1. I once had a girl break up with me because she wanted to fuck on acid and I didn’t.
2. I’m really embarrassed when I look back and realize how many girls I basically coerced into having sex. (In at least one case, it may have been more.)
3. I’m also really embarrassed at the number of women I am friends with that I’ve made passes at. Or friends of friends. A lot of times I wasn’t even consciously doing it (see also 2), which makes it worse.
4. I’ve never made a pass at a girlfriend’s close friends. Or asked a woman out at her place of work. I’m glad I had some boundaries even as a young, walking hard-on.
5. I’ve never kissed a man, or made out with one, even drunk. (Nothing sexual either.) The only time I ever kissed a man on the mouth was lips only. It was in jest. It didn’t turn me on at all—though there are men I’ve absolutely lusted after, generally slim and tallish and strikingly beautiful. But that’s maybe three men total.
6. I’m a top. I’ve been one more or less my entire sexual life but it wasn’t until a decade ago that the woman I was fucking essentially put it to me in so many words. There are times when it kind of depresses me; I feel like I have to play a role that I don’t always feel like playing. And because I’m bald, overweight, and don’t smile much, I worry that I am a kind of walking stereotype, in a way that’s uncomfortable, especially since I have a bad mean streak. But I enjoy being a top. And no, I’ve never done heavy-duty BDSM. I probably never will; I’m not really a sadist.
7. That said, being a top has made me lazy; I fuck better than ever, but am so used to being on my back while being sucked and tongued by willing, needy women that I exhaust easily. The women haven’t seemed to care, but I worry.
8. I’ve felt threatened by the past experiences of women I’ve slept with. It’s probably common but it always bothers me because I like to think I’m above it. It’s come up again recently with my girlfriend and I’ve definitely had a couple of moments.
9. Whenever I answer a floating questionnaire meme and it asks, “What is your best-looking body part?” I never give my real answer, which is: my cock. I have a nice face, my upper body is no prize (though apparently some women like bellies like mine), but I do have nice legs, and none of it ever looks as good to me as my erect cock. I’m sure most men feel this way, too, but none of us are quite stupid enough to admit it in public.
10. Most of the women I’ve been with over the past ten years have been late bloomers that didn’t lose their virginity until their early or mid-20s. Apparently I am a walking daddy issue.
11. I’ve practiced monogamy and will practice it in the future, but I have never believed in it. But feelings get in the way even when it isn’t an argument, and given the choice between being non-monogamous and not having sex, and monogamous and having it, it’s no choice at all.
12. I used to talk about my sex life with anyone and everyone who’d listen, but not after the first woman I ever dated who was really and truly a shut-in. I’ve become one in the time since, and I wonder if I didn’t pick it up from her.
13. Oh, whom am I kidding? The reason I became a shut-in is that I got fat and felt horribly unattractive. Another reason has nothing to do with my own sexuality, though sexuality was, indirectly, one of the causes of it.
14. For about two years I decided I was tired of coming off like a gloomy Gus without even meaning to. So I forced myself to smile, look people in the eye, and be nice—none of them things that come naturally to me at all—and got a job dealing with the public. It worked: I was happier than I’d ever been, and got laid pretty much constantly. Sometimes I think I should try to do that again, but it’s hard to imagine now that I’m a 12 years older and more set in my ways. And the fact is that when I made myself smile for two years it was because I was desperate to get laid, and now, even at my loneliest, I’m not.
15. I’m still really lonely a lot of the time—girlfriend is in another town a few hours away (job related). I have a standing offer I am probably going to say yes to soon. I don’t mind it but the gf would, not that I plan to tell her.
16. I’ve cheated twice. The first time was awful—partly because I didn’t know how to handle it with my then-gf, partly because the woman I cheated with was a self-centered airhead. (She was also terrible in bed.) The second time was with someone I’d slept with before whom I bumped into shopping. We did it in secret for a couple months and I wish it had lasted longer.
17. I like things in my ass: tongues, fingers, vibrators. I knew this from about nine, when I would penetrate myself with sweeper handles and, later, my mom’s dildo. I hadn’t thought of any of that in a while until I was 19. The girl was named for a fabric and had a Tintin hairdo; she was also the girl in 1, and the third I ever had sex with. I was on top of her and she slowly reached down and pushed her middle finger into my ass. I did the same thing to her, and then we kissed. I’ve never felt more completely whole, sexually.
18. I have had sex with 25 women.
19. One of them, when I was 22, was with a severely fucked up girl—at 19 she’d been molested, raped, married and divorced (and engaged beyond that), had two abortions, and she was generally attracted to scummy older dudes. She was one of the most alarmingly thorough and skilled fucks I’ve ever had. The second time, in my rented room, she took her clothes off and matter-of-factly said, “Vaginal or anal?” Luckily I had lube. Watching my come pour from her ass over her pussy and thighs is still the hottest thing I’ve ever seen.
20. I’ve never gotten a blowjob from a woman without having sex with her, but I’ve eaten a lot of pussies I never got to fuck. I prefer it that way.
21. The first older woman I ever slept with, by five years, sent me a very dirty fantasy letter after our brief fling; another woman, also five years older, gave me her underwear after a particularly creative night on the phone. No other gifts, but those two have sustained me for a long time.
22. I started wearing glasses again in my mid-20s because I was trying to fuck a girl who liked guys that wore them.
23. I have no greater desire than to be considered a complete slut.
24. I wish more total sluts would out themselves to me so we could degrade each other at last.
25. I use my mouth, hands, and cock all equally well, and I’m proud of that.