A First Time for Everything...

First and foremost let it be known this is a 100% true and accurate story of my first sex with a man. First of many at this point...

So no surprise here I'm sure but this story of experimentation happened my senior year of college. As a brief description of myself, I'm 5'10" and about 175 lbs, slightly muscular but no gym diva. I have bright blue eyes, light brown medium length hair, and hey, not trying to sound conceited but I'm good looking. I've been with more women than I can count. But hey this story isn't about girls is it?

As part of the story though I do have to tell you about Nikki because everything that happened was because of her. Nikki is an absolutely gorgeous petite brunette with perky c cup tits and a tight ass that just NEEDS to be eaten. She and I dated when we were in high school, when we both went off to different schools we decided together that things just weren't going to work out like that. But there were no hard feelings and we continued a great relationship as friends and we would fuck like rabbits any chance we got.

Now I've always been a very sexual person, but Nikki just did something for me that made me want to do or try anything she wanted me to do. If it's kinky, we've probably done it. When we weren't together we had a habit of sexting all the time and especially playing "would you rather" and asking each other about perverted hypothetical situations. I remember very well when this happened because it opened up such a whole new and exciting world of sex. It was just a random Saturday and we were playing would you rather like we always do and she asked me if I'd rather fuck another man or let a man fuck me in my ass. At this point in my life looking back it's hard to believe, but up until that moment I had never even thought about sex with another man. But hey that's the game, and you have to answer. So I was thinking about it, it wasn't easy for me to answer, and I noticed the longer I thought about it the harder I got. It was literally exhilarating; I was breathing heavy and felt so kinky even thinking about it when I finally told her I'd rather be the one getting fucked. The way I saw it, if I want to fuck someone, I'll fuck a girl like I always had, but being the one getting fucked, that was something new that I found very exciting.

To my surprise she was very excited about my answer! Apparently she had some ulterior motives in asking the question in the first place. She told me she wanted to have a threesome with me and another guy. But she didn't want two of us so she could fuck two guys at once, she wanted to be in the background, watching me be, in her words, "a little slut."

At first I told her outright, not a fucking chance, and that was the end of it for a long time. But secretly, and I didn't tell her this, I kept thinking about what it would feel like to basically switch roles and be the one with my legs in the air, or bent over on the bed, and I got comfortable with the fact that this was something I wanted, badly. I finally told Nikki I was game, but I was not about to do anything that my friends could ever find out about, and between my concerns and the fact that we lived a couple hundred miles apart, it was clear it was just too hard and it was never going to happen.

At this point I had really embraced the idea of sleeping with a guy, I was watching gay porn every now and then, and I was wondering how, or where I might meet the right to take my virginity. I knew there was no way I'd ever be so open to hit on a guy at a bar, or even to let a guy hit on me in public so I posted an ad on craigslist. Even though I was in a college town it took literally weeks before I got a response from a good looking guy. But eventually it did happen and we swapped numbers with him giving me his address. He was around my age but a little bit older, probably mid 20s. He was fit, not incredibly good looking, but he had this amazing cock I couldn't wait to get closer to. He (and I keep saying "he" because I never even got his name) had a townhome not too far from my place and for whatever reason he wanted to fuck in the garage. I had no problem with that so I got in my car and I drove to his place.

I have definitely never felt anything like the feeling of anticipation as I made that drive to his house. My mouth was dry, I was nervous, but I was excited and I was hard as a rock! When I got to his place he met me outside and walked me into the garage, closing the door behind us. I wont lie at this point I had some serious second thoughts. But I was there, and he was feeling me up, grabbing my ass like a girl and I was loving it. He told me he wanted to "see what I was working with" so I turned to face him, taking my shirt off first, the whole time keeping eye contact with him, then stripping out of my boxers and jeans so I was fully naked in front of him, some guy I had never met, whos name I didn't even know. I turned around and shook my ass a little bit and he grabbed it, one hand on each cheek and spread me open. I will probably never forget how that felt, it was so liberating.

After just a couple moments of him feeling and admiring my ass (and asshole), I turned around to face him again, got down on my knees and began to undo his belt so I could get his jeans off. I was down on my knees, basically eye level with his crotch, and for the first time in my life I reach into another mans boxers and pulled out his dick. He was partially hard, but by no means hard enough for sex so I asked if I could suck it and he of course said yes.

Keep in mind, for the visual effect of this scene, I'm completely naked, I am absolutely as hard as a rock, and I'm on my knees with his dick in my mouth for the very first time. And I sucked him like a pro. The longer it went on the more I got into it. By the end I had both hands working him while I slid it in and out of my mouth, periodically letting go of it to take his balls in my mouth. It took some time but eventually he was fully hard and I couldn't wait any longer. If you have never been on the receiving end of a hard cock then you might not be familiar with this feeling, but if you've ever been fucked, then you know the way your asshole is just begging to be filled.

He told me to bend over against the wall and I did like I was told, arching my back and sticking my ass out as far as possible. Now like I mentioned, this dude was THICK and probably above average in the length department too, and the biggest thing I'd ever had in my ass so far was one of Nikkis slender fingers. And unfortunately, he wasn't exactly gentle getting started. He slammed his dick right in and it hurt, really, really, bad. I pulled away, he pulled out, and I paused a minute for the pain to reside, before I started fingering myself to warm up a bit. First one finger, then two, and finally three, all right in front of him of course and I could tell it was a turn on for him. When I was finally ready I told him to be still and I backed up into him slowly working his cock into me until I had the whole thing. He started pumping slowly and I couldn't help but moan it was so raw and sexual being penetrated, bent over against a wall. I reached back between my legs to hold his balls and gently stroked them the entire time.

I was loving every inch of him and feeling every bit like a submissive little boy when he pulled out and stopped. I turned to look at him, hoping he hadn't cum yet. He told me to get down on all fours so he so I did. He pushed back inside me but he started to soften up and it wasn't working very well so I had him stop, I turned around, and I took him in my mouth again sucking until he was ready to go. We fucked in that position for awhile but I wanted to try other positions as I wasn't sure I'd ever have the balls to go through with this again. From doggy style, we switched to me getting on top, cowboy, and then reverse cowboy. We didn't spend too much time doing this because I wasn't sure how long he would last and I wanted us to finish with me on my back, legs in the air, and him fucking me hard with that big dick he had. And that's exactly how it happened. I was basically screaming by the end and when he told me he was going to cum, I grabbed myself and it took all of about two strokes before I had one of the best orgasms of my life all over my chest, with one burst even landing on my cheek, oops.

I laid there a couple minutes, breathing heavy and covered in cum while he stood up and got dressed. There would have been some regret on my part, I'm sure, if the whole experience hadn't been so fulfilling, and if it hadn't just felt so damn GOOD. And heres where this story ends, I cleaned myself off and got dressed, and he let me out with almost no words, almost like we hadn't just had some very raunchy gay sex on his dirty garage floor. I never saw him again or even attempted to contact him, but he was the first of one of, at this point, a pretty long line of dicks that I've had a lot of fun sucking and fucking! If you've never tried it, I highly encourage you, but be careful. You mind end up loving it like I do. Thanks to Nikki for proofreading this and if you liked this story tell me about it. Like I said this was the first of many encounters, and if theres an interest I'll write about other experiences as well.