Prostitutes, teen interns, aristocrats, even a woman named ‘Pooh’ – cheating JFK’s long list of sex partners detailed in new book which also reveals nickname he gave his private parts

He was the original horndog-in-chief.

And now the extraordinary extent of John F Kennedy’s ‘nearly uncontrollable’ sexual appetite has been laid bare in a new book detailing his thousands of alleged conquests and affairs. 

From losing his virginity in a Harlem brothel at 17 to a revolving door of young women at his disposal, Kennedy pursued what his friend, the late Senator George Smathers, described as a sexual appetite that spiraled ‘out of control.’ 

Veteran Kennedy biographer Laurence Leamer chronicles the 35th president’s exploits in eye-popping detail in Ladies’ Man: The Careless Heart of John F Kennedy, to be released October 20. 

By Leamer’s estimate, Kennedy bedded thousands of women in a ‘never-ending stream of lovers’ that included aristocrats, models, secretaries and even White House interns. 

While in the White House, Kennedy liked to have three ‘teenagers’ lined up at any given time, according to the book, and even instructed one intern to give oral sex to a top White House official. 

‘It was like the Rolling Stones on tour,’ one former Kennedy official recalled. 

Leamer argues that ‘one cannot come close to understanding Kennedy without coming to terms with [his] sexuality.

‘Through them we can trace Jack’s compulsive sexual behavior from his early years until his time in the White House where it became nearly uncontrollable,’ he writes. 

Kennedy learned early on that infidelity was tolerated if you were a Kennedy man: His father, Joseph P Kennedy, was a serial adulterer whose affairs are said to have included Hollywood stars Gloria Swanson and Marlene Dietrich.

But Leamer suggests the source of JFK’s own insatiable sexual appetite was his battle with chronic illness, which gave him a carpe diem spirit on steroids.

The future president was diagnosed with Addison’s disease, a rare and debilitating condition where the adrenal glands do not produce enough cortisol.

His sexual exploits began while attending Choate, the prestigious Connecticut boarding school where, as a teenager, he christened his penis ‘JJ Maher’ after a strict housemaster. 

At the age of 17, he took his classmate Kirk LeMoyne Billings, who would go on to become a lifelong friend, to a brothel in Harlem to ‘rid themselves of the affliction known as virginity.’

Billings was gay and, according to Leamer, was ‘possibly in love’ with Kennedy. But Kennedy had once rebuffed an earlier proposition, telling him: ‘I’m not that kind of boy.’

At the New York City brothel, Kennedy insisted they have sex with the same prostitute, paying $3 a piece. But while he went through with the encounter, Billings  just masturbated and closed his eyes, the author writes. 

Ever the reckless lover, Kennedy did not use a protection, a habit which led to him catching several bouts of venereal disease including gonorrhea, according to the book. 

In a remarkably candid letter to Billings in 1936, written after a visit to another brothel in Mexico, Kennedy joked about the establishment’s reputation for spreading gonorrhea. 

‘I ended up in a 2-bit hoarhouse [sic] and they said that one guy in 5 years had gotten away without just the biggest juiciest load of claps,’ he wrote, referring to gonorrhea. 

‘Always get your piece of arse in the most unhealthy place that can be found,’ Kennedy added. 

His womanizing and partying continued at Harvard University, where his father’s aide Eddie Moore set up dates with ‘young women open to adventure’ for him at the Kennedy family compound in Hyannis Port, Massachusetts.

In another letter to Billings, Kennedy boasted about a weekend of sexual encounters, writing: ‘One guy got f***** 3 times, another guy 3 times (*the girl a virgin! + myself twice.’

‘One guy is up at the doctor’s to see if he has the clap. And I am not too secure myself.’ Not to be deterred, he added: ‘We are going down next week for a return performance, I think.’

Kennedy enrolled for a time at Stanford Business School in California, which was, much to his delight, co-ed.

According to fellow Stanford student Henry James, the future president had little time for sentimentality with the opposite sex.

‘His (Kennedy’s) favorite phrase was: ‘Slam, Bam, Thank You, Ma’am,’ James said.

‘I’m not interested once I get a woman. I like the conquest. That’s the challenge. It’s the chase I like – not the kill,’ Kennedy reportedly told him. 

Those early escapades set the stage for a lifetime of sexual adventures, even as he climbed the political ladder and went on to marry Jacqueline Bouvier in 1953. 

Among those who he had flings with was Inga Arvad, a twice-married Danish journalist, who once wrote a flattering profile of Hitler.

According to Leamer, Kennedy became ‘terribly dependent’ on Arvad because she was so motherly to him, all while the FBI listened in covertly because they suspected she was a spy.

Kennedy later fell hard for Gunilla von Post, a Swedish aristocrat he met on a last jaunt before his marriage to Jackie. 

According to Leamer, Kennedy was so smitten with von Post he offered to set her up with an apartment in New York’s famed Carlyle Hotel and get her work as a model, but she declined.

In an interview for the book, von Post described how Kennedy, who flew to Sweden to have sex with her, made love ‘with his hands, with his marvelous, healthy Irish skin, with his mouth, with everything.’

Kennedy later met the stunning brunette Diana de Vegh, then a junior at Radcliffe College, at the Statler Hilton Ballroom in Boston in 1958 while serving as a first-term Senator.

He was so brazen that he asked de Vegh’s date, James Alley, to give up his seat so he could sit next to the ‘pretty girl.’

So began a months-long affair where Kennedy would pick her up for sex whenever he was in Boston.

De Vegh initially thought he was seriously courting her, but soon came to realize it was all about sex – and she went along with it.

Speaking to Leamer, De Vegh says: ‘There were no deeply meaningful conversations… it was chit chat and then some sex and go home. 

‘I went for the daring adventure outside of my world. If it involved sex for attention… well, okay,’ she told the author. 

One of the most outrageous episodes of Kennedy’s life happened in 1956 while Jackie was heavily pregnant with their first child, Caroline.

Kennedy declined to stay by his wife’s side in Massachusetts and instead flew to Europe to party with his friends on a yacht, including having sex with a blonde woman who went by ‘Pooh.’

Meanwhile, back in America, Jackie gave birth – but their daughter Arabella was stillborn.

Kennedy’s friend Smathers had to urge him to return to America.

According to Leamer, once he arrived it became clear that Kennedy had ‘gone too far’ and Jackie was furious over his ‘disdain and disregard.’

There were rumors that Joseph P Kennedy paid Jackie $1 million to stay with his son as he knew Kennedy couldn’t become president if he were to get divorced.

Yet even this didn’t slow Kennedy down. After being elected to the White House in 1960, his appetites became only more ravenous.

In one extraordinary arrangement, Kennedy hired Pamela Turnure to be his wife’s press secretary while secretly having an affair with her.

Another lover, Helen Chavchavadze, a brunette divorcée with two young daughters, was shocked that Kennedy would drive to her house – with the Secret Service and reporters in tow – for sex.

Former Secret Service agent William T McIntyre remembers seeing ‘hookers’ brought into the White House, where they would party in the pool with the president, who liked to go into the water to ease his back pain.

Kennedy’s other alleged conquests included Marilyn Monroe and Judith Exner even though she was having an affair with mob boss Sam Giancana at the same time.

Milt Ebbins, the manager of the late actor Peter Lawford, who was married to Kennedy’s sister Patricia, claimed that Exner was paid $200 to sleep with Kennedy in 1959, when the then-senator was in Las Vegas to hang out with Frank Sinatra.

The implication is that the mob could have potentially blackmailed Kennedy, yet Leamer says no specific instances have been identified.

Then there was White House intern Mimi Beardsley who, according to the book, would have scored a perfect 1600 if Kennedy had devised an SAT score for potential mistresses.

‘He liked young women who were lithe and unworldly,’ Leamer writes, describing women whose sexuality was ‘reserved for him to awaken’ and who had ‘hardly even been kissed.’

On a tour of the White House on her fourth day there, Kennedy took Beardsley into Jackie’s bedroom and began to undress her, leaving her ‘stunned into acquiescence.’

It was her first time having sex but would not be her last with Kennedy, who moved her into that White House that summer as Jackie was away.

Kennedy would take long baths with Beardsley, listen to Broadway show tunes with her, but never once kissed her – and she called him ‘Mr President.’

She became a ‘pleasurable escape’ from the difficult problems he had to handle as president because she didn’t ask difficult questions, Leamer writes.

Two months into their affair, Kennedy instructed Beardsley to give oral sex to David Powers, his senior adviser, according to the book. 

Leamer writes this showed ‘total disregard’ for Beardsley, but she did it.

Another time, Kennedy told Beardsley to ‘take care of my baby brother’ – meaning to do the same for Ted Kennedy as she did for Powers.

The request was delivered as casually as if Kennedy was ‘ordering room service,’ but Beardsley refused.

It was one of the very few times a woman said no to him. 

Ladies’ Man: The Careless Heart of John F Kennedy by Laurence Leamer is available for pre-order at Amazon.com.