The 60-year-old English model first appeared in the nude magazine's pages way back in 1981, before her transgender identity was revealed.
A decade later, details of her gender reassignment had been made public, making her the first transgender model ever to appear among the famous Bunnies.
According to Daily Mail via AsianTown, Caroline said that when she was little, she identified as male because she had a penis.
But as she got older, she realized that she preferred dressing up and playing with dolls over anything her brother was doing. This meant that, as a teenager named Barry, she was bullied.
It wasn't until she took a sex education class that she realized she was attracted to boys, not girls. She thought that she must be gay, though admitted 'that wasn't right for me either'.
As she grew more, she started letting her hair grow longer, but found that the gay men she was attracted to didn't like her back and preferred men who actually looked like boys.
Gay clubs wouldn't even let her in, she said, because they thought she was a drag queen. She only first made the connection that she was transgender after meeting another transgender person for the first time.
So she started saving while working as a showgirl, during which time she was always billed as a woman - not a transgender or transsexual person.
First, Caroline earned enough money to get breast implants, thanks to an unexpected windfall. She explained that a man told her that his rich friend 'would pay anything to see that someone like me exists' - and he followed through on that promise, netting Caroline enough cash to enhance her figure.
She then fell in love with a man and followed him to Kuwait, where he showered her with gifts like jewelry, dresses, and a penthouse apartment.
However, the man told her that if they continued the relationship, she couldn't have her SRS procedure, and she wasn't ready to sacrifice it and they split up.
After the break-up, in 1974, she finally raised enough money for the surgery by doing a striptease act in Rome - and that's also when the idea to model was first put into her head. People told her she should get into the business, and she quickly started working with an agency.
After landing a role in a James Bond film, Caroline was invited to pose for Playboy for the first time, appearing in the magazine in 1981.
However, the triumph was short-lived. In 1982, the now-defunct British tabloid News of the World spent 'a ton of money' to buy one of her old hospital files, which proved she she was born male.
'Once that happened, I went into hiding and even attempted suicide,' she said.
'I woke up in my bathroom in vomit. I just felt ashamed and embarrassed... And then at a certain point, I just got sick of being ashamed of something I'd never had any control over, which was my assigned gender.'
After attempting suicide, Caroline found her confidence again and eventually revisited the popular magazine.
Unfortunately, when she was ready to work again, she was only being offered 'gimmicky' transsexual roles - including a beer ad that said: 'She's coming your way, but she's a he.'
She constantly came up against ignorance, like when Howard Stern interviewed her while dressed as a woman and said that he'd had surgery, too. He even joked about cutting off his penis and handed her a sausage.
'I just felt like, I don't need this. I need to keep my sanity. I've got somebody who loves me, and I don't want to continue in this circus, and I stopped my career right there,' she said.
Luckily, 'times have changed' since then. She went on to pose for Playboy again, this time earning her own pictorial in 1991. Naked save for a leopard scarf creatively wrapped around her, Caroline posed sensuously in the groundbreaking feature.
'I wanted to do it because I wanted to show all the jocks and heterosexual Playboy readers that transgender people could be sexy and attractive and help them lose the preconceived notions they had about us,' she said.