My First Orgasm with Another Man

I Made Love the Way I Knew How

This was my very first published article on Medium, back in March of 2020. I was excited to revise it for my new followers and subscribers in 2024. Enjoy!

I’m trying to remember when I first learned about Christopher Street, and the Stonewall Riots and Gay Liberation. When did I start thinking of that history as my history? When did I start referring to queer people as “us”?

I do remember vividly the first time I stood on the Christopher Street Pier.

It was the day after I had my first orgasm with another person — an older man I met at a film festival in Boston. He caught my eye at the after-party and asked me to dance. The next thing I knew, we were around the corner, in an alley, up against a doorframe, with his hand down my pants.

“The things I would do to you,” he moaned, running his hands all over me. He convinced me to come to New York the next day, to sleep with him. And then his friends came around the corner and dragged him away, teasing him — “Oh my God, why are you making out with a 12-year-old.”

They were right — I looked young, and felt young. I was far too old to feel so young — a year out of college, and still a virgin. That night I road the train home thinking, “It’s finally going to happen!”

But in the harsh light of day, on a four-hour Greyhound, my enthusiasm was diminishing. This man was thirteen years older than me. Imagining his saggy belly on my back, and his thick hands pawing me in the dark, the euphoria was gone completely.

I got off the bus at Port Authority in the afternoon, and he called me to clarify that he wouldn’t be done with rehearsal until 8 pm. So I had time to kill. I had coffee catch-ups with a couple old friends, and then wandered through the village, dawdling on Christopher Street.

I tip-toed over the cobblestones, past the leather shops, and neon rainbow signs. I bounded across the highway to the Hudson River and walked out on the Pier. I stood at the head of that phallic slab of concrete penetrating the dirty river, and bounced up and down to ward off a chill, as the clouds gathered over the sun and the breeze blew heavily on my cheek.

Sitting on the ground, a few paces away, were two frail-looking men, with sunken features, wrapped in a blanket, kissing. When a gust of wind surged over the Pier, they snuggled together, in their little cocoon, with their heads against each other, and they gazed at the sunset as if it were their last.

I had never experienced that kind of tender intimacy with another gay man. There were a handful of gay guys at my high school and college, but we never connected in that way, for whatever reason. Every now and again, we’d get drunk and make out at a party, but that didn’t mean anything. And then on the other hand, I had good friends who were all heterosexual, and we loved each other, and we’d hug and rough-house and carry each other around on our backs — but of course, there was always a very clear limit.

Looking back, I can’t tell if I was stuck in the cultural mindset that tells us hetero-masculine people are more attractive…or if I was too sensitive and earnest to relate to my queer peers, who were more spiky and sarcastic…or if I was under the impression society had progressed far enough that queer people shouldn’t have to seek each other out in seedy bars on the outskirts of town, and so I never did...or if I was just petrified of sex!

But whatever was holding me back, it hadn’t triggered the scarcity mindset I would struggle with in the years ahead. I wasn’t going to desperately cling to anyone who came along and showed the slightest bit of interest, even if they were wrong for me in a million ways. I wanted a beautiful man, who found me beautiful — someone special, who doesn’t come along every day.

So when I looked at the two men watching the sunset on the Pier, I realized I had no interest in that sort of intimacy with the man I had come to New York to see. So, as the sky began to darken, I started thinking about how I could get out of this whole thing without hurting his feelings.

When he emerged from his theater’s stage door on 46th street, all of my misgivings were confirmed. He looked nothing like how I remembered him. When he kissed me, it felt like kissing my father. We walked to 42nd street and waited for a dinky bus outside a Burger King. He was groping me like a trophy, but also the way a parent manhandles a child in a crowd.

When we arrived at his place in Jersey, I noticed his hands, rough and calloused, and his cheeks, porous and jowly. We sat on the couch and I made conversation to delay the inevitable. I asked him about his former lovers and he told me he had a partner who recently committed suicide.

I felt like a child again. I’d never lost anybody, I’d never been committed to anybody, I’d never even had a blow-job. I was utterly ill-equipped to handle any of this, yet somehow I’d become the object of this man’s salvation. Suddenly, I was saddled with the emotional weight of being the first person this man was going to have sex with after his partner killed himself.

So, I came out and told him why the night held emotional significance for me. When I said I was a virgin, he wasn’t completely surprised. Then I told him he was the first person who’d ever given me an orgasm — and that gave him pause. You don’t just take somebody’s virginity on a whim when you’re feeling desperate and looking for momentary gratification from a stranger.

Neither of us was ready to bear the responsibility of what this night would mean for the other. But I felt guilty. So, I found myself straddling his lap, unbuckling his belt, and bearing those paternal kisses — a musty smell of day-old sausage on his breath, and his chin like sandpaper.

He led me to the bedroom and took off all my clothes, and then his own. He grabbed my hips and sucked on the side of my ass like a leg of lamb at a monster truck rally. He put his lips around my flaccid penis. And when he tried to penetrate me, I finally said, “I don’t think I want to do this.”

And I felt a bit ashamed, but he said it was okay and pretended like sex was only partly on his mind. He attended to his sturdy erection, stroking and moaning and making that oh-my-god-I-can’t-believe-it face. It was the first time I watched another man come.

He got a towel, wiped himself off, got back into bed and we did the small talk that usually precedes this kind of thing. I told him I was about to do a national tour with a Shakespeare company, doing four shows in repertory, including Romeo and Juliet. And then, I can’t remember how I got started…but suddenly, I was reciting the balcony scene to him —

“Oh speak again, bright angel! For thou art / As glorious to this night, being o’er my head, / As is a winged messenger of heaven / Unto the white upturned wondering eyes / Of mortals that fall back to gaze on him / When he bestrides the lazy puffing clouds / And sails upon the bosom of the air.”

I played all the parts: Romeo, Juliet, even the offstage Nurse — “Juliet!”

“Anon, good Nurse — sweet Montague be true. / Stay but a little, I will come again.”

“Oh blessed, blessed night. I am afeared, / Being in night, all this is but a dream, / Too flattering sweet to be substantial.”

Every time I thought to stop short, he nuzzled his face deeper into my shoulder, and I pressed on to the end —

“Tis almost morning, I would have thee gone. / And yet no further than a wanton’s bird / That lets it hop a little from his hand / Like a poor prisoner in his twisted gyves, / And with a silken thread plucks it back again, / So loving-jealous of his liberty.”

“I would I were thy bird.”

“Sweet, so would I, / Yet I should kill thee with much cherishing. / Good night, good night, parting is such sweet sorrow / That I shall say goodnight ’til it be morrow.”

“Sleep dwell upon thine eyes, peace in thy breast. / Would I were sleep and peace, so sweet to rest.”

He lay his head on my chest, wiped the tears from his eyes, and thanked me. We got dressed and went outside. He hailed down that same little dinky white bus, and I rode it back to Manhattan to catch a late-night Greyhound to Boston. As I lay in that coarse-carpet seat around 4 in the morning, with the sky lightening, charcoal to navy — the euphoria was back.

I stopped telling myself the debilitating story, that I had “waited too long to have sex, and now no one will ever love me.” The rewritten version was — I have so much love in me. I didn’t force myself to do something I would’ve hated just to “get it over with” and satisfy somebody else’s expectations.

I showed up as myself. I made love the way I knew how.

Two years later, I was living in New York City, having a summer of love. For the first time in my life, I was surrounded by gay men I thought of as “us”.

The Pier was my favorite place to go with someone to make out. The late summer sun would explode like a cherry bomb, the sky a vibrant saffron, sweet as pumpkin pie. And everything in the world felt like it was flirting with everything in the world — the water lapping on the cement, the rain clouds teasing the towers, the birds wetting their stomachs on the river— everything was adoring something. Everything was making love.