NSFW: The 10 Biggest Sex Bloopers Of All Time

by | Sep 27, 2016 | Sex & Love

These 10 guys let the whole team down. Learn from them.

I’mma Let You Finish

Self-proclaimed a-hole Kanye West digs a digit up his derriere. Now, we don’t judge… but y’all do. His preference was exposed on Twitter after a public row with his ex, Amber Rose. Pro tip: don’t call out your former flame if she’s packing that calibre of ammo.

U Got It Bad

Filming your sexcapades is fun. But keep that homemade foot- age homeward bound, or you’re in trouble. R&B star Usher found this out the hard way, when his laptop went AWOL, and his video went, well, everywhere.


When former model Tyson Beckford decided to rub one out in an online video chat, he reckoned his privates were private. Then his accomplice leaked the recording. Yeah, she shouldn’t have done that, but he should have seen it coming – because now we all have.

Don’t Become a Wiener Joke

… which is what happened to former congressman Anthony Weiner, after it was found that he had sexted images of his dick to a few strangers. He had to step down obviously, and deal with all the jokes too.

#Winning? Nope

Charlie Sheen turned his carnal adventures with pornstars and prostitutes into a hashtag. Turns out all that time he was hiding his positive HIV status. Cue more than a few well-deserved lawsuits.

Peek-a-Boo is for Pervs

Rock ’n roll legend Chuck Berry installed cameras in the ladies’ of his restaurant, for “security”. He was sued for millions, so remember: a camera is only fun when she knows about it.

Don’t Be Like Bieber

The baby-faced pop star lost his towel on a Bora Bora beach. How do we know this? Paparazzi – and papa, too, who tweeted all about his kid’s schlong. Can we buy these guys some class?

Dishonourable Discharge

Former US VP-candidate John Edwards didn’t only have an affair with his campaign videographer, but had a kid with her too. Oh, and his wife had breast cancer at the time. Not happy in your marriage? Man up and talk about it.

Little Pee-Wee’s Big Adventure

Paul Reubens in a porn theatre is one thing. The real problem (including a public indecency charge) is that Pee-Wee Jr. made an appearance too. Keep it in your pants.

The Even Later Show

David Letterman had an affair with an intern. Really, bro? Really? The only thing more cliched is the divorce that followed, which cost him a few hundred million.

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