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Kiss and Tell: “We had sex behind Burrito Boyz”

Luke, a 43-year-old advertising professional, was looking for love. Instead, he got a crash course in public fornication

Kiss and Tell: “We had sex behind Burrito Boyz”

Welcome to Kiss and Tell, a new series about the steamy, surprising and frequently absurd world of Toronto dating. Send your most memorable stories from the pursuit of love and lust in the city to .

—As told to Isabel Slone


When I matched with an attractive lawyer on Bumble, I was looking for the one. I was fresh off a couple years of singledom—punctuated by a few short situationships—when we connected. In our early messages, she mentioned modelling overseas and studying abroad, which I thought displayed a certain level of worldliness. It was summertime, so we met in Trinity Bellwoods with a bottle of wine. She arrived wearing a dress and was as good looking as I had hoped—tall, brunette—with a warm, enthusiastic presence.

About halfway through the date, a flash thunderstorm hit and we were forced to seek cover under a nearby tree. It was cute—almost like a scene from a rom-com. Then, as we were starting to get wet, she quipped, “I don’t wear underwear, so I’m not exactly sure how much you’re going to see.” I thought, Okay, she has a saucy side. To escape the rain, she invited me back to her swanky apartment near Yonge and Bloor. We made out for a bit, and then I went home.

A week later, she invited me back to her place. After a full day by the pool, the inevitable happened: we hooked up. It was a lot of fun—and it made us both even more excited to spend time together.

On our third date, events took a surprising turn. Since we’d already established that we had good chemistry, I figured it would be a more chaste, innocent affair: there was no pressure to make sure we clicked physically. We met up on a Sunday afternoon near Queen and Roncesvalles. The plan was to walk along the waterfront and grab an ice cream cone. She was wearing a lovely long white-lace dress, but the vibe was, as I expected, pretty well-mannered. By halfway through the date, the sexiest thing we’d done was hold hands.

We walked the full loop over the Humber Bay Arch Bridge and found ourselves back at the Palais Royale. Then, all of a sudden, she looked at me and said, “Want to do something kind of bad?” She pointed to a wheelchair ramp at the side of the Palais Royale and said that, if I wanted, we could “crawl under there and have sex.” I was immediately taken aback—this is not what I was expecting, and to be honest, it was pretty brazen. The area was shadowy but still very exposed. Plus, based on the people milling about in fancy attire, there was clearly a wedding happening in the building.

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I was torn. Worst-case scenario, a family with kids stumbles upon us mid-coitus. But I was also exhilarated by the suggestion. I’d had moments of intimacy in not-entirely-private spaces before, like making out at an outdoor movie screening, but nothing even close to letting someone hike up their dress and straddle me in public. I wasn’t morally opposed—the opportunity had just never presented itself. But my doubts got the better of me, and I started having performance anxiety. I made a counter-offer to find somewhere just a little more discreet. She agreed.

On the other side of the Palais Royale, there’s a grass field with a couple of boulders that lead toward a more secluded part of Sunnyside Beach. I directed us that way, thinking that, if we went past the rocks, we might find somewhere suitable. Meanwhile, I couldn’t stop thinking of the wedding happening just 100 feet away: here we were, a couple of dirty dogs, just as two other people were pledging their lives to each other in the most formal way possible.

We found a spot that felt safe and started to make out a bit. We undressed to the point where we could start having sex—that is, until she told me that some guy was watching us. We were busted. The man, wearing a suit and a judgmental expression, made eye contact with my date, so she hopped off of me and we did our best to compose ourselves. Luckily, he seemed content with that reaction.

At that point, it was unclear to me whether this raunchy episode would continue. I suggested that we move on but felt like a wet blanket for shutting down the adventure she was so keenly trying to facilitate. I looked for an alternative locale to satisfy her desire. After we’d walked for a bit, she pointed to the alleyway behind the Burrito Boyz at Queen and Roncesvalles. I thought, Are you kidding me? You want to downgrade to a back alley?

We scouted it out and found a gap between two garages. She ushered me in and, in a movement now familiar to me, hiked up her dress. We started going at it again. It felt surreal, like an out-of-body experience. The unprecedented raciness of it all, plus her palpable enthusiasm, made my head spin. Meanwhile, past one of the garages, I noticed a backyard with a couple of toys strewn about. I kept thinking, What if a kid comes out here?

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She finished fairly quickly. We got up, dusted ourselves off and acted as though nothing had happened. There was this sense of camaraderie about our newly created little secret. That was part of the fun—knowing we had done something bad and got away with it.

After the date ended, I struggled to decide how I felt about the ordeal. I wasn’t full of shame, exactly. If I’m honest, I was kind of chuffed at having expanded my repertoire of sexual experiences. Plus, the fact that she was so into me that she had to have me, logistical impediments be damned, was an ego boost. But it was all so forward and aggressive that it made me question the viability of our dynamic. I started to think that this woman might be a little too wild for me. Had we already reached the terminal velocity of her desires, or was there even crazier shit ahead?

She reached out a couple of days later, saying she wanted to see me again. I was definitely interested, but I had to bail on our date because I legitimately had too much going on at work. I ended up being swamped for the next little while, and we never went out again. It wasn’t a stone-cold ghosting; it just sort of fizzled. On the bright side, I was left with quite a story.

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