I feel like the more that I reread the James Bond novels, the less I feel I understand Ian Fleming as a person. I mean it's obvious that there are certain elements of the bond novels that would not be considered acceptable, for example the diatribe about how women getting the vote caused homosexuality to flourish or the random and seemingly out of place line in Casino Royale about how Bond's sex with vesper would always have the "sweet tang of rape," so it'd be easy to write stuff like this off as the rantings of a deeply prejudiced man, but at the same time I find it difficult to just do that because of how inconsistent such elements are throughout Fleming's writing.
I think some of these elements are less deeply-believed rants than attempts to shock the reader. "Sweet tang" thoughts aside, Bond isn't anything close to a rapist. The sex-equality line is pretty outrageous though a bit more nuanced--Fleming is saying that gender equality and the breakdown of gender roles is creating sexual misfits who aren't fully homosexual or heterosexual. Swap out "misfits" for a more positive term and you'll have something any gender studies might approve of.
A good illustration of this appears in the novel Live and Let Die. Fleming makes a point of having 2 different characters at different points of the novel give a speech about how African-Americans are just as capable as white people are, so it seems clear that he's trying to make a point about the inherent equality of the races, but inbetween those two points his characterizations of PoC seem to mostly consist of harmful stereotypes
I think that stems from Fleming being caught between an Imperial viewpoint--where every nationality and earth was meant to be subservient to the British--and the emerging consensus on civil rights. I think it's clear that he likes African-Americans and other black nationalities, but he also patronizes them and has no real connection to them as equals. Most of the black people Fleming knew were his servants at GoldenEye, and there was a class divide alongside the racial one.
Furthermore in Goldfinger he includes some very bigoted sentiments towards Koreans (though always given through a character rather than exposited by a narrator), and makes the character of Dr No a blatant "yellow peril" style villain, but then later goes on to write You Only Live Twice which is essentially a love letter to Japan in the form of a james bond novel.
I used to be puzzled by that as well, until I recalled Fleming's usage of the word "races," which implies races within the usual races we speak of nowadays (white, black, asian, etc). And he obviously had his favorites within those races. Why he should have disliked Koreans, especially when the Japanese had a far worse war record, still puzzles me. But perhaps he viewed Koreans as more exotic and more amenable to being viewed villainously.
Then we get to the sexist undertones of the books..Fleming is quite fond of using the "rape as backstory" trope for his female characters. He also seems to have an affinity for making his female protagonists entirely uninterested in men until bond comes along, at wich point they fall for his charms. Obvious examples here would be Tiffany Case, Solitare (potentially. It's stated by Mr. Big that while she Lived in Haiti she was completely uninterested in men, which is how she got her nickname, but later she specifically states that she's always wanted to be with a man), Pussy Galore (who is specifically stated to be a lesbain), and potentially Vesper Lynd but I may be misremembering that one.
Vesper's interest in men is actually what dooms her--recall her Polish boyfriend held hostage by SMERSH. But the larger point is that most of Fleming's heroines are either not interested in men or have had terrible experiences with them (sometimes rape, but also bad previous relationships, as with Vivienne, Domino and Tracy). Regardless of circumstance, Bond represents the first genuinely caring and decent man they come in contact with, and they often leave the books happier and more fulfilled than how they entered them. In that larger sense, the idea of Bond being the first "real man" the women encounter is more along the line of wish-fulfillment than misogyny.
Due to this it's very hard for me to get a handle on who Fleming was as a person and what his attitudes were, and it's also making it very hard to get through the series again at points, as the more positive aspects can draw me in and put me at ease, allowing me to essentially be sucker-punched as a reader by the negative, prejudiced aspects of his work.
Fleming was someone caught between the world of Edwardian clubland and the jet-age. He was anarcho-Tory Imperialist who held extremely permissive views on sex and morality. The fact that he and his books are full of striking contrasts and incongruous attitudes helps them remain interesting and provocative.