For someone who really loves cross dressing, sometimes it isn't enough to just dress up. It's a fantasy and an idea that can take up a lot of thought. One of the great ways of indulging in this is by watching films with cross dressing, either as a plot point or as part of a transvestite character.
Sifting through and finding the ones that meet your interests can be difficult, though. A movie about a trans woman is very different than one about a drag queen or a man dressing as a woman to hide from the police. Yet all might superficially appear the same at first glance.
Most films that center on cross dressing rather than on other transgender topics are marketed as comedies. A man in a dress still tends to be played for laughs. Films where a woman is disguising herself as a man tend to be treated more seriously, in part thanks to often being inspired by Shakespeare but also because of societal ideas of appropriate gender behavior.
Even a comedy can still be satisfying if done well, though. Classics like "Tootsie" remain popular for a reason. Still, films of this caliber are few and far between. Far less visually appealing cross dressing along the lines of "Mrs. Doubtfire" or else the poorly reviewed "Sorority Boys" are more common. "M. Butterfly" is one of the rare dramas to take on male to female cross dressing and also have a satisfying story, in large part because it was based on an existing play and a true story.
As far as pornography goes, there is an entire genre of "sissy" films in which a man is either forced to cross dress or does so of his own free will. Many of these generally have a domination theme and involve a woman punishing the transvestite in some way. A sub-genre of the domination oriented sissy pornography is "forced feminization", in which the man is actually forced into cross dressing and then humiliated over it. This is certainly not everyone's cup of tea, but for some it can fill an aching void left by the shortage in good transvestite films.
Lesser known independent films of a more innocent nature are always possible to be found, but much more difficult without word of mouth due to their lower advertising budgets.
As with so many things that are related to transvestism, sometimes connecting with other people with the same interests online can be the best way to get what you're looking for.
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