Disclaimer: I do not own Supernatural or any character from the show, Supernatural. They belong to Kripke and crew. I'm also not getting any financial benefits, by posting this story. No copyright infringement is intended.
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Sam paused. He nervously looked up from the book he'd been reading and anxiously eyed the man tied to a chair.
"What?! Don't stop on my account. Go ahead… continue reading. When I get to hell, I promise to pay your brother a visit." The man smiled wickedly. "As I slowly peel the skin off his body, I'll be sure to mention that you sent your regards." The man slowly licked his lips, as though he longed to see his statement come to fruition. "I'll even mention how much fun you and I had and that you personally sent me to make certain that Dean had just as much fun as possible in hell. Although…" The man paused, as though a thought had just occurred to him. His face changed, as he realized the implications of his thought. "I'm not sure that Dean would call what we demons enjoy as 'fun'. Sure, we love to torment people and their souls. Who doesn't enjoy slowly roasting a person over a red, hot fire? Who doesn't enjoy seeing hope fade in another person's eyes, as you dash it all away?" The man gave his shoulders a slight shrug and kept a small smile on his face. He kept his focus on Sam, as he continued. "Demons are loads of fun. We break all the rules, since they are, after all, made to be broken. In hell, we have one rule. And that is, to have as much fun as possible, especially if it's at the expense of some one else. And now that you're brother has joined our eternal party, it's all at his expense. I can't begin to tell you how many demons have lined up to spend some time with your brother." The man's smile grew, as he saw how his words were affecting Sam.
"Demons are bickering amongst themselves over who gets to torment your brother next. But, in the end, we all get a turn. You see. Your brother is a bit like a slate. A demon does whatever he wants. Then, when it's the next demon's turn, Dean is cleaned up and the fun starts all over again. Sure, on the outside, Dean will look untouched and his body will be back intact. But, his mind… well, that's another story." The man lowered his voice and leaned towards Sam, as though revealing a secret. "You see… he'll always remember ever detail about what's been done to him and what he's been told. His body gets restored to its pre-hell condition. But, his mind and soul doesn't. Ah no… those get to remember ever little detail and experience that takes place. Wouldn't want him to forget all the fun that's being had. There are countless numbers of demons. And each has their own definition of fun. Some are even more creative than others. So, you're brother will rarely experience the same exact thing more than once. Like I said, us demons are party animals and we wouldn't want Dean to have a boring time in hell." The man's smile grew bigger and more wicked. With a quick nod towards the book in Sam's hands, the man continued. "And once you finish your reading there, I'll get to join in the fun. A little rule was added that said, 'any one sent back to hell by the hands of one Sam Winchester, gets to jump to the front of the line and gets to meet Dean, immediately upon their return to hell.' So, you go ahead and finish what you're doing. And, less than a second after you're done, I'll be with your brother and getting to have the fun that you wouldn't let me have up here."
"Sam, finish it." Bobby said, as he entered the room. He had been surprised to enter the room and see Sam just standing in front of the possessed man. Until now, Bobby had been outside and had confirmed that no other demons had remained. He'd been with Sam, since Dean had been taken to hell. Dean had asked Bobby to look out for Sam, and Bobby was living up to that promise. Sam had taken Dean's death, as well as could be expected. Bobby hadn't been surprised, when Sam had insisted on getting back to hunting, after taking care of Dean's corpse. Sure, there were moments where Bobby could tell that Sam was remembering something about Dean and a few times, Bobby had seen Sam lovingly hold an item, which had once belonged to Dean. But, that was to be expected. The two brothers had been very close. And had Sam not been affected by Dean's death, then Bobby would have been worried. Until now, Bobby had felt that Sam really was ready to continue hunting and killing demons. But now, Bobby wondered what the demon could have said that had caused Sam to stop the exorcism. Bobby quickly walked across the room and took the book out of Sam's hands.
Sam barely acknowledged Bobby's actions. Sam's heart had broken, as the demon stated what Dean was going through. Sam knew that demons lied, except when the truth was more affective than a lie. And this time, Sam was fairly certain that the demon's statements were more truth than lies. Sam's imagination and excerpts from books had given Sam an idea of what Dean would experience in hell. But now, Sam was hearing firsthand what the demons were doing to his brother. Sam's heart felt weak and his stomach felt as though he had eaten a ton of cement. Sam was even feeling a little light-headed and weak in the knees, as he realized his own actions could be adding to the torment that Dean was experiencing. He could feel a slight tremor in his hands and felt his throat tighten, as he realized that every demon he sent to hell would then take their frustrations out on Dean. Dean had done so much to protect Sam and keep Sam safe. And this was the way Sam repaid him?! Sam was sending demons to hell, who were out for revenge and had their sights set on Dean! Sam began to have second thoughts about sending demons back to hell. He couldn't stand the thought of adding more demons to the list, of those who were tormenting his brother. Sam may not be able to go into hell and save Dean. But, the least Sam could do was limit how many demons returned to hell and tortured Dean, right? There had to be some other way to exorcize a demon and not send it to hell, right? Sam turned pleading eyes towards Bobby and prayed that Bobby held the key to Sam's dilemma.
Bobby had begun to read the exorcism, when he felt eyes upon him. Glancing up, he saw Sam's pleading look.
"Now, don't disappoint me. It really is rude to tease a person. You bring me here, tie me up, and then taunt me with an incomplete exorcism. We all know, that Dean's waiting for me in hell and is longing to see what I have in-store for him. And, we wouldn't want to disappoint good, old Dean, now would we?" The man mockingly looked at his two captors. "Tsk. Tsk. Gentlemen, I'm now at the top of Dean's dance card, and I hate to leave him waiting. So, what do you say we wrap up this little book reading group, and I can move on to the party that's going on downstairs?"
Bobby looked back at the book and continued to read. He had heard what the demon had said and assumed that similar remarks had caused Sam to stumble with the exorcism earlier. Seconds later, a black cloud came out of the man's screaming mouth and then, the man's head dropped lifelessly to his chest.
"Sam, get the gear out of my truck, so we can clean this mess up." Bobby watched Sam leave the room. Looking down at the floor, Bobby said, "Sorry, son. I know the last thing you need is another one; but, we didn't have any choice. Hang in there Dean. Sam and I aren't going to give up on you. So, you just hang in there 'til we find some way to get you out."