Sailing Your Boat

There are Different Stages to Sailing Ones Boat.
Similar to the Bases in Baseball.
If you go all the way around the world, well guess what, you've had sex.
The other stages are up to you. You can pretty much make it up and Elaborate as you wish.

"Dude, last night at the dance Eve almost sailed her boat, thank god the Coast Guard was there."

"So, are you sailing your boat this weekend?"
"Ya, but were just going to an Island off the coast"*Wink Wink*

"You Let Your Anchor Up?!?!?! You Slut!"

by Kortney J May 1, 2007

Sail Boating

Swimming on your back while having a massive erection.

"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."

by Sarpa May 26, 2016

Sail boating

The act of farting against the scrotum during Anal sex, turning it into a spinnaker sail.

After a delicious taco Tuesday meal, she took me sail boating

by TeamCook January 21, 2019