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Some prostitutes cater to highly exclusive clientele, make a good enough living, and may to a certain extent pick and choose their clientele. Others take who they can get and do whatever they have to in order to survive, often living miserable lives. Many prostitutes in Essos are enslaved.
Prostitutes in Westeros.
Prostitutes are normally on the bottom rung of the societal ladder, even the wealthier ones, and are looked down upon by most people because of their trade. Tywin Lannister is well known for his disdain of whores and those who take advantage of their services.  It is considered dishonorable for a nobleman to openly frequent whores and brothels, hence the secret passageway that runs from Chataya’s brothel in King’s Landing to a nearby stable. Despite these attitudes, Westeros teems with brothels and whores.
Many of the Night’s Watch visit the whores in the Mole’s Town brothel. Despite their vows to remain celibate, a blind eye is turned to it out of pragmatism. 
Attitudes about sexuality are more relaxed in Dorne  , so the view of Dornishmen toward prostitutes may be more liberal.
Some brothels in Westeros cater to more exclusive clientele, such as Chataya’s. In contrast, the Lazy Eel is renowned for offering some of the oldest whores in White Harbor.  Oldtown has unsavory black brothels. 
On Maiden’s Day maidens of noble houses are required to go to the sept to light tall white candles at the Maiden’s feet and hang parchment garlands about her neck. Mothers, whores, and widows are barred from the sept along with men.  A virgin prostitute’s maidenhead can cost a golden dragon. 
Female whores feature most in Westeros, but it is mentioned that Satin was a boy-whore in Oldtown before joining the Night’s Watch,  and the whore Hother “Whoresbane” Umber disemboweled in Oldtown was a man. 
Known whores in Westeros.
Alayaya Bella Cass Chataya Dick Crabb’s sister Dancy Jayde Leslyn Marei Penny Jenny The queen of whores Shae.
Known brothels in Westeros.
In the Free Cities and other places in Essos, the attitude towards prostitution is different, and there appears to be less ignominy in engaging the services of a whore. This may be because many of the Free Cities practice slavery and where there is slavery there will be sexual abuse and exploitation. Slaves who are whores have tears tattooed beneath their right eye.  
The practice of slavery has created a thriving business in trained male and female bed-slaves, particularly from Lys,  whose pillow houses and pleasure gardens are famous.  Whether all enslaved whores are also trained bed-slaves is unlikely. Many slaves are forced into prostitution during childhood. Most have little or no hope of escaping this way of life, aside from suicide, and are crushed by the abuse and despair they endure. 
The Ghiscari Red Graces are religious prostitutes housed in the Temple of the Graces in Meereen. There is no shame in their prostituting themselves, but the same cannot be said of the Westerosi counterpart, the septa. 
In Braavos there are no slaves, so all the prostitutes are free people. However, there are three classes of prostitutes on Braavos: the highly esteemed professional courtesans; whores kept in a brothel; and the lowest street-walking dockside whores. Braavosi courtesans enjoy high status and are renowned worldwide. 
Known whores in Braavos.
Summer Islanders esteem the art of lovemaking; there is no stigma to prostitution there. 
Known frequenters of prostitutes.
The ironborn reavers of old took captured women to be their whores and thralls. 
King Baelor I Targaryen attempted to outlaw prostitution in King’s Landing, resulting in at least a thousand women and children sent from the capital.  King Aegon IV Targaryen slept with all types of women, including princesses and whores. 
After the death of Lord Tytos Lannister, his heir, Tywin, forced his father’s mistress to walk through Lannisport on a walk of atonement to show the city she was a whore.  Tywin later had his elder son, Jaime, convince his younger son, Tyrion, that Tyrion’s bride Tysha was a whore. Tywin forced the crofter’s daughter to service his barracks, who paid with silver, and forced Tyrion to go last and pay with gold. 
Petyr Baelish, the master of coin for King Robert I Baratheon, owns many brothels. After Lord Eddard Stark is imprisoned by the Iron Throne, Petyr hides Jeyne Poole in one of his establishments. 
The camp follower Shae becomes the lover of Tyrion Lannister. 
Tyrion brings Shae to King’s Landing against the wishes of his father, Lord Tywin Lannister. 
The dwarf’s penny is a tax imposed on prostitution in King’s Landing.  When Tyrion is on trial for the death of King Joffrey I Baratheon, Shae claims that she was forced to pleasure him.  After Ser Jaime Lannister releases his brother from the Red Keep’s dungeon, Tyrion kills Shae after learning she had been sleeping with Tywin. Having also learned from Jaime that Tysha had not actually been a prostitute, Tyrion kills Tywin when his father says Tysha went “wherever whores go”. 
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