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Dan Savage Lost His Virginity in a Cosplay Threeway

Photo: Heinz Wohner/LOOK/Getty Images

Dan Savage has been writing his sexual-advice column, Savage Love, for 26 years. This week on Sex Lives, the godfather of all sex columnists looks back at his love life, his career, and how each influenced the other. He recalls coming out to his mother and discovering that a beloved family priest was gay; falling in love with unattainable men; and screwing up his son’s “sex talk.” And how he lost his virginity: In a tent in a field in Indiana with his brother’s ex-girlfriend and another guy, while cosplaying as knights and ladies from the Middle Ages.

This is a partial transcript of New York Magazine’s Sex Lives podcast. Call 646-494-3590 to leave a voice message.

What’s your earliest personal sexual memory?

There was a crossing guard when I was in kindergarten that I was obsessed with. And my mother couldn’t understand why I was so obsessed with this crossing guard, but I would just moon at him. And he had a look that is still the look of the guys I like today: He’s got this, like, giant Muppet mouth and long shaggy hair. I was completely crushed on him when I was 5. And I’m sure I wasn’t thinking, at 5, the things I would think now if I saw him or someone more age-appropriate. But there was obviously that kernel of who I was romantically, if not sexually.

Do you remember if there was a moment when you realized that was also sex?

You hit puberty, and you start having erections, and you start masturbating, and the cinema of your dirty mind starts to play. And you’re tormented by it. I remember trying to masturbate about girls. I remember forcing myself to masturbate about a couple having sex, not just a guy alone. That was a real effort, and an unsuccessful one.

What was losing your virginity like?

It was hilarious. I lost my virginity when I was 15, to a woman who was 22 or 23, and a guy who was 21 or 22. It was a threeway. They took my virginity. I had sloppy seconds the first time, and I was desperate for him not to realize that it was him I was attracted to. At 15 I still thought [that] I had to learn how to have sex with women because I’m not going to be able to have sex with men. (That lasted about six more months after actually having sex with a woman.) And there was this moment when he had finished, and I was fucking away in the missionary position in a tent in a field in Indiana somewhere —

What? Why were you in Indiana in a field?

Oh my God, it’s so embarrassing. This is even — I can’t tell you this part. I was camping at an event that I was attending for the Society of Creative Anachronism. The people who dress up like knights and ladies and go to the woods? I was in SCA, as it’s called. I was a LARPer before LARPers were a thing.

Were you in, like, a codpiece?

Mm-hmm. I was until we were fucking! I removed the codpiece, it would have been a really awkward sort of velvet diaphragm to try and jam into her if I’d had sex with the codpiece on. I was a considerate 15-year-old.

Tights and hose and a hat with a giant feather on it. I’m a geek and I still am. But he was really sexy, and she was my older brother’s ex-girlfriend, which was really weird, and which was by design. I wanted it to get back to him — and get back to my whole family — that I had sex with a girl. I was not discreet about it because it was buying me time and making me safer. This was 1979, 1980. It was not a safe time to be an out gay teenager, or to be suspected to be gay as a teenager. And still, today, it’s often not safe to be suspected of being queer as a teenager. It’s better in some places, sometimes, but not everywhere. And so, yeah, I fucked my brother’s girlfriend.

They initiated it. I had been flirting with her, and she had been flirting with me, and he was flirting with her and flirting with me, but [at the time] I didn’t get it. I wrote about this — there’s a book called Things I Learned From Women Who’ve Dumped Me and I wrote about this experience.

I was terrified that he might think I was gay and then kill me. That if he realized he was naked and having sex in a room with a gay guy, he would kill me. So I wouldn’t look at him or touch him. But he touched me and I thought, Oh, that’s okay. He knows he can touch me because he knows he’s not gay. How stupid is that? He helped me finish, because they were getting impatient. And literally what my 15-year-old warped, closeted brain thought was, Well, he can do that because he’s not gay. If you do that, he’ll realize you are gay, and kill you.

Did you know him after that?

No. And I’m not on Facebook, so people I had sex with when I was 15 can’t find me. I mean, they can, they can write me at Savage Love. But I probably won’t answer.

Dan Savage Lost His Virginity in a Cosplay Threeway