Supernatural Stories and Imagines

Crowley 6/ demon in love part 1

Idea: Instagram

Prompt: Imagine Crowley meeting Dean and Sam's sister for the first time and falling in love at first sight.

Being a female Winchester was not easy, in the slightest. It was basically a miracle you existed in the first place. You had a grandfather on your mother's side that was still living, but your mother was locked up. Your father, on the other hand, you didn't know much about as he had died before you were drawn into the supernatural world. You met your half-brothers and after a while, the three of you were really a family. You were a nice addition, helping out with research and kicking ass. It was strange being the youngest but being the most mature out of the three of you. You had heard of another brother, but he was a story from a time years before you stumbled into the strange world of hunting. 

Another aspect that separated you from the boys was your focus on self-care. You knew hunters had a shorter life span, so you wanted to look good while you were around. That meant routine trips to the mall and nail salon. It wasn't that hard to wield a knife with acrylics. Or to have good aim through sharp eyeliner and heavy eyeshadow. You liked to think your highlight was a fresh addition to the element of surprise when destroying monsters. Sure, you got dirty, but there's nothing wrong with an edgy and rugged look as well as glam and glitz. If being stylish was what you were known for in your family, you would gladly accept it. 

However, you had learned to love your brothers. It was a difficult trial to try to accept each other when you first realized you had similar genes. You feared stubbornness would be too big a factor to allow the three of you to work together. Fortunately, you proved that you could be a trustworthy and helpful edition. It had taken months of back and forth but you believed that you now had an unbreakable bond. 

Speaking of breaking, there was a crash from another room in the Bunker. You jumped away from your desk, grabbing your knife and running towards the sound in designer combat boots. So much for a quiet afternoon to yourself and your thoughts. 

"Who the hell are you?" You demanded. An attractive, somewhat older well-dressed man stood in one of your research rooms. Surprisingly, you did not sense an immediate threat, although you were worried that your brothers weren't here. Was it possible the crash came from another room? Well, yes, because there were hundreds of rooms and this was the closest. 

The man turned around, also surprised. He had an answer prepared but it died at his lips when his dark eyes took you in from your boots to your dark and ripped jeans, to your striped sweater and leather jacket. You took the opportunity to admire his outfit as well while still focusing on the fact that you had the advantage if this became a fight since you were closer to the door. The stranger lifted his hands to show no obvious weapons. 

"Hello, darling. The name's Crowley. And who might you be, lovely?" There was the tiniest of smiles you could barely make out from the distance as he spoke. Crowley slowly stepped towards you, still posing no potential harm. 

You were tempted to give a variety of sarcastic answers. You took yourself by surprise when you even thought of a few flirty responses. You did your best to relieve your senses and focus on whatever your priorities were while still holding your knife high. "Were you the cause of the crash?"

His hands were back down at his side, apparently wanting to have a casual conversation. "I'm afraid not, dear one, but I'm sure you will find out momentarily. Now would you offer me a name?"

You pondered if you should trust him with this. Yeah, you were already overthinking about a conversation with a guy you just met. Most strangers you interact with tend to be monsters, so you weren't sure why this felt different. You decided to test Crowley by offering him a name that wasn't truly yours, but one that you often went by. "The only name that's important is Winchester." 

Now only a few feet away, Crowley paused. You did your best to study any changes in his behavior, such as his slight eyebrow raise. "Well, I'm certain neither Moose nor Squirrel are married. Are you telling me it's possible they have a sister and failed to ever mention it?" 

Okay, so he knows Sam and Dean. That's a start. Think this through, Y/N. If he's met with them multiple times, that means they have to be at least acquaintances, right? But what was with those very strange yet shockingly accurate nicknames? Answers, you needed answers. You were still struggling with finding out the cause of the crash and interrogating Crowley. Your mind was running quickly. Don't get distracted kept repeating in your head. You knew it could happen easily so it was probably best to get out of this situation before the potential turn for the worst. 

"Yeah, let's go with that. Who are you, Crowley, and why are you here?" You remained staring at him with a steady, serious face that you had mastered over the years. It worked especially well in situations where you were not meant to laugh. His smile grew and you sensed sincerity behind it, an action you weren't used to from men besides your brothers. He might not be human. Thanks, mind, for the reminder. 

"I truly would like to tell you, darling Winchester, but I'm afraid that would not work out in my best interest at the moment. That's a pretty knife you got there," said Crowley. 

Crowley eyed the weapon carefully, still giving no indication of fear. There was no way the two of you could continue just standing and staring at one another giving short answers for much longer. For better or worse, there was another crash from nearby. You squinted suspiciously at Crowley before instructing him to remain where he was, slamming the door behind you before you took off to the noise. Sam and Dean were in their new 'man cave' standing in front of the tv screen with chairs kicked over as they cussed and yelled at the screen. You could not even form the words to express how ridiculous the pair appeared, trying to box each other by holding a remote and swinging it back and forth. Sam was the first to notice you and quickly paused their game. Their t-shirts were forming sweat stains from how intense they had become in this. They flashed guilty smiles. 

"You're joking. This is what the crash was? I thought you two idiots were in trouble!" You stammered. You took a few breaths, realizing how worried you actually had been. Dean was in comedian mode. "Aw, thanks for the concern. Although it took you a while to get here if something had been going on," he noted.

"About that-" You would have jumped out of your skin if it had been possible. Crowley was behind you in the doorway. "Hello, boys." 

Sam turned his remote towards Crowley as if it was an actual weapon, making this whole scene that much more laughable, before realizing what he was doing and lowered it. Dean let out an exasperated sigh and set down his remote. "Crowley, what do you want?" 

You side-stepped into the room further to allow him more into the room. "My initial reason is no longer important. The two of you have kept quite the secret from me and I'm disappointed." He turned to you. "Would you do me the honor of accompanying me to dinner tomorrow night?"