Questions about comming out to a friend, could use a GG's help.

So I've been thinking about telling a friend about my crossdressing but here's some background info first. I am a 34yo and two of my best friends are females close to 50, up till a few weeks ago I was their boss. But within a few days I lost my wife and my job back to back, they have been very supportive of me like family. The one I'd like to open up to recently told us she was in a relationship with another woman for 14 years. and her good friend and neighbor now is a lesbian. I felt like this was important information because it shows her outlook on things. But here's where it gets terrifying, I've never told anybody I know. And I do care for her as she does me, strictly as great friends though. And I cannot let it get out that i crossdress, my family and ex-wife whom I share a child with could never find out. And I dont want her to freak out and feel weird either.
So my questions are,
1: should I even tell her?
2: how would I bring it up?
3: what if it all goes wrong?
I've always read that older women are more open to odd "sexual" things. Not that I want to have sex with her but I mean she would hopefully be more understanding than a younger woman. Long story short. I would love it if they were both open to my crossdressing now that I'm not their boss and I am separated from my wife. But I'm so terrified they will think I'm crazy and weird. I'm open to any advice but I really want a GG's take on this.

Thanks!
Jessi

think twice before saying anything, once you put it out there you cant get it back. and you answered your own question...………... {{{ I cannot let it get out that i crossdress, my family and ex-wife whom I share a child with could never find out. }}}

(I am not a GG) I would try to sound her out first. LGBT folk in general are likely to be more accepting, and will almost certainly understand the courage required to come out at all. I came out to a lesbian GG, in a moment of crisis, after it became clear from her reaction to other things that she was very unlikely to be judgmental. Even that was difficult, but she reacted so positively it changed my life (about this and other things) completely. The relief of being able to discuss it at all, with someone I knew and trusted, without any hint of shame or guilt was/is incredible (I doubt I'd have plucked up the courage to appear here without it).

So, without being obvious, you could find some CD related news and discuss it with her, and use her reaction to decide whether to proceed. Make sure you assess her stance on confidentiality as well. You need to be absolutely certain you can trust her.

My ex-wife once outed me (without consent) to a mutual friend who was also a gossip, who allowed her desire to tittle-tattle to override the privacy you'd expect from a friend; this incident put me firmly back in the closet (not that I'd got further than my wife at that point) for nearly 10 years, isolated me socially for a while, and lost me several friends (some permanently, others appear to have mellowed and become more broad-minded as they've matured, not that I discuss it with any of them). Amazingly, this didn't immediately end our marriage, though in retrospect it should have.

Whatever, don't rush it, but I cannot say enough how positive it has been for me to have someone I trust to talk to (different again from any sort of professional counselling relationship).

From the little bit that you've shared about yourself, it seems to me that you are still in a crisis mode and need someone to open up to. Maybe this GG friend will be ok with your secret but then - maybe not.

Being a lesbian is different than being a CD. It may be a better option to watch and wait. Don't rush to "tell all" to this lady since you absolutely are afraid of being outed. Once you tell her, there is nothing stopping her from telling her special friend. Then all bets are off, her friend has no obligation to you and the secret is out.

Of course, do what you want. However, if you have the pressing need to tell someone, perhaps contacting a therapist would be beneficial. Your secret would be safe and you could get the support you seem to be craving.

GG here
My take/ your saying that older women are more open to odd sexual things / says to me you see your cding as mostly just sexual ( nothing wrong with that) So no I definitely would not share this with a friend.
And
Your saying it can not come out I just would not chance it to trust a secret to a friend who might not perceive the potential consequences of not keeping it to herself.

I get you want someone to know ....that is normal but I like Chars idea of telling a therapist or go to a local cd support group. Some let you dress there as to be safe but my gut instinct from what you wrote is do not tell your friend.

I'm not a GG .... Remember once you ring a bell it can't be un-rung. She my be accepting and keep your secret. She may be accepting and tell the whole world. She may not be accepting at all and still tell everyone. Tread lightly on this. I agree with Char and Di you might want to talk with a therapist or seek out a CD support group in your area.

Good Luck

Jessi, I agree with the consensus you are drawing here. Don’t do it. A few points: Try not to make make major life decisions in the midst of a life crisis. There is probably not a correlation between somebody being a lesbian and acceptance and understanding of crossdressing. In fact, and I realize there is not much discussion of trans politics on this forum, some lesbian groups have been quite anti-trans. And lastly, ask yourself why you want her to know, how will it benefit you and your friendship. I hope that you have the ability to find a competent and supportive therapist. Good luck and sorry for your recent hard times, Nancy

Thankyou for the replies, I'm actually glad to hear alot of the reactions are not to. I kinda wanna be talked out of it, but the other side says do it! and I hope I didint offend anyone with the lesbian or "older" woman parts, i just felt like they were key points to share to show her possible insights. And it's not so much sexual as in true sex, but in a sexually uplifting way of seeing myself. It would be the positivity of talking about it with someone I know very well who is not family, but treats me as such. And I feel like she could keep the secret, cause when she came out to me as a lesbian she asked that I dont tell anyone, and I haven't, (except you all of course, but no names here right) but I think the best course is to wait and see. I wouldn't say I'm in a crisis as much as alot has changed and I've have a lot of time to think and dress up.i know crossdressing is a part of me cause I've done it for so long as most of you have. But i dont know how to branch out at this point. Having you all to talk to is nice but its lacking that personal touch. I guess I should find a support group but I dont know where to start there.

I would be on the side of not telling her yet. i made the mistake of telling one women in the church i was in, and she said she would not tell anyone.RIGHT! She told others. Maybe bring up the topic of other men CD, that you know, and see what she says about the topic. Maybe say you saw a few cds that day. This thing we do, can sure isolate us, and be lonely. I have not met a woman yet near my age, who accepts it/

Alice, thankyou for your input. I feel like when I write here I never give the best information. These two women are my second family and I dont want anything to mess that up. The point I'm making is we all said the same thing, if it makes you happy. So with that fact mabey it will shed some light on how we are. Very open. Not 100% obviously though. But I've never heard his admission scince then without him being around. These girls love me like a brother and care for me like a mother. Which is a good and bad thing for my current topic. But I believe you are all correct in one way or another. Comming right out and saying it - definitely a bad idea. Testing the waters for a while longer and seeing if the right topic leads into it - mabey. But for now I think you all talked me into a no-go. But if I ever do I'll tell yall how it went.

Jessi, your profile says you are on the east coast. There are definitely groups and meetups, depending on where you are. If you are near New England, there is the Trans Club of New England. We have a website, and our own club house in a safe neighborhood. We have open house every Tuesday and Saturday evening. You can come dressed, or not. There is also the option of changing at the club. The phone # is on the website.

I think a lot of us understand the need to be out to someone and just to be SEEN and ACKNOWLEDGED for our true selves, but this isn’t the circumstances. You say you were these women’s boss up until a few weeks ago. Coming from someone else who has held a position of authority, you don’t really know how much these women are really your friends and how much of it was just work deference. You should take some time to be friends with them outside of a work environment for a while. If the friendship is still strong in a few months, then maybe consider coming out to them.

Micki, we've been friends for a while outside of work. For a few years, but in a position of authority I would have never considered it, but now that I have left that job(terminated actually) there is no work connection.

You seem to be reacting and not thinking clearly.
If your secret 'can't get out' then don't tell anyone.
Most women I know can't keep a secret. I'm sure some can but none I know can.
I know some feel they have to tell someone but really is that the best option?
No in your case I would say no.
I think you are wrong on your assumptions about older women and gay or lesbian women.
Your assumptions are generally what men would think but never assume anything when it comes to women.
I am not speaking badly about women but they do think very differently than men do.

You're absolutely right Traci. I have come to the conclusion that for now it's best to remain silent. And look for a better way to express myself and find others who enjoy the same in a safe environment. It's true that my comments about women and their mindsets mean nothing, because I am not a woman and my brain operates on different wavelengths. But with that said how would one go about finding a local support group for crossdressers? Is there a place on here or another good site I could possibly check out. I'm not looking for any kind of hook up so to speak and it seems like that's alot of what's out there, I just want to find a group of people that share my interests that I could meet with in person and have a good time.

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Originally Posted by Tracii G

If your secret 'can't get out' then don't tell anyone.

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Agree 100%



Just search: "crossdressing (or transgender) support group in" [your nearest large city or state]

Jessi google the LGBT and do a search for CD or trans groups in your area.
The group I joined helped me a great deal in the beginning and it gave me a place where I could go and figure myself out.
I made a lot of new friends just like me and still call them friends to this day.

Hi Jessi,

I'm a gg... wife to a cd-er and want to chime in... I know you've said that the 2 ladies are like your family and that you will wait it out before telling them... just know that while my friends dont know my husband is a cd-er Ive definitely brought up the subject before with my friends after I found out about Sam. So while they may not tell others.. the topic might come up for discussion with others....

Also... when my friends have told me things in confidence.. at times I have still shared that fact with Sam... knowing it absolutely will not go further than him. Especially if I am not comfortable with the subject or want to discuss how I can help the other friend. I would agree with the others to say.. try bringing up the subject discreetly and in 3rd person first.

I think I find younger ladies in general to be more adventerous sexually than older ladies.. and more accepting about LGBTQ relationships and crossdressing... but that might just be in my environment that I grew up in... Ive talked about crossdressing and drag queens/kings etc with younger and older female friends before and its the older ones who usually are more offended or not as open to the subject..

Good luck getting through everything!

I with the girls who recommend "NOT" outing yourself at this time. Once the Jeannie is out of the bottle, she's cannot be put back. I view these urges for self outing to be a cry for self acceptance and an attempt to counter self doubt, whether conscious or subconscious. Since your wife left and you lost your job I suspect you're under a lot of psychological pressure. Cross dressing always seems to be an antidote to stress and depression. You also have some sudden freedom to explore your boundaries.

You say you have a relationship with these older women. Since the boss-underling relationship is no longer there you may want to cultivate the friend relationships further. That may give you some insight as to whether they would be receptive to this personal information. As to the belief older women are more open to odd "sexual" things don't bank on it. I know many older women (married to one) and not too many appear to be receptive to the concept of a man wearing women's clothing.

I would recommend joining a support group with like minded people.

If you want to take a chance at self outing yourself you may want to give it a try under the guise of attending a Halloween function. Not too much time to set it all up, but, at least you can have some fun.

If you tell just one person its then its no longer a secret and you will never know how far round it has gone.
I fought this for ages and told one, and it was a mistake.
I would suggest that from what you have told us it would be too risky, although i totally understand the need to have to tell someone, but please wait a bit longer and then see how you feel.
Once you take that path theres no going back.
In the case of ex wives it may become ammo against you.

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Originally Posted by Jessifox85

I would love it if they were both open to my crossdressing

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What does being open look like in your mind's eye exactly.

• Are you wanting to just tell them and then not talk about it again? In other words do you just want someone to know and then continue to be a guy every time you see or talk to them?
  
  
• Or, are you hoping it will somehow pop-up in conversations and if so, what do those conversations look like?
  
  
• Are you hoping they will want to do things with you dressed?
  
  
• If so, would you like it to be out in public, or are you hoping to have "girly" times with them, for example putting on makeup, trying on clothes, etc?
  
  
• How close to your family and friends are any of the people at work, including these two women.

My answer as to how you should handle this will depend on what, exactly, you want from them.

Dear god Jessi, no.

If there's even the remotest HINT that MAYBE PERHAPS your secret getting out could POTENTIALLY do something regarding your being able to see your kid? Nope. Keep quiet.

I'm a million miles away from being an expert of any sort, but what char said sounds right - you've lost your job, your wife and are in a bit of a spiral. A lot of us have our dressing urges spike when stress kicks off (I know I do) so there could be a bit of "pink fog" at play. If you feel you need to talk to someone about being a crossdresser, or just need to talk in general, I'd suggest talking to a therapist where they'll be fully able to talk through stuff with you AND it'd be strictly confidential.

Now that you are not in a relationship sexually you are still an ex and a Dad so your relationship is still active in a sense because you will see each other from time to time.
Its not really fair of you to tell them your secret because maybe they would rather not have to carry the burden you have thrust on them.Not everybody wants to know deeply personal stuff.
We all know the urge to tell someone but its not always the best thing to do.

I've decided against telling her, thank you all for talking me out of it. I'd talk more but I'm fully dressed right now and I dont really know how to type with these nails. But I wanted to go head to toe tonight to see what it felt like again. I'll keep y'all updated!

yes you would , you look nice. if you need to talk to some one come back here ,or find a group ,or therapist ,or pm me

Indeed you would... you have a very lovely presentation!

If you need the secret, keep the secret, but you look beautiful.

The number of people that know a secret, in order for it to stay a secret?

ONE.

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Maybe this GG friend will be ok with your secret but then - maybe not.

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and

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Once you tell her, there is nothing stopping her from telling her special friend. Then all bets are off, her friend has no obligation to you and the secret is out.

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and

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I made the mistake of telling one women in the church i was in, and she said she would not tell anyone.RIGHT! She told others.

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and

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Most women I know can't keep a secret. I'm sure some can but none I know can.

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Every woman that I've ever known, when faced with something either upsetting, disturbing, something they're confused about, or very interesting, will feel the need to talk it over with someone; often, their best friend, sister, whoever she trusts. But then that person will also feel the need to discuss it with someone. And then you wind up with this:
https://youtu.be/IrNI1coLYJA?t=4

And then you're out.

So, the advice remains the same: Before telling a secret, consider the worst possible outcome. If you can accept that, then proceed.

Lexi, and everyone else who has weighed in. Thank you, seriously thank you for advising me, and just talking with me, I've come to accept and realize the pressure I'm under right now. From my wife, to my son, to my job. I'm reaching out from loneliness and anxiety, possibly some depression. But reverting into CDing more and expanding that realm has opened my mind so much. And it's also confusing. But what I need... is time. Time to figure out what I want out of life. And where I want to be. Again I appreciate all of you for your input and I will not be sharing it with anyone else (but you all of course!)
Hugs!
Jessie

Jessi

If those older women have been for you through your lowest darkest moments : reveal the news.

But if they are not on the day to day with you socializing: keep it to yourself .

It?s a slippery slope when they use your revealing secret in a verbal argument and you?ll wish to have never revealed anything about your dressing.

Slowly and subtlety induce them about Cding topic to test the waters
I wish you the best

That's just the thing, now even though I've decided not to share with them, they care for me so much, I've been out of work for a few weeks now and they still call or text daily to check in. We still hang out about twice a week or so and we did that when we worked together. We share plenty of other secrets or mabey intimate things with each other, I mean not about anything sexual about each other, but one of them has discussed her and her husband's activities with me. The other, her relationship with a woman, that she asked me not to tell anyone(she's still anonymous here).

So obviously, they care for me and know me very well (so they think!). And that's why I felt comfortable talking about it with at least one of them. If not both. And we all know it's hard to explain a friendship to strangers, especially in written words. But like I had said earlier I think it might just be best to give the topic and myself some time.

Jessi, if and when u do tell someone? Be sure not to confuse the word "sex" with "gender"!:doh:

If u do that it may help with your explanation!:heehee:

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Originally Posted by frax24

Jessi

If those older women have been for you through your lowest darkest moments : reveal the news.

But if they are not on the day to day with you socializing: keep it to yourself .

It?s a slippery slope when they use your revealing secret in a verbal argument and you?ll wish to have never revealed anything about your dressing.

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I think this is a great point, i couldn't agree more.

I told a GG (my best friend at the time). She then told her friends. I was pissed but got over it. Since then she's moved across the country and started a family. I don't hear too much from her now. I know...some friend :(

There is one right answer that you can count on. I've been lucky in that I've lived in a lot of places and have been acceptedted for who I am. None of us who can provide a sure fire answer. My wife suggested that I should befriend (tell) one of our neighbors. She also outed me with a large number of friends. Some didn't know how to deal with it. I was always open which helped. I was in a position I couldn't be fired..

I have an amazing friend, we are extremely close and have been for a long time, never anything more than friends but we have been there for each other through some tough times and that makes a bond that is very tight, even with this level of closeness it took me a long time to feel confident enough to share my secret with her, I wanted her to know and I was convinced she would be okay and she is very okay with it, she is very supportive and very understanding, she has asked some obvious questions that she didn't understand about cross dressing but she has never been anything other than respectful and I trust her with my life so why not my most closely guarded secret

I say all this because I was totally sure of her, we are very close and to be fair I know some of her secrets too, but even with all that it still took me some time to share, she asked why I didn't feel confident enough to share sooner but she understood when we discussed it, I think you need to know your audience quite well because as one other said, once a bell is rung you can't unring it

I don't regret for one minute telling her, she is brilliant and we can have proper girly chats and it is a fun part of our relationship, she has never seen me dressed by the way, just knows that I do and what I wear, the good thing is sharing is wonderful, like on this forum, it is great to be able to be yourself but the down side is if you choose someone who doesn't quite see it the way you do

Good luck with whatever you choose, we will be all interested to know ho you get on