It isn't until the next day that Michael and Saeko's date actually ends. After their time at the arena was finished, they immediately left and began hunting nearby bandits at Saeko's request... They may have gotten too 'into it', judging by the fact it was now mid-afternoon of the next day.
Saeko had let her Werewolf instincts and bloodlust free, and Michael had happily gone along with it, ending up with them killing the vast majority of bandits around the centre of Cyrodil. Michael's ability to fly made it incredibly easy to spot the obvious criminal encampments, and with Saeko's urging, he wasn't all that keen on stopping either.
By the time they returned, Michael had collected enough souls to satisfy Shadow Fiend for like, a month... Maybe?
Regardless, they were greeted by a tired Tiffania as they returned to the tower, the girl having stayed up all this time so she could hear how the date went. Needless to say, she wasn't all that amused after hearing all the violence and murder that was involved.
Still, it could have gone worse. Screwing up the date was far worse in Michael's mind than the tens of thousands of murders he and Saeko had committed in under a day.
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Winterhold got the funding they requested from Surtr and so the Navy was being built far bigger than Kunkka and Ennura had originally anticipated, not to mention the few volunteers who'd joined up upon hearing Surtr's intentions.
Of course, a large percentage of the gold was being used to renovate the city, but that was being kept hush-hush by those who managed Winterhold. No one was that keen on revealing this to Surtr, thinking the High King could spare some coin for reconstructing what was once the greatest city in Skyrim.
During this, Michael also met with Durnehviir who'd returned after completing his task. He'd been told to go observe the waters around the Summerset Isles to see if they'd be sending another attack their way...
What Michael hadn't been counting on was Durnehviir's misinterpretation of his orders. The Thalmor had tried sending out their navy again, a far larger one compared to last time comprised of all the ships that'd once been used against Hammerfell... That was past tense, as Durnehviir had destroyed the whole fleet over a series of days.
He'd waited for them to get far enough out to sea that turning back would be incredibly difficult, then began picking off boats on the outskirts of their formation, not allowing their mages or cannons the chance to get a shot off at him.
Once he'd whittled them down to a few Man O'War sized vessels, he'd begun diving underwater and biting large holes into their hulls. This was the advantage of essentially being an undead dragon, dragons in the first place didn't really need to breathe, but it was much less so for Durnehviir due to his links with the Soul Cairne.
Needless to say, the Thalmor wouldn't be attacking anyone for long while, even if they put their full efforts into rebuilding a navy, they'd have to train soldiers to operate them. A time-consuming effort.
Once the dragon had returned, he'd sent him off again, this time to Solstheim to see just what Miraak was getting up to. He wasn't afraid of the dragon being controlled, since he'd made his claim as soon as he could. But it wasn't without problems...
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Flashback :
"What is this supposed to do...?" Durnehviir suspiciously asks as he stares down at the piece of paper Michael was presenting him.
"It's a contract. Sign it and Miraak won't be able to fuck with your mind. Plus, there's a high chance it'll free you from the Ideal Masters."
"Hi tinvaak vahzah? Are you certain?" Durnehviir asks, now with acute interest.
Michael nods, "Just made sure to read it properly then sign your name..." he palms his forehead, "Right, how would a dragon sign his name...?"
"That is of no concern, lay it down on the floor."
Michael does so and the dragon quickly reads through the contract, it's eyes squinting slightly when it reads a few lines, "You wish to claim my soul wholly for yourself? What difference is this to the treatment of my former masters?"
"The difference is that I'll let you live in Tamriel. Plus, if you die you'll just end up in my own realm as opposed to theirs. You're already mine so signing it doesn't change much." he shrugs.
"You are wrong. We have a verbal agreement now, a Kalyul, putting it in peluth, writ, makes it far more powerful... You could end me with but a word..."
"Well, if you don't sign it Miraak could end you with three. So just sign the damn paper."
Durnehviir lets out a sigh, "If you wish... Deyra. DUR NEH VIIR." he speaks, his words printing themselves hotly into the paper below him, scarring the pale page with his fiery Thu'um.
Things should've concluded there. But an angry ephemeral shout made itself known, Durnehviir let out a similar roar as his body quickly folded in on itself, tens of thousands of shadowy hands pulling the dragon apart like he was paper-mache.
Michael tried to stop it, but realised the process wasn't stoppable after the initial scream... The problem was, Durnehviir's soul was still technically owned by the Ideal Masters, and he'd only been in Tamriel due to a loophole Michael had presented.
His attempt to claim the dragon's soul went directly against their will, causing his body, which was formed from the energy of the Soul Cairne to return to its origin.
Michael wasn't about to let his pet dragon get sent to the slaughterhouse however, he wouldn't be much of a Daedric Lord if he let those pussies push him around!
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