Smooth Sailing

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

smooooooooooooooooooth sailing, smooth sailing

by Roberto Esteban Rodriguez April 3, 2008

Sailing with the Captain

A Song by the Celtic rock band Dust Rhinos about Drinking lots of Captain Morgan Rum

I was sailing with the Captain, he'll show me the sights, I wish tomorrow morning would be as good as tonight

by btm321 December 1, 2010

Sailing the sea of brown

The awkward run that you make when attempting to hold your sphincter shut while running to the bathroom when suffering from a case of explosive diarrhea.

Oh wow, looks like Bob is sailing the sea of brown!

by Steve Chuttney April 7, 2011

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

Sailing

Entering into a sexual relationship with another person. The act of "sailing," of course, makes reference to the piloting of a ship, not unlike the sort of maneuvering or establishment of control inherent in the act of sexual intercourse.

"If you sailing her that's an L chief."

by john quan the first September 5, 2018

sailing

easy riding - doing something with out problems

We lost the pigs its smooth sailing from here on

by Anonymous November 7, 2003