"Here suffer those who did not sin yet did not have the required portal of our faith. Their punishment is the denial of Paradise." – Virgil
Dean didn't know how it happened. One minute he had the witch pinned, the other he was being flung through the air and crashing against a wall due to a spell, giving the witch enough time to get away. The last thing he remembered was hearing Sam calling out to him before passing out.
Waking up, Dean grunted and rubbed the back of his head where he had hit it against the wall. Looking around, he quickly realized he wasn't in the motel room with Sam. Standing up as fast as he could, he knew he had to figure out where he was. He checked if he had any weapons with him but found none. If shit hit the fan he had nothing to protect himself with.
Walking around, he found a road and decided to take it. After walking for a while, he came upon a citadel. Being as careful as he possibly could, he walked up to the gates and was surprised by who was waiting for him.
Dean wasn't sure if he was seeing who he was seeing. The reaper Tessa was standing in front of him, with a kind smile on her lips. Dean smiled at her, cautious of his surroundings, walking over to speak with her.
The last time he had seen her, she had impaled herself on the First Blade, ending her life. Seeing her again, made him question where he was or if he was dead. He didn't think the witch had hit him that hard, but he could be wrong. It wouldn't be the first time.
Dean asked Tessa what that place was and why he was there. Tessa's answer surprised him. Apparently, he was in a new and improved Hell, as Tessa put it, in Limbo to be more precise, and she had an important mission for him.
He was going to have to conquer each of Hell's nine circles if he was going to win not only safe passage out of Hell but also all the souls in the world. If he failed, he would never leave the circle he would be in when he failed and every soul will come to Hell instead of the normal order.
Dean was stunned for a moment. Not only was his own life and soul on the line, so was the rest of the world. It wasn't the first time the fate of the world was laid on his shoulders, he and Sam had saved it before, but this was different. For one, he was all alone, and two, he had no idea what awaited him.
He had no other choice. Telling Tessa he would do it, she warned him that it wouldn't be easy, that he would face many different temptations, for that is the purpose of the Devil himself, but if he was true of heart and remembered all he had learned about the nine circles, he could come out victorious.
Dean sighed, hoping that he could just get this over with and go home. Saying that he was ready, Tessa nodded and led him out of the citadel. Now, the fight for everyone's soul begins.