The trip was a “traumatic experience,” Madison told Insider. “Of course,” Portnoy said, and he bought her a first-class plane ticket to visit him at his $2.2 million Nantucket home. “But I will say, in order to do that one I have to be pretty comfortable with you,” Madison said. “You and I are going to get along so well,” he responded. “Like a rape fantasy, where I don’t have any control of what’s going on.” “I mean actually this ones kind of common,” she wrote. He sent her graphic videos of other women he’d slept with, according to Madison, and in messages reviewed by Insider, he pressed her to tell him about her sexual fantasies. The conversation soon moved to Snapchat and text, where it quickly turned to the topic of sex. She was a 20-year-old college student at the time, Portnoy a 43-year-old multimillionaire. In the summer of 2020, Madison sent Barstool Sports’ founder, Dave Portnoy, a direct message on Instagram complimenting his famous “one bite” pizza reviews.
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