smooth sailing

adj.
The lack of teeth dragging during fellatio.

"That bitch was smooth sailing!"

"She wasn't smooth sailing and now I'm not going to be able to fuck for two months!"

"That homeless bum can smooth sail all night for some crack."

by C Witt November 08, 2005

Ass Sailing

The act of performing oral sex on a man while an object is inserted into the rectum of the one performing the oral sex.

My boyfriend loves it when I blow him, the fact that it's usually ass sailing only makes it better for both of us!

by redditperv August 24, 2012

Fire-Sailing

Burning California’s Democrat-nursery to disperse Democrat voters into red states.

Instead of gerrymandering to move the districts every ten years, we can do some Fire-sailing to move the voters whenever we want...

by SweetAtAll September 10, 2018

Home sailing

A portmanteau of "home free" and "smooth sailing". It means the same thing as its component words: the rest is easy.

Oh really? Well after that it's really easy! It's pretty much just home sailing from there.

by SlauterHouZe101 April 14, 2011

Set sail

to leave with all there people

lets Set sail once werve gathered everyone

by 201HH November 26, 2020

Sail Boater

A person that owns a sailboat, who acts better than everyone else, especially on race day; one who thinks they are the king of the marina; someone who thinks driving european cars are better than anything else; someone who is a complete rude stuck up asshole snob.

Norbert loves to sail. He is from Nantucket, Home of the majority of Sail Boat snobbs. He always thinks he is the boss of the road and the marina. Because he drives a European Car that is highly over-rated and sails. Which to him is better than anyone else can do.

Roy thinks Norbert is an asshole, because he is a Sail Boater. Roy is correct, Norbert is an asshole...because he sails and Roy doesn't.

Roy The Power Boater: (Walks past Sailboater) "Hey man how'ya doing?"

Norbert The Sailer: (Looks down real fast at his Sperry Top Siders) "arghhh"

Roy Power Boater: "Heyy mann, wtf you can't say hi? I was just trying to be nice!"

Norbert The Sailer: "Leave me be, I'm busy and I don't know you"

by Kevin Baines March 15, 2006

garage sailing

beats me.

I dint know what happened I must have been garage sailing.

by Anonymous August 25, 2003