Prince Andrew flirted with a Jeffrey Epstein associate on a visit to his private island—according to an unearthed 2015 email.
Gwendolyn Beck, a former money manager for the financier, wrote that she would have been tempted by the Duke of York if she had not been in love with someone else at the time.
However, she disputed claims the royal took part in an orgy on the island, as claimed by Virginia Giuffre in sworn testimony.
Quoted in the Daily Mail, Beck wrote in the email: "As I remember, he arrived very late at night (on Little St James) spent the next day/night, and left early the following morning.
"He was in the bungalow next to me, and I heard no strange noises or anything unusual. If anything, he was flirting with me, but . . . I was in love with someone else."
Her 2015 account came the same year Virginia Giuffre testified under oath that Prince Andrew and Jeffrey Epstein took part in an orgy on Little St James.
Giuffre said French model agency boss Jean-Luc Brunel brought Russian models to the island for a photoshoot which she was told to take part in.
She said: "The third time I had sex with Andy was in an orgy on Epstein's private island.
"I was around 18 at the time. Epstein, Andy, approximately eight other young girls, and I had sex together.
"The other girls all appeared to be under the age of 18 and didn't really speak English.
"Epstein laughed about the fact they couldn't really communicate, saying that they are the 'easiest' girls to get along with.
"My assumption was that Jean-Luc Brunel got the girls from Eastern Europe (as he procured many young foreign girls for Epstein).
"Afterwards we all had dinner by the cabanas. The other girls were chatting away among themselves and Epstein and the Prince chatted together . . . Prince Andrew must have flown early the next morning."
Prince Andrew denies ever having had sex with Giuffre and sources linked to his legal team recently told Newsweek he wants to return to public life having quit royal duties in disgrace last year.
The duke gave a car crash interview to BBC journalist Emily Maitlis in which he failed to express remorse for his friendship with Epstein and said little about the impact on the abuse on the victims.
Asked whether he had sex with Giuffre first in London, again in New York and then with her and "seven or eight other girls" on the islands, Andrew replied: "No."
When Maitlis said "No to all of those?" he added: "All of it, absolutely no to all of it."
Beck said in her 2015 email reported in the Daily Mail: "I used to manage money for Mr Epstein when I worked at Morgan Stanley (1995), and had the great pleasure to meet Prince Andrew a few times.
"After the business relationship ended, I didn't see either one of them.
"Mr Epstein was kind enough to donate to my campaign, but I never spoke with him (it's very common in the U.S. for politicians to reach out to all the wealthy people they know).
"The Prince was always charming, polite and a gentleman to me. Just can't imagine this is an accurate story, after all prostitution is illegal in the U.S.
"If I hadn't been in love at the time, I certainly would have given the Prince my number . . . actually, is he single now?"
In a second email, she added: "I can't imagine the allegations regarding Prince Andrew are true — as I said before, he was a total gentleman.
"As I remember, he arrived very late at night (on Little St James) spent the next day/night, and left early the following morning.
"He was in the bungalow next to me, and I heard no strange noises or anything unusual. If anything, he was flirting with me, but . . . I was in love with someone else.
"We did have a lively conversation that day after the market closed (New York Stock Exchange)—I explained the four things you can do with your money and what a 'derivative' is.
"He said: 'Brilliant, you should write a book'."
A Daily Mail investigation into the evidence underpinning the allegations against Prince Andrew has called into question elements of his alibi, stating he had several hours of private time blocked out on a trip to New York when Giuffre says they had sex.
The newspaper claims he cut short a family holiday with ex-wife Sarah Ferguson and his daughters Princess Beatrice and Princess Eugenie in order to visit Epstein's island.
However, the coverage also highlights that Giuffre has given different accounts of the orgy on the island at different points and in her first, in an unpublished memoir, did not mention Andrew's participation.
