Top Definition
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
9 more definitions
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
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
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
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
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
The male equivalent to motorboating, where a woman puts her head between a man's legs and moves her face side to side resulting in the man's penis (or "boom") coming about, so to speak.
I told Gladys to get down there and start sailboating me. She manned my jib all night long.
by Bob Wylie June 10, 2011

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