An inscribed copy of Oscar Wilde's The Importance of Being Earnest will star in a November 24 auction at Sotheby's London.
Wilde presented the book to his first lover, Robert Ross.
Robert Ross was Oscar Wilde's first lover
Ross and Wilde are thought to have embarked upon their love affair in 1886. Their relationship ended a few years later, but they remained devoted friends.
It was Ross who broke into Wilde's home after his arrest to ensure his documents did not fall into the hands of the police.
After Wilde's death Ross commissioned the statue that stands over his grave in Paris. Ross' own ashes were later interred inside the sculpture.
The inscription reads: "To the mirror of perfect friendship: Robbie: Whose name I have written on the portal of this little play. Oscar. Feb. 99"
It's expected to make £150,000-200,000 ($229,568-306,091).
Earlier this year a copy of the play given by Wilde to his prison warden sold for £55,000 ($93,266).
A copy of Ian Fleming's You Only Live Twice, signed by the author to the inspiration for one of the characters, is valued at £20,000-30,000 ($30,599-45,898).
Richard Hughes, the book's recipient, was written into the novel as the Australian spy Richard "Dikko Henderson" Lovelace.
Hughes wrote for the Sunday Times, but had been a boxer in a previous life.
He was also an accomplished drinker and had accompanied Fleming on a booze-soaked jaunt round Asia in 1959 - immortalised in the Thrilling Cities series for the Times.
The inscription reads: "To Dikko-San from Fleming-San. With all Affection".
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