From my observations and limited interactions with other cross dressers, mainly via the web, I find that the vast majority of men that have a compulsion to wear women’s clothing are otherwise pretty normal, considerate, hard working people. Most are heterosexual, educated, and respectful of others. Still, cross dressers continue to be looked down upon and considered acceptable fare for jokes and distain. And in this day and age of political correctness and acceptance, that seems out of order.
I’ve seen some very masculine appearing women that have very short cropped hair, wear what appears to be men’s clothing routinely live their lives without anyone even blinking an eye. Yet if I were to be seen in my neighborhood in a skirt and heels, the gossip would spread like wildfire. I’ve heard from lots of gurls that have been shut out by members of their families or divorced when they revealed their desire to dress enfemm.
To be honest, the times that I went out in public I did get some double-takes but didn’t experience much negativity. I guess it’s different if it is a stranger rather than a family member, friend, or acquaintance.
So what’s the difference between a woman wearing men’s clothing and a man wearing women’s clothing? I think the there are 2 societal norms that explain the difference.
The first is that men have traditionally been the more powerful sex of our species. They have made the most money, held the majority of public offices; lead the military powers, etc. And women have been submissive to this role and secondary in stature. For a man to eschew the naturally born advantage of his male-ness and seek to emulate a “lesser” component of society is not considered admirable generally. When a woman seeks to emulate a man’s role, there may be some resistance but more respect for her desire for the greater stature that she seeks.
Secondly, there is the effort and expense involved. For a woman to appear masculine it is more a matter of lack of effort to look feminine. One may not find it appealing but can understand that a short hair cut, no makeup, and simple, utilitarian clothing is a lot easier to maintain for a woman whose priorities or finances do not allow for the luxury of femininity. It is not difficult to imagine that the resources saved by not looking feminine are being used in way that is more productive for that person. However, for a man to look feminine it takes a great amount of effort. And the value of that extra effort and expense is less understandable.
Additionally, people naturally are distrustful of other people whose basic perceptions of reality are dramatically different. Many people think of gender as a black and white, set in stone constant. And when someone doesn’t adhere to that ideology they are suspicious that other basic “constants” such as morality and concepts of right and wrong may also not be shared. But that is a true when any group is singled out and discriminated against. Eventually, when there is enough personal interactions between the two groups of people they find out they are not that different and the discrimination subsides. Unfortunately, the majority of crossdresser partake in their hobby in secret and there never is the chance for the misconceptions to be disavowed.
Finally, the concerns people, especially wives, have about crossdressers abandoning their responsibilities and commitments are not without some basis. Although the primary source of exposure to the idea of crossdressing comes from television, I have also witnessed acquaintances via the internet allow their progression of crossdressing to cause major disturbances in their lives and those around them. I don’t judge them for making the decisions they feel is necessary but I can see why others feel a level of discomfort towards cross-dressers. Admittedly, for many men that wear women's clothing there is an element of sexuality involved and people frequently have less than perfect judgement in such situations. However, through my contacts with other transgendered individuals I believe there is a great silent and invisible population of CD’s that are as upstanding, if not more, than most people.Update.
My wife recently was watching an interview with black TG actess Laverne Cox. Laverne said she's received more negativity from the black community than any other and that she believes it's not because blacks tend to be less accepting of TGs but that any minority community "polices itself". There may be some truth to that. I don't know about the "policing" term but I think when one of the people on your "team" decides they want to "play for the other team" then it can be hard to take. Almost like an insult. Or at least a disappointment that their pride in their "team" is not shared.
Sure there are some women that have distain for men that become CDs or TGs because they think men should maintain their stereotypical roles...and there are some men that appreciate a man that can embrace a more feminine side but I believe generally women are more accepting because of those wanting to at least temporarily join their team and generally men are less accepting and even feel betrayed when one of their own wants to leave their team to join the other one.