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The Year’s 100 Biggest Moments in Sex—Part Three

The Year’s 100 Biggest Moments in Sex—Part Three: Miss May 2016 Brook Power, shot by Aaron Feaver

Miss May 2016 Brook Power, shot by Aaron Feaver

2016 has been called a lot of things: A dumpster fire, a soul-sucking abomination, a relentless killer of heroes and the result of an ancient curse. 2016 has also been a monumental year for sex—in both great and no-so-great ways. We’ve seen our attitudes shift, adopted new technologies, installed new apps and discovered new kinks. From Amber Rose’s promotion of ass play to Anthony Weiner’s addiction to sexting, there were also a lot of WTF moments. But for all of the low points, the year boasted an equal bonanza of sexual highlights, including huge leaps toward a cure for HIV/AIDS and more public celebrations of body positivity than ever before.

We’re counting down the greatest moments in sex in 2016, in one definitive, authoritative, all-encompassing list.

So far, we’ve brought you part one of the 100 Biggest Moments in Sex and part two of the 100 Biggest Moments in Sex

This week, Playboy continues our countdown with numbers 49-26.


49. Niykee Heaton Seduced Us With Her Centerfold Tour

u my nbk groupie or nah?

A photo posted by Niykee Heaton (@niykeeheaton) on

This year, social media star Heaton travled across America, spreading the sexy with her Centerfold tour. But she’s no empty-headed pop star relying on her body to sell tix. Niykee’s legit talented. Lucky for us all, she also likes to share glimpses of her life on the road, like, when she’s just chilling and eating a burger and fries in bed…naked.

48. Science Asked “Why Do Women Have Orgasms?”…Again

In August, researchers from Yale announced that they may have answered the question “Why do women have orgasms?” It’s the year’s best feel-good story of evolution. The study, published in the journal Experimental Zoology/Molecular and Developmental Evolution, claims that our female ancestors chose the moon over men and were rewarded with orgasms. Like with most mammals, it used to be that an orgasm triggered a woman’s ovulation. Good sex shook the eggs loose. But thanks to evolution, women began to ovulate monthly. They relied on the moon rather than men to time their egg-dropping schedule. This freed up women’s orgasms for pleasure. Subsequently, the clitoris became more of a joy button rather than a trigger for babymaking. Well, that’s the theory.

47. Amber Rose Got Into a Twitter Feud Over Kanye West’s Twitter Booty

To help kickstart the crazy of 2016, in January, Amber Rose and Kanye West got into some Twitter beef over whether she did or did not stick fingers in his booty. They used to date. In fact, his album My Beautiful Dark Twisted Fantasy is about his time with Rose. So people paid attention when the exes started beefing. It was very, he said, she said with no comment from Kanye’s butt. The beef started with Wiz Khalifa. Kanye was firing on Wiz and Ye dragged their mutual ex Rose into their fight. Bad move, Yeezy. Of course, Rose clapped back.

To wit, Kanye defended his booty’s virginity…

As with much of what West says on Twitter, we have no idea what that last tweet means.

46. Madonna Offered Blowjobs To Hillary Voters

In the past, politicians tried to buy votes by offering “a chicken in every pot.” (It worked for Herbert Hoover.) But that hokey shit doesn’t play in 2016. Instead, we had Madonna pledging to give oral sex to anyone who voted for Hillary Clinton. Madge later rescinded the offer.

45. Free Condoms Overran the Rio Olympics

More than 11,000 athletes competed at the 2016 Rio Olympics. Since a lot of them were fit, tight, sexy specimens of the human species, one can only imagine how much hooking up happened. With so much humping in the Olympic Village, organizers thought it wise to hand out free condoms to the athletes: 484,848 of them. That’s 42 condoms per athlete.

44. Pokémon Got NSFW

At the beginning of the summer, the world became a much cooler place, after the Pokémon Go app launched. The augmented reality game was a ton of fun for users. So much so that things got pretty ridic quick. There was a Marine who crashed into the sea chasing Pokémon and the story of two dudes who fell off a cliff in California.

But then things got sexy with the Pokémon Go nude selfie game. An entire NSFW thread on Reddit is stacked with examples. Here’s Exhibit A:

43. The Kinsey Institute Reported That Women Are More Likely To Reach Orgasm If They Have Anal Sex

In a study from the Kinsey Institute, 94 percent of women reported they had an orgasm if their sexual encounter included anal sex. But before you try to convince your significant other anal sex would be good for her, the findings are a bit misleading. When you check the data, the women who had anal sex also enjoyed a lot of other stimulation as well, such as kink and foreplay. So, anal sex was an indicator the women were open and playful in bed—and that’s the key.

42. Anthony Weiner Got Caught Sexting Again

What the hell is wrong with Anthony Weiner? That’s what MSNBC’s Lawrence O’Donnell once asked the former New York congressman and mayoral candidate live on the air. It’s a legit question. The dude’s sexting problem got so bad it threatened Hillary Clinton’s presidential campaign. After his lust possibly affected the course of world history, Weiner decided to check into a cybersex rehab program.

If you ever wonder what your sexting says about your relationship, check this article for some perspective.

41. Piers Morgan Went Head-to-Head With Susan Sarandon

In one of the strangest celebrity beefs from this year, Piers Morgan thought it was a good idea to attack Susan Sarandon’s cleavage. (Of all the problems in the world, the bombastic Brit decided to focus on Sarandon’s breasts?) Yeah, we’re confused too.)

Being chill and sexy AF, Sarandon responded with this tweet:

Soon after, women around the world posted pics of cleavage in solidarity with Sarandon. That’s three things we love: Women supporting women, cleavage and anyone telling Piers Morgan to STFU.

40. Zika Became the New ‘It’ STD

In February, as fears of the Zika virus spread quicker than the illness itself, the Center for Disease Control released this Clinical Guidance for Healthcare Providers to sort rumor from fact. It stated, “Zika can be sexually transmitted from a person who has Zika to his or her sex partners, even while they are not symptomatic. Sex includes vaginal, anal, and oral sex and the sharing of sex toys.”

Of course, Zika showed up first in our horniest state: Florida.

39. Troublesome Allegations About That Rape Scene in “Last Tango in Paris” Reignited

Recently, an interview from 2013 with Italian film director Bernardo Bertolucci resurfaced. In the vid, he suggests that he and Marlon Brando conspired to film a nonconsensual sex scene with actress Maria Schneider that involved a stick of butter. Sites like Jezebel jumped on the story and savaged the late actor and Bertolucci for essentially filming what they viewed as rape.

The old story exploded with new life. It was reported in the New York Times. But since both Brando and Schneider passed away, they aren’t hear to clear the accusations. To hear her side, we’re left with her words. As as far as eyewitness accounts, the cinematographer, who’s still very much alive, said it was consensual and the story is not true at all.

38. Foot Fetishists Fell in Love With Hillary’s Feet

This story’s further proof of Rule 34: If you can think of it, someone finds it erotically stimulating. Case in point: Hillary Clinton’s feet. Look, we’re not saying Hillary isn’t (or is) sexy. But it surpsied us to learn that her feet are pretty popular with foot fetishists. Guess some folks get off seeing a powerful foot in a sensible heel. We don’t judge. But this was, um, surprising.

37. Donald Trump Admitted He Likes to “Grab ‘em by the…"

You knew this quote would make the list, and it would have ranked higher if bragging about sexual assault had actually disqualified him from becoming president of the United States. But as we learned in November, more Americans cared about Hillary’s emails than believed all the women who claimed they’d been sexually assaulted by Donald Trump. The story came to light when an old tape was leaked of Trump speaking with Billy Bush, a host of Access Hollywood. In very clear terms, Trump claimed that women allow him to do whatever he wants, and that he often feels like he can just “grab ‘em by the pussy.“ Typically, that would be political dynamite. But not for the Donald. Somehow, as if he was wearing a bulletproof vest made out of sexism, the scandal never really hurt him. He’s now our next president.

36. “Insecure” Steamed TV Screens With Sex Scenes

She made her name with her web series Misadventures of An Awkward Black Girl. This year, Issa Rae brought her brand of smart to her HBO show Insecure. It was one of the big breakout hits of 2016. One of the most talked about moments of the first season was in episode five, when her character steps outside her relationship to sleep with her crush. Their sex scene was some of the hottest black love ever shown on American TV. It was so good, Issa was still having sex flashbacks the next episode. And her cheating lit a fire of debate on Twitter.

35. American Doctors Performed A Successful Penis Transplant

This year, a team from Massachussetts General hospital performed the first successful penis transplant in America. And the second in the world. Rather than make cheap jokes, let’s focus on the realities of the life-changing surgery. The first recipient was able to father a child with his transplanted penis. Since a penis is so important to a man’s sense of his body, this surgery could be huge news for a very specific population of men: veterans who suffer devastating groin injuries from IEDs that detonate under vehicles.

34. Millennials Engaged in a Disappointing Amount of Sex

Dubbed the Hookup Generation, we’ve all grown accustomed to the media making fun of millennials for their casual Netflix and chill game. A lot of that talk began with Nancy Jo Sales’s Vanity Fair piece from September 2015. She theorized that Tinder and other apps have made hooking up too easy and drained sex of its meaning and power.

Of course, Sales is wrong, and this year, researchers set out to prove how wrong she was, which led to a raft of studies that proved, in fact, millennials are less likely to have sex than previous generations.

33. Women and Men Stood Together to Fight Slut-Shaming

One of our comandements? As long as no one is getting hurt, don’t get your tighty whities in a bunch about what someone else is doing with their body. For example, when a woman shows off her body, it doesn’t lower her value as a woman. Or as a person. Period.

There’s no reason why online commenters should feel okay attacking actress Ariel Winter for what she chooses to wear to Coachella.

Coachella 🎶🎶 (follow me on Snapchat winter.ariel)

A photo posted by ARIEL WINTER (@arielwinter) on

Or judge her for however much skin she chooses to show in a picture. Which is why we were so glad to see her clap back.

We also loved it when Channing Tatum pointed out the sexist double standard that people don’t slut shame him for his stripper past the way they do to Amber Rose. Making many of the same points, Rose penned her own op-ed about how she learned to overcome slut-shaming. Also, model Emily Ratajkowski wrote a LennyLetter against slut-shaming. And she posted a nude selfie with Kim Kardashian to make her point.

If you don’t agree, check how the Playboy Advisor defended Kim Kardashian from slut-shamers.

The bottom line is stop slut-shaming in 2017.

32. Chelsea Handler Penned An Essay About Abortion

For Playboy’s Freedom issue, Chelsea Handler wrote a brave essay about having had two abortions. It garnered a huge response. Over at The Frisky Kylie Chung wrote, “Handler’s essay is so incredibly important because piece-by-piece, it dismantles just about every cultural myth about abortion in existence.”.

31. Oklahoma Kinda, Sorta Legalized Rape

Meanwhile, over in Oklahoma one of their courts effectively legalized rape. Yes, non-consensual sexual assault was deemed legal in Oklahoma, if a person had been drinking and passed out. Regardless of what Oklahoma says, no unconscious person can grant consent.

30. Zayn and Gigi Hadid Made “Pillowtalk”

Former One Direction member Zayn Malik became a grown-ass man this year. For his single “Pillowtalk,” he asked model Gigi Hadid to play his love interest. In case you don’t know it, Gigi is all kinds of sexy.

And, since Zayn also got it like it that, when you put the two of them together, the sexy takes over the screen.

29. Tinder Launched 37 New Gender Identities

Male and female are designations of biological sex. Masculine and feminine are types of gender. Don’t forget that just a few hundred years ago, in Europe, the ones wearing high heels, wigs and makeup were men. Gender is a performance. That’s why it’s so dope to see companies like Tinder recognize that human beings require more than two modes of gender to express ourselves. When this story broke, Newsweek asked, “What Do Tinder’s 37 New Gender Identities Mean? The answer is that more people are now able to be true to themselves. That’s sexy.

28. The United Nations Asked the World to Decriminalize Prostitution

For years, advocates have urged lawmakers to decriminalize sex work around the globe. This year, that fight got a few major allies. The United Nations and Amnesty International both urged world leaders and governments to rethink sex work. They argued that sex workers deserve respect, full legal protection and to have their human rights protected. They’re right.

27. Arianna Grande and Nicki Minaj Dropped the Super Sexy “Side to Side.”

Arianna and Nicki in a steam room—that alone offers up a big hit of sexiness. When pop music videos are good, they’re really good. This one was easily one of the sexiest of the year.

26. Millennial Sexperts Took Over YouTube

2016 saw the rise of amateur millennial sexperts. Self-certified sex ed instructors like Shan Boody and Laci Green want you to be a better lover. They keep their sex talk, frank, fun and informative. We recommend you find one or two or three you like. Here’s a sample to get you started.

25. Bella Thorne’s Playboy Shoot Broke the Internet

Former Disney star Bella Thorne set the internet on fire when she made her Playboy debut. The redhead def turned heads and spoke her mind when she posed for the Bunny, saying, “There’s this effort to try to shame a woman’s sexiness by pulling a cover over it, but I’m a woman who loves skin. I love skin on me, I love skin on girls, I love skin on guys. If you’re confident enough to show off your body, you should. Be confident.”

Chloe Aftel / Playboy

Chloe Aftel / Playboy


Come back next week for the final installment to find out which was the biggest moment in sex for 2016!

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