Worst Sex Ever: ‘He Lost a Condom Inside Me’

As told to
Illustration: Sarah Maxwell

Sex Negative is the Cut’s series on the messy, clumsy, unromantic reality of boning.

In college, I wanted to be the kind of girl who would take a guy home from a bar without a second thought, but it always felt like a bad idea. At a party one night when I was 22, I decided it was time, and settled on a relatively tall, relatively handsome grad student who seemed like the kind of guy I’d go on a date with anyway. In hindsight, I should have stuck with my instincts.

We left the party and took a cab to his apartment, and after doing that nervous thing where you watch three scenes of a movie and pretend you’re not only there to bone, we started making out. I kept trying to reach for his dick, but each time I did, he swatted my hand away and told me to slow down. Eventually, we got into the bedroom and he took his pants off, but still seemed hesitant. No eye contact, no hands on my hips, and he wasn’t hard. When we had finally made out enough to produce a serviceable erection and he got on top of me, I was optimistic that instinct would take over, but we had sex for approximately 30 seconds and then he asked to go back to kissing. Then he explained what was wrong: While I was still pinned to the bed, the sad stranger on top of me told me about his recent breakup. I’ve never been so desperately cuddled and so thoroughly annoyed in my life.

I offered to leave, but he was determined to finish. The same scenario repeated several times: We’d have sex (always missionary), he’d get emotional, and we’d take a break. After a couple cycles, he hit his stride and we had a few minutes of convincingly enthusiastic sex, during which I faked an orgasm. When he came, I was relieved until he tried to pull off the used condom and panicked while still between my legs — it was gone.

We both leapt up, turned on all the lights and started rifling through the sheets in what was, in retrospect, a very optimistic belief that the condom had fallen off. He and I eventually came to the conclusion that that wasn’t the case, at which point I excused myself to squat on the floor of his bathroom (in privacy, like a lady) and search my vagina. After a while of poking around, I came up with nothing. As I stood up, I found myself face-to-face with the art he had chosen for the room: a framed portrait of Ronald Reagan. I had let a Republican lose a condom inside my body.

I went back in to enlist his help and got in the full gynecological position on the bed, knees in my armpits. This shouldn’t have felt like the most undignified part of the evening, considering he had nearly cried over his ex while still inside me, but shame is unpredictable. He, too, looked thoroughly embarrassed, which irritated me — he wasn’t the one spread-eagled in hopes of avoiding an emergency gyno appointment. After a few reticent attempts, he got in three knuckles deep and produced the missing tube of latex. I’ve never gotten dressed so quickly.

I got Plan B the next morning and texted him when I got my period to let him know we were in the clear, but he didn’t respond, which was probably for the best. A year later, I found myself hiding behind a Froot Loops display at a grocery store in order to avoid him, and I decided then and there that it was time to move out of my college town and get on with my life.

Worst Sex Ever: ‘He Lost a Condom Inside Me’