I am a submissive crossdresser who has spent many years in this lifestyle, on and off. Once upon a time I went out dressed up frequently and served Mistresses as a personal submissive. Then I got out of the scene completely. After a long break, I've started dressing again more actively and seeking to serve a Mistress in earnest once again. I still barely have my toe in the water but I think it's time I was properly re-immersed.
Recently, I figured out that my desire to be feminine stemmed from an aversion to being pushed to be masculine. Forced feminization as a reaction to forced masculinization. The stereotype of maleness - being athletic, assertive, aggressive - has never applied to me. If anything, I presented myself as a sissy - the sensitive one who got picked on and cried too easily - and I lived this out in private during my adolescence by secretly dressing up.
I felt I had to transcend the way I was perceived in daily life, and in general I succeeded, but I realized I was essentially trying to pass as male, the same way I was trying through crossdressing to pass as female.
I've come to the realization that I cannot hope to really be the girl I've always longed to be. In contrast to those I've known who've been far more deeply committed and involved than me, I am a mere dabbler. (I'm still trying to accept the idea that that's OK… isn't it?)
And while I enjoy the feeling of being all dolled up and putting on those clothes that feel so good to wear, ultimately the effort for me to pass as female and the effort to pass as male are not that different in scope or scale. And each is fraught with just as much frustration, feelings of inadequacy, and fear of being judged on how well I pass.
Having figured this out, I came to another realization: that my real gender is neither male nor female, but neutral, and that my genuine inclination is just to be a woman's submissive puppydog. Curled up at her feet, looking up at her with puppydog eyes, serving, doting on her, fetching, running errands, being her loyal adoring pet.
I must admit, though, that I'm not averse to being encouraged to wear a camisole and panties as my daily underwear to bring out my feminine side more. Or to being reminded that I may not be what most women seek in a male companion, but that's OK.