bag sailor 

one who's nutsack is so big they can use it as a sail on a boat

we got off the island because it was windy and Gene was an old bag sailor...

bag sailor by genopetralli September 30, 2015

Mud Sailing 

When you pee and take a shit at the same time. Most notably when you have food poisoning or had a beefy 5 layer burrito from Taco Bell.

Dude how's your stomach? Bro I been mud sailing all day from that burrito.

Mud Sailing by Jermeiser October 6, 2016

tub sailor 

Members of the coast guard. Bath tubs are about the same size of a Coast Guard cutter.

Well if you can't get into the Navy, you might want to be a tub sailor.

tub sailor by mighty mighty SEALtone November 24, 2016

Scamming Sailors 

A famous Tripfag on 4chan, mostly visiting /OPGG/. Known for his Blackbeard posting and baiting underage kids falling for his "It's okay If I cheat" bait.

Scamming Sailors !Scam/X6css
>I hate cheaters they are the scum and should quit the game, it's only okay If I do it.

Scamming Sailors by JewJulie November 28, 2016

clam sailing

When a woman with a skirt and no underwear (or naked) stands over a vent that's blowing air.

Marilyn Monroe was holding her skirt down because she was clam sailing to dry off.

clam sailing by DoomEngin33r March 31, 2017

cum sailed 

A woman that gives a blowjob to everyone in the room all in a line.

Bitch, you totaly cum sailed that party the other night!

cum sailed by Yermum69n July 13, 2017

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.

ship sailed by Shtevun 69 June 29, 2017