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12 Famous Hugh Hefner Hookups Ever

Sunday, Aug 23, 2020, 11:24 am

Hugh Hefner may be a 90-year-old man, but he's more sexually active than many of you younger guys who are reading this topic. At an age where an average old man struggles to stand up and walk, Hefner not only stands up but also makes things stand up and work for his pleasure! The original "Playboy" reportedly had sex with more than a thousand gorgeous women. Although his former girlfriends complain about his inability to have coitus and call him a "serial wanker," we all still need to agree to the fact that he gets more women than any other top Hollywood celebrity ever has. We take this opportunity to present you with the details of 12 famous Hugh Hefner hookups. He's like a great-great-grandfather to some of the girls when in regards to age! Some of the hottest pornstars were once his playmate.
1.Hugh Hefner, Kristina And Karissa Shannon Twins

High Hefner found himself another set of twins, when he met Kristina and Karissa Shannon. The identical twins were glued to Hefner's side like white on rice for a little while. They reportedly became his girlfriends around 2008. The awkward relationship didn't last and the twins moved out and moved on. In 2012, Shannon began dating Playmate Ida Ljungqvist.

Hugh Hefner, Kristina And Karissa Shannon Twins-12 Famous Hugh Hefner Hookups Ever

2.Hugh Hefner, Sandy And Mandy Bentley Twins

Sandy and Mandy Bentley are twins. Although their last name sounds like they are heiresses of a billion dollar fortune, the Twins are nothing more than Hugh Hefner play dolls. The two were featured on May 2000 cover of Playboy magazine, which helped them gain some attention. The opportunity hadn't come quickly to them, as the duo had to spend one year with Hugh Hefner in his mansion as his in-house playmates! Although the two tried their luck in the entertainment industry scouting for some roles on TV, it never worked out their way. We don't think even Hugh remembers them, let alone the Playboy subscribers.

Hugh Hefner, Sandy And Mandy Bentley Twins-12 Famous Hugh Hefner Hookups Ever

3.Hugh Hefner And Barbi Benton

Barbi Benton was one of Hugh Hefner's favorite Playmate. Lately, many people criticize Hugh Hefner, calling him a slimy old lizard for dating women who are younger enough to be his great-granddaughters. Hefner's date choices have been controversial from a very long time, even during the time when he was young. Hugh Hefner dated Barbi Benton between the years 1969 and 1976. Barbi Benton was barely legal at that time. Born Barbara Klein, actress and the former Hugh Hefner's girlfriend, Barbi, was even featured on the Playboy magazine cover four times.

Hugh Hefner And Barbi Benton-12 Famous Hugh Hefner Hookups Ever

4.Hugh Hefner And Tina Marie Jordan

Nearly a decade before, Tina Marie Jordan was an ordinary person like most of us. She wanted to become a millionaire, but she had no idea what she needs to do to become one!  She changed her career paths as frequently as we change our underwears! Tina worked at a business college, cosmetology school, and even as a loan processor. She met Hugh Hefner while she was trying to obtain a real estate license. For Tina, Hugh Hefner was a filthy rich old man who could help her to get the grant. For him, she was yet another pretty young woman with big boobs! He quickly showed her a new road to becoming wealthy.  Tina Marie Jordan became a Playmate and was featured on the Playboy magazine's centerfold in 2002. A decade later, Tina Marie Jordan is neither a successful model nor a real estate agent!

Hugh Hefner And Tina Marie Jordan-12 Famous Hugh Hefner Hookups Ever

5.Hugh Hefner And Izabella St. James

Izabella St. James had a very productive life ahead of her, and then she met Hugh Hefner and it went down the toilet. The pair met in September 2000. Two years later, she finished law school and St. James became one of Hefner's girlfriends and began traveling with him on a regular basis. She eventually got bored with Hefner and ended the relationship in May 2004.

Hugh Hefner And Izabella St. James-12 Famous Hugh Hefner Hookups Ever

6.Hugh Hefner And Brande Roderick

Brande Roderick is a model, but she is best known for her work on the TV show, Baywatch. She too is one of the few women who spent some quality time with Hefner. Unlike the other Playboy Bunnies whom he would just use and throw, Brande Roderick managed to move up the rank quickly to become one of his favorite Playmates. She was Playmate of the Month in 2000 and went on to be the Playmate of the Year in 2001. Roderick has never confirmed being Hefner's leading lady, but the pair made many red carpet appearances together on multiple occasions.  

Hugh Hefner And Brande Roderick-12 Famous Hugh Hefner Hookups Ever

7.Hugh Hefner And Kimberly Conrad

Kimberly Conrad stole Hugh Hefner's heart and then broke it into a million tiny pieces. The twosome married in 1989 and would go on to have two children together. They separated after nine years of marriage, but remained married for the sake of their children. Hefner later on revealed that Conrad was not faithful and that is what led to their breakup. Conrad and Hefner finalized their divorce in 2010.

Hugh Hefner And Kimberly Conrad-12 Famous Hugh Hefner Hookups Ever


8.Hugh Hefner And Millie Williams

Mildred Williams a.k.a. Millie Williams is Hugh Hefner's first wife. He married her in 1949. Remember, Hefner served the country during the World War II. While he was out serving the nation, his former wife Millie cheated on him. When Hefner was back, she told him that she told him about her de . He was devastated by her confession. To ease her guilty conscious, she allowed her husband to sleep with other women! This odd and ridiculous arrangement didn't work out, and the couple divorced in 1959. Don't you think it was this incident that turned the Playboy founder into a Pussy slayer?!

Hugh Hefner And Millie Williams-12 Famous Hugh Hefner Hookups Ever

9.Hugh Hefner And Bridget Marquardt

Bridget Marquardt shared Hugh Hefner with fellow Playboy mansion dwellers Holly Madison and Kendra Wilkinson. Bridget Marquardt was not (and still isn't) the sharpest knife in the drawer. She began chasing her 'dream' of becoming a Playboy model at the age of 25. After several failed attempts, she kept trying and lowered herself to become one of Hefner's arm candy girls. Did you know Hugh Hefner once kicked out Jason Statham out of his mansion?

Hugh Hefner And Bridget Marquardt-12 Famous Hugh Hefner Hookups Ever


10.Hugh Hefner And Holly Madison

Former Hooter's employee Holly Madison is probably one of the only women in this world who loved Hugh Hefner for him and not his money. She was one of Hefner's three girlfriends during the E! show, "The Girls Next Door." Madison was adamant about marrying Hef, but at the time he said he wasn't interested in marriage. Madison finally came to her senses and broke off the relationship in 2008.

Hugh Hefner And Holly Madison-12 Famous Hugh Hefner Hookups Ever

11.Hugh Hefner And Kendra Wilkinson

Former stripper Kendra Wilkinson was one of the many Ladies that happily shared Hugh Hefner's affection. The pair met at Hefner's 78th birthday party in 2004. He was so smitten with Wilkinson that he asked her to be his girlfriend and moved her into the Playboy mansion. She was later featured on the E! show, "The Girls Next Door." Wilkinson is now happily married to Hank Baskett and pregnant with her second child.

Hugh Hefner And Kendra Wilkinson-12 Famous Hugh Hefner Hookups Ever


12.Hugh Hefner And Crystal Harris

After years of proclaimed bachelorhood, Hugh Hefner took Crystal Harris to be his wife. The two were supposed to get hitched in June 2011, but Harris called off the wedding. She then went on to slam Hefner's lovemaking skills and looks to shock-jock Howard Stern. The smell of Hefner's money led Harris back to Hefner and they wed on December 31, 2012.

Hugh Hefner And Crystal Harris-12 Famous Hugh Hefner Hookups Ever


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