Donald Trump has made numerous crude and misogynistic comments towards women, including agreeing that his daughter Ivanka Trump is 'a piece of a**' while appearing as a guest on the Howard Stern radio show.

Trump has engaged in lewd conversations with the shock jock over a 17-year period that focused on his daughter Ivanka, his preference for younger women, his sex life, how he 'couldn't care less' if he satisfies the women he sleeps with and losing his virginity to a 'hot little girl' when he was 14 years old, according to a review of the interviews by CNN.

While being interviewed for a September 2004 show, the billionaire businessman who was 58 years old at the time, told Stern that his then 22-year-old daughter was 'beautiful.'

'Can I say this?' asked Stern. 'A piece of a**?'

'Yeah,' replied Trump.

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Donald Trump has engaged in lewd conversations with Howard Stern on his show over a 17-year period. Above Trump and Stern are pictured together at a 2005 basketball game with Melania Trump and Stern's wife Beth Ostrosky

During a September 2004 show, Trump told Stern that Ivanka was beautiful before Stern asked if he could call her 'a piece of a**' and Trump agreed. Ivanka is pictured above in 2004 at age 22

Roughly two years later in a October 2006 interview, Stern and Trump discussed Ivanka's breasts on the show.

Stern remarked that Ivanka 'looks more voluptuous than ever,' and asked if she had breast implants.

Trump told Stern that she never had surgery for breast implants.

'She's always been quite voluptuous,' said Trump.

'She's tall, she's almost 6 feet tall and she's been, she's an amazing beauty.'

Trump on Howard Stern in 2003: On how he'd date Ivanka if she wasn't his daughter

In another Howard Stern interview from 2003, Trump bragged about his daughter's figure, saying: 'You know who's one of the great beauties of the world, according to everybody? And I helped create her. Ivanka. My daughter, Ivanka. She's 6 feet tall, she's got the best body. She made a lot money as a model—a tremendous amount.'

He's also suggested that he might be dating his daughter, if they weren't related.

'I've said if Ivanka weren't my daughter, perhaps I'd be dating her,' Trump said in an appearance on The View.

In that same 2006 interview with Stern, Trump said that Ivanka has 'always been quite voluptuous.' Above Ivanka is left, Trump is center and Melania is right in 2006

Trump on Howard Stern in 2006: On having sex with 24-year-olds

During an interview also from 2006, Stern asked Trump, who was aged 60 at the time, if he would be willing to have sex with 24-year-old women.

'Oh, absolutely,' Trump replied.

'Would you do it?,' Stern asked.

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

The shock jock followed that up by asking Trump if he had 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.'

Trump said that his daughter is 'an amazing beauty.' Above Ivanka sits on her father's lap in 1996 during a concert

Trump on Howard Stern in 2002: On 30 being the 'perfect' age

During a 2002 interview, the two men talked about leaving relationships with women after they pass a certain age.

Trump said the 'perfect age' was 30 for women, until someone interrupted and said 'until she's 35.'

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

Trump on Howard Stern in 1997: On having sex with women on their menstrual cycles

In that same interview, Stern asked Trump if he would have sex with women on their menstrual cycles.

'Will you have sex with a woman if she's having her period? Go ahead,' Stern asked Trump.

'I thought he was looking at Kate when he said that,' Trump replied while 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.

Trump on Howard Stern in 1997: On having sex with black women

Also in that same interview in 1997, Stern asked The Donald if he had ever had sex with a black woman.

Trump said, 'Well, it depends on what your definition of black is.'

'Interesting. I like this discussion. His bed is a rainbow,' Stern replied.

'The rainbow coalition, as Rev. Jesse would say,' Trump stated.

Trump on Howard Stern in 1997: On how he lost his virginity

In that same conversation with Stern from 1997, the pair discussed how he lost his virginity to a 'hot little girl'.

'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.'

The Republican also discussed in an April 2005 interview how he barged in on nude Miss Universe beauty pageant contestants in their dressing rooms. Above Stern and Trump in 2000

Trump on Howard Stern in 2005: On seeing Miss Universe contestants nude

The Republican also discussed in an April 2005 interview how he barged in on nude Miss Universe beauty pageant contestants in their dressing rooms.

He characterized those visits as 'inspections' since he owned the contest.

'Well, what you could also say is that, as the owner of the pageant, it's your obligation to do that,' Trump said.

'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.

'You know, I'm inspecting because I want to make sure that everything is good.'

He added: '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.'

Trump on Howard Stern in 2005: On if he had sex with Miss Universe contestants

In that same interview, Stern asked Trump if he had ever had sex with a Miss Universe or Miss USA contestants.

'I never comment on things like that,' Trump replied.

Later on in the interview, Artie Lang interjected and said, 'Give us the first letter of the country you had sex with.'

'How many letters are there?' Trump joked back to Lang.

Stern then proposed a scenario to the real estate mogul where one of the beauty pageant contestants went to him 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.

Another person on the show asked if Trump having sex with contestants could be considered 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.'

He discussed in an April 2005 interview how he barged in on nude Miss Universe contestants in their dressing rooms. Trump is pictured above with Miss Teen USA, Miss Universe and Miss USA in 2005

Trump on Howard Stern in 2005: On not being interested in education level of Miss Universe contestants

During that same interview in 2005, Stern asked The Donald about how the pageant contests would be 'almost naked' to reassure his audience.

Stern added that prior to Trump owning 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 on the show. 'And I wasn't interested.

'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 agreed with Trump's approach and said:'I'd rather have a retarded hot woman than a slob who's a doctor.'

In a 1993 interview, Trump complained about his ex-wife Ivana's accent and said it 'grew worse as she grew older.' They are pictured above together in 1992

In that same conversation from 1993, Trump said: 'I was actually faithful to my wife for many years, until I realized the marriage wasn't gonna work.' They are pictured together in 1984

Trump on Howard Stern in 1993: On his ex-wife Ivana's accent

In a 1993 interview, Trump complained about his ex-wife Ivana's accent, as she was born in the Czech Republic.

'The funny thing about Ivana is the accent got worse as she grew older, and some people said she wanted it to happen,' he said.

'The accent actually became more pronounced as years went by.

'It was like the Chinese torture. You know, the water drops on your head.'

In that same conversation, Trump said: 'I was actually faithful to my wife for many years, until I realized the marriage wasn't gonna work.'

During a 2008 interview on Stern's show, Trump shared that he was having 'a lot' of sex with his wife, Melania. Trump is pictured above with his wife in 2008

Trump on Howard Stern in 2008: On having threesomes

During a 2008 interview on Stern's show, Trump shared that he was having 'a lot' of sex with his wife, Melania.

He was asked later on by Lang if he had a threesome, and described it as multiple women together weighing 300 pounds.

'I wouldn't say 300, I would say could be about 375,' the real estate mogul said. 'I figure 125 a piece as opposed to 100.'

'Haven't we all,' Trump added in reference to men having threesomes.