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drakestories:

I was 21 before I lost my anal virginity. It had been a tough year at school and a tougher year coming out to my family and teammates. They were cool about it all, I guess, but I felt like I had no one to relate to. 

I’d read about Palm Springs. An all-gay, clothing optional resort. I saved up my money and went. Day One was a disappointment as the place was kind of empty off season. Day Two I hit the jackpot as a group of about a half dozen hot men arrived from LA for a long weekend.

I got up the courage to sun myself nude and felt a swell of pride to realize that all of the buff guys were checking me out. Some were surreptitious in their glances but one guy openly scoped me out, his erection poking up to reveal his sexual interest in me and my body. He was a big tan muscle guy, bald with a couple days facial growth to give him a rugged look. He nodded in acknowledgement from across the pool. I nodded back. Soon he was joining me. Leaning over me, kissing me, pushing my legs apart and humping my crotch and ass crack. Then pushing inside me.

The penetration hurt at first but somehow soon felt fantastic. Neither of us were in a hurry, but we weren’t holding back either. Especially Mr. Top Man. He fucked me with a sense of purpose and raw masculine power. I could sense his pace quicken and his breath rise. I knew he’d be cumming soon. 

The very made my sperm shoot out between our heaving bellies as I had my first, majorly intense anal orgasm. 

"Nice one, kid," the man growled, right before he orgasmed. 

That week, I got introduced to all his buddies.