I've heard this expression used several times and even though my own brain translates it to "most awesome chick on the planet", when I've heard the expression the context seems derogatory.  Why?  No matter what age, we all still want to be pirates.  We all love dirty girls.  Little bows in your hair and no sex just don't cut it.  Maybe they should say dirty pirate provider, then it wouldn't sound derogatory.  I don't know.  Maybe I should get back to work.  Keep flying the jolly Roger, all!  Uh oh, i hear a "clean executive yenta" coming down the hall...