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A term used to describe a situation that is possible, but unlikely to happen. Popularized by the tv show Glee.
Based on the 1988 Winter Olympics team who fell short of winning any medals but did surprisingly well.
"What do you think the chances are that Jennifer will say yes if I ask her to go out with me?"
"Jamaican Bobsled Team, dude..."
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v.
similar to a tobagon
the act of four black guys gangbanging a chick on top of a staircase and then riding her down.
The hooker asked, "Would you negros care for a jamaican bobsled team?"
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While hooking up with a chick, drop a huge log on her chest and then titty fuck her with it
Oh man so I was watching Cool Runnings with my girl and I asked her if she's ever been introduced to the Jamaican Bobsled Team, she replied no, so I went ahead and fulfilled her wildest dreams.
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Find a steep gravel road and lay on it flat stomach with your cock facing up. Have someone push you done then the gravel will tear the skin off your penis.
“How’d you get into the hospital”
“Oh I did the Jamaican bobsled”
The use of Vaporub as lubrication.
She didn’t have any KY, so we raided the medicine cabinet and took the Jamaican Bobsled for a spin.
The act of using toilet paper to “bobsled” your turd into the water so it does not leave a shit stain.
Brandon-You know sometimes you gotta Jamaican Bobsled it on the toilet
Mike- WTF is that?!
Brandon- You know, when you use toilet paper to bobsled your shit into the water so it doesn’t leave a stain. Then you sing the song”
Mike- There’s a fucking song?
Brandon- You know, from Cool Runnings”
When you shit so hard you shit up your back
We had a farting contest and Joe pushed so hard he made a Jamaican bobsled track up to his neck.