Madonna begged Tupac Shakur to have a child with her, it has been claimed.
The Hung Up singer is said to have briefly dated the rapper a year before his death in 1996, and was desperate to start a family with him.
Lucy O'Brien claims in her new book Madonna: Like an Icon: "In her mid-30s Madonna desperately wanted children and had various relationships with unlikely men, in the hope she would conceive."
But Madonna, now 49, was allegedly dumped by Tupac for not fitting in with his bad boy rapper image.
The singer's friend Alison Clarkson claimed: "She was going out with him but homegirls were saying to him, 'I can't believe you're going out with a white girl,' so she got dumped!"
Madonna went on to form a relationship with her personal trainer Carlos Leon and in October 1996 gave birth to his daughter Lourdes.
The book also documents Madonna and actor Sean Penn's wedding day in 1985, which was witnessed by a host of star guests, including Martin Sheen, Andy Warhol and Carrie Fisher.
Guest Bill Meyers recalled: "Martin was freaked out by the media
helicopters. He was flinching and jerking involuntarily. He said it reminded him of filming Apocalypse Now during the making of which he suffered a heart attack.
"Madonna was giving them the finger and Sean was running in the house for his shotgun."
Madonna is now married to British film director Guy Richie, 39, with whom she has a seven-year-old son Rocco.
Last year, she was granted temporary custody of two-year-old Malawian boy David Banda.