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Etymology
In analyzing the origin of the molly house denomination, it seems important to investigate the first component of the compound. According to the Oxford English Dictionary, the word molly (also spelt as molley, mollie, mally) is considered a pet-form of the female forename Mary, and had two main connotations in 18th century English. The first one is close to the word moll, designing a lower-class girl or woman, occasionally a prostitute. The second one, also seen in the pejorative form a miss molly, is classified as slang, defining an effeminate, usually homosexual, male. Along with the possible perception of intrinsic female features deriving from the association with the name Mary, another possible origin of this denomination for a homosexual man could be found in the Latin form mollis, indicating the supposed passive-effeminate partner in male homosexual relationships. However, the question is quite complex when considering the translation of molly given in some dictionaries of the time, particularly in 1762, in a Swedish/English dictionary by Jacob Serenius, and in a French/English dictionary by Thomas Nugent, in 1767. The word was present, but simply defined a sodomite, without effeminate connotations.

In this sense, it is possible to see that the notion of molly house seems to be deeply rooted in a social phenomenon that some critics in gender studies consider crucial: the developing of a distinctive identity according to gender and sexual orientation. Mollies, and other third gender identities, could be interpreted as precursor to the more defined homosexual identity of the last two centuries.

Homosexual subculture in London
Molly houses could be considered the most organised phenomenon of the 18th century homosexual subculture in London, as they were enclosed spaces gathering individuals with a common purpose, that is to say, socializing and seeking pleasure with same-sex partners. As this common purpose was treated as a capital offence, the organisation of homosexual men and their activities had to be a crucial point, in order to keep the community as safe as possible from prosecution. Consequently, "molly districts" seemed to appear, and eventually grow, in areas in which their business could be acknowledged and at the same time tolerated: such connivance could be often found in the district with a high rate of criminal acts (such as theft and prostitution). Six or seven areas could be identified in central London in the eighteenth century, from an editorial in The London Journal: the Royal Exchange, Moorfields, Lincoln's Inn, the south side of St James's Park and the arcades of Covent Garden. Other hints to identify molly areas are given by the places in which pillories related to sodomitical offences took place, as pillories were often organised near the crime locations attributed to the accused.

The adoption of specific codes in relating to each other was another feature allowing cohesion among the group. They would take on a female persona, have a female name, and affect feminine mannerisms and speech. Marriage ceremonies between a Mollie and his male lover were enacted to symbolise their partnership and commitment. The impersonation could at times include a ritual called "mock birth" (or "lying-in"), where a Molly would be dressed in a nightgown, laid on a chair, and assisted by fellow Mollies as "midwives" during a highly ritualized enactment of a woman's labour until finally a wooden doll representing the baby was born. This ritual almost certainly originated as a couvade, designed to collectively relieve the extreme stress this particular social group was forced to live under.

The role of law enforcement
Molly houses at that time were intrinsically related to the sin, but also offence, of sodomy or buggery (a specific common law offence encompassing both sodomy and bestiality). Before 1533 it was dealt with by the ecclesiastical courts, then, from that year the country's first civil sodomy law was first introduced, as An Acte for the punishment of the vice of Buggerie (Buggery Act 1533). Being a capital offence, most of the information concerning molly houses and the community around them is available through an indirect form, that is, mostly through the accounts given during the Old Bailey Proceedings relating to sexual offences, such as sodomy, assault with sodomitical intent and keeping a brothel, or sometimes the ones related to theft cases. Other important sources are satires and pamphlets, such as An Answer To A Late Insolent Libel by Jonathan Wild, Edward Ward's Satyrical Reflections on Clubs, Chapter XXV Of the Mollies Club, John Dunton's ''The He-Strumpets. A Satyr on the Sodomite-Club'' and other works. While molly-houses continued to exist throughout the 18th and early 19th century, some of them even operating semi-publicly, patrons were often prosecuted. Homosexuals condemned to stand in the pillory appear in court records as often as once a week for years in the mid-18th century. Convictions for sodomy in London resulted in frequent hangings at Tyburn.

Trials and personalities related to molly houses
On 9 May 1726, three men (Gabriel Lawrence, William Griffin, and Thomas Wright) were hanged at Tyburn for buggery following a raid of Margaret Clap's molly house. The controversial figure of Charles Hitchen (alternative spelling Hitchin), former Under City Marshal, member of the Society for the Reformation of Manners and notable thief-taker, was also convicted of assault with sodomitical intent, on 12 April 1727.

Mother Clap's molly house
The most well-known molly house was Mother Clap's, which had been open from 1724 until a raid sustained by the Societies for the Reformation of Manners in 1726. It was located in Field Lane, near to another tavern The Bunch of Grapes in Holborn, a suburban parish of Middlesex a short distance from the City of London. This area came to be renowned as a rookery in the next decades, and described as  a sort of distinct town, or district calculated for the reception of the darkest and most dangerous enemies to society; in which when pursued for the commission of crimes they easily conceal themselves and readily escape. A literary example can be interpreted as a sort of confirmation of the reputation of this lane, since Charles Dickens placed here Fagin's den, an old Jewish man earning a living as a fence, in his 1837 novel Oliver Twist.

This peculiar meeting place, however, became well known to the public during the 1720s through the trial of its keeper, Margaret Clap, indicted for keeping a disorderly house and for encouraging her customers to commit sodomy; and, particularly, through the account given by an agent provocateur, Samuel Stevens.