Charlie Sheens wild life – group sex, escorts and eye-watering £255k romps

He is known for his impressive work starring on the hugely popular comedy series Two and a Half Men and the hit Hollywood movie Wall Street.

At one point, Charlie Sheen was the highest paid TV star in the world, raking in a reported $1.8m (£1.5m) per episode of the CBS TV show.

But it’s fair to say that the actor has gone on to make a name for himself away from the cameras following his explosive exit from the sitcom in 2011 which led to his serious drug and alcohol abuse.

During his downward spiral, the actor found himself becoming quite the sex addict after he allegedly spent thousands on romp sessions with sex workers in addition to a questionable alleged porn addiction.

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As the actor celebrates his 56th birthday with a bang, Daily Star have taken a deep dive into his biggest sex confessions over the years.

Porn allegations

In 2006, Denise Richards and Charlie Sheen decided to go their separate ways calling an end to their marriage after four years.

However, their split was anything but easy as their divorce papers filed by his ex-wife came to light back in 2017.

In the explosive papers, the American actress – who shares two daughter’s Sam and Lola Rose with the Two and a Half Men star – claims she was concerned by her partner’s use of gay porn which appeared to her to involve young male stars who looked underage.

In her sworn declaration – which was filed at Los Angeles Superior Court in April 2006 to support her argument to take a restraining order out against him – the starlet shared her fears about his online habits.

She wrote: “In December of 2005, the Respondent and I took a vacation to Barbados without our children.

“It was my intention to discuss certain serious matters with the Respondent during this trip and to try and understand why the Respondent was participating in certain activities, which were repulsive to me and to convince him to seek help for the sake of our children.

“Prior to our trip, I learned that the Respondent was accessing gay pornography sites which I found even more disturbing because I felt that the boys looked underage.”

The divorce papers also claimed that Sheen had signed up to “disturbing” porn sites “which promoted very young girls who looked underage to me with pigtails, braces, and no pubic hair performing oral sex with each other.”

She also contended that her ex-husband used “gay pornography also involving very young men who also did not look like adults.”

In September the following year, Sheen said the FBI were “aware” of her claims but had taken no action against him.

Speaking at the time, the actor revealed: “The FBI was aware of these issues. I provided them with every computer I owned.

“The computers were returned two weeks later. Haven’t heard from them since. Period. The end.”

HIV diagnosis

In November 2015, the disgraced Hollywood actor revealed that he was diagnosed HIV positive four years earlier.

After the news hit the headlines, the Platoon star went on to claim his diagnosis was down to two occasions when he had unprotected sex.

In an explosive interview with The Sun, the actor confessed that he could only think of two occasions where he engaged in sexual intercourse without using condoms.

He told the publication: “A couple of times, twice. And we would be having a different dialogue.

“I was always the guy that promoted it and said you’ve got to use condoms, this and that. I was too drunk or too bored one night and here we are.”

In a heated interview with Piers Morgan, the Golden Globes winner told the sold-out crowd at London Town Hall that he had “never” given the life-long disease to any of his previous partners.

He confidently professed: "I never did. I wouldn’t do that to someone, I would not.”

However, there have been claims that Sheen refused to tell some of his ex-partners that he was HIV positive before having sex with them.

When the former Britain’s Got Talent star pressed him on this, he admitted: “The only times I didn’t tell them was because the last 25 times they used it against me and used my medical condition for their own folly and financial gain.

“Here’s the great news – no one has been infected by me. No one. They claim, the sorrow and the pity or whatever, but that’s on them. I know the truth.”

Sex fund

In 1994, the star opened up about the extensive amount of money he spent on late night romps with sex worker while testifying against Heidi Fleiss.

While under oath, the actor said he spent $53,000 (£45,000) however it has since emerged that the figure could be much higher according to the sex positive worker.

Speaking to The Hollywood Reporter, she said: “The only reason his name came out is that when I was arrested, I had travellers’ cheques in my purse with his name on them.

“On the stand he said a much lower amount than he actually spent with me.

“He probably spent closer to $300,000 (£255,000) or $400,000 (£341,000) on girls. He said something like $60,000 (£51,000).”

50-person orgies

During the height of his fame, the star would reportedly host wild sex orgies at both his family home and in plush hotels in the late noughties.

According to a well-known Hollywood transvestite Sham Ibrahim in 2015, Charlie is interested in to the many kinky fetishes which he often likes to involve in his sex life.

They told Radar: “Charlie would have these raunchy and wild sex orgies that included up to fifty people and this went on for hours. He would open his home or would have them at hotels, but he was always ready to party.

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“I know so many people that have been to his gathering and although it has slowed down over the past four years, they have not stopped entirely.”

He added: “Charlie is very into all sorts of fetishes and kink. He loves his trans girls. He is very into dildos, S&M, leather and just about anything that goes along with it.”

“He would invite anyone who was attractive but they had to be into kinky s**t like him.”

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