The most cringe-worthy leaked celebrity sexts of all time

Think your drunk texts are bad? You’ve got nothing on these X-rated leaked celebrity electronic missives.

Never have celebrities appeared to be more like us than when the screenshots of Amazon founder Jeff Bezos’ rumoured sexts to his rumoured girlfriend Lauren Sanchez were leaked.

According to the National Enquirer — so take it all with quite a large grain of salt — the alleged sexts read: “I love you alive girl. I will show you with my body, and my lips and my eyes, very soon.”

Let that sink in for a second. I love you … alive girl. ALIVE girl. The sexiest thing the multi-multi billionaire (his billions have billions of their own) Bezos could allegedly think to write is that Sanchez, his gorgeous girlfriend, is alive. Hot stuff.

Jeff Bezos sexts like he's an AI in a human suit pic.twitter.com/UjfOQv0UZk

— Dana Schwartz (@DanaSchwartzzz) January 10, 2019

But in the great canon of saucy celebrity missives, where does it sit in terms of the cringe factor? Is it number one, or is it eclipsed by other shudder-inducing messages? We rank the most embarrassing sexy conversations between celebrities of all time.

PRINCE CHARLES AND CAMILLA

Charles and Camilla are the picture of respectability now, but back in 1989, things were seriously saucy. Picture: Clarence House/WPA Pool/Getty Images

The year is 1989, the date is December 18, and Prince Charles and Camilla Parker-Bowles are in the midst of quite a racy conversation. Picked up by a random scanner user, the exchange was recorded and eventually found its way into the pages of New Idea and, after that, press in Germany, America, Italy, Switzerland and Ireland.

Finally in 1993, barely a month after Prince Charles and Princess Diana announced their official separation, the full transcript of the conversation was printed in the British newspapers. And what a doozy it was.

In between talk about an upcoming speech Charles was giving about “rebuilding communities”, the pair discussed the logistics of planning their next tryst, and then Charles attempted a little bit of dirty talk. “I want to feel my way along you, all over you and up and down you and in and out,” he said.” (“Oh!” was Camilla’s response.) “Particularly in and out!”

The piece de resistance was Charles musing over whether he could be reincarnated as a pair of Camilla’s knickers or even a tampon so that he could “just live inside your trousers”.

“My luck to be chucked down the lavatory and go on and on forever swirling round on the top, never going down,” Charles moaned, pushing the metaphor to its absolute limits. “Oh darling, I just want you now,” Camilla laughed, finally cutting him off.

PRINCESS DIANA AND JAMES GILBEY

James Gilbey. Picture: Supplied

Diana. Picture: Anwar Hussein/Getty Images

Not to be outdone, Princess Diana got caught in a cheating scandal of her own on New Year’s Eve 1989 with her close friend James Gilbey. Like Prince Charles and Camilla, Princess Diana and Gilbey were recorded by a hapless radio scanner enthusiast in this intimate conversation later referred to as ‘Squidgygate’, courtesy of the nickname Gilbey referred to the princess by. The transcript of their conversation was printed in The Sun in 1992.

Mostly, Princess Diana complains about Christmas with the royal family and a lot of discussion of their mutual friends while Gilbey listens loyally on, occasionally blowing kisses down the phone to his lover. “I can’t tell you what a smile that has put on my face,” Gilbey tells her.

There’s a little bit of ‘what are you wearing’ chat (“a pair of black jodhpur things,” Diana responds, “and a pink polo neck”) and a strange moment when Gilbey tells Diana that he hasn’t masturbated in 48 hours, before things turn utterly romantic.

“I want you to think of me, after midnight,” Diana says.

“You don’t need to encourage me to think about you. I have done nothing else for the last three months … Laugh some more! I love it when I hear you laugh. Do you know, I am happy, when you are happy?”

TIGER WOODS AND JAIMEE GRUBBS

Tiger Woods got embroiled in quite the scandal. Picture: Donald Miralle/Getty Images

In 2009, the New York Post got the scoop of the century when it published the transcripts of a cache of raunchy messages sent between golfing legend Tiger Woods and Jaimee Grubbs, a waitress from Los Angeles. They texted for 31 months while their affair was ongoing. (Woods also had affairs with several other women, including Holly Sampson, Erin Rotherham and Joslyn James when he was married to Elin Nordegren.)

The texts with Grubbs were a strange melange of the everyday and the explicit. In one message, Grubbs suggests they watch an episode of Desperate Housewives, and in another Woods wishes her a happy thanksgiving. Others talk about new piercings and the removal of underwear, so it’s not all TV guide and Hallmark cards.

The most awkward exchange happens when Grubbs tries to get Woods in the mood with the very suggestive message: “Take a break from watching boring old golf”, which she follows up quickly with “I mean the amazing sport of golf ;)”.

An hour later, with no response from Woods, Grubbs texts again: “Babe I was kidding”.

Woods responds: “I know sexy”.

ASHTON KUTCHER AND BRITTNEY JONES

Ashton Kutcher reportedly sent some saucy messages of his own. Picture: AP Photo/Mark J. Terrill

The sexts sent between Kutcher and Jones are remarkable not for their content but their brevity. Towards the end of his relationship with Demi Moore, Kutcher and Jones reportedly started an affair and began firing sexy messages to each other on their Blackberries. (It was 2010, after all.)

Just a few months after they met in July, Jones was on the cover of Star magazine in the US, brandishing the few sexts allegedly from Kutcher she had managed to save. The rest, she told the magazine, Kutcher had made her delete from her almost-smartphone in front of him.

The alleged messages are brief and to the point. “R u busy?” and “What r u wearing now?” are two of the perfunctory missives. In another, Kutcher reportedly tells Jones that he can’t talk because he is “w/ my daughter”.