I had several cases where I flirted with wearing a more feminine article or accessory. However, I'd have to say the first time I went out that really made a difference was going on a walk, outside at night. It was in a nicer part of town, on a walk that was a couple of miles in total. I had a couple of passers-by to whom I said hello or nodded my head, as I would do anyway. It was a great thrill knowing that people driving past could see me, although it was dark enough that I doubt anyone recognized me. The experience gave me the first inkling that I could do this!
Sami