Im pretty sure that my new friend is an mtf transexual. I feel like it would be rude to out her but as a cross-dresser myself who is seriously considering more of a transition at least to a full time ->-bleeped-<- i want to talk to her about it.
I just dont know how to bring it up without being offensive. I can usually tell even the most passable of TS's are TS's except for in a few cases.
She's only seen me in male mode though.
Should i open up to her about my crossdressing? i fear that shed get angry about that and think im mocking her or something. Should i wear a dress around her?

If you are comfortable sharing the truth with her then I think you should. I would open by telling her that you are glad to have found such a wonderful friendship, and that you have something you would like to share. Are you in counseling or anything? If so, maybe let her know you have been seeing a counselor, that you have been working to figure out your gender identity, and that you would love to have her support as a friend. If she is Trans, hopefully she will be able to support you in that way, if she isn't Trans, hopefully she can understand and do the same.

It's up to you how you want to broach the subject, either way I would try to be delicate about it.

Hugs, and best of luck to you Bethany,
Jacquelyn

I can't spot a transexual if my life depended on it. That's funny because I lived and worked around Hollywood most my life and I have never seen a transexual (until this last year) in person or at least didn't know I seen one.

  I agree with Jacquelyn,  approach it gently on sincerely and I think she won't take ofence, either way it turns out.

  Hugs, Roxy

Hi  Bethany W

Short answer you do not bring it up and yes it would be extremely rude to out her.

Long answer.  It does not matter whether she is or she is not and you must accept that she is a female first and foremost and treat her as such.  If you wish to reveal that you are a cross dresser or that you are considering transition then do so on the assumption that you are revealing your personal life with no expectations that your friend will reveal anything personal about her life and as you have said she is a new friend.  So I would assume that trust has not developed that deeply at the moment, between both of you.

If you decide to tell her about yourself, then as Jacquelyn said, tell her what you have done, what you are considering doing and your gender issues.  Your new friend will either help you or not and maybe tell you something personal about herself.  Her reactions are unknown at this stage as you have not really known her for that long.

Why?  Because from my perspective or personal views.  It is my decision and my decision alone whether I tell anybody about my past.  Regardless whether they know, think they know or they don't know, it does not matter and if they are an understanding, compassionate person and a real friend they would not say anything anyway and if they said anything then they would not be a friend of mine.

I hope things turn out well for you and your new friend.

Kind regards
Sarah B

If she says she is female, she is female.  Under no circumstance should you bring it up or ask.  If she wants to tell you, she will, never assume.

Do not tell her as a crossdresser to a transsexual, tell her as a crossdresser to a new, close friend, if you feel your relationship is strong and close.

People are also more open in the younger generation, though I do not know what age you are talking about.  All the usually untraditional things you see in pop-culture now-a-days is changing the world! Good luck!

Yeah I'd say if you are willing to open up to her about your crossdressing that she may in turn reveal herself to you.

Then again, she may not....and then again even more so, maybe she isn't! lol

But how you bring it up is important too. She may wonder why you are bringing it up with her and not anybody else....

Personally i don't know why you need to know. If she wants to share about it to you or whoever that should be her choice. She might not be one and if she is and you bring anything up and she doesn't like it, your done as far as friends go.

Hi Bethany

I would say too just let the friendship grow for now and don't think about it... The subject may or may not come up at some point in the future

But as others have mentioned, you don't want to spoil a new friendship by pressing the issue and you definitely don't want to out or embarrass her either way

I would just relax awhile and wait to see how the friendship develops 

To out her may upset her very much - best not to do it. You can reveal your own crossdressing side if you wish, and see how it goes from there.

Hopefully you are not starting a relationship together,
coz lies or no basis for a relationship...

And she should be wise enough to let you know about
her beforehand...
and you should be open too, about your situation.

I would not be hurt btw if someone asked me if I was a ->-bleeped-<-, simply
because I AM a ->-bleeped-<-!

When she is a straight girl:
How on earth can you expect
that she would like you to be a crossdresser or ->-bleeped-<-?

She then probably wants a normal man,
And I would be hurt if I found out my boyfriend was crossdressing after dating,
and that that was the reason he was drawn to me in the first place.

And to some degree the same counts for normal friendships as well.

Birgitta