Love & Sex

My First Time: Female • 24 years old • Tokyo, Japan

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Illustration by Thomas Pitilli

Female • 24 years old • Tokyo, Japan

I was living alone in Tokyo, knowing almost no one, when I met this guy on a dating website. He liked breasts. I have nice breasts. It seemed like a good match. He was older and more experienced than I was. But when I talked to him, I felt amazed by how alike we were. We were different too, but he felt like a real person to me. So few people seem fully real to me. I might have loved him a little bit, for all his flaws. We kissed in a karaoke room at 5 a.m. I was tired and drunk, but I knew he wanted me. It excited me — I wanted him too. He touched me on a bridge in the city, pressed against the railing, his hands in my hair, and I knew this was it. I felt ridiculously, breathlessly turned-on. I could do this thing. It wasn't impossible.

He liked breasts. I have nice breasts. It seemed like a good match…

We made out like teenagers on the couch in my apartment. I kissed him, and he put his hands down my pants. He put his mouth on my breasts. I told him I was a virgin via email. It was almost impossible; I didn't think I could actually type the words. I felt incredibly awkward about it. My chosen partner was not a comforting person, either. But maybe I didn't want comfort. I wanted it to be over.

So I went with him to a love hotel. It was almost comically awkward. I was going to a love hotel for the specific purpose of losing my virginity. It was okay. I was going to be okay.

We watched TV and he held my hand and touched my hair. We started kissing, and I liked it a lot this time. I licked his collarbones and I took off my shirt. There was another first — shirtless in front of someone who wanted to have sex with me. Then he put his hands down my underwear. Another first. For a second, I was terrified. I wanted to stop him. Was I really going to do this? For that moment, I was here and alive. It felt like reality was ten times more intense than usual. All that overlay of narration that my mind usually places over my existence was stripped away. I felt that way you do sometimes when you look in the mirror — a kind of mental vertigo. How is it possible that I exist here and now in this universe? It's madness.

Then I realized it felt really good. He fingered me, and I wasn't sure what to do with my hands or the rest of my body. I was still a bit terrified. I ran my hands over his back and just held on. He kissed my breasts and then he went down on me. It felt almost impossibly good. I wasn't really sure if I came or not — it didn't feel like my usual orgasms did — but when he stopped touching me, I felt pretty satisfied. Then I touched him, my palm against bare skin. Then I didn't really know what to do. It was weird and awkward, and I was obscurely afraid of hurting him somehow, or ruining the mood. He put his hand over mine and showed me. And then, before I knew it, I was giving a blowjob. After he came, we made out some more, and he fingered me a bit again.

Then he wanted to fuck me. I was pretty scared. I knew it was probably going to hurt. I was afraid it would just hurt and hurt and be really unpleasant.

We started out in the missionary position, him between my legs. At first it wasn't so bad. It felt strange, but a little familiar, not much different than a few fingers inside of me. But when he pushed further inside, it started to hurt. It really hurt. It felt like he was pushing against something solid, like something was ripping inside of me. I put up with it for a while, presuming that it would end, but it didn't, and I eventually pushed him away when an extra-hard thrust really hurt. He pulled out, and it was really awkward for a second.

Then we realized that it was supposed to be easier with the girl on top, so that's what we did. It still hurt at first, but I could control the amount of penetration, and maybe it had started getting better by that time anyways. I can still remember when it started feeling good. I couldn't tell at first if it was really pleasure or pain — just another cliché that turned out to be surprisingly true. Then it became a bright pleasure that ran up the back of my spine like bright sparks. Feeling him pull out of me was the weirdest experience.

Somewhat oddly, my first feeling after we finished was relief. I said, "Oh, thank God. That started feeling really good." An awkward end for an awkward beginning. When he left that morning, I already suspected I'd never see him again, and I didn't.