My first time

Back about 20 years ago when I was a young man, and Craigslist still had personals, I hooked up with a guy who was at least 30 years older than me. We talked for a bit, and I built up the courage, got in my car and drove over. I got out of my car and he was there waiting at the doorway in a robe. It was a sort of apartment or condo like set up so any of his neighbors could have seen him, and if he opened his robe they would have seen he wasn't wearing anything underneath it... that was for me to find out.

So I went up the stairs, we greeted one another, and he let me into his home. After what must have been the longest three seconds of small talk ever, I was on my knees in front of him with his cock lording over me... begging me to taste it. So I did... I licked it... I kissed it... and I took it into my mouth and started to suck on it. I licked it up and down the shaft, licked his balls, and tried to deep throat it as best I could. He told me that for a first timer I was really good and it made me really proud. There I was, fully clothed sucking off an older man's cock through his robe in a dark room with a full length window right next to us... the slats were only slightly angled, so anybody could see if they really tried.

After a few minutes he guided me over to his bed and I knew what was about to happen so I started getting nervous. He offered me some poppers but I declined. He helped me undress and I sucked him off a little more now that I was naked and then I got onto my hands and knees on top of his bed and supported my chest with a pillow and waited. I kept looking forward, wondering what it would feel like, and I wasn't even thinking about what he was doing... I heard him open a condom, and put it on... I heard him take a bottle of lube and I felt him preparing me as I sat there waiting... and then finally I felt his cock press up against my ass and my back stiffened up instinctively.

He told me to relax, and I did my best... and next thing I knew I felt him slowwwwly enter me from behind. I felt his head penetrate my ass and I moaned a bit... and slowly over the next few minutes he worked his way into my ass little by little by little... until I could feel his length fully inside me and his hips pressed against my buttocks. It felt good, but it was still felt a little weird... like a tingling around the rim and I just had to force myself to relax and not flex my anus. But slowly he started working himself in and out... in and out... in and out... and now he was legitimately fucking me.

Things got hotter from there, because he started talking dirty to me. Asking if I liked feeling his cock in me, and telling me what a dirty slut I was. I begged him to fuck me harder. Eventually I could hear his hips clapping against my ass and it still felt weird, but the tingly sensation was gone and it started getting a little sore. We went on for a while like that, until we changed positions. He put me on my back, pushed my legs up so my knees were practically touching my chest and he fucked me missionary style, breathing in my face. It was so hot, and we kept talking dirty to one another until he came inside the condom which was inside me. That was the weirdest sensation of all, but the most memorable...

I haven't been fucked like that since.