Summary: Castiel never showed up that day to pull Dean from hell. Dean was left there, losing a little peace of him everyday. Sam was left alone, following Ruby toward is true destiny, killing a few head demons along the way, Alistair being one. This is a DARK what if story. Not real romance, Dean and Sam are OOC. You are warned. This contains dark themes, sexual content, and other.

Warning! Dark Dean, Sexual Content. Don't like then move along : ) Thanks.

**Prologue**

It was once said that the longer you are in hell the more your humanity slips away. That is what happened to Dean Winchester. After he said yes to Alistair he started ripping people apart to try and get rid of his own pain. Soon that pain was gone. He felt nothing any more. No pain, no sorrow, no feeling what so ever and that worst part of it was…he liked it. He liked it a lot. He liked the power. There was a new torture master in hell and his name was Dean…THE Dean.

My name is Jennifer Jackson and I have been here in hell for fifty years now, twenty years less that Dean who was on his seventieth. I came here after I made a deal to have my parent killed. Believe me when I say it's not what you think. They weren't perfect and did some bad things to me. Sure that's not a reason to kill them but I was young. I was only fourteen years old. Ten years after the hell hounds killed me and dragged me here. That is when Dean first saw me. When those evil eyes connected with mine I knew it was over. I was his forever and there was nothing I could do. But just like Dean I lost all feeling after so long. I was his slave and you know what…..I kind of liked it.

I knelt there on the cold floor waiting in the mess of my own arousal. I knew what was coming. The hot wetness all over my legs still flowed slowly from between my thighs. I whimpered pitifully, waiting for the next assault to my battered body. Out of the darkness he touched me, tugging hard at my nipples that were bruised and sore. Only one person had a touch like his. I yelped and the heat of his palm across me face sent stars before my eyes and fireworks exploded across my pussy. Punish meI thought. Every atom of my being buzzed with want for the pain he could inflict upon me. What was wrong with me? This was not normal. I was changing inside and out. I felt it everyday.

"You are not to speak, to moan, to groan or scream." he growled at me, his voice almost a whisper it was so low. I tried so hard to obey him, God I tried hard to be the good little slave to be used as he sought fit. Some days were harder than others. His request were sometimes difficult for me but I tried.

I nodded quickly as he pressed his hard cock roughly against my mouth, I opened for him willingly. My lips curled back like the petals of a flower on a spring day. The head of him prodded the back of my throat thrust after thrust and I tried to swallow him, desperately tried to fit all of him down my throat but he was so large.

His hands, those big strong hands clutched at my hair tight, fingers intertwined there in ever curly lock as he pulled my face to meet his thrusts. "Take it baby." He said. It was a order and I tried not to moan as rivers of my excitement poured from me. Sucking him had become a turn on to me. I don't why but it was. The taste of him was like a drug to me. Pain always made me so excited but we all like it a little rough from time to time. This pain was better than the pain others were feeling, the pain of losing someone or just being ripped apart. I would take sexual pain any day.

I could here him breathing steady and even but my breath was coming in short quick gasps, not from lack of air because deep throating. The sheer power of him I could almost feel him deep in my pussy. 'Take me please!' my mind screamed over and over again. My clit throbbed and my pussy pulsed I couldn't help. I had to touch myself. As soon as my finger tips brushed across me clit my orgasm slowly ripping through me, a scream was forming in my chest and rising up to my throat and on one of his thrusts as deep moan erupted from me as wave after wave of orgasm pushed through me. My extreme pleasure squirted down my thighs and my juices washed across my knees on the hard cold concrete floor. I knew Dean had heard me and he knew what I had done. It was a rule. I was never to cum unless he touched me and told me too but I couldn't help it. The thing he made me feel were sinful….almost evil.

"Jennie, Jennie, Jennie. You Bitch!" He said pulling himself from my mouth, depriving me of the taste of him.

I groaned and leaned toward him desperately trying to wedge him back in my mouth but the only thing that filled my mouth then was the metallic taste of my blood as he slapped me so hard that I fell backwards onto the floor. Another moan escaped me as I lay there quivering. A light came on above me and I could see in his hand the belt that often left such delicious welts across my body in places that another man would never see. He wanted them to see it. It was his mark and his only, warning other to stay away from me or else.

"Get up!" His commands were like words from the Gods or I should say the Devil. I knew I had to do what he asked and do it fast. I stood up and was face to face with Dean, the gorgeous evil man. "Turn around and lean on the bed" he smiled at me.

I did what I was told and my breathing quickened with fear….excitement.

"Why must you constantly disobey me?" He asked just before I felt the belt strike me hard. "Maybe because you like it rough." He said and hit me again. It was the truth. Maybe I liked keeping him happy and fear is what he loved. He loved control. As long as I was the only one we could both be happy.

"Do you like it?" he asked. I could see the grin across his lips without having to see him. I knew him so well, my perfect, handsome, sexy Master. "Well?" he expected and answer this time from me.

"Yes." I whispered as a small shudder moved through me. "Oh yes."

My legs felt so weak and I almost could not stand. My mind reeled and I could see him in my head. My pussy throbbed again and I felt myself losing control and then the blows stopped. His lips were dangerously close to my ears his breathing was heavy and ragged, his voice was the deep growl. "Spread your legs." He growled calmly.

I did and I felt him press against me, his chest to my back, his cock teasing my wet center. I was his property, his slave to use as he saw fit. He caressed his way to my collar bone and closed his hand on my throat squeezing. "So beautiful….so mine." He said as he thrust hard into me. I screamed out loud that I was sure people on earth could hear me. He pounded and pounded away at me. "Say it." He growled.

I knew what he wanted and I was happy to give it to him, "Yours! I'm yours! Take me!"

"Yes." He said as he pulled he against him, never slowing down, "I know you like it."

"Yes…Dean!"

"Say it again." He said and gave my ass a hard slap.

"Dean!" I screamed.

"I want you to cum now, harder than before. Soak me." He commanded.

As always I did what I was told. My body convulsed and cum flowed from me down my legs and pooled at my feet. I felt him cum inside me and it made my orgasm stronger. He loosened his grip on my neck and I moaned over and over again, each time it became louder and louder.

Once we were done I collapsed, shuddering as the strength of my orgasms weakened. He let me go and I slumped to the floor in the cold wetness of my own excitement. He stepped away from me and got dressed. I could hear his foot steps fading toward the door. I whimpered as he unlocked the door. Just as he was closing it he said, "This room better be clean by the time I come back down here."

"Yes, Dean. Anything you want." I whispered trying to bring myself to my knees. Who knew when he'd come back down here. There was nothing or no one down here but me. I was his own personal slave, punished for his pleasure, a human rag to clean the mess off of his cold concrete floor. This was my hell…. or was it my heaven? I was lost. I could feel everything good inside me slowly slipping away. Maybe that's what he wanted. I was never really sure. I was here to serve him. There was no changing that. At least not now and even if I could I can't say I would. I was fucked up inside. But that's the point of hell isn't it? To take everything away from you?

I thought of many things as I sat here alone, wrapped up in nothing but a dirty sheet. My cave, my room. No one knew where Dean slept or even if he did. Where ever it was it had to be better than this. One day maybe I will be taking up to the main part. Then I would be with him. As for now I was a pet, a toy and that was it. I can live with that for now. As long as I got more of him. I wasn't afraid of him. I was afraid of being alone.

Sometimes I would wonder when I looked into his eyes and saw a hint of a human and it made me wonder, who was he and how did he get here? What did he do that was so bad? I had many questions. Maybe one day I would have answers. One day things were going to be different, I could feel it. I just wished I knew how right I was.

*So this will be the only chapter with Jennifer's POV unless you like it like that. This was an intro. Coming up will be more or Jennifer and Dean and the master salve relationship. Sam will come into the picture and you will find out what is going on up on earth. So stay tuned for that. Ok Review time. This was sooo different for me and like I said don't look for candle light dinners and lots of romance in this one. At least not the good kind. SO PLEASE REVIEW AND YOU WILL HAVE MORE : )