My first Time

My first time with a guy was a great experience, even if I wasn’t trying to be gay. We were best friends, Dave and I. I never considered myself gay, nor did I have feelings for Dave other than we had fun chatting together, and spending the night at each other’s hours playing video games as we were growing up. When we went off to college, we got the chance to be roommates. We were freed to do as we wanted together. One night, we were discussing sex, and looking at the Playboys and Penthouses we had saved up . It was a warm summers day, and school was just starting. I was sporting some wood. I could tell Dave was having a ‘hard’ time too, so I brought up how some of our other friends always joked about ‘being gay’ with each other. I asked if he wanted to try “being gay” as long as we held some ground rules. No kissing and no butt sex. He seemed to want to do something to relieve the pressure of his hard on as much as I did, so we knelt in front of each other and slowly exposed ourselves to one another. He was more developed than I was, longer than me, and way hairier. I reached over to stoke his penis and he did the same, we slowly pulled on each other, unsure of what we were doing, and not sure if we liked it or not. His hand on my cock was sensational, the only person to ever touch me, besides myself. It was amazing, and very hot. We were both sweaty and breathing very heavily, and it was very quiet. It was a slow stroke from both of us, and sort of awkward. You’re not used to the angle that way, and it was sort of clumsy. Eventually we got into a rhythm, and as one of us went a little faster so did the other. We were looking down and not at each other, when all of a sudden; he made a moan and started cumming. It sprayed all over my shirt. It smelled different than mine, and I wasn’t brave enough to taste it, yet. Meanwhile he kept stroking me and I was overcome with the need to let loose. I closed my eyes and had the most intense orgasm ever. After 4 years of doing it myself, this was wild. I convulsed like never before, and I actually shot cum out. It usually oozed out when I stroked. This was totally different. We cleaned up our mess and got dressed again. Dave wasn’t too please afterward and seemed put off by what we had done. I was still quite aroused. That night in bed I tried to quietly let another one loose like that, but it wasn’t the same as when he did it..
We continued to be as friends, never really speaking about what we had done, and one night we were busy studying and it was late. It was time to hit the sack, and I got in my bed and he crashed in his. I hadn’t tried to bring up “being gay” again, and usually waited till I knew I was going to be alone to jackoff. I waited a few minutes and thought he was asleep, and started stroking, I was feeling really horny. All of a sudden, he startled me by asking if I was playing with myself. Busted, I sheepishly said yes. He looked up from where he was laying down, and said, he too wanted to masturbate, but was afraid to bring it up again. It wasn’t my intent to do this again with him, since I figured it was a no-go, but I wasn’t letting this chance pass me by. I suggested he get into bed with me, and we lay next to each other and slowly started stroking each other, him on my right. Luckily, he is left handed and I am right, so it worked out that it was not as awkward as the first time. After a few minutes and almost getting close, he stopped and leaned up on his side. He told me to do the same, and we were facing each other. Our dicks were touching, and he grabbed them both in his hand. We were both breathing heavily at that moment and looking down in the pale light at or erect cocks together. He slowly started pumping them both and that was getting me hotter and hotter. I could feel my balls tighten and that tingle start that told me I was going to cum, but I wanted this to last. I looked over, smiled and said, I want to try something. He didn’t have to do it as well, but I wanted to suck his dick. He thought about it, and finally agreed. I grabbed his cock while I started licking und sucking his nipple. I circled it a couple of times and then worked my tongue down his stomach and toward his cock. I reached the pubic trail at his navel and then started kissing my way down to his cock. The heat and the smell were rising up to my nostrils and I took it all in. His skin tasted different than if I licked my own hand, and it was very heady. I was getting ready to put his cock in my mouth when I decided to tease him. I am not sure what came over me, but it seemed like the thing to do. I kissed and licked around and all over his thighs, balls especially underneath. I slowly worked my way kissing up his balls, and then let go of his cock as I slowly ran my tongue up his shaft. When I reached the head, I put my lips around it, swirled my tongue around the head, then opened my mouth wide as he slowly thrust his meat into my watering mouth. I sucked for as much as I could, slowly moving my head up and down. As it was my first time, my teeth got in the way several times, and he let me know. But otherwise we were both enjoying it. I didn’t know it at the time, but as I was cupping his balls, I could feel them tighten, and he let out his load. I gagged a little and spit out some, but then swallowed what I could. I didn’t enjoy it like I thought I would, but then my own cum never tasted good to me. His breathing finally slowed down as I lay back next to him, and I started stroking myself off. He stopped my hand, and what happened next was unbelievable. He bent down, and while he didn’t tease me and lick me all over or anything as I had him, he took my cock in his mouth and started sucking! I was floored, but didn’t want to ignore the fact my cock was in a soft, warm mouth. He too didn’t know what to do, and of course, I had no idea this crappy bj was crappy, I was in heaven. He sucked for what seemed like forever, and I finally started feeling the urge, he seemed to tell as he let go with his mouth and finished with his hand. It was awesome. We went to sleep and got up the next day but didn’t speak much about what we did..
As fall progressed, and we would study or whatever in our room, we would take a quick jack break, and look at Hustler and Penthouse and then race to see who came first (who knew that was the wrong game to play…), but we never really touched each other like before. Then came February, and a streak of cold and snow that ultimately shut school down for a week. We hung out almost the entire time together, but it wasn’t till the third night, we had the video games going again, then we watched Late Night with Dave Letterman. We discussed some of the penthouse letters we were reading over the week and both of us lamented that we had yet to score with any pussy. He said it would be so cool to slide his dick in a nice warm hole. Lightbulb. I asked if he wanted to try sticking it in my ass, which of course he didn’t have to reciprocate, I said that it violated one of our rules, but as long as we didn’t kiss, it wasn’t really gay. He thought about it for a while as we stoked ourselves and finally said yes. I got some petroleum jelly from the closet where I kept my stuff. When I came back he was totally naked. We got on the floor and I laid on my back and stuck a little of the lube on my asshole, and he stroked some on his dick. He positioned himself above me and put his dick in between my ass cheeks. I moved his dick around until the head of his cock was targeted and whispered to go ahead and push. And push he did. He pushed so hard my eyes started watering, then he finally got the head of his dick past my rim. Man, that hurt. When I fapped, I never stroked or even really touched my ass, so this is the first time of really using it in a sexual way. He slowly pushed back and forth and finally got all the way in. I kept him very slow, till I could finally figure out how to relax and let his dick do its thing. And actually, it was kind of cool feeling his bush tickle my balls. After a few moments I slowly pushed and let him rock back and forth, and after a while he got a nice rhythm going, and was really going smoothly. He then started to increase his pace, and I wasn’t feeling near the pain, if anything an intense pleasure as his cock rubbed me hard and his balls slapped against my ass cheeks. i started stroking myself in time with him and it felt so good. He finally arched his back and came inside me. I let him gush all the way and he laid on top of me just as I was cumming. It felt so good to have him there, I didn’t want it to end. We fell asleep, and got up the next day and hung out all day. It was bitter cold and snowy, so it was all indoor stuff. We went from my house to his and I ended up sleeping there.
That night after we watched a movie on HBO and it was time for bed. I again waited till he was asleep, or so I thought, and started jacking, this time he grabbed my hand, bent down, and started kissing my dick. Then licking and sucking me. I got totally hard in his mouth. I never expected this from him. I always figured he was doing me because it got him off, but that he really wasn’t into it that much. He reached from under the bed, grabbed some jelly and I thought, oh man, another ass fucking. What I didn’t expect was that it was my turn on top. He started lubing my dick then he got on all fours, and said, “your turn, go slowly please.” If I was never hard before, I was hard now. I never had such a raging boner. Just the thought of sticking my dick into a warm hole was unbelievable. I kneeled behind him on my knees, and guided my dick up to his asshole. I smeared a little lube on his hole. I let him push back on me to get comfortable. I pushed ever so gently to try not have it hurt him as much as he hurt me at first, cause I so wanted my shot at this. I slowly worked my head past his tight hole and slowly he moved back and forth and we started slapping our bodies together, but then, he stopped. Oh, man, it was too much for him. I waited, and he was breathing hard, but didn’t say anything. I then felt him cup both our balls together and he squeezed his ass around my dick to kind of suck it in. it was wild. I almost came right there. He then said “nice and slow, let’s do this.” We started moving together and it was the greatest feeling ever. His ass was so hot and tight, my cock was feeling so good, every stroke getting me closer and closer, and just as I was about to cum for all I was worth he pulled my out, and said it was all he could take. Arg. It was dark so he probably couldn’t see my face, but I lied and I said it was alright, I knew how much it hurt, but then it would give way to pleasure, just ride it out, I told him. I kept going for a while, then I figured, why not, and asked if he wanted to fuck me again. So we switched positions and he got his dick inside me. Two nights a in a row, and I was a regular ass fucker. I stroked my dick for all I was worth. And the feeling of his balls slapping up next to mine were priceless. When his balls stopped slapping against mine and finally tightened I could tell he was going to go and I pumped for all my fury so I could cum with him. I felt his hot semen gush in my ass and seep out and down my thigh as I let out a huge load on the floor beneath me. The smell of our enjoyment still lingers with me today. . He rested his chest on my back for a few minutes as we caught our breath and his cock finally slipped out of my ass. I reached back and patted it and said, “thanks.” I don’t know why. I wasn’t in love with him, nor did I want to kiss him, really. Not even to practice because I had at least kissed many girls. And the few minutes I did stroke my dick in his hole would have to hold me over till I finally broke the pussy barrier.
That was the last time we got together for the remainder of the school year. Again, we never spoke of our deeds outside of the initial rule making, and never did we share secret moments outside of our bedrooms to touch each other or anything. That summer he was busy with his job and football, and I was busy with my job and getting ready to go away to a different college. I went over to his house the morning I was to leave and we talked about life, and his second year, his football, my job and my going away, and all those big plans kids our age had. I kept looking at his body. It had developed nicely since we started “playing gay” with his football and all, and I was admiring his shoulders and noticing how well he filled out. He must have caught me checking him out, and he did something surprising. He stuck his foot out and started rubbing my crotch. I did the same with my foot and before you know it, we were both hard as a rock and ready for some action. He took me up to his room, and no sooner did he close the door but I dropped my shorts, landed on his bed with my legs up and demanded to be taken by him. His dick was much bigger now, and I was hungry for it to stuff my ass. He pulled out some lube and we went to town. It was the middle of the morning and I was in heaven. I can still see his face as he fucked me hard, those eyes as they lustily took in what was happening down at our crotches, and the look of total satisfaction as he came in heap on top of me. I cleaned up, said good-bye, and I never laid eyes on him again, never having the chance to cross paths, as he avoided me the few times I got to come home from college. I hear he is married with kids somewhere near where we grew up. I too am married with kids, in another part of the country. But I still get off to that glorious year of “playing gay.”