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Part of being a supervisor is that occasionally you may have to discipline or call out your co-worker. It's not going to work if she has this kind of information about you, that she could use against you when the matter is escalated to management level. As the others have said, don't do it!
Supervisors need to keep a clean nose.
There is a saying that "the only way three people can keep a secret is if two of them are dead."
OTOH, I told the wife of a close friend (and not the friend) because they have a Trans child and I thought I might have some knowledge about Transgender issues that would help her deal with their nonbinary child. The wife appreciated my honesty and it could not have turned out better.
My phone outed me to my wife's best friend. Has not been an issue.
There are others who know the male me who know I dress. It's not been an issue.
But as with the others, I would not confide in a direct report, unless you were to disclose to HR and ALL your direct reports. Not a good idea.
In my opinion, before doing any sharing of this sort I think you should ask yourself "Does this person need to know?"
My wife knows I underdress and is not supportive. Other than that, I don't think anyone else has a "need to know".
I do think it could be fun to have a GG to go shopping with me, but that's another thing that would upset my wife. I don't want to create the illusion of something more intimate going on.
So, I happily underdress for my own enjoyment.
She's a coworker, you know her husband, she knows your wife (-> maybe some of your wife's friends too), you are her supervisor. Let's see, mmmh, what could go wrong?
I think if your idea was to paint the worst conditions to come out to someone, the only thing that would be missing would be your wife not knowing, other than that you got the perfect recipe for a disaster. Or maybe make it even worse by having feelings for this lady (do you?). Because, you know, men can't be friend with women, Harry explained that in detail to Sally when he met her for the first time.
Told my wife. Wouldn't want her finding a bra and
think I was having an affair.
No one else needs to know.
As a child, one of the strongest rules on our family is that anything you say or do can be used against you. That has been the case in my married life also. I told my wife after foolishly believing nonsense about having no secrets in a marriage. Huge mistake. I will not do something like that again. After nearly 50 years married, I never reveal anything that is not easily found otherwise. My daughter knows about my CDing because she is an excellent detective, not because anyone told her. No one else knows enough to correlate me to CDing. I am on this forum because solely there is a standard of anonymity and decorum.
You have to be careful with the disclosure thing. Truly, there's a rush when you mention that you're a CD and then get the "OMG!" when showing a picture. When I was working in a large corporate situation full of nepotism and back stabbers, I was pulled into HR and threatened on some of the most unsubstantial alleged infractions. At a company function, I showed a few of my best images to the HR director and mentioned to her that the continuous harassment was from CD haters that had figured it out somehow.
Never had another single issue for the rest of my career.
Only my wife and you fine ladies need to know.
My BF and his wife know. I haven't felt the need to "share" beyond that.
No one needs to know, but sometimes we need someone to know. If you don't tell anyone, you will always be in the closet. Whatever small world you've created for yourself will never get any bigger. Decide what you want from this (and life) and take calculated risks. If you choose wisely, you may be rewarded. I would be nowhere if I told no one. YRMV
Absolutley not. Do not mention it.
Close friends maybe, or a partner, but you may find yourself wishing you could turn the clock back and say nothing.
It will haunt you forever.
I see a lot of people saying no you shouldn’t tell them. And I’m not saying you should, but I do want to provide advice from the another perspective. My first point is to say is that dressing up is not wrong, being a crossdresser is not morally problematic. I am not saying anyone else here thinks it is either. I think we can all agree it’s a societal acceptance issue but we, as crossdressers, are not doing anything wrong. We have been programmed to protect ourselves, our loved ones and our jobs. Especially in recent times. I just want to state to everyone, there is nothing wrong with us or what we do. So much of our fear is tied to how other people see us.
As I have gotten older I have become more rebellious in my attitudes towards conservatism. I will wear a skirt with my male tee shirt or shoes, or heels with nothing else feminine, or a dress and no makeup out in public. I will go to PetSmart, Target, Chipotle, wherever, with a goal of being seen as just another person shopping or buying lunch. Beyond what I wear, I don’t try to draw attention to myself, I want society to change and accept what I choose to wear.
I have also had two groups of friends, one who knows I dress and those who don’t. I realized that the people who don’t know was not based on would they accept it or not, but because that’s how it’s always been. I’ve known them since high school and was more closeted back then. I didn’t tell them then, and it just stayed that way. So I changed my attitude and decided to tell them. I’ve know them for years and had a pretty good idea of how they would react. I didn’t expect to lose friends, and I didn’t. Some were more curious than others and I was happy to share more with them. Some said that’s cool and didn’t choose to follow up. Which is fine too. I’ve told five couples so far and not one bad reaction.
Rule #1 is know and respect your audience. You know how people will react, for the most part. Just because they know, don’t show up at their next party in a ball gown. But you can be honest with them.
The work question is another issue. How do you think HR would react if you wore a skirt to work? I work for a pretty progressive company, they have actually removed any reference to specific genders from their dress code. I could go to work in a dress, and I would have HR support, but I may not have acceptance from co-workers who are more conservative. Ultimately it’s your decision to tell your friend/subordinate at work. If you think there is any chance they would not be accepting, then I would likely pass on telling them.
As far as getting out dressed up. Look into burlesque. I am in a big city and I think I would be hard pressed not to find a show almost every night of the week and multiples overlapping on the weekends. They are huge in the LGBTQ world and friendly and accepting. You could go to these shows all dolled up and they wouldn’t bat an eye, you might even make some friends and get to go out more.
You be you, enjoy life.