Playing gay chat roulette (Part 1)

The largest peep show on earth

I was in a jockstrap doing push-ups on the floor with the webcam pointed at me. “Master Steve,” who I just met, was counting from the other end: “Nine . . .10 . . . 11 . . . ,” and so on.

His cam was only showing his nose, mouth and chest from a dimmed room in Montreal. It was as hot as it was silly, considering that only 30 minutes before I was reading Hanya Yanagihara’s A Little Life on my bed.

I took a break and we started talking on ChatRandom, an online gay chat roulette. I then had my clothes off and he kept saying how he wanted to make me his “boy.”


A chat roulette is a one-on-one webcam chat where you’re randomly matched with a partner from around the world. If you’re not digging them, you click the “Next” button to get another guy, and this can repeat indefinitely until you find the right one — the possibilities are endless. While cruising, if you stop on a someone that you like, you can give them a thumbs up to let them know that you’re interested; it’s very common. If they’re interested too, then great — but you need to retain this interest.

Simply jerking off doesn’t look that interesting on camera. Standing up, jerking a bit, then sitting down again sometimes does the trick — it creates the illusion of action — movie magic. Also, bringing the lens close to your cock helps; moaning and twisting your nipples are an added touch, too.

If someone really likes you, they may ask to move things over to Skype, so that you can both potentially chat again, right away or in the future. I built a collection of five guys since I started using the site. Never ask for a phone number though; even if you’re hitting it off and they’re from your city — this will lead to an immediate “Next.”

ChatRandom played perfectly into my anti-social tendencies too; it was personal but not too personal, and once you’re sick of someone, you just click them away. In the online sphere it seems fair enough.

There are so many men on there that I was getting sucked into this addictive world. I soon found myself jerking off two to three times a day in front of the cam, going through hundreds of men from all corners of the world (though I developed a preference for closeted men from rural Ontario or Quebec).


I started by only logging on during my free time but soon it interfered with my work, since I work from home. Even after I came, I wanted to do it again, never really quenching that thirst. It felt like if I did it just one more time, I’d satisfy whatever it was I was trying to satisfy.

I’ve been back in Toronto for a few weeks, and was staying in the city through most of November before heading off to Bangkok for the winter. I felt like I was living in limbo and was wondering whether I’d been in Toronto a little too long. I was missing the nomadic life, wishing I was still in Berlin or even Sitges, wandering anonymously through the gay world.

Perhaps that’s why ChatRandom resonated so deeply? You can be jerking off with someone in Argentina, watching a guy dancing in panties in Alabama, or witnessing some dude shoving a massive dildo in their ass in Israel. It was the brave new world of perversion, with all these portholes leading to the largest peep show on earth. It played with my imagination, allowing me to escape this purgatory that I was in.

The first time I logged in, I noticed that it activated my microphone along with the camera. Of course I didn’t show my face, but I was also afraid to speak; it was too real. Instead, I would quietly whack off.

I remember landing on this one muscle bear from Florida who shouted, “Nice cock!” This segued into more dirty talk, and he asked questions like, “How old are you?” or, “Where are you from?” I responded by typing on the keyboard — I didn’t want to disrupt this fantasy with my ordinary voice.

It took me a couple of weeks to finally speak. I was getting kind of bored of the whole thing, to be honest, and needed to elevate the experience to keep me engaged in this world — it was really my only escape.

The first words that came out of my mouth via the webcam were, “Hot crotch!” It was with a guy from Brazil, but he couldn’t understand English. Still, it was sexy because it sounded like I was reading from a script, very porn-like. Perhaps that was the point — you become someone new online. I started to say all kinds of things to guys, like:

“Nice fur,”

“Yeah, jerk that!”

“Fuck, man, so hot!”

“Wanna see me spew?”

They’re things I’d never say in real life, but that’s probably what made them even hotter.

I found that just speaking eventually become boring too; I needed more. I needed to show my face. The day that I met Master Steve was the first time that I actually did this . . .

Next: Playing gay chat roulette (Part 2) >

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

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