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 05, 2018
by Rockmjd23 October 04, 2003
the act of when a guy is skinny dipping and has boner then lays on his back so that his dick is out of the water and his dick acts like a sail of a ship
guy1: Dude i was skinny dipping yesterday and i saw cody sailing away like a pro
guy2: yeah thats the way to sail!
guy2: yeah thats the way to sail!
by codythegreek October 30, 2011
by Anonymous November 07, 2003
by thidr0 June 15, 2009