An Ambush in the Ratway
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An Ambush in the Ratway

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Idk if anyone already did this, butâŠ
Esbern
3D render for The Elder Scrolls V: Skyrim
Design credit unclear
I love the theory that Delphine used to be involved in the thieves guild. I think it gives her more depth and flavor, and I think it makes Esbern hiding in the ratway all the better.
Skyrim fun fact; if you spare the guy talking to the interrogator in the Thalmor Embassy he'll show up in the Ragged Flagon when you ask around for Esbern. When you're done, he'll get up and head to the Ratway to report to the Thalmor who'll head in to question the Thieves Guild members, and might lead the Thalmor to you.

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Round six, before i lose signal:
Caius Cosades, Esbern, and Calcelmo
Current or younger versions of themselves is up to you.
Also, what other fandoms can be submitted?
Oh, drat! Not the lost signal! đ
Hmm, good question. Some might tell me to keep it TES, but I'm chaotic, so idc. Lord of the Rings, Star Wars (except Disney Star Wars), Doctor Who (pre 2017), Hazbin Hotel. I'd say Harry Potter and Avatar: The Last Airbender, but only for adult characters. Just because 17 year old me would be extolling Draco Malfoy doesn't mean adult me should, you know? Oh what else...Once Upon a Time? Pirates of the Caribbean? The MCU through Endgame. I'm not into a lot of things. I stick with what's comfortable.
Now...
Slow burn: Caius Cosades over the span of years, waiting on letters with no return address and posting replies to different drop off points detailed in the post script. Missing the long ago carefree days of youth. Pining. Holding out hope. Maybe marrying someone else anyway because Caius doesn't want my life wasted on him (like he wasted his on Skooma to cope, but I don't ever know that). Maybe finding each other again when he returns to the Imperial City, but where can we go from here if I'm married to someone else?
Fake dating: Calcelmo. I'm after the research. I flatter his ego. I'm looking for a payday only his access to select Dwemer artifacts can get me. Wait, what are feelings? I didn't plan for THIS
Enemies to lovers: The funny thing of Esbern is that I wrote about him in my Leara Crackship Collection. I think it'd be hilarious to have a super dubious opposite sides of the war enemies to lovers between Esbern and a Dominion sorcerer during the Great War. Does she inadvertently help him escape Cloud Ruler Temple before it's burned because she has a quirky passion for knowledge that makes her disobey the order to burn the Blades archives and capture the loremaster? Could be interesting
FMKâFanfic Trope Version
The Dragonborn does not speak at the council, for all the trouble she went to arranging it.
She sits in a straight-backed chair at the head of the table, her sword in its scabbard resting against the stone. (She was the only one permitted to carry a weapon into the assembly.) Lydia, her sharp-faced housecarl, is seated to her left.
Itâs the Dragonbornâs council, for all intents and purposes â it may not have been her idea, but it was she who petitioned for it, persuading Arngeir and then the war-leaders and the dignitaries they dragged with them. It was for her sake alone (Dragonborn, Ysmir, legend come to life) that some agreed to attend at all.
"petty victory" you tried to have me killed three separate times.