I've been interested in cross dressing for... well, awhile. I'll leave it at that. However, I've never actually took the initiative to go out and buy some clothes/makeup/anything at all. So here's my situation. I am happily married but my wife only tolerates my "little habit." I don't want to go and mess things up by asking her to shop for me. I guess the look that I'm going for is more formal wear, with gloves, stockings, like a retro style. I'm a fairly tall guy with broad shoulders (swimmers build) but on the thin side. Any suggestions?
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willingANDable
You need a girlfriend who will help you out with this! Girls love to play dress up whether it's a man, woman, cat or dog. Even better if you can make friends with a woman who is kind of your size so you can swap clothes.
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I've worked in retail for a long time so I've helped alot of guys out with this. The first thing you need to do is to take your measurements so you can figure out your size. Even a very slim guy is usually alot bigger than the average woman so you'll probably be at least a size 10. Here's a link to a woman's size chart:

http://www.overstock.com/sizing.html

I'm tall for a woman with pretty broad shoulders and I've always had good luck at http://www.jessicalondon.com/ because they make tall clothes that aren't so dowdy like other places. Cute dresses in there. Good luck!
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On the make-up tip: I've had lots and lots of friends that did drag and they all swore by MAC, especially the foundations and the "Spice" lip pencil. If you can find a MAC counter where you live just swallow your pride and ask them to help you find a good foundation that matches your skin tone. They are pros. And don't cake it on! That's the first mistake guys make when putting on make up for the first time. The softer the better. Fake eyelashes are good for feminizing your features too.
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If you're nervous about it just go online for your shopping. There's a million places that cater to TG's now. As they say "No clerk-no smirk."
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