Sex Lives: A Guy Who Did a Stint as a Hawaii Cabana Boy

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.