The weirdest is a difficult question to answer, but I'm fond of giving out personalized punishments basted on the severe dislikes and hangups of my slaves. As I've said before, I made a slave Shave her head for dyeing it and getting it cut without asking permission.
Well for me this is just something really demeaning and just pisses me off, so an effective punishment I guess but I absolutely can't stand when Top fucks me with parts of his clothing on like socks/shoes, shirt etc. It just makes me feel not worthy of the full effort, ugh! I know its very vanilla but I hate it!!