Everyone remembers their first time, good or bad.
Mine was great and totally unexpected. I was 15 and hitchhiking home from school. I got picked up by a guy who started asking sexual questions and eventually got me to pull out my cock so he could suck on it. It was just a quick roadside thing as I had to get home. He asked me if I wanted to try more at his place the followiing Saturday. I did.
He picked me up in town and drove to his place, two towns away. I couldn't believe I was going off with a total stranger. Before him, I'd never done anything with a guy, and not much with girls either. When we got to his place, he gave me a beer to relax. He showed me some gay mags and commented on the pics, asking what I liked. I told him I liked the oral pics but the fucking pics were kind of scary. He said he'd like to suck me again but wanted us to both be naked. That was fine with me.
I had a huge hardon and he was all over it. I came like a rocket in no time. He gave me another beer and we looked at more pics until I got hard again. It didn't take long. He sucked my cock again but this time much slower. I wanted to suck his cock but he told me to wait. His mouth went from my cock to my balls and eventually down my crack. When he tongued my asshole, I thought I died and went to heaven. He took his time and moved back and forth from my cock to my ass. At some point, while he was sucking my cock, he started circling my asshole with a finger and gently poking at it. The finger slid in and it felt great. He reached into the nightstand and pulled out a jar of vaseline. He took his time, lubing my ass and sliding one, then two fingers inside while still sucking my cock and balls. He asked if I wanted more and I practically begged for it. I couldn't believe I was about to let myself get fucked and was dying for it.
He was very patient and gentle as he put my legs over his shoulders and just barely poked his cock at my virging hole. He slid it in so slowly that I barely felt any pain, just a quick jab as the head of it slid past my ring. He stopped to let me adjust to it, telling me to relax. As he picked up speed and depth slowly, my head was spinning. Finally, he drove it in all the way. I couldn't believe anything could feel that good. He started pounding and I responded. I shot out a huge load without even touching myself. It shot so hard it got both of us in the face. That put him over the top and he pounded like a jackhammer when he came. It was a strange sensation as he got soft and slid out but I didn't hurt at all. I was hooked!!!
I spent the next year getting fucked by him (and some of his friends) until I moved away. I went back and saw him many years later. He was in his 60s at that point and really couldn't get hard enough to fuck but I gave him the best head he'd had in a long time as a little gift for all he'd done for me.
That was a lot of years ago, and I still remember it as one of the best I've ever had. I would really like the opportunity to do the same for some young guy some day (although it wouldn't be a 15 year old.)
I'm now 54 and still love it all.
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