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My First Time
Illustration by Thomas Pitilli
Female, 17, New York
I met him on the internet, but to our friends, we met at a small coffeeshop one night. In reality, at seventeen, I had finally accepted the fact that all high-school boys were shitheads. I had barely any female friends, and therefore no one to discourage me from lying about my age online. A dating website used for an occasional ego boost transformed into a way I could potentially meet interesting guys for real.
We met at the Museum of Modern Art, only after talking extensively via text. I understood the potential danger of the situation, but wasn't discouraged. Charlie was tall, blond, and impossibly thin with a light beard. Argumentative and difficult at first, babbling about sci-fi novels and fonts, Charlie was an accomplished programmer who, I learned, knew next to nothing about art. I was the creative type, sharing with him my love of writing and design. He was the technical, logical boy who wanted to learn about the beauty of the world.
Our first date involved getting lost on the subway, finding the coffee shop we'd soon lie about, and a party where I lied to my parents through the nose just to keep the night alive. Over the next three weeks, Charlie and I saw each other on weekends, texting often. We mused about summer road trips and adventures throughout the city.
One weekend, Charlie was invited to a birthday celebration at a coworker's apartment, and invited me along. Arms around each other on the walk over, we discussed our story. "Yes, that coffee shop. I told them you were eighteen." (He was somehow okay with the fact that I wasn't.) Eventually, my curfew loomed. I had a train ticket and schedule in hand, but Charlie insisted on driving me home. He had done this once before, romantically whisking me home but leaving just shy of four in the morning, his main concern to avoid upsetting my parents.
He was allowed to sleep over, as long as he stayed in the basement. Slightly drunk from the evening's activities, I dragged my bedroom blanket and pillows to the basement carpet and plugged in my lava lamp. We lay making out for a while on the floor before he started to eat me out, despite the fact that a missed birth-control pill had lead me to bleed earlier than I expected.
Something changed. We had talked about sex before, our conversations surprisingly open and constructive. I felt so strongly about Charlie. Our plan was to wait awhile until things between us were more definite. But in my basement, pink lava lamp illuminating us, I realized that it was okay. Charlie was convinced I had some sort of perfect first-time fantasy in my head, but the truth was that I'd known from maybe the second time we hung out that he would be the one to take it from me.
"Are you sure?" he asked me, and I said yes. I crawled upstairs for the condoms I had received as a gag birthday present when I turned seventeen.
Slow at first, we were both sitting up. He moved slowly inside of me. I had heard other girls complain of sharp pain, but I only felt pressure. It was different, and pleasant. "Different from fingers, right?" he asked. I nodded.
We moved in different positions, trying to find what would be most comfortable for me. Charlie was an absolute gentleman, and read my moans as pain or pleasure almost perfectly. My legs draped over his neck, around him, I tried riding him from the top. Sitting on his lap, we both were close to coming but neither of us did.
I must have lasted at least a half hour before the pressure became uncomfortable. At one point he put his white t-shirt underneath us to avoid bloodying up my sheets. But I told him we had to stop, and he obliged. We lay holding each other, naked, making quiet conversation. He was deeply disappointed that I didn't come, personally offended.
Orgasming had been difficult for me; I'd been unhappy with my body for years. Anxiety had created a mental block, making it near impossible for me to even get myself off. But lying there with Charlie, I felt proud that my body could make him moan the way he did. I reassured him that it wasn't his fault. He understood.
It was five a.m. Charlie insisted I go upstairs to my room to sleep. I made him a bed on the basement couch with one of my pillows and tucked him in. Kissing him goodnight and ascending my stairs, I didn't feel different. No regret flowed through my body. I felt serene and exhausted. Slightly sore, I crawled into bed. The next morning, his car was still there.We're looking for stories about the first time you had sex. Email firstname.lastname@example.org with 500-1000 words. (Don't worry, we won't print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.