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Mukhannathun (مخنثون "effeminate ones", "men who resemble women", singular mukhannath) was a term used in Classical Arabic to refer to men who were perceived as effeminate. Mukhannathun, especially those in the city of Medina, are mentioned throughout the ahadith and in the works of many early Arabic and Islamic writers. During the Rashidun era and first half of the Umayyad era, they were strongly associated with music and entertainment. During the Abbasid caliphate, the word itself was used as a descriptor for men employed as dancers, musicians, or comedians.
In later eras, the term mukhannath was associated with the receptive partner in gay sexual practices, an association that has persisted into the modern day. Khanith is a vernacular Arabic term used in some parts of the Arabian Peninsula to denote the gender role ascribed to males who function sexually, and in some ways socially, as women. The term is closely related to the word mukhannath.
The origins of the term are disputed. The 8th century lexicographer Al-Khalil ibn Ahmad al-Farahidi connected mukhannath to khuntha, meaning hermaphrodite. According to the 9th century Arabic scholar Abu Ubayd, the term mukhannath instead derives from the verb khanatha, meaning "to fold back the mouth of a waterskin for drinking", indicating some measure of being languid or delicate. This definition attained prominence among Islamic scholars until medieval times, when the term came to be associated with homosexuality.
Mentions in the ahadith
Mukhannathun existed in the pre-Islamic and early Islamic eras. A number of ahadith indicate that mukhannathun were used as male servants for wealthy women in the early days of Islam, due to the belief that they were not sexually interested in the female body. These sources do not state that the mukhannathun were homosexual, only that they "lack desire".
Various ahadith say Muhammad cursed the mukhannathun and their female equivalents, mutarajjilat, and ordered his followers to remove them from their homes. 
- The Prophet (May peace be upon him) cursed effeminate men (mukhannathan) and women who imitated men, saying: Put them out of your houses, and put so-and-so out.
According to one hadith, this incident was prompted by a mukhannath servant of Muhammad’s wife Umm Salama commenting upon the body of a woman. This comment may have convinced Muhammad that the mukhannathun were only pretending to have no interest in women, and therefore could not be trusted around them.
Aisha says: Amukhannath used to enter upon the wives of Prophet. They (the people) counted him among those who were free of physical needs. One day the Prophet entered upon us when he was with one of his wives, and was describing the qualities of a woman, saying: When she comes forward, she comes forward with four (folds of her stomach), and when she goes backward, she goes backward with eight (folds of her stomach). The Prophet said: Do I not see that this one knows what here lies. Then they (the wives) observed veil from him.
This story places the incident around the time of the Siege of Ta'if. However the scholars say that this only refers to those mukhanathun who are pretending and not actually lacking desire for women. As for those who are not pretending, they are allowed to enter upon women. 
Early Islamic literature rarely comments upon the habits of the mukhannathun. It seems there may have been some variance in how "effeminate" they were, though there are indications that some adopted aspects of feminine dress or at least ornamentation. One hadith states that a Muslim mukhannath who had dyed his hands and feet with henna (traditionally a feminine activity) was banished from Medina, but not killed for his behavior.
A mukhannath who had dyed his hands and feet with henna was brought to the Prophet. He asked: What is the matter with this man? He was told: Apostle of Allah! he affects women's get-up. So he ordered regarding him and he was banished to an-Naqi'. The people said: Apostle of Allah! should we not kill him? He said: I have been prohibited from killing people who pray. AbuUsamah said: Naqi' is a region near Medina and not a Baqi.
Other ahadith also mention the punishment of banishment, both in connection with Umm Salama’s servant and a man who worked as a musician. Muhammad described the musician as a mukhannath and threatened to banish him if he did not end his unacceptable career.
Beyond these incidents, there are few sources elaborating upon the mukhannathun during Muhammad’s lifetime.
In later eras
In the Rashidun and Umayyad eras, various mukhannathun of Medina established themselves as celebrated musicians. One particularly prominent mukhannath with the laqab Tuways ("little peacock") was born in Medina on the day Muhammad died.
There are few sources that describe why Tuways was labeled a mukhannath, or what behavior of his was considered effeminate. No sources describe his sexuality as immoral or imply that he was attracted to men, and he is reported to have married a woman and fathered several children in his later life. While he is described as non-religious or even frivolous towards religion in many sources, others contradict this and portray him as a believing Muslim instead. His main association with the label seems to come from his profession, as music was mainly performed by women in Arab societies. Tuways is described as the first mukhannath to perform "perfect singing" characterized by definitive rhythmic patterns in Medina. He was also known for his sharp wit and his skill with the tambourine, which had previously been associated only with female musicians.
Some scholars believe that Tuways and other mukhannathun musicians formed an intermediary stage in the social class most associated with musical performance: women in pre-Islamic times, mukhannathun in the Rashidun and early Umayyad caliphates, and mainly non-mukhannath men in later time periods. While many still disapproved of the mukhannathun in general in this era, the musicians among them were nonetheless valued and prized for their skill. Some of the more well-known mukhannathun also served as go-betweens and matchmakers for men and women.
While Tuways is typically described as the leading mukhannath musician of Medina during his lifetime, historical sources describe others who served a similar role providing musical and poetic entertainment. A man with the laqab al-Dalal ("the coquettish") is mentioned as one of Tuways’ pupils. He is portrayed as a witty but sometimes crude man who "loved women" but did not have sex with them. Unlike Tuways, some tales involving al-Dalal do suggest that he was attracted to men.
Persecution and decline
While sporadic persecution of mukhannathun dates back to the time of Muhammad, their large-scale governmental persecution began in the Umayyad caliphate. This may have been prompted by "a perceived connection between cross-dressing and a lack of proper religious commitment", according to the scholar Everett K. Rowson. Some sources associate the beginning of severe persecution with Marwan I and his brother Yahya, who served as a governor under the caliph Abd al-Malik ibn Marwan, while others put it in the time of Abd al-Malik’s son, Al-Walid I. The governor of Mecca serving under al-Walid is said to have “issued a proclamation against the mukhannathun”, in addition to other singers and drinkers of wine. Two mukhannathun musicians named Ibn Surayj and al-Gharid are specifically named as being impacted by this proclamation, with al-Gharid fleeing to Yemen and never returning. Like al-Dalal, al-Gharid is portrayed as not just "effeminate" but homosexual in some sources. Beyond these two men, relatively little is known of the mukhannathun of Mecca, compared to the more well-known group in Medina.
The most severe instance of persecution is typically dated to the time of al-Walid's brother and successor Sulayman ibn Abd al-Malik. According to several variants of this story, the caliph ordered the full castration of the mukhannathun of Medina. Some versions of the tale say that all of them were forced to undergo the procedure, while others state that only a few of them were; in the latter case, al-Dalal is almost always included as one of the castrated mukhannathun.
Some variants of the story add a series of witticisms supposedly uttered by the mukhannathun prior to their castration:
- Tuways: “This is simply a circumcision which we must undergo again.”
- al-Dalal: “Or rather the Greater Circumcision!”
- Nasim al-Sahar (“Breeze of the Dawn”): “With castration I have become a mukhannath in truth!”
- Nawmat al-Duha: “Or rather we have become women in truth!”
- Bard al-Fu'ad: “We have been spared the trouble of carrying around a spout for urine.”
- Zillal-Shajar (“Shade Under the Trees”): “What would we do with an unused weapon, anyway?”
After this event, the mukhannathun of Medina begin to fade from historical sources, and the next generation of singers and musicians had few mukhannathun in their ranks. Rowson states that though many details of the stories of their castration were undoubtedly invented, “this silence supports the assumption that they did suffer a major blow sometime around the caliphate of Sulayman.”
By the days of the Abbasid caliph al-Mamun, the mukhannathun working as entertainment were now more associated with court jesters than famed musicians, and the term itself seems to have become synonymous with an individual employed as a comedian or pantomime. The Abbasid caliphs al-Mamun and al-Mutawakkil employed a famed mukhannath named Abbada as an actor in comedic plays. He served as a buffoon whose act depended upon mockery and "low sexual humor", the latter of which involved the flaunting of his "passive homosexuality". These characteristics would define mukhannathun in later eras, and they never regained the relatively esteemed status they held in the early days in Medina.
The eighth-century scholar Ibn Shihab al-Zuhri stated that one should pray behind mukhannathun only in cases of necessity. Some thirteenth and fourteenth-century scholars like an-Nawawi and al-Kirmani classified mukhannathun into two groups: those whose feminine traits seem unchangeable, despite the person’s best efforts to stop them, and those whose traits are changeable but refuse to stop. Islamic scholars like Ibn Hajar al-‘Asqalani stated that all mukhannathun must make an effort to cease their feminine behavior, but if this proved impossible, they were not worthy of punishment. Those who made no effort to become less "effeminate", or seemed to "take pleasure in (his effeminacy)", were worthy of blame. By this era, mukhannath had developed its association with homosexuality, and Badr al-Din al-Ayni saw homosexuality as "a more heinous extension of takhannuth", or effeminate behavior.
Ibn 'Abd al-Barr stated that mukhannathun in his era were "known to be promiscuous", and resembled women in "softness, speech, appearance, accent and thinking". These mukhannathun were the ones initially allowed to be the servants of women, as they did not demonstrate any physical attraction to the female body.
While sometimes classified as transgender individuals, mukhannathun as a group do not fit neatly into any one of the prevailing categories of gender or sexuality used by modern LGBT communities. Although they were probably not predominantly cisgender or heterosexual, it cannot be said that they were simply either homosexual males or transgender women. There was too much variety between one mukhannath and the next to determine a specific label for their gender or sexual identity, and the term's meaning changed over time.
Likewise, while some mukhannathun are said to have engaged in homosexuality, others did not, complicating efforts to label them gay men. According to Muhsin Hendricks:
Muhammad did deal with a group of effeminate men in Medina called "Mukhannathun". However, while this group of Mukhannathun did possess qualities of modern gay men, it cannot be said that the Mukhannathun fully represent modern homosexual men, as they were involved in practices not common to contemporary homosexual men.
In the late 1980s, Mufti Muhammad Sayyid Tantawy of Egypt issued a fatwa supporting the right for those who fit the description of mukhannathun to have sex reassignment surgery. Tantawy seems to have associated the concept with hermaphroditism or intersex individuals. Ayatollah Khomeini of Iran issued similar fatwas around the same time. Khomeini's initial fatwa concerned intersex individuals as well, but he later specified that sex reassignment surgery was also permissible in the case of transgender individuals. Because homosexuality is illegal in Iran but transgenderism is legal, some gay individuals have been urged to undergo the surgery and transition into the opposite sex, regardless of their actual gender identity.
According to the fatwa website islamqa.info:
The word mukhannath (“effeminate”) refers to a person who behaves like a woman in gentleness, speech, appearance, movements and so on. Effeminate people are of two types. (i)Those who are created that way; there is no sin on them. (ii)Those who were not created that way; rather they choose to imitate women in their movements and speech. This is the type which is cursed in the saheeh hadeeths.
Some modern Islamic authorities say that if an individual deemed a khuntha or intersex has an unclear gender, it is not permissible for him to marry a woman until a medical professional confirms that he is male.
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