Erotic Crossdressing Stories

Many a crossdresser have noted the misconceptions that abound about crossdressers, especially the one about them being gay men. A young heterosexual male crossdresser related the story of how he was picked up one night in an up-market and well established bar by a middle-aged businessman.

While they were busy making small talk, he expressed his disdain of gays, transsexuals, crossdressers and the like. He could not imagine him ever being intimate with another man, he went on.

Later in the evening, when they were alone in his hotel room, he said he was tired and only asked him to fondle him and to give him oral sex. He agreed. Afterwards he expressed his gratitude and said how pleased he was that he had met him, and hopefully he would meet him again in the near future.

There are several issues relating to sexuality and gender that can be unpacked from this event. One simply relates to how flawlessly crossdressers in general come to master the art of looking like women. Another points to our relation to sexuality and gender in particular, and raises a question: if a heterosexual straight man gets oral sex from a crossdresser or transsexual without him knowing that they are  not "real" women, where does that place him in terms of conventional sex and gender categories?

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