Skyrim X Reader

Brynjolf x Reader

(As requested by Souleaterlover482482 and smolgay_sinner)
(Again, spacing problems, I apologize for that)

The Thieves Guild wasn't so bad, right?
Wrong.
It was falling apart. And they blamed you. They as in Mercer, Vex, Sapphire, all of them. They all blamed you because you stole the less. You were too busy with the Dark Brotherhood contracts, and jobs from the Companions. You barely had time for the Thieves Guild when you were the Harbinger and the Listener. It wasn't totally your fault, right? At least, that's what you thought. But everyone else thought different. Mercer and Sapphire already started a petition to kick you out, possibly even kill you since you knew too much about the Guild. Fortunately for you, there were a few members of the Guild that despised the idea of losing you. Rune and Brynjolf specifically. Sure, they still blamed you for the Guild's problems, but neither of them wanted to lose nor kill you.

It was early Sun's Height, making the weather very hot. The Thieves Guild armor, everyone agreed, was very hot to wear during this time. Being a free day for you, you decide to join the Guild in the small body of water in the Ragged Flaggon. It was the coolest place they could think of, so they all gathered there, wearing very thin clothing. As you enter, pairs of glaring eyes were glued to you, some full of hatred. Vex scoffs something under her breath, resulting in Sapphire cracking a devlish smile. You frown, moving away from them as you scurry to the corner of the pool, where nobody was. Dipping your feet in, you stare at your reflection in the water, a sad look on your face. Behind you, as you could see in the reflection, the familiar ginger that took you into the Guild hovered over you.
You turn your head to see him, offering a weak smile. He smiles back, it being sympathetic and forgiving.
"Hey lass," he murmured quietly, taking a seat next to you. That's when you noticed he was without a shirt, only wearing ragged pants that he probably stole from Mistveil Keep. Well, it was hot.
The weather. Not him.
The weather... right?
No, no, he was pretty hot too.
"Hey," you respond, looking back down at the reflection. Now his feet were in the water, making the water move, blurring your reflections.
"Why the long face?" He asks softly. Most likely he knew why you were upset, but he cares so much as to ask.
"Everyone hates me," you shrug, trying not to seem too hurt about it.
"I doubt that's true, lass," he smiles again as your (e/c) gaze meets his green one.
"No, everyone does. You know what Mercer and Sapphire are planning, they basically want me dead," your brows furrow as you frown.
"You know how they are. They hate everyone. You know how much Rune and I care about you, you're not completely hated. Sure you're not the most active member, but you're still a member. Mercer and Sapphire need to understand that."
As he speaks, you nod in agreement, looking down at your reflections in the water. At least he was understanding, right? He's your favorite member in the Guild, it's good- great, actually- that he understands so well.
"Should I leave the Dark Brotherhood and the Companions?" You suddenly blurt. "Aela can take over the Companions, and the Night Mother will-"
"No," he interrupts you before you can go on. He had a frown on his face, emphasizing his disapproval of the idea. "You belong there. Just as you belong here."
You give off a sigh, absent-mindedly resting your head on his shoulder, suddenly feeling a bit drowzy. The heat is probably getting to you, you think to yourself. Obviously Brynjolf didn't mind that you had your head on his shoulder. He didn't mind at all.

~months later~
(I forget what quest, but this takes place during when you SPOILER battle and kill Mercer... it's not completely on point, I apologize for that, but I did try my best)
"Just give up, (y/n)!" Mercer shouted at you, his Dwarven Sword unsheathed, reflecting off the light coming from cracks in the Ruin's walls.
Mercer had betrayed you all, he turned against the Guild. You are with Karliah and Brynjolf, though they stood on a ledge, while you and Mercer shared a level below them. They watched, fear and worry clouded in Brynjolf's eyes, while hunger for revenge gathered in Karliah's.
"Never!" You spat, quickly bolting for him. He climbed up the statue, knocking out a gem eye, causing the ruin to start to flood. You follow behind him, and being faster, you caught up to him and started a quarrel, the only sound being the clashing of swords and water splashing as it filled the room's floor completely, now making it impossible to see the floor. The clashing continued until you make a final blow, stabbing him right in the stomach. The water was now almost to the ceiling, so you had luckily killed him just in time. Karliah and Brynjolf sigh in relief, jumping into the water with you as you grab the gem, swimming to the top of the room to make your escape.

~back at the Guild~
"And bam! He's dead!" Brynjolf grinned, telling the tale of what the previous events were to the Guild. You smile shyly next to him as you get pats on the back in approval- even from Sapphire. Karliah leaned against the wall, arms crossed as she caught your gaze. She smiles at first, but quickly shifts her gaze to Brynjolf, then smirks at you. You blush, glaring a bit playfully at her before you look away.
Okay, so now, thanks to Rune, whom you vent to about all sorts of stuff, the whole Guild knows about your "crush" on Brynjolf. Well, everyone *besides* Brynjolf. It was nearly impossible to think Brynjolf didn't know, but he didn't. Which was good for your case.
"I couldn't be more proud," Brynjolf grins again, hooking and arm around your shoulders as he pulled you closer to him. Everyone- besides Vex and Sapphire- were smiling about your victory.
"I need to speak to you alone, lass," Brynjolf whispers in your ear discreetly, sending goosebumps down your spine. You gave a quick nod before he slipped away, though the others continued to congratulate you.
"It's late, guys, we should get some rest. Keep to the shadows, my friends," Vex announced before going to the next room. Most agreed, following her, but some stayed in the Ragged Flaggon for a few more drinks. Not knowing where Brynjolf was, you follow Vex and the others to go to sleep. Before you have a chance to get in bed, Brynjolf takes your arm and quickly pulls you into the training room. He looked a tiny bit nervous, but the rest was pure cockyness. Yes, that's a word.
"Hey, (y/n)," he smiles. "I was wondering if you'd like to have a few drinks with me tonight. Up at the Bee and the Barb?"
You didn't know how to reply.
"U-umm.. sure?" You smile, trying to show your excitement more than your confusion.
"Great," he smiles even more, motioning you to follow as he left the training room. You quickly follow as he heads for the ladder that leads to the Riften cemetery, also known as the secret entrance/exit for the Thieves Guild. Once there, he smirked and motioned you to go first. Obeying without question, you climbed up first as Brynjolf watched.
Oh damn.
That ass of yours.
He loved the perfect view of it.
Of course, you didn't know where he was looking, but you waited for him at the top.
"Excited, lass?" He chuckled at you.
You let out a small giggle.
"Is it showing?" You smile cheekily, making him chuckle again as he led you through the graveyard, down a path, across a bridge, and to the town center where the Bee and the Barb was. He opened the door for you like a gentleman, reminding you of old memories of Vex scolding him for not ever doing it for women. He finally learned, huh?
You sit at the bar, containing your excitement well as he sat next to you, ordering the both of you a drink.
"Thanks," you smile as he hands it to you. Before you take a sip, he grabs your wrist, allowing him to clink his bottle against yours gently.
"Cheers to your victory," he smiled, then let go of your wrist as he took a swig of the alcoholic drink.
You copy, not too worried about getting drunk. You weren't that bad about it... right?
Drink after drink after drink, you both got... wicked fucking drunk, to say the least. You both laughed at everything. Absolutely everything.
"H-hey Brynjolf," you stutter, a sluggish smirk on your face. He looks at you with the same expression.
"I bet you-" you pause to gulp down another swig, "300 septims that you can't make me moan. In bed," you add quickly, wiggling your eyebrows at him.
He quickly grins, standing, and taking a moment to balance.
"It's on, lass," he says sluggishly, placing ten septims on the bar for a room before hurrying up the stairs. No, he didn't even ask. He just paid.
Being drunk is a blessing in this situation, you see. Well, until the hangover. And the realization of what happened the next morning.

The two of you wake up, naked, legs intertwined with each other's under a Saber Tooth Cat's pelt blanket. His arm was under your neck, heads nearly touching on the pillow. Your heads pounded in a migraine, thus starting your hangovers.
"What... what happened?" You ask groggily, looking at him in a bit of confusion.
Oh... oh no. No. You guys couldn't have possibly-
"I'm so sorry!" You say quickly, sitting up as fast as possible. Your head pounded harder, making you lay back down before you passed out.
"(Y/n)," he said quickly. "No, no, don't be sorry. It's okay, I promise! We were drunk and.. and.. well, I'm not complaining about what happened."
You pause, trying to take in what he said. Were you still drunk or did he actually say that?
"R-really?" You stutter again, looking up at his green gaze. Oh Mara he looks so gorgeous...
Before anything else happened, his lips were on yours as he pressed himself against you gently.
You weren't drunk.
No, he was actually kissing you.
"Yes, really," he smiles against your lips before kissing you again.
Okay, so all it took was a bet, and some alcohol.
Oh.
The bet.
"You owe me 300," you grin against his lips. Brynjolf pulled away to laugh, not caring about his migraine.
"I'll pay you tomorrow," he said right before he kissed you again.

(I AM SO SO SO SORRY I feel like I did a horrid job on this one, so I apologize for that.. I really hope you enjoyed though!!)