Summary: The youngest Winchester sibling has a crush on Ruby and is jealous she spends all her time with Sam. Meanwhile Cas warns Dean about Ruby’s influence over his younger siblings.
Pairing: Winchester Sibling x Ruby
Warnings: Angst, Yearning, Swearing, Lazily edited. As always, if you think a warning needs to be added, hit my line.
Word Count: ~700 words
A/N: I hope you don’t mind I made a modification changing sister to sibling to make the character gender neutral. Thank you for the request <333 n extra thanks for making it sapphic! Remember, I was high for this :3
Divider Credit: @/cafekitsune @/anita-lenia
They were fuming as they watched Sam leave with Ruby. Why did he get to spend so much time with her? Didn’t she know that she was killing them? With her cherry perfume and self assured attitude.
The youngest Winchester was plagued with the misfortune of being enamored with the demon. The demon tasked with strengthening Sam by feeding him demon blood, sometimes even her own, and training him to be the perfect vessel for Lucifer. Sam was special, important, and worth risking it all for. As long as he listened, remained obedient, and stuck to the plan.
This meant Ruby and Sam spent a lot of time together. Alone. Thinking about him receiving all of her attention made their insides twist with jealousy. The Winchester just wanted a minute of Ruby’s time. They wanted to be close to her, look into her beautiful brown eyes, and make her smile. They wanted her undivided attention.
That’s why when Dean is getting annoyed that Sam is no where to be found and all of Dean’s calls are going to voicemail; with zero questioning they tell Dean that Sam left with Ruby. Dean is gone, out of the motel room immediately. They stared at the door until all they heard is the ambient silence of the room. They didn't know how Dean was going to find Sam or where he was going, but right now they didn't care.
They only cared about the way Ruby touched Sam, her hand against his back as she pushed him through the door. Or the way her hair perfectly framed her face. The Winchester had a severe inability to think about anything other than Ruby. They wanted to touch her, to hold her, to be at her beck and call.
After a while of indulging in their thoughts of, they realized something. If Dean was able to find Sam, there would be a confrontation. There was no doubt that Dean, who hates Ruby, would do anything to get Sam away from her. As they began to imagine worst case scenarios, they sprung up from their resting place on the bed and called Dean’s phone. They grew worried as their calls kept going to voicemail.
Three calls.
Three calls and no answer.
Dean was stressed, pissed, confused and damn tired. He felt an intense amount of pressure and he didn't know what to do about Sam. He had no clue how to help or fix any of this. So, he prayed. He prayed to the one thing he believed in right now, Castiel.
The angel appeared soon after and asked Dean what was wrong.
“Am I the only one that knows demons are evil lying sons of bitches?” Dean asked as soon as he saw his youngest sibling.
“What?” They asked, “Dean, where have you been?”
“That doesn't matter, tell me, am I? Am I the only one that hates demons? That remembers they killed mom and dad?” Dean did nothing to mask the disbelief and anger he felt.
“Dean, this is ridiculous! What crawled up your ass and died?” They fought back.
“Cas warned me of something interesting today,” Dean began speaking, being dramatic and leading up to his point instead of just getting to it.
“Is that where you were? You were with him?” They again tried to get this information out of Dean.
“Yea, we were uh talking,” Dean answered, “and he warned me to watch out for you, that Ruby already has influence over Sam, it would be a shame if she gained it over you as well.”
“I’m thinking, what the hell does he mean by that? Are you working with the demon skank too? So, I ask him, I ask Cas if you're working with Ruby and he tells me that you have the hots for her!” Dean finishes up the story angrily.
They felt their cheeks heat up and their eyes widened. “Seriously, Dean? What the fuck? I do not have the hots for her!” They said using air quotes around ‘have the hots for her.’
“Why would feathers lie about that?” Dean asked clearly vexed.
“It’s a small crush! That I wouldn't do anything about because she’s a demon! But you gotta admit, forbidden fruit is more fun,” Their answer annoyed the crap out of Dean.
The two siblings stood in silence for a moment. Dean was honestly shocked speechless for once. And the youngest sibling had nothing else to say in their defense. Even though they knew it was wrong to get with a demon, they still hoped one day, they’d get to feel Ruby’s lips on theirs.
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Last night had been a messy hunt. You, Sam, and Dean, taking on a particularly sly wendigo. Dean had limped away with a strained ankle, Sam had been slammed into a wall hard enough to make your own ribs ache in sympathy. And you? You weren't doing much better yourself. Bruises mapped their way across your skin, exhaustion fogging your mind.
But damn it, you were hungry.
So you let the boys sleep. Left a quick note taped to the motel door—Gone for food.
You’d considered taking the Impala, but Dean would probably jolt awake like some kind of creepy cryptkeeper if he heard the engine. You didn't want his indignant bitching, you wanted some damn food. So you walked.
The diner was the kind of place that had probably looked exactly the same since the ‘80s—faded checkered floors, a counter lined with chrome stools, and a coffee pot that had likely seen things no coffee pot should. The morning light slanted through the window beside you. Winter was starting to lose its grip, the cold giving way to something softer, lighter. Even your aching muscles felt a little looser, the quiet hum of the diner settling into your bones. For the first time in what felt like days, you exhaled.
The bell above the door jingled. A pleasant sound, soft and unassuming.
Instinctively, your gaze flicked toward the entrance, half-expecting Sam or Dean to come shuffling in, still looking half-dead and demanding coffee.
They didn't. Instead, she walked in.
Ruby.
She strolled through the door like she owned the damn place, blonde hair catching the morning light in a way that made her look almost angelic—if angels were the kind of creatures that manipulated their way into your nightmares.
She dropped into the seat across from you without ceremony, propping her elbows on the table as she leaned towards you.
“Wanna see something cool?” Ruby asked, taking a seat next to you on the couch. Today has been a mellow day, and you were looking forward to doing nothing with the love of your life.
“Sure,” you shrugged, pausing the TV. She shoved her phone in your hand before pressing play on the video she already had loaded. “What is this?”
“Just a video I thought was cool. I don’t normally like commercials, but this one was funny.”
The video started off with a car driving in the countryside. Calm music started playing, and you had a hard time figuring out why Ruby liked this commercial so much. This car kept driving for about 10 more seconds, and you were just about to turn away from it when an ugly zombie-looking woman popped on the screen and screamed as loud as she could.
Screaming along with her, you jumped in your seat which caused Ruby to laugh hard. There was no commercial, this was all a prank since she loved pulling them. It was all part of her demon nature.
“I fucking hate you,” you pouted, going back to your jump scare-free tv show.
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Summary: Ruby tries to teach you how to enjoy the finer things in life this Christmas.
Pairing: Ruby x Reader
Word Count: 265
Warnings: Fluff. Implied smut.
Bamby
Dressed in a rob, you watched Ruby with a wide smile as she laid across the bed and painted your toe nails. “This has got to be the weirdest Christmas present I’ve ever gotten.”
Looking up from where she was painting your nails deep red, she met your gaze with a smile smirk. “How is this weird?”
You didn’t answer with words, but simply gestured to her and your feet.
“This is weird?” she asked, genuinely confused. “I thought human girls like the whole pampering thing.”
“I’m not just a human girl… I’m a human hunter girl. The closest thing I’ve ever gotten to a ‘pampering’ is when I scrub a few layers of skin off after bad hunts,” you noted.
Shrugging, she closed the bottle of nail polish before climbing up the bed and over you. Straddling your hips, sitting in your lap, she twirled her fingers around your hair delicately.
“Being a hunter doesn’t mean you don’t get to enjoy the finer things in life,” she countered, leaning in to brush her lips against yours. “Let me help you enjoy them.”
Eyes fluttering closed at the feel of her lips against yours, you caved. “Okay. Just… no more feet.”
“Fine by me.” Her lips curved into a grin. “How about we work on the thighs?” Reaching between the two of you, she slipped her hand underneath your rope and scraped her nails against your inner thigh lightly. “I bet they’re very tense.”
“Mm-hmm.” You nodded, letting your head fall back against the wall behind you. “Very tense.”
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“We’ll let you know when she walks in,” Sam said into your earpiece. Without letting anyone know there was a man talking to you in your ear, you grabbed a few dirty glasses off the bar counter to clean them. Looking up, you spotted the two brothers at a table in the way back.
It’s been a while since you’ve heard from the Winchester, but you’re glad that you did. Someone has been making demon deals at your crossroads, and you didn’t want that kind of energy coming into your bar. In your days, you’ve seen a few things, killed a few monsters, but you liked doing bartending. You meet a lot of interesting people this way, and Sam thought it would be the perfect cover to find the demon they’ve been looking for.
There were a lot of people in the bar tonight, but there was only one person you were interested in finding. Never having seen her face, you only knew of her name. Ruby. She was supposedly a dangerous demon that Sam was so into catching. As long as it gets her off the streets, you’ll do anything to subdue her.
The door opened, and a black-haired woman entered before heading to the bar.
“That’s her. You know what to do,” Dean spoke to you. Nodding slightly, you made your way over to the mysterious woman who just sat down.
“Rough night?” you asked as you set down a glass in front of her.
“You have no idea,” she sighed.
“I have just the drink for you. You’ll love it,” you smiled before taking out the special bottle that Sam had given you to use on her. On the outside, it looked like a normal bottle of whiskey, but on the inside, it was laced with holy water. Something that would take a demon like her down. Pouring the mixture into the glass, you slid her the drink.
Without thinking twice, she grabbed it and downed it. It took a few seconds to work, but she began coughing up the liquid, her throat sizzling from the inside.
“What did you do to me?” she coughed as her eyes turned black.
“Hello, Ruby,” Sam said from behind her, snapping on some demon handcuffs so that she won’t be able to smoke out or use her powers.
“Shit,” she muttered as her eyes went back to normal.
“For your troubles,” Dean said as he slid you a nice chunk of change.
“Pleasure doing business with you, Winchester.”
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“Damn, these seals are getting harder to break,” you sighed. Lilith smirked at you before placing a hand on your shoulder comfortingly.
“Y/N, I would be worried if it wasn’t hard. Don’t worry. With you and Ruby out there, I have nothing to worry about,” she smiled sweetly.
“You must know how this ends, right?” you asked with a sad sigh.
“I am fully prepared to do it.”
“I’m not. I don’t want to lose you. You’re my best friend,” you shrugged hating the fact that you felt something for the demon. You loved Ruby with all your heart, but she wasn’t the only demon who held a special place in it.
When she introduced you to Lilith, you were all for helping Lucifer rise. As the seals began breaking, you got to know Lilith and started forming a bond with her. It would be a shame to see her go after everything she worked for.
“Don’t worry. I don’t go out without a bang. I’ll make sure to show you a good time,” she laughed, causing you to giggle. Ruby stood on the other side of the door, fuming. If Lilith thinks she could just steal you away, she had another thing coming. You were hers, and she was going to make sure you knew it.
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