Love & Sex

My First Time: Female, 18, San Francisco

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 "He had a muscular build, a paperboy cap on, and a glow stick necklace around his neck. Stupid? Yes. Hot? Definitely."

Female, 18, San Francisco

I was a cute, braces-laden sixteen-year-old when we first met at a party. It was the first time I really went out with my friends to a party at some acquaintance’s place. Regularly, weekends were reserved for basking in my awkward adolescence with my friends, watching movies and smoking cigarettes in their backyards. But I noticed him quickly. He had a muscular build, a paperboy cap on, and a glow-stick necklace around his neck. Stupid? Yes. Hot? Definitely. His name was shortened to two boring letters: AJ. After talking the whole night, we made out on the cold floor of an empty bedroom in this shitty pool house while the party raged on outside. He was two years older, fresh from Florida, and the second penis I’ve ever touched up until that point.

Our romance (if you could call it that) consisted of hooking up on and off for two years. I was never quite sure of AJ’s feelings for me, but he would always come over when my parents went out of town. Surprisingly enough, he’d come over to talk or watch movies. It wouldn’t be until the wee hours of the morning that we’d find ourselves dry-humping on my couch with my shirt off. Or I’d sneak off to meet him after school for our so-called “coffee sessions” to catch up on our lives. After I got my braces off, he complimented me saying I had the best smile he’d ever seen. It was a pleasant friendship and I was probably too naïve to believe it was friends-with-benefits situation. To this day, I have no idea what to call it. But he made me feel sexy.

However, as the years progressed, our phone calls and hangouts slowly decreased. He found a job and went to school part-time. I was busy being a senior—hanging out with friends, applying to college, etc. But one night, my phone rang. It was AJ. We caught up for a couple of hours and before I knew it, I proposed we meet up the following week, which was my spring break.

I remember being extremely nervous to see him. He suggested I come over to his apartment (which he shared with his grandmother) since he wrecked his car a couple of months ago. We sat on his couch and settled back into familiarity of catching up on life. Luckily, his grandmother wasn’t home but it was still awkward seeing her old panties hanging to dry on a makeshift clothesline or their framed pictures all around us.

Conversation quickly turned into kissing. Then my shirt came off. He unclipped my bra with expert hands. I was used to this routine with him. Then I slowly undressed him, kissing him on my way down. Before I knew it, we were both completely naked. I had never been completely naked with him before, and for the first time I actually saw his chiseled body in bare daylight. Then I started to panic in my head. I knew what was coming. Would it hurt? Would I bleed? Could it fit in me? I didn’t know what to expect but I felt a longing for him to just do it already. He laid me down on his couch and told me to relax, reassuring me that he’d be gentle and that I had a beautiful body.

He got up to get a condom and expertly put it on. It felt like ages to get all of it inside me. It wasn’t painful but a bit uncomfortable. He whispered to me that I was bleeding a bit so he’d stop. We repositioned so I’d try from on top. But it wasn’t much better. I told him, “This isn’t working…” He kept reassuring me it was alright and if I wanted to stop then we should. But I was determined. I led him to the shower and we continued there. I don’t know what it was about the water or the shower but the discomfort of constant thrusting started to feel better. Pleasurable almost. But after about five minutes of fumbling on my part, we decided to stop. He didn’t come but he said it didn’t matter because he wanted me to enjoy it at my own pace.

We eventually got dressed and kissed a little more on his couch. I left his apartment shortly after. He walked me to his car and opened the door for me. He kissed me goodbye and sweetly told me to call him again so we could hang out again. We kept the phone calls going on and off for a year but we never met up again.