Trailer Trash Tranny Ch. 02

Chapter 02: Truck Stop

Jeannie grew up poor in a trailer park just outside Omaha. That made it tough at school. So did being born with the wrong gender. She was a girl trapped in a boy's body. Even though as a kid she only dressed up as a girl in private (what little there was of that in the small trailer she shared with her mother), it was obvious to everyone at school she was a sissy boy. So Jeannie was teased relentlessly at school, both for being poor and also for being such a sissy.

By the time Jeannie was 19, she had dropped out of high school and was dressing full time as a girl. She made a pretty girl, slender with long legs and a tight ass. She had shoulder length blonde hair and pretty blue eyes on a pretty face. She didn't grow much hair on her body anyways, so it was easy to keep her skin smooth and hairless.

After dropping out of high school, Jeannie wasn't sure what she was going to do with her life, but then she learned that some boys were willing to pay to save sex with her. There were boys out there that liked to have sex with a tranny. At first, Jeannie would give it up for booze and cigarettes, but Jeannie realized that to get out of the trailer park, she would need some money. So she started exchanging her body for cash.

Next Jeannie discovered her dream. She saw the movie "Breakfast at Tiffany's," and was enthralled by the character of Holly Golightly. Holly, played by the beautiful Audrey Hepburn, was poor, white trash too. Holly moved to New York and became a socialite and party girl. That was Jeannie's dream. She would move to New York and become a fabulous girl on the party circuit.

Jeannie decided that she need three things to get to New York. The first was a really pretty dress. The second was a bus ticket. The third was a set of tits. Jeannie decided the thing she really needed to make it in New York was a set of boobs. Jeannie needed to save up for a boob job. She didn't want really big tits, just a nice B or C cup.

So Jeannie decided to focus on her work as a sex escort to save up money. There were a few boys at the trailer park that would pay her for sex, but there was only a few of them and they were mostly poor as well. Jeannie needed more customers who had money. The obvious choice for Jeannie, the truck stop down the road.

So Jeannie got dressed in a really short jean skirt with no underwear. She put on a black top that showed off her flat stomach, and put on a bra with falsies to give herself some boobs. She strapped on a pair of 6 inch heels. She did her makeup, and looked in the mirror. She looked very feminine and a lot like the beautiful strippers she saw working at the nearby strip club. Jeannie always thought the girls working at the strip club just off the highway were the prettiest girls in the world.

Jeannie drove down to the truck stop, and started to wander around between the trucks. There were a few other girls working the truck stop, but Jeannie was pretty sure she was the only tranny there.

Jeannie saw a trucker lumbering towards his rig. He was huge, probably close to 300 pounds, and unshaven. Jeannie saw him looking over at her, so she flipped up her skirt to show him her cock. The trucker stopped and motioned Jeannie to come over. Jeannie walked over to him. He was unshaven and not very good looking. "Oh well," thought Jeannie, "sacrifice for my new life in New York."

Jeannie and the trucker agreed on $50 for sex, and moved to his truck. They climbed into the cab and Jeannie moved into the back where the trucker slept. The 300 pound trucker moved towards Jeannie. He roughly grabbed her face, and tried to kiss her. He was a mixture of awful smells - coffee, stale cigarettes, bad breath and body odor. Jeannie pushed him away. "No kissing," she said. "Where's my money?"

The trucker pulled out two twenties and two fives, and gave them to Jeannie. Jeannie shoved the money in her bra, dropped to her knees and undid the fat man's pants. She took his cock in her mouth and started to suck him off. Jeannie could barely stand the smell. His balls radiated a strong smell of body odor. She ran her hand along his balls, and felt a slimy film of sweat. "Oh god," Jeannie said. "Don't they have showers in the truck stop?"

"Shut up whore and suck my cock," the driver said, pushing her head back on his cock. Jeannie tried to look up and lock eyes with the driver, as she knew that guys usually liked that, but she couldn't see past his fat stomach.

Jeannie kept sucking and the fat fucker was getting hard, but Jeannie couldn't take the smell anymore. She stood up and turned around, bending over and flipping up her skirt to reveal her ass. "Just fuck me now," she said, still gagging from the smell of the dude.

The fat trucker entered her from behind. "At least my nose if much farther away from him now," Jeannie thought. The trucker pumped her ass for 30 seconds, but was soon breathing really heavily and his rhythm slowed.

"What's the matter," Jeannie asked.

"Getting... Tired..." the trucker huffed out between heavy breaths.

"Oh for fuck's sake," Jeannie said. She turned around and grabbed the trucker's cock. She jerked him off while playing with herself. The trucker seemed to enjoy watching Jeannie whack herself off. He started adding grunts and moans to his heavy breathing, and then shot a small splatter of come out of his dick.

"Thanks," Jeannie said, climbing out of the cab and leaving the fat trucker standing there panting with his pants around his ankles.

"Hopefully they aren't all like that fucker," Jeannie thought as she started moving back around the trucks. Next she saw a young kid, probably no more than 22 checking her out. She flashed him to let him know she was a tranny and motioned him over. He didn't move towards her, but kept looking at her. Jeannie figured he must be shy, so she would have to do some work for this one. She wandered over to him, lifting up her skirt and playing with her dick as she did.

Jeannie got close to the kid. He was good looking, thin with a good body. He had light blond hair and was clean shaven. Jeannie didn't smell any body odor, which was a good sign.

"Hey honey, looking for some company?" she said.

The boy didn't say anything, just nodded.

"You have a truck?" Jeannie asked. Again the boy just nodded.

"Are you willing to pay me $50?" Jeannie asked.

The boy finally spoke. "For what?"

Jeannie smiled. "You're cute, so for whatever you want."

The boy nodded. They went to his cab, and after he paid the $50, Jeannie lay down on his bed. The boy just stood there.

"Come on over here," Jeannie said.

The boy came over, and lay down beside Jeannie. He seemed so nervous. Jeannie leaned over and kissed him on the the mouth. Soon the boy's tongue was exploring Jeannie's mouth. Jeannie moved her hand down the boy's body and undid his pants. She reached in and felt the boy's hard cock. Jeannie stroked him off as they continued to kiss.

"Do you want me to suck your cock," Jeannie asked. The boy just nodded.

Jeannie pulled his pants down and started to suck the boy. The boy lay motionless and completely silently on the bed. Jeannie wasn't sure if he was enjoying himself. "Are you liking this?" Jeannie asked the boy.

The boy nodded.

"Is there anything else you want to do?" Jeannie asked.

"I want to... suck... you," the boy said.

Jeannie moved herself so that they could 69. The boy, who seemed so nervous and timid before, was not so when it came to sucking Jeannie's dick. He went crazy on it, sucking and licking and kissing her dick and balls. The kid was good at it, and Jeannie was finding herself distracted as she sucked the boy's cock.

Jeannie was soon rock hard, and started to get ready to come. "I want you to fuck me," Jeannie said. She straddled the boy and sat on his dick. His cock slid into Jeannie's ass, and Jeannie started to bounce up and down on the kid. The kid couldn't take his eyes of Jeannie's dick as it bounced up and down. It didn't take long for the kid to come into Jeannie's ass.

"Did you enjoy that?" Jeannie asked, pulling off the boy.

The boy, silent as always, just nodded. Jeannie kissed him on the lips and exited the cab.

Jeannie walked around for about 30 minutes before finding her next client. He was a guy in his 40s with a bushy mustache and a small paunch. He wasn't interested in sex, but paid Jeannie $30 for a blow job. Jeannie blew him as he leaned against his trailer. Jeannie loved sex when people were watching, and a couple people walked by during the act. The guy finally came in Jeannie's mouth, and Jeannie stood up and let him watch as she let the come dribble out of her mouth and down her chin.

Jeannie turned around, wiping off her chin to come face to face with her next client. He was a big, muscular trucker in his 50s. "I like what you did for that guy. You wanna do that for me?" he asked.

"Sure, no problem. $30 for a blow, $60 for full sex," Jeannie said, pulling up her skirt so the guy could see her cock and know she was a tranny.

The guy smiled. "How much for you to fuck me?" he asked.

Jeannie didn't really enjoy fucking guys, but a buck was a buck. "$100," Jeannie said. She was sure the guy would say no, but he agreed. The went to his truck and entered the cab. He paid Jeannie the $100, and then bent down over his bed. At the back of his cab was a huge mirror, so the guy could watch as Jeannie fucked him from behind. The guy pulled down his pants and spread his legs. His ass gaped open with Jeannie even getting close to him. Jeannie lifted up her skirt, and stroked herself until her cock was hard enough to enter the guy.

Jeannie moved up behind the dude and started fucking him. Jeannie didn't really enjoy being a top, but she tried to think of things to keep her hard. Finally she found something to engage her. In the mirror, she could see the guy staring at her. His eyes were wide and he had a huge smile. It was obvious he was enjoying this very much and was very turned on by Jeannie. This turned Jeannie on, and she was soon pounding his ass deep and hard.

Jeannie was close to coming, so she pulled out of the guy and stroked her cock. She spewed her cum up on the man's back. He moaned with pleasure.

Jeannie was getting ready to leave when the man called out to her. "Hey, thanks for that," he said, handing Jeannie an extra $20. "If you feel up for it tonight, come by later and fuck me again. I'd gladly pay another $100 to have that pretty face fucking me."

Jeannie memorized where the guy's truck was, and went out looking for some more clients. There wasn't anyone around. Jeannie noticed some of the other hookers working the truck stop knocking on the trucker's doors. Jeannie decided to try this. At most of the cabs, there was no answer or a "no thank you." A few checked Jeannie out, but weren't interested when they saw she was a tranny.

Finally Jeannie came across a cab that was interested. Jeannie entered and checked the guy out. He was in his 30s, balding and fat, but at least he didn't smell like the first guy.

"I want to fuck you," he said.

"$80," Jeannie replied. The guy balked at the price, and Jeannie and he haggled back and forth until they agreed on $60. The man paid the $60, and Jeannie put it in her bra.

"Ready," the guy asked. Jeannie nodded, and the guy grabbed Jeannie and threw her roughly on the bed. With one hand he held Jeannie down by her throat while with the other hand he pushed her jean skirt up. "You fucking dirty whore, are you ready to get fucked? You dirty little slut want my dick in your ass, don't you?"

Jeannie didn't mind being dominated a little bit, so she was kind of enjoying the roughness of the experience. She smiled and moaned. The guy slapped her across the face two times, and Jeannie felt her dick get hard.

The guy pulled down his pants and pulled out a large and already hard cock. He jammed it into Jeannie's ass roughly. Luckily Jeannie was already loosened up from the previous experience. The trucker's large cock reached deep into Jeannie's butthole. Jeannie reached down and started to stroke her dick.

"Oh, you dirty little slut," the man called out. "You love having this big dick in your ass, don't you." The man slapped Jeannie across the face again, and then started to slap her ass as he fucked her. Jeannie's cock was rock hard, and she stroked it furiously.

The man pounded Jeannie for 20 minutes before shooting a load into her ass. Jeannie's cock and ass were aching from the experience, but it felt good.

"Dirty slut, let's see that ass dripping with cum," the guy said. Jeannie bent over to show the man her ass. She pushed the cum out of her ass and let it run down her butt to her legs. The man smile and ran his finger into the cum. He licked the cum off his fingers, and then got another helping which he fed to Jeannie. She licked the cum off the guy's fingers.

Jeannie stood up and readjusted her skirt. The guy seemed to change completely. He sweetly thanked Jeannie for the experience, and asked her if she worked at this truck stop often. "I come through town about once every couple weeks, and I would love to see you again. I quite enjoyed our experience," he said.

"Enough for a tip," Jeannie asked. "Then I'll make sure to look out for your truck next time you are in town."

The guy agreed quickly and gave Jeannie another $20. Despite his dominating personality during the sex, it was obvious to Jeannie that this guy was putty in her hands, and would do anything she said.

"Can you give me a pack of cigarettes?" she said. The guy nodded and handed Jeannie an unopened pack from a carton the guy had. Jeannie looked at the pack, and then looked at the carton. The guy grabbed another pack and handed it to Jeannie. Jeannie was enjoying playing with the dude's mind, but there was more money to make, so she left the cab.

Jeannie wandered around the lot again and came across two guys. She flashed them her cock, and the guys came over.

"Looking for some company, boys?" She asked.

"Sure, how much?" one of the guys said.

"$30 for a blow, $80 for a fuck," she said.

"If both of us go, how about a group discount? $100 for both of us?"

Jeannie smiled. "$120 and you got a deal." They agreed and wandered over to a car at the back of the lot. The two boys weren't truckers, but were on a road trip. Jeannie got the $120 from the guys, and got down on her knees. She started sucking them both off, back and forth between their cocks as they leaned against the hood of their car. Both of the guys were soon rock hard, so Jeannie started sucking them both at the same time, both cocks in her mouth banging off the walls of her mouth and the other cock.

Once the boys were nice and hard, Jeannie stood up and lay down on top of the hood of the car, throwing her legs in the air. The one guy got between her legs and soon was fucking her ass. The other guy started to suck on Jeannie's cock. Jeannie loved the sensation of having a mouth on her dick and a dick in her ass. "If only there was another guy here so I could have a cock in my mouth," she thought. The one guy pounded at her ass for 5 minutes before the boys switched positions. The other guy entered her butt while the first guy started blowing her.

After four minutes of furious pumping, the guy in her ass came. The guy sucking on Jeannie's cock seemed a little pissed off, punching his friend on the shoulder and asking, "why do you always get firsts and I get stuck with sloppy seconds?"

The guy who came leaned back against the car and watched as his friend started to fuck Jeannie's ass again. "Do you like that I lubbed it all up for you," the friend asked.

"Fuck off," his buddy said, concentrating on fucking Jeannie's ass. Despite being pissed off about getting sloppy seconds, it didn't take long for the dude to shot his load in Jeannie's ass.

Jeannie was about to climb off the car, but the one guy told her to wait. The guy ran off into the parking lot and came back with a dirty looking crack head whore. They walked over to the car.

"Hey, tranny slut, how many dudes you had come in your ass tonight?" he asked.

"Four," Jeannie said.

"Okay. Here's the deal. I'll give you another $20, and give this crack head $20 if you let the crack whore suck all that cum out of your ass."

Jeannie agreed, and the guy paid both Jeannie and the whore $20. The whore got down on her knees and started licking and sucking at Jeannie's asshole, feltching out the cum from Jeannie's ass. The tongue felt good in her ass after the poundings it had received that evening.

After the boys were satisfied that the crack head had sucked out as much as she could, Jeannie jumped off the car hood and wandered away. Her ass was tired, and it was getting very late, so Jeannie decided to call it a night. She then felt her hard cock rubbing against her jean skirt and remembered the guy who liked to get fucked, so she went back to his trailer and give him another ass pounding for $100.

After finishing off, Jeannie went to her car and counted up the money in her bra. An aching ass, but $560 in her pocket. Jeannie was happy with her take. She was well on her way from transforming from the Trailer Trash Tranny to Holly Golightly.