Hugh Hefner Biography: Family Foursomes And A Gay Tryst

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First Posted: 06-22-08 08:28 AM   |   Updated: 06-30-08 05:12 AM

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Hugh Hefner

HUGH Hefner has gleefully enjoyed a sexually liberated life, but few know it all started with a little erotic dabbling within the Playboy czar's own family.

In his upcoming book, "Mr. Playboy: Hugh Hefner and the American Dream," Steven Watts writes how after Hefner wed his first wife, Millie, in 1949, he enlisted his friend Eldon Sellers, who would later help him co-found Playboy, into a staging a foursome.

The book relates: "One night after [Hugh] and Millie watched a stag film with Janie and Eldon Sellers, he suggested that the four of them make love on the same bed, each husband to his own wife. They did and in Sellers' words, 'It was different and exciting.' According to Millie, Hugh began to hint at switching partners, apparently suggesting it with the Sellerses, although the swap never materialized."

Hef then went further, trying a foursome out on his own family. "It did happen with his brother, Keith, and his wife, Rae, one evening," Watts writes. "[But] while Millie ultimately backed out of having sex with Keith, Hugh slept with his sister-in-law."

The book also claims Hef once tried a gay tryst. "Hefner's thirst for sexual experience became so strong that he even had a one-time homosexual experience," Watts writes. "One evening in downtown Chicago he was propositioned and, according to Sellers, he 'thought, what the hell. Found it an interesting experience. As far as I know, the guy just gave him [oral sex].' "

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Product Description
When Hugh Hefner quit his job at Esquire to start a magazine called Playboy, he didn't just want to make money. He wanted to make dreams come true. The first issue of Playboy had a Sherlock Holmes story by Sir Arthur Conan Doyle, an article on the Dorsey brothers, and a feature on desk design for the modern office, called "Gentlemen, Be Seated." Hefner wrote much of the copy himself and drew all the cartoons. But the most memorable part by far was the set of pictures he bought from a local calendar printer of a scantily clad Marilyn Monroe.

In this wise and penetrating biography, intellectual historian Steven Watts looks at what Hugh Hefner went onto become, and how he took America with him. Hefner became one of the most hated and envied celebrities in America, dating a long list of his magazine's beauties and always standing just barely on the wrong side of decency and moral uprightness. He also, at one time, had 7 million subscribers to his magazine. Though in time he would lose readers to more explicit magazines on one side and "lad" magazines on the other, the Playboy brand never lost its luster.

HUGH Hefner has gleefully enjoyed a sexually liberated life, but few know it all started with a little erotic dabbling within the Playboy czar's own family. In his upcoming book, "Mr. Playboy: Hugh H...
HUGH Hefner has gleefully enjoyed a sexually liberated life, but few know it all started with a little erotic dabbling within the Playboy czar's own family. In his upcoming book, "Mr. Playboy: Hugh H...
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- Azmom I'm a Fan of Azmom 11 fans permalink
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Are there people who care?

    Favorite    Flag as abusive Posted 10:13 PM on 06/22/2008
- gun I'm a Fan of gun permalink

( I dedicate this to Heidi Becker, June, 1962 -- the first exhibit in my personal pantheon of pulchritude)

For that, thanks Hef, but oh you were such a fool

To think that disproportionate breasts were some golden rule

From eccentric to plastic the myth that you minted

Into ignorant American male brains was so unfortunately cemented

(-- and only experience was a cure for those you demented)

...and now from the look of your blonde child escorts

you've grown so old, yet never learned to improved your bawdy ports.

Badder but not wiser,

Hugh:

you've become our senile old Kaiser

still shooting your gun
baiting it with mon
and never getting past
the hon

(But thanks for the memories)

    Favorite    Flag as abusive Posted 09:34 PM on 06/22/2008
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You mean "thanks for the mammarys".

    Favorite    Flag as abusive Posted 12:05 AM on 06/23/2008
- GuyFawkes I'm a Fan of GuyFawkes 28 fans permalink

That tv show is so bogus. First of all, Hef looks like a fossil. Second, of the three girls, one seems to be into him genuinely (for some odd reason), and the other 2 seem like they couldn't pick him out of a police line up. It's so fabricated, much like the reports of Hef's continuing sexual prowess.

    Favorite    Flag as abusive Posted 09:11 PM on 06/22/2008

I don't believe that girlfriend you're speaking of is really into him. She just wants to marry him so she'll be set for life. Hef is so old, homely and shriveled with a cheap, ill-fitting broadloom, that not even a woman his own age would find him attractive if he weren't rich. You're right about the other two. One really fakes liking him and the other two just seem to like to party and be in the limelight. Hef is pathetic. The thought of sleeping with that old geezer makes my skin crawl. UGH!

    Favorite    Flag as abusive Posted 11:10 PM on 06/22/2008

Well, hopefully you'll never get old yourself, then.

    Favorite    Flag as abusive Posted 07:08 AM on 06/24/2008
- Theda I'm a Fan of Theda 17 fans permalink
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I don't think that one girl (Holly?) is "genuinely into" Hefner at all. It's a fabricated TV role that she's playing. I'll bet all three girls have boyfriends their own age on the side! Hefner is just an old geezer that they get their paycheck from. It's a scripted TV show, after all, NOT real life, despite the fact that it's called a "reality show."
The show is kind of pathetic. The girls romp around Hefner's house. He's slowed down, physically and mentally. He just sits there like an old Grandpa while the girls act silly.

    Favorite    Flag as abusive Posted 10:07 AM on 06/23/2008
- JimR I'm a Fan of JimR 38 fans permalink

Um... I don't think people tune in to see him. He's barely in it, really.

    Favorite    Flag as abusive Posted 11:41 AM on 06/23/2008
- dora rice I'm a Fan of dora rice 10 fans permalink
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He won't be missed.

    Favorite    Flag as abusive Posted 07:44 PM on 06/22/2008
- dgsweet I'm a Fan of dgsweet 3 fans permalink

More accurate statement: he won't be missed by you.

The guy has a mixed record, to be sure, and he has carried immaturity to unseemly lengths, but there's a lot more to the story than just the hedonism.

    Favorite    Flag as abusive Posted 12:54 PM on 06/23/2008

I never thought I would consider Hugh benign in the pornography category. Profane, true profanity is easily seen in any of the E channel shows. The Lohans, the Kardashians and some of the other shows about rich fools spending big money on theme parties. Hugh though is surrounded by airheaded bimbos of the very high maintennace kind. I like a gal who can drive stick and back up the horse trailer.

    Favorite    Flag as abusive Posted 06:02 PM on 06/22/2008
- ROBOT8 I'm a Fan of ROBOT8 18 fans permalink
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WHO CARES??????

    Favorite    Flag as abusive Posted 05:14 PM on 06/22/2008

So, ole' Hef is GAY?

    Favorite    Flag as abusive Posted 05:03 PM on 06/22/2008
- dgsweet I'm a Fan of dgsweet 3 fans permalink

If one homosexual experience makes you gay, then my one perfect strike in a bowling alley makes me a championship bowler.

    Favorite    Flag as abusive Posted 06:00 PM on 06/22/2008
- WireDolly I'm a Fan of WireDolly 5 fans permalink

LMAO! The perfect response.

AND to all these people here commenting things like "Who cares?"--well, you obviously do, otherwise you wouldn't be here. "Gay Tryst" certainly works to grab some attention :-) and y'all fell for it, lmao!

    Favorite    Flag as abusive Posted 10:36 AM on 06/23/2008
- JimR I'm a Fan of JimR 38 fans permalink

LOL

    Favorite    Flag as abusive Posted 11:41 AM on 06/23/2008
- Eric8869 I'm a Fan of Eric8869 25 fans permalink

One gay experience doesn't make a man gay or most miltiary men would be gay. (and all prisoners)

    Favorite    Flag as abusive Posted 06:08 PM on 06/22/2008
- SwingVoter I'm a Fan of SwingVoter 19 fans permalink
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are you speaking from experience? lol j/k

    Favorite    Flag as abusive Posted 07:04 PM on 06/22/2008

the 'blue pill addict' wants to sell a book, eh

    Favorite    Flag as abusive Posted 04:45 PM on 06/22/2008
- BobSF94117 I'm a Fan of BobSF94117 10 fans permalink

It's remarkable that a man with a world-wide reputation for sexual excess would have so little to back it all up. A tribute to the power of marketing, I suppose...

    Favorite    Flag as abusive Posted 04:24 PM on 06/22/2008
- avraamjack I'm a Fan of avraamjack 21 fans permalink
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.
Were you the "once" Bob?
.

    Favorite    Flag as abusive Posted 04:50 PM on 06/22/2008
- BobSF94117 I'm a Fan of BobSF94117 10 fans permalink

Nah, I'm more into reciprocity than Heff apparently is.

    Favorite    Flag as abusive Posted 07:20 PM on 06/22/2008
- Tages72 I'm a Fan of Tages72 18 fans permalink
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Hefner became a parody of himself once he began hanging with women young enough to be his grandkids. The fact that he does so while still wearing that stupid robe doesn't help matters much.

He was a product of a time long gone. If anything, Hefner's contributions to the arts are his only worthy legacies. Jazz artists and illustrators owe him a great deal and have often expressed their gratitude. The same goes for minorities in Hollywood, in particular, black comedians. Those are the things he'll be remembered for in the long run, not this pathethic image of the crazed swinger going into senile mode. This book is just another attempt at reviving his public standing.

As it stands now, though, Hefner is to Playboy what Mickey Mouse is to Disney: Their trademark mascot.

    Favorite    Flag as abusive Posted 04:10 PM on 06/22/2008
- dgsweet I'm a Fan of dgsweet 3 fans permalink

Oh, I think there's more to the legacy than that. In the late Sixties, he shifted the magazine to politics and some of the leading writers of the time -- hoping to reach a young, male audience (especially including those serving in Vietnam) -- made it one of the most desired outlets for political opinion. And the extended Q&A interviews frequently made headlines and influenced a lot of other journalists.

Also his foundation has sent lots of money to support the legal defenses of people victimized by red-baiters, censors and puritans of all stripes. Some significant legal battles were at least partially financed by him,.

My hunch is that he has a significance and influence he himself doesn't completely understand. Some of what he has embraced is juvenile, but when you have a record as long as his it would be hard not to find a fair amount of dumb and ill-advised stuff.

    Favorite    Flag as abusive Posted 06:05 PM on 06/22/2008

Oh crap, I triggered the "BAD WORD" filter again. Forgot not to type S-E-X.

What I tried to say is:

Grandkids by now! Those women must only be interested in the money and the lifestyle. Ugh, makes my skin crawl if I let my imagination run wild.

This topic is hilarious. Its brought out everyone from the "HEF AS S-E-X GOD AND HERO" motif to the "HEF IS A DISGUSTING PIG" believers.

Too funny!

    Favorite    Flag as abusive Posted 09:31 PM on 06/22/2008

Sigh, in retyping that post, I forgot that I meant to say GREAT GRANDKIDS because you already said Grandkids. geez. That darn "BAD WORD" filter is really messing with my concentration.

    Favorite    Flag as abusive Posted 09:36 PM on 06/22/2008
- jackstpaul I'm a Fan of jackstpaul 9 fans permalink

The trademark mascot is the Bunny.

    Favorite    Flag as abusive Posted 08:51 AM on 06/23/2008
- tkondaks I'm a Fan of tkondaks 20 fans permalink

There's got to be something seriously wrong with a man who insisted upon dressing women up as bunny rabbits. Only one gay tryst? Please. That bunny costume fetish is obviously repressed homosexuality.

    Favorite    Flag as abusive Posted 03:49 PM on 06/22/2008

Really? Bunny costumes = repressed homosexuality?
Thank goodness you don't think it's repressed bestiality ...
I always thought it represented kind of a whimsical sense of humor for the 1950s ;-)

However silly he might seem today, I suspect that in the end we'll realize he did more good than harm.

    Favorite    Flag as abusive Posted 08:33 PM on 06/22/2008
- mikekev58 I'm a Fan of mikekev58 8 fans permalink

Yeah, it was a different time. Cripes, Gloria Steinem was a playboy bunny.

It was all in good fun. Appearances to the contrary, Hef supported women's rights. And unless you believe that the many women he's bedded and the many women who have graced Playboy are self-loathing nitwits (can you be self-loathing AND a nitwit?), I think that the magazine and the proposed lifestyle was a healthy alternative to the uptight (and hypocritical) America then and now.

IMHO.

    Favorite    Flag as abusive Posted 09:41 PM on 06/22/2008
- tkondaks I'm a Fan of tkondaks 20 fans permalink

He was just a high-class pimp, that's all.

    Favorite    Flag as abusive Posted 04:00 AM on 06/23/2008

LOL, I forgot about the Bunny Costumes!! I was too focused on the NAKED WOMEN! Repressed lesbianism? Hmmm...

    Favorite    Flag as abusive Posted 09:21 PM on 06/22/2008
- JimR I'm a Fan of JimR 38 fans permalink

What are you saying? That Bugs Bunny cartoons were gay propaganda?

I guess when he said "What's UP, Doc?" we now know what he was talking about!

    Favorite    Flag as abusive Posted 11:43 AM on 06/23/2008

Bugs was kinda bi.

    Favorite    Flag as abusive Posted 03:26 PM on 06/23/2008
- SPQR1052 I'm a Fan of SPQR1052 17 fans permalink
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And it surprises one how - Hef ridin' dirty? Please!! Half the US Navy has done more in TJ on leave than this man's "once."

    Favorite    Flag as abusive Posted 02:11 PM on 06/22/2008

Really? Why don't you tell us about it?

    Favorite    Flag as abusive Posted 02:19 PM on 06/22/2008
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Obviously you don't know anyone who's ever been in the Navy, otherwise you wouldn't have to ask.

    Favorite    Flag as abusive Posted 02:23 PM on 06/22/2008
- Quaoar I'm a Fan of Quaoar 28 fans permalink
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Don't ask, Don't Tell.

    Favorite    Flag as abusive Posted 08:20 PM on 06/22/2008
- mikekev58 I'm a Fan of mikekev58 8 fans permalink

This is my third effort at stating something pretty innocuous, because HuffPo has a bad word thingy.

Anyway, tons of American boys have lent each other a hand from time to time during adolescence, what's the big deal?

    Favorite    Flag as abusive Posted 09:55 PM on 06/22/2008

MODS, please change the "Bad Word" filter!! Even on a story about Hefner, I can's use the word "S*X", as in "women as s*x objects". I forgot that happened yesterday in the Lance Armstrong story wondering if his condition had affected his s*x life, and so I just wrote a couple of paragraphs on this story, tried to post, and got deleted.

    Favorite    Flag as abusive Posted 02:07 PM on 06/22/2008
- SifSkade I'm a Fan of SifSkade 6 fans permalink

Seriously! The filter is lame and childish enough in and of itself, and the fact that it's seriously overbroad is not helping things. S-E-X is not a "bad word" and it has an equally valid non-provocative meaning anyway (synonym for gender, hello?). So stupid.

    Favorite    Flag as abusive Posted 04:46 PM on 06/22/2008

We need a list of the "BAD WORDS" so we stop wasting our time posting here at HuffPost. Its not like we're children trying to shock by writing dirty words. Gimme a break!!

    Favorite    Flag as abusive Posted 09:19 PM on 06/22/2008
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