Mukhannathun (Arabic مخنثون "effeminate ones", "men who resemble women", singular mukhannath) is classical Arabic for people who would now be called transgender women, perhaps poorly distinguished from eunuchs. Various "mukhannathun" appear in several hadith. In one hadith the prophet Muhammad banishes a mukhannath to a region near Medina, but prohibits people from killing them. They could be said to be Muslim transwomen accepted as they are "within the boundaries of Medina and Mecca".  Outside of the religious text they are strongly associated with music and entertainment.
Reports of Mukhannathun from the Qur'an, Hadith and Sunnah
There are many references to these people, both directly and indirectly, in the Qur'an, Hadith and Sunnah. In the Qur'an:
The Qur'an Sura 24 verse 31 (as translated by Shakir): And say to the believing women that they cast down their looks and guard their private parts and do not display their ornaments except what appears thereof, and let them wear their head-coverings over their bosoms, and not display their ornaments except to their husbands or their fathers, or the fathers of their husbands, or their sons, or the sons of their husbands, or their brothers, or their brothers' sons, or their sisters' sons, or their women, or those whom their right hands possess, or the male servants not having need (of women), or the children who have not attained knowledge of what is hidden of women; and let them not strike their feet so that what they hide of their ornaments may be known; and turn to Allah all of you, O believers! so that you may be successful.
Two reliable hadith are.
Sunan Abu-Dawud, Book 41, Number 4910: Narrated AbuHurayrah: A mukhannath who had dyed his hands and feet with henna was brought to the Prophet (peace_be_upon_him). 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 (in other words not referring to Jannat al-Baqi cemetery.'
Sunan Abu-Dawud, Book 32, Number 4095: Narrated Aisha, Ummul Mu'minin: A mukhannath (eunuch) used to enter upon the wives of Prophet (peace_be_upon_him). They (the people) counted him among those who were free of physical needs. One day the Prophet (peace_be_upon_him) 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 in her stomach), and when she goes backward, she goes backward with eight (folds in her stomach). The Prophet (peace_be_upon_him) said: Do I not see that this (man) knows what here lies. Then they (the wives) observed veil from him. 
Analysis of Scholars
This curious fact about the early history of Islam did not escape the notice of Islamic scholars past and present.
According to the scholar and hadith collector An-Nawawi:
A mukhannath is the one ("male") who carries in his movements, in his appearance and in his language the characteristics of a woman. There are two types; the first is the one in whom these characteristics are innate, he did not put them on by himself, and therein is no guilt, no blame and no shame, as long as he does not perform any (illicit) act or exploit it for money (prostitution etc.). The second type acts like a woman out of immoral purposes and he is the sinner and blameworthy.
Furthermore there is the observation of Ibn Abd Al-Barr who was a contemporary of An-Nawawi:
The mukhannath is not only the one who is known to be promiscuous. The mukhannath is (also?) the one who looks so much like a woman physically that he resembles women in his softness, speech, appearance, accent and thinking. If he is like this, he would have no desire for women and he would not notice anything about them. This is one of those who have no interest in women who were permitted to enter upon women. "
In the current era, scholars in Iran, and Egypt have issued Fatwas supporting the right for those who fit the description of Mukhanathun to have sex reassignment surgery. In Pakistan to this day, there live Hijras. The Muslim Hijras have been known to refer to themselves as Mukhannathun when speaking Arabic.
The mukhannathun as a group do not fit neatly into any one of the prevailing categories of gender or sexuality used in the West at this time. While they were certainly not straight, it cannot be said that they were simply homosexual males. While they are gender variant, it seems that the intensity differs from one mukhannath to the next.
In "The Effeminates of Early Medina" Everett K. Rowson describes the very same Mukhanathun who appear in the Hadith, and who were companions of the prophet Muhammad. Rowson describes several other Mukhannathun who were contemporary to the Prophet Muhammad, in particular Tuways and Al-Dalal. Tuways was a talented musician and singer who lived to the age of 82. Tuways is known to have married and fathered children. From what is written, Al-Dalal clearly preferred men. Specifically it is written that though "Al-Dalal enjoyed women's social company any sexual demand made of her was in vain". Al-Dalal is said to have had a sexual encounter with a woman on her wedding night. Al-Dalal then later that same night had sexual relations with the groom. Similar stories exist about the other Mukhannathun of Medina. 
According to Imam 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 gay men, as they were involved in practices not common to contemporary gay men. 
At one point in time during the Umayyad dynasty, a caliph, usually identified as Sulayman ibn Abd al-Malik, reportedly ordered that all Mukhannathun should be castrated. He had been angered by them in some way or other - the motive varies between the different accounts. According to Rowson:
Several sources name some or all of the victims (besides al-Dalal, who is almost always included). A number of these also report a series of quips said to have been pronounced by them on the occasion. The fullest version of these statements is offered by Hamza, whose list is as follows:
- Tuways: "This is simply a circumcision which we must undergo again."
- al-Dalal: "Or rather the Greater Circumcision!"
- Nasim al-Sahar: "With castration I have become a mukhannath in truth!"
- Nawmat al-Duha: "Or rather we have become women in truth!"
- Bard al-Puad: "We have been spared the trouble of carrying around a spout for urine."
- Zill al-Shajar: "What would we do with an unused weapon anyway?"
Interestingly Rowson goes on to write about this story:
A third account, dependent on the "ta~hif" version of the castration story, reports that the caliph Sulayman was grieved by the accidental castration of the charming al-Dalal, and had him secretly brought to his court. When the caliph asked him how he was, al-Dalal replied, "Now that you've truncated (jababta) me in front, do you want to truncate me in back?" Sulayman laughed, and ordered him to sing. Unable to decide whether he was more charmed by his wit or his singing, the caliph kept him, with him a month, rewarded him richly, and sent him back to the Hijaz." 
- ^ a b c USC-MSA compendium of Muslim Text: Partial Translation of Sunan Abu-Dawud, Book 41:General Behavior (Kitab Al-Adab),Number 4910
- ^ a b Hadith on this matter, USC-MSA compendium of Muslim Text: Partial Translation of Sunan Abu-Dawud, Book 32:Clothing (Kitab Al-Libas),Number 4095
- ^ a b c d e f g h i j k l m n o Rowson, Everett K. (October 1991). "The Effeminates of Early Medina". Journal of the American Oriental Society (American Oriental Society) 111 (4): 671–693. doi:10.2307/603399. JSTOR 603399. http://www.williamapercy.com/wiki/images/The_effeminates_of_early_medina.pdf.
- ^ [|Al Muqni, Matan]. al Sharh al Kabeer. volume 7 347–348.
- ^ [|Hendricks, Muhsin] (July 2006). "Islam and Homosexuality" (PDF). ILGA's preconference on religions: ILGA. http://doc.ilga.org/content/download/4522/27322/version/1/file/ILGA-July06-Religions.pdf. Retrieved 2007-06-22.
- Hadith on this matter, USC-MSA compendium of Muslim Text: Partial Translation of Sunan Abu-Dawud, Book 32:Clothing (Kitab Al-Libas), Number 4095
- Hadith on this matter, USC-MSA compendium of Muslim Text: Partial Translation of Sunan Abu-Dawud, Book 41:General Behavior (Kitab Al-Adab), Number 4910
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