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We have seen a myriad of sexual orientations and genders in the world GRRM has created.

One thing however seems virtually unheard of, that's transgender people.

Are there any characters from the current timeline or history who have shown indications that they might be transgender? I know some people argue that Brienne is transgender given how she feels awkward about feminine identity but I think they are wrong. Brienne has shown us that she is a female down there, when she thinks about the life she might have had, had she been married off to Blackhaven to wed Lord Dondarrion's heir. She pictures herself as a mother there. And then she pours her heart out in front of the Elder brother of the monastery, which pretty much confirms that she is a female both by birth and deep down in her heart. And of course, she was attracted to Renly Baratheon as well, so she is straight. Another candidate often presented is Lysono Maar, a sellsword associated with the Golden Company who looks like a woman and paints his nails. But Lysono has explicitly said in TWOW preview chapters that he is not a woman. He just appears to be a guy born with feminine looks, who is confident about the way he looks. Then of course we have Cersei who has shown resentment that she should have been born a man over a number of times but that's mostly when someone denies her something they wouldn't deny a man or when she regrets that she could have been Lord Tywin's heir if she were born with a penis. Therefore, she doesn't seem like someone with trans tendencies either.

Those three aside then, do we have anyone else?

NOTE: I am not the most well-versed person around regarding the modern take on sexuality and gender. My question is about people who are born in one gender but want to be another. Keeping that aim in mind, If you believe that I may have used some terms or labels incorrectly in the question, please feel free to correct that by editing. Thank you.

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    There is a huge difference. Transsexual is changing your sex, transgender is changing your gender. Sex is determined by your genitals. Gender is how you feel. Brienne is definitely transgender, i.e., she feels more like a man than a woman. If she likes Renly, we can say she is a transsexual gay man. (Does it make sense to you?) Varys can be considered as transsexual, but it is hard to say 100%. – C.Koca Feb 10 '18 at 18:27
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    @C.Koca Thank you for enlightening me. I believe that makes my question about Transgenderism, rather than transsexualism given that they couldn't change their sex in Planetos. Brienne is however most definitely not transgender or a trans-gay-man. If she were, she wouldn't picture herself as a mother. A mother, I think, is still a woman whether biological or trans – Aegon Feb 10 '18 at 18:30
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    @ApproachingDarknessFish given that the characters are written by an author living in the current day and age who’s explored some pretty “modern” (and archaic) themes, there is every possible he chooses to write in and portray a transgender character. It’s setting is irrelevant given the author is creating a fantasy based on our medieval history, they can and may cry easily introduce the notion of non-binary genders. – Edlothiad Feb 11 '18 at 17:13
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    @Naib Er, you do realize there is more to Westeros than just "Ermahgerd, wintuh iz koming"? Whitewalkers were seen only in the Dawn ages and it has been 8,000 years since, for majority of the population, they are just a myth. I don't see the Westerosi people being paranoid for 8000 years about something they believe to be fairytale creatures, made up to scare children at night\ – Aegon Feb 13 '18 at 9:00
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    @C.Koca I really disagree about Brienne - in the TV show she might be a masculine woman with a negative attitude to femininity (though unlike real-life historical trans people, she never tried to present as other gender; if you must apply a label, maybe 'gender nonconforming'..?), but in the books (particularly AFFC), we see she has a strong feminine side and tastes, deeply suppressed from years of rejection and taunts, emerging on the rare occasions someone treats her kindly (e.g. Renly & the shield painter); and how her un-macho "focussed professional" fighting style helps vs macho rivals. – user56reinstatemonica8 Feb 26 '18 at 23:37
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There is no character from the current timeline who might be considered transgender, given that we have already ruled out Cersei, Lysono Maar and Brienne.

But we do have someone from history who might fit the bill.

Meet King Loreon V Lannister, who was known as Queen Lorea instead.

He was grandson to King Loreon IV, known as Loreon the Lackwit. It is unclear if Loreon IV's son (Loreon V's father) ever inherited the throne or not but nevertheless, Loreon V took the throne either on his father's death or his grandfather's death.

The King was however fond of dressing as a woman and acting as a woman. Needs of the state of course required him to marry a woman and sire heirs and spares but he soon took to dressing in his wife's clothing and wandering the port docks disguised as a common prostitute. Before too long, his subjects began calling him Queen Lorea instead King Loreon.

Some of the Lannister kings were famed for their wisdom, some for their valor, all for their open-handedness...save perhaps for King Norwin Lannister, better known as Norwin the Niggardly. Yet Casterly Rock also housed many a weak, cruel, and feeble king. Loreon IV was better known as Loreon the Lackwit, and his grandson Loreon V was dubbed Queen Lorea, for he was fond of dressing in his wife's clothing and wandering the docks of Lannisport in the guise of a common prostitute. (After their reigns, the name Loreon became notably less common amongst Lannister princes.)
TWOIAF: The Westerlands

He is the closest that we get to a transgender character in Planetos.

He appears to have been inspired from the Roman Emperor, Elagabalus. It is said that Elagabalus used to paint his eyes, dipilate his body hair and wore wigs. He also took male lovers, chief among them was Hierocles. The Emperor is described to have been "delighted to be called the mistress, the wife, the queen of Hierocles". It is said that he also used to pretend to be a prostitute in the Palace where the courtiers and guards would play the role of the patrons. He also reportedly offered large sums of money to any physician who could equip him female Genitalia. Which is why some modern historians argue that he may have been a transwoman.

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