Love & Sex

My First Time: Male, 14, Massachusetts

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Male • 14 • Massachusetts

In January of my freshman year of high school, my girlfriend tearfully informed me that her dad had changed jobs and that she would be moving to New Hampshire the following summer. The distance was not too far in adult terms — maybe a ninety-minute drive — but as far as we were concerned, she might as well have been moving to the moon. We'd been together nearly two years (minus a truly awful three-day breakup) and I was convinced, as only sensitive fourteen-year-olds can be, that she was The One. After we got over the shock of her moving, we'd talk on the phone for hours about how everything would be fine once we were old enough to have cars. We'd be able to visit each other without asking our parents to drive us, we'd go to the same college, and then we'd get married. We thought it was magic that the Beach Boys had written "Wouldn't It Be Nice" about us, before we were even born.

“My hands were trembling and my face was burning with embarrassment…”

I'd kissed one other girl, but she was my first for a lot of things. One miraculous afternoon I was over at her house and her mother had to leave us home alone for about fifteen minutes to go and pick up her younger brother from soccer practice. We made the most of it: we sprinted to her bedroom, lay down on her bed together, and… took our shirts off! It was the first time I actually saw her breasts. It was the first time I felt my naked chest against hers — a wonderful feeling. On other occasions we would sneak into the crawl space below her back porch and spend ten or fifteen sweaty minutes with our hands down each other's pants. It never took much effort for her to get me off, but my clumsy, nail-bitten fingers cannot have brought her much pleasure. (I still remember how bad I felt several years later when my first college girlfriend patiently explained how women's bodies actually work.)

On the first Wednesday of every month, our high school had a half-day. For the April half-day, we conspired to meet at my house (I was a latchkey kid, if anyone still uses that term) and we agreed that that was the day we were going to do it. I don't remember ever saying out loud that we were going to "have sex." On the way to school that morning I stopped at the convenience store and asked the guy behind the counter for condoms. I was fourteen; I don't even think my voice had changed yet. He said he wasn't sure he was allowed to sell them to me, and I'm still proud of my response: "Then it'll be your fault if I get her pregnant." I left with my condoms, and I don't remember much from school that day.

That afternoon, we rode the bus to my house and went to the basement. We actually set up a half-played Trivial Pursuit game so that if anyone came home we'd have an airtight cover story. I can't imagine how hilariously ineffectual this story would have been if we'd gotten caught alone in my house.

So this was it. It was actually going to happen. We undressed in silence and lay down on the couch. More firsts: it was the first time we'd seen each other completely naked; it was probably the first time I'd been naked in front of another person since I'd started bathing myself. I was really fucking nervous. I got it in my head that I wanted to go down on her, even though we'd never talked about or done anything like that before. When she realized where I was headed she lifted up my head and said, "Don't do that — it's gross." I felt terribly ashamed and silly that I'd tried it without even asking her if she wanted me to. My hands were trembling and my face was burning with embarrassment. I fumbled with the condom wrapper, and to this day I don't understand the physics of applying a condom to a penis as flaccid as mine was in that moment. But I made it to half-mast and I was inside her for about thirty seconds, long enough for me to come and for her to say, "I don't think this is working."

Afterward, we drank fruit punch and talked about it over a game of Trivial Pursuit. We agreed that it was weird and that it hadn't gone well, but that we would try it again if we had the chance. She moved two months later; that day I cried so much that when I wouldn't come downstairs for dinner, my mom brought a fried-egg sandwich (my favorite) upstairs and let me eat it in bed.

We broke up shortly after, but we stayed friends; when she came to visit me at my college seven years later, we finally got it right.