Love & Sex

My First Time

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Male • 16 years old • Baltimore, MD

The main thing I remember from those years was being constantly, embarrassingly, throbbingly perpendicular to myself. Every time I stood up, my hard-on reached straight out. I was hard while surveying my lunch options in the cafeteria, hard while failing to learn to skateboard, hard while shuffling up to the whiteboard in math class. Luckily, this was the nineties, and the late-grunge uniform of baggy cargo pants and oversized flannel shirts made it easy to hide my yearning cock. I feel sorry for the sixteen-year olds in skinny jeans today.

Illustration by Thomas Pitilli

Somehow, I attracted a girl. And not just any girl — Gretchen looked like a teenage Björk. She was short, and sweet, and sullen in the endearing way sixteen-year-old girls can be sullen. In seventh grade her dog bit me, and from the moment she told me I deserved it — and I did — she had me. I still don't understand how I got her. I can look back and decipher how I charmed some girls, what they fell for, but I have no explanation for Gretchen. I know she liked my scruffy beard, my brown leather jacket, and the way I ostentatiously read the newspaper every morning in homeroom, but it's hard to imagine any of that actually worked. Ours was my longest, healthiest relationship.

She taught me that sweet, sullen, dark-haired girls can have dirty plans. I remember my genuine shock when her searching hands first found my dick while we were making out on a picnic blanket on our third date. Until then, it was difficult for me to believe that my hard-on would ever be something I didn't have to hide. That Gretchen went looking for it was a revelation.

After months of play, she decided that it was time to move on to sex. I wasn't ready, but that seemed like a ridiculous thing for a teenage boy to say. We nuzzled on her mattress, lying below her Red Hot Chili Peppers poster in her mother's brick row house. I could feel my heart thumping in my ears. As I climbed on top of her, my mouth on hers and my hands up above her head struggling with the condom wrapper, my ever-hard dick softened. It just shrunk from her. I silently begged it not to play this game. Not now. The only part of my body I had any interest in was deliberately and spitefully failing me.

Gretchen broke my hot, frustrated tugging, dragging me back to her mouth, silently making it clear that nothing had to happen that night. We kissed until my anger and shame subsided, then I went down on her and we fell asleep. Her wordless embrace was the most reassuring thing anyone has ever done for me.

Two weeks later, my parents were out of town. We lay on my twin bed, jutting out into the middle of the room. I remember feeling like the whole world was organized around this moment. This time, my hard cock barely noticed the pressure, or the condom. One of her hands wrapped tightly around my shoulder, her other palm pressed against my pelvis. I tried to be as gentle as possible while still doing what I needed to. I don't think it hurt her too much, and, after that first push, we got some actual grown-up sex in. I came, and she shook with a deep, quiet, tectonic stirring somewhere in her core. Afterwards, we sat in bed, with my cock spent and soft, pressed against my inner thigh.