I Had a Threesome with My Boyfriend and the Girl He Was Cheating on Me with

She looks at me and says, “Is it okay if I kiss your boyfriend now?” My gut is twisting, and I can’t really look, but I also have to look.

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Nov 23 2017, 11:12am

Illustration by Niallycat

My First Time is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your "first time" is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that's how sex stays fun, right?

This week, we're talking to feminist dating coach Hayley Quinn about the time she had a threesome with her boyfriend—and the girl he was cheating on her with.

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I’ve had some good threesomes and some ones that have been a bit of an error of judgment, in my wilder youth. I always think threesomes are like normal sex. You can have really good ones, really awkward ones, and everything in between. In my earlier years I was a human guinea pig when it came to the world of dating and love.

When I was 18, my first boyfriend, who I really loved, was into the pickup artist community. He went to a pickup artist convention and there was a porn convention being held in the same hotel. He told me—over AOL Messenger, which we used at the time—that he’d had an orgy with three female porn stars he’d met at the convention. It blew my mind and broke my heart at the same time.

Suddenly I became exposed to the world of pickup artists, porn, and polyamory. I wanted to find out more about something that had been quite painful for me to experience, so I threw myself into learning about these worlds. Weirdly, I actually looked into joining and becoming a more practicing member of my church, but I went down the pickup artist route instead. I went to work and live in a pickup community and they taught me their craft.

Living in the nomadic pickup artist community, I started exploring, often with lesbian and bisexual relationships. I’d tell myself I was having fantastic adventures, but deep down I was out of my depth and panicking. I’ve always had a desire for a certain intensity of experience, but quickly that can spiral and you’re just looking for new thresholds to break.

Many years ago, I found out that my boyfriend at the time was cheating on me, and it was the worst kind of cheating: He’d been on a date with a girl behind my back, and he hadn’t slept with her, but he was really attracted to her. So I contact the girl and I invite her to go to a party in a country hotel with us, where I knew something debauched could happen. I think I was wildly trying to exert control over the situation.

She’s totally beautiful, an Oxford University student, five or six years younger than me. We’re in this big old house, and we’re greeted with champagne and Oysters. I’m wearing this Dior dress—it cost more money than I’ve ever spent on anything in my life—and she’s wearing very high, cheap, black patent shoes, and a skimpy, quite cheap dress, and she looks gorgeous. She looks super-hot. She has this insane genetic material. She smashes every beautiful standard.

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There’s this moment at the party where we’re both doing our makeup in the mirror at the hotel, and it dawns on me that something is seriously wrong: We’re both doing this for the same guy. Then she looks at me and says, “Is it okay if I kiss your boyfriend now?” My gut is twisting, and I can’t really look, but I also have to look. It was like I was having an out-of-body experience. I don’t think my partner was enjoying it either. He seemed really uncomfortable.

At every stage, like the first time I saw her kissing him, or when I saw her naked, I wasn’t sure if I was going to go into the next stage. But then because I had said yes, it was like the next thing had to happen too—a chain of yeses.

After the party, we ended up back at the hotel room. It seemed like the inevitable thing was for us to have some kind of sexual experience. My boyfriend was on edge, he couldn’t maintain an erection—he just kept pacing the room. So I tied her up and had sex with her while my boyfriend watched.


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So, I think this is the most fucked up thing I’ve ever done. But after we had sex, I’m looking over at him, and I know him—I know he’s thinking, he probably can’t perform sexually. I say, “Do you want to fuck her? I’m going to sit here, and watch you fuck her.” And I’m sitting there, actively trying to ruin the experience, but at the same time doing something desperately wrong and really hurting myself.

Anyway, he couldn’t really fuck her, and as we’re falling asleep we realize there’s not enough room for all of us in the bed, so I have to sit on the window ledge as the sun is rising, literally watching them spoon. I remember that she had her hair in a long plait, and I could hear the crows outside, and I felt super fucked up.

The next morning it’s like an eight hour drive back to London. She’s sitting in the back of the car and it’s all so weird. We’d stop for food and they’d sneak off together, and it just summed up how ridiculous the scenario was. I was trying to be all cool and edgy, but it was like—they have the emotional intimacy, and you’re on the outside. In future if my partner ever cheats on me I’ll go down the traditional route of putting their things in a bin liner and breaking up with them.

After the threesome, I tried to reconfirm my relationship with my boyfriend by moving in together. We lived together for a year and during that period she became this figure of torment for me. He was semi-obsessed with her. I found out afterwards that he’d seen her at least once behind my back after the threesome. The relationship ended pretty quickly after that—I found out I was pregnant, and he left me. I decided to keep the baby, but I ended up miscarrying quite late into my pregnancy.

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The miscarriage basically woke me up. I just thought, What the fuck have I been playing at for so long? I don’t have a partner, I don’t have anyone who can love and support me. I’ve kept this relationship alive like a half-dead thing, and look what I’m left with now. The moment for me to let go of him wasn’t when he moved out and left me, pregnant. It was a year before, around the time of the threesome, when things started to get unhealthy. But instead I started to play this game. The threesome and the pregnancy, for me, was like a hardcore reset to my sense of self.

I got interested in the world of threesomes because some guy had an orgiastic experience with all these porn stars. And then I entered into this quest to learn about sex, seduction, and love, and along the way I lost my perspective on excess. What excess does is that it allows you to escape self-reflection. The cool girl thing was just a front, an image. I’ve popped out the other side of that period now. The threesomes began and ended a period of my life where I felt like I was living out something and exploring something I don’t regret. But now, I feel like I’m the person I was before this thing began.

This interview has been edited for clarity and length.