Pussy Sailing 

a term that means looking for girls/pussies.
looking for wiling girls to have sex.

"Man, It's been a rough week."
"Yes, we should go pussy sailing."
"Indeed"

Pussy Sailing by De Jay Hemmingston January 18, 2010

Pussy Sailing 

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.

Pussy Sailing by Druidbegone December 18, 2009

pussy sailing 

when lads go out in their car's looking for some pussy

"Got my car fixed earlier mate, fancy going pussy sailing tonight?"
"Yeah! Pick me up, and we'll go!

pussy sailing by pussysailer April 4, 2011

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

smiling pussy 

Post orgasmic labia...
A sexual satisfied females lady parts.

Look at that smiling pussy, she has been properly satisfied!

smiling pussy by The eggplant August 4, 2017