2 definitions by Gary Flongtard

Top Definition
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
The mans penis
Friend 1: "Yo, come check out my sailboat after school?"
Friend 2: "Fuck No!"
Friend 1: "Oh. But i just put a new finish on it."
Friend 2: "Maybe."
by Gary Flongtard December 07, 2011

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