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Jamaican Bobsled 

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."
Jamaican Bobsled by Santo Mafioso February 27, 2008

Jamaican bobsled 

When you are having sex with a girl then flip her over and break her leg. Then you and three of your friends carry her by her orifices towards a cheering crowd.
Man: bro he is a legend
Man 2: why?
Man: he pulled off a Jamaican bobsled on stacy
Jamaican bobsled by Dirty Chaos September 18, 2017

jamaican bobsled 

a sexual act that consists of three people, 2 of which are male. 1 man is having anal intercourse with the women in the doggy style. durring this the second male lies parallel and under the women with his cock in her mouth. the second male also proceeds to lick the first males testicals.
"dude i gave you a call last night and you didn't pick up"
"ya srry i was asleep"
"well you missed out we were gonna give this chick the jamaican bobsled"

Jamaican Bobsled 

When a black male titty-fucks a white female
Jamaican Bobsled by thephiz4$hiz February 16, 2014

Jamaican Bobsled 

When a woman has missing bowels, and your erect pulsating cock breaks the kidney lining causing complete organ failure and loss of cognitive function. There is a strong history of Jamaican originating Australia, despite the name. It was popularised in the 19th century in the industrial revolution.
"At a morgue"
Doctor "Sever scar tissue among the kidney lining"
Investigator "cause of death?"
Doctor "Jamaican bobsled"

Jamaican Bobsled 

She didn’t have any KY, so we raided the medicine cabinet and took the Jamaican Bobsled for a spin.
Jamaican Bobsled by Grim Tiswold January 21, 2022