Ten Illustrated Stories About First-Time Sex

Funny, sad, and nostalgic tales submitted by Nerve readers.

Do you have a great first-time story? Tell us! My First Time runs every Tuesday on Nerve.com.

Illustration by Thomas Pitilli

Male • 18 years old • Maine

It was the end of winter break, and I was meeting a girl at the airport to head to NYC for a week of sightseeing before school started up again for the spring term. She had been my best friend for the past six months, and I think she'd known all along that I had a massive crush on her. She hadn't acknowledged my interest, though, except to say that she wanted to be single after a bad experience breaking up with her last boyfriend. I arrived an hour late, and as we were loading her luggage into the trunk of my '94 Volvo, it stalled out, so we were stuck waiting in the front seat until it would start again.

While we waited, we talked. I asked her about her vacation (she lived in Hong Kong, so any story was interesting), and told her about mine. And then it was silent. "I missed you," I said. "A lot."

"Me too," was her answer, and she leaned over and gave me a quick hug. In the darkness I fumbled for my keys and tried the ignition again; the car started and we headed for our college.

That night we were staying in the dorms, planning to make the trip to NYC the next morning. I dropped my two duffel bags off in my room, then went upstairs to hers to keep her company as she sorted through her three suitcases and two boxes of clothing, electronics accessories, and documents. Hours later, she finished putting everything into its proper place, and it was time to sleep so that we could get an early start in the morning. We hugged, said goodnight, and then I hesitated before going out the door. "You don't want to go downstairs tonight, do you?" she asked.

She had a liberal attitude when it came to physical affection. All sorts of hugging and holding hands and kisses on cheeks were acceptable, which was very different from my upbringing. So I'd been surprised the first time she had asked if she could just fall asleep in my bed (we'd been watching the Colbert Report online and she said she was too comfortable to get up). But I'd gotten used to it, and understood that it didn't mean anything. I thought that that night would be no different. I wanted to stay with her, even knowing that my affection wasn't reciprocated.

Imagine my surprise thirty minutes later, when, after lying in the dark talking for what seemed like an hour, without warning, I felt her lips against mine. It was just a quick peck, but it stopped me mid-sentence. "What was that?" I asked.

"What was what?"

I rolled over and pulled her head toward mine, and kissed her as passionately as my inexperienced lips would allow. "That," I answered.

We made out for hours, and I felt and saw real breasts for the first time in my life, but we stopped short of going further that night. The next night, after driving to a friend's place in NYC, I audaciously reached down and teased her with my fingers, but she prevented me from pulling off her underwear when I made an attempt. The third night began the same way. We kissed, I fingered her, she ground against me for all she was worth — and then abruptly she was still. "I can't help myself," she whispered in the darkness. "I want your dick."

I was stunned momentarily, but my instincts took hold and I started to fumble with my pants button in the dark. But she grabbed my arms. "You have to understand that I don't love you," she said. "If you don't want to do this with someone who doesn't love you, I'll understand."

It was at that moment that I realized that I, tragically, truly did love her. But my body didn't give me time to think about how miserable that would make me in the near future. I wanted her more than I had ever wanted anything before in my life. Every fiber of my body was screaming at me to stop stalling, to pull this girl against me as tightly as I could and never let go. I pulled down my pants, peeled off her underwear, and lay on top of her, hard as a rock. I whispered breathlessly, "That you would ask that question means that you care. And that's enough for me," and slid into her.

My unrealistic expectations and her relationships with other boys spelled disappointment for me and disaster for our friendship. We had sex a few more times, but it was never like the first time again. It was worth it though, for that one night, that one hour of honest innocence and senseless happiness. I'll never forget it, and I'll never forget her.