A portmanteau of "home free" and "smooth sailing". It means the same thing as its component words: the rest is easy.
by SlauterHouZe101 May 3, 2011
Get the Home sailing mug.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
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Sailfin
• SAILF
• sailfi
• sailfish
• Sailfished
• Saif
• Sailor Moon
• sailor
• sailing
• Sail Boating
I shafted that combat sailor the other day. Thought I would give him something to do as he doesn't do anything useful these days.
by Jdyfbdk November 20, 2017
Get the combat sailor mug.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
Get the Fire-Sailing mug.A sad setting of sails (or sad setting’ of sails) is a mess, or even an eyesore. It’s something that’s completely messed up. It’s the opposite of Ship Shape.
by DeadHead68 June 24, 2021
Get the sad setting of sails mug.Blue or white hats that children under 13 would wear from 1950-1980. These children were usually expected to help mom cook and clean or do hard labor. They were often beaten if they didn’t do it.
Dad in 1969: Son, don’t forget to put your asshat injun sailor Jew hat on before school.
Son: I won’t father.
Son: I won’t father.
by Braydong44 October 19, 2023
Get the Asshat injun sailor Jew hat mug.The act of attending a meeting directly after having consumed some amount of alcohol, especially if drank with others also in attendance.
"This meeting's going to be such a headache- let's go sailing to make it go a little smoother."
Or
"You seemed pretty content in that judicial meeting..."
"It helped that I was sailing it."
Or
"You seemed pretty content in that judicial meeting..."
"It helped that I was sailing it."
by 52008 April 27, 2010
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