I have been pondering this. My folks are pretty old school, although they raised me to be very tolerant of others, even of folks who might be a bit unusual. I've worn heels in public, told my ex-wife about them shortly after we met, and yet, I've never told my family. My sisters might have their suspicions; my little sister actually asked if she could borrow a pair of sandals I used to wear which came out of the women's section, and one Halloween many years ago I tried on a pair of my older sister's heels, to which she gave me the "ew..." response. Otherwise, I've never told my folks, and I'm trying to decide if I should. My ex-wife and a priest friend of mine (whom I confided the heels to) think it's really none of their business. My friend the priest was cool with it, although his first reaction was "how do you even walk in them??".
I guess the main reason I ask is although they started out as more of a bedroom thing, I've realized they really are part of who I am, and I often wear them around the house. I've worn them in public several times, but I still feel like I have to hide them from my family. Last time my parents visited I had to round up and hide all the shoes, lest they walk past my bedroom and see that the cats have pulled the closet doors open.
So, does anyone have any thoughts? I feel like it would be a load off my shoulders if I could say "hey, I'm still your son (or brother), and I just happen to like wearing women's shoes". My guess is they might get a chuckle out of it, and I'm certain they aren't going to get all bent out of shape about it, but I guess I don't want to disappoint them. Maybe if I point out my ex (whom they liked very much) was OK with it, then maybe they will be more inclined to believe it's a harmless quirk.