Private Sessions 2

After drugging a newly hired professor, Tomoya takes his place at the College of Sacred Maidens — a school full of women he's already decided are his personal targets. From there, the whole 2-episode OVA is essentially him working through that list. Yumi the cheerleader, Seira from the swim team, Asuka, and several others are all in his sights, and he has zero hesitation about using his fake authority to manipulate them. The setup is dark from minute one and doesn't pretend otherwise — this is a predator fantasy, explicitly framed as one, and the tone stays consistently bleak underneath the explicit content. The character designs are detailed and each girl has a distinct look and personality, which at least gives the scenarios some variety across the two episodes. It's adapted from a visual novel, so there's a bit more structure to the encounters than you'd expect from a typical OVA — each character gets her own setup rather than things just happening randomly. If you've watched Discipline: The Record of a Crusade or Bible Black and you're used to that darker, manipulation-heavy style of hentai OVA, this fits comfortably in that same space. It's not subtle about what it is, and if that specific subgenre is what you're looking for, it delivers on those terms. Just go in knowing the premise is genuinely uncomfortable — that's kind of the whole point.