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Trying on wedding dresses wouldn't excite me, but going out in a group shopping or to a restaurant might.
Of course, we are on the "world wide web" so location would be important. I don't think many of us would travel very far to do this. Maybe a hundred miles at most.
What Char said.
You can literally run into someone you know ANYwhere. It can and does happen. That's not to suggest throwing caution to the wind, but it can happen. I know of at least a couple stories of people I know running into people they know on ... other continents!
Reasonable precautions of course are in order. I'm trying to get out more (partially en femme) in a major city about an hour away from me. But, last month I ran into my nephew in the downtown area...a city of over a million people. Go figure. It happens. I think I'll avoid the downtown area :)
Hopefully, when you go out in public as a woman, your presentation is good enough that you won't be recognized by people who know you, at least with a brief encounter.
Now if you are driving a distinctive vehicle or hanging around familiar places, you are more apt to be recognized, but with boobs and hip padding, women's clothes and makeup and a wig with a different color and style from your natural hair, you should be fairly safe.
If you are "partially en femme", that's a different story altogether.
Krisi,
A few weeks ago I was out fully dressed at a mall 25 miles from where I live. I twice walked right by a couple I've known for 30+ yrs. and they didn't have a clue.
Way to go, Candy--some creative ideas.
What about a Marilyn Monroe look-alike contest?
Or a giant private thrift store meet-up with special backgrounds for photography. Try on anything you want. And maybe some professional photographers, too.
Plenty of wigs and shoes to try-on and maybe buy.