There is a thread here about underdressing and I didn't want to hijack it but I am looking for some advice along those same lines.
I am in the exact same boat a MichaelM in the other thread, I came out to my Wife a few weeks ago, we haven't discussed boundaries yet, and she does not know I underdress (I do it in the morning prior to getting ready for work, it is something I have done for a couple years recently, something I also did a lot in the distant past).
My Wife and I are talking about US, more than we ever have, with good results so far, although most of that is non-crossdressing topics, more along the lines of life & relationship topics. Things about our pasts we never shared (I was 34, she was 26 when we met).
As for the crossdressing she knows I have a stash of clothing but hasn't asked any real questions about it, questions like about wigs, forms, pictures, makeup. I have stated I need to be all female and passable when I dress up, it's not just a clothes thing, I am assuming she realizes I have all the accoutrements needed to do that. That's fair isn't it?
She does acknowledge that I will be dressing up when away on work related travel and has said she is not especially happy about it but is OK with it as it is a part of me being me. I think one of the keys is letting her know why I want to do this as best as I can. My feelings and attraction to crossdressing go back 50 plus years, she knows this. We both know it is unrealistic to just simply ask me to stop (I have tried that myself, it never works?) and we know we will both have to compromise to keep each other happy (and married).
So, do I tell her about the underdressing? Do I somehow bring up all the other 'stuff'? Or keep is as kind of a DADT thing? I do think I need to tell her, again not really sure how. We are only in our third week of me being out, do I keep slowly peeling back the layers to reveal what has been hidden for so long? Or leave it buried?