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We met at a New Year’s party in high school and in two and half years, he went from being my first real kiss to my first sex. I grew up in a very Catholic family and had always planned on being a virgin until marriage, but then college happened and I decided I want it to be with someone I trusted and kind of loved instead of drunk with a virtual stranger on campus. He said all the right things — told me he loved me, etc — and was very gentle about the actual sex. Which happened on his living room couch, while his mom slept upstairs. It hurt so much initially that I almost backed out, but by the end I kind of enjoyed it. We slept together a few more times before he drifted out if my life forever, but it was always incredibly awkward and not terribly enjoyable. We were much better at making out.
My first musician. I met him at a Christmas party on the campus of a nearby arts college where he was ironically on the baseball team. He complimented my red dress and gave me his number when we shared a cab back to the dorms. I couldn’t sleep and ventured down to his room at 3 a.m. where we had aggressive, drunk sex. I left before he woke up,
Also at the arts college, but this guy was on the lacrosse team. He was a shy, skinny, bearded guy from Vermont who once quasi dated my friend at that school. He was borderline obsessed with her and as we arrived at the party, she said: “I’m getting so sick of Josh, can you please take him home and get me out of his system?” I obliged after some tequila and found that he was just as shy in bed. I also found that I really like being fucked with my legs over my head.
We went to senior prom together in high school and I had a consuming crush on him for about a year and a half. We only kissed/groped in high school, but at the end of our freshman year of college we somehow ended up super drunk at my parents’ house fucking with reckless abandon. This was terrifying to both of us in the morning and we agreed it wouldn’t happen again, though it did several more times, culminating in quite the New Year’s Eve where I ended up having to take Plan B. Three and half years and a few long term relationships later, we met up for drinks when I was back in Boston and he shyly asked me to stay the night. God bless his ex-girlfriend, because the mediocre lover I remembered turned into a very skilled, very generous guy in bed. First and only to use handcuffs on me. We were both shocked by how much better we had become in bed and high fived in the morning.
Friend’s ex boyfriend. Lots and lots of body hair. Liked to pick me up.
Oh Alex: He had dated and hooked up with a few of my friends already when I was introduced to him at a party. I don’t remember what we talked about, but I do remember that less than an hour after meeting him, I was blowing him on my best friend’s bedroom floor. We continued to have sex on and off for the next two years and though as an adult I’m not even attracted to him, he’s wrecked me a little bit. We’re still friends now and it’s always in the back of mind — what if it had been something more?
I met him on a pub crawl in Dublin spring break of sophomore year. He was 27 and I was 19. First adult man I had fucked and consequently the first to very enthusiastically give me oral sex. I’ve been ruined ever since. He wrote down his e-mail in the morning but I wouldn’t give him mine.
We knew each other through a theater group in college. He reminded me very much of Ben physically, which I think is why I didn’t mind that he was certifiably (get arrested) crazy. Crazy meant rough, gymnastic, marathon sex, and my 20 year-old self loved every minute.
I met him at a bar downtown, three weeks after I turned 21. He had a charming smile and was an excellent dancer. A few hours later, he sexually assaulted me and it broke me for quite a while. At this point, I can say that I’ve healed from the experience, but it has definitely shaped me and factors in the way that I enjoy sex now. Group therapy was the only thing that saved me, and helped me come to the realization that what happened to me wasn’t sex — it was violence. That said, the fact that I enjoy borderline rough sex now is a little confusing.
The first person I slept with after the rape. He had been a friend for most of college and I never really thought about him in a sexual context at all until one night at our party. I didn’t tell him that he was the first in quite a while and it was all very normal and slow and helpful. Unfortunately, he would be the first of many insignificant guys that semester — in asserting that it was my choice, I couldn’t stop choosing.
One of the most attractive men I’ve ever slept with. On the floor of my apartment living room, while all of my roommates slept upstairs. It happened a few more times, and each time I was almost too distracted by how pretty he was to enjoy myself.
Erik’s roommate. A little bit out of spite. Very drunk. Twisted my ankle on the way home.
Literally a foot taller than the first Alex. We went to middle school together and after reconnecting on Facebook, met in New York City to bang, er, remember old times. He’s from Rio, and is the first and only non American I’ve slept with at this point. The sex itself was very slow and sensual and full of intense staring. He made all of these grand statements about how beautiful I was and as much fun as I had, the whole thing felt kind of ridiculous and contrived.
I met Sean freshman year of college, made out with him junior year, and we finally had sex at the end of my senior year. He’s lovely — we always got along really well and he made me laugh to no end. Much like Ben though, the kissing was better than the sex. I liked him a lot and embarrassed myself when I drunkenly made a few jealous comments to him at a party later on.
The first person I slept with when I moved to D.C. He impressed me by taking me to an obscure concert on our first date, and out of appreciation, I brought him home. Like Sean 1, we got along really well, but weren’t really compatible in bed. He was really, really, really into dirty talk. Needed a monologue as we were fucking in order to get off. It’s a shame, because the sex itself was pretty great, but I prefer not to have an in depth dirty conversation during. I gave him three more dates to figure out that I wasn’t into quite the same thing, but he only got more vocal.
Surgical resident at the hospital next to mine. Very handsome. Very, very timid in bed.
Harvard doctoral student studying one of my favorite authors. Slept with him the week my best friend died, mostly out of distraction. We met at a bar on Harvard Ave and danced all night. When it was time to leave, my friends wouldn’t let me go home with him, so I told him my address and lo and behold, he showed up on a bike 20 minutes later. Great calves and gorgeous green eyes.
We lived down the hall from each other senior year but didn’t meet until spring break in Cancun when we almost got arrested for getting naked and (almost) fucking on the beach. I ran into him a few times in Boston and called him when I was back for Anna’s funeral. Sex is the best medicine.
Met him online. He was very worldly and adult and I did like dating him, but he seemed to have a bit of a complex in bed. Much preferred going down on me to actual fucking which was great for a while, but it does get old, believe it or not. I found out after we broke up that he had been married before and never told me.
A 21 year-old intern. Terrible life choices, but the biggest cock I’ve ever seen to date. He was very sweet but it felt like a quarter life crisis on my part.
The chef of a popular D.C. restaurant. He’s in a relationship but has been eying me since I moved here and started hanging out at his bar. One night we shared a cigarette in the alley outside and he asked what it would take to come home with me. He dominated me in bed and though I had a handprint on my ass in the morning, I was surprised by how much I loved it.
My old roommate. We never spoke while we lived together, but he wandered into a bar I was at one night and I woke up in my old apartment the next morning. Really fun, but obsessed with one position I’m not terribly fond of.
Currently dating and happy on all counts. He’s very trainable.