Sorry about the lengthy post...
First, let me say that I have been with my wife since we were in high school, and now and we have now officially been together more than half our lives. In our younger and freer days, she would participate in my dressing as a fun little thing to do but as time when on, my dressing got pushed further and further into the closet. I think she thought it was just a phase and as we settled down, it would kind of go away. I think I thought the same thing, but of course, most of us know that it is never just a phase. Over the past couple of years, I found myself dressing on my own without her knowing and coming to the realization that dressing up was more than just a phase for me.
Recently, my wife found a couple of my things I have used to dress up with around the house. After the initial shock and surprise, the "talk" kind of got swept under the carpet and we both moved forward like nothing really happened. At that point, I knew what my wife found would always be in the back of her mind and I didn't want her to have any doubts that I was only dressing alone, so I figured I better explain myself and see what happened.
It should be noted that I was prepared for all possibilities during the talk. I had already made up my mind that if my wife had a real problem with my dressing, I would give it up forever, no matter how hard it would be. Preparing myself for that possibility ahead of time actually made it a bit easier to have the talk because no matter how my wife reacted, her love was more important than anything. Since she participated in my dressing in the past, I was hopeful that she would be at least open to my dressing in private, but I didn't go in with any expectations.
The talk went well. It was a lot more difficult to actually spit the words out of my mouth than I anticipated, but it felt great to get it out in the open. I got the usual questions, "You don't want to be a girl, do you?" and "You're not gay are you?" I tried to explain my feelings and then waited for a reaction. I explained that I would still be the man she has known for all these years and has been married to the past 7 years. However, I do have a different side to me that likes to come out now and again.
Much to my surprise, the reaction was positive. She told me that as my husband she would support me and stand by me no matter what. She wants to have a "dress-up" night very soon and said she would love to see me dressed and would love to do my makeup for me. I still plan on taking things slow. She hasn't decided if she wants to see me fully dressed or not, and I am not pushing anything. At this point, anything is a step in the right direction and I don't want to risk pushing too hard, too fast and turning her off to the notion completely. I think baby steps is probably the best way to go about things and that way I won't risk crossing the line of her acceptance.
So, I am planning on a "girls" night around the house very soon. I'm not sure what to do exactly, and I'm sure it will be a little awkward the first time being dressed around her again but I'm very happy that my wife is supportive and willing to participate at any level she is comfortable. Now that it is out in the open, I feel like a completely new person. I feel like if I am on this site and my wife happens to walk into the room, I don't have to dive across the desk and unplug the monitor just so she doesn't see what I was doing or reading about.
I was kind of hoping the reaction would go that route and knew my wife well enough that it wasn't a complete surprise, yet having that "talk" was a lot tougher than I even anticipated. I do feel like my wife and I are closer now then we were before the talk and as long as I keep myself in check and go at her pace of acceptance, I think we will have an even stronger relationship.