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.

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.

by Goochstroker October 30, 2020

Big Sailor Baby

Better rapper than most

He’s a big sailor baby compared to Drake

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

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.

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.

by Mel G. July 10, 2022