This story contains spoilers for Malleus Maleficarum. So if you haven't seen the eppie and don't want to be spoiled you have been warned.

A/N: The wonderful Winchesters and anyone else you recognize belong to the amazing Eric Kripke and the CW.


Dean was still trying to figure out if he believed everything Ruby had just told him when curiosity got the better of him. If what Ruby said was true about demons having once been human, then what did she do to end up in hell in the first place? "So what did you do?"

"What do you mean?"

"Well how'd you end up down south when you died instead of up north?"

"You mean why did I end up in hell instead of heaven?"

Dean gave small nod.

"I killed my husband and then I committed suicide."

"You what?" Dean wasn't sure if he heard her correctly.

"I killed my husband. I slit his throat from ear to ear and then I hung myself with the bloody bed linen."

"Why?" Dean couldn't help, but ask.

"Would you believe me if I told you he had it coming?"

"I don't know, slitting a man's throat is kind of harsh."

"Yeah, well the Middle Ages were kind of harsh." Ruby gave a sad laugh.

"Seriously, what happened?" If Ruby was going to be involved in Sam's life after he was gone, which looked likely, he wanted to know as much about her as he could.

For a moment it looked like Ruby wasn't going to say anything and Dean thought she might just leave then she spoke. " My father died when I was fourteen leaving my mother with five children. I had four younger brothers. The oldest was eight. My father had been the village blacksmith and had made enough money so that we never went hungry, but after he died my mother couldn't seem to make ends meet. There wasn't much work for women back then and my brothers were too little to work."

"So what did your family do?"

"My mother took in laundry from some of our neighbors, but it was nowhere near enough to feed the six of us. There was a wealthy man who lived in my village named Colin Brimstone. He was the talk of the village being unmarried at thirty-five with all that money. One day he showed up at my house with a proposition for my mother."

"He wanted to marry your mother, didn't he?"

"A widow with five kids? No, he wanted to marry me. He told my mother he would give her twenty-five pieces coins of gold for my hand in marriage. With my father dead and the oldest of my brothers only eight, it fell to my mother to decide if I was allowed to marry. She said yes."

"Wait your mother let this man have you for some gold? You were only fourteen." What was her mother thinking?

"Yeah and she was a woman trying to feed five kids. With me gone it would only be four and that gold could really help them. I don't blame her for doing what she had to."

"Still that guy was old enough to be your father," countered Dean.

"I told you the Middle Ages were harsh."

"So was life better once you married the rich guy?" Dean was guessing it wasn't otherwise why would she have killed the man.

"No. My husband was a cruel man who took what he wanted by any means necessary. I was miserable there and had the scars to prove it."

"He abused you?"

"Yes. He said he needed to break me in. I had never so much as kissed a boy before I got married. Every night I was forced to do things that made me sick. There was no love in it. I hated myself."

"Why didn't you leave?"

"I had no where to go. Besides Colin would have tracked me down and punished me for it."

"So you stayed."

"Yep and then something wonderful happened."

"What?"

"I got pregnant when I was sixteen. Colin was thrilled. He was so sure it was going to be a boy. For the first time since we got married he didn't lay a hand on me. He had the servants wait on me hand and foot. In fact I was hardly allowed out of bed. I was scared at the thought of being a mother, but as the baby grew in my belly I came to see it as blessing. Finally I had someone to love and someone who would love me."

Dean was having a heard time picturing a Ruby as a mother. She was a demon after all. However he reminded himself that she was once human.

"However after three months straight of lying down I grew restless and one day while my husband was conducting a business deal I went for a walk in the upstairs of the house. The servants were all downstairs. No one would ever have to know, but of course that would be the day I went into labor. My scream of pain brought the maids running and they quickly escorted me back to bed. After what seemed like an eternity I finally gave birth to a little girl. I saw a quick glimpse, but there was no noise. When my brothers were born they made so much noise screaming and crying, but my baby was silent." Ruby paused for a moment.

Was she …." Dean couldn't bring himself to finish the question.

"Dead? Yes. She was stillborn. Colin was furious. One of the servants had told him I went for a walk and he said that was the reason the baby died. They wouldn't even let me hold her. I wanted to hold her just once. The doctor gave me something and the next time I awoke three days had passed."

"Did you miss the funeral?"

"They didn't hold funerals back then for unbaptized babies. She was buried somewhere on the estate. Colin refused to tell me where no matter how much I begged. After that things grew even colder between us. Blaming me for the baby's death Colin was even crueler than before. I overheard one of the servants say I was lucky that it was a girl and not a boy because the master would have killed me if it was boy. Boys being preferred over girls back then."

"I wasn't your fault. There's no way taking a walk killed your baby."

"Again Dean, it was the Middle Ages. People believed things like that. Two years later I got pregnant again. This time I was not allowed out of bed from the moment I told my husband. I spent nine months just laying there, but I didn't care. I'd do anything to keep my baby healthy."

"Did it work? Was your baby born healthy?"

"No. I had another girl and she had been born sickly. She was so tiny. This time at least I got to hold her. She lived one day. Again my husband blamed me. Not only had I lost two babies, but they were both girls."

Ruby paused once again seeming lost in her thoughts and Dean gently prodded her to continue wanting to know the rest of the story.

"There was a local woman who believed that she could read the secrets of the stars and for a small fee she would predict your future. She was full of it, but desperate people will believe anything. Colin went to see her to find out if he would ever have a son. She told him that he would, but it would not be by me. She said my problem is that I was not properly trained. If he gotten a hold me when I was younger and trained me properly things would have been different. She knew of a girl in the next village whose parents couldn't afford to take of her. The girl was eleven almost most twelve. Just the right age to train her into the perfect wife."

"That's sick. I don't care it if was the Middle Ages or not. That's just sick."

"I know. I was disgusted too, but I was also afraid. I knew if my husband bought this girl from her parents and brought her into our home I was as good as dead. I also knew what would be in store for this girl."

"So that's why you killed him?"

"Yes. One evening after Colin had taken his nightly pleasure, I waited for him to fall asleep. Once he did I grabbed a knife that I swiped from the kitchen and had hidden under the bed. While he slept peacefully, I slit his throat from ear to ear. I found a strength I didn't even know I had."

"Why did you kill yourself?" asked Dean. "You were finally free."

"No one would have believed me when I said I didn't know what happened to Colin. I would have ended up at the gallows pole anyways so I decided to get it over with. I hung myself from the rafters on the ceiling."

"And that's when you were sent to hell."

"Apparently heaven has standards. They didn't want a murderer who committed suicide."

"Were you scared?"

"I was terrified, but what hurt the worst was the thought of my babies in that place."

"Your babies went to hell?" Dean had a hard time picturing innocent babies being sent to hell.

"Back then the church taught you that children who died before they were baptized didn't go to heaven. They went to limbo, a place that is just outside of hell. I searched everywhere for them for years, but I could never find them. I never found any babies. Eventually I realized came to the conclusion that the church was wrong and that my daughters were in heaven."

Dean was trying to wrap his mind around everything Ruby just told him. Maybe she was lying, but somehow he didn't think she was. Her babies and the love she still had for them was what kept a part of her humanity in her when she became a demon he thought. "Do you regret it?"

"Do I regret giving up the chance to spend eternity in heaven with my babies?"

Dean wouldn't have put it that way exactly, but he nodded anyways.

"I don't believe in regretting things you've done. It doesn't change anything so what's the point?"

Where as Dean could tell she was being truthful before now he could tell she was lying. It was written on her face. When Ruby killed her husband she didn't care that she was going to be excluded from the paradise that was heaven because her daughters weren't there. To find out she was wrong must have devastated her as much as losing them the first time did.

A strange feeling came over Dean. He never thought he could feel sympathy for a demon. A demon who was once a girl. A girl who was forced to grow up way before she should have had to. However that didn't change a thing because she was still a demon. A demon who was interested in his brother.

"You know I didn't tell you all of that so you would feel sorry for me," said Ruby as if she could read Dean's thoughts

"Who says I feel sorry for you," replied Dean.

Ruby gave a sad smile, but didn't say anything.

"So if humans evolve into demons does that mean Colin's a demon?" There's no way that bastard went to heaven thought Dean.

"He was a demon, but I had to test my demon killing knife on someone."

The End

A/N: Thank you for reading. Reviews are always greatly appreciated. Please let me know what you think.