If he can walk up to mom, unbutton her shirt himself and lift up the bra... it might be time to stop... lol. BUT, with that said, I don't think this is
WRONG - it simply starts crossing the lines of general (read:typical) social acceptability.
I also don't think crossdressing is wrong (just freakin weird and an indication that something upstairs is likely broken), nor is it necessarily wrong to put a cute outfit on your german shepherd, but both will garner strange reactions from the average Joe. At least until enough people are sufficiently brainwashed so as to accept it as "normal."
PS. First guy to argue with me about crossdressing is going to have a hard time convincing us that he isn't a closet cross-dresser...