Sunday, August 21, 2011

1. The first time I had sex was when I was 17. It was with a prostitute--"escort"--who was probably fifteen or twenty years older than me. I found her online. I am nearly nineteen now and that is still the only instance where I have had sex.

2. When I arrived at her small apartment, she had already been drinking a bit even though it was only 3 in the afternoon, which probably helped me convince her I really was a college student, and she was bad at math so when she looked at my ID she didn’t realize I was under 18. My God, does that sound awful. Oh well, it’s true.

3. After a bit of small talk and a couple “you're not a cop, right” questions, she suggested we go upstairs. I got naked on the bed and she stripped to her underwear and proceeded to go down on me. After about ten minutes I stopped her and went enthusiastically down on her, until even she stopped acting like she enjoyed it. Actual penetrative intercourse happened next. It started and ended in missionary and was over way too soon (five minutes would be generous). Despite having an extremely active libido 99% of the time, and usually being able to jerk off 3+ times in under an hour, I couldn’t get it up for another go.

4. It didn’t help that I felt an overwhelming feeling of shame and paranoia about STDs (even though I used a condom ) immediately afterwards. Also I had a running challenge with myself to see how long I could go without masturbating, which after a month of torture led me to paying a woman to take my virginity, and left me sexually exhausted.

5. Afterwards I realized I had also just paid a woman $140 to basically just masturbate inside of her. Not that I regret it though, really.

6. I masturbated to the experience twice six hours later. I still couldn’t believe it had actually just happened.

7. I’ve only dated three girls since eighth grade. The first was from my neighborhood, the second was a girl I met at a party, and the third went to my school two grades below me. None of the relationships have lasted longer than a month.

8. Partly this was because the school I went to was 45 minutes away from where I lived, and very small, which made it hard to hang out with friends after school and on weekends. And since I had gone there since I was in fourth grade, most of the friendships I had around the neighborhood sort of died off.

9. Mostly the relationships stopped because we had nothing in common with each other. I dated them because I was bored, lonely and horny, and they were cute. I think they were doing the same, but neither of us would end up having much in common. After a month we didn’t have much to talk about anymore.

10. This terrifies me, however, that all my future relationships will end up this way. I have met a few girls that I do have an instant connection with, and this does help to stem the fear a bit. On the positive side this fear is a motivating factor behind me trying to be a better person both physically (lifting weights) and mentally (actively trying to be more outgoing and more confident).

11. Moving on to other firsts, I first kissed a girl when I was 16. It was girl number two that I dated, at a party, and wonderful. A bit late, but that’s the story of my life, I suppose.

12. I first started to masturbate when I was twelve or thirteen. It happened the same way I found out about escorts--I stumbled across an internet article on the subject and got a butterfly/adrenaline rush in my stomach as I thought holy shit, I can actually do this.

13. I then spent a large amount of time researching techniques on how to jerk off, and jerking off. Oddly enough, internet porn never really came into the equation until later.

14. It actually probably took a month or two of steady practice before I was able to orgasm, and I started ejaculating soon after that.

15. Another first was the time I found two Penthouses under my older brother’s pillow instead of the Harry Potter book I had been looking for. What a revelation those magazines were. Before, I would try and make mental images of naked girls whenever I was lucky enough to watch an R-rated movie. I remember the full frontal scene from Life of Brian had me sexually frustrated (since I didn’t know about masturbating then) for weeks. When I found those magazines, I could finally study every part of the female anatomy in extremely explicit detail to my heart's content. I was in fifth grade at the time, and every time I looked at a girl from my class for a week following that I would see the pictures from Penthouse, which definitely freaked me out a bit.

16. I’ve always liked anal penetration. I remember soon after I started masturbating, I would be in the shower and alternate between stroking my cock and playing with the entrance to my asshole. I think my justification for exploring my asshole was that I wanted to feel how a girl feels being fucked.

17. I experimented with anal masturbation in full two years ago. I never found my P-Spot after a pretty long time exploring, but I did realize that orgasming with a finger in my ass does actually lead to a different orgasm. I also generally enjoyed the feeling and new sensations of having something in my ass.

18. I would like to be fucked by a woman with a strap-on. I think that is ridiculously hot.

19. Additionally, I would love to be in the middle of a MMF threesome. Being fucked by a real cock while simultaneously fucking, licking, or getting sucked off by a woman would be sexual heaven.

20. I’m not entirely sure where I would rate my sexuality. I do think men can be beautiful but they simply don’t have the gut punching effect as when I see a beautiful lady. And in my hornier moments I definitely wonder/fantasize about giving blowjobs, and receiving anal sex. But even then intimate things like kissing or swallowing tend to gross me out for some reason. I find it odd that I would love to have a cock in my ass but have no desire to kiss who that cock belongs to.

21. My preferred porn is erotica. Visually it tends to rotate between vanilla, prostitute, amateur porn, hardcore hentai (this is probably what I’m most ashamed of and I don’t really know why), and strap-on porn, usually in a random order.

22. I’ve also read The Multi-Orgasmic Man and attempted to become multi-orgasmic, but I usually lose interest in the exercises and stop trying after about a month. I do love having strong PC muscles though.

23. The college I’m going to attend has a tumblr where students can submit naked photos of themselves. I am considering submitting a photo of myself for some of the same reasons I am submitting this. Plus the thought helps keep me motivated for going to the gym and keeping things trimmed down there.

24. Because 25 things are surprisingly long, this one is kind of filler. There were four girls that sat in front of me during grammar my junior year, and one at least once a week always popped a thong. This destroyed any chance I had about learning grammar, and once I saw that it would be very difficult to tear my eyes away for the rest of the class. Since there were only 12 people in the class, it was probably painfully obvious to the teacher, but she never said anything. Random tangent: The teacher was arrested last year for dating and sexing up a fifteen-year-old like seven years ago. She was pretty good looking, too.

25. I don’t know how to say this without sounding like an asshole so I’m just going to say it: Assuming I’m not in a monogamous relationship, and if I have large amounts of cash to spare, I could see myself using prostitutes again in the future, even if I am getting regular sex from multiple partners. There is just something sexy about no-bullshit sort-of-sex sort-of-masturbation and being in the position to choose a girl exactly to what your sexual desires are at the moment, and acting on those desires when you feel like it.