Great game so far, Sumodeine!
You might have more plans story-wise than we can see currently, but I felt a little confused that the MC is essentially forced into a relationship with Ashley, whereupon Molly (probably) sees him in bed with her in underwear. Given her incredibly sheltered and strict upbringing, her character should at the very least remark upon it. What she says would be dependent on the player's choices (like if they had a date, she'll be outraged and disappointed, etc.). I hope in the future the player will have the option to screw up the interaction to the point where the date doesn't happen, and the MC can go with Nikki and Molly.
Honestly, I think I'd be happy with the MC having a couple different routes where he gets to screw different girls depending on the deviant / gentleman score, with some that reject him because he's not deviant or gentlemanly enough. Like, the conversations with Jessica would have a special option that leads to sex if your score is above a threshold value, and during your date with Molly a special conversation option would appear if your gentleman score was high enough that would lead to her talking about what it would take to get into her panties.
Again, given her upbringing, I would think that Molly would be really difficult to romance, having really strict all-or-nothing rules that she's looking for in a partner. I know there's an element of self-discovering going on with her, but there's a great opportunity for both the MC and his sister to corrupt her from a perfect church girl into a more normally socially adjusted girl. I know the usually harem thing is to get ALL the girls, but you could stand out a bit by forcing the player to first entirely corrupt Molly before she would be open to multiple partners for the MC, otherwise she would freak out and close down all contact (and maybe even work to sabotage his other relationships) if her heart was broken badly enough. A lot of great potential here!