Female • 18 years old • Canada

I had been eyeing a friend of a friend for weeks. He was six years older than I was, and had just moved back to town after a stint in the States. I thought he was pretty much the coolest guy ever — well-travelled, well-read, lanky and wide-eyed, and a great story-teller — the opposite of every guy I'd dismissed in high school.

At the time, my parents were going through a rough patch in their marriage. My dad had moved out, and I wanted to be anywhere except home. As a result, I started hanging out with this guy at his downtown apartment, drinking and getting rowdy, learning what it was like to belong to no one. As far as I was concerned, this was my stab at youth.

As much as I was intrigued by him, I figured he would never want to be with a girl as young and inexperienced as me. It was no secret that I was "the virgin" of our group of friends, whereas he had played the field quite a bit. When he actually expressed interest in me, I was ecstatic, but also wary. I didn't really believe he liked me at all. The first time we hung out alone together — it would have been uncool to go on a real date — we ended up back at his apartment in his bedroom making out.

Illustration by Thomas Pitilli

Suddenly I sat up on top of him. "You don't even like me," I said, kind of sadly. He paused for a second, then assured me that he did, and I wanted desperately to believe him. Within the next week or so, we decided together that I would lose my virginity to him. Secretly, I was terrified that if I didn't sleep with him soon, he would move on. There were already other girls who'd made it clear that they wouldn't make him wait.

For some reason, it felt really important for me to keep things going with this guy. So one Tuesday afternoon, my mom dropped me off at his apartment after an appointment with my therapist. We did all the things we had been doing up to that point: had a cup of tea, talked for a while, and fooled around. Eventually he stood up and looked at me and asked if I was ready. I was nervous, but wasn't I supposed to be nervous? Would I ever not be nervous? I remember kneeling on his bed in my underwear for a minute, staring at the floor before I looked up at him and nodded silently.

He disappeared to the bathroom to get a condom. When he came back, I couldn't really relax enough to let him inside me. "You have to loosen up your legs," he said, and I tried. It hurt every time he moved to push his way in. "I'm sorry," I kept saying, "I'm really nervous. It hurts, and I can't do this if I don't know what we are. I don't know what I mean to you."

He looked at me for a second before he shrugged and said it might as well be a relationship. I still didn't believe him, but hearing him say it made me feel a bit better, even if the nagging voice in my head told me he was only saying it because I had sprung it on him at the worst possible time. We plugged at it. Eventually he gave up, and neither of us had come. "I'll get better," I said. "We just need to practice." He took the condom off rather dramatically, and I think I went down on him to get him off so it wasn't a total disappointment. Mostly I just tried to be cute and make him laugh about it. "Teach me!" I giggled once or twice.

Not two weeks later, I stopped hearing from him altogether. Then he called me one day after school to say that he wasn't interested in a relationship and he wanted to end things. Surprised that I was surprised, I cried my heart out for days before discovering that he'd been hooking up with another girl for about a month already. Then I completely fell apart. But for two and a half years after that, we continued a vicious cycle of sleeping together, going out, and then breaking up again. Our antics brought us close and kept us distant at the same time. There seemed to be no escape. He had slept with numerous other women since I lost my virginity to him, but he was the only notch on my bedpost until I fell in love with someone else and left for good. It was only then that I discovered that sex was much better than I had been led to believe. In fact, I learned that when your mind isn't clouded with doubt, it's amazing.