Deception, Domination, and Dragons (Skyrim Self-Insert)

Chapter 1: Prologue



A/N: This story is an old free write of mine that I wrote over the course of 61 days from January 1st to March 2nd of 2022.

It is now completely transferred over to this website, so enjoy the ride!

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“-y, you! You’re finally awake. You were trying to cross the border, right? Walked right into that Imperial Ambush, same as us and that thief over there… and the Altmer too, I suppose.”
 
“Damn you Stormcloaks… Skyrim was fine until you came along! Empire was nice and lazy! If they hadn’t been looking for you, I’d have stolen that horse and been halfway to Hammerfell!”
 
“I don’t… w-what’s happening? I don’t understand what’s going on…”
 
The first two voices, as I swim in and out of consciousness, are strangely familiar to me. Almost like I remember them from something I watched or played. They’re also coming from above me… which is more than a little disconcerting, considering there shouldn’t be anyone standing over my bed. Certainly not talking about… about Skyrim of all things.
 
Except this isn’t my bed. The surface beneath my head and back is hard and uneven, not soft and comfortable like it should be. Slowly opening my eyes, I’m greeted not with the sight of my bedroom ceiling, but a blue sky overhead. What… what the fuck?
 
With a loud groan, I interrupt the three talking as I move to sit up. That’s when I find out my hands are bound together with multiple coils of tightly wrapped rope. That’s also when I discover that my hands… are no longer my hands.
 
Except they are. Those are the hands that I remember having… in one life. Blinking rapidly, trying to get my bearings and only drowning in memories that were splitting my head in half, splitting my very sense of self in two. On one hand… on one hand, I was a purveyor of smut, an erotic writer who made a living via my debauched writings. I was a human man in my late twenties who had just spent the last year working on improving my health and losing the majority of the hundred plus extra pounds of fat I’d been lugging around for a decade and a half.
 
On the other hand… I was none of those things. Instead, I was a Thalmor Agent, an Altmer who had grown up within the Third Aldmeri Dominion, indoctrinated into their beliefs. I was convinced of my superiority as a member of the Thalmor, and that all who were not my kin were beneath me in every way.
 
At nearly seventy years of age, my Thalmor side had a lifetime of experience compared to my human side, but ultimately with a life span of three hundred to four hundred years on average, I was far from old by any means. Certainly, I was neither aging nor growing frail like I would be if I were still a human.
 
The only thing truly protecting my human memories from the supremacist thoughts of the Thalmor half of my mind… was the bone deep certainty that this, all of this, was just a game. I may have only had just under three decades of human experiences, but they were so outlandish and far flung from my Altmer experiences that it was impossible for either to overwhelm the other.
 
“Come on, friend. Up with you. Here, help me get him onto the cart.”
 
“Urgh, fine.”
 
As equally bound hands both reach to grab my arms on either side, I have to quell my initial reaction to jerk away and bark at them not to touch me with great difficulty. I can’t be in the business of making enemies right now, not if this is what I think it is… and after a moment, the Thalmor in me reluctantly agrees. And so, I’m yanked up and shoved onto an empty spot on the bench between two men who are both bound at the wrist as well.
 
Across from us, on the other side of the wagon, are two women… and I can’t help but do a double take as the man on my left slaps my arm and gestures with his hands to me and one of those women.
 
“I’m telling you both… we shouldn’t BE here. It’s these Stormcloaks who the Empire wants!”
 
This is… Lokir, the Horse Thief. The guy who gets himself shot at the start of the game by trying to pull a runner. Which makes the man on my right who is quick to answer him Ralof, the Stormcloak.
 
“We’re all brothers and sisters in binds now.”
 
I have to admit, I’m only paying the two bickering on either side of me half a mind at best. Most of my attention is on the two women sat across from me. One of them is completely unfamiliar to me, but nevertheless incredibly gorgeous. Even the Thalmor in me is rather taken with her features, despite his instinctive prejudice against so-called ‘inferior’ races. But then, just because the races of Men and even the other types of Mer are all naturally inferior to the Altmer, didn’t mean they couldn’t be admired for… aesthetic purposes.
 
Heh, shit, I think the two halves of my mind had just found something else they could agree on. Indeed, even dressed in the sack cloth that our captors had clearly changed her into, the unfamiliar girl is beautiful, with shockingly red hair and a perfect face, complete with bright wide eyes and a button nose. She’s also looking singularly out of her depths, though from what can be seen of her arms, she doesn’t look soft.
 
Indeed, the trained agent in me says that she’s capable of putting up a fight, for all that she’s doing a remarkable job of seeming small, helpless, and scared right now. It just wouldn’t be a very honorable fight. Instead, I find myself imagining her with daggers, or perhaps a bow… and a set of form fitting leathers designed to keep her steps quiet as she pads along, taking only what kills she needs to on her way to her target.
 

My Thalmor instincts, honed from decades of training, were telling me that the girl was a thief, likely a much better one than the Horse Thief to my left. But my human instincts, honed from multiple playthroughs of this whole thing as a video game were telling me something else.
 
Because if I was sat between Ralof the Stormcloak and Lokir the Horse Thief, and the other woman sat across from us was who I thought she was, as impossible as that seemed… that could only mean this seemingly unassuming girl was the Last Dragonborn, destined to save all of Tamriel from the World-Eater’s Return.
 
While the part of me that is supposed to be a deep undercover Thalmor Agent reels from the thought, Lokir gestures to the other woman in the cart… the one currently wearing a thick, heavy gag over her no doubt pretty mouth.
 
“What’s wrong with her, huh?”
 
Ralof, of course, is quick to jump to the gagged woman’s defense, confirming my suspicions and at the same time shocking me to my core.
 
“Watch your tongue! You’re speaking to Ulfrida Stormcloak, the true High Queen!”
 
Reeling back as if struck, Lokir shakes his head wildly.
 
“Ulfrida?! The Jarl of Windhelm? But… but you’re the leader of the rebellion! If they’ve captured you… oh gods, where are they taking us!”
 
Ralof gives his customary doomer answer and Lokir starts to panic, forcing the Stormcloak to try and calm him down. I’ve already tuned them both out at that point though, to be honest… especially as we’re finally entering Helgen, and something, or rather, someone has caught my eye. As our cart passes through the town gates and begins to turn left along the road, I see General Tullius astride his horse, speaking with First Emissary and Thalmor Ambassador Elenwen astride hers.
 
For a brief moment, the briefest of moments, her eyes flicker away from the General and manage to meet my own. Its only for a second, but once again my decades of service as an Agent to the Thalmor come in handy, and as it turns out, my Thalmor side is able to get quite a lot from that glance… which my human side is then able to provide further context on.
 
Elenwen looks grim… but also resigned and almost content. Like she’s willing to let what happens here today play out in its entirety. Which… given what I know from the lore as well as from serving the Thalmor, DOES make sense. Skyrim is in the midst of a Civil War… and the Thalmor want nothing more than for that Civil War to continue.
 
Not only does it serve their interests to see the Empire further weakened, but it allows them to continually meddle in Skyrim’s affairs. One of the concessions they’d forced from the Empire after what was known as the Markarth Incident, was the ability to send what were effectively Inquisitorial Death Squads into Skyrim.
 
Usually traveling in groups of three, the Thalmor Justicars had free reign to root out all Talos worship… and used that free reign to be menaces and in turn prop up the Stormcloak cause, driving more and more Nords into their arms and forcing the Empire to dedicate more and more manpower to retaking the province.
 
 Now, my role was not to be one of those Justicars, which is why I had been trying to cross the border into Skyrim on the sly, only to be caught in that damn ambush. Fuck, it was freaky having two conflicting sets of memories of the last few days. In one, me playing my latest playthrough of Skyrim. In the other, me planning my entry into the province on the sly so I could further the Thalmor’s plans on the down low, rather than out in the open like my peers.
 
Ironically, if only I’d experienced this meld a few days before, I might have avoided that damn ambush altogether. Then, I wouldn’t be in this position, hung out to dry apparently by the First Emissary who clearly knew who I was from that moment’s glance, but also wasn’t going to do anything to help me.
 
Tch. This was bad. Like… really bad. Ralof is still blabbering along in the background, but the cart is almost to its ultimate destination now. Which means… it’s almost time for the execution.
 
Relying on a dragon to swoop in and save the day, let alone the World-Eater himself, sounds like insanity to my Thalmor half. But at the same time, what the fuck else am I supposed to do? I have… I have magic. I’m not some level one player just starting out. Heh, I’m not even the Dragonborn. That’s the cute redhead across from me.
 
As a Thalmor Agent intended for long-term deep undercover work, I am fully trained in the Illusionary Arts. In fact, I have a favored spell that I’m pretty sure wasn’t even in any Skyrim playthrough I ever did. Charm Magic… that wasn’t from Skyrim, that was from Oblivion. Still, the ability to change the target’s disposition towards me would be insanely useful and from my Thalmor memories HAD been insanely useful… and pleasurable, many times before.
 
But not right now, not surrounded by so many guards who would almost instantly see me casting a spell and fill me with arrows just like they were about to do to poor, poor Lokir.
 
Right on schedule, as we’re told to get out of the cart, Lokir’s panic comes right back.
 
“You’ve got to tell them we weren’t with you! This is a mistake!”
 
The Imperial Captain, much like both the Dragonborn and Ulfrida, is much more beautiful than she was in the game. Whether that’s because this is now the real world or might be a sign that something I’m hoping for with all my heart is indeed true, I don’t know yet. Still, for all that the Captain is beautiful, she’s still also a complete hardass.
 
“Step towards the block when we call your name, one at a time!”
 
As she reads out Ulfrida’s name, and then Ralof’s name, I straighten up, briefly considering stopping Lokir and saving his life. After all, if all goes to plan, literally only one idiot of a Stormcloak is going to die here. Too eager to visit Sovngarde for this own good, that one. But… no. I don’t try and stop Lokir. I don’t say a word, as the Horse Thief’s fear of death finally gets the better of him.
 
“N-No! I’m not a rebel! You can’t do this!”
 
“Halt!”
 
“You’re not going to kill me!”
 
“Archers!”
 
And like that, Lokir is littered with arrows before he can so much as make it a dozen steps up the road. I watch him fall dispassionately, leaning heavily on the half of me that’s currently Thalmor… because honestly, my human half is quaking in my boots. For all my knowledge, I was never very courageous. I was an introvert who stayed in my room all day. Sure, I was interacting with technology beyond even the Thalmor’s wildest imaginations, but there was still a massive breadth of experience between my two sets of memories.
 
I was honestly a little grateful for it… if I was just the human me, I would have already thrown up by this point, and been absolutely quaking in fear. If I were just the Thalmor me, I might have already tried something and likely died for my troubles. As it is, I’m just me… and the me that’s me knows to wait and remain calm.
 
“Wait. You there. Who are you?”
 
I perk up at that, as Hadvar calls out to the girl I think is the Dragonborn. Fidgeting in her bindings, bouncing from foot to foot, she puts on her best puppy dog eyes and even affects a wobbly lip.
 
“M-My name is Svanna sir. F-From Riften.”
 
Well now, that had all sorts of implications, didn’t it? The Thalmor in me is VERY interested in what the human in me takes away from that, to say the least.
 
Looking to the Imperial Captain, Hadvar frowns.
 
“She’s not on the list, ma’am. In fact, neither is the Altmer. The list ends here.”
 
The beautiful Captain’s dispassionate eyes flicker over both of us… and then her gorgeous face contorts in an abject sneer.
 
“Forget the list. They all go to the block.”
 
As Tullius steps forward to give his speech and we all assemble near the headsman’s block, I confess, I’m not actually listening to the General. Rather, I’m doing two things at the moment. One, I’m stepping a little closer to Svanna then is strictly necessary, and when she glances my way, startled, I give her my warmest, kindest smile. A smile that I have used many a time to get a woman’s guard down, in fact.
 
Svanna blinks, and for just a moment there’s something akin to suspicion in her eyes… but then she’s hesitantly smiling back, still looking like the scared little girl she’s pretending to be.
 
The other thing I’m doing… is listening. And sure enough, there it is. A distant roar that all but guarantees my foreknowledge of this moment is correct. As the Priestess begins to give us our last rites, only to be interrupted by the foolhardy Stormcloak who rushes straight forward to his death, I clench my hands together into fists.
 
On one hand, I’m convinced now that the events I remember from the game are about to play out right here and now, in this suddenly very real world I’m stuck in. On the other hand… while that DOES mean an indefinite stay of execution, it also means the arrival of the World-Eater, the destruction of Helgen, and the death of who knew how many NPCs. And hey, would you look at that, I was pretty sure I wasn’t the fucking main character of this goddamn story.
 
And so, even as the Stormcloak’s head rolls and Svanna is immediately called up next, just as scripted… even as the roaring sounds of an approaching Alduin continue to fill the skies… I tense up. Not because the headsman is about to bring his axe down on Svanna’s neck… but because I see Alduin ahead of time since I’m looking for him. I see him coming for us, coming to land on the tower.
 
Before Svanna can lose her pretty little head, Alduin lands with a crash and only my foreknowledge lets me avoid stumbling like everyone else does. Instead, I rush forward and yank Svanna to her feet as Alduin roars out a raging gout of fire over our heads.
 
This is it. Execution interrupted, Massive Fuck-Off Dragon aiming to burn us all to a crisp. And unfortunately, I couldn’t just run for the hills as much as I wanted to. There was only one path I was SURE that would get me out of here… and it was right next to the Dragonborn’s side. If I stayed glued to her, then maybe, just maybe I got to live. If I deviated even slightly, then I most likely died.
 
It was time to see if I could survive this first encounter with the World-Eater with zero plot armor and zero prophecy backing up my survival. Fuck my life.

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