My First Time

Female • 16 • Washington, DC

Between my excessive love of eyeliner, his vintage band t-shirts, and our matching giant headphones, we were a pair made in alterna-heaven. Dylan was a year ahead of me in our small private school, and quietly mysterious. He was my indie hero in a sea of Lacoste polos and Lilly Pulitzer dresses. We made eyes at each other from across the room at play rehearsals and lit-mag meetings, but we knew each other only from afar, until a literary-magazine convention one weekend at Columbia. 

After a late-night talk on the train back to New York, we began a month-long courtship  via the written word. He wrote me cryptic emails, I wrote him poems. We barely spoke in public but shared our deepest secrets over email. On my sixteenth birthday, Dylan took me out to the park and confessed that he was in love with me. We knew were soulmates. We were in love utterly, completely, disgustingly, like only artsy theater kids could be. We knew in our hearts, or maybe our libidos, that we would be together forever. 

For some reason we thought we had to keep our burgeoning romance a secret, because we were both in prominent roles of the school play and we thought it would be a conflict of interest. Since we kept missing cues due to our frantic hookups backstage, it didn't stay hidden for long. 

We talked about having sex the same way we did everything else: in the high-stakes terms of teenage Shakespeareans. We planned the moment in excruciating detail. I made sure to brush up on internet porn. We both read sex books and discussed them as intensely as we did Hamlet. (I remember one he lent me had lurid penis illustrations and hairy bodies on display throughout. It seriously grossed me out but I pretended to be more progressive than I was.)

Finally, one weekend, Dylan's parents left for a business trip and we had his house to ourselves. He lit candles and we positioned ourselves in front of the view of the Potomac. He had bought condoms weeks ago, and I had been on birth control for a month and a half. We lay on his bed, making out and gazing soulfully into each others eyes. Suddenly, Dylan stopped and sat up, announcing that something felt wrong. The moment was off. We could not have sex. We debated it for hours, deciding that we should wait for a more perfect moment — like on top of a mountain during a sunset, possibly, or after prom. 

It was another two weeks of making out on the metro and fumbling with our clothes in the prop room before our hormones got the better of our romantic imaginations. We ended up consummating our epic love without fanfare or candles, in my twin bed while my parents slept downstairs. In a fit of free-love permissiveness, my hippie mother had allowed Dylan to sleep in my room, and within an hour of getting into bed the waiting period was over. 

The act happened quietly and quickly, with little blood and minimal pain, and my cat watching from across the room. When he finished, I had expected to feel everlasting love and profound connection. Instead I felt kind of sticky and uncomfortable. It was summer, and my attic bedroom was humid and hot. I tried to figure out the most romantic way to clean the blood off of my legs, and failed to be even remotely graceful.

On our anniversary, he got me a weeping cherry blossom tree, my favorite, and planted it in the backyard to symbolize our lasting love, a spectacularly romantic gesture from anyone, let alone a teenage boy. I was not so thoughtful. After he left for college, I ended up dumping him heartlessly and abruptly for the guy who played Romeo to my Juliet in the fall production. Our love was less about eternal romance and more about his muscular arms and sexy foreign accent. 

I'll always be grateful to Dylan for giving me an amazing starry-eyed first love. It may not have been prom night, but my awkward bedroom de-virginization was perfect in its own way.

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."