Back in high school, the times I would come home with my nails polished just about every color under the sun, my parents had me take it off immediately. I did it quite frequently, that then they caved only under one condition, only on and around Halloween.
When I was with my wife, she would help me do my nails, and fit me up in girls clothing, she was always jealous of my small stature that she expressed every single chance she got. One day she was helping me get dressed up, and thankfully our room door was locked, but my aunt almost walked in on us. (was living in a family house at that time.)
But since the split back in February, and divorce going to finalizing in August, and that I had come out to her as transgendered a week ago, she wasn't shocked, or surprised, but kinda glad and happy for me that I finally found who I am, and very supportive. She's going to throw the jealousy thing out again when she finds out I'm a size 4. It might be better that I don't say that I did slim down even more.
Edit; Past high school though, my mom has slightly understood that I was into girls clothes, and would try and make an attempt with getting me hello kitty shirts, of any color, and well that was about all she would get me.
On the main note I was trying to get to though, past 2010, I've been rather more open in my cross-dressing, like I would wear my girly outfit to family reunions, well the one I did go to. Otherwise I make no attempt to hide it.
Though I still haven't come out to my immediate family, nor extended family that I'm transgendered yet. The only people that truly know are the lot of you lovely people, my work (all my immediate co workers), My wife, my cousin's best friend, and my wife's sister.
Kate ♥