tl;dr I still don't think Simon can be cucked.
Well, that's the thing- is it? As I understand it, being cucked means being too weak to do anything if your woman is fucking some other person male or female, even if they're doing it in front of you. But does Simon consider the women in his harem 'his' women? Remember, this is the guy who let his wife bring a lot of other people into their bed, and he never mentioned if all of them were women. He also has a habit (at least, up to around the middle of the game) of questioning whether or not women are being with him voluntarily, hardly the ideal of a man who wants his women to be his and his alone. Heck, after her transformation, poor Aka has to make it her own personal quest just to convince Simon that she truly loves him, and that his IK powers have not changed her mind before or after.
I mean, maybe I have a different read on the guy than most, but I simply cannot see Simon getting pissy if, say, he found out Hilstara was seeing some hot young stud while he was away assembling a national economy (or whatever he does in his spare time). Even moreso if we're talking about the succubi with him, who literally need sex to survive. Hell, Trin could be fucking an entire army of dudes and dudettes in another room while simultaneously giving Simon some attention, and the worst I think he'd react is telling her to pace herself.
See, I think the key here is that they were
never 'Simon's women' in the first place- they're a group of talented women who Simon has a sexual (but by no means exclusive) relationship with, and whose goals align with his own, to the point where it's simply more convenient to be near him as shit goes down. And I think Simon's mature enough to know that, as independent women with minds and desires of their own, they will make their own decisions about things- which, yes, might mean they might choose to have a go at someone other than Simon. Just remember the early chapters, where poor Yarra was trying to convince Simon to make Megail, Janine and practically every other powerful woman he met into his obedient fuckslaves, and Simon kept refusing because that's not how Simon rolls.
Of course, I doubt they would, since this is an RPG with a strong focus on the protagonist, but there's always a chance, because Simon lets them have the chance to explore new things and meet new people. If he didn't, he wouldn't be Simon anymore, he'd be the Incubus Emperor, or the Fucklord.
I mean, I get it- I play Free Cities, I've finished all the Kangoku Senkan games to date (not the Taimanin series though- the character designs never really did it for me), I've gone through Rance, I can understand the charm behind having an exclusive harem. It's just that I don't think Simon is anything like Donny Bohgan or Rance, and that's what makes him truly special as a video game protagonist, much less one from an H-RPG.
In short:
View attachment 596740
Let's not confuse one for the other.