Arts & Entertainment


Like Darlinghurst, Kings Cross and Surry Hills, Woolloomooloo has always been a popular location for Sydney’s once bourgeoning number of brothels. Prior to the decriminalisation of prostitution in 1979, the city’s knocking shops were a largely rough and tumble affair. Many were owned by gangsters like Tilley Devine who by the late 20s had built an empire of some eighteen bordellos in precincts bordering the CBD. As with many businesses COVID-19 has certainly impacted the sex industry but the colourful history of Sydney’s one time houses of ill repute is bound to continue – albeit with some modifications. 

Prior to the pandemic I was a long time resident of Cathedral Street Woolloomooloo, which housed one of the suburb’s busiest bordellos at 110, directly opposite the East Sydney Hotel. Throughout the day and into the early hours of the morning there was a steady stream of customers, using the brothel’s discreet entrance behind a couple of large shrubs. Unfortunately I had a street number very similar to the actual brothel and I would often get potential patrons buzzing my intercom by mistake, often well past midnight. After a while I got sick of redirecting punters and would reply with comments like, “Sorry we are closed tonight due to a rat infestation.”

Sitting in the East Sydney Hotel and observing the streetscape through the window of the main bar it was not hard to pick those customers, arriving for their service at 110. For many their sheepish body language was a dead giveaway as they strolled casually past the discreet entrance, looking to see if anybody was watching, then turning and making a quick dash behind the shrubs. Clearly for a number there was still a sense of guilt or shame in visiting such an establishment and horror or horrors if they were ever sprung doing so. 

Anybody who has driven a taxi in Sydney at night for a period of time will no doubt have a road map of the city’s brothels indelibly inscribed in their brain. Having done so myself whilst a student in the 80s, I soon got to know where both the up market and the low budget establishments existed. The more discreet passengers would asked to be dropped off at a street corner close to their preferred brothel – come on, you knew exactly where they were going. Those less inhibited or often highly inebriated would have no problem in asking to be taken straight to a particular venue. 

In the 1980s the infamous Touch Of Class in Surry Hills, run by the celebrated madam Zara Powell, was Sydney’s best known bordello, popular with customers from all walks of life. One night behind the wheel I got a call to pick up a group of visiting Japanese from a five star CBD hotel and take them to the Touch Of Class. Three or four other cabs also got the call and for the next five hours, directed with military precision by the Japanese tour guide, we shuffled what seemed like dozens of giggling, high spirited businessmen to and fro. There was a sizeable tip at the end of the night and I got to learn what the Japanese often refer to as “night shopping.”

Back in 2019 the Cathedral Street brothel at 110, went on the market for $5 million with the highly prized real estate comprising the bulk of the asking price. I am not sure what the result was but today it is still operating under its original name of Five Star City, now billed as “Sydney’s leading contemporary art studio.” Elsewhere in the City Of Sydney a number of brothels have closed down and sold off their freehold – seeing more value in cashing in on the still high property prices or simply cutting their losses incurred during the lockdowns. 

Many of the best known establishments like the Touch Of Class and the Golden Apple in Potts Point were housed in grand old terraces and embellished with period furnishings. In fact, going right back to the days of Tilly Devine the iconic Sydney terrace house has been the preferred real estate for the brothel industry. The rise of mega brothels like Stilettos in Camperdown might herald a new direction that will eventually see the old school boutique bordellos disappear for premises of industrial proportions. In the meantime there’s still time for a bit of old school night shopping in Cathedral Street in the Loo. 

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