Beginning Note: Tag to 3x09. Spoilers for everything up to that episode. My usual quirky sense of humor decided to flee at the sight of poor Dean standing all forlornly in the parking lot. In it's place was my darker more depressing writing style and voila! here is the result. The scene where Sam tells Dean that he's preparing himself to continue fighting once Dean was gone sparked this little oneshot. Set directly after Ruby and Dean talk.

To Leave And Let Go

Even after Ruby was long gone Dean stood outside the motel room. After a few moments of uselessly gazing blankly into space he'd finally had the presence of mind to move from the middle of the parking lot and over to a wall, leaning against it for support.

Dean ran his hand over his face, a worry habit he'd picked up over the years. What did he do now?

He knew he needed to go back inside. Sam was already packing, gathering up all their gear. They'd be leaving this town soon, probably as soon as he returned. But Dean couldn't face Sam right now, not yet. Not until he'd had a chance to absorb what he'd just heard.

There's no way to save me, is there?

He'd finally asked it. The question that had been hanging over his head all these months. And the answer was more painful than it had been to force himself to ask the demon bitch, aka Ruby.

No, there isn't.

'Well that' Dean thought, choking off a strangled laugh. When had he actually started to believe he could be saved? When had he allowed that small flame of hope, so tiny he hadn't realized it was even there, that he wasn't going end up in the pit?

Somewhere along the way Sam had managed to make him believe that his brother could find a way. No matter how much he'd told himself that it wasn't going to happen, don't let yourself even freakin think about it, Dean found himself drawn in by the beautiful lie of a loophole that Sam talked on and on about.

Weeks earlier Sam took the Colt, used it on the Crossroads Demon Dean had made the deal with. For that brief moment, when he had realized what his brother has done, Dean had believed that it could have worked, that Sam might have saved him like he'd promised in the cowboy grave yard. Guess it's my turn to save your ass for a change.

It hadn't worked. And in all honesty, if Sam hadn't looked so devastated, forcing Dean to remember his job, watch out for Sam, the disappointment might have finally crushed him.The all-consuming defeat, the knowledge that his brother was desperate enough to carry out something both must have been thinking about ever since the Colt was fixed In Dean's mind it had represented the last ditch attemptsomething he would never dare try himself in the fear Sam would suffer for it.

From the very beginning, way back to the night hell's gate opened, Sam was ragging on him not to give up, not to accept that going to hell was inevitable. Dean had done his damnest to get the kid to understand that it wasn't happening, to wake up and face reality. Yep, he'd really made it his mission to squash his brothers hopes and dreams. Always flinging his one-year deadline in Sam's face. He'd told himself it was the only way to get Sam to toughen up, keep him from wallowing in denial.

'Guess what, Dean,' a snide voice in his head said, 'it finally worked. Sam's realized that you're a lost cause. He has finally given up on you.'

He wished he could tell that voice to just shut up and get lost, but it was right. So freakin dead on that it hurt.

From the moment he'd first told Sam what he'd done, that he'd sold his soul at the crossroads, his brother had always flatly refused to accept that Dean would die. Over the months he had come to rely so much on that faith, Sam's faith, dependant on the younger man's assurance that he thought Dean was even worth saving.

Life after the deal had become so fraught with fear, dread, and exhaustion leaving Dean an emotional wreck even if he refused to let it show. The only shining light, what had made it all bearable, was Sam. He would have given up on living long ago, let the terror just consume him, but every time he found himself slipping down into the shadows Sam had refused to let him go.

Sometimes Sam forced him to talk, and sometimes Sam just talked to him. But Sam always showed in actions or said in words what Dean needed to know; that his brother needed him, wasn't ready to just let him go. Even if Dean still thought that his future was in the hellfires, the knowledge that Sam wasn't giving up had kept him going. As much as he knew he didn't deserve it, knew he was a damaged soul, Dean could let himself believe that he might be worthy of the devotion and love he would see in Sam's eyes when he said that he still looked up to Dean, just as he had as a kid, still wanted him to be around.

I've been following you around my entire life. I've been looking up to you since I was four, Dean. I wish you would just drop the show and be my brother again.

At the time Sam had also said that Dean thought he had nothing to lose, because he was already a dead man in his own mind. It was true, almost. There was nothing that Dean could lose except for that look, and those words. Most days it was all he was holding onto. He'd felt safe in the knowledge, false security as it was, that if Sam still needed him, then he couldn't leave.

His conversation with Sam earlier had brought doubts to his reasoning. And questions he didn't want to be answered but couldn't stop his mind from asking.

Does Sam need you anymore?

But Sam had already answered that hadn't he?

Dean, you're leaving. If I'm going to fight this war once you're gone I'm going to have to change.

'Once you're gone...'. Sam had resigned himself that Dean wasn't going to be around in a year. Sam was taking over Dean's job, and hell, the kid would probably do a better job at it than he ever had. Dean didn't know whether to be angry at Sam, or at himself. He was supposed to have already known he would die, accept it and move on. So why did he feel betrayed that Sam was doing the same?

Tonight, for the first time in a long time, Dean thought he finally had lost everything. He was falling, tumbling back into the shadows, but this time he didn't think Sam would catch him, pull him back up.

This time Sam was letting him go.

When Dean finally walked back into the motel room, back to Sam, he said nothing about what Ruby told him. He wasn't ready for that conservation, and he might never be.

The place looked like ground point zero for an explosion. Covers and mattresses alike were ripped to shreds and small pools of blood, his blood, stained various surfaces. He looked away from the mess and focused on his brother, who was just finishing putting the weapons away in a green duffle. Sam frowned a little, probably pissed that he'd left him to do all the work, but Dean was too drained to care.

"Are you ready to leave?" Sam asked him, carryall bag in hand.

The words struck the rawest nerve Dean currently had. What he really wanted to do was ask Sam, 'Are you ready for me to leave.' But he couldn't. He was too afraid that the answer might be yes.

If anyone had asked him earlier, Dean might have said he was ready, and to bring the hellfire on. Eternal torment was a horrible fate, but the way Dean figured it, his life was almost hell on earth anyways. And it was worth it, right? Sam would be alive, like he was supposed to be, would have been if Dean had done his job right and saved his brother like he'd promised John.

But things had shifted with Ruby's 'sold souls become demons' revelation. The worst thing in Dean's mind was that he could become the very thing he'd made his life's purpose to eradicate. Demons killed without conscious or guilt, they destroyed the lives of families - had destroyed his family. Was it really possible that he, Dean Winchester, guardian of the innocent, would eventually turn into the thing he most hated?

Dean lowered his eyes, hiding the despair and desolation that was threatening to swallow him whole. The new cracks in his soul were steadily widening and he was terrified for the day they became too large, became visible. For one moment he considered letting them show, letting Sam see what was happening. But that moment passed and was gone, leaving him feeling even emptier.

Dean grabbed his own bag, sitting neatly on the bed, and faced Sam.

"I guess I'm as ready as I'll ever be." He said quietly.