What do you think?

[Maria 60]

I closed my gazebo with a tarp and put a gas fire pit in there so I could smoke a cigar or just enjoy the winter weather with a bottle of wine warm in there. Last night I was opening a bottle and going in it and my wife told me the niebours were away for the weekend and if I wanted to dress.
I went out in a dress and thicker tights for the cold and she handed down to me one of her winter coats that made it more fun.
A couple of weeks back she was upset with me about not being careful with my fem stuff and to sit down with myself and ask myself where I want to go with my hobby.
She asked if she put out the green light what would I do, would I want to tell the children and if yes would I want to dress in front of them? Would I go out dressed and maybe meet up with some friends on the community like I had mentioned to her in the past. Would I dress in front of our parents and tell family and friends and dress in front of them? Wouldn't I feel uncomfortable being dressed like a women in front of my friends and family?
Well that sure was a lot of questions but I did want to answer them as honestly as possible. I told her I don't want to dress in front of my children and family and friends. BUT and this is a big BUT, I told her I would probably like to at least tell them so if they do see a hint of pantyhose sticking out from somewhere on my body or we meet in a mall and they see a bra strap it won't be a total shock.
I wouldn't have to totally be so careful with my stuff and not have to worry if I don't delete the history on our laptop. I asked my wife a few years back since we are traveling together more maybe it would be a good idea to tell maybe one of our daughters so in case something happens she could do some damage control.
I also told her I know of a few sisters here on this community who are from our city and I would like to at least try going out dressed once but would feel better if our children knew so in case I do get spotted out it won't be a shock.
I answered of course I would feel uncomfortable dressed like a women in front of my childhood and family, that's not what I want. All I want is to share this with her and maybe spread my wings a little on my own and not put her in a embarrassing situation. I thought I was very honest and reminded her that I'm also very happy where iam now with her now. I could see she was in deep thought and she told me she wants to keep this line of communication open and maybe we could consider telling our oldest daughter and see how she feels about the situation. I could see why she chose our oldest because she is more strong emotionally and has proven she could keep a secret and very down to earth. I could see lately with us getting older my wife has been wanting to do more and her saying is "what are we waiting for when it's too late that we can't do it". We left it at let's leave the line of communication open and let's just think about it and not rush into anything and sleep on it.
I'm not sure what to think about this one, on one hand maybe I should just be happy I'm able to dress in my own home at anytime and she will support that. But it would take a lot of pressure off of me if we did get an option from one of our children and see what the reaction of one, that could go good or bad.
On the other hand with the children knowing and not seeing it, it would open the door for me to maybe fulfill some fem bucket list.
I'm wondering if anyone here could help with some advice if our plan with telling our oldest daughter is a good idea or any other suggestions going forward. Maybe someone here did something like this and tell me the good or bad of it. Just not sure if it's a good idea and would anyone here even consider it.