Love & Sex

My First Time: Female, 16, Pennsylvania

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Female, 16, Pennsylvania

We met in mandatory art class in middle school, where my uncertain stick figures paled in comparison to his naturally-inclined drawings. He was pale, and skinny, and neither of us had quite gone through puberty yet, nor had we been in relationships before. He confided that people had made fun of him for thinking he was gay. I felt happy that a boy was finally paying attention to me for the first time since, well, since ever. My good friend and I both wrote our instant messenger screennames on his worksheet during health class the next semester, and soon he and I were talking every day. 

The next year, we started dating. It was a wonderful first relationship, full of going out to dinner with his family, ice skating, and school dances. We had a number of physical firsts, all of which were unexplored territory for both of us, but we didn’t have sex. We were happy exploring each other in other ways, and neither of us was quite ready to go that far.

Fast forward 15 months to him breaking up with me because he can’t handle my constant depression that was triggered by my male best friend moving across the country to Idaho. He couldn’t deal with me being so upset all of the time, and he didn’t understand why I was so affected by another guy leaving. Two weeks later, he started dating my formerly-good friend that was in health class with us two years earlier. I was extremely hurt. He had been my best friend, my confidant, and more than anything, I had trusted and loved him in a way that my 16-year-old self didn’t know was possible, despite plenty of exposure in teen romance novels. We stopped talking because it hurt me too much to have him exist and not be with me; I tried as best I could to put him out of my head, and distracted myself by making out with a boy from my AP World History class every few weeks.

A few months later, I missed him so much that I couldn’t stand it anymore, and texted him to tell him so. After him lying to his girlfriend and us hanging out a few times, I came over before one of our friend’s Sweet 16 birthday parties, while his parents were at an amusement park with his brother all day. We were lying on his bed, our faces inches from each other, but I wasn’t about to be the one that initiated him cheating on his girlfriend. So he did it. We started remembering what it was like to be together, when he abruptly took me by the hand and led me into the bathroom adjoining his room. We nervously stripped each other and got in the shower.

I had my period, but he didn’t care, and I didn’t either. I laid down in the bathtub, and he sat on top of me and entered me for the first time. He didn’t wear a condom. I don’t think either of us finished, but I was so happy to be back with him in any capacity that I didn’t care how it was. We were together, again, how it was meant to be.

The cheating continued over the next month or so, which culminated in his girlfriend snooping in his phone, finding some incriminating text messages, and getting furious at me for tempting her boyfriend. She called me a slut and didn’t understand how it could possibly have been a two-person collaboration. He told her that they were breaking up and she literally thought he was joking, until a few hours later when she talked about making plans for next week and he said he wasn’t comfortable doing that. I thought that they were breaking up so that he and I could be together, but afterwards he and I stopped hooking up. Now that he was single, he could pursue other girls. He was very popular among the girls in marching band with him, as he had slightly buffed up by this time, due to long hours of carrying heavy drums. 

He dated more girls, but he was always on my mind, and six months later, we were together again. We finally were having a lot of sex, but always sneaking around, and while I was happy with it then, I look back now and realize that it was terrible, with neither of us usually finishing. It only lasted a few months, and he finally broke up with me at the end of the summer before our senior year of high school, saying that he didn’t want to have a girlfriend. Two weeks later, he started dating a girl that would follow him to art school in Brooklyn, and they’re still together. I often wonder if he ever told her about all of this, but somehow I doubt it. 

Image via Amy