In order to preform the dirty toboggan you must first have yourself a toboggan. Once you have done this step you then have to grab your partner (May be male, female, tranny, etc.) and vigorously penetrate them anally. When you are close to ejaculation you have to take your penis out of the anus and ejaculate into a pile of snow. Then you take your partners head and smear it in the jizz covered snow, and yell "DIRTY TOBOGGAN!".
Jessy: "So where did you bring Anna last night?"
Jeffery: "I brought her to the hill and gave her a Dirty Toboggan".
Jessy: "No way man I'm so jealous!"
Jeffery: "I brought her to the hill and gave her a Dirty Toboggan".
Jessy: "No way man I'm so jealous!"
by TobogganMan December 25, 2013
When having sex, doggy style at the top of a flight of stairs, the man proceeds to put the female into a full nelson, thus rendering her arms helpless, and then rides her down the stairs. Caution the female will usually sustain heavy damages and will need to seek medical attention, leave this to the professionals.
My wife though she was getting kinky when she let me fuck her doggy style at the top of the stairs. Little did she know,a toboggan ride was in her future. This is why I am now divorced.
Sandra: My boyfriend showed no mercy last night and gave me horrible rug burn on my knees.
Molly: You think your boyfriend's bad? At least he didn’t put you in a full nelson and toboggan ride you down the stairs. He almost ripped my nipples off.
Sandra: My boyfriend showed no mercy last night and gave me horrible rug burn on my knees.
Molly: You think your boyfriend's bad? At least he didn’t put you in a full nelson and toboggan ride you down the stairs. He almost ripped my nipples off.
by Alex Mutha fuckas September 4, 2008
by thatsteelersguy February 6, 2019
This can only be performed by men living in a northern region with frequent snow such as Alaska, the upper peninsula, or Watertown. On a cold winter night, to spice things up in the bedroom, the man puts on a condom, applies a liberal amount of top quality hot sauce instead of lubricant, then thrusts fully into the wanting vagina of his lover and holds on for the ride.
"Becky said she was cold last night and wanted me to warm her up, so I gave her a hot toboggan with some Ghost pepper sauce, and she definitely wasn't cold anymore."
by Dylan Kaczynski August 19, 2017
A group of close friends partakes in a special 4-way. This maneuver is optimal in a locker room on a bench. The young lass should also have large breasts. The woman lays on the bench with her head tilted back over the edge, she is then fucked by one of the men while another takes a sweet sweet blowjob. The third man will then proceed to drive his wagon train through the woman's mountain pass (fuck her tits). When the time all three men create a snow storm on her face.
by Constable and the Mosquito May 5, 2009
An alaskan toboggan is when a woman/ or male poops in a condom, freezes it, then uses it as a dildo for sexual pleasure.
by BackCrackaa. October 17, 2010
its a super slutty chick that is so easy and skanky that you could ride her down the hill like a toboggan
by cumdumpster444 December 4, 2008