OK this is my first fanfic. Not sure why my first try had to be dark but this is the story that flowed out. So, here we go. Reviews are appreciated. :)
Dean closed the door to his shop, making sure the door was locked before walking to his Baby. Another day, another round of (hopefully) satisfied customers. All in all it had been a good day with no major customer issues as Winchester Auto Repair, a fact for which Dean was thankful. He tried his best to keep his customers happy; charging reasonable rates and never suggesting repairs that were unnecessary, but even then that was sometimes not enough. Still, today had been good, so he could not complain.
Driving home he passed the Roadhouse and contemplated stopping in for an after work drink but, being Friday, it would be packed and Dean's limit for social interaction was at its limit. It wasn't that he disliked people per se, but he apparently had a knack for saying or doing the wrong thing. Besides, he needed to save his strength for tomorrow. Alistair did not like him to be unprepared. He was the one cutting out the parts of Dean that were wrong, and there was much about Dean that was wrong.
Lisa certainly thought so…he thought ruefully. Jo had tried to assure him that Lisa had been a nasty twat, but Dean new better. No matter how hard he tried he could not really please anyone.
He'd watched over Sam as best he could growing up, but it was never enough. Any problem in Sam's life, no matter how small, no matter even if John himself was the cause, was blamed on Dean's inability to be a good brother. Sam himself had always pushed dean to do better in school, to take better care of himself, to be more thoughtful, and Dean had tried, he really had. Dean thought that maintaining B's and C's while taking care of Sam and working the odd job here and there was pretty good. Sam hadn't said anything negative but Dean could see he was disappointed and that his "Yeah, sure Dean that's great" was forced. After high school Dean was admitted into the local Auto Diesel College and was pretty happy about it. He loved cars, and wanted to learn everything he could about them. Some of his best memories were of spending summers at his uncle Bobby's house and helping him work on the cars in his shop. When he showed the letter to Sam and his dad thinking they'd be proud that he was continuing his education, his father had sneered at the idea of dean being a mechanic when his brother was certain to have a "real" career and Sam had said "It's alright Dean. I know you tried your best". It was like being punched in the gut, but Dean did what he had always done, shoved the disappointment down and walked away.
No matter what he did, how hard he worked, it was never enough. That point had finally been driven home by Lisa. She thought he was too messy so he tried to be neater. She didn't like his diet, his clothes, and the way his apartment was decorated; there were times when Dean thought she just didn't like him. She's stayed with him though Dean could never really figure out why, but he was not about to leave her. She was the one thing about his life that his father and Sam approved of. They seemed to think she could make his life better, so Dean kept his head down and tried to make it work.
All of that had come to an end one night at dinner. He'd gotten a loan to open his own shop and to celebrate Dean had taken her to the nicest restaurant he could afford, gotten her flowers, and was going to propose. Instead he's gotten a lecture about how she needed more than just a small town mechanic and that she had hoped he would eventually go back to school for something like Pre-Law just like Sam. All of her friend's boyfriends were going somewhere big. Bankers, doctors, lawyers, business managers; they were going somewhere, would have lucrative careers and be able to provide a certain "lifestyle" that Dean's meager earnings as a mechanic would not. That wasn't all though; she'd met someone else, someone better. Dean hadn't heard anything after that because of the rushing in his ears, he barely remembered leaving the restaurant and going home.
He didn't bother telling his father or Sam right away, he knew what their reactions would be. He rarely spoke to them much anymore, save for the family dinners his father insisted they have once a month. The one after his breakup was predictable, and Dean did not like to think about the looks he'd gotten from Sam and the lecture he'd gotten from his father about remembering his duties as a partner. They thought it was Dean's fault, Dean thought it probably was too. So he'd learned his lesson, there was something wrong with him. Something that kept him from doing anything was never going to make anyone really happy so he gave up thinking that one day he might.
He still worked as hard as he could at his shop, and tried to please his customers but he knew that eventually it would fail. Dean was bad, rotten somewhere inside and he deserved to hurt because if it. Eventually everyone would see that and that was why he needed Alistair.
He'd met the other man one night in a bar on the other side of town from where he lived. He'd needed to get away from everything and wanted to make sure no one he knew would see him. Alistair had slipped on to the stool next to him at the bar, said he's been watching Dean since he'd walked in and that he knew what Dean needed. Said he could see the desperation and loneliness from a mile away and that he knew the way to make it better. When Dean asked him how he could do that Alistair had leaned in and whispered in his ear that he could see into Dean, all his weakness, his pathetic need, everything that was wrong inside. Dean was inherently bad, flawed, broken, and needed to be punished because of it.
It had started out relatively easy, and at first Dean had gotten off on it. Alistair would give Dean commands: kneel, crawl, suck, beg, and Dean would try his hardest to do as Alistair wished. Dean was expected to take whatever Alistair wanted to give ("You like this toy baby? I found it just for you. I know it looks big but don't worry, I'll get it to fit") and if he couldn't ("Safe wording? Honestly Dean you don't need that much preparation. Can't take it like a man? Can't say I'm surprised, you're not even taking it like the bitch you are") then he was tied down and whipped. After a few sessions Dean was expected to list his faults after each strike.
(Needy. Pathetic. Useless. Stupid. Ugly. Disgusting. Worthless. Worthless. Worthless. Worthless.)
After each session Alistair would lean in close to Dean's ear and whisper "That's alright though baby. I'll carve you into a new animal."
Eventually Alistair moved to ignoring Dean's safeword, gagging him when he cried out too much and beating him harder when he didn't cry out enough. He used whatever toy he wanted, sometimes with no prep at all and the longer it went on the more Dean thought he deserved it. He could see the proof every day that this was working.
Sam and his father seemed to be nicer to him, his business was starting to do really well, hell even his car was working better. Sometimes a small voice in the back of his mind would say that everything else seemed so much better because his time with Alistair was so bad, but he ignored it. He deserved what he got during that time, and he was certain that all the good in his life was a sign of some kind of universal approval of Dean finally getting the pain he deserved.