ship sailed

While getting a handie from your girlfriend while laying on your back inverted (like being on a decline bench at the gym) and she has you edged to the point of cumming but immediately water boards you and you don't know if you are gonna cum or die.

Last night was amazing. Angie ship sailed me to the point of climax. I didn't think I was gonna survive.

by Shtevun 69 June 29, 2017

Urban Sail

When a breeze kicks up and your umbrella becomes either uncontrollable, inverts itself in your hands, or flies from your grip.

Synonyms: urban kite, umbrella sail, umbrella kite

"Umbrellas are a pain in the ass. Sure, they protect your head and shoulders from the rain, but the second the slightest breeze kicks up, you suddenly find yourself the unwitting mast for an urban sail that, best case scenario, inverts itself in your hands, and worst case scenario, flies from your grip, whips down the street and spears the Pope in the neck." - Tracy V.

Source: Cracked.com, Tracy V. (Invictus99)

by notfeelingcreative June 4, 2014

Tag Sailing

Tag Sailing is like a pub crawl but with tag sales. One right after another. Usually on a weekend.

The town-wide tag sale is today. Who wants to go Tag Sailing?

by Randwulf0969 June 24, 2023

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

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 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