Based on this post from annieloveswinchester on tumblr
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Dean had followed Sammy to California permanently a year ago. Originally, because Sam had tumbled into life away from John like Alice down the rabbit hole. They'd gone a month and half without hearing from him six months into his semester, and Dean had only meant to stay for a couple of weeks and sort out what the hell Sam was thinking, worrying their mom like that.
Mary had been secretly thrilled to see her eldest boy leaving town. She hoped he'd get a taste for life outside of Lawrence and stay. Make a decision that John didn't nudge him into. Leaving in the first place to find Sam himself had torn him apart for weeks and weeks. He and John had fought and argued and finally, Dean had stalked out one morning with a duffel over his shoulder and that set in his jaw that screamed Samuel Campbell.
John had wordlessly thrown him the keys to the Impala.
A couple of weeks turned into a couple of months when Dean met Sam's 'girlfriend' Ruby and damn near broke both his hands beating some sense into his fool brother's head.
"Drugs, Sam?! Drugs! What happened to a full ride?! What happened to being a freaking lawyer you asshole?!"
Needless to say, he'd stayed in California, gotten a string of crappy apartments and held down three jobs while scrubbing Sam clean with his bare hands and gritted teeth.
He made Sam tell Mary. Dean had been in California for a month and called Bobby to tell him to find someone else to help at the scrap yard: Mary and John knew something was wrong.
John screamed and ranted when Mary told him about Sam's budding addiction. He's demanded that they both get their asses back to Kansas before he went to Cali and dragged them back. For the first time in his life, Dean refused. John had gotten probably the drunkest Mary had ever seen him that night, but the next day they were agreed as a family; Sam would stay in California, at Stanford, with Dean. He'd get clean, he'd finish his degree, and he'd get that full ride to law school.
Which he did.
Dean decided to make the change permanent when his brother started law school. He'd confided to Mary, making her swear to secrecy of course, that he was pretty sure it was redundant anyway, because Sam had come back to their shared place mumbling and blushing about some girl named Jess.
Sam and Dean were making a life for themselves in California.
Mary had to laugh at herself, getting teary over the realisation, because for goodness sake, Dean was twenty-seven years old, Sam twenty-three. Still, she missed her boys.
The year went by. Sam's first year in law school, and her boys were home for Christmas—they drove because Dean still hadn't gotten over his fear of flying—and Mary was out the door to greet them before they'd even unwrapped themselves from their seats.
John made some gruff comment about rust on the Impala, Sam snapped something snark, and Mary cut them both off before it could escalate any further. With a heavy heart, she realised they weren't going to get through Christmas without John and Sam having a blow-up, and Dean seemed to realise it too, because he caught her eye and smiled grimly.
It was a lovely holiday regardless of the argument that ended in Sam spending the night at Bobby Singer's. Mary's father came around, heartsick from missing Deanna this time of year, and Sam still worshipped the ground his namesake walked on. Dean talked about the weirdos he got coming through the bar where he tended at night, keeping them all entertained. The Harvelle's came around and Jo flirted with Dean, making Ellen eye him warningly. She'd dragged Bobby out by his beard, so he and John huddled up in the corner with a bottle of Old Number 7 and were grumpy old men together. It snowed, and Dean played in the snow with Sairie and Ritchie from down the road.
Jo Harvelle managed to drag the brothers out for drinks at New Years. They met up with friends from high school and came home two days later hung-over, red-eyed and exhausted. John had laughed heartily at their hangdog expressions and talked loudly about salting the driveway.
It was that night, when Dean was helping her with the dishes and Sam and John were having an actual conversation in the other room, that he mentioned Castiel Novak for the first time.
"-and Cas was sayin' that uh, it's actually caused by some chemical thing that I don't get" he'd said it with an affectionate laugh.
"Who's Cas?"
She'd pretended not to see the way he glanced at her, a little spooked as he read her expression.
"He's a friend. Goes to Stanford with Sammy, but he's a physics student, at Stanford"
"So you said" she noted. Dean had blushed and changed to subject.
They left a week before the new semester started because Dean had to get back to work.
Two months later, in their tradition Sunday afternoon conversation, Sam confessed that he was seeing Jess Moore. In the background, Dean shouted ' 'bout fuckin' time!' and Sam's breath huffed as he threw something across the apartment at him.
He worried he wasn't good enough for her, in a soft, unsure little voice that sent Mary rushing back to the days of a wide-eyed, messy haired little boy who followed Dean around like a shadow. She reassured him, because that's what mothers were for.
Then Dean's voice, teasing and loud from exertion, echoed in the background. She couldn't understand what she was saying, but she smiled when she heard Sam's tone change to 'I'm gunna tell mom on you' :
"So, has Dean mentioned anything about his friend that he's totally platonic-ow, dammit, Dean!"
"Shut your mouth, Sammy"
"It's Sam!"
Jess came home with Sam and Dean for Thanksgiving. They'd flown for the first time, and John had been tactful enough not to say anything to Dean when he'd picked them up from the airport. Jess had the gruff ex-Marine charmed in the first five minutes, Sam bragged with his wide, easy grin. Mary hadn't seen that smile in a long time, and adored the young woman who'd brought it back the second she saw her. Sam loved Jess, that much was obvious, but what really put Mary at ease was the way that Jess was equally as in love with Sam. They gravitated around each other like planets, constantly aware of the others presence. Mary curled her arms around John's waist as he stood silently in the doorway, watching Sam, Dean and Jess arguing over a movie and popcorn. He stroked her hands linked on his barely-there paunch and she felt his smile in the give of the muscles on his back.
When Sam and Jess started talking about getting their first place together, Mary waited until Dean had a day off and Sam was at school before she called him. She wanted to know what was going through his head, not what was going through Big Brother Dean Who Looks After Sammy's head. To her relief, he was relaxed and easy.
"Yeah, it's great for them. They've got their eye on this place just off-campus, but there's apartments going about ten minutes away that have car-parking for Baby, so me and Cas are gunna look there"
"Oh, Castiel? Your physics friend?"
"Yeah. He's been sharing with four older brothers and his sister, so when I said I was looking for a roommate, he was pretty relieved" he'd laughed, but there was something in his voice, something slightly reverent about the way he said Cas' name that made Mary curious. She kept it to herself though, remembering that spooked look Dean had gotten when she asked about him at Christmas last year.
So it went. Castiel Novak, who normally went by his middle name James or Jimmy—and Mary had to struggle not to comment on that, seeing as how Dean and Sam both called him Cas, with a lilt of affection and brotherhood—and Dean got their place together. Sam and Jess fell even more ridiculously in love, and Mary realised that Sam understood his father now that he had his future standing beside him. She had long conversations with Jess some days when Sam was busying studying or in the shower or at the casual job Dean had gotten for him.
John found her crying one day in Dean's silent, still bedroom one day and comforted her as well as he knew how. What really fixed it though was the plane ticket he left on the kitchen table before he left for work.
"I've got a lot goin' on at the shop, but Sammy said he and Jess would love to have you" he muttered when she confronted him in the afternoon, when he came back from work covered in grease and sweat. She kissed him hard like she used to when they were teenagers and called Sam to tell him she'd be there in three weeks.
Dean had picked her up from the airport in the specially cleaned Impala. The old familiar rumble of her brought back all Mary's teenage memories, and she'd laughed till she cried teasing Dean by recounting the glory days of the backseat.
They went to Sam and Jess' place and dropped off her things—Sam and Jess were at school and work respectively, but would be home around 4—then drove around listening to Metallica too loud because contrary to popular belief, Dean had gotten his musical tastes from his mother, thank-you-very-much. He dropped her off and showed her where the happy couple kept the spare key, apologising that he had to go to work. She'd shooed him away as he promised to take her out for dinner that night, then settled on the couch with a book, enjoying the sunshine coming through the windows.
Sam got home first and they talked for an hour while he surprised her by making dinner. Jess came through the door, bearing a nice wine and fresh tomatoes. Sam had jokingly shooed them out of his kitchen, so the girls settled with the bottle of wine and talked decor and sight-seeing.
She slept heavily that night, tipsy and warm from the way Sam had buried his face against Jess' neck when Mary told her about the time he'd performed 'Our Town' at school.
"You were a drama dork! You told me Dean was lying!"
There was a cooked breakfast the next morning and Jess insisted that Mary take the car because she and Sam could walk to their classes from here and it was no problem. Sam gave her the number of Dean's friend Charlie who'd offered to show her around.
The brilliant red-hair, lazy smile and eclectic language of the young woman who showed up about an hour later wasn't exactly what Mary had expected. She quickly understood why Charlie and Dean got along so well, however, because Charlie was Dean had he been a girl. More or less. She was in IT and complained loudly about the cassette's in the Impala until Mary told her they belonged to hers, just to see what she'd do.
"Okay, that explains so much about Dean" she'd laughed.
Then she talked about Dean and Castiel, except the way she said it was more like Cas-and-Dean, and there was a big difference between the two. Mary wasn't sure exactly how to approach the subject. Luckily, Charlie broached it for her;
"So, like, you totally don't have to answer this or anything but has Dean said anything, you know...dreamy...about Cas?"
She tried to read the red-head's expression for a moment.
"Do you think there's something going on between them?"
Charlie shrugged.
"In a 'I may or may not be slightly in love with him' sort of way? I don't know"
She side-eyed Mary indiscreetly.
"Would you go all Deep South on them if there was something going on?" she asked, protectively. Mary turned and narrowed her eyes at her.
"Let me tell you something, Charlie; I love my sons. I would die for them. If something makes them happy, and that something isn't going to destroy them-" from the quick hardness in Charlie's eyes, Mary knew the other woman was aware of Sam's old demons.
"-then I will do whatever I can to make sure they get it"
Charlie was quiet for a moment, indicating a turn. They'd ended up taking Charlie's loud yellow rust bucket because Sam's car apparently had a mind of it's own and didn't like Charlie.
"You might have your work cut out for you. Coz Dean's...he's like Narnia deep in the closet"
"You think he's gay?" Mary tried not to sound too shocked.
"He has a really good sense of fashion, but no. I think he's, like, Cas-sexual or something"
Mary cocked an eyebrow in a way that made Charlie chuckle because she'd seen that exact same look on Dean's face.
"And what about Castiel?"
Charlie shrugged.
"I don't even think Castiel knows what he is. You're going to dinner at their place tonight, right?"
"Yes"
"Well, watch them. Anyone would think they've been sleeping together for months" she complained.
"You don't think they are?"
"I don't think they know" snorted Charlie.
Mary called Dean when Charlie was still in the car, listening with a slowly growing grin on her face as Mary cajoled Dean into inviting her to the apartment for dinner, rather than going out somewhere.
"Okay, you gotta high five that shit, lady, that was awesome!"
Castiel was a perfect gentleman and very handsome, with brilliant blue eyes and mussed black hair. He was wearing a dress shirt and slacks and looked nervous. She spotted a blue tie shoved into the back pocket of his trousers, like he couldn't decide whether to wear it or not, and Dean was forcing himself not to be flustered as he grinned over the six pack of her favourite beers.
The place was small and smelled a little like mildew, but the windows were open and brought the smell of the ocean in.
Mary perched on the arm of the couch and watched them interacting in the kitchen. Dean teased Castiel lightly and Cas would frown and sometimes stood too close to Dean. Castiel excused himself to the bathroom and Dean leaned on the bench, looking at her frankly. She smiled.
"Castiel's a charming young man-"
"Mom-" he cut her off gently.
"-You've been brainwashed by Charlie. There's nothing going on. We're just roommates, okay?"
Mary raised an eyebrow and reworked her thoughts. Charlie was wrong.
Cas and Dean had been sleeping together for months. At least. Dean had a tic in the corner of his mouth that he'd never figured out how to hide from her. She let the lie slide, however, but really: she thought she'd raised her boys better than to underestimate her.
They had a lovely dinner, and Castiel drove Mary home afterwards. In the Impala. Which Dean handed him the keys to. What was that old saying? If you're holding the keys to a man's ride, you hold the keys to his heart. It was the icing on the cake.
"Thank you for a lovely night Castiel"
"You're welcome, Mrs Winchester" he said formally.
She leaned over the console and kissed his cheek.
"My name is Mary, love. I don't think either of us need to stand on ceremony really"
It could have been a strange light from the dashboard of the Impala, or the couple of beers she'd had with Dean, but Mary was sure that Castiel blushed at the heavy emphasis in her voice. It was affirmation enough for her.
"Look after my Dean, Castiel. Though I'm sure you will"
He looked at her hard in the milky light. She'd noticed he had a habit of looking very directly at people—though, mostly Dean—and let him. She looked right back and finally he glanced away, out the windscreen.
"I swear...Mary. Thank you" he muttered. She paused before opening the door.
"I used to tell Dean that angels were watching over him. I'm glad he found one for real" she said and got out of the car. It took Castiel a moment to put the car back into gear and drive away. She watched him go with a little wave and shook her head.
"Did you have fun?" Sam asked as she slipped inside. He was sitting on the couch with a heavy textbook on his lap.
She kissed his head.
"You didn't have to wait up, darling. Yes, I did"
"So on a scale of one to sickening, how nuts about each other are they?" he asked as she walked towards the spare bedroom. She laughed in response and judging by Sam's chuckle, they were on the same page.
They all went out for dinner together on Mary's last night in California—as a family, Mary had insisted, making Dean's face burn as he scratched the back of his neck like he used to when she caught him kissing girls behind the big old tree in their front yard. Cas had sat between Sam and Dean and Jess sat between Sam and Mary. The mother watched with a glowing heat in her chest as Dean traded sharp, flickering glances across his plate with Castiel, who was far less discreet about watching her son's mouth around a fork of pie. Sam teased Castiel for his tie, Dean defended Cas, Jess rolled her eyes and caught Mary's with a scheming grin.
She was beginning to think her grand plan had backfired when she returned to Kansas without hearing anything about it from Dean, or Castiel for that matter. Everything was ready for the two of them to finally pull their heads out of their asses and admit their feelings.
To Mary's shocked elation, John had come to the same conclusion as she had. He'd struggled, he admitted, with the prejudices he was raised with but apparently Bobby beat some sense into him.
"He's my boy, and if this Castiel's good enough for you, than that's alright by me" he'd declared. She narrowed her eyes at him and inquired sweetly if she'd been sent to California on reconnaissance or as a birthday present.
John had winked.
"Hey mom"
"Oh, Dean honey, how are you?"
"Yeah, I'm good. How's things?"
Mary smiled and gestured to John to quieten down. It was a Wednesday afternoon and while it wasn't completely unheard of for Dean to call outside their tradition Sunday catch-up, she'd let John in on the grand plan, so he turned in his armchair to listen.
"Same old, same old. Your father's got some Impala parts for you next time you're home"
"Awesome. That's great...so, uh, listen; I'm not saying you had anything to do with it, but Sam swore on a stack of first editions that he hasn't touched it, so thing is, that little angel thingy of ours has been missing since you were around for dinner the other night"
Mary's face broke into a grin and John snorted, shaking his head. He turned back to the TV with a grunt of 'Boys thinkin' they can outsmart their mother'
"Well, sweetheart, I'm not saying that there's something going on between you and Cas, because if there were your father and I would love to have him for the holidays, wouldn't we John?-" she held out the receiver and he called out his agreement, which melted into a curse at a jump of static on the box. She settled the phone back to her ear.
"-but the thing is, if Castiel had been sleeping in his own bed, he would have found it under his pillow"
Castiel and Dean drove to Kansas together that holiday, arriving a few days after Sam and Jess. John shook the young man's hand and was surprised when Cas didn't cow. Apparently, Castiel's father was bigger and scarier.
Mary cried when Jess lifted her and Sam's hands off the kitchen table to show off her engagement ring. John clapped Sam on the shoulder. Dean hugged his little brother hard and turned around to kiss Castiel full on the mouth in celebration.
The day before they drove back to California, Sam gave Dean and Castiel a small porcelain angel. It made Castiel blush and Dean punch his brother in the arm, glaring accusatory at Mary.