Celebrity Prison Stories

Apart from the famous "conjugal visit" trailers, prison isn't a place much associated with consensual romantic encounters between men and women. After all, incarceration is essentially a punishment, and inmates are denied as many pleasures of the outside world as possible. But Mike Tyson, the heavyweight boxing champion of the world, found a way to make jail — where he served a stint in the early '90s for a rape charge — work for him. 

Behind bars, Tyson enrolled in a drug counseling system, even though he didn't do drugs, because it would "get time taken off your sentence," he wrote in his memoir, Undisputed Truth. After a few days in the class, Tyson developed a crush on his teacher, and arranged for the woman, a single mother with a collapsed roof at home, to receive $10,000. The next day, she began allowing Tyson to, well, romance her, repeatedly, for a long stretch of time. "She'd be calling me back three times a day," Tyson wrote, adding, "I was having so much sex that I was too tired to even go to the gym and work out."

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