For me, it's not much of a concern about my being comfortable around her, but the other way around is a different story. My wife, by her own admission, isn't very girly and is most often in a t-shirt and sweats. Makeup may appear once every other month and heels perhaps 3-4 times a year. So she can't quite figure me out on several levels, but she tries, even though I can be a bot pushy at times. She's come to a point where she's fine with almost everything except:
1) Breast forms - not a huge deal, but she's not a fan.
2) Makeup - she's tried to help me once or twice but I can tell it bothers her.
3) Wig - the big no-no. As hard as she's tried she just can't get over this. She says she'd like to get over it for my sake, but not yet. I certainly appreciate her effort.
It was only when she got to the point that she said I should go meet others like myself so I can have someone else that could look at me and discuss our 'hobby'. I love her dearly for this.
Anyways, my advice is be patient, listen to her, and just love her for everything she does.
-Bree
