Was 18 at a party of a friends. Not much of a partier and don't drink so I mostly just socialize and wander. Went outside for a break from people and this guy comes out for a smoke. We get to talking and end up really hitting it off and go back inside. End up talking about random crap, which led to talking about which girls were hot, which led to him pointing out which guys he thought were hot. I was curious at this point so I joined along. I guess he sensed my nervousness and asked me iff I found him to be hot, and I agreed that he was. Start talking about how I have been curious about being with a guy and so we decided it would be fun to fool around. He leads me out of the house and into the backyard again, this time going past the fence into a local park. It is around 1am and just barely enough moonlight so you could only see what you are close to. Well we get to the spot he was leading me and he turns around, grabs my waist, pulls me in, and begins to make out with me. Now I am not much of a fan with kissing, even with women, but at that point I was pretty much instantly hard. He starts unbuttoning my pants and pulls my dick out and I do the same to him and we start jacking each other off and rubbing our cocks together.
Now I will mention that at this point the most I figured we would do is this or maybe I would try giving him a blowjob so when he told me to turn around I wasn't really expecting much. So as my back faces him I feel him force me to bend over and I feel him start to rim me. I was freaking out as I wasn't expecting this but I just let him continue. Started to feel really good but after a while I feel something new and slippery, this time pushing its way inside of me. Turned out he started to finger me which again freaked me out but it felt pretty darn good still so I just let him continue. After a while of this I feel him pull it out. Figured he was done so I just stood back up started to turn and face him. At this point I feel him put his hand back on my shoulder and give me a stern nudge back to being bent over as well as feel something even larger pressing against my whole.
So before hand when we were jacking each other off, the dude was pretty big. Bigger than me and I am around five inches and decently thick, but his made mine look small. Well I am still standing there, pants around my ankles, bent over with something prodding my hole and a hand on my right shoulder... only now I feel his other hand touch my left shoulder and my hole still has something against it. All of a sudden I feel something big enter me, and seconds later feel his waist pressed against my butt. I look between my legs and see his balls against mine and it finally clicked, he just shoved his cock inside of me... I was panicing at this point in my head. It didn't hurt at all, felt a bit weird but no pain and I from all that I had heard the first time you have something in you is supposed to hurt so I was worried that I would be in pain. But he started pulling himself in and out of me slowly and the pain hadn't come yet. I started to breath heavier and heavier as he continued, kind of out of my own control, after a while I started pushing back against him, started to get a good feeling in my hole, and even began moaning. I guess he took the hint that I was enjoying it, because at this point he stood me up, pulled my shirt off of me, stepped back as I felt his cock slide out of me. and told me to leave my clothes and follow him to the field.
I indeed followed him, naked, out into the middle of the field. Sure it was dark enough where you couldn't recognize anyone from far away, but you could easily make out two people fucking even at a glance. I wasn't at the right state of mind though, what he was doing to me felt really good and I wanted more of it, so left my clothes, strolled across the field naked, still having a rock hard erection. He tells me to get on my hands and knees and I do, he knees behind me, fingers my hole a bit, then stuffs his cock back into me. This time though, he is a bit more forceful about it. He really picked up his speed, to the point where his waist is making a very audible smacking noise against my ass. He starts talking really dirty, mostly common stuff like how I was a good bitch, his dirty slut, all the while he was grabbing my ass, spanking me, and thrusting into me pretty hard. This was really turning me on, I was dripping at this point but what really put me over the edge was when he said "You must have been born to take cock considering how good you are taking mine your first time". Guess I am a sucker for dirty talk because I felt some kind of electricity come all over me and lost strength in my arms and had to lay my head in the grass. My hole was feeling amazing, he has his weight on one hand pushing me down keeping my face down and ass up while the other was around his waist pulling me back into him. After a few minutes of this, his pace began to slow but each time he pushed it in it was harder than the last until one final time he pushed it all the way inside of me and held it there. Could feel him convulsing behind me which could only mean he was cumming, which for what ever reason really turned me on. It was at this piont while he was still inside of me than he reached around and started to jack me off, though it didn't take him long and I was cuming in seconds all over the grass. Now at this point I am on my knees in ecstasy but now leaning on one arm and looking underneath me watching my dick drip last bits of cum out, him still pressed against me which his cock still inside. Couldn't help but look it looked very sexy to me, but then I feel him start to pull out and out comes this at least 7 inches of pretty thick uncut meat come out... with no condom. So the first time I let a guy fuck me was the first time I let a guy cum in me as well

Good times. Ended up cleaning up and going back into the party with the guy and had a good night talking shit with him.