I watched him sleep. "How did I get here?" I asked myself. "What happened to the badass demon I used to be?" As I looked down at him, his long hair falling over his forehead with the moon light shining over his prone form, I cant help but be amazed at the man before me.

This broken man had provoked so many forgotten feelings from my past as a human. I never thought it was possible for the feelings of remorse, empathy, pity.. who knows maybe even love, to come back to me. The Boy King, the chosen leader of the demon army, had captured me.

My intentions when I first came to the youngest Winchester were anything but honorable. Using Sam to kill Lilith had been the plan. Use him at all costs, maybe leave him in shambles, I never cared what was the outcome as long as I achieved the goal that I have been striving for. At least that's what I told myself. The only problem was that all of the time spent with Sam on this journey to rid the world of Lilith, the little bit of human that was still inside of me had been re-awakened.

Before the death of Dean, my interaction with Sam had all been a game, he was easily manipulated and being a demon dishonesty was my second nature. I knew all of the right things to say. " I can help you save your brother" I had claimed. That was enough for him, that one simple promise had him going against everything he had ever been taught. We were demon and hunter working together for a common cause, he just didn't know what it was yet. He laid himself open to me in hopes of saving his brother from going to hell. And when that failed, when Dean was sent to the pit, all innocence that was left in Sam was gone.

I am the epitome of a true conwoman, I was able to claw my way out of hell with a promise to Lilith that I would get rid of Sam myself. But strangely my thoughts as I was being tortured in the pit in worst ways possible day after day were only of Sam. This was the first warning sign that I should have noticed. A connection to the human world was not part of the plan, especially when the connection was to a Winchester boy. When I returned I was shocked by the vision of the once strong, beautiful man that stood before me.

The light in his eyes was gone. He was offering up himself for death. The Sam I knew, the one I had fought to get back to was no longer inhabiting this body. All that was left was a soul broken by the constant loss in his life. He had lost everything and everyone and all that remained was the shell of a once innocent, caring, intelligent, and great man. No longer was there the optimism there once was, all hope of one day becoming normal had gone to hell the moment Dean made his deal.

Suddenly I didn't know what I had been fighting for, I was confused by this pathetic version of Sam. I had felt loss before, but I had forgotten the affects that grief had on a human soul. Especially on those as close as Sam and Dean had been. It was easy to see what grief had done to Dean, hence his road-trip to hell on the backs of Lucifer's hellhounds.

Sam was different, he was drowning. As we drove down the highway after I killed my partner that Lilith had chosen for me I had a real chance to take in Sam's appearance. This version of Sam had swayed under the influence of alcohol, the stench of it on his breath. The dark shadows under his eyes were evidence of constant unsleeping nights and it seemed that the pit of grief that had begun in his soul was beginning to show on the outside of this weak shell.

"Whose body are you riding?" he asked me. This was the first sign that someone still resided in the seemingly void body. He had never cared before, he never asked whose body I was in before but in his inebriated state he had somehow asked this question of me and I was oddly grateful for it. It had never mattered before, but the look in his eyes, his shattered stare delivered the another blow to the shield that remained around my soul that lay forgotten.

"How is it that I have remained so strong against the hundreds of years of torture in Hell, but I cant withstand one look from Sam Winchester?" I berated myself as I searched for my new host. "Why do I care enough to try to comfort his unease about whose body I claim as my own? I've never cared before." I was quick to brush off these questions, to continue to think about them would force me to admit that I was beginning to care about Sam as more than just a means to an end with Lilith and that was just not possible. I'm a demon for hell's sake.

When I showed up at the run down shack that Sam had made his temporary home, I couldn't help but think about how self-destructive his behavior was. He could never defeat Lilith in the state he was in. He would definitely need some shaping up if he was to ever going to put up a good fight against Lilith or the countless other demons that were to come his way.

When he opened the door, I lost my breath. He looked slightly more rested but the red circles under his eyes were the tell-all of his extracurricular activities. My theory was supported by the large amount of liquor bottles that sat on his makeshift table in the center of the room.

He was vulnerable and this gave me the perfect opportunity to once again propose the idea of using his Psychic powers. His past track record had shown nothing but resistance, but his decision never seemed to be of his own volition. Sam's reason for resisting his so-called destiny was no longer here. Dean had given up his right to influence Sam's decisions when he sold his soul to the crossroads demon the year previous. Sam's newly found passion for revenge only fueled his susceptibility to my plan to exercise his powers.

If Sam cared about what Dean would have thought if he saw him now he definitely didn't show it. He was eager to kill Lilith by whatever means necessary. I saw the first spark of the old Sam that day. But I needed the majority of that old spirit in him to come back, learning to use his powers would be no easy feat and he would need that strength that held constantly held him together his whole life. Patience and sobriety is what I made him promise. At this point I wasn't sure he could accomplish this small task. The bottle had been his faithful companion since the day he buried Dean and I wasn't sure that I could get him to part with it. But the idea of defeating Lilith had revived his determination and soon enough Sam regained his legs on dry land.

He was an awful student. Now that he was sober I think the truth about what he was doing was starting to sink in. His heart was completely into killing Lilith but I could see the affect his brothers words, that had prevented him from using his powers in the past, were still having on him. He was losing focus and he needed to concentrate or he would never learn.

I felt hesitation of my own, when I saw that pain that exorcising these demons was causing Sam. The headaches that would remain for days after a particularly difficult pull. I felt the urge to comfort him but Sam never allowed it. I could see in his eyes that he believed he didn't deserve it. He blamed himself for the death of his brother and no one could make him believe that is wasn't his fault. Dean's own accountability was completely lost on Sam.

In his mind the evidence stacked against him. His mother, Jessica, his father, and now Dean were all people whom he had lost. They now plagued his dreams every night asking him why, not that he'd ever tell you that. How many things could one observe in another person's eyes? Well I was finding out, Sam's eyes were truly the window to his soul, well what was left of it. And now that we had come together in a way he had never thought he could let himself, I was often able to observe him in his most innocent form.

When he was sleeping, while he was drifting in and out of dreamland I could see the deep lines of stress building on his face. I could now tell when the nightmares were beginning to take hold. After coming back to him I have been able to hear him night after night crying in and out of sleep. Not that he slept much nowadays.

I remember the night everything changed. This night I was drowning in my boredom and I had dared to sneak up to the mold infested room that Sam had claimed as his refuge. I was expecting to see him laying on the bed as he did most nights. He usually laid there wide awake staring out of the one window that let the moonlight cascade throughout the room. But tonight I rounded the doorway only to witness him sitting on the side of the threadbare bed, letting gut-wrenching sobs wrack his body. I felt another crack form in my stoney interior. How could this man evoke such feelings within me?

"Sam" I said quietly "what's wrong?"

His head whipped around, and he quickly wiped his eyes on his sleeve, a look of shame flashed crossed his face. "Nothing's wrong." he lied. "Just leave me alone Ruby…" he begged a small hiccup escaping him.

In the past I would have let him work it all out on his own because before I didn't care. But not this time. The full weight of the feelings that I held in my heart(?) for him hit me with excessive force. I felt myself change in that moment. I wanted to comfort Sam. I wanted to hold him and make his pain go away. How strange, that the demon could fall for the human, especially when that demon is me.

I quickly crossed the room and knelt between his legs, recreating an action that I had performed not so long ago. Only this time the feelings were completely different. He had almost gotten himself killed today going after Lilith alone. I was grateful that I was able to save him, but he had to face the fact that he wasn't going to be able to find release through suicide, or by throwing himself into these kamikaze attacks. Not as long as I was around.

I took his tear trodden face between my hands, and brushed his tears away with my thumbs. I watched him flinch, which was inevitably followed by him trying to pull away. "Typical" I thought and I fought to keep my eyes from rolling. I gripped his face, holding on with all I had in me. When I looked directly into his eyes, he looked away just like I knew he would.

"Look at me" I commanded

He obeyed. "What do you want from me?" he whispered letting his gaze fall back to the floor.

I simply shook my head. I truly didn't want anything. Well I didn't want anything that had to do with me. Who knew that could happen? I dropped my hands from his face to his shoulders and continued to slide closer until my arms were wrapped around his neck. I felt his back stiffen and quickly my body was flooded with the fear of his rejection. But ever so slowly I felt his arms wrap around my back and his head drop to my shoulder. My stomach churned with the pride I felt over my small accomplishment, and soon it was hard to breathe with his large arms constricting around me. I felt as if in this moment I had become his lifeline.

We remained there for several minutes, just breathing together finding solace in each others arms. This was an amazing feeling that I had never felt before. This was even better than French fries and that is saying a lot. But I didn't want to push my luck with this small step forward. I started to pull back and he let me. With him in this fragile state I didn't want him to feel rejected so I assured him of his action by simply resting my forehead against his closing my eyes once again allowing us to fall again into a simple rhythm of breathing.

I slowly stood and once again placed my small hands on either sides of his face and bent slightly and pressed an innocent kiss to the center of his forehead. I heard his sharp inhale of breath, so I quickly pulled back and turned to leave the room. I had crossed too many of his invisible lines lately and I didn't want him to retreat.

But as quickly as I had turned I felt a large hand wrap around my wrist. I met his eyes in surprise they were begging for something that I was unsure of.

Soon my question was answered when a barely intelligible request came from his mouth that he directed at the floor "Please stay" he asked me.

Once again he raised his eyes, hazel and brimming with tears. There was no question in my mind of what I was going to do in that moment. I slowly pushed his shoulders indicating that I wanted him to lay back on the bed. I slipped off the shoes that he had forgotten to remove earlier and then my own, then I rounded the bed and slipped in next to him. I instantly felt the springs of the ancient bed digging into my back, but I didn't care, this night wasn't about me. It was about him.

He was facing away from me his broad shoulders still heaving in distress. I hesitantly rubbed my hand over his back, this action feeling dangerously close to something a human mother would do to comfort her ailing child. But it must have been the right thing to do because Sam's distress seemed to be lessening. And as if the night wasn't full of enough surprises I was again startled by Sam's actions as he quickly rolled over to face me. For the second time that night my breath caught in my throat as Sam's eyes came to rest on my face. It seemed as though his shield had dropped if only for a moment. I was able to see every ounce of grief, anger, shame, and loss that he was experiencing. I wanted to take that away but the one way I knew how was not an option at this moment, plus I was learning that this kind of relief was only temporary. He needed true healing if he was ever going to win this war against Lilith and also against him own demons. Me included.

Feelings of compassion were foreign to me and I wasn't sure what to do, so I imitated my earlier actions and pulled him to me, this seemed to have brought comfort before. I was relieved when without any protest he gently laid his head down on my chest where I had directed him. I was afraid to move in fear of breaking the trance he seemed to be in, but my hands needed to do something. I was not used to being idle. I followed the first idea that came to mind and I placed my hand on top of his head. I started to stroke his hair, this must have soothed him because the next sound I heard break through the silence was Sam's shuddering sigh. His arms tightened around me and soon he was asleep.

What is this feeling I was experiencing? Contentment, happiness? I didn't deserve anything like that. Without words, more and more everyday Sam was showing me that I didn't have to surrender my soul anymore. I could hold it within me. He was bringing my human side to life. This wasn't good. I was getting sidetracked. I was losing sight of my goal, but with Sam laying here in my arms I was finding it hard to care. He was bringing my lost soul to life and I had a feeling I was beginning to return the favor as he sighed my name in his sleep. What was a demon to do?