1. I lost my virginity about an hour or so after I kissed a girl for the first time.
2. I came of age, sexually, during the age of AIDS. It always seemed that people a little older than myself had had wonderful, last hurrah unworried sex with anyone they wanted. In the age of the internet, it seems people younger than myself have lots of carefree, guilt-free sex with whomever they want. But there was a kind of dampening effect for kids of my age caused by the close proximity of sex and death everywhere we looked. I'm glad that is over.
3. I haven't had sex with very many women and it does not bother me. I have had all sorts of challenging and comforting and mind expanding and dangerous dark experiences with my little number of five women. I used to spend a lot of time wishing, for no real reason, I had had sex with dozens of women. But I don't care anymore about numbers. I have a maddeningly clear memory, and would rather have gleaned much from few experiences than little from a lot of encounters.
4. I am often quiet in person but I love to flirt and write dirty emails. Sometimes, I start little craigslist affairs and realize I hope they don't have to be consumated before I run out of enjoyment with the flirtation.
5. The second woman I slept with intimidated me on many levels. One of which was the great number of men she had fucked. Yet, she had never had an orgasm and it became a kind of mission for me to give her her first. I thought that she purposefully did not want to give up that power, that she derived a control over being much more wanted and much more skilled at fucking than any man who wanted her. I remember the intense red of her cheeks and the wild look on her face as she came for the first time. It made her vulnerable to me and though our relationship was completely incendiary in every way, we are friends eighteen years later.
6. The last woman I had sex with would literally drool at the idea of giving head. She recalled with anger a guy she had once dated who did not like to receive blowjobs. She gave amazing head, went at it like she was starving, and sucked every last morsel of cum down greedily. By the third time we had fucked, I felt almost guilty if I did not cum in her mouth. On the other hand, she was usually smiling warmly as I lost myself deeply in her butt or nearly shouting with pleasure and orgasm if I came in her cunt.
7. I think I am the only person who claims anti-depressants improved my sex life. Before I had to take them, the great endless whir of lips and butts and tits that ran through my head controlled me, sent me off to the bathroom to masturbate all the time. Now, though I think of sex less, I enjoy it much more. When I first started fucking the woman mentioned above, it was such a pleasure to be able to last as long as I wanted, to not be nervous about my own performance.
8. I can imagine having sex with men in only an abstract way. It's like a movie which is very interesting if the camera is only focused tightly on a couple of penises and butts, but becomes horrifying when zoomed out to catch a real face in the picture. This doesn't really much matter to me, though I would like to have know what it feels like to give someone a blow job.
9. I would like to be fucked by a woman wearing a strap-on, but the idea of procuring the whole get up is too funny and cumbersome to imagine really getting around to. Besides, that stuff is expensive.
10. I had a threesome once. It was a bad experience and I prefer to imagine it never happened. I hope to erase the memory someday with a better one.
11. An old friend, who was briefly a lover, recently got in touch with me. It was one of those affairs that had to happen, given how close and affectionate we were, but ultimately killed our friendship. We had not spoken in about 16 years but I was glad to hear from her. She told me that prior to us becoming lovers, my best friend had date raped her. He had taken her hiking and forced himself on her. It explained some oblique comments on both their parts when we were together. I felt both violated and somehow complicit in having created a safe environment for her—the three of us had taken many similar hikes to that which he used to lure her— that my friend used toward horrible ends.
12. The first time I masturbated, I wondered if there really was a devil if I could feel that great. My parents were not religious, I was not religious, I have no idea why I felt guilty or scared.
13. The first time I had butt sex, it was kind of an accident. No I really don't remember clearly how I mistook one hole for the other—I think we had been fucking for a long time already and everything was very moist and I was exhausted—when I realized what I was doing I stopped. “It's okay,” she said, “keep going.”
14. Despite such an embarrasing start, I have always found the off-kilter, trust-neccesary aspect of butt sex mind-blowing. I have it every chance I get, partner willing.
15. The first butt partner, mentioned above, was fairly willing but I am ashamed to admit that I often pushed her past her boundaries, used the dominating aspect of it for darker motives of control and revenge.
16. I live in a rural community whose women are mostly really young, really old, really married, or really crazy. I would not even know where to begin to try and get laid, semi-ethically, here. It drives me crazy.
17. Before my marriage fell apart, I happily cheated on my wife. I say happily because it put a smile on my face when I really needed one and allowed me to not endlessly resent her disinterest in sex. Some of the last best days of our relationship were after I spent the mornings getting well and truly laid by another woman.
18. I would usually rather have really good sex than really unusual sex. One time, though, I met my ex at the airport after we arrived on separate flights. She was wearing a little skirt that drove me bananas. On our flight together, I put a blanket over her lap and started to rub her labia through her panties. She was generally pretty shy about being caught having sex, and when she got up rather abruptly and went to the bathroom I thought, oh well. When she came back she put my hand back in her lap and the panties were gone. She was sopping wet, and I took as long as she could stand to rub her to orgasm. She came with a delicious little moan.
19. I lived for a time in a semi-communal, college owned cabin in the woods. One morning my girlfriend and I awoke to the sounds of two people giggling on the other side of a thin partition. We peeked through the partition and watched another couple saying all sorts of stupid things to one another while she slowly rode on top of him. “Look how perfectly my tits fit in your hands,” she said. Shit. We tried not to laugh at them, and to make my girlfriend stop, I started fucking her. I don't remember which of us came first, but I stopped watching before they did.
20. I don't really smoke much weed, but I once in a blue moon I like to get high while fucking. It gives me the most wonderful orgasms and there is something pretty hot about watching a naked woman smoking anything, especially while I am sucking on her nipples or fucking her from underneath.
21. Sometimes, especially lately, I wish just had someone to make out with. I never really “dated” as a kid and part of me wants to drive to town some nights and just make out, kissing and groping only, at a movie or a beach or some such place.
22. The older I get the more I enjoy kissing for its own sake, the less I care about having an orgasm during sex, the less seriously I take anything to do with sex. I like this; soon I think maybe I will be ready to go to college and fuck my brains out. Except for being a creepy older guy, I would be much better at this now than I would have at 18.
23. A friend gave my ex and I an otter-shaped vibrator after we gave her an octopus-shaped one for Valentine's Day. I enjoyed using it on her but she became concerned that it desensitized her to tongues and penises and other more subtle stimuli. I experimented with putting it in my butt and found I could almost get it to reach my prostate, which gave me incredible orgasms. Then I broke its poor little rubbery head. You don't know what a dilemma really is till you are looking at a shitty broken otter head in the bath tub trying to decide what the fuck to tell its co-owner. I would have told her the truth, but I decided to clean it up, put it away and see just how long it would take her to notice first. I doubt she even remembers the poor little critter's existence.
24. When I was about 16, I was one of really only two hippy kids at my high school. The other was a mouth-watering girl one year older than me. I look back and realize that all those afternoons we spent hanging out at her place stoned she was trying to get naked and sweaty with me. I didn't think there could be any way she wanted to fuck me, but looking back the walking around in her underwear, leaning her head on my shoulder, telling me provocative stories...these were obvious signs. I really regret being too stupid and shy to fuck her brains out.
25. The last woman I really wanted to fuck turned me down for being too unforgettable. Not as in “You are just such an amazing person” but as in “You should have stopped talking awhile back and fucked me already because now I think I would like you too much to make it a casual thing.” I have a feeling that eventually I will make her eat those words.
