My First Time

Illustration by Thomas Pitilli

Female • 17 • Florida

I fell into my first serious relationship directly before my senior year of high school. He was a late-bloomer and our school's much-maligned valedictorian. I was passing the time until graduation by working the prop table for the school musical and cultivating my image as a nonchalant bitch. While we'd known each other for seven years, we were only beginning to hang out. That led to an awkward courtship, which preceded a wonderful, caring, surprising relationship. I had always thought of him as critical, and, well, there was a lot about me to criticize. I was relieved at how wrong I was. He fell for me rather quickly and didn't merely tolerate my eccentricities: he found them adorable. I was his first kiss. He was everything I could have wanted — intelligent, witty, and secure all wrapped up in a package with broad shoulders and a thick cock. With each passing day, it became clearer that we were going to lose our virginities to one other.

Painstakingly planning ahead, we had decided to do it one night when my parents were out of town. It would be after one of the play performances, in which he was playing saxophone in the orchestra pit. My best friend had dated her long-term boyfriend for a little more than two months when they first slept together. In the grand tradition of competitive teenage girls everywhere, I was determined to hold out longer than my friend, thereby proving myself more pure. So he and I decided on a date three months and one day after we had declared ourselves monogamous.

He was the very definition of an overachiever. As I was overseeing the props for the show, I would occasionally harness his enthusiasm to make my job easier. That night, I sent him to the nearest store to pick up something for the show, plus an item for later that night. Twenty minutes later, he came back to my table with a grocery bag and a crestfallen face. "Do you realize what you just made me do? I just bought hot-dog buns and lube. Just hot-dog buns and lube."

He always knew the best way to get me to giggle. "Did the clerk look at you like you were going to have a good night?" I asked.

He raised his eyebrows, so dark against his pale complexion. "I am going to have an amazing night." I watched him walk away, taking care to check out his ass. I wanted to skip the next three hours, and just get him in my bed. 

Once the curtain fell, we cleaned out our lockers and drove home in his shiny red car, excitedly discussing what was to come, arguing about whether we should put down a towel. We wasted little time upon arriving to my house, immediately winding our way towards my bedroom in the back of the house. I had waited far too long for this moment, and I was sure that I wanted him.

That's when things started to get weird. Our foreplay, normally a delightful mix of tenderness and hormones, had suddenly become stilted and forced. Earlier that day, when we were hooking up in his car, I'd begged him to have sex with me. Neither of us had had a condom, so we stopped. How was it that before, when I wasn't expecting it, I was so ready but here, with buckets of preparation, I was terrified? 

He guided himself into me, a moment we had practiced for what felt like forever. "Are you sure?" he asked. His voice was a whisper, though we knew my parents were gone for the weekend. I nodded. But apprehension loomed over me. My body was stiff, but my brain was going a mile a minute.

Inch by inch, he slowly pushed into me. It felt like a battering ram was breaking through me. Screwing my eyes shut, I bit my lip. "Come on," he pleaded. "What's wrong?"

I snapped at the most compassionate person I had ever met. "I wish you were the one who had to deal with the pain!"

His face crumpled like I had hit him, and I murmured, "I'm sorry, I didn't mean that." 

"We shouldn't do this if you're going to get hurt." His huge blue eyes bore into mine. It was then that I started to feel that familiar, warm sensation behind my belly button. Jesus Christ, he was perfect. I pulled him into me, melding our lips together. I pressed against him, closed my eyes, let myself go. It was like a wall crumbled inside of me. It certainly didn't feel remotely like the amazing sex I enjoy now. Rather, a dull yet moderately pleasurable sensation, like the brief moment of relief after you scratch an itch. He finally was able to fit all seven inches inside of me. "There." He murmured above me.

And then the unexpected happened: I started to giggle. He let out a tentative chuckle, which grew into a full-blown laughing fit. Together, with his cock stuffed inside of me, we were laughing in relief. Two hours after we started this quest, mission accomplished. We high-fived. It was love.

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."