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A former manager of one of George Soros’ investment funds has been accused of human trafficking, violent rape and assault in an extraordinary $27million lawsuit filed by three Florida models.

Howard ‘Howie’ Rubin, 62, is accused of sexually assaulting three women, two of whom are former Playboy bunnies, at an $8million penthouse in Manhattan in 2016 which contains a secret ‘dungeon’ of sex toys, masks and BDSM ‘apparatus’.

The women claim Rubin and his associates lured them to New York on JetBlue flights after contacting them on Instagram.

Once in Manhattan, they say he drugged them then violently beat them while they were gagged and bound in the sex dungeon, hitting woman so hard that she passed out as he demanded she call him ‘daddy’.

Two of them say he warned them: ‘I’m going to rape you like I rape my daughter,’ before attacking them and one says he punched her breast so hard her implant ‘flipped’.

They say he then covered up the alleged rapes and attacks and hushed them by paying them up to $5,000 each. His associates then gave them money to cover medical expenses incurred by the injuries he inflicted on them, they said.

They detail their allegations in a 63-page lawsuit filed in Brooklyn, New York, on Thursday which DailyMail.com has seen.

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Howard  Rubin, 62, pictured with his wife Mary Henry, has been accused or rape, assault and human trafficking in a sensational $27million lawsuit filed by three Florida women including two former Playboy bunnies

Rubin, a notorious Wall Street trader who is blamed for incurring $377million of losses at Merrill Lynch in 1987 and who is featured in Liar’s Poker, has not yet responded to their allegations.

He is named alongside associated Stephanie Shon, Jennifer Powers,  and lawyer Yifat Schnur in the lawsuit.

Rubin has been married since the 1980s to his former Harvard Business School classmate Mary Henry. They have three children together.

The lawsuit describes four different incidents in 2016. The women sometimes traveled to meet him in pairs and on other occasions they went alone, they said.

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The suit says Rubin’s ‘chief crime location’ was the Metropolitan Tower (the glass tower on the left) in Manhattan where the women say he beat and raped them in an $8million penthouse

Each claimed they returned after the first violent encounter because they needed money.

All say they were first contacted by Rubin’s staff on Instagram through its direct messaging function.

Rubin’s associates Stephanie Shon and Jennifer Powers, a former model herself who claimed to have slept with Rubin before starting to work for him, allegedly offered them thousands of dollars and free flights to New York to appear in photo-shoots and offer him ‘companionship’.

Once they were in the city, they say they were took cabs to the penthouse from the airport and were met by his employees who forced them to sign NDAs before they could meet him.

The women say they then went to a nearby bar for dinner and drinks then returned to the apartment where they claim Rubin drugged, beat and raped them before leaving ‘to go home to his wife and kids’.

Once in the penthouse, the women say Rubin turned on them and had violent sex, often beating them so severely that they required medical treatment.

His associates then offered them more cash in exchange for their silence and paid their medical bills, they claim.

One alleged victim says he once beat her so badly that her breast implant ‘flipped’. Another says he once threatened: ‘I’m going to rape you like my daughter.’

Rubin allegedly ordered co-defendants to contact the women on social media, initiating the contact.

One says that in August this year, she received a direct message from Stephanie Shon on Instagram.

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The view from Metropolitan Tower in Manhattan where the women say the abuse took place. They allege that Rubin bought the apartment through the company Blue Icarus in 2010

‘Shon indicated that she worked for Howard Rubin, and that Rubin, who had seen images of her on Instagram, would like to meet her in New York. While Shon initially identified Rubin by name, she then insisted that the woman refer to him only as “H” so as to protect Rubin’s identity’ the lawsuit reads.

Shon then allegedly told the woman her boss ‘loved spending time with Playboy models’.

The initial payment for the trip was $2,000 plus expenses, she said. If Rubin ‘liked her’, she would receive an additional $3,000, she claimed.

The alleged victim refused because she had never heard of him, she said. Rubin then allegedly had Powers contact her on the phone and over WhatsApp to persuade her to change her mind.

‘Powers assured her that Rubin was “a great guy,” and would not do anything to make her feel uncomfortable. Powers told her that if she ever felt uncomfortable she could simply ask to leave, and would not only be allowed to do so, but would still be paid the initial $2,000 for her time,’ it continues.

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The women say they met with him for dinner and drinks first at the Viceroy Central Park (above)

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Another says Rubin took her to Tao Uptown (above) before bringing her back to the ‘penthouse’ to rape her

She reluctantly agreed on the condition that she could bring one of the other Plaintiffs, who she was friends with, with her.

That woman had already received a similar request from Shon and Powers, she said. In their messages to her, they said Rubin liked ‘large breasted’ women.

To her, they allegedly insisted that she would not be required to have sex and that ‘at most’ Rubin wanted to engage in ‘fetish play’.

The two women then flew to New York from Florida on JetBlue flights paid for by Rubin, they said.

Once they arrived at the penthouse, they claimed they were given a cocktail by Powers. Inside the apartment were photographs of famous playmates, they said. Rubin also appeared in some of the images.

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The women suggested Rubin violently beat them and one alleges that he raped her with a cattle prod

They were then presented with NDAs, they said, which they signed. They were then taken to the Viceroy Central Park where they claim they met Rubin on the roof.

After dinner and drinks, where they said he was ‘cordial and respectful’, they claim they all returned to the penthouse and Rubin’s demeanor changed.

He then allegedly ordered them to change into fetish clothes and fixed them drinks out of sight which they believe were spiked.

The woman say he then opened the door to a previously locked dungeon which contained sex toys ‘labeled A-Z’ and ‘a large x-shaped machine with straps, a bench, full-face masks with zippers, and metal hooks.’

‘Rubin brought the women into this side room (the “Dungeon”) and immediately slapped [one of them] across the face.

‘Not only had the slap been unexpected and hurt, but [she] had recently undergone a cosmetic treatment to her face, known commonly as fillers, and was concerned that Rubin would damage the treatment,’ the lawsuit reads.

He then allegedly ordered that woman to hit the other. When she refused, he said he hit her too.

They say he then tied them up, gagged them and said: ‘I’m going to rape you like I rape my daughter.’

He then punched them in the backs of their heads, breasts and rib cages, calling them c**ts and becoming more violent if they screamed, they said.

Rubin then allegedly threw one woman to the ground and ordered her to call him ‘daddy’ while he beat her in the back of the head until she lost consciousness.

‘He continued to punch her, stating that: “Howie is the daddy. The daddy has to beat his baby.’  The woman says he then raped her so violently it caused ‘tears to her vagina’.

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Rubin is seen here with his eldest daughter at her debutante ball in a throwback photo she posted to wish him a happy Father’s Day

They say that after an hour of abuse, he left to ‘go home to his wife and children.’ Powers, the aforementioned employee, then stepped in to try to ‘soothe the traumatized victims’.

The women stayed in the penthouse for the night then flew back to Florida the next day as planned, they said.

Despite their ordeal, one of the women introduced him to another of her friends, claiming she was afraid of what he may do to her if she did not appear to appease him. Rubin allegedly paid her $2,000 for the introduction to the third woman.

She then flew to New York by herself in September 2016 and met him the same restaurant where he’d had dinner and drinks with the two other women.

She claims she knew how violent he had been with the others and told him she was ‘nervous’ about what he would do to her but was assured she would be in safe hands, the lawsuit claims.

When she went back to the penthouse, she said she drank all of what he gave her because she was nervous.

Once she was drunk, she claims she began talking about her daughter. She says he said he ‘slapped’ her, told her he was ‘completely turned off’, left $2,000 on the table then told her to leave which she did the next day.

Despite their first meeting, she agreed to go back weeks later, this time taking back with her the woman who says he raped her in August 2016.

Both claim they returned to New York on September 24, 2016 and met him for dinner at Tao Uptown, an upscale restaurant on the Upper East Side.  Afterwards, they claim he angrily raped one of them after tying them up in the master bedroom of the penthouse.

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Rubin and his wife are regulars on the New York City social circuit. They are pictured at a 2013 event

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The women say that after raping them in the penthouse, Rubin returned to his home on the Upper East Side. It is another multi-million dollar apartment inside this building

In December 2016, he allegedly attacked another of the women with a cattle prod while she visited him by herself.

He raped her with the prod, then with a dildo and finally raped him herself, she claimed.

On other occasions the women say they met with him in Miami and had dinner with him and Wes Edens, owner of the Milwaukee Bucks.

There was no answer at Rubin’s Upper East Side home on Friday.

He began his career in mortgaged-backed securities at Salomon Brothers in 1982.

He joined the Mortgage Department at Bear Stearns, becoming a Senior Managing Director and head of the CMO Trading Desk before retiring in 1999 as one of the most-respected men on Wall Street.

In 1987, Rubin caused historic losses at Merrill Lynch through a series of unauthorized trades which cost the company $250million. The figure was later reported by The New York Times to be as high as $377million.

At the time, Wall Street insiders told how he bought billions of dollars worth of mortgage bonds without receiving approval from his seniors.

When the market plummeted, he was unable to sell them off and incurred astronomical losses for the company.

He was fired and the matter was turned over to Wall Street watchdogs but Rubin was never criminally prosecuted.

Despite the loss, he was appointed Senior Managing Director at Bear Stearns, where he ran the Collateralized Mortgage Obligations desk from 1987 to 1999.

In 2008 he came out of retirement to manage a Mortgage-Backed Securities Fund for financier George Soros, run by Soros Fund Management, LLC. He quit the firm in 2015.

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In 2008, Rubin came out of retirement to manage a Mortgage-Backed Securities Fund for billionaire financier George Soros (pictured). He left in 2015, before the alleged sex attacks

Rubin has been married to philanthropist and fellow Harvard Business School graduate Mary Henry since 1985.

Before attending Harvard Business School, he attended Lafayette College in Pennsylvania.

The couple raised their three children in New York on the Upper East Side and also have a house in the Hamptons.

They have two daughters and then a son, the oldest child just graduated college.

Jeremy Saland of Crotty Saland PC, who is representing the women, told DailyMail.com in a statement: ‘While arrogance and self-import may convince certain men otherwise, neither money nor power gives any person the right to victimize a woman.

‘It is our collective responsibility to ensure that victims’ voices are heard, and that abusers’ positions of privilege do not exempt them from the grasp of justice.’

John Balestriere of Balestriere Fariello, another of the women’s lawyers, added his fear there were other victims. ‘We implore other victims of the Enterprise to contact us,’ he said.