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.

by Druidbegone December 18, 2009

garage sailing

The act of "hopping" from one garage sail to another, often with the assistance of a newspaper listing.

Dave and Theresa got up brigh and early every saturday and went garage sailing.

by arcan August 25, 2003

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!

by pussysailer April 4, 2011

Sailing

Drinking an abundance of Captain Morgan Original Spiced Rum.

Yo dude, Me and Donald went sailing with the Captain last night!!

by Travis November 23, 2004

Sailing Away

A song by the band Styx that is considered a classic. It is so happy and cheery-sounding that it makes people want to punch something.

Song: "I'm Sailing Awayyyyy....."

Person: "AHHH GOD!!!!" *goes nuts and punches a wall*

by Fruuze March 4, 2009

The bigger the boat, the smoother the sailing.

A response to the phrase "it's not the size of the boat, it's the motion of the ocean".

Implies that "size matters".

Woman - "Wow dude, that's a really below average penis."

Man - "It's not the size of the boat, it's the motion of the ocean!"

Woman - "Maybe. But the bigger the boat, the smoother the sailing."

by Dakron July 11, 2014

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.

by jeffery r. sutherfizzle March 15, 2010