A/N: First official chapter! It took a little longer then I thought it would, but this is it. There's the big even that leads for the rest of the story in this chapter. It's kind of interesting how one decision can change so many things really. Expect plenty of little companion oneshot stories to come out with Jimmy as a demon that are branched off, or in some way related to this story. Read, review, and enjoy!

Chapter 1

Sitting up, Jimmy looked at Dean with a frown. He had a feeling the older Winchester knew he had a nightmare and shifted uncomfortably under his watchful eye. "What?" he asked, adjusting his old gray t-shirt.

"Nothing," Dean shrugged. "You were mumbling in your sleep."

"Oh, sorry." Jimmy lowered his head and looked at the floor. He'd been spending almost every waking moment with the brothers for the past three weeks since his family was killed by demons. The angel Castiel hadn't reared his head since the incident and frankly, Jimmy was happy about that.

When he leaned back against the couch and looked over at Dean, that same concerned look was on his face. "It that bad?"

Jimmy exhaled and rolled his eyes before standing up and pacing the room. "Can we not talk about it?" he said, snapping a little. After a quick look around the room, Jimmy noticed Sam wasn't there. "Where's your brother?"

Dean shrugged. "He went out to do some research. We might've found a case."

There'd been a bunch of cases Jimmy got to hear about and tag along with, but he never got to actually help. "What kind of case? Another ghost?"

"He thinks it's a crossroad demon collecting again, but we're checking it out to be sure."

"Crossroad demon? You guys never told me about that… What is it?" he asked with interest. Jimmy had been learning about a lot of hunting related things, but not this one. "They're a demon, right?"

Dean seemed to hesitate for a moment. "It's just what it sounds like. A demon that can be summoned to a crossroad. They make deals with whoever summons them. But their price is steep." Jimmy watched Dean curiously, waiting for him to say what the price was. Huffing, Dean said, "They drag you to Hell in a given amount of time. Look, can we stop talking about this!"

A look of defeat spread on Jimmy's face and he nodded. "Sure. No problem." He looked at the door and then back to Dean. "Is it alright if I go outside, or are you still trying to make me a shut in?"

The older Winchester went to grab his jacket and said, "I'll tag along."

"No," he said. Dean froze and looked at him with a raised eyebrow. "I'll stay right outside in the motel parking lot. Any demon pops up to attack me, you'll know it." The suspicious look on Dean's face lingered as he gave a slow nod. Jimmy got up after giving Dean a pat on the shoulder and left the motel room, pulling the door shut behind him with a little bit of hope swirling his mind.

Sam got back, putting the Impala into park in front of the motel room that he shared with his brother and the ex-angel vessel. He got out of the car, grabbing the few newspaper articles that he copied during his time at the library. Using the key, Sam let himself into the room.

He found his brother, sleeping on the couch with the television on. It was some old black and white program, and Sam could only assume that it bored him to sleep. After leaving the papers on the coffee table and nudging Dean's leg, he turned off the television with the remote. "Huh, what?" Dean twitched awake and he squinted. "Oh, hey Sammy."

"Have a nice nap?"

"Yeah." He looked around for a moment, rubbing his face.

Looking towards the bathroom, which was vacant, Sam got a little anxious. "Where's Jimmy?"

"Jimmy? He went for a walk, he said. Isn't he back?"

"No! Dean, he's not here!" Sam glared at him and huffed before turning, pulling the keys for the Impala out of his pocket. "We need to find him."

Dean got up, stretching slightly as he walked. "Calm down. Quit jumpin' to conclusions. I'm sure he's right outside and you just didn't see him."

The look on Sam's face was pure annoyance as he tossed the keys to Dean. "I am calm. This on top of the case isn't exactly good to deal with right now."

His eyes lit up as he led the way out the door. "Wait, the case? What'd you find out at the library?"

"A few things, but we need to focus on finding Jimmy." A nod was only response, because Sam knew that deep down, he was probably feeling a little guilty.

Never has he done something so illegal in his life. Something that wasn't during a hunt under an alias, that is. Jimmy was behind the wheel of a car that he broke into and hotwired in the motel parking lot. Although, he couldn't feel bad since the door wasn't even locked. That just seemed like a bad decision on the owner's part.

He had almost a half hour drive until he got to his destination from where he was. Jimmy had been hiding in the back of the town's library, far from Sam and hidden beyond a stack of books so he could find what he was looking for. And thankfully, he found it. The task hadn't taken long and now, now he just needed to go there.

The necessary things he needed were already picked up on the way, too, so Jimmy had nothing to worry about. He just drove and quietly hummed along to whatever song was on the radio.

Until he got to the crossroads. As soon as he stopped the car and got out, his mood went somber. It wasn't like he wanted to do this, but he didn't see any other choice. Taking a few steps, Jimmy found a spot where the dirt looked moved and did a little digging by hand to find a small metal box. The box had the objects from whoever buried it last still inside and he dumped them out, only to put his own quickly inside and rebury the box.

Jimmy stood up again, glancing around. He didn't have any idea on how the crossroads worked, but he read that the demon would just appear. A few minutes passed and doubt started to take over his hope.

"Isn't this a sight for sore eyes," a voice said. Jimmy turned around, only to see a woman standing a few steps away from him. She wore a bright, long white dress that made her brunette hair and blue eyes stand out. "Everyone wants to get their hands on you and you come right to me. That's kind of you."

"Okay, I don't need the chatter. I need a…deal. Can you do that?" His voice faltered for a moment, almost unsure if he really wanted to ask it of her.

The demon tilted her head with a small smile forming on her lips. "Of course, James. I know exactly what you want. Or would you rather tell me?"

"If you know, why should I waste time to repeat it?" He was in a hurry. The brothers would find out where he was soon enough and he couldn't have them interrupt anything.

"So it's said, you want your family alive?" Jimmy gave a swift nod. "If I do that, they'll live a long and happy live, but I can only give you…twenty four hours."

He frowned at the demon. Only twenty four hours… "Yes. As long as they'll be okay. And not zombies or strange like that."

Taking a few steps closer to him, the demon shook her head. "No tricks. You'll have to…"

He wasn't dumb and knew how demons sealed the deal. With a kiss. And that's exactly what he did. Jimmy pressed his lips to the demon's, shutting his eyes and imagining his family happy again. That's the only thing that kept him from being half disgusted by the kiss.

The demon pulled back first, raising a brow. "Okay. Once you get home, they should be there. I'll see you soon James." Her voice drifted and she disappeared, leaving him alone at the crossroads.

Wiping his mouth on the back of his jacket sleeve, Jimmy turned and started back to his car. His timer was already ticking and all he had were twenty four measly hours. But it was better than nothing. There had to be a light for the situation and he knew he'd find it.