Trailer Trash Tranny Ch. 07

Chapter 07: Odyssey

Jeannie boarded the bus in Omaha, excited to be finally moving to New York City and starting her dream. In her hand, she was clutching her tickets to New York and a catalogue from a school in New York that offered a fashion design degree. She could feel her heart beating quickly in her newly enhanced chest.

Unlike the clothes which Jeannie wore working the truck stop and strip club parking lot as a prostitute, Jeannie was dressed conservatively. She was dressed in a red sweatshirt, blue jeans and a pair of sneakers. Her blonde hair was pulled back into a short pony tail that bobbed on the back of her head as she walked down the aisle.

Jeannie took her seat by the window. She looked out the window and saw her mother standing on the platform, tears streaming down her cheek. Jeannie knew that her mother loved her, but Jeannie also knew that she had to leave. She could never be anything other than a transexual hooker in Omaha, but in New York, she could remake herself completely.

The bus pulled out. Jeannie sat back with a huge smile on her face. She opened up her course catalogue and rested it on her lap. She started picking out courses that she might want to take. Jeannie didn't have much money left, but she figured she'd be able to make some quick cash once she got to New York and could start taking courses soon after arriving.

Little did Jeannie know that just getting to New York was going to be an adventure. In the eighth century BC, Homer wrote a poem about the hero Odysseus and his trip from Troy to Ithaca (the Greek place, not the place in New York). Poor Odysseus faced many obstacles on his trip home, and it took him a full ten years to get home to his dear wife Penelope. While certainly Odysseus' trip was more odious than Jeannie's upcoming bus trip, in an age when one could fly from Omaha to New York in a few hours, and week ahead for Jeannie would prove to be a test of hope and endurance.

The bus pulled out of Omaha just after nine o'clock in the evening, destined for Chicago. A couple of hours after leaving Omaha, the bus pulled into Des Moines, Iowa. The bus driver said they were making a 20 minute stop, so that if people wanted to get a drink or snack before the long overnight trip to Chicago, this would be a good time.

Jeannie got off the bus and headed into the station. She looked at the schedule. The bus arrived in Chicago at 6:45 in the morning. Jeannie was tired and wanted to sleep, so she skipped over the coffee and bought a bottle of water. She was about to walk back to the bus when a man bumped into her.

"Excuse me, Miss," he said. He was about to continue to walk on, but he paused and gave Jeannie a look up and down. He smiled and raised an eyebrow. Jeannie knew that look, he was interested in Jeannie. Jeannie looked up quickly at the clock on the wall. There was still 15 minutes until the bus would leave. She thought of her wallet, which contained very little money now. It would be nice to have some cash once she got to New York City.

"Travelling through?" Jeannie asked. The man nodded.

"Do you have any time for some quick fun?" Jeannie asked.

"What do you have in mind," the man asked, moving closer to Jeannie.

"Give me $40, and I'll give you a nice oral treat," Jeannie said, licking her lips.

"Sure, okay. Let's go to the handicap bathroom," the man said. Jeannie followed the man to the bathroom. They entered and Jeannie locked the door behind her.

The man gave Jeanie $40. Jeannie stuffed the $40 in her pocked, and then got down on her knees and undid the man's fly. She took his cock in her mouth, and started to suck. The man enjoyed the blow job for a few minutes, stroking Jeannie's hair.

"Oh baby, you are so good. I want to fuck you," the man purred.

Jeannie looked at her watch. 10 minutes until the bus boarded. "I don't know that I have enough time. I have to be on my bus in 10 minutes," Jeannie said.

"Don't worry, I'm close. It'll be quick. I'll give you another $40?" the man said.

"Umm, one thing you should know is that I'm a transexual," Jeannie said.

The man looked shocked for a second, but then smiled and shrugged. "Whatever, I'm so horny I'm ready to go."

Jeannie wasn't sure this was a good idea, but could use the $40, so she agreed. The man gave Jeannie another $40. Jeannie put the money in her pocked, and then pulled down her jeans and underwear. Jeannie faced the toilet and bent down over it, steadying herself on the back of the toilet tank. Jeannie thought she heard something click, but before she could turn around she felt the man behind her. He tried to enter Jeannie, but was having trouble.

"It's too tight. You need to spread your legs further apart," the man said.

Jeannie was not amused. "I can't with my jeans around my ankle," Jeannie said.

"Just kick them off," the man said. Jeannie did as the man suggested. The man then spread Jeannie's legs wider apart, and entered her. The man started making loud grunting noises. Jeannie thought she heard a few creaks, clicks and a thud, but the man was grunting so loudly that she couldn't be sure.

Jeannie looked at her watch. 5 minutes until boarding. "Are you close? I have to get going," Jeannie said.

The man pulled out of Jeannie. He hadn't come yet. "That's good enough. Gotta run," Jeannie turned around long enough to see the bolting out of the bathroom. Jeannie looked around and realized that her jeans weren't anywhere in the bathroom. She didn't see the man with her jeans, so those noises must have been someone else coming in and stealing them.

Jeannie felt tears well up in her eyes. Only 2 hours outside of Omaha, and already Jeannie had lost all her money and her bus tickets for the onward journey. Jeannie felt her legs go wobbly, and collapsed in a heap onto the bathroom floor. The tears started streaming down her face.

"How could this happen? How stupid am I? I'll never make it in New York," Jeannie told herself. She was dejected. After a minute of crying, Jeannie stood up. She walked over to the sink and started to dry her eyes.

Jeannie looked at herself in the mirror. Her eyes were puffy and red. "Damnit," Jeannie said. "You are better than this. You've picked yourself up from being nothing but a cheap trailer whore fucking guys for bottles of beer to being a beautiful woman with a dream and a new set of boobs. You can beat this too."

Jeannie stood up, took a couple of deep breathes and walked out of the bathroom. She marched across the station and onto the bus platform. The bus driver was leaning against the bus, smoking. He looked at Jeannie coming and his eyes grew wide with surprise at the sight of a woman marching towards him with nothing but a sweatshirt and panties on.

"Excuse me, sir, but I need to get something out of my luggage," Jeannie said, staring at the driver in the eye.

The driver nodded slowly, and then opened the compartment under the bus. Jeannie pointed at her bag, and the driver pulled it out. Jeannie opened it up and pulled out another pair of jeans. She slipped them on, zipped back up her bag and handed it back to the driver.

The driver put the bag away and closed the door of the compartment.

"Sir, I have one more issue. It seems that I have lost my tickets to New York City. Is there a way I can get a replacement?"

The bus driver frowned. "I don't know. I remember you from before and checking your ticket, so I can take you to Chicago, but as for any tickets onwards from that, I can't help you. You can talk to the ticket office in Chicago when we arrive there in the morning."

Jeannie boarded the bus. The bus drove through the night, but Jeannie couldn't sleep. She was upset at herself for letting that asshole steal her money and tickets. She was also concerned about how to get money for the rest of the trip, which still had two days. She didn't know if she'd be able to get replacement bus tickets. She spent most the night shaking with anger and nerves as the bus made stops in Iowa City, Wallcott Junction and Aurora before pulling into downtown Chicago.

Jeannie got off the bus and retrieved her bag. The driver smiled at her, and wished her luck with the rest of her trip. He handed her a piece of paper. She looked at it and saw it was a copy of the ticket that the driver had taken from her in Omaha. "Hopefully this will help prove that you had a ticket," he said.

Jeannie wandered into the Chicago bus station. This was as far from Omaha as Jeannie had ever been. Omaha had always seemed like a busy place, and it had tall buildings, but Chicago was amazing to Jeannie. The bus station was full of people all moving around. She looked out the front door, and saw the massive skyscrapers of downtown Chicago reaching up into the clouds. She felt her heart jump up into her throat.

Jeannie walked over to the ticket counter and explained that she had lost her tickets. The ticket agent didn't even look up from the crossword puzzle she was doing, "go to the customer service office near the south entrance. NEXT!"

Jeannie wandered towards the customer service office. As she was walking, a man knocked into her and spilled some of his juice on Jeannie's sweater.

"Oh, I'm so sorry," the man said, grabbing some napkins out of his pocket. He started dabbing at the spill. Jeannie was trying to push the man away when she felt a hand in her pocket. She grabbed at the hand and spun around, seeing a woman with her hand in Jeannie's pocket.

Jeannie smiled at the woman. "Don't bother. I've already had everything I own stolen." Jeannie pushed the woman away, glared at the man and then walked away.

The man in the customer service office wasn't very helpful. Jeannie paid for the ticket with cash, and with no names on the ticket, there was no way to prove who the ticket belonged to. "I'm afraid you are just going to have to buy a new ticket," he said.

Jeannie looked at the clock. It was almost 8:00 AM, when the bus she was supposed to be on was leaving. Jeannie had no money in her pocket, and no way to buy a ticket.

Jeannie found a pay phone, and placed a collect call to the only person she thought could help.

"Collect call from Jeannie, do you accept the charges?" Jeannie heard the operator say.

The squeaky voice cracked on the other end, "of course, yes."

"Go ahead," the operator said.

"Dalton, thank god you are home. I'm in a lot of trouble, you have to help me," Jeannie said to Dalton, the nerdy computer geek that lived in the same trailer park as Jeannie. Jeannie knew that Dalton had a crush on Jeannie and she felt bad taking advantage of him, but she was the only person that Jeannie knew with a credit card.

"I'll do anything for you, Jeannie. You know that," Dalton replied.

"I need you to buy me a bus ticket from Chicago to New York. You can do it online with your credit card, right?"

There was silence on the line.

Jeannie frowned. "Dalton, please tell me you can help me."

"Ummm. I'd love to, Jeannie. You know I would, but I have a problem with my credit card. Remember when you downloaded that movie of yourself from the internet for $11.00? Turns out the $11.00 was a monthly, recurring charge, and now I owe them over $60. The credit card company has frozen my account until I can pay my back balance owed."

Jeannie felt her eyes get wet. "Dalton, you are a computer whizz. Can't you hack into the bus system and get me tickets or something? Anything?"

"I'm sorry, Jeannie. I wish I could, but I can't. Listen, I have to go. I have to leave for work, and I can't really afford to pay for any more long distance. Sorry."

Jeannie heard the phone click, and Dalton was gone. Jeannie's last hope was crushed.

Jeannie looked up at the board showing bus departures. The bus to Cleveland which was the next leg of her journey was leaving in 15 minutes. In less than an hour there was a bus leaving for Omaha. Jeannie was torn. She felt dejected and defeated, and going home seemed easy, but Jeannie knew that if she turned around and went home, she'd always wonder why. Jeannie knew there must be a way to continue her journey to New York. There must be someone heading from Chicago to New York despite the bus company.

Truckers!

Jeannie remembered all the nights working in the parking lot of the truck stop, blowing truckers who were heading all around the country. All she need to do was find a place where truckers hang out and she could find a ride.

Jeannie grabbed her bag and headed out into downtown Chicago. It seemed unlikely that there would be a truck stop in downtown Chicago, but if she could get to the outskirts of the city, then she could find one.

Jeannie knew that Chicago had a big subway system that run far from the center. She took a seat outside a subway stop and started asking folks for change. Business men were a sucker for a pretty, young girl with big blue eyes, and soon enough Jeannie had enough for a subway ride out to the suburbs and even enough left over for an Egg McMuffin sandwich.

Jeannie sat on the Chicago El eating her breakfast sandwich. On the train, two young kids were rapping. They finished up their song, and then walked through the train collecting money from the passengers. Jeannie reached into her pocket, and pulled out the $0.63 she had left over after buying the sandwich and paying for the subway. Jeannie happily gave it to the boys. Jeannie was feeling elated now. She had a plan, and she was back on track.

The subway dumped Jeannie off in the suburbs. She looked up and down the street. Nothing but strip malls. Definitely no truck stops right her. Jeannie looked around and saw a delivery driver making his morning package deliveries.

Jeannie undid her pony tail and tried to make her hair look neat. She walked up towards the truck, trying to look as sexy as she could in an oversized sweatshirt with a big juice stain on the front.

"Excuse me, sir," she said, "do you think you could possibly aid a helpless young girl this morning?"

The driver looked suspicious. "Whadya want?"

"I'm wondering if you know where there is a truck stop around here?" Jeannie said.

"Sure, there is one about 3 miles down by the highway," the driver said, pointing down the road.

Jeannie looked. Three miles was a long walk. "I don't suppose you could give me a lift?" Jeannie said.

The driver shook his head. "I'm really busy. I need to get all these packages off the truck by 10:30 AM. I really don't have time."

Jeannie ran her hand along the arm of the driver. "I could make it worth your while," Jeannie said.

The driver looked up and down at Jeannie. He smiled. "What the fuck? I can rush and get these done afterwards."

Jeannie and the driver climbed into the back of the truck. Jeannie got down on her knees and started to blow the driver. Soon the driver was hard and starting to twitch with anticipation.

Jeannie pulled off him. "Okay, now drive me to the truck stop. I'll finish you off when we get there."

The driver looked incredulous, and stammered some objections, but gave up when he saw Jeannie wasn't budging. The driver climbed into the cab and drove with such speed and recklessness, Jeannie was afraid for her life, but driver arrived at the truck stop without crashing. He pulled into the back and whipped off his pants, the truck still rolling to stop.

"Finish me, please?" he cried.

Jeannie put her face in the driver's lap, and with a few expert motions had the driver spewing. Jeannie pulled away, stroking the driver to completion. Jeannie grabbed her bag and jumped out of the delivery truck.

Jeannie looked at her watch. It was just after 9:00 in the morning. The truck stop was huge, but because it was already late in the morning, a lot of the trucks were already on the road. Jeannie entered the truck stop itself and surveyed the scene. She saw a couple cute guys, and started approaching them. "Where you headed," she would ask. Unfortunately, most of them were headed in directions Jeannie wasn't interested in heading, South or West or towards Canada.

Jeannie was trying to be discrete, as she knew that sometimes truck stop owners frowned upon people trying to hitch rides in the truck stop. She looked over at the counter, and saw the owner staring at her. Time to head back outside.

Jeannie walked out. There was a guy standing away from the door having a cigarette. Jeannie walked over and asked to bum a smoke. The guy handed her a smoke without a word. He was tall and muscular. He had a strong jaw and was unshaven. He had a John Deere cap pulled down to cover his eyes. Jeannie thought he was cute.

"Where you headed," Jeannie asked.

The man looked at Jeannie and frowned. "I don't take hitchhikers," he said.

Jeannie knew that a lot of the drivers were unhappy with hitchhikers, especially the kind that got in their cabs, smoked their cigarettes, drank their bottled water, ate there food and didn't contribute anything to the ride. "I'd be willing to pay for the ride," Jeannie said. She put her hands on hips and, cocking them to the right said. "I don't have any money, but I'm sure I could figure out another way to pay you."

The guy shook his head, "you ain't my type."

Jeannie frowned. This was proving to be more difficult than she had hoped. "What is your type?"

The guy just shrugged.

Tough customer, solid as a rock and showing no emotion. Humor would break the ice, Jeannie thought.

Jeannie looked up at the guy, grinning. "You should reconsider, because I can be lots of different types. What do you like? Slutty school girl? Intellectual college girl? Dirty whore? Put on a leather bra and panties, whip your ass and call you a sissy?"

The guy laughed. Jeannie could see he was starting to lighten up.

"I'm not sure you have the equipment to be my type," the guy said, staring down at Jeannie's groin.

Could it be this easy? Was this guy looking for cock?

Jeannie looked around. No one was looking, so Jeannie undid her pants and quickly pulled out her dick. "You mean equipment that this?"

The guy's mouth dropped open. He stared at her cock. He reached out, and touched it. The guy shivered when he touched it, and sighed loudly.

Jeannie heard the door of the truck stop diner opening behind her, so she shoved her dick back in her pants and did up her zipper. The guy and Jeannie stood there smoking while a couple of truckers headed out towards their trucks.

Once they were out of earshot, Jeannie looked at the guy. "So, what do you say? If nothing else, you should at least give me a ride for 2 miles because you've touched my dick."

The guy smiled. "Oh, I will drive you a lot further than 2 miles, and plan on doing a lot more than just touching that cock of yours," he said.

The guy, who introduced himself as Robert and Jeannie headed to his truck. He was heading to Toledo, Ohio. Jeannie looked at her bus schedule. The bus to Cleveland passed through Toledo. Jeannie didn't think she would be able to catch today's bus, but she might be able to pick up the bus tomorrow, which would give her a night to make enough money to buy tickets for the bus.

Robert was about to start up the truck, but paused. He turned to Jeannie and asked if Jeannie if they minded having a little fun first. Jeannie said sure. They moved into the back of the cab. Jeannie asked Robert what he wanted to do. He looked down at Jeannie crotch and licked his lips. Jeannie pulled down her pants and lay on the bed in the back of the cab.

Robert put his head down between Jeannie's leg and started licking her soft cock. He took the cock and swirled it around in his mouth. Jeannie cock started to grow. Robert licked on the shaft, and then moved down to suck on Jeannie's balls. Jeannie stroked her cock as Robert sucked and kissed her cleanly shaved sack.

Robert moved back up to the tip of Jeannie's cock, and started to lick and kiss it. He worked the tip of the cock for a bit and then started to deep throat Jeannie's cock. Jeannie grabbed Robert's head, and started to push his head up and down on her dick. Robert's mouth was wet and warm and Jeannie was soon on the verge of coming.