When you're doing a girl on the top of the stairs from behind and you randomly grab her arms and put them behind her back and ride her down the stairs.
by Greg August 22, 2003
(v.) when your life is careening out of control in the same way you would be if you tried to bobsled down your icy driveway. usually caused by the behavior of either the opposite sex, or yourself when drunk.
1: how did the talk go with that guy whose been making your life hell lately?
2: i'm in complete bobsled territory.
2: i'm in complete bobsled territory.
by luc and ribs December 10, 2006
When you're giving a girl anal, punch her in the back of her head to knock her out, then ride her down the stairs.
by OC99 May 30, 2009
The act of grabbing your partners legs with the intent of engaging in sex and sliding her between your legs, launching her clear off the bed until she is stopped, usually, by furniture. Normally requires the woman and the bed to be covered in silk or satin. Automatically becomes a Jamaican Bobsled if her head moves side to side and strikes your testicles and she slides through.
by King Dick and Crow Empress January 25, 2009
by Ross_14985 February 13, 2018
A sexual maneuver: one person lays face down with butt cheeks spread. The other with a well lubed shaft, slides said shaft between the cheeks careful to not insert into the butt hole. This is similar to a bobsled going down an ice shoot. Automatically turns into a Jamaican Bobsled if the two individuals smoked marijuana before attempting the act.
by Siriusly_Ensayne March 14, 2018
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 08, 2019