Sailors

In short, Sperm. The word 'Semen' closely resembles seaman which is where the word sailors got its name

Billy: Wow look at that girl over there i'm gonna go talk to her

Joseph: You gonna have her catch those sailors tonight or what ?

by Bigballer2427 September 16, 2017

Sailorboat

A person who identifies as Transgender or anything other than male or female. Can also be used to describe feminine men or masculine women.

Person 1: Hey dude, see that person over there?
Person 2: Yeah?
Person 1: I can't tell if that's a guy or a woman.
Person 2: Oh, that's cause they're a sailorboat.

by Loli Mage April 20, 2018

sails'd

getting ditched by your best friend

Bryan totally sails'd me last night!

by h12445 November 10, 2017

Sailor’s Cannon

After you cum inside a condom, blow it up like a balloon and pop it in you’re partners face.

i could not wait to get Debbie home and give her a sailor’s cannon after the office party.

by shifty hobo November 30, 2017

Sailing the cart

Used when referring to a golf cart that has been taken off of (specifically) private property and driven down public roads illegally.

1. I saw Buddy sailing the fucking cart down the street like a champion who gave zero fucks.

2. Bill asked “how will we be getting there?” And Michael answered “fucking sailing the cart boiii !!!”

by harry pot June 5, 2018

Sailboating

As opposed to the pedestrian act of motorboating, sailboating, shuts off the motor and gets back to nature. First, you drop anchor in preparation for a little sunset rose and cheese. The captain puts his or her face down between the butt cheeks. Whilst the first mate uncorks the wine and cuts the cheese, you just let the wind blow across your face and through your hair enjoying all that nature has to offer.

Chad took up Thadeus on his offer to go sailboating...they had a great time!

by chappynyc September 20, 2018

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