Chris,
first off, hi and welcome to the Cafe.
chrisinkilt wrote:I'm ready. The wife is not...
From experience, you need to take this very gently. As you are aware, there is a whole host of associations in most people's minds that link skirt-wearing with crossdressing or, inexplicably, to homosexuality. Without meaning to put words in your wife's mouth, bear in mind that you have had some time to get used to the idea of you in a kilt/skirt and she has not. It doesn't matter how many times or in how many different ways you say "it's just cloth", you both know that isn't entirely true. If it was
just cloth, you wouldn't have a problem with going back to trousers for the rest of your life.
Significant things about skirts on men is that they are very visible and very unusual. For yourself, you are willing to be seen and to face the consequences of your actions. That is a good starting point. Your family, however, also have to face the consequences, and they don't have the luxury of choice. This puts them in something of an uncomfortable situation, which can lead to conflict and discontent. Handled sensitively and slowly, this can be overcome and it can be a valuable lesson for all in deciding how much control of our identities we are willing to cede to society at large. Handle it badly and it may be years before you can broach the subject again.
If you already know all this, just ignore me and move on, I don't want to come across all preachy, just to urge a little caution. This is a marathon, not a sprint. Of course, given the timescale you outlined above, this is already obvious to you, so I'll shut up and let you get on with your day.
Again, welcome.
Paul.