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.

He was allowed to sleep over, as long as he stayed in the basement.

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 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 (39 Comments)

Mar 29 11 - 12:07am

Awww! i quite like this one. i wish she said how old HE was though. and how long the relationship lasted.

Mar 29 11 - 12:35am

Great story and great job as usual on the illustration Thomas.

Mar 29 11 - 12:48am

So the author was 17 and Charlie was old enough to be an "accomplished programmer"? Sorry, but these sorts of situations never sit well with me. Regardless of how much of a gentleman Charlie was, he was very nearly a statutory rapist, as the age of consent in New York is 17.

I wish this young woman could've had such a positive experience with someone who was closer to her own age, as I don't believe that ALL high-school boys are "shitheads." Certainly, a lot of them are, but not all. And certainly, if she couldn't meet any non-shitheads in her own immediate peer group, she could've extended the search to the Internet and found one there just as easily as she found Charlie.

Moreover, I wish Charlie, a grown man with a career, wouldn't have been as blase as he apparently was about fucking (1) a high-schooler, who was (2) just barely legal, and who, for all he knew, was (3) still lying about her age and was actually younger than the age of consent.

Mar 29 11 - 1:44am

Well, I think it's totally icky. Especially since she didn't say just how far apart they were. I think teenagers should be encourage to play amongst themselves since they're all so new to this and still not quite adults. It's definitely icky when anyone, who is probably a few years out of college, is willing to date a high schooler who probably hasn't experienced that much of life yet.

Mar 29 11 - 2:27am

I think both of you missed the forest for the trees, here. Yes, they were at different ages, nearly straddling legal barriers. But it's quite clear that it was a respectful, satisfying relationship for her, which is more than most girls can say of their appropriately-aged high school boyfriends. It doesn't matter if ALL high school boys are shitheads. She found someone who made her happy. Their respective ages change nothing about that fundamental truth.

Mar 29 11 - 8:47am

Who said he was a grown man with a career? I was an accomplished programmer with my own business well before graduating high school. I'm not necessarily condoning anything, just saying don't be so quick to judge. And I totally agree with 'dude' above.

Aug 03 11 - 3:58pm

Excellent point.

Nov 10 11 - 9:51pm

Everybody is surprised at their age difference. I am flabbergasted at how her parents were ok with their 17 yr old daughter coming home with a guy in his mid 2os.

Mar 29 11 - 1:06am

You're absolutely right "concerned". American consent laws are perfect in every regard. Every human being in this country isn't ready for sex until the second they turn 17, and us prosecuting kids for sexting and couples who are only a couple years different in age has been a flawless excercise in ruining lives over a victimless crime.

For real though, go away. If you want to get your moralizing rocks off over age differences in sexual relationships, go somewhere else.

Mar 29 11 - 2:49am

Here here! f her parents were okay with it, and the age gap was close enough for them to be seen together in public, and he made her feel so much better about herself and her body, then who cares!?! I thought this was ace :)

Mar 29 11 - 10:09am
Still "Concerned"...

Ryan and R, age-of-consent laws exist in order to protect kids/teens from adult exploitation. The line has to be drawn somewhere, and if you think otherwise, then we should end this discussion now.

I've already conceded that no laws were broken in this case. And I'll go on to concede that when it comes to age-of-consent laws, they are as imperfect as most laws. (Though, I would like to point out that in the present case, we're not talking about a 17-year-old sexting a 15-year-old. We're talking about an adult man fucking a 17-year-old high-schooler.)

And yet, regardless of the exceptions (the relatively mature/outgoing/confident teens, and the relatively immature but well-meaning grown-ups), of which there are some, I maintain that, in general, a 17-year-old high-schooler should not be allowed to pursue a romantic/sexual relationship with an adult. Because even if the kid doesn't know any better, the adults (her parents and Charlie) should, if only to prevent this barely legal teen from waking up years from now, and seeing Charlie in the predatory light that he may need to be cast in, and seeing herself as the oblivious, self-deluded, desperate little kid that she may have been.

And anyway, are we really prepared to encourage men like Charlie to seduce and fuck teenage girls who have to turn to the Internet for a self-esteem boost? That sounds exploitative, almost predatory, to me, since a 17-year-old's emotions can (in general) be manipulated more easily than someone who was, say, Charlie's own fucking age.

Moreover, whose to say Charlie wasn't putting on an act just to prey on an insecure kid, whose pants were apparently pretty easy to get into? That he lied to his friends about her age tells me that he knew there was something wrong with the whole situation and with what he was doing.

And that the author didn't think twice about sleeping with a man who "was somehow okay with the fact that [she] wasn't [18]" tells me that since she wasn't mature enough to appreciate the possibility that she may have been being exploited for her age and for her easy-to-get pussy, she had no damn business with grown-ass Charlie.


Mar 29 11 - 1:11pm

And yet it's funny that you think you know better than all of the adults involved here (Charlie, her parents) despite knowing next to nothing about her situation or their relationship. If you thought that he was seducing and fucking 17 year olds for a self-esteem boost, or was just exploiting her because she was "easy" (they dated for months before having sex, excuse me, what?) it was entirely a construct of your mind. You imposed an entire persona on him that did not exist in the story. I think you have some personal shit to unpack, and that is the only thing revealed by your angry, paranoid and overreaching rant.

Apr 03 11 - 6:18pm
agree with dude

Yes. And furthermore, this part of the site is for sharing personal stories. She didn't post the story for your blind judgment and cruelty. I think she's very generous for sharing such a personal memory.

Mar 29 11 - 6:50am

Fake enough to not be worth getting yer panties twisted!

Mar 29 11 - 11:12pm

Why do you think it's fake?

Mar 29 11 - 9:22am

Ok, the majority of this story aside and all...quick little question. I'm a grown ass woman (30) and I am comfortable with my body, not offended by any word, act, proclivity, fetish, NOTHING...but the phrase "eat me out"? Not only does it sound completely vile to me, but like what 12yr old boys call it before they really know what it is.
Anyone else?

Mar 29 11 - 1:13pm

Well you're clearly offended by some words. And some seriously mild ones at that.

Mar 29 11 - 5:57pm

I agree.
It's at best unappealing.

Mar 29 11 - 9:52am

What is with the obsession about her cumming? Who comes their first time?

Mar 29 11 - 11:15pm


Mar 29 11 - 11:23pm

yeah, that whole taking offense at her not having an orgasm thing is what turned me off about the sound of this guy, not the age of consent stuff.

Mar 30 11 - 8:21pm


Mar 29 11 - 10:05am

In editing this, I cut a line indicating that he was 20. Don't nobody panic. :)

Mar 29 11 - 10:29am

All due respect, that Charlie was 20 seems too pertinent a piece of information to have cut, given how this story can read without it. I wish I would've known his age at the outset...

Oh well. Bygones. My opinions on age-of-consent stand. Carry on.

Mar 29 11 - 5:32pm

I think knowing that he was 20 and she was 17 is an acceptable age difference, he made her happier than lots of high school boys would have. It appeared to be a healthy relationship, one she dose not sound like she regrets or felt like she got used.

Also using the divide by 2 than add 7 rule that is acceptable.

Mar 30 11 - 12:54am

Illustration is wonderful!

Mar 30 11 - 2:26am

There is a big difference between offended and grossed out. Having a guy say "can I eat you out?" is not at all sexy. Either just do it or call it something (anything) that sounds a bit more mature, is all I'm saying.

Apr 04 11 - 3:46pm

Out of curiosity, I looked up the statutory rape laws for each state. It's interesting to see how different states regulate this issue, both in the ages they designate as appropriate and the words they use to refer to the people involved. Check out the wording on the law in Massachusetts. Here's the link:

Apr 10 11 - 12:57pm

I feel so weird reading about all of these folks who lost their virginity at 17. The stories always have a strange innocence about them. I would love to hear from others who lost their virginity a bit later in life (25-30) so I'd have something to relate to.

Apr 13 11 - 7:55am

Glad I've fnially found something I agree with!

Apr 13 11 - 2:42pm

Kudos! What a neat way of thniikng about it.

May 01 11 - 4:00am

I agreThis is this the worst age of losing virginity

May 24 11 - 5:39pm

this story creeped me out. i pictured an overweight, nerdy 17-year-old banging a 30-year-old, skinny, weird, computer programmer.

Jun 16 11 - 10:45am

have you seen david karp, creator of tumblr? in the modern age of technology, some programmers (despite the stereotype) manage to be quite attractive.

Jun 15 11 - 5:59pm

How nice if yls (8/9/87) give her first time to me. I, shp will love and take care of her till end of our life...........

Jun 23 11 - 2:08pm

Lovely story, thanks for telling.

Jul 20 11 - 1:27am
Steve P

If she waited another year she can shag this 46 year old programmer.

Mar 12 12 - 12:40pm

Things to read before sex.. makes our orgnism pumped-up..!

Aug 24 12 - 9:38am

I did not get the story...