My First Time

Male • 15 years old • New York City

The first time I had sex... well, almost had sex — I'm counting it because it's the closest I ever came with a woman — was in the mid-'80s (of course it was), in the back room of a strip club off Times Square, with a dark-skinned hooker called "Baby," who, true to her name, reeked of the powder-fresh goodness that can only be found in a bottle of Love's Baby Soft.

Illustration by Thomas Pitilli

I was fifteen and fighting with every ounce of my power not to be gay. This brought me here, two-and-a-half hours south on the bus, to a sad little side room with a mattress, an apple crate, and — I don't exaggerate — a lamp with a bare light bulb and no shade. There, I listened as my best friend and object of my every secret carnal desire, George, lost his virginity, quite loudly, with a German named Daisy, just opposite the wall to my right.

My heart could barely stand it. I thought he was like me. Hadn't he too been dodging and shifting around in his make-out sessions with girls, petrified a fumbling hand would land on an obviously soft penis? "What's wrong?" "Are you okay?" I'd cover with everything from a stomach ache to Catholicism, knowing full well this was another girlfriend I'd never call again, number seven on a sexual-amends list that was projecting way too far in the future.

I was always hoping something would stir in my pants. I wasn't cruel — I liked these girls. I kept waiting for one to fix me. I'd hoped two weeks ago it was Marlene. At a pool party, I pulled her aside for five minutes of carefully orchestrated "Oooo, this is so hot, we could get caught" time so I could fingerbang her and gauge just how I felt. (Sad, and like I needed a Wet-Nap.)

This was my last-ditch effort. Baby looked like Coco from Fame. I thought she was exquisite. She looked at me and smiled and I lifted her chin and kissed her. It was sweet, which I knew was probably wrong, so I pressed down hard with passion. I took her pretending she was George, not the George in the next room but the one who'd ask me for a T-shirt to borrow. I couldn't get past my nerves, the voices of coaches, of brothers, of God, the pressure exploding in my head that made everything go limp down below in my loins. I truly believed if I couldn't perform with Baby then I might as well pack it in.

Finally, I stopped. I couldn't avoid Baby's hands any longer. Nothing she did made a difference. My dick was a dismal wreck. There was nothing to do but roll off her, and crumble in a ball at her feet.

"You gay?" she asked in a voice so soft she was my mother.

"Yes," I said simply, before I could think. There it was, no denial, in front of me, for the first time out loud, for someone else to judge and to mock me.

"It's okay!" she practically screamed, dismissing my angst so succinctly I had no other choice but to believe her. Baby was wise to the future. I heard taxis and laughter and night. George was finally quiet, I heard city and possibility, and I smiled. It was okay. Best money I ever spent. Baby showed me it's okay.

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 (24 Comments)

May 25 10 - 12:50am

Funny, sweet, vivid, well-written.

May 25 10 - 5:01am

Good for him.

May 25 10 - 7:33am

I read all of these, and I think this is my favorite yet. I thought it was touching.

May 25 10 - 9:48am

I wish my coming-out story was so sweet!

May 25 10 - 10:31am
Johnny Chicago


May 25 10 - 12:29pm

Beautiful. Sweet, funny and so well written. Thank you.

May 25 10 - 1:59pm

Many an epiphany has been delivered by the hands of a hooker. Nicely written.

May 25 10 - 2:09pm

Loved it. It's my favorite First TIme.

May 25 10 - 3:04pm

This was tenderly and beautifully written. A pleasure to read.

May 26 10 - 2:15am

This is the only one of these stories that I have ever liked, but I really, very much liked this one.

May 26 10 - 5:09am

Absolutely wonderful writing.

May 26 10 - 6:28am

Meh. Fake.

May 26 10 - 6:39am

I loved it. (and I don't love most of these.)

May 27 10 - 5:01am


May 27 10 - 11:19am

How do I get the writer's number?

Jun 20 10 - 11:19pm

baby was wrong

Jul 06 10 - 4:35pm

That story gave me a woody

Jul 27 10 - 9:21pm

Oooooooh, that's sexy in at least a dozen different ways!

Sep 01 10 - 4:09pm

Aww, that's sweet :]

Feb 10 11 - 7:32am

Looks like, your trackback doesn't work. Can I ping your site?

Feb 18 11 - 11:33am

Whay are you don't publish actual news?

Jun 08 11 - 7:21pm

fucking fantastic.

Jun 30 11 - 4:11pm

Interesting story, even though not a First Time in the sense of this column, right?

Sep 18 11 - 5:19am

I liked this story. No I loved it. I know how awful it is to be in love of someone who is not into you. I've been there before. I give the writer props for being able to admit it to himself and baby. I hope he ended up with someone right for him.