The bigger the boat, the smoother the sailing.

A response to the phrase "it's not the size of the boat, it's the motion of the ocean".

Implies that "size matters".

Woman - "Wow dude, that's a really below average penis."

Man - "It's not the size of the boat, it's the motion of the ocean!"

Woman - "Maybe. But the bigger the boat, the smoother the sailing."

The bigger the boat, the smoother the sailing. by Dakron July 11, 2014

pussy sailing 

The act of tying a very loose woman to the mast of a ship and pulling her lips apart in order to catch wind

we went pussy sailing with Bianca last weekend and we went faster than my buddys speedboat.

pussy sailing by jeffery r. sutherfizzle March 15, 2010

Torrey Pines Sailing Team 

A bunch of retards banded together to sail boats, who fight over retarded things, led by retards, funded by retards, and supported by rich retards

Did you hear about the torrey pines sailing team?
Yeah can’t remember the last time they stopped fighting and won a race

Torrey Pines Sailing Team by Dipdip123 September 24, 2018

car sailing

To open the sun roof, sticking your head out, sitting on the arm rest while driving by looking out the top and pressing the gas and brake with your left foot, only.

chris romano is a gay sloor. car sailing

car sailing by Ryan Brody October 13, 2008

Smooth Sailing 

masturbating with sand paper in hand
See smooth sailin' for a more extensive definition

smooooooooooooooooooth sailing, smooth sailing

Smooth Sailing by Roberto Esteban Rodriguez April 3, 2008

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