look up any word, like darude - sandstorm:
 
1.
masturbating with sand paper in hand
See smooth sailin' for a more extensive definition
smooooooooooooooooooth sailing, smooth sailing
by Roberto Esteban Rodriguez April 03, 2008
 
2.
easy going, an unbumpy ride into the future.
"I've finally got that out of the way". "Well, now it's smooth sailing from here"
by shortanstuff February 06, 2009
 
3.
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 07, 2005