2. Hank Baskett – The Transgender Mistress
When Hank Baskett married Playboy model, Kendra Wilkinson, the world thought it would be her sexual past that would be the catalyst to ending their marriage. From being just one of the ex-girlfriends of the elderly Hugh Hefner to having two separate sex tapes leaked, Kendra didn’t exactly make it easy for Hank during the early stages of their marriage. Just when the public thought it couldn’t get any more dysfunctional, a transgender model named Ava Masaniai (born Paul) came forward revealing intimate details about an affair with Hank. Whether or not you believe the fondling stories or the supposed drug purchase excuse given by Hank (which was his response as to why he paid Ava thousands of dollars on two separate occasions), the result is a tarnished reputation that might not ever be fixed. While Kendra used to be the black sheep in this relationship, Hank’s bizarre sexual encounter with Ava has quickly changed public perception so that she is now the victim we all feel sorry for.
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