Sex Lives chronicles the evolution of one person's sexual history. This week: Bill, 52, Montreal.

My first introduction to porn was some kid boasting about it in school. He was like hey, "I can get porn but it's really expensive." He was trying to get kids to pay $100 for porn that he would bring to school for them. I remember thinking, I'm not really sure what the point is…but I’m not paying $100 for it. And then I went to boarding school and there was a classic corner store and they didn’t give a crap and it was like, “Oh they’ll just sell me these magazines?” It was classic 80s stuff. The really cool kids would get the local bum to buy beer—the other kids would go and get porn. It was at an age where you could possess it, but that’s it. 

There was no talk of what we were doing with it. We didn’t have that discussion as 14, 15, 16 year old boys. No masturbation, nothing. “But check out all this porn I have!”

I was training to be a skier and in the summer I’d go to Whistler and ski the glacier and I met a girl. It was that high school juvenile thing where you’re kind of bitchy to each other because there’s some attraction and you don’t know how to process that. It just sort of happened. I don’t remember anything in the way of foreplay or discussion. It was just two high school students who didn’t know what they were doing, slapping their bodies against each other. She wasn’t a virgin; she was already on the pill. It was pretty clear she was like, “I’m going to get this.” I didn’t make any moves; I wasn’t the instigator.

I’ll be honest: I was a good-looking guy. I’d been at an all-boys boarding school when I got to college, though, so it didn't occur to me that I was attractive to women. But I guess I had a lot of fun in college, as one does. I mean, I spent years waiting tables and I was in theater, where I was one of the few straight guys. My mom wanted me to be a dancer and I was like “I can't” and it broke her heart because she did ballet. But looking back, you get in really good shape and there’s barely dressed women draped over you! I was asked once if I got creeped out because there were so many gay guys in theater and I was like, “How would that creep me out?” 

After college, I was dating someone and we went to Hawaii to visit some friends, but she left me there. First, she shaved my head because she thought it would look really cool. And then she left Hawaii because she got a job. I got recommended to an [acting] agent, and I walked into her office and she happened to be on the phone with people who were looking for prisoners of war for a movie. She looked at me and said, “Well, you look like a POW. Would you like to audition?” And I had a great job in LA that didn’t start for a couple months, so I thought, sure, let’s do this. So I got cast in a crappy Kiefer Sutherland movie on Kauai. One of my fellow actors brings this beautiful woman over from another island while we’re filming— she was 10 years older—and we’re drinking and playing poker in his room. She asked me, “I’d really love to get some sleep tonight. Do you mind if I stay in your room, just until you’re done?” I agreed. At the end of the night I went back to my room and told her we were done, you can go back. And she was like, “Oh there’s two beds here, why don’t I just stay?” I said sure. Then she said, “Why don’t you get into this bed?” I said sure. “Why don’t you come a little closer?” Ok sure. “I want to take you in my mouth.” I don’t know if anyone had ever spoken to me like that.

When the movie was over, I got a call saying “Why don’t you come visit?” And so I went to go visit the island she was on and in short order I basically became the cabana boy. I had been living up the hill in the jungle with a friend and it was really buggy and she was like, “Why don’t you stay here? I know you’ve got this job coming up in a few months. Why don’t you hang out for a bit and do some community theater here?” So I lived in a ballet studio adjacent to the house where she and her husband lived. Her husband would leave for work every morning and she’d come out to me with a fresh cup of coffee. That went on for a couple months. Their relationship was already done. He was disappearing every night to go play music with the boys—He didn’t know or he didn’t care. It became a really passionate affair between her and I. It was very torrid. Tango lessons under a lemon tree during the lunar eclipse; completely romantic. We were madly in love and would have run off if not for her daughter; it wasn't entirely a fling. We are still in touch and the sex, while wonderful and amazing and exciting, was the icing on the whole thing. A true love if such things are a thing.

One night, after those dance lessons with some friends, we wandered down to the water and started making out and I put her up on a park bench and ate her out, then we had sex and then I stood up on the bench and came in her mouth. Looking back, this is probably on hotel surveillance footage. Totally public. But I just didn’t care. I felt like a rock star. We had a few times like that. Another one was driving back from a party and pulling over to the side of the road and having sex in a lava field. Well, on the hood of the car in a lava field.

After that, I became a bartender. A crazy woman walks into my bar one night. Well. A beautiful woman walks into my bar one night and orders a champagne cocktail and says, “What do I owe you?” And I said, “Gosh, there’s only one other person who’s ever ordered one of those. I don’t charge her, I don’t see how I could charge you.” And she said, “I thought you’d say that.” And then she left. I turned to my buddy like what the hell was that? And he said, “That is a train wreck dude, stay away.” Naturally, I invited her to my birthday party a few weeks later and she showed up and then she started just doing the dishes. We had a strange, crazy affair. She asked me to move in with her and I was getting ready to do that. Then one night the phone rang around 11:30 pm while we were bed and she hung up the phone and said, “Look, my 19 year old boy toy just got out of jail. Feel free to finish the vodka and cigarettes if you want.”

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For most of my 30s I didn’t have sex. I ended up moving to Vancouver almost on a whim; a buddy I’d gone to school with worked in the video game world and said, you should come check out Vancouver and I was there for the better part of a decade. But sex-wise, it was one of those Groucho Marx things. I wouldn’t want to be part of any club that would have me as a member. I was testing video games making like eleven bucks an hour in my 30s in a very expensive city. I couldn’t afford relationships.

Then I moved back to the East Coast, started doing yoga, met the local yoga teacher, and then stopped doing yoga because we were dating. We had a great relationship. She moved in with me. We were together for seven years—great sex. Neither of us had been with anybody in a while and once we were just hanging out and it was one of those whirlwind things where next thing you know we’re upstairs in bed. We’re talking dozens of orgasms. I’ve never been like that; it was kind of an eye opening experience. I guess some things click later in life. But for the next month every time she talked to her friends she would mention it was the greatest sex of her life. And she’d had a lot of sex. But then it became a thing where we were looking for that result. Like OK: I come, you squirt. We’d be like, “You want to do that thing?” We’d actually refer to it as “That Thing.” We weren’t even married. Also we had a miscarriage, which kind of signaled the end. She ended up moving out the first year of Covid.

I did a Covid year of nothing and then I thought, “Fuck it!” and tried the online dating world to see what it was like. The first person I matched with on Tinder was Russian-supermodel-hot. I was like this is great, she lives nearby. And she messaged me with “I want a guy who can tie me up and dominate me, not too hardcore.” I was like OK. Wow. I wrote back something like, “Do you like bubble baths and rose petals?” I just wanted to make myself seem really fucking lame and she disconnected thank god. I mean that was her opening salvo. Not “What do you do?” or “I like your smile.” I was not ready for that. I fumbled the ball on that.

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