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Go do other things and it should eventually unlock. I don't remember exactly what it was - maybe drinking with Clyde a certain number of times or something. But it got triggered by advancing one of the other questlines enough.

As far as the armour being recognizable, even Matt didn't recognize it on sight. The user of that armour was a legend but kept a pretty low profile.

As for the rest, they suspected he had one other companion in hiding, which would make it 3-on-2 in their favour, all of them being companions. And the military armour is not a huge factor - they presumably don't know what it is, and ordinary military armour is probably not significant protection against companions. To them it's effectively a costume. So, yeah, they're being cocky and overconfident, but expecting a 3-on-2 to go in their favour is fairly reasonable.

I mean, harem is a form of poly. Any harem game is a poly game. Me saying poly didn't mean that the girls are also in relationships with each other. There are a couple of lines that indicate sapphic content and/or threesomes might be a possibility at some point, but as of chapter 8 it hasn't happened (I haven't played through ch 9 yet). Rather, I emphasized the poly because it doesn't quite follow the standard "harem game" format.

There's not a clearly defined group of women you are dating who all live their lives in proximity with you as you progress all of their stories. Rather, a number of characters drift in and out and back into your life as events and circumstances dictate. Often you have the option to have romantic and/or sexual entanglements with them. No one seems to care too much if you are doing so with multiple people. And it's left unstated whether the women in question are doing the same or not.

As someone who is poly IRL, it feels like a more realistic depiction of one form of what poly can look like than the vast majority of harem games do (the only one I can think of that competes on that front is Out of Touch, but that's a very different form of poly).

On my current replay, I noticed a bit of an inconsistency in a couple characters' sexual preferences. Which, people can be multi-layered but they still seem odd.

When you first meet Amy, she identifies herself as a sadist and says that she likes to be in control. It's presumably a significant trait to her because it's one of the first things she tells you (although she seems to equate sadist and dominant). But when you actually sleep with her later on, there's almost no trace of that. In fact, she almost immediately tells you she wants you to be dominant. I suppose there was a tiny bit of dominance in the shower scene if you don't choose to extend the scene by taking control, but even then it was pretty mild especially compared to her submission if you do.

Then also, with Eda, the first time you meet her she comes across as a switch. She asks which role you'd like and seems to be happy either way, going so far as to say "Good. I like it that way" if you choose to take the lead. But then in the scene at the start of Act 2 where she's trying to cheer you up, she specifically says that she prefers to always be in control but will make an exception given the circumstances.

Personally, my preference would be towards OCs over other franchises when you want to go beyond OW characters. So far you've done a pretty good job with them.

Review:

MC accidentally bonds with a symbiotic spirit (called a Dark One). Initially he tries to keep his new powers under wraps and live a quiet life but when he avenges a SA attempt against his friend, he unintentionally gets drawn into both Dark One and Companion politics. (Companions are the people who are bonded to Dark Ones.) These political spheres are well-realized, with various factions and powerful individuals and no clear "good guys" or "bad guys". Main character's motivations throughout are largely to survive and protect his loved ones, but to do that he has to do some fairly aggressive things at times.

Does a good job of making you care about the characters and of presenting decent stakes (things don't always go right for our protagonists all of the time). Primarily caters to a harem/poly romantic approach (and purely hetero), but doesn't make all of the LIs feel like they're just there to check boxes off our MC's collection - they feel like they have their own lives that don't revolve purely around him. The only exception to this is his Dark One, whose life does revolve around him, but that's because she's literally bonded into his soul. Even then she has her own wants and needs that don't always align perfectly with his. Additionally, all of the LIs feel very distinct, in their personalities, their capabilities and their sexual preferences.

As a con, it's worth noting that this game is very kinetic - there aren't many choices and those that are there don't change the story much at all.

Overall, if you want a fantasy AVN that focuses on intrigue and action with a gothic/horror aesthetic, while still having decent romance/sex, I don't know of a better option. At least not if you're okay with your choices not really mattering.

If you want high levels of interactivity, I can recommend Ravager, Third Crisis and Seeds of Chaos. All three are substantially more interactive than the Headmaster. Third Crisis also has the bonus of being completely finished.

Fair warning, though: all three also go hard on the kink (yes, more so than the Headmaster). For some reason the more interactive games also tend to be the ones with the more extreme kinks.

I can also second Rusty's recommendations of Corrupted Kingdoms and Harem Hotel. That said, the interactivity in Harem Hotel is kinda fake interactivity. You can move around and choose what order to do things in, but ultimately everything plays out almost exactly the same no matter what you do. And Corrupted Kingdoms is somewhere between that and the three I listed above.

Eternum, Once in a Lifetime and Ripples are all good games but are traditional visual novels - you make a few choices here and there but there's not a ton of interactivity.

My guess is that the game uses pre-rendered images for its graphics (I don't know for sure but most games like this do). Those don't lend themselves well to customizable characters as each combination of appearance traits requires another version of each image. So it's probably a technical limitation.

Meddler's an interesting one - it's one of the weakest T1 heroes on its own but it's one of the strongest if you can cover up the bones sides, which isn't that hard to find a item for.

The bones sides also aren't as bad as they seem. Sure, assuming you only have Burst it takes 4 mana to remove the bones and it only gives you 1 mana, but they don't attack the turn they're summoned. So you can use that mana killing things that are actually going to kill you this turn and deal with the bones later. And when you do, you get a bonus 2 damage killing the bones (assuming something else has been summoned above them). So summoning a bones is really a net loss of 1 damage as a tradeoff for getting to get that damage now and pay it back later.

Weirdly people are giving you incorrect answers here.

Yes, there is rape. It's not done by the main character, it's taken seriously, treated as a bad thing, and not shown explicitly on screen, but it does happen and recovering from the consequences is pretty central to the arc of one of the characters.