Sailboating 

A three-some consisting of two girls and a guy. The guy lays on his back while one girls rides him and the other sits on his face. The two girls face each other holdings hands, creating a triangle or "Sail".

The same thing as Eiffel tower but for 2 girls, 1 guy.

ddannnggggg! Dina and Snooks really know how to go sailboating!!

Sailboating by Sailboatking August 14, 2011

Sailfin 

The full male genitalia through the front hole of your boxers. While having the back end of the boxers rolled and jammed up your asscrack like a thong.

Hey Jimmy, If I show you my Sailfin will you show me yours?

How bout I whipout the Sailfin and get this party started.

Sailfin by Nicholas J May 13, 2005

Sailview 

the coolest place you could ever fucking live!!

dude i live in sailview
fuck thats cool
i'm soo jealous
i live in westport ohh wait lincolnton

Sailview by jiggaloulaslou June 6, 2009

Sailing Tee Pee 

When someone grabs a roll of toilet paper in between each of their pointer fingers, rolls the vehicle window down, and proceeds to let it 'sail' out from the roll and in to the wind.

Taylor screamed as my sailing tee pee flew in to his face, I told him to roll his window up.

Sailing Tee Pee by Krowvin February 20, 2011

Sailboating 

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."

Sailboating by Gary Flongtard December 7, 2011

Sailor Julia

BEST ROBLOX YOUTUBER EVER! (she is Byebyelittleadrien.)

Person: hey wanna watch “SAILOR JULIA”.

Other Person: OMG THE BEST YOUTUBER? OFC!

Sailor Julia by Byebyelittleadrien December 18, 2021

twat sailor 

a male sailor that is also a prostitute

The women in town go crazy when the navy boys come back so they can pay twat sailors for sex.

twat sailor by tim and josh August 21, 2008