Bobby likes to keep most of history a secret. Before Karen, honestly not many know what went on his life. That's the way he likes to keep it. What's the sense in dredging up his abusive childhood? A father who liked to drink and hit women and children. Well that's not much to talk about, and that's exactly what his childhood was. His mother was so emotionally abused, that after Bobby killed his father and buried him in the shed out back, his mother only claimed that God would punish Bobby.
Well in that regard - she didn't seem to be wrong.
After killing his father, Bobby and his mother basically became estranged. Sure he lived there, and when he was old enough he got a job to help put food on the table, but his mother passed on not long after Bobby came of age.
With his parents gone, Bobby continued doing what he always did, working at the salvage yard, fixing cars - which was probably the only thing his father ever taught him that was useful. Still there was a deep seeded fear in him of becoming like his father. That he would find a wife and hurt her, have kids and hurt them. That was something he never wanted.
In fact, Bobby never meant to fall in love with Karen. The woman just had a way about her though. She easily moved past all of his defenses, and before Bobby knew what had happened he was proposing. They were married and she was coming to live with him. The house suddenly wasn't a bachelor pad anymore, but had feminine touches, and the scent of fresh, home cooked meals every night.
Bobby was living the high life. For the first time he was truly happy. It was something he had been so scared to have, but now that he did - hell he never wanted to let it go. Course that happiness was short lived. Karen wanted babies - Bobby still thought God was punishing him thanks to what his momma had told him. Course, with what came later, maybe she wasn't far off.
Bobby came home one day to a demon possessing Karen. Of course he didn't know it at the time. She just had black eyes and was trying to kill him. Bobby stabbed her quite a few times, before Rufus came in and did the exorcism. By then it was too late for Karen. She was already dead.
They buried her body and Rufus tried to tell Bobby that now that the supernatural world had touched him, well he wouldn't be able to get away from it. Rufus was looking for a partner at the time, someone to train and work with him, but Bobby didn't want none of it.
Bobby took off, finding work on a barge heading to Japan. What could happen out in the middle of the ocean. He reckon'd it was about as far away from the rest of the world as he could get, at least for a while. Well - as it were, he'd been wrong. While on the ship to Japan they'd been attacked by Ondines - or mermaid like creatures that they could only see when they were drunk. Seemed big momma Ondine wanted Bobby for herself, but Bobby luckily, managed to kill em' off and get all the way to Japan.
It was then he realized that Rufus was right. Well hell if he was going to be a part of this world, than he reckon'd he was going to be a part of this world the right way. Bobby stayed in Japan a year, learning the language, learning what he could. Then, he finally went back home and called the number that Rufus gave him.
Luckily for Bobby, Rufus was still looking for that partner.
From then on, Bobby and Rufus were inseparable. Rufus taught Bobby everything he knew about hunting, introduced him to the other hunters of their world. They traveled around, never hit the same town twice, and had each other's backs. Course, back then Rufus had a bit of a family. Not somethin' he really talks about, but Rufus had a woman he had a daughter with and he and Bobby stopped by every so often to see her.
Then there was that incident in Omaha. The incident that tore Bobby and Rufus apart. Truth was, Bobby never should have let that youngin' come. Especially not being Rufus's daughter, but he did, and now she was long dead. Rufus never forgave Bobby for that. To be honest, Bobby couldn't blame him for that.
It was about that time Bobby stopped huntin' so much. He started making the command center from his home. He met that bastard John Winchester, and wound up babysittin' the boys a whole hell of a lot. John - who Bobby wasn't so fond of - always wanted the boys to be trained in the ways of huntin'. Dean especially. They tried to shield Sam as much as they could. The littlest one still learned his self defense and such, but Dean was carrying the weight of the world on his shoulders.
Bobby watched the boys a lot while they were growing up. John would go off on hunts, and Bobby celebrated plenty a birthday and holiday with the boys that their father missed out on. Dean was determined to be the perfect soldier. It was always hard for Bobby to try and get him to do even the simplest things - like toss a ball around. He even had Dean run off on him once when Bobby spoke ill of his daddy. Guess Bobby couldn't blame Dean, at the end of the day, John was their father. Cept Bobby had grown accustomed to bein' their father too.
Honestly, when Sam went off to College, Bobby was pretty proud of him. Didn't hear from him, but he was still proud. Dean followed in his fathers footsteps, huntin', and the like. It was hard to watch the boys come into this life, but it was what they were raised for, and eventually Sam got dragged back into the hunting world. Bobby reckoned that Sam never really did have a chance to get away from it.
Seems though, that old Y.E.D. wanted Sam back for a reason. Bobby never suspected, but demon stock or not, Sam was his boy and Bobby wasn't going to turn his back on him. They did the best they could to stop the devils gate from openin', but they weren't fast enough. Bobby figures that's when the world started to change.
When Sam died though - well that just about broke Bobby. Then Dean went and sold his soul to bring his brother back. He swears them boys are gonna be the death of him one day. It wouldn't be a monster. No, it'd be a heart attack or a stroke from the stress these boys put him under.
Try as they might, they weren't able to find a way to keep Dean from getting dragged away by a hellhound. Bobby didn't much know what to do with himself. He tried helpin' Sam, but the boy refused to burn Dean's body. He mostly isolated himself. Damned if Bobby didn't feel more than a little useless then. So he did what he always did, continued hunting and helping hunters. He took the occasional call from Sam, glad to hear that his other boy was still alive.
Then Dean came back from hell. Bobby was hard pressed to believe it, but it was Dean. Castiel, an angel came into their lives and they had to try and stop Lilith from breaking the seals. That didn't much happen, but Bobby figured a while ago that heaven and hell were using his boys as pawns in their apocalyptic chess game. All he could do was try and deter it.
Dean broke the first seal, Sam the last. Lucifer rose from his cage and all hell broke loose. Omens, signs, monsters, demons, devils, all of them running rampant. Then there were the horseman. War, Famine, Pestilence, and of course Death. Death who rose all the dead of Bobby's home town. Death who had the zombies eventually turn. It was amazing how well his town took to the dead. Amazing especially how Sheriff Jodie Mills was so accepting of it.
In the end though, Bobby made a deal with Crowley to get Death's location for Dean. They needed his ring to defeat Lucifer.. Hell, Bobby didn't like the plan. The idea of Sam saying yes to Lucifer made his stomach turn. In the end though, he had to trust his boys, trust that they knew what they were doing.
When Sam let Lucifer in, they thought it was over. Sam wasn't strong enough to take over and jump in the pit. Dean couldn't believe it though. It just wasn't in his nature to give up on his brother, no matter what the circumstances. So they went out to the old boneyard in Lawrence. CAs and Bobby distracted Michael who had taken Adam as his vessel. Then, Bobby was dead.
When he woke up, it was over. Sam was gone, Dean was heartbroken. The boy was desperate to find a way to pull Sam out of the pit. Bobby tried talking sense into him, Sully tried to be there for him, but in the end, Dean lost himself and went off on his own. It broke Bobby's heart.
Of course that damn bastard Crowley still ain't gave his soul back. That's something Bobby's gotta worry about. He don't much care what Crowley said, they didn't kiss. It was photoshopped. Either way, damn demon went back on his end of the bargain and now Bobby needs to find some leverage. On top of that he's trying to find Dean and pull him out of whatever dark hole he dug himself into.
Just another day in paradise.
Bobby rubbed his face tiredly and wondered how he’d become the center of the hunter’s crisis network. Seemed like anytime someone had a problem they brought it to his door step. Every time they had a problem they somehow got his name, whether he knew them or not. They called him, they came to him. He was starting to feel like he was the leader of a Boy Scout troop.
“Oughta change the name from Singer’s Salvage Yard to Singer’s Crisis Center for Idgit Hunters.” He looked at Sastre once more, but Bobby wasn’t a Den Mother. The man didn’t look much like he was fit to patch up himself. Then again most hunters are stubborn.
“Patch yourself up.” He told Sastre. “Then we’ll head outside.”
Bobby wasn’t leaving someone he didn’t know in his house by himself. He was still wary of this man being Sastre, though he remembered him coming with the old man. Still didn’t think it was right the way the man treated them youngin’s. Even John hadn’t been so cruel to Dean and Sam.
John didn’t have much of a choice in the matter. Them kids hadn’t been the old man’s though. He’d chosen their fate for them. They had a chance, and the old man took it away. Bobby didn’t figure any who didn’t have to be in this life should be brought into it. More than likely the man sitting on the couch would be dead before the age of forty.
Bobby and Rufus were the exception. Maybe the cursed. Growing old and watching most of your friends die wasn’t exactly easy. Living with the regrets and the mistakes wasn’t easy. They trucked on though. Wasn’t much else they could do. Someone had to clean up the mess that the monsters left behind.
Walking over to the desk, Bobby grabbed two glasses and poured the whiskey. Taking them he brought one over to Sastre. “You oughta start keeping ducktape with you. Goes a long way when you don’t have the means to patch yourself proper like.” He sipped his whiskey the taste lingering on his tongue.
It helped take away the bad taste that the word Ducati had left in his mouth.