When I was younger and was crossdressing I underdressed at times for work (retail/loss prevention) as it made me feel closer to who I wanted to be (or at least thought I wanted to be). I think the allure of also doing something daring, risky was there too. Then I stopped crossdressing for about fifteen years and didn?t underdress at all.
I started cross dressing again about three years ago, and have also been underdressing as it is the only outlet I have at home. I truly do not know where I am on the trans/crossdresser spectrum, but underdressing makes me feel feminine, and that feels good. And in a way it helps me express who I am, even if it is only to me, and even if I am only a confused crossdresser.
The one thing that really makes me feel complete is a wig. Once I have done my makeup and am all dressed up that completes the transformation for me, it makes it feel real, maybe not as a woman, but as me, for a time...
