by De Jay Hemmingston January 18, 2010
The act of "sailing" many female genitalia's in the width of one cruise. To have sexual relations with many woman in one sitting
Andrew: Dude, Broken told me the other day that he was going pussy sailing for some ass and I laughed hysterically.
Sandy: Broken can't go pussy sailing, hes missing the sail.
Andrew: that is not all he is missing.
Sandy: Broken can't go pussy sailing, hes missing the sail.
Andrew: that is not all he is missing.
by Druidbegone December 18, 2009
"Got my car fixed earlier mate, fancy going pussy sailing tonight?"
"Yeah! Pick me up, and we'll go!
"Yeah! Pick me up, and we'll go!
by pussysailer March 19, 2011
The act of tying a very loose woman to the mast of a ship and pulling her lips apart in order to catch wind
by jeffery r. sutherfizzle March 16, 2010