Chapter 8: This Part Is Pretty Gay

So, I’ll tell about one of my first “real” experiences with another guy. When I was in high school I was pretty independent - my parents gave me a lot of space - and I definitely got around. Mostly with girls, but in my senior year I had a friend who shared a lot of interests. Met him in a class we shared and we quickly bonded over computer stuff. I remember when I first saw him thinking he was kind of cute!

We lived pretty far apart, so after hanging out at his house I used to sleep over fairly often, and I guess since he was kind of diffident I sort of kept pushing the boundaries with him. When it was time to turn in he’d always sleep in his bed and I’d be on a mattress on the floor. Now I had always slept nude (at home too), and even though when I first started sleeping over there I would just take off my clothes after I’d gotten under the covers, at some point I felt the urge to be a little exhibitionistic and I let the covers slip more and more until, sort of pretending it was an accident, I “flashed” him a bit.

This didn’t seem to bother him so I gradually started being a bit more demonstrative. Maybe the third or fourth occasion I slept there, when it was time for bed I simply got fully undressed in front of him, before he turned out the light, and just sat on the mattress with the sheet only partially draped over me, casually continuing our conversation. He was definitely checking me out and didn’t seem too disconcerted by what he saw, so I sat in a way that revealed that I had a semi hard-on, which certainly seemed to intrigue him. He was still dressed but I had the distinct impression from the way he was shifting around that he was getting hard himself. Plus his face was getting a little red. It was cute! I remember both of us just continuing to talk about computers or whatever and studiously pretending that there was nothing else going on.

Eventually I just said something like “Dude, just get undressed and let’s go to bed” but unfortunately he got up and turned out the lights before he stripped down to his underwear (he always slept that way). As we was getting into bed, I could see in the darkness that he had a full erection, though. I made some joke about it being unfair to make me sleep on the floor but he didn’t take the hint.

I don’t remember if it was on that occasion or a subsequent one - but at some point I got so horny lying there naked on the mattress next to my friend’s bed that I just “took matters into my own hands” and jerked off in front of him (in the dark). I came almost immediately and after a short while I heard him going at it too, but we didn’t say anything more about it that night. I do remember the next morning he told me he’d dreamt that night about having sex with his mom, which was a little bit of a weird thing to share (his mom was cute though!) and I remember sitting on the couch in the living room with him and he got kind of close to me, so I just put my arm around him and he didn’t seem at all bothered by it. We just sat there like that for a while until his dad came in (must have noticed we were sitting awfully close, but didn’t seem too concerned about it).

So after that I got bolder. One afternoon we were hanging out in his room and he just randomly showed me some girlie magazine he had secreted away. I took it as a signal. his parents weren’t around and I knew we wouldn’t get interrupted, so I made some joke about not being able to resist, unzipped my jeans, pulled them down, and started masturbating (that’s what you do with a porn mag, right?) Yep, right there in front of him. Of course I had been gauging the situation all along - I wouldn’t have done it if I had had any doubt about his interest. But nothing exhibitionistic I’d done up to that point had fazed him, so I wasn’t too worried. And sure enough, without a word, he pulled down his sweatpants and underwear and sat next to me on the couch. Not only did I find him cute, I now realized he had a really nice penis.

I scooted over a bit closer so that we could both see the magazine, but pretty soon just put it aside and we just watched each other and stimulating ourselves. It turned me on to see how hard he was, because I could tell he was really excited by the situation - by looking at me, in a sense, and that was a turn-on for me. He came first, pretty quickly, and started to pull his pants up. I remember I asked him to let me keep watching him a bit longer, and he obediently stood right in front of me, pants down. I looked at his nice, softening cock and his clothed upper body as I finished myself off, carefully cupping the head of my cock to avoid splashing him - I came pretty hard! Afterwards we were, I guess, both a little embarrassed and we just went and showered (separately), pretending that nothing out of the ordinary had happened.

It wasn’t too long after that that he came to my place - first (and only) time that ever happened. had dinner with my family and everything - then we went to my room to do computer stuff and later to listen to music. We had a big house, and my parents were always good about giving me my privacy, so even though they were home I wasn’t too worried about being interrupted (although thinking back i’m a little surprised I wasn’t worried about my nosy sister in the room next door). Sometime in the course of the evening, as it got close to bed time, I just stripped naked as I always did. I was quite the exhibitionist - made sort of a show out of walking around in front of him, undoubtedly with a hard-on or at least a semi, each time I went to change the CD.

Eventually my friend stripped down to his underwear as we got ready for bed. Somehow he took it for granted that he was going to sleep in my bed, even though it would have only been fair for him to take the floor at my place! I didn’t say anything, but I pushed the spare mattress right next to the bed and was sitting there naked with my elbows on the bed as he was lying in my bed. as we talked about the music or whatever I got kind of touchy - just kept lightly touching, and sometimes out-and-out stroking his shoulders and upper arms and chest (the rest of him was covered with a blanket). I remember he made some kind of lame joke about how I probably wanted to sleep in the bed with him. I probably said something similarly jokey back, but the whole time I was sitting there, touching him more and more frequently while we talked, and he was clearly responding positively to my touch.

Eventually I started massaging his chest, over the blanket, and he seemed to like it so I got further and further down until - electric moment! - I encountered his hard penis pushing the blanket up. I’ll never forget the little gasp he let out when I touched it! I began to stroke him through the blanket, and it was an incredible feeling, but very soon he blurted out “no, don’t.” I was very sensitive to the precariousness of the situation, and I felt a little ashamed - this was the first time he’d ever shown any hesitation - so I just stopped cold right there and we just kept talking about unrelated stuff. I think neither of us really knew what to do at that point, and indeed nothing further happened that night - we just went to sleep after a while. I didn’t even jerk off - if he did, I didn’t notice.

I felt rather guilty and confused all of the next day, but when I saw my friend in class in the afternoon, he invited me to sleep over at his place that same night. I think I couldn’t do it that day for some reason, but later in the week I went over. It was so funny - we were both obviously very nervous and unsure about ourselves, but also expecting something to happen. We just played with his computer and talked about random stuff, totally avoiding the elephant in the room. When it was time to get ready for bed, I didn’t get naked as usual, just stripped down to my underwear as he did. he made a joke out of saying “aren’t you going to take off your underwear” and I came back with the obvious rejoinder: not unless you do! I was actually quite surprised when he proceeded to take his briefs off! I watched intently - that was the first time I’d seen him completely naked (of course I’d seen him often in just underwear, but the one time I’d seen his penis he was otherwise dressed). It was an attractive sight and I remember feeling a sudden urge to get close to him. I just wanted to feel what it was like to hold our naked bodies together.