25 years ago

Azazel, occupying the body of then-20-year-old Nathaniel Price, stared down at the twins with a mad grin on his face. He already dealt with the first set of twins and their families, now it was just the Winchester's.

Soft footsteps echoed towards the nursery and Azazel paused from reaching inside Molly's crib.

"John?" The tired voice of Mary Winchester whispered. She squinted in the darkness, trying to see the figure of whom she assumed was her husband standing by the cribs.

"Is he hungry?" Mary asked a little loudly since Azazel hadn't moved. He raised a slim finger to his lips and stayed silent. "Well... Alright."

Mary turned away and started walking towards the stairs. Azazel turned towards the nursery door, his yellow eyes glowing in the darkness as a smirk appeared on his face.

"Sammy! Sammy!" Mary screamed from downstairs and Azazel turned to Molly. The little baby started to whimper and cry. Azazel caressed Molly's head as Mary rushed into the room, gasping loudly when he turned to her.

"I told you I'd be back." Azazel spoke in a voice that didn't match his face. It was dark and it sent a horrified chill up Mary's spine and he raised his hand out. Mary crashed into a wall of the nursery before sliding up. She cried out for her children, for John to save her.

She was silenced by Azazel, muffling her cries as a pool of blood started to soak her white nightgown. Azazel grinned and turned back to Molly, picking the child up as Mary choked on her own blood.

Azazel looked up to Mary as John's footsteps stormed upstairs. "Say goodbye to Mommy." He disappeared just as John threw the nursery door open. Azazel was nowhere in sight, and John walked to Sam's crib.

"Hey, Sammy." John whispered, caressing his son's cheek. John turned to Molly's crib, eyes widening quickly when she was nowhere in sight.

Something dripped onto John's hand, causing him to look up and see the horror of Mary, who was still alive and trying to speak. John fell to the ground, terrified.

"Mary NO!" John staggered up as Mary burst into flames. Sam began wailing, and John lifted his son up before running out of the room.

Dean was running down the hallway when John rushed to him, giving Sam to his oldest son. "Take your brother outside as fast as you can and don't look back! Now, Dean, go!"

Dean rushed down the stairs with his baby brother as John ran back into the nursery. His face burned from the fire and he rushed to Molly's crib, looking around in a panic. "MOLLY!"

———

Molly had fallen asleep again by the time Azazel reached his destination. The infant hadn't gone unnoticed by the demon that sat outside the Gate of Hell.

"I didn't know there was a guard." Azazel spoke quietly to himself. The Gate had been abandoned years ago, why a guard now?

The demon revealed her black eyes and walked up to Azazel, who had yet to reveal his own. "What's a man like you doing out here with a child?"

"I don't have time for this." Azazel seethed, the demon backing away as his yellow eyes had startled her.

"What's your business?"

"I don't need to explain why I'm here. Let me through." The demon looked down at the baby in Azazel's arms and scoffed, shaking her head.

"That baby is well and alive. You plan on just waltzing into Hell with a live newborn?" The demon raised a brow as Azazel shrugged.

"Can't kill her. She won't age in Hell if I kill her now." Azazel argued, quirking a brow at the demon. "Move."

"Can't. You know the rules."

"And you know I can kill you faster than I can kill the baby in my hands. Move." Azazel threatened through his clenched jaw and the demon stayed still for a moment. She eventually turned around and opened the large gate, only enough to let Azazel slip through.

———

By the time two months had passed in the real world, twenty years had gone by. Molly, wearing worn out clothes that could only fit an larger adult, wiped her hands on her pants. Blood soaked her skin and clothes. She stood in a pool of blood, looking down at the man that was gurgling and choking on it.

She had no idea who this man was. What he had done to be brought to hell after death. If he sold his soul or just died violently. He was reasonably young, so he didn't die of natural causes. Not that Molly cared in this moment.

She just did what she was told to do. Beat people senseless. She didn't enjoy doing it, but it was better then than her, right?

"Winchester." Molly turned her head towards the gate, where a demon dressed in a dark suit stood behind the door. "Azazel needs a word."

Molly didn't speak as she walked out of the cell. The man she had finished torturing was still attempting to beg for his mercy. As his vocal cords started to reattach themselves together, she could hear him more.

"I... can't..." He spoke, sputtering blood. Molly turned to him, a merciful look in her eyes as he begged with his. His blood was on her face. It stained her clothes along with hundreds of others. She wasn't allowed to talk to them, except to only ask one question.

"Given up yet?" Molly asked. The man, whose wounds had started to close, began to sit up. He was on his hands and needs, blood pooling from his lips still.

"Yes..." He spoke breathlessly. Molly looked to the demon, who gestured for her to leave and entered the cell.

Molly started walking down the hallway, listening to the man start to scream again, cries of agony in every door she walked past. She didn't flinch. Her eyes didn't tear up. She was fully used to the shrieking and the noise of blood splattering the walls.

But she still felt bad for every one of these people. Not all of them that were down here deserved this punishment.

"Molly. You're filthy." She turned her head at the sound of her name. Azazel was walking up to her, holding something in his hand. "I have something for you."

It wasn't like him to gift Molly something. He may have only done it one other time, and that was when he gave her a knife. A demon killing knife, specifically. But she had lost that a few years ago, and she knew exactly who had it. But she was never allowed to go after Ruby.

"What is it?" She asked quietly. Azazel opened his hand, revealing a small hex bag. Molly raised her brows and looked up at him.

"Immortality." He spoke quickly, a small smirk appearing on his face. Molly's heart immediately sank to her gut. He couldn't have possibly discovered immortality. And she couldn't be immortal. Not when she lived down here. "I'm giving you immortality."

"I can't—"

"You are." He interrupted with a deathly glare. Two demons suddenly appeared behind Molly and grabbed her by the arms. She called out in fear, kicking her legs as they hoisted her up onto a table and forced her down.

"No! I don't need this!" She begged, watching as Azazel pulled out a knife from his pocket.

"I could carve you open myself, but I have other matters. There's a demon that escaped yesterday, and after your last 'mission,'... I feel it's best you stay young." A third demon walked into the room as Molly kept shaking her head, thrashing her arms as Azazel handed the demon the hex bag and knife. After a moment, her turned back to her.

"Now you can work with me for eternity. Just as I promised." Molly's eyes widened in horror and she shook her head.

"No. No! Azazel!" She screamed as he walked out of the room, trying to move away from the demon as it walked towards her. "Get away!"

———

Molly wasn't entirely sure how much time had passed by now. Ten years for every month. It had to be at least three thousand years for her. She knew it had been, at least twenty-two years in the real world.

She was still stuck looking twenty. There was a scar on her abdomen from where the demon had shamelessly carved into her and shoved the hex bag in. No stitching, no anesthesia. Nothing to keep her from bleeding out on that table. She could barely move for a week. She guessed immortality didn't come with super healing.

Molly walked down the dimly lit hallway of wherever the literal Hell she was. Despite living in Hell for nearly three hundred years, she had never gone outside of 'The Temple' as she called it.

The lowest part of The Temple was where the worst prisoners of Hell were kept. Rapists, pedophiles, abusers, murderers and traffickers. People like that. Anything that could get you to serve a long time in prison in the real world, served you an eternity of agony in Hell.

That's where they usually put Molly. She had hundreds of years of dealing with the worst kinds of people, so by now, she spared no one any mercy down in Hell. When she was 'younger' maybe. But now she learned that no one here deserves mercy.

The level above was for people who had been arrested for their crimes. Because even He'll knows that they served their time but it still wasn't enough. And those that weren't caught deserve worse treatment, apparently. Genocide, mass murder, terrorism. Any god awful crime you could think of.

Depending on what kind of crime some people committed, demons loved to reap what the prisoners sowed. Molly wasn't one to do that, torturing was enough. On occasion, she would ask about the person she was handed, just so she knew when enough was enough.

But it never was. They always deserved worse.

Molly rounded a corner and towards a flight of stairs that led up. The level she was going towards was for people who had sold their soul for good reason. She hated this floor the most because she knew all of the people in there only wanted to help.

Some were in there for their children. For their husband or wife. Some were in there for selling their soul for a stranger or themselves. None of these souls had been sold for selfish reason. But the floor below was.

There were many people in the floor below that had sold their soul to get someone killed, or for fame. Celebrities were a frequent occurrence on that floor.

The cries of agony became louder as Molly ascended, walking down the hall for a long time before finally getting to a new cell. A man was in shackles that were strung up on the ceiling. His dark blue denim jacket was torn and bloody, as well as his shirt and pants.

Despite his weak appearance, he slowly looked up to meet Molly's eyes. She walked into the cell, shutting the door behind her. Her back was turned to him for a while, and the man continued to stare at her.

"You're... Not a demon." He whispered. Molly said nothing and knelt down, picking up a rebar spike. "Are you a demon?"

Molly turned around to face the man. She only shook her head slightly. Just enough for him to see. The man dropped his head, and huffed. "John."

John looked up and met Molly's eyes. She didn't seem phased. Many people tried talking their way out of being tortured because of how long it always took Molly to start. "My name... Is John Winchester."

How fast Molly dropped the rebar made John flinch. He hissed in pain as the shackles rubbed against his raw, bleeding skin. After a moment, he looked at Molly again. He frowned in confusion, unsure as to why she looked so scared.

"Oh my God." She mumbled, pressing her back against the door. She shook her head in disbelief. Her throat closed up from the lump that had formed but she couldn't force a single tear out, even if she tried.

John continued to stare at Molly. "What's you're name?" He asked. She turned towards the door, looking out of the peep hole before turning back to him.

"It's—" Molly silenced herself quickly. Her mind was racing with questions and thoughts and she wasn't sure if now was the best time to ask any of them. Molly walked up to John and he tried to pull back, but couldn't from the shackles.

"Molly." John froze as she said her own name, his breath becoming heavy as Molly stared at her father. "I'm Molly... It's me.. Dad."

"No." John shook his head, oiling on the shackles. "My daughter is dead! She died over twenty years ago!" His voice shattered at the memory of his lost daughter, and Molly shook her head, a pleading look in her eyes.

"Please, you have to believe me. I was taken by the yellow eyed demon when I was a baby I didn't die in that fire!" Molly whisper yelled, looking back to the door every few seconds. She was afraid they would know she was talking to him.

"She died with my wife. You are not my daughter!" John shouted, trying to free himself from the shackles.

"I have brothers, don't I? Two older brothers! They— They know about me, don't they?! They have to know. Do they know they had a sister?" Molly asked quietly as John stopped thrashing around. Molly dug through her pocket, pulling out a key to the shackles and released John.

"I wouldn't be doing this if I wasn't your daughter." John stared at Molly for so long. He looked her up and down, grabbing her by the face. Tears swelled into his eyes as pain washed over him. He missed her entire life. He never got to see her take her first steps. Say her first words.

She lived a life far worse than he could have imagined.

"Molly..?" She nodded quickly and John was quick to hug her. She stood there frozen, unsure of what to do. It's not like she had ever received any sort of affection in the 300 years she existed in Hell. This was her first hug ever.

Molly held John's arms as he released the one-sided hug, a soft smile appearing on his face. "You sold your soul." Molly whispered, stepping away from him. "Why?"

"For Dean. He was dying, Molly. I couldn't let him." John shook his head as Molly nodded in understanding.

"It must have been a good decade then, if you saved him." John stayed quiet for a long time. "Right?"

"I died the same day I sold my soul. Dean lived."

"But deals don't work like that. If he was dying then he was still alive. You should have been given ten years! Who made the deal?"

"Yellow eyes." Molly's eyes widened, turning to the door and walked out, locking it behind her. "Molly— Molly don't leave me here!"

"I'm sorry. If I let you out they'll— I need to go." Molly raced down the hallway as John continued to scream her name.

Molly never saw him again.

Not having Jenny in a chapter feels weird. But? this is just the first chapter of Molly's backstory! I had to fix a few past chapters due to the fact I did math wrong, but it's all good now! Hope you enjoyed this chapter and I really hope it made sense 💀