Michael Caborn-Waterfield was a colourful character in post-war London, a gentleman adventurer who had relationships with Diana Dors and Samantha Eggar, smuggled guns into Cuba, served time in a French jail and set up the first Ann Summers sex shop. He also had a short stint as an amateur rider under National Hunt rules.

Michael George Kimberley Caborn-Waterfield was born on New Year’s Day 1930, the son of Vivian Conrad George Colnaghi Caborn-Waterfield, a pilot in the Fleet Air Arm who died in 1944. Kim was educated at Cranleigh, from which he ran away aged 16 to a racing stable where he briefly pursued an ambition to become a jockey.

When that did not work out, he became an actor and a trader in black-market nylons. Reputed to have several West End stage-doormen on his payroll, by the late 1940s he had three cars and a flat in St John’s Wood.

In 1949 he began dating teenage Rank starlet Diana Dors. The relationship ended after two years, though they remained good friends, and she went on to marry Dennis Hamilton, a door-to-door salesman with whom Michael would become involved in a fracas at the Embassy Club in 1955, resulting in a conviction for “insulting behaviour”. In the meantime, Michael had become the leader of a smart Chelsea set, throwing parties attended by the likes of Lord Lucan, his good looks and natty dress sense (a friend recalled his collection of 25 handmade suits) earning him the nickname “Dandy Kim”.

He had a succession of lovers including the actress Samantha Eggar. In the mid-1950s he took up with Barbara Warner, daughter of the Hollywood mogul Jack, and in 1956 was found guilty in absentia by a French court of the theft of £23,000 in francs from Warner’s home on the French Riviera and sentenced to four years in jail.

In 1960, after running guns for the Cuban dictator Batista, opening a water skiing school in Tangiers (from where he claimed to have been spirited back to Britain by the Kray twins after the French authorities tracked him down), Michael was eventually extradited to France, but only served 12 months of his sentence.

After his release he bought a manor on the Dorset-Wiltshire border and became a keen rider to hounds with the South and West Wilts Hunt. Back in London he returned to the Chelsea social scene, cruising the King’s Road in his Bentley and hosting parties frequented by, among others, Stephen Ward, the society osteopath, who turned up with Mandy Rice-Davies and Christine Keeler.

By the late 1960s he was ready for a new venture. In 1970 he opened the first Ann Summers sex shop near Marble Arch, naming the enterprise after a former girlfriend who was working as manager of his Dorset estate. He felt that his own name and notoriety might be bad for business.

The ex-girlfriend (Annice Summers) agreed to help with the new venture and for 12 months Ann Summers and “her” shops were a sensation. In the face of horrifying opposition from church groups and councils, the “convent-educated” Ann became famous as the standard-bearer for the sexual revolution. In 1971 the London Evening Standard named her Woman of the Year. But later the same year she resigned, saying that she had become concerned about some of the products sold under her name, as well as the fact that the financial rewards Michael had promised had not materialised.

In 1972 Michael married Penny Brahms, a model and actress who had co-starred with Joanna Lumley in the 1971 sex comedy Games That Lovers Play, and with whom he had a daughter, although the marriage did not last.

On January 1, 1974, he celebrated his 44th birthday by riding his 13-year-old Mandrill in a handicap hurdle at Windsor. After being prominent to the third flight, they were tailed off from the fifth and trailed home well behind the rest of the field, anchored by the rider’s 23lb overweight. He rode Mandrill in five more races between January and May, usually finishing tailed off, his best placing being seventh at Wincanton on Easter Monday. His mount was possibly better than the bare form suggested but his ability was compromised by his owner-rider constantly putting up anything between 9lb and 22lb overweight.

In 1976 Michael proposed a Miss Topless World beauty pageant, which did not, in the end, come off.

Described as a “restless spirit”, he had a somewhat cavalier attitude to banks and when he was short of funds had a habit of “evaporating” into thin air. He lived in Australia for a time. In 2000 the Daily Mail reported that he had “eschewed his natural milieu of a flat in Chelsea’s Kings Road to pursue the life of a ‘tax exile’ near Dublin”.

Michael Caborn-Waterfield later moved back to London. He died on 6 May 2016, aged 86,