Originally a comment by Artymorty on The reality.
I think this is why so many men kill themselves after the operation. They’re told that by changing their genitals, they will “truly” change sex, but that’s not how the dating world works. For the vast majority of humans, their partner’s sex is his or her most vital characteristic, for obvious evolutionary reasons. Some gay men might date a feminine-presenting man, but none would date a masculine-presenting woman. For most humans, when it comes to sexdrive, sex trumps gender.
The gay men who tend to date feminine-presenting men are more likely to be fairly feminine-presenting themselves, however. The more stereotypically masculine gay men generally go for other stereotypically masculine gay men. This is the notorious “masc-for-masc” problem, and it generates a lot of resentment among feminine gay men who are primarily attracted to stereotypically masculine men. The tension between their own instinct to present femininely while at the same time finding excessive feminine presentation in others unattractive can lead to self-hatred. They sometimes feel marginalized in the gay dating market (though that feeling is often exaggerated and distorted by their own self-hatred: in reality, feminine gays get fewer dates than the beefcake dreamboats — duh! — but they still do ok). Adopting a transgender identity for them is a way to try their luck in a different dating market — a brand new me in a brand new town, kind of thing.
And to an extent, some of them do find short term luck, so long as they remain young and thin, shave themselves completely, get breast implants or stuff a bra, and most importantly, retain their genitals. Anyone who remembers the old alt-weeklies (NY Village Voice, Seattle Stranger, LA Weekly, NOW Toronto, etc.) knows that they were largely funded by the back page ads, a substantial number of which were for “shemales” — a fetishistic fantasy for ostensibly straight men who want to try… er, other positions… with women, or the closest simulacrum of a woman for sexual purposes they can find.
These connections rarely become solid, long-lasting, psychologically healthy relationships, though. There’s money involved; there’s shame and secrecy involved. (Money, shame, and secrecy go both ways in these pairings: when the “straight” men aren’t covertly buying sex from “shemales,” the “shemales” are covertly bribing young “straight” deadbeat freeloaders to stay with them as lovers.)
I myself was a feminine-presenting gay man attracted to much more masculine men than myself, and for a time I felt guilt, shame, and confusion about the mismatch, so I can somewhat understand what these men are feeling. But in the late ’90s I worked at a trans bar, and what I saw there was profoundly sad, in a deep, fundamental way not easily remedied with flags and parades and campaigns for better “representation.” I came to suspect that there was a fundamental dysfunction at the heart of the transgender subculture.
Lately I’ve come to see that this whole thing is mostly driven by straight men with fetishes. They’re the johns perusing the back pages for “shemales,” who exploit and give false hope to confused feminine gay men; they’re the pimps who hang around the community centres and the seedy bars to coax vulnerable gay men into transgender identities. They’re the ones who pressure the medical profession to look the other way at the fact that gay men seldom do well with transgender identities in the long term.