More please?

"I came here to read more of your story and steal your property. And I already stole your property" - Blood Raven

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Blood Raven from Diablo II?

If he chooses to meet a Daedric prince I vote Azura! She, Sheogorath and Nocturnal are my favs.

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A fair assumption. You can learn a lot from looking someone in the eyes.

So by how the two are acting I assume this is going to be Ash x Luna or Ash x Luna x Celestia? With how their ruling system works I also have to Assume that if ONE chooses a Lover they BOTH have to choose one so why Ash?

Also if and I mean IF you have to contact a Deadra then Either Sheogorath, Azura or Hircine. I say Hircine as I think he would be good for Equestria and Terra as any of his Werewolfs (the ones He turns or has his Champion Turn) would be able to keep the more....Dangerous Creatures and Monsters in check AND Ash would likely be Granted lycanthropy which in my opinion is worth it!

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Well, I'm not going to tell you whether or not there will be a romance nor how that theoretical romance would play out, now would I? However, I will say this; the situation may not be as simple as you might think, if said situation even happens.

As for the Lycanthropy... Well, remember that not all humans can control themselves while changed.

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W40k Dawn of War

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If I remember right, The Change is based on Willpower and your Magika levels. Though there is also Hirceine's Ring, but Assuming this Fallows Skyrim Logic then He should be able to Turn at will.

Also I think Celestia and Luna would be Perfect for him, He seems really Comfortable around them and from their actions they seem the same. I just don't see him being able to be himself around any one else.

Also I can't wait for Book Pone to find out about his magika, I expect her to write it, The Atherium, the aedra and the Daedra off as Nonsense and piss him off

If I may make a suggestion... Instead of going by game mechanics, why not go by how the lore describes how Magicka works? Magicka is described as to be dangerous if not approached with caution for first timers.
Now, this is just my own headcanon though based on research I did long ago when I started writing Magic-Eye's story.

I've always believed that spellcraft was done by a mage who channeled their magicka and bounding it to a word, words, or sentence and written into a spellbook. That spell created would only be unique to that user, but if anyone stole the spellbook and tried to use magicka that isn't their own, it would either be less effective or they'll gain severe backlash. Magicka can also be drawn from aetherious passively if you have a strong will.

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As for going by game mechanics, I've already got plans for that. The game mechanics made Magicka easy to learn and safe to learn. I have no desire for Ash to learn all the spells in a week. Sure, he could do that with Novice spells, but higher spells are harder to learn.

Oy, like it's so hard to contact your neighbor Sheogorath. Just chant Discord three time and he'll be there.

Really liking this fic so far. Different and not self-indulgent like many other inserts, and the character is actually smart enough to weave his own story to explain his powers to have a solid cover story

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Lawl!

Interesting. I certainly didn't know all that lore, so thank you for that.

Ash was really surprised that neither of them interrupted him to ask questions, though they were likely waiting to he finished before asking questions. “Hermaeus Mora is considered the most evil and is the Prince of Knowledge and Memory. His realm is Apocrypha, an endless library of all knowledge, most of it forbidden, where he traps the souls of those who desire to know more.”

Jokes on him just send twilight there

Funnily enough, Hermaous Mora was always considered the most NEUTRAL daedra as well as the most reasonable, since all he cares about is gathering knowledge no matter the cost, even if that means helping or harming mortals in any way.

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Really the only evil ones are Boethia, Dagon, Vaermina, Clavicus, Molag, Namira, and Mephala. All the others fall into a gray area or a good. Meridia, Azura, and maybe Jyggalag. The rest aren't exactly good or evil and Sheogorath doesn't fall on this spectrum of good, evil, or neutral because he switches sides or just destroys the scale whenever he's bored, probably even when having the time of his life.

Why did you forget Talos?