Playboy's first centrefold featuring a topless Marilyn Monroe was auctioned for $17,925 at Christie's in New York on Wednesday. The centrefold was from the adult magazine's 1953 inaugural issue.
Almost $2.7 million was collected in the auction, which saw more than 300 items from the Playboy archives going under the hammer.
The sale included original manuscripts by such 20th-century literary figures as Jack Kerouac, Ian Fleming, and Ray Bradbury, and a stretch limousine customised for Playboy founder Hugh Hefner.
An image from nearly 30 years later, an iconic photo of "10" star Bo Derek, taken by her husband, John Derek, for the cover of the March 1980 issue, fetched $11,950.
The top seller among the literary offerings was Kerouac's typed manuscript of 'Before the Road,' a prequel to the legendary 'On the Road', which sold for $71,700.
Hefner's limousine, a converted 1988 Mercedes Benz 560 SEL, fetched $77,675. The winning bidder was also entitled to an exclusive tour of the Playboy Mansion in Los Angeles and two tickets to the invitation-only New Year's Eve party held there every year.
The auction was held in celebration of the 50th anniversary of Playboy magazine.
"We are thrilled with the success of the sale," said Christie Hefner, Hefner's daughter and chief executive officer of Playboy Enterprises, Inc.