The word may have started to acquire associations of immorality as early as the 14th century, but had certainly acquired them by the 17th.[2] By the late 17th century, it had acquired the specific meaning of "addicted to pleasures and dissipations",[11] an extension of its primary meaning of "carefree" implying "uninhibited by moral constraints". A gay woman was a prostitute, a gay man a womanizer, and a gay house a brothel.[2] An example is a letter read to a London court in 1885 during the prosecution of brothel madam and procuress Mary Jeffries that had been written by a girl while slaved to a French brothel:
"I write to tell you it is a gay house...Some captains came in the other night, and the mistress wanted us to sleep with them."
The use of gay to mean "homosexual" was often an extension of its application to prostitution: a gay boy was a young man or boy serving male clients.[13]
Similarly, a gay cat was a young male apprenticed to an older hobo, commonly exchanging sex and other services for protection and tutelage.[2] The application to homosexuality was also an extension of the word's sexualized connotation of "carefree and uninhibited", which implied a willingness to disregard conventional or respectable sexual mores. Such usage, documented as early as the 1920s, was likely present before the 20th century,[2] although it was initially more commonly used to imply heterosexually unconstrained lifestyles, as in the once-common phrase "gay Lothario",[14] or in the title of the book and film The Gay Falcon (1941), which concerns a womanizing detective whose first name is "Gay". Similarly, Fred Gilbert and G. H. MacDermott's music hall song of the 1880s, "Charlie Dilke Upset the Milk" – "Master Dilke upset the milk, when taking it home to Chelsea; the papers say that Charlie's gay, rather a wilful wag!" – referred to Sir Charles Dilke's alleged heterosexual impropriety.[15] Giving testimony in court in 1889, the prostitute John Saul stated: "I occasionally do odd-jobs for different gay people."[16]