If you want to have discussions with your familair you've really gotta play Planescape Torment. You get a skull familair who tutors you and has a whole own personality (and is extremely usefull in combat, he swears at the opponent, who's gotta make a will save or only be able to attack the skull, which has a permanent blur on him).
Also in PT you've got magic tattoo's, how's that for a subclassed item?
Btw, in regular DnD (the PnP one) you can make your clothes magical, they're just armor with a bonus of 0 (remember 3d edition armor class), as well as many other things (but I'm yet to encounter a magical nipple ring


).