We’re looking for stories about the first time you had sex. Email with 500-1000 words. (Don’t worry, we won’t print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.
I grew up in a small town in Florida. By my senior year, I hated everyone I went to high school with. So my best friend, my sister, and I made a bunch of friends who didn’t go to school with us. They were older bad boys who had, for whatever reason, stuck around after high school doing nothing but working and partying and selling drugs. We were rolling with the bad news bears.
We had a core crew, with random appearances by a larger group. We would hang out or go dancing at least twice a week. When summer began, it became more like every day. Sexual antics abound — dating, cheating, and drama — the usual for late teens and early twenty-somethings in small town USA. Everyone I knew had pretty much dated everyone else I knew. Except me. I’d fooled around with one of the guys, but it was very casual and short-term.
I was a confused girl. I had decided that I didn’t want to have sex until I was ready to deal with the consequences, which included STIs and pregnancy, not to mention the emotional baggage that I’d seen some of my friends carry around. But there was more to it than that. I liked the attention I got from hot guys. It felt good. But I wasn’t as into it as the rest of my friends. Later in life, I realized that was because I’m mostly gay, but that’s a story for another day.
Rob* was friends with all of my friends, and had dated most of my gal pals. he was sweet, and gorgeous, and very funny. At the end of the summer, just before I was going away to college, he and I ended up making out at a party. That led to a few weeks of fooling around during the day at his house while his parents were at work. We had decided not to tell our friends, for what turned out to be two very different reasons.
We had always had long, intense, meaningful discussions and challenged each other. So when I turned him down for sex, he said “you say that, but you keep coming back over here. It makes me wonder why. Is it because you don’t want to, or is it because you’re nervous?” I no longer remember what my answer was, but the question bounced around in my brain for hours.
The next morning, on the 30-minute drive to meet up with him for our last “date”— I was leaving for college the very next day. I pondered my answer to the question and realized that I was just in the habit of saying no. I did, indeed, want to fuck him.
I didn’t tell him right away. We fooled around for a while, and I enjoyed my secret. When I couldn’t wait anymore, I told him I was ready. He was incredibly sweet, asking me if I was sure, and was very considerate.
He was experienced. I’d fooled around with a few guys, but had never gone further than 3rd base.
I’m positive there were candles lit and some sort of downtempo music playing (probably Portishead). He put on a condom. It hurt. Not horrendously, but it hurt. It wasn’t great, but I could tell that it would be later. It’s probably the only time in my life I didn’t come. I don’t think he finished, but I don’t think I told him to stop, either.
He and I ended up dating for 2.5 years. We had a lot of really great sex after that. But it came at a price. I found out much later, after we’d gotten serious, the reason he didn’t want our friends to know we’d been seeing each other.
He’d slept with my sister.
