I love wearing dresses and presenting myself as a woman. I love it so much, in fact, that for many years I absolutely longed to be a woman just so I could rid myself of the gender confusion, and wear these things without the social ramifications. But after long thought and inner debate, I have arrived at the conclusion that I will not transition. I don't believe I'm transexual. I'd have like to have been a woman instead, but I will not seek a surgical route to make that happen. There is much more to being a woman that simply flitting around in dresses and high heels. While that may be enjoyable, I probably like wearing this stuff a lot more as a man than I would if I transitioned and lived my life as a woman. As a crossdresser, womanhood for me IS all dresses and high heels. That would change if I transitioned. And simply put, an overwhelming desire to wear these clothes and present as a woman isn't enough reason to go through all the hardship that transition and surgery would bring with it. Many transexuals describe how their sexual desire changed as they transitioned. They had much less desire to get all dressed up. For them it was much more a sense of bringing their physical self to match what they felt they were on the inside. And for me, while I may have some very feminine tendencies in my soul, I don't feel that my feminine being necessarily outweighs my male being. I have aspects of both, but my reward for transition would not be enough to put myself, my family, and my friends and loved ones though the upheaval of transition.

So you go ahead and make your lists. Do whatever you have to to sort this all out in your head. You should be 100% sure of what you want to do here before you make any rash decisions. Transition might be exactly what you need, but until you're sure, it's not something you should pursue.

Here is a link to some stories where it didn't pan out for the patients:

http://ai.eecs.umich.edu/people/conway/TS/Warning.html

There are a lot of online resources for those considering transition. I suggest you do some heavy reading.