A couple questions for those in the Don't Ask Don't Tell situation

[GretchenM]

I think you should go ahead and get a wig and some makeup. Don't spend a fortune on it but it needs to be better than a Halloween wig. It is an experiment to see how you react to that addition and, in my experience, that addition adds a lot to the experience. Your mileage may vary.

In my opinion, if you are married your situation can become horrendously complicated. Good communication between your wife (husband) and yourself is very important. And be respectful of their feelings; after all, you want them to respect your feelings as well. More important to talk about feelings than facts. The facts are important, but the facts are just facts. The feelings are where the rubber hits the road. That is what and where you live and interact. Use analogy. "Putting on some feminine attire makes me feel like ..." Here is an example. "... like I am naked on a vast empty beach and I can be totally free to be nothing but myself." Using analogy really works. It also works with things that are not so positive like being rejected in some way. And try to avoid using the word "you." That is a bit of an accusation and immediately puts the person on the defensive.

[Jenny22]

I'm lucky. My dear wife passed on 5 years ago. I dress every day. While I could do full makeup, I only use lipsticks. No wig, although i have 5 or 6. I only wear one and use makeup when I go out. No sense in doing all at home, unless I want to spend a lot of time in front of a mirror.

[ChrisX]

I work at home and usually dress, but no makeup or wig for me. Wigs are hot, and I'm in a don't-ask-don't-tell situation with my wife and worry about getting the makeup fully off.

[Veronica Lacey]

I do not wear a wig or any make up; just not my preference.

My wife tolerates my dressing desires even so far as to say she is reasonably accepting. She does not wish to see my wardrobe (or know of its size) nor see me dressed but will offer times to be out of the house or let me dress upstairs while she is downstairs for a while. She would not be as supportive if I wore make up and/or a wig. Things would get a bit strained if I did.

[HollyGreene]

I don't often get the chance to do full make-up.
My wife usually goes on vacation to her home country for about 4 weeks in the summer, so that's my cue to bring out the make-up. I spend a lot more time dressed during that time, too.