playboy - Page 5

Hef’s Ex Karissa Shannon Is Pervin’ On 12-Year-Old Jaden Smith

Playboy Playmate (and Hef’s ex) Karissa Shannon makes no bones about being a cougar-in-training as she broadcasts her affections for 12-year-old Jaden Smith. Sexualizing children doesn’t suddenly become acceptable if it’s a boy being sexualized instead of a girl, Karissa! [Sociological Images] … More »


Playboy Launches New Safe-For-Work Website Without Naked Women

Playboy Enterprises Inc. has been struggling in recent years, now that porn is everywhere you click. Sure, plenty of dudes (six million, to be exact) still visit Playboy.com every month, but they’re less likely to do so when they’re at work, what with all the naked ladies and whatnot. So, the always-thoughtful Playboy guys created… More »


Quotable: Hugh Hefner Would Date His 70-Year-Old Secretary

“Well, if there was, it’s the one that’s sitting right across from me, Mary O’Connor. She’s my secretary, and she’s the wonder of my life.”
Hugh Hefner explaining that there is one woman over the age of 70 that he’d consider dating. Mary, I think it’s time to make your move. Though I secretly hope… More »


“Mad Men”‘s Crista Flanagan Gets Naked For Playboy

But what will the boys at Sterling Cooper think? “Mad Men“‘s Crista Flanagan, who plays switchboard operator Lois Sadler on the show, poses topless on the cover of the August issue of Playboy magazine. I guess she didn’t take it all off inside, though? “If I tell a friend I did this, they think I’m… More »


Quotable: Hugh Hefner Isn’t The Marrying Kind

Hugh Hefner: I think there is no single answer, no single road to Mecca. I have been married twice, and those were not the happiest times of my life. Part of the problem, quite frankly, is that when you get married, the romance disappears and the children arrive and the love is transferred. It shouldn’t… More »


Portuguese Playboy Is Getting Crucified

The Portuguese publishing partners of Playboy are getting crucified for their July issue. Their in-poor-taste cover features a racy pic of Christ cradling a nakey Mary Magdalene type. Inside the issue, there is allegedly a photo spread featuring the lord and savior observing a lesbian kiss.

Playboy Enterprises Inc. is less than thrilled… More »


Jake And Vienna Race To Get Naked In “Playgirl” And “Playboy,” Respectively

Jake Pavelka and Vienna Girardi will stop at nothing to boost ratings for the upcoming “The Bachelor Breakup” special extend their 15 minutes of fame. These two are no longer flying high on the wings of love. In fact, they are looking to make an emergency landing into the pages of Playboy and Playgirl, respectively. More »


Alexandra Richards Models Nude In French Playboy

When your dad is the Rolling StonesKeith Richards and your mom is model/photographer Patti Hansen, posing nude in French Playboy is an interesting career choice. But whatevs, maybe Alexandra Richards really likes her nakey time.

After the jump, more of Alexandra’s NSFW French Playboy pics: … More »


Justin Bieber’s Mom Offered A Playboy Spread

Justin Bieber’s parents had him young—when his mom, Pattie Mallette, was 18 and his dad, Jeremy Bieber, was 21. Justin was raised by Pattie—she’s the one who posted the video that launched his career on YouTube. Now, Playboy is giving Pattie her own shot at fame. They are reportedly offering her $50,000 to appear topless… More »


Would You Rather: Appear Nude On A Vogue Cover, Or Fully-Clothed In A Playboy Spread?

Welcome to Would You Rather, a game in which we concoct hypothetical style dilemmas and ask you to choose which option’s worse.

Today’s challenge: Would you rather appear completely naked (we’re talking full-frontal, vag-in-view nudity) on the cover of Vogue, or appear fully-clothed in a Playboy spread? Strip for a classy mag, and most… More »


Do Boobs Have Their Own “Eras”? Let’s Ask Playboy!

Bored at work? A little horny? Head right on over to Playboy’s website for a gratuitous boob photo spread on the “Evolution of the Boob”! Playboy dipped into their old photos to show us breasts from the past six decades because, apparently, “boob shape” is as cyclical as fashion. Now, I looked at those mammaries… More »


“I Love Plastic Surgery”: New Video Of Debrahlee Lorenzana, Citibank’s Sexual Harassment Accuser

Remember Debrahlee Lorenzana, who recently filed a sexual harassment lawsuit against Citibank? A promotional video for Long Island Plastic Surgical Group featuring Lorenzana has now surfaced, in which she gets her second boob job and says she wants to be — and I quote — “tits on a stick.” … More »


Kendra Wilkinson’s Sex Tape #2: This Time With A Woman

Kendra Wilkinson’s “home videos” keep on leaking out, don’t they? Gossip blog RadarOnline.com has revealed the “Girl Next Door” has starred in a second sex tape — this time with some woman named Taryn. Damn, does this chick have a new season of her reality show (“Kendra”) coming out, or what? This is her second… More »


Holly Madison Debuts A Jewelry Line … Candy Jewelry, That Is

Aww, that’s sweet: Playboy babe Holly Madison is debuting a line of edible candy necklaces for the Las Vegas candy store, The Sugar Factory. Random, no? It only kinda-sorta makes sense when you consider she lives out in Vegas, performing in the striptease “Peepshow” and filming her soon-to-be-aired reality show, “Holly’s World.” An edible candy… More »


Rachel Uchitel In Playboy?

Supposedly, Rachel Uchitel has always dreamed of posing for Playboy. Now that she’s been involved in sex scandals with two separate celebrities, Tiger Woods and David Boreanaz, it appears that she is getting her wish. According to reports, she has a Playboy photo shoot scheduled in three weeks. She won’t be baring all, but will… More »


Hugh Hefner: The New Poster Boy For Monogamy?

I never thought the day would come when Hugh Hefner would become the face of fidelity and sexual morality; but, alas, pigs have flown. At 84 years old, Hef has finally decided to settle down with one woman. Yes, folks, he’s given up his harem of bimbettes for girlfriend Crystal Harris. Sure, she’s bleached-blond and… More »


The First Look At Ashley Dupre In Playboy

So her hair might have caught on fire Michael Jackson-style, when it came in contact with a candle on set—but Ashley Dupre hardly looks singed on the cover of May’s Playboy. (Which will, uh, not feature Kate Gosselin.) “I had a lot of fun doing these pictures,” said Ashley. “You’re naked and you’re in front… More »


8 Ladies Who Were Rejected By Playboy