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.
I used to try to put my cousins small cuck in my ass but I remember when the first time it really happened. I was older and was playing with myself a lot and putting various objects in my ass. Then I went looking for it, in bars, clubs and movie houses and found it in a dark movie theater. My first man's size cock. He sat beside me and started rubbing his hand up and down my leg. I was hard and started rubbing his cock. I took his cock out and he took out mine, I loved the feel or it in my hand. We then got up and went to a downstairs area where many other people were having sex. I could hear moans and whispers, it was dark, and we found a spot. He leaned me up against the wall. His tongue pushed deep in my mouth we passionately kissed. He turned me around, I undo my pants and he pulled it down. He did the same to himself and then slipped on a condom. He lube up his cock and my ass pushing his finger into my ass. I was surprised how open and inviting my ass was. I loved the feel of his finger in my ass, fucking me and wanted more. I started moaning, he then slide his cock into my ass and again shocked how damn good it felt. He fucked me while reaching around to play with my nipples and my cuck. He was fucking me, a man was fucking me, I was hard and I wanted more cock. He pushed hard and came but I wish the condom was not on. I wanted to feel his cum in me, he then sucked me and I came in his mouth. We then kissed and went our separate ways. I wish we had exchange numbers but we did not. I went back to the place hoping to find him but did not. So, I went back to ushing various objects up my ass while jerking off.
My first time receiving anal sex wasn't quite the erotic experience I'd hoped for. My partner, Dave, also an anal newbie, seemed to thoroughly enjoy topping me. (Actually, we fucked in the "cowboy" position, so technically, I was on top.) I've got to say, I never saw a man get off quite so loudly or enthusiastically. But as receptive anal sex was, for my part as the receiving partner, largely a feeling of fullness and pressure that I didn't particularly enjoy. Even after receiving some coaching from a gay friend experienced in such matters, I didn't find anal sex anywhere near as enjoyable as other activities I'd explored to that point; mutual masturbation, oral and cock-to-cock play. I'll concede that I did enjoy the intensely intimate, even taboo, nature of the act itself, and reveling in the realization that another guy had just came inside me!
Okay, I'll concede that I did derive some enjoyment in providing a friend with such an intense level of pleasure, and I'll never forget the look of gratitude in his eyes as he announced he was close to cumming and I told him to go for it -- completely bareback! Indeed, I loved the feeling as his cock began twitching , throbbing and pulsing, and realized he was, at that very moment, pumping his seed inside me. I don't know if it's common or not, but later that evening, when it was my turn to cum, I had a strangely powerful orgasm and expelled a copious amount of semen, which I'm told was probably due to prostate stimulation. Afterward, I also enjoyed the feeling of Dave's cum trickling out of my backside and running into my ass crack after he withdrew. As they say, somebody has to sleep on the wet spot, and that night the pleasure was all mine.
Last edited by Orgasmus; May 6, 2024 at 7:01 PM.
Originally Posted by jjourneyman
Wow what an experience! This is much like my second time receiving anal sex at about the same age, older gay guy, but I was more reluctant and had been strongly coerced into it by him. He got me bent over his couch and I know that popping sound well. He was big and it hurt, I remember wondering if he thought it was tight or loose since I’d been playing with my ass a good bit by then. He obviously enjoyed reaming me out back there.
I don't think he was gay, he just wanted a tight hole to fuck and a willing mouth. I continued to see him throughout that summer and for a few months into that fall. That's when he sold his business and they moved to the Midwest.
My first time was at 14 and was failed attempt. My bud was a couple of years younger than I was and surprised me one night while we were sleeping outdoors in a tent. He tried getting on top of me while I was on my stomach but we didn't have any lube and I think he was just to small so eventually we just made out for a bit. Later in life I met a guy on CL and we got together. At first is was just for oral but we both knew we wanted to experience the other inside us. Finally we had the chance and we tried anal but we were unsuccessful. I think we were just to nervous for our first time. Weeks later though we got together again. We showered together and used our fingers in each other to get ready. When we went to the bed and I lubed myself and him, then I laid back, spread my legs for him and watched him climb up on the bed and between my legs. Once he positioned himself he shoved his cock in hard and fast...I gasped from the sudden force of being speared but it still felt great! I remember him not being real thick nor long but he was hard as hell and still causing wonderful feelings inside of me. He alternated by lying down on me and we would kiss passionately and then he would push up to support himself on his arms and we made intense eye contact then. This continued for about 15-20 minutes until he stopped and pulled out of me. I'm not sure if he came or not but we embraced and made out for a bit before finally getting dressed cause I had to leave. Unfortunately, a death in his family caused him to stop our encounters and I've never seen him again. I've always regretted not knowing if he came inside me or not (I really don't believe he did) but I would have really wanted him to and would have let him stay inside me until he had completely gone soft. Just the feel of him on top of me, his arms wrapped around my shoulders while passionately kissing spurs my desires over and over again, even to this day.
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