Madonna almost had sex with John F Kennedy Jr, but they stopped because they did not have a condom, it has been claimed.
The singer and John, whose father was assassinated US president John F Kennedy, had checked-in to a cheap Chicago motel behind their partners' backs in 1988, but their steamy rendezvous was cut short due to a lack of protection. Rob Littell - who was a close friend of John's when they were both students at Brown University - revealed the incident to C David Heymann, the author of new book American Legacy.
Rob claims, "They were working their way around the bases, and as they rounded third and headed for home, she asked him if he had any protection. He didn't, so now they began discussing how they were going to get a hold of a prophylactic."
"She was still legally married to Sean Penn, and he had a steady girlfriend. They were afraid of being busted. They couldn't very well just meander into a pharmacy and ask for a pack of Trojans. They were too well known. To John's great chagrin, the relationship was never completed."
Madonna separated from Sean at the end of 1988. The couple divorced the following year. John married Carolyn Bessette in September 1996, but the pair died in a tragic plane crash in July 1999. Madonna, 48, is now married to British film director Guy Ritchie.