I think you are just filling in plot holes yourself, which is fine
I haven't filled anything in, it's all explained in the game.
His aunt explains what happened with Rachel and the deal she made with Lileva. He wasn't a virgin either, his mother had fucked him but he doesn't remember, Lileva blocked the memories.
What happened with Cherry was a mistake. She was supposed to be obedient but she did the one thing she wasn't born to do, she fell in love with her father. She was supposed to breed with him but because he didn't love her back she stopped it then risked her life to save him, that happened just before he had sex with her.
Having sex and showing her love broke Lileva's hold over Cherry and gave her more power than she should have had.
Lileva is a goddess, Cherry wasn't designed to have that much power, it all went wrong thus the reversal.
The only thing not fully explained is Jason's role in all this. The only people the dev has confirmed not under Lileva's control are Ella and her mother, I assume Lilith too.
Not sure about Selina as she's also a good choice Cherry wanted him to pick.
Put simply, Cherry wants him to pick love, Lileva wants the whole fuck fest. I've been playing for a year, that's all stuff that's in the game.
Granted it is a theory over why Ella was pissed at him but it's the only one that makes sense. I can't say I blame Ella given her mothers circumstances but we still don't know what she did to her husband to take over his business. I guess she either had him killed or did it herself.
I also don't know the role of the girl with the short red hair though it seems she's also a demon. Whether she's there to keep Jason in line or not I have no idea.
Jason is another I have no guesses about. He knows Selina will never sleep with him yet still agrees to go out with her. She's doing it to get MC jealous and that's all I know from what she said. I also have no idea about his role in the bigger picture.
There is still a lot of story left to go so not everything is going to be explained. Some of the threads will take time to clarify.