Top Definition
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 man places a strap on backwards as to be able to have sex with two women. The women straddle him from alternate sides while linking hands over the mans shoulders creating a triangle shape. When the legs and as are both linked the man stands creating the shape of a mast and sail. He then has sex with the two women.
I need to work on my leg strength if I want to do some sailboating tomorrow night
by Mypenisisapizza November 23, 2014
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
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
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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