Speaking in general, there would be quite a few games taking advantage of Live2D(Flash animations' spiritual successor) to implement that feature. But seldom in lasting fashion.
3 from the top of my head,
just for the facial expressions: (all are easy to find in ULMF)
- Ason's Cursed Blackmith(WIP): quality animations and expressions. Voice acting slows down the development (given the current circumstances) but helps further in setting the mood.
- Any excessM work. That's very subjective, but they somehow excel in giving a distinct vibe to every girl's face. OK, most of them are looking down on MC, but they do that with very varied expressions.
- Monster Girl Dreams (WIP). Facial expressions were a relatively recent addition, but it feels like Threshold is having much fun playing around with that. They're simple but help a bunch for immersion/empathy.
Not much of a progression for individual girls, I'm afraid...
If it's about the progression, you might want to look into dating sims or games around Corruption, or raising sims/slave trainers... Or even NTR, since psychological/emotional damage would be the keystone.
Now that I think about it, the Hentai world is pretty harsh on its girls
PS: maybe clothing damage too, since the artist would typically draw a new face for the new posture.