Leading a normal life, Mary finds, is a lot harder than Hunting ever had been. Wendigos, vampires, werewolves, ghosts these things she knew how to confront and take down with weapons and incantations. Shopping malls, carpools, and soccer moms? Though she, at times, wanted nothing more than to draw out her disused blades and parse her way through the lot, she had no clue how to deal with any of them. Oh she tried, of course, and mostly it was a success but mostly it was a disaster. Mary Winchester was not normal.
Still, she made it work. Had to, really. She had two little boys to raise and a husband to share a life with and Mary knew, first hand, how hard it was to do either, let alone both, while trying to take down the creepy crawlies that seemed to be never ending. So she made a choice, swallowed her pride, and joined the local PTA once Dean was old enough for pre-school. It was probably the singular most excruciating experience in her life and that included the comparison between childbirth and the one time she'd been caught between a Wampus Cat and the jagged edge of a canyon wall back when she was sixteen; thirty-seven stitches, a broke wrist, and a crushed cheek bone was less painful than listening to the incessant whining some of the dowdy housewives and trumped up Papas did over their precious little angels. Christ, most of the time Mary truly empathized with serial killers and mad men.
But normal ended when her old life came crashing into her new one, literally. A murderer had set up shop two towns over, or so the local reporters had intoned on the six o'clock news, and Mary knew it wasn't some hopped up human with mental problems; it sounded more like a deranged werewolf than the modern day Jack the Ripper. But Mary forced herself to ignore the signs of the supernatural as she had since she ran away with John to get married. It almost cost her her youngest, Sam, and her husband when the goddamn Nunyenunc (and she fucking researched the hell out of that thing to know exactly what it was called) had swooped down on John's old truck and tried to pry her husband out of the cab. To say that it had freaked John out was an understatement but, like the Marine that he was, he shunted his fear to the back of his mind and did what he had to in order to protect his family.
Mary was scared out of her mind, ashamed, but ultimately proud when she sat him down, before he could actually go out hunting that thing with his .22, and explained all about the things that regular people just didn't want to know about, and about Hunters. John hadn't taken it particularly well that she'd lied to him all those years, or the fact that she knew something about those murders that might could have helped prevent more or get rid of the creature that was causing them, but he forgave her then pumped her for everything she knew, grilling her for what felt like days, until he felt himself better equipped to tackled the beastie that tried to take his head off.
To say that things were never normal for them after that was an understatement. The Winchesters family joined one of the oldest, most secret societies on God's green Earth; they became hunters. Mary reestablished contact with the Campbell clan and, though they didn't welcome her with open arms, helped her and her family get established within the hunter networks and even took John under their wing for awhile before her husband hit the road towards South Dakota where a man had lost his wife and was looking for some help with demons. It was hard letting him go but Mary learned long ago that marriage, like love, was all about give and take. She let him leave her with their two boys back in Lawrence and he gave them a good friend and an Uncle when he returned. Fair exchange in her opinion.
They boys grew up in equal parts hunters and normal kids. She tried to provide them with just enough normal to balance out the shit storm that was the supernatural and, for the most part, she thinks she succeed. Dean was a natural, much like she'd been, with hunting. He was quick witted, dependable, and could seemingly do the impossible when he was fighting to save people lives. Though she was scared to let him go off with John on hunts, she knew Dean would do everything he could to get them both back safe when John got a little obsessive and forgot that not everyone was bred with the 'Do or Die' mentality that was stomped into the men of the Core.
She loved John, really she did, but the man could be a right stubborn bastard sometimes. Mary thinks that's where Sam got it from because that boy was just as pigheaded when it came to things he thought were right or how they should be. 'The World According To Sam' was an orderly place where people were meant to do right by their fellow man and when they didn't, were pursued and punished to and by the letter of the law. And Hunting, though necessary, shouldn't interfere nor really interfere with his life. Oh he still begged to be taken on hunts when he was little and was a pretty good Hunter in his own right as he grew, but that boy was more about the 'Real World'. It was a point of contention between him and his father, and poor Dean was in the middle of their rows trying to calm both sides down while Mary tried, and mostly failed, to make them all pull their heads out of their asses and get along. Sometimes it worked and sometimes everyone involved was left emotionally raw and bleeding, figuratively and literally. But they were a family and that meant that they eventually remembered that and things got better.
Twenty years plus and a lot of growing, both together and apart, the Winchesters are still living in Lawrence in that home she and John bought before Dean had been born, and still hunting. Well most of them. Sam was off at Stanford trying to become a lawyer - he'd succeed too because Mary knew that boy was both stubbornly determined and wickedly smart - and John and Dean were traveling the countryside in search of things that went bump in the night while Mary stayed at home doing research and keeping house, imparting answers over the phone and waiting for her boys to come in. She made a lot of connections, friends - Bobby Singer and the Harvelles chief among them - so she wasn't lonely, but sometimes she wishes for 'Normal' instead of worrying when she'd get that late night phone or, worse, an actual visit from the authorities to inform her something bad had happened to her family. But, she wouldn't give this life up for anything.
Well, not until she got the shock of her lifetime. Apparently she was a grandmother. Huh.