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1. Famous boxer Mike Tyson was in jail from 1992 to 1995 on a rape conviction, though he strongly maintained sex with the woman was consensual. But jail didn’t stop Iron Mike from getting a fix for his sexual appetite. Aside from having sex with various women who visited him in jail, he also had an affair with his drug counselor while locked up. It probably helped that he paid her $10,000 to get her roof fixed. His former manager even claimed Tyson suffered from sex addiction. While fighting, he had to have guards stand outside his hotel room to make sure no women got in… and Tyson didn’t get out. He even said he was having sex with his ex-wife Robin while the two were going through a divorce. Says Tyson: “I was getting a divorce, but…every day, before I would go to my lawyer’s office to say, ‘She’s a pig and stealing,’ I would go to her house to have sex with her.”

2. Remember O.J. Simpson? The great Buffalo Bills running back who was believed to have killed his ex-wife and her lover? Yeah, that’s him. Well, he wound up in jail for armed robbery and kidnapping… and he remains locked up. And while behind bars in Nevada, a transsexual former inmate claimed a fling with Simpson while she was HIV positive and may have infected him. The former prostitute, Jazmena Jameson said she had a sexual encounter with Simpson in 2013. She would deliver his laundered clothes to him daily and after several flirtatious encounters, Jazmena said she showed him her breasts and later gave him oral sex. Looks like O.J. is still carrying the balls past the goal line.

3. Rapper T.I., whose real name is Clifford Joseph Harris Jr. – can someone please tell me how you get the name T.I. out of the name Clifford Joseph Harris Jr.? – Anyway… T.I. was serving out a 2010 sentence in Arkansas for drug possession when his wife, Tameka, gave him a conjugal visit. Trouble is, that was a no-no. The two were caught going at it after sneaking into an empty room at the prison. After the encounter, T.I. was moved to another area of the prison, with fewer privileges. That’s what happens when you’re a bad boy. Oh, and here’s a strange fact that has nothing to do with the topic of our list. In 2006, T.I. was able to talk a Creed band member out of attempting suicide by jumping from a balcony. Four years later, he heard on the radio that a suicidal man was threatening to jump from a 22-story building and he rushed to the scene. He asked police there if he could talk to the man and they let him, convincing the man to get back into the building. How about that? Fun Fact!

4. While serving an 11-month sentence for fraud, Teresa Giudice of Real Housewives fame got a big eyeful of sexual debauchery committed by her fellow female inmates. But, she insists, she never partook in the fun. She said early on she would say her nightly prayers and soon after would see and hear all the sexual shenanigans from many others. Yet even though she did not participate – she says – she spent quite a bit of time writing down some new sexual positions she observed from her prison pals, and even created Kama Sutra-laced card to her husband, Joe. Bet old Joe was real glad to see her when she got released.

5. While spending time in a Georgia juvenile detention center after breaking one of his teacher’s arms, Atlanta rapper Young Thug claims he did nothing in jail but smoke, gamble and screw. He admitted having sex in jail during an interview with Rolling Stone magazine. He does not write down lyrics, but is known to use shapes and signs instead. He claims he can write a hit song in 10 minutes. Let’s see… Young Thug’s real name is Jeffry Lamar Williams. Hmmm… Never heard of either of ‘em. But I’m sure his songs are great!!


Hey, have you guys ever seen that Paris Hilton sex tape? Yeah, I know…. Anyway, in 2007, Paris was sentenced to 45 days in jail for probation violations regarding her fast driving issues. While on the Oprah show afterwards, she said, “I could deal with giving up coke and vodka, but going without sex made the time I spent in jail seen like an eternity. I was totally not ready for that.” And asked by an audience member if she had sex while in jail, Paris asked, “By myself…or with someone else?”