If only has he received the massage on time… all this could've been avoided. Sam's girl would still be dead (as if that's not awful enough, god, Sammy)- but Dean could have found him, take care of him, fixed him (if theres anything left to fix).
Sam dead. The thought is unbearable, unfathomable.
Dean is not freaking out. Defiantly not. He is going to find Sam, find dad, make everything better.
It sure couldn't get any worse.

"Its Sam. Leave a massage."
"Sammy, it's me. Listen carefully- I need you to pick up the phone, you hear me? It's real important, man, I mean it. Dad's on a hunting trip, and he hasn't been home in a few days. Answer the phone, damn it, I need your help."

He first heard about what happened from a demon (demons lie. however, sometimes they don't). There had been so many demons around lately, and without dad around, without Sam to do the proper research, Dean felt… misplaced, rough around the edges.
He missed having somebody to discuss his morbid theories with. He even called Bobby (who did pick up, god bless that old guy) who promised him help in finding his father.
Then he got a text from his dad, first one in weeks. Coordinates. Turned out to be a hunt, that seemed… easy. Too easy. Dean couldn't have guessed it would be a demon, he though it was just another case of a witch gone crazy (god, he hates witches).
I was a demon, though. And she was… beautiful. Scratch that, she was stunning, practically dripping with sex appeal. She lifted her green eyed gaze from the TV screen towards him as soon as he busted the door into a neat, organized, catalog page living room. Cocky, he always was too proud. He smiled when he aimed his gun on her, ready to fire.
Then he heard the familiar voice, oh so familiar-
And the screaming-

"Its Sam. Leave a massage."
"I have been calling none stop for three days, you freak! Answer your phone, Dad's in trouble. I can't do this without you. I'm so pissed at you, you have no idea, you little piece of-"

The demon shook her head, a smile stretching those rosy lips over too sharp teeth in a round smile. She took a long sip from the cup between her long, fragile looking fingers. Her teeth are stained red when she put the cup down.

"Its always fire," she says. "Look at her, so young, so innocent. Fire tends to claim the innocent ones."
It's a security tape recording, going on repeat. A bedroom catching on fire, a young, blond women pinned to the ceiling, slowly, oh so slowly, her mouth opens in a silent plea. she burns then, horrifically, beautifly.
Sam's voice is barely audible over the crackle of flames, but Dean could hear him nonetheless, loud and clear and so desperate-
"No! Jess- please- no!"
Dean shot the demon's head when the The recording ended. Then he went ahead and puked all over the expansive looking carpet.

"Its Sam. Leave a message."
"Fuck you, Sam, you care for nothing but yourself. Dad needs your help, and you can't pick the god damn phone for a whole week!? You don't care abut him, and it's pretty clear that you don't care about me, either. So don't you dare call me, you hear me? I don't want to hear a damn word from you, you useless freak. You walked out, you keep your distance- fine. But you better stay gone, Sam. "

Dean called his dad, sobbing, left a hysterical voice mail, then called the university. The secretary that answered was overly excited to tell him the gory details.
"Sam Winchester's brother? Finally!"
Dean wiped his eyes, starting the car and pulling out of the driveway, hands staining the wheel red. "Please," he said in a clipped tone. "Please, what happened?"
"Oh, you don't know yet? Sam Winchester was sharing a dorm apartment with Jessica Moore, his girlfriend. Things sure were steamy," she added, the gossip obviously still new and exciting." And they were cute together, too. He was one of the most promising students, really. But a fire overtook the apartment and they were both locked inside. He tried to save her, poor kid. She is dead now, dead and gone."
"Where- where is he now?" dean asked, overwhelmed with selfish relief. Sam is alive, that was a good start. Anything else, Dean could fix. (could he?)
"I don't know," said the secretary, apology pouring out of her voice. "I'm so sorry. Nobody knows. We have been trying to get hold of you for weeks, sir, where have you been?"

He investigates the local police, the hospital staff, Sam's friends, Jess's mourning family. Sam had burns on his forearms, pretty serious ones, too, when he arrived to the hospital. All his savings burnt down- and apparently, he didn't have a bank account. He couldn't afford anything, really, but he did show up to class twice more after the fire. "looked like a zombie," said the young professor, shaking her head sadly. "I hadn't known. I would have offered him to stay, at least to spend the night. But he seemed so… tired. Lost. I came to talk to him afterwards, but he was already out of the classroom. That was the last time I saw him. Nobody knows where he is now."

Panic was babbling up in Dean's throat. Sam was gone, he was lost and hurt and heartbroken, unreachable. And Dean had no leads as to where might he checked his phone. Thirty three unanswered phone calls, four of which were from Sam's number. And one unread voicemail.

"This is Dean Winchester. If this is an emergency, leave a message. If you're calling about 11-2-83, please page me with your coordinates."
"Dean—" a long, stuttering breath. "I can't- I don't remember, I don't remember how- oh god, Dean, please pick up- you hate me- he hates me- she's dead, Dean, she's dead-" then the sound of retching, over and over and over again.

At the end, Dean finds him by accident. It has been two months since the fire, four weeks of fruitlessly searching. Dean decides to go to Jess's grave, put some flowers on it (he buys white roses, Sam once told him that was the appropriate flower to respect the dead).
The graveyard is quiet and peaceful, rain clouds gather in the sky up above him.
He turns a corner and swallows bile. A homeless person is curled up against one of the graves, holding a teddy bear to his chest and softly mumbling under his breath. The smell of rotten flesh tints the air, sweet and sour and despicable.
"Hey," says Dean. "Are you ok, there?"
Hazel eyes land on him, young, so young and fragile looking. Cheeks bright red, lips dry and cracking, gaze confused and uncomprehending.
"Oh, oh god-" yells Dean, the flowers dropping from his hands. he then breaks off into a sprint. "—Sammy!"

""I'm so sorry, I'm so sorry, I didn't get your massage up until now- oh god, Sammy, what happened, what happened to you-"
Sam's arms are swatted with bandages, thick and battered looking, and he is thin. Real thin, like he hasn't eaten in weeks, (maybe he hasn't), every single knob of spine showing through his once white hospital shirt. Dean lays his fingers on every side of Sam's face, forcing his brother to look into his eyes. Sam's voice isn't louder then a whisper, wrecked and painful sounding. "Not real, not real- "
"Sammy-" Dean is crying, he can feel the wetness on his cheeks. "Sam, please, look at me, man."
"She was j-just here," Sam explains, hopeful, face lighting up (as a fucking charismas tree) and he grins a dimpled smile that spears right through Deans heart. "Baking cookies for the c-crows. Dean hates m-me now, he's not coming. Don't y-you lie- Liar- liar pants on fire," he giggles, then breaks into a coughing fit that stains his teeth red.
"look at me, Sam, just look, please- I'm here." Dean curls his fingers around Sam's shoulders. Sam is so thin, the bones underneath Deans fingers are practically grinding together, he can hear it. Dean tries his best not to vomit. That smell, though-
Sam's face crease up, as if he is staring into a too bright light. 'N-no," he whispers, "I can't do this. I can't-"
Dean can see how the grin is starting to shutter, the safe (insane) place that Sam build in his mind quickly dissolving into nothing.
"Oh, Sammy," says Dean, softly, cruelly. "Jess is dead. I'm so sorry."
"Stop," cries Sam, pressing his eyes closed, shakes his head, shivering. "No, stop-"
"Sammy. Listen to me. Look at me. Look." Sam is sobbing so hard it seems that he has trouble breathing, but he still wont look at Dean's eyes

"its Sam. Leave a massage."
" I never meant any of it, I was drunk out of my ass, I'm so sorry. Please? Are you okay? Can you call? I swear I didn't mean it. I swear. I'm sorry, Sammy-"

"Sammy." He says softly, forcing Sam's eyes open. "Jess is dead."
And Dean is grateful, selfishly, pathetically grateful, when Sam buries his face into his shoulder, and cries.