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 05, 2017
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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
by Dirty Chaos September 18, 2017
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A humourously named sex-act found on Russel's list, from the show Rules of Engagement.
Russel: Alright, we both agree your fiance is a horn dog. Which is why I think we should ask for the Manitoba Snowcone...
Adam: Stop saying 'we', okay? And I'm not asking for anything off of your list of humourously named... sex acts.
Russel: Why not? It took me ten years to fill this thing out... ten *beautiful* years. See if she's up for... the Peppermint Bobsled.
Adam: Noo, I can't do that- I love this person... This would ruin Christmas forever...
by Robyn I May 14, 2007
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To sit on a toilet and defecate in tandem. When one person sits with their back against the water tank and at least one other sits in front of them on the toilet seat and they defecate in a synchronized fashion. If it is two men, the genitals may rest above or below the seat at the individuals discretion.

CAUTION: do not attempt to do with more than 3 people unless you have trained with John Candy.
My friend and I had to shit at the same time and there was only one toilet, so we pulled a Haitian bobsled.
by El Gallo Loco May 05, 2011
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When you are banging a chick from precariously positioned at the top of a flight of stairs, and just as you reach climax, you give her a nudge forward and ride her down the steps while inside her. The ensuing vibrations feel.... just terrific.
So it was really hard to trick Jane into me preforming a midnight bobsled on her, because who the fuck has sex by the top of the stairs. I told her to trust me and she fell for it. I came buckets.
by GonePostal21 July 09, 2010
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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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Similar to titty-fucking a bitch, after shitting on her chest. The only difference is....instead of shitting and then titty-fucking a bitch, you, after ass fucking a girl, if and only if she gives the shitty d. You then rub your shit encrusted member, in digust, up and down her ass cheeks.
Aww, man after I ass fucked Janet, she gave me a shitty dick. So I gave her the chocolate bobsled. All over her ass.
by natetron May 02, 2007
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