Minimum of 4 participants, run beside the bed, jump onto it and fuck the partner in front of you.
Me and a few friends are going to do the Jamaican bobsled tonight, want to join?
4 guys in line. Guy in the back of the line inserts a buttplug into his own ass and his thumb into the ass of the guy in front of him whilst masturbating. That guy does the same to the gentleman in front of him, and so on down the line. The guy in front of the line is in charge of the speed and tenacity of the group. He may also call out cadences. "Feel the rhythm, feel the rhyme. Let's all get off, it's bobsled time!"
Me and the fellas at work got bored and tried the Jamaican Bobsled in the conference room. A real team building experience.
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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.
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The act of sending your significant other out on an errand while you secretly install a fuck swing in the foyer of your house so that you can get in face down and surprise them with a new place to put the tv remote when they return.
"Man, frank really screwed up a Jamaican Bobsled last night. He forgot to lock the cat up and it got ahold of his frank and beans."
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.
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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."
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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.
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