Diamond Spoilers:
The first and easiest to get is in the Docks under the building where the auction is taking place. The second diamond you have to earn, the winch that runs the brothel in the main town has it, after you retrieve the 3 items she wants she will reward you but you have to pursuade her to get the diamond from her. You might be able to kill her for it but I can't say I've tried that.
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