Hi guys,
I live in the middle of a city and have long dreamed about going out during a sunny day wearing my skirt*.
I often cycle to the university wearing my skirt but that's typically late at night.
Today (sunday at around 2pm) I decided to go out. Without thinking too much about it, I grabbed my bike and cycled across town wearing a t-shirt and my short pleated skirt.
The ride to the park was a good 40 mins and there were plenty of people about. I walked some of it.
It was so great! I got a few looks (and one double-take) but most people didn't seem particularly bothered.
My point is this. If you want to go out cross dressing, just do it. You have nothing to lose.
*I don't wear dresses, makeup or heels and don't try to pass as a women (although I have no problem with people who do!). I just like wearing short skirts. I'm not sure if this is the right forum for this - tell me if I'm wrong.