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1. A sled

2. A woolen hat similar to a beanie.
I went for a ride on my tobogan wearing a tobogan.
by itsjustluck April 16, 2005
when a woman lies on her stomach at the top of stairs and the man sticks his penis in her asshole and rides her down the stairs
Wendy got a black eye from the tobogan last night
by Jay February 02, 2004