Weekend on Fire Island

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"You and Edge?"

"Were you at one time, yes. Giving it up to get ahead. Selling our asses to important men--being boytoys. I did. Edge did. Don't be down about it. You're young and gorgeous and sexy as hell. Make use of it. Play Edge for all he's worth. If you'll go a couple of rounds with me, I'll help you get parts on stage. Of that's what you want. You told me you're taking acting lessons. That's how it works in the Big Apple. I don't want you to live with me; I just want to fuck you now and again. I want to fuck you tonight."

I didn't say anything. I was digesting that. Barclay was being totally honest with me on hard truths. I should be grateful to him. He was the next one to speak.

"After your gig here tonight, I'd like you to come back to my apartment with me. It's not far away. Can you do that?"

"You put enough in the bowl for that not to be a question at all," I answered. "But..."

"But what?" he asked.

"The money cheapens it. If you're not going to break my heart, you should take the money back."

"If I do, will you come home with me tonight? My balls are aching. I need to lay someone. I want to lay you again."

"You'll fist me again?"

"Maybe. It means more to me that you'll give it all to me."

"Yes." I watched him fish the bills back out of the bowl.

"I'm going back to Fire Island for the weekend," he said. "I don't want to go alone. Would you--?"

"Yes," I interjected. I know, I just can't learn my lessons. This man probably was going to break my heart. But, truthfully, I didn't give a shit if he did. He was going to screw the stuffing out of me, and, in this phase of my life, that's all that mattered. At least I knew he'd give me attention along with cock and he wouldn't lie to me.

But to be as honest with myself as he had been with me, I would go with him in the weekend on the chance that I could build something deeper, more intimate and... yes... loving with him. I had seen signs with him that it might be possible--signs I'd yet to see with anyone else.

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AnonymousAnonymous8 months ago

Had a similar experience on fire Island. I worked as a server in an upscale restaurant in Manhattan. An older gentleman became a regular customer and was a very good tipper. We became pretty good friends and sometimes he took me to dinner and back to his apartment. I always spend the night as we sucked and fucked. One night he mentioned he was going to spend the weekend on fire Island and would I like to join him and his friends. On Friday he had a limo pick me up at my house.. He had a friend with him and in the limo was a blackout curtain. I was sitting between the two of them, and we were drinking martinis. It wasn’t long before his friend put his hand on my cock and was massaging it through my jeans. Within about 15 minutes they had me naked playing with my cock and massaging my ass. His friend and I were making out as he was pinching my nipples and the other gentleman was sucking my cock. We spent the entire ride, sucking in fucking. When we got to the house, they were two other gentleman there. I spent the entire weekend being their play toy as they had their way with me. They all fucked me at least a couple times a day and I slept every night with a different man. I also fucked all of them at least once a day. I had an awesome weekend and think about it all the time. I often get hard and jerk off. Just thinking about it.

AnonymousAnonymousalmost 2 years ago

Wow on the story! Just after getting out of NYU in 2019, I was invited by an ex-prof (~40) to stay with him at a place he rented on Fire Island, so I took him up on it and took a water taxi over. I'd never had sex with a guy before but wanted to give it a try, he was a good teacher too. He sported a nice hard cut 6" cock which I was sucking within the hour, my first bj & I swallowed his load! The next day he was fucking my ass. It was a nice three day trip for me, too short but I could see being with many other guys next time. I'd drop by to see him once a moth during Covid.

Dpj49Dpj49almost 2 years ago

Still excellent writing sir. I always enjoy your storytelling.

AnonymousAnonymousalmost 2 years ago

This was very good, very intense, moving and quite HOT. What is it about the beach that lets us lose our inhabitations? For me it was Rehoboth Beach, also a popular gay destination. I would go to my family's vacation home there and engage in things I'd never do back in town. Maybe it's the heat, or the lack of clothing or the more casual lifestyle, or maybe a combination of these. Whatever it is, it seems to work a kind of magic on some people. It certainly worked something on this young man, and it worked him good. Jeff's journey is really starting to get interesting, so I hope you're planning om continuing this ***** story. MLF

AnonymousAnonymousalmost 2 years ago

Fire Island! First time I got fucked was there, and the second...then several times a day. Left my girlfriend.

Finally met an older guy, a HS art teacher, on the beach and when I wasn't working, I spent the rest of the summer on my knees at his place. He had a nice long cock, not thick or fucking huge just the right size to learn about get the gag reflex and take him deep. My fingers could feel the bulge passing down my throat. I really loved it. However, when he was fucking me, it was like he hit the wall and couldn't get it all in, it hurt a lot.

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