So Sophie,

I am a normal, attractive, straight male with a good job, house, car, lots of friends and tons of hobbies. However, I feel that there's one aspect of my personality that I've always wanted to explore but never quite knew how to. I have a deep desire to dress like a woman and don't really know how to even go about starting to find any sort of information. How do I find clothes? Where does one look? What kinds of things would I even need to buy to make my look convincing? I don't want to be one of those men who tries cross dressing but just looks like a man wearing women's clothes. What do I tell my friends?

-Wanna be a Drag Queen

Hey Queen,

ell, congratulations. I firmly believe that more people should spend time exploring all facets of their personalities. With you wanting to be a drag queen, I can't thank you enough for wanting to do it properly. Too many men dress in women's clothing and botch the job so thoroughly that no one is taken in for a minute. These poor souls don't get the desired effect; instead, they elicit feelings of mixed pity and mirth. No one wants that.

To start off your new life as a woman, you need to think about whether this is something you want to make into a permanent lifestyle change, or whether you just want to go out as a woman occasionally. Either way, there are some basic things you will need to have. First off, you will need to invest in some decent wigs. A good drag queen always has perfect hair. Next, shoes. If you're a man and you don't live in either New York City or San Francisco, it will be challenging to find shoes in your size in regular stores. Wigs might be tricky, too. So will evening wear. You will need to find properly sized dresses, too. And, don't take this the wrong way, but there is no way you're going to make anyone believe that you are a woman if you're built like a man. You're gong to need to add curves to your hips and butt and get yourself a set of nice breasts. You're also going to need to learn to act like a woman. Don't worry, this is what the Internet is for.

There are myriad sites out there to help cross-dressing men get the things they need without making them feel self-conscious. They cater to this demographic, in fact. Try www.drag-queen.com for starters. They have a wonderful selection of basic items and even an area where you can buy instructional materials to help you with your transformation. For starters, try the Art & Illusion: A Guide to Crossdressing series. Volume I, "Face and Hair," is a comprehensive guide to developing your feminine image. It contains in-depth discussions on makeup and hairstyles for all types of skin and faces. Volume II, "Fashion and Style," demystifies the process of figuring out what size clothes to buy. It discusses reshaping your body so you look feminine and picking the right style clothing so you look fabulous. Volume III, "Behaving As a Woman," was six years in the making. This book covers the psychological and physical work necessary to create a public feminine persona. It also covers all aspects of bodily movement.

There are other things you are going to need to think about in addition to your look. You mentioned that you were not entirely sure what you were going to tell your friends about this new side of yourself. While I do not encourage having to hide who you are, if your friends will not react positively to this then you have two choices. The first is to live in secrecy and never breathe a word of this to anyone. You will need to keep all of your clothing, wigs and makeup in a separate closet in your home, since you don't want your mom or girlfriend finding this stuff hidden in your regular closet. Then you will need to sneak out of the house, hoping that the neighbors never catch a glimpse of you and live in fear of discovery forever. (You didn't really want to ever run for political office, did you?) The other choice is to tell your friends; if they don't react in a supportive manner then tell them off and get new friends. Real, true friends will like you for who you are and it won't matter to then that you like to go out as a woman. But be prepared to take some ribbing from them since even your real friends will not be able to resist making the odd joke or two at your expense. This is no different from any other thing that you do that they don't quite understand, so I wouldn't bother getting overly sensitive about it unless you think the teasing is malicious.

Good luck with this, and let me know how it turns out.