The act of laying the erect penis along the buttcrack and essentially titty banging the butt-cheeks. This takes place until ejaculation, resulting in a winter wonderland.
If you'd like to titty fuck her, but her boobs are too small, try Bob Sledding.
by wtfdeejay October 18, 2011
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Doing doggystyle at the top of a set of steps, whereby the "catcher" has their hands on the second step down. Lay down with your chest against said catcher's back and knock their arms out from under them. Hang on and enjoy the ride.
It's a good idea to wear a helmet when you bobsled.
by Drew August 5, 2004
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Two guys, one girl, multi-head action.
She joined Tim and Ed for some Bob Sledding.
by c c millett March 14, 2004
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This is when You have anel sex with a woman or a man at the top of a stair case and when u are about to ejaulate u take their knees out and ride them down the steps like a bobsled
Man I was banging my girl hard in the ass last night and as a joke i gave he an olympic size jamaican bob sled
by Draven X September 4, 2006
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Wedging a poop covered penis in between a butt crack and sliding it back and forth, which leaves a little poop trail behind.
The other night I performed a mexican bob sled on some chick's behind. Awkward, to be sure, and she won't shit right for a week.
by Wookiestick1 September 17, 2011
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The act of sticking a non-flaccid penis in your partners anus, then proceeding to ride them down the stairs.
WOW, did you hear Suzie got rusty bob sled down 7 stairs and wanted round 2
by sweeney billy May 6, 2015
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jerking off into the buttcrack of a pale white male, and then sliding your dick in between the asscheeks to simulate a bob sled run.
hey pale white man, remember when i jerked off into your buttcheeks and then stuck my dick in there to simulate a bob sled run? that was a great alaskan bob sled pillow sandwich.
by tim "fuckface" roy April 20, 2006
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