Hitchhiking Boy

by ChrisCross

Copyright© 2019 by ChrisCross

Erotica Sex Story: By using his Internet hookups, fourteen-year-old Caleb Meyers makes a nice profit selling his body and scores an Xbox One console in a seven-hour, hundred-mile hitchhike across southern Virginia.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/mt   Consensual   Gay   Fiction   Farming   Light Bond   Rough   Interracial   Black Male   White Male   Anal Sex   Analingus   Oral Sex   Petting   Safe Sex   Public Sex   Size   Prostitution   .

“No, we’re not getting you an Xbox One console for passing all your freshman classes in high school this year. Do we look like we’re made of money? You can earn it yourself. Mow lawns this summer.”

“Earn it yourself” struck a bell with fourteen-year-old, blond, curly haired and blue-eyed Caleb Meyers. “I don’t want to just work all this summer. I want to go someplace and have fun,” he responded to his father. He did know how to mow lawns. He’d just finished mowing his parents’ lawn, and he stood there, behind the mower, in just athletic shorts and sneakers, looking tanned and trim and as good as any fourteen-year-old on the cusp of transitioning from a child’s to a man’s body could look—the muscles starting to show but not taking the smooth-bodied, willowy aspect of a boy’s body yet.

“Like where? Your mother and I can’t take off from our jobs. Summer is high work season for both of us. Where could you go other than to your Uncle Frank, near Roanoke?” Frank wasn’t a real uncle. He had married Caleb’s Aunt Rose after her husband, Caleb’s dad’s brother, Steve Meyers, had died. That meant Frank was just somewhere on the side of the family, but there wasn’t much real family left, so Frank got included. Frank had been considered “in” the family ever since even though Caleb’s mother didn’t like him all that much. Caleb liked him ... a lot, for various reasons.

Caleb gave a little smile, which he hid from his father. His father had fallen right into the trap. “Yeah, I’d like that. Two weeks now at Uncle Frank’s farm near Roanoke would be good. I could work for him and both get my gym work done and maybe he’d pay me something.” Uncle Frank was perfect for what Caleb wanted. He was cool and lenient and several other things too that Caleb wouldn’t mention to his father or, god forbid, his mother. They’d never let him go near Uncle Frank again, if they knew.

“I don’t know how we’d get you there. It’s a hundred miles from Farmville.” Farmville, Virginia, was where Caleb’s family lived. It was a sleepy little college town in the south central area of the state that was dead when the university students from Longwood weren’t there. The next two weeks would be between sessions. Caleb did things with guys at the college and got things from them. That wouldn’t be happening for the two weeks, though, and, even after the summer session at the university started up, it would take him time to establish connections there again.

“You wouldn’t have to take me. I could get the bus to Roanoke and Uncle Frank could pick me up there. How about it?” Everything was still working out good. Caleb didn’t want his parents to drive him to Roanoke. He wanted to get there on his own. If he worked it right, he could keep the bus money and hitchhike there. “I’ll check on bus tickets from Farmville to Roanoke.”

“OK. I’ll call your Uncle Frank.”

Caleb already knew there was no bus from Farmville to Roanoke. The nearest bus service to Roanoke was from Lynchburg, half way there already. But, if he worked it right...

His father came back to say it was OK with his Uncle Frank, who would pick him up at the bus station in Roanoke when Caleb called him from there. Caleb did have a cell phone, a primitive one, his parents let him have. They didn’t know, though, that he had a far more powerful one, a smart phone, that he’d gotten through his Uncle Frank. Frank had been great about tacking Caleb onto his account and not telling Caleb’s parents he had. Frank was cool that way. And he and Frank had other secrets too.

He now went up to his tree house in the backyard to make some calls of his own on a plan to get to Roanoke. The ladder up to the treehouse was a rickety one, which he’d fix, except that both he and his parents knew the ladder wouldn’t support their weight, and thus, what he kept in the treehouse could be kept secret from them.

Once in the treehouse, he used his smart phone to start making some travel arrangements of his own. He had contacts—lots of contacts—his parents didn’t know about.


Luke King pulled his Cadillac Escalade past the “for sale” sign and behind the house in a farmette outside the outskirts of Appomattox, Virginia, where General Robert E. Lee had surrendered the South to General Ulysses Grant of the North in the American Civil War and there fourteen-year-old Caleb Meyers surrendered his body to King in the first leg of his hitchhike from Farmville to Roanoke. Putting the car into park, King turned to the boy, twisted Caleb around to where his back was pressed into the corner between the passenger door and the edge of the seat and his left leg was raised and bent, pressed against the back of the seat.

King, a large, florid red head with a perpetual “you want to buy the house I’m selling” smile on his face, a robust former football player at the University of Richmond, now in his early forties but still an avid, in-shape sportsman, wrapped his right hand around the boy’s neck and dipped down with his face to take Caleb into a deep kiss. His left hand was busy unbuckling and unzipping Caleb’s shorts and fishing the boy’s cock out. As he continued controlling the lip lock and Caleb moaned as he knew the man would want him to, the Realtor from Farmville fondled the boy’s cock and balls intimately until Caleb started rocking on the hand. King’s fingers went under Caleb’s balls and his index finger penetrated the boy’s passage and rubbed his prostate.

Gasping, Caleb pulled away from the kiss and murmured. “Shit. Fuck. Put it in me. Fuck me.” He was rocking on the finger inside him.

King laughed. “Yeah, that’s what I’ll do. I want you to suck me off first, though.” He had gotten himself unbuckled and unzipped and his dick was out. It was a thick slug of a dick rising out of strawberry blond pubic curls. He guided Caleb over and down with the hand on the back of his neck, and Caleb took the thick cock in his mouth and sucked it like it was a lollipop.

Caleb knew what to do. He’d done this before. And Luke King knew how to enjoy taking head from a beautiful, small fourteen-year-old blond. He lay back in his seat, held Caleb’s curly head to his crotch and gave direction on what he liked and what he liked better. He liked deep throating, and Caleb was game for taking all he could into the back of his throat.

“Gonna come,” King growled through clinched teeth, and Caleb pulled his mouth off the cock and took the cum on his face.

“Let’s go into the house,” King said. “It’s empty but I’ve got the key.” King was a Realtor. The house outside Appomattox was one of his listings.

“OK,” Caleb said. The man had paid him $100 and agreed to get him as far as Appomattox. He was due more than just a blow job.

After his dad confirmed with Uncle Frank (who wasn’t really an uncle) that Caleb could come work on his farm for a couple of weeks and that Frank would pick the boy up at the Roanoke Greyhound Bus station, Caleb went up into his treehouse to use the smart phone and laptop his parents didn’t know he had up there. They were busy people with full lives of their own. They didn’t pay that much attention to what fourteen-year-old Caleb did—which was a whole lot naughtier then they could ever imagine he did.

Caleb had a network of attentive male Net friends all over Virginia and North Carolina who were interested in meeting up with him on the strength of his photo, his acknowledged age, and his claimed (for real) sexual experience. It took him less than two hours to set up a relay hitchhiking route across southern Virginia from Farmville to Roanoke on his designated day. This method saved him the bus fare his dad would give him without checking to find out that there was no bus service between Farmville and Roanoke. Caleb also would pick up other money along the route and arrive in Roanoke able to finance what he was doing this all for in the first place. Uncle Frank—good old Uncle Frank—would facilitate Caleb getting what he wanted.

Caleb also wanted the action with the men. He enjoyed being worshipped—having men want him, having men want to put their hands on his body intimately, having men wanting to be inside him. It was probably a phenomenon of his age and tenderness that men who lay with him—and there had now been more than he could count on both hands—were as interested in intimately fondling his body as they were in fucking him and, when they had the time and opportunity, they tended to spend more time with their hands roaming his body than with their cocks inside his channel. For his part, Caleb loved the attention.

On the day, at the appointed hour, Caleb’s dad drove him to the city bus station.

“You want me to come inside to make sure you can get a ticket and sit with you until the bus leaves?” he asked.

“No thanks, Dad. I’ve already called and reserved the ticket. The bus is on time. You have other things you need to do. I’ll call you when I get to Uncle Frank’s.”

Mr. Meyers did have other things he needed to do. He was glad Caleb was getting old enough to look after himself. “And you’ll call me if you have trouble along the route?”

Caleb waved his old cell phone that did nothing much else other than make calls. “Sure thing, Dad.” His smart phone, piggybacking on Uncle Frank’s phone account, was buried in his backpack. He was taking some clothes. There were more clothes of his at Uncle Frank’s—and work clothes for when he was working on the farm. Uncle Frank didn’t wear much, if anything, in the house and neither did Caleb when he visited there.

Caleb stood outside the front of the bus station for some fifteen minutes before a new, black Cadillac Escalade pulled up beside him. The Farmville Realtor, Luke King, was swiveling his head around, looking in all directions for who might be seeing Caleb get into his vehicle. Caleb pulled himself up into the SUV and closed the door. Satisfied they hadn’t drawn attention, King said, “Everything all right?”

“Yes. No problems,” Caleb answered.

“You said a hundred. It’s there on the dashboard, in twenties. Look at it. You put it in your pocket, we’ve got a deal, you’ve got a ride, and I’ve got a blow job and a ride. You put that in your pocket and I’ll drive you to Appomattox, like you want, and you’ll give me what I want.”

The two didn’t need introductions. They both were local to Farmville. They weren’t strangers. They’d hooked up before. King knew Caleb—biblically. King’s initial desire, although with all the others, to explore Caleb’s body with his hands was a fetish of the past now. Now he wanted to fuck him.

With that, Caleb’s hitchhiking day from Farmville to Roanoke had begun.

After Caleb had given King a blow job in the front seat of the Escalade parked outside the house for sale on the edge of Appomattox, King used his pass key to let them into the house. There wasn’t any furniture, but some of the rooms were carpeted. King took a couple of king-sized towels in with them as well as a picnic basket. He’d promised to feed Caleb his lunch too.

King fucked Caleb on the carpeted floor of the master bedroom, with one of the large towels under them. They had stood facing each other after they’d stripped, and kissed and fondled each other. King, large and robust, towered over the smaller, fourteen-year-old trim blond. He covered Caleb with kisses and explored him intimately with his hands, going down on his knees to taste the boy’s cock. Rising and turning Caleb then, he bent the boy over and plastered his face between Caleb’s butt cheeks and ate him out. From there it was just a matter of coaxing Caleb down on his hands and knees, mounting him from behind and above, grasping the boy’s slim hips to hold him in place, and fucking him to a sheathed ejaculation.

They remained naked as they ate the sandwiches and drank the beer King had brought. They were crouched down on their haunches, backs against the walls, across the room from each other, not saying much of anything, just taking each other in with their eyes. King was large, starting to go heavy, but muscular. He gymed and golfed and played tennis regularly. He had a ruddy complexion and his body was covered with a reddish-blond fuzz. He had his hair in a buzz cut because it was starting to recede from the center to the sides on his head. He’d come dressed for Realtor business—a business suit that he had carefully folded when they’d stripped. He sat against the wall, with his knees spread, his cock thick, still in erection, angrily projecting out and curved a bit up from a flaming red, unruly pubic bush. He made no effort to hide himself from Caleb. This was the fourth time he’d fucked the boy in the last two months. Caleb had every reason to be intimately familiar with every square inch of the man.

King was fondling his cock and his balls while he ate, keeping himself hard and throbbing. “That was good. Very nice.”

“The sandwich?”

“No, not the sandwich, Caleb. The fuck.”

“I’m glad you thought so.”

“Satisfying. But I’m still hard, as you see. Not fully satisfied yet. We’re already here. You don’t need to be dropped off for another half hour.”

“Fifty dollars. Another fifty dollar,” Caleb said.

King smiled. He wiped his hands with a napkin, set the remnants of his sandwich aside, fished his wallet out of his folded trousers on the stack of clothes within his reach, and took two twenties and a ten out. He fanned them out for Caleb to see and then folded them and tossed the wad a few feet toward the other wall, where Caleb was squatting.

“Come here. Sit on it,” he said.

Caleb slowly unfolded from where he was sitting and sauntered forward. A can of lube and a string of condom packets were on the carpet by where King was sitting and he tossed the can to Caleb while he slit open a condom packet. Caleb reached around with a handful of lube and greased up his hole while King crowned himself. It was all a routine. They’d done this before. The can went back to King and he lubed his sheathed shaft.

King was sitting, his buttocks extending from the wall, his shoulder blades against the wall, and his legs bent and spread. Putting his hands on King’s shoulders, Caleb crouched down into his lap. There was groaning and a bit of gasping, and low moaning as Caleb descended on the shaft King held steady with one hand encasing the base of his cock. They held there for a few moments as Caleb’s passage stretched to accommodate the cock once more. Then King grasped Caleb’s slim waist between his hands, Caleb leaned back, between King’s bent legs, and placed his palms on the carpet behind him, and they both concentrated on the fuck—King raising and lowering the boy’s body with his hands on Caleb’s waist, and Caleb using the support of his hands and the leverage of his feet to help with the rise and fall of the cock inside his ass.

They started slow, but the fuck became intense, with both of them gasping and panting and groaning and grunting, and Caleb flailing about and digging his fingernails in King’s shoulders as King slammed him up and down on the shaft. With cries—Caleb’s tenor against King’s bass—they announced and celebrated their near-simultaneous comings. Caleb wasn’t into sex with men just for the money.

“That’s what I like about you,” King murmured. “You’re a regular little firecracker.”

They showered in the master bath together, King knowing the water to the house was still on because he was one of the listing agents. King wanted them to shower together and Caleb had agreed. King also wanted to fuck Caleb again in the shower, but Caleb said, “I got a long trip ahead. We can hook up again when I get back from Roanoke.”

He didn’t want to wear himself out on what was just the first leg of a randy men-assisted hitchhike across southern Virginia.

Just under two hours out of Farmville, fifteen minutes before noon, a quarter of the way to Roanoke, a bit sore but ready for the big one on the next leg, and already $200 to the good, including the bus fair and Luke King’s need to have seconds.


Luke King drove Caleb to the parking lot of the McLean House in Appomattox. This was a historical preservation of the house where Lee formally surrendered to Grant to end the American Civil War and here King surrendered Caleb to his next ride—and to be ridden—on the boy’s hitchhike to Roanoke.

It was less than a three-hour drive from Caleb’s family’s house in Farmville to Uncle Frank’s farm near Roanoke and would probably cost $18 in gas money for a car or $50 for bus ticket money, if a bus went between the two towns—at least that’s how much Caleb’s dad gave him to buy a ticket on a nonexistent bus. Caleb planned to make the trip in seven hours, though, and to make about $550 off the trip. He already was $50 up on his estimation because Luke King had paid him a $50 premium for seconds, a fuck that Caleb had enjoyed enough to have done it for free. The whole scheme was to make enough money to buy the Xbox One console his parents had said he couldn’t have—that they couldn’t afford.

He would have to lie under four men—well, five, really—to get all of this done. Each of four men, each driving him on a half-hour or forty-minute segment of the journey were going to pay him to fuck a willing fourteen-year-old boy they’d met and conversed with—and shared photos and preferences with—on the Internet. They had to drive him on the road and, for a price, they could drive him for an hour where and how they liked.

Three of them had signed up for a $100 fee. The fourth, the one taking the Appomattox-to-Lynchburg segment of the trip, was paying $200. There was a special reason for that.

Justin Clark was sitting in his 2019 BMW i8 coupe in the McLean House parking lot when Luke King let Caleb off. Caleb had been told what car to look for, and he’d seen the car in the lot, but he hadn’t told King about the car. He didn’t want these guys connecting with each other. He had King drive on by and over to the nearby courthouse to let him off.

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