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zepskies · 9 months

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Choosing Him

Pairing: Dean W. x Reader, Sam W. x Reader

Summary: You and Sam have been dating and living together for a few months, when Dean shocks you with a confession. Now you have to choose.

AN: This was requested by this beautiful anon! (And also by my friend! ❤️)

Read this as a stand-alone or see this imagine for context: Dean gives you an impossible choice. (In which Dean is in love with Sam’s girlfriend.)

**Note: This contains two alternate endings: Sam vs. Dean.

Song Inspo: “I’m on Fire” by Bruce Springsteen

Word Count: 4,300 Tags/Warnings: Angst, hurt/comfort, unrequited love, as well as love requited.

Imagine: Choosing him.

“Dean, just talk to me. What the hell happened?” Sam asked.

No, he implored. Angrily.

But he implored, nonetheless.

Dean was good at being stubborn. In fact, he was a professional. His lips were tight in a frown, his brows just as knitted as his brother’s.

He sat cross armed on the couch while Sam stood, using his hands to punctuate his exclamations, as he often did when he was frustrated.

“Nothing, man. I already told you,” Dean tried.

“No,” Sam said sharply. “She’s actively avoiding you. And you’re taking any excuse you can not to be within three feet of my girlfriend. So either you said something, or you did something.”

Dean looked up at his brother with a heavy sigh through his nose.

They’d been at this for a while now. So long that he was surprised you hadn’t come barreling into the living room already to break up the argument. Because he had a feeling that just the sight of you would shut them both up. (Not in a good way.)

Dean’s throat was tight, his stomach churning with unease, though he tried to show none of it on his face. He could see that Sam was on the verge of losing his shit. Just a hair away from assuming the worst.

And the worst of him.

That, Dean couldn’t abide.

“Look,” he gritted out. “I didn’t do anything.”

Sam paused, tilting his head. He took in a breath that was only slightly calming, enough that he lowered to a seat on the coffee table, across from his brother.

“Then what’d you say?” he asked.

Dean felt even guiltier just remembering.

Three weeks ago…

You wanted to know why he was drinking alone. Why he’d downed nearly an entire bottle of Jameson in the kitchen on a Tuesday night.

“You really wanna know?” Dean asked. His voice was both a rumble and a coarse whisper. His green-eyed gaze fell to your lips.

He watched you suck in a subtle breath. Your eyed widened, and your body froze. He also saw the blush staining your cheeks.

So he leaned in, slowly. He was mere inches away from finding out how sweet you really were.

He heard your shallow breath. His eyes flicked up to yours, and instinctively knew that he’d captured you. He was making you think about it.

“Tell me no,” Dean said. Tell me to stop, or I swear to God...

“Dean, what...” you whispered. But that wasn’t a no.

Still, he couldn’t. He just couldn’t do it. Not to Sam.

Dean merely reached out with a hand to soothe a gentle thumb across your cheek. He realized then that he loved you. He loved you enough to let you go, if he had to.

"It comes down to this," Dean said. His voice was deep, full of grit and desire. He saw the conflict in your eyes.

He swallowed. His heart was pounding against his ribcage, but he used every ounce of self-restraint he had left, forcing his hand to fall away from your cheek.

"You've got two choices, sweetheart," he said. And he pulled away, leaving you there at the table.

You never told him to stop…but he just couldn’t do it.

“It doesn’t matter,” Dean eventually answered his brother.

He ultimately couldn’t bring himself to voice the desperation of a drunken idiot.

He met Sam’s gaze directly. This much, he could say.

“All you need to know is I’d never…even drunk off my ass, I’d never hurt you,” Dean said.

Sam turned those words back and forth in his mind. His mouth firmed as he read between the lines, as he so often had to with Dean, who struggled to express the deeper parts of himself. Sam realized then what his brother was finally confessing.

“She loves you,” Dean added, with a self-deprecating smile.

That fell between them for a moment, as Sam rested a hand on his knee and processed all of this in record time. He glanced up.

“What about you?” he asked.

Again, with that quirk of a smile that didn’t reach Dean’s eyes.

“Don’t you worry about that either.”

He got up, clapped Sam on the shoulder, and left him there to continue thinking. Dean passed the kitchen and continued down the hall.

Neither man realized that you were standing behind the kitchen doorway. You’d been about to attempt a bit of stress baking. A chocolate tart, maybe. Or a cheese souffle. Or even the new cherry pie recipe you’d found for Dean. Anything to take your mind off your current predicament.

However, now you knew you couldn’t put it off anymore.

You didn’t want this, for either of them. You couldn’t let yourself be a coward.

Steeling yourself with a deep breath, you left the safety of the kitchen…

And you ventured into the living room, where your boyfriend was still brooding. He raised his head when he saw you out of the corner of his eye.

“Hey,” he said, clearing his throat. Even now, he was relieved to see you. He also felt like he was standing on unsteady ground.

“Hey, yourself,” you greeted back. You tried to smile, but your heart was in your stomach with nerves. “I need to tell you something.”

Sam seemed to realize what you wanted to talk about. He sighed.

“Look, don’t worry about it. Dean and I talked it out—”

“No. No, because I need to say this. Because you deserve to hear it from me,” you insisted.

You also paused, as you didn’t quite know where to go from here.

Sam’s brows furrowed, but he tried to be patient. He watched your gears turning as thought to thought shifted in your eyes. It was one of the things he loved most about you, how open and expressive you were. He could usually tell what you were thinking…except for today. And the past few weeks.

That was what had him more nervous than he’d like to admit. If a blow was coming, he’d really like to be prepared…but he just couldn’t fucking tell.

Until you began speaking.

“Okay, first of all. Nothing happened,” you assured. You rested your hands on Sam’s shoulders. He looked up into your eyes, but before he could even nod in response, you kept going.

“Dean was drunk, and I wasn’t. Which probably won’t make you feel all that better, but the point is, all I did was ask him what’s wrong? And he didn’t want to tell me. But then I pushed the issue, as you know I do sometimes. I’m working on it, I really am.”

You levied a finger at Sam, at which he could only nod. Again, before he could offer a reply, you kept going.

“Well, finally he was all, you sure you wanna know?” you said, mimicking Dean’s deeper voice. Sam was tempted to smile, if but for what you were actually saying, and the way your gaze averted from his.

“And there was a moment there when…I thought maybe he might try to…but he didn’t. The problem is, I didn’t say no,” you confessed. Your brows knitted as you revealed how disheartened you felt at that, how guilt-ridden.

Sam’s eyes softened a bit, even though your words stung.

“I should’ve said it,” you knew. “I should’ve pulled away, but I didn’t. Though in my defense! I was in shock. He was saying shocking things without saying them, you know? And I don’t want to be in this cliché…teen drama-esque, love triangle bullshit! You’re not Edward and I’m not Bella and this isn’t goddamn Twilight. And I refuse to be treated as such.”

You were huffing and puffing by the end of your little rant. Your eyes widened a fraction when you caught Sam trying to stamp down a smile.

“Is this amusing to you?” you snapped.

“Not at all,” Sam said. He shook his head, and with a sigh, drew you back to him with his hands on your hips. You stood between his open legs and grasped the front of his shirt.

“Look, thank you for telling me,” he said. “I know that we kind of rushed this a little. The moving in thing, I mean. It just…it felt right, at the time.”

“Yeah, I was kinda there for that,” you quipped. Your smile made him smile in return.

“Well, I guess I just need to ask you…if it still feels right,” he said.

He looked up into your eyes, still not quite sure what he would find. His heart was in his throat, no matter how many times he cleared it. He was good at looking calm when he wasn’t, and maybe his face was composed, but inside him was a tempest.

You calmed it with one touch. A gentle hand on his chest.

“Sam,” you said. Your smile was beautiful and warm. “After you left Stanford. After what happened to Jess…I didn’t know that her funeral was the last time I was ever going to see you.”

Despite that melancholy memory, your lips soon curved into a grin.

“Well, not for a long time anyway.” You both lightened at that.

Then you became more contemplative. Your gaze wandered beyond him for a moment, lost in the past.

Sam’s hands moved up to your waist and squeezed gently. You came back to him with a brighter expression.

“But when I saw you again, I thought…damn, he’s amazing,” you said with a giggle. “Even more amazing then when I knew him.”

Sam looked down at that, despite his smile. You picked him back up with your hand on his cheek. It was overgrown with stubble, a week or so past when he'd usually shave.

You didn't mind the scratchiness, but you wondered if you'd been distracting him too with your indecision. That thought made you feel all the more guilty.

“I still think that when I see you. Get to wake up next to you, research mythology and symbology and dead languages, and other things that should be impossible,” you said. “So yes, it still feels right for me. Very much so.”

Sam’s more genuine smile lightened you. He nodded and let you tilt his head back, slipping your fingers through his hair. He liked the way you touched him freely, both reassuring and affectionate.

He didn't want to admit it, but he'd been quietly afraid. Afraid he'd read you wrong, that his heart had somehow lied to him. Now he knew that it rang true.

“Okay. Good,” he said. And he reached up to touch his lips to yours.

At least, it was a simple touch at first. It soon grew in passion, becoming a more claiming kiss. He pulled you in flush against him. A hand tangled into your hair, brushing against the back of your neck, and you hummed in delight.

Your hands sunk further into his hair, just as your mouth wordlessly claimed him back. His long fingers trailed down your back and made you shiver against him. You gave more and more of yourself with each kiss.

"I love you," you whispered against his lips. Because he deserved to hear that too.

Sam paused. His eyes were still closed as he recovered some of his breath. He rested his forehead against yours and brushed a tender hand down the soft column of your neck.

"I love you too," he admitted. He had resisted saying it, and even felt a bit ashamed that he'd doubted your feelings. Now, he felt like an idiot for not fighting harder before.

This, what he had with you, it was worth fighting for.

He smiled at the way you kissed his cheek then, soft and slow and with purpose.

After a moment, you pulled away to stroke his cheek once more…and also to tell him one last thing.

“When I saw you again, I did have another thought,” you said. “He’s amazing, but…how can I think that about my best friend’s boyfriend?”

Sam frowned then, as that reality had crossed his mind as well, back when he reconnected with you last year. You held a hand to your chest, over your heart.

“Jess was like a sister to me. So how could I think about you like that? It didn’t matter how much time had passed since her death. That thought, and those feelings still had weight, Sam,” you said. “My point is…try not to be too hard on your brother for this. I think he’d rather lob off an arm than cause you any pain.”

Sam considered your words with a nod.

“I’ll talk to him. Don’t worry,” he said.

“No, I…I’d like to talk to him, if you don’t mind,” you said. “That is, if you trust me.”

Sam’s brows rose, and then furrowed slightly.

“I do, baby,” he said. “You can talk to him if you want, but…I have to. He’s my brother. He should hear it from me too.”

No need, Dean couldn’t help but think.

He pushed off from the wall, twisting a wrench in his hand as he made his way back to the garage.

It stung. Actually, it fucking cut and twisted. More painfully than Dean would ever, ever admit.

However, he knew when he needed to bow out. This was one of those times.

He’d just have to learn how to let you go, for good this time. He wouldn’t risk hurting you, or his brother again.

So once he made it to the end of the hall, he shut the door, once and for all.

Or…

You didn’t want this, for either of them. You couldn’t let yourself be a coward.

Steeling yourself with a deep breath, you left the safety of the kitchen…

And you ducked out the back way, heading down the hall.

You found Dean exactly where you’d expected—in the garage, getting ready to work on his Baby. He was sitting on a stool with his box of tools beside him. Tools he didn’t let anyone touch (except for that one time you hid his power drill, just to mess with him).

You crossed your arms.

“We need to talk,” you said.

Dean sighed, and spied your stern face over his shoulder.

“What fucking now?” he muttered. You didn't quite hear him, but you recognized his surly frown.

“Yes, right now,” you said. “Why did you do it?”

“What?” Dean asked, raising incredulous brows. “Why?”

“Yeah, why.” You stepped up to him while he swiveled in your direction. “If you supposedly had feelings for me, why did you wait so damn long? Why did you wait until we got here?”

You weren’t just casually dating his brother. You were living with him. Even if it had just been a few months, you loved Sam…and yet, you hadn’t pushed Dean away when he almost kissed you.

Why, why, why? you thought. Your teeth ground together when you thought of how tenderly Dean had touched you. The fire in his eyes, just barely held back by a thin wall of self-restraint.

“Tell me no,” he’d said.

And now, annoyance made his face tight.

“Look, just forget about it, all right? I was drunk—”

“No. You weren’t that drunk,” you refuted. “I’ve seen you slaphappy, laughing at nothing, grinning like the Joker and falling onto the couch face-first, passed out drunk. You were coherent that night. You were honest. So tell me, how long have you felt this way?”

Dean tensed. He didn’t want to do this. You both knew that, but he also knew that you weren’t giving him much of a choice.

And yet, you were waiting on him, as patiently as you could manage (something he knew was difficult for you). He sighed deeply.

“Pretty much from the beginning,” he said.

“What?” you said, ever so eloquently. You wanted to cringe at yourself. (And you called yourself a linguist.)

Your lips pursed in disbelief. “What part of the beginning?”

Dean glared heavenward, as if that could stop you from asking questions.

“From the first damn second I saw you,” he snapped. The longer he looked at you, however, he couldn’t help but soften. “I remember, you argued with Sam about dead languages, that Latin was for pussies. Ancient Greek was the tougher beat.”

That was true, you thought. And that argument stemmed back from when you and Sam were in college. Ancient history, you could say.

“The Greeks were more fun too,” you added. It triggered a smile to briefly lighten Dean’s face.

“Yeah, you said something about mass orgies,” he said, his brows furrowing.

You bit your lip at the memory. You might’ve winked at Dean with more confidence than you’d felt at the time.

Now, the man shook his head.

“Right then, I wanted to know you,” he said. “Problem is, the more I did, the more I liked what I saw.”

You stared back at him in dismay.

“Why couldn’t you have just told me from the beginning?” you asked.

Dean made a sound of frustration, carding a hand roughly through his hair.

“Oh, and what, break up the show?” he snarked. He waved haphazardly beyond you, to the moose of a man somewhere beyond the closed doors of the garage. Remembering his brother made Dean’s irritation start to fade, back into self-deprecation.

“You and Sam…you’ve got history,” he said. “He’s smart. He takes care of you, protects you. He’s uh, more the boyfriend type, anyway.”

Dean looked away from you then, crossing his arms. You relaxed yours and couldn’t help but draw near to him. A frown took over your features as you tilted your head.

“Okay, Sam and I have history,” you said with a nod. “But…you don’t think you’re smart too?”

Dean’s lips pursed somewhat as he glanced back up at you. You met his stare.

“You don’t think you’re capable of all those other things?” you asked.

Dean didn’t have an answer for you. At least, not one he was willing to say.

For the past few weeks, you’d been fighting with yourself. You’d turned that moment in the kitchen over and over in your mind, and why you couldn’t do what you were supposed to do.

Now, looking at Dean’s face, you understood why your heart broke for him. Why your heart ached with ridiculous longing for him in equal measure.

You knew then that he’d take care of you. That he’d protect you. And maybe…

“Sam and I don’t make a habit of going after the same girl,” Dean said. Even that, it seemed, was difficult for him to get out.

It broke you from your thoughts, again with your frown.

“Yeah?” you asked. A bit of your temper sparked once again. “Is that why you’re making me Yoko Ono? I’ll tell you something right now. You’re not John and Sam’s not Paul and I refuse to break up the band, Dean!”

“No one’s asking you to!” Dean said, finally raising his voice to match you.

He got off his seat and stood to his full height. Though he wasn’t as tall as his brother, he still towered over you. You craned your head up to glare at him.

His green eyes were once again full of fire. You tried to resist it, but that look made a jolt of electricity zip down your spine, and between your legs.

“Oh, really?” you retorted. “That’s what you want? For me to forget you didn’t shake me the hell up?”

“Yeah, I really fucking would,” Dean gritted out. Even though his heart leapt at your admission, that he’d shaken you up at all.

“Why?” you said. “If you claim to care about me, why would you—”

“Why would you?” he shot back. He gestured at you with a dismissive hand. “The second you saw him, it was like your face lit the hell up. I’m not gonna get in his way. And by the time the you two were together, I just…I didn’t think you…”

Dean cut himself off, turning from you to wipe a frustrated hand over his mouth.

You watched him very closely, all while you made efforts to take in some deep, even breaths. You followed him, and more tentatively, you grabbed onto his wrist to tug him back around.

“Why would I what, Dean? You didn’t think I’d what?” you all but pleaded. Your grip lowered and tightened on his hand.

“Just talk to me,” you said. “Because this is your one and only chance.”

He was reluctant. For once, you could see it written all over his face. Or maybe you were just getting better at reading him.

“It’s fine. I’ve made my peace with it,” said Dean.

Liar.

He shook his head and slipped his hand out of yours.

“At the end of the day, you saw him, not me,” he said. “So go back upstairs, and we’ll never have to talk about this again.”

Your frown deepened as he sat back down and tried to turn away from you. You were so goddamn mad. At yourself, or at him, you didn’t know what percentages of each.

So you closed the distance between you and Dean and turned him back around, with a firm hand on his shoulder. Even with that small touch, your insides fluttered at the firm muscle there, and the broadness of his frame when he let you move him. He blew out an exasperated breath.

You wavered just slightly, as you contemplated the confession you were about to make. It shamed you, but at the same time, you were woman enough to admit your mistakes.

“I did see you,” you said, meeting his eyes. “But Sam never hesitated to show me what he wanted. And maybe…maybe he was safer. Familiar, and less dangerous.”

Dean’s brows furrowed, incredulous and confused.

“What the hell are you talking about?” he asked.

You couldn’t fault him for it. Your hand eased on his shoulder.

“Dean, seeing Sam again was like getting my best friend back,” you told him. “Back in college, we were thick as thieves. Me and Jess, Sam and Brady. And when you two found me to help with that case, I wouldn’t have ever seen him as anything more than my friend…until he did something about it.”

Your gaze was pointed. Dean’s lips pursed.

“When I met you,” you continued, “it was like the Godfather ‘thunderbolt.’ When you flirted with me, I didn’t know what to do with myself…whereas with Sam, I could fall back on my old habits.”

Dean’s face knitted further, making you sigh.

“With Sam, I’m the person I was when he knew me. The me that never faltered. That had all my shit together,” you said. Your small smile then was self-deprecating at best.

You felt vulnerable. Dean could see it in the way you held yourself. It was costing you something to be this honest, and that meant something to him. His face might've been stoic, but he was hanging on your every word.

“With you…with you I can’t hide," you said. Your voice was softer, slightly trembling. "And that terrifies me, more than monsters.”

Looking into Dean’s eyes again, you found him actually listening. He seemed to be digesting your words, and trying to make sense of them. You reached for him, clenching a hand in his shirt.

“So what was it that you thought I wouldn’t do?” you asked.

Dean studied your face a moment longer. He hesitated.

But he couldn’t keep lying to you either. What you’d just said gave him hope that he wasn’t about to fall flat on his face here.

With a deep, defeated breath, he shook his head and leaned his elbows on his thighs.

“I just got to thinkin’…” he said. “Why would you give up what you’ve got with him, for me?”

You didn’t know quite what to feel when you looked down at him. Disheartened, sympathetic, annoyed…but most of all, you felt your heart clench.

Your hands framing Dean’s face brought his eyes back to yours. You stepped in between his open legs.

“I’m going to try something. Just once,” you said, biting your lip. “And if it doesn’t work, we won’t speak of this again. Understand?”

A true smile finally twitched at the corner of his mouth.

“All right,” he agreed. You nodded.

Slowly, ever slowly, you leaned down and brushed your lips with his. It was chaste and sweet. Your hands were soft curving along his jawline. His hands found their way to your waist, molding to your shape. That steadied you, and encouraged you to dive back in.

You tilted your head and kissed him a bit deeper. He held you more securely against him, like he was afraid you were going to think better of this and pull away from him.

But you didn’t. His lips were soft and supple and knew how to move against yours. He soon guided you down for a seat on his strong thighs, even though the stool he was sitting on creaked at the added weight.

Then his tongue begged entrance past your lips. If this was his one chance, then damn it, he was going to make the most out of it.

You let him in with a moan. Your fingers tangled in his short hair, your nails dragging down the back of his neck and making a tendril of heat run down his spine. He squeezed your hips, down your thighs, while his lips continued to ravage yours.

It was one hell of a kiss.

But it wasn’t just lust either. At least, not for you. It was warmth, and an overwhelming feeling being right where you were always meant to be.

For Dean, it felt like a craving he wasn't meant to indulge in...but even so, having you in his arms felt as natural as he feared it would be. He didn't just want you. He wanted this. Today, and every day.

When his lips finally dragged away from yours, it took you a moment before you could even open your eyes, let alone catch your breath.

“Damn it,” you whispered.

Dean chuckled, and pulled back just far enough to graze your cheek with his curled fingers.

“Guess I’ll take that as a compliment,” he said. You smiled, but it soon fell.

“Oh God, Dean. What’re we gonna do?” you asked. Already there were tears stinging in your eyes. And still, you held him back with your arms curled around his neck. “I don’t want to hurt him.”

Dean’s relief, and a hidden swell of happiness, also dimmed. “That ship’s sailed, sweetheart."

You sniffed, wiping at your face. “Don’t joke right now, please.”

“I’m not joking,” he said. He held you a fraction tighter. His deep voice rumbled, with desire, longing, and remorse all at once. “I’m actually serious beyond fucking belief.”

You saw everything you needed to see in his eyes. It gave you the strength to be honest.

“So am I,” you nodded, sniffling again. “I’ll talk to him.”

Dean shook his head. “He’s my brother. I’ll do it.”

You stroked his cheek, feeling the rasp of stubble against your fingers.

“Together, then,” you compromised.

And with an unsettled breath, you reluctantly detangled yourself from Dean. Before this went any further, you needed to talk to Sam. It was easily one of the hardest things you’d ever contemplated doing in your life.

Dean seemed to have similar thoughts as he let you up, then stood along with you. He dragged a hand through his hair again and heaved a sigh.

“It’s not gonna be easy,” he said. His brows drew together as he considered every alternative reaction his brother might have. None of them were pretty.

You rested a hand on his arm.

“Look, Dean. If we’re going to do this…if I need to leave the bunker, I will. I’ll do whatever it takes to make this work, as long as you’re in this with me,” you said.

Both your gaze and your will were unwavering. Dean didn’t doubt that you meant every word; that you were willing to jump into the fire with him. And that was just a small fraction of what had made him fall in love with you.

He took your hand, and pressed a lingering kiss to the inside of your wrist.

“I’m with you,” he replied.

AN: So while it was painful to contemplate both of these scenarios, I hope I did them justice! 🥲

Which ending was your favorite: Sam, or Dean? 😘

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