by BarrettAll November 27, 2011
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.
by Bob Wylie June 10, 2011
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.
by Mypenisisapizza November 23, 2014
Friend 1: "Yo, come check out my sailboat after school?"
Friend 2: "Fuck No!"
Friend 1: "Oh. But i just put a new finish on it."
Friend 2: "Maybe."
Friend 2: "Fuck No!"
Friend 1: "Oh. But i just put a new finish on it."
Friend 2: "Maybe."
by Gary Flongtard December 7, 2011
by zipp06 December 6, 2010
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.
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.
by captainjackoff October 17, 2011
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!
by The J Team May 19, 2016