This is the true recounting of my first time with a guy...
First I want to preface this story by saying that this is absolutely true, this is my real first encounter with a guy.
I lost my virginity early in life to my mom’s best friend, she was bi and she liked to “share” me with her friends, so by the time I hit my 20’s I was well experienced with older women and loved it. One of my mature friends had a thing for anal sex, not just receiving it but also giving it. It started out simply enough with her licking and fingering my ass but it soon turned to dildos and strap-ons. I was enthusiastic at first but when she pulled out the thick 8” dildo she wanted to use on me I was apprehensive. But she could be very convincing so I gave in and after a few attempts she managed to get it in painfully for me. However being a trooper I sucked it up and eventually started to enjoy the experience. This got me curious about doing it with a guy. I love watching big cocks in porn and though I have never felt attracted to the guys in the films I was extremely attracted to their cocks
So I went online onto the prodigy chat rooms and found a room for gay guys looking to hook up. I started talking to this older gentleman in his mid to late 30’s (I was 20) and we hit it off pretty well. He liked younger guys and I had a thing for older partners so we decided to meet. He invited me to his condo which was about 20 mins away. We never exchanged photos and barely even described ourselves to each other. So I was basically going in blind so to speak. Having never done anything like this before I was a little nervous and excited at the same time. There is something incredibly exciting about going to meet someone for sex that is a complete stranger and that you don’t even know what he looks like.
Following his directions I easily found his condo and knocked on the door. To my appreciation and luck a tall thin very good looking, very dark skinned, black man opened the door and invited me in. He was wearing a t-shirt and a pair of cut off sweat pants shorts and he was sporting the biggest erection I had ever seen. He asked me if I wanted to go upstairs and I readily agreed and followed him up the stairs and into his bedroom. He layed on the bed and started to watch the TV which was already on. I took my eyes off of the huge tent in his pants long enough to look around the room and saw many pictures of him and a very attractive black lady. I asked if she was his wife and he said yes, I then asked if she knew he did this and he said “no, this will be our little secret.”
I couldn’t help myself and I asked if I could touch his cock, he said sure, that’s why we’re here. And he slipped his shorts off. His rock hard black cock sprang up slapping against his belly. I guess I was just staring with my mouth open and he asked if I had ever seen a cock up close before and I said no. He reached over and took my hand and guided it to his cock. I slowly started to explore it and stroke it, asking him how big it was. 10” he told me. It was very long but thankfully not very thick, not as thick as the dildos that had been used on me anyways. He asked if I wanted to try sucking it and I enthusiastically agreed hopping up onto the bed and doing my best to suck this big black cock. I could only get maybe a third of it into my mouth before I started gagging and he told me to slow down and relax. At this point he started to undress me pulling down my shorts and letting my cock out. I’m pretty well hung (which is why the older ladies became interested in me in the first place) but I was a good 2” shorter than this guy but about twice as thick. He started to suck my cock doing a much better job of it than I perceived myself doing. It didn’t take long before he got me to cum and swallowed every drop. Then he told me it was his turn and that I should get on my knees. He wanted to take me doggy style. I asked him to be gentle as this was my first time and he said no problem. I got up on my knees and laid my chest down on the bed while he fished some lube out of the night stand. He thoroughly lubed up my ass, fingering me with first 1 then 2 then 3 then 4 fingers until he thought I was ready to take his cock. He lubed up his cock and then I felt the head pressing against my tight little asshole. He slowly pushed in and I would be lying if I said it didn’t hurt, but I was there for this reason and I really really wanted to get fucked by the hard black dick. He was very gentle, slowly stretching me out until his fat mushroom head popped into my ass and then he just slid the rest in until I could feel his hairy balls rubbing against mine. I was in heaven, I never thought it would feel this good, pain aside it was much better than the dildos. He asked if I was ok and I said yes so he started to fuck me, slow at first with long slow strokes all the way in and out and I was going crazy my cock was rock hard again and I was feverishly stroking it under me. I begged him to go faster and harder and he obliged until he was seriously pounding into my ass and I started to cum all over the bedsheet and he unloaded into my ass. The sensation of his cock getting harder inside me and then spasming and shooting deep into my ass made my orgasm all the more intense. He held my hips and just ground that big cock into me as he shot that huge load inside me. Then he collapsed on top of me and started to nibble and bite my neck and ear and was really turning me on. I could feel his cock getting soft inside me and when he went to move I asked him to keep it inside me. I just wasn’t ready to let him slip out. He said ok and continued to work his mouth on my neck and ears. I turned my head and for the first time ever I kissed a guy. It was different than kissing a girl but not unenjoyable. As we kissed he started grinding into my ass and I could feel his cock coming back to life inside me. I started to grind back against him and before long he was holding me down flat on the bed as he savagely fucked me hard and fast and deep. It took him longer to cum the second time but I didn’t mind as I was grinding my rock hard cock into the mattress. I finally got his second load in my ass as I shot another load into the sheets. He rolled off me and said that I needed to go as his wife would be home in a couple of hours but offered me his shower. I jumped in to clean up and as I was stepping out of the shower he was waiting for me. He dropped to his knees and started to suck my cock until I was hard then her turned around and bent over onto the sink and handing me the tube of lube he asked me to fuck him. I lubed him up just like he lubed me and I slid my hard fat white cock into his black ass. I had fucked many an ass in my day but this was by far the tightest, hardest ass I had ever been in and he squeezed my dick so hard it felt like he had a hand in there jerking me off. Being my 4th cum in about 2 hours it took me a little time but he didn’t complain and when I finally did unload in his ass he was pushing back against me as hard as I was fucking him and he basically dragged the cum out of me. I literally collapsed to the floor my legs giving out on me. He took a soapy washcloth out of the sink and cleaned me up then threw me out of the condo as his wife was surely on her way home. I never saw him again though I did try. He never responded to my emails or IMs. Too bad I would have loved to been fucked by him many more times. That was my first cock and the biggest I ever had. I did have another black guy once I met on craigslist that was almost as big but he wasn’t nearly as much fun. He was kind of a jerk and basically fucked my mouth til he came then kicked me out of his car. Actually I have had very few good experiences with guys. Which is why I don’t see guys anymore. I was lucky to start out with the best.