Rating : NC - 17 / M

Genre : Slash, angst, romance, some humor

Pairings : Dean/Castiel , Dean/Lisa , Sam/Jess, some minor pairings

Spoilers : Some for characters from all seasons, but otherwise none, this is AU

Warnings : Mentions of underage sex, prostitution, language, smoking and alcohol, sexual situations, general weirdness (yes, you have been warned). Additional warnings will be added to chapters when needed.

Summary : Dean lived what seemed to be a perfect life with his wife, Lisa. Everything changed when he picked up a young man walking by the road in the rain. That was the day that marked the beginning of a long, painful romance full of secrecy and doubt between a married man and a high-class prostitute.

Disclaimer : Kripke owns everything, I'm just playing with his toys. No profit is made with this story.

A/N : All mistakes in grammar and spelling are mine (feel free to point them out though). This was supposed to be an original story, but I've got a writers block for original stories so I turned this into fan fiction. The prologue is pretty much straight from the original story I tried to write, but I did some major changes to the story to fit the characters better.

Where Do We Draw the Line

Prologue

Dean Winchester had always wanted to be someone his younger brother could look up to. That's why he joined the football team instead of the school band, started dating the hot cheerleader and tried to do well in school. He learned all about cars from their father and his friend Bobby, and their mothers friend Ellen introduced him to one of his best friends in all time, Jo.

Dean took good care of his brother when their parents weren't home, their mother worked as a paramedic in the local hospital, and their father owned a garage with Bobby. Everything was fine, Dean was one of the popular kids and his brother was most likely going to be the new Einstein. When Dean turned sixteen his father came home one day and told him that he would give his son the impala if he would graduate high school and do something worth while with his life, and that he should really marry the nice girl he has been dating. Dean took this to his heart, not because he wanted the car, but because this was what his father wanted for him.

So when Dean graduated from high school he went off to college where he took business as a major. Unfortunately his relationship with the nice cheerleader, Cassie, didn't last for very long after they got in to different colleges. Dean still did his best to study hard, but it was difficult not to give in to the call of the parties all around the campus. Later he was glad he went to some of them, since he got to meet Lisa. The two of them agreed to go out and see if things would work out between them. They got married six months after graduation and Lisa's father promised to get Dean a job if they moved closer to Lisa's family. They agreed simply because it seemed like the reasonable thing to do.

They lived what seemed to be an idyllic life in the suburban areas of a big city. All that was missing was a dog and two and a half kids. Somehow this didn't bother Dean too much, Lisa an he both had a lot of work to do and a child at their situation just didn't seem like a good idea. They had talked about it and agreed to wait until Dean would get promoted and Lisa would be ready to raise a child.

Dean got his first promotion in eighteen months, because Lisa's uncle was convinced he deserved it, and if people gave him weird looks because of it, he didn't pay attention to them. That evening Lisa brought up the subject of having children up for the first time in months, and Dean was suddenly terrified. They decided to wait for a little longer.

A year later Dean was in a rather high position at work and when he saw Lisa smile at him when he got home after a long day at work he thought he was the luckiest man on earth.

Everyone called him Angel. It had started with his mother before he was born, or so he had heard.

He lived in a rather classy apartment near downtown, went to the local college and carried an expensive camera almost everywhere with him. His life hadn't exactly gone as he wished it would have, or rather, like his rather religious parents and family wanted it to go. His life had been planned for him the moment he was born, and it was supposed to go something like this: Go to church, go to school, graduate with straight line of A's, go to church, graduate high school with straight line of A's, go to church, go to college and graduate with straight line of A's, marry the nice girl that goes to the same church with you (and don't even think about having sex before your wedding night), get a respectable job, have a bunch of kids, never forget to go to church and do charity and most of all, never ever are you to stray from the teachings of the Bible.

He failed his family's expectation for him at the age of thirteen when he had his first crush. It wouldn't have been so bad if he would have fallen for the nice, decent girl sitting next to him in the history class, but that was not the case. The little angel fell for the rebellious boy sitting in the back of the math class. This is where his troubles started. It took him a long time to catch up with what was happening, but when he did, he ran to the church he went every Sunday and prayed obsessively for two hours before heading home with no idea what to do. That was the first time he lied in his life. You see, he was sure that his father would burn him alive like they did to the witches in the old days if his perfect son would tell him he had a crush on another boy. So the angel lied when he was ordered to tell the reason he was late.

He hoped and prayed for the torment to go away, but it never did. When he was fifteen and going to high school, he had managed to overcome his crush for the rebel boy in the back of the class. No one knew about it either, so it was a victory. Everything went as planned up until the concert the school provided for the students to ease up the start of new torturous year of studying. The school band played rather provocative songs, and the little angel was blushing at some of the lyrics. But then his eyes met the gaze of the guitarist, and his world seemed to come to a halt. They looked at each other for a long moment, and the guitarist smiled. Three weeks later they held hands for the first time, after spending all their free time at school together. His name was David, and he was the kindest soul on earth. He understood the fact that his angel came from a religious family, so he did his best to make the young, very confused boy to understand that their feelings for each other were not wrong, for God had created them as they are and He loves every single one of His children.

They shared their first kiss two weeks later. It was a quick touch of lips, but it was still enough to cause both of the boys to smile brightly enough to light up the night. A week later the whole world came crashing down, when the angel of the family turned out to be a demon in disguise. The young lovers were walking down the road, shyly holding hands and putting distance between themselves when someone came to their way. They still got caught by Angels mother coming from grocery shopping. She pulled the old ford to a halt and dragged her panicking son away from the evil child who had dared to tarnish him.

In the end it would probably have been nicer to be burned alive. The former angel was sent to bible camp, and when that didn't work he was sent to an institution that was designed to deal with 'difficult cases'. Ice water baths, shock therapy and rubbing a long corridors with toothbrushes didn't lessen the desire in the young boys heart to be in David's arms again and be told that he was alright as he was. He was allowed to continue his studies, as a distraction from the unhealthy workings of his mind, and ironically he graduated a month before most of his classmates.

A few weeks after his seventeenth birthday he was released as cured. He went home, fell to his bed and faked sleeping when his mother came to check on him. At midnight he packed his clothes, took his most important belongings with him and stole the money he knew his mother kept behind the cookie jar. It was enough to get him away from this life he didn't want anymore. He couldn't live in there, not after what he had been through.

When the nice gentleman at the train station queried his name he hesitated for a moment before answering in a charming tone.

"Call me Angel, everyone does."

He got a free lift to the next state and a job offer that he accepted after careful consideration. He spent two weeks wit the nice gentleman and learned things that would have made his mother pass out in terror. He left to find his very own apartment with a considerable amount of money in his pocket.

Six months later he had a nice, small apartment and solid incomes, he had decided to save up for college intuitions so he could study literature or arts, he wasn't sure which one yet.

These two very different lives collided on a rainy Saturday through a series of highly unlikely events that started months before one even knew the other existed.

A/N : This is basically ripped from my original story, but starting from the next chapter I've re-written most of it to fit the characters better without changing the storyline.

So, what do you think? I'll give cookies for reviews!