In pre-Islamic Arabia and Mesopotamia, women encompassed the majority of the ranks of professional musicians used for court entertainments. Music performance, particularly for entertainment, was closely associated with women and this did not substantially change with the advent of Islam. "Singing girls" (pl. qiyan, sing., qayna), acquired through trade and conquest, formed a special class of slave courtesans trained to perform at court. Though men were not actively prohibited from becoming musicians, it was not socially acceptable for a free man to make a living as a musician. Men who did risked becoming social outcasts. The most visible of these were referred to by the pejorative mukhannathun (effeminates) because they imitated women by adopting feminine dress and mannerisms; with some even performing on "women's" instruments. This type of musical cross-dressing, however, as with use of singing girls, also had ancient roots. During the late 7th century, their dual performance as musicians and "women" made mukhannathun targets for persecution, yet their skill earned them enough patronage that by the 9th century, subsequent generations of men were accepted as professional musicians. Music became central to courtly entertainments during the early Abbasid era (750 - 950CE), and soon such entertainments became lavish affairs; employing large numbers of both male and female musicians in gatherings that could last for days. Some scholars believed that these excesses were stimulated by music, and soon began to question what types of music, if any, were acceptable within Islam. Though the ensuing debates took place in the realm of philosophy and religious law, the rhetoric used was influenced by the continuation of gendered musical performance practices and associations of music performance with sexual identity that had existed on the cultural landscape for millennia. In this paper, I will discuss the links between musical and sexual identity in the early Abbasid court as seen through the different roles and expectations for musical performance for male and female court musicians and the contexts in which these performances took place. Using observations and opinions from select texts, I suggest that the intersection of performance, gender and music were important factors in the development of a musical semiotics used in subsequent debates surrounding the acceptance of music in Islam.