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.
by Sanka Coffie November 8, 2019
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."
by DickDouche22 July 6, 2017
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.
by Michael 34S April 10, 2011
When a person defecates on the chest of a large breasted woman and it slides down through her breasts toward her stomach.
by csimi February 8, 2009
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.
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 7, 2010
Fucking a chick in a shitty bunghole, pulling it out and then sliding your cock between her ass cheeks.
"after screwing that chick in her dirty bum, my cock looked like a Jamaican bobsled sliding through her cheeks."
by Santo Mafioso February 28, 2008
When a black male titty-fucks a white female
by thephiz4$hiz February 17, 2014