Love & Sex

Everyone I’ve Ever Had Sex With: Female, 26, California

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Trey and Laura
20 years my senior and married, we met on MySpace when I was 18 and looking for a band to play with. We became close friends over several months until they offered to rid me of my virginity curse. What was a ridiculous proposal at face value – lose your virginity in a threesome with a married couple twice your age – made a shocking amount of sense to me. By then I was 19. We spent the next 6 months having dates and traveling together discreetly. It was very sweet and there was a lot of love there. To this day, I still can’t say I’ve met someone who gave better head than Trey. I came out of the experience knowing that I wasn’t as bisexual as I’d previously thought, and that I wasn’t really into sharing partners.

James was a good friend of mine in college who I’d had a crush on for a while. He was a super-eccentric gentle giant with crazy blonde hair, a fiercely intelligent human being and a genius musician. He played games with me for a few months before we finally sealed the deal, and it was awkward to say the least. We managed to stay close friends for several years. He ended up developing strong and persistent feelings for me. I couldn’t reciprocate in good conscience, as by then he’d begun to spiral into the depths of bipolar disorder.

I met Denny on my 20th birthday, sitting out on the grass and doing homework, when he pulled his blanket up next to mine and struck up a conversation. He was 25 and a grad student, with an incredible body and a kilowatt smile. When we kissed in the park on our second date, he told me he wasn’t looking for a relationship. For a month, we would go to his loft in Bushwick and fuck. His dick was the biggest I’ve ever seen, but the sex was pretty average. It turned out he didn’t want a relationship because he already had a girlfriend, who he ended up marrying. It was always a little awkward when I saw them around town.

It was the middle of the semester and I had spent my entire Sunday cramming in the library. I was just walking back to my dorm when a guy coming from the other direction asked me, in a London accent, if I knew of any good places to get a drink, and invited me to go along. He looked like Damon Albarn and I grilled him about Britpop. We got pretty drunk and I took him back to my dorm room, where we fucked and fell asleep. In the morning, I realized the condom had broken. He offered to pay for half of the Plan B, but never did.

Mauricio had a great name. His dad was from a wealthy Mexican family with a super aristocratic surname that was like five words long. He was a composer pursuing his doctorate. He eyed me for a few months during my shifts in the campus music library, finally asking me out to a show when he realized we had the same taste in music. He was a fun guy to hang out with, but I dumped him after three weeks because he was by far the worst sex partner I’ve ever had. And he always kept his socks on, a habit I hate with a passion.

Charles was the lead singer of a band my friends and I were really into. I was kind of shocked when I went to one of his shows and he began hitting on me really intensely. He was classically handsome and incredibly smart, so it didn’t take me long to reciprocate. Things were really hot for a few weeks, but it went downhill fast and we broke up after two months. After six months of me feeling angry and sad, we ended up being pretty good friends.

I was so upset after breaking up with Charles that I didn’t have sex for a year. Enter Kenny. Kenny grew up on a farm in Iowa and played varsity football in high school. This was novel to me. Archival photographer by day, talented painter by night, Kenny and I met through mutual friends at a Wooden Shjips show. We spent the entire night ignoring each other until he offered to share a cab when the night had come to its predictable end (friend puking all over herself and getting us kicked out of a bar). At the end of the ride, I practically begged him to take my number. We were off on our first date a couple of days later. We dated for three months, and the sex was predictable but very fun. He was unfailingly kind and had his shit together, which was a huge turn-on initially. But he was 14 years older than me, and I had just graduated from college, and it became clear that it just wasn’t going to work out. I still miss him.

The first guy I slept with who was my own age. Andrew and I were classmates from kindergarten to 4th grade, when he moved to South Carolina. In college, I found him on Facebook and discovered not only that we had a lot in common, but that he had morphed from a hyperactive child with a severe speech impediment into a smoking hot astrophysicist with great taste in music. He lived in nearby Boston, and over several years we made a few aborted attempts to hang out. It finally happened at age 23. It did not take a lot of effort to get him in my bed. The sex was disappointing but when he left in the morning, he kissed me so passionately and impulsively in the stairwell of my building that I’ll never forget it. I went to visit him a couple of months later in South Carolina, where he pulled a Jekyll and Hyde and became a massive dick. He’d started seeing someone else and was too chicken to flat out tell me.

It’s my first day working at an arts camp outside the city, and I’m assembling a salad plate in the mess hall. I’m interrupted by Brian, who ‘helpfully’ points out that the tip of the salad dressing bottle I’m about to use is clogged. When I finally turn to look at him, I’m immediately smitten (our conversation, reduced to its subtext: oh, hello. I think we can both agree that we will one day tear each other’s clothes off). He’s half-Mexican, with golden skin, dark hair, and beautiful hazel eyes, one of which is made of glass and droops visibly (his glass eye ends up being something that makes him even hotter to me). He’s funny, speaks slowly, has a great laugh, and is aloof in a way that is simultaneously frustrating and alluring.

I’ve never been so immediately, viscerally attracted to someone as I was to Brian. He made me feel like a stupidly lovestruck seventh grader. It took the entire summer for us to hook up, because as it turned out, we were both pretty damn nervous and shy when it came to each other, which, in hindsight, was kind of cute and made the buildup that much more exciting. When we did finally have sex, it was fucking awesome, but it only happened once at camp because he had taken some other girl’s virginity earlier that summer and she was upset that he was seeing me.

Nikhil and I hooked up once in the month between the end of camp and my trip to see Brian in LA. We were coworkers in the music library one summer. I was really looking to get my mind off of Brian until I saw him again, so I logged onto my long-defunct OKCupid account and starting looking through matches. Nikhil popped up and was a 96 percent match, so I messaged him and was like, ‘Hey, I know you’, and we went out to a bar the next night. We had fun and ended up making out passionately on the waterfront. When we went back to his place, though, he showed no interest in getting me off. I wasn’t cool with that and declined his invitation to a second date.

Martin was a super nerdy engineer who lived on my floor my freshman year of college. We became pretty good friends, and even though he was totally not my typical type, I was always attracted to his self-actualized confidence and kindness. I harbored my crush on Martin for years while he went through a couple of long-term girlfriends. It had been a few months since I’d last seen Brian, and I was really beginning to feel the dry spell. I asked Martin to go see the Lemonheads with me, a band he knew absolutely nothing about, and we flirted and held hands after we’d both had a few drinks. When we began making out in his bed later that night, I explained that he shouldn’t expect it to go anywhere, which he was totally cool with, and we had an okay time together. Not really compatible sexually, but he was kind and caring and got me off.  I forgot my underwear when I left.

Jim was a comically attractive model from Nova Scotia who lived in my neighborhood. I played a show at the bar where he worked, and though I had definitely noticed him, I was firmly convinced that he was well out of my league. But a few months later we hung out again and had drunken sex on the bunk bed he and his roommate shared – while his roommate was sleeping on the top bunk. I was pretty mortified afterward but they were both cool about it.

Ugh. George. What on Earth was I thinking? Why did I date him for nine months? And why did we live together? I was only ever mildly attracted to him, at best. There was a long stretch of time when I genuinely liked him. But I was beginning to get tired of being broke in New York and wanting to progress to some slightly more adult phase of life. When I realized that my boyfriend was a clingy man-child with no similar aspirations and that nothing was going to change were I to stay with him, I knew it was time to finally follow through on my years-long desire to get out of New York. George said he was cool with it, but he didn’t handle it well. After I refused to live out our post-relationship ‘relationship’ on his terms, he began to act passive-aggressively, culminating in the destruction, via USPS, of a bunch of my stuff. I eventually had to tell him to stop contacting me.

Abelardo was a beautiful Mexican exchange student almost four years my junior. He had the most amazing hair I’ve ever seen on a guy, long and light brown with natural blonde highlights. Playful, funny, whip smart, and a little cocky, we immediately clicked despite his imperfect English (but impossibly sexy accent) and propensity to overshare. We met at the same camp where I’d met Brian and started talking about halfway through the summer. I didn’t want to make the same mistake I’d made with Brian of waiting too long, so after about a week of hanging out late at night smoking weed and playing guitar, we kissed while sitting in his bed. After getting off to a bumpy start sexually, we hit our stride and spent the rest of the summer fucking like rabbits, developing feelings for each other despite our mutually agreed upon nonexclusivity.

When camp ended, we used up the rest of his visa taking a roadtrip to California, stopping to have playful, kinky, athletic sex in dozens of hotel rooms along the way and generally getting too close for a relationship whose future prospects were nebulous at best. Saying goodbye was hard, the word ‘girlfriend’ was thrown around once or twice, and we’ve stayed loosely in touch. In two weeks, we’ll both be back at camp again, so we’ll see what this summer has in store for Abelardo and I.

Wendell was a Craigslist casual encounter that I invited into my hotel room on the way home from SXSW, where I’d flirted with a few guys but accomplished nothing. The opportunity presented itself, and it was long past time to break my post-Abelardo dry spell. He was cute and we got along well. He was a musician from LA who made ends meet as a traveling rug salesman, which was why I had found him there in Beaumont, Texas. Toward the end of the night, after a very long and interesting conversation, he nervously confessed that he was 35, not 33 (as he had indicated in his listing). We hooked up again about a month later when he drove through my town. He still drunk texts me occasionally, even though he lives in North Dakota now.