This is probably going to be short. Maybe three or four chapters, but we'll see how far we get. I also plan to make another story gearing toward Dean/OC rather than Sam/OC—catering to both preferences. I can't seem to choose a favorite between the brothers.

Also I'm trying to work on my third person p.o.v. I might later reconstruct the whole thing to be in first person, but I've already written so much.

Sam Winchester never thought he would be in this situation. Sam Winchester never thought he would ever go against Ruby's will. Sam Winchester never thought he would be looking at the past, but here was his last connecting to his beloved Jess, dying in his arms.

"Dean!" Panic shot through Sam's body and voice. He dreaded the thought that his brother would turn him away. After everything he did, all the angst he brought up, he wouldn't blame his brother. However this was an emergency and in the first time in a very long time, Sam felt pathetic and abysmal.

"Sam?"

"Dean! Don't hang up!"

Silence fell through the air. Dean I need you. "Sammie what's wrong?"

Relief flew through his body at his older brother's concern. "I… I killed her. I killed Ruby."

"What-?"

"Dean I need you to send me Cas. He needs to heal her- Not Ruby! Jess's friend. She-" A hand grasped Sam's shoulder. He spun around to see Cas backing away from him.

"Where is Ruby?"

Sam blinked a couple times, taking in the fact Cas was in front of him. "Church… down the road." The angel disappeared. "Dean?" There was no answer.

"Sam?" Levi, Jess's friend, whispered.

Relief flooded his body upon hearing her voice again. She stopped talking minutes before Sam called Dean. He was on foot, unable to get anywhere that could save Levi quickly. "Yes, Levi?"

"I'm sorry I stopped talking…"

He stroked her hair and shushed her. "No, no, it's okay Levi. You're going to be okay."

"Sam." Cas looked closely at Levi. "She is not fully-"

"I know! Will you heal her or not?"

Cas sighed. "I will not and cannot heal a demon, but Dean told me to do this."

Locked away in the panic room of Bobby's basement, Sam watched over Levi. She was sleeping now. On the stiff mattress, Levi was in a dreamless sleep. Cas suspected the wards against demons from entering the room didn't work on her because of her partial human heritage. Dean became very silent when Cas informed him his little brother was here.

Sam began wondering about how much Levi knew about the truth, and for how long since she was part demon. He also wondered about how many signs he missed. He let Jess get near his past and didn't even notice…

A day later, Dean observed Sam fawning over the half demon. Sam remained in the vault with her. His older brother suspected that he was punishing himself by remaining in there, but in truth Bobby, Cas and himself felt better that he was down there.

Dean thought back to the times he was bound in there, and the times Sam was. Every minute made the time spent in there worse and worse. However those situations did not include a half breed girl.

Levi was now bandaged, thanks to Bobby who brought a first aid kit. Her wrist was nearly healed, but her stomach was a different story. While she was not near death, she was in an immense amount of pain. Sam had coaxed her to sleep through most of it; seemed to speed up the healing processes. Thanks to the demon blood in her no doubt.

"Sammie." Dean interrupted as Sam was finishing up her bandages. "We need to talk…" There was a pause. "Alone."

Sam looked from his brother, to his lap, to Levi. "I'll be right back with some food and water okay?" She nodded, sadly then laid back down on the bed, her back facing the Winchester's.

Upstairs, Sam stood in the middle of the kitchen while Bobby and Dean stood across from him—arms folded. Cas was elsewhere.

"Sam." Bobby nodded to the younger brother as a hello. "Who is that down there?"

"Jess's friend. And apparently-" Dean cut him off.

"A half-breed demon." Whipping his face, he turned away from Sam.

Bobby's face grew furious. "What?"

"She's part human to."

Bobby's voice matched the rage he displayed on his face. "Human or not that girl will be stirring up-"

"Trouble! I know. We were left alone for a day—kind of had a lot of time to think." He raked his fingers through his hair and sighed. "Ruby wanted me to drink her blood because I guess it gives me certain abilities we could use for the seals, but then she wanted me to kill Levi."

"The girl?" Bobby asked. Sam nodded.

"I asked myself how Jess would feel about this- What she would want me to do… I chose to protect the last connection I had with Jess."

"You chose a girl you barely knew over your own brother?" Dean spun back around, glaring at his little brother.

Sam fell silent for a while, looking at the floor. "I guess… I guess I did." An awkward silence fell over the room. "Dean I-"

"Don't." With that, Dean walked out of Bobby's house.