I was in my mid-teens he was in his 40's and married. He caught me in my mom's stockings. Ended up giving him a blow job the next day he came around and bent me over the arm of the sofa and lubed me up along with his cock it hurt going in but after he was balls deep it started feeling good. He made me cum by fucking me then he came in me.
Well my first time wasn't exactly great as he didn't use enough lube so to say he burned up my ass is a bit of an understatement. Don't get me wrong it was still a lot of fun and we've been together a half dozen times since then but haven't hit upon the right amount of lube just yet, if anything I use too much lube so that's a good thing from my perspective, I'm sure we'll get this "issue" resolved soon, it's just going to take more practice. We'll just say for now every time since the first time has been better than the last. He isn't real big, which I'm OK with but he knows what he is doing and that's what matters the most. This was/is still all new to me but it's as enjoyable as I had hoped it would be.
Even with lube it was painful at first, but once he broke thru it was AWESOME! After he came and pulled out, I pulled the condom off of his cock and licked the remaining cum off of his cock!
The very first time I had sex with a man was because I had questions. I wasn't the school jock or anything near it so I was designated the school queer and beaten on a regular basis. I was curious, duh, who wouldn't be? So I wandered into the local adult theater and went to a smaller side theater for gay flicks. Gay porn never does it for me. But I was curious about what acts were involved. I already knew I throughly enjoyed women. After a few minutes a man sat down next to me. We chatted briefly as he fondled my crotch. I told him I'd never been with a man. He said he understood and we walked back to his place. He was well hung and an excellent teacher. He sucked my cock then let me suck his. Rimmed my ass and Let me rim his. And he showed me how to fuck his ass then he fucked mine. God it drove me wild. I loved getting fucked and if I met a man today, I would want to get fucked. I do myself with dildos and vibrators. I love anal and especially rimming as the perfect foreplay to get me all horny and fuck me all night with.
I was 14 +2 days. My best friend's stepdad. My friend and his mom were out of town for the weekend, but they had a pool that I was invited to use anytime. The day earlier, I had been to their house to use the pool and his stepdad was sunning nude on a lounge chair. I couldn't help but stare at his thick cock and large balls.
I knew he knew I was there, but he didn't stir. As I swam a few laps catching as many glimpses as I could, he eventually got up and walked over to the edge of the pool and sat down, cooling his legs in the water.
That first day, I don't know what came over me, but I waded over. I stood next to him and neither of us could ignore the fact that his cock was just inches from my face. I'll skip over the details except to say that was the first time I'd ever sucked a cock to completion.
The next day I went back. This was the make it or break it point. Again, we started poolside, but quickly went into their dining room / kitchen area. I removed my swimming trunks while he went upstairs to get some lube and a few towels. He also got a pair of his wife's high heels, panties and a bra. He came down, helped me fit into them, which except for the bra, everything matched pretty nicely. Once I was dressed, I slipped into the heels and waited for what was to come.
I will say, he was very gentle and meticulous. There, bent over their kitchen island, I got my first taste of what it was like to get fucked. He first rubbed the head of his cock against my hole, then grabbed me by the shoulder with one hand and forced his way into me. I never really felt any pain, like others have described. But I did feel or hear a popping sound after had penetrated me fully. I literally saw stars and nearly blacked out.
Only later, after doing some research on human anatomy, did I realize that he had penetrated my rectum and was fucking me in my lower intestine. He eventually backed off and fucked me in a downward position, causing me to ejaculate spontaneously.
Later that day as I rode home on my bike, I could feel his cum leaking out of me. When I got home, I ran upstairs as fast as I could and jumped onto my bed. I waited until after dinner that evening, but I masturbated at least 10 times to the scenes that had played out to me from the previous couple of days.
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