Dean was enveloped in nothingness. The giant web he was attached to felt like it was burning his skin. The more he struggled against the bonds that held him, the more it felt like his skin was being ripped off. He could feel the heat rising in his body. All he could see was the thick black web that trapped him, and nothing beyond it. He wondered if everyone's hell was different. He had been promised a lot of suffering by a few demons over the past year, and he was betting that this was only the beginning.
Out of the darkness a figure came toward Dean. It was that of a woman. Her long blonde hair fell over her nude breasts, and her eyes were a piercing green. Dean gawked at the gorgeous, naked woman in front of him.
"Since when do they send you hot naked chicks in hell?" he said aloud to nobody in particular. When she was close enough so that her breasts were almost touching Dean's face, she whispered seductively into his ear.
"Remember me? We had a little fling about a year ago..."
Dean immediately recognized the voice. It was that of Lust, one of the seven deadly sins.
"I thought I vanquished your ass with all of your friends," Dean spat back. "And to clear the air, I'll try anything once, but I'll never be desperate enough to screw a demon."
Lust climbed up onto Dean, pressing her body onto his. He wished his hands were free so he could touch her perfect form, move his hands all over her, but the more he struggled to free them, the more his bonds ripped into his skin. He could feel blood trickling down his arms as she tempted him with her voluptuously perfect breasts. He wanted them. He could feel himself getting turned on by her. And then, as suddenly as she appeared, her beauty melted away, revealing a writhing, scaly-looking creature.
Dean screamed for his life. He wanted her off of him. Lust gave a shrill laugh, almost piercing his eardrums, and instantly disappeared. Catching a breath, he was almost glad she was gone. And he knew she wouldn't be the first demon to pay him a visit. He had killed a lot of them in his day, and now it looked as if he were going to pay the price, as each of them tortured him slowly.
As he tried to get the image of Lust's true form out of his mind, Another demon appeared and came toward him. He sucked in a short breath when Meg came out of the darkness. Dean stared her up and down. He thought she kind of looked like Mystique from those X-Men movies. Meg wasted no time in exacting her revenge on Dean. She pointed her finger at him, and fire shot out from her fingertip. The fire shaped itself into a sword, and Meg jumped onto Dean and started to stab him with it.
She stabbed him many times, but unlike a real knife, the fire sword simply left third-degree burns in the places it touched. Dean screamed in terror and pain every time he was stabbed. The stabbing seemed to go on forever. When it finally stopped, and Meg had disappeared, Dean had burns on his chest and stomach, and his arms and thighs as well. She had spared the lower halves of his legs for some reason.
In desperation Dean continued to struggle against the bonds that held him to that web. They cut further into his wrists, and there was blood all over his arms and legs. He knew what was coming next, and he didn't want to stick around for it. There had to be a way to get loose. He didn't want to be there when Lilith came to torture him. He could handle Lust's true form, and Meg's fire sword, but he was terrified of what Lilith might do to him.
Dean closed his eyes to stop the tears from falling. He wasn't sure who he was trying to impress by not crying. He didn't want to let those sons of bitches know they were getting to him. He thought of Sam, who was probably crying over his dead body right now. He wasn't sure what Sam would do next, but he hoped he'd try to find a way to save him. Dean's family had gone through great lengths to keep each other out of hell: his father for him, and Dean for Sam. He knew Sam wouldn't make a deal for him. They had talked about that just the other day. No more deals.
"Dean." At the sound of his father's voice, Dean's eyes shot open. His father was standing before him, looking very broken. Next to him, holding his hand, was Mary Winchester. Dean's mother.
"Dad...Mom..." the tears came back and flowed down his cheeks at the sight of his parents. "I...I'm sorry..."
"Look at you, Dean. Look what you've done to yourself," Mary scolded him.
"I thought I was doing the right thing. For Sam." Mary walked right through the web and stood next to her oldest son.
"Your father sacrificed his entire life to protect you and Sam. He gave up his own soul to save yours, Dean. And you turn around and give it away."
"I'm sorry!" Dean shouted in anguish. "Sam was dead! I wanted him back! Maybe making the deal wasn't such a hot idea, but I had no choice!"
"What's dead should stay dead," said John. "I'm sorry son, but I don't think Sam can get you out of this one."
Dean started sobbing wildly. Mary ran her hand through her son's hair, soaked with sweat and blood. Dean's sobs subsided a bit as he felt his mother's touch. It was something he hadn't felt since he was four years old. And just as suddenly as his parents had appeared, they vanished. He could no longer feel his mother's hand running through his hair. He opened his eyes, and there, standing before him, was Lilith.
"Pity...your parents don't seem to care too much about you, Dean," she said. She was still in human form. Dean struggled against his bonds with all his might, and shouted in pain when he heard his left wrist finally break. "You're not going to be able to get out of this. You're mine. For eternity. And your hell begins now!"
A blinding light emanated from her body, and Dean's surroundings were no longer visible to him. Then he fell unconscious. He had surrendered his soul to Lilith a year ago, and now she was ready to use him to her full advantage. Dean's hell was just beginning.