28- Captain’s Wench
This is an upscale dockside working girl (oxymoron?). She will only "be with" a Captain or Officer. She is prettier, cleaner, and more refined than what one would expect. She is more of an escort, making the captain buy her drinks and food (as well as others). She actually works for the house to promote people to spend.
Draw the party together as debtors to the local lord, king, head of the thieves guild, or mercenary clan, who is forcing them to work together to pay off their debts.