Playing gay chat roulette (Part 2)

A sign for change

I recently discovered gay chat roulette, which is basically an international circle jerk-like site with up to 14,000 people from all over the world. I found the whole thing somewhat addictive at first; I had been back in Toronto for a few weeks after spending six months out of the country. The chat site made it feel like I was still traveling, virtually, creating the illusion of same sort of excitement one might feel in Berlin’s sex scene. I thought that maybe I’d taken it too far though when I found myself doing push-ups on cam, in a jockstrap, for a guy who calls himself “Master Steve.” He was counting on the other end.

When I first discovered gay chat roulette, it took me a while to speak on camera because it felt like my regular voice would disrupt the online fantasy. The best way to get over this was to talk like I was in a porn film, which created a new persona for myself. Later I decided to show my face too, which I’d been reluctant about. I pointed the cam at my upper chest, showing my face along with my crotch, and started browsing. Seeing myself like that in front of others made me look like I was a porn star.

I was online for about 20 minutes before I finally landed on “Master Bruce.” He only showed his chest at first. He had a muscular bear physique, though more bear than muscle. I took my hand off the “Next” button and got comfortable. Soon, he showed his face. He turned out to be a handsome Middle Eastern man from Montreal, who was in his late 40s.

He then asked if I ever had a daddy or master. I was just trying to get off, and I was liking where this fantasy was going so I said, “Yeah, dude.” He told me that he was looking for a full-time slave. The idea of that was hot too, so yes, I said. Sure, I can maybe be that slave.

He started telling me that if I were his slave I would need to not only service him but his buddies too. “Sure,” I said. He asked what I’d do if his buddies came over. “Um, take their clothes off?” I responded.

That was correct, he said, but how would I do that?

“Oh, I don’t know. With my teeth?”

That wasn’t the right answer.


He explained something called, “S-S-S” which stands for “shirt, shoes and socks.” That was the order in which I was to undress his buddies. He stressed that it was forbidden for me to remove their jeans though. He got me to repeat what S-S-S stands for.

“Um, shirt, shoes, socks,” I said.

“That’s my boy.” He seemed genuinely proud of me.

“Cool. I’m really close to coming by the way,” I admitted.

“Stop!” he yelled, startling me. “Don’t you dare come until after I do. Got that?”


“Yes, what?”

“Um . . . Yes, sir?”


“Oh. Yes, master?”

He ordered that I stand to get a better look at my body, while asking for details like my height and weight. Next, he got me to do this agility test where I was to lift or lower one of my arms at his request. He’d try to throw me off by asking me to raise my right arm, and then ask to raise my right arm again, causing me to either lower it or lift my left arm instead.

He started slow but soon he was asking me to lift and lower at a rapid speed — that’s when I started to question what the hell I was doing. On one hand it was exciting because it was so strange, but on the other, it was just so strange.

He told me to put on a jockstrap and do those push-ups, followed by sit ups and squats — very porn-like. He finally asked me to bend over in front of the cam because he was close to coming.

“Don’t move.” He just kept saying, “That’s my boy . . . that’s my boy.”

He warned that his loads were abnormally large. It seemed pretty average to me.

After he wiped himself, he said that I could come too, but I had a bit of trouble. After I did, he gave me his phone number (a huge no-no for chat roulette) and told me that I was to visit him in Montreal as soon as possible.

“Yes, master,” I said with no intention of doing so.

When I closed the browser, I found myself sitting alone in the apartment, with a jockstrap at my thighs. At first, it had seemed spontaneous, but in the end I just felt kind of sad. The reality was that I wasn’t a porn star and this wasn’t like being in Berlin. Had I become so bored back in Toronto, away from my travels, that this was exciting now? I took it as a sign.

After I cleaned up, I booked a ticket to Bangkok, just like that. I needed to keep moving.

Next: Falling in love with a stripper (Part 1) >

Hole & Corner appears on Daily Xtra every Wednesday. Follow Mike Miksche on Facebook or on Twitter @MikeMiksche.

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