Shopping for Clothes in All the Wrong Places

As a transgendered cross dresser, I have made an amazing discovery: it seems that almost any article of women's clothing or shoes will fit perfectly well on the internet. The problem comes when it doesn't always fit when I unpack it and try it on. Kinda funny how that works.

I can only guess at how much money I have wasted because I sought the safety of the internet for shopping. If you are like most of us, I bet you have also. Like many guys, I have too-long arms and I have a tendency to over compensate. I always wanted a black skirt-suit and finally saw just what I wanted on-line and waited a year for the price to come down which it did. Just to be sure that the arms on the jacket were long enough I ordered what I thought would be two sizes too large. When it got here and I eagerly unwrapped it I found that the sleeves were actually a bit longer than necessary and that the entire outfit looked awful on me. It was huge and I never wore it. I was devastated. I felt so bad that I kept it in my closet for a year before I finally left it at Goodwell's doorstep. It was a hard lesson to accept since it was not the first time something like that had happened. So here are some thoughts which might be helpful if you just happen to be a guy shopping for women's clothing and really can't get yourself to tell the clerk that your wife is the same size as you. (She probably will doubt you anyway.)

I am assuming that you go shopping dressed like your usual guy self who is trying not to attract any attention.

Shoes. Always wear black opaque trouser socks and slip off male shoes when you do this. I hope you have discovered Payless because you might find an excellent selection of your size (up to ladies 12). I say might find because their stores vary wildly in the selection of larger sizes. Anyway, pick up a pair of heels that appeal and walk over to the men's section. Put the box down and simply slip them on. If you stay put and don't go walking around then chances are that no one will notice you. Really! After I did this for a while I reached a point where I could get myself to try them on for a moment right at the ladies rack. I mean, you will not see any of those people again anyway. I also have been passed by clerks on two or three occasions and they would smile and offer to be helpful. I must admit that it made me feel very good and I am still working out the lesson that has taught me.

Pants. This is easy. I usually do a lot of shopping in places like Target and I pick up a couple of pair of guy pants to carry around. I just place a pair or two of ladies pants in between the guy pants on my arm and walk into a men's fitting room to try them on. This works best when the person in charge of the rooms seems to be either very bored or nearly blind. But seriously, it works well and avoids a lot of mistakes caused by guessing.

Underwear. Do this one just like the pants only use guy shirts instead so that they sort of wrap around the lady things. It's easy and it's non-stressful.

Wigs. I can't think of any way to do this other than to go into a wig salon dressed and let it happen. You can check on-line first to see which stores are TG/friendly but you will find that most of them are. Our money spends just like anyone else's and we spend a lot of it. If you are concerned about passing - who isn't - then call the store first or drop by in boy stuff and ask the owner if you can be seen after hours or in a private room. The answer is usually "yes."

Cosmetics. Well, I have a wonderful wife who actually goes with me and acts as my expert. It has saved me tons of money. If you lack such an angel, then check out the cosmetic departments of good department stores. There might be a room where you could receive some private treatment and advice. You will pay more for the cosmetics, of course, but you will be well rewarded by wearing the "right stuff". BTW, if you are in a strange town and want to shop with no thought to being remembered, go on-line and look up places such as PaylessShoes or Dillard's or Target and use their store locater link. If you combine that with Mapquest you will do just fine.

Shopping great fun even if it is one of the forbidden fruits. In fact, that probably contributes to making it fun. Enjoy yourself. And, if you do get "busted", you might find that the average person is a great deal more understanding and helpful than you ever imagined.