In searching for material, I came across this excellent essay: Why do some men like to crossdress?
A few interesting paragraphs:
The regrettable truth is that there is simply no straightforward, one simple answer to these types of questions. If there was, you probably wouldn’t be coming across this article, and the discussions on this subject would have been settled long ago.
Some men cross-dress because they are unhappy at being men. Others didn’t mind the male state, but also like to put on women’s clothes occasionally. Some men cross-dress simply to make a passing social or fashion statement, and some because they have emotional needs that can only be met by the comfort that wearing women’s clothes gives them.
After their initial cross dressing experiences, transvestites will progress to one of 3 main groups:
He will stay with the type of garments he first used and have a fetish-like attachment to them.
His initial preferences will expand and he will slowly move on to other clothes and finally into the wish to be dressed completely as a woman and to pretend for periods of time that he is a woman, but he will not want to go beyond pretending and will wish to retain his male personality.
The third group will fringe on trans-sexuality in that they will live and pass as women for extended periods of time. The only real difference between these so-called crossdress“secondary” transsexuals and the full transsexual is that, again, like all the less extreme transvestites, they have no wish to actually be women.
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