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

The Year’s 100 Biggest Moments in Sex—Part Two: Miss December 2016 Eniko Mihalik as shot by David Bellemere

Miss December 2016 Eniko Mihalik as shot by David Bellemere

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. Last week, we brought you part one of the 100 Biggest Moments in Sex.

This week, Playboy continues our countdown with numbers 74-50.


74. Iskra Lawrence Helped Body Positivity Go Mainstream

👋 good morning Austria🌳💐⛰🏞 #iskralawrence #everyBODYisbeautiful no retouching

A photo posted by Iskra lawrence🦄✨ (@iskra) on

English model and activist Iskra Lawrence stripped down on a busy subway in the vid below to prove a simple point: every human body is beautiful, or as she put it, “Every single one of us has so much value and so much worth that is so much more than just skin.” Body positivity trended throughout 2016 and will surely be all the more central to cultural conversations in 2017. That is a beautiful thing.

73. Rise of the Sexbots

What happens to a society when sexbots are as common as blenders and washing machines? We’re about to find out. Whether we’re talking about that sexbot orgy scene on HBO’s Westworld, or an Angelina Jolie-lookalike Lara Croft sexbot, or that dude who invented a Scalett Johansson-lookalike sexbot, in 2016, pleasure robots made plenty of headlines. Next year, expect to read more articles like this one about a man falling in love with his sexbot.

Experts are even wondering if sexbots can teach us to be better lovers. Perhaps most interestingly of all, a futurologist (whatever that is) is also predicting that by 2025, women will be more likely than men to have a robotic sexual partner. All in all, the advent of artificial lovers will def remain a top story of 2017.

72. Sevdaliza Released Her Music Video For “Human”

There is a certain futuresexycool vibe in how we’re merging with our technology to embrace our strangest fantasies. Riffing on this idea, singer Sevdaliza made one of the sexiest videos of the year for her song “Human.” For the lead single off her debut album, Sevdaliza played with the male gaze and the mythical aspects of female sexuality.

71. Science Determined That Morning Sex is Good For You

When we have sex, why do we say we slept with someone? Good sex should be the exact opposite of sleep. This year, we learned too many people are missing out on the magic of morning sex. Not only does it chill your mood for the day, it also floods your brain with feel-good chemicals and performance-boosters. Plus, soft morning light is flattering; as research suggests, light can make men perform better. It’s time to ditch the coffee.

70. Bisexuality Became More Acceptable

The latest research suggests that sexuality is fluid and on a spectrum and as homosexuality loses its stigma, more people are feeling comfortable exporing bisexual behavior. A 2016 study showed that the rate of bisexual behavior has doubled since 1990.

69. Hugh Hefner Beckoned the End of the Conservative War of Sex in Playboy’s Freedom Issue

Since our first issue, published in December of 1953, Hugh Hefner has battled to make America a freer, sexier place. In this essay, Hef looked back at his fight with the religious-minded conservative sex movement. Despite the progress, he concluded that the struggle is not yet over. Politicians like Ted Cruz and Mike Pence are proof of that. But as Hef put it, “We have already won those battles, and we will win them again.”

68. Ecosexuality Became a Thing

Ecosexuals believe we can save the planet if we start humping it. Well, kind of. The new kink made a big splash in the news, but it’s actually the brainchild of performance artist duo Pony Express. They erected an installation called Ecosexual Bathhouse in Melbourne, designed so visitors can discreetly fuck the Earth. Although fingering orchids may not save the Earth, their message is clear: it’s time we save our environment.

67. Fergie Released Her M.I.L.F. $ Video

The Black Eyed Peas vocalist came back this year with a roar, releasing a super-sexy video for “M.I.L.F. $” It features her and a parade of seductive moms like Chrissy Teigen and Ciara showing off their M.I.L.F shake. But the real show-stopper is when Fergie and Kim Kardashian pour milk on themselves. Don’t ever say moms aren’t sexy.

66. Science Made Sperm From Women’s Cells

A number of studies published this year centered on what affects the quality of sperm. We learned that coffee and alcohol don’t affect sperm production, but your cellphone does. So do carbonated beverages.

That may not matter much because scientists found a way to make sperm cells out of skin cells. The big story is: you don’t even need a man to make sperm these days. If women and robots ever decide to team up, men better watch their asses; they’re no longer needed to keep the flame of humanity burning bright.

65. Some Women Used Tinder To Con Men Into Doing Chores

A few women tried using Tinder in a new way this year. They’d swipe to meet a guy, invite a match to come over and get busy…by asking them to complete some home projects, like a leaky faucet, for example. That’s no euphemism. They’re really doing that—but at least it shows men are still handy to women with or without their sperm.

64. Lindsey Pelas Killed in the Cleavage Game

20 minutes into Netflix and chill and she gives you this look… What do you do? 👀😂👄 @leelhgfx

A photo posted by lindsey (@lindseypelas) on

This year, Lindsey Pelas owned being a busty beaut, going so far as to remind men and women that large breasts can be downright annoying. Check Pelas talking about it here for Cosmo.

63. Pro Athletes Dropped Some Major Dough On Baby Mama Drama

Long before Kim K ever met Kanye, she dated NFL running back Reggie Bush. They broke up because his conservative family was embarrassed by her sex tape. Bad move, Reggie. This year, the married athlete’s own sex life made headlines when his extra-marital baby mama drama blew up on TMZ.

Rather than dwell on Mr. Bush, let’s play a game. Which pro athlete do you think dropped the most dollars on their baby mama drama this year? Hint: he’s in the NBA.

62. Rihanna and Drake Broke Up…Again

At MTV’s VMAs, Canadian rapper and former child star Drake confessed to the world his love for Rihanna as he introduced the singer. But when RiRi stepped out to accept her Video Vanguard Award and Drake tried to kiss her, it looked like she curved him. Weeks later, rumors turned into fact when the sexiest couple in music broke up. Just like she is in her vid for “Kiss It Better,” Rihanna was once again alone—but still undeniably sexy.

61. An American Woman Auctioned Off Her Virginity

After seeing a Facebook advertisment for a legal brothel, Katherine Stone, then a virgin, moved to Nevada to become a sex worker. She then set a price and auctioned off her virginity. But this story has a twist. Stone auctioned off her virginity to raise funds to rebuild her family home after it burned down in a fire. As she told CNN, “People say you are suppose to do it for love, but, if you think about it, I am doing it because I love my family.”

60. Cunnilingus Was Determined to Be Good For a Man’s Health

According to research, the bacteria in a woman’s vagina, lactobacilli, is the same as the bacteria in commercial yogurt. And it’s just as good for you.

59. Hulk Hogan Shuttered Gawker With His $115 Million Lawsuit Over a Sex Tape

In one of the most stunning legal battles in recent memory, professional wrestler and moustache icon Hulk Hogan (silently backed by Silicon Valley titan Peter Thiel) defeated Gawker in a landmark trial. The case questioned the legality of Gawker’s publication of Hogan’s sex tape. And it was their undoing. Gawker was ordered to pay Hogan $115 million dollars, which bankrupted the company.

58. Ciara Slayed the Grammys With a Thigh-High Split

Singer-sex symbol Ciara showed up at the 2016 Grammys ready to slay, turning heads and straining necks in a thigh-split dress that fully captured imaginations, including ours.

57. Polyamory and Open Relationships Got Trendy

2016 may go down as the year the human race broke monogamy. A study published this year concluded that one in four Americans under the age of 44 would be cool with their partner having sex with someone outside their relationship. In comparison, only one in 10 Americans over the age of 65 would be okay with an open relationship. That’s a huge generational shift.

Consensual non-monogamy is also on the rise among single people too. The next question to ask: What does it mean for society if open relationships are the new normal?

56. California Voters Rejected a Law Mandating Condoms in Porn

California measure Proposition 60 would’ve required porn performers to wear condoms. Proponents of the law argued it would stem a public health crisis and promote condom usage, citing studies that show when porn performers use condoms, viewers are more likely to use them.

Critics argued it was an attempt to legislate morality, and if it passed, state revenue-generating production companies would leave the state. Voters rejected the law in November, and since most adult films are made in California, it means you won’t be seeing condoms suddenly flood your PornHub page anytime soon. But hey, you should still use them.

55. Britney Spears Grabbed G-Eazy’s Python at the MTV VMAs

Guess who’s back, bitch? That’s right. First, she wore a barely-there dress to the Billboard Awards. Then, at this year’s MTV VMAs, she brought a showcase of sexy while performing her single “Make Me” with G-Eazy. Even though she lustily grabbed his crotch on stage, when the lazy-mouthed rapper went in for a kiss, Britney gave him the air. Yo G, don’t forget: she’s Britney, bitch!

54. Science Concluded That It’s Better For Women to Have Big Butts

In one of the best science stories of the year, leading researchers at Oxford University published a paper that determined it’s not only healthy, but naturally-advantageous for a woman to have a big butt. Spread the word.

Photos @gavinglave ☀️

A photo posted by Anastasiya Kvitko (@anastasiya.kvitko) on

53. The Male Birth Control Pill Flopped

The goal to develop a male birth control pill was once again put on hold when news broke that a study was discontinued after men quit after experiencing adverse side effects—which women have dealt with since the invention of the pill.

Here’s the thing: as we pointed out, no one should have to deal with the side effects of birth control.

At the other end of the spectrum, young couples started celebrating vasectomy parties. Remember when a tattoo of your lover’s name was considered the ultimate relationship whoops?

52. Young M.A. Coined the Summer’s Funniest Meme About Sex

Brooklyn rapper Young M.A. broke on the scene this year with her independently-released hit single “OOOUUU.” It’s catchy AF and packed with attitude and sick couplets. One line in particular left its mark: “You call her Stephanie? I call her Headphanie.”

Just like that, a new meme was coined. Young M.A.’s hilarious reference to oral sex grew so popular that liquor-maker Hennessy, whose product makes numerous appearances in the vid, created custom Headphanie bottles to catch some of those dollars.

51. Rough Sex Became Good For Your Brain

According to the latest research, BDSM offers a ton of benefits for you brain. Kink is not only fun, sexy and thrilling, but it also lowers stress, increases arousal and can induce what scientists and athletes like to call “flow state.” For more on the value of BDSM, check this interview we published with “Sex With Shakespeare” author Jillian Keenan.

50. Hef Let Go of the Mansion

Marya Gullo / Playboy

Marya Gullo / Playboy

It was one of those stories everyone heard about. This year, Hef sold the Mansion for $100 million dollars to his neighbor, who agreed that Hef can continue to live there and enjoy all the parties he’s famous for hosting at his home, like the annual Midsummer Night’s Dream party—which, this year, was celebrated concurrently at the Mansion and in Las Vegas.

To reminisce about the good times, check out Antje Utgaard taking over the Mansion in this super-sexy photoshoot.


Come back next week for part three, featuring Amber Rose and Kanye West’s booty feud, Pokémon Go, Niykee Heaton and Donald Trump talking about…well, you know what he talked about.

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