FOR CROSSDRESSERS: HOW DO I GET STARTED?
FEBRUARY 2008

For those of you who identify as crossdressers, but have never gone out in public, I can relate to you. I shared many of the same feelings as you do now back when I first stepped out in public. Walking out my door into the chilly nighttime world, I was a little scared, a little hesitant, and a bit unsure of myself. I said to myself, "What the hell am I doing wearing women's clothes out in public?" This was back in 1991 when much of the world still looked at us as freaks or oddities.

If you identify as a crossdresser, you probably have no desire to transition and that's fine. Snobby trannies who reject crossdressers as friends just because they are crossdressers are often lonely trannies. Everyone has to start somewhere and it's safe to say that most every transsexual on the planet started her life out as a crossdresser... just to see what it was like... just to see if it felt right.

Without turning this month's column into another ad for my books and videos, I'm going to say that there are a larger number of helpful resources than ever before. Bookstores used to carry just a handful of makeup book titles. Now you can find a book by every celebrity makeup artist out there. It is startling to see all the new titles and if I had the money, I'd buy them all because each book contains useful tidbits of information not found anywhere else.

There is a vast number of makeup brands out there. Some makeup brands refer to their shades by numbers, others by chic names. It is interesting to see all the marketing and promotion that goes on in the beauty world. My motto with makeup is work with tools you feel comfortable with. I have my recommendations, but you might discover something else that works better for you. If so, stick with it. Great tools can only help a master get her job done easier, not turn a novice into a master.

Be a student of makeup. Your best teachers might not be books or videos, but simply watching the world around you. There are plenty of examples of nice makeup jobs as well as looks to avoid. Study how women make up their eyes, lips, and cheeks. Does it look appropriate for their facial features? Their outfit? Their age? These are considerations that women need to factor into their look. Most women don't achieve their perfect look until their thirties. Stop and look at a makeup demonstration in your local department store. You might be surprised at how much you'll learn just by watching someone else do it.

When doing your own makeup, never be afraid to take chances. Try new shades and new makeup techniques. See how good you look with a lot of makeup on and then tone it down to something that you feel conveys the image you want and looks good. While I always advocate a "natural look" of minimal makeup these days, I know that the natural look is not for everyone. As a crossdresser, you might have a lot of fun making yourself look like your fantasy dream girl. As a transsexual, you might prefer wearing little to no makeup to allow your natural features to shine through.

Enroll in a makeup course or pay for hourly lessons from a makeup artist you admire. Hands-on instruction is always the best way to learn. Learning from videos is also a good way to learn so long as you devote plenty of practice time to perfect what you've learned. Do not be afraid to use any and all available resources to expand your knowledge on makeup. You can never have too much knowledge and over time you will learn what works for you and what doesn't.