The first time I went out totally en femme with the intent to encounter humans was on Halloween. I wore a mid calf jade and black long sleeve print dress, black stockings and strap on heels- and a brunette wig. I had on full make up. I went into a Winchell's doughnut shop and bought some doughnuts. The young woman complimented my presentation. The second outing to encounter humans was also a Halloween. I wore a knee length black dress with black stockings and heels. I wore a blond wig and had on full makeup. I went into a Safeway and bought a bottle of Coke. An immature young guy cracked up and actually made an ass of himself. A third time I drove to a different Safeway on Halloween which turned out to be closed. It was the time before 24 hour stores. I was dressed in a knee length white sleeveless dress, beige hosiery, white strap on pumps, blond wig and makeup. A local cop pulled up next to me at a traffic light and looked me over. Although there was no reason for him to initiate an encounter, I nearly died.
If you're wanting to get a taste of being out as a woman, I'd go en femme on Halloween. There is an element of psychological protection to one's ego. I would forget the Halloween costumes and dress as the inner woman you are. And with Halloween on a Monday this year, there is the opportunity to start off with bay steps on Friday and work yourself up to full encounters on Monday.
I know my wife would not approve of cross dressing outside the home, so I'm stuck at home handing out candy. When I made my Halloween forays those many years ago, I could never figure out why my wife didn't miss me on my side of the bed. With hindsight I guess she figured it out.
Now I mostly take drives
