Isn't that a great question? I've often wondered the same thing myself. I think that anyone that does anything out of the norm questions why they do what they do. It would be so much easier to just be normal. It would be so much easier if I was just like every other guy and just did normal guy things.
Dressing up as a woman is obviously just a choice. It is obviously something that I could choose to do or not do. These things are obvious aren't they? I always thought they were. I always thought these things were just a choice, something I could turn on or off. But the older I get, the more I am unsure of how much of a choice I do have in this. Obviously, I do think I have the choice to dress as a woman or not. But what I see is that if I choose to not dress as a woman then I am denying myself something that makes me happy.
That is the best answer that I have come up with for why I do what I do; it makes me happy. I think it is as simple as that. But it is so far from simple. It has taken me many years to come to this conclusion and many more years to be okay with it and when I really press myself it is something I still constantly work on being okay with.
One of the things I struggled with was thinking that I am making it up. That dressing as a woman doesn't really make me happy, there is no real reason why I am doing it other than maybe some sort of bizarre sexual fetish. But one day while I was in a shoe store, dressed as a man, and I tried on a pair of women's shoes and I realized how happy it made me feel inside. That it just felt right. That is really how I started pickng out many of my clothes, when I put it on did it make me happy. Did it make me feel good? Did it make me smile? If so, then the price tag was essentially irrelevant.
This practice helped me get over the fear of myself, and get quite a few pieces of clothes, but it certainly did not help me to get any style. I ended up with many items of clothing, but not many outfits. And I also did not have clothes that worked very well for my body shape. Over time I have worked to increase my ability to dress with style while flattering my figure and also making myself happy.
One of the big things I have learned through all of this is that you need to listen to yourself. You need to allow yourself to give yourself the gift of happiness even if it risks everything you have ever known or been told is what is right.