Jimmy in the Pool

by ChrisCross

Caution: This Gay Sex Story contains strong sexual content, including Ma/mt, Consensual, Gay, Fiction, Interracial, Black Male, White Male, Anal Sex, First, Masturbation, Public Sex, Size, .

Desc: Gay Sex Story: Living in the British Virgin Islands is a great help to British banker Robert Duncan, whose sexual fetish is robbing fourteen-year-old boys of their virginity. The natives are willing to lay down for him for money. Fourteen-year-old blond angel Jimmy, who is visiting his divorced and remarried mother, is looking for help to gain favor with the randy upper form boys at Eton. Robert is willing, but he's in a race with Jimmy's stepfather for the honors.

His name was Ajay. He was fourteen, a deep chocolate brown, a native of the British Virgin Island of Tortola, the island I lived on. He had built up the mound of hard, water-saturated sand himself for him to nestle on, his pelvis raised. He lay there, docilely, eyes wide open, snuffling but not crying out because I had told him not. He was lying on his side, his legs bent, his knees together, his buttocks elevated on the mound of wet sand. we were in a little sandy area between tall basalt rocks in twisted formation, worn into grotesque shapes by the pounding surf when the tide was high. The secret little area was below my house and just up the beach a way. Very secluded, very private. I don’t think my wife even knew it was here. Still on property I owned.

Ajay clutched what I was paying for him--for his virginity--in one of his hands: five ten-dollar bills in U.S. currency, the U.S. dollar being the currency unit for both the British and American Virgin Islands. It would feed his family for a week. I had made the deal with his father but had made sure in separate questioning that the boy was willing to do it. After this I’d only pay twenty-five dollars to fuck him. But after this, he’d no longer be a virgin.

He wasn’t a virgin now for that matter. I was kneeling behind his raised buttocks, crouched over his little brown body. We both were naked. I held my head close to his, the fingers of one of my hands were buried in his course black bush of hair, holding his head in position, cheek to sand. My mouth was at his ear, giving him encouragement and praise. My other hand was pressed to his brown belly, holding him in place there. My left leg was covering his curled legs. He wasn’t going to move until or unless I released him. He lay there tense and trembling, like maybe he would bolt if I weren’t holding him down. He was a beautiful, brown, perfectly formed fourteen-year-old Virgin Island boy.

But he no longer was a virgin. He’d been a virgin when he came to me here. He was a virgin twenty minutes earlier. But not now, not anymore. The worst was over for him. It had taken time an effort to get inside him. I’m built big. A fourteen-year-old male virgin’s anal opening is small, his passage tight. That was much of the thrill of deflowering him--the difficulty of the first penetration, the feel of him trembling and sobbing underneath me, even though he had agreed to it, as I had my shaft inside him, filling him and stretching him, making him a man’s boy.

I was inside him still, slow pumping him, my pelvis nestled into his buttocks. He was breathing hard, his breath ragged, his eyes open wide in the shock and surprise of it all. But he had come willingly--or at least not grudgingly--not only for the money that would put food on his family’s table but also because he knew he would want to be with men and he knew that he could go into Road Town and be with men for money. He could come back to me a few times too and I’d pay him money. But only a few times. I preferred them fresh and I had no trouble getting them fresh here.

I wasn’t in as deep as I could be. I adjusted our position, first by taking my leg off his and lifting his left leg straight up. He gasped and groaned as this opened him up a bit more and I gave him two more inches of the cock. He was clutching his money for dear life, this giving him context for what he was doing this for.

But both he and his father had come to me. I hadn’t picked him out. The boy had declared that he wanted men, that he wanted to make money in Road Town from men. He and his father heard that I bought the virginity of fourteen-year-old boys and that I trained them to take cock. They wanted Ajay’s first to be the white man, the Englishman, with the big cock. There was status in that. And I’d pay more than another island native would. In fact, if Ajay didn’t lose his virginity at fourteen, a gang was likely to take it away from him for free before he was fifteen.

I changed position again, turning him on his stomach, his lower belly over the mound of sand he’d built up--soon to dry up, though, and blow away. All evidence of what we’d done here, what I had done with--to--Ajay, would be erased by the evening’s high tide. For now, however, it served the purpose. I went on my knees behind him as he was bent over the sand mound, on his knees too, his arms stretched over his head, his cheek to the sand, a resigned look on his face. His right hand clutched the five ten-dollar bills tight.

I pressed my thumbs into his round little brown buttocks, one on each butt cheek, and separated the cheeks enough to inspect the hole that had been tiny at the start but now was gaping enough to take the thickness of me. I loved the contrasting before and after of this view. I lived to ream a small fourteen-year-old passage for the first time. His pert little dick hung down between his legs. It had filled out nicely while I’d stroked it with my hand, and he had come for me.

I had come once already too, but not when I was in deep. I had come, excited myself, when he was still thrashing around from the pain of the first shallow plowing. Now I wanted in deep, though. And I wanted to breed him deep. I jutted my pelvis forward, penetrating him a few inches. He gasped and grunted but he held. The pain of the first breaching was past, and he was beginning to experience the pleasure of the act--the act that he claimed he wanted to make money off of in Road Town. He had declared that he wanted to feel the pleasure of it and knew there would be initial pain. I was doing all of this by agreement--from both he and his father.

It was just when it was real, was really happening to him, that the shock of it also was real. I loved pulling that out of a boy, however.

I gave him several more inches and began to plow him slowly. I urged him to open up and gave him instruction on how to do so. He followed directions well. I told him to start pushing back, and he did so. I moved in deep and stepped up the pace, grabbing his hips, my thumbs still pressed into the flesh of his buttocks. We were in a rhythm together now, and I could tell that he was settling down, understanding what to do, taking pleasure himself.

Still, when I came; pulled out and then slid in and out a couple of times more, enjoying the friction of my cum-augmented passage work; and pulled out a last time, patting him on the butt, telling him he’d done a good job, he hopped up like a bunny and, still clutching his fifty dollars, sprinted through an opening in the rocks and was gone.

I knew he’d be back within a week, however, seeking more instruction from the Englishman’s big white cock--and two ten-dollar bills and a five.

When I walked back up to the house, my wife, Nadia, and my sixteen-year-old son, Nathan, were loading up the Jaguar with picnic supplies.

There you are, Robert, she said. The Stephensons have invited us to a picnic at the residence to meet an old friend of Marge’s--and the friend’s son, Jimmy, who is here for summer break and who Marge hopes can be set up with Nathan for activities.

Ah, Conrad Stephenson, the deputy governor. Not an invitation to be turned down. I wondered how old this son, Jimmy, was. Nathan was sixteen. Was Jimmy that old too?

“No,” Nadia said, “This Jimmy is fourteen, but he’s precocious, Marge says. She thinks that the boys will be a good fit.”

Hot damn, I was thinking. Maybe this Jimmy and I would be a good fit. Fifteen minutes from having humped a virgin and already I was horny again.


I thus came into contact with Jimmy’s family through the Stephensons. Claudia Maxwell had been Marge Stephenson’s friend here in the British Virgin Islands before I had been sent out to manage a UK bank here. And now my wife, Nadia, was a friend of Marge’s. Claudia, divorced from her husband, headmaster of the prep school here, was bringing their son, Jimmy, back for a summer visit with his father--contact that was mandated by the courts. She wasn’t at all pleased about being here, but then I found that she was naturally crabby and, thank God, not all that doting on her son.

Marge Stephenson wanted to make Claudia and her new husband, an official of the Foreign Office in London, and Claudia’s son, Jimmy, welcome and comfortable, so she had invited us to meet them. The Stephensons’s children were older and away at school. Nadia and I had a son, Nathan, who was two years older than Jimmy Maxwell’s age of fourteen, but in development was very close to the Maxwell boy. So, it was natural for Marge to have brought us in to try to match the boys for the short time the Maxwells would be here.

Conrad Stephenson was the deputy governor, so they lived in a provided house--and a very nice one indeed--in the island’s administrative city, Road Town. It was an old mansion with formal gardens but without a swimming pool or any real play area for early teen boys. Nadia and I lived in a sprawling bungalow on the beach east of Road Town, and we had a swimming pool, a basketball court, and a tennis court--the works--so it was also natural that we invited the Maxwells to bring their boy to our house for the boys to play to their hearts’ content.

.... There is more of this story ...

The source of this story is Storiesonline

For the rest of this story you need to be logged in: Log In or Register for a Free account