My First Time With A Guy

Back in the late 90s (99 to be exact) I had my first apartment bout an hour away from my home city. I worked a lot so I never got a chance to make any friends so my time off was spent at a coffee shop typically. On the weekends they’d have live music from local bands (never very good, but still) and a lot of people frequented it. I struck up familiarities with some but no friendships extended beyond the coffee shop.

One day I met Greg. He was older, I think mid50s but never really asked. We met during the week when it was quieter in the shop and just started small talking. A couple days later I saw him again and soon it became regular to see him and chat about whatever. It was nice. Through convo I had picked up that he was gay but he never outright stated it. At the time I considered myself straight but never gave any of it much thought. He often paid for my food or drink if he was there before me and for whatever reason I eventually opened up to him about not having any friends here and all that. He asked if I considered him a friend and I said I do but I meant people to hang with outside of the shop. He quickly suggested we do. So we set up that weekend for me to come out to his place and he’d teach me about day to day things we had discussed that anyone should know.

Greg lived about 15 min away but out of the city on some wooded property. He had a nice cabin-style home, hot tub out back, and it looked like he was building a sort of structure over it, like a roof and walls, prob for privacy. We talked about various things and as it was getting into night and I was thinking bout heading home he goes “Would you like your dick sucked?” At first I just went “I’m not gay” but he just shrugged like “so what?” and then I was like I guess no one would know, right? He smiled.

He sat me on the couch, took my cock out, and started to suck on it. I put my head back, closed my eyes, and thought oh my god I’m letting a guy suck my dick. But he was really good. He was swirling his tongue around my shaft, sucking on it, stroking me, and when I warned him I was about to cum, he held my shaft at the base and in a steady rhythm bobbed his head up and down on me until I exploded in his mouth. All told I lasted like 5 minutes. It had been a couple years since I last came from something other than masturbation.

When I was standing to put myself away and do up my pants Greg mentioned we could chill in the hot tub. It was fall Time so the weather would be great. I told him I don’t have my suit, but he said he didn’t use one so who cares, come on, it’ll be relaxing. I don’t have the room to say all the thoughts that went thru my head but I fell on how good the bj felt so if I got another one I wouldn’t argue. If I had to I figured I could jerk him off. After all I do that to myself daily.

He was a bigger guy, not muscular and not fat, but not in shape, if you know what I mean, and he had an uncut cock that was pretty girthy with a really big head. He sat right next to me and fondled my cock and balls as we talked. All the talk was sexual and he got visibly aroused. He told me he loved guys like me, small, thin, what he described as a “Twinkie”. He told me he loved my “bubble butt” the first time he saw it and asked if I’d lean over the edge so he could stroke off on it. I was hard from his fondling and horny so I said ok and leaned over the edge of the hot tub. He positioned himself behind me, rubbing his cock against the crack of my ass. He put his giant tip against my hole and I went “what are you doin-ung” as he pushed his girthy uncut man meat straight up my ass, balls deep. His one hand pushed down between my shoulder blades, his other reached around and stroked me. He told me he couldn’t resist and that he liked the tightness but I should relax. It’ll feel better. I came pretty fast again, over his hand, my belly, the side of the hot tub. I moaned out that he was so big. He fucked my ass for a bit then I felt it, him “expanding”, throbbing, releasing a flood of cum into my ass with a loud “ohhhhhyes!” I felt every throb, every squirt, and thought “a guy just came in me”. He collapsed against me and whispered in my ear “ I just conquered your ass and it was as great as I imagined.”

Greg continued fucking me for 2 years. To this day I’ve never had more arousing sex.