How do you ask?

[prettytoes]

I have a friend that I suspect may share the same affinity towards women's clothing. His parents are friends of mine, and as hes grown up, he also became a friend.
His mom has pictures of him in a frilly dress when he was very young...she wanted a girl. When he was just at the end of trick-or-treat age, he and a friend came around at Halloween dressed as girls. Both wearing mini skirts, and looking really good...almost too good. He has recently had some meme's posted on social media about "being yourself". His hair is growing really long as well. His girlfriend is very fun-loving, and strikes me as the type that would have fun dressing him up.

I'm just not sure that I would want to ask him about it....it could offend him if I'm wrong, or worse, it could out me.
Has anyone else had a similar situation?

[Dana44]

I would bring it up sometime when you two are together. i not sure if it would out you. That would be a typical question. But if does answer it and discus it with you. then you could probably tell him a bit about yourself..

[Marie-Jo]

You could start asking or discussing transgender as such and how it seem to have been more open in society compared to in your childhood. Maybe mentioning the Halloween you are remembering? Depending on his references, give example from the Scientific American September Issue. You can find more on that in this thread: https://www.crossdressers.com/forums/showthread.php?252297-Scientific-American-about-gender-in-September-2017
By judging the reactions you could go a bit further and probe the sentiments or stop and leave the topic.

[Tracii G]

I would think outing yourself to him would be a pretty safe bet because you know he did it in the past.
What could he say that would be damaging to you?
Just have a discussion on TGism and see how it goes.

[NicoleScott]

So you want to out this person without outing yourself? Thst doesn't seem quite right.

[Micki_Finn]

Would you want someone prying into your own habits? If he wanted you to know about that aspect of himself (assuming you're right) he'd tell you. And if you're wrong you could potentially really offend him. Best to just let it go.

[AllieSF]

Ask him sincerely what he meant by "being yourself" in his post. Then go from there following the advice above as it may apply. Good luck and please let us know how it goes.

[Fiona123]

How old is this person? If he is a minor I would not talk to him about crossdressing. You say you are friends with the parents. Are you out to them and out in general? How accepting are they? Coming out too their child could have unintended consequences.

[Jean 103]

Really not a good idea. You will be outing yourself, maybe that's ok if you are out. If you are right you are asking this person to out them self. You may look at it as it is just to you but, some people are not good at keeping secrets. I agree if this person is minor do not talk to him.

[Territx]

I agree with Micki Finn on this -- if he wanted to be outed, then he would do it himself. I think that you should let him have his own life, just as you have chosen your own way to live.

[Gillian Gigs]

How do you ask...you don't ask. You would look like an idiot if you are wrong! If you wish to out yourself to this individual, then you are the one taking all of the risks. Is that something that you want to do? Just because someone was once in a barn, doesn't mean they are a cow!

[Pat]

Here's the only scenario that makes sense to me: you come out to him yourself, tell your story and ask if he understands. Then if he has something to say, he might say it.

Don't want to out yourself? Then why do you think he should out himself?

[Jaylyn]

Nicole's right if you out him/ her then you need to fess up and see and be ready for the consequences. Could go two ways good or bad. Myself and several football players dressed one time in a cheer leader outfit and did a skit at the pep rally every one had a good laugh. I enjoyed it but I can say I know others that are not dressers in any form although they did that day. Be careful.

[prettytoes]

He's in his mid 20's. Not the type you'd expect to cross dress, but then again, neither am I. I'm thinking I'll just hold on to my thoughts for now, and wait to see if he "opens a door" in a conversation. The whole family likes to drink around the campfire (their house is near mine, and their cabin is right across from ours), so maybe I can work it into a conversation.

[Nikkilovesdresses]

You could ask him (when no one else is within earshot) if he's celebrating Hallowe'en this year...

[Tracii G]

I have given it some thought and is it any of our business really if someone CDs or not?
You might assume they do but do we really have the right to pry into their private life?

[Stephanie_V]

Put yourself in his shoes. If he approached you and began hinting that he believes you may be a crossdresser, how would you respond? Also wondering what is the purpose? Are you looking for a confidant? If you aren't prepared to out yourself to him, you can't expect him to out himself to you.

[Krisi]

What do you have to gain by knowing if he is a crossdresser?

I think if he is and wants you to know, he will tell you or let you find out some way. If he is not a crossdresser, asking would be pretty embarrassing. For both of you.

[Barbara Jo]

IMO the best situation wold be if you both saw - heard of something related to TS/CD and you would say that you had absolutely no problems with that.... live and let live etc...
Then, if they wanted to and felt comfortable, they might confess to whatever. :)

[Zoe72]

In Australia, we are having a postal vote to see the if gay marrage should be legal or not,of course it should already be, what a bloody joke. But you can bring it up in a conversation, like your you believe everyone is equal and you are open minded about life and peoples way of life.
or even talk about halloween and your plans and if he would like to join in and have fun.

[ellbee]

Yes, you two should rent a place together... Just make sure there's a room with 2 side-by-side closets, so you can hang out in there. :brolleyes:


I understand some prefer to stay that way, living their life behind closed doors & on the internet. Of course, those same people will give that kind of advice to others, as misery loves company. It also makes them feel better about their own decisions.


So many always comment on what you potentially have to lose (being outed, etc.)... Well, what about what you have to potentially *gain*?

Would you like a CD'ing buddy that you can talk with & hang out with? That you could go out in public together with & actually have some fun?


Some of my most positive & memorable CD moments have been while all dolled-up in the company of others (CD'ers & non-CD'ers, alike). Men, GG's, gay, straight... Doesn't matter who they were & how they were dressed at any given time, or where we were or what we were doing. We had... FUN!!! *gasp* :confused3:

And you know what? None of that would have ever been possible had I instead stayed at home behind closed doors by myself. Even venturing out into public by yourself gets old after a while. If I had never sucked it up & purposely "outed" myself, I never would have had those great experiences, friendships & lasting memories.


So, yeah... If that's sorta what you're looking for, even if it's simply talking about CD stuff (like we do here on this forum!), but face-to-face (which is sooo much better!), even just both of you in guy-mode... Then, yeah, you're gonna have to take a bit of risk sometimes. Nothing ventured, nothing gained. ;)

This is what I would do: Talk to your friend in-person, alone, sometime. Have you ever dressed up for Halloween? If so, simply out-of-the-blue, bring up your friend's experience with that... "Hey, remember that time when you were like 12 years old, and you & your friend dressed up like a chick for Halloween? I thought you looked really good! You know, I did that before, myself, one Halloween... Definitely a thrill!" Blah blah blah...


Where's the harm in that? :strugglin

If nothing comes of it (at the time, or even never), then so be it. No biggie.

But if you two then start opening up more with one another, as CD'ers or whatever? Good things can happen. :thumbsup:

[sometimes_miss]

You could ask him (when no one else is within earshot) if he's celebrating Hallowe'en this year...

^this might be the way to go. Of course, HOW you say it will make all the difference. Perhaps, 'So, do you still like to celebrate Halloween the same way you did when you were a kid?' with a look that's not contemptuous, but just inquisitive. Everything will have to be just right, including any body language which will make him feel better about opening up to you. Anything that makes him feel uncomfortable about talking to you will probably shut him down.

[Bobbi46]

Word your approach just right and you could have a cd friend right on your doorstep to exchange thoughts and things.

[Darling Micki]

So the company is having a Halloween costume party. Costumes are mandatory. I was contemplating going as a woman, and remembered you did that once or twice as a kid. What do you think?

If you do approach the subject maybe start with something like that

[Tracy Irving]

Halloween is the perfect time to bring this up. Last year I was invited to a costume party. There were a bunch of new friends that would be there. In late September I was with one of them and we were discussing lots of different costume ideas. Naturally, one of them was me being the bride and she would dress as the groom. When she loved that idea we were then able to discuss her doing my makeup and we made plans to have lunch and go shopping together. I didn't get crazy excited. I just owned it.

The night of the party I arrived in my normal clothing. It didn't take long before everyone was begging me to get my wedding dress from the car and put it on. What a great night!

[BrendaPDX]

Just wait and see, and does it really matter? We always want to share:)

[Ressie]

"I thought it was so cool when you dressed up like a chick on halloween that one year." "I'm thinking about doing that this year too, in fact I already have a wig".

[Sarah Doepner]

I'm with the folks who suggest you decide to tell him about yourself first. If he wants to share with you, fine.

When you feel confident enough to do this you could go to him and say something like this. "I respect you and trust you. I'm looking for an ally and you seem to not be ashamed that you dressed very convincingly as a girl on Halloween once and seemed to enjoy the experience. I'm transgender and if you have questions or reservations I'd like to talk about them because you are my friend and I don't want to damage that relationship."

Or something like that. Be patient. You may have the opportunity fall into your lap some day, or you may decide to never tell him, but it doesn't show respect to put him in a corner like that.