Sixteen-year-old Hitchhiker
Copyright© 2026 by Kathleen Simpson
Chapter 11
Action/Adventure Sex Story: Chapter 11 - Cindy Taylor is sixteen years old. Having lived all her life in a small Missouri town, she is drawn by the lure of excitement to Los Angeles. Innocent and naive at the time of leaving home, she soon learns what it will take for her to get along.
Caution: This Action/Adventure Sex Story contains strong sexual content, including Ma/Fa Ma/ft Coercion Consensual Drunk/Drugged NonConsensual Rape BiSexual Fiction Group Sex Anal Sex First Oral Sex Prostitution
Saturday night brought Cindy’s initiation into the world of prostitution.
At first, when Janie suggested it to her, Cindy was shocked. It all seemed to be so cold-blooded. And then it occurred to her that what she had done in the not-too-distant past was just about the same. She had screwed guys for rides and money.
“What should I wear?” Cindy asked.
“How about that low-cut red mini you have?
That really makes you look sharp. You’ll have them drooling to bed down with you.”
“All right. But are you sure I won’t get into any trouble with the cops?”
“Don’t worry. We haven’t had any trouble yet,” Janie said, smiling and trying to be comforting.
“Are you going to be with me?”
“You bet. Maybe we’ll even do a gig together.”
“Yeah, that would be fun, I guess,” Cindy said, her heart not really in it.
“I’ll tell you what. Let’s go ahead and get dressed, and then we’ll eat downtown. How does that sound?”
“Fine.”
“Good. Come on.”
Twilight was beginning to set in, as the two of them walked out of the apartment. Janie with a tailored suede coat, and Cindy, with a multi-colored shawl, left no doubt about what their evening concerned.
“Come on, we’ll take a bus.” Cindy followed Janie, trying to hide her nervousness.
“You know, with any luck at all, we should each make a hundred—maybe two, tonight.”
“That much?”
“You better believe it. In fact, there have been a couple of times when a guy would pay a hundred and then give me another hundred for a tip. And I would still have time to turn a couple more tricks.”
“Whew! That’s a lot of money.”
“Feel better about the idea now?”
“Yeah, a little. A hundred bills just for a fuck. Wow!” Cindy hook her head from side to side.
“Good, here’s the bus. Come on.”
Together, the two of them climbed on board. Paying the fare, they went to the back of the bus and sat down. “You nervous?” Janie asked.
“A little, I guess. I don’t know why, though. It’s not like I’m a virgin or anything.”
“Yeah, still it’s the first time you’ve ever done anything like this. Balling for money, I mean.”
“No, not really. There were a couple of times when a guy paid me after screwing him. You know, when I was thumbing.”
“Yeah, but that’s different. You didn’t know you were going to get paid.”
“Yeah, but still—”
“Well, there’s a difference. Here a guy is going to try and pick you up, and you’re going to tell him flat out that it’ll cost him fifty bucks. A hundred if you think he’s got it. One thing you gotta learn about these guys is that they’re all looking for a good time, and they’re willing to pay for it.”
“Well, I’ll do my best,” Cindy said, feeling herself relax somewhat.
“Don’t worry. You’ll do fine.” Janie winked at her.
When the bus reached Market and Powell, the two of them got off. It was just beginning to get dark.
“Come on. Let’s get something to eat. I’m starved.”
“Sounds good,” Cindy said, following Janie.
“How does barbecue sound?”
“Fine.”
“I know a great place. Follow me.”
Crossing Market, the two walked over to Powell and up about half a block. “This place has the greatest barbecue I’ve ever tasted,” Janie said, licking her lips.
Inside the restaurant, the floor was covered with sawdust. The smell of meats cooking slowly started Cindy’s mouth watering. If the food tasted as good as it smelled, she knew she would love it. Sitting down at a booth, they waited for a girl to come and take their order.
When the girl came over with a menu, a moment later, Janie and Cindy weren’t long in making up their minds.
“I’ll have the combination plate with French fries and coleslaw,” Janie said.
“I’ll have the same,” Cindy said, handing back the menu. “Boy, just being in here is making me hungry as hell.”
“I know what you mean. I just love it here. There’s something about a good barbecue, you know?”
“Yeah, I know.”
It wasn’t long before two platters heaped with steaming hot meats were set down in front of them. Cindy wasted no time in digging in.
“This is good,” she said.
“I thought you’d like it.”
To Cindy, it seemed her plate emptied all too soon. Still, she was comfortably full. “Boy, that was good,” she said, wiping her face with a napkin.
“You want a cigarette?” Janie offered.
“Not your usual brand,” Cindy said, laughing.
“No, but it will have to do out here.”
“Yeah, thanks,” Cindy said, taking one and putting it to her lips. Leaning forward, Janie lit it for her.
For the next ten minutes, the two of them sat there, quietly smoking their cigarettes, while waiting for their food to digest and their stomachs to go down.
Finally, it was time.
“Well, are you ready to hit the streets?”
“I guess so,” Cindy said, feeling her nervousness rising inside her once again.
The Tenderloin in San Francisco is not unlike any other hot spot in any other city. With the coming of darkness, the streets are lit up by thousands of steady and flashing neon lights, all advertising the same thing: girls, girls, and more girls.
All available for a price is the order of the day. Along with the scores of B-girls and hookers, there was sufficient supply for every one of the hundreds of men anxiously prowling the streets, looking to score. Cindy looked over the situation, feeling confidence swell inside her with every passing glance from every passing male.
“How do we do this?” she asked Janie.
“All right. Just walk nice and slow. Keep your shawl around you, but don’t cover up your tits. Let the guys know that you’re working. That’s the main thing. But don’t you start any conversations.”
“Why?”
“Look, if the guy is a cop, he can bust you for soliciting. Dig? If a guy asked you if you’d like some company or anything like that, let him know that you don’t come cheap, but don’t mention money right away. When you’re sure he’s not fuzz, then you can pop your price on him. A good way is for you to just ask him what he thinks you’re worth. That way, he’ll be the first one to mention money.”
“I think I got it.” Cindy tried to absorb the information she had just been given.
“Don’t worry. You’ll be all right.”
A half block up, Janie whispered to Cindy not to say a word, that she would do the talking.
“Well, hello, Janie. I haven’t seen you around for a while. You working tonight?”
“Why, Officer Dunlop, what makes you say such a thing?”
“Call it instinct, huh?”
“Send me two tickets to the Policemen’s Ball, huh?”
“Okay, Janie. Take it easy.”
That was it. Janie and Cindy resumed their walk. “What was that all about?” Cindy asked.
“Oh, he’s just an old friend of mine. Nothing to worry about.”
“Okay.”
“All right. There’s a mark-up there. You watch me, and if I score, you’ll be on your own, all right?”
“Sure.”
He was about forty, medium height, standing against a wall. As Janie and Cindy walked toward him, his eyes moved up and down their bodies, trying to undress them with his eyes.
“Hi,” Janie said, walking up to him. “You look lonely.”
“Maybe I am, maybe not. What are you offering?”
“Company,” Janie replied, smiling seductively.
“Company’s usually expensive. What’s the cost?”
He was acting cool, but Janie could see the eagerness in his eyes. “What do you think I’m worth?”
“I’ve got twenty-five.”
“You’re getting close. Want to try again?”
“All right. Fifty, but that’s all!”
“You just hit the magic number. You staying around here?”
“Yeah, I got a room at the Hopkins.”
“Classy! Let’s go.”
Putting his arm around her waist, they headed off toward the hotel. Cindy, alone on the sidewalk, watched as they walked off. For a short time, she was tempted to run off. Once again, she was alone and afraid. Usually, it was she who got picked up. Not the other way around.
Come on, she thought to herself. Pull yourself together.
Taking a deep breath again, Cindy resumed her leisurely stroll, eyeing the possible candidates for her attentions. All the while, she thought about the fifty dollars Janie was going to get for an hour of her time.
“Hey, baby, looking for someone?” The voice came from a man who had just walked out of a topless joint. Cindy turned and looked at him.
“Maybe. What did you have in mind?”
“It’s your game, honey. You working?”
“Huh?”
“You look like you’re working.”
Cindy didn’t know what to say. “Could be,” she finally stammered.
“Good. How does thirty-five sound?”
Cindy wanted fifty. The same thing Janie had gotten.