My wife and I just had a talk because I expressed a need to crossdress more often and to be out in public during. Well for a variety of reasons my wife thinks that unless I am willing to out myself to everyone in town, I am not yet ready to go out and about. I don't think she meant this in a bad way and the reasoning seems logical as our town is "everyone knows everyone" size.
However her suggested solution is that once a month or once every two months (finances permitting), we would take a drive to one of the large metropolitan cities in our area and stay in a cheap motel/hotel for a few days. We live very close to several big cities including two capital cities where they are not only more trans-friendly but the larger population allows me to blend in more easily and I have no relatives or friends there who could accidently spot and then out me.
I've been out in public while crossdressed with my wife twice and we both had a great time but that was on our honeymoon and a "for-fun" trip, both of which happened in different cities. During these "trans-trips" I would be allowed to crosslive for as long as I wanted to or was comfortable with. We'd still do our normal couple things and she thinks it would be good "real-world" experience for me. I can still crossdress as much as I want to in the privacy of our own home.
Has anyone had experience doing something like this? Does it seem like a good idea?