Love & Sex

Fifteen Stories: Memorable One-Night Stands

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Hooksexup readers share stories of scandal and adventure.

We met at a bar. He was very upfront about telling me that he had a boyfriend… until two drinks in, when he was asking me to leave first and meet him around the corner. He was Swedish, hung like a prince, and had a beautiful bed with giant city-view windows. Somehow, he knew to be just the right amount of dominant, knocking me back and holding my head without ever freaking me out or seeming mean. When I left, feeling like a joyful, wrung-out rag, he kissed my forehead and said, "That's the most fun I've ever had in two hours. I hope I never see you again." — Kevin

 

I met Pablo while on a Mediterranean cruise with my extended family. The tall, smug Uruguayan was the bartender in the Schooner Cocktail Lounge, which, not coincidentally, became my favorite bar on the ship. One night, my cousin and I took our grandfather to visit for post-bingo drinks. Laying on the charm, Pablo put his arm around Grandpa's shoulder and stage-whispered into his ear: "You have beautiful granddaughters. You better watch them."

"And you," he said, clutching my hand in both of his with mock gravitas, "you stay out of trouble." I nodded and discreetly stashed away the note, bearing simply a time and a room number in the crew's quarters, that Pablo had slipped into my hand. Duly impressed, I let Pablo show me his other tricks later that night. — Jess

 

I experienced only one free year between losing my virginity and meeting my long-term partner, during which time I only had one one-night stand (and I managed to sneak it in a mere week before meeting said partner, at that). He was a sexy Ukranian import with a wicked sense of humor and a great body. It was fun and casual and we never bothered one another again.

I'd established one rule for myself in that one-year period: never sleep with someone whose last name you don't know.  I remembered this rule moments before the act, pushed against his chest, and yelled, "Stop! What's your last name?" I haven't forgotten it since. — Morgan

 

It was my first night living in a new city and I was at a party at a friend's place. One of his friends had been flirting with me all night, but it wasn't normal flirting — she wouldn't say a word to me. She'd only touch me and giggle as I walked by. Towards the end of the party, she took my hand and quietly led me to her room, which, oddly, didn't seem to have a door or a bed — just a bunch of clothes everywhere. Less than sixty seconds into making out, she started to go down on me. Which I accepted. I realized how creepy and weird the situation had been to that point, but it was head. What twenty-four-year-old dude turns down head?

She finished up, and put her head on my chest to rest. At that point, I was thinking this girl was a loony tune, but I didn't want to be an ass, so I began to reciprocate. But she grabbed my hand and stopped me, and said, "Sorry, I have a boyfriend and I wouldn't feel comfortable doing that." I looked at her totally dumbstruck. She must have misinterpreted my dropped jaw to mean that I was hurt, because she immediately came back with, "But it was really nice sucking your cock." These were the first words she'd said to me all night. — Steve

 

While at a bar one night, I ran into Abe. He was this hot guy from a class I was taking, but I had never talked to him because I was too shy. After quite a bit of vodka, I decided to dance with him. Instead of asking him to dance like a normal person, I slid my hands into the back pockets of his jeans and pulled him down off the stage. We danced together for the rest of the night. Turned out to be the best sex I ever had! — Melissa

 

I had a one-night stand with a Freemason. It seemed like one of those things a person should cross off her to-do list. He was sweet, if a little socially awkward. (Though, "socially awkward" in my book = "clean.") Anyway, it was terrible. He was a two-pump chump, and then just kept wanting to get me off, when I just wanted him to leave. Also, every time he touched me he would whisper, "Give me that come." That was the last thing I wanted to do. He was probably going to use it for some Freemason ritual or something. — Jessica

 

I met a girl at a house party. We went to her house, got naked, and had sex. After we finished, she proceeded to tell me that she had a boyfriend whom she'd dated for seven years. She also said that I should get dressed and get out cause he'd texted her and said he was on his way. I couldn't leave through the front door without risking bumping into him, so I had to leave through her window. She had a very large house, and she lived on the second floor. — Jay

 

My own one-night-stand stories are pretty boring, but when I studied abroad in London, my roommate had plenty of adventures. She'd bring a different man back to our flat every week. Almost all of them were bartenders, many of them Brazilian (which was strange, considering we were nowhere near Brazil — two of them were named Joao). Many of them she'd meet at gay bars — they'd be the one straight man there. I think my favorite of her hookups was Joao, the bartender. After their one-night stand, he began to act really strange and jealous. According to my roommate,  this was because Joao could "astral-project," and he had astral-projected his soul into the room while she was with someone else — she could feel his aura — and got jealous. — Adina

 

Most of the internet dates I went on didn't lead to anything, but there was one that I really hoped would. From the first moment of this date I was charmed. We stayed out late into the night drinking, playing darts, and getting to know each other, and our chemistry and inebriation brought us past the normal first-date boundaries and into her bed. I figured there was no way this would be our only date. But in the middle of the act, she must've felt self-conscious for a moment, because she asked me, "What do you like about me?"

It was my chance to tell her how great a night it had been. How welcome and warm she'd made me feel right off the bat, and how badly I hoped we'd hang out again soon. But I didn't. My drunken brain went somewhere else. I thought I was being funny and that she'd know I was parodying a less sensitive man than myself. So I said, "Your boobs." Silence followed. It was exactly what she didn't want to hear; she rolled over and put her face in her pillow. I didn't know if she was awake or asleep. I lay beside her for what felt like a wordless eternity before asking if she wanted me to stay. She shrugged. I left. After the third or fourth unreturned phone call a few days later I began replaying the end of the evening in my head and understanding where I'd gone wrong. Over five years later, I still think back to that night and wonder how different my life might be today if I'd answered one question differently. — Paul

 

Practically a mail-order one-night stand. A friend of mine from Denver asked if I would show his new Australian friend around NYC. Being the kind Midwesterner that I am, I said I would. Boy, am I glad I did! This man was beautiful, and the accent didn't hurt either. His time in New York was spent mostly in Queens and not very far outside of my bedroom. Wait, does a one-night stand have to be just one night? Because sex was amazing enough to repeat on nights two through six before shipping him back down under. — Raydene

 

New Year's Eve, Mexico, two-for-one margarita specials at every bar. I was nineteen. I saw him and I knew I wanted him to be my New Year's kiss; the kiss turned into jacuzzi sex in a stranger's hotel room. The following morning I invited him to drive farther down the coast with us for lobster. Then I ran to my friends and insisted we leave fifteen minutes earlier than I'd told him to meet us. I never wanted to see him again, even though it was good sex and he was a sweet guy. It was my first one-night stand. A couple months later I got my disposable camera developed, and there he was. It was all the evidence I needed. — Chloe

 

I was in the lone gay bar in my Midwestern college town, drinking with friends and waiting for something interesting to happen. Eventually I noticed a guy who was looking at me a little too deliberately, and I sensed an opportunity. We start talking and drinking and laughing until he paused and asked me, out of nowhere, "Do you want to come back to my place and watch Whitney Houston videos?" I agreed immediately. We watched Whitney's greatest hits, and the sex that followed was fine, but that remains the single best pickup line I've ever heard. — Paul

 

A few years ago I ran into a friend/employee of my ex-boyfriend, whom I'd dated long-term and lived with. This friend and I were both very drunk. He lived out of state, and was in the middle of touring with my ex's band. The rest of the band had crossed over into Canada, where he was not allowed thanks to a DUI. Toward the end of the night, I agreed to go back to the place he was staying, and we wound up having sex on the couch. I fell asleep. When I woke up, I looked at the pattern on the couch. Incredibly familiar. I rolled over and recognized the table, the TV, the glasses on the counter — I was in my ex-boyfriend's new place. The shock must have been obvious, because the guy was like, "Hope that's not too weird for you." After fighting the urge to steal back my wine glasses, I drove the guy to the alcohol-awareness meeting he was court-ordered to attend. Class. — Jenny

 

I had just returned earlier in the day from a lackluster visit to a long-distance boyfriend in Vegas. I was at a gathering of friends who introduced a tall, handsome man visiting from out of town. After a quantity of liquor that would have brought down Andre the Giant, Tall-and-Handsome and I somehow made our way up the ladder to my loft bed. Drawing from a script reminiscent of a bad Cinemax soft-core, he was over-enthusiastic and I underwhelmed. The best part is, a handful of years later, I repeated the situation almost exactly — with the guy's brother. — Sarah

 

We had been having sex for a couple minutes when I looked down and discovered that he was playing with his broken iPhone. With this revelation, I dismounted, ignored his pleading, and passed out. — Jen

 

Submit to our next round-up: People I Never Intended to Sleep With. Everyone should dream big. We want to hear your stories about people who you didn't mean to give the time of day, who somehow managed to charm their way into your heart/bed. Send us all the hilarious specifics in 300-500 words to  or click for more details

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