Toronto
3 min

Taking his gay virginity

It seems in these sexually saturated progressive urban days that the idea of a gay virgin is almost unheard of.

However if one were to type “gay virgin” into a search engine the on-line adult world would certainly have us believe quite the opposite. Where exactly does this obsession with virginity in popular culture come from?

To be honest I’d never given virgins much of a thought. When I talk to my queer friends I’m shocked that many of them had their first sexual experience even younger than I did.

I’d been so against any kind of casual encounter, holding out for even the slightest romantic prospect. But from a practical perspective I knew I had to make sure this whole “gay thing” was really my cup of tea. At 15, driving with a skateboarding A&W manager/poli-sci major to a spot nestled next to million-dollar houses overlooking the ocean, I got my first taste of what would soon become my preferred dish of choice.

I told him on the drive back it’d been my first time and he got noticeably flustered and quiet. Sure, it was loveless, slightly awkward and I never did get my Suicidal Tendencies tour cap back from his backseat. But I knew without a doubt afterward that I wasn’t just gay in theory but in practice. I was thus thrilled and didn’t care if I ever saw him again. I wouldn’t understand why he was so nervous until years later when I met my first virgin.

A friend of my roommate’s, he showed up at my house and immediately I was intrigued. He was a shy 22-year-old scruffy tree-planting vegan punk who was also a curiously intellectual old-school gentleman and an award-winning poet, the exact opposite in every way to my previous love interest and therefore situationally perfect. When I was told he hadn’t had a boyfriend before I assumed he was just picky and therefore a challenge, which I could, of course, not back down from.

We finally got time alone and sitting on my patio in the glow of the adorably low-fi Christmas lights we talked about famous painters and humanist philosophy until you could cut the tension with a knife. I broke and reached over to kiss him. We kissed long and deep as I grazed his scruffy cheeks slowly with the palms of my hands until after a few minutes he spoke.

“I’ve never done this before.”

I looked him square in the eyes, pausing for a moment, and with a sly smile responded, “Doesn’t matter to me.” His face registered approval and we continued. Hard was not an appropriately descriptive enough term.

After years of dealing with overly confident, overcompensating and completely subtlety-free assholes his honesty was just as exciting as the “new car smell” factor. As I reached my hand down his leg and up his shorts he calmly grabbed my hand.

“I’m not ready for that,” he spoke softly.

“I’m happy just kissing you,” I replied, making sure to register my acceptance with my eyes. We would continue to simply make out for three hours and it was one of the most erotic experiences of my life despite being completely ejaculate-free.

It was only a few days later that on the roof of my house looking out over the summer glow of downtown skyscrapers that we would have sex. With every action and every touch I tried to exude all the feelings and sensations I’d collected from lovers over the years into what I knew would become part of his inescapable personal history. I was trying to create the ultimate experience, the experience I wish I’d had.

There is a lot of pressure in being someone’s first anything and I was scared as our love affair began. I wanted desperately to give gay men a good name and not accidentally create another bitter and jaded queer. In the end we were too different; a myriad of experiences separating our goals and points of view.

With me it wasn’t being the first that got me off so much as it was about being able to emotionally and sexually set the bar high in hope of giving someone hope and the strength to never settle. After my first time I still thought I’d never find anyone I could connect with on a real level who was a “normal” queer as I understood it. I still felt like an outsider among outsiders. We may not have stayed together forever but my biggest fear is that I didn’t do enough to show him there are good guys out there somewhere. If I’m his first memory of love and sexuality I can only hope I’m an inspiration and not a regret. Not knowing which I am is the scariest part.