Warnings: un-beated, so beware the bad grammar and incorrect spelling. Also, some swearing and implied torture.

"The First Seal shall be broken when a righteous man sheds blood in Hell. As he breaks, so shall It break."

- Supernatural; Season 4, Episode 16: On the Head of a Pin.

Everybody breaks. No matter how honest, how just, how pure they are; in hell there are no exceptions. That's just facts.

Granted, hell wasn't really the place for honest, just and pure people, but every now and then some poor good soul would end up down there along with the greedy, malevolent, and selfish rabble that Hell is usually host to. And no one, even those do-gooders who somehow end up in the pit, last long under the indescribable agony and torture subjected to them. They, like all those before them, eventually find themselves broken and twisted, so far removed from the person they once were that they stop being human and become demons – fellow creatures of death and destruction, revelling in blood, pain and tears - as long as it wasn't their own of course.

Some broke mere minutes after descending to hell, a few rare ones took decades, but they all broke in the end. Humans were greedy, self-obsessed and fragile creatures after all. It was only human nature to look out for ones best interest, even at the cost of someone else's. Survival of the fittest and all that jazz. And Hell wasn't really the place to promote all that brotherhood of man and love thy neighbour crap anyway.

As time went on Hell became worse and worse; more souls would arrive, eventually becoming more demons that would conflict, torture and fight for supremacy with each other in the pit. Even Earth was a haven comparatively and those lucky few who managed to claw their way out to the surface were eager to avoid being sent back 'home' at all costs.

Lilith was one of the few that didn't mind hell. As the first demon, she was the most powerful and so the problems lesser demons had with being tortured and tormented by stronger demons weren't issues for her. She was also able to go to Earth pretty much whenever she felt like, though she preferred to send faithful followers – primarily Azazel – instead, and stay to watch over her father's domain. And speaking of father, she was the only one who had truly met Lucifer since God had him sealed away soon after her rebirth as the first demon.

Ever since his imprisonment, Lilith had been trying to rescue Lucifer. It shouldn't have been too hard; though 600 seals kept the exiled angel trapped, only 66 had to be broken to free her father. But while she could pick and choose 64 of the seals to break, the First Seal and the Sixty-sixth were set in stone; the first needed a righteous man to spill blood in hell, and the last required her to die at the gate of Lucifer's prison. She was more than willing to die for her father, and she wasn't the least bit doubtful that the other 64 seals couldn't be broken within one Earth year; but the first seal, that one was proving to be a pain.

You would think that the first seal would be easy to break. True, Hell wasn't really the place for righteous souls, but it wasn't an impossible requirement. As they say, the road to hell is paved by good intentions, so it should have been only a matter of time before a righteous man found himself down in the pit. And many times over the past endless centuries since Lucifer's imprisonment Lilith had thought that the time had finally come for the first seal to break. But, she had eventually learned that good souls weren't necessarily righteous souls.

1. Performing the duties expected or required of one; characterized by doing one's duty.
2. Required by duty; proceeding from or expressive of a sense of duty.

The first time Lilith had thought the apocalypse was at hand was thousands of years ago; even by Earth years. The man was a soldier; loyal, strong and fierce. He may as well been an angel born human. He hadn't been an important figure, born as the third son of a farmer, and he didn't believe in the One God; the idea of a single God not even introduced to his country at that point in history. But for all the people he killed in battles, he never got lost in bloodlust nor was he needlessly cruel to his enemies like other soldiers. He fought because he was loyal to his country and fellow countrymen and showed mercy and compassion to friend and foe alike.

Such a man seemed ideal to break the first seal; Lucifer had been banished due to his doubt and perceived unfaithfulness, so someone like this soldier who lived, killed and died for the sake of duty and loyalty would be perfect. Unfortunately it hadn't worked; the man had broken, had eventually tortured others like he himself had been tortured, but the first seal had remained intact.

Free from or not deserving blame; guiltless.

Hell played host to a few more "good" souls over the years, but the next time Lilith had been sure the seal would break involved a child so young that it could have been born mere days or hours before arriving in the pit. Infants were usually too pure and guiltless to get sent to the pit should they die, but this child's soul had been sacrificed by its mother in exchange for power and good fortune, and the deal had gone through despite the child's innocence.

But while the infant's innocence and purity should have made it able to break the first seal, it also worked against them. Though the boy had grown quickly in hell compared to how he would have in the slower Earthly timeline, all he had ever known was Hell and pain. The boy hadn't even understood that tortutring others was supposed to be wrong and hadn't had any qualms hurting others as long as he himself wasn't hurt.

The child grew up to be Hell's best torturer, Alastair.

1. Honourable in principles, intentions, and actions; upright and fair. Showing uprightness and fairness.
2. Sincere; frank.
3. Genuine, or unadulterated.
4. Respectable; having a good reputation.
5. Truthful or creditable.
6. Chaste; virtuous.

Centuries passed and more souls broke and became demons, yet the First Seal remained intact. Some had more potential than others, but they all failed. Including one seventh century man.

Lilith hadn't held out much hope for the guy anyway, but he had been the best candidate for a while. He was a young man, worked hard at his apprenticeship, went to church every week and obeyed the 10 commandments religiously. He was a good, honest man.

But that honesty put him into trouble one day; he witnessed another man stealing food and reported him to the authorities who had the thief hanged. The hanged man's wife and children starved to death, much to the grief of his mother-in-law. Consumed by grief and a need for vengeance, the mother-in-law became a witch and lost herself in black magic, determined to send the good man to the depths of Hell even if she had to drag him there herself. She succeeded.

He may not have been the one to break the seal, but at least Lilith got the pleasure of seeing another 'good' person become a demon.

Deserving praise, reward, esteem, etc.; praiseworthy. Respectable and worthy of esteem.

Lilith figured Jesus was right; it must be hard to get into heaven if you were a rich man. She had seen her fair share of emperors, nobles, kings and queens. Those born into privileges usually lacked a certain empathy or concern for others. But there was one noble who had been a good man.

Before the word philanthropist was even a word, the man had been one. He was loved and respected by his peers and subjects, willing and eager to share his wealth and good fortune with others. Unfortunately for him, his beloved little sister contracted the Bubonic plague and was dying rapidly. Desperate to save her, he searched high and low for a cure. Finally he came across a small coven of witches who convinced him that through the power of their Dark Master, the girl could be saved. He believed them and became a fellow witch soon after.

Though his power was demonic in origin, he used it to help people and still lived respectively and honourably until his dying day. But despite his good soul, he had sold his soul to a demon and when in hell wasn't deemed righteous enough to break the seal.

- adjective
1. Conforming to moral and ethical principles; morally excellent; upright.
2. Chaste.

It was always a pleasure to host a man of the cloth. It was practically as good as spitting in God's face as far as Lilith was concerned. Her dedication and loyalty to Lucifer increased each time one of the men who had dedicated their mortal lives to God's teachings strayed and ended up in Hell.

The priest most memorable to her had arrived in the fifteenth century based on Earth years. He hadn't stolen from the collection plates, nor had misused his influence or power as a symbol of the Lord. His crime had been burning innocent women.

He had thought he had been doing God's work; the Bible did say "Thou shall not suffer a witch to live". Unfortunately, the priest hadn't really been stopping real evil and instead condemned dozens of innocent women. His expression when he had arrived in Hell and realized his sins had been priceless.

Like all others he broke, and as always the First Seal remained intact. Lilith was getting very impatient.

1. In accordance with or characterized by principles of honour; upright.
2. Of high rank, dignity, or distinction; noble, illustrious, or distinguished.
3. Worthy of honour and high respect; estimable; creditable.

One of the last type of person you'd usually classify as honourable would be a politician. But that was the case for one soul Lilith had been hoping to break the first seal with.

The man had come from a small, war-ridden and poor country; somewhere where, had it been wiped off the map by an act of God few people would have noticed or cared. Overrun with crime and misery, it would take nothing short of a miracle to get the pathetic economy on track. But one politician hadn't been willing to wait for one. He had loved his country and was willing to sell his soul to a crossroad demon to ensure that he'd get a chance to make it better.

In the ten years the man had to work with, the country did a 180 and became a virtual paradise compared to how it was before. It was quite inspiring really. Unfortunately, soon after arriving in hell all the man's hard work had ended up in shambles due to mismanagement causing a civil war. That information had been used to help break the man.

Too bad the seal hadn't broken too.

1. Guided by truth, reason, justice, and fairness.
2. Done or made according to principle; equitable; proper.
3. Based on right; rightful; lawful.
4. In keeping with truth or fact; true; correct; actual, real or genuine.
5. Given or awarded rightly; deserved, as a sentence, punishment, or reward.

It always amused Lilith how much evil in the world was blamed on demons and Lucifer, when the grand majority was all humans being humans. Like slavery for example – no one forced those 'masters' to treat others like possessions, whipping posts or free labour. They did it because they were just regular, selfish humans.

And though Lilith could care less about the suffering of the slaves as a whole, the soul of one slave had caught her interest. He was a good man, loyal, brave and fair. Maybe the one to finally break the seal. He had been born into slavery, and after years of watching women get beaten and raped, men being worked and whipped to the bone, he decided to do something about it. He helped stage a massive escape, freeing dozens of people from an inhumane life. But, he had killed his master and others in cold blood, even though it was no less than they deserved and was necessary to make sure everyone else got away, condemning himself to hell despite how justified the murders were.

The man held out longer than most, used to torture and torment, but when he did finally break it didn't start the Apocalypse either.

1. Free of deceit, hypocrisy, or falseness.
2. Genuine; real.
3. Pure; unmixed; unadulterated.

Then came the good doctor. Despite dying in his late seventies, the man had kept an ageless baby-face and a sort of innocence that made hearts melt his whole life. He was the picture of concerned empathy and cared deeply for the wellbeing of others, which was why he had become a doctor in the first place. Even while serving as a medic in the greatest war the world had ever seen, the man had kept his morals intact and aided all those in need he came across, ally or enemy. It was only after the war had officially ended that he committed his first murder.

His mother and sister had been at home in their small town outside of Nagasaki when the atom bomb had hit the city. They did not die in the initial blast but had suffered for years afterwards due to radiation poisoning. Unable to stand their anguish, the doctor euthanized them for their own good – without asking permission first. That was just the start of his secret mercy killings which he continued doing throughout the rest of his career whenever the man believed it was in the best interest of the patient.

The seal didn't break with him either.

1. Having adequate or great merit, character, or value.
2. Of commendable excellence or merit; deserving: a book worthy of praise.

Lilith had truly thought that John Winchester would be the one. The man was admirable, sacrificing himself for his son. He was just and honourable, fighting for a worthy cause all his life, saving lives and protecting innocence. Sharp as a tack and slyer than a fox, the man knew all about 'The Master Plan' by the time he died, when only a handful of high level demons had known about it. He had conquered hundreds of evils in his lifetime, helped hundreds more people, and raised two sons into fine upstanding hunters throughout. Few people had had such a positive influence on so many lives or the world as a whole as John Winchester.

Add the fact that Azazel had been positive that Lucifer's vessel had been born in 1983, meaning that the Apocalypse was meant to start soon, made John's arrival in Hell seem preordained. That John's son was the primary suspect as vessel only added to the delicious irony for why he should be the one to get the ball rolling. It was only fitting that a man who had spent half of his life relentlessly pursuing and banishing evil, raising his two sons and legacies to do the same, would be the one worthy enough to break the first seal holding back Lucifer. All the demons of hell had been practically salivating at his arrival; not only for revenge against the one who had sent many of them back to the pit, but with his breaking they were convinced that finally, the first seal would fall and Lucifer, their salvation, could finally be free.

It had taken years to break him; an entire century in fact. And that was truly something, considering that over ninety-nine percent of the souls in Hell usually break within one year – it was a place of indescribable torture and torment after all. But no one, whether friend or foe, could deny the fact that John Winchester was the most stubborn sonuvabitch they had ever met. So what usually took less than one year took a full one hundred for John; but in the end he did succumb. Stubborn sonuvabitch or not, everyone breaks eventually; even John Winchester.

But the celebration of finally breaking the toughest hunter they'd ever seen died when the first seal failed to break with him. And their good mood diminished further when John was able to escape Hell less than 20 years later with the opening of the Hell's gate before the hunter could turn into a demon.

But there was still hope; not long before John escaped hell, Lilith became the contract holder for Dean Winchester's soul.

1. Characterized by uprightness or morality.
2. Morally right or justifiable.
3. Acting in an upright, moral way; virtuous; free from guilt or sin.
4. Slang. Absolutely genuine or wonderful.

Synonyms: dutiful, blameless, honest, meritorious, virtuous, honourable, just, sincere, worthy.

Dean Winchester was like the Robin to John's Batman; sure he was skilled, smart and a pain-in-the-ass to evil supernatural forces everywhere in his own right, but he just didn't seem like much of a threat compared to his dad/mentor. He was like a sub-note in the lives of John One-Of-The-Greatest-Hunters-Ever and Sam Probably-Lucifer's-True-Vessel Winchester. Yes, he had the potential to one day surpass his father in terms of skill and knowledge in hunting since he was raised in it, and he had always been better at hunting that Sam, but Dean's emotional vulnerability and dedication to his family (easily picked up and exploited by demons) didn't make him seem like much of a threat.

But despite the general consensus of Dean being the consolation prize and unlikely to break the seal, Lilith had made damn sure that his soul would end up in Hell anyway. A Winchester in Hell was still a Winchester in Hell after all.

So imagine her surprise when 30 years of torture later, the First Seal broke with the breaking of Dean Winchester.

With the first seal broken, Lilith was swept away in a flurry of activity and hope. Finally she could free her father and help him arrange the world as it should be. Dean was left with Alastair and promptly forgotten as she eagerly went to the surface to start breaking the other seals. Had she not been so busy, she might have wondered what had made Dean so special as to break the first seal when the countless numbers of good souls that had come to hell before him could not.

What she didn't know was that although Dean may not have been the likeliest candidate for breaking the first seal, he fundamentally understood something that the other good souls before him hadn't. That even though loyalty and duty were important traits, they meant nothing if it was for a bad cause. That being blameless didn't mean you didn't feel guilty, and instead of stressing over it you need to learn from your mistakes and do better next time. Honesty and virtue were overrated and only worth following if no one got hurt. Respect and esteem from others meant nothing if you couldn't face yourself in the mirror. That it wasn't his place to mete out justice, no matter how many people deserved a good ass-kicking. Sincerity and honour weren't worth the lives of others. And just because you are doing good deeds doesn't make your reason for doing them worthy. For all that Dean had been accused of being a mindless soldier, a smart-mouthed punk and a greedy whore, nearly everything he did was for selfless reasons; he only hunted to keep others safe and his family close, he never killed anything that wasn't already dead (unless it was self-defence) and he never sought revenge no matter how justified.

The truth was that while he may not have been the most dutiful, blameless, honest, meritorious, virtuous, honourable, just, sincere or worthy soul to have ever ended up in the pit, Hell had never hosted a soul so righteous as that of Dean Winchester.

A/N: I know that the show implies that John never broke in Hell, but I'll list my reasons as to why I don't believe it. First of all, it's hell people. I just don't see how it's possible to be tortured non-stop for years (without even being able to fall unconscious or die) and still remain unbroken. Secondly, demons lie. In 'On the Head of a Pin' Alastair was obviously trying to torment Dean even while being tortured, and being Hell's chief torturer and having personal knowledge of Dean, Alistair would know of Dean's insecurities, especially in concern with letting his father and family down. Taunting him with the fact that he broke when his father supposedly didn't was an effective way to get under Dean's skin. Thirdly, assuming that Alistair didn't lie there is still the possibility he didn't tell the whole truth. According to Wikipedia, the date of John's death was July 19th, 2006 (apparently that date is shown on John's heart monitor at the end of the episode 'In My Time of Dying'). There are a lot of contradicting dates on Wikipedia, but I'm going to say that John escapes hell early July 2007. In the episode 'Time is on My Side' Dean and Sam have a receipt that checks them into a hotel on June 11th, 2008. In the same episode, Dean states he has 3 weeks before he goes to hell, meaning that 11 months and one week ago (at the beginning of July 2007) was when he made the deal with the crossroad demon and a few days later the hell's gate opened up and released John's soul. Which means that John spent around a hundred and fifteen years in Hell, if one month on Earth equals 10 years in Hell. In the episode 'On the Head of a Pin' Alastair states "I had your papa on my rack for close to a century", leaving about 15 years unaccounted for when John was in Hell during which he apparently wasn't on the rack any longer. So I'm going to say that John finally broke at the hundred year mark even though Alastair didn't outright admit it. If you still don't agree with my reasoning, well you can blame artistic licence and the fact that it's just fanfiction as a last resort.