hi, all. Long time listener, first time caller.
TechGirl, this is a fascinating topic for me, thank you for raising it. I've been trying to "figure out" my identity for, gosh, decades, and I've always been really uncomfortable with the term "crossdresser". It seems too cheap, sordid, trashy, demeaning. I prefer to think of myself as somewhere on the trans* spectrum, even if I'm not sure where.
After spending a few months talking to a gender therapist, I am making a lot of progress. I don't think I need to transition. I do think it is extremely important that I incorporate the femme side into my life somehow. I think that leaves me in a place some would call "ambigendered", and some would call "crossdresser". I'm getting more comfortable with that.
Even the subject line you chose for this topic sort of blows my mind! A crossdresser on HRT... wow, that is a level of investment in my femininity I hadn't thought possible until just recently. It took me a while to realize that most of the books I've read on "transgender" or "transsexual" start with a very inclusive view -- "you're embarking on an amazing journey!" -- and they all end with SRS. That doesn't speak to me very much. When I started (very reluctantly) looking for books using the keyword "crossdresser" instead, I found a wider range. I was really amazed by Baby Steps in Sky High Heels: A Crossdresser's Guide to the Tgirl Lifestyle which spoke to this new understanding: living as a man, going out as a woman. The idea that it might be possible also to do HRT, and maybe some surgery, really opens up the possibilities.
I'd be interested to hear about other role models. I know there are a lot of folks in the "genderqueer" space, but my interest is in the ends of the spectrum, the male men and the female women. But I am definitely excited about exploring this more, and I think 2016 will be a big year for me. I'm already hard at work on it :-)
Terri, to respond to your question from my own point of view... for me, crossdressing is not a salve or a halfway step to a transition, but something different. I want to be a woman. But I am fairly comfortable being a man and I do not have much physical dysphoria: longing, perhaps, but not dysphoria. I don't think I need to transition or live full time as a woman, at least not enough to go through that process. I could be wrong, and I could change my mind. For now, being able to play both roles is very appealing. Finding a highly gendered in-between space that allows me to still do both, and incorporate my existing equipment -- "pre-op" or "ladyboy" or something like that -- seems like the best of all possible worlds.