Disclaimer: I do not own Supernatural but Gabriel is mine, all mine!
A/N: Facts about Gabriel latter on in the story may change due to what I learn in the show, so that she may better fit in the world of the boys.
Gaining Trust
Pilot
The first thing you have to understand about Gabriel is that her father had a horrid sense of humor. Her name was made to be very ironic, and not in the fun way. The second thing you need to know is that she's not like the fool Azazel, she has no plans, she hasn't had plans in a very long time. And another thing: she's not so twisted that she can't be redeemed. Her very human soul was just born so twisted and so fucked up that it was hard for her to find her way out of the darkness from which she was born. She was created to act like a killer; to enjoy something she knew was wrong. But as she grew she honed her craft, became smart, became clever, and was able to create her own rules and laws that governed her heart. And as her mind grew so did her very human emotions. And, well, Gabriel has been alive for a very long time now.
The first time Samuel Winchester met Gabriel her body was that of a seventeen year old. She had gotten into Stanford full ride, a natural born genius the school said, pushed by her aunt to work harder than any human should. She was sitting in the back of his class staring ahead at the whiteboard, copying down the notes studiously. Every once in awhile she would look up and copy something else. She was very young to be in law school let alone in the age group that Samuel was part of, and for that she was though of as an outsider from the social norm. Even Samuel was not able to let go of the idea that she didn't belong. However from what he had seen of her he could tell that she didn't seem to mind, and he saw her a lot, she was in two of his four classes. He knew it wouldn't last, he was going to be going to a new school by the end of the year, and she would never been seen again.
Which is where Dean Winchester came in, Dean Winchester was the brother of Samuel Winchester. Dean was everything his brother wasn't, he had been born into the world of the hunters, and had embraced it unlike his brother who had run away from it the second he had been given the chance. Gabriel had been waiting for him, and when she saw his car in the area she put her books down, and went home, fell asleep and dreamed. When Gabriel dreamed she dreamed of war and the future and of everything in between, and when she went to work that day she worked with a smile. She walked outside, checked the trunk of her car and was off, she never looked back.
Gabriel had always loved the road, it reminded her of freedom and choice and everything her life before had not been. It stretched on and on and gave her a place to let her hair back (what little of it there was), let her mind wander, to the changing of the leaves or the upcoming summer and how the weather would slowly get hotter and how it would remind her of home but would also remind her of how much she didn't wish to go back ever again, no matter what. Love was a funny thing after all.
The second time Samuel Winchester met Gabriel she was shooting a woman in the white full of rock salt. He looked at he like he was seeing her for the fist time, "You're a hunter?"
"Born and raised. You have room for one more?"
Dean scoffed at that, "We don't take on charity cases, or people we don't know."
"I understand."
And was that. Or it would have been, had sweet Jessica not gone up in flames on the ceiling. Nothing holding him here any more Samuel made a choice, one his father had made years and years ago. Revenge, Gabriel decided, was quite the motivator. That day Gabriel dropped out of college.
Wendigo
There's a fine are of stalking, you have to stay just far enough away that the person you are following doesn't know that you're watching them but close enough that you can jump in to help at any moment. Years of watching Samuel had taught her that. This case was rather open and shut Gabriel realized as she watched the boys work. They talked to the people in peril like a fine tuned machine; Samuel would act the kind concerned citizen and Dean would play his second so well. She loved watching them work she decided.
She chose to stay away this case, she wasn't needed, and there was little that she could do to help.
Dead in the Water
"Stop following us, I don't know why in the hell you're doing it, but if you don't stop I'll stop you myself"
"If I haven't done anything bad yet, do you really think I'm going to start now? "
"Listen I don't know who you are and I don't really care to find out. Stop watching us."
"Dean."
"What?"
"Maybe she just really doesn't mean any harm?"
"Fine, but this stops now, this isn't a game."
"I understand that."
"Good."
"My first offer still stands."
"Not going to happen."
"Okay."
"Good."
"Good."
Phantom Traveler
She kept her distance even further while they grappled with a demon that had taken over a plane. She didn't want to deal with demons, not quite yet. It turned out; she discovered that Dean was scared of heights.
For the whole case they didn't realize that she was there, but she still watched them. She hadn't said she really would stop following them. She understood all to well that what was going on wasn't a game; she knew what hunting coast those who chose to take that path, most of them lost what little bit of connection to humanity they had. Hunters were warriors, they fought well but like any warrior race they had an early expiration date.
Samuel and Dean were lucky to have each other; they could depend on each other to keep the other one alive. Dean was the one who was best at fighting and Samuel was best at research. It didn't mean that the other was bad at the other activity either; just that one was better than other when it came to those two things. Dean had his moments of genius and Sam could hold his own on occasion. Gabriel smiled, they were quite amazing the two of them.
Bloody Mary
She knew by the way that the case was going that it was hitting too close to home for Samuel. She wanted to reach out and hold him, to tell him that everything was going to be okay. Watching him for so long she had started to care for him more and more. And this case was hard for him; she could feel his sadness every time she looked at him. It was this sadness that told her it was time to step in. The ghost of Mary was following a girl, and she was causing people to cry tears of blood, and while she knew she could do nothing to protect Samuel…
She stepped out of her car popped open the trunk and pulled out a bag, unrolling it she pulled out her favorite shot gun and loaded it with iron rounds. Satisfied she looked at the house in front of her and then walked inside. She found herself face to face with Samuel and Dean, "I thought you could use some help."
There was the sound of the safety on a gun being turned off and then Dean pointed said gun at her head, "I though I told you to stay away."
"You need help Dean, and I'm not even going to do the dangerous job. I'll just watch her, that's all."
Samuel looked at Dean, "It's a good offer."
"I know."
"So?"
There was the sound of gun being pulled away from where it was and the safety being turned back on.
"Just don't do anything stupid."
"Yes sir."
"Let's go Sam."
Before they had the chance to leave completely Gabriel spoke up, "Be careful."
A half-hearted wave from Dean was her answer.
Gabriel turned to the woman who was sitting on the bed, "So, just how did you fuck up?"
The girl just looked at her, and Gabriel sighed.
Later when Dean and Samuel were done speaking to the woman they had saved they turned to Gabriel, "She's not dead."
"No, she's not."
A smile, "You okay Sam?"
"I've had worse."
"Of course."
Dean looked back and forth between Gabriel and Sam and shook his head, "Okay Sammy it's time to go."
"Offer still stands Dean."
"And just why is now any different from before?"
"It's not."
"You give me any reason to not trust you you're gone."
"I know."
"You screw up and end up getting yourself killed it's not on me."
"I know."
"No questions about what's going on."
"Couldn't care less."
"We need you gone, you're gone."
"Your car your rules."
"Grab you shit, get in the back."
The sound of a trunk being opened, a bag being pulled out, the sound of the trunk closing and the doors of a car opening and closing, "You okay with Boston?"
"I love Boston."
"Good."
A/N: And that's that. Don't expect the boys to trust her right away. She's going to have to work for it.