Sydney Man-woman (Evening Post, 11 May 1921)
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Summary: Sydney Man-woman (Evening Post, 11 May 1921)
On 3 May 1921, a bizarre case unfolded in Sydney involving a 68-year-old man, George Augustus Rocake, who had been masquerading as a woman under the alias Winifred Wileon. Rocake, who worked as a jobbing motor mechanic by day, meticulously crafted his nighttime persona, donning female attire complete with elegant accessories such as a fashionable black hat, silk stockings, earrings, and a wig. His dedicated efforts to disguise himself involved substantial time and financial investment in makeup and clothing, allowing him to convincingly blend into his new identity. Detectives became suspicious of Rocake’s evening activities, as he frequented dark and secluded areas while walking with various women. After careful observation, they arrested him for offensive behavior during one of these nighttime excursions. Upon raiding his accommodation in Rushcutters Bay, authorities discovered an extensive cache of female clothing, makeup, and accessories, indicating the extent of his masquerade. In court, Rocake maintained that his actions were merely for fun, insisting he was completely sane and that there was no malicious intent behind his behavior. When questioned by the Magistrate, who seemed perplexed by the circumstances, Rocake confirmed he had engaged in this activity every fortnight, sometimes weekly. He was subsequently fined £2 for his conduct, which drew both curiosity and amusement from the gathered crowd. This odd incident has since contributed to Sydney's reputation for eccentricities, reflecting the era's challenges surrounding identity and social norms. The case intrigued many and highlighted the lengths individuals might go to break societal conventions, even in a playful manner.
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