My First Time

Illustration by Thomas Pitilli

Female • 21 years old • Washington, DC

Henry and I grew up minutes from each other, yet somehow had never been friends. But after a chance encounter, he was night-swimming with me hours after everyone had left the Fourth of July party, and I was remembering the tiny crush I had on him in high school. Days later, as we hesitantly shared my squeaky bed, we confessed our kinky fantasies and special skills. We were perfect matches in the bedroom and that seemed like enough of a reason to start a long-distance relationship.

But our perfect match was a bust in one way: I wanted to wait until marriage to lose my virginity. I'd learned to perfect the "everything but" routine, but for the first time, it just wasn't enough. Henry was a good-looking man, tall with a beard and glasses. At five-foot-two, I was a whole foot shorter and loved being able to climb his long limbs. I was so physically attracted to him that we spent most of our rare time together naked in my room. While apart, we spent hours on the phone talking and quickly came to know almost everything about each other. After giving it just the right amount of thought and a heavy dose of hormones, I decided that Henry would be my first. Since we were dating long-distance, I decided that the night that he came down for my work party would be the night it happened, exactly two months after our reunion. We talked about it a little, but I stressed that I didn't want to make a big deal of it. I wasn't a romantic person and got nauseous at the idea of candles and flowers strewn around the bedroom. Unfortunately, when the day finally came, traffic made him run late and nerves made me drink enough gin and tonic to have me fast asleep minutes after giving him a hello kiss.

The next morning I woke up a little thirsty, but not a bit hungover. I woke Henry up with kisses and in no time at all we were at the point of no return. I told him that I wanted to fuck him and he looked at me, trying to gauge my seriousness. I asked him one more time and smiled as he leapt off the bed to retrieve the condoms. We tried a couple of different positions, but each seemed just as uncomfortable as the last. I had reasonable expectations for the first time, so we kept at it like resolute adventurers. After a while, I got on top and it started to feel better, even good. Henry looked up at me in a weird way. "Are you okay?" he asked. I nodded and couldn't understand why he was asking until I noticed his eyes glance at the sheet next to his face. There, in the most vivid red hue, was my handprint, cave-painting-style.

I quickly dismounted and started apologizing profusely for my virginal artwork. Henry seemed just as apologetic as I was and couldn't stop asking if I was okay.

We stripped the sheets, laughed at the perfect form, and threw them into the wash. We couldn't wait for the dryer to finish before we tried having sex again, so we ended up doing two loads of laundry that day. It became one of our many inside jokes, and we were never able to look at cave art the same way again.

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."