The entertainment website claims the liaison happened last Friday in San Diego, California after a booze-fuelled night out.
The 23-year-old woman, who has not been identified, has reportedly hired a high powered Hollywood attorney and has gone into hiding.
Radaronline says it received the information from 'multiple friends of the woman.'
According to one unnamed source: 'She is due to meet with an attorney tonight (Tuesday). She is freaking out.'
The Two and a Half Men star's wedding anniversary was on Saturday, September 24, one day after the alleged encounter happened.
'Ashton didn't look like someone who was celebrating a wedding anniversary,' one club goer told RadarOnline.
The scandal also comes as Star magazine, a sister publication of RadarOnline, is working on an explosive new report claiming the marriage between Ashton, 33, and Demi, 48, is 'officially over.'
The issue will hit newsstands tomorrow (Wednesday).
According to Star: 'Ashton and Demi have separated and the marriage is over.'
MailOnline contacted Ashton's representatives, but so far they have not responded.
A source close to the pair reportedly told Star magazine: 'The relationship ended because of Ashton's serial cheating. It's a painful time for Demi.'
In September 2010, as Mailonline previously reported, Ashton was rocked by another cheating scandal after Star reported that he had had a fling with a 21-year-old woman named Brittney Jones.
The young woman told the magazine she had sex with the actor inside the Beverly Hills home he shares with his wife.
The magazine also claimed that Ashton was so worried that the alleged affair would be exposed that he made her delete their text messages, but Star reported that she didn't remove all of them.
Brittney told Star: 'He looked over the texts and said he wanted me to delete all the messages from him,' she revealed. 'He then told me he wanted me to delete the texts I had sent to him. He said they could hurt him.'
Despite the explosive report, Ashton and Demi brushed off the allegations with Ashton making sure to express just how he felt by taking his Twitter to make a statement.
He said, 'I think Star magazine calling me a 'cheater' qualifies as defamation of character. I hope my lawyer agrees.
'STAR magazine - you don't get to stand behind "freedom of the press" when you are writing fiction.'
Kutcher's representative also denied the story, while his wife of nearly five years came out in support of her husband.
'Excellent point my love!' and 'No question!' she wrote in response to Kutcher's comments.
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