Shemale is a term used most often in pornography to refer to trans women and other people with male secondary sex characteristics(penis) (including breasts). The terms shemale, tranny, and ladyboy are often seen as offensive. However, many of these terms are used within the transsexual community, and some transsexuals don't find the terms offensive at all. There are no set rules for which words should be used to describe a transsexual person, and a person should always defer to a transsexual person's preference. Some transsexuals choose to use words like tranny and shemale to describe their sexual activities. According to the Encyclopedia of Sex and Gender, shemale is a term that is commonly used in sex work. The term has been used since at least 1914, when it was used to describe transgender women in the US. It was often used as a derogatory term. It is unclear whether the term was adopted by sex workers or popularized by the general public. Often these terms are used in a humorous way to describe their gender transition, and the use of the words shouldn't be taken as derogatory. Many transsexuals choose such terms to emphasise their sexuality and gender identity. To other transsexuals, these terms are insulting and demeaning because they don't use their preferred terms. It is essential to know what these terms mean to the person using them, and the context in which they are used is critical. Some prefer ladyboy, and others would not use any of the words listed here. This is a very sensitive subject, so it is not recommended that anyone make fun of a transsexual person for using the words listed below. Be respectful and do not assume that a person using one of these words is a transsexual. If a person uses one of these, it is ok to ask if that person is a transsexual.
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