smooth sailin'

When someone jacks off with sand paper. Typically one who is in to masochist things would perform this.

Hey, what aisle is the sand paper on? I want to go smooth sailin'.

by Krl Wnslw February 17, 2008

sail

To all you dumb fucks who think it is sexual, it is a piece of material extended on a mast to catch the wind and propel a sail boat. Or as a verb it means to go sailing.

"Do you sail?"
"Yeah, I went sailing last weekend and came back soaked and tired."

"That dude has a giant sail on his sailboat!"
"Yeah, I bet that boat does great in regattas!"

by Ija Renrut December 9, 2013

sail cat

A dessicated and totally flat cat that has spent a few months lying in the road. When scraped up and thrown, it sails like a Frisbee.

There's a great sail cat in the makin' down on Dongbuster Road. We should go and get it some evening.

by Bumkicker Slade May 10, 2005

sailor

What hookers often call a potential customer.

Hey sailor, looking for a good time?

by Elitist January 27, 2004

Poop Sailboat

A sexual act in which a Male/Female defecates on themselves with their legs closed and leaning over an object. Followed by a partner Male/Female that urinates on the fecal matter; causing the feces to slide down between their legs like a Poop Sailboat.

Mr. Van Den Berg's Poop Sailboat caused a rash down the back of his legs, that was visible while he wore shorts.

by Mr Van Den Berg February 25, 2010

Old Sailor

Someone who likes to motorboat a woman's tits.

John: Claire's mom just made me grab her hooters.
Jeremy: Well snap out of it! What, a hot older women made you feel her cans? Stop crying like a little girl.
John: I wasn't crying like a little girl.
Jeremy: Why don't you try getting jacked off under the table in front of the whole damn family and have some real problems, jackass. Hey, what were they like anyway? They looked pretty good, are they real? Are they built for speed or comfort? What'd you do with them? Motorboat? You play the motorboat?
makes sputtering motorboat noise
You motorboatin son of a bitch! You old sailor you! Where is she? She still in the house?

by Sandbaggin' son of a bitch January 18, 2009

Sailor Man

A male, usually horribly overweight, who insists on 'cross-playing,' especially one that persists in wearing a fuku or Japanese schoolgirl uniform.

That 300 lb. man in the miniskirt, knee-high boots, and blouse you see at ACEN every year? Yeah, that's Sailor Man.

by PwF September 9, 2007