I recently responded to another post elsewhere about how crossdressing and marriage can mix. I liked my answer so well, I stole it from myself to repost here:
I see so many tragic stories about crossdressers whose relationships fell apart over crossdressing, so I want to share my own experiences in the hopes that it will help.
The first rule of saving your marriage is: TELL HER NOW. If you are not yet married but you expect to, even if you’re just in the pre-engagement stage, this is the time to tell her. There is a chance that she will not be able to deal with it under any circumstances, and if you care for her feelings at all you will give her the chance to get out before she is trapped in a marriage. You can also save yourself some expensive attorney’s fees and alimony if she chooses to end it before it begins 🙂
If you are already married, TELL HER NOW. The longer you wait, the worse it will be when — not if — she finds out on her own. All she will be able to focus on is the years of deception. Even if you think you are over it and you purged before you got married, if the thought ever crosses your mind (you wouldn’t be here if you didn’t still think about it), she needs to know. If you want to stop, she will be your anchor in helping you; the main thing is that you do not hide anything from the person who shares your life. And if you have been hiding it from her, apologize every way you know how and invent new ways to apologize and promise (and mean it) that you will never deceive her again. I know, you hid it from her because you were afraid you would lose her… explain that and hopefully she will forgive you.
I will concede there’s a chance that no matter how soon you tell her, no matter how little dressing you need to do, it will freak her out so much that she will never want to see you again. I still say, better to end it honourably than to spend a lifetime lying to your wife.
Before you tell her, do your homework. Try to anticipate all the questions she might have, and think seriously about yourself and your answers so you’ll be prepared. What happens when you do without for a long time? Are you gay? Really? Are you super sure you’re not gay, or bi? Do you want to have surgery / hormone therapy to become a woman? The questions about being gay and transsexual are big ones, because they will tell her how likely she is to lose you to someone else. Also be prepared to share with her your thoughts on what causes it, what can be done about it, etc.
The second rule of saving your marriage is: SHE IS MORE IMPORTANT THAN THE CLOTHES. If there is a conflict between your wife and your dressing, which would you be prepared to give up first? There is no wrong answer; if you would rather be lonely but pretty than married and masculine, that’s fine too. But if you really do want to save your marriage, if you really do love her, you will put her first. That means honoring boundaries (more on that in a minute), that means making sure that every day, every chance you get, you are doing something together that *she* likes. This should be true for any marriage: Put your spouse first. That’s what love is all about.
The third rule of saving your marriage is: HONOR HER LIMITATIONS. The key here is to find a compromise somewhere in the middle where you can get time to dress the way you need to feel fulfilled, and she isn’t pressured into putting up with something she can’t stand 24×7. Ask what bothers her, and suggest ways you can do what you need to that won’t aggravate that sore spot. Maybe she’s OK with seeing you dressed but doesn’t want you to be seen in public — if you can live with that, great. If you need to be with your friends, see if it’s OK for you to have a weekend once a month where you go out far away from home where nobody will recognize you. Maybe she’s OK with dressing, but not going full female mode with wigs and breast forms and calling you Sally. Don’t push her. Ask if it’s OK for you to go full female when she’s at work, or again maybe you could arrange some time when you go away from your city and she won’t have to see you like that. The list goes on… OK to dress around the house but not in bed? OK to underdress? OK with her but not in front of the kids? (that last one is mine — my wife didn’t want our kids to be uncomfortable or burdened with keeping a secret, so I put on pants when they are home). And when I say to honor those boundaries, I don’t just mean when you think she’ll find out. If you have agreed to her boundaries, a genuine love means you will live within those boundaries even if you think there is no possible way she will ever find out. If you can’t do that, then you don’t really love her.