Everyone I've Ever Had Sex With: Male, 31, New York City

"We flirted, she put her hand on my leg, and we got off at her stop..."

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Laura

Laura and I had been together for six months when we had sex. We were in love, passionately and reliably, after meeting at Jewish summer camp. She was sweet, smart, beautiful, and easygoing. We were naked one evening in my bed when I slipped in her, a genuine accident. I asked her immediately if she wanted me to stop, and she said no. I'll never forget the sight of Laura bouncing up and down on top of me, leaning over to kiss me and tell me she loved me. It was as great a first time as one could hope for.

Ilene

A few weeks after Lauren and I broke up, after two years of a great relationship, I was hurt and determined to prove my manhood. Ilene and I only had a single session. The first time I fucked her, I came in literally ten seconds. I told her I just needed time to recharge. I then proceeded to fuck her again, and again came in two seconds. She soon got back together with her ex-boyfriend, which I encouraged because I knew we had no real connection. We later got in a fight and she told me I "sucked" in bed. I did.

Shawna

Shawna was easily the worst sexual experience of my life. She was unresponsive and boring; still, I did her again, because, hell, it was better than nothing. We remained friendly after, as I am proud to say I have done with most of the women on this list.

Jenny

Jenny was smart, easygoing, and kinky. I ate her out while she lay on a pool table, which wasn't sex but is still cool. She was great in bed, loving dirty talk, having her hair pulled, and being spanked. But she was big and not good-looking, and I was shallow and flaky with her. Later, she married an Orthodox Jewish guy.

Chloe

Chloe loved me when I was in the throes of a terrible anxiety disorder and depression, and I'm forever grateful to her. She was also a great fuck, and the first girl to tell me she liked being called a whore, which lit a fire in me for D/S that has yet to go out. I am ashamed to say I did not treat her as well as I should have, leading her on to think that I would be in a relationship with her. The fact was that I often felt gross after fucking her, my first realization that I wasn't crazy about fucking someone I didn't have deep feelings for. She, too, is married now. We talk once in a while.

Marissa

I took Marissa's virginity, basically because she wanted to get rid of it. She's the only selfish lover I've ever had, but she was hot and I gave her her first orgasm, a nice feather in my proverbial hat. Marissa was not a nice person, but she liked me. And I was flaky with her, too. I don't get mean in the sense of insulting and angry, but I'm not proud to say that I do get flaky, and hook up with girls whose feelings I don't reciprocate. I've gotten better with that. We lost touch for a few years, but I called her up the last time I visited Washington, and we had a great lunch. She is happy, and hopefully we'll remain in touch.

Meaghan

Meaghan was the first, and so far only, woman I thought I could marry. She was so basically decent that I'll never stop loving her. Her downside: she had a bad eating disorder and got depressed. It still brings water to my eyes to think about how she was suffering. After six months, I broke up with her because she wasn't Jewish, and my parents wanted me to marry someone Jewish. They'd sacrificed a lot for me, and I felt it was my duty to do what they wanted. Meaghan and I continued for another six months, so deeply in love and unable, or so I thought, to end up together. It was a fucking terrible mistake on my part, and I've regretted it ever since, eight years and running. I learned my lesson to live my own life. She's married and, from what Facebook suggests, is happy. That gives me both a deep contentment and a profound sadness.

Woman on subway

I was on the subway in Toronto, visiting my friends for a poker game, and a thirtysomething woman saddled up to me and told me I was great-looking. "You must get that a lot," she purred. (I'm not, and I don't.) We flirted, she put her hand on my leg, and we got off at her stop. I called my friends and mystified them by telling them I wasn't coming over. They were worried when I wouldn't explain the reason for my absence. My best friend asked over the phone, "Are you being kidnapped? Cough if you are being kidnapped." I reassured them, and went over to the woman's house. (I don't recall her name). She loved to suck cock and take it in the ass, and gave me a rimjob. We talked about speaking again but both knew it would never happen. This is when I realized I was a crazy motherfucker when it came to sex.

Thai woman

She was a masseuse, and I was walking by her shop. I went in and flirted with her, and somehow convinced her to come to my villa. She whispered passionately in my ear in Thai, which of course I didn't understand but found hot. We might have done it one other time before I avoided her until I left the island after a few days.

Kinky woman #1

I met a late-thirties woman on a kinky site. She came over. She was poly, and I was not. It was a one-time thing and a terrible experience.

Kinky woman #2

I met this woman in the same way I met the previous lady, and I was disgusted with myself in the same way. She squirted when I was fingering her while she sucked me off, and, I'm sorry, I found it gross. Also terrible, and also a one-time thing.

NEXT: "I didn't want to touch a woman for months after..."

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