Jesse's section has been a ton of fun to work on, and I'm glad you love playing through what's available for it! The next update will feature a lot more content for him, and yes, there will be different endings available for either giving in or resisting :)
The paid demo for each release will have more "paid exclusive" content added to it; for the time being, if you want access to that new exclusive content, then you'll need to pay again when the game is updated.
However, I'm toying around with the idea that if you sign up for a monthly pledge amount/donate a certain amount (working on a Buy Me A Coffee page for donors to support the art and development for this project), then one of the benefits of that recurring donation/pledge amount would be free access to the paid versions of the demo builds as they're released (as well as sneak peaks at future content plans/advanced access to releases/etc.). Do you think that kind of support/reward model would be something folks would sign up for?