First, I want to say that I like this game and thank you for all of the work you have done. My liking it is pretty rare, as the only other feminization game I like is Surrendering To My Crush (STMC). Personally I have no problem (and in fact enjoy) the lesbian content. The story is decent (I don't look for great literature, just a plot that makes sense and yours does for the most part so far).
Also, to your question about AI images, I feel it makes total sense to let AI help you like an assistant if you make sure its contribution is true to the artistic values you have for the game.
Suggestions, for what they are worth (longer and not necessarily worth reading lol):
First, you have a lot of lesbian content, and the story so far, it seems, kind of skirts around Jamie, at least sexually. It is currently lopsided in my opinion. As I said, I really like lesbian and really like D/s lesbian dynamics, so I am not saying it is bad, just lopsided right now, especially given the title. I prefer Jamie stay with women, so that isn't the point. Just that his sexual situations, save one (intro to anal) are not too evident.
Second, I love the role of a "Therapist" helping in his corruption, and there are a lot of lewd, erotic, overwhelming etc things she could do to him to condition him. But she isn't. Have that Therapist get sensual, diabolical, edge the shit out of him, make him lose control, make his mind melt, and so on. Call in a female assistant and talk to him in a brain washing way as she does things to him per her instructions, try medical devices (real or made up), and so on. She is erotic gold. I thought you were going for it when she introduced him to anal pleasure, but she has pretty much faded away since, as far as I can tell. I hope she gains a role again.
Third, you hint at Jamie's gf's Mistress wanting to control them both. If you plan on the Mistress doing all of the sexual training and corruption, that should start soon, in my opinion, again because things are quite lopsided. You can also incorporate that Therapist again to set up clinical situations with them all, which can hold a ton of erotic tension if you do it right. Remember, talking to Jaime, messing with his head as his body is overwhelmed, can be really erotic if the dialog is good.
Finally, and I guess a bit redundantly, use STMC as a guide of sorts, work on sustained situations that really mess with Jamie's head and body in the most sexual ways. Create the kind of interactions I describe above in both D/s relationships being tracked in your game (you have done some of that with the lesbian side, I feel).
Having suggested all of that, let me say again I am really enjoying your game regardless of the suggestions, none of which are criticisms. I definitely look forward to each release, pun not intended but definitely there