I've been mostly at home dresser, although I have driven places dressed up before, but have never really went out otherwise. Lately my wife has been very positive about my dressing and has encouraged us to go out. This weekend we had an overnight sitter and while the bulk of our evening was a more standard boy-mode date night, later in the evening we decided we should go on a short trip we me dressed up, we decided to go a very friendly dessert place in nearby gay neighborhood. I drove us there, we are able to find parking only about a block away. After getting out of the car we walked right past a large gay bar on the way and the doorman was friendly as we walked past, then we got to the dessert place and we were greeted to "good evening ladies", I'd never been addressed that way before, so it was nice. When we made our order, I let my wife do most the talking and checking out and the guy at the counter asked how the night was going, complimented her earrings she made herself, took a business card from her, while I sort of shyly stood nearby, but it was nice.
After that we decided we didn't have enough booze at home, so we decided to extend the outing to include a trip the drug store across the street. It was late, but there were a good amount of people there, but everyone was focused on their own thing and in that neighborhood a crossdresser isn't exactly the most exotic thing to see anyway. So we got our alcohol and walked back to the car and finished the evening back our place.
It was a small simple outing, but it helped break the ice for me and for my wife and it was all positive, so I expect when he have the child care set up to do it again, we'll probably try to go out again and try to extend how much of it is dressed up.
