Ann Charteris, the eldest daughter of Lawrence Charteris (1886–1967) and his first wife, Frances Lucy Tennant (1887–1925), was born at Stanway, Gloucestershire, on 19th June 1913. Her father was the second son of Francis Wemyss-Charteris, 9th Earl of Wemyss. After her mother died, she spent long periods at her grandparents' home in the Cotswolds.
Ann only spent one term at Cheltenham Ladies' College, before being educated at home by governesses. In 1931 she ‘came out’ as a débutante at a party given by her aunt, Kathleen Manners, the Duchess of Rutland. On 6th October 1932, Ann married Shane Edward Robert O'Neill, third Baron O'Neill, a wealthy peer with a job in the City. His father, Arthur Edward O'Neill, was the first MP killed on active service in the First World War. According to her biographer, Andrew Lycett: "Settling into a conventional social life in London and Northern Ireland (where the O'Neills had a hereditary seat), Ann gave birth to two children, Raymond and Fionn." Ann was strongly attracted to other men and had affairs with Esmond Cecil Harmsworth, heir to Lord Rothermere, owner of The Daily Mail and Ian Fleming, a young stockbroker.
Shane Edward Robert O'Neill joined the armed forces on the outbreak of the Second World War. Ann took a house in Gloucestershire and spent most of her time with Esmond Cecil Harmsworth at the Dorchester Hotel. She also continued to see Fleming, who was now assistant to the director of naval intelligence. Lieutenant Colonel O'Neill was killed in Italy in October 1944.
After the war Anne married Esmond Cecil Harmsworth, who was now Viscount Rothermere. According to Andrew Lycett: "She lived in great luxury at Warwick House, off Green Park, London, after their marriage on 28 June 1945. She fought post-war austerity with sumptuous parties, which mixed her husband's associates, the more interesting aristocrats, and a new generation of writers and artists - among them Lucian Freud, Frederick Ashton, Francis Bacon, and Peter Quennell."
Anne continued her affair with Ian Fleming. She enjoyed three months' holiday every year in Jamaica, where she pretended to visit her friend Noël Coward while in reality she stayed with Fleming. Ann wrote to Fleming in 1947 after one of her visits: "It was so short and so full of happiness, and I am afraid I loved cooking for you and sleeping beside you and being whipped by you... I don't think I have ever loved like this before." Fleming replied: "All the love I have for you has grown out of me because you made it grow. Without you I would still be hard and dead and cold and quite unable to write this childish letter, full of love and jealousies and adolescence." In 1948 Ann gave birth to his daughter, Mary, who lived only a few hours.
In 1951 Esmond Cecil Harmsworth, who discovered her relationship with Fleming, divorced Ann. Her £100,000 divorce settlement enabled her to live in luxury with the unemployed Fleming. On 24th March 1952 she married Fleming. The very next day, he sat down and began writing Casino Royale. The author of Ian Fleming (1996) has argued that whenever he was in Jamaica, he sat down after his morning swim for three uninterrupted hours, often writing 2,000 words a day on his gold-plated typewriter.
The journalist, Christopher Hudson, has claimed the Flemings were practitioners of sadomasochism: "Those who were lucky enough to visit Goldeneye, Ian Fleming's Jamaican retreat, could never understand how the Flemings went through so many wet towels. But those sodden towels were needed, literally, to cool their fiery partnership, used to relieve the stinging of the whips, slippers and hairbrushes the pair beat each other with - Ian inflicting pain more often than Ann - as well as to cover up the weals Ian made on Ann's skin during their fiery bouts of love-making." She wrote to Fleming: "I long for you to whip me because I love being hurt by you and kissed afterwards. It's very lonely not to be beaten and shouted at every five minutes." Hudson goes on to argue: "The pregnancy which led to their marriage resulted in Caspar, their first and only child. The birth, Ann's second Caesarian, left wide scars on her stomach, to the disgust of Fleming who had a horror of physical abnormality. Ann said it marked the end of their love-making."
Fleming's novel, Casino Royale, featuring the secret agent James Bond, was published to critical acclaim in April 1953. The Flemings bought a Regency house in Victoria Square, London, and Ann gained a reputation for giving lunch and dinner parties attended by new literary friends, including Cyril Connolly and Evelyn Waugh.
Fleming spent a lot of time in Jamaica where he had an affair with Millicent Rogers, the granddaughter of Standard Oil tycoon Henry Huttleston Rogers, and an heiress to his wealth. He also had relationships with Jeanne Campbell and the novelist, Rosamond Lehmann. However, his most important relationship was with Blanche Blackwell who he met in 1956. Blanche told Jane Clinton: “Don’t forget I met him when he was 48. In his early life I believe he did not behave terribly well. I knew an Ian Fleming that I don’t think a lot of people had the good fortune to know. I didn’t fawn over him and I think he liked that.... She (Ann Fleming) disliked me but I can’t blame her. When I got to know Ian better I found a man in serious depression. I was able to give him a certain amount of happiness. I felt terribly sorry for him.” It has been claimed that Fleming based the character of Pussy Galore from Goldfinger on Blackwell.
Ann Fleming developed an interest in politics through her friend Clarissa Churchill, who had married Sir Anthony Eden, the leader of the Conservative Party. However during this period she began an affair with Hugh Gaitskell, the leader of the Labour Party. Brian Brivati, the author of Hugh Gaitskell (1996) has pointed out: "Friends and close colleagues worried both that the liaison would damage Gaitskell politically and that the kind of society life that Fleming lived was far removed from the world of Labour politics. Widely known in journalistic circles, though never reported, his attachment did not outwardly affect his marriage, but it did show the streak of recklessness and the overpowering emotionalism in his character that so diverged from his public image."
Gaitskell and Fleming would sleep together at the home of Anthony Crosland. Her biograpaher, Andrew Lycett, has argued: "Ann used to joke that when she went to bed with Gaitskell, she liked to imagine she was with the more debonair Crosland. Much as she enjoyed her unexpected romance, she could only cope with it by being slightly disparaging." Fleming told Lord Beaverbrook: "I suppose I shall have to go dancing next Friday with Hugh Gaitskell to explode his pathetic belief in equality, but it will be a great sacrifice to my country."
Ann continued to live with Ian Fleming. In 1962 he wrote to her: "The point lies only in one area. Do we want to go on living together or do we not? In the present twilight we are hurting each other to an extent that makes life hardly bearable." In an attempt to make the relationship work they purchased a house in Sevenhampton.
Anne continued her relationship with Gaitskell. Senior figures in the Labour Party became concerned about his involvement with someone who was known to be a right-wing supporter of the Conservative Party. Gaitskell's biographer, Philip M. Williams, the author of Hugh Gaitskell (1979) has argued: "At home at Frognal Gardens his guests were mostly progressive and few were actively Tory. But he kept up a few personal friendships across the political divide, largely through Anne Fleming and her circle. Crosland chided him about it; but, with his Wykehamist sense of rectitude and distaste for the idle rich, Gaitskell was not in the least worried that he might yield to the embrace of the social Establishment, or might be sourly suspected of doing so. He appreciated its comforts, and its intellectual stimulus still more."
Andrew Lycett saw the relationship very differently: "He (Hugh Gaitskell) saw her (Ann Fleming) as a spirited and amusing antidote to his dour professional life; she liked his brains and political clout, and considered it a challenge to wean him from his puritanical socialist principles to an enjoyment of the more overt pleasures in life. On one level, she promoted Gaitskell with Beaverbrook and ensured that his policies received favourable Express group newspaper coverage in any internal Labour Party dispute with his left wing. On another, she subverted the Labour leader's pretensions to seriousness. Ann Fleming, the political hostess who split the Labour Party and kept the Labour right wing in business: it is an interesting and not implausible thesis."
Hugh Gaitskell died at the Middlesex Hospital, London, of the rare disease lupus erythematosus, on 18th January 1963. Her husband, Ian Fleming died of a heart attack the following year. According to Christopher Hudson: "Ann never recovered from grief that she had not made Fleming happy... took to the bottle".
Andrew Lycett has argued: "Unhappy at the exploitation of the Bond franchise, Ann nevertheless welcomed the ensuing wealth. Her social gatherings metamorphosed into relaxed weekend house parties, attended by Oxford friends such as Maurice Bowra and John Sparrow. Despite right-wing views, she extended her political circle to include Labour Party spokesmen such as Anthony Crosland, Roy Jenkins, and the lawyer Arnold Goodman, with whom she was particularly close. In 1975 she experienced further tragedy when her depressive son, Caspar, killed himself."