A Few Months Ago

A hollowed out shell of a man is what Sam would have described Dean. Two days ago, he had buried his life-long friend, high school crush, and fiancé.

Sam never thought Dean would gain the courage to date Jenny. Of course, Dean went after every girl he fancied, but Jenny was always different. Maybe Sam once thought Dean viewed her as a sister. Now he understood.

He didn't go after her for so long because he was afraid of getting to close.

Dean hated getting close to people for this very reason. He blamed himself for Jenny's death, and for good reason, too. She saved his life, he couldn't not blame himself.

And there he was again, two weeks later, still in the fetal position on that motel bed in Pontiac. Jenny had been dead for two and a half weeks. Dean started to understand why Jenny didn't eat when she was upset.

That feeling of hopelessness and pain clouded his urge to shovel his mouth full of a good burger. He couldn't even begin to express how he wanted to puke rather than eat. And he didn't have anything to throw up. His stomach was as empty as his soul.

His mind though. That was a different story. He was drowning in memories of Jennifer Price. Of the badass woman he had fallen hopelessly in love with. The girl that never thought about the consequences to her actions. The one that was always willing to make the hard choices to keep others safe.

She was perfect in every way possible. And the world took her from him. Lilith had taken his Jen. And he didn't have the energy to get up and find that bitch.

He didn't have the energy to do anything. Walking was like having millions of needles prick his legs, only for the pressure of more needles to slice through his feet. His shoulders were heavy with the weight of his shirt. Something so light and delicate was causing him to stay glued to his bed.

Another memory washed over Dean, and he felt something graze his hand. No. He imagined something grazing his hair. When he opened his red and puffy eyes, the vision of Jenny caressing his hair with that soft smile she always had, was gone.

Dean's phone vibrated on the nightstand and he ignored it. After a while, it went to voicemail.

"Dean. It's Bobby... Look I know you're dealing with... With coping. But don't be like Sam, alright? Running off when the going gets tough. Why don't you come and stay here for a while? I can make the guest room up for ya.. Just call me back, okay?"

Dean shifted uncomfortably and turned away from the nightstand. He reached for a pillow before stuffing it between his arms and chest, and went back to staring.

Dean's stomach grumbled for the first time in too long. He let out a long, heavy sigh before very slowly sitting up. His head throbbed with an ongoing migraine, probably from dehydration.

Dean moved at the pace of a turtle. He struggled to put his shoes on. And even after that, he continued to sit on his bed for another twenty minutes, simply staring at the empty bed his brother had been occupying one week, and four days ago.

Sammy just had to leave, right? He wasn't Dean. He couldn't sit, locked up in this motel, and cry day and night. He wasn't weak. He lived, he lost, he moved on.

Dean turned to face a mirror, staring at his reflection. He didn't recognize himself. He was never one to just sit around and cry. Was this out of character of himself? To cry and cry and cry? He couldn't stop crying. Would he ever?

Dean slowly let himself stand and grabbed his wallet. His hand slid against the nightstand before he mistakenly dropped it. A wallet he hadn't opened in weeks flew to the ground and sprawled itself out, the inside staring up at Dean.

Jenny's face was looking up at Dean with a bright smile. A picture he had taken of her years ago, haunting him now. Dean turned away from the wallet, and fell back onto the bed, covering his face with a pillow.

———

"Was this endless pain if suffering worth it in the end?" Jenny thought to herself. Her face was covered in blood. A demon stood before her. This demon didn't have a meat suit like a few of them did. This one was in its true form, and Jenny didn't have the stomach to look up and see it's 'face.'

"Given up yet?" The demons voice was low but it reverberated the room the two were in. Jenny flinched hard enough for the demon to laugh at her, but she refused to speak. The demon scanned Jenny's naked body. Her clothes were aimlessly thrown around the room and coated in a thick amount of her blood that, if she were alive, she most certainly wouldn't have survived that much blood loss.

"No." She spoke hoarsely, and felt like she was forcing herself to say it. It hurt to speak, and she didn't know if it was from the demon before, who did have a meat suit and wanted to use it to his advantage, or from this demon slowly slicing her throat open.

Maybe it was both. or maybe it was from her refusing to speak in the last few months she had been down in Hell. How long had it really been, though?

The demon said nothing and simply walked out to go to another soul. After a few moments, the door to Jenny's cell swung open, and a pair of boots clicked against the cement.

"Given up yet?" A voice Jenny would forget asked. She rested her head against her arm, which was raised above her head. A dark haired woman with deep brown eyes was staring down at her.

Jenny glanced to the open door, then to the woman, who she knew wasn't a demon. Slowly, Jenny swallowed all of the blood that had pooled into her mouth.

"How long... Did you last?" She asked, her galea's dropping from the resting position it was in. The woman didn't say anything. "You... Look like uh... Someone that gives up quickly."

The sound of metal scraping against concrete echoed in Jenny's ears. Silence filled the room, but the sounds of begging and screaming seeped in through the cracked door. After a moment, Jenny gasped in agony as a metal pipe went straight through her chest.

———

Molly walked past a cell with an open door, only looking long enough to see the soul inside had a pipe going through her bare chest. The soul was filthy with blood and the woman that was torturing her looked towards the door. That woman have Molly a crazy smile before shutting the door completely.

Molly walked into the next room. The room once occupied John Winchester, but since his escape from Hell and assistance with the killing of Azazel, he was sent up to Heaven.

Molly stared at the soul that was coward in a corner. For a moment, she was thinking. The soul slowly looked up at Molly and started to weep, begging for her to not do anything.

"Give up then?" Molly asked as she walked into the cell. The soul started nodding quickly, and crawled over to Molly.

"Please. I can't go another day of it." The man clasped his hands together, resting on his knees and stared up at Molly with glistening tears in his eyes. Molly yanked the man up and walked out of the room, and many other demons had been doing the same.

Molly marched down the hallway of the torturing souls, occasionally glancing inside a room to see if it was being occupied. The soul she was dragging next ti her kept asking questions until they eventually made it to a door.

Molly opened the cell and tossed the man inside. "Do what you want to it." Molly gestured to the other soul in the room. The man quickly turned, eyes wide.

"T-Torture? No! I can't. I can't please there has to be—"

"Torture or be tortured." Molly interrupted the man harshly. She's had to repeat that line thirty-six times today. And the day just started for her.

"Please... There must be something else." The man begged. Molly simply tilted her head and raised her brows.

"Welcome to Hell."