A/N: I can't apologize enough for an update for this story taking so long! I've edited this completely now, most of the original is the same, but there are some parts that are different. ~storywriter713

The lighting is dim, but a small jail cell can still be seen. There is a filthy toilet in one corner, a sink right next to it. On the other side of the cell, there is a narrow bed that looks like a plank of thin steel held up by a single bar attached to the wall. On it sits a thin, slightly yellowed sheet and a pillow that looks as if it's made out of rocks. In the cell, there is a man named Dean Winchester, who paces around his tiny jail cell, cursing himself for being an idiot. He mumbles obscene insults about homophobes – or more specifically, Castiel Novak's family. He slams his fists into the steel bars, causing a loud rattling sound and eliciting a, "Shut up you scumbag!" from one of several prison guards. Dean ignores the grumpy security and tries to figure out where he and Cas went wrong, searching through his memories.

~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~

Dean Winchester had always been a poor man. Since his mom had died in a house fire when he was barely four years old, it was just him, his little brother, Sam, and his dad, John. John was always out working various jobs trying to earn enough money to support his sons, but he always wasted at least half of the earnings on alcohol. Dean was left to look after Sam, essentially raising him, dropping out of high school soon after starting his senior year to get a job to pay for his younger brother's education. He worked seven days a week, always arranging sleepovers for his little brother so he wouldn't be left alone.

His first job was dog walking, which was a bust. The dogs hated him, and he hated picking up the dogs' crap. His next couple of jobs were testing out brand new roller coasters, where he almost died twice. Eventually he met a man named Bobby Singer, who taught him about all cars and hired him as a mechanic. He worked six hours a day, everyday, two hundred dollars a week. Dean was happy that Sam would be able to have three meals everyday thanks to him. His boss ended up being more of a dad, always giving them food and paying for Sam's school supplies.

One day, when Dean was almost nineteen, he saw an ad in the newspaper. Some rich family needed a butler, aged 18-25, no previous experience necessary. They'd pay one thousand dollars a week, five times the amount he was earning from Bobby. He applied for the job right away. He needed that job so he could save up the money Sam needed to go to Stanford. His little brother was planning on becoming a lawyer. Bobby understood and told Dean that if he didn't get the job, or he was fired, he could always come back. He got the job and was about to start his first day.

"Good morning, Mr. Winchester. Here is a map of the Novak household. I trust you will serve the Novaks well and will have and hold their full trust," a constipated-looking woman said.

Dean assured her that he would be a good butler. He listened carefully to his instructions. He was told to meet the Novak family in the east wing's living room, where he would then be fully interrogated by Castiel, who was apparently very good at judging people, before he got assigned his butlering duties. Even though he was awed by how huge and expensive the house – no, castle – seemed, he made it to the correct room in no time. Luck was on his side that day… hopefully.

"Mr. Winchester, thank you for getting here on time. I am Michael Novak. These are my younger brothers Lucifer, Raphael, Uriel, Gabriel, and Castiel. This is my younger sister, Anael. We are a religious family, hence the names," the oldest-looking man explained. "Tell us about yourself and why you applied for the job."

Dean took a silent deep breath in and began to speak. "My name is Dean Winchester. I have a little brother named Sam who I look after when he's not in school. I applied so that he could concentrate on getting into Stanford and not worry about paying for what he needs, or if he's going to eat tomorrow," he answered.

Michael, Raphael, and Uriel seemed annoyed, but everyone else seemed touched; they could see Dean's love for his little brother. Four children walked in and Gabriel stepped forward to introduce them.

"This is Raguel, Michael's son. Remiel, Raphael's son. Sariel, Uriel's son. Samandriel over there is my son. They're ten, nine, six, and eight, in that order," Gabriel announced with a proud smile, gazing fondly at his son.

"It's nice to meet you all." All the children, except for Samandriel, were giving him the stink eye. Dean knew he would be avoiding everyone but Samandriel, Gabriel, Castiel, and Anael; they seemed nice enough. The others glared at him with a lot of hate for someone they just met.

Dean mentally prepared himself for his one-on-one with Castiel. Dean was very nervous that he wouldn't be accepted since he was bisexual, something he hadn't told anybody. He glanced at his future interrogator, and saw blue eyes looking deep into his very soul. Crap, he wouldn't be able to lie when asked a direct question.