The provocative image was taken by fashion photographer Steven Meisel but was never included in her controversial 1992 book Sex.
The 1990 pic is expected to fetch over £5,000 when it goes under the hammer at Bonhams in New York next month.
Madonna – who would have been around 32 years old when the photo was taken – is featured sporting bleach-blonde hair and dark eye make-up.
A strategically placed bed sheet saves the shot from indecency as she sprawls out starkers on her mattress.
She stares seductively at the camera as she places a lit cigarette into her mouth with a pair of manicured fingertips.
Her tome Sex contained a series of provocative images, all captured by Meisel.
Despite a poor critical reception, the book went on to shift 1.5 million copies in a matter of days.
It coincided with the release of her equally raunchy fifth studio album Erotica
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