Well, I did it and considering I'm a shy person with little confidence, part of me is proud of myself, although the other half is plagued by the guilt which affects many of us.
Anyway, here's the story surrounding my first public walk. At home, I put on a bodysuit, thick, opaque pantyhose (120D), breastforms, a silk blouse, a V-neck jumper and a unisex down jacket (but in purple), and wore black women's pants and unisex boots for the short walk to my car, so the neighbors didn't see anything I wouldn't want them to.
I drove for 5 miles and then parked in a secluded place to put on my wig. I took makeup with me but have never applied any and didn't want to make a mess of it, so arranged the long, curly wig I was wearing, so the hair obscured some of my face. Obviously the small, tight hood of the jacket helped obscure my face a bit, too. Remember, this was my first ever time out in public, fully dressed, with forms, a wig and no makeup. Besides, my car is also distinctive, so it took a lot of courage.
I drove another 10 miles and parked in a city side-street, where I waited a while until my confidence felt strong enough. I put on a pair of caramel colored, knee-high boots with 3-inch heels and went for a walk for ten minutes, up and down a busy main road with lots of passing cars and trucks, but okay, not a huge amount of actual people walking around. It felt amazing, feeling the skirt, the heels and the whole feeling of being like a woman, walking like one and feeling great.
I looked at truck drivers and at passing cars to see if anyone was staring or even glancing, and they weren't, which is good, as my aim was to blend. Apart from two Asian men walking together who looked at me a few times, maybe as they thought I was a woman, nobody stared or even looked twice at me, not even two trendy young couples who walked past me, nor any builders, nor businessmen.
So I think my mission to blend and be regarded as a woman unless someone looked carefully at my face, was a success. For anyone who has never been outside in daylight dressed and has the facial features to blend even if they are obviously male on closer inspection, this post about a rainy or windy day is an inspiration.