An embellishment of a Dutch rudder: the act of a man holding his own penis wrapped in a warm wash cloth while another person pulls up and down on his forearm(s), creating a masturbatory experience. Can also be used with the double Dutch rudder. The 'Caribbean' comes from the warmth of the wash cloth, the 'rudder' from the original Dutch rudder. Apparently, with two men, neither is gay when forearm manipulation is solely employed.
"I was just trying to clean up a bit, but all of a sudden it turned into a Caribbean rudder and my arm wasn't even tired!"
by Slummervillian February 18, 2009
Splitting a handjob from a hooker with your homie to save money. The hooker will jerk both of you off simultaneously (that's why the have two hands) thus allowing you to split the hourly rate. This is typically only practiced within the Caribbean islands.
Friend 1: "Damn bro, I spent so much money on lap dances I don't have enough to get a handy. You wanna go to that whore house and split something?" friend 2: "sure let's go there and get a wankin' Caribbean Dutch rudder style!!"
by Bigsticky December 15, 2016