Letters From James Bond Creator Ian Fleming Detailing His Infidelity Hit the Auction Block

If the adage “write what you know” truly applies, then James Bond author Ian Fleming took it to heart. Like 007, his famously womanizing character who later went on to star in a hugely successful movie franchise, Fleming was apparently prone to finding himself in choppy relationship waters, according to a collection of private letters coming up for auction.

Sotheby’s is offering a collection of 160 pieces of correspondence belonging to Fleming, including a series of exchanges between the writer and his wife, Ann, that detail his infidelity.

“You mention ‘bad old bachelor days’—the only person you stopped sleeping with when they ceased was me!” Ann wrote, apparently referencing Fleming’s indiscretions. Other letters seem to hint at a more stable, if lurid, coupling, with Fleming affectionately referring to her as “darling baby” and opening his messages by addressing her as “Dear Monkey” or “Darling Pig.”

Before they married, Ann expressed hope Fleming would arrive to take her away from her then-husband, Esmond, Viscount Rothermere, and “put me in your bed with a raw cowhide whip in my hand so as I can keep you well behaved for 40 years.” Clearly, that plan didn't succeed.

Fleming and Ann were married in 1952 and remained together until his death in 1964. The letters were often exchanged while the writer was on retreat at Goldeneye, Jamaica, where he wrote many of his Bond novels. The letters also frequently reference his work and some of Bond’s origins. In one, he explains work is going so well he’s completing a chapter a day. Describing a boat given to him by a friend, he wrote that “I have christened Octopussy.”

The salacious letters will be auctioned from December 3 to 10 and are expected to fetch between about $260,000 and $400,000.