Chapter Text
“Why are we in Riften? This place wreaks of pollution, and crime” Sam scrunched his face as they entered into Riften for the first time. He had decided to accompany Dean on his journey to slay Alduin the World-Eater, as was Dean’s destiny as the Dragonborn.
“When Dean infiltrated the Thalmor Embassy he found the dossier of Bobby Singer. As my contacts have told me there is a man by that name living in the Ratways.” Castiel spoke up, stepping between the brothers. He had joined them on their journey, leaving behind the comfy lifestyle of a court wizard for a life on the road traveling all of Skyrim. And if he got to see some dragon’s up close, that was a personal win.
“As long as we beat those Thalmor bastards here, everything will be fine. We just need to find a way to find this Bobby guy.” Dean grunted as they headed across the bridge into the center of town where the market stalls were. It was good a place as any to start their search.
"Let’s split up to cover more ground" Dean suggested, "Cas, you head to the Keep, and try talking to the house-carl, or the steward, they must know what goes on in this city better than anyone. Sam you head to The Bee and Bard."
"What about you?" Sam asked, watching as Cas set off towards Mist-Veil Keep without a single hesitation.
"I'll head over the market place. One of these merchants must know something. I'll head over to The Bee and Barb when I'm through in the market place."
"Alright. Be safe Dean."
"You as well Sam."
Dean made his way to the market place, eyes scanning the morning crowd of shoppers."
"Weapons for sale!"
"Finest jewelry in all of Skyrim!"
"Please, just one Septim, that's all I ask."
“Excuse me? Did I hear you right? You’re looking for Bobby Singer?”
Dean turned his head to a see a woman leaning over a market stall, chin resting in her hands, ample bosom on display for any prying eyes that walked by. No proud or proper women would put herself on display in such a way; if Dean had been a man of honor he would have averted his gaze. But just because he was Dragonborn, didn't mean he was celibate like the Grey-Bread up on High Hrothgar. He respected the way of the voice.
But he didn't follow it.
"And how can you help me?"
"Well, it would just so happen that Bobby Singer, and I are quite acquainted. I know where exactly his set-up is in the Ratways."
"If you could point me in the direction, I would be eternally grateful." Dean leaned in close to the woman now.
"Not so fast. I will give the information. In fact, I'll take you to Bobby myself. But you must do something for me first; you seem like a man that can get things done."
Dean eyed her warily. "What is it you require?"
"Well you see, a while ago I gave out some very generous loans to some people who were struggling to keep their businesses open."
"So you want me to shake them down for what they owe you?" Dean demanded incredulously.
"Heavens no! I want you to speak to them for me, I gave them those loans out of the kindness of my heart because I didn't want to see my friends fall into poverty. But if they don't repay what they owe men, it'll be my business that goes under!"
Dean wasn't sure of the woman's story, but she seemed genuine.
"Very well. Who must I speak with?"
A grin spread across the woman's face. "Oh thank you very much..."
"Dean. Dean of clan Winchester."
"My sincerest gratitude sir Winchester. The people I would like for you to visit are Bersi Honey-Hand owner of the Pawned Prawn, and Balimund the Blacksmith. They're both on the other side of town – you can't miss'em."
"Will you be here when I return miss...?"
"Y/N my name is Y/N. And I will be awaiting your return in my home, Honeyside, just across the bridge from The Bee and Barb."
Dean offered a smile, looking the woman up and down one last time. "I shall see you soon."
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"You're working for her." Balimund accused.
"What do you mean?"
"Y/N. Rumor has it that's she a member of the Thieves Guild."
"Thieves Guild? And where would I find them?"
"Down in the Ratways of course. You don't know much do you stranger?"
"I haven't been in Riften before. Never had the occasion."
"Well let me tell you a few things about the thief’s guild. They'd sell their own mothers if the coin was good enough. Don't under estimate them-their guild may be on a decline, but they know what they're doing."
"So...about the debt."
"You're still going to collect even after what I told you?" Balimund was shocked to say the least.
"Well you wanted the thieves’ guild to do something for you, and you didn't pay up for what you bought. It doesn't matter if they're thieves, that's just poor business on your part."
Balimund rolled his eyes, throwing a coin purse at Dean, "Tell that bitch Y/N, I hope she chokes on that gold."
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"She's a member of the thieves’ guild." Sam said for what must've been the fifth time.
"Allegedly" Cas reminded, "And she knows where to find Bobby. The sooner we find him, the sooner we can get back to Ellen, and then the sooner we can stop Alduin."
Sam sighed, running a hand through his hair. "Very well, but this doesn't mean I will trust her.”
“No one said anything about trusting the girl Sammy. She wanted her money, I have it, now she’s going to keep up her end of the bargain.” Dean grunted as he knocked once more on the door to Honeyside.
The door opened shortly after revealing a haggard looking y/n hair askew, and dressed in pure black leather armor holding the design of what appeared to be the deadric prince Nocturnal. A cape fluttered behind her, and in her hand she held a cowl that must’ve only covered her face moments ago.
“What the hell?” Dean demanded.
“I could ask the same of you! You didn’t tell me you were the Dovahkiin!”
“And you didn’t tell me you apart of the thieves’ guild!”
“Allegedly” Cas piped in. The woman smiled at him.
“I like him, he’s polite. Unlike you – you… brute of a Nord!”
“Brute? Lady, I got your money for you, would a brute do that?”
“Yes!”
Dean was taken aback, his words failed him as Sam stepped forward. “Where is Bobby? You promised my brother you would take us to him.”
“Well as it would happen, those Thalmor bastards burst into my Ragged Flagon, harassed my guild members, and had the nerve to try to kill me when I demanded why they wanted to go into the Ratways. So I killed them, and I found your friend Bobby. He’s inside.”
The three men rushed past her, “Of course, no need for a thank you. I’m sure this was nothing important. It’s not like a bunch of High Elf wizards tried to kill me with fire or anything!” She snapped shutting the door to Honeyside, and the darkened streets of Riften.