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She passed away in at the age of 58 but her pictures will live on forever. Even if looking at them now may end up putting you in jail. Holly Madison was perhaps the most well known girlfriend from the E!

She began dating Hef in and was his main girlfriend for a pretty long time. Surprisingly, Madison was never actually a Playmate herself, just like the other two members of the show — Kendra Wilkinson and Bridget Marquardt.

She then turned on Hef after they broke up — especially after Hef got engaged to Crystal Harris. One of the main parts of her allure, outside of the fact that she was naturally gorgeous was that she was a Sunday School teacher.

The least popular of the Girls Next Door stars, Bridget Marquardt perhaps weathered that show better than the other two in terms of her reputation.

Marquardt mostly disappeared from the limelight. Like Madison and Wilkinson, Marquardt was never officially a Playmate herself, at least before she became one of his girlfriends for five years from to Jordan met Hef while she was attempting to obtain her license to practice real estate.

She only starring in pictorials for the magazine after they started dating. She took Playboy by storm in as the centerfold in January of that year and eventually the Playmate of the Year in It was after she had an affair that he thought about branching out sexually, and boy did he.

While they would later divorce, it perhaps should be lauded for how long it lasted: nine years together and two sons. One of those sons now runs the magazine and was responsible for temporarily removing nudity.

Brande Roderick exploded onto Playboy in , after leaping into somewhat mainstream consciousnesses thanks to her role on Baywatch. Either way she was the perfect women to transition Playboy into a new millenium.

She has parlayed her time on Girls Next Door into her own reality show that chronicles her life as the wife of — sometime — NFL wide receiver Hank Baskett.

Baskett is mostly known for fumbling the onside kick in the Super Bowl he played in and basically ruining the game. A genuine person, her tenderness shined through on Girls Next Door and endeared fans to her.

Izabella St. James was another member of this list that was neither girlfriend nor wife at any point. Despite that, though, she did achieve one major and historic Playboy feat: she was the first Bunny to write a book.

Titled Bunny Tales: Behind Closed Doors , her book was a tell-all about the lifestyle at the Mansion that are often not the most flattering.

James wrote about the two and a half years stay she stayed at the Playboy Mansion. She said that despite that time, she only hooked up with Hef once for about 15 minutes.

He asked her for a date when he was 42 and she was 18 — which is actually good for Hef, who married Crystal Harris when he was 85 and she was She was on the cover four times, from July through December but never achieved Playmate status.

She may be one of the longest serving models the magazine has ever had, though. That nearly two-decade career landed her roles in movies and even a career as a country singer.

She was in the magazine quite a bit especially at the earlier part of the decade. She tried to look like the ex-girlfriends he liked the most.

She kept emulating their looks, his favourite girlfriends from the past. One of the most shocking claims in Holly's book, were the strange sexual routines that took place at the Playboy Mansion.

She described how Hef would gather all the girls in a semi circle and put "graphic porn" on the TV. He would then smoke weed and "tend to his own business" while the girls around him would pretend to make out, before he invited specific girls to his room to have sex with him.

Holly described life in the Mansion like a prison , saying that "everyone thinks that the infamous metal gate was meant to keep people out.

But I grew to feel it was meant to lock me in. In fact, she says Holly took up the position as Hef's main girlfriend by default, because no-one else wanted to.

And if you need to know why the others didn't want that position, it all comes back down to the sexual obligations that it seems to involve.

Brace yourself. You are sharing his bed everyday. Whereas the other girlfriends return to their bedrooms, you have to have sex with him everyday, or when he wants.

It meant that it also entailed sexual activity that no one else wanted to participate in: anal sex. Hefner like to use dildos and other sex toys on Holly and have her use them on him too.

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