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For nearly 17 years, Legendary worked a conventional corporate career, but he harbored other desires. His side hustle began in what he calls the "hotwife lifestyle," a personal kink he enjoyed on weekends. "I was in the hotwife lifestyle, I would f*ck wives while the husbands would film me," he recalled. "I was comfortable with husbands filming". He soon realized that not only could he continue this hobby for free, but he could also get paid for it.