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For the maids outfits you complete the "Milking Time" quest (level 3 guild quest thing), and I think you complete the two birds one stone quest (level 2 or 3) and probably something to do with the prisoner npc guy you save during the quest

I only got one maid dress from the quest milking time, do I have to repeat it or buy the rest from some where else?

I got the one I wanted by milking her with THAT certain princess

I did the two birds with one stone and have not gotten the prisoner outfits was there a specific choice I had to make?