I don't think that is a geisha in the middle. Just a Japanese lady in a kimono.
Often these are used as gifts commemorating peoples' retirement (usually from military service). But in those cases the cups would be marked with a commemorative message. Since there is no message on this, and the imagery is kind of generic Japanese "memes" (dragon, kimono, cherry blossoms, phoenix), I guess it might be a pre-war souvenir for tourists?