http://www.cnn.com/2016/10/08/politics/trump-on-howard-stern/index.html?adkey=bn

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.
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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.
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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.”
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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.
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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.
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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.”
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n 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.”
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“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.”