Author Topic: Hugh Hefner Reveals The Insane Number Of Women He's Slept With  (Read 15048 times)

BIG DUB

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Hugh Hefner, 86, is currently on his third wife, but that's nothing compared to the amount of women the Playboy founder has slept with throughout his lifetime.

“Over a thousand, I’m sure," Hefner revealed to Esquire of the number of women he's had sexual relations with. But it's not an exact number, as he says,  "How could I possibly know?"

But Hefner's sexual escapades have nothing to do with him being unfaithful to his wives.

“There were chunks of my life when I was married, and when I was married I never cheated,” explains the publishing icon. “But I made up for it when I wasn’t married. You have to keep your hand in.”

Hefner was  first married in 1949 to Northwestern University student Mildred Williams , with whom he has two children, before divorcing in 1959.

40 years later, Hefner said "I do" again to Playmate of the Year Kimberley Conrad,  whom he  separated from in 1998 and finally divorced in 2010 .

During the separation, Hefner dated up to seven women at once (with the help of Viagra) and featured his relationship with  Playboy Playmates Holly Madison, Bridget Marquardt and Kendra Wilkinson on the popular E!  reality series "The Girls Next Door."

On New Year's Eve, Hefner married Crystal Harris, 60 years his junior, a year after the couple reconciled after she called off the wedding days before the initial ceremony was set to take place.

“He believes in love,” 26-year-old Harris told Esquire. “Hef loves me more than anybody else in a relationship ever has. It took me time away to realize that. I think I realized that here is where I’m meant to be.”

Adds Hefner, " All our friends think it’s made in heaven. It’s only people who don’t know us, who simply see us as stereotypes in terms of age and beauty… I just feel very, very fortunate to have found her at this stage in my life. I saved the best till last.”

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #1 on: March 26, 2013, 07:48:10 PM »
He probably blew twice as many dudes

Mr Nobody

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #2 on: March 26, 2013, 07:53:34 PM »
He hasn't revealed how many thousands of dollars he has spent on them just to have sex.

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #3 on: March 26, 2013, 07:56:10 PM »
He hasn't revealed how many thousands of dollars he has spent on them just to have sex.


Exactly!  he wants to be seen as a pussy magnet when is the $  sign that brings them to the yard.



WOOOSSSHHHHHHHHHHHHHHHHH HHH

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #4 on: March 26, 2013, 08:02:32 PM »
How many I'll be 18 yrs old  in yada yada days and i would do anythig to be in your magazine did he bang?

BIG DUB

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #5 on: March 26, 2013, 08:16:15 PM »
He hasn't revealed how many thousands of dollars he has spent on them just to have sex.

all paid for by the millions of horny bastards who bought his magazine! 8)

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #6 on: March 26, 2013, 08:45:25 PM »
He probably blew twice as many dudes
you dont think he is a top? ???
A

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #7 on: March 26, 2013, 08:51:14 PM »
How many I'll be 18 yrs old  in yada yada days and i would do anythig to be in your magazine did he bang?

not only that, but they were eager to impress him, so they gave it their all. 

the average girl knows she doesn't have to try that hard to get laid.  The girl with one shot at Heff is going to be sucking garden balls thru a hose while begging for anal in order to make the right impression on him. 

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #8 on: March 26, 2013, 08:53:48 PM »
you dont think he is a top? ???

There was an artical a while back I think rolling stone magazine, and they asked Hugh about his famous orgy room/parties, he said he would have them all the time an the room would be packed with so many guys and girls it was hard to keep a head count

They asked if he ever fucked any of the guys during the orgy and he said that he would penetrate holes and didnt know if they were male or female holes and sometimes he felt his own anus being penetrated but didn't know if it was a girls finger or a guys dick

They asked him if he ever looked back to check he said no

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #9 on: March 26, 2013, 08:56:05 PM »
Don't hate on the man. You know we all wish we were hitting that kind of ass regularly.

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #10 on: March 26, 2013, 08:57:38 PM »
Man I bet the Mr Herbert character was drawn after him just like quagmire is drawn after a young Bob Hope

"

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #11 on: March 26, 2013, 09:19:05 PM »
There was an artical a while back I think rolling stone magazine, and they asked Hugh about his famous orgy room/parties, he said he would have them all the time an the room would be packed with so many guys and girls it was hard to keep a head count

They asked if he ever fucked any of the guys during the orgy and he said that he would penetrate holes and didnt know if they were male or female holes and sometimes he felt his own anus being penetrated but didn't know if it was a girls finger or a guys dick

They asked him if he ever looked back to check he said no
:-\
A

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #12 on: March 26, 2013, 09:20:44 PM »
There was an artical a while back I think rolling stone magazine, and they asked Hugh about his famous orgy room/parties, he said he would have them all the time an the room would be packed with so many guys and girls it was hard to keep a head count

They asked if he ever fucked any of the guys during the orgy and he said that he would penetrate holes and didnt know if they were male or female holes and sometimes he felt his own anus being penetrated but didn't know if it was a girls finger or a guys dick

They asked him if he ever looked back to check he said no

sheesh.... my brain can't even fathom such a room...

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #13 on: March 26, 2013, 09:21:56 PM »


Inside the Playboy Mansion: Dog Piss, Boring Sex

Posted on December 31, 2010

You'd be hard pressed to find a man who more dudes wouldn't mind being than 84-year-old Playboy mastermind Hugh Hefner. After all, Hefner, who got engaged to Miss December 2009, 24-year Crystal Harris on Christmas Eve, is rich, famous and has a never-ending stream of young beautiful women at his disposal. Perhaps most envied of all, is Hefner's abode, the iconic Playboy mansion, home to infamous bacchanalian orgies, exclusive celebrity parties and the women who comprise Hefner's harem. And in recent years, with the success of the TV show The Girls Next Door, which documented the lives of three of Hefner's women, the female residents of the Playboy mansion have become as widely envied as Hefner himself. After all, they get to live in one of the world's most famous residences, have access to seemingly limitless plastic surgery, get waited on hand and foot and their only real job is to be a companion to Hefner. But a new book by one such mansion resident, former playmaye Izabella St. James paints a somewhat different picture of life at the Playboy mansion, and as Hefner's "companion" as the one portayed on TV.










James (pictured with Hefner above) says that despite it's seeming opulence, the mansion itself is something of a moldering relic:

    'Although we all did our best to decorate our rooms and make them homely, the mattresses on our beds were disgusting — old, worn and stained. The sheets were past their best, too.Eventually I persuaded Hef to pay for a new mattress and bed linen — but I had to turn in every single receipt before I was reimbursed. Hef also eventually permitted us to have the rooms painted and recarpeted. But for some reason he insisted on creamy, white-coloured carpets. He liked the girlfriends’ rooms to look very girly, all white carpet and pink walls. It looked great at first, but with two dogs (most of the girlfriends had pets that lived in their rooms — I had two pugs), butlers delivering food, dirty shoes and occasional spillages, the carpet was grey and stained in a matter of months.’
    She adds: ‘But then Hef was used to dirty carpets. The one in his bedroom had not been changed for years, and things became significantly worse when Holly Madison moved into his room with him as Girlfriend No. 1 soon after I moved in, bringing her two dogs. They weren’t house-trained and would just do their business on the bedroom carpet. Late at night, or in the early hours of the morning — if any of us visited Hef’s bedroom — we’d almost always end up standing in dog mess. Everything in the Mansion felt old and stale, and Archie the house dog would regularly relieve himself on the hallway curtains, adding a powerful whiff of urine to the general scent of decay.’

And Hefner himself was equally something of a crumbling, crusty facade of carefree extravagance:

    ‘Every Friday morning we had to go to Hef’s room, wait while he picked up all the dog poo off the carpet — and then ask for our allowance: a thousand dollars counted out in crisp hundred-dollar bills from a safe in one of his bookcases,’ she says.

    ‘We all hated this process. Hef would always use the occasion to bring up anything he wasn’t happy about in the relationship. Most of the complaints were about the lack of harmony among the girlfriends — or your lack of sexual participation in the “parties” he held in his bedroom. If we’d been out of town for any reason and missed one of the official “going out” nights [When Hefner liked to parade his girls at nightclubs] he wouldn’t want to give us the allowance. He used it as a weapon.’

    The allowance was also withdrawn if there was any infringement of the strict rules imposed by Hefner on all his girlfriends.‘Little did I realise that by moving into the mansion I was losing all the freedom I associated with the Playboy lifestyle,’ says St James. ‘Strictest of all was the curfew. Everyone had to be on the Mansion grounds by 9pm every night — unless we were out with Hef at a club or a function. People honestly did not believe us when we told them we had a curfew at the wild and crazy Playboy Mansion.’

According to James, and other former residents, these "sex parties" in Hefner's room weren't really parties so much as they were drug fueled indulgences of Hefner's waning sexual desire, with the girls provided quaaludes and Hefner taking heavy doses of Viagra.

    ‘Quaaludes were supposed to give you a nice buzz,’ says Izabella St James. ‘Hef told me once that they were meant to put girls in the mood for sex.’

    The thrill of being out after curfew was tempered by Hefner’s wearying habit of going out to the same few clubs, night after night. And his ever-present security guards ensured that no other men were allowed to pay the girls any attention.

    At around midnight, according to St James, Hef would take his Viagra. ‘After that, he would constantly check his watch to make sure we left at the right time because if we didn’t, or the timing got messed up, he wouldn’t be able to perform later. As with so much else in their time with Hefner, the girls followed strict rules before entering his bedroom for the sex parties.One of those who witnessed these preparations was Jill Ann Spaulding, an aspiring model who wrote to Hefner in 2002 asking to be a Playboy centrefold.

    Though 20-year-old Spaulding had enclosed a naked photo of herself, she claims to have been unprepared for what happened when she was invited to stay at the Playboy Mansion for a few days, and was asked to one of these private parties.

    Beforehand, all the girls were told to take a bath. ‘I got in, then another girl appeared from nowhere and jumped in with me,’ recalls Spaulding. ‘Then Hef stepped around the corner and took a photo of us naked in the bath together before disappearing. It was all very strange.

    ‘Another girl led me into Hef’s master bedroom. The only light was coming from two TVs on which adult films were showing. All the other girls were there, dressed like me in pink pyjamas. If you kept your pyjama bottoms on, that was a sign that you didn’t want to have contact that night.’ According to Spaulding there were 12 girls there on that first night, and only she and another girl declined the offer to have sex with Hefner, who did not use a condom. ‘There was no protection and no testing for sexually transmitted diseases,’ she says.

    Izabella St James, it seems, was much more open about having a physical relationship with him.

    ‘I wanted to see if this experienced King of Sexdom knew anything the rest of us did not,’ she recalls. ‘But he just lay there like a dead fish.

I guess it just goes to show that you can buy a lot of things, including fame, women and admiration, but at the end of the day, you're still gonna end up an old man who can't get it up. Bummer.


booty

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #14 on: March 26, 2013, 10:16:24 PM »
Gross!  Just all of it  :-X

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #15 on: March 26, 2013, 11:41:30 PM »
Gross!  Just all of it  :-X

 ::)

if he paid your rent, you'd blow the old, dry skin off his dick.  just like a woman pretending.

WillGrant

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #16 on: March 27, 2013, 03:46:06 AM »
Man I bet the Mr Herbert character was drawn after him just like quagmire is drawn after a young Bob Hope


;D

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #17 on: March 27, 2013, 03:47:29 AM »
There was an artical a while back I think rolling stone magazine, and they asked Hugh about his famous orgy room/parties, he said he would have them all the time an the room would be packed with so many guys and girls it was hard to keep a head count

They asked if he ever fucked any of the guys during the orgy and he said that he would penetrate holes and didnt know if they were male or female holes and sometimes he felt his own anus being penetrated but didn't know if it was a girls finger or a guys dick

They asked him if he ever looked back to check he said no

Hahaha oh brother

booty

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #18 on: March 27, 2013, 04:02:47 AM »
::)

if he paid your rent, you'd blow the old, dry skin off his dick.  just like a woman pretending.
No would rather struggle financially than have to do that and have someone own me. If I am with a man it's because I want 'real happiness' not just acquire materialistic items which give you 5 mins of happiness.

TrueGrit

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #19 on: March 27, 2013, 04:02:56 AM »
There was an artical a while back I think rolling stone magazine, and they asked Hugh about his famous orgy room/parties, he said he would have them all the time an the room would be packed with so many guys and girls it was hard to keep a head count

They asked if he ever fucked any of the guys during the orgy and he said that he would penetrate holes and didnt know if they were male or female holes and sometimes he felt his own anus being penetrated but didn't know if it was a girls finger or a guys dick

They asked him if he ever looked back to check he said no

Maybe Tbombz has moved in to the playboy mansion and Heff has him on a getbig  curfew..
O

Tito24

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #20 on: March 27, 2013, 04:54:49 AM »
There was an artical a while back I think rolling stone magazine, and they asked Hugh about his famous orgy room/parties, he said he would have them all the time an the room would be packed with so many guys and girls it was hard to keep a head count

They asked if he ever fucked any of the guys during the orgy and he said that he would penetrate holes and didnt know if they were male or female holes and sometimes he felt his own anus being penetrated but didn't know if it was a girls finger or a guys dick

They asked him if he ever looked back to check he said no

hahahaha

The_Punisher

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #21 on: March 27, 2013, 06:18:07 AM »
There was an artical a while back I think rolling stone magazine, and they asked Hugh about his famous orgy room/parties, he said he would have them all the time an the room would be packed with so many guys and girls it was hard to keep a head count

They asked if he ever fucked any of the guys during the orgy and he said that he would penetrate holes and didnt know if they were male or female holes and sometimes he felt his own anus being penetrated but didn't know if it was a girls finger or a guys dick

They asked him if he ever looked back to check he said no


LOL......oh shit, that's funny......his son can't carry the same Protocol

TrueGrit

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #22 on: March 27, 2013, 06:34:16 AM »
 Well what can you do? It's a dark room and something goes up your ass. Woman's finger or a guy's cock, how can you be expected to tell? Heterosexuality remains intact and it feels great - like a deep tissue massage, except it's in your ass!
O

Benny B

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #23 on: March 27, 2013, 06:59:07 AM »
No would rather struggle financially than have to do that and have someone own me. If I am with a man it's because I want 'real happiness' not just acquire materialistic items which give you 5 mins of happiness.
Webcam-bitch/ho, stop frontin'.  ::)
!

pedro01

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Re: Hugh Hefner Reveals The Insane Number Of Women He's Slept With
« Reply #24 on: March 27, 2013, 07:36:26 AM »

Exactly!  he wants to be seen as a pussy magnet when is the $  sign that brings them to the yard.



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