With my first wfe, we were engaged at 18/19 back in the late 60's and one evening I finally plucked up courage to tell her I liked cross dressing. She said nothing but just looked at me for a while and then finally said " With your blue eyes you'd look lovely with makeup". I thought I'd died and gone to heaven. A while later ( can't remember how long) she saw me completely dressed for the first time and totally freaked out, crying and carrying on for ages. To her eternal credit, we did get married and she tolerated my dressing ( but didn't want anything to do with it) for about another 25 years.
With my current wife, it started as almost a bet. She knew about my cross dressing past and as part of a jokey conversation she said I wouldn't still be able to wear heels after several years break.... of course, I had to prove her wrong ( she was!) and it kind of grew from there. She doesn't mind but I think she is kind of jealous because her health prevents her from doing/wearing the kind of things she would like, plus she is wary that I might go off the rails with it.
With my current wife, it started as almost a bet. She knew about my cross dressing past and as part of a jokey conversation she said I wouldn't still be able to wear heels after several years break.... of course, I had to prove her wrong ( she was!) and it kind of grew from there. She doesn't mind but I think she is kind of jealous because her health prevents her from doing/wearing the kind of things she would like, plus she is wary that I might go off the rails with it.