I was previously unaware of The Moneypenny Diaries which is a short book series that tells James Bond adventures from the perspective of Miss Moneypenny (did anyone know her first name is apparently “Jane”?).
It doesn't seem like the series got too far, but there some short stories published in British magazine. One of them is entitled For Your Eyes Only, James which sounds vaguely like Bond and Moneypenny might have consummated their flirtation.
(I did some looking, but that particular installment seems to be hard to find. Several people are trying to find reprints of it.)