First-time Boy for Sale

by ChrisCross

Copyright© 2018 by ChrisCross

Erotica Sex Story: Fourteen-year-old Boston boy Davey toys with the question of how often you can sell your first time.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/mt   Consensual   Gay   Fiction   Crime   Anal Sex   Analingus   Cream Pie   First   Oral Sex   Hairy   Size   Prostitution   .

“OK, that enough for me for now,” Davey called out, tossing the frisbee one last time to the older man further down the Boston Commons green and loping over to a park bench, where he’d left his backpack, running shoes, and T-shirt. He’d been out on the park green in just shorts for the past half hour, tossing the plastic disk around. With a salute, the man drifted out of the picture.

As the short, lithe fourteen-year-old reddish-gold blond boy sat on the bench to pull his shoes on, a dark-haired man in tailored white shirt and slacks came over to the bench. He’d been in the area for some time, looking at the activity out on the green from several angles. He watched the man Davey had been throwing the frisbee with disappear over the hill before he came up to Davey. He stood out because he was dressed more for the club or the office than for a stroll in the old city Boston park. He was probably in his early forties, slim, dark-haired, and well cared for. He also noticeably had made a beeline for the bench Davey went to when he saw the boy leave off the frisbee play and head for the sidelines.

“Davey?” he said as he approached.

“Yes? You are Bob?” the boy said.

“Yes,” he answered. He wasn’t, of course, but he wasn’t about to give the boy his real name. “The man you were throwing the frisbee with. Your father?”

“No, he was just a man who had a frisbee and no one to throw it to. My dad’s in Europe.”

“And your mother?”

“Traveling in Europe too. They think I’m at my prep school, but that’s on vacation. So, as they say, I’m home alone. My parents don’t pay much attention to what I’m doing.”

“You know why I’m asking, don’t you?”

“Yes. You know I’m fourteen. You want to know who’s taking care of me now.”

“Right. You’re really fourteen? You were telling the truth on the tape? And you play with men in the park?”

“The tape wasn’t supposed to go where it went. Ben and I were just playing around. The tape was just for him. Yes, I’m fourteen. And I like older men. I just haven’t messed around with them—well not much.”

“You messed around with the man on the tape. Did you—?”

“No, not more than you saw on the tape.”

“You can understand why I am being careful here, I’m sure. You responded to my e-mail. You wish to continue the conversation?” Steven Ames, a downtown Boston lawyer asked.

“Yes, if you do,” Davey answered.

“May I sit?” Steven asked.

“Yes, please do.”

The man did—not too near where Davey was sitting. Davey reached down to his backpack and pulled his T-shirt up, preparing to put it on.

“No, please don’t,” the man said. “I like you that way. You’re a beautiful boy. You moved beautifully out on the green as you were playing catch with that frisbee.”

“OK, if you like. But you have your shirt on.”

“You’re right. It’s hot out here. And if it will help you decide.” He slowly unbuttoned his shirt, pulled the tail out of his trousers, shrugged out of the shirt, and draped it over the back of the bench between them. “Is this OK?”

“That’s fine, thanks. Very nice. You must work out.”

“I do.” He flexed his muscles—his chest was filled out, tapering down to a thin waist, the abs sculpted. Swirls of curly black hair encircled his nipples, and a line of hair ran down into the waistband of his trousers. “Do you like hirsute men, Davey?”

“What kind of men?”

“Men with some hair—like what I have on my chest and arms.”

“I like what you have. Very ... sexy.”

“Thank you. David.” He pronounced the name slowly, lovingly.

“Yes, that’s what Davey is short for,” the boy answered. “I’m named after my grandfather. My mother’s father. He was the one with the money, so they named me after him.”

“It’s a lovely name for a lovely boy. I immediately thought of the statue—Michelangelo’s ‘David’—when I first saw you on the tape—before you ... did what you did and went down on your knees to whoever was holding the camera.”

“Really?” Davey asked. “Even though I don’t ... well, you know.”

“Because you aren’t built like a man ... down there?”

“Yes. I know I’m not big.”

“You’re just fine for fourteen. You’re still developing. There are men who are attracted to boys your age precisely because of ... and Michelangelo’s ‘David’ is sculpted that way. And we consider that perfection for a boy your age.”

“Men like you—?”

“Yes, I saw you on the tape. I’m here. I think you are perfect.” He paused and they did a little dance of looking out onto the park briefly and then at each other before gazing out onto the green again. “You are a virgin to a man being inside you—inside your rear, right? I saw what you were doing on the tape, but—?” Steven finally asked.

“I haven’t done anything more than what’s on that tape—with anyone.”

“And you want it to be an older man who does that?”

“Yes. I like older men—men in good shape. Like you.”

“So you said on the tape. I’m forty-one, but I do stay in shape.”

“I can see that,” Davey responded. There was another pause. A volleyball game started up on the green, and they watched that for several moments, both working at giving the impression they were interested in the game, while both were really interested in this encounter.

“Over seven inches. And thick.”

“Excuse me?” Davey said, looking startled.

“I’m seven and a half inches—and thick. I thought you should know that right off the top, so it doesn’t shock you later. That’s above average, I think, and if it’s really your first time ... You stressed that on the tape you put on the Internet. I will ... I would be very careful, though, for the first time. Later, if we continued. I do normally like to be a little forceful. But at first ... and what you did on film, with whoever was holding the camera ... I wondered.”

“I don’t really know what’s considered big,” Davey said.

“What the man showed on the tape isn’t as big. Not quite as thick ... or as long.”


“So, I just wanted to be sure you would know. I couldn’t promise that you wouldn’t have to take it all. Not if I’m paying for it.” “Oh. Well. I’ve given blow jobs, but no, I’ve never taken it up the ass before,” Davey said. “And I didn’t know until you called that Ben had put the tape on the Internet and on that local site with a hookup offer. He was right. I have done blow jobs like I did to him while he was holding the camera before, but not the other. It was his idea to sell my first time and to say so on the tape.”

“But you’re here. You realize that it’s just normal for men who like to go with other men—and with boys, like you. You answered the call and agreed to meet me.”

“Yes I did.”

“And I mentioned that my interest was in being first—to pop your cherry.”

“Yes, you did.”

“And I said I wanted it bareback.”

“Yes, you did.”

“And we’re still sitting here, talking.”

“Yes we are.”

There was a long pause again, as they both were suddenly interested in the volleyball game. The players were young men, most of them handsome and cut and most of them just in shorts.

“We didn’t settle on a price,” Steven said. “You said that, since you’d never done it before...”

“That I had to check out the rate,” Davey finished the sentence for him.

“Did you?”

“Yes. How much were you thinking?”

“I was thinking $300.”

Davey snorted. “See the boy in the middle of the back row in the team on the right?”


“I know him. He’ll do you for $300, but he isn’t a virgin to the ass fuck. Far from it. I was thinking more in terms of $1,000.”

“I wasn’t suggesting that you move into my bed for a year,” Steven countered. “That’s surely just your starting price.”

“It’s for starting me, yes. I know how important this is to men.”

“I mean an opening negotiating price. No one told you your ass was worth $1,000, I’ll bet.”

“You were talking like I had a very nice ass.”

“You do. You’re an angel. I’ll pay you $500 to be the first one to fuck you. Not a penny more. And I’ll have the cost of the room to cover.”

“I have an apartment near here we can go to,” Davey said. “I have the key to an apartment on Boylston that belongs to someone who is in Europe with my parents. So $600—and another $100 if you want seconds.”

“How far away is this apartment?” Steven asked.

“This is the same place where the tape was made.” Steven was moving around the second-floor studio apartment just to the west of the Boston Commons. “This won’t be filmed, will it?”

“Yes, it was here,” Davey answered. “The camera was held by the other man, so it wasn’t planted anywhere. And he told me it was just for his use. I didn’t know he was going to put it up on a local hookup site and say my virginity was for sale. I didn’t know that until the first man e-mailed.”

Steven had made his circuit of the one-room apartment, with the bed placed in an L off the main living-dining-kitchen room. The bathroom was behind the kitchen inset, beside the bed alcove. Davey was standing in the middle of the room while Steven walked around him, the older man finally coming to a stop in front of Davey and brushing one of Davey’s nipples with the fingers of one hand. Neither one of them at put their shirts back on during the walk over here from Boston Commons. Steven was using his other hand to hook his shirt over his shoulder.

“I wasn’t the first man who called?”

“No,” Davey answered. “Ben and I argued after the first couple of calls.”

“You didn’t want to lose your virginity?”

“I was ready for that,” Davey answered. “Just not to any man.”

“And I’m not just any man?” Steven asked, giving Davey a smile and moving his hand up to cup Davey’s cheek and then around to the back of Davey’s neck to release the band that was holding the boy’s shoulder-length hair in a ponytail. Davey’s hair cascaded around his face, and Steven moved his hand so that his fingers could stroke the boy’s cheek. “Beautiful. Simply stunning.”

“No, you’re a guy who will pay me at least $600 to crush my cherry. Speaking of which...”

Steven took his hand away, his smile having gone a little tight, and pulled his wallet out. “Here. There’s $800 here—in case I want to have you all night. And I mean to have you. Do you have a problem with that?”

“No problem,” Davey said, taking the money. “Hold that thought and position. I’ll be back in a minute.” He took the money and went around into the alcove, opening a closet door, and disappearing for a minute. When he came out of the closet, he was naked.

Steven sucked in air. “God, you have a beautiful body. Tanned all over.”

“There’s a place at school where we go to get an overall tan. Just the boys know about it, of course.”

“And yet have never been fucked.”

“I’ve saved myself for you,” Davey said, as he came back to the center of the room. “And to get back to your question about not being just any man, can you tell that it’s not just the money ... that you aren’t just any man?”

“I did notice the erection,” Steven said. “Very nice.”

“And you, Steven, are you hard too? Are you hard for me?”

“You know I am.”

They came together. Steven ran his fingers into the hair on the back of Davey’s head and cupped the boy’s neck, bringing their faces together in a kiss. Davey took the tail of Steven’s shirt out of his hand, which had been keeping the shirt draped over his shoulder, and Davey dropped the shirt on the carpet. Pulling out of the kiss, he murmured, “Can’t you think of anything you’d prefer to be doing with that hand,” and, taking the hint, Steven took the boy’s cock in his hand and reengaged in the kiss. He groaned as Davey undid his belt, unzipped him, pushed his slacks and briefs to the floor, and took possession of his cock.

Stroking cocks, they swayed against each other and kissed. Davey showed that he wanted to be lifted up, and Steven picked him up, pulling the boy up his body, his hard cock going up against the boy’s taint under his balls. Davey hooked his knees on Steven’s hips and flung his arms around Steven’s neck. They kissed and swayed together.

“Are you going to fuck me now, Daddy? Like this?”

“Not yet. Let’s go slow. I want you to be able to take me.” Steven set the boy down on his feet and his hands went to Davey’s shoulders. He pressed down, sending the boy to his knees in front of him.

“I know that you know what to do down there,” he said. “You did it on the tape to the man filming you, and it looked like you knew what you were doing.” Davey took the older man’s cock in his mouth. Steven groaned, running his fingers into Davey’s hair and keeping the boy’s head in place. “Hell, yes, you know how to do that.”

After a few minutes of this, Steven lifted Davey up, guided him backwards to the bed, and pressed the boy down on his back at the foot of the bed. “Reach up and hand me the pillow above your head,” he murmured.

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