Oops x 2, Whup Jambouree is possibly outside of your remit. I guess when I heard Rachel sing it I kinda read it from the other side of the story so to speak - or in other words the invitation of the prostitute on shore. Which incidentally reminds me of The Four Old Whores of Baltimore which despite being presented from the female perspective might be a tad too 'salty'..

Otherwise check my thread on 'Anti-Heroines' for possible songs of interest: http://mudcat.org/thread.cfm?threadid=127154#2832816