Donald Trump engaged in crude and demeaning conversations about women over a 17-year-period with radio shock-jock Howard Stern, according to a review by CNN's KFile of hours of newly uncovered audio.

Among the topics Trump discussed: his daughter Ivanka's physique, having sex with women on their menstrual cycles, threesomes, and checking out of a relationship with women after they turn 35.

Trump's long track record of making misogynistic comments and engaging in lewd conversations about sex took on a new and much darker tone on Friday night, when the Washington Post published audio of Trump, caught on a hot mic in 2005, bragging about how women let him do whatever he wants to them because he's a celebrity.

While Trump's comments — in which he describes forcing himself upon women — stand apart from anything he has said in the past, Trump has long engaged in sexually explicit banter over the years, particularly on Stern. Trump appeared on Stern's radio program for decades, and while many of his appearances have been reported on, KFile's review has turned up previously unreported examples of Trump engaging in crude conversations.

On Ivanka Trump's physique

In more than one interview with Stern, Trump took part in conversations about Ivanka Trump's appearance, including one about the size of her breasts.

In an October 2006 interview, Stern remarks that Ivanka "looks more voluptuous than ever," and asked if she had gotten breast implants. Trump is willing to engage in the discussion about his own daughter, telling Stern that she did not get implants.

"She's actually always been very voluptuous," Trump responds. "She's tall, she's almost 6 feet tall and she's been, she's an amazing beauty."

In another interview, from September 2004, Stern asks Trump if he can call Ivanka "a piece of ass," to which Trump responds in the affirmative.

"My daughter is beautiful, Ivanka," says Trump.

"By the way, your daughter," says Stern.

"She's beautiful," responds Trump.

"Can I say this? A piece of ass," Stern responds.

"Yeah," says Trump.

On women's ages

In his interviews with Stern, Trump discussed leaving women after a certain age and dating younger women.

In a 2002 appearance, Trump calls 30 "a perfect age."

"Until she's 35," a co-host interjects.

"What is it at 35? It's called check-out time," Trump responds.

In a 2006 interview, Stern asks Trump, "Do you think you could now be banging 24-year-olds?"

"Oh, absolutely," Trump says.

"Would you do it?," asks Stern.

"I'd have no problem," Trump said.

Stern then asked Trump if he has an age limit.

"No, I have no age — I mean, I have age limit. I don't want to be like Congressman Foley, with, you know, 12-year-olds."

On his own sex life

Trump frequently talked about his personal sex life on Stern's radio program, which included him willingly engaging in a discussion about having sex with women on their menstrual cycles.

"Will you have sex with a woman if she's having her period? Go ahead," Stern asks Trump in a 1997 interview.

"I thought he was looking at Kate when he said that," Trump responded, looking at his "Art of Comeback" co-author and fellow guest Kate Bohner. "She's done that."

"Donald, seriously, you would not, right, am I correct?," asked Stern.

"Well, I've been there. I have been there Howard, as we all have," Trump responded.

"You don't like it?," asked Stern.

"Well, sometimes you get there by mistake," Trump said.

In the same interview, Stern also asked Trump, "Have you had a black women in bed?"

"Well, it depends on what your definition of black is," responded Trump.

"Interesting. I like this discussion. His bed is a rainbow," Stern said.

"The rainbow coalition, as Rev. Jesse would say," Trump said.

Later in the interview, Trump says he lost his virginity at "about 14."

"It was a young woman, who was really beautiful, she the hot little girl in high school or grammar school or whatever," Trump said. "She was hot. I haven't seen her. I haven't seen her."

In a 2008 interview, Trump said he was still having "a lot" of sex with his wife Melania. Later, when co-host Artie Lang asked Trump if he ever had a threesome -- describing multiple women together weighing 300 pounds -- Trump willingly responds in the affirmative, and actually suggests he has slept with three women collectively weighing 375 pounds.

"I wouldn't say 300, I would say could be about 375," said Trump. "I figure 125 a piece as opposed to 100."

"Haven't we all," Trump added about men having threesomes, "are we babies?"

In an 1993 appearance, Stern and Trump discussed wealthy men who cannot get dates, when Stern says the difference with Trump is that he satisfies the women he sleeps with.

"And I couldn't care less," Trump replied.

On Tiger Woods

In an April 2010 show, Trump engaged in a discussion on the marital infidelities of pro-golfer Tiger Woods. In the discussion, Trump engaged in extremely explicit discussions with Stern on Woods's sexual habits.

"Do you believe in sex addiction?" Stern asked Trump during a discussion of Woods and his then-wife, Elin Nordegren.

"No, I believe people like sex a lot," Trump said. "People like you, people like me. Tiger."

Asked if he ever slept with two or three women in one day, Trump responds, "I have no comment. Look, I like sex, so do you."

"She's hot, she's hot though right?," Stern asked Trump of Nordegren, after Trump said he's talked to Woods since his sex scandal broke in the news.

'Yeah, she's fine," said Trump.

"You don't think she's that hot?," Stern asked.

"It depends by what standard," Trump replied. "What standard are you judging?"

"I have a very high standard," added Trump. "Howard knows, because he got me in a lot of trouble once, he went over a list of 15 supermodels. You remember the list of supermodels. And he'd ask me, 'how was she?' How was she?' And I was married at the time, you know this was not a good question to be asking."

"I think she's good," Trump added of Nordegren's attractiveness.

"No, I'd say she's a solid nine, solid nine yeah," Trump said, when asked how he'd rate her.

When Stern suggested to him he should do a show where he just rates women, Trump said, "That may be the best idea of all I would say I'm the all-time judge, don't forget, I own the Miss Universe pageant."

"Mr. Trump I'm asking you directly, is her ass too big?" Stern asked.

"No," Trump replied.

"Body perfect?" Stern asked.

"Very nice," responded Trump.

"She's very nice, is she a 10, you know what a 10 is?" Trump asked.

Stern then brought up one of Woods's mistresses, saying, "She does a position where Tiger Woods— I'm gonna be a little bit graphic— Tiger stood her on her head -- listen to this..."

"Spun her around," Trump interjected while laughing.

"No, no, no," said Stern. "He put his penis in her behind and then put his fingers in the vagina..."

Trump responded by laughing, saying he's never done that position.

Trump added that Woods is definitely "not gay."

On beauty pageant contestants

In an April 2005 episode, Stern asked Trump if there was ever a time when he had sex with Miss Universe or Miss USA contestants.

"I never comment on things like that," Trump answered.

Later, Artie Lang interjects from the background, "Give us the first letter of the country you had sex with."

"How many letters are there?" Trump joked.

Stern then posed a scenario wherein one of the beauty pageant contestants went up to Trump and asked to have sex with him.

"Now you're not the type that would say no," Stern said.

"I don't want to hurt their feelings," Trump replied.

Co-host Robin Quivers then asked Trump if sleeping with the contestants could be construed as a conflict of interest.

"It could be a conflict of interest," Trump said. "But, you know, it's the kind of thing you worry about later, you tend to think about the conflict a little bit later on."

Stern then put on a fake foreign accent, saying that "some of these foreign girls" say hello "with vagina."

"Well, what you could also say is that, as the owner of the pageant, it's your obligation to do that," Trump said, before discussing how he got away with going backstage when the contestants were naked.

"Well, I'll tell you the funniest is that before a show, I'll go backstage and everyone's getting dressed, and everything else, and you know, no men are anywhere, and I'm allowed to go in because I'm the owner of the pageant and therefore I'm inspecting it," Trump said. "You know, I'm inspecting because I want to make sure that everything is good."

"You know, the dresses. 'Is everyone okay?' You know, they're standing there with no clothes. 'Is everybody okay?' And you see these incredible looking women, and so, I sort of get away with things like that. But no, I've been very good," he added.

Later in the episode, Stern asks Trump to assure his audience that "the chicks will be almost naked" at his pageant, saying to Trump that before he bought the contest, "they were starting to take women who were educated over women who were hot."

"They had a person who was extremely proud that a number of the women had become doctors," Trump explained. "And I wasn't interested."

He continued, "I actually went on the 'Today Show' with Katie Couric a while ago, six years ago, and we had a woman running the pageant who was really into the whole thing of education and everything and I said, 'Look, if you're looking for a rocket scientist, don't turn in tonight. But if you're looking for a really beautiful woman, you should watch.'"

Stern approved of Trump's approach, saying, "I'd rather have a retarded hot woman than a slob who's a doctor."

In a July 2008 appearance, Trump said he got a case of the "the shakes," when it was said Miss Universe would be held in Vietnam.

"The contest of all places was in Vietnam, which was very nice, I got a case of the shakes," Trump said. "It was in Vietnam. Vietnam's a hot country. But, you know, when I was going to high school, when I was going to college Vietnam was like the big deal. Like you have to leave college and go fight --. And I said, 'excuse me?' Now I'm going to Vietnam for a beauty pageant."

On Paula Jones

In a 2002 episode, Trump discussed the celebrity boxing match of Paula Jones, who in the 1990s accused Bill Clinton of sexual harassment.

"It was interesting. That Paula Jones fight, she was not very talented. That was pretty pathetic," Trump said.

"It's funny because Paula Jones would get hit, she'd run," Robin Quivers said.

"She would run, it's too bad she didn't run like that from Bill (Clinton)," Trump replied.

On infidelity

In a 1993 interview, Trump and Stern engaged in a conversation about fidelity in marriage, with Stern relaying how Trump was shocked when he told him that he doesn't cheat on his wife.

"Donald asked me during the commercials — and I don't think you mind me saying it — he says to me, 'so you don't get it on with anybody?," Stern says. "I said 'I'm really faithful to my wife' and he goes 'you're kidding? Really? What's that all about?'

"I can say to Howard's wife, that's true," Trump responds. "He did say that to me. It's great."

Trump adds, "I was actually faithful to my wife for many years, until I realized the marriage wasn't gonna work."

Later in the interview, Trump complained about his ex-wife Ivana's accent

"The funny thing about Ivana is the accent got worse as she grew older, and some people said she wanted it to happen. The accent actually became more pronounced as years went by," Trump said.

"It was like the Chinese torture. You know, the water drops on your head," Trump said.