Ok, here's my positive contribution...
Before you run out and buy a lot of wigs and makeup, do some research so you can make the right choices. The last thing you want is to look like the bastard love child of Tammy Faye Baker and Bozo the Clown. Well, that is, if your goal is to be passable. If your kink is to be humiliated because you look like crap, then disregard everything below.
The first thing you'll need to do is find out your "color palette" -- the colors which are most flattering for your skin tone based on how much melanin and carotene you have. For example, if you have dark hair and olive skin, you'll probably need a "cool" palette, while a red-head with a peachy skin tone is a "warm" palette. Many makeup brands divide their products into "warm," "cool," and "neutral." Neutrals look good on almost anyone. Take a trip to the library and look up color analysis books such as Color Me Beautiful by Carole Jackson for help.
Once you've determined your palette, pick wigs and makup colors that work with your skin. I strongly suggest you invest in some high-quality foundation designed for heavy coverage that will help disguise your beard. The average bottle of Cover Girl or other brand you see advertised in fashion magazines is made to be sheer or very lightweight and won't look good on you. Ben Nye is a well-known company that produces stage makup for theater, television, and movies and is probably the best for your purposes. It's expensive, but it's worth the price. For blush, eyeliner, eyeshadow, and lipstick, you can use the less expensive brands you'll find at your local drug store. While you're at it, invest in some makeup sponges and brushes. They'll give you better coverage and a more put-together look than your fingers and the little sponge applicators that come with most cosmetics.
Once you've got your tools, go back to the library. Pick up books on applying stage makeup. These will teach you the basic techniques for applying makeup, as well as more advanced techniques like shading to help soften your jawline to appear more feminine. If you live in an area with a good community theater, I also suggest you start volunteering and learn as much as you can about applying stage makeup. You don't need to out yourself, but learning the skills will help you with your own transition when the time comes.
The first several times you "put your face on" will probably take an hour or more to get it just right. Practice these skills until you can apply your makeup from start to finish in 20 minutes or less. Once you have it down, you can experiment with different looks like the ones you find in fashion magazines. If you want to be able to pass as a woman, go for a muted, natural look. Only hookers and Tammy Faye spackle on eyeshadow and lipstick with a trowel. Play around and find the look you like best.
Hope this helps. Good luck.
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