"Shemale" is a portmanteau of "she" and "male". In adult media, it describes transgender women who have female secondary sex characteristics (such as breasts) while retaining male genitalia.
The portrayal of transgender women in media has shifted significantly over the decades: How Far Have We Really Come with Trans Representation? youporn shemalle
The early 1990s brought transgender characters into the mainstream like never before—in all the nightmarishly wrong ways. In 1991, The Peabody Awards "Shemale" is a portmanteau of "she" and "male"