It's all really complicated - I think anyone with an identity that doesn't fit the stereotypical expectations of society has to struggle with some of these issues - whether it's something as supposedly "minor" like a male womenswear designer, for example or all the way to someone who identifies as genderqueer.
I had just a mega-clear sense of "transness" from when I was 5 or 6 onwards, maybe earlier. I was convinced I'd grow up into a girl until I was at least 10 or 11 and realised the world didn't work that way. Then when puberty hit I didn't really develop properly. I had to have growth hormone injections to try and spur it on a bit (they didn't work fully), so it was all incredibly confusing. I came out as gay when I was in my late teens (I think!? memory not good) and at that point I thought drag was where I was. I got even more confused! In the end, I just went back to where I started. It was pretty obvious that I was just "vanilla trans"; I've always had little to no connection to my body (including "down there") and even when I was a tiny child used to try and "take off my willy" (TMI I know). But I guess what I'm saying is that it's a really complicated business. In the end, all you can do is follow your heart and do your best to not think about all the different labels too much. I've driven myself mad (and still do) wondering why I am this way, but I'm learning to just roll with it.
Hope that's helpful Abe Bly. Just follow your instinct and you should hopefully be OK.
Oh: and Fonda/Eric rocks. Amazing talk and glad you enjoyed it MisterGrey!
These are definitely complicated issues that many (especially laymen like many of us) still don't understand very well, and going with the flow is a technique that can be extremely beneficial to many of us.
People sometimes end up coming to terms with their intrinsic feelings in unique and unexpected ways that are sometimes hard to predict, but I think for me it's just intellectually honest to think about why we may feel needless awkwardness/anger/shame/confusion for being who we are (especially considering that we live in a society full of big fat contradictions from both a gender and sexuality perspective.)
I don't think dressers like Abe would be questioning or hiding their cding or feminine gender expression if the world we lived in was more educated about the fluidity of the gender, the arbitrary nature of social constructs, and the differences between gender identity and gender expression.
Mtf or just male cd's generally tend express some of the same feelings Abe seemed to express in his original post, and I was hoping my post regarding how our society feels about this stuff might give him some perspective to take with him on his journey.
I firmly believe that society's uneducated and archaic stance on these concepts plays a huge role in the taboo nature of non-cisnormative behavior and the way feel about not fitting into boxes.
I don't consider that cross dressing though. It's only cross dressing to me when she's making a point to dress in a masculine fashion. I think most clothes that males wear are actual unisex, primarily because men en large go for function over form.
You know what feels like females cross dressing? When they put shoulder pads in their suits to give them a stronger look. When they bind their chests to be flatter. That kind of thing.
Our idea of female crossdressing now is much more extreme than it was before (as your well-defined more "detailed" criteria for female cding shows)
It might be why you feel that bound breast and shoulders pads combined with clothes that give a masculine silhouette is real female crossdressing where as many in our society feel that just simply wearing a pair of heels is taboo crossdressing for men/boys.
65 or so years ago men's clothing was not "unisex" in any sense of the word (it's only recently become unisex, and even then a lot of it is feminized or paired with traditionally female-aimed clothing). It was specifically for men/boys and
stuff like this would have been considered straight up crossdressing if she was warped back to the 1950s regardless of whether or not she bound her breasts or put shoulder pads in her T shirt.
Heck, 1920s flapper girls (the style that extremely feminine icons like Minnie Mouse and Betty Boop was based on) were actually criticized for (what many people at the time saw as) their "masculine" androgynous silhouettes and short hair; a lot of young women used the flapper girl look as a sort of passive way to fight the gender norms of the time.
As I said in the above post, I think examining the way our society feels about this stuff can give us quite a lot of perspective on gender issues and stuff like them.