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Tiffany Shepherd showing off her contest ready physique at Emerald Cup 2017 (www. . craigproductions. Tiffany Lea Shepherd, 32, generated an avalanche of news coverage in spring 2008 after claiming she was released from her teaching contract in Port St. Lucie County School District for working on a boat, wearing a bikini. A teacher thrown out of her teaching job claims it is because she also works as a 'bikini hostess' on fishing trips. Is that legal? Who can forget Tiffany Shepherd, the curvaceous school teacher who donned a bikini and went to work on a charter fishing boat and later worked as a porn star. 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