AFTER trying out the idea in the forum "What female clothes can you wear without drawing attention?" [and my reply #45]--and Wendy's 'daring' exploits {I think in # 46 and elsewhere}... And also after many times of dressing as women actually do in casual wear [in my case this means: women's jeans or pants, blouse or top with silky material and sometimes a bit of lace, sometimes with bra [but no padding] and sometimes just a chemise; loafers with two inch wide heels; handbag; scarf on head [no wig]], I've found two things happening: a) it gets easier and easier, less and less of a big deal, and I add more and more places I can go ; b) but if I want to get that thrill I have to add something more fem/less strictly androgynous--which I of course do.
What's interesting to me is that I've gone out dressed many times in club wear [shorter, clingy dresses, stylish skirt/heels, etc going out occasionally in the hot-nite-date type of attire]--but there was nothing like a) and b) happening.
what progress! [some or most would say regress]. Last nite for example I did something I'd never have done a few months ago--went to the supermarket at 2 am--its a large 24 hour store, and not too many shoppers at that time but a lot of stockers around. i had light mascara/makeup, very tight jeans, flats, a shoulder bag, blue women's tailored top and gray jacket that is part of a skirt/jacket outfit. Some of the stockers looked as I walked past and the check out lady looked me right in the face and must have seen my makeup and was friendly. Tonite I took a long walk in a below the knee skirt gray skirt and blue sweater with sequins. Of course in a safe area. But who knows WHAT I'll be doing in 3 months. Its a little scary but really appropriate and reasonable in other ways.