It's a great question isn't it (and one I don't remember C.S. Lewis posing!) but I guess the 'kind of society' would be a ruling class one, whereas I doubt whether the same freedoms and female agency would be envisaged or countenanced for the rest of society. While the female in what Lewis saw as the 'allegory of love' was attributed with powerful choice and discretion, I tend to see the elevated role of the woman in these traditions as operating a kind of chivalrous choreography, affording exercise of knightly qualities and an iconic object of knightly desire that doesn't quite sit comfortably with me (though I admit I love the concept of gentilesse).
Andreas Capellanus’ “The Art of Courtly Love” addresses the question concerning the separation of historical portrayals from social context. From what I can remember without going directly back to the essay, it's all to do with the structure of feudal society. What Capellanus is apparently saying is that it's ok for a knight to take a peasant girl by force if he wants to. Contrast with pining after the unobtainable lady. Secondly, because this was a feudal society, aristocratic men were often away at the wars, with their wives running things in their absence. So, women of a certain class could and did wield actual political power. Then there's something connected to Christianity and the redeeming power of love that I don't remember well (I’ve got to hunt down anther copy of the essay; mine vanished a long time ago). The Occitan women troubadours (such as Beatriz de Dia) are a good example, but their very existence goes to show that women, for their part, could and did elevate men in the courtly love lyric.
Courtly love’s legacy is still with us today, in what have bedded down to become largely unconscious relationship expectations among men of women and women of men; for my money, it's hardly very healthy for men to be pining after women because they have rather romantically and lyrically mistaken them for the embodiment of all that is good and pure and delightful in the universe - and nor is it especially great for women to be divested of their particularity in this way and idealised into something that barely corresponds to the living, fleshly, and flawed. It made for some beautiful - beautifully choreographed, as you say - writing several hundred years ago, but all power to those writers (and I might argue that Tiptree is one) who risked introducing a little more vulgarity and filthiness into their own narratives/allegories of love. My own take on Tiptree, after having read 500 pages of her stories contained in this volume, is that I applaud her for her desire to muddy the waters of sexuality and identity in her stories; and we can’t say she got bogged down by adherence to formal orthodoxies on the levels of the sentence and story construction when she wanted to have fun telling a story between Man and Woman in all their guises.