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Charlie Sheen’s Shocking Confessions: Virginity Lost to a Vegas Hooker and Life’s Wild Ride

Charlie Sheen’s Shocking Confessions: Virginity Lost to a Vegas Hooker and Life’s Wild Ride
  • PublishedSeptember 9, 2025

I’m Sage Matthews, a cynical observer who’s seen it all, and I’m here to guide you through the latest revelations from Charlie Sheen’s memoir, “The Book of Sheen: A Memoir.” As I read the news at 2 AM, shaking my head, and muttering, “Of course this happened,” I’m reminded that some stories are just too wild to ignore. Charlie Sheen, the 60-year-old “Two and a Half Men” alum, has always lived a wild life, but his latest confessions take the cake.

In a passage from his memoir, Sheen recalled losing his virginity to an escort in Las Vegas when he was just a sophomore in high school. He and his friend Joey “borrowed” his famous dad Martin Sheen’s credit card to pay for the services of a gorgeous red-headed Vegas escort named Candy. According to Sheen, Candy “responded with a level of physical generosity neither of us knew existed.” Sheen admitted that he was unable to return the favor, but his friend Joey got a turn with Candy as well. “For the record, I went first,” Sheen explained, implying that Joey had intercourse with Candy after him.

The encounter was facilitated by Sheen’s use of his father’s credit card, which he described as a “Mastercard swiper.” Sheen wrote that the experience was “everything I’d hoped for, it was everything I could have imagined.” After the encounter, Candy asked if they could “wake Dad up for an autograph.” Martin Sheen was not thrilled with his son when he learned about the escort, and Sheen shared that he was given a two-hour lecture from his father about “sex vs. love.” Sheen remained unscathed, stressing how gorgeous Candy was and what a great deal he and his friend got for the price.

This is just the latest revelation from Sheen’s book, released the day before his Netflix documentary, “aka Charlie Sheen.” In the streamer’s two-part doc, Sheen admitted to having sex with men for the first time ever. He said it was “f–king liberating” to finally tell his truth, noting that it’s like a weight has been lifted off his shoulders. Sheen shared that his first same-sex encounter happened when he started smoking crack, and he struggled to come to terms with his actions.

Sheen also spoke about contracting HIV, which he came clean about 10 years ago. “I do know for a fact that I never passed it on,” Sheen said. The star goes into detail about overcoming his addiction battle while navigating his fall from grace following a wild life in the spotlight and his hopes for the future in both his book and documentary.

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In a recent interview with Page Six, Sheen revealed that he’s been celibate for nearly a decade. “Oh my gosh, for so long [sex] was all I cared about, or it was near the top of the priority list. And so I just saw [celibacy] as a needed break from those pursuits. That’s not me slamming the door on anything in the future. No, I would absolutely welcome some type of companionship,” he said.

As I wrap up this article, I’m left wondering what’s next for Charlie Sheen. Will he continue to shock us with his confessions, or will he finally find some peace? One thing’s for sure: his life story is a wild ride that’s hard to look away from.

Sources: Celebrity Storm and New York Post, People Magazine, Page Six
Attribution: Creative Commons Licensed

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Attribution: Creative Commons Licensed
Written By
Sage Matthews

Sage Matthews is a creative journalist who brings a unique and thoughtful voice to the world of celebrity news. With a keen eye for trends and a deep appreciation for pop culture, Sage crafts stories that are both insightful and engaging. Known for their calm and collected demeanor, they have a way of bringing clarity to even the messiest celebrity scandals. Outside of writing, Sage is passionate about environmental sustainability, photography, and exploring new creative outlets. They use their platform to advocate for diversity, inclusivity, and meaningful change in the media landscape.