My First Time


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.

We're looking for stories about the first time you had sex. Email 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.
According to just about every pre-college advice manual, floorcest is a bad idea.
"So no, I didn't lose my virginity in the most traditional way."
"He looked like if Ian Somerhalder and Gerard Butler had somehow created a baby."

Commentarium (27 Comments)

Dec 07 10 - 4:40am

i don't get the point of going all the way to the love hotel after a hot makeout session in one's own apartment. fake much?

Apr 11 11 - 8:08am

popular culture in japan. i don't know if that was the case for the author, but i do know that it is for some others.

Dec 07 10 - 4:46am

Did it... did it hurt? Did it really hurt? Not sure if the awful, clunky, fucking FAKE writing conveyed that it HURT so much.

Can we please stop having 15 year old boys submitting this shit now?

Feb 10 11 - 10:41pm

i concurrrr

Dec 07 10 - 4:58am


Dec 07 10 - 7:48am

Love hotels are places in Japan specifically where couples may have privacy to have sex. From my understanding, apartments in Japan tend to be small and there's some privacy but maybe not enough to suit Japanese ideas of politeness. Nobody wants to hear you getting it on in the next apartment, so to speak. Therefore, love hotels. Didn't sound fake to me.

Dec 07 10 - 8:22am
random but

Nice illustration! Seems to go with the idea in the (albeit doubtfully true) story of her slowly letting go of her fears. Also reminds me of that Beach Boys song: "flowers in her everywhere!"

Dec 07 10 - 11:54am
conspiracy theory

I love how people always claim 15-year-old boys are writing these. Like 15-year-old boys a) are fantasizing about women unsatisfyingly losing their virginities during ambiguous relational brokering with emotionally distant older men, or b) don't know how to point their browsers to YouPorn.

Dec 07 10 - 4:34pm

"flowers in her hair" was from "The rain, the park, and other things" by The Cowsills, not The Beach Boys.

Dec 07 10 - 5:14pm
@conspiracy theory

You beautifully stated what I was thinking. Haha.

Dec 07 10 - 11:44pm

This is not unlike my first time. Not every first time has to be completely dreadful and thus fake, if the woman enjoyed it at all)--I image it's often a mix of icky, painful, fun, scary, and hot. Like mine, like this girl's. And yeah, it hurt. A lot. Really, a lot. And I was not a shrinking violet--I knew how to make myself come, I really thought all those years of riding horse and whatnot had done in any hymen. Nope.

Dec 07 10 - 11:48pm

This is kinda eerily similar to the way i lost mines except i had a two-night stand haha

Dec 09 10 - 4:14am

i live in japan. there are many reasons i think it's fake, but one is that a) the fact that she lost her virginity at 24 leads me to believe she's japanese, and b) i've never met a japanese person who can use that much english slang correctly, especially not sexual slang from someone who waited until she was 24 to lose her virginity. i could be wrong in that she isn't japanese, but what's the chances of someone adventurous enough to live in tokyo by herself still being a virgin at 24? i maintain: fake.

Apr 11 11 - 8:10am

my cousin is 26, a virgin, living in tokyo by himself.

Jun 26 11 - 4:07am

strangely enough I came to tokyo and lived alone and also lost my virginity at 24. I am not Japanese, but the guy was. I think the story may be legit. The part about never seeing the guy again...that rings oh so true.

Dec 09 10 - 12:42pm

what a weird batch of assumptions to make. you have be japanese to lose your virginity at 24?

Dec 09 10 - 1:30pm

agreed, also, you have to be completely ignorant of basic sexual slang most people learn at age 10 to be a virgin at 24? You need to be a complete hermit with no sense of adventure or wanderlust to be virgin at 24 instead of just a regular person who had some bad luck on the dating scene?

Dec 09 10 - 5:35pm

So much cynicism....Shut up and let you mind enjoy the fantasy. Sheeeee!!!!

Dec 11 10 - 5:21am

I would have hated to lose it to a stranger-esque guy! :<(

Dec 17 10 - 9:20pm

Who cares if it's fake or real when it's written this poorly?

Dec 23 10 - 7:08pm

Really! I totally agree. No one should give a shit when its not even worth reading all the way through. Whether 15 yo or true Japanese woman, they can have this weak story BACK!

Jan 07 11 - 4:37am

Wow... was I the only one who liked this? I related to the part about stripping away the usual narrative that hangs over reality. I have some questions as to the details, but it didn't seem entirely unplausible. I've known girls who were plenty adventurous, liked to travel abroad, etc. but hadn't had sex by age 23 or 24.

Jan 07 11 - 4:38am

Wow... was I the only one who liked this? I related to the part about stripping away the usual narrative that hangs over reality. I have some questions as to the details, but it didn't seem entirely unplausible. I've known girls who were plenty adventurous, liked to travel abroad, etc. but hadn't had sex by age 23 or 24.

Feb 13 11 - 2:21am

yeah, we 23 year old virgins do exist. and we do travel, asshat.

Apr 11 11 - 8:11am

thaaaank you!

Jun 23 11 - 5:16pm

Thanks for confiding, enjoyed the read.

Oct 07 11 - 2:36pm

Iam the most happy person of the world b'coz i ever listened to my parents