The dark haired teenager with the flinty eyes stares up at the camera, clad in nothing but a man’s
striped shirt and burgundy tie and chewing seductively on a pair of glasses.
The steely expression that she went on to perfect while en route to becoming one of the world’s biggest stars, amassing an estimated fortune of $500million, is already present.
Aged 18, in late 1977, a University of Michigan dance student named Madonna Louise Ciccone posed nude at $10 an hour for photographer Herman Kulkens - only for the pictures to surface less than 10 years later after she became a household name.
More Photos after cut...
In another never-seen before picture, now up for auction, superstar Madonna, now 55, is nude as she brushes a woman's hair.
While another shot shows her standing naked with her back to the camera with just a wide-brimmed hat on her head - and a blanket draped around her legs.
And with a smile on her face, the young girl poses topless for Kulkens for pictures that would be at the center of a legal battle in 1985 when both Penthouse and Playboy attempted to print them.
The sensational images are among the haul left behind by Penthouse founder Bob Guccione who died of cancer aged 79 in October 2010, and now owned by Wall Street trader turned entrepreneur and financier Jeremy Frommer who bought Guccione's entire estate from his creditor last year.
Long-lost images of Arnold Schwarzenegger, President Bill Clinton's mistress Gennifer Flowers and Lauren Hutton among others were found among the papers, photos, slides and letters belonging to Guccione that Jeremy and associates have carefully spent hours sifting through.
For Madonna, the publication of the nude photos would not have come a shock. She posed naked for three photographers between 1978 and 1980.
For Kulkens, he once recalled how he was impressed by the girl he met in a sculpture class at Art World, a school in Ann Arbor, Michigan.
Her face, he said, 'reminded me of Cleopatra'.
At the time, Kulkens and his photographer wife Susan got a signed release from Madonna that granted them rights to 'sell or use the photos as they saw fit' in return for a small amount of money.
However, the Kulkens went on to sue Guccione for $2million in 1985 as well as attempting to block publication - just as Madonna's star was on the ascendent and she had released some of her biggest hits, Holiday, Like A Virgin and Into the Groove and was embarking on her Like a Virgin tour - claiming they had never signed a binding agreement and wanting to publish with Playboy.
In the end, pictures from the set were published in both Playboy and Penthouse - with Guccione defending himself by claiming he had a signed agreement from the Kulkens, as Playboy raced to the newstands and breathlessly proclaimed it had published first.
Madonna's long-time publicist Liz Rosenberg, who still works with Madonna to this day, said of the furore: 'Madonna has acknowledged in past interviews that she did pose nude for art classes when she was a model.
'Her feeling is she's never done anything she's ashamed of.'
Jeremy Frommer is now putting the Madonna images up for auction on November 9 on Guccionecollection.com and told MailOnline: 'We will also be selling 21 35mm slides, only six have ever been published...the craziest thing is that we still don't know who the mystery girl whose hair Madonna's playing with is.