the act of pressing you nose against a flat chested woman and just blowing
Did you motorboat sarah's friend last night? Nope, just went sail boating, there where no boobs!
by Touge_Drifter September 19, 2012
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When a girl gets on her knees and blows on your balls so hard they swing like a mast of a sail boat.
Last night my girlfriend got on her knees to suck my cock and instead she blew on my nuts..sail boating.
by titsmcgee555 November 12, 2010
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when you take the toilet paper that you wiped your ass with and put it on someones face while they are sleeping.
man!!! did you see Raymond give Sam a sail boat last night? It was fucking awesome!!!!!
by Shadow44_z December 25, 2008
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I went to motorboat my girl last night but I was laughing so hard that I just blew on them instead...sail boating!
by Letsgeauxmunging2night November 14, 2009
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When you are only able to exhibit your gay behavior while on a sail boat. Phrase coined on New Adventures of Old Christine.
My chiropractor can't be gay on dry land. Because of people like you he has to be sail boat gay!
by Sisco Kid December 11, 2008
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There are Different Stages to Sailing Ones Boat.
Similar to the Bases in Baseball.
If you go all the way around the world, well guess what, you've had sex.
The other stages are up to you. You can pretty much make it up and Elaborate as you wish.
"Dude, last night at the dance Eve almost sailed her boat, thank god the Coast Guard was there."

"So, are you sailing your boat this weekend?"
"Ya, but were just going to an Island off the coast"*Wink Wink*

"You Let Your Anchor Up?!?!?! You Slut!"
by Kortney J May 01, 2007
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