A game in involving three or more people, including at least one male; one male sits while the others take turns giving him oral sex, for thirty seconds each. The person providing head when he attains orgasm is the winner.
by Anonymous June 14, 2003
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One of Earth's most ridiculous websites that randomize a video chat session with another random person in the world with a webcam. No downloads required. Anything goes.

Things to expect while on chatroulette.com
-4 out of 5 are male
-about 1 in 6 odds that male is jerking off or showing full frontal
-about 1 in 4 odds the male is looking for a set of nice titties
-a video on repeat (porn, something misleading, often ridiculous)
-that token 50+ year old
-college dudes
-less college chicks
-dudes looking to chat someone up
-girls looking for attention and compliments (see: tease)
-pre-pubescent middle school girls
-people from other continents (duh)
-a short conversation
-a long conversation
-racists, insecure people who act racist because they are behind a computer screen. (See: chatroom thug,tool,poser)
-people with ridiculous costumes
-people you wonder why the fuck the are on chat roulette
-non-sexual entertainment (rare)
-rejection
-a good laugh (LMAO, die laughing)
-and on rare occasion a girl who puts on a show

Similar websites: tokbox, omegle, etc

You never know what to expect from this site.
Guy 1: Dude, let's fucking chat roulette right now, I wanna see what some titties and/or asian girls!

Guy 2: I didn't know you were that anxious to see some dude jerkin it while sitting in his dark bedroom. But yeah I can go for some titties.

Guy 1: I have a feeling we'll see some titties from tits mcghee today.

(five clicks later)

Guy 1: Ah fuck! some dude jerkin' it...Do you think he does this all day?
by Sexual harassment Pandaa March 2, 2010
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when on chatroulette you press next about 10 times to probably try and evade yet another cock, and the same partner's cam keeps coming up .
man,some dude on CR just kept jerking off at me. so I tried to next the fucker but got totally stuck on a roulette roundabout.
by savagehenry April 9, 2010
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An unusual game usually played at the office, where one person tries to get rid a smelly chair by switching it with someone else's
I almost got rid of my smelly chair, but somebody played funkychair roulette while I was at lunch.
by OCHAGunny1313 January 8, 2011
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Having sexual intercourse without the use of a condom with a child bearing able female that is not on birth control. Leaving the pregnancy possibility in the control of a higher power or the questionable fertility of the partner. Known as gambling with parenthood. Can come in many forms, i.e. drunken hook up, bear-hug blast, fake rape, etc.
"Virginia is pregnant?!"

"Yeah, that lawyer wasn't so lucky in his game of sexual roulette."

"I don't have a condom."
"Fill me up, Gambler. Let's play sexual roulette!"
by Gleaven May 15, 2014
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a potentially lethal game of chance in which participants partake in events that could kill them emotionally.
Person 1: "Hey where's your roomate at?"
Person 2: "Oh, she is at her ex-boyfriends house."
Person 1: "Didn't they break-up like 2 years ago and he's married now?"
Person 2: "Yeah, but shes always liked to play emotional roulette."
by Mel Berner January 18, 2009
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Playing Russian roulette with a semi-automatic pistol.

A semi-automatic pistol, unlike a revolver, automatically inserts a cartridge into the firing chamber when the gun is cocked, removing the chance of living.
In Latvian roulette, player always lose, suffering end.

Such is life in Latvia.
by winterd August 3, 2013
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