Homosexual transsexual is a taxonomic category used in sexology, psychology, and psychiatry, to classify transgender or transsexual people who are attracted to members of the same biological sex. It classifies trans women attracted to men (and less often, trans men attracted to women), based on assigned sex at birth, rather than gender identity.

The concept of categorizing trans women by sexual orientation originated with Magnus Hirschfeld in 1923, and was further developed by the sexologist Harry Benjamin in 1966 as a component of the Benjamin scale. The specific term homosexual transsexual was coined by Kurt Freund in 1973, and used from 1982 onward by him and others.

In the DSM III, published in 1980, transsexualism was to be diagnosed and the sexual orientation of a transsexual specified using the terms homosexual, heterosexual, asexual, or unspecified. This convention had its origins in the taxonomic work of researchers like Hirschfeld, Benjamin, and Freund, which found that grouping trans women by sexual orientation revealed important qualitative and statistical differences between them. These differences have been maintained by various researchers as indicative or suggestive of multiple, distinct etiologies. The term homosexual transsexual has since been used in publications by a variety of academics, including Benjamin, Freund, Blanchard, and Anne Lawrence, as well as J. Michael Bailey and James Cantor, among others. Sexologist Ray Blanchard uses the concept in relation to one type of male-to-female (MTF) transsexual in his transsexualism typology developed in the late 1980s.

The term homosexual transsexual has been criticized by sexologists, linguists, and transgender activists as confusing and insensitive toward trans identities. Milton Diamond proposed the alternatives androphilic (attracted to men) and gynephilic (attracted to women) as neutral descriptors for sexual orientation that do not make assumptions about the sex or gender identity of the person being described. Terms such as androphilia and gynephilia are sometimes used instead of, or concurrently with, homosexual, heterosexual, or non-homosexual in current research, such as research which has used the Modified Androphilia Scale to assess the attraction to men of a given trans woman. S. J. Wahng contended in 2004 that the term homosexual transsexual is "archaic". Though the term transsexuality was removed as a mental disorder from the DSM-IV and was replaced with gender identity disorder as a diagnostic label, attraction to males, females, both, or neither was specified in the DSM IV-TR.

Most of the research on "homosexual transsexuality" has been conducted on trans women. They are usually socioeconomically disadvantaged, born later in a series of male siblings, are unlikely to display cross-gender fetishism or autogynephilia, and come out at a younger age than non-androphilic trans women. Relatively little research has been done on gender variance in assigned females, although the prevalence of female-to-male gender dysphoria is comparable to that of male-to-female GD.