Loopholes

Bobby made his way from the overbearing silence of the hotel room, quickly drawing a breath from the crisp night air. They had all decided that driving back to South Dakota, after what they had just been through, was not in the cards, so they had found the first available motel along the highway and stopped for what was left of the night.

Sam had insisted on driving, arguing triumphantly that Dean had cracked his head hard enough to warrant at least a slight chance of concussion, and Bobby had been surprised when the older Winchester had only put up a token battle. He knew the boy was probably exhausted – selling your soul kinda did that to a man – but he figured Sam was pretty close on the concussion thing when Dean had nodded off in the passenger seat only minutes after they had hit the road.

Bobby stopped a moment outside the doorway, the dim light from the bedside lamp spilling out into the blackness of the night.

"Couldn't sleep either, huh?"

The older man jumped at the sound of the soft voice, quickly recovering and squinting into the darkness to his left. "Sam?"

There was a low chuckle and a slight shift in a shadow near the wall of the motel. "Sorry, Bobby. Didn't mean to startle you."

Singer rubbed a hand across his face, wincing at the tiredness he heard in the kid's voice. Slowly, he pulled the door closed, bathing the parking lot in darkness once again. There was only the one streetlamp, but it was hidden behind a tall oak, forcing the exposed face of the motel into mostly darkness. He made his way down the narrow walkway, coming to a stop a foot or so away from Sam. The younger man was sitting on the cement, his back against the rough motel wall. His long legs were pulled up in front of him allowing his arms to rest across his knees.

Bobby couldn't really see Sam's face from this angle, but he was pretty sure he could imagine the kid's expression. "You okay, Sam?"

The younger man didn't answer right away and Bobby crouched down to get a better look at him in the darkness.

"Yeah," came the reply. "I'm just…" Sam's voice trailed off, obviously at a loss to describe everything he was dealing with at the moment.

"Yeah," Bobby agreed. He shifted until he was sitting shoulder to shoulder with Sam before continuing. "What about your brother?"

The smile that came to Sam's face was obvious despite the low light. "He's asleep. I woke him up a little while ago. He seemed okay, so I let him go back to sleep. He's pretty wiped."

"You don't look all sunshine and sparkles yourself, kid."

Sam chuckled at the description. "Yeah, I'm tired." He shrugged. "I just can't seem to close my eyes. I guess I'm just…"

…afraid they won't open again.

Bobby nodded silently. He didn't need to hear the words to know what was running though the younger man's head.

"Dean told me."

Bobby took a slow deep breath, not really knowing what to say. He had promised Dean he wouldn't tell Sam about his deal. He still wanted to throttle the older boy, but the despair in Dean's eyes when he had confronted him in the scrapyard had caught the older hunter off guard. He had never in his life seen that kind of love and devotion in anyone. Dean's desire to save his brother outweighed everything – including his own well being – and who was Bobby to say he was wrong.

"It's okay, Bobby." Sam sighed and relaxed one leg, stretching it out in front of him. "I figured Dean probably asked you not to say anything to me."

Bobby nodded, even thought he knew Sam couldn't see it in the dark. "So, he told you."

Sam shrugged. "I guessed." He admitted. "After what Jake said, about severing my spine and everything, and then Dean wouldn't look me in the eye… I just kind of figured he'd done something like what Dad…"

"I'm sorry, Sam." Bobby's voice was laced with guilt. He'd been kicking himself since the boys had shown up at his place. He should've known Dean would do something desperate. Hell, he'd seen how devastated the kid was. "I should've never left him alone after…" He took a deep breath and turned his face to Sam. He could just make out Sam's sad smile in the shadows and he returned one of his own. "I swear I never thought he'd do something so…"

"Stupid?" Sam finished for him.

They both managed to laugh, but there was no humor in their effort.

"Did Dean tell you he met up with a crossroads demon before?" At Bobby's shake of the head he continued. "It was a few months back. We thought we were after a black dog at first, but we connected all the victims to this bar which just happened to sit right at a crossroads. We were trying to save one of the people who'd made a deal ten years before. A guy who'd sold his soul to save his dying wife." He leaned his head back against the wall as he continued his soft narrative. "Dean went to the crossroads and summoned the demon –"

"He did what?" So this wasn't the first time Dean had dealt with the damn thing.

Sam just shook his head. "He wanted to trap it, force it to make a deal to save itself."

Bobby relaxed, nodding in understanding and motioning for Sam to go on.

"He didn't really give me all the details, but from what he said, the demon offered him a deal. It offered to bring back Dad."

Both men sat in silence, reflecting on how that offer would impact the older brother. They both knew how close Dean had been to his father, and they had both seen first hand how John's death and nearly destroyed his son. It was Bobby who broke the silence first.

"Why didn't he make the deal then?"

Sam shrugged. "He never said. Never really wanted to talk about it." Sam rubbed a hand over his face, scrubbing away the wetness Bobby had tried not to notice. "But I think he did it for me. No matter how much he wanted Dad back, he didn't take the deal because he still had to watch out for me."

Bobby nodded, That's pretty much the reason Dean had given him for making the deal this time. "That sounds like Dean."

"Yeah," Sam agreed. He took in a shaky breath. "I know that this war is important, Bobby. I understand that we have to do everything we can to send this army back to hell where it belongs." He hesitated for a moment, then turned and faced his old friend. "But I'm asking you to help me find a way to save Dean. I promise we'll be there for this fight. I promise we'll do whatever is necessary, but…" Sam took a breath and swallowed and Bobby could see the emotion in his eyes even through the darkness. "But I can't do this without my brother." Sam's voice was barely a whisper. "I won't let him sacrifice himself for me."

Bobby didn't know if he could trust his own voice. It was obvious that Sam was in a tremendous amount of pain over his brother's actions, and he wanted more than anything to tell the kid that they would find a way, but he just didn't know if that was possible. "Sam, Dean made a deal –"

"I don't care." Sam's voice was suddenly stronger. Bobby watched in awe as the boy swallowed his emotion and replaced it with a fierce determination that rivaled what Bobby had always seen in his daddy. "There's gotta be something, Bobby. Some catch we can use, some kind of loophole. Dean may believe that my life is more important than his, but I don't. He's spent his whole life sacrificing for me. I can't let him sacrifice his soul. I will not let Dean go to hell for me. I don't care what it takes, but I'm gonna save him, Bobby. I'm gonna save my brother"

Bobby stared at Sam, noting the fire in his eyes. Hell, the kid was a Winchester. And it was a Winchester who had killed the yellow-eyed demon. As far as he knew, killing a demon outright was a feat not many other hunters could lay claim to. Besides, these boys meant more to him than he cared to admit. He'd never let anyone close to him – always figured it was easier that way, less entanglements, less pain. But, despite all his defenses, these boys had snuck up on him somewhere along the way and gotten under his skin. He'd be damned if he was going to let them go it alone now.

He nodded, a slow smile lifting a corner of his mouth. "We'll find something, Sam. I promise. We'll fight this war, we'll send every single one of these things back to where they belong. But we take care of our own. Dean's family. And damnit, family comes first."

Sam nodded and breathed in a sigh of relief. He looked back at the door and pulled himself from the cold cement. "I need to go check on Dean." He opened the door, pausing at the threshold. He looked back at the older man, still sitting against the motel wall. "Thanks, Bobby." He gave the mechanic an awkward smile before quietly stepping through the door and closing it behind him.

Bobby took a deep breath and blew it out forcefully. He scrubbed a hand over his face and adjusted his cap as he leaned his head back against the wall. He'd never heard of anyone outwitting a crossroads demon, or, for that matter, making one reverse a deal. But apparently Dean had managed to do just that. And if it could be done once… Bobby couldn't stop the soft chuckle that came from deep within. If he were a betting man, he'd put his money on the Winchesters; these demons had no idea what they were up against.

The End