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There is no simple way to tell because you do not understand it yourself. You have no idea why you want to dress up in women’s clothes so how can you explain it to someone else?

Are you gay? Do you want to be a woman? The inevitable questions come up and you answer them in the best way you know how but there is no perfect answer as you try and verbalize the unexplainable.

You are at odds with your sexual orientation and want to somehow emulate what you love. It all makes no sense but that is the beauty of gender expression and human sexuality; there is almost every variation under the sun and you are simply one of those variations; strange as it may be.

Consider however, that there is no formula under which you can come out ahead if you think that keeping your spouse means you need to suppress who you are. Eventually you will become supremely frustrated and depressed.

If she needs to divorce you because you crossdress maybe she is not the person you should be with.

It’s true that most women would have nothing to do with a crossdressing male and if they had their druthers the entire thing would go away. Most accepting partners do so hesitatingly and would prefer not to be involved if at all possible.

But even if for many the wearing of clothing of the opposite gender is tantamount to committing a cardinal sin, you are doing nothing wrong. You are doing what your psyche demands of you.

For N and I, this has meant that she has had to accept that this aspect forms part of the package. She has no trouble accepting it intellectually but viscerally it is still not a simple thing to digest.

To anyone facing wanting or needing to tell and not knowing how I would simply say to start as delicately, slowly and honestly as possible. Hiding this important part of your makeup will only lead to bigger problems down the road.

I know because I’ve been there.

Hiding encourages guilt and shame and produces stress which is worse than the original sin of crossdressing. Better tell her from the beginning and risk rejection at the outset than end up divorced down the line.

The freedom that comes with being open is worth much more than money to me. It means everything.

I should have done it much sooner but better late than never.


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For the record she was also very complementary regarding my choice of attire.

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