Top Definition
A fully strected out ballsack, resembeling the sail on a sailboat.
I cant believe he showed your mom the sailboat.
by tom clancey February 10, 2004

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A version of motorboating where you blow on a girls tits.
Last night I got her bra off and started to sailboat her tits.
by ktrain11 July 18, 2009

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it's like the eiffel tower, but it's where a guy lays down on the floor, one girl sitting on his face, the other on his dick and the girls high five, thus making the triangular sail shape.
We should totally sailboat that dude
by Awesome Brandon March 18, 2006

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pocket fours in texas hold'em
Randy: Ohhhhhhh, I just got beat with sailboats against my two pair, worst beat of my life!!!
by Baker Rawlings January 26, 2006

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sort of like motorboating, but you instead of placing your face in between the breasts, one just leans back and "blows the wind into a girls sails" aka breasts less awakward and easier to do in public
hey jess, can i motorboat you?
no way! we're in the middle of a bar, but you can sailboat me!
blow away!
by J BOMMBZ January 27, 2010

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A dick trick.

The man's (or she-man's) penis is wrapped underneath the ball sack till the penis is pulled perpendicular to the body. This is the "boat." Note, the balls remain behind the dick. Then, the scrotum is then stretched into a triangle where base is held against the penis. Note, the top requires pinching the scrotum and pulling up hard, which can be enjoyable or painful. This is the sail. When completed, the penis sailboat appears to be cruising at about 3 knots across the pubis. It's very popular and appropriate for most parties.
Hey, this party needs a kick, should I bust out a sailboat?

Cody's balls are so big his sailboat would be hella' fast.

I was surprised how much she liked my sailboat trick, then she let me dock my boat in her lady bay.
by ucla sailor January 02, 2012

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(n.) (synonym for sluts)
-referring to sluts in the manner or basis that girls (sluts) are just like sailboats; riding a sailboat is great fun, just as sailboats are great to look at and examine it's special unique features that every boat does not retain(same with hotties when enjoying tits, ass and facial features); but messing with the masts, the angles, wind direction and whatnot gets old quick.

Similar to playing with the same hottie for an overly extended period of time, you get bored and wanna jump off the boat just as why you always anchor the sailboat, jump off and go for a swim. Even though your sailboat(slut) may be very intriguing and fun to play with, you always want to upgrade.
hence the reason why large sailboats will have a jet ski or jet boat on the back, just as we keep hotties on the backburner.

friend A: Bra, that sailboat wanted to wife me up
friend B: Jesus dude, same here man. thats why i had to sail asap
friend C: ya man, thats why you gotta get on the boat, go for a quick sail around, then hit the docks to find a new boat to sail for a few days
Random Guy: F*cking sailboats
Random Guy's friend: oh sluts sluts sluts
Used in a sentence: got some sexy sailboats out here today
sluts gap
by suzy greenberg114 February 01, 2011

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