As I posted about a month ago, while the wife and I were on vacation, she suggested that I get dressed up and enjoy myself while we were driving to her mom's place. Out of the 4 days of travel time I only interreacted one time with others, and it was a positive reaction, but that was only because of the support and encouragement of my wife.
Yesterday I sat down and told my wife I would like to go out in public with her again while I was dressed as a woman. She kind of rolled her eyes and said she thought this would probably happen. She wasn't against the idea and kind of gave me the impression she would be willing to do it again. But I told her if she really didn't want to do it, then that would be okay too.
I told her she could pick the time we do this, and I didn't care if it is in 1 month or a year, and she said it probably wouldn't be that far away. I also told her; she could pick the activity and how I was dressed. I suggested that I don't wear a dress if she plans on wearing sweatpants and a t-shirt. I told her that we should be dressed similar as not to draw attention to us.
I figured that I won't bring up the subject again for a while (if ever), so not to put any pressure on her.
I told her that her comfort level (and sanity) was more important to me than us going out as a couple of girlfriends. I know we will have to leave this small town we live in, because neither of us is comfortable for me to be seen as a woman by friends, family and/or co-workers.
It took me a couple of weeks to get the courage to ask her this, but again she was supportive, and I am not sure why I get so nervous to ask her these types of questions.