Love & Sex

Fifteen Great Moments in Sex

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Nerve readers share the highlights of their sexual careers.

Last summer, I was working a huge concert festival on Governors Island. An ex-girlfriend and her new girlfriend were there because I’d put them on the VIP list. It was an extremely grueling day, busy and nearly 102 degrees by midday. When I got a text from my ex saying her new girlfriend thought I was hot and they had both eaten ecstasy, I told my boss I was going on walkie silence for an hour. We left the concert venue to retreat to the hammocks at Picnic Point. For an hour we could hear Sleigh Bells in the background as the three of us took sweaty and naked to the summer evening. The great moment came when two fifteen-passenger vans drove past and honked, with one of my colleagues yelling my name and clapping out the window. — Nicholas


My new girlfriend and I were at a summer party one night on a rooftop. For whatever reason, I’d been insanely horny — walking around with half an erection — for hours. When I finally grabbed my girlfriend and slid around the corner to take care of it, I was nearly running to get my pants off. When I came, I closed my eyes for a second and half-passed out. It was so good I actually fell down, bare-assed, onto the gravel of the roof and sprained my wrist. — Donald


My best ever sexual moment — which definitely belongs in the humor/irony category, occurred while I on the phone with my aunt. She was giving me a lecture that could have been summed up as: "It's okay to like girls, but don't you think life would be easier if you liked boys?" This was funny, because my girlfriend was going down on me at the time. — Jessica


It was an affair. No two ways about it. I was studying abroad in Argentina, boyfriend back home. The whole program got to go on a trip to this idyllic little inn in Uruguay  —everyone sleeping three or four to a room. Except for me and James — a boy I’d had my eye one. We were paired alone, in the most spectacular room in the place. The best moment was when we opened the door, suddenly alone, and both realized what was going to happen. Illicit sex and vacation sex are the two best kinds of sex. That night, I got to do both. Twice.  — George


In boarding school, a guy named David climbed out his window, along a ledge, and woke me up by knocking on mine. We climbed together up the fire escape to the roof, and had the craziest sex of my life, looking out towards the woods. It was my first time. — Steve


I was with my boyfriend in a hotel during his family reunion. We didn't have our own room, but I noticed there was an extra key to a room that some of his relatives hadn't checked into yet. I grabbed the key, and told my boyfriend to meet me in room fifteen. He walked in and I was naked on the bed waiting for him. The excitement of possibly getting caught was an amazing aphrodisiac and we ending up coming at the exact same time in under five minutes. A real feat, I'd say.  — Samantha


I was at camp the summer before my freshman year in high school and I started hooking up with my Quaker camp counselor. We made out a few times and I gave him a successful handjob, but the real magic happened one night, when I was sitting on a table and he gave me my first orgasm. All I can say is that he was very good with his hands. — Kaitlin


I went for a snorkel with my old boyfriend, off a sailboat moored near a Caribbean island. The sun was setting. We turned a corner and were just out of sight of the boat (with parents/friend/his siblings, etc.), when I stripped. He followed suit — he was wearing trunks, I was in a bikini, so it wasn't all that hard. Then we boned in the shallows, fins still on, masks pulled down. Not the best sex ever per se, but definitely among my most memorable moments. No aquatic animals or corals were hurt during this exercise. — Lindsay

At the end of my junior year of high school, I developed an inexplicable crush on a nerd in my physics class. He was a year younger than me, with glasses and braces, but a nice face and strangely muscular arms. Even though he was a nerd, he was really funny, which made me feel incredibly nervous. It wasn't until over the summer at a house party in the middle of nowhere that I worked up the courage to make a move. After talking all night, I pulled him into my friend's empty car and straddled him. We starting kissing just as it started to pour. It's a huge cliche, but that's probably why I never forgot it. — Megan


He was sort of rugged, young Paul Newman-esque, drank Budweiser and smoked Marlboro Reds. We met at a friend’s party and, at 4 a.m., were the only two awake and went looking for a place to "sleep." Finally, we decided the small entryway by the back door was our best option, and my partner procured what appeared to be lawn furniture cushions from the back of his car, and some towels. This gallantry ended up backfiring when, mid-coitus, I realized we were doing it just like Sarah Silverman and Matt Damon — "on the floor, on a towel by the door" — thereby throwing both of us off with my subsequent uncontrollable giggling. Hot. — Rachel


Quiet weeknight chill sessions can really get out of hand given the right ingredients. (This is especially true when your friends are hot and you wouldn't mind touching their bodies.) For instance, given a healthy supply of Four Loko and a bottle of rum, four friends can turn into four naked friends in a bed pretty quickly. Now I strictly call four-ways "Four Lokos." — Baron


The Empire Hotel lobby bar was playing terrible music, so we left and went exploring. We weren’t guests, but managed to slip by the guard and out onto the roof. We tip-toed around but it was all quiet. I pulled her into the furthest cabana from the door and sat down on a lounge chair. I started kissing her through the material of her skirt, then lifted it and went down on her. She had a cocktail in one hand, my head in the other, and started moaning quietly. She's usually very loud, so the silence was a huge turn on for me. She came and a few minutes later, returned the favor. We smoked three or four cigarettes on the roof, in the peaceful darkness. — Greg


In general, you don't go to a gay bathhouse called the "Pleasuredrome" to have sex with someone who's already your boyfriend. But when you go at 4 a.m. on a weeknight, options are limited. The night, however, turned out well. The moment I remember is looking up to realize that, unknowingly, we’d amassed quite an audience. It's very liberating to have sex in a semi-public place without worrying about the cops. (Or cleaning up.) — James


Apparently, in New York Oktoberfest means “feel free to dress like a Centurion.” One night, my (absurdly gorgeous, former-model) personal trainer and I drank innumerable pints, a handful of shots, and in the wee morning hours as we wobbled toward his apartment he whispered into my ear what he wanted to do to me, but that we couldn’t go into his apartment. (In retrospect, it wasn’t clear why.) He guided me into the stairwell. It wasn’t your typical up-against-the-wall affair: I woke up with bruises on my spine and the backs of my legs from having sex completely naked on the stairs… and the bare floor. — Sarah


My roommate and I were super-depressed and were both having months-long dry spells. We felt like shit and we fought all the time. Then a friend invited our silly cover band to play a party at his house. So the two of us and our bassist drove over there and our friend introduced us to his five beautiful female roommates (!). We played an unusually great show, and then we both got laid in adjacent bedrooms, which was really incredible because independently we'd been batting zero for an outrageously long time. Rock music. — Paul