So I'm past 60 and have been really in the closet since I started dressing, although my SO knows and is really supportive. I went walking dark streets a couple times when I was younger, and had some skanky experiences. But, reading the stories here made me more and more interested..
Last night, I got home from work early. I shaved again, including my hands and wrists. I put on a waist cincher, hip pads and breast forms, my nice purple suit, grabbed black patent heels, wig, jewelry, and headed out. I drove up to Arlington Heights and called Transformations by Rori: "Hi -- I'm outside, and dressed. Is it okay to come in?" On being assured it was, I finished myself off and got out of my car. Walked across Arlington Heights Road in wig, suit and heels right through the headlights.
Rori was wonderful! She greeted me warmly, asked my femme name, and told me about the specials. When I expressed an interest in a new wig -- careful to explain that I wasn't ready to buy then -- she plopped me into the salon chair and tried on several looks, meanwhile explaining proper wig care and wearing. When I asked "How far away would someone have to be before I passed?" she laughed, then gave me hints on female deportment: "Be confident. Look people in the eye. Smile."
After spending an hour as Cynthia, in public, interacting with (admittedly) friendly people, I headed back to my car and went home. I'm thinking of trying the Shabari conference next May. Maybe I'll make it to some of the Transformations parties first to build confidence.
It was a wonderful experience. Any of you girls in or coming to the Chicago area or NW 'burbs should pop in to Rori's!