In a new John F. Kennedy Jr. tell-all entitled ‘American Legacy’, one his closest pals from Brown University, Rob Littell, revealed to author C. David Heymann that during the summer of 1988, Kennedy and the Madonna stopped off at a “cheap, dinky” Chicago hotel for a secret rendezvous during which they planned to finally have sex. “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,” Littell told the author, according to The New York Post. “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.” Read more.
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