Trailer Trash Tranny Ch. 07

The story was pretty inspiring for Jeannie to hear. Anthony had overcome some amazingly long odds to get where he was. Jeannie had some stuff to overcome, but nothing like what Anthony had overcome. She could do it.

When they got to the restaurant in Allentown, Anthony showed Jeannie to a table and then went into the back to get some guys to help him unload the pig in the trunk. A waiter came by and put down a glass of white wine on the table. "Hello, my name is Nicolas. Anthony asked me to take care of you this morning. Anthony has put in an order for some food for you, and I've matched the first course with this wine. Should be a good meal."

The meal that came out was excellent. There was three courses and Nicolas did an excellent job of picking a matching wine. Anthony came out as Jeannie finished up her meal, and grabbed a seat. "I don't have much time to talk. It's almost 11 in the morning, and we are about to open for lunch. Did you enjoy the meal?"

Jeannie nodded. "Very much. I think it's the nicest meal I've ever had. Usually I just eat at fast food places."

Anthony laughed. "Well, once you get to New York and become a famous fashion designer, you'll probably have a lot of really nice meals. I hope that you always remember this one with some fondness."

"I wish I could pay you for the meal," Jeannie said.

"Nonsense, it was my treat," Anthony said.

Jeannie leaned forward and took Anthony's hand, stroking it. "Isn't there something I can do for you?" she asked.

Anthony patted her hand, and leaned forward and kissed her on the forehead. "Your company on the car ride was payment enough," he said.

Jeannie and Anthony talked for a few more minutes, but then the restaurant was about to open so Anthony had to get back to the kitchen. Jeannie thanked him again for the meal, before grabbing her stuff and heading for the door. She walked out of the restaurant feeling elated. She had a full stomach and was less than 100 miles from New York City. True, she still only had $6.00 on her, but she'd done pretty well getting this far without much money. Making it to New York City seemed like destiny now.

Once Jeannie started traveling again, Jeannie's mood turned darker. Getting from the restaurant back to the highway was a bit of a hassle, however, as most folks were just puttering around town and not willing to pick up a hitchhiker. It was almost 1:30 PM when Jeannie finally made it back to the highway, having spent two and half hours without getting any closer to New York city.

Jeannie surveyed the scene. There was a truck stop just down the road, so Jeannie walked towards it. She wandered through the parking lot, holding the New York City cardboard sign in her hands. A few of the trucker's took a look, but shook their heads. Finally one of the trucker's motioned her over.

"Headed to New York," Jeannie asked.

"I can get you to pretty close," he said. "I'm headed a place just outside of New York, maybe 40 minutes to an hour into Manhattan, depending on traffic."

Jeannie nodded, "sounds good, thanks."

The driver looked up and sighed. "Gas is pretty expensive, though. It's hard to make ends met as a driver nowadays."

Jeannie winked at him. "Well, I can't afford to help pay for your gas. But I'm pretty sure we could come to some sort of agreement, don't you think?"

The driver nodded and smiled. "Sure, sure. Why don't you climb into the cab, and we can talk about what you think a ride to New Jersey is worth."

Jeannie climbed into the cab. As she was climbing into the cab, she saw that the guy had a huge pile of porno magazines and DVDs in the back of the cab. She quickly scanned the titles. There was a lot of verity in his porn collection, Jeannie could see. She was happy to notice a few shemale videos. Jeannie reached back and grabbed a video called "Rio's Shemale Craziness."

She held up the video and looked at the back. The driver blushed at the title she had chosen, and stammered out that he thinks someone gave that to him.

"Oh yeah, that's too bad," Jeannie said.

"It is?" the driver asked.

"Oh yeah. You think Rio has some crazy shemales, you should see what you'd find in Omaha's trailer parks. Did I mention I was from Omaha?" Jeannie said, looking in the trucker's eyes.

The trucker looked up and down Jeannie's body, putting together what Jeannie was saying. The driver reached back and pulled out another video, this one called "Blonde on Blonde Shemale Action." He gave the DVD case to Jeannie, and pointed at one of the girls on the cover.

"You look kind of like that girl," he said. He ran his finger down until it was point at her penis. "Do you look like that girl EVERYWHERE?" he asked, tapping his finger at the girl's penis on the DVD.

God, this guy is slow, Jeannie thought. She nodded, and told the driver that she looked EXACTLY like the girl on the cover, though maybe Jeannie was a little bigger.

The driver smiled. "So, what do you think a ride to New Jersey is worth?"

Jeannie smiled. "You can do what you want to me for a full half-hour, how's that? You can stick whatever you want in me, in any hole you want, or if you want me to I'll stick what I have in any of your holes. Your choice. I just want to hit the road in the next half hour."

The guy smiled and said okay, and they moved to his cab. The guy shuffled through his video collect and put on a DVD of a shemale gang bang. He pulled off his pants and asked Jeannie to suck him off as he watched the film. Jeannie obliged, and soon the guys rod was hard in her mouth. He stroked her hair as she bobbed up and down on his cock.

The guys cock continued to grow, and soon Jeannie was having trouble fitting it all in her mouth. He must have been 10 inches long and he was as thick as a beer bottle. Jeannie pulled off his cock and said, "Holy fuck, you are huge! What are you doing as a truck driver. With a dick like that, you should be in porn!"

The guy blushed. "Really, you think so?"

Jeannie stroked the monstrous cock. "Hell yeah. You'd be a super stud in porn. Big cock porn is huge."

The guy smiled. "Maybe I will," he said. "Sometimes girls complain about it being too big."

Jeannie pulled down her pants and moved her ass over the head of the guy's dick. "Well, you won't hear that complaint from me," she said, as she lowered herself down on the monster cock. It was huge, and Jeannie had to work herself slowly down on the dick. It took a while for her ass to open up enough just to get the head inside. She had to work herself very slowly down the shaft, but once she got it inside her, it became easy to push it deeper inside her.

Once she was comfortable with the cock inside her, she started to move up and down on his shaft. She accelerated her rhythm, and soon had the monster cock moving in and out of her ass pretty quickly.

Jeannie started talking dirty to the driver, telling him all about what a popular porn star he would be with his massive dong, and how many dirty porn whores he would drench with his come, both shemale and genetic girls.

The driver was loving it. He started thrusting his dick deep into Jeannie's ass. "Yes, take all of my monster cock," he screamed, pushing himself all the way into Jeannie's butt. Jeannie didn't think she could fit it all in, but somehow it managed to push all the way back.

The guy pulled half way out, and then started pumping fast and furiously into Jeannie's ass. Jeannie started to grunt and pant and moan, unable to verbalize the feeling of having this guy's thick flesh inside her.

With one last deep thrust, the driver unloaded himself into Jeannie's butt. As Jeannie had suspected, a massive cock like that was going to release a massive load, and she could feel her ass fill up quickly with come. The come kept coming out of driver's cock, and soon the come was flowing out of Jeannie's asshole and running down Jeannie's ass and all over the guy's balls and stomach.

Finally the guy had released his entire load. Jeannie pulled herself off the monster cock and sat in the passenger seat. The cool leather of the seat felt nice on tender ass. The driver pulled up his pants and sat in the driver's seat. He started up the truck, and they hit the road.

Jeannie kept her pants off for the rest of the trip, letting the truck's air vents blow cool air on her butt to cool it down. Traffic got pretty bad as they got closer to New York, and it took almost two hours to get to a spot just outside of Newark. Jeannie pulled on her pants, thanked the driver and jumped out of the cab. She checked her watch. It 4:30, and the sun was already getting close to going down.

Jeannie stood at the side of a highway entrance with her New York City sign. She knew she was very close. If she could get into Newark, she knew that she could get a train into the city for less than the $6.00 she had in her pocket.

As the sun was going down when the next ride stopped for her. Jeannie was surprised to see that it was a motorcycle, and even more surprised when she walked up and saw that the rider was a woman. The rider took her helmet off. She was probably in her mid-40s with a short haircut and wearing no make up. Jeannie noticed a sticker on the bike that said, "DYKES ON BIKES."

"I can give you a lift to Jersey City, where I live. From there, you can take the PATH train into New York for $1.75. Sound good?" The woman held out a helmet for Jeannie to wear.

Jeannie agreed, took the helmet and climbed on the bike behind the woman. Jeannie put her arms around the motorcycle rider and off the went. The ride was pretty quick, and soon the rider pulled up outside a small apartment block.

The driver put the kick stand down on the bike and climbed off. She took off her helmet and helped Jeannie off the bike. "The PATH station is about a 20 minute walk that way. Or, if you want, you could come up for dinner," the woman said, running a finger along Jeannie's arm.

Jeannie blushed. "I would, but I don't think I'm the kind of girl you're looking for," Jeannie said.

The woman raised an eyebrow. "What, you don't think young and pretty is my thing?" the woman asked, running finger along Jeannie's cheek.

Jeannie shook her head. "It's not my young and pretty face," Jeannie said. "Rather, it what's between my legs. I don't have the usual equipment that girls have. I have boys equipment down below."

The woman smiled and pulled Jeannie close. "You look like a woman to me. You smell like a woman. I'm pretty sure you'd say you're a woman, correct?"

Jeannie nodded.

"Then you are a woman. All the extra equipment means is that you don't have to put on a strap-on dildo to fuck me." The woman took Jeannie hand and led her into the apartment building. They walked up to an apartment on the third floor, and entered the apartment.

There was no dinner for Jeannie that night, though. As soon as the door to the apartment was closed, the lesbian biker pinned Jeannie up against the wall and started making out with her. The lesbian kissed her hard, holding Jeannie's arms pinned against the wall. The lesbian was quick to take control of the situation. She pulled off her jacket and t-shirt, and pushed Jeannie's head down to her breasts. Jeannie started to suck on the lesbian's nipples.

"Suck them. Nibble my tits," the lesbian called out. Jeannie took the lesbian's right nipple between her teeth and applied some pressure. The lesbian gasped and called out, "yes!" Jeannie, with the nipple still between her teeth, pulled away from the lesbian's breast, pulling the nipple and tit out with it.

"Fuck yes, that's good," the lesbian screamed. After 5 minutes of sucking and biting on the lesbian's tits, the lesbian pushed Jeannie's head down. Jeannie started kissing the lesbian's stomach, working down her stomach. Jeannie reached the lesbian's jeans, undoing them and pushing them off her hips. The lesbian was not wearing any underwear and Jeannie was facing a bushy, black mess of hair.

The lesbian grabbed Jeannie's head and forced it into her snatch. Jeannie started licking and sucking on the lesbian's clit and pussy lips. The lesbian started screaming with pleasure. "Yes, yes, yes! Suck my pussy!"

The lesbian's pussy was soon dripping wet. Jeannie could feel her cock grow hard in her pants. As Jeannie sucked on the lesbian's clit, Jeannie reached down, undid her pants and started to stroke her cock.

After 5 minutes of eating the lesbian's bush, the lesbian shuttered. "Oh God," she screamed out, and fell back onto the floor. The lesbian started fingering her clit furiously, and about 20 seconds later a gusher of pussy juice came streaming out of her. The amount of liquid shocked Jeannie. The lesbian's pussy and legs were soaked with the ejaculate.

The lesbian lay back for a second, trying to catch her breath. Jeannie wasn't sure what to do next, but the lesbian soon cleared that up. "Get over here and fuck my pussy with your she-cock," she cried. Jeannie crawled on top of the lesbian and pushed her cock into the lesbian's pussy. Her pussy was slick with her come, and Jeannie's cock slid in easily. Jeannie pumped in and out of the Lesbian's pussy, and Jeannie started to lick, suck and nibble at the lesbian's hard nipples again. The lesbian started slapping Jeannie's ass with her hands. "Fuck me, fuck me, fuck me. Fuck me with your she-cock," the lesbian screamed.

It didn't take long for the lesbian to have another gushing orgasm, spraying her come out of her pussy again. The lesbian pushed Jeannie off her, and told Jeannie to get on her hands and knees. Jeannie got on all fours, and the lesbian went to a drawer and pulled out a big, black strap-on dildo. The lesbian got behind Jeannie and entered her ass with the dildo. Soon the lesbian was pumping in and out of Jeannie's ass quick and hard. The strap-on apparatus had a piece that was rubbing right against the lesbian's clit, and so she was getting a lot of pleasure fucking Jeannie's ass.

Jeannie reached under her self and started to stroke her cock. The lesbian pushed the dildo into her. Jeannie's cock was slick with the juice from the lesbian's pussy, and it slid easily in Jeannie's hand.

Jeannie felt an orgasm rise up within her. She started to buck her hips up and down, and then released a stream of come onto the lesbian's floor. The lesbian, seeing the come shooting from Jeannie's cock and stimulated by the clit massager on the strap-on apparatus, quickly followed suit, letting another stream of female ejaculate from her pussy. Some of the juice ran down the dildo and entered Jeannie's ass.

After resting for a bit, and then cleaning up, Jeannie was on her way. She realized as she was half way to the PATH station in Jersey City that she had no idea what the lesbian biker's name had been. Jeannie shrugged her shoulders and walked on.

Paying the $1.75 fare to get on the PATH train, Jeannie rode under the Hudson River towards Manhattan. Jeannie looked up at the map that the PATH train took, and realized she had no plan once she got to New York. She didn't even know where to get off the train.

Jeannie choose to get off the train at 9th street. She exited the PATH station and out onto the corner of 9th Street and 6th Avenue. She looked around. The sun had already gone down and the street lights were on.

A man walked by, and Jeannie stopped him. "Excuse me sir, where am I?"

The guy looked at her strangely.

Jeannie clarified. "I mean, where in New York City, what part? I just arrived in town."

"You're in Greenwich Village," he said, and then hurried away.

Jeannie looked around her, soaking in the atmosphere of the city. She knew that she was a small town girl with nothing but $4.25 in her pockets, a few changes of clothes and a course catalogue from a fashion college, but she felt a world of possibilities open to her.

She looked back at the stairs leading down to the PATH station. The girl who walked up those stairs just a moment before was no more. Jeannie, the trailer trash hooker from Omaha was dead. She had been reborn. She was now Holly Hepburn, New York City citizen and future fashion designer.

The trailer trash tranny was dead. Long live Holly.