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.

I’ll have to say that the Maxwell boy discontented my heart greatly. To be blunt, I’d always had a fetish for boys--and ones far enough into puberty to be assured of being capable of sexual arousal, an erection, and an ejaculation but young enough to have a boyish body and innocence, and, with luck, still to be a virgin. My libido had settled on fourteen-year-old boys. I had been hard pressed to satisfy this fetish in London, but found it not nearly that hard here on the island of the British Virgin Islands, with native boys. What really turned me on, though, were angelic blond boys, so I went all burners when I saw Jimmy Maxwell.

The boy was both angel and devil. He had the looks of an angel, a beautiful face, with a curly mane of blond hair, with reddish highlights, and a lithe body. His smile lit up a room and his hazel eyes were orbs to be lost in. On the other side, he had a knowing demeanor that far exceeded his age. He was a sexual being, even at fourteen, and he knew it and used it--and he mostly used it with men. In our first visit at the Stephensons, he was using it on me and on his stepfather, Maxim, and it was working with both of us. Jimmy seemed to be aware that it only would work with men who had a sexual interest in him. He didn’t use it on Conrad Stephenson, for instance.

It didn’t disturb me that he used his charm on me. I had made an art form of seducing and fucking fourteen-year-old boys when the risk was low--which it was in the British Virgin Islands. The age of consent here was sixteen, but the native population was poor. Couples commonly married anywhere from twelve up, with their parents’ consent, and it didn’t take much money for parents to consent to prostitute their children, female or male, at fourteen. I humped a fourteen-year-old boy at the rate of about once a week, and a virgin at least monthly. So, I was considerably beyond feeling guilt for anything I could afford and get away with.

It did disturb me that Jimmy’s stepfather seemed to be trapped by the boy’s wiles. I could only think of them as wiles, because, although it likely was a game Jimmy was playing and he hadn’t been initiated yet, he certainly was aware of his sexuality and knew how to work it to his advantage. I drew the line at incest. I had never had a carnal thought about my own son, Nathan, even when he was fourteen. My observation of Maxim Maxwell, being in the game myself, was that he definitely had carnal thoughts about his stepson. I left that first meeting with the Maxwells at the Stephensons’ house wondering if Maxwell had married Claudia, who was somewhat of a cold bitch who I thought deserved being divorced, for her charms or for the chance to get into Jimmy’s briefs.

I didn’t feel outraged at that prospect; I only felt the competition of getting there first. I didn’t think Jimmy, because of his own ways, would get much older with his virginity preserved, if in fact he hadn’t already experienced having a cock up his ass. He didn’t give me the impression that he wanted to wait too much longer.

For that reason I chimed in enthusiastically when my wife was setting up pool dates at our house for Jimmy and arranging pickup--I said I’d be delighted to do it--so that his parents didn’t have to worry about driving him around. I wondered if my wife had forgotten that she was taking Nathan to Miami on a shopping spree during the period the Maxwells would be here, but, with luck, she hadn’t thought to tell either the Maxwells or Stephensons about those dates of absence.

I told her on the drive home that I would take care of the telling.


For the pool date Nadia suggested I just throw some pool toys out to the boys and leave them to entertain themselves. Jimmy and Nathan did seem to manage to be happy to go through the rota of sports we could support at home, and they’d tried tennis and shot some basketballs before heating up and coming to the pool. I already was there, in a Speedo, with water toys out to give them, but stretched out on a pool bed after swimming laps. Just because they were going to use the pool didn’t mean I couldn’t as well.

My surmise was that Jimmy wanted an older man to show him what was what and I had confidence that I had maintained a body that would empress a boy his age who was into muscularity.

I went into the pool with them with the toys and showed them how to use the water shooters and a few other things. Nathan knew, of course, but he was good that I showed Jimmy. This meant that Nathan could act like he was learning too and wouldn’t come across to Jimmy as a know-it-all. Nathan didn’t have all that many friends. He wanted to get on well with Jimmy.

During the instruction and demonstration, Jimmy gave me the eye and was touchy feely. I looked damn good in a Speedo and knew that I did.

Instruction over, I made like I was leaving the pool even though I’d made comments that most of the toys were more fun the more you had in the pool playing. They both had absorbed this and pleaded with me to stay in the pool and play with them. I agreed too. We had a good and active time playing in the pool, which accorded several “hands on” opportunities, some of which had hands accidentally applied to sensitive spots. By the time we got out of the pool to have a drink and rest, it “accidentally” was established that both Jimmy and I were hard. For “some reason” I hadn’t accidently brushed up to Nathan’s crotch.

We talked about “stuff.” Jimmy blamed his father for his parents’ divorce. That was natural enough; he was living in England with his mother and his father was far away, in the Caribbean.

He thought his stepfather was handsome and they had a good time together in England when he wasn’t at boarding school. His stepfather “did stuff” with him. What that told me was that I’d better move fast.

He was about to start his second year at Eton, near Windsor Castle, on the Thames, and the school was “all right,” but he wasn’t too keen on the older boys there--or rather, he was keen to be friends with him, but they were into “things” he wasn’t into yet. I couldn’t believe it was pranks, because Jimmy came across as probably the chief prankster in his form at Eton. He talked in more glowing terms about his tutors than the older students, which assured me he was interested in older men. His eyes didn’t glaze over in talking about any of them individually, though, so I don’t think he’d been by one yet.

Nathan was at Rugby, and the two boys spent time comparing those notes.

We went over onto the lawn next to the swimming pool and, in our swim suits, and barefooted, kicked a soccer ball around a bit. Jimmy was a beautiful boy--and knew it. He posed in various provocative poses, acting like he thought he was being a clown, but he and I knew better. I did some posing for him too, and I could see that he was interested.

Nathan made what happened later possible by going for a ball on the stone terrace around the pool, taking a fall, and sliding a bit, scraping up his leg. He didn’t cry, but Nadia heard the commotion and came out and took him back in the house to dress the wound.

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