This takes place in Season 3, although the deal happens in Season 2 (just imagine that Stiles already has long hair) and Season 2 of Supernatural. Stiles is 18 years old and the timeline takes place in 2006. There will be some scenes of the Pack mentioned in the story but it wouldnt maily be about Stiles and his brothers! Okay, thats all for now. Enjoy!

Prologue:

No one ever told Stiles that it would end this way, of course not. Because no one ever knew. And you're probably wondering what the hell am I talking about but I'll get to it later. Stiles made a stupid decision, but it wasn't a bad decision either. He did it to save his brother, his half-brother, and Stiles would never regret making a stupid decision like that.

His brothers spent so much time bickering at him that they were going to get him out of it. "Maybe I don't want out of it." He told them which broke their hearts. He was definitely telling the truth. He didn't want his brothers to keep sacrificing themselves over and over again and Stiles thinks that maybe it was his turn next. "I'm going on with this deal whether you like it or not." He stated sternly.

What deal, you ask? A demon deal, of course. To save his older brother Sammy from crossing paths with death. He didn't want to see Sammy drop dead like his biological father, John Winchester. He couldn't lose anyone else.

He was currently in his bedroom looking over the various red strings of wool connecting to different pictures on the board. He was going to miss this. He was going to miss it a lot. The board reminded him of many things. His mother, Claudia, would always give him fake cases to solve every single day and when he solves them, he would always get an extra cookie or maybe two. Claudia was the best mother he could ever hope for but she died. Many people thought she died by frontotemporal dementia but truth is, she died by the hands of a demon. Which is how Stiles knows about Sam and Dean and them being hunters and all. He remembered watching one of the demons cover his mouth as the other one torture his mother with its demonic powers. He remembers how loud his muffled screams were or the fact that the monitor was beeping so loud that it drowned out the sound of his own sobs. He was only nine at that time, watching as the life in his mother slowly drain out of her.

How was he going to tell his pack that he only has a month to live? Weeks even.

"There's a Pack meeting," Scott said from out of the blue. Stiles would've been 'freaked out' by his anonymous arrival but the fact that Winchester's don't normally get scared of anything else, really helped. With him being the not-so-helpless-human-but-the-pack-doesn't-know-it spaz wasn't really cutting it out for him. "Derek is expecting you to come."

"Well, tell Sourwolf to wait," Stiles answered back as his eyes flickered around his room. "I'll be there in like… ten minutes."

"He wants your there, now." The frowning puppy told him and Stiles sighed, nodding his head a bit. He would've had put up a fight to go to Derek's loft for a Pack meeting but he just wasn't feeling it. Somehow, he knew something wrong was gonna happen tonight. He muttered an 'alright' and walked down to his Jeep, watching Scott drive away in his dirt bike.

"Let's hope for the best," Stiles sighed and cranked up the engine, pulling out of his driveway and onto the asphalt road.

ELEVEN MONTHS AGO:

Stiles looked at the rusty old box he was holding in his hands. A fake ID that Sam and Dean made him lied it in with some other stuff like a cat's bone. He didn't hesitate to dig a small hole into the gravel road and tossed the box in there before replacing the hole with new gravel rocks. "Get out here!" He yells as he looked left to right to search for the demon. God damn it, he needed to save Sam. He already heard Dean talking that he was gonna make a deal with a crossroads demon and Stiles didn't want to lose another brother. "Come on!"

Suddenly, a beautiful lady with black hair and a black dress that hugged her body in the right places appeared with a smirk on her face. "Easy sugar, you'll wake the neighbors." She responded with her eyes flashing red for a bit. "Stiles. It is so good to see you. I mean it. Look at you," she said with a chuckle. "Gone and got your family killed. All alone in the world with no one but Dean-y who's trying to find out where is his little brother. It's too sweet. Excuse me." She walks toward Stiles, the lanky teenage hunter who didn't give a rat's ass if she insulted him or anything as long as it wasn't about Sammy, Dean, his mother, his father or his friends. Now, she was standing face to face to him as if she was ready to kiss him. "Sometimes, you just have to stop and smell the roses."

Stiles scoffed making an unamused noise at the Crossroads Demon in front of him. "I would love to send you straight back to Hell." He replied with a hardened glare.

"Oh, you should." She smirks. "But you won't. And I know why."

"Well, then why don't you enlighten me, Ms. Know-it-all?" He smirked and the demon chuckled darkly.

"Following in daddy's footsteps. You wanna make a deal. Little Sammy back from the dead, and – let me guess – you're offering up your own soul?" Stiles wanted to say that only him and Dean could only call Sam that but he decided against it.

"There are a hundred other demons who'd love to get their hands on my little innocent soul." He smirked sarcastically but it soon faded away as he became serious. "It's all yours. All you got to do is bring Sam back. And give me ten years – ten years, and then you come for me."

The demon laughs, "you must be joking."

"That's the same deal you give everybody else." Stiles replied.

"You're not everybody else." She leaned into his ear and whispers: "Why would I want to give you anything? Your soul is already tarnished."

"Nine years," he offers.

"No."

"Eight."

"Keep going," the demon laughs, "I'll keep saying no."

"Okay, why the hell not? How about five years? Five years and my time is up. That's my last offer or no deal."

The demon kept the amused look on her face and leaned in once more, as if she was about to kiss him and whispers again, her breath hitting his face. "Then no deal."

Stiles' heart panged. Was it seriously this hard just to make a fucking deal? She was seriously messing with him and he didn't like it. Not one bit. "Fine," he grits his teeth and she replied with the same answer and started to walk away. But something in Stiles stirred. "Wait." He called out and the demon stops, turning around with a sick sardonic grin.

"It's a fire sale, and everything must go. Even innocent teenagers like you," she replied in a – surprisingly – soft tone.

Stiles took a deep sharp breath and looked at her. "What do I have to do?"

"First of all, quit groveling. Needy guys are such a turnoff. Look… Look, I shouldn't be doing this. I could get in a lot of trouble. But what can I say? I got a blind spot for you, Genim." – he rolled his eyes at his real name, the name he wanted to keep locked up forever –, "you're like a… puppy. You're just too fun to play with." She sighs a moment later. "I'll do it."

"You'll bring him back?" Stiles asked, much more hopeful than before.

"And because I'm such a Saint, I'll give you one year and one year only. But here's the thing. If you try and welch or weasel your way out, then the deal is off. Sam drops dead, and Dean is gonna be devastated. He's back to rotten meat in no time. So…. It's a better deal than your dad ever got. What do you say?"

Stiles took a moment to consider it. One year to live. One year to live his life. One year to spend time with his family and his friends.

Just one year. Stiles looked at the demon and pulled her into a kiss to seal the deal. "One year." He repeats to the Demon.

Stiles took a deep breath and hopped out of the Jeep. The deal he made seemed like it was only a day ago but now it's been eleven months and Sam and Dean are trying to find out a way to take him out of the deal. If only they could get it in their right minds that Stiles didn't want out of the deal. He wanted Sam to stay alive and breathing and not dead and rotting.

As soon as he entered Derek's loft, heads turned to him which freaked him out and it turned silent. "Why is Stilinski here?" Jackson asked with a brow cocked, "this is Pack only."

"I am Pack, jackass." Stiles replied, "I-,"

He gets cut off by Derek who didn't need to try and break his heart. "We're kicking you out of the Pack, Stiles."