It Happened to Me: I Tried To Have Sex With My Gay Male Best Friend

Nick and I put our shoes on in the foyer and I asked him if I could sleep over because the thought of sleeping next to him was nicer than sleeping alone.
Publish date:
August 13, 2012
best friends, loneliness, hook-ups, embarassment

My friend Nick and I met in our first year of college when we were both chain-smoking teens with monotone voices and bad attitudes (this still describes us pretty accurately except now we’re closer to 30).

Nick identified as bisexual during college even though he later told me, “Girl, I was NEVER bisexual.” I initially had a crush on him and half-heartedly pursued him. We used to make out on dance floors to try and incite jealousy in the boys we liked, which in retrospect never worked.

It was pretty clear that Nick never had the intention of dating girls, and other than those drunken lapses we had a platonic and comfortable friendship.One night, I went over to Nick’s before a party to pre-drink. I remember looking at all his shoes scattered at the front door and I thought of all the parties, bars, parks, venues, cabs, alleys and restaurants we’d been to together. It made me realize that there was definitely no straight male equivalent to Nick in my life.

We were sitting at his kitchen table drinking some beers and smoking some cigarettes and talking about boys and feelings. Our love lives mirrored each other’s; they were an endless string of unreciprocated crushes punctuated by brief stints of things working and then fizzling out. Although our morale was pretty low we decided to go out, anyway. We were driven by the endless hope of young single people; if you go to one more party you might find what you’re looking for.Nick and I got to the party and although we had hoped different people would be there, we instead found the same people who were at every party we went to. We spent our evening dancing in the kitchen, smoking on the back porch,and texting romantic prospects who weren’t texting back. At 4 am, there were no beers left in the bathtub and the apartment was a dead zone.

At that time in my life it seemed like if I didn’t find someone to go home with or make out with, my night was a failure. Nick and I put our shoes on in the foyer and I asked him if I could sleep over because the thought of sleeping next to him was nicer than sleeping alone. When Nick and I got back to his house I put on some of his boxers and a T-shirt that smelled like the stuff he put in his hair, and crawled into the bed with him. We lay in bed together for a few minutes, not really saying anything, until he asked me if I wanted to make out with him.

When we kissed, even though we’d done it before, it was so bad. We kept laughing and our teeth kept smashing into each other’s; our mouths didn’t match up at all. Nick moved his hands over my breasts as if he was touching something slimy and told me they were freezing. We made out in the dark for a while; no matter what we did to try and make each other feel good it just felt more and more awkward and unnatural. I think we were both kind of hurting each other.

There was nothing I could do to make him hard and I became increasingly frantic. Nick was at more of a disadvantage than me, but I felt like I had no excuse, I had to get him off somehow. I tried to go down on him but all I could hear in my head was Margaret Cho’s voice in your head saying “You're like a baby bird trying to pull a worm out of the ground.”

I remember the expression on Nick’s face as he was confronted with female anatomy in the flesh for the first time. He examined me like I was a rare insect: equally fascinated and repulsed. I felt like I was a patient of the world’s most amateur gynecologist. It made me feel objectified in a really bizarre way; the way he touched me was so un-sexual. Unable to create desire in him, I felt like I had failed at something I prided myself on.

Art by: Walter Scott

After flailing around for a few more minutes, we finally accepted that nothing was going to work. It felt more like we were wrestling than trying to have sex. Aside from the fact that Nick was gay and a close friend of mine, the let-down feeling that filled my chest was similar to what I felt after other frantic post-party trysts.

Nick asked me in his most deadpan tone “So, did you come?”

We both started laughing because we had failed so miserably at making each other feel good but we didn’t have to hide it from one another. He said he thought it could have worked, but his logic of, “A hand in the dark is a hand, isn’t it?” obviously fell through. We were now even more sexually frustrated then before, but at least we were laughing.When Nick and I woke up the next day we felt half dead. We looked at each other and said, “Oh god, oh god, oh god” for a few minutes but then got up and went out for breakfast like we normally would on a Sunday morning.

His roommate asked us what the hell we had been doing last night and jokingly asked if we had sex, and I just laughed it off. I initially felt kind of ashamed about what had happened between us, and I kept it to myself for a long time.

But it made me examine this almost compulsive need I felt to be close to people. I already knew deep down that the choices I was making only ever made me feel lonelier and more ashamed than I had felt before. At least in this instance, I had been with someone I cared about and felt comfortable with and there was none of the usual dread associated with heterosexual friend hook-ups.

Nick and I were lucky it turned out that way because we potentially could have ruined a great friendship if things had gotten weird afterward, all for the sake of not wanting to sleep alone. That experience was kind of the first step to untangling a whole bunch of things that needed to be addressed.

Nick and I still reference our failed sexual experiment when we need to be reminded of how ridiculous we used to be ... and how we will probably always be friends.