Well put Euchrid. I started by going out only at night, but have had a few daylight excursions. I do agree with the part about stilettos, they don't look right on a larger framed guy. I only wear block heels outside, but do enjoy skinnier heels sometimes at home.
And yes most of the fears are in our own heads, but they are there nagging that we may get "outed" and it's not socially acceptable to be different etc. in my case it would upset my wife if the neighbours were aware.