The Bobsledder is when a guy is tittyfucking a big chested milf while his friend is behind him nailing her in the puss. The 2 keys to it are you need to have Cool Runnings playing on dvd in the background, and before you both finish you need to proudly recite the famous line "Feel the rhythm, Feel the rhyme, Get on up, its bobsled time! COOL RUNNINGS!"
Me and Sanka were down at Dempseys and picked up this milf and took her back up to my apartment to bust out The Bobsledder.
Tom: Man, I had the best time in Kansas City last weekend. Totally went Colombian Bobsledding on this waitress at a truck stop. Hit it so hard between those big, sweaty jugs the coke turned into paste.
Jim: Hey babe, you ready for the Extreme Alaskan Bobsledding?
Jane: Sure, but try to take it easy, I don't want to tear my back up that much this time.
Jim: Well you don't have a choice, because your going to be unconscious Jane: Fuck