A sexual endeavor in which the male participant informs the female that he will be performing a "Sneaky Castro", but instead of wasting a perfectly good Cuban cigar, inserts his finger and carries on similarly top the Sneaky Castro.
Where a man dresses like Castro then procedes to have sex with a woman in various ways while smoking a cuban and singing the cuban national song. This must take place on cubas birthday which is the 28th of June.
An extra extra extra sneaky Castro is where you tell you girlfriend you will be performing a “sneaky Castro” but instead you shove 3 Cuban short range smoking missiles into her oriface.
Performing a cunnilingus or analingus from behind in the doggy style position. "Ass up face down" Then inserting a cigar in the recievers anus during oral. Used in the The Duece Biggalo, movie European Giggalo.
Vanessa had never experianced a sneeky castro before. Let alone oral sex from this position. After the act she smoked the cigar.