Love & Sex

My First Time

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Illustration by Thomas Pitilli

Female • 20 years old • Upstate New York

The guy was my first boyfriend. We met before my senior year in high school. He was twenty-two and I was seventeen; this appealed to my badass, alternative sensibilities at the time. He was an artist, virgin, and chronic pot smoker who lived in an apartment above his mother's. Most of his days were spent constructing sculptures of bleached and glittered animal skeletons he had found in the woods, recording noise mixtapes, making his entire backyard into a freeform garden, and sewing himself clothing. I found him very intriguing, but wasn't sure how well I could handle his "personality" (insanity?). I decided that I was just being close-minded and needed to push myself.

He was an artist, virgin, and chronic pot smoker who lived in an apartment above his mother's…

Senior year ended and we still hadn't had sex, but had done most else. I was never very enthusiastic about any of it. I felt it was a chore that needed to be completed before I could move on in life. We decided to stay together when I went off to college, and I would call him every night before bed; we'd talk about his various conspiracy theories and fears. He was a sweet guy, but his life was going nowhere. He refused to get a job, but we had excellent communication and he was the most creative person I had met. I was starting to get annoyed, but stayed with him because I knew it would be even longer until I lost my virginity if I didn't just do it with him. My friends at college were all rooting for me every time I went home on the weekend. I was torn but decided it would be the better choice just to get it over with.

We would always plan to have sex when I was home, but then we'd end up putting it off with excuses like "I have a headache" or "We'll just do it when you're home for a month over Christmas." Eventually Christmas vacation rolled around, and then suddenly it was the last week and we still hadn't done it. The last few days of break, we scrambled to "get it in," but he had trouble keeping it up, probably due to my lack of excitement.

On St. Patrick's Day, we finally did it, though "it" was hardly anything. The dick was in good enough; I was super-relieved it was over. We high-fived multiple times. I mostly just wanted to tell my friends at school I had lost it. At the time I was very confused over whether I loved this guy or not. Now that I've had time to think, I don't think I did love him… and that's probably why it was such a hassle.