Top Definition
This is when You have anel sex with a woman or a man at the top of a stair case and when u are about to ejaulate u take their knees out and ride them down the steps like a bobsled
Man I was banging my girl hard in the ass last night and as a joke i gave he an olympic size jamaican bob sled
by Draven X September 03, 2006

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Riding a black woman down a flight of stairs.
She wanted some more crack, so she let do a jamaican bobsled on her for it.
by Alkl April 11, 2006

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Where one person sits on the front of a skateboard and the other one stands on the back and pushes. Used to travel places when only one skateboard is available.
Joey and I didn't have a ride to the party last night so we Jamaican bobsledded there.
by Michael 34S April 10, 2011

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Step 1: Take a huge shit.
Step 2: Find a nice big long piece.
Step 3: Place shit in freezer.
Step 4: Wait until frozen.
Step 5: Use as a dildo on your lady friend.
Renee was using her toys the other night, when one of them broke. Doesn't matter. We can still make a Jamaican Bobsled.
by leeden82 December 06, 2010

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Where four black guys get in a bathtub and have sex with a female.
It was crazy I walked in the bathroom and there was a jamaican bobsled going on.
by Hopkins and Cruz December 29, 2009

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When a black male titty-fucks a white female
"I heard Jamal gave Ashley the Jamaican Bobsled last night"
by thephiz4$hiz February 16, 2014

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When a person defecates on the chest of a large breasted woman and it slides down through her breasts toward her stomach.
"Last night my Jamaican Bobsled was clocked traveling at 30 mph."
by csimi February 07, 2009

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The Urban Dictionary T-Shirt

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