"We flirted, she put her hand on my leg, and we got off at her stop…"
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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.
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 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 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 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.
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 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.
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…"
For a year, I lived in Western Canada and wrote for a magazine. Lauren was the office manager. We got along immediately, laughing together in the frosty air and generally enjoying each other's company. She was sweet, laid-back, and beautiful, but not interested in the outside world, one of my prerequisites. I knew I would leave Calgary soon, and she did, too, so she ended things to avoid getting hurt. We're still friends and talk about getting together to rekindle our flame, but we never follow through. A great girl, and a great fuck.
I was twenty-six, and she was in her late thirties or early forties. A kind, divorced woman with a child, she was as uninterested in having a serious relationship with me as I was with her. She would come over, we would fuck, I would command her to tell me how much she loved my cock, and she would orgasm quickly. It ended when I left town, and that was a good thing, because I was getting disgusted with myself. I didn't want to touch a woman for months after. We're still on good terms, though. She just added me on LinkedIn.
Amanda and I met on J-Date and had sex on the first or second date. Once I mentioned my handcuffs, she wanted to come over. I believe I fucked her four times in one evening, a record for me. We hooked up a few times after that, but neither of us really cared deeply. She cut it off for reasons she never explained to me.
Woman in Springfield
When I moved to Springfield, I was on a casual-encounters site. The only black chick I've been fortunate enough to get with came over for what I thought was a friendly visit, but she insisted on having sex. (Okay, it didn't take much insisting.) She liked being called a slut, and I liked calling her one. She told me it felt good when I fucked her, and it felt good when she was on her knees blowing me. I never called her again, which I regret, because as I write this list I realize I've been unfair to people. I've always prided myself on treating women well, but I can see that that's only been true with girls I've really cared for. The stories we tell ourselves in order to live!
Kristina was the first Hispanic chick I'd dated. She liked me, but I didn't like her. I introduced her to D/S, and she loved it. Soon she was asking me to write dirty things on her body and take naked pictures of her; I generously obliged. I kept it going because she was soon departing for London, which gave me an easy out. We still stay in touch on Facebook.
I've never been more disgusted with myself; my one-nighters and casual women declined significantly after this. We met one night after emailing on a fetish site called FetLife. She wanted me to force her to do things while she struggled — slap her around, take it in different positions, etc. She lived in New York, so there was no chance of us dating, thank Christ. Even in play, I find forcing women to do things horrible.
Girl I don't recall how I met
We went out to dinner, she came over and had sex with me. She was vapid, and I was rapid. Never happened again.
Marcy was a pretty, intelligent early-thirties schoolteacher who, she told me, had never given a blowjob or been fucked from behind. She was into me, but I wasn't into her, so I ended things. She seemed bitter about it. I'm not sure why.
I met Rhianne on Fet, and it was the best kinky experience of my life. I got to try a lot of stuff we both wanted to — leashes, ball gags and the like. She started to like me, so I ended it. I'm not sure why I wasn't into it — she was hilarious and cute, with a killer body and smart things to say. But she took it well, thanking me for restoring her faith in men in casual relationships who would treat her nicely. I'm glad.
I've never wanted to like a woman so badly. But there was just no chemistry, no matter how hard I tried. The sex was good; she was into trying new things and wanted to be fucked well and often. I ended things when I just knew I could never like her. We're still good friends, though. She rocks.
I had pathetically not been in a real relationship for eight years (!) until I started dating Alex, two months ago. We met online, and I felt instant chemistry. She's smart but not intense (I am, and I don't want to date another me), beautiful, ambitious, accomplished, funny, fun, warm, and kind. But she also has a history of abuse, has been attracted to assholes, has cheated in the past, and spends money more easily than I do. I can see myself falling in love with her and getting married. Who knows?