What Ian Fleming’s racy letters reveal

From extra-marital affairs to a penchant for bondage

Ian Fleming
(Image credit: Express Newspapers/Getty Images)

More than 160 letters between James Bond creator Ian Fleming and his wife, Ann, are to appear at auction.

The collection spans more than 20 years and details the rise of Bond and the decline of their previously passionate marriage.

They letters - which are set to sell for up to £300,000 say Sotheby’s - detail how the 007 novels became a point of frustration for Ann, who said she was “desperately tired of that ass Bond”.

Subscribe to The Week

Escape your echo chamber. Get the facts behind the news, plus analysis from multiple perspectives.


Sign up for The Week's Free Newsletters

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

Sign up

Gabriel Heaton, a specialist in books and manuscripts at the auction house, said the Bond novels served as “both as an outlet for his libido and imagination, and also... an attempt to make money for a woman who was used to being unthinkingly rich”.

Ann cheated on at least two husbands

Ann and Ian Fleming had an intense love affair while she was married - to two different men. Her first husband was the 3rd Baron O’Neill, who died in military action and was followed by newspaper magnate Esmond Harmsworth, the 2nd Viscount Rothermere, says The Guardian.

During both marriages, the pair were lovers, with Ann becoming pregnant with a baby girl, who died eight hours after her birth.

“I have nothing to say to comfort you. After all this travail and pain it is bitter. I can only send you my arms and my love and all my prayers,” Fleming told her after the child’s death. The letter was written on Gleneagles stationery - Fleming was there playing golf with Ann’s cuckolded husband, Rothermere, says The Telegraph.

Ian and Ann dabbled in BDSM

The letters reveal that the couple enjoyed a touch of sado-masochism.

“I long for you even if you whip me because I love being hurt by you and kissed afterwards,” Ann once wrote to Fleming.

And Fleming was explicit about his desire for Ann in his letters to her. “I love whipping you & squeezing you & pulling your black hair, and then we are happy together & stick pins into each other & like each other & don’t behave too grownup,” Fleming wrote.

In later correspondence, Ann said: “I wish a fairy would arrive with a wand and make everything alright, give Esmond [her second husband] a perfect wife and put me in your bed with a raw cowhide whip in my hand so as I can keep you well behaved for forty years.”

Fleming had more affairs than Bond

Fleming had numerous affairs with women while he was Ann’s lover, and didn't stop when the couple were married in 1952.

Ann once complained to the author: “You mention ‘bad old bachelor days’ – the only person you stopped sleeping with when they ceased was me!”

To continue reading this article...
Continue reading this article and get limited website access each month.
Get unlimited website access, exclusive newsletters plus much more.
Cancel or pause at any time.
Already a subscriber to The Week?
Not sure which email you used for your subscription? Contact us