WITH his long, grey hair, scrawny build and unkempt appearance, John Middleton cuts an unlikely figure as an underworld Mr Big.

To those who do not know him, it is hard to believe the 60-year-old businessman was the boss of a prostitution racket supplying men with sex-on-tap and, in the process, lining his pockets.

It is unclear what drove the company director to close his double-glazing showroom in Darlington and re-open it as a sex shop, but a motivation to make money seems the most obvious conclusion.

He certainly did not seem shy about advertising the sex shop and the services that went on upstairs.

Confident he would not get caught, Middleton advertised his mobile telephone number on the firm's website and encouraged clients to call for appointments with his girls.

In September 1998, Middleton shut down C Thru Windows, in North Road, and re-opened as the Pleasure Zone shop selling skimpy clothing and adult products.

He denied it was a sex shop and, following a visit from Darlington Borough Council, was told to consult a lawyer because he did not have a licence to sell some of the raunchier products.

The concerns were later said to be unfounded because the shop mainly sold clothes and did not require a licence.

In November 1999, Middleton decided to expand his business and open a massage parlour in the upstairs rooms of the shop.

This again sparked controversy, but the council said there was nothing it could do because the business was in a commercial area and did not require planning or licensing approval.

Middleton tried to alleviate the fears of residents. In an interview with The Northern Echo in 1999, he said: "This is a genuine massage parlour, and there is a call for such a service in Darlington.

"When we were forced to close down last time, we had people contacting us for three months after we shut the doors."

He later said the massage parlour would be legitimate and legal.

He said: "We all know that escort and massages can cover anything, but there will be no sex involved. It will be purely dinner dates."

In August 2000, he vowed to write to Prime Minister Tony Blair after the employment service refused to run adverts in job centres for a masseur and a shop assistant.

Two months later, his blatant advertising landed him in trouble again when Hambleton District Council began proceedings following complaints that his caravan near the A1 in North Yorkshire, which advertised massages, could distract drivers.

A year later, high on the earnings he was making from prostitutes, Middleton said he wanted to expand his business and open a lap-dancing club in North Yorkshire.

The project, which was to include bedrooms and a massage room for visitors, never got off the ground.

By the start of last year, Middleton could have been forgiven for thinking he had avoided detection.

But detectives were watching him and, following a raid at the shop in February, his vice den was exposed.

Clearly not the unassuming figure he appears, Middleton now faces jail, and the seizure of his earnings from prostitution are likely to leave him penniless.