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1.
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"
by De Jay Hemmingston January 17, 2010
 
2.
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.
by Druidbegone December 18, 2009
 
3.
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!
by pussysailer March 19, 2011
 
4.
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.
by jeffery r. sutherfizzle March 15, 2010