CNN's KFILE has now uncovered two more Playboy videos in which Trump makes an appearance, including one in which he is depicted photographing fully clothed models with a Polaroid camera and conducting an interview with a potential Playmate.
In that video — a 1994 VHS tape obtained by CNN titled "Playboy Centerfold" — Trump takes part in Playboy magazine's search for its 40th anniversary Playmate.
The scenes featuring Trump do not contain nudity or sexually explicit content, but other scenes in the movie depict fully nude women seductively rubbing themselves in different scenarios.
In one scene, Trump interviews a potential model, asking her what qualities she possesses that would make her the right choice for the 40th anniversary cover.
"I believe that it's not just beauty, I think it's an attitude," the model says. "I think it has a lot to do with personality and an attitude. I think Playboy really represents that, and I believe that I have that, and I have what it takes to represent them."
"Well I think you have what it takes too," Trump replies. "And I think everyone in this room thinks you have what it takes also."
Bridget Marks, one of the models Trump interviewed, said in a phone interview with CNN that she had a positive experience with Trump that day and whenever she has seen him since.
"I thought he was thoughtful. I thought he was respectful. I had a very good time," said Marks, a registered Democrat who said she is remaining neutral in the presidential election. "He has remembered my name and been very nice to me and my family whenever I've seen him."
Jeff Cohen, a senior photo editor for Playboy who was at the event, said that the magazine wanted the publicity generated by Trump to launch its search for the 40th anniversary playmate.
"We sat around and decided, 'Let's launch the search in New York City,'" Cohen told CNN. "Obviously, the media capital. We'll get a lot of press, we'll get TV, we'll get radio. What's the best way to do that? Aha, I know, we're gonna ask Donald Trump whether he would come and photograph, do the test pictures, of the first girl that comes in.' And that's basically what we did."
Cohen, who said he's voting for Hillary Clinton, also added that Trump was very professional and businesslike in his interactions with everyone there.
Trump also appeared briefly in a 2001 Playboy video centered on a fashion show Playboy did with Betsey Johnson. The Republican nominee appears backstage, alongside two Playmates and his current wife and then-girlfriend, Melania Knauss. CNN's KFILE reviewed the video. Trump appeared at the fashion show along with other celebrities. Other scenes in the film, which do not feature Trump, depict fully nude women.
The Trump campaign did not respond to a request for comment from CNN.
The revelation that Trump has appeared in several Playboy videos comes as Democratic nominee Hillary Clinton seeks to make Trump's derogatory statements and actions toward women an issue in the campaign. At the first presidential debate, Clinton hit Trump over his past treatment of former Miss Universe Alicia Machado, whom Trump called "plumpy" and an "eating machine" after she won the pageant in 1996.
Last Friday, Trump attacked Machado on Twitter, telling his followers to "check out" her "sex tape" — an apparent reference to her appearance on a reality TV show in which she was filmed in grainy, night-vision footage having sex with another contestant on the show.
The latest CNN/ORC poll, conducted after the first debate, found that 62% of women viewed Trump unfavorably.
Trump has a long history with Playboy magazine, famously appearing on its cover in 1990. That interview made headlines when Trump infamously replied, "I don't have to answer that," when asked if his marriage was monogamous. His cover issue even appeared in television ads for the magazine in the early 1990s.
In an interview at the 2001 Playboy catwalk event with CNN correspondent Jeanne Moos, Trump was asked if he have ever dated a playmate.
"I refuse to answer that question," he replied.
"On the grounds that it may be true?," Moos asked.
"It may be true," Trump said.