I Was 27, He Was 19: What It's Really Like To Sleep With A Virgin

He kept asking: "Am I doing okay?"

I Was 27, He Was 19: What It's Really Like To Have Sex With A Virgin VGstockstudio / Shutterstock

I was 27 when I met "David." He lived in my neighborhood and we seemed to have the same schedule because we would see each other all the time.

Whether I was grocery shopping, getting cash from an ATM, enjoying Happy Hour, or just simply wandering around on a Saturday, I would always see him.

It became a running joke with my friends that I was stalking the pretty boy. It also became a joke between David and I, because after several months of awkwardness (it was really that often), we finally started acknowledging each other with smiles and nods that eventually evolved into waves and small talk, and soon, full-fledged banter.


One night, while waiting for my roommate to meet me at a bar just a block away from my apartment, David approached me.

He had definitely been putting a few back and was, apparently, ready to officially introduce himself.

He was from New Hampshire, like me, and had only been in the city for the six months that I had seem him around the neighborhood.

We didn't really talk about our present lives or what we did professionally, but more about the things from our past we had in common: the summers along the Kancamagus, the high school trips to Canobie Lake Park, and Bill Cahill's Super Subs in a town not far from both of ours.


We made out on the sidewalk that night, exchanged numbers and went for brunch the following day.

Soberly, I realized David was a little younger than I originally thought.

At 27, I had lost that idealistic way of looking at the world, and yet he still clung to that perspective.

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I assumed he was maybe 24, so I asked him. He agreed he was 24, then he laughed and said it was more like 23, then he laughed again and said he wasn't quite 23 either.

I was getting nervous. I wasn't sure what the New York State laws were on making out with an underage boy and started figuring out what I would do if he finally revealed he was 17 or something.

He kept laughing; I didn't. I wasn't about to be the neighborhood Humbert Humbert, I told him. The literary reference went completely over his head.

Finally, after much discussion, several fits of laughter on his part, and my threats of getting up and leaving, he handed over his license.

I'm not so good at math, so it took me a second to figure it out based on his birth year: he was 19.


And not just that, he had just turned nineteen a couple months before, while I would be 28 in a few months.

I was appalled. I was an adult, I was a woman, I had been out of college for years, I practically had a career (if one considers "answering phones and reading Gawker all day for $15 an hour" a career).

I decided I would finish out the meal and walk on home; and when I told my friends the story later, he'd be a respectable 23 and we would laugh, and I would've been able to say I once made out with a boy born in the mid-80s.

When I told him I was 27, he seemed shocked. "I thought you were my age," he said sweetly.

Since he was very cute, with this light brown wavy hair that sort of swooped nicely over his brow and lovely green eyes with little specks of orange in them, I did what any rational 27-year-old would do: I took him home after brunch.


We fumbled like teenagers, because, well, he technically was.

There was this long, extended dry-humping session that I thought was never going to end, so being the adult, I started to remove his clothes.

He was a phenomenal kisser: more lip than tongue, and he peppered his kisses with little bites, so based on that, I wanted more.

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Just as I started to pull off his boxers, he stopped me. This was a first.

"I've never done this before," he said.

"Never had sex with someone you barely know?" I asked.

I wasn't exactly an expert in the field either, but he was so pretty and tall and thin and his golden body was stretched out so perfectly in my white sheets, so how could I not?


Then the ball dropped, as they say. "I've never had sex." I laughed. I thought he was kidding.

I mean, look at him! How it was that some lucky girl hadn't nailed him didn't seem to make sense.

He explained that he wasn't religious, he wasn't a prude, it just never happened. He had dated girls, but being so shy it just never "got that far."

Despite all this, he wanted to do it now, but he thought I should know. So I took off his boxers, threw them on the floor and proceeded to have sex with a virgin.

I felt this strong sense of responsibility.

I knew that he was going to be stuck with this memory for the rest of his life, so it was my job to make sure it was a good one.


I had slept with two virgins in my life: my high school boyfriend John, when I was also a virgin; and David. In between John and David, I had definitely acquired quite a bit of experience.

So while I never thought John sucked in bed, I also didn't know any better either at the time; experience taught me otherwise, of course.

But he was a virgin, we both were, I'm sure I sucked, too. Hell, maybe I still do and no one has been brazen enough to tell me.

Once we got to the actual intercourse part, things got shaky.

While he was able to move his hips with mine during the two plus hours of dry-humping, when he was actually inside me, he lost all sense of rhythm.


He kept thrusting himself so intensely that I thought for sure he was going to throw-out his 19-year-old back.

And he couldn't stop trying to reach for my boobs, as if he were scared they were going to go somewhere if he didn't hold onto them for dear life.

So there I was, straddling this boy, being thrust all around like some sort of rodeo ride gone awry, with my boobs cupped in his hands and him asking me, "Am I doing OK?"

Honestly, he should've been asking me that, because I was seriously considering my life choices at that point.

Just as I was about to suggest we do something else and try again later, he came. He lay there looking up at me and smiling, and all I could think was, "Great. Someone in this room had an orgasm."


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I wasn't being harsh. I wasn't being rude. I was just confused. I also wasn't looking for anything serious; I just wanted to get laid.

And when you want to get laid on a Saturday afternoon, you don't want the pressure of being someone's "first time" hanging over your every movement.


After we lay there a little too long for my liking, we went out, got some coffee and hung around Tompkins Square Park. I preferred David outside the bedroom.

Surprisingly, our bedroom activities got more and more fun and less awkward. He smoothed out the rough patches, finally learned how to move his hips and be less nervous.

I wouldn't say he was the best lover I've ever had, But I imagine he's come along quite nicely and whoever is sleeping with him now is probably not disappointed in the least.

We dated for a few months. And the whole time I did so with my foot out the door.

I wasn't looking for something else, someone better, or even someone closer to my age  I just knew in the long run it wasn't going to work.


He was still in college, he had his life to live and all these experiences to have, even if I had allowed myself to love him, it would've been so selfish to keep him from all the fun life had in store for him.

If it had evolved into something more than a few months, I would've trapped him and he would've resented me later for it.

Had we met in any other place, our short-lived relationship would've been near impossible.

New York City tricked us into believing the age gap wasn't there, but it was. It wasn't about the numbers attached to us; it was about the life in-between.

We exchanged emails for a while, even after he couldn't take the city anymore and moved back to New Hampshire to continue his education at Dartmouth.


I still hear from him from time to time. Once, not too long ago, I got an email from him where he said I was his first love.

I wanted to tell him I wasn't at all; I wanted to tell him the difference between sex and love, but realized it wasn't my place to do so.

To quote Oscar Wilde, "I'm not young enough to know everything." By that rationale, I should just keep my mouth shut.

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