Trailer Trash Tranny Ch. 04

Chapter 04: Jail

Jeannie was working the parking lot at the truck stop one Wednesday night. It was pretty slow. She had been there for 2 hours and had only made $30 blowing some smelly doofus who took almost 20 minutes to come.

Jeannie decided to wander out by the highway and see if she couldn't pick up a client there. Sometimes guys would cruise by at night looking for some company, and there were a few girls that worked out by the road. Jeannie knew that most of those guys were looking for real girls, but if all the client wanted was a blow job, how would they know what she had under she jean skirt.

Jeannie stood at the side of the highway, her thumb out. A car slowed down and then stopped a few feet from her. Jeannie ran up to the car and leaned in the open passenger window.

"Looking for a ride," the driver asked. He was a good looking guy in his late 30s. He had a full head of hair and was wearing a nice shirt and slacks.

"That depends," Jeannie replied. "You looking for some company?"

"Maybe. Depends on what you are offering," the guy said.

"If you want some company, we could have good time. Would you be willing to help me out with some rent money if we party," Jeannie asked.

"What does my money get me?" he asked.

"$40 for a blow," Jeannie said.

"Yeah, okay. Hop in," the guy said. Jeannie opened the car door. Suddenly a van pulled up behind the car with the high beams on. The doors slide open an 4 guys poured out. Jeannie looked at the guy in the car, and he held up a badge.

"You're under arrest for solicitation," he said. One of the guys from the van grabbed Jeannie and pushed her against the car. A female officer came over and asked Jeannie if she had any weapons. Jeannie said she didn't. The female officer than searched her. When she patted down Jeannie's jean skirt pocked, the officer paused. The officer slid her hand a little closer to Jeannie's groin and felt Jeannie's penis.

The female officer stood up. "She's clean, and she's not a she," she said to one of the other cops.

"What do you mean?" the cop said.

"It's a guy," the female said.

The cop laughed. "I'd never of guessed. Alright buddy, let's go." The cop handcuffed Jeannie and put her in the back of the van.

30 minutes later Jeannie found herself sitting at a desk in the police station. One of the officers was looking at her license, which still listed her as a male. "Unfortunately, I have to put you in one of the male holding cells," he said. "Despite how you look, you are legally a man and I can't put you in one of the female cells. I'll put you in one of the emptier cells."

The cops led Jeannie to a cell and locked the door behind her. There were three guys in the cell. One of them was passed out snoring on the floor. The other two looked over at Jeannie. One was a big muscular guy with a bald head and lots of tattoos. The other guy was skinny but wiry. Both looked pretty tough.

The bald guy stepped forward. "Well, well, what do we have here? Are you a boy or a girl?"

"I'm a girl," Jeannie said.

The bald guy smiled an evil looking grin. "Well, either you must be lying or I must be getting a hell of a gift. Either way, I think we might have some fun, don't you think?"

Jeannie was scared and backed herself towards the corner of the cell. The bald guy walked up to Jeannie. He ran his hand down the side of Jeannie's face. It was surprisingly gentle. "Don't worry, baby. I won't hurt you. I just want to protect you. In return for my protection, you treat me nice. What do you say?"

Jeannie felt the cold metal of the cell wall against her back. The bald guy's breath was hitting her neck, and the small hairs on the back of her neck stood on end. The bald guy's hand continued to gently stroke her cheek. Her fear evaporated, replaced with a feeling of security.

Jeannie looked up into the bald guy's eyes. "You know that I'm a transexual, right?"

The guy smiled. "Baby, I know that you are pretty and young and blonde, and that's all I care about. What's between your legs, that doesn't interest me. As long as that mouth can suck a good cock, that's all I care about."

Jeannie smiled. The bald guy leaned forward and kissed Jeannie. Jeannie let her tongue slip into his mouth.

Just at that moment a speaker cracked to life. "Cell 4, break it up. Cell 4, break it up. Keep your distance from each other."

The bald guy moved back from Jeannie. He was still smiling. "Don't worry, we can avoid the gaze of the cameras," he said. He motioned for Jeannie to walk over the to far side of the cell. "Go and stand in that corner," he said. Jeannie did. The bald guy waited for a 30 seconds or so, and then moved over to meet Jeannie.

"The camera's can't see what's going on right here. As long as they didn't see both of us heading towards the blind spot, they won't say anything."

Jeannie and the bald guy waited for a minute. Nothing came over the speakers. "Okay, we're good," the bald guy said, and started kissing Jeannie again. Jeannie put her hands over the man's big, muscular shoulders and wrapped them around her neck. The man's hands moved down Jeannie's body. His touch was tender, and Jeannie felt a tingle run through her body as his hands traced along her back.

The man's hands reached Jeannie's ass, and he pulled up her skirt. He gripped Jeannie's ass and squeezed it. Jeannie moaned. The bald guy massaged Jeannie's butt cheeks. Jeannie was soon dry humping the guy's leg. Her cock was rock hard, and she could feel his hard cock through his jeans.

The bald man moved a hand off Jeannie's ass and undid hid fly. He pulled out a massive cock, probably 9 inches long and thick. Jeannie got down on her knees and took the cock in her mouth. She could barely fit her mouth around the cock. She took as much of the guy's cock as she could. The bald guy massaged the top of Jeannie's head. Jeannie moved up and down on the massive shaft. The bald guy moaned lightly, trying to keep quiet so that the guards wouldn't be alerted.

Jeannie's jaw started to ache from having to keep her mouth so wide open to fit in the huge cock, but she didn't stop sucking the bald guy. His breathing was starting to get rapid, and she was pretty sure that it wouldn't be long under he shot his load.

"Oh fuck," he said, pushing himself deeper into Jeannie's mouth. Jeannie nearly gagged on the huge rod of flesh being rammed down her throat, but managed to suppress the reflex to gag.

Just then a guard started banging on the glass at the front of the cell. "Hey, stop that you two. No contact between prisoners," he called out.

The bald guy was startled, and stumbled backwards. His cock was spraying massive amounts of come. Some of the come landed on Jeannie's face and shirt and some on the floor. The bald guy was spinning around, and a big gob of come went flying through the air and landed on the cheek of the drunk snoring on the floor. A final big wad of come shot through the air and landed on the glass right by the face of the guard. The guard, startled, moved back.

Jeannie stood up and walked over to the glass. She ran her finger across her face, collecting the bald guy's come that had landed on her. Then, looking directly at the guard, she put the come soaked finger in her mouth and licked it dry.

The thin, wiry guy in the cell, who had been crouching down watching Jeannie suck the bald guy stood up. "Okay, now it's my turn!"

The guard looked in the cell. There was a drunk lying on the floor with come running down his cheek. The bald guy was slumped against one of the cell walls, breathing heavily as his massive cock, still hanging outside his pants, started to get soft. The thin guy was standing up, stroking his hard cock through his pants. And Jeannie, staring at the guard with her blue eyes and come on her t-shirt.

"Okay, this isn't going to work," The guard opened the door and pulled Jeannie out. He then moved all the men in cell 3 to cell 4, and put Jeannie in cell 3 by herself.

Jeannie was happy to not have to be put in a holding cell with a bunch of guys, especially seeing as she didn't have much interest in fucking the skinny guy, but she was going to miss the big bald guy. She had hoped to find out what that massive hammer would have felt like inside her tender, little ass.