Wife and I been together for 10 years. She has always known I have dressed. Recently I brought up that I would like to take things further and start wearing norm day clothes, a wig and makeup. My wife says she wants to grow with me but is very reserved. How can I talk to her and make her more comfortable with expressing how she feels too?
Patience.
Understand that while you may want to go a zillions miles per hour and dive right into dresses and eyeliner and wigs and stilettos, she will likely need and want to take this very, very, very slowly. And gradually.
Let her take the lead, if you will.
Encourage her to seek support, whether it is with counseling for herself or for the pair of you.
Be prepared to hear things you don’t want to hear. Be receptive of what she tells you. There may be times where she needs a break from seeing you en femme.
Marriage is something we work for every single day. Gender identity is… it’s enormous. The two together is going to take a lot of communication and effort. There are a lot of aspects and nuances to this that would take a long, long post to cover and even that would be the tip of the iceberg. I’ve written a lot, and I mean A LOT about marriage and gender identity and have discussed everything from sex to boundaries to making mistakes. If you want my perspective on this, please spend some time reading about marriage and crossdressing here.
Love, Hannah
Have a question for me? Oh yes you do. Ask me here!
Hannah McKnight 
Perfect, Hannah, I could not agree more with your advice and wisdom.
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Be very cautious indeed. I compare this to a guy who doesn’t cross dress, and finds out his wife wants to cross dress. Think about this: how would he react? Interesting…
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Yes go slow, don’t push boundaries she may not want to cross.
Be happy that some support is better than none at all
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I’ve been thinking more about this and why patience is so important. I don’t know how old the questioner is; let’s say 40. In that case they’ve had around 30 years (more or less) that they’ve been considering what all this means to them, their gender dysphoria (perhaps), and maybe other. Whereas for the wife, she’s had about ten years of presumably happy marriage.
Coming out as trans is a huge thing to partners. For the questioner it can be like a massive relief. Finally, they are accepting and moving toward authenticity. Their’s apprehension, sure, but also excitement to finally be letting themselves out of the closet. The wife has tons of catching up to do. Likely for her, having gender dysphoria and all is totally foreign and hard to digest let alone imagine.
Healthy and patient communication between them is absolutely key. I suggest seeing a marriage therapist together to help facilitate, teach, and moderate such communication.
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But remember, if you go too slow you are putting someone’s life on hold
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