Biggest Bombshells From Charlie Sheen's Memoir 'The Book of Sheen': Sexual Encounters With Men, His Romance With Denise Richards and More

Charlie Sheen dropped shocking revelations in his debut memoir, The Book of Sheen.

Out on September 9, the book included the highs and lows the Two and a Half Men actor went through over the years. It also unveiled bombshells, including Sheen's sexual encounters with men.

"I flipped the menu over," he wrote in the book.

Sheen also spoke about the subject in his two-part Netflix documentary, aka Charlie Sheen, admitting it was "f------ liberating" to "just talk about this stuff."

"It's like a train didn't come through the side of the restaurant. A f------ piano didn't fall out of the sky. No one ran into the room and shot me," he said.

Sheen also reflected on his past romance with ex-wife Denise Richards, including their meeting on the set of the 2001 romantic comedy Good Advice.

Although they kept it professional while working together, the actor admitted in the book, "The more time we spent together on set, the more challenging it became to hide our unchaste chemistry."

Sheen and Richards' romance further blossomed when they watched a baseball game between the San Francisco Giants and the Houston Astros on October 4, 2001, for their first date.

"I carefully explained to D that if we were at a restaurant unable to watch, the main thing on my mind would be the game. (The main thing I could say out loud.)," he reminisced. "She completely understood and loved the idea of joining me to celebrate my passion for baseball. We ate our Zone meals from plastic bowls and hung on every pitch when Bonds was at the plate."

The Red Dawn actor wrote, "As we were saying good night at the elevator, D grabbed my face and pulled me into a long passionate kiss. The Baseball Gods had sprinkled some magic on our night. I was no longer thinking about the game."

In The Book of Sheen, the 60-year-old Platoon star looked back at the time he attended a private men's addiction group hosted by Matthew Perry, saying they "shared a deeper truth we saw in each other."

"We were both, as Bobby Dee Jay used to say, 'veterans of the unspeakable,'" he added.

According to Sheen, the Friends actor had the ability to "turn every frown upside down" and that he had "never met anyone who more masterfully used humor as a deflector-shield."

In an excerpt shared by a news outlet, Sheen also cast his mind back to his nights out with The Brat Pack, which had an "all-star lineup" consisting of Rob Lowe, Demi Moore, Judd Nelson and Andrew McCarthy.

"As a group, they couldn't have been nicer to me; it was the gauntlet of hysteria they incited that had me constantly seeking shelter," he wrote.

Detailing one of the parties they had, Sheen recalled, "As soon as we'd exit the limo, I'd be relegated by their screaming fans to the role of stray dog, bringing up the rear for their crowd-parting, bar-hopping rambles. The night always began at the Hard Rock Cafe, then sashayed its way across the landscape of the gotta-be-seen popular hot spots. I felt so small and left out as I watched the Emilio [Estevez]-steered throng, redefining what a copious and decadent bask in the limelight could look like."

He also mentioned Chris Penn, who "was a passenger as well on many of those nights," though it changed after his film Footloose was released.

"That one hit me the hardest — my best friend in life was suddenly one of them. I was torn between hoping he was ready for it and knowing deep down that he wasn't," Sheen continued.

The Young Guns star called himself the "invisible valet" who carried the bags "for a clob of celebrity that had the masses hypnotized."

Sheen added, "I wanted to be told just once by their babe-squad that I mattered too. Knowing it wouldn't happen until my celebrated film had a line around the block required a patience I hadn't developed yet. To be in the crush of LA's insane mid-eighties club scene with Rob Lowe and a bevy of gorgeous gals was like being shipwrecked with a fat guy — you're gonna starve."

In The Book of Sheen, the Eight Men Out star revealed when and how he lost his virginity with "a gorgeous red-headed Vegas escort named Cindy" during his sophomore year of high school. It occurred after he and his friend Joey "borrowed" his dad Martin Sheen's wallet.

"[Candy] responded with a level of physical generosity neither of us knew existed," Charlie wrote in his book, adding, "She was Ann-Margret in her prime with a Mastercard swiper. (I didn't care that the swipe took longer than the s--.) It was everything I'd hoped for, it was everything I could have imagined."

After having their intimate moment, Candy reportedly asked if he could "wake dad up for an autograph."

"For the record, I went first," said Charlie, who received a two-hour sermon about "s-- vs. love" from Martin after the patriarch found out what happened.

He wrote, "I kept stressing how gorgeous Candy was and what a great deal dad and I both got for the price. The look on his face told me we were done."

On the final night of filming Rated X in Toronto in 2000, Charlie decided to use "the matchmaking Yellow Pages of Bell Canada" to end his celibacy streak. He got a "gorgeous brunette" and hooked up with her in his hotel room.

In his memoir, the Machete Kills actor recalled enjoying a "post-euphoric cigarette" when the woman "reached over and slapped [his] stomach with a room-filling thwack to get [his] attention."

"Whattya say, fatso — you up for round two?" the woman reportedly asked him.

Charlie wrote, "Wow. Jeez, lady, you had 10,000 nicknames to choose from and you went with that? I wanted to blow my brains out. It's amazing where one word can send a guy."

Upon returning to Los Angeles after the incident, he reportedly consulted a liposuction doctor and underwent the weight-loss procedure.

Before Charlie learned about his HIV diagnosis in 2011, the Golden Globe-winning actor said he suffered from "nonstop clusters" of headaches and "delirious night sweats that redefined 'waterbed.'" While he thought he had a terminal illness, discovering he contracted the infection left him at a loss for words.

"As shocking and depressing as my new status was," Charlie wrote in his memoir, adding he felt a sense of relief once he was diagnosed correctly.

Charlie revealed the depths of his drug use in The Book of Sheen, confirming he first tried marijuana at 11 and cocaine in high school.

"The main issue with the drug for me was how cunning it was," he shared. "I'd be going about my day handling a bunch of not cocaine things, and in the next second be launched into a hair-on-fire obsession to get that drug into my bloodstream."

He divulged he felt he was in "another galaxy" when he tried crack for the first time in 1992.

"People will claim their greatest feelings in life as 'my child's first steps' or 'saving that kid from a fire,'" Charlie wrote. "To quote Matt Hooper from Jaws: 'I got that beat.'"

Charlie — who has been married and divorced three times to Donna Peele, Denise and Brooke Mueller — has five children: Cassandra Estevez, Sami Sheen, Lola Sheen and twins Bob and Max Sheen.

According to the father-of-five, failing his children "was only one thing that felt worse than betraying [himself]."

In 2017, he had to ask a friend to drive him and his daughter Sami to her appointment as he had been drinking at the time.

"In that car, on that day, with my best friend and a child I adore, I joined Sam in those mirrors and saw a guy who was desperate to finally come home for real," Charlie recalled.

On December 12, 2017, the day after the car ride, Charlie ingested "two Valium" and drank "three beers." He then decided to "quit drinking for good" the following day — on his daughter Cassandra's birthday.

While Charlie infamously clashed with Two and a Half Men co-creator Chuck Lorre before his dismissal from the show, he wrote in The Book of Sheen that his addictions were the actual root cause of his firing.

"[His split from his third wife, Brooke] left me numb, both in spirit and from the amount of booze and dope I showered my brain with to quell the debilitating frustrations. It was the flashpoint that left me unable to show up and execute my job with any focused consistency, and as a result Two and a Half came to a screeching halt with eight episodes still on the production schedule," he recalled.

Then-CBS chairman and CEO Les Moonves offered him the use of Warner's private jet to fly to rehab, though Charlie declined and decided to quit all the drugs he was doing cold turkey.

The Three Musketeers actor, however, continued using a testosterone cream he had been using to get his body back into shape.

"Not knowing that at the same time I was being shape-shifted," he recalled. "That drug is known to metabolize into the identical psych profile an anabolic steroid will produce. Anyone who bore witness to the raging demon I melded with will hopefully glean some clarity for what my state of mind was up against."

Charlie added in the memoir that he is not "making excuses or asking for a pass" but "putting it out there as a detail that may have been confused with a laundry list of other potential suspects."

"I've heard great things about the drug when used responsibly, but let's keep it real — drugs and responsible are two words I never made [a] habit of cramming into the same sentence," he continued.

He was officially fired from the hit sitcom following the very public 2011 meltdown.