@lipstickandwhiskey this is my Demon Dean one 

Almost Him

Warnings: descriptions of blood, torture, ANGST

Characters: Demon Dean, Sam Winchester, Sister!Reader, Crowley

Summary/Request:  hiiii!! i was wondering if you could write an imagine with demon!dean and a little sister (age: 15) and he’s a total asshole and he doesn’t care about her until crowley captures her and tortures her in front of him. he almost like snaps out of being a demon and gets defensive. you can choose ur own ending. thanks ❤️

Word Count: 1,461

Y/N: your name

Y/N/N: your nickname

You had to say the last few months haven’t been the best. Not only had Dean got the Mark of Cain, but, he also died. Well not really, the mark stopped that from happening by turning those who have it into, well, into a demon. Now you and your other brother Sam were looking for everywhere to finally turn him back to “normal”. Normal didn’t really exist for any of you now.

Word says he’s been working with Crowley and being a total dick, he’s been hunting people and saving monsters. Everything feels like it’s going to hell, maybe even literally.

Although all this has happened, you couldn’t help but feel that maybe, just maybe, there was a chance of getting him back.

Now, it’s been about three hours of researching about looking for Dean and you were getting sick of it. “Hey Sam, I’m getting kinda’ hungry. Imm go out and buy something, want anything?” You said to your brother, that being the only excuse to get out.

“Oh, no thanks. Be careful ok? And don’t talk to any strangers.” He responded to you adding in the last part as if he just wanted to make sure you wouldn’t.

“Yeah, yeah. I won’t.” You said absentmindedly already leaving for the door with your jacket. Little did you know that that would be exactly the thing that got you in trouble.

You arrived at the little convenience store near the gas station, you stepped into the small shop and felt as the air conditioner touched your skin. You walked around and chose a collection of things. You took your chips, mac and cheese and a coke to the cashier and placed them on the counter, but right as you looked at the cashier their eyes flashed black. Then, darkness.

You woke up a few hours later in a wide dark dungeon, you arms and legs tied up against the chair you were placed on. “Good morning darling,” You heard a voice say behind you, “I thought you’d sleep over all the fun.” The voice said, finally reaching nd leaving goosebumps on the back of your neck.

You felt a the “person” walked around you, you were familiar  with the person infront of you. He was short, grey hairs taking over the small amount of hair on his head and his beard. He wore a long black coat, he smiled at you as you inspected him flashing his red eyes when you landed on his eyes.

“Crowley, it’s been awhile since I saw you old friend.” You said to him sassily rolling your eyes when you said friend. He just laughed.

“Alright, what do you say if we cut to the good stuff my dear?” He asked, not really waiting for an answer.

“What do you want? I have nothing” You said to him, and it was true, you had nothing to give, no information to keep secret.

“It’s not what I want from you, it’s what I need you to do for me.” He said turning around and walking to a small tool box that you hadn’t noticed before. “You see your brother, Dean, has been acting up lately and doesn’t want to cooperate with me.”

“How am I supposed to help?” You asked, he was a demon now he didn’t care what you did.

“Oh you’ll see.” He said shortly, “Bring him in!” He yelled turning back to you as the door at the end of the room flew open, two suited men with your brother in between struggling to loosen their grip.

“Remember her Deany? It’s your sister!” Crowley yelled at him, Dean looked up at you glaring as the demons tied him up right infront of you. You just stared at him, it was the first time you saw him in months.

“Oh right her, wow she was annoying.” He said, you felt as your eyes were glassed over with tears. You knew he was a demon but it still hurt. “Why am I here anyway?” He asked as confused as you were about the entire situation.

“Oh you see, since you’ve been quite naughty recently I’m going to confiscate something you love.” He said with a parent-like voice pointing at Dean.

“Something I love? Wheres the liquor then?” He talked back laughing at his own joke.

“Oh well, I’ll just- you know- do this for fun.” He said finally looking back at you, taking out a knife from the rusty old toolbox he had in his hand. You saw as Dean moved closer to look at you better. He seems as if he was analyzing you.

You were too distracted looking back at Dean to see that Crowley was advancing to you, and slashed the sharp knife against your arm. Thick velvet drops of blood swimming down your arm, making you whimper slightly. “See that Squirrel? How she’s in pain?” He asked Dean, you saw has he relaxed slightly as if he was relaxed.

He repeated the cuts over and over again on your arm, leaving a pattern of red on it. You only whimpered to the cuts, trying to be strong for Sam, for Dean.

“Well, how about we make her scream huh?” He asked Dean again but not really asking for an answer. He took the knife once again and slashed it on your cheek deeper than ever. You screamed in pain tears beginning to slide down your cheeks, stinging the cut that had just been made.

“Ok, I get the point.” You heard Dean say, a tone of urge in his voice. But, Crowley just kept on going, slashing and stabbing every and any place he thought of.

“Really? I thought you didn’t care, besides I’m having so much fun already.”  Crowley said with a psychotic smile on his face. He let go of the knife and just started punching you, then pressing and pushing his fingers into your cuts. Leaving a stinging pain in you, making you scream louder than you ever have. Your head was left hanging as you tried to breathe.

“Crowley stop. I’ll work with you I promise.” He seemed angry and had hints of worry in his voice. You smiled slightly at the the thought, maybe there was a part of the real him in there.” Crowley pulled your hair back making your head look up.

You cried at the slight pain that erupt from the action “Hear that princess? He wants me to stop! Wow he really has nerve doesn’t he?” He laughed, you felt as Crowley caressed your cheek with the cold tip of the knife which was now stained with your blood. Pressing it back into the cut he had made, making you scream again.

“Crowley! I said STOP!” you saw as he ripped off the ropes that were keeping him still and stood up moving quickly to Crowley.

Suddenly you heard as the door broke open, a tall figure walking in. Sam finally cared to come and save you, he saw the state you were in moved his eyes to Crowley and then to his older brother beside him. Immediately Crowley began to run out, not out of fear of Sam but because of fear of Dean- who was actually chasing after him close behind.

“Y/N/N.. It’s gonna be ok, it’s gonna be ok.” He cooed into your hear as he untied you. When you were finally freed from your restraints you wrapped your arms around his neck and began sobbing uncontrollably. “It’s ok you hear me? What did they do to you?”

He felt your body go limp on him and began carrying you to Baby.

You then woke up in your bed, stitches on your cheek and cleaned up. Sam was right there next to you holding you hand. “Oh, hey kiddo. Feeling any better?” He asked you with a small smile on his face.

You began crying again, remembering what had happened. “hey hey, what happened? What did they do you?” He asked you caressing your hair.

“No, it was just Crowley. Dean was tied up in front of me. Crowley tortured me so he’d cooperate. I thought it wouldn’t work but he, he.” You suddenly stopped to continue crying.

“But it did. He got mad at Crowley, told him to stop, that he’d work. Crowley just kept on going though and he got really mad. He broke the rope he was tied with and was gonna beat him up. It was like, like it was almost him.” You finished looking at Sam whose I eyes had started watering as well. You hugged each other for what felt like hours, the little hope their was before was now huge. Maybe there was a way to bring him back again.


I think I’m getting back on track on tumblr and I’m soo happy! Hope you guys liked it! If you’re going to request turn off anonymous so I can tag you! Hope you people have a good week!

Remember how big of an asshole Dean was when he was a demon? And how his love for Sammy couldn’t even overcome it? Now just imagine how profound Meg’s feelings for Cas had to be in order for her to admit that she fell in love with him and that he was her Unicorn

It makes me cry every time I think about it.