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SEXUAL PERVERSITY ON A TRAIN GOING TO CHICAGO

Introduction

Inside, Sharon Thomas knew there was a dirty, skanky slut waiting, wanting, to come out and go wild; the problem: she’d only slept with two men, at the tender age of nineteen, and she was too shy to approach anyone for sex. Her whore persona remained in her mind, creating nasty adventures as she lay in bed, fucking herself with a silver vibrator.

Inside the Passenger Car

For the first time in her life, Sharon was on a train. She was en route to a university in Chicago for an interview; she had the grades, the recommendations, and they wanted a face-to-face. Taking the train seemed like an adventure. She wore a short skirt and a sweater. She was a quite attractive and alluring, there’s no doubt about it—much of it was an air of innocence about her, and the fact that this young woman had no desire to be innocent, she really wanted to be bad.

A man named Gerald Rhines knew this.

Gerald was forty-eight and on his second marriage; he was returning to the windy city from a business trip. His second marriage was in danger because he had a nasty knack for fucking other women. He couldn’t help it; he loved women. He loved his wife, as much as he loved the first one. It wasn’t like these “other” women meant anything to him; he met them when he traveled (which was required often in his job: regional sales rep for an academic publishing company) and many of them were married as well, these women, out to have a little meaningless fun. They tended to be younger than him.

Gerald liked younger women—what man didn’t? He noticed Sharon in the bar section of the diner car, ordering a mixed drink. He was discreet, following her back to her seat. She seemed to be alone. He liked the way she glanced out the window, at the passing land—her naiveté.

He got himself a drink, returned, and sat across from her.

“No one’s sitting here?”

“No.”

“Do you mind?”

“No.”

Sharon was attracted to him from that moment; she didn’t let it show, of course. Older men made her circumspect; they’d made the moves on her before, but she’d never succumbed. She was going to play it cool with this one. She knew what was on his mind, the way he was looking at her. She crossed her legs for the effect—and yes, his eyes quickly glanced down, the skirt riding high. Maybe he saw her underwear? She hoped so.

“What are you drinking?” he asked.

“White Russian.” She stared out the window, sipped her White Russian. She asked, “What’re you drinking?”

“Tom Collins.”

“Oh.”

“Ever have one?”

“No.”

“You should.”

“It has a lime and a cherry in it.”

He said, “I’m Gerald.”

She liked the streaks of gray in his dark hair. She said, “Sharon.”

They talked a little—why were they on this train? She told him about the interview.

“I had fun in college,” he said.

“I bet you did.”

“Can I get you another drink?” he offered.

She noticed her glass was empty. “Well.”

“A White Russian?”

“I’ll try a Tom Collins.”

He took her glass. She sat there, wondering what the hell she was doing. The man was twice her age! More even! Maybe he wouldn’t come back. Her nipples were hard under the sweater.

Gerald returned with a Tom Collins for her, a White Russian for himself. This made her laugh. She really did like him, and because she liked him, she allowed what happened next to happen.

She said she had to go to the bathroom. She gave him her empty glass, made her way to the bathrooms. She didn’t know Gerald was following her. At the women’s restroom, he pushed her in, closed the door and kissed her. They kissed for a good long minute, his hands on her back and her ass. Their lips parted; they looked at each other.

“I’m sorry,” he said, “I couldn’t help myself.”

She thought: Am I really doing this?

The bathroom was very small. Gerald was quick to get to business. He lifted her, sat her butt on the sink. He pushed her skirt up, yanked her panties off. His cock was red and hard; it was thick with veins and had a giant head. Sharon was worried; the two young men she’d previously has sex with didn’t have cocks the width of Gerald’s. She wondered if it would hurt, if she could stretch that much. She heaved when he put it in her, almost telling him to take it out. He told her to relax and she did, her cunt forming comfortably around the thing. But it wasn’t easy. Fortunately, the whole matter was quick—a three-minute fuck, really, but she came twice, and he came inside her. He kissed her on the nose when he was done. He bunched her panties, put them in the pocket of his suit jacket. “That was great,” he said. He left the bathroom, left her alone there. Just like that.

She sat on the toilet and let Gerald’s semen drip out of her.

She walked back to her seat and realized she had no underwear and Gerald’s discharge was still coming out. It started to run down her thigh. She hoped no one noticed, and wasn’t sure if she cared. She found her seat. He wasn’t there. She thought he would be. She reached into one of her bags, found tissue, and cleaned the cum from her leg, being discreet.

Gerald appeared then, and sat down next to her.

Motion

“Listen,” he said, “close your eyes and just listen.”

“Okay.”

“Are your eyes closed?”

“Yes,” she said.

“Listen to the train. Listen to the machinery.”

“It’s sexy,” she said. Her hand reached over to his crotch.

Three Weeks Later

“Are you following me?”

Sharon jumped, and turned. It was Gerald, on the train. She couldn’t believe this. She couldn’t help it—she embraced him, and kissed him.

“Hey, hey,” he said.

“I’m sorry,” she said. She blushed. She looked around. No one was watching.

Gerald straightened his tie.

“What are you doing here?” Sharon asked.

“I was wondering the same.”

“Another interview at another college,” she told him.

“Work,” he said. “The usual.”

He was looking her over. She was wearing a long skirt this time, and a sheer-fabric blouse, black bra showing through. He leaned forward and whispered, “Wish to go into the bathroom, my dear?”

She could only nod.

He led the way to the men’s restroom. He opened the door, and—to her surprise—roughly shoved her in. Her face hit the wall. She breathed in. She turned to him. His face was carnal. He grabbed her by the hair, pulled her to him, and kissed her. “You little bitch,” he said, “you horny little bitch.”

“Yes,” she said.

“Say this: ‘I’m a horny little skank.’”

“I’m a horny little skank.”

“A slut.”

“A slut.”

“I’m.”

“I’m.”

“A.”

“A.”

“Little.”

“Little.”

“Fuck bunny.”

She laughed.

He pulled her hair harder. “What’s so funny?”

“Kiss me,” Sharon begged.

“I’ll do more than that,” he said, and kissed her. His hands were under her skirt, pulling her panties down.

“Gerald, wait,” she told him. “I’m on my period.”

“I might like that.”

“I don’t.”

“I’ll fuck your behind.”

“What?”

He squeezed her rear end. “I’ll fuck your little brown bunny,” he said. He pushed her toward the sink, and played with her ass. He bent, and kissed the flesh. There wasn’t enough room in here for this. He tried to stick a finger into her. Sharon flinched.

“You’re a virgin here,” he said.

She didn’t know what to say.

“No one has broken your ass cherry yet?”

“No,” she said, ashamed.

“Sit on the toilet,” he ordered her, and she did. He had his cock out, just as huge and veined as she remembered. “Suck it,” and he grabbed her hair; “suck it right now.”

She took him in her mouth, eyes opened; she wanted to see all of this, even though his eyes were closed. Both his hands were on her head, pushing her so that she had to keep taking his cock in deeper with each penetration of her mouth. She gagged. Salvia drooled out of her mouth and on his penis. He opened his eyes once. Looking into those eyes, she knew, right then, that she could love this man—that she would love this man. It was one of those things. He closed his eyes again and continued to roughly fuck her mouth. Her lips were burning. Gerald started to come. As she ate his discharge, something very strange happened—she began to pee. She had no control. Piss flowed out of her, into the toilet, and it made her scream—a muffled scream. She pulled back, his cock popped out of her mouth and she spat cum onto his crotch as she had an orgasm and urinated simultaneously. She pressed her face into his pubes, catching her breath. Gerald stroked her hair.

“Lick up the mess,” he said, softly.

She looked at the sticky cum on his pubic hair, his stomach. She stuck out her tongue and lapped away.

After a while, Gerald pulled up his underwear and slacks.

Sharon stood, noting that her tampon had slipped out, fallen into the toilet. She took another from her purse. She was self-conscious, but Gerald wanted to watch. She put the new one in, crouching, skirt hiked up. She was about to put her panties on and he stopped her.

“Let me keep them,” he said; “a memento.”

“You did that last time.”

“I do it all the time.”

“You must have quite a collection.”

“You think I do this a lot?”

“I’ll be naked under my skirt,” she said.

“That’s the idea.”

“Okay,” she said. “Okay.”

“Here,” he said. He took some toilet paper, wadded it, and wiped traces of semen off her chin. “We don’t want people to see this. That wouldn’t be decent.”

“Yeah,” she said, “they’ll just see my cunt.”

“It’s a wonderful view,” he noted.

Golden Heart and Soul

She had lunch with him in the dining car. She was hungry. She had a bacon sandwich and Gerald had a baked potato, smothered in cheese and sour cream. The train rocked beneath them; like sex, she thought. What she really wanted was to be back in that bathroom. Gerald could tell.

“The wonderful part,” he said, “is when you began to piss.”

She looked at her sandwich.

“This bothers you?”

“It was so strange,” Sharon said, voice low. “I didn’t think I had to go. Maybe because I was sitting on the toilet.”

“Maybe.”

“It was weird.”

“But you liked it.”

“Yes.”

“Look at me.”

She did.

“It was very sexy,” he said.

“It felt sexy.”

“I wish I could’ve had my mouth on your cunt,” he told her. “To taste it.”

“Really? That’s weird.”

“You’re so young.”

She made a face. “Don’t say that.”

“But you are.”

“I don’t say: ‘You’re so old.’”

“I am old, honey,” he said.

“Does it matter?”

“You have a good attitude,” Gerald said. “You are a good person. You have a golden heart and soul.”

“I want you to fuck me,” she whispered. “I want to suck your fat dick again.”

“Have you ever been fucked while on your period?”

“Yes,” she said. “I don’t like it.”

“Why?”

“Blood.”

“It’s only blood.”

“Blood on a cock?”

“I like blood on my cock. And other nasty things.”

“You’re testing me,” she said.

“No.”

“I’ll do anything with you. You know more than me. So teach me.” These words felt so alien coming out of her mouth.

The Second Man

“He’s looking at you,” Gerald said.

“Who?”

“That man.”

“I know,” Sharon said. “He’s been looking at me for a while.”

They were at the bar. Sitting at the counter. The man, in a dark suit, sat across from them. Sharon was drinking wine; Gerald had a martini.

“He’s handsome.”

“He’s okay.”

“He’s handsome,” Gerald said again.

“Yeah? So why don’t you fuck him?”

“You’re going to fuck him.”

Sharon sipped her wine.

“I know you want to.” He leaned close to her ear. “Close your eyes, and listen to the train.”

She did.

“You’re hot,” he said.

“I’m wet,” she said.

“You will fuck him.”

“You want me to fuck another man?”

“I want you to fuck,” he said.

She opened her eyes. “So what do we do? Go over there, make a proposition?”

“Don’t be coy.”

“This is your game, Master.”

“We don’t want him to feel set-up. We want it to seem natural. We’ll go back to our seats and wait a bit. Ten minutes. You’ll come back, alone, and let it play as it lays.”

They left the bar. Sharon quickly glanced at the man; he was admiring the contour of her ass. She made eye contact.

The Indecent Encounter

His name was Andrew and he didn’t take too long to approach her. Sharon was at the counter, having another glass of wine, alone this time. Andrew used the excuse to get another drink and sit next to her. Sharon ignored him.

“I can’t drink wine,” he said.

She sighed. “Why?”

“Bad memories.”

“Wine?” She looked at him.

“Silly high school nights.”

“So what do you drink now?”

“Bloody Marys.”

“I prefer margaritas.”

“Can I get you one?”

“I’m drinking wine.”

He nodded. “Can I ask you something?”

“Sure.”

“Your name.”

“Sharon.”

He told her his name.

They drank.

“Can I ask you something again?”

“Sure.”

“The guy you were here with, not long ago,” he said.

“Yeah?”

“Husband?”

“No.”

“Boyfriend?”

“No.

“Lover?”

“Eh.”

“Father? Uncle?”

“Why do you ask?”

“Stranger?”

“You’re the stranger,” she said.

“Okay, so this is bad,” he said.

“Why is it bad?”

“I’m making a fool of myself.”

“What’s a fool?”

He laughed.

“Funny?”

“You’re beautiful,” he said.

“So are you,” she said.

“I’m going to see my mother.”

“That’s nice.”

“She’s dying.”

“I’m sorry.”

“Cancer,” he said. “Stomach.”

“Oh,” she said.

“You don’t want to hear this.”

“No,” she said, “I don’t.”

“I’d like to kiss you,” he said.

“Not in public.”

“Where else would we kiss on a train?”

“We could always squeeze into a bathroom.”

“Really?”

“You’re not as naive as you act,” she said.

“I never picked up anyone on a train,” he confessed.

“No? It’s fun. Right?”

“What?”

She leaned forward. “Isn’t this fun?”

“It is,” he said.

She whispered, “Wish to go into the bathroom, my dear?”

He said, “Yes.”

She took his hand, and led him into the women’s restroom. Once in, she pushed him against the wall, his face hitting it. She locked the door. He turned around. She slapped him across the face “Kiss me,” she said, “you dirty pervert.”

She grabbed his head, and brought their mouths together.

“It’s so cramped in here,” Andrew said.

“Yeah.” Sharon got down on her knees. She undid his trousers, pulling them down, as well as his boxers. His thin, curved cock sprang in front of her face. It stank of sweat. She took it in her mouth. She was afraid he was going to come fast. She got up, pulled her skirt up and leaned against the sink.

“No underwear,” he said.

“You noticed.”

He saw the tampon string dangling out of her. “Um.”

“Hurry,” she said, “fuck me.”

He grabbed her hips, and shoved his cock into her. It was all very fast. There was blood.

They exited the restroom and didn’t say a word to each other, didn’t look at each other, went their separate ways.

She found Gerald and sat down next to him.

He ignored her the rest of the way to Chicago.

She felt like a dirty, skanky slut and she liked it.

How to Have an Affair and Other Instructions

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