The footballer met Playboy models Carla and Melissa Howe, 21, last Saturday at London's Jet Black Club.
On Tuesday, Cole apparently requested they parade outside their home in front of his driver, who chose a 'winner' to spend the night with Cole. Melissa was selected and drove to his Surrey home.
"The way she was chosen was sick, but she says she had a really great time with Ashley," a friend of Melissa's told The Sun.
"She's obviously starry-eyed now and is hoping a relationship develops. He's told her it's no problem for them to see one another again. Cheryl didn't come into it."
Meanwhile, Cole spent Thursday night with one of Rihanna's dancers after attending her gig at The O2 Arena.
After checking with a friend that she was "not a bar girl", Cole, who last week told ex-wife Cheryl he doesn't want children with her, took the dancer back to his house.
"When he found out she was a dancer, he escorted her to his chauffeur-driven car and off they went," an onlooker said.
Cole was widely thought to have rekindled his romance with Cheryl following their divorce last September.
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