In response to your first question, no one but your husband (and he may not even know) what his needs and desires are in terms of when and how much he dresses. He is lucky, very lucky, to have a wife who, obviously, loves him and who wants to understand this pleasurable quirk. I am not that lucky so my dressing is sporadic as opportunity presents itself. I've gone years at a time without dressing due to career and children, but I wanted to dress every day of every one of those years. It's a lot of work, though. At this point in my life I dress as much as I can (it's not enough) and that can range from underdressing all the way to totally presenting as a woman and going out in public to shop. With your support your husband will find the proper level for himself and, hopefully a level that is acceptable to you, as well. Good luck to both of you.