My First Time

Illustration by Thomas Pitilli

Male • 18 • Columbus, OH

I had completed a year of college without having sex. The movies had lied. Now my birthday was less than a month away, and I was turning nineteen, which would make me approximately seventy-two in virgin years. I resolved to step up my game. As I was fairly awkward, this step up did not involve going out and meeting a nice girl, but rather perusing Craigslist and responding to as many casual-encounters ads as possible. I didn't really care much about the age range, or looks for that matter.

My virginity wasn't special. In my mind, it was a stigma and needed to be shed as quickly as possible. Most of my replies to ads went ignored, and the "women" who responded always turned out to be spam. I would come home from work and spend a few hours almost every night crafting e-mails to potential lovers who were either underwhelmed or non-existent. Then one day, I got a response. A real response. From a girl. With pictures. She was twenty-three and cute. We corresponded a few more times, and then she asked me to meet her at a bar.

I was given big Xs on the backs of my hands marking me as under twenty-one by the bouncer when I entered, and she spied me at the door. She broke off from her friends and we grabbed a table. We spent about half an hour engaged in mindless banter, almost as if there had never been a sexual purpose behind our get-together; we were just two prospective acquaintances. I nervously sipped my Coke, too nervous to bring it up. Then, seemingly out of nowhere, she asked me if I wanted to go back to her place. I said yes, and we hopped in my car and drove to her apartment, where we sat on her couch and engaged in more chitchat. I had had high hopes coming back here, but maybe she had brought me back for nothing more than a discussion.

Then she began to rub my leg, and said, "This is always kind of the awkward part." I looked at her. She leaned closer, and from there it was on. I started kissing her, and almost as quickly began pulling at her clothes. Eventually, she was standing completely naked in the middle of her living room.

I stood up, fully clothed, and kissed her, and as I did I slid a hand down, thinking, Oh, so this is what a vagina feels like. She took me by the hand and led me into her bedroom. More kissing as I disrobed. Then back to me fingering, until she handed me a condom. I lay on the bed and she climbed on top of me, and rode me for perhaps a minute until I came, apologizing profusely and saying, truthfully, "That's never happened before." She asked me to take her back to her friends at the bar, which I did, before returning home to gloat to myself. We never spoke again.

I don't really regret the way I lost my virginity, but I find it somewhat embarrassing. As a less awkward guy who can now communicate with women without the aid of electronics, I'll only ever share this story anonymously.

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."