1. I have had a much more boring sex life than most people who post here. The first time I masturbated I was eleven years old. I had been reading those "What's happening to my body?" books about puberty for boys. I remember I lay in bed and rubbed up against the bed sheet. The orgasm was so intense that it pulled every muscle in my body taut. It stayed that good for a while, but later I got used to it. Now I masturbate usually once a day and it's the same kind of routine like going to the bathroom or grabbing lunch. Now I only get that kind of orgasm with oral.
2. When I was twelve and thirteen I'd fantasize about girls in my classes. I stood in front of the shower and lined them up in my mind and fucked all of them, getting them all off before I came in my favorite.
3. My aunts made fun of me when they found the puberty books, saying I probably went straight to the small section they had about girls. I hadn't even thought of that, but then of course I looked. We had just gotten the internet, so I started exploring online, first with softcore and then got more and more explicit.
4. When I was fourteen years old after watching the movie "The Messenger" with Milla Jovovich I couldn't bring myself to masturbate for a month (ironically, just a couple years before I had scoured the internet looking for naked pictures of Milla after seeing "Fifth Element"). "Messenger" features a scene where the young Jen d'Arc hides in a cabinet while her sister gets a sword run through her (into the cabinet of course) to shut her up while some invading German type rapes her as she dies. I was horrified but also very carefully watching myself to make sure I wasn't turned on at all. I still remember a crawly feeling in my testicles. For a while after I managed to start masturbating again I had to keep my eyes open to keep from seeing that scene.
5. I read a lot of erotic stories. Once I read a story about a man who was tested in some pseudo religious voodoo tantric thing where he had to get his wife off without getting himself off in the process. He failed, so he had to watch the master priest (some well-hung black guy, naturally) fuck his wife and get her off many times before coming himself and getting her pregnant. The husband had to bear his shame constantly for the rest of his life every time he looked at his child. Even now, probably nine years after reading it and seeing the obvious hole in the plot, it still bothers me.
6. The first time I kissed a girl I was thirteen. She wouldn't let me do more than peck her until I was fourteen. We made out for the first time after seeing "Episode I" in the theater opening weekend. The first time I showed her my penis at age fifteen she froze immediately, in horror or fear or what I never did find out. She touched it hesitantly like it was some decomposing sea creature. That same night I talked her into letting me touch her. It was the first time I felt a girl's vagina. It felt weird but worthy of further investigation. I wouldn't lose my virginity for more than three years.
7. After a long time I talked her into giving me a real handjob. She still wouldn't look, so she would close her eyes or look away. I had to pull her hands off me at the last second and use a tissue to catch all the semen so she wouldn't get any on her.
8. For all my pushing, I refused to ever try to convince her to go all the way. I read a thing online (I think it's from the Red Cross) about how whenever you have sex with someone you are having sex with every person that person has ever had sex with. That made me very paranoid about where I was putting my penis, and I didn't want to push that kind of thing on her. One day, out of the blue, she said she wanted to have sex (sorry, "make love").
9. I lost my virginity at age eighteen in the same treehouse I'd had my sixth birthday party in.
10. We mostly had sex in my old house, because we were both homeschooled and could never get away from our parents any other way. It was dank and musty and unpleasant (I'm talking about the house... mostly). One time she sneezed and the force somehow crushed my penis and she squirted out a bunch of mucousy yellow stuff. I still fucked her after that.
11. We had sex less than a dozen times before she finally left me and ran off to another city with her girlfriend. The last time we were together we just gave each other oral. I still had to talk her into doing it, even then. She spit. Most of our sex life had been cyber- and phone-sex. She was never interested in anything without prompting (obviously). I think I instructed her through her first orgasm with an electric toothbrush. I always wondered if she'd been molested. Now I just figure she's a lesbian. To date I don't know if she's figured it out herself. Or she might be one of those few truly asexual people in the world. I don't know. Doesn't matter now.
12. The next time I was with a girl I was twenty-one. She never just kissed me without giving me full mouth-to-mouth. It was exhilarating. We made out on her stairs, but when I started feeling her up she stopped me. I don't think it's that she didn't want to rush, more that she wanted me to be in love with her before she'd go any farther.
13. That was the first time I lied to someone about loving them.
14. Talking to her was a chore, as she was not a native English speaker. I was only interested in her mouth for oral. She gave me the best blowjob I'd ever had. One night I found out she'd lied about her age and was more than twelve years older than me (she said she was twenty four). I left her then. I said it was because of the age but I was looking for a way out anyway. As a fuck buddy or a friend with benefits she was great to be around, but I couldn't stand the idea of being in a real relationship with her.
15. I wanted "one more for the road" so I came back another time after that night and she went down on me again. I cut off ties with her shortly after. I still feel like a jerk.
16. A few months later I met my second real girlfriend. She was with someone at the time, but the attraction was undeniable. One night she came over and we drank a little, but I was a perfect gentleman (a fact I don't think anyone subsequently believed). When I took her home, we both wanted to kiss each other, but we didn't. She said she was in a bad relationship, so I just figured I'd wait and catch her on the rebound.
17. Not long after I started traveling. A couple weeks into it she wanted to know if I was attracted to her. I said I was. We started cybering when I traveled. I never quite figured out what happened with the breakup, just that I almost lost my best friend over it. I was so lonely I was willing to do almost anything.
18. I was in Amsterdam before we got together, and my father offered me €50 to bang one of the prostitutes. I declined, partially because I just didn't want to, but mostly because I was loyal to someone who I'd only really had a relationship with online. I still feel a little stupid for the second part. Later I got stoned and ended up flirting with a really cute girl. She was the one I really regret not pursuing.
19. When I came back I could never really fall for her. Whatever magic we had that first night seemed to have dissipated. I still felt for the person on the screen, but I couldn't translate those feelings for the real person for months. That was the second time I lied about loving someone.
20. She was almost impossible to get off. Sometimes I would fuck her for fifteen minutes without even getting her close. I would get so sore that when I eventually did just let myself go it always hurt. Whenever she drank she'd get ravenously horny and make orgasm completely impossible. I began to dread her drinking. She always said it was fine, that I could just get myself off and it wasn't a big deal. I never believed it. Though, now that I'm writing this I'm beginning to see where I got the obsession of getting a girl off.
21. Combining the fact that she was hard to get off with her refusing to shave under any circumstances, going down on her was incredibly arduous. I only did it a few times. Of course getting her off by hand was out of the question. As a result she naturally refused to do anything of the sort for me. I didn't bother asking.
22. One time the condom slipped off after I came and we had to run to get Plan B at night when only the Wal-Mart pharmacy was open. She didn't say a word to me for a week after that. I figured we were through, but we stayed together for another couple months. I don't know if that's when it was really over though.
23. The last two times we were together she didn't even bother trying attempt getting off. She used her vibrator after I was done. I got the message.
24. Right after my first girlfriend left me I had bought a Fleshlight that I didn't like, so I never used it. I got a different insert after I broke up with this one. It was awesome. After laboring at sex for so long it was like a breath of fresh air, even if I was by myself. I fantasized about fucking a girl I met a couple times on my counter. She was skinny enough that it would have worked (being anorexically skinny has got to be good for something). We never got that far.
25. My current girlfriend is awesome. I can get her off multiple times without even working for it, and she goes down on me with zero prompting. It's gotten me wondering if this is what sex is supposed to be like. She's the first person I ever considered having sex with while not using a condom.
