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.
I'm Sun-Dee at Kandi's Land; read about my outings here:
https://www.kandis-land.com/author/dee/
In my opinion, before doing any sharing of this sort I think you should ask yourself "Does this person need to know?"
www.flickr.com/people/194195593@N05/
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.
I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
My new maid's outfit is cute. Sure fits tight.
And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
Smile, Honey! You look fabulous!
Only my wife and you fine ladies need to know.
Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".
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
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