The hard moment came for me at about 18 years old, when I was leaving the house to go to college. I now had the freedom to do as a wished, not totally, but more than at home (or so I thought at the time). But that meant I had to face myself squarely and admit to myself what was going on in my life, and thus taking the responsible steps to deal with it in at least a legally approved - even if highly awkward - manner. I knew from researching ->-bleeped-<-s that many were so embarrassed to be seen buying women's clothing that they would steal it from stores or from other people just to keep it a secret, and I confess to shoplifting a thing or two myself. However when they got caught - and you always get caught - they were really in for problems, as few things in life are more public than being busted. So I resolved for myself to go ahead and buy it myself, after all, it had to at least be far less nerve racking that trying to seal it and certainly less risky.
Allowing even that little bit out in the open by making such a candid and obvious public acknowledgment (it really wasn't, but it sure seemed like it to me), began to change the texture and detail of my dressing. To begin with, I could finally look for stuff I really liked. At first, I would only shop in towns far removed from where I lived, usually hitting the stores on the fly as I passed through so there was zero possibility of ever being recognized, at the time, or at any later point. I have often thought that it was ever so nice of them to build shopping centers right on top of the off ramps of the interstate highway system.
Even at that though, I constantly worried about "getting caught" at the beginning- back in my college years. Now though I'm not even sure exactly what I would have been caught at. At root I'm just being a consumer and, at any rate, what would the punishment have been? "All right young man! Extra football games and no more hanging out on the girls dorm floor for you!" Gradually I came to understand that most sales people don't care or don't notice, despite how incredibly self-conscious you feel at the time. Which is true about most things in life, dancing in particular - which also explains why I'm such a dancing fool.
As it turns out, it's not like you have a neon sign over you that announces that you are a crossdresser and are buying this stuff for yourself - regardless of how much you feel that's exactly the case. The easiest place to shop is Lane Bryant, where I never found their staff to be the least bit rude or inattentive, or even look me strangely. A few have been very nice to me and several have been extremely helpful. Lingerie is really the only "raised eyebrow" item, and really only bras and panties, the fancier stuff they always assume is some sort of a gift I think. In retail stores, business people are only interested in the bottom line and so I've found that if you're spending real cash they're are always willing to sell. And, as time went on, I came to the realization that I didn't even really care what some clerk making minimum wage in K-Mart or Target thinks in the first place. I've gradually come to accept a philosophy that if you're willing to take it to the dry cleaners without being embarrassed, you should be able to buy it in the first place.
