Same concept as a motorboating (where you bury your face between a pair of boobs and vigorously shake your head from side to side) except sailboating is slower so you can take it the view.
I wanted to motorboat the girl, but her bazongas were so nice that I opted to slow down and ended up sailboating her instead.
by Lake Partiers May 4, 2021
Get the Sailboating mug.by talbot999999999 May 17, 2023
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Tailgater: This guy's gonna pass the gate, lemme be on his tail to sneak through the guards
Guards: Yo this guy's so close to that guy, man's prolly tailgating
Guards: Yo this guy's so close to that guy, man's prolly tailgating
by ThatHugo542 November 8, 2024
Get the Tailgating mug.The tender act of gently laying one's face against another's breasts. Akin to motorboating, but without the noise of the motorboat. Rather than revving your emotional engine, you're drifting peacefully upon emotional waters.
by dAni5742 April 15, 2025
Get the Sailboating mug.When there is a line of cars behind one person driving slow, and you're somewhere several cars back so you tailgate the person in front of you, who tailgates the person in front of them and so on and so forth until someone is tailgating the slow driver.
Joe: Man, I was five cars back from some old granny today and I couldn't pass... it sucked.
Pete: Dude, you totally should have tried vicarious tailgating.
Pete: Dude, you totally should have tried vicarious tailgating.
by albert mcpassingpants June 21, 2010
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