Fire Island Boy - Cover

Fire Island Boy

by ChrisCross

Copyright© 2022 by ChrisCross

Erotica Sex Story: Fourteen-year-old Rob is willing to lose his virginity to his school headmaster, Greg, on a vacation to Fire Island, but it takes a hunky superhero movie star and his fourteen-year-old TV actor sidekick to get it done.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/mt   Teenagers   Consensual   Reluctant   Gay   Fiction   Celebrity   School   Rough   Gang Bang   Group Sex   Anal Sex   First   Oral Sex   Petting   Voyeurism   Public Sex   Teacher/Student   .

Mr. Griffith was reclining on the lounge bed on the deck of hie beach-side Fire Island cottage. Kneeling between his knees, I was giving him languid head. He had told me to call him Greg, but he was the headmaster at Westhaven Hall, a boy’ prep school in Riverhead, on Long Island, and I was just one of his fourteen-year-old students. I couldn’t think of him as anything but Mr. Griffith, even with his cock in my mouth. He must be fifty. I was fourteen and unfucked—at least as yet—although I’d done about everything else he wanted me to do for him.

That had been what had turned him on and had had him pursuing me to the point that here we were on a long weekend. I was a virgin—not to hand jobs and cock sucking, but to anal fuck. He was paying me big bucks to give it up to him this weekend. He’d devised a way of telling everyone I was somewhere else and had brough me here to get it all done. I was having trouble getting there, though.

Not to cock sucking, though. He’d sucked me and now I was sucking him. I knew he wanted more and this was when he thought he was going to get it. I was nervous and shuddering. Sometime this weekend I’d be ready, but not yet, I didn’t think.

He was pulling me up and turning me on my side on the lounge bed, facing away from me. An arm was embracing me, holding me there. His other hand was grasping his cock, moving it into position. I panicked and tightened up.

“What’s wrong, baby? I thought this time.”

“Maybe later. Yes, to it but ... maybe later. I’m all tense. I think a walk on the beach would loosen me up.”

“I think doing it once and getting it over would loosen you up, Rob,” he said, with a heavy sigh. But he was moving carefully here. I was a virgin to ass fucking. He was excited about being first. I hadn’t said no, only not yet. He’d try to patient.

“If you go out on the beach, you might want to walk east.”

“Why east?” I asked, rolling up to sitting on the side of the lounger. He’d snaked a hand around my hip and was stroking me off.

“So nice. You’ve got a beautiful, small, supple body, baby. So, so nice.” Then it was as if he’d heard my question for the first time. “You’ve told me what a hunk you thought that superhero movie actor, Kyle Kingsley, was.”

“Yeah. Now there’s a body. Over six and a half feet of glorious muscle.”

“Yes, well, he lives up the beach toward the east. I’ve heard he’s in residence. You might catch a glimpse of him from the beach up there. It’s a gray A-frame, all glass toward the beach, with a terrace and a big swimming pool.”

“Really? He might be there?”

“Yes, he might. But you’re getting hard for me again, baby. Let’s move into the bedroom and get this going.”

“Maybe after my walk. I need to loosen up.”

“That’s damn right you do,” Mr. Griffith muttered. It was the first sign of the weekend, which had just started, that there was evidence that his patience was fraying.

He got a blow job. I would have taken that all the way if he hadn’t been hoping for more. He was getting some sex. We’d get there, but it would be my first time, dammit. I was a bit scared of what that involved, the inevitable change it would bring to my life. This wasn’t something that should happen lightly. I’d given him a blow job, dammit. He could have taken it to unloading if he wasn’t pushing for more.

I rose from the bed, pulled on my Speedo, and went into the cottage. I remembered that there was a pair of binoculars on the top shelf of the entrance closet. I pulled on a beach shirt, grabbed a couple of towels, one for drying and one from lying on, found the binoculars, pulled on flip-flops, and walked out onto the beach. I stood there for a couple of minutes, looking out on the ocean, and then, turning east, I began to walk.


I didn’t have any trouble finding the house. No one was out on the terrace when I got there and I set my towels, the drying towel covering the binoculars on the beach well below the end of the house’s terrace, raised a good four feet about the sand of the beach. Wooden steps went up to the terrace.

I walked into the surf and then swam out into the ocean for about as far as I thought I should before coming back in. As I was walking back up onto the beach through the surf, I saw him. Kyle Kingsley had come out onto the terrace and was stretching beside a lounge bed. He was naked and he was magnificent. He was a giant of a man and body-builder muscular. He played superhero parts in Sci-Fi movies and he obviously didn’t need any padding to do so. I felt myself go hard as I reached for my drying towel and wiped off. I don’t know if he could see me—he didn’t seem to be looking in my direction—but I fought not to make it obvious I was watching him with my tongue hanging out.

Another guy—younger, smaller, perfectly formed, no older than I was—came out the house. He too was naked. He strutted around the pool while Kyle Kingsley lay down on his back on the lounge bed and sipped from a beer can. The second guy was being far more observant of his surroundings than Kingsley was, so I lay down on my towel, facing the house, and surreptitiously held the binoculars so that I could watch what was going on on the terrace without the two there seeing that I was watching them.

What was going on rather quickly was that the little guy—the boy—was kneeling on the foot of the lounge bed, Kingsley had put his ankles on the boy’s shoulders and the boy was leaning over, obviously giving Kingsley head. After a while, the boy moved up to straddle Kingsley’s hips with his, Kingsley was grasping his waist between his hands, and the little guy, leaning over to palm Kingsley’s pecs, was rising and falling on his cock. After a while, he reversed his position, clutched Kingsley’s knees, and resumed rising and falling on the shaft that way. In that position, the boy was looking directly at me, so, regretfully, I put the binoculars aside, turned on my back, and baked myself, staring at the blue sky and wishing it was me riding Kingsley’s cock. That would be a great initiation. I was sure I could handle that. Mr. Griffith was OK, but he was no Kyle Kingsley.

I kept my head down low then and the next thing I noticed were two feet stopping in front of face in the sand. I had the drying towel draped over the binoculars but not enough for someone standing there not to know what they were.

“Mr. Kingsley wonders if you’d like to come up to his house and have a drink. You’re a cute little thing, aren’t you?”

The voice was recognizable and I looked up in surprise to see a familiar TV actor standing there. Lane Logan played on a stereotypical TV drama-comedy of the time, “Just Us Guys,” in which a motherless family of guys was being blended into the fatherless family of girls. Logan played the second oldest son. I knew he was fourteen, just like me, because when I watched that program, I imagined myself in his part. I had checked his age out. What this now said to me was that he was the boy I’d just seen doing the cowboy ride on Kyle Kingsley’s cock and that that meant Kyle Kingsley did boys my age.

“Excuse me?” I said, which was brilliant, I know, but I couldn’t think of anything else to say in the moment.

“You were watching us through those binoculars of yours. You’re a cute little trick. You obviously know who we are and what we’ve been doing. Mr. Kingsley wants to know who you are and what you’re doing here—whether you are here to spy on him. Inviting you up for a drink is more friendly than calling in the cops, don’t you think?” He reached down and pulled my wallet out of the pocket of the shirt I’d worn down to the beach, so he had me trapped. “It says here that you are Rob Townsend, age fourteen. A real or a fake ID?”

“It’s real.”

“You’re fourteen.”

“Yes, I’m fourteen.” I knew why he asked. He didn’t ask if I was a virgin or not, though. I was a little excited by all of this. I was OK with seeing how this might play out.

“I’m fourteen.”

“Yes, I know you are.”

“And you saw what Mr. Kingsley and I were doing.”

“Yes, I did.”

“And you’d be OK with doing it too?”

I didn’t answer that, but he took that, rightly, as an answer.

“Well, this may be your lucky day. Mr. Kingsley is more in the mood for partying than prosecuting. Are you working for the media? Are you after a scoop here?”

“No. I’m just a school student. I’m here with my boyfriend and he told me Kyle Kingsley lived nearby. I’m a fan, so I came to take a look. Just that, nothing else.”

“A student? You got a boyfriend—at fourteen?”

“Yes.”

“Older than you?”

“Yes. Probably old enough almost to be my grandfather.”

Logan laughed. “So, you want to come up for a drink and a once-over from Mr. Kingsley?” He was still holding my wallet.

“Sure, that would be nice,” I answered. And as far as I could figure, it might be nice. I know my dick was quivering like it thought it might be nice.

 
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