The Sailboat Technique

When an circumstanced male grips the tip of his foreskin, and the bottom of his ballsack and tugs in opposite direction, thus creating a triangle shape similar to the sail of a boat.

Dude bro 1: "My girlfriend caught me doing the sailboat technique, she hasn't talked to me in a week."
Dude bro 2: "Yarr, a captain always goes down with his ship.."

The Sailboat Technique by drippy boy March 17, 2019

Racing Sailboats

The act of pretend racing large model sailboats between individuals, in which the finish line is the other participant's entire colon. First racer to take the entirety of their opponent's vessle loses. Smooth sailing!

Man, this day is really dragging. I cant wait to get home so me and my boy can be racing sailboats.

Racing Sailboats by Milk Money Mike March 22, 2019

Backward sailor

When you good lady slips a finger or two into your ass during sex.

Oi love give me a backward sailor it will make me blow my load.

Backward sailor by Goochstroker October 30, 2020

Big Sailor Baby 

Better rapper than most

He’s a big sailor baby compared to Drake

Big Sailor Baby by Artistdigest November 28, 2021

Chris sails 

He had like 45 girlfriends in the past 3 years and he was thicker than all of em

Oh that’s Chris sails big booty ass

Chris sails by Run2drake March 20, 2022

Garage Sailing 

The act of going to multiple garage sales, usually involves waking up early on the weekends and bargaining for lower prices on items you can flip on eBay.

I went garage sailing one weekend for a few hours and made over $100 selling that shit online.

Garage Sailing by Mel G. July 10, 2022

Garage Sailing 

The act of going to multiple garage sales, usually involves waking up early on the weekends and bargaining for lower prices on items you can flip on eBay.

I went garage sailing one weekend and made over $100 selling online.

Garage Sailing by Mel G. July 10, 2022