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Day One:
Sitting beside Dean after he ‘died’ isn’t what I had planned for the evening. However, if he were to wake up with only his moose of a brother around, he would most definitely be out of my reach. Once Sam realizes that he’s back it’s going to be hard enough to keep him from taking Dean from me. I guess I’ll just have to bring him over to my side. I’ll take him to hell for a while and let him acclimate. He’s about to get a crash course in true demonology. It’s nothing like the books in the bunker describe. We couldn’t let the hunters know all of our secrets now could we? However, I have to time it just right, so we have the longest amount of time between when we leave and when the enormous moose starts looking for us.
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Day Two:
Hell time is a lot longer than time in the bunker. So when he woke up we had only been gone for a few seconds there. I’m hoping I’ll have a little while to let him see that I’m not the enemy here before Sam starts summoning us. It probably wouldn’t work with him anyway, but I don’t want to have to face him until I know I’ve won Dean over. Going by the fit he’s currently throwing, that isn’t going to be the easiest task. Without the need to eat or sleep I may have my hands full with the new knight of hell. If he realizes he can ‘pop in and out’ as he calls it, I may not be able to keep him long.
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Day Five:
Luckily, Dean and I have always had something of an understanding. He knows I’m not the worst of the baddies and I know he’s not the best of the goodies. There has been some conflict in the past, not going to lie, but I believe we can look past that and strike a deal. That is what I’m known for after all. He’s starting to calm down a bit, it shouldn’t take long now. He has been asking more questions in between his bouts of throwing things around my home and killing any demons who come looking for me. It definitely isn’t looking good for my subordinates. I’ll have to reign him in soon or there may be an attempt at a coup.
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Day Ten:
I believe Dean may have realized how strong lust is as a demon. Without the nasty feelings that can be associated with sex, it is so much more freeing. I do believe he is trying to fuck his way through all the female demons now instead of trying to kill them. I will let him have his fun for now, but I won’t stand by and watch this for long. He’s supposed to be mine. From the things he’s saying, I think he’s realizing those social norms that kept him from expanding his experience from women while he was human are no longer holding him down. I don’t believe it will take him much longer to change his sights from women alone. When he decides that he can experience the male body as well, that’s when my patience will wear thin. I can watch him fuck any woman he likes, but I refuse to watch him fuck, or be fucked by, a man.
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Day Fourteen:
I really should be teaching him more about being a demon. We have been, what I would call, distracted lately. It turns out the little masochist likes being thrown around. You would think with as many times as he’s been tossed by creatures that would no longer be the case. When he started in on one of the male demons, I decided I had shared enough. Maybe turning one of my more loyal subjects into a pile of dust wasn’t my best move, but things happen. At least I don’t have to worry about Dean playing with that one anymore. I have to get him past this new appetite of his. I think tomorrow I may show him a little trick that isn’t in those books of theirs in the bunker.
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Day Fifteen,
Probably not my brightest idea, letting him see how we turn into hell hounds. I had forgotten his fear of the beasts. This morning I showed him my beast, thinking he would realize it was me and not be frightened. I was definitely wrong. It took me nearly the rest of the day to get him calmed down. However, there was a positive to come from today's lesson. When he was so deathly afraid, it wasn’t his brother that he called out for. No, it was me. I know it seems like that would be the most plausible thing to do since I am here and he is not, but for the longest time he has been calling for Sam to come get him. Well, when he wasn’t otherwise occupied that is. So him looking for me to help him is definitely a step in the right direction. I’m going to try to explain to him a little better tonight about our shifting and see if he wants to try. Maybe if he realizes that he too can be a hell hound, then hopefully he won’t be as frightened of them.
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Day Twenty One:
It has been six days since I showed Dean my beast, five days since he discovered his own. I believe he liked the fact that his was slightly larger than mine and had very menacing flames that engulfed it. I personally had never seen a knight’s beast before, so it was a learning experience for the both of us. Since he realized there were things he didn’t know about demons, he has begun asking more questions. In the last few days we seem to have bonded a bit, which is a really good thing. I felt the pull of a summoning today for the first time since we left. I believe I can resist for a little longer, but eventually I will have to surrender to the pull and see what Sam knows.
For now, I am enjoying having Dean by my side since I’ve returned to the daily grind so to speak. I’m dealing with the normal day to day operations in hell, the only difference from before is that Dean is there to give his input. Usually that input comes in the form of a snarky comment, but we are getting there. He no longer kills my minions or tries to fuck them into oblivion, so it is an improvement. I believe I can trust him to be alone long enough to answer Sam’s summons, but I want to wait a little longer if possible. Just because he is comfortable with me now does not mean he wouldn’t try to go back with him.
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Day Twenty Six:
The pull of the summons was finally too much for me to deny. Luckily, Dean was off with a new friend of his. The fact that he has made friends with a few of the demons that roam around the offices doesn’t bother me. They are all mated to other high ranking demons in the organization, but they have shown Dean some things I never would have thought to show him. Kiana, one of the demons, decided to take him to the kennels.
The kennels are where we keep those demons who have changed to their beast form and cannot change back for one reason or another. He seemed to bond with them and even changed into his beast for the first time in front of someone other than myself. The ones in the kennel immediately respected him, but he also seemed to make some friends while he was there. This is where he was when I finally allowed myself to succumb to the pull.
Sam had figured out that there was a hint of sulphur in the air where Dean had been laying and was convinced that his brother’s body had been taken by a demon. It had of course, but that wasn’t why there was a distinct sulphur smell on Dean’s pillow. That was all Dean. I was able to convince him for now that there wasn’t a rogue demon wearing his brother’s meat suit around. Luckily, that seemed to be all he knew and I was back fairly quickly.
Dean had asked where I had gone and I didn’t lie to him. He was surprised I went and saw his brother, but those ties are starting to wane. He’s replacing them with other familial ties here. He sees the ones in the kennel as younger siblings that he is trying to help. It’s a way for him to release the good parts of himself that just won’t seem to go away.
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Day Seventy Four:
Sam knows. I didn’t think it would be something I could be this calm about. When I felt the pull of another summons I thought maybe he had figured something out. As soon as I arrived he started spouting off about how I had lied about his brother. Apparently, when we were topside for the first time, we were unlucky enough to be spotted by a group of hunters who were in town tracking a vampire nest. The nest of course was already gone because they were causing trouble for my minions in the area, but they didn’t know that.
What they did know was that Sam was looking for his brother who he thought was being ridden by a demon. Dean is the rider not the one being ridden, but Sam doesn’t need to know the details. So they contacted him and it wasn’t long before he called on me again. I asked if he wanted to talk to his brother and again he informed me that he didn’t want to talk to some black eyed bitch. I informed him that I would bring Dean and he could decide for himself. Surprisingly he let me out of the devils trap and I stood true to my word.

I now felt more confident in Dean not wanting to leave hell, so I took him to see Sam. Dean now has a whole pack of followers in hell. Not just the hounds in the kennel, but also many of my minions are loyal to him as well as myself now. I’m not sure demons can have friends, but they do make bonds of loyalty and those bonds go both ways.
Just as I had expected, Sam saw his brother and immediately threw holy water on him. It surprised Sam when Dean walked right through the devils trap. He just kept looking between me and Dean the whole time his brother scraped the paint allowing me to exit as well. When Dean told him that he was happy in hell I think the moose almost had an aneurysm. Dean didn’t hang around long after that, leaving me with a very pissed off Sam when he popped out.
By the time I had explained all that I was going to and returned to hell, Dean was already back at the kennels. I believe he was upset with me, if the cold shoulder was anything to go by. He was in his beast form and refused to return to his regular form. It’s fine, I will wait him out. He needed to have a talk with Sam so the moose wouldn’t keep summoning me.
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Day Ninety Three:
It took a while for him to come back to me. I would never have been comfortable allowing him so much time at the beginning of his stay in hell. Now, I’m glad that I was able to let him have his space. He came back with a better respect for me and how I do things. It’s strange, but those poor hounds in the kennels seem to have a profound effect on him. It’s been two weeks since he came back to me. He hasn’t asked to see Sam again, but he did say he understood why I took him with me.
He’s started spending a lot more time in his beast form, I believe it helps him connect with hell better. He tells me that his pack needs him, and that’s fine by me. He always includes me in his pack and as long as that is the case I’m fine with it. I look at the message log on my phone and the long list of unanswered messages from Sam. I decide it’s a good idea to finally respond to those, even if the content of my message has nothing to do with the messages he sent me. This will be the only message I send so it has to mean something. We are moving on with our life so he needs to move on with his.
He has a new pack now, Sam. Move on.
