Hey there! This is just something I've been pondering for a while since replaying Skyrim. It's based off the thieves guild story line with a particular focus on Brynjolf & Gallus, I intend for it to cover the past when Gallus was still alive, to the present storyline that takes place in the events of Skyrim. There is an OC in this, in case you are adverse to such things and there will be some deviations from canon (but I intend to work with the canon as much as possible, just with slight changes - the same outcome for everything is still the same)

Basically, it's a story about Brynjolf's life from when he's first joined the thieves guild to the Mercer/Karliah/Nocturnal mess (and maybe a little bit after that too)

The plot will be quite slow at first in order to establish what happened before Gallus died, however it will start to pick up after that!

Thanks for taking the time to read it!

Nightingale's Song

Part One

Chapter One

A City of Thieves

It was a thieves world. Or, it was in Riften at least. The entire city was in the pocket of the Thieves Guild – nothing went on there without them knowing, and every guard was bribed or threatened into complacency. The merchants all paid protection money and if anyone tried to work against them, they found themselves in jail pretty quickly.

It was a good place to be a thief. Here, Brynjolf could walk the streets without being cautious – and some other thieves even didn't mind if it were public knowledge they were a thief. In Riften, being a thief was merely a career choice, not a heinous crime. And it made seducing young maidens quite a bit easier, they all seemed to have this notion that being a thief made one seem dark and mysterious, or romantic, or something along those lines.

Brynjolf didn't really care as long as it helped him into their beds.

This particular morning he was walking down the streets with an arrogance in his step to join his fellow guild members. His path took him through the market, where he saw a foreign merchant selling a yellow fleshy looking fruit. It was imported from Hammerfell according to the merchant – apparently very delicious.

Skyrim, as a rule of thumb, did not have the best of climates, and the food was none too different. The frost killed most plants during the winter apart from the hardiest and natives species, like apples and berries. In the colder months, very little grew in terms of food, and most people survived off preserved vegetables or fruits from the warmer months, tubers, or cured meats. In certain parts of Skryim, a particular traditional method of burying orca meat in the sand with salt for the better part of a year, then digging it up and eating it in winter, was quite popular. Brynjolf had never acquired the taste for it.

Still, Riften was more temperate than the more northen areas of Skyrim. The summers were warm(ish) and during it the sun seemed to believe it had a personal mission to shine for the entire day at times, only to completely bugger off in winter when the snow came – as if to say, I did my part and gave you four months of constant sunlight, so figure it out for yourselves in winter.

But either way, Brynjolf was used to it. It was all he'd ever known.

The merchant selling the fruit was distracted with a costumer, so he casually snatched a piece of fruit as he passed the stall. Nobody brought him up on it because it was Riften, though some people probably noticed. He took a bite out of the yellow fruit as he walked to the graveyard. It was quite sweet and juicy, he had to wipe his mouth with the back of his hand after a few chews. He'd finished it by the time he'd entered the secret entrance to the thieves guild, and chucked the core in a pile of trash in the corner. Somebody would get rid of it later, hopefully not him.

He was probably one of the youngest people in the guild, but he'd been there for a long enough time that people treated him like family. He was only a teenager when he wound up joining, so even if he was an adult now, some people still treated him like the little baby brother – he hated it.

Gallus, their somewhat eccentric but friendly guild master was standing near his desk, speaking to Karliah, a dark elf of a similar age to Gallus. They were both probably ten years older than Brynjolf, maybe a little less. It was common knowledge in the guild that Gallus and Karliah where a 'thing', though it was considered a bit odd. Most thieves didn't take their relationships beyond a casual screw.

Regardless, Brynjolf hadn't really intended on joining them, until Gallus beckoned. So he obliged and wondered over.

"Excellent," Gallus started warmly. Karliah gave him a polite nod. "We were just speaking of you."

Brynjolf cocked an eyebrow. "Good things, I hope."

A chuckle left Gallus' lips but he didn't specifically reply to his statement. "An opportunity has presented itself to rid Pontus Felskog of a valuable falmer artifact he has recently acquired."

Of course it was about falmer. It was always about falmer with Gallus. Well, perhaps not always, but it sometimes felt as if he were always going on about some scholarly thing or another. Sometimes Brynjolf wondered why he'd even become a thief in the first place.

"He's holding a gala at his estate in Windhelm," Karliah continued. Pontus Felskog was a nord of some wealth and standing, remarkable for being enthusiastic about multiculturalism in Skyrim, and considered to be a quite annoying man who talked too much and too fast by many people. But however annoying or well meaning Pontus was, he was also incredibly fond of his numerous artifacts and possessions and employed a small army of personal guards to watch them, so they had realised earlier that breaking into his estate was not really feasible.

"I want you to go," Gallus said. "I would myself, but Karliah and I have... prior commitments."

The two of them often left for periods of time together. Nobody really knew what they did, most people thought it was something to do with them being a couple, but Brynjolf wasn't so sure. He didn't really worry himself with what they did though. Still, he was a little bit flattered Gallus would choose him in his place. Gallus wouldn't ask just anybody to recover this particular artifact, it would be somebody he trusted not to take it for themselves – it was worth more to him personally than just some expensive item to be pawned off. But Brynjolf had always been close to Gallus so it probably wasn't that surprising.

"You can attend the gala and take it right under his nose," Karliah continued. "But-"

"We're sending someone with you," Gallus finished for her.

Brynjolf narrowed his eyes. "Why?"

"His gala is about celebrating multiculturalism in Skyrim," Karliah started. "You're a nord so you're not exactly an immigrant or part of a minority group, you'll need a better disguise to get in without looking out of place."

He nodded slowly, but allowed Gallus to continue with their plan. "Pontus would be especially thrilled if you went with someone as a couple, but it won't help much to take anybody else in the guild as your partner, a nord and another nord, or even an imperial isn't so uncommon."

"I hope you have a plan other than kidnapping somebody off the street," Brynjolf offered. Gallus chuckled brightly in the way that he did.

"No, that won't be necessary. In fact," he smiled, "we're thinking we can kill two birds with one stone. Mercer seems to think he's found a potential recruit." Brynjolf could see exactly where this was going, though he didn't mind that much. "She's a wood elf, you can take her along and see how she performs."

"A wood elf?" Brynjolf frowned. He wasn't sure he could convincingly pull that off, elves in general weren't so popular in Skyrim (in fact amongst some groups of nords they were very unpopular, and wood elves were considered only marginally better than the high elves.) "Do you think anybody will believe that? Most bosmer won't even leave Valenwood willingly let alone mate outside their race, and some nord men are more likely to stick an axe in an elf than court them."

"Unless they have a fetish," Karliah muttered a little bitterly.

Brynjolf gave her a somewhat horrified look. So help him, he'd pretend to be a couple with some woman to get this artifact, but he wouldn't pretend to be some screwed up nord who got their kicks out of screwing tiny little bosmer women who he'd hurt more than pleasure.

"Which is precisely the reason why this is going to work so well!" Gallus was possibly enjoying this too much. "Pontus is an arrogant creature, he won't be able to resist boasting about the wood elf and nord couple he invited to his party."

Brynjolf wasn't sure what expression seemed appropriate for his emotions at the moment or the situation. Eventually, he just murmured, "this is ridiculous," to himself and went along with it.

o0o

The wood elf that Mercer had found (Mercer was the second in charge behind Gallus in the Thieves Guild) was to be inspected and interviewed before they committed to the plan. They decided to have it take place in one of the rooms above the Bee and Barb, the local tavern (the owners were well and truly paid off to keep quiet.) Brynjolf accompanied Gallus the next morning when it was scheduled. They entered the room together and took a seat each at the same end of a small table. A bosmer woman sat on the opposite end.

She was quite tiny, probably even by elven standards, though all bosmer were slight and short so that didn't mean much. Brynjolf would probably tower over her if they stood side by side. She wore a plain but fine set of leather armour and there were some scars on her features. Her fingers, in particular, had hard callouses on the tips and looked weathered, as if she used them everyday in manual labour. He guessed she was probably an archer, though it wasn't a particularly grand deduction because she was an elf and had a bow on her back, the callouses just confirmed it.

"Hello," Gallus started. "My name is Gallus," he gestured to Brynjolf, "and this is Brynjolf. Mercer tells me you're quite talented."

"I imagine I wouldn't be hear if he didn't," she replied. It was not arrogant or cold, just simple, neutral and matter-of-fact.

"Quite true!" Gallus became serious then. "Now, we have business to discuss."

She did not reply, but held their gaze steadily. She had black eyes. They were a bit unnerving.

"You're going to accompany Brynjolf to Windhelm, were you will steal an artifact of particular value to me. If he thinks you're good enough, you'll be invited to join our guild on your return. If not, he'll probably just leave without you."

Brynjolf studied her reaction carefully. She was not reacting the way most people did. Her features were careful but calculating without being malicious. Usually they had two kinds of recruits, people who were so nervous they almost vomited, or people who were so arrogant it made Brynjolf want to punch them. She wasn't really either.

"Okay," was her reply, then she paused in thought. "And what if I, say, revealed you to the guard?"

Gallus smiled, though this time it wasn't so much friendly but a warning. "Then we contact the Dark Brotherhood, savvy?"