Teddy, Jordan, and Me (b/b) (Please redistribute freely.) Author: Red Boy I met Teddy and his little brother Jordan when I first moved to that neighborhood. It was around 1980, and I was 10 years old. Teddy and I were the same age, and his brother, then, was in kindergarten, I think. Teddy was the first boy I ever had sex with. I don't remember who initiated it. I don't remember talking about it first. I think we were playing truth or dare...that's what our sex play eventually ended up as. I'm pretty sure that it was Teddy's idea. Where my memory begins (and I have NO idea why I can't remember earlier) is in a shed where high jump pits were stored next to the track at the high school we lived near. My memory is of Teddy, his brother, and me naked, with Teddy and I taking turns lying on top of each other. We were both about 10. I remember really having no idea what we were doing, but I was enjoying it. At that time, I didn't know how to masturbate, although I had once, when I was seven, spent about an hour in our pool jetting the hose onto my dick. I also didn't know anything about sex, with males or females. That first day, we didn't touch each other's penises. We just took turn laying on top of each other and sort of moving around. Sometimes we stuck our boners between the other's legs. Often, Teddy's boner would poke me in the stomach. I would jump, because it hurt. As I said, we eventually went to playing truth or dare. We lived near a school, and in the summer, after it got dark, we would go to a secluded place, just the three of us. Teddy would dare me to do things with Jordan, and vice versa. Jordan and Teddy never did anything with each other. We pretty much only did this kind of play in the summer time. I don't know why we didn't do it at other times. I guess `cause it was too tricky to do it inside, although eventually we did do it at my house sometimes. Another boy moved into the neighborhood a few years later, and somehow he became a part of our sex play, but he clearly wasn't really into it. We did a few things with him (by now we had discovered laying on the other's back and pushing our dicks into the other's butt. This really wasn't that great...it didn't occur to us to use lubrication). Ironically, this other boy was really into being naked. We used to play naked at his house when his parents were at work. As summer after summer rolled on, it became pretty clear that I was into it more than Teddy. I usually had to persuade him to do it. Although, there were times when he did all the initiating, but not often. One night he begged me to do it with him. I know he was afraid of being gay. He was certainly anti-homosexual. I didn't consider myself gay then. I just knew what felt good. I wasn't "attracted" to Teddy, or to other boys. Teddy was really cute, though. He had sandy blond hair, straight white teeth, freckles. His brother was even cuter. But I certainly didn't have feelings of love or lust. It was all purely physical. By the time we were 12, Teddy and I started to figure out there was more we could do. We never spoke of it before, but each of us had started jacking off. When I found out he did it, I asked him when he did it, and he said every night before going to sleep. "Me, too," I said. It was really difficult to get him interested in messing around at this point. I used to steal Penthouses from my dad. That was my favorite magazine because the stories turned me on more than the pictures. Actually, the pictures didn't turn me on at all. I remember one story was homoerotic...it was about a man reminiscing about high school, when he and his friend used to drive out to country and have sex in his car. "See?" I said to Teddy. "Here's a story about two boys having sex. It's no big deal." He read it, and after a while I convinced him to pull his pants down. I think it was under the pretense of measuring our dicks. Once we both got hard, it was easier to convince him to mess around. Then, the most exciting thing that's ever happened to me happened. "Have you ever given head?" Teddy asked. I was pretty sure he knew I hadn't. How many boys did he think I was messing around with? Actually, we tried it once, when we first started the sex play. I put my mouth on his dick, but I didn't like the taste. I don't know what made us think to try it...it was when I knew nothing about sex. "No. Have you?" He said his cousin had sucked on him once. In fact, he mentioned his cousin quite a bit. To this day, I have no idea why I didn't ask him more about this cousin. Who was he? Where did he live? How often did they do it? Thinking about it now, I wonder if it was an older cousin who molested him. Or maybe not. I'll never know. "No," I answered. And I knew with Teddy that I would have to go first. So, I did. And it didn't taste bad. He had a great penis. We measured our dicks. I think when we were 12, they were about 3 1/2 inches long, but to me they seemed pretty big. His dick was really white, and had a huge, bulbous, light purple head. I wasn't very good at sucking him off. I kept my lips only on the shaft, and never licked the head (I didn't learn about the sweet spot, the frenulum, until a sex ed class in college). He sucked me the same way. Although our lips only touched the shaft, it was pure heaven. Nothing compared to a blow job. We did this off and on for a few months. It was always difficult to get him to do it, though. Once, I was sitting on the edge of my bed, pants around my ankles, Teddy kneeling down in front of my dick. He said, "This is disgusting." I figured he was just scared about being gay, though. "Just suck on it," I said. And he did. Once, we did it in the early afternoon, in my room, on the floor. We had developed a method, so to speak. We would lay on our backs, in opposite directions, so that I could reach out and grab his cock, and he grabbed mine. We jacked each other off until one of us was about to cum. Then, one of us sucked on the other for about five minutes. We alternated this until we wanted to cum. Not once did one make the other cum. When we'd had enough, we just jerked ourselves off. He used to make a nice puddle of cum on his stomach. Later that same afternoon, we were sort of talking about it, you know the way boys talk about something they want to talk about but are afraid the boy doesn't want to talk about it. He asked, "Wanna do it again?" I was so excited, first of all that he wanted to do it again, and that he rarely initiated it. We went back to my room. Since we had done it a few hours earlier, it took me a while to cum. He was intent on making me come, and grabbed my dick hard and pumped me as fast as he could trying to make me cum. He couldn't do it, and it wasn't until I was in my late teens that I let another boy bring me off. God!!! It's just unbelievable to think about what I had, and how I never really got to enjoy it. We were just into pleasuring ourselves. I want so bad to be able to go back in time and relive those days. Back then, I didn't feel love, and I wasn't into hugging or kissing. Once, when we was laying on him and grinding away, I asked him if he wanted to kiss. He asked me if I wanted to. I said I didn't know. We ended up not kissing. I wonder what it would have been like? Would we have figured out how to French kiss? Would we have enjoyed it? Clearly we each wanted to do it, but were afraid of what we were. I haven't said much about his brother, Jordan. He was in first and second grade when we did most of this. Later, when Teddy and I were 12, Teddy never wanted to do it with Jordan around. We never sucked each other when Jordan was around. A few times, Jordan and I grinded on each other, when Teddy wasn't around. We even stuck our dicks up the other's butt, but without lubrication, of course. One day, in the summer, we were hanging out at the school yard. Jordan was standing in front of me, with his back to me. I pantsed him. He just sat there, and didn't pull his shorts up. That was the first time I ever noticed how cute a boy's butt is. From that day forward, I was hooked. That's pretty much it. We did it countless times over those summers, each summer adding more to our bag of tricks. I can remember most of the experiences. I'm just not writing them down because most are pretty much the same. The summer when I was 12, I moved away and I've never seen or talked to those two since. I really would like to talk to Teddy. I have so many unanswered questions. If you're reading this, Teddy, look me up on the Internet.