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67midnightwriter · 4 years

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Bygone: Teach Me

A/N: This was originally intended for @thoughtslikeaminefield for her birthday before the world exploded. It was intended to be a quick one shot, but as I was writing I fell in love with Dean, Leia, and Cas’ relationship, so this will end up being a snapshot series. It won’t be written in order, but eventually it will all be written lol. Thanks to @mskathywriteswords for the deep beta!

Dean x OFC x Cas no destiel

Warning: feels and squirting

Smut

W/C: 4,269

There are many things Dean Winchester is good at: drawing out both pleasure and pain, locating both good drink and good food no matter where you plop him down, shrugging off compliments he’ll never believe he really deserves, and battling demons, of both the metaphorical and physical varieties. These are the things he (mostly) prides himself on, the base stones with which he builds the foundation of his character. Good or bad, they’re solid and steady through the storm of time.

He won’t admit it, but among the other qualities lays the fact that he is a good teacher. One might even venture to say that he is an excellent teacher, with seemingly endless pools of kind patience, an uncanny ability to know how to reach even the most challenging and troubled of students, and oceans of knowledge from which to quench the thirst of the curious. It’s his unintentional personal oversight of this key flagstone that has birthed the confusion knotting his forehead currently.

“Look Cas, I’m honored, really, I am...” Dean’s hand runs through his hair and then down his face, a nervous habit he’s picked up over the years, though he’s not sure where or when. He takes a deep breath before gathering the courage to continue. “But when I told you some things are better learned from watching, this...” He gestures to the room, unable to articulate the words he needs, unsure if any are actually needed, “is not what I meant.”

“I need you to teach me.”

Dean tries to keep his face blank, but it has a habit of thinking out loud. His eyes grow wide, his eyebrows fly high, and his bottom lip ends up pinched between his teeth to hold in a startled laugh. He steadies himself with a deep breath, slowly letting it out of his nose while he counts to ten.

“Cas, man, it’s pretty self explanatory…”

Leia, currently lying back on the bed she shares with Cas, her honey eyes taking in the awkward exchange between Dean and his best friend. Her deep red hair cascaded over her shoulders like a mane of fire, as she chortled over Castiel’s unamused huff and eyeroll.

“Dean, I’ve been watching humans mate and reproduce since before they were bipedal. I understand and am perfectly capable of bringing Leia pleasure through standard sexual intercourse.”

Dean suppresses a wince over Cas’s blunt wording; even years of friendship can’t take away the resounding feeling as though he’s talking about sex with a parent.

If he’s seen so much, shouldn’t he be teaching me?

The unwelcome thought crosses his mind, paired with an image of Cas in a full bodied latex suit, and he physically shakes it away.

“Then I don’t understand why I’m here.”

“Cas, I think you’d better just show Dean. It’ll be easier that way.”

Castiel frowns as he considers this, nodding as he settles on a decision. “I suppose you’re correct. Dean, may I?”

Dean closes his eyes to think, rubbing at his hairline like it will help ease his thoughts. He realizes the confusion is going to eat at him until he barges back in and confronts them anyways, and decides that he’d rather skip the forty minutes of pacing and get straight to the point. He still has a list of things to get done today, one that leaves little room for such distractions. “I guess. Let’s get this over with Feathers, I’ve got guns to clean.”

Cas’ lips thin at Dean’s use of the nickname, but he moves past without comment. “You might feel mildly disoriented.” He presses two fingers to each of Dean’s temples, and the world around Dean shimmers, causing his stomach to roll. His eyes close against the sensation, and it vanishes before he can even be sure he really felt it to begin with.

Dean opens his eyes and finds himself sucked into one of his favorite memories; quite literally. His lips are sealed around Leia’s clit as she writhes underneath him, her cunt clenching around his fingers as she cums. He doesn’t stop, even when she tries to pull away. Instead, he shifts the arm not currently three fingers deep, and pins her hips in place. She breaks from panting to whine his name, high and desperate, but he knows she’s been holding out on him. Her thighs squeeze, one on top of one shoulder, one underneath the other, and he replaces his mouth with his thumb so he can turn and bite the thigh against his ear. He’s rewarded with a sharp, ragged gasp, his thumb circling relentlessly as his fingers push against her g-spot. Her shoulders lift part way off the bed and for a moment she looks like a marionette, her eyes open but unseeing, her mouth hanging slack. He can feel her whole body tensing around him, and he can’t help but grin.

“Come on, Honey, let go for me,” he drawls, his accent thick and voice ragged.

He can feel her let go with his finger tips, and his eyes study her face as his skin tingles in a mix of awe, pride, and lust. Castiel chooses that moment to rip him back into the present, and he uses the guise of disorientation to close his eyes and steady his beating heart. His fingers twitch at his side with the urge to wipe phantom moisture off on his jeans, and his cock stirs in his jeans. He rattles off the safety features of the newest Dodge minivan in his head, willing an awkward erection away.

Traction control, tire pressure monitoring, rear child safety locks.

Since the universe decides against opening a black hole directly beneath his feet, Dean opens his eyes. He looks first at Leia, her warm eyes filled with concern, before turning to meet Cas’ cool blue gaze.

“Will you teach me?”

“Cas...” Dean runs his hand across his face, his eyes flicking between his friends. “I don’t know. Even if I could, I’m not sure how I would.”

“I could always take the information straight from the source.” Castiel, Dean was sure, was immune to any and all awkwardness.

“Castiel! I told you that if Dean didn’t want to help, you would let him go, without any brain spelunking.”

“If you would let me use my grace-”

“You can use your grace to- nevermind. I don’t want to know.” Leia smirks and shoots Dean a wink, and he shudders mentally.

Dean sighs again, his mind battling with its southern counterpart, and blessedly Castiel and Leia stay silent. He gazes at the angel before him, thinking of all the times he’s been saved by his hand, how Castiel has rarely ever asked him for anything but trust. He thinks of Leia, who has been by his side for the better part of 20 years, spent the prime of her life trying to keep his ass alive, and how much she deserves someone who could give her all the things he can’t (or in this case, all the things he can) do. She’s happy with Cas. Cas wants to give her everything she could want. Dean refuses to think about where else Cas would turn for advice, and realizes the decision has been made.

“Alright. If everyone is okay with this...” Dean gestures to the room again, still unsure there are appropriate words to describe the situation. “I’ll help you.” Leia smiles softly at him, relief washes over Castiel’s face. Dean swallows hard, and thinks there might be a rock settled in his stomach. “How…?”

“Some things are best learned by watching.”

Of course that would be the one piece of advice Castiel would latch on to.

“Right. Okay. Well…”

Attuned to his emotions after so many years living beside him, Leia gets up from the bed and stands between him and Castiel. Headstrong, with no room for nonsense, she grasps the open sides of his flannel, pulls him flush against her body, and presses her lips to his.

It’s been eleven years since they shared a kiss, but it seems as though no one informed their mouths. They fit together the same, and Dean finds himself running his hands up her arms, across her back, pulling her closer, one hand traveling up to the back of her head. She relaxes against him, and it would be so easy for Dean to pretend Castiel isn’t there, to believe that they never fell apart, to find safety and solace in her touch once more, to break down the walls he spent so long building that he can no longer remember if they’re for her sake or his.

He stiffens, but Leia already knows. She kisses her way across his jaw on up to his earlobe, nibbling softly just behind the curve. She pulls his earlobe with her teeth, before speaking in a heavy low voice.

“It’s okay, Dean. I want this. Please.” She breathes the last word. Dean wonders briefly if he imagined it, before his resolve crumbles.

Dean nods, not trusting himself to speak. Leia slips his shirt from his shoulders, and he lets it fall to his feet. He stops thinking, instinct taking over. Her shirt joins his, and he grins when he finds she’s decided to forgo a bra. He backs her on to the bed, his lips trailing hot against her skin as he makes his way up to meet her lips. Castiel shifts behind him, the rustling of his trench coat as he places it on the back of the chair reminding Dean that he’s doing this for a reason, not just living out fantasies. Dean gives control back to his brain, and slows the urgency of his kisses while wondering how to give Castiel a step by step guide on how to make his girlfriend squirt.

“The first-“ Dean’s voice is too low, too thick with lust, so he clears his throat and attempts to continue. “You gotta start-“ Leia stops his stuttering with a kiss.

“This isn’t going to work if you spend the entire time stumbling over a play by play like it’s your first day on ESPN.”

Dean hangs his head in defeat, the tips of his hair brushing against Leia’s nude chest as it rises. An apology is clawing its way out when Castiel speaks from a spot behind him.

“Just pray to me.”

Dean turns to meet the cool blue gaze over his right shoulder, and Cas nods at whatever emotions are swirling over his own eyes. Dean finds no doubt in Cas’, no uncertainty, just oceans of trust with swells of excitement that Dean is still sure he doesn’t deserve. He turns his attention back to Leia, who turns a similar trusting, warm gaze on him. She smiles, lips puffy and face relaxed in a nostalgic lust.

“Okay?” Her voice is sweet, safe, and Dean smiles as the rock in his stomach cracks.

“Yeah. Okay.”

Dean leans in for a deep kiss, invading her mouth with an expert tongue before making his way down her neck. He prays as he goes along, explaining every touch to Castiel. Leia moans beneath him, leaning in to his touch as he strips her, blunt nails coaxing goosebumps to her skin. He trails kisses and bites down her body, the thumb of his right hand brushing over her nipple, his left resting on her hip as he settles between her thighs. She feels hot and and solid beneath him, and the way she’s relaxed, honey eyes half lidded and full of lust, calms him. Dean bites the inside of her thigh, soothes it with a kiss, and then the absurdness of what they’re doing hits him.

He nearly laughs. It creeps up his throat from deep inside him, threatening to break this tender moment, and he’s not sure that he can hold it in.

If anyone would have told me, at any point in time, that I would be praying to an angel while demonstrating how to make his girlfriend squirt-

Leia’s hands in his hair bring him back from the edge of hysterics. She pulls, hard enough to move his head, and he twists her nipple in retaliation. She hisses, arching, and she chuckles.

“Focus, Cowboy.”

Dean grins and gets to work. He tightens his grip on her hip, uses his tongue until she’s keening for more, pulling his face closer and fighting against his hold to grind against him. He squeezes her nipple once more before he adjusts himself, latching on to her clit and thrusting the two middle fingers on his left hand in her sodden cunt. He can feel her clenching desperately already, and within a few moves of his fingers she’s cumming.

Once the first one is out of the way, the main key is to keep going, Cas. No matter what she says, or if she tries to pull away, keep going.

Her low pitched guttural groan fills the room, and her thighs clench around his head. He can’t help but chuckle, letting her hip go long enough to force his left arm between her thigh and his ear, pressing the length of his forearm down across her hips and grabbing tight to her right. He adjusts, filling the emptiness where his left hand had been with his right, kissing and nipping at her thigh while rubbing her clit in rough circles with the pad of his thumb. She fidgets, trying to pull away from the overstimulation, desperate whimpers falling sweetly on the air, her body trembling around him. She begins to buck, fighting to pull away, and he can sense Cas stiffen behind him.

This is where you make your mistake. She’s so close Cas, you can feel her tightening and trying to fight it, but if you really want to make her happy you’ve got to push her into it. Rub her gspot harder, make sure you never let up on her clit, and tell her what you want. She loves that.

“Come on Honey,” Dean purrs, his voice deep and heavy with lust, his accent dripping from his words. “Let go for me.”

Present mirrors the past, and Dean is awash in deja vu.

Leia’s mouth opens, her whines cutting off to a silent scream. Dean can feel every one of her muscles clenching, her fingers gripping so hard around the bedsheets that the fabric is protesting. The pressure continues building, her shoulders coming off the bed of their own accord, turning her into a marionette of pleasure, a memory come to life. He can feel the release on the tips of his fingers, bringing a grin to his face.

“That’s my girl.”

Her silent scream breaks into a desperate cry as her release sprays down his arm. She gasps, falling apart from the inside out. Dean runs his hands up her body as she finally relaxes, the human version of a spring that’s been wound until it snaps. She collapses back down on the bed, her legs extending to either side as her muscles relax. Her chest heaves as she pulls in desperate gasps of air, aftershocks of pleasure still vibrating through trembling extremities.

Dean smiles softly at her, pressing a soft kiss to her thigh before standing. His cock aches, his erection pressing uncomfortably against his jeans that seem two sizes tighter than this morning. He backs away as Castiel sheds his trenchcoat and settles on the bed, pulling Leia to his chest and murmuring praise between kisses. Dean watches as he feels jealousy blanket his shoulders. It’s her soft begging that finally gets his feet moving again, though his eyes and ears stay fixed on the couple in the bed, his heart aching for it’s happy ending. Sorry buddy, you’re going to have to settle for another long shower.

“Dean.” Her voice reaches him as his hand settles on the door handle, a tangible echo, just as sweet as it was when she was his. “I need you too.” He stops and turns, his heart rate skyrocketing, his cock twitching excitedly. “Please.” She’s always begged more with her eyes than her words, and Dean sees that old flame brought back to life, an ember fanned to raging inferno.

Every fiber of his being is singing all the praises Heaven doesn’t deserve, but still he hesitates.

“It’s okay, Dean.” Blue eyes ground him, just as safe and steady in the bedroom as they are on the battlefield.

Dean turns from the door, his hands already working at the button of his jeans as he floats back toward the bed. Their clothes are gone before his jeans make it over his hips, and he decides that maybe grace has more advantages than those that are tactile. He pauses at the foot of the bed, the logistics overwhelming his lust addled brain. Shower sex isn’t the only thing that’s complicated. Hell is still just hell, though.

“What do you want, Princess?” Castiel murmurs low into Leia’s ear, and Dean is close enough to see the bumps rise on her skin.

“Deep.” Her tongue stumbles over the single word, her endorphin overloaded brain struggling to process anything more than action and touch.

“I need you to ask for it.” Castiel rolls, throwing one of her limp legs over his hip, dipping two fingers into her cunt and making her eyes fly skyward. “Or you’re not going to get what you want.”

Dean’s cock twitches against his abdomen, and he slowly strokes himself as he watches Castiel’s fingers move, listens to the wet that he caused, feels his body heat under the angel’s sharp gaze.

They seem to spend an eternity in that moment, washed in lust, excitement, and anticipation. Everything is tense, but Dean feels lighter than he has in years as he allows himself to stop thinking and simply wait to be given a command.

“I want Dean to fuck my ass,” Leia finally manages to gasp out as Cas continues to tease her. “While I ride your cock.”

Castiel pulls his hand out and settles her slowly onto him. Leia gasps, her hands gripping his shoulders as he guides her hips down, inch by agonizing inch, Dean’s mouth falling open and a grin crawling across Cas’ face as they both watch. Cas maneuvers them until they’re at the end of the bed, his legs hanging over the end and her knees propped on the edge. Dean runs his hand down her back, along the curve of her spine, her skin soft and smooth beneath his time roughened palm. He cups her ass, firm from decades of hunting, and his thumb rubs over a wayward freckle. He spreads it, his tongue darting out to wet his lip as he takes in the view before him, savoring it.

“Dean.” Castiel’s voice breaks through his trance, and when he finds that sharp gaze, Castiel is holding out a bottle of lube.

Dean nods as he accepts it, his tongue too heavy in his mouth to form words. He lubes his fingers, teasing her hole before pushing one in. He would gladly go to hell again to hear the moan that left her lips as she pushed back onto his hand. He slowly works her open with one hand as he strokes himself with the other, his bottom lip pinched between his teeth.

“Dean, please I need you,” Leia whines, her forehead settled on Castiel’s shoulder as the angel busies himself kissing and nipping her neck, teeth grazing one of her favorite spots.

“Okay, darling. I’ve got you.” He preps, takes a deep breath, and pushes forward.

It feels like coming home. Dean gasps and he’s surrounded by tight heat, his hands digging into her hips, his legs settling against the bed, sandwiched between hers and Cas’s. Dean, a corner of his mind once worried about the possible awkwardness of sharing his past love with her present one, the small rational part of his brain speeding through the consequences of fucking his best friend’s girl while he’s in the room, is suddenly certain that if he moves, he will cum instantly, something he hasn’t done since he was 17.

Dean tries to think of a witty comment, the sudden vulnerability of the situation overwhelming him, the need for a protective wall of humor urgent, even though he knows it will destroy this precious moment. His mouth opens, his tongue threatening to sabotage this perfection, but instead of words Dean moans incoherently as Castiel grabs his hips and forces him to move in sync with his own thrusts.

Dean decides that it’s okay to turn his brain off. He stops thinking, and instead he starts feeling. He reaches a hand around to rub at Leia’s clit, tightens his hold on her hip as she falls limp, her body unable to hold itself up between them. Tears are rolling slowly down her cheeks, drool slipping out of the corner of her mouth as her eyes unfocus and she succumbs to the intense pleasure.

“Such a good girl.” Cas’ voice is deeper than Dean imagined would be possible, rough and breathless as he throws his head back. “More, Dean. Harder.” Cas guides Dean’s movements, pulling his hips in. Dean plants his feet, adjusting the angle of his thrusts, giving himself leverage for more powerful thrusts, pulling a deep moan from Cas’ lips. “Yes, Dean, good.”

Dean’s balls tighten at the praise, his thighs begin to burn as his pace quickens, desperation driving him. He feels Leia cum again, hears her hiss at the end of a silent scream, but it seems far away. His only focus is chasing the high, getting relief from the pressure that’s settled on his groin, because right now everything is tightening, every muscle is tensing. Dean grasps both of her hips in his hands, his knuckles turning white as his pace begins to falter. He hears Castiel call out, feels the hands on his own hips tense and relax, and finally he’s breaking.

Time is meaningless. He falls onto the bed, years of tension seeped from his body. He feels like he’s floating, relaxed and happy, a constant pain numbed in a way that whiskey cannot help. Castiel cleans up Leia with a snap, and she wakes enough to cuddle against Dean, nuzzling her way beneath his arm just like she always has. Castiel lays behind her, bringing with him a sense of safety Dean craves.

------

Dean is staring at the gun in his hands, but he hasn’t moved to clean it. He glances at the clock, surprised to find that he’s been unfocused for fifteen minutes. He’s not been able to make it through a quarter of his list, but he can’t bring himself to count the day as wasted as he normally would. He’s been trapped in his mind today, bouncing between nostalgia and present, doing his best to not linger on the new, overwhelming amount of ‘what-if’s and ‘what does it mean’s buzzing around his mind.

He finds himself falling into another spiral, wondering if this was a one time romp, or if he’s not the only one with unrequited feelings. If Leia still has feelings, what does that mean for Cas? They make each other better, they need each other, and Dean does not have enough room in his mental guilt chest to add that.

A small knock at his door makes him jump, and he clears his throat and busies his hands before telling them to come in.

“Dean?” Leia’s voice is tentative, her eyes troubled. She settles herself on his bed, and Dean forces himself to stay where he is at his desk. His heart is racing nearly as fast as his mind, anxiety restricting his lungs and drying his mouth. “Can we talk?” There it was. The death sentence.

“Of course.” Dean zeroed in on the gun in his hands, focused on the familiar movements.

“I talked with Cas about what happened this morning. It...” She paused, biting her lip as she struggled with what to say next. A hundred scenarios began playing through Dean’s mind, each one worse than the previous.

It was a one-time thing. It was a mistake. It was something I regret. It was the final straw, I can’t do this anymore, we’re leaving.

“It stirred up some emotions that I buried a long time ago. I hope that I don’t offend you by saying this, or that this makes you uncomfortable.” She took a deep breath, and Dean began to oil the pieces of his gun, glad to have something to do with his hands so that she couldn’t see them tremble as he waited patiently for her to continue, every muscle tensed and prepared for life’s usual kick to his metaphorical (and sometimes physical) balls.

“I still love you, Dean. I’ve talked it out with Cas. If you’re interested, I’d like to … make sure this isn’t a one time thing. Cas is okay with this. He understands that each of you are important to me, and each of you fulfill different areas of my life. I want you both.”

Dean’s hands stop moving. He distantly hears the piece of gun clatter to the floor. Every thought screeches to a halt as he looks up, searching her face for any hint of a lie or a prank. Instead, he finds raw vulnerability, one he had chased away long ago. The walls he had watched her build between them over the years, even the bricks he had had purposefully caused her to lay, were now mere crumbles of brick and mortar.

A smile begins to slowly spread across Dean’s face.

Taglist:

@impala-dreamer @adoptdontshoppets @supernatural-idjit-95 @team-free-will-you-idjits-67 @missjenniferb @tumbler-tidbits @maddiepants @crashdevlin @thoughtslikeaminefield @there-must-be-a-lock @cracksinthewalls @stunudo @mskathywriteswords @rockhoochie @itmighthavebeenintentional @wanderingcas

#Supernatural Fan Fiction #supernatural #spn fic #spn fanfiction #spn fanfic #dean winchester #castiel #Smut #Supernatural smut

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waywardnerd67 · 6 years

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Destiny

Summary: A mysterious woman is emails Sam Winchester needing to meet with him and Castiel. When they find out who she is and where she is from they must decide how to handle telling Dean and (Y/N). The shock of the truth and a great threat to the world has all the Winchesters panicking. The fate of their futures depends on this mysterious woman. Characters: Dean Winchester, Sam Winchester, Castiel, Samantha Mills (OFC), Reader Pairing: Dean x Reader Warnings: Angst/Tiny bits a fluff thrown in Word Count: 4126 A/N: I was listening to Kelly Clarkson’s “Piece by Piece” and this story popped into my head. The song has a lot of meaning to me since my own dad and I did not have a great relationship. The point of view is a little different so I hope everyone will like it. As always this is unbeta so all mistakes are mine. Likes, comments and reblogs are splendid and I will love you doubly for them! Enjoy!

Walking into the small diner, she looked around spotting the two men she was meeting with. Her stomach churned as she approached the table, “Hello Sam, Castiel.” She said as she sat across from them.

They looked to each other then back at her. “How do you know us?” Sam asked the ache in her heart growing as she stared at the man she had admired for so long.

“You can say that I’m a distant relative of sorts. Look, I don’t have all the time in the world to explain everything to you. The world is in great danger as is all of our futures.” She looked to Castiel smiling feeling more at ease with him there.

Sam sat back holding up his hands, “Look I don’t know who you are or how you got my email address but I think you better start telling us everything.”

“Cas, press your fingers to my forehead and see who I am. I trust you completely if you tell me to tell Sam everything.” She said closing her eyes.

She felt his fingertips touch her head hesitantly and then she became lightheaded for a moment. When she opened her eyes again his deep blue eyes were wide staring at her.

She took his hand, “Cas should I tell him?” she asked as he looked bewildered then nodded. She looked back to Sam who had his forehead scrunched and arms crossed as she took a deep breath.

“My name is Samantha Cassie Winchester-Mills and I am your niece from the future.” Saying it out loud sounded ridiculous to her and from Sam’s expression that is how it sounded to him as well.

He scoffed glancing over to Castiel, “This has to be a joke, right Cas? She can’t possibly be… wait did you say my niece?” He snapped his head back to Samantha who nodded.

“My father was Dean Winchester and my mother is (Y/N) Winchester. I am the oldest of their two kids, my brother’s name is Henry Bobby Winchester.” She explained as Sam sat back taking all of it in. She knew it was going to be difficult convincing them of who she was and if she needed to, she had a last resort to use.

“Sam, she is telling you the truth. Looking at her now, I can see Dean and (Y/N) within her.” Castiel said as she smiled at him.

She leaned forward, “I know this is hard to wrap your head around, but thirty years in the future the world is at war. Lucifer is back and ruling most of the world, hell and heaven has shut its doors to everyone. I need,” she paused thinking of Henry and swallowing the lump in her throat, “I need to know how to get Lucifer out of my brother so I can save the world.”

Sam’s jaw slacked for a moment before stuttering, “Lu-Lucifer back?”

She nodded, “Yes and I need to save my brother no matter what the cost is.” Samantha looked up into her Uncle’s hazel eyes watching as the shined over from holding back his emotions.

Samantha followed Sam and Castiel through the familiar Bunker door and she looked out over the landing memories flashing before her mind. She missed the Bunker a lot, but in the future, it was just a heap of concrete piles destroyed within the first year of the war.

“Are you okay, Samantha?” Castiel asked her as she smiled softly nodding.

As she walked down the stairs she stopped suddenly hearing her mom’s voice echoing throughout the corridors. Samantha bit her lower lip nervous reminding herself that even though they were her parents they also were not yet. Taking a deep breath, she walked down into the War Room standing close to Castiel as Sam went to get who would be her parents.

Seeing her mom at the same age she was made her smile brightly. She was beautiful with her long (Y/H/C) hair and soft green eyes. When Dean came from the far corridor by the library, Samantha sucked in a deep breath. The anger, resentment and emptiness she felt most of her life hit her like a tidal wave. Her hands began to tremble and bile was rising into her throat. She expected to have some kind of reaction to seeing him again but she was not prepared for how overwhelming it was.

“Cas, who’s your girlfriend there?” Dean asked as she balled her fists at her side. (Y/N) smacked Dean’s shoulder playfully.

Shaking her head, she came up to Samantha sticking out her hand, “Don’t mind him. I’m (Y/N) Winchester and that man-child is my husband, Dean. What is your name?”

Samantha shook her hand and looked to Sam who spoke up, “I think we all need to sit down for this.”

They all took a seat around the large map table as Sam explained everything. Samantha watched as (Y/N) placed her hand over her mouth and instinctive touched her stomach. No one else seem to notice the gesture as Dean’s skeptical face narrowed his eyes at her.

“This is crazy. I know we’ve traveled to the past before, but this is beyond crazy. How do we even know this woman is who she says she is? She could be anyone.” Dean’s disbelieving tone sent her anger sky high as she reacted before thinking.

“Well, it’s no surprise that you wouldn’t know your own daughter if she slapped you across the face. You sure in the hell would not know your son who, by the way, is a meatsuit for Lucifer right now. If you don’t want to believe me that’s fine, but if family means so much to you then you will help me save my brother!” She yelled standing up and walking off towards what would be her room.

She heard her mom’s voice called out to her, “Samantha, stop.” Immediately, she stopped in her tracks and turned around seeing her mom gasp.

“(Y/N), how did you know her name? I never said her name.” Sam asked stunned as Dean looked to her in a similar fashion.

(Y/N) looked to Dean and gently took his hand placing it on her stomach, “I’m six weeks along. I just found out a couple of days ago and have been planning out a way to tell you.” She said softly.

Samantha walked back over sitting back down next to Castiel. Dean was motionless as he stared at (Y/N). Samantha could see his hand trembling against her stomach as (Y/N) had tears coming down her cheeks.

“I’ve already thought of a few names I liked. Henry for a boy after your grandfather and Samantha,” Her voice cracked slightly looking up into her eyes, “for a girl after Sam. Dean look at her. She… she’s our daughter. She has your olive eyes and my body shape.”

(Y/N) stood up walking towards Samantha and she could no longer hold it in. She missed her mom desperately and she got up hugging her tightly. They were sniffling with tears running down their faces. (Y/N) could her face in her hands letting out a strangled chuckle wiping away her tears.

“Hi mom.” Samantha whispered hugging her again then they heard the scraping of a chair against the floor.

She turned seeing Dean walking away, “This… this is all too much for me.”

Samantha watched as he walked away bring back vivid memories of the last time she had ever seen her father.

May 2029

Samantha held onto Henry small hand as their parents were arguing. Neither of them aware they were standing there.

“Dean, there has to be another way! I can’t live this life without you dammit!” Her mom yelled through tears streaming down her face.

Her dad sighed heavily and pulled her mom into his arms, “(Y/N) I wish there was another way, but there isn’t. Sam and I jumping in is the only way to save the world for good this time. You will take the kids far away from here with Cas and you give them the normal life they deserve. You live the normal life I could never give you and all of you live nice long lives.”

In all of Samantha’s ten years of life she had never seen her dad cry. He had been hurt badly and never once cried making him the bravest person in the world in her eyes. Her vision blurred as tears fell from her eyes. That is when her dad noticed them standing there and he smiled at them.

“Come here you little stinkers.” He called out kneeling down picking Henry up as he ran into his arms. “Alright little buddy, daddy is going to have to leave for a while. That means you’re the man of the house and you need to take care of your mom and sister. If you ever need help, then ask Uncle Cas. Okay?” Henry nodded throwing his little arms around their dad’s neck hugging him.

Samantha stood by her mom whose body was quivering watching her dad and brother hugging. She took Henry from her dad and he looked down to her. His bright green eyes wide and shiny from crying.

“C’mere Sammi.” He said as she launched herself into his arms. Her arms wrapped around his waist and her face pressed against his stomach hiding her tears. She heard him take in a shaky breath before speaking, “Sammi, I need you to be strong. I know you won’t understand why this needs to happen but know that I love you so much. I love you, I love Henry and I love mommy more than anything in this world. Try to remember that when you look back on this day.”

Samantha started sobbing and he picked her up with ease as she wrapped herself around him. He rested his chin on her thin shoulder and she could hear her mom crying behind her. He pulled her mom to them all four of them hugging one last time before he let go of them. He kissed each of them and then started walking down the corridor towards the garage.

Samantha ran after him screaming, “DADDY! DADDY DON’T LEAVE ME! DADDY!” That is when she felt a pair of strong arms grabbed her around her waist and she looked up seeing Castiel. She struggled against him until finally giving up and falling against him crying.

Present Day – 2018

“I will go talk to him.” Sam said as he went to get up but Samantha stopped him.

She shook her head and started walking towards what was her parents room, “I will.” She said simply as no one stopped her.

Walking down to the familiar corridors was weird for her and seeing the door to room number eleven partial closed she knocked on it before entering. Her dad sat on his bed with his legs outstretched and his back resting against his headboard. When he looked up at her, she was not prepared to see the agonizing sadness on his face.

“May I show you something?” She asked pulling up a chair next to his bed. He swung his legs over the edge and nodded sitting up.

Samantha reached into her jacket pocket and pulled out several pictures. Laying them all out on the bed for Dean to see. Pictures from her childhood in the Bunker. Pictures of their family smiling together and having birthday parties with the Jody Mills and the family she built with wayward children. Summer trips to her cabin with all of the kids swimming in the nearby lake. As Samantha explained each picture she could see her dad’s face changing into the man she remembered.

“This is my favorite picture.” She handed him it to him as she watched as tears slipped down his face. It was her tenth birthday and she was sitting in the driver’s seat of her dad’s Impala. He was sitting in the passenger seat as Sam and Castiel were in the back. She was smiling brightly pretending to drive as the rest of them were acting like they were scared.

Samantha stood up leaving the pictures for him to look at, “I know this is a lot to take in. I’m sorry that I lashed out at you. It took me a long time and getting married myself to come to terms with you leaving. As we speak, my husband and daughter as living in an underground shelter hiding from Lucifer who has brought on the Apocalypse while I’m here trying to not only save the world but my brother. Not to mention a psycho crazy Archangel trying to wear me to the prom.”

She paused seeing Dean’s head snap up and she held up her hand to continue, “As much as I would love to have a heart to heart with you right now I don’t need my dad. Right now, I need Dean Winchester and Sam Winchester the legendary hunters who defeated Michael and Lucifer.”

He gathered her pictures handing them to her, “Okay. Sam and I will help you in any way we can.” She nodded as they left the room walking back out to the War Room where everyone was waiting for them.

“Now, Samantha tell us everything that happened.” Dean said once they were all seated.

Samantha shared with them everything that happened with Henry and Lucifer. It was a day she would never forget no matter how much she tried.

March 2049

Samantha drove the beat-up Impala up to the gates of an old cemetery outside of Lawrence, Kansas with Def Leppard’s ‘Rock of Ages’ blaring out the windows. It was the exact spot that her dad and uncle had jumped in together trapping Lucifer and Michael in the cage. The same spot her Uncle Sam had jumped in trapping Lucifer in the cage with his half-brother Adam having Michael inside the cage.

She saw her brother staring over to her as she killed the engine and got out of the car. She casually walked up with her demon handcuffs in her pocket and angel blade at the ready up her sleeve.

“Sammi, I have to do this. I know you don’t understand but everything will be better. We will have everything we wanted as kids once I complete this.” He said as he ran his hand over his chocolate brown hair.

She shook her head, “You know dad said the same thing to me when he left. He had to leave and it was all for the better but it’s not. Whatever Lucifer is promising you is a lie. You’ve read Uncle Sam’s journals about Lucifer. Everything that comes out of his mouth is deception and lies.”

She watched as her brother squared his broad shoulders. His jaw set in a stubborn straight line just like she could remember her dad doing when she was set in his ways. She dropped her angel blade as Henry laughed.

“You’re going to kill me? I don’t think so sis. You’ve been out of the game too long now. I promise if you leave now then you and your family will be safe. Lucifer will bring dad back, Uncle Sam, mom and we can all be one big happy family under his rule.” A wicked smile spread across his face as he turned his back to her beginning to chant his incantation.

Samantha hesitated for only a moment and then she lunged forward aiming for the middle of her little brother’s back. He turned quickly blocking her knocking her blade out of her hand.

“Samantha, please don’t make me hurt you.” He snapped at her and resumed his incantation. The ground began to rumble and open right at his feet. It was splinter in every direction as she scrambled to get up running from Henry. She looked up just in time to see the ground swallow the last thing connecting her to her dad. The sounds of crushing metal ringing in her ears then she felt herself being pulled away suddenly.

She looked around seeing she was in an open field. Turning around she saw Castiel standing behind her, “Cas I have to go back! He’s going to release Lucifer!” she yelled.

Castiel shook his head and grabbed her shoulder roughly, “It’s too late Samantha. Henry has already said yes to Lucifer allowing him in. I have to get you to a safe space where Michael cannot find you.”

She felt her heart drop and her mind was racing with thoughts. She looked up panic setting in as she held onto Castiel, “Take me to Jacob and Jody.” She said as Castiel whooshed her away.

Present Day – 2018

Samantha looked around the table all of them looking shocked and puzzled. “Uncle Sam, I need to know how dad was about to reach through to you when you were possessed by Lucifer the first time 2010?” she asked.

The brothers looked to one another as Sam spoke, “It’s kind of hard to explain. I saw one the plastic army men that I stuck into the ashtray and something about seeing that made me think of Dean and everything we had been through. From there I just fought my way to the surface, but it sounds like things are different with Henry. He wanted Lucifer to come into him where I had every intention of fighting Lucifer for as long as I could.”

Samantha sighed heavily feeling defeated, “There has to be something I can do to save my brother.” She whispered as she felt her mom’s hand start to rub her back.

“There may be something to defeat Lucifer, but it won’t save your brother. I know how this may sound coming from a Winchester but for the fate of the world you may have to choose between it and your brother.” Sam explained as Samantha sat up straighter.

Her daughter’s face flashed before her mind and she pursed her lips, “I will do anything to save my little girl and my husband. Whatever you got to defeat Lucifer I will take.” She said with determination.

She glanced over to her dad who was smirking proudly as Sam and Castiel got up, “Cas and I will look for the item in our storage room. We’ll be right back.” Sam said as they got up walking off down the side corridor.

Samantha looked from her mom to her dad as they both were anxious looking. She snickered, “Whatever you both want to say please do because I can’t take the awkward silence.”

They all laughed as (Y/N) asked, “You said you have a little girl and husband?”

“Yes, I do. Jody adopted a boy when I was six years old who is a year older than me. His name is Jacob Mills and we were always best friends until that turned into more in high school.” She looked over to her dad as he growled in disapproval making her and her mom laugh.

“Anyway, we’ve been married for six years and our daughter Cassandra will be five in a few months.” She pulled out her small wallet and showed her mom a picture of the three of them.

Dean leaned forward to look at the picture as well and a small sigh came from him, “I need a drink. Would either of you like one?” (Y/N) shook her head as Samantha nodded.

“Whiskey for me, please.” She said once again earning a smirk from her dad.

(Y/N) and her spoke briefly about what Samantha did before everything happened with Henry, “I guess I’m more like my dad and Uncle than you ever wanted me to be. I got a degree in computer science so I could freelance my skills to make money in order to hunt. Jacob and I hunted together until I got pregnant then everything changed. We stopped hunting all together like you and dad did when you found out about me.”

Dean handed her the glass of whiskey, “I stopped hunting?” he asked his eyebrows knitting together.

Samantha nodded, “From everything mom would tell Henry and I you did. I think you and Uncle Sam still went out on little hunts because I would hear mom and you loudly talking to one another.”

(Y/N) rolled her eyes as Dean looked away guilty, “Sounds like something I would do.”

She laughed, “Don’t worry dad, I’m the same way. Jacob is always mad at me whenever I sneak out to take out a werewolf or a vamp nest.”

Dean laughed nodding proudly at her as (Y/N) muttered, “Great, two peas in the same damn pod. Good to know in the future I won’t have any peace of mind either.” Dean leaned over kissing (Y/N)’s cheek.

Samantha and her dad were talking about different hunts when Sam and Castiel came back in holding a gold blade that twisted into a point.

“Holy crap, is that an Archangel blade?” she asked as Sam handed it to her.

Sam nodded, “It is and the only thing that can kill Lucifer, but you will need one more thing.”

“What?” she asked feeling hope creep up in her heart.

Her dad placed his hand over hers, “You need an Archangel to wield it in order to kill Lucifer.”

Samantha shrugged nonchalantly, “No problem.” They all snapped their heads to her in surprise.

“Do you have an Archangel on speed dial or something? If you dare say you’re going to say yes to Michael then I will lock you in the dungeon because I know from personal experience that he will just screw you over.” Dean said shivering.

She shook her head adamantly, “No, I would never say yes to Michael. Hell no! He’s coo-coo for Cocoa Puffs. However, the boy that Jody will adopt is a Nephilim.”

(Y/N) gasped, “You’re married to a Nephilim and had a baby?”

“Yes, the angels aren’t as uptight about Nephilims since Jack took over running Heaven. They can see the benefits of them and how having a nurturing influence will help them control their powers. Jacob’s real father is the Archangel Gabriel and let me tell you the apple doesn’t fall from the tree.” Samantha explained.

Samantha stood up looking to Castiel, “Cas, I will need a lift forward to 2049.” He nodded to her as she turned around facing her parents and uncle.

She hugged Sam first thanking him for all the journaling he will do in the future. She stepped over to her mom who pulled her into a hug whispering to be careful. Samantha smiled nodding her heart hurting as she knew going back meant her mom no longer being around. Finally, she turned to Dean who was awkwardly standing with his hands in his pockets.

Samantha threw her arms around his neck hugging him and he wrapped his around her holding her tightly. She whispered, “I forgive you for everything daddy. I understand now why you had to leave and I just want to thank you for what you did.” She pulled back slightly kissing his cheek and hugging him once again.

She stepped out of his embrace and looked around at her family not wanting to leave them but knowing she had too. “I love you. I love you all.”

She stepped beside Castiel and just before he placed his hand on her shoulder she heard her dad call out, “Sammi, kick it in the ass!”

The next thing she saw was her husband and daughter standing with Castiel in their version of the Bunker in 2049. Jacob rushed to her as she slumped into a chair.

“Baby, you okay?” he asked as Castiel walked over to her placing his healing hand over her head.

She felt her body warm up and get tingly then she felt back to normal. “I’m fine and I have a way to defeat Lucifer. Jacob, you will need to wield this,” she handed the golden blade over to him, “and I’ll stay home with our baby. It’s your turn to save the world. I’m going to take a break since I time traveled to get the weapon.”

Jacob laughed kissing her as he went over to their small group arranging a plan to defeat the devil. Cassandra ran over jumping into Samantha’s lap hugging her. Castiel said next to her smiling slightly.

“So, how did everything go back in 2018?” he asked curiously.

Samantha hugged her daughter tightly, “Awesome.”

Castiel laughed, “You really are the spitting image of your father.” He got up to help Jacob with the others as she sat back enjoying holding her daughter.

“I know and that is why I am choosing to stay with my daughter.” She whispered resting her head on top of hers.

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