My First and Only Gay Experience

I was 18 and had just finished my freshman year of college in New England. The terms of my financial aid offer required work-study, so I got a job at an Inn on campus busing tables. The money was good, so I elected to stay on campus that summer and continue to work full-time in order to save for college.

A few staff would sometimes go out for drinks after the dinner shift and side work was complete. One coworker who would sometimes join us was the executive chef. He was older, in his mid-forties, but attractive and quite fit. A small group of us had a few rounds at a nearby pub and as the group was dispersing, Chef asked me if I would like a nightcap at his house. Since I had no classes that summer, I happily agreed. We drove a few minutes outside of town to his house and Chef fetched a bottle of single-malt and asked he I wanted to have a dip in his hot-tub. I mentioned that I did have any trunks in my backpack and Chef assured me that it would be no problem.

We disrobed and slipped into the roiling hot water, began sipping that outstanding whisky and continuing our conversation from before. He allowed as how he was married, but his wife had some high-powered banking job in Manhattan and was only able to join him on average one weekend a month. It was tough on his marriage, he allowed, but indicated that his wife was not willing to give up her glamorous executive job and join him in rural New England.

I was feeling no pain at this point and my curiosity was piqued. I am a heterosexual male, but I would be lying if I said I have never wondered what it would be like to have my first same-sex encounter. Emboldened by the scotch, I cautiously asked Chef that if was ever feeling horny and frustrated, he could always give me a ring. He paused, and asked me if I was gay. I told him no, but was willing to try it. He smiled and said that it sounded like fun and he would consider doing just that.

Nervous as hell, I reached my right arm over beneath the water and slid my hand slowly up his left thigh. He startled a little bit but soon relaxed as my hand found his slightly tumescent cock. It was much bigger than I expected and grew steadily as I gently stroked him until he was fully erect. After a few minutes, his breathing was getting a bit ragged and I asked him if I could see it. He hoisted himself up onto the first step of the tub so that he was sitting in a few inches of water and his 7" cock was fully exposed in the air. I continue to gently stroke him, running my thumb up the underside from his scrotum to the tip, expressing a thick bead of pre-cum. My curiosity and teenaged hormones overcame my anxiety and I slowly lowered my head onto his member and gently began sucking. He moaned softly and I experienced my first head. I quickly got the hang of it and could feel his cock begin to throb as Chef's thigh muscles stiffened. He called out my name as he shot his first load into my eager mouth. I continued to work his cock until he began to soften and he slid back into the water and sighed deeply. I straddled him kneeling on the bench underwater, wrapped my arms around his neck and confessed that I had never done anything like that but had really enjoyed it. It surprised me that embracing another man 25 years my senior and naked felt completely natural and quite pleasant.

After a few minutes of canoodling like that he asked me if he could return the favor. I hopped up on the stair just as he had and Chef got the chance to experience giving his first head as well. By this time, I was so horny I probably only lasted a few minutes and Chef swallowed every drop.

After a few minutes of conversation and another round of scotch, Chef was visibly erect once again. I asked him if he was ready to fuck me and he could only nod at that point. I reached over to the deck of the pool and pulled my backpack over the pool's edge and fished around for a tube of Vaseline lip balm, which I always carried with me for the New England winters. I squeezed a generous dollop onto my fingers, applied it to my virgin asshole, and resumed my earlier straddle position over Chef's lap on the bench seat under water. I positioned myself over his now fully erect cock and wrapped my arms around his neck. I reached down and guided his cock to my anus and gently lowered myself down. I could feel his head pop as it passed the rectum and was initially startled by the sensation of having this middle-aged man's erect cock inside me. I whispered to Chef to go slow and allow me time to get comfortable with all the new sensations I was experiencing. Gradually I was able to take his full length as my ass came to rest on his lap. I gradually began rising and falling as my ass began to first accept and ultimately welcome this alien presence.

Chef gently began stroking my cock, but I removed his hand and said that tonight was all about his pleasure. That gesture quickly became moot as I began building to my own no-hands orgasm from the glorious sensation of his cock stimulating my prostate. I placed my forehead on Chef's forehead and breathlessly urged him on - deeper, harder, faster. He was now thrusting balls-deep in my virgin asshole and beginning to breathe very ragged. Soon, I could feel his cock begin to throb with the onset of his second orgasm and that sensation sent me over the edge. We came simultaneously, my rectum spasming with the intensity of my orgasm sent Chef to a totally new place of ecstasy and I collapsed in his arms, overcome with deep and surprising feelings of tenderness. I surprised myself and Chef by kissing him deeply as his cock slowly deflated and eventually popped out.

He drove me back to my room in my frat house on campus and we said our goodbyes. I wondered if it would be awkward to see him at work, but surprisingly, it wasn't in the least. We saw each other a few times a month that summer, really enjoying each other's company until he got transferred to another hotel in the fall.