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1.
When a girl's breasts are insufficient in size for motorboating, hence the next lowest denomination of aquatic transportation is used.
Andrew: Why didn't you motorboat her last night?
Corey: She had little A cups, I tried...
Andrew: You sailboating son of a bitch
by gack513 January 05, 2011
 
2.
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
 
3.
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
 
4.
The acting of rocking a mans member (aka sailboat) back and forth inside a womans vagina (aka cum-boat), this process is refered to as surfing her seas, after which the man finishes within her, this process is refered to as "unloading cargo"

*all aspects must be followed to be considered sailboating
Friend 1: "Dude, what'd you do last night?"
Friend 2: "Not much, just some sailboating."
Friend 1: "Idiot! Think she'll get pregnant?"
Friend 2: "I dont care, not my bitch."
by Gary Flongtard December 07, 2011
 
5.
Much classier than motorboating. To gently blow on a woman's nipples.
Nothing puts Amanda in the mood like sailboating.
by BarrettAll November 27, 2011
 
6.
Blowing on boobs.
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
 
7.
A three-some consisting of two girls and a guy. The guy lays on his back while one girls rides him and the other sits on his face. The two girls face each other holdings hands, creating a triangle or "Sail".

The same thing as Eiffel tower but for 2 girls, 1 guy.
ddannnggggg! Dina and Snooks really know how to go sailboating!!
by Sailboatking August 11, 2011