winchester

The Winchesters and the Milligan

A/N- The fifth part of Long Lost Sister. I recommend reading the rest of the series.

Series Summary- Sam and Dean meet their sister, Adam’s twin, on a hunt and things don’t go all that smoothly.

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Long Lost Sister Masterlist 

Masterlist

Y/N swung the demon blade through the air, swiping the demon standing in front of her. She ducked as he lunged toward her and then jammed the knife up through his rib cage. The demon crumpled, dead, on the floor. Y/N straightened up and looked around. The other three demons lay dead on the ground. She headed over towards her brothers, Dean checked over his younger siblings, “Everybody okay?”

Before they had the chance to respond, a new, heavily accented voice called across the warehouse, “Did you really need to take out Anna? She was one of my best.” The siblings stood on defense against the Scotsman. “Well, well, if it isn’t the littlest Winchester. Reunited with big brothers at last.”

Y/N narrowed her eyes at him, “Crowley. For the last time, it isn’t Winchester, it’s Milligan.”

Sam and Dean shared confused looks, Y/N and Crowley had meet before? When and where had she run into him?  Either way, the brothers were not too happy with Crowley being around their sister. Dean stepped forward toward Crowley, “Have you two meet before?”

Y/N shifted uncomfortably, “Yes, we’ve run into each other before on a few hunts.”

“More like hunting for me.” Crowley mumbled under his breath.

“What was that?” Sam asked. The brothers knew there was something Y/N wasn’t telling them. Of course the brothers didn’t know everything about Y/N, Sam was aware of that, but Y/N’s mysterious past with Crowley was making him uneasy.  

Y/N threw Crowley the signature Winchester bitch face, “You’d think as the King of Hell he’d be more well connected, but he’s kind of useless. Why have you guys even left him alive this long?”

Crowley made a face at the young women and leaned closer to her. Dean and Sam instantly moved forward, trying to step between the two, but Crowley bent closer to her and said, “Now now, no need to be rude. It’s not my fault, we both know nobody can help you with what you want.”

“What does that mean?” Sam asked, looking back and forth between his sister and the King of Hell. Crowley winked at Y/N and disappeared. Before Y/N could even suck in a breath, Dean and Sam turned on her, questions pouring out of their mouths.

“What was that about?”

“How did you meet Crowley again?”

“What did he mean by you hunting him?”

“Yeah and what was that about nobody being able to help you?”

“Help you with what?”

“What exactly are you trying to do?”

Y/N took a deep breath and sheathed the demon blade, “It was nothing, it’s all nothing. Don’t worry about it.”

“Don’t worry about it?” Dean gave her an incredulous look. “Seriously? Our little sister has some obvious beef with the King of Hell and you want us to just not worry about it? Are you kidding me?”

“Yeah, Crowley’s nothing I can’t handle. I’m perfectly capable of taking care of myself, I’m not some little girl.” Sam sighed, rubbing a hand down his face, this was a common fight between Dean and Y/N. He’d say something about her being their little sister, or him looking out for her and she’d automatically bite back that she could take care of herself; it would just escalate from there.

Sam stepped in before it got bad, “We’re not saying you can’t, but the point is you don’t have to worry about Crowley on your own anymore. You’ve got us now and we know from past experience how much of a headache he can be. We just want to know that you’re safe. Dean didn’t mean to imply that you couldn’t look out for yourself.”

“That’s kind of you Sam, but really it’s nothing. Seriously. Let’s just get out of here okay?” The brothers knew that there was more she wasn’t telling them, but decided to wait till they got back to push for more information.


The boys didn’t try again until they were settled back in the bunker the next day. The siblings were seated in the library, researching and enjoying burgers. Sam and Dean exchanged looks over the books they were hiding behind, each trying to get the other one to ask.

Finally, Dean cleared his throat, but Y/N continued to read, obvious to his attempt to get her attention. When she didn’t look up Dean tried again, louder this time. Y/N raised an eyebrow at him, “Yes?”

Dean looked nervously at Sam, who nodded at him, “Well, we wanted to talk about the run in with Crowley yesterday.” Y/N slouched back in her seat, crossing her arms over her chest and the Dean braced himself before continuing, “I know you said you it was nothing and we know you can take care of yourself, but we are still worried. What exactly were you all tied up in with Crowley? What did you go to him for help about?”

“Guys, there is nothing to worry about. It was all in the past.”

Sam leaned forward in his seat, “Y/N, you didn’t make a deal with him, did you?”

“What?!” Y/N looked between the two brothers, shocked. Dean wouldn’t look her in the eye, terrified she’d say yes. “Of course not! Like he said, Crowley couldn’t help me. There was nothing to make a deal about. He couldn’t offer me anything.”

Again, the brothers shared uneasy looks, “But there was something you were willing to make a deal about? What was it you so desperately wanted?”

Y/N threw her arms up, exasperated with the relentless questioning, “Fine, yes I went to Crowley for help and probably would have made a deal.”

Y/N pushed back her chair and stood up angrily from the table. Sam and Dean followed her lead, both standing from their chairs.

“For what?” Dean’s voice was gruff and angry, it set him on edge that she, or Sam would ever do that.

“I was looking for someone that could help me free Adam from the cage. I thought Crowley as King of Hell might be able to, but just like everyone else he’s been a dead end.”

At the name of their mutual brother Sam and Dean both went rigid. The three siblings had never really discussed Adam and realistically the conversation was inevitable, but that didn’t make it any easier. While they never talked about him, Sam and Dean both individually felt guilty about their youngest brother’s fate.

“Y/N…”

“Don’t, okay? There really isn’t any need to even be having this conversation. There’s a reason I didn’t bring it up to you. I know you don’t care and I’m not going to make you talk about it, about him. Now you know how I meet Crowley. Happy?”

Y/N turned on her heel and went to storm out, but Dean reached out and grabbed her arm stopping her, “Just stop, you didn’t even give us a chance to say anything. Look, I know it’s a rough subject, but we don’t not care.”

Y/N let out a humorless laugh, cutting him off, “Oh you care? Wow, y’all have a weird way of showing it then. Leaving him to rot in hell with Lucifer and Michael is your way of showing you care?”

Dean’s hand dropped from Y/N’s arm, and both averted their eyes, not able to look Y/N in the eyes. When she continued her voice was harsh, with a cold edge to it, “No, if you cared you would have tried harder, hell you would have tried. You never really did. You made a half assed attempt with Death once, but quickly gave that up for Sam here. Let’s be honest with each other, if that was one of you still down there you would die trying to free the other.”

“Y/N,” Sam started, but he honestly didn’t even know what to say. How was he supposed to defend them? She was right. If Dean was trapped in the cage he would never give up trying to free his brother and Dean had done everything to free him before.

Dean tried to blink about the tears starting to form, “It’s not that black and white. Hunting never is, we wanted to save him, we really did, but you said it yourself, there is no way of getting him out.”

“Don’t. You didn’t try and exhausted all your resources and try to set him free. You figured there was no way, but you didn’t try and find a way. Don’t even try and give me that bullshit. That’s my twin brother you’re talking about and you left him in the cage for all of eternity.”

Sam and Dean were shocked into silence. The guilt they felt for Adam before now multiplied. Sam stepped towards Y/N, but she quickly stepped back from him, “I was down there Y/N, I know what it was like. If there was some way we could have saved Adam we would have done it. I wouldn’t wish that on my worst enemy, and certainly not my brother.”

Y/N’s voice kept rising as she got angrier and angrier, “Don’t call him that. He wasn’t your brother, you never treated him like a brother. Like you treat each other, but then again no one will ever be as important to you to as each other is.”

“What does that mean?” Dean snapped.

“It means unless you’re Sam and Dean Winchester, you better watch your back, because you two will screw over anyone to save each other.”

Sam gave her a lost look and tried again to reach out for her, “C’mon, that’s not true. Y/N-”

“No, it’s a hundred percent true. You’ll always pick each other, like with Adam, hell like with the apocalypse. You will risk everything, even the safety of the whole world to protect each other. I can’t trust you two; I can’t trust that you’d do anything for me. I never will be able to, because if push comes to shove one day, I’m the extendable one here.”

Sam and Dean stood there in shock, not sure how to respond, “That’s what I thought.”

It was the slam of Y/N’s door that finally shook the boys out of it.


tags: @27bmm  @exploratiionist   @winchesters-favorite-girl  @iamflanneltrash  @fabulouslycassie   @jesstherebel  @nothingiswrongwithit  @vvinch3st3r

Daydream

A/N: Another part for the back-story of the crossover series or however you want to read it ;) the main point is that you have fun with it!

Words: 1.585

Warning: swearing, smut (really pure smut)

Pairing: Reader x Dean Winchester

It was dark around you. Everything was black. You laid on something soft but your wrists and ankles were strapped strong on something. You opened your eyes but it was still dark around you. A noise next to you caught your attention and you moved your head in its direction. Seemingly you had a blindfold around your head. You tugged on the straps and tried to escape but they were too strong and digged deeper in your sore skin. A helpless feeling rose in you but you tried to push it away. You swallowed thickly to remove the lump in your throat. Something appeared next to you, you could see the dark shadow towering above you and the bed dipped under the weight of the shadow. Something soft moved over your bare skin and tickled you softly. Sexual tension spread through your body, through every fiber of your body, from your head to your toes and your back arched upwards a little of excitement.

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personally, I like the disease. ❞
— Demon!Dean