. His other hand started slapping Jeannie's ass. Jeannie grabbed her cock and started to stroke it. The guy let out a muffled grunt and shot his load up into Jeannie, the sensation causing Jeannie to release her load. Jeannie's cum shot arched up high in the air, landing several feet away on the greasy pavement. With the guy's hand wrapped around Jeannie's throat, the sensation of the ejaculation was amazing.

The guy stood up and started to walk away. Jeannie, light headed from both the cum shot and the light choking fell backwards against the dumpster, sitting on the dirty pavement.

The guys started to walk away. "Hey, what about my money?" Jeannie called out.

The main guy pulled a wad of bills out of his pocket. He wiped his cock with the bills and threw them on the ground. "There you go, you fucking cunt whore." The three guys walked away.

Jeannie collected up the money. It was more than $300. Those stupid fuckers had paid more than they agreed on.

Jeannie wandered back to her car. Her face and hair were covered with dirt and grease from the pavement, her knees were scraped and bleeding and her ass was aching from the pounding it just received, but Jeannie was happy. When she added the money from the 3 college boys to what she'd already made that night, it was a good haul.

She slipped the money from the college boys into her bra, and squeezed her false tits. "Don't you worry, soon I'll replace you with real boobs and then we'll be off to New York City and out of the trailer park for good."

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