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

Sailing Your Boat 

There are Different Stages to Sailing Ones Boat.
Similar to the Bases in Baseball.
If you go all the way around the world, well guess what, you've had sex.
The other stages are up to you. You can pretty much make it up and Elaborate as you wish.

"Dude, last night at the dance Eve almost sailed her boat, thank god the Coast Guard was there."

"So, are you sailing your boat this weekend?"
"Ya, but were just going to an Island off the coast"*Wink Wink*

"You Let Your Anchor Up?!?!?! You Slut!"

Sailing Your Boat by Kortney J May 14, 2007

sailing mishap 

from Teen Girl Squad

SAlLING MISHAP

sailing mishap by cheeseguy June 8, 2004

sailing the ship 

driving whilst most intoxicated

The bar is closed and I now rely on a more Divine compass, for I am sailing the ship home!

sailing the ship by cap'n joe November 10, 2008

Sailing buddies

Code for friends with benefits. Usually used in front of parents, teachers and peers to hide the truth.

Person 1: Are you and Alice in a relationship

Person 2: Nah, we're just sailing buddies

Sailing buddies by Trollmaster919 October 12, 2012

Sailing at half-mast

A partial erection.

I’m trying to get it in, but I’m sailing at half-mast.

Sailing at half-mast by Red Bastard July 4, 2020

Sailing the cart 

Used when referring to a golf cart that has been taken off of (specifically) private property and driven down public roads illegally.

1. I saw Buddy sailing the fucking cart down the street like a champion who gave zero fucks.

2. Bill asked “how will we be getting there?” And Michael answered “fucking sailing the cart boiii !!!”

Sailing the cart by harry pot June 5, 2018