So I was at San Francisco Comic Con the other day. I don't think I find conventions themselves to be as fun as a lot of other people seem to (I didn't even last all of Saturday at BABSCon 'fourteen and 'fifteen before getting ponied out and BARTing home, and didn't even bother attending this year), but I had never cosplayed before, and had been thinking lately that I have exactly the right body type to play Pearl from Obnoxious Bad Decision Chil—I mean, Steven Universe, on account of being my being tall, thin, white, and having a big nose. (She's even pretty flat-chested!) So I ordered the Pearl dress from Hot Topic (I maybe should've gotten the XXXL instead of merely the XXL), a pink (really should be more peach, but close enough) wig, yellow gym shorts, and pink socks; improvised a gem from medical tape and the bowl of a plastic spoon; and set off Saturday morning to catch the train to the city and a short walk to the San Francisco Marriot Marquis.
The con itself was about what you'd expect, with the usual events and the usual vendor hall. The part that I found striking (enough so that I'm bothering to blog about it) was just how many compliments and photo requests I got for my costume, wholly disproportionate to its actual quality. (I enjoyed the opportunity to ham it up, proclaiming "We are the Crystal Gems!" or singing a few bars from the extended theme during photo ops.) Since this was my first time cosplaying, I don't have calibration, so it's quite possible that I got the ordinary amount of positive attention given costume quality and character popularity, but I suspect that there was something more than that going on having to do with gendered cultural expectations.
Femininity in males is stigmatized more than masculinity in females; that's why I changed in the bathroom at the con rather than wear a dress on the train, and why I don't feel like including any photos in this post despite having shared them on Facebook (visibility settings: "Custom: Friends; Except: Family") and sent them in for the next Beach City Bugle cosplay compilation post. So incompetent MtF crossdressing is "loud" relative to men playing male characters, women playing anyone, and the competent crossdressers (who were clockable on the timescale of ten seconds, but didn't instantly read as "man in a dress" the way I did), and loud things that would be stigmatized in everyday life (probably even everyday life in the Bay Area) are celebrated at Comic Con. Thus, "man Pearl is best Pearl," as I was told by a young woman (who was cosplaying a male character), even after I insistently pointed out that the other Pearl was way better than me.
There are at least two obviously-male-bodied people around my neighbourhood who routinely wear women's clothes and I never see anyone bat an eye at them, although I don't exactly follow them around and watch others' perceptions. Which is to say, I don't think crossdressing on the train would have earned you much notice in the Bay Area.
To your larger point -- I think that acceptance of male crossdressers is [semi-]consciously overdone because it's one of the few arenas in which men are disadvantaged (to quote, "[f]emininity in males is stigmatized more than masculinity in females"), and overcompensating sometimes feels like (and perhaps also is!) progress to a certain brand of progressive.
also, your css is screwy when I go to enter my name/email.