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 25, 2016

Floor Sailing

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

sails and cervix

What a horny dude would hope dat da hot female skippers of a schooner-tours company would offer.

When booking an outing with a seaside shop offering “sails and cervix” package-tours, one should make sure to ask if their standard price includes having your gorgeous guide spread her legs for you, or if said delightful “extra” actually COSTS “extra”!

by QuacksO October 8, 2023

Sailing

sail·ing
/ˈsāliNG/
The fine art of getting wet and becoming ill while slowly going nowhere at great expense.

Sailing is my friend's hobby, but I can never figure out why he does it every weekend.

by TheValGal November 12, 2023

Hoisting The Sail

When you super glue one ball to each leg and you proceed to run a marathon.

“Man, that marathon was such a pain I don’t think I trained enough!”
“Tell me about it! I was hoisting the sail the entire time.”
“Not surprised, you’re a dirty hoister.”

by SwagRK July 13, 2025

Sail

Slang for suicide, or a suicide attempt. Similar to the slang associated word, "off, offed, offing".

"Yeah did you hear? That guy sailed"

by Nomicaluran December 23, 2023

Sail the porch

To spend long periods of time on one's front porch. Usually involves music, conversation and some form of inebriates. May also involve food, especially food produced from a grill.

I'm just planning to sail the porch tonight, you can come hang, too.

by tehamahreha February 28, 2009