Love & Sex

Everyone I’ve Ever Had Sex With: Male, 22, New York

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If there’s three things I love, it’s runners, redheads, and older women.

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I was twenty when I lost my virginity to Dianna.  Dianna was a little older, a triathlete and neuroscientist, and had played on the women’s team at my university before transferring to a school in the city. We’d been making eyes at each other before she left, but we never got farther than making plans to “hang out.”  One day, months since I’d last seen her, she sent me a Facebook message saying she was coming to visit campus and that she was staying with me for the weekend.  We made out in the library and then had sweet, tentative, inexperienced sex in my bed. 

Being athletes and knowing there is only one way to get better at something, we spent the next 48 hours practicing. We spent the next six months in a sort of open relationship; I’d visit her in Harlem, cook her dinner, fuck her on the fire escape, she’d visit me, we’d go running, have sex in the grass. Eventually the “casual” thing started to break down.  I’d call her late at night on weekends when we were apart and she asked me to go to Spain with her. Just as it seemed we were about to fall for each other, she moved away to grad school in the Midwest.  Sometimes I still daydream about her core strength.  

Finally losing my virginity after so many years of adolescent frustration really opened the floodgates. Sandra responded to an ad I posted on Craigslist for an “older woman.” She was 35ish, had a live-in boyfriend, and had me over to her swank house in the Catskills a few times. On our first “date,” we role-played me breaking into her house and taking advantage of her while she was asleep. Her boyfriend was listening on the other end of a baby-monitor downstairs.  It was hot, but I left feeling a little used for their cuckold fantasy.  I never called her after that.  


Anne was a tiny, waifish blonde dancer and one of the genuinely weirdest people that I’ve ever met.  She had just broken up with her long-term boyfriend, who had started serially sleeping with her gay friends, and she was looking for a rebound. I wasn’t attracted, but I was horny and amused by her. I sent her a text message that said “I’m down.” The sex was hilariously bad. Having sex with her was like trying to brush the coat of a hyperactive puppy. There was blood drawn and quite a few queefs. It was depressing at the time, but we’re still friends and we laugh about it.

Liz was a tiny, adorable brunette dancer and painter who I’d been crushing on since day one of college, when her towel-clad shoulders floated by my dorm room on the way to the shower. After two years of a tangled, intimate, tension-fueled friendship, when we finally started making out, something went really wrong. Things were complicated by the fact that I was still hooking up with Dianna at this point. 

It all came to a head one night when Anna called me in a tequila and coke-fueled haze begging me to come over and take her virginity, then threatening to do all the coke alone if I didn’t come. (On my way over, I got a text from Dianna, who was on her way up to visit me, asking me to fuck her ass.) I went, and she ripped off her clothes and latched on to me. She was very distraught, and I found it very sexy, but Nerve readers, I didn’t do it. I coaxed Liz down from her coke high, fed her and myself some more tequila, and brought her out to find her friends.  

After the debacle with Liz and Dianna’s subsequent moving away at the end of the semester, I joined OkCupid, looking to fuck indiscriminately and irresponsibly.  Andrea was not the kind of person I was expecting to find on the internet. She was 39, a married polyamorous mother of two, a college professor, and pretty well-known and well-published third wave feminist poet. I had read her work in some journals and she knew all of my poetry professors from school.  I’m not going to lie, this was a student-teacher affair beyond my wildest dreams. 

She took me to a poetics conference that she was presenting a paper at.  I followed her around from reading to reading, was rather vaguely introduced to all sorts of semi-famous writers, and then she took me to a hotel room, read me her erotic poetry, then we fucked for hours. In the morning, she gave her lecture about feminist poetics in my blue Oxford shirt.  I drove her to her house that afternoon and I met her husband and played with her two young kids. When I’m 90 and bedridden, this is the one I’ll be telling my nurse about.


After my dream date with Andrea, I became a slave to OkCupid.  Christina was a bored pothead who lived a few towns away. I wasn’t particularly attracted, but she messaged me offering to smoke me up and draw me in charcoal. We had sub-par sex in the loft of her barn and then never spoke again.  A few months later, I saw her in a webcam-capture porn video on a tube site.  

Nina was precocious, bored, and a hyperintelligent manic-pixie-dream-girl who turned out to be quite a bit younger than her OkCupid profile suggested.  But age is a watchword, right? We walked in the cemetery and talked about French poetry, then hooked up on the papasan in the basement of her parents’ house while they were at work.  I was really into her inexperience, the roots on her blonde dye-job and her long flowery skirts.  


If there’s three things I love, it’s runners, redheads, and older women. Which is why when I came upon the profile of a single, 39 year-old ginger-haired New Yorker and marathoner who was spending her summer up along the coast near my house, I had to have her.  She accepted my urgent OKC proposition message (I was leaving to return to school in a few days). I drove to her apartment, we drank a beer on her balcony, and she took me to bed. Man, you don’t know the meaning of “marathon sex” until you’ve had it with someone who’s running 70 miles a week.  I tried to fall asleep in her big king-sized bed, but she nudged me awake, got me dressed, put a beer in my hand, and sent me off into the night. We never spoke again, and I don’t remember her name. I hope she broke four hours and that she tells her friends about me.  


Molly was the last of the OkCupid girls, and she was sexy.  She had a pornstar body: super-tan, bald pussy, huge buoyant DD tits, and a round ass, and a serious sub streak. We spent the last few weeks of the summer hanging out, playing with her dog and having rough sex.  She liked anal, choking, and light punishment. I was eager to please, but trying to dominate a girl who has probably 25 pounds on you is a weighty task. We stopped hanging out when the semester started in earnest, even though she only lives five minutes down the road.  I should call her some time.  

I am very rarely spotted at college parties, but when I do go out, I always try to make it worth my while.  I picked up Kate at a rugby party and took her home at the end of the night.  She was blonde and had that downhill-skier pear shape going on. We had forgettable sex that night and average sex again in the morning. She was on her period and left garish streaks of menstrual blood in my sheets.  I made her a luxurious breakfast in the morning and sent her on her way. Her friends told me she was really stoked to have slept with the captain of the soccer team.