I am a fifty something individual who came out to their spouse 15 years after starting the relationship. She did not take it well and never wanted to discuss or deal with it. For 10 years after that it was the white elephant in the room that caused the relationship to go in to a tail spin and eventually end. While cross dressing was not the single cause of the split it was the catalyst that affected communication which in turn created many other problems that eventually made being together no longer an option.
We split in 2007.
The last two years I have been in a relationship with a woman who accepts, who sees me dressed up all the time, who shops with me, shares the dressing experience with me - the total opposite of my experience from my 25 year relationship. While I did not tell her right from the start I did tell her about this shortly after we met and while she was surprised she was also open to the whole thing.
The challenge that I have in the current relationship is that I want to dress 7/24 (something that I was up front with her from the beginning might be a possibility) and she does not want that. She is fine with me dressing much of the time but not all of the time. That is the new challenge that I must weigh carefully and decide upon.