Sharing. Who did you tell, who shouldn't you share with

I love to dress and go out late at night. I love the feeling of women's clothes, but not do the make up or wig; just wearing of the clothes. I am married for a long time and wife is aware, but not truly supportive. I have underdressed at work and only the wife knows. I have a very good friend at work (female) and we share almost everything. I really want to share me dressing with someone outside of home, but am guarded about my work friend. Any advice on testing the waters? Work friend is married, has spoken with the wife on the phone, but not met in person, is married and I regularly see and speak with her husband in person. My concerns is risking our friendship and being outed at work. I am the friends supervisor.

My family knows and a few female friends. I am not anxious to be out at work (though I retire in two years)

Hmmm, bring her supervisor would seem to complicate things. Maybe just my first reaction and you certainly would have to be the judge in this regard. I totally understand your desire to out yourself however. Hard keeping it all inside. I know.

In my case only my wife knows and her fear is someone will find out and judge her for putting up with it all these years. May or may not be an issue with her family and our kids etc. Who knows.

Yes, I would have love to have a female friend to confide this all too. My wife would not endorse it however.

Firstly, does your wife know you are thinking about telling your friend? Be sure she is comfortable with you telling your friend before doing anything. Secondly, being her supervisor complicates matters, you are in a position of power over her, so it's not straightforward. You are in the best place to judge how she is likely to react. I think it's the dream of most of us to have female friends we can share this with, but, most women often think men crossdressing is weird and perverted, they are much more accepting of gay men dressing in drag than straight men crossdressing.
Best case scenario she accepts you crossdressing and you can share your crossdressing adventures with her, but, would your wife be happy about this? Worst case scenario she rejects you, tell everyone you know and there might be negative consequences at work, possibly even losing you job, plus the fallout from that on your marriage. It's a massive decision to make, think long and hard about this as you can't undo this. Whatever you decide hope it goes well for you, but, be prepared for possible negative consequences.

Personally, I think sharing with your friend is high risk with minimal reward. I always met people outside of work because I did not want to complicate my work environment.

It really depends on two things. One , could it wreck your friendship and two, could this out you to everyone else at work. Only you can assess the risk vs reward. I always tried to not involve friends, work, or people in the neighborhood. Every one else was fair game. It is easy to open up to people you do not know.

Sandi

This is a bit of a sticky situation and I'll give you my past experience. Same as yourself I felt like I wanted to share this with someone. We had this niebour that we were very close with and when she divorced with her husband I became one of the girls in conversation with her and my wife. We went away together my wife had her like a sister. Our children were the same age and one night we were alone the three of us and I asked my wife since she's always with us and a loyal friend maybe we could tell her like that I could dress with her around because she's was always with us and I couldn't dress that much. My wife told me friends are friends and as much as we are close most people aren't to good at keeping secrets and she didn't trust anyone with this. Well she was right because I don't know what happened but all at once we are hearing from other people that she is back talking us and bashing us to our close friends and other niebours. Imagine if we would have told her that and she would have had a field day with that one. After that we decided we will only trust others if I decided to come out to my immediate family first.
I hate to say this but a lot of people will use anything to weaken another person and at the end of the day you must weigh out how telling her will advantage you in anyway.
Now that's my experience and I will not tell anyone not even a close friend and especially a co-worker.

My opinion is that you should never share anything in confidence with a "work friend" - Especially since you are the friend's supervisor. You are risking a lot if you want your CDing to remain a secret. Someday, she may not be a work friend any longer, and there would be no incentive for your "work friend" to keep your secret.

Find another person outside of work if you really feel the need to out yourself.

My motto is ....... need to know basis...always.................Debra

No, absolutely not. Hmm. Let me rephrase... HELL NO, NEVER IN A MILLION YEARS!

Sorry, I in no way mean to expressing anything negative about you in any respect Jennifer, but this is a really, really bad idea.

First, work is work and home is home. Neither should cross into the other, as a general rule. By doing this, you are giving up power over the knowledge. That power then falls to your subordinate, and the chances of this information falling into the wrong hands just went up by A LOT. Further, as others have noted, the dynamic of you being this person's supervisor just makes this wrong. Worse, if your revelation of this to her gets to HR you could be looking at harassment issues. This just isn't something you discuss with coworkers...ever.

I also agree with Sandi; there's minimal reward to be had from this. The risks are enormous. Not only could you lose your job, you might not be able to get a similar job once a potential employer inquires. As Jasmine noted, the fallout here could be tremendous and affect your marriage.

Telling your subordinate has absolute disaster written all over it.

No Jennifer, really really bad idea for all the reasons everybody else have already mentioned.

Ho Jennifer :hugs:,Read Line #4 in my Signature, Then Read it again !!

>Orchid**O:daydreaming:O**

You dropped a bomb shell there when you said your her supervisor.
Sorry but I would not even give a hint of you crossdressing things can turn real ugly.

hello Jennifer,
the only person I have ever told is my wife.
I think many people might suspect but they have never asked me.
Who wouldn't I tell - the work's bully or violent transphobic bigots. We can choose how "out" we wish to be but there s no need to take risks.
luv J

When I retired I let as many people know I wore woman's clothes. I visited every department in the building and chatted with a senior staff member I knew on my last day of work!

My wife is the only other person on the planet who knows of my dressing, and I plan to keep it that way. When I was working, I would have never told my coworkers. You did the right thing by asking here, and we’re doing the right thing by telling you no.

I would NEVER mix this with anyone I worked with. So many ways this could
backfire on you. I even waited many years to tell my wife, for fear she would out me and
my work would be affected.

Later on I did tell her. And now after many years, All the people that I really care about know.
I am finally at a place where I can enjoy my life without the fear of rejection. If one of those
people tell someone. I will deal with it. So be it.

But again, NEVER in the mix for the work environment. That surely would be playing with fire.

I would definitely discuss this with your wife, If you told a woman at work without you wife's knowledge
that would be throwing fireworks into the fire. No way could that end well.

A co worker is the LAST person I would come out to, after spouse, siblings, parents, in-laws, neighbors, the mail carrier, or the guys down at the sport bar.

However it goes with any of them, at least it won't affect your livelihood. With the co worker, there's no telling. What if a work situstion arises that changes your relationship?

If you're her supervisor, I would not broach the subject at all.

Jennifer, Don't To It! The best kept secret is between "Me, Myself and I." Once, the Genie is out of the bottle you cannot get her back in. Ever try squeezing toothpaste back into the tube? There is no guarantee this information will be accepted or appreciated. I know some just need to draw some approval into one's life...affirmation. I would recommend finding a support group or finding an accepting social club.

Well Jennifer, it seems almost all respondents here are saying it's not a good idea, and the few that aren't directly saying that are at best being equivocal. There's really not much support for this idea. Ok, I get the desire. I really do. But, I hope you can find some other outlet for this desire than work.

I'd like to offer another perspective that I thought of this morning on the way to my own work;

It's very easy for us CDers to get into a CD mindset that seems logical to us, and we can explain our CD thoughts to ourselves easily and it all makes sense. We've had many, many years to process this. The problem comes in when someone from outside of this experience base is exposed to us being CDers; they've not had that many years of experience to draw from and it can seem extremely radically different from their world view, even though it makes perfect sense to us. Even with the best subtle testing, dropped hints, etc. we really have no idea how a person might react to this knowledge. They're not in our frame of minds, and we're not in theirs.

I?ve had the same feelings over the years, but with the exception of my wife, who?s supportive, I?ve chosen to keep this top secret. A lot has to do with where we live. The conservative Midwest is not the most open tolerant section of this great country. Bottom line, Don?t. Keep it to yourself. Once the cats out of the bag, there?s no going back. Good luck.

It's a bit different for everyone, Jenn.:straightface:

But, THIS advice is true for ALL of us!:thumbsup:

Once u tell someone? Undoing it is like putting toothpaste back in tube. U CAN'T un-say it!:doh:

My wife knows as does a woman part-time employee at a place where I volunteer. Long story short: She saw me buying a dress (20 miles from home) and asked me if I often bought dresses for my wife. I will not lie, so I told her the truth. She immediately became my ardent supporter and is still a wonderful friend 4 years later. I have shared pictures of Heather with her and last month she met Heather for the first time. Had she not asked me about the dress, she would not know I CD. My feeling is you need a reason to share this part of your life with others. What that reason is, is up to each person.

Nope, do not share personal information with a subordinate.

You telling the coworker is a hit that will weaken your relationship with your wife in my opinion. If I were you I would invest time and effort into building better communication and mutual understanding in your marriage. Work environment is a bad to share anything personal, let alone this subject.

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