My fiancee and I have a DADT/out of sight, out of mind agreement in regards to my dressing. Things have been going pretty well the last few months. Have kept my legs and armpits free of hair with no complaints from her. Clothes have been hanging out of sight in a corner of the walk in closet and I'm not sure she's even seen them. She came back from getting a make over, something she's never done before, and we had a wonderful discussion about the make up and the whole process. The other day she was doing some online shopping while I was sitting next to her and like usual she would ask if I liked this or that item for her. She picked out a few things to order and said she really liked another item but didn't want to spend the additional money to get it. I later ordered it for her along with a top for me.
The day before the package was set to arrive I told her it would be in the mail the next day. Her package also arrived that day and she was home and instantly wanted to open them both up. So I opened the one I got while she stood there and opened her order, and I kept the flaps just so that she couldn't see in the box and pulled her item out and handed it to her and then picked up the box and said I would be right back. Went into the bedroom and tucked the top into a dresser drawer.
When I came back out with the empty box she asked, "Did you order something for you?"
To which I replied, "Yes. I got a shirt."
"A woman's blouse?"
"Yes."
"Ah."
"I wasn't trying to be secretive about it, just with our agreement..."
She cut me off, "I wasn't upset. I was just curious."
The whole exchange was pretty awkward but nothing changed in her mood and she was just as happy as she has been lately. She's never really been able to hide from me when she's upset. Later that evening, I asked her if she would mind if I shut the bedroom door and tried on the top I got or if she would rather I waited until she was out of the house. She said she didn't mind. I did a quick in and out. Just long enough to check the fit and a quick look in the mirror and done. When I came out she still didn't have any sort of mood change and boy was I riding a high. Later when I was driving to pick up our dogs from boarding I couldn't concentrate on the audiobook I was listening to, kept thinking about how she had said she was curious and then I started to worry that maybe my awkwardness might have come across that I didn't want to talk about it with her. The next morning the thoughts were still racing around my head and I started to think that maybe I could just make a brief comment to reiterate that I'm always happy to talk to her about it, maybe she's coming around to talking about it more. I should have stopped myself.
"I just wanted to mention real quick that I am always happy to talk to you about my dressing when you are curious in case my awkwardness yesterday made it seem like I wasn't."
Her response wasn't any different than what she had stated in the past. "It's not something I'm comfortable with. I would rather you didn't do it but I don't want to prevent you from doing it. It's not detrimental to our relationship unless you want to be a woman or want to dress all the time like a woman."
"I don't want either of those things and it really means a lot to me how you have handled this aspect of me."
"How often do you do it?"
"A couple times a week, for a few hours at a time."
"Ok."
She was a bit distant for a bit after that but it didn't last as long as it has in the past. I'm still hopeful that it will get better in the future as her reactions to things have lessened over time but I shouldn't have pushed.
Edit to clarify a little: My post here is more of a let me tell a little story and not so much that I feel like I screwed up majorly. I am very fortunate in the quality of the DADT my SO and I have. This is the only outlet where I can talk about this aspect of myself so sometimes its nice to just ramble a bit. I really appreciate the thoughtful responses I've been getting but as a lot seemed to be running along similar lines I thought this edit might be helpful. You all are great and I'm glad that you are here.