When a man takes his erect penis and in a smooth "sailing" motion runs it along the butthole of a prone person.
The other day Kenny tied a little sail to his dick and went dirt sailing before throwing a piece of eight on her back!
by Habberstamp July 9, 2022

point of sale: in an establishment that sells goods or services, the location at which payment for goods is made.
sail: the power harnessed by a sail or sails, or the use of this power for travel or transport.
point of sail: the location at which a sail harnesses power.
sail: the power harnessed by a sail or sails, or the use of this power for travel or transport.
point of sail: the location at which a sail harnesses power.
by Pseudonymthewild@gmail.com February 9, 2013

When the fat guy in the hot tub lets his mid section rise to the surface and creates"Balls Island" He then pulls his scrotum vertically,thus creating a "Full Sail"
On a cold winter night in an outdoor hot tub at the Las Vagus Holiday Inn.Hendrix and his quarter ton comrades were concerned about the direction of the frigid desert air that was blowing across their tub.Hendrix,being the only one who finished high school,but was in the Navy for a short time before being dishonorably discharged had an idea.Being the most resourceful fella in the bunch he gently lets his mid section float to the surface of the hot tub,creating "Balls Island" from which he is able to yank his large scrotum skyward creating a "Full Sail" which gathers wind that he can now confirm is coming from an easterly direction.
by Turd Blossum January 7, 2020

by DoomEngin33r March 31, 2017

Floor Sailing is the next submission to the Olympic Games Committee defined by the distance a person travels while tripping or slipping on a smooth, slick or slippery surface!
Dude if you had only practiced a little more you could have gotten a Gold Medal in “Floor Sailing“ for that record slide in class!!
by OneVisionVideo November 27, 2020

"Dude, did you see Jenny in her new bikini at the pool?"
"Yeah man, I saw her while I was practicing my backstrokes. She had me Sail Boating."
"Yeah man, I saw her while I was practicing my backstrokes. She had me Sail Boating."
by Sarpa May 25, 2016

by Neverendbro December 15, 2010
