Sex & Relationships

The Most Awkward Sex Ever? 8 Epic Holiday Hookup Tales

"I asked if he wanted to have sex — while he was talking about his dad having a stroke."

Photo Credit: Maksym Poriechkin/Shutterstock

It happens to the best of us: Home for the holidays, overwhelmed by clucking family members, one thing leads to another, and we hook up with people. Exes. Old friends. New friends. Neighbors. These sexual experiences happen for any number of reasons — curiosity, stress, desperation or straight-up opportunism — and are, so often, totally regrettable. But they are almost always hilarious.

Salon recently asked friends and readers for their most memorable holiday hookup stories. Below are amazing amazing anecdotes that run the gamut: Sex with an ex in his little brother’s bed. A bloody first time with a virtual stranger. The inadvertent taking of virginity. Each is as cheery as it is awkward.

Happy holidays, and enjoy:

(Editor’s note: The following responses have been lightly edited. Subjects’ names have been changed.)

1) The bloody sucker

Like many young ladies, I went off to college a little more demure than some of my friends. I had boyfriends in high school, but I had never looked a penis directly in the face. It was harder to meet people in college, though, so when I went home for winter break freshman year, I decided just to get it over with and lose my virginity to a guy there – preferably a boy I never had to see or talk to again, which would be a relief to me.

Late one night I got a text from Jack, a guy I had worked with at my shitty retail job the previous summer. We would flirt all the time, but had never seen each other socially, or at all outside work for that matter. We made plans to meet up later that night. Once I got to Jack’s house, it was only a matter of minutes before he was pawing at me vigorously. He picked me up and tossed me onto his bed, which I found to be hot, and tried to suck various pieces of flesh from my body, which I found to be aggressively un-hot. He pulled down (not off) my panties and shoved his whiskey-dick into and around my vagina. I wasn’t sure he was doing it correctly, having had no point of comparison, but it didn’t matter — less than two minutes later, it was over.

I went into the bathroom and peed, and saw, to my horror, a toilet bowl and a piece of toilet paper that couldn’t keep a secret. So. Much. Blood. It was like I’d gotten my period, but I knew I wasn’t due for another couple weeks. I came out of the bathroom mortified and apologized for having bled on him. He said, “Oh, that’s OK, I fell down a lot as a kid and I’ve gotten really good at getting blood out of my clothes.”

2) The mood-killer(s)

There was this guy, Adam, that I was friends with since I was 14. In college, we stopped talking, but one year, after I had just broken up with my boyfriend, Adam texted me to see if I was in town. I was incredibly depressed about the breakup and figured having sex with someone would make me feel better. I asked Adam if he wanted to meet up and he said yes. I went over to his parents’ house while they were gone. We smoked pot and had terrible conversation– not like we usually had. We got along great before I decided to be gross.

Anyway, I asked him if he wanted to have sex while he was talking about his dad having a stroke. It was a pretty bad time to ask that, but I was totally and blindly selfish at that moment. He said that he’d been waiting for this moment since he was 14 so he was definitely down. He was really into being told what to do so I ordered him to go down on me. I also ordered him to turn out the lights and keep his clothes on so I could maybe imagine him as anyone other than Adam. It’s not that he was ugly — he was just that guy who was like my brother for four years. When he went down on me it felt creepy. He said, “You have a lot of hair Laura. I’m not saying that’s a bad thing, there’s just … A lot of it.” If there had been a mood, that would have killed it.

3) A “Titanic” Christmas

One time in college, during winter break, I met a guy on Grindr who I learned was my former AP European history teacher’s son. He was just a year younger, but I never saw him in high school, only heard her talk about him and never gave a thought to the fact that he may attend the same school. She had also never mentioned he was gay. Anyway, my parents were at home (I don’t think I could ever sneak anyone into their house, especially since I feel like a guest there now), so we decided to have sex in his car. When he picked me up, the only place I could think of to park was the parking lot of the country club I used to work at in high school. I definitely remember there was snow on the ground and the windows fogged up, “Titanic”-style.

4) Digressing (into being a huge ass)

I decided to see my high school boyfriend for the first time in five years when we were both home for the holidays. I had heard he was having major mental health problems, and I felt like I should check in. We had lost our virginity to each other when we were 16, so I figured it would be nice to see him even though we hadn’t spoken since before we left for college.

I had long since moved on. I had a few boyfriends while I was in school, and by the time I saw my ex, I had recently fallen in for-real grown-up love. When we met for drinks, I saw that his hair had begun to fall out, and the whispy bits that remained were hot pink. He seemed mostly the same, though.

We talked, and it was good; I told him about my problems and he told me about his. Then the conversation got very frank, and we began talking about sex and how much we had learned about it from one another — which was also good, I thought. But then I offered my ex a ride to his car when we were leaving, and of course things got weird. He asked me if I was still attracted to him, despite the fact that I had told him I was seeing someone else. I dodged the question and he called me on it. Then he asked if we could have sex in the backseat of my car, which was actually my sister’s car. I said, “That would feel like digression. I can’t do that again. We aren’t 16.”

Because he kissed me on the mouth anyway, I didn’t realize I was being an asshole. But then I told him that I thought he should get out of the car, and I sort of started feeling bad.

5) Coolest older cousin

It was my first winter break home from college, so I had just learned to drink “for real.” Every year, we go to my aunt’s house for a Christmas party, and I was looking forward to being the coolest older cousin, who knew what drinking was really like. I had like seven gin and tonics and got embarrassingly bombed (so much so that it actually brings my family shame to recall, even today, many years later).

When I was in the car with my family driving back home, I drunk texted my vaguely icky high school boyfriend and told him to come over, with my whole family very much aware, and disapproving of what I was doing.

He came over, but my parents wouldn’t let us go upstairs, because I was trashed and they didn’t want me to be manipulated. So we had sex on a couch in my den — which doesn’t have a door  —and then he left.

6) The yearbook virgin

I had a crush on this guy all through high school, but he had a super-Christian girlfriend. Senior year, during our yearbook-signing party, I got really drunk and wrote in his yearbook that I had always had a crush on him. A few weeks later, at graduation, he came up to me—you can literally see us talking in our caps and gowns in the background of someone else’s picture on Facebook somewhere—and told me he also had a crush on me for years. Nothing happened, though.

Then five years later, at our high school reunion, I saw him again. We started talking and flirting, and eventually we left the party and got in his car. We drove around for hours—until, like, 6 in the morning—and pulled over occasionally to have sex. Except we sort of didn’t really have sex. He, like, got it in, but I wouldn’t really call it full-on sex. It happened a few times.

A few weeks later, on New Year’s Eve, he texted me to say he was in New York. We went out and I got really drunk and brought him back to my apartment with me. That’s when I found out why we hadn’t really had sex at the reunion: He was still a virgin, and he was really nervous. But nonetheless, we had sex.

I took his virginity. And it was fine—until I realized that this virgin might be my only one-night stand of 2014. (I was casually seeing someone else at the time.) So, to rectify matters, I went out again on New Year’s Day, and went home with a random guy I met at a bar.

7) Just friends, touching balls

The winter after I came out, I was hanging out with my good friend Colton. He’s insanely hot, but not at all attractive; too much of a meathead. He’s also definitely straight. But I guess we were at an age where dudes just show each other their balls, except I had just realized I was gay and so that was pretty cool for me. One night Colton and I were sitting in his car in a parking lot somewhere — probably about to go somewhere else but I don’t remember — and he showed me his sack. He wasn’t, like, trying to get me to touch them or anything, he just pulled ‘em out. But then I did touch them, one of them — just for a second. Then he put his balls away, turned on the car and started driving. We never talked about it again.

8) Crusty Norman’s brother

Freshman year of high school, I briefly dated this guy, Norman. I broke up with him shortly after we started dating, because I was 14 and fickle. We stopped speaking, and I regretted breaking up with him for the next year and a half, up until I started dating someone else. Still, I pined for Norman.

Almost two years later, during winter break of my senior year of high school, he sent me a Facebook message. He was home from college, my boyfriend and I had broken up fairly recently, and so I agreed to get coffee with him. When I saw him, I quickly realized he and I had nothing in common, but I told myself that was OK because I was still into him. A few minutes after I left, he called me and asked me to come back because he wanted to tell me something. It was very dramatic. As I had lied to my parents about where I was and was already late for my curfew, I couldn’t go back. But I agreed to go over to his house the next day instead.

As soon as I arrived in the morning, we went upstairs to Norman’s outrageously messy attic room and sat on his couch “to talk.” Eventually, we started making out. I suggested we move to his bed, but he countered by suggesting we go to a different room—his little brother’s room. He said the bed was bigger. I can only assume I obliged because I had been fantasizing about this moment for the better part of three years.

Six years and plenty of sexual experience later, I can still say that sex with Norman was the worst I’ve ever had. Just fucking awful. He gyrated a lot—just sort of shimmied inside me and exhibited so little rhythm I remember being shocked he was a musician. Then he told me to talk dirty to him, and I actually (literally) threw up in my mouth a little. I basically jumped out of the bed and directly into my pants as soon as it was over. I lied about having an appointment and left his house without one of my socks.

Two days later, after I had vowed never, ever to speak to or about Norman again, he showed up outside my bedroom window on ecstasy. But that’s a whole other story.


Jenny Kutner is an assistant editor at Salon. Follow @jennykutner or email [email protected].

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