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.
by john quan the first September 5, 2018
by Rockmjd23 October 4, 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 May 31, 2011
by Anonymous November 8, 2003
by thidr0 June 15, 2009