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

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.

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!

pussy sailing 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!!

Sailing 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*

Sailing Away by Fruuze March 4, 2009

Scifing 

to scife; be an out of line female; to ditch a planned setup; to annoy a male; to think you can order someone to do something; be totally and utterly out of line.

__ex. 1

bro 1: Damn bruh, this breezy is dodgin' me now. Shes forsure scifing us.

bro 2: Scife'n hoe!

__ex. 2

bro 1: Wow, this broad is blowin me up.. even after she tried to get me to come over. In the daytime!

bro 2: Shit mane, you definitely got a scifer on your hands.

__ex.3

bro 1: This girl thinks a house date with her friends is acceptable.. even before she let me clapskie.

bro 2: Tell that girl to get her scife'n ass outta here!

__ex.4

Scifer no Scifing!!!!

Scifing by Rusty T. B. Shackleford September 19, 2010

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."

The bigger the boat, the smoother the sailing. by Dakron July 11, 2014