Leaf Rake Boy

by ChrisCross

Copyright© 2018 by ChrisCross

Erotica Sex Story: 14-year-old Jamie works on a leaf-removal crew to try to support himself and his sick mother. He doesn't make enough and it's Christmas time. His boss has already seduced him and now tells him he has a rent-boy add-on service for the business and Jamie could cover his financial needs. Will Jamie sign up? A customer contracts for a sample to help Jamie decide.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/mt   Consensual   Gay   Fiction   Rags To Riches   Workplace   DomSub   Interracial   White Male   Hispanic Male   Anal Sex   Analingus   Cream Pie   Oral Sex   Size   Prostitution   .

“I’ll drive the other guys home first and then you, Jamie,” Jose Hernandez said as the lawn care crew piled into his double cab Dodge Ram.

Jamie knew what that meant. He didn’t mind. In fact, he was getting the hang of it and giving it space in his life. Mr. Hernandez, the owner of the seasonal lawn care business, who now, between Thanksgiving and Christmas, was concentrating on leaf removal from private house lawns, had taught the fourteen-year-old Jamie a lot about growing up and making choices. He also had given Jamie a job that the boy dearly needed. He and his mother, sick with something that the clinic doctors hadn’t been able to diagnose yet, had been living on disability from when his mother had been able to work in a school cafeteria. What Jamie brought in from raking leaves for Mr. Hernandez this fall was the difference between having to choose between heat in their apartment in the projects and food on the table.

Besides, Jamie had been thinking he wanted to go that way anyway, and after Mr. Hernandez had initiated him to it, he decided that he did—and it wasn’t just that Mr. Hernandez gave him some things after that, like some clothes Mr. Hernandez said he’d like Jamie to wear and like the cellphone Jamie was given so he could be in touch.

Not many fourteen-year-old boys got paying jobs. Jamie had started on his own by mowing lawns, which was something someone his age could do in the summer. Even this was a little hard for Jamie, though, because, although being perfectly formed, he hadn’t grown out of a boy’s body yet and it wasn’t that easy to handle a power mower. Mr. Hernandez’s business slowly took over the lawn-mowing business in the neighborhood Jamie could reach from the apartment complex, pulling his mower. But, when seeing Jamie and knowing that he would be putting the handsome, blond-haired, blue-eyed boy out of business, Mr. Hernandez offered Jamie a job for Saturdays and part of Sundays to be sort of a “go for” for the rest of the crew. During this seasonal leaf removal work, for instance, Jamie was put on the rake, working on tight areas where the blowers the others were using weren’t getting the job done.

It was after Mr. Hernandez had bedded Jamie, which quite assuredly was on his agenda from the beginning, that he added hours to Jamie’s schedule, found more that he could do, and gave him gifts now and again of stuff, like the cellphone and some new clothes, that Jamie needed but his mother couldn’t afford to give him. His mother didn’t seem to notice that Jamie was receiving these things—or she just accepted that they were stuff covered by his job. She was having trouble just breathing.

After Hernandez drove the other members of his crew home that Friday, where Jamie had joined them after school, it was just him and Jamie in the truck. There was a wooded area in parkland between where the last man had been left off and Jamie’s apartment complex. The park was deserted this far into the fall, where the leaves were coming off the trees like it was snowing. There was a ranger’s trail that went deep into the park that had a log across the road at its head, but Jamie got out of the truck and moved that and then moved it back again after Hernandez had pulled the truck into the trail.

They drove deep in the wooded area. Jamie didn’t bother to ask where they were going. He knew. They’d been here before. He was busy looking at the wrist watch that Hernandez, a tall, thin, but hard-bodied Hispanic man in his late forties, had given Jamie after they were the last ones in the truck.

Hernandez stopped the truck where the trail went through a thick stand of trees. He talked to Jamie for a bit about how the boy was doing in school, how his mother’s health was, and what other interests the boy might have—topics that a father would ask his son about at the end of a work day, if the boy had a father at home. Jamie didn’t.

After a while, Hernandez had a hand on Jamie’s shoulders, massaging them, and was whispering about how nice Jamie was—how handsome a young man he was, how beautiful his perfectly formed body was, and how he drove Hernandez crazy with need and arousal. Jamie wasn’t resisting any of it. They’d been here and beyond before. Mr. Hernandez paid attention to him and was good to him. And Jamie had been curious about the things the man did to him, and he found that they gave me pleasure and made him feel wanted.

He didn’t resist when Hernandez cupped the back of his neck and pulled Jamie’s face to his for a kiss, or when Hernandez unzipped himself and pulled himself out and guided Jamie’s face into his lap. And Jamie went with the flow after he had given the man the pleasure of sucking his shaft as Hernandez had taught to do when he moved Jamie into a reclining position against the passenger door. He stripped off the boy’s shorts and briefs, moved his own mouth to the boy’s cock ... and pert little balls ... and, rolling Jamie’s pelvis up, to his channel opening caused the boy to moan and pant.

Jamie enjoyed the attention. They’d been here before—and beyond. All of this ground had been covered and had gone into the “permissible” and “pleasurable” zone.

“I want to move this into the backseat,” Hernandez said in a hoarse tone.

Jamie knew that the translation for this was “I’m going to fuck you in the ass now,” and he didn’t resist. Mr. Hernandez had given him a wristwatch, he even told Jamie to tell his mother that it was a cheap one—which it was—that his boss didn’t need any more and had given to Jamie to help him be at work when he should be and to be precise when he filled in his time cards. Hernandez had said to tell his mother that it was just something that went with the job out of company money. Jamie knew, though, that it was payment for letting Mr. Hernandez fuck him again.

There was a duffle bag with canvas leaf tarps in them that Hernandez wedged into the corner of the backseat. He reclined Jamie on his back on this. He ran his hands between Jamie’s legs, coaxing the boy to spread them for him, which Jamie did. Jamie sighed as Hernandez kissed and licked his way up the boy’s inner thighs and did some more preparation work of the boy’s cock and his channel opening with his mouth. Hernandez moved his knees between Jamie’s thighs, came in for a kiss and maintain control over the boy’s mouth as Jamie tried to cry out at the penetration of his passage. The Hispanic man was overendowed, but he was the only man who had been inside Jamie, so the boy’s passage was still at the stretch when Hernandez was fully erect.

Then Hernandez fucked the boy and Jamie let him, turning his face to the side, groaning and moaning and grimacing, but moving his hips as Hernandez had taught him to do, participating in the fuck. He sobbed a bit at the size of the shaft as it entered him, but Hernandez commanded him to relax, and when he did, it wasn’t so bad. And when the shaft was in, filling him and stretching his channel walls, and when it began to move inside him, it wasn’t bad at all. It got more pleasurable with each time Hernandez fucked him, so Jamie was fine with the man continuing to fuck him as they had the opportunity.

“Shit. Fuck, you’re big,” he whimpered.

Hernandez laughed. “You want me to stop?”

“No, don’t stop,” Jamie responded, wrapping his legs under the hard-bodied man’s buttocks and latching onto Hernandez’s shoulder blades with his fingernails. He just had heard or read, he didn’t remember which, that a man who was fucking you wanted to hear that he was big—almost too big.

“No, I didn’t think so,” the Hispanic boss said as he continued pumping Jamie, picking up speed and intensity. “You’re such a sweet little piece.” Jamie collapsed under him, his arms and legs giving way, totally open and vulnerable to the working of the cock, and Hernandez took advantage of the boy’s freshness, need, and vulnerability, taking everything he wanted.

When Jamie entered the apartment, he found his mother sitting at the table in the kitchen, where they took all of their meals in the small, one-bedroom apartment. She was smoking a cigarette and listening to a six-inch-high ceramic Christmas tree play “Joy to the World” over and over again as it revolved on a base containing the music box mechanism. It was all the Christmas tree they had. She was smoking a cigarette, which Jamie knew she wasn’t supposed to do. But it seemed to be the only pleasure she got out of the world these days, so he said nothing.

Instead, he held up his arm and said, “Look, Ma, what I got at work today. It’s a watch. It’s OK, it’s a cheap one. They gave them out so we’d all manage to meet our work schedules better.”

“That’s nice,” his mother answered, winding up the Christmas tree again and setting it on the table to listen to “Joy to the World,” one more time. “Did you bring home anything for dinner?”

“No, sorry, Ma. Shall I go see what’s left in the kitchen and cupboards?”

“You do that. You’re a good boy, Jamie.”

As he was looking, his cellphone rang. It was Jose Hernandez.

“I forgot to ask you if you’d considered the job I’d said you could have to make more money, Jamie. What do you think?”

“I’m still thinking about it,” Jamie answered. It was another step into a new world. Jamie just didn’t know about what to do. But he was tempted. Something in the back of his mind told him it would be wrong to take money for it, but he couldn’t quite understand why it would be. They certainly needed the money. Mr. Hernandez gave him stuff to do it. If, as Mr. Hernandez said, other men would like to do it do him, and they were nice to him, and when they did it to him, he felt special ... and was increasing getting more pleasure than pain from it...

“I forgot to ask you if you and your mother have enough for dinner. I’m nearby and can stop at a fast food joint and bring you something, if you like.”

“Gee that would be terrific of you,” Jamie said. He was standing in front of an open and empty kitchen cabinet.

“And then you’ll give serious consideration to my proposal and get back to me on that leaf removal job we have out in the Gannymead development tomorrow?”

“Sure thing, Mr. Hernandez.”

“Because there may be some more money you can make tomorrow. Christmas is coming. I’ll bet you can use extra money.”


“Wake up Jamie.”

The boy came out of his daydream with Jose pulling on his arm. “He’s in the window, looking at us. Everyone needs to look like they are working flat out. No, don’t look. He’ll know we’re talking about him.”

“Look, don’t look. Which one? Which window?” Jamie said. He sounded a bit groggy, because he had, in fact, been daydreaming. He was irritated that Mr. Hernandez had caught him thinking about his situation, which included what Mr. Hernandez was taking from and was proposing to him, and he had zoned out. Jamie was the rake guy of Hernandez’s seasonal business, which currently was focused on leaf-removal. The other guys were on the blowers and the small, fourteen-year-old blond boy was working the stubborn areas with a rake. They were working on the wooded lot of a high-end house in the Gannymead enclave. The house belonged to Noah Bartlett, owner of a string of power gyms in this and surrounding towns. Presumably he was the one in the window, watching the crew work. Mr. Hernandez had very pointed said there was no Mrs. Hernandez living in the house.

All of the guys in Jose’s crew were quite watchable. Staffing up with hunks was key to the success of his seasonal lawn-care business.

What Jamie had been thinking of were two intersecting issues. He was worried about his mother’s health and about how they were going to cover their needs let alone make anything special out of Christmas. Chances were good that this was his mother’s last Christmas and he’d gotten it into his head that he had to do something special for her this year. What he really needed was some extra money coming in for Christmas, enough for him to get the cupboards stocked up. He’d like to have a Christmas tree and he knew that would cheer his mother up too, but he couldn’t hope to get that—unless...

This need for extra money was where the separate thoughts that had Jamie zonked out intersected. He was still mulling Jose’s offer of getting him extra money. Hernandez knew Jamie’s mom and he were strapped at Christmas. And he also knew Jamie was willing to give him head and to let him cover him. It wasn’t just that Jamie put up with it from Jose; Jamie was a willing submissive bottom. Both Jose and Jamie realized there was opportunity for Jamie in that. Jose’s seasonal businesses had a lucrative add-on service and he was offering to cut the cute and yielding fourteen-year-old in on that.

Jose was offering to cut Jamie in on that added company service here, today, at Noah Bartlett’s house. It was quite a decision to make, though, and Jamie had to try to separate out what he wanted to do from what he should do. A lot of adult responsibility and decision making was being placed on the shoulders of a fourteen-year-old boy. It didn’t help when Jamie took the chance to look at the house and then at the man in the window, not knowing if he was still there. Jamie had never met Noah Bartlett before. He had no idea what the man looked like, although Jose said that Bartlett did the TV ads for his gyms himself, so that told Jamie something right there. The man couldn’t be fat and ugly and be able to sell his gym memberships.

Jamie just didn’t know if he’d let a man paw him and be inside him if he was an ugly toad. So far it had only been Jose who had covered Jamie, and he was a well-built hunk.

When he looked at the window, a huge wall of glass overlooking the wooded front lot, he saw that he—or at least some man—was still there and that he was looking at Jamie. Jose had told the boy that the man had signed up for the extra service and that Jamie could have the job if he wanted it—that Bartlett had been shown the portfolio of the guys working for Jose and had picked Jamie out as the Number One choice. He’d said the younger the better and Jamie was the youngest one of the crew, all of whom, other than Jamie, were already signed up to provide the extra services as required.

The man was standing on the other side of the window just in long, baggy sleeping pants that looked like they might be for Christmas. They were white with what looked like reindeer on them. He had a coffee cup in a raised hand, and he was looking right at Jamie. He was smiling. Just that was enough to make Jamie tremble and start to stir below. So, that part was answered. He was a man who could turn Jamie on.

The boy had no trouble seeing how Bartlett would be a winner in doing his own TV commercials. He was probably better at advertising his product, which was honing and maintaining bodies beautiful, than any actor they could have found would be. Any guy looking at the commercial would be invited to think he could look like that at forty plus himself.

He wasn’t young, maybe forty or a little above, but not being a twenty-something athletic-cut stud was being set on its ear by being a forty-something athletic-cut stud. Jamie don’t know for sure what color hair he had because he had a marine buzz cut and was smooth shaved everywhere the boy could see. He had the muscular, bulging biceps and pecs torso of a warrior god. The sleeping pants hung very low on his waist, accentuating how ripped he was and showing a line of pubic curls that seemed to be a reddish auburn as seen through the window glass. Just seeing the man naked down almost to “the goods” had Jamie breathing hard. The imagination that let loose was probably more arousing than if he’d seen the man totally naked.

He was sexy to Jamie’s mind in ways that Jose hadn’t been. With Jose so far, it had been mainly readjusting clothing in the back of the truck to get the necessary parts together. It hadn’t been a sexy fashion show like this. Jamie supposed his jaw had dropped in seeing how cut the man was, because he saw Bartlett laugh and raise his coffee mug, seemingly to Jamie. The boy thought he also saw one of Bartlett’s hands go down to frame his basket.

“Is that him? Noah Bartlett?” Jamie asked Jose out of the corner of his mouth.

“Yeah, that’s him. The gym king. Really something, right?”

“Yes, really something,” Jaime murmured. “And he chose me out of your lineup?”

“Yep. He said the younger and smaller the better. And we both know what you like. So, are you on? You’ll go in to get the check for the service when we’re done? The guy I send in to pick up the check is the one I’m offering to him to use for two hours as he likes. But at that point either the customer or the guy can decide not to do it.”

Jaime paused to let that sink in, but finally sighed and agreed. “I guess I can. No promises, though, beyond picking up the check. I just don’t know. It would be like being a rent-boy.”

“Yeah, right,” Jose said, and laughed. “It will be exactly like being a rent-boy, Jamie. And you’re dynamite. You and me can make a lot of money off this.” He turned his blower back on and went back to work.


“I’m not going to beat around the bush here. Hernandez is running a business and I’m a customer if it works to my satisfaction. I’ve written two checks here. I’ll give you one and tear up the other one. This one’s for $400 for the leaf removal, plus a tip for the crew. The other one’s for $700 for the leaf removal plus the service Jose Hernandez told me was available. He showed me photos of those available, and I picked you. You’re how old?”

“Fourteen,” Jamie answered, a little hesitatingly.

“Sweet,” Noah Bartlett responded. “I shouldn’t, of course, but you’re a real honey, and fresh and young is the best. Your name is Jamie, right? It’s your pick on which check I give you. The extra service arrangement is fine with me. But maybe you’d like to come in and have some refreshments before you choose. If so, you can take your boots off here and come on in to the living room. Coffee’s OK? Or something stronger? A beer maybe?”

“I really couldn’t ... a beer, you know.”

“For what we might be doing, a beer is the least of the age problems. Have whatever you want. We’re in my house and what happens here doesn’t concern anyone but you and me—and Hernandez. So, what would you like to drink?”

“I guess what I’d really like is just some ice water, if that would be OK.”

“Low maintenance, heh? Sure, that’s fine with me. Make yourself comfortable in the living room up there and I’ll be back with the drinks in a minute.”

Jamie pulled his boots off and left them by the door. Although it was the fall leaf removal Hernandez’s crew had been doing and it was after Thanksgiving already, the temperature had come up and Jamie was in a T-shirt and athletic shorts.

Following Noah Bartlett’s monologue, he’d padded off into the house, presumably to the kitchen to fetch drinks. He was still just in the baggy sleeping pants that hung low on his hips. He was barefoot.

Jamie drifted into the living room, which was two steps up from the lower foyer, where the entrance to the house was and an upper foyer, with doorways into various rooms and a staircase to an upper level were located. It was a really classy, expensive-looking house. Jamie was completely out of his element and just stood there, inside the room, afraid to touch anything, amazed that anyone would have all of this fancy stuff.

The living room was its own wing of the house. It had that nearly full-wall window out onto the wooded front yard, which showed a trimmed-out garden now that Hernandez’s crew had spent three hours removing the leaves. Azalea and rhododendron bushes provided a base of foliage under the trees. The land sloped down to the street, which was hidden from view by the bushes. It was like the house was completely isolated in a wooded paradise when it actually was located in a development just outside of town. The thought that anything could go on in this house and nobody on the outside would know it was going on made Jamie tremble with anticipation.

He knew why he was here. What had gotten him this far wasn’t just the need for money. It also was the wonder of what else in this male-on-male world might happen than what he’d let Hernandez have thus far. Was the Hispanic man the best that could be or were there men who could give Jamie even better attention?

The loveliness of nature outside contrasted with the spare but lush Oriental-style furnishings in the living room. The front yard was terrific and the backyard, which was accessible on the opposite side of the living room through French doors was even more like a park, with Japanese maples added to the azaleas and boxwoods, a high ivy-covered, wood fence in a basket weave pattern surrounding the yard, and stone and brick patios swirled on various levels around a swimming pool and koi pond. All very beautiful but also all very isolated.

The living room was dominated in one corner by an ebony baby grand piano and the opposing corner by a seven-foot decorated and lit Christmas tree. Jamie ached to be able to have a Christmas tree too. He knew his mother would love to have one. Not as big as this one, though. The living room of his apartment in the projects couldn’t hold this one. In the space between the piano and the tree, two sofas sat facing each other, set on a gigantic Oriental rug and with a large Chinese Chippendale-style rosewood-finished teak coffee table between the sofas. Bartlett had placed the two checks on the coffee table, which was otherwise clear. Drink coasters were placed on the surface of side tables at each end of the sofas, so Jamie assumed the coffee table was meant to be left bare.

“This is really a nice place,” Jamie said as Bartlett padded back into the living room. “You live here alone?”

“Off and on,” he said. “Sometimes I have a boy living with me. I like having young, in-shape boys around me. I like experiencing them moving from boys to young men. You’re a really cute one, with your small body, blond hair, and blue eyes. I picked you out of Hernandez’s book right away.”

Jamie didn’t know what he should say to that. The man was being very direct. So, he said nothing, as Bartlett continued.

“No one’s with me at the moment, though. Jose tells me that you are a player. I that right? You have some experience?” The transition was rather bald. There wouldn’t be much buildup conversation here—and Jamie hadn’t made up his mind yet—or at least he’d told himself he hadn’t decided. He was being rushed. In some ways that scared him; in others it aroused him. That had been what had worked for Hernandez. Once the man had made clear what he wanted and Jamie hadn’t shrunk from him, he just took what he wanted from Jamie. That helped mitigate any guilt Jamie might have felt about going this way.

When Bartlett had returned, he handed the boy a glass of water with ice in it. He had poured himself another cup of coffee. Jamie was standing by the coffee table, unsure of whether he was supposed to sit or not.

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