I actually prefer the "plays it straight" aspect Headmaster takes. The game and the character. Most porn games have a "huh, huh, boobies" Beavis and Butthead attitude towards it. Where whatever thin veil of story they offer, usually none, is cloaked in "fuck it, time to strip off and make with the sex."
The Headmaster character's focus on "I'm doing this to help the girls. They're unfocused, they're unruly, they're letting themselves be distracted with (insert issues) and I can fix that with my methods" is fun, refreshing, and even makes a certain amount of sense within the universe. He punishes, then pleasures, to help the lesson, the correction, stick. Does it work that way in real life? No, or at least probably no, but this is a game! A story! Better, a porn story!
If he strips girls down to their bare bottoms, paddles them, then fingers them, and they then go on to improve ... that's funny. Sexy as well. Look at Debbie, or Cassandra. He is (in an obviously perverted way) helping them. They're getting closer to their goals, becoming better people. Yes it's porn, so it's very porn, but within the universe of the story, it plays kind of straight and works within the story. Which makes it fun. That's what stories are for; playing around with ideas and concepts.
Do we do what HM is doing in real life, even to college students? NO! But this is a story, a game. Arguing about reality is boring and off-topic. Here, in Headmaster, the headmaster himself plays it straight and that makes it interesting and compelling compared to the Beavis and Butthead approach that's obvious, droll, and dull.
I want the story to continue. And I hope it doesn't devolve down to "insert obvious sex scene" like most games do. Which is all most games do.
It's also why the graphics we have now, which are maybe "bare bones" don't bother me. Pretty graphics without the context of a story are boring and uninteresting. Headmaster has a good story that makes even graphics that aren't lavish and eye-popping more than enough to be interesting and sexy, because when you look at Rachael or Priti or Amy it's not just "naked girl" but characters we know. Rachel is inexperienced, innocent, and jealous. Priti is shy and repressed. Amy is wild and horny. Not just words, but a whole story that we've read making us feel them like people, like real characters.