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The term transvestite first appeared in the early 1900s to describe a male who dresses in female clothing. Today, the term transvestite is still used, but the more commonly used term is cross-dresser. Transgender describes individuals who live in a continuous state of dressing as the opposite sex without surgical or hormonal treatment to reassign sex characteristics, while cross-dressing is reserved for those who still identify themselves according to one sex but occasionally dress as a member of the opposite sex. Transsexual is the term used for a person who has gone through some form of reassignment procedure (surgical or hormonal).

The historical origins of transvestism or cross-dressing are not exactly known, but historians believe that this behavior has existed for centuries, if not longer. There is also evidence that cross-dressing is not isolated to the United States, Canada, and Western Europe. Studies of cross-dressing have been conducted in other parts of the world, but research on cross-cultural aspects of cross-dressing remains limited.

Most of the attention given to cross-dressing, transgender, and transsexual behaviors pertains to males cross-dressing as females. There are undoubtedly instances of female cross-dressing, but it is treated as less of a clinical issue than male cross-dressing. Generally speaking, females have more flexibility in gender bending behaviors than do males. Therefore, unless a female makes the transition to transsexual, cross-dressing behavior is likely to receive relatively little social attention. Males, on the other hand, are less free to deviate from the culturally accepted presentations of self as a masculine gender. Males who choose to wear female-assigned clothing subject themselves to criticism, psychiatric evaluation, and ostracism from families and friends.

There are two forms of cross-dressers: fetishist and transgenderist. Fetishist transvestites are males who are sexually aroused by wearing female clothing and seek sexual gratification from this behavior. Transgenderist transvestites are males who cross-dress for purposes of experiencing life as a female. There are cases of fetishist cross-dressers who develop a sense of transgender, but it is uncommon for a male to cross-dress for the purpose of the feminine identity and also gain sexual gratification from the act. It is possible that, over time, a fetish transvestite will gain more than sexual gratification from the behavior, and it is unclear whether sexual gratification remains a part of their cross-dressing or not. Masturbation is the typical sexual outlet for fetishist transvestites, but there are some who seek out partners (male or females) who are willing to allow for the cross-dressing to be part of their sex life. Also, prostitutes have been known to be a sexual outlet for some fetishist cross-dressers.

Among the many misunderstandings about cross-dressing behavior is the belief that cross-dressing is a parallel behavior with homosexuality. It is not uncommon for the cross-dresser himself to believe he is homosexual when he first engages in this behavior. However, most cross-dressers are heterosexual, especially those who don't progress to transgenderism or transsexuality. Homosexuals who do engage in cross-dressing are more often referred to as drag queens, and their cross-dressing is for the purpose of exhibition and entertainment of others. Furthermore, there is a difference between cross-dressers and drag queens in that the drag queen wants to be seen as a male wearing female clothing, while the heterosexual cross-dresser wants to pass as a female.

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