Escort jailed for over five years after conning 'sugar daddy' of £2.5m

Escort girl, 35, is jailed for more than five years after conning retired Deloitte’s millionaire businessman ‘sugar daddy’ 35 years her senior out of £2.5million

  • Louise Caplan, of Buckinghamshire, was jailed for more than five years for fraud 
  • Escort Caplan, 34, was booked by millionaire banker Henry Sless on a website
  • He invested £2.5m into fraudulent businesses and gave her £1m worth of gifts
  • Mr Sless was under the impression they were in a relationship and would marry 

An escort has been jailed for more than five years after conning her ‘sugar daddy’, an elderly Deloitte’s millionaire businessman 35 years her senior, out of £2.5million.

Louise Caplan, 34, from Chalfont Saint Giles, Buckinghamshire, was booked by Henry Sless through escort website Adult Works in November 2017 after he agreed to pay her £400 for sex, and they started dating.

Caplan asked the retired banker, who was 65 at the time, to be her ‘sugar daddy’ in exchange for £150,000-a-year but Mr Sless managed to negotiate the fee down to £10,000 a month, the court heard. 

The millionaire, who lives in expensive riverside Marlow, Buckinghamshire, put £2.5million into her fraudulent business ventures in Dubai and Dublin and showered her with more than £1million worth of gifts.

But prosecutors told the court Caplan bought herself a £1million house and artwork worth £300,000 with the money she claimed she was investing in her interior design businesses. 

Escort Louise Caplan (pictured) from Buckinghamshire, was booked by Henry Sless through a website and he was so smitten that he was conned out of millions of pounds, the court heard

Prosecutor Stefan Weidmann told the court that when Mr Sless gave Caplan enormous loans, he believed the pair were in a long-term relationship and had a future together.

Millionaire Mr Sless, who was accountancy firm Deloitte’s global tax portfolio holder for more than ten years before retiring, believed the pair would get married and raise Caplan’s daughter together.  

A statement from Mr Sless, read to the court by Mr Weidmann, read: ‘It felt like we clicked immediately and within a few days of our first meeting Ms Caplan sent a message saying she would have married me if I would have been 10 years younger and she was 10 years older. 

‘We met five or so times in the first year and we were in contact on a daily basis. I instantly fell for her.’

As the relationship developed, the court heard how Caplan began to demand money from Mr Sless, often in erotically charged messages that were drenched in affection. 

It was also revealed that the couple had met on at least six occasions for sex, although Judge Francis Sheridan suggested it could have been many more times.

Caplan (pictured) asked the retired banker to be her ‘sugar daddy’ in exchange for £150,000-a-year but Mr Sless managed to negotiate the fee down to £10,000 a month, the court heard

Over the course of their relationship, the wealthy tax executive showered Caplan with gifts worth £1million. But the court heard that the escort defrauded him out of at least £2.5million.

A tearful Caplan looked heartbroken as she sat weeping the dock as the court heard she had spent more than £1million on a luxury house in Farnham Common, Buckinghamshire.

She also splashed out nearly £313,000 on artwork and £619,000 on luxury retail goods, despite having previously had an annual income of only £7,000.

The astonished judge was told that despite the enormous scale of the loans Mr Sless was handing out, the veteran accountant did not demand any paperwork. 

Prosecutor Stefan Weidmann said he gave the loans on an informal basis on the understanding that they were in a long-term relationship.

But Judge Sheridan, dismissing claims that the victim was ‘vulnerable, questioned: ‘Of course he would have had paperwork, he was an accountant? What am I missing?’

Mr Weidmann admitted that Mr Sless was a man of ‘staggering naivety’, despite his vast experience. 

He had believed that the money was going to be spent on property development in Dublin and Dubai, despite having seen only very limited evidence of their existence. 

Defending John Swaine said she attempted to use the money to pursue her dream of becoming a successful interior designer, and it was only when the bills began to catch up with her that she turned to fraud.

Prosecutors told the court Caplan (picutred) bought herself a £1million house and expensive artwork worth £300,000 with the money she claimed she was investing in her businesses

He said: ‘She intended to use this money in a business but she was hopelessly out of her depth. She hired expensive accountants who advised her that she had no hope of success.

‘Her huge error was not to go to Mr Sless and say I have been stupid and I have let you down. She had no hope of paying this all back.’

Caplan had earlier admitted one count of fraud and was sentenced to five and a quarter years in prison.

Judge Sheridan said: ‘I am in no position to tell the truth of how many times he took advantage of your sexual services.

‘It was at least six times but I am strongly suspicious about that given the extremely large figures in this fraud. This had all the hallmarks of a business arrangement and if it was business, it was certainly not done properly.’

A tearful Caplan remained standing in the dock, before she waved to her mother, who sat in the public gallery, and told her to pass on her love to her daughter.

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