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Y/N sat alone in a dimly lit and drably furnished room. The clock, illuminated by the dancing light of a selection of candles spread across the table, read 11:47 P.M. “Et ad congregandum…” With a sigh, the hunter lit a match as they began to recite in Latin. “Eos coram me.” When they’d finished, they dropped the match into a metal bowl at the center of the table, surrounded by carefully-drawn sigils. It was filled with a mix of herbs and fruits, and when it caught fire the scent rushed up into the air in a smoky sweetness. Y/N coughed a little, then closed their eyes.
“Why, hello, darling.”
Upon reopening them, they found themselves caught between feelings of satisfaction and regret. Before them stood the demon king himself; Crowley. Immaculately dressed as per usual, he glanced around the room before his gaze finally settled at the floor below, where a devil’s trap had been painted. He tsked. “Really, love, you should know by now that those things don’t tend to hold me for very long.”
“That’s alright, I won’t take up too much of your time.”
He smiled. “No? We’d better get right to business, then.”
They shifted a little in their seat. “Herakles’ Club. You know of it?”
“Yes.”
“Do you know it’s location?”
“I might. What do you and the boys need it for?” He paused, putting up a hand. “Nevermind, I don’t want to know.”
Y/N shot him a look and began to speak.
“Say, where are the boys, anyhow?” Crowley continued before they had a chance to, taking a step towards them. “Unusual of them to ask you to dirty your hands like this.”
“Well…” They swallowed. “They’re at the bunker.”
He looked at them for a moment, face expressionless. “Oh.”
“‘Oh’? ‘Oh’ what?” They questioned.
The demon continued his advance in drawn-out strides, a grin spreading across his face as he did so. He stopped right at the edge of the devil’s trap and leaned forwards. “They don’t know you’re doing this.”
They unfolded their hands and glanced away. “Crowley--”
“My, my, my… You know, I never thought the little hunter would venture very far from the nest, but clearly I was mistaken.” He cocked his head. “Tell me, darling. What prompted this act of rebellion?”
“I’m not rebelling against them, I’m just giving them help when they’re too stubborn to see that they need it.” They snapped. Crowley raised his eyebrows, an unspoken request for Y/N to elaborate. With a sigh, they did. “Sam and Dean refuse to work with you.” They glared at him. “I mean, it’s no wonder why, but they’re not acknowledging the fact that without outside assistance, we don’t have any workable leads. And you’re the best help we have access to at the moment.”
“I see,” He said. There was a glimmer in his eyes that worried Y/N. “So, strictly professional.”
“Yes.”
He hummed, biting the inside of his mouth softly in contemplation. Finally, he returned his focus to the hunter. “Well, luckily for you, I’m willing to lend a hand. Granted, not without a little something in return.”
Y/N rolled their eyes. “Of course.”
“First, let me out of this devil’s trap.”
They eyed him for a moment, then in one swift movement stood up and took their knife from its holster. Cautiously, they knelt besides the trap and chipped away a line in its outer ring, then stood back up. However, when they did, it was immediately clear that Crowley was gone. Narrowing their eyes, they turned around, walking right into something solid and warm.
“Careful, love. I thought you hunters were supposed to be aware of your surroundings?” The demon teased, placing a hand on their upper arm to help them steady themselves. They immediately shook it off and scowled.
“Just cut to the chase, Crowley. What do you want?”
“A favor.”
“No.” He frowned at their response. “Who do you take me for? ‘A favor’ is far too vague for my liking,” They crossed their arms and backed away. “I’ll only take it with the condition that it can’t involve my betraying the boys, or otherwise acting against them. Alright?”
“You must be the life of the party.”
“Is this a deal or not?”
“Fine,” He began to close the distance Y/N had just put between them, but they stood their ground as he approached. “It’s a deal. Now…” He trailed his eyes over their face. “Shall we seal it?” Hesitantly, they nodded. Crowley brought his hand up to cup their cheek, and began to lean in, but Y/N ducked their head away. He furrowed his brow. “What’s wrong?”
“Nothing,” They said quickly, turning back to face him. “Sorry. You can, um...” They gestured vaguely.
“It’s clearly not ‘nothing’,” He replied. His tone was unusually soft as he continued. “What’s wrong, Y/N?”
Their eyes widened slightly. It was rare to hear Crowley actually call them by name. “I, um…” They looked down at their hands. “I’ve never done it. Before.”
For a few seconds, there was an awful silence. But then they felt the hand on their face caress it softly. “You’ve never kissed someone before?” They shook their head, face flushed. “Really? Someone as gorgeous as you?”
“Shut up,” They laughed a little and smacked his arm. “I just, I don’t know. I never got the chance.”
“Well, love,” He traced his hand over their jaw and under their chin, directing their gaze back to meet his. “I will relish being your first kiss, if you’ll have me.”
They bit their lip. “I mean, I don’t -- I don’t know what to do.”
“Just follow my lead, darling. Alright?” His smile, for once, didn’t seem to hold any trace of malice. Comforted by this, they nodded. “Good.” He muttered as he moved to kiss them. It was a tender moment, more tender than Y/N thought possible for a demon. They rested their hands on his suit lapels as he placed his other hand on their lower back. It didn’t last for nearly as long as Y/N would have liked, almost painfully evident to Crowley by the way they followed after him when he pulled away. He ran his hand through their hair and exhaled. “It’s been a pleasure doing business with you, pet.”
They blinked and nodded. “Yeah, um. You too.”
“I’ll be in contact with you regarding Herakles’ Club. And don’t worry, I’ll be discreet. Wouldn’t want the boys to know about our little rendezvous.” He smirked and placed a kiss upon their temple. “Until next time.”
Y/N closed their eyes in an attempt to savor the moment, but when they opened them they were alone once more.