I'm a fairly shy person and would go bright red when embarrassed. When I bought female attire, I always did so on-line as I felt I would not be able to carry it off to remain calm buying in a department store etc. as I'm too self-conscious. Most of what I bought came from the UK (I live in Ireland and the on-line selections are very poor for someone of my stature) and before I came out to my wife, I ended up paying fairly high shipping costs as well as post box charges as I did not want them to arrive home and have to explain to my wife. Anyway, this turned out to be a very expensive way to shop as frequently the items I ordered did not turn out the way I expected, did not fit etc. and returning them could be nearly as expensive as just writing them off.
With a few hard lessons learned, I decided I had to bite the bullet and buy more locally. That way I see what I'm getting and is easy to return if not right. Anyway, I started doing this and after once or twice it became easy. I read advice that the shop assistants are generally happy just to make a sale, are more likely to think you are buying for some girlfriend/wife (though mine would need to be a very large one!) and/or would simply not care or give it a separate thought. Anyway, so far so good.
I recently decided I wanted to buy a wig. As these can be fairly expensive, I really wanted to go to a wig shop, get fitted and see what I'm getting. Again, in my case, I need a fairly large size and if I went on-line I could see myself spend a lot of money without satisfaction. I have overcome the shyness to some extent having successful shopping outings. When buying a wig, there is no real way of presenting for sizing without admitting to being a cd. I decided I would take the plunge.
As I'm still very self-conscious I wanted to be fairly sure that whatever place I choose would be cd sympathetic. Therefore, I researched some wig shops in Ireland on the internet bulletin boards for wig shops that are ok with cd clients. I live quite a ways from Dublin and to my surprise there were a lot of threads about how un-cd friendly a lot of wig shops were. Anyway, I came across a thread with some positive recommendations by other cd'ers / tgs about a wig shop in Dublin. I looked them up on line, and posted a query through their on-line contact form just providing my e-mail address and stating I'm a cd and my interest in getting fitted for a feminine wig. Anyway, after a week I received no reply to my query. I don't travel to Dublin too much, but I did need to go on the following day and so was disappointed to not hear back. Anyway, I was thinking I would just show up as I had seen some positive recommendations and my own confidence was growing.
However, at the last minute, I was having some doubts and decided that if I admitted to being a cd to someone else in person and it wasn't well received that I would probably die of embarrassment. This would have a devastating affect on my confidence. So luckily, I decided to phone the shop and talk to a sales person. Once I explained what I was looking for, the SA told me that while they did cater to cd/tg in the past they no longer would serve these clients. Boy, did I feel relieved that I made the phone call.
Just sharing the story, as I feel it was an experience of where some success and over-confidence could lead to rash actions. I must remember to think before I leap!
Anyway, in the case of a wig, I'm back to online. I did find a place that provide off the shelf large wigs (25" cap circumference) in the UK ... I've placed my order, so here's hoping it turns out ok.