The first month of Y/N's attempt at espionage hadn't gone exactly as they had hoped.
The first time they'd met was exactly a week from their first meeting. She'd told him that she'd yet to find anything more substantial, but had told him the story of the night she had found out how Dean "helped" Benny.
He had begged her to get into Crowley's private office, a statement that sparked off an argument that would've devolved into a shouting match had Ellen not walked by and smacked the older man upside his head.
"What do you expect, Bobby?" she grumbled, handing the young singer some eggs and bacon and the federal agent nothing. "It's not like she's got the keys to the kingdom."
Bobby frowned, but couldn't argue with that. He had already brought up the idea of getting closer to Crowley, but Y/N had told him exactly what he could do with that idea, and the subject was swiftly dropped.
In the end, they separated, the singer frustrated and the federal agent disappointed.
And Y/N had been reticent to meet as often as they did. She'd tried to talk Agent Singer into meeting every other week or possibly even once a month, since the trickle of information had been stoppered. She had practically heard a gasket pop, and that idea was shelved as well.
She was worried, though. Ever since meeting with Agent Singer, Dean had yet to invite Y/N back to his place. Every night, he pressed a soft, chaste kiss to her cheek and wished her sweet dreams, and then drove off.
She'd then trudge up the rickety stairs to her room, frowning. Of course he'd take her saying that he hadn't pushed her into anything as the exact opposite of what she said. But she hadn't had a good excuse for acting the way she had, and Dean had practically gift-wrapped that one for her.
Unfortunately, it was still a lie. She was just as ready for Dean to be her first a month later. However, any time she tried to broach the subject with him, he'd just given her that stupid smile that never failed to make her weak in the knees and simply pulled her in for a hug, telling her that they didn't need to rush.
So, here she was, a month later and frustrated on several fronts.
Life at the club hadn't changed too drastically. Meg still supplied Y/N with the appropriate gossip (which, if important, she'd pass on to Agent Singer); the band still drew in enough crowds to fill a lesser place for a month; and the group still communicated mostly through light-hearted insults.
Crowley was still hidden away from the rest of them, rarely showing himself. His mere presence seemed to suck any life out of a room, and she thanked her lucky stars that they didn't often cross paths. It was hard enough when he made his rounds during business hours, schmoozing and making shady deals with faceless patrons.
But, at the end of every night, Dean would go sit at the bar with whoever was still there (usually Benny, Castiel, and Meg, though it varied night to night), and Y/N would try to gather up the courage to get into Crowley's office.
Or at least make it down the hall.
Or even look in the direction of Crowley's office.
Baby steps.
The night of May thirtieth was exactly like all the others. The band crooned, the booze poured, and a great time was had by all. Benny and Dean helped a particularly drunk patron out to the curb to hail a cab whilst Chuck and Gabe made their home at the bar with Castiel and the girls.
Gabe had made a joke about Y/N sitting on his lap, but a swift glare from Castiel ended that. "Whoa, easy there, brother," Gabe chuckled.
Meg had rolled her eyes and Y/N did the same as she laughed.
"Just because we are brothers does not mean that I will allow you to act in such a manner, Gabriel," Cas frowned, his low, gravelly voice completely monotone.
"Wait, you two are actually brothers?" Y/N's head cocked to the side in confusion.
"You didn't know?" Chuck was incredulous.
"It's never come up!" she defended.
"Plus," Meg added, walking behind the bar to join Castiel. "These two couldn't be more different. Who'd ever think it?"
Gabe raised his glass. "I'll take that as a compliment, doll."
Meg clinked her glass with his, grinning. "Take it however you want."
They all laughed at that. Castiel had even pressed a kiss to Meg's temple.
The doors opened, revealing Benny and Dean as they entered, both looking a little frazzled.
"The old guy finally get home safe?" Chuck asked.
"It took us twenty minutes to convince him that his taxi driver wasn't, and I quote, a 'cock-eyed kraut out to gas us all,'" Dean groaned, taking a seat at the bar next to Y/N.
Benny chuckled as he took another free seat, next to Chuck at the other end of the bar. Castiel was on it the moment they walked in, and Benny was greeted with a full glass of whiskey upon his seat. Benny thanked him before drinking from it like a man who hadn't seen water in days.
Castiel turned to give Dean the freshly-poured drink a moment later. Dean thanked him gruffly and turned to his girl. "And you ain't even changed yet," Dean groaned, running a hand down his face in frustration.
Y/N looked down to see that, damn it, she hadn't changed yet. "Oh, I'm sorry! We just got distracted! I'll be back in a jiffy!" she practically dropped her glass onto the bar, gave Dean a quick, close-mouthed kiss, and hustled off to the back room.
"Hurry back!" he'd shouted after her. There was a beat of silence after that, but, before she shut the door to the hallway behind her, she heard a shout of pain from someone (probably Gabe), followed by laughter.
She was in and out in a moment, faster than usual. She was about to run out and join her friends once more when something caught her eye.
The way the hallway leading to the part of the nightclub she rarely visited worked was simple: it was straight down the line, with exposed brick making it feel claustrophobic. Then, at the very tail end of the hall was a ninety degree turn to the left, back towards the club. At that turn lay Crowley's office. Y/N had only walked down to that end of the hall once and had chickened out long before the idea of actually trying the doors entered her mind.
Tonight, though, there was a sliver of light stretching around the corner, drawing her eye.
She had never seen the light like that. It was like a call, a message: Y/N, get your ass over here.
She took a deep breath, closing her eyes as she did. When they opened again, she was walking towards the source, praying that everyone would be too occupied with each other to notice her extended absence.
Her footsteps made no sound as she tip-toed down the hall. Usually, she couldn't keep her shoes quiet on the hardwood floor, but, without trying, her shoes suddenly decided to cooperate with her. A part of her wondered if it was the walk of a dead man, and the thought gave her chills.
She peeked around the corner and through the slit caused by the open doors, looking for any other living creature. There were none.
She took another deep, shuddery breath, and pushed through the door.
The inside of Crowley's private office was simultaneously nothing and exactly like she imagined. A juvenile part of her assumed it to be a throne room surrounded with flames and the cries of his victims. In actuality, it was a room that oozed comfort and intimidation. Everything had a sharp edge and was either red or black. His dark mahogany desk reminded her of a war table-large and with many sinister bits and pieces covering it. The only plush thing in the room was his chair, which had a high back and was covered in a deep red felt and looked comfy enough to sleep in.
She walked around to the back of the desk, her Y/E/C eyes scanning the desk for something, anything noteworthy enough to jump out at her.
Some of it was in code and there was no way she'd remember what they said. She knew she couldn't take anything in case Crowley noticed something was missing. He didn't seem the scatterbrained type, so she doubted that he often lost important documents.
Here was a golden opportunity, and here she was, woefully unprepared.
She chewed her bottom lip in contemplation, deciding to just try and figure out as much as she could and then come back another night with perhaps a notepad or something to take notes on.
She picked up a few things but was careful to leave every bit of paper exactly where she'd picked it up once she was done. She saw the name of a bank appear over and over again, and that would be easy to remember. It was a lead, which would be more than she's given them so far. She was actually happy, actually proud of herself. She had been so afraid, so petrified, but she could do this. She could save Dean.
Then came a single sentence that turned her blood to ice.
"What the hell are you doing?!"