Sallyboating 

Motorboating of the anus or cheeks of the buttocks.

Jacob: What did you do last night Brandon?
Brandon: I went SALLYBOATING all night, bro, with these totally hot babes.
Jacob: Oh, thats just nasty.

Sallyboating by saylboat December 13, 2010

Sailboating 

A three-some consisting of two girls and a guy. The guy lays on his back while one girls rides him and the other sits on his face. The two girls face each other holdings hands, creating a triangle or "Sail".

The same thing as Eiffel tower but for 2 girls, 1 guy.

ddannnggggg! Dina and Snooks really know how to go sailboating!!

Sailboating by Sailboatking August 14, 2011

Sailboating 

The acting of rocking a mans member (aka sailboat) back and forth inside a womans vagina (aka cum-boat), this process is refered to as surfing her seas, after which the man finishes within her, this process is refered to as "unloading cargo"

*all aspects must be followed to be considered sailboating

Friend 1: "Dude, what'd you do last night?"
Friend 2: "Not much, just some sailboating."
Friend 1: "Idiot! Think she'll get pregnant?"
Friend 2: "I dont care, not my bitch."

Sailboating by Gary Flongtard December 7, 2011

Sailboating 

The art of coercing a monkey to blow his load into you mouth so you can get high off his jizz.

Bill and Jerry like to go sailboating in the jungles of Costa Rica, because they prefer the old fashion way of getting stoned.

Sailboating by Agent O November 15, 2010

Sailboating 

Much classier than motorboating. To gently blow on a woman's nipples.

Nothing puts Amanda in the mood like sailboating.

Sailboating by BarrettAll November 27, 2011

Sailboating 

The male equivalent to motorboating, where a woman puts her head between a man's legs and moves her face side to side resulting in the man's penis (or "boom") coming about, so to speak.

I told Gladys to get down there and start sailboating me. She manned my jib all night long.

Sailboating by Bob Wylie December 7, 2011

Sailboating 

When a man places a strap on backwards as to be able to have sex with two women. The women straddle him from alternate sides while linking hands over the mans shoulders creating a triangle shape. When the legs and as are both linked the man stands creating the shape of a mast and sail. He then has sex with the two women.

I need to work on my leg strength if I want to do some sailboating tomorrow night

Sailboating by Mypenisisapizza November 23, 2014