Hi Candy,
I have known a few such people in my life, and like everyone else they are unique individuals, and it is very hard to paint them with a broad brush. The reasons why they choose to dress the way they do are many. I think the link that Val provided is excellent. The best advise I could give to you is to continue to love and support them for who they are. Because believe me, they need your support and acceptance.
People often misunderstand their intentions, and terms are interchanged and confused quite freely, but I think the link clears up a few such questions.
I assure you, he likely is straight. Gay men engage in drag more as a form of social recreation, pure entertainment. As both a complex homage to and light-hearted parody of femininity.
Crossdressing is far more complex. People dress to different degrees and for widely differeng reasons. A crossdresser is typically a man who enjoys expressing his feminine side, though is likely often fairly turned off by the prospect of becoming a full-time woman. He likely enjoys his masculinity on some level, and may even revel in the fact of what is concealed beneath his garmnets. It's about the illusion. Crossdressers often have an almost compulsive need to dress occasionally, as a form of extreme relief, a release from the pressure of being forced to be a man in an aggresive, take charge sense. Typically, dressing itself is the pleasure, it is very tactile and image oriented. There is very often relatively little erotic pleasure gleaned from such rituals.
This is where transvestites differ. Transvestism is entirely about the erotic pleasure derived. They tend to dress far less elaborately, often have little desire to pass as the opposite sex, and can be very fetishistic in their choice of clothing. Whether it be simply wearing panties under a business suit, or fixating upon a particular type of footwear (high heels, ballet boots, etc.)
People who are truly trangendered, exhibit a life-long sense of having been born into the wrong body. They will go to just about any legnth to fulfill their goal of achieving consensus between body and mind. Though long considered by many a psychiatric disorder, scientists are now beginning to discover that, like homosexual men and women, there may in fact be genes that code for such attractions or behavior. Sexual identity is believed to be asserted or expressed individual of one's bodily gender. And in some cases, they don't always "coincide", or so society would teach us. In certain Asian countries such as Thailand, where transgendered people are more visible and often more accepted, such cases are often looked upon simply as a peculiar form of "karmic punishment" for transgressions in past lives.
Regardless, many of these behaviors begin to express themselves very early on in childhood. People who crossdress typically struggle strongly with issues of self-esteem, and will often go through periods of "purging" in which they will attempt to forgo such behavior, often dispensing of their entire alternative wardrobe.
The most important thing to understand is that, your friend needs to feel accepted and cared for, needed like everyone else. He's certainly not crazy, dangerous or weird. Just a little different than many. It's up to you to decide whether that is good or bad. An asset to your relationship or not.
Give him a chance. But most of all, let him know you're there if he needs to talk with someone.
Good luck.
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