I've seen many threads about going out and about, what article of clothing one first wore, but I have not seen one before about 'how old were you when you first stepped out to the outside world en femme'.
In my case, I was a few months shy of 13...way, way back during the summer of 1964, when, enthusiastically encouraged, aided and abetted by Mom, I spent the whole summer en femme.
I will never forget my first time out, to Burdines to buy heels. At that age Mom and I were the same dress size but were different shoe sizes, so I had to buy shoes. Dressed in a two-piece brown dress, girdle, long-line bra, stockings, wig, made up as a young woman of maybe 20 and wearing shoes that Mom had borrowed from my aunt with the excuse that her feet were horribly swollen, Mom and I went to buy some heels for me.
Those were the days when shoe shoppiing always meant male attendants kneeling over to help fit the shoes and I distinctly remember on the way over to the store, Mom telling me all about how the attendant would try to peek up my skirt as he was fitting the shoes, to mind my legs, not flash anything, be mindful of exposing my stocking tops and girdle, etc etc.
To this date, still an extremely vivid -and I must say, erotic- memory....
How old were you?