So the world is saved, nobody is dead and there is no big bad hiding around the corner wanting to destroy the world, humanity or what else. To be completely honest Dean is feeling a little out of his depth. These last few years of his life have been like a roller coaster from Hell that seemed to go on and on, never stopping and always with a new twist around the corner but now, now everything is normal (or as normal as there is for them) and he doesn't know what to do with himself.
So they go back to the basics: hunting things saving people, teaching Jack how to blend in, keeping up with Cas' humans lessons and helping their mother become accustomed to a life in the future.
So they hunt, ghosts, werewolves, cursed objects (nobody mentions the time Dean was a she for a few days until they could reverse the effects but sometimes he can see Sam smirk at him even though he has his poker face on, the little jerk). They hunt until a poltergeist throws Sam from a two story building and he walks away with a limp that never goes away. They hunt until Dean gets stabbed in the chest and can't always seem to breathe properly.
So they open an occult shop filled with odds and ends from the Bunker, from Bobby's house, from their time spent on the road.
It's a small shop filled with books and scrolls and How-To manuals. They have protection amulets and different plants and herbs that help in a lot of ways.
They even have music. Cassettes and CD's filled with different bands from different times. Everything and anything they can get their hands on (they don't do it for the money but they need to do something and this is a compromise)
(In the back room they keep the heavy stuff, stuff that only hunters deal with and it takes some time until word gets out but soon enough, at least every week, there is a hunter who stops by to ask information about a monster, or to buy a weapon. Sometimes they just stop by to say hello and look around).
The sign is something Dean finds tucked under a Led Zeppelin t-shirt in a basic thrift shop. It's a circle with a hand drawn bull head in the middle with the words "Something will blow up and if it doesn't you're doing something wrong" written in cursive. He hangs it on the door, above the open sign while ignoring Sam's bitch face number 23 (the "i-don't-understand-how-we're-related" one).
The Shop (because they don't have a name for it and they never will because every name they can think of makes them sound like those new age pretentious douches, not that Dean or Sam have anything against them but they don't want to be associated with it) is of course warded to Hell and back (literally). Dean spent a whole day painting a devil's trap on the entire ceiling while Sam painted the walls in Enochian symbols and Jack was doing something glowy on the door. The only thing better warded is the Bunker (and even that's debatable).
The only thing Dean hates about it is that he has nowhere to park his Baby and he grumbles about it constantly which drives Sam crazy (if he rolls his eyes one more time they're gonna get stuck that way).
At first clientele was nonexistent (because really, who in Lebanon, see a shop without a name open up and decide that they just need to come in) not until, while they were closing down one night they hear a scream and without even thinking about it they run towards it (because it was always about saving people with them and that is something that never goes away). Sam gets first around the corner, despite his limp, Dean a step behind him and it takes them a second to realize it's not a monster but some boy trying to assault someone. The issue is resolved fast and without any complications. There aren't many people who don't stop and falter when faced with two men taller than the average dude and built entirely from muscle acquired over an entire life of fighting (the Winchesters haven't become the most scary hunters in the community by knitting).
The person they save is a five foot something wisp of a girl, who despite the fact that she was nearly assaulted is spitting mad and swearing enough to make a sailor blush.
What they are shocked to find out is that the girl-Andra "Don't-call-me-Cassandra"-is the Sheriff's daughter, who arrives with screeching tires and nearly hits an observer with the door of the car in his haste.
The story is straightened out in minutes, the guy, who is already pale from dealing with the Winchesters, pales even further at the sight of the Sheriff and gets shoved none to gently in the back of the squad car. The Sheriff thanks them profusely and Andra hugs them both.
The incident is nearly forgotten until Andra skips into their shop dragging a tall, straight faced girl after her (the sight makes Sam grin because Andra is half the height of the girl). They spend nearly an hour in the shop and while Andra buys everything that catches her eyes, the girl, Samantha (Dean chokes on his spit at that), buys two books older than her and three anti possession amulets.
After that people trickle in slowly and while some sniff and turn their nose like they smell something bad, others are just curious (they also get a lot of teenagers that want to be edgy). Some believers and every once in a while someone who is new to this and genuinely wants to learn about this stuff (Sam, the nerd, is happy to talk anyone's ear off, at the slightest indication that they're willing to listen).
Dean manages the books and the money, after all it's something he has been doing all his life and he nows how to do it right.
Cas comes back from his trip on a rainy day exactly when they are ready to throw in the towel and close the Shop early. After that he's always lurking around correcting any mistake in the lore, no matter how slight. Dean loves those moments, he especially loves how Sam looks when Cas indignantly stares at whatever offended him (Dean thinks that Cas is also swearing under his breath in Enochian but can never really catch him).
Andra and Samantha (who have become regulars, though Sam thinks they only come in because they run the shop, not because they really have an interest in any of the stuff they sell) come in right in the middle of one Cas' rants about the stupidity of an author and the inadequacies of the human race in gathering historical facts. Andra is shocked for a moment then jumps in enthusiastically, Samantha simply raises an eyebrow (and this is the most expression Dean has ever seen on the girl) while Sam looks like a kicked puppy (apparently that was one of his favorite books).
The girls take to Cas and his quirks without battling an eyelid (though Dean sometimes catches Samantha eyeing Cas, a strange expression on her face, like she knows Cas is different but can't quite put her finger on it).
It's a sunny Saturday morning when Andra skips into the shop and tells them, in a no nonsense tone, that they are coming to the barbecue her father is organizing later that day. Then she skips out again leaving the brothers gobsmacked. They shrug and when the time comes they close down the shop, get in the Impala and go.
Andra lives in a typical small town house, complete with a white picket fence and a massive Great Dane (whose name is Spock) to which Sam falls instantly in love.
Samantha and her parents are both present and apparently the barbecue is an excuse for Sheriff Whillis ("call-me-Walter") and Samantha's dad, Robert, to argue over who better knows how to fire up the grill for over 40 minutes.
After an awkward moment when the boys ask about Andra's mother and it turns out that she skipped out on them when Andra was five, things settle into a nice rhythm (Dean hovers near the grill, already eyeing the still not done meat and Sam engages the girls in a debate about some lore that he found about recently).
Samantha's mother, Elena, is a constant joker with an amazing poker face (and now Dean knows where Samantha gets it from) who can never seem to sit still. The only time she seems completely relaxed is when she fires up a cigarette which gets her a lot of side eye from her husband.
The barbecue runs well into the night and by the time they return to the Bunker they are both tired and content.
Their mother arrives a few days later with a bag full of different knick knacks from her hunts and a few new scars. She stays in town for a few days until she can't take it anymore and books it to another hunt in the middle of the night (a few years ago Dean would have dealt with this by drinking and tuning up Baby and Sam would have buried himself in research, now they simply clean her room for the next time she comes into town and go and open their shop).
Jack is taking online classes and is thinking of applying to college and Dean is thinking of ways to pay the tuition and Sam is researching for the best colleges but there is still time because he still doesn't know what he wants to do (Samantha is perfectly happy to provide pros and cons for every idea that he has and Andra is already thinking of ways to help him move).
They are content. But Dean can't say he is surprised when signs start popping up that something is not right in Lebanon and by the time the first body shows up he has resigned himself to the knowledge that Fate would always screw with the Winchesters.
They buckle down and get to work because they might be retired but this is their town, they have started to lay roots here and they have to send a warning to the other nasties that they won't accept this kind of shit on their turf. It doesn't take them long to realize it's a demon wreaking havoc but it's still too late until they figure out that the demon is in Walter.
The Winchesters are pissed because Walter is their friend and he's Andra's father and this is simply unacceptable.
They go to the Whillis' home and Dean gets to the door first, breaking in without waiting for Sam and Cas. He finds the girls in the living room, both of them tied up and apparently unharmed, aside from Samantha who appears to be unconscious. Ignoring the sounds of screeching and swearing he quickly unties the girls and gets them out of the house, trusting Sam and Cas to take care of the demon (he is fighting every instinct he has to go back into the house and put the motherfucker through a wall but he stays put, checks Samantha's pulse and wraps Andra in his jacket, because the girls need him and he's not about to let them alone right now).
Samantha is just coming to when the sounds stop and Sam limps out of the house to give him the all clear.
When they enter Walter is sprawled over the couch with Cas standing vigil at his head. Andra runs to her father while Samantha sways gently on the spot, eyes narrowed.
The explanations aren't fun at all, when Walter wakes up, but there is no better proof for the supernatural than a demon who takes you for a joy ride (Dean laughs for twenty minutes when he finds out that the reason Samantha was unconscious was because she kept screaming Christo at the demon).
The revelation that Cas is an angel goes much smoother, or as smooth as it can be, the only one who isn't surprised is Samantha (apparently she could sometimes see the shadows of his wings which Cas tries to explain but he looses Dean after the first few words), Andra takes it in stride and Walter is still in too much shock to really process it all (it helps when the boys tell him that they know how it is, to have something else take over you and do horrible things, they know what it's like to watch your body move and be unable to stop it, they understand the powerlessness that comes from it and the distrust in your own body that comes after).
The boys spend the night warding the Whillis' house while Samantha watches carefully so she can do the same to her house. They leave in the morning, after extracting promises from everyone to get an anti-possession tattoo as soon as possible.
They don't open the Shop for the next few days (they have gotten complacent in their retirement, they have forgotten that they have enemies and they need to prepare for other monsters stumbling over their new home). They reach a compromise with Crowley, they don't come after him and his business unless the town is safe from demons (they still bless the water supply of the town, they are not naive) and Crowley agrees because even retired, even with Sam's limp and Dean's health issues, he still doesn't want the Winchesters after his ass (he is not stupid, there is a reason why he had survived so long, he is the only one who doesn't underestimate them and their ability to pull a miracle out of their asses when faced with something bigger and stronger than them. He is perfectly aware that he lives and reigns over Hell only because the Winchesters allow him to and really it's not that big of a request that a small town remains demon free, he has the whole world at his disposal).
Things go back to "normal". Every Saturday they go and make barbecues at the Sheriff's house, where Samantha is a regular presence along with her parents (when she is present Elena watches them like a hawk, curiosity mixed with understanding and a hint of something else hidden behind her gaze, Dean knows that should something happen to either girl under their watch they would be scrapping up bits and pieces from the floor).
Samantha spends nearly all her free time at the Shop now learning anything and everything about the supernatural. The boys are reluctant to teach her in the beginning but after an argument that lasts nearly a day and Dean learning a few new curse words from the girl (which he didn't think it was possible) Cas is the one who intervenes and agrees to teach her. After that they all teach her everything they know (which is a lot). Sam is, of course, extremely happy (the nerd) and takes her under his wing. When they run out of material at the Shop they take her to the Bunker and Dean laughs when he sees the first open reaction on her face as she takes in the library and then he wants to bash his head against the wall because it turns out Samantha is a bigger nerd than Sam (and he didn't think that was possible).
Time passes and Jack finally decides to go to medical school, because he grew up with the Winchesters and he wants to help, he wants to save people, he wants to make a better world (Dean is unbelievable proud and can't seem to stop talking about it to everyone around him how his little brother is going to medical school while Sam researches everything and anything he can get his hands on and gives Jack tips on how to study better, how to cope with the stress of exams and everything else that entails going to college). Andra throws herself in finding him a place to stay and the logistics of moving him there but it's Samantha who shows him the reality of medical school, she patiently explains the hardships that he will face, the constant competition between students and doctors, the egos that intervene, the feeling of never being good enough, of pushing yourself to the breaking point and then further not because you want to be the best but because you want to help. She explains that he will face constant put downs by the older practitioners who don't want to retire, who were crushed in their youth and now they crush others just because it gives them a sense of power. She also shows him the good side, the side of how a simple "Good morning. How are you today?" can brighten a patient's day, the relief that crosses someones face when you tell them good news, the feeling you get when you help someone when you can because not everyone can be saved. She paints a picture the boys are familiar with, good mixed with bad, people enduring the bad because it's not about them, this job is so much bigger than that.
And so Jack goes to medical school. They all help when the time comes for him go, even Mary comes to help him settle in.
Andra hugs him for nearly 15 minutes and after nodding her approval at the apartment Samantha does too (which doesn't surprise anyone. After so much time spent together everyone knows that under the extremely good poker faces and sarcasm she is just as big a softie as Andra).
They leave him with a warded apartment and the order to call them daily or anytime he needs it. They are worried, of course they are, Jack is family, but they also know that he needs to live his life and well he is a nephilim so there aren't many things that can hurt him and that helps them sleep better at night (and if Dean texts him constantly song lyrics and Sam sends him books and Cas texts emojis well nobody has to know).
Time passes, they continue with the Shop and helping the hunter community. Every new hunter is sent to the Winchesters with the instructions to listen to everything they have to say and not piss them off. You piss them off you are on your own because nobody wants them on their asses (the older hunters remember Roy and Walt, how they bragged about killing the Winchesters and then went mad thinking they were being haunted by their ghosts). When needed Cas goes out and helps whoever needs it but there is no need for the big guns, the big guns are retired thank you very much (though everyone knows to not mention the word retired around Dean unless they want a three hour lecture on how a hunter never retires, complete with a PowerPoint presentation and a minimum of twenty curse words. Sam is one hundred percent sure that Dean does it on purpose but he can't prove it).
And then another shit train comes because why not?
Elena stumbles into the shop, interrupting an academic argument between Sam and Cas, face drained of blood and Andra trailing behind her looking half-crazed and with a blossoming bruise on her face. The story comes out in short clipped details. Elena, Andra and Samantha were window shopping at the few magazines in town when three guys in ski masks attacked. They tried to fight them off but were unsuccessful when a van came out of nowhere and they shoved Samantha in and took off. Elena is sitting on the only chair behind the counter, silent and starring into thin air and Dean's blood boils. Because this, this is a different kind of monster but Samantha is family and nothing, nobody hurts their family.
So they get to work. Sam immediatly works up a tracking spell, while Dean checks the weapons.
Elena is still silent and Andra nearly breathes fire. She tries to argue with them, to come with them but they won't have it. They leave Elena and Andra in the relative safety of the shop and go to bring Samantha home.
They find her in a shack on the outskirts of town, unconscious and tied to a chair in one of the rooms while four guys drink beer in, what was one time, a living room. Because Cas is a little shit all the time sometimes, he goes in full angel on the dudes while Sam and Dean get Samantha out.
At the end the bad guys are tied up, the Sheriff is called and Samantha is brought home safe and sound though extremely pissed off.
What they later find out is that the douchebags were paid by another douchebag to kidnap her who apparently has a grudge against her father. Which is of course the reason Samantha has three new bodyguards for at least a month. Or at least until she very pointedly tells them that she can take care of herself and if they don't stop following her they will not like the consequences. They stop.
Somewhat, as Cas still shadows her, what with him being capable of turning invisible (which doesn't always work on Samantha if the rolling of her eyes is a sign). So the boys turn to improving her fighting skills and teaching Andra some self defense moves (Dean will deny to his dying breath that Samantha made him see stars and put him on the ground. Sam laughed and filmed it until Andra kicked him in the nuts and dropped him to his knees. Cas filmed that).
Time passes, Jack graduates, Mary hunts, Andra goes to law school, Samantha becomes a hunter, Cas helps out the few angels in Heaven and they run the Shop.
They grow old and they bicker and Dean steals Sam's cane and Sam puts pink dye in Dean's shampoo. They open the Bunker to other hunters, they still help people, they help each other heal and they are happy. Samantha breezes in and out, a new story on her lips, a new scar, a new tattoo. Jack calls and tells them about the people he helps, the kids he heals and he visits when he can. Andra turns into a thunderstorm of a woman in red high heels, briefcase in hand. Mary hunts and hunts and hunts until she doesn't. She dies on a rainy day but her funeral is on the sunniest day of the year. They mourn but the grief doesn't choke them anymore. They no longer drown in their mistakes and what could have been's. They move on.
They make sure to have their affairs in order (which is something Dean never thought he would do). They leave the Shop and the Bunker to Samantha who comes home one day, dragging a wide eyed man after her named Steve. After the necessary interrogation questions they find out that Steve was a Navy SEAL who stumbled across Samantha while on hunt and never stopped following her (and going by the way he looks at her he never will).
Andra comes home on Christmas to introduce her fiancé, Calliope, who is a doctor whose mother is a psychic who knows everything about the Winchesters (because why not, the world is a small place).
They make Jack and Cas promise to look after the girls when they are gone (it's not really needed but it makes them feel better).
When they die, they die together because, at least, the universe grants them that, because even after all this time they couldn't bear to be apart. Death comes for them (it's always Death, not a reaper, because this time it's their time and there is no coming back) and Cas waits for them in their Heaven.
Now they can rest.