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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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Jan 18 Word of the Day
1. Blue Monday is the most depressing day of the year, calculated by Dr. Cliff Arnall, a researcher at the University of Cardiff's Center for Lifelong Learning.
Factors used to calculate the date included weather conditions, debt level, time since Christmas, time since failing our New Year's resolutions, low motivation and feeling the need to take action.

In 2005 the date was calculated as January 24th, in 2006 it was January 23rd, and in 2007 it was January 22nd.

2. A song by the hard rock band Orgy from their album Candy Ass.
1. Guy: "Aw man, I feel like absolute shit today."
Friend: "Yeah, same here. I hate Blue Monday."

2. "I wish I could sing Blue Monday to my ex-girlfriend, she's such a bitch."
by L_Roku August 31, 2007
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2
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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3
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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4
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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5
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.
by Awesome Brandon March 18, 2006
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6
(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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