Are there any transgender characters in Westeros?

Question

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.

Answer 1

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.

Answer 2

The Jogos Nhai, the mounted nomads who live east of the Dothraki.

Each tribe of the Jogos Nhai is led by a jhat (war leader) and a moonsinger (combination of priestess, healer, and judge). The jhat is usually male and rules over external affairs, while the moonsingers are usually women, who rule over internal affairs. If a young male wishes to be a moonsinger, he can – although he must dress and live as a woman. Similarly, a young female who wishes to be a jhat must dress and live as a man. Zhea the Cruel, one of the most famous Jogos Nhai war-leaders in history, who united them all as jhat of jhats to smash the armies of Yi Ti, was himself born a biological female.