Although I have been dressing as a woman for nearly 5 months now, it has taken a while for me to see myself as a woman, not as a man dressed as a woman.
Now when I see myself, I do see a woman. Sometimes I even catch myself wondering how other people can see me as a man.
My longer hair does help some but that's not all it is. I think it's mainly overcoming the years of being told that crossdressing is wrong or that I would never look good as a woman and being able to see myself as the woman I am. It's not about trying to copy someone else but learning to appreciate the things that make me a woman.
Another thing that happened recently that boosted my confidence came after speaking in front of a class of 250 undergrads. After my talk, I was discussing it with the professor and she said she noticed that I was saying "I feel," which to her is a very feminine way of speaking, instead of "I think," which to her is more masculine. She asked if I had made a conscious decision to do that and I said no because it's something I hadn't even realized I was doing, it's just the way I talk. I often get asked during the Q&A portions of my talks what I feel is most different about being a woman or what I like more about being a woman over being a man. It's always difficult for me to answer these types of questions because I don't feel that I act all that differently; I feel in many ways that I've always been a feminine person, it just seems to match better now that I'm living as a woman instead of as a man. I may not have ever really known/understood what it meant to be a man.
As good as I may have been feeling recently, life always wants to remind me that others don't always see me the same way that I see myself. This evening I went to see a friend in a community theater production. When I got to the box office to pay for my ticket, the woman behind the counter said "Can I help you, sir?" That little honorific was all I needed to be reminded once again that not everyone will see me for the woman I feel I am.