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.

Sailorboat by Loli Mage April 20, 2018

Sailboat fuel 

Another word for air. Smart ass remark truckers often give to cops.

Cop: What are you hauling?
Trucker: Sailboat fuel
Cop: Let's have a look

Sailboat fuel by zipp06 December 7, 2010

Sailboat tea grinding mill 

The man sits with his legs stretched out. The woman sits opposite the man and places her hips onto him and spreads her legs wide apart. The man puts both hands under either her lower back or legs and draws her to him.

John: My wife wants a new sex position tonight and I'm out of ideas.
Jake: How about the Sailboat tea grinding mill? It's a rare position. I use it sometime with my wife and she loves it.
John: Never heard of it, but I'll give it a shot.

Sailboat tea grinding mill by WouldntYouLike2Know August 20, 2013

Sneaky Sailboat 

A quite pleasurable sex act involving a "crew" of three consenting adults of legal age. In order to perform the Sneaky Sailboat, you need a Captain, a Wench, and a First Mate. The captain and the wench begin intercourse in the captain's quarters while wearing sailor hats. NOTE: it is imperative that the partners do the nasty while standing in order to create the "mast" for the actual sailboat. When the seaman is halfway to Port Jizztown, he lets out a hearty yell of "hoist the sails" at which point he throws a bed sheet over the wench's head, thus blinding and disorienting her. At this point the First Mate relieves the captain of his duties and brings with him the "sneaky" aspect of the event. In a manner similar to a Houdini or a Prestige, the Captain pulls out and leaves the room. The First Mate, who until this point has remained hidden, reveals himself, yells "Avast ye scurvy dogs!" and proceeds to steal the booty and dock his member in the wench's rear port. When properly executed, a Sneaky Sailboat can be great fun at parties, family gatherings and childrens' birthdays.

Captain: Dude, there's nothing on tv tonight, what should we do?
First Mate: I don't know we could always call that girl from the party last weekend and try and pull off the Sneaky Sailboat.
Captain: Yeah that's a great idea, and so wholesome too.

Sneaky Sailboat by captainjackoff October 16, 2011

Tijuana sailboat 

When a man, attempting to hit on a woman who is much too young or much too hot for him, pops an obvious boner while wearing loose-fitting pants.

Omigod, Ashley, that creepy old dude would not stop talking to me. He just kept standing there in his old man pants sporting that pathetic looking tijuana sailboat. It was disgusting!

Tijuana sailboat by The J Team May 18, 2016

Sailboat Shooter 

When you stretch out your ballsack into a cup, pour in a shot of rum, and have a girl take the shot

Sailboat Shooter by Anonymous August 21, 2003