My First Time

Illustration by Thomas Pitilli

Male • 19 • Delaware

I was a nobody, the kid in your freshman year at college who didn't fit in anywhere, wore poorly fitting clothes and glasses about seven years before it was cool, and had hair that was too short to be an afro but too long to be fashionable in any way, the result of a stint with dreadlocks in high school. By the time October rolled around I had realized that I was out of my depth in college — skipping every class but Japanese, changing my major three times, and convincing myself that the best use of my time was getting high and watching daytime television with my roommate, my best friend from high school. Despite all the partying and dating that went on, I was somehow still a virgin while everyone else, including my socially awkward roommate, seemed to be falling into sex without trying. I was convinced that if I conquered this particular problem, everything else would fall into place.

I got an answer to my prayers right around Halloween. Ashley was the girlfriend of a high-school friend who'd chosen to enlist in the military rather than go to college. She was a short, slim brunette with wavy hair, an eternal tan and freckles in all the right places. We'd all spent time together during the summer and while I was certainly attracted to her, it never occurred to me to go any further than friendship. Once school started and her boyfriend shipped off we talked online or on the phone almost every day, ostensibly to help her maintain her relationship while the boyfriend was away. Things escalated when she came to visit one weekend, staying in my dorm room. The first night was harmless, drinking and playing board games. She even slept in my bed uneventfully.

The second night we threw a party in our suite, with most of our dorm mates joining in at some point. Eventually the party migrated to someone else's house, but Ashley and I volunteered to stay behind to clean up. Cleaning up turned into dancing to classic R&B songs which turned into us in my bed, pouring out our hearts to each other about how lonely we felt and doing everything short of having sex. The next morning we were giddy and light-hearted, sneaking kisses and touches behind my roommate's back. He also knew Ashley's boyfriend and was undoubtedly suspicious, but gave us the benefit of the doubt. I drove her home and we made plans for me to visit soon.

A few weeks passed and it was Ashley's birthday, so I used that as an excuse to drive down to her campus for a visit alone. By then my roommate definitely suspected that something had happened during the previous visit, to say nothing of our mutual friends who also knew all of the parties involved. I had spent the intervening period playing dumb and innocent, but I knew that it was only a matter of time until the dam broke. Half of me wanted it to break, wanted to go shout from the rooftops that she was with me now and to hell with whoever didn't like it. But the other half was terrified of the consequences.

Conflicted emotions in tow, I drove an hour away to her campus. She gave me a tour, introduced me to her local friends and showed me the town. It was a pretty good night until I came down with a fever and chills. Whether it was stress, nerves, bad food, or an actual cold, I'll never know, but I spent the night bundled up in her bed and we fell asleep having done nothing more than kiss. By the next morning the fever had passed and we began to pick up where we had left off, working our way up to sex. I'd had plenty of instruction and advice on what to do but no idea what to actually do. I didn't even have a condom. Luckily she had some. I put one on and she guided me from there.

I had heard that most first times were bad, but this just seemed beyond terrible. It lasted maybe ten minutes; neither of us came and I remember thinking "That's it? This is sex?" We were cuddling and working ourselves up to a second round when the phone rang. It was her boyfriend. He had just graduated from basic training and had called home first, only to be informed by our mutual friends that I had spent the night with Ashley.

I sat on the edge of the bed and listened as she consoled her sobbing boyfriend over the phone, promising that nothing had happened, that she loved him and that she and I were just friends. Eventually the call ended, but it was clear that whatever infatuation there might have been was gone, replaced by the guilt and realization of what we had done. The rest of the weekend was a disaster, culminating in an argument over the phone between her boyfriend and me, in the middle of Ashley's birthday party. The next day I drove home to find myself a social pariah, most of my friends unwilling to even speak to me for months and Ashley slowly distancing herself from me.

I used the disastrous events as an excuse to do poorly in school, barely skating through fall and winter sessions, failing out of school in the spring and spending the following year working and taking part-time classes before leaving the country and eventually joining the military. My friends eventually forgave me and I reconciled with Ashley's boyfriend, apologizing for what I had done. Looking back, I still I don't know what to make out of all of it.

Female • 16 years old • Israel

We became friends right from the start. We found that we had the same cynical and sexual sense of humor.

Female • 22 years old • New England

"I can't tell you how glad I am that I never signed that 'True Love Waits' pledge."

Male • 15 years old • Washington DC

"I had never planned to lose my virginity to a guy—let alone Rob. I planned to pretend to be straight for as long as possible."