Sailboatin 

When you talk about someone coming over and talkin to yo dime piece then they do

I was chillin with this bitch and i saw a dude creepin so i started sailboatin and said this nigs gonna come over here and talk to you, and he did.

Sailboatin by young co September 16, 2010

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

sailboarding

To use a piece of cloth(ex. bedsheet) and tie one end to your longboard, and to hold the other ends up with your hands.

Allows you to skateboard without needing to kick, as the wind pushes you.

Did you guys see that guy sailboarding down the road?

I used my extra bedsheet to sailboard yesterday.

sailboarding by bombsite March 23, 2011