Kim, I would say that you would want to take the boy to a vet. My second comment would be that it could be hot spots (merged into big ones)......and they can be caused by a few different things. Once you rule out fleas, I would ask the vet for a cortisone shot or two...long acting......and then if that does not work, then a kitty prozac of sorts. Some cats (Miley is one of them) are obsessed with licking....and lick themselves and usually others, including humans. All this is just a guess on my behalf and I would take the boy to the vet soon. He could get a nasty infection going....then $$$$$$$$$$$$$$$$$$$$$$$$!

Keep us posted!