spn ✩ the middle sister [part 1]
sam & dean winchester x oc!sister
author's note: so what if sam & dean had a sister with lorelai gilmore's personality? (things i think about in the middle of the night). since i don't have the time to write a series re-write, i worked on this long headcannon/mini fic. it will probably have at least 3 parts.
warnings/tags: canon divergence; spn canon violence; mentions of bullying, su1cide and death; angst; john winchester being father of the year (i’m being sarcastic); language; english is not my first language. trust the process!
⭐️ pics aren’t mine, credits to their owners.
🚫 please do not copy, repost or translate my work without my permission.
now, without further ado...
John and Mary’s daughter was named Camille, as a tribute to John’s mother, Millie. Throughout her life, though, she’s rarely been called like that. She was simply Mila.
She was two years younger than Dean and two years older than Sam.
At first, the-two-year-old Dean was reluctant to have siblings. Sharing his parents, especially his mom, seemed unfair since he hadn’t been able to enjoy them for that long. The night Mila was born that changed completely.
John led Dean into the Maternity Ward room where Mary cradled his newborn sister against her chest. Despite his short age, he remembered thinking she was the smallest thing he’d ever seen. When he stepped closer to introduce himself as her ‘big brother Dean’, Mila’s tiny little fingers curled around his slightly bigger ones, and from then on, Dean swore he’d always take care of her, no matter what.
Dean and Mila grew up side by side.
He was fascinated by her – her laugh; how smart she was, even for a baby; and the way she’d repeat everything he uttered. Whenever he had to introduce her, he’d say 'She’s my little sister’, standing a bit taller and his chest puffed out with pride. If he heard her cry, even in the middle of the night, he'd be the first one to comfort her.
Mila was just as captivated by her big brother. She’d follow him around the house, whether to play with him and his army men toys or simply to check what he was doing or where he was going.
Mila’s relationship with her parents also developed smoothly. Both John and Mary would always deny having any favorites, but it was crystal clear that Mary saved a certain softness for Dean, just in the same way John did for Mila. She was a complete ‘Daddy’s little princess’, as he’d often call her. Yet, she still found some bonding moments with her mom, like when she helped Mary bake chocolate-chip cookies or when they’d walk around their block on a summer evening.
Then, Sammy was born. Dean, already protective of Mila, felt the responsibility double on his small four-year-old shoulders.
Mila, at two years old, couldn’t quite grasp the concept of sharing her parents yet, so she’d sometimes tug, with a puzzled frown, at John’s trousers while he was rocking the baby to sleep, demanding some of his attention.
Dean, witnessing how John asked Mila to go to her room, promising he’d read something to her later, was quick to explain to her, while holding her hand for reassurance, that they were ‘the big kids’ so they had to take care of Sammy. Dean described it as if it were the coolest thing in the world, so Mila’s eyes lit up at her new role in the family.
Needless to say, after that fateful night in November 1983, the Winchesters’ precious family dynamic was forever shattered.
Dean’s freedom and innocence were replaced by duty and obedience the moment John told him to ‘watch out for Sammy and Mila’. That order became the core of his identity. He wasn’t just the older brother anymore. He was the one who had to make sure they were fed, bathed, and kept safe while their father was away.
As Mila grew older, and as John started to tag Dean along on the hunts, she had to step into the caregiver role as well. She carried that vow with pride, just as Dean did, but beneath all that, the ache of a boy and a girl who had been forced to grow up too soon, too fast lingered.
It was during her teenage years that Mila’s prominent features began to consolidate. Each day, she grew more and more like her mother – she had Mary’s eyes and smile as well as her gentleness. But she had also inherited her father’s stubbornness and anxiety. She was unmistakably her brothers’ sister, too. She shared Dean’s bravery and sharp wit, their reliable way of masking pain and fear, and she matched Sam’s restless curiosity and the hope that their world could orbit around something other than hunting.
It was also during this time that her relationship with her father became more strained. John deemed it almost impossible to look at Mila without seeing his beautiful Mary, so he banned Mila from hunting 'for her sake'. Instead, he’d always put her on research duty in the safe confines of whatever motel they happened to be at. At first, Mila accepted her place almost without question. Her hunger for knowledge made the old lore books and newspaper articles feel like a puzzle she had to solve to prove her worth to her father. But, as the years went by, the paper grew heavier under her fingers, and the motel walls tightened more and more around her until the room started feeling more like a cage rather than a refuge.
Doubts about her father’s stance slowly crept in when he started allowing Sam to go hunting. Watching her two-year-younger brother walk out the door with John and Dean stung more than she cared to admit. She did pitch the idea of joining them, at least on ‘milk-run cases’, but John would always brush it off, saying that he’d think about it later, but he never did.
Fed up with being the only one that stayed behind, only feeling useful when she had to pass information along or when she had to patch up her father and brothers' wounds, Mila asked Dean to secretly train her. “Hell, no. I’m not disobeying Dad. Are you nuts?” Dean snapped, his brows knitting together tightly. “Deano, come on! Think about it for a sec. Neither you nor Dad will always be ‘round to protect me. I need to know how to take care of myself if somethin’ happens. Don’t you think?”She had a perfectly reasonable, valid point. Dean huffed – that was all it took to convince him. And her puppy eyes, of course.
From that day on, whenever John was away on a hunt, Dean and Mila would get up very early in the morning to go to the nearest park so he could teach her hand-to-hand combat, how to identify the different creatures, and how to kill them. Weeks later, curiosity killed the cat, and Sam caught them sneaking out of the motel room, which resulted in him tagging along. Sometimes, Mila’d find herself wrestling against both her brothers, at the same time, 'for the sake of practice'. These training sessions usually ended up with the three of them lying on the grass, with their breath ragged and a big grin on each of their faces.
Digging through old books and newspaper articles wasn’t Mila's only skill. She definitely had the fighter’s instinct that ran in her family’s bloodline. Dean saw it in the way she’d learnt to anticipate his moves and in how resourceful she was when she was caught between the hammer and the anvil. Even Sam realized his sister was far more capable than John had ever given her credit for.
And then, the long-awaited moment came. Dean allowed her to go on her first hunt – her 17th birthday gift, as she liked to say. Not that he was 100% onboard with it, but they’d found a series of mysterious deaths in a boarding school for girls in the proximity of their motel, so she was the only one who would be able to get in. Besides, it wouldn’t take more than a weekend. So, John, being away on his own case, shouldn’t have any way of finding out either.
Once she was ready, Dean took her to the school, asking the Headmaster to kindly admit his little sister. Their cover story was simple: both of their parents had died in a tragic accident when you were younger, so your older brother had to step up and take care of you. Not that far from the actual truth, huh? As Dean charmingly looked into the older lady's eyes, he said he wanted to ensure that his little Beth had the best education possible. Mrs. Vernon ate every bit of the story up and started her registration with glassy eyes. Once everything was set up and she said goodbye to Dean, Mila had to blend in and talk to the other girls, ask around about what they knew and had seen, attend a couple of classes to keep an eye on the teachers, and check for any signs of what she might be up against. Later in the evening, she called her brothers to pass the information along. She found out that a year ago, five of the students had bullied another girl to the point she ended up taking her own life, so now, the spirit was probably coming back to get its revenge. That night, while everyone was sound asleep, Mila helped Dean get into the schoolyard, where this girl had been buried so he could dig her bones up to salt and burn them. Despite her enthusiasm to finish the job, she was crazy if she thought he would let her see a body. He still praised her for the great job she had done.
The following morning, Dean went to pick her up, using a not-so-believable excuse, but surprisingly, nobody refused to let her go. Once they were back at the motel with Sam, they bought some burgers and fries to celebrate her first successful hunt. Dean couldn’t contain a chuckle from escaping his lips when he caught her devouring her food. She threw him a questioning look.
“After all that crap you learned ‘bout good manners and ‘social etiquette’,” his fingers mockingly curled into inverted commas, “you end up eatin’ like that?” She huffed, but then she lifted both her pinkies up, holding her burger in a more lady-like manner. “Happy now? Man, being a lady is hard,” she exclaimed as she shook her head and then proceeded to give the burger another big bite.
The months, and then years, kept passing by, and Mila continued secretly hunting with Dean.
Everything was going fine – well, as ‘fine’ as it could be for the type of life they had, but then, one night, when it was just Sam and her at the motel room, he revealed she was thinking of going to college. The moment caught her by surprise but she wasn’t really shocked by the news itself; it wasn’t the first time that her younger brother said something about a life outside of hunting. She’d be lying if she said it wasn’t the first time she had ever considered one either. Working with Dean was ok, even a bit fun at certain times, but she was tired of going behind her dad’s back. Not that she hadn’t circled back on the idea of hunting now that she was older; the old man was too set on his ways and turned her request down again. So, she had been feeling like she was wasting ‘the best years of her life’ trapped inside a motel, without a real home, friends, a normal job, or any of the mundane things girls in their early twenties should experience.
And she would also be lying if she didn’t admit the other reason why she wanted a way out of her current life. She didn’t enjoy being around her dad as she used to. Although he always claimed to be ‘keeping her safe’, he was actually controlling her movements, her decisions, and almost how many times she took a breath. The obsession with finding the thing that killed Mary made him sharper over the years, less patient. Every time he said something, it felt like he was barking orders rather than speaking to his children. She also began disliking the way John spoke with or of Dean: dismissive, belittling, sometimes outright cruel. Dean took whatever his dad said without questioning because the man was his hero, but to Mila, it was clear John saw him more like a low-rank soldier rather than his son. The realization hit her like a blow to the gut: the father she once knew was long gone, replaced by a stranger whose voice she could recognize anywhere, but whose warmth had disappeared years ago.
Sam and Mila made the decision to go away together, and they wished to talk to Dean and try to convince him to join them, but unfortunately, John found out before they got the chance. He overheard how Mila reassured Sam that there was nothing wrong in pursuing his own dreams, and all hell broke loose.
“So you think you can just pack your bags and leave?” John’s voice thundered through the room, his anger barely masking the betrayal. “You think you can abandon your family?” “We’re not abandoning anyone, Dad. We just want something different.” Sam explained, using the same soft tone he employed with victims or their families when talking to them during a case. “Yeah, we can still help you with research and -” John interrupted Mila with a scoff. “Don’t you dare say anything, Camille.” He spat, deliberately using her full name as if it was just another weapon, a curse he needed to get rid of. “After everythin’ I’ve done to protect you, this is how you repay me?” Mila fell silent, her fists tightening at her sides and anger bubbling inside of her. But, when John turned around to ask Dean if he already knew anything about this, ready to tell him off, that was when she lost it. “Oh, no—no, no, do not dare bring Dean into this. It’s not his fault,” she found herself biting back. “There is no one to blame here. Hunting is simply not our thing.” She saw John open his mouth to speak but she cut him off immediately. “I’m not done talking. It’s your turn to listen.” She shot him a glare that seemed to pin him in his place. “I get it – whatever we’re doing here, we’re doing it for Mom, but this is no life, Dad,” she made a pause as she sighed, her voice breaking, “not for me, not for Sam, not even for Dean and you.” She searched his eyes, desperate for something: regret, softness, anything, but he had a habit of proving her wrong. “You wanna find that apple-pie life? Fine. Don’t dare comin’ back when it crumbles down.”
The youngest Winchesters left shortly after that fight. They could tell Dean was pissed off too – his jaw was tight and his silence weighed heavily with disappointment – but at least he pulled both of them into a hug before they walked out. It wasn’t too long, ‘no chick-flick moments’ as he often said, but it was tight, even a bit desperate, clearly not ready to let them go. Their father, on the other hand, was nowhere to be found, and this echoed louder than any words or screams.
Within weeks, Sam had already started studying at Stanford, aiming for a law degree, and Mila was able to get a job at the school’s library. She had also managed to find a small, affordable apartment near the campus. For the first time in years, they both felt their lives were moving forward, shaping towards something that resembled a happy and normal future.
Mila hadn’t stopped talking to Dean, though. He was still her big brother, and she loved him a lot. She usually called him once a month to check if he was still alive and to share her life updates. And Dean sat and listened. Because, despite disagreeing with her and Sammy’s decision, he could always detect the pang of guilt in her voice when she asked how he and their dad were doing, and, because he also loved her a lot, he couldn’t add any more pain to her plate. Besides, she was the only connection with his younger brother those days since he wasn’t so keen on talking to him. It seemed that Sam held a grudge against him for still being ‘Dad’s good little soldier’.
She had once or twice voiced the idea of Dean joining them. He could find a job he actually enjoyed and live with her until he found his own place, but Dean always shrugged it off, saying that somebody had to stay to ‘take care of the old man’. Their conversations would usually end with a ‘Stay safe’ and a toothless smile that masked everything left unsaid.
Over time, and away from the ghosts of her past, Mila grew up to be a quick-witted, charismatic and confident woman, who made everyone want to fall in love with her or be her.
Sam swiftly became the main receiving end of her playful yet sarcastic remarks and high levels of energy.
One regular Tuesday afternoon, Mila dropped by Sam’s dorm demanding to spend some quality time with him, as if they hadn’t hung out already during the weekend. Although he was busy studying for an upcoming test, he still invited her in. She said she was going to quietly watch TV in the small living room. Sam should’ve known better than to believe her. “Oh, the news is on!” She turned the volume louder than he would’ve liked. “For our top story tonight,” she started speaking as if she were a news reporter, “a grisly horrible thing happened in a small town where no grisly horrible things ever happen. Everyone shocked!” She talked over the actual reporter’s voice, eyes fixed on the screen. “Wonder if it was actually a werewolf or a wendigo.” Sam sighed, trying to bring his focus back to his textbook. Seconds later, Mila turned off the TV and tossed the remote control on the other side of the couch. “Hey, let’s get ice cream!” She exclaimed before getting up from the couch to walk towards her brother. “I’m bored…” As he paid no mind to her, she knocked on his book. “Hello???” “Mila, I’m studying,” Sam replied, his tone more serious than usual. “Yeah, but I’m talking ice cream,” she repeated, as if she were explaining the best idea ever. “Can’t you take a break?” “I can’t take a break right now.” “Ok… when?” She threw him a hopeful smile. “What are you, 4?” He retorted, slightly more annoyed. “No, I’m hungry!” She protested, pouting at him. “Well, there’s some leftover pizza in the fridge.” “But it’s cold.” “Then heat it up.” “But it’s not the same.” “Camille, go to my room.” Sam almost yelled, as if he were a parent telling off his kid for her insistent behaviour. “Wow, nerds are mean!” He sighed for the second time. “Tell you what… if you let me study now, we’ll go out for dinner later. It'll be on me.” “Alright, you’ve got yourself a deal, mister.” “Good.” She started backing away, but then she turned around again. “So, I’m sorry. Where have we landed on the whole ice cream issue?” Sam rolled his eyes, grabbed all his books from the table, and went to his room, slamming the door. Mila stood there, watching the door with an incredulous look on her face. “Ugh, guys are so sensitive these days.’
Not only did Mila match Dean’s devotion to food, but her love for coffee was extraordinary, too. She started drinking it from a young age, during all-nighters spent scanning through lore books or after long drives in the Impala, when she had to push through the day without any proper sleep. Over time, it became so much more than a drink. It became her ritual, her lifeline, the only constant that followed her from the crappy motel rooms to her own apartment and the campus library. Sam had actively tried to save her sister from liver failure, offering her tea, but it was pointless.
“Sammy – please, please please!” She begged, handing him her mug, her puppy eyes making a stellar appearance. “How many cups have you had today?” “None.” She replied quickly, but he wasn’t buying it for one bit. “Plus?” “Five… But yours tastes better!” “You’ve got a problem.” “Yes, I do.” She put the mug straight in front of his face this time, batting her eyelashes at him. Sam sighed, finally understanding how Dean hardly ever said no to her, and took the mug from her hands to fill it up, not to the top, but enough that she’d be content. “Junkie.” “Angel.” She said with the biggest smile on her face and took the first sip. “You’ve got wings, baby brother.” She threw him a wink before going back to the living room where she had left her book open around page 100.
Then, one of the days Sam had been unnecessarily dreading arrived: the day she'd met Jess, his girlfriend. He knew Mila would like her; how could anyone not? Jess was charismatic, optimistic, and made Sam want to be a better man every day. She also had a particular sense of humor that surely wouldn’t go unnoticed by his sister. But he couldn’t avoid doubts and old fears from creeping in. When the moment of Jess and Mila meeting finally came, it went worse than he had pictured it.
“So this is the famous Jess,” Mila said, her tone dripping with mock suspicion. “I’m actually glad you’re not a figment of my brother’s imagination.” “It’s soo nice to finally meet you, Mila!” Jess replied enthusiastically while she gave her a quick hug. “Honestly, I’m glad I’m real too. Sam would crash and burn without me.” “Ohhh, good luck trying to save him from turning into a full-time robot. That’s the real challenge.” She linked her and Jess’ arms and got closer to her, as if she was about to reveal a secret. “He’s been practicing his ‘serious face’ since he was twelve. It’s exhausting.” “I knew this was a mistake.” Sam fake-groaned, faking betrayal. “You two have known each other for five minutes, and you’re already plotting against me.” “You'd better get used to it, baby brother. You’re officially outnumbered.”
Not so long after, Jess invited Sam and Mila to spend Thanksgiving with her and her parents. It would be Sam’s official introduction as her boyfriend. Mila would be there for moral support. And the free food and wine, of course. At some point, they were doing the typical small talk about what they did for a living, and Jess’ mom asked Sam about his degree.
“So, Samuel, you want to become a lawyer, right?” “Uhm, you can call me ‘Sam’, ma’am.” He offered her one of his sweet smiles. “And that’s correct. I’m in my third year.” “Good for you, honey. A good education is the most important thing in the world, after family.” “And pie.” Mila let the comment slide past her lips before she could even process it. The room fell into an uncomfortable silence while Sam shot daggers at her from across the table. “Sorry, just a joke.” She clarified, and everyone nodded before going back to their plates. Jess, however, stifled a laugh and shot her a look that said ‘Don’t worry, I get you’. It was true. Mila loved pie, maybe as much as she loved her brothers and coffee. She instantly thought of Dean and how she hadn’t spoken to him in quite some time, which made her a bit sad. She made a mental note to call him later in the evening.
Fast forward to a random Friday night in 2005, Mila was coming back home from her shift at the library when she felt somebody following her steps. Her old hunter instinct kicked in, and she took a different path to double-check if the stranger was actually following her. It turned out they were. She hid in a dark corner, trying to keep her breath steady. When the person passed by, in one swift motion, she grabbed them from behind, pressing the sharp, cold edge of the blade she carefully kept in her boot against the stranger’s throat.
“Why the hell are you followin’ me?” she hissed, her voice low and as sharp as the knife. “Mila, wait. It’s me!” Her eyes widened as she recognized the voice. She loosened her grip just enough to see the face in the dim light. “Dean?” Relief and anger collided in her chest. “You idiot! Couldn’t you call like a normal person? I almost gutted you.” He gave her a sheepish smile, though his eyes were tired. Mila wrapped her arms around his middle while his own slipped around her shoulders, and he kissed the top of her head. “Y’know I like makin’ an entrance.” “Why are you here? Did somethin’ happen?” “It’s Dad. He’s on a huntin’ trip. He hasn’t been home in a few days.” He said with the most serious tone she has ever heard him use. “Are you sure he’s not just -,” She didn’t want to blatantly say ‘ignoring you’, but it wouldn’t be the first time. “No,” he interrupted her before she could find the right word. “He wouldn’t spend so much time without callin' or textin'. You have to help me find him.” “Dean…” she sighed. “Even if I did help you and we found him, I don’t think he’ll be very happy to see me… not after what I’ve said to him.” “That’s water under the bridge, Mila.” He gave her an apologetic smile. “I know you think he was disappointed in you, but he never was. Not even in Sammy. He was just scared.” “What are you talkin’ ‘bout?” “He was afraid of what could’ve happened to the two of you if he wasn’t around. But, even after you left and you weren’t talkin’, he used to swing by Stanford and your place whenever he could… to make sure you were safe.” “How - Why haven’t you told me any of this? Have you talked to Sam?” Dean shrugged. “It’s a two-way street. And he hasn’t been picking up his phone. So, are you gonna help me or what?” “Yeah, but we need to get Sammy too.”
Sam put up more of a fight when his siblings tried to convince him to go with them, especially because of his interview the following Monday, but Mila assured him they would make it back on time for that.
Sooner than later, the three Winchesters got in the Impala and started driving up to Jericho, California, where their dad had been working on a case for about a month.
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end note: i'm sorry i had to end it like that, but tumblr wouldn't let me include all the scenes i wanted for the first part so it made more sense to divide it there.
what do you think? did you like it? would you be interested in a part 2?
i know it's still pretty early, but do you like ila's character? what do you think about her relationship with the three winchesters?
thank you for taking the time to read it and if you liked it, please leave a reblog, like and/or a comment. i’d love to read your feeedback and interact with you ❤️
lots of love,
lina.
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