I've noticed that when cross dressing is portrayed on TV, it's almost always for laughs and supposed to be a weird thing. Often times they get trans and cross dressing confused too. Also barely any cross dressing women are shown. Some examples would be 30 Rock, where Jenna's boyfriend Paul is a cross dresser, and they have scenes where they kiss eachother passionately while he's dressed up as her. They portray it as a bizarre sex thing, even though there are a lot of reasons why someone would cross dress. Another show the Big Bang theory wasn't quite as bad, but in the first episode they mention how much of an improvement the new tenant (Penny) is over the last tenant, a 200 pound "transvestite". What an old and dated term. Do you find this kind of portrayal offensive?
There's always something offensive! It's not cross-dressing specifically, but one of the best examples I can think of was an episode of "The Closer." It's a major network. One of the characters old police partners came back... As a woman. He handled it in a stereotypical way - like many would. But it was beautiful how it changed and went on. I loved it. So, not all portrayals are bad.
All these tv show writers have such an old and outdated way of thinking they really need to realize some things.....I always get a bit upset when someone calls a drag queen a transvestite or a crossdresser (or vice versa) because they are not the same sort of people....
I've noticed that many producers, directors and actors CAN'T tell the difference between transgender, cross-dresser, drag queen, transexual and gay. For most people non-heterosexual=gay This lack of understanding turns out in shitty material, stereotypes etc, I think only LGBT people should tell these stories on TV, films, plays, novels etc. Or maybe EDUCATED straight people I have yet to find a GOOD LGBT film/tv show made by non-LGBT people