I still don't know how to tell her.....

Hey y'all! :)

Here a while back, I made a post, pretty much asking advice on how to tell a close friend of mine that I'm a CD'er. She's a GG, really sweet and understanding and accepting of LGBT, but I haven't told her yet. However, she has been going through a really rough time lately, she had Covid back in January, thank goodness she survived it. Plus, she has recently had a couple of friends to pass away. :( Now, I've never met this friend face-to-face, I chat with her in a chatroom that she owns, plus I've spoken with her on the phone so she's not a "catfish". LOL

I mean, I really want to tell her but given what she's going through right now, I don't know how..... Just thought I would tell y'all. LOL

If I am reading this correctly you are friends and not a girl you want to date?
I will come back and check and revise my answer if need be.
By all means tell her if you want to have someone to share it with.
BUT maybe wait a bit since she just experienced two deaths of people she is close to.
Make it about her right now and listen to her as she probably needs a good friend right now.

As a supporter of our community she will all likely be happy for you and your friendship.

Kimberly,

It is certainly possible that she will be warm and receptive to the news, given her openness with LGBT people. In fact, it could even give her an opportunity to smile and enjoy becoming more close to you in the midst of a difficult time. Telling her might make her feel like she has been entrusted with something important to you, and that she is developing a deeper friendship with you.

But at the same time, you don't want to just drop this on her when she is still reeling from heartache. The best friends make sacrifices for one another, so you might need to be patient and just support her during her suffering. No one can really determine when would be the right time to share this part of your life with her, so you will just have to use your own wisdom and discernment.

You mentioned that you don't know how to tell her...once you've determined that the time is right (meaning that you have put her needs before your own, discussed her feelings and perceptions, and she is at a place where she can actually discuss other topics) you might consider a conversational plan that goes something like this:

1) Tell her that she is a trusted friend to you, and that you respect her and cherish her friendship
2) Inform her that there is an important part of your life that you don't discuss with others, and that because she is such a good friend to you, you feel like you are safe to entrust this part of yourself with her (this will not only pique her interest, but make her aware that this is sensitive information, and a good woman respects that)
3) Explain your lifestyle to her. Be calm, but vulnerable. Allow her to ask questions or to get excited on your behalf

At least, that's one way that you can consider approaching the topic.

I think it would be best to wait at least a few months. Also you mention she is not a catfish. While I agree you are most likely correct, using a video call is much more effective.

You may want to read the link in my signature which might help.

And be sure to exaggerate the money you have. Women appreciate men with money. Take her out to lunch, explain your real self, and pay with a hundred dollar bill.

Maybe just send her flowers. Big flowers.

was this a joke Jennifer?

hello Kimberly,
tell your friend if you think it will help her. The right opportunity will arise.
If you think it will not help her, ask yourself why you want to tell her.
luv J

Di, yes that's correct..... I am friends with her, but I don't want to date her, although I wouldn't mind that. LOL She and I are just too different, plus I live in Mississippi and she lives in California. But I am still very happy and lucky to have her as a friend. Also, I do listen to her and care about how she's feeling and what she's going through right now. I'm not her only friend; as I said, she owns a chat room and her chatroom is able to have a lot of people chatting in there all at once. But, I am one of her closest friends. Also, she has friends and family physically close to her that she could physically be with, if it weren't for the pandemic.

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I agree, mdmeen12..... Although I'm not LGBT at all, I'm a straight guy who crossdresses, when I do tell her I'm sure she'll be understanding and supportive.

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Elaina, I totally agree..... I'm being patient and just trying to wait for the right time to tell her about my CD'ing. Right now though, imho, it would be horrible timing as I want to be sensitive to her feelings and don't want to make it about me.

But, thank you for your advice and input, I appreciate it. :)

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Thank you, Shelly I agree. I don't know if she would agree to a video call though..... Well, she might because she's a dancer, (not exotic, mind you LOL) and since the pandemic, she has been teaching and participating in dance classes via Zoom.

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Jennifer, why on earth would I wanna do that? My friend knows I'm a truck driver and I'm not rich by any means..... Her friendship to both her and me is worth a lot more than money. Also, she lives in California, I live in Mississippi and it would be impossible for me to take her out to dinner.

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What are you insinuating, Micki?

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Jacques, I agree. I already know why I want to tell her..... She's a close friend, I want to get her opinion on my CD'ing, plus I would just like someone outside of this forum to talk to about it.

If your friend is still engaging in her chat room, why not mention it to her? Why would this put a great weight upon her? She has a chat room and presumably has been communicating with many others. You're basically unknown to her. If you casually drop the fact you're a plain vanilla cross dresser rather than open up as if you're at a counselor's office, it would be up to her to further engage the conversation. You make it sound this would be a heavy weight upon her after her illness and loss of friends. All I see is this would open up another line of conversation. You make it seem as if you're going to unload some pertinent information on a wife or girl friend. I just don't see it. To me it would be just another topic of discussion.

Stephanie yes, she is still very engaging in her chatroom and she talks with a lot of different people, most of whom she's known for a long time..... Also, I'm not unknown to her, she is a close friend to me and I've known her for a quite a few years, although it is likely that I will never actually meet her face-to-face. I'm sure she would further engage the convo, but I still feel as though it would put a weight on her shoulders and I feel like I would be being a bit insensitive at this point in time if I were to tell her about my CD'ing. She knows that I'm a sensitive and compassionate person and given what she's going through right now, the last thing I want to do is come across to her as insensitive and selfish.

It seems to me your friend might be among the most sympathetic people you know, and would be the most supportive of you, even though she is going through a bad patch (gross understatement).

How do you think she would react if you took a selfie of you in your best dress and just sent it to her. You have to do yourself up as perfectly as possible, and then accompany the pic with the caption, "How do you like my new dress?" Boom, now its out there, and im willing to bet that she will react with shock and surprise, followed by, "OMG, you look nice". Women are far more willing to support a male friend in a dress. The biggest obstacle is your own fear of the unknown, and I know its a biggie.

I know its a suggestion that's really out there, maybe too long a stretch. But I think its a low risk. You only contact each other online, so if she ghosts on you, what you lost wasn't really a friend. True friends listen and support. You've heard that misery loves company. Maybe what she needs to draw herself out of her funk is to invest a little time in the things in YOUR life that matter.

You make it sound as if is going to have some negative thoughts about you if you tell her. It is a platonic relationship. Are you sure it is not about how you would feel if she were to have negative thoughts about you? She may not have as much invested in the relationship as you do.

I have to add my two thoughts...
you said: I've spoken with her on the phone so she's not a "catfish"
I say: Um - talking to someone on the phone doesn't mean the AREN'T a catfish, (but it doesn't mean they ARE either.)

you said: She's a GG, really sweet and understanding and accepting of LGBT
I say: well, here's your opening. Next time the subject comes up in conversation, simply say something along the lines of "me too" or "Yeah, it's nice to be a girl for a while", or something such.
It lets her know that there is something more than plain vanilla in you - and she can pursue further inquiry if she wants to.
She can also let it drop if she doesn't want to go there.
Keep it casual. It doesn't need to be a MAJOR issue, and if you treat it as if it isn't, she probably won't either.

Suzanne, yes my friend is a very sympathetic, kind and supportive person. I do believe that she would support my CDing.

I do think that it wouldn't be the best idea in the world if I were to text her, (yes, I do have her phone number), a pic of Kimberly and just be like, "Hey guess what? I'm a crossdresser". Imho, I think that might be a bit much...? I just kind of want to gradually ease her into it and not just throw it at her all at once.

"Maybe what she needs to draw herself out of her funk is to invest a little time in the things in YOUR life that matter." Yes, I agree with you there and I have heard that misery loves company..... However, I still don't want her to think that I'm selfish or trying to make it about me. But, you know what? I'm almost to the point to where I wanna say, screw it, she's my friend, I want her to know and just put on my big girl panties and tell her! ROFL

Anyway, thank you for input, I appreciate it. :)

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Stephanie, you're right, it's just a platonic relationship between myself and my friend..... And while she does have a lot of friends, some of whom she has known longer than me and she's closer to, she still puts her 100% into her friendships as do I.

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SaraLin, thank you for your comments as well and I agree..... Well, she really isn't a catfish because believe you me, I've been catfished online before and my friend is legit. But you are 100% correct, just because a person has spoken on the phone with an online friend, doesn't mean they're not a catfish. LOL

Anyway, it's hard for me to just casually bring up something like this in a conversation. Idk, I'm just the type of person who just comes out and says it, although I'll probably beat around the bush about it a little at first..... Like, I want to tell her that I trust her with what I'm about to say, but I want it to go no further until I'm ready for it to. As I said, she owns a chat room and quite a few people chat there all at once and I am acquainted with most people who chat in her room, because we all chat there pretty regularly.

Could be something as simple as an offhanded comment to break the ice. Something like, "Did you see (whoever would fit in this spot) and the dress/outfit/skirt/blouse they were wearing? Sure wish I could wear something like that." Or maybe something like the above, but saying, "That was a nice (blank). Wonder if it comes in my size?"

If she responds positively, there's your in. If not, at least you'll know, something.