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Humpday Hookup Horror Stories: Involuntary Threesomes

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If you’ve got a hookup horror story, send it in using our submission form, and be sure to select “Column.” All stories will be made anonymous. Try to keep it under 500 words. Thou shalt not judge lest ye be judged.

Guard Dog
“Mike” from Brooklyn, NY

I was in the process of starting a new job, and had two weeks in between my end date at my old job and start date at the new one, so pretty much I took advantage of the opportunity, spending one weekend back in my hometown of Pittsburgh and spending the other 10 days drinking and galavanting around NYC, effectively wasting a large chunk of my severance package from my now-downsized former position. I was in the throes of yet another 72-hour bender and decided to hit some bars or, gastropubs/emporiums, as they’re called in Brooklyn. Fucking hipsters.

I was out in Williamsburg one night, mixing it up with the douchiest hipsters the borough of Brooklyn has to offer. I don’t judge people very often, but these people are unbearable. It’s not a libation, it’s a cocktail, you pretentious dickhead.

I digress. I was out with my buddy “Blake,” and he and I were already very much drunk and headed into a pretty awesome bar. It used to be a fire station or something that the hipster owner reclaimed with his hipster wife and will send their hipster baby to college because of it. But as soon as we walked in, it was like an oasis of normal people. A beautiful sight.

So after a few drinks, we made the acquaintance of several gals who were also from Brooklyn and completely normal. I ended up hitting it off with one of them. A short, stout brunette with the most annoying laugh in the world, but I have no shame. I made my move and we ended up back at her place.

She had a roommate that was gone somewhere, but we got down to business. So we’re getting into it and we hear the door fly open at the front of the apartment, and her roommate comes storming into the room, shrieking about how this was the “third time this week” and how she “couldn’t believe how irresponsible” she could be.

This feisty little brunette jumped out of the bed, completely nude, and had it out with her roommate right there. Apparently she had just broken up with her boyfriend a couple of weeks ago and had been on quite the sexual escapade ever since. I soon realized that I was probably in territory that many men had explored before and thought it was best to clothe myself and exit stage right, I walked right in between the both of them on my way out of the apartment, vanishing like a ninja in the night.

That certainly was awkward.

High Society Sex
“Carrie” from Atlanta, GA

I had been invited to a very high-society event in Atlanta my first year out of college. A friend of mine from college had recommended me to a friend of a friend to invite me to a large gala. One of the quirks about the event is that every female in attendance is paired with an escort.

I was horrified. I’m not exactly a regulation hottie by any means, but I’d describe myself as a well-above average looking young woman. Still, I was nervous to meet my escort. I was told story after story each week about some escort couples getting married after attending the gala together, and how it was one of the biggest postgrad hookup nights of the year. Oh, God. It was like the pressure of prom night all over again. Please let this guy at least be decent looking.

We emailed back and forth for a couple of days and met for coffee (#PGP) one night after work. He was cute. Oh, praise Yeezus, he was cute. He was rich, too. A 27-year-old junior executive with Coca-Cola, in fact. I had hit the jackpot. We were very cordial to one another and we even went out for a beer after coffee. I would’ve hooked up with him right there, but decided to play hard(ish) to get.

The gala was the next weekend and we didn’t see each other until then. He picked me up in a black Jeep Grand Cherokee that was obviously fresh off the lot (so hot) and took us to the hotel for the event. It was my first experience with high society. I grew up middle-class, went to a decent-sized state school and am still currently up to my eyebrows in student loan debt. I was a fish out of water. I played the part in my little black dress, charming the pants off of Atlanta’s finest.

The event went well on into the night and morning, which shocked me. My date had gotten a room at the hotel and I was into him enough to accompany him back to his room that night. He was a phenomenal dancer, charismatic and smooth. I was ready to jump his bones once the event was over.

As the event was dying down, I noticed he kept ducking away to make phone calls. I thought nothing of it. Then, he made his move, “I have some champagne back in the room. Join me?” I acted like a drunk schoolgirl and put my arm in his to head back up to his suite.

The room was massive, on the top floor of the 30-story hotel, overlooking the skyline. It was luxurious. I was going to let this guy do anything he wanted to. I wandered from room to room, as he poured me a glass of champagne. We clinked glasses and started making out. Here we go.

As we were probing each other’s mouths, I heard another voice from the bedroom. A female voice.

“Oh, what’s this? A friend joining the party?”

My mind raced. Oh, my god, I’m getting murdered.

This chick looked a little out of place. She was a little bit on the heavy side, her makeup was caked on and was obviously wearing a wig. Hooker. Dead giveaway. A goddamn hooker, and not of the high-priced variety. This was one busted-ass hooker.

Logic took over and I saw what this bachelor had in mind. He wanted a three-way. With a hooker. Sorry, guy, but I don’t fuck like that. I was legitimately shocked and disgusted.

I put the champagne down and left the room, as he tried to convince me to stay and “take a walk on the wild side.” Those were his actual words.

This guy had guaranteed, 100% legal and consensual, hot, impressed-by-his-money, STD-free sex and he blew it with a $20 dollar hooker.

Not much later, I found out through a mutual friend that he had gotten arrested for solicitation, but we could never confirm it. What a loser.

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