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A few more or less relevant thoughts on the topic of shopping for undies, shoes, makeup etc while in male mode.
I started doing this as long ago as 1974 and while I have often lacked the courage to ask for help, on the occasions when I have done so, the shop assistants have almost invariably been helpful. In this period I have tried on clothes in London, Oxford, Birmingham, Manchester and Leeds, as well as in some smaller places. In particular, I have had few difficulties in trying on bras or shoes. On one occasion, rather to my own surprise, the assistant allowed me to try on a girdle. (This was some years ago in Leeds, from memory in Debenhams.) I lived for some time in Prague and found the atmosphere there even more congenial. I was quite a well known customer in a couple of shoe shops and one lingerie shop. In the latter I could and did try on anything - bras, corselettes, girdles, suspender belts... However, I suppose that's a long way to go to buy a bra!
I think the secret is first of all to have the courage to ask. Most shop assistants are, as other posters have noted, quite willing to be helpful. At the same time, it is I think a good idea to be careful about the time and place. The assistants are more likely to be helpful if there are not many other customers around to be disapprove. After all, while the assistant may be tolerant, she cannot know if the customers are, and may err on the side of caution. (The girdle episode described above was at a time when the shop was quite empty.)
At the same time, I find that as I get older I am less embarrassed about showing my preferences. While I cannot easily pass as a woman, I have taken to going shopping in about 75% female mode - light makeup, a bra sufficiently padded to show, suspenders and stockings, a blouse, ladies' trousers and low heeled shoes. I also carry a handbag. If anyone in the streets has noticed me in this garb, they haven't said anything. I recently got into a lift with two ladies. In the mirror it seemed to me that my makeup (light?) was very obvious; but they didn't seem to notice. When I am dressed like this, the shop assistants (when they notice) are likely to understand my needs more quickly.
I would recommendd in particular Derby Market in the Westfield Centre (formerly the Eagle Centre). It has a few old fashioned ladies underwear shops, where I have taken to buying bras and girdles. The assistants there are perfectly tolerant and although they don't in general have fitting rooms it is easy to take things back.
One recent discovery is the Natural Image wig shop in Debenhams in Nottingham. (I see there is one in Selfridges in Manchester.) I called them to explain my neeeds and they were very encouraging. When I visited them things also went very well. My essentially female garb did not attract any comment. Everything was perfectly natural, so much so that when one of my suspenders came undone just as I was leaving, I was able to ask without any embarrassment if I could pop back into the fitting room to adjust it, a request which was granted just as naturally.
So my advice is - don't be afraid to ask, but be sensible.
Incidentally, does anyone know where I can buy directoire knickers?
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