A/N: It really bothered me that Sam never looked for Dean when he went to purgatory. I felt it was completely out of character. There were moments of the Amelia story I could understand and appreciate, but the overall arc just didn't work for me. So here's my own version of what might have happened. AU after the end of 7.23, spoilers through 8.01. Dialogue from various episodes in bold. I own nothing, just playing in the Supernatural sandbox.
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"You got what you wanted – Dick's dead, saved the world. So I want one little prophet. Sorry, moose. Wish I could help. You certainly got a lot on your plate right now. It looks like you are well and truly... on your own." With those words, Crowley snapped his fingers and disappeared.
Sam stared in shock at the spot where Crowley had been seconds before, then around the empty lab in growing horror. Dick had been killed, yes, and apparently the remaining Leviathans were being dealt with, but where was Dean? Cas? Kevin had disappeared with Crowley's minions to who-knows-what kind of hell…probably actual hell. He paced over to where Dean had been standing, but there was nothing there. Glance towards the spot opposite, where Cas had been, but again, nothing. The silence of the building was deafening. LEFT BEHIND it screamed at him, ALONE.
Frantic, Sam whirled on his heel and tore out of the horrid lab, desperately looking everywhere for any sign of life. There were bodies, black goo, even some red blood, but nothing moving or breathing. Meg, he thought, where is Meg? He grimaced. It must be bad when I'm looking for a demon bitch again… That thought almost took him to his knees, his breath knocked out of him as memories of Dean dying and his descent into darkness under Ruby's influence flooded his mind. Gathering himself, he continued at a slower pace toward the front of the building where he assumed the Impala had been left per their original plan. He found it as expected, but it was nearly his undoing. There were shattered side windows, a couple stray bullet holes, and deep dents and scratches from the sign Meg had apparently decided to halt her progress with. Dean's pride and joy, so injured…no matter, he would fix this. He would fix it all.
Prying the driver's side door open, he brushed the glass off the seat and then held his breath as he pulled the wires and tried to start her. A sigh of air rushed out of him as the engine caught and started, and Sam carefully backed away from the sign and pointed the car towards the highway. Once on the open road though, he only made it a few miles before pulling over. Where am I going? He wondered. Bobby is gone. Dad, Dean, Cas, Rufus, Ellen, Jo… Sam stared out the broken window, feeling as if he was the one shattered. The view was bleak, much like the future…empty, barren fields in all directions as far as the eye could see.
When Dean had died last time and gone to hell it had been awful, but Bobby had been just a phone call away, had left him a million concerned voice mails. Even though Sam had ignored him, he had known there could be support and help in a heartbeat if he wanted. Now, however, there was no one to care if he lived or died. No one to turn to for advice. No clue where to start looking for Dean and Cas - assuming they were not just obliterated into nothing along with Dick Roman. Were they dead? Alive but hurt somewhere? In hell? In heaven? How do I possibly begin to search for them?
If asked, Sam could not have told someone how long he just sat there…far after he'd grown cold from the wind blowing in the damaged windows. He finally shook himself from the paralyzing indecisiveness, restarted the engine and easing the car back onto the road just drove. The gas light indicator finally awoke him to the need to pull off, and after climbing out of the vehicle and noticing his stiffness, Sam realized he probably needed to find somewhere to stop for the night. Enquiring at the counter, the station clerk pointed him to a motel that had seen better days just a few miles up the road. He quickly and efficiently checked in, entering the room only to stop abruptly, realizing he had automatically gotten a room with two beds. The ache in his heart intensified, making him almost feel nauseous. Rallying briefly, he readied himself for the night and curled up on the bed furthest from the door, realizing afresh just how much his brother's steady presence had given him a sense of safety and protection. The tears fell then, and he wept for Dean - wherever he was and whatever he was having to experience. He wept for Cas, who had become a dear friend in spite of his many failures, and who had just started to become himself again. He wept for Bobby, who had wanted so badly to stay with 'his boys' yet had started becoming the very thing he spent his life hunting. And he wept for himself, knowing there was no comfort to be had, the years ahead one long lonely road, with no one to watch his back or to rely on. Eventually the tears ran out, and exhaustion took hold, and finally, finally, he slept.
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Three weeks later Sam was almost a permanent fixture in the old cabin they'd called their latest 'home' since Bobby's house burned. He had combed through every book he could get his hands on, trying to find a starting point for what possibly could have happened to his brother. The problem was they had found almost no literature on Leviathans to begin with, so beyond the obvious knowledge that they came from purgatory and so - perhaps - returned there when killed, he could find nothing. He had tried summoning another angel, but the feathery crowd clearly had no use for him (if they ever had) and refused to answer. He had also summoned Crowley, which had gone less than stellar. He had been pissed…understatement…to have been pulled away from his nefarious schemes, and his beyond-cryptic responses left Sam desperately hoping that at least meant Dean was not in hell.
Fixing up the Impala and immersive research became his daily routine. Food and sleep happened when his body wouldn't allow him to continue. A polite exchange at the Gas-N-Sip brought home the reality of his total isolation when his response came out raspy, his voice rough from disuse. By six weeks he was at his wits end, finding no promising leads in the vast amount of books he had poured over day and night. Sam then started searching the internet beyond practical and logical, looking into the out-there, arcane, strange, and obscure trails he could follow. It was slow going, and invariably when he would happen across a mention of a book or manuscript or talisman that might have promise it had 'been destroyed in the fire of aught nine' or some such stupid bad luck. He tried finding another genuine psychic to see if he could connect with Dean that way, but although he did finally locate someone, there was no answer from 'the beyond'.
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Sam returned back to the cabin after yet another dead end trail completely done. It had been twelve weeks - three months! - of being completely alone and not finding one possible answer. He curled up on the bed his brother had used, trying in vain to still smell that mix of gunpowder and musk that was unique to Dean, but it had faded over the weeks, just as his hope was fading. No leads, no further than when he started looking months ago.
"I don't know what to do, Dean!" he cried into the empty room, punching the pillows in frustration. "What do I do now?" he yelled, "What do I do?" He sank back tiredly onto the bed, knowing he hadn't been sleeping well…or eating well, for that matter. Food had become very much an only-as-necessary afterthought, and sleep happened when his body forced him to. Dean, where are you? I need you, man. I can't keep going like this. Help me, please, he thought as he reluctantly let his eyes drift shut and he succumbed to his body's need for rest.
