I just tried fully dressing for the first time in the fall of 2002. Even though I'm an otherwise "normal" heterosexual male, fully dressing up as a woman is something I've always wanted to try since about age 4 or 5. After borrowing a few things from a sister at that age I quickly learned that is not something boys are allowed to do, however. The last year or two the urge has really built up (midlife crisis thing?) so I finally went and did it! It's cheaper than a psychologist, I figured.
Rather than waste a small sum of money and time trying to develop a look, I went straight to the professionals for my first time, at Transformations in Chicago. What a bundle of nerves I was that day! Once I had determined that nobody followed my car to report me to the proper authorities, I quickly got inside the store to gladly find that no one else was there other than Soto, who was to do my makeover. The store caters to TG people like me, and it was nice to have the place to myself.
I have a wife who doesn't know about this for now, but I've read enough other sites to know it gets to be a bigger problem the longer you wait to tell someone. The fear of the potential rejection and humiliation that could await keeps me in the closet for now (but that seems to be a good place for CD types, anyway!).
Other than that, the biggest problem is buying a wardrobe, since I am in the closet. I doubt I could pass so I dare not go out dressed and try shopping.
I so far have enjoyed trying both "everyday" looks as well as as a few dressier ones. I want to have some fun with this but not go off the deep end in the amount of time and money spent on this pursuit. It's just one additional aspect of my personality popping out more but I insist on it not taking over my life. Lucky for me my employer makes me work tons of overtime at night and on weekends, so I don't have much time for this pursuit once the wife and kids get their share of time.
So many of you have been great inspirations with your pages, and I particularly want to thank Lowla Valentine and Mary Michaels. Lowla started fading off the Internet around the time I got started (update- she's back!), but Mary is around and gets younger looking every year!