Reminds me a bit of the good old days of playing Flash dating games! You've got a good sense of time and variety to the story with the Barbara always taking you to new places.
There's a lot of dialogue choices to make, but many of them have a clear right and wrong answer. You can try to trick the player a little more and maybe introduce problems that occur from earlier decisions that seemed right at the time. The story's a bit too wholesome at the moment to be called horny, and you've ended it right at the best part!
The ai-generated backgrounds are nifty. They've got too much of a photographic feel to them to fully match Barbara, but you can try running them through some sort of filter to give them a bit more of an anime look. Barbara's own illustrations are pretty, and there's some real variety to her clothes and poses!