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Title: Ride With Me (part 29) Fandom: Supernatural Timeline: 2008 Pairing: Dean x Reader Word count: ±8450 words Summary series: Y/N is a talented horse rider who is on her way to become a professional. In order to convince her father that she deserves the loan needed to start her own farm, she goes to Arizona for six months, to intern at a ranch owned by Bobby and Ellen Singer. Her future is set out, but then she meets a handsome horseman, who goes by the name of Dean Winchester. A heartwarming series about a cowboy who falls for the girl, letting go of the past and the importance of family. Summary part 29: After the accident with Cain, ranch life returns back to normal. Ellen and Bobby are going on a business trip, leaving Dean at the helm. The wrangler’s bond with the intern is slowly rekindling, leading up to a long-awaited and difficult conversation about what happened between them. Meanwhile, Congress is just around the corner, but fate might have different plans. Warnings series: NSFW, 18+ only! Fluff, angst, eventually smut. Swearing, smoking, alcohol intoxication, alcohol abuse. Mutual pining, heartbreak, slowburn. Crying, nightmares, childhood trauma. Description of animal abuse, domestic violence, mentions of addiction. Financial problems, stress, mental breakdown. Description of blood and injury, hospital scenes, character death, grief. Music: The Scientist by Boyce Avenue (conversation by the fence between Dean and Y/N). Follow ‘Ride With Me Playlist’ by Kate Huntington on Spotify! Author’s note: This chapter is packed with sibling banter, Dean getting sweaty and dirty while working on the tractor in just jeans and a white tank top (you’re welcome). Add plenty of emotion and an unexpected turn of events, and you have 8.5K of Cowboy goodness! Beta’d by my mom (yes, you read that right. My mom reads my stuff and is on Tumblr) and @winchest09 and @girl-with-a-fandom-fettish. Also a special thanks to @jules-1999 and @rebel4fandom, who has offered me her knowledge about reining and rodeo. The wonderful gif is by.

Ride With Me Masterlist

A couple of days have passed since the incident with Cain, and life is returning to normal. Dean is back at work, and despite that he hasn’t felt dizzy in days and the headache is mostly gone too, he’s taking things easy. That way there is less pressure on him, which makes Ellen happy, and it gives the ranch’s intern the opportunity to develop her riding. Thankfully, he has been able to sleep somewhat better, and he doesn’t feel so tired and worn anymore. The swelling on the side of his face has disappeared, the bruises fading as well. Y/N removed the butterfly stitches yesterday, the cut under his brow the only scar left to remind him of his kamikaze stunt. Even Jo is doing chores again, despite only having one functioning arm for the coming month and a half. The stubborn cowgirl even climbed on her horse’s back yesterday, but Dean - being as protective as he is - instantly called her out and demanding her to get back on the ground. Of course, she threw his own words back at him, that she didn’t hurt her riding hand and will not need a pair of them to train a horse. The argument between the two who act so much like siblings soon turned childish when Dean yelled ‘I’m telling your mom!’. It does work when he pulls that card, though, because if there’s anything Jo doesn’t want, it is Ellen getting wind of her rebellious behavior. Her mother would ground her in an instant.

The ranch owner’s daughter decided to wait for the opportune moment instead, which is right around the corner. Her parents are heading upstate to meet with Donna and Jody, to talk about co-owning a couple of horses in order to help the Gold Canyon Ranch get through the economic crisis the country is currently suffering from.

The truck is packed already, Bobby turning the key in the ignition and switching on the air-conditioning before he gets out of the driver’s seat to address his daughter and adopted son. “Hold the fort, you two,” he says before eying his nephew. “Dean, you’re in charge.” “Why does he get to be in charge?” Jo mutters, placing a hand on her hip. “Because I’m the oldest,” Dean answers before Bobby can, triumph in his voice. “And because he’s not the one with an arm in a sling,” her father adds, throwing his daughter a stern look. “So? He’s the one who hit his head. Doesn’t seem smart to let him do the thinking.” She shrugs, giving the man next to her a dirty look before she adds another jab. “With or without a concussion.” Dean glares at her through narrowed eye lids. “At least I wouldn’t be dumb enough to get on a h--”

He’s interrupted when Jo stomps his foot, causing the cowboy to swallow down the final word that would expose the blonde cowgirl. Her fiery gaze that says ‘don’t you dare’ waits for him when he’s about to snap at her, their intense stares battling out a wordless argument.

“Are you two idjits done?” Bobby cuts in, sternly glancing from one to the other. “Truth be told, I don’t give a rat’s ass who decides what, and I certainly don’t wanna know what you inept klutzes are not telling me, but I want this place exactly the way I’m about to leave it. So you are both gonna suck it up, work together, and make sure the ranch doesn’t burn down to the ground, am I clear?”

Dean focuses on his uncle again and gives him a nod, but Jo sighs, aggravated. “Don’t roll your eyes at me, Joanna Beth. I’m serious; no unpleasant surprises when we get back,” the ranch owner warns while circling the car, pointing a stern finger at the two. “Understood,” his nephew states, confident and reassuring. The female wrangler nods, too. “Yes, Dad.”

The sound of a closing door draws their attention to the Singer home, where Ellen descends from the steps with a weekend bag in hand.

“There’s a pot roast in the fridge. The oven is already set, if you pop it in after lunch, it should be perfect by dinner time,” Ellen instructs as she drops her baggage behind the seat of the large four by four. “You be good, okay?” “We will,” Jo promises, lying through her teeth. First thing she’s going to do when her parents have turned down the driveway, is tack up her horse, Bullet.

After saying their goodbyes, the two who behave so much like brother and sister watch the Ford exit the parking lot. When Mr. & Mrs. Singer are out of sight, the pair returns to the barn, side by side. There’s plenty of work waiting for them after all.

“Tattletale,” Jo sneers at the man next to her, sticking out her tongue. “Oh, real mature.” Dean scoffs. “You’re just saying that because you can’t think of a comeback,” Jo counters, her eyebrow cocked victoriously. “So see ya later, asshead. I’ve got horses to ride.” “Jo! You are not--” he starts to scold her, but then blows out a vexed sigh as he watches his little cousin skip towards the stables. It’s no use, she’s not going to listen to him anyway.

Shaking his head, he follows her; she’s impossible. God help him to keep that girl out of trouble during the coming days. Now that he’s the leader of the pack, whatever happens on the premise, will be his responsibility. He’s praying for an easy weekend, but experience has taught him that once Bobby and Ellen are gone, problems are bound to arise.

The morning goes by without a hitch. Their regular veterinarian, Cas Novak, has paid a visit to check on Led Zeppelin’s recovery process, and thankfully the ultrasound showed that the stallion is doing well. The palomino will still need to be handwalked for another month, but after that time, Led can be ridden again.

Dean trains two horses under the saddle and two more on the ground in the round pen. The intern has gladly taken on the opportunity to train a few of his animals, which he left in her care when he was recovering, and the head wrangler doesn’t mind it one bit. Seeing the joy in her eyes whenever she’s on one of the talented Quarters is more than worth not being the one in the saddle himself. He helped her out with AC/DC, a young stallion who tends to act up every now and then, and taught the rider how to properly handle his juvenile behavior. She’s acing it, though, sitting out the occasional buck like she’s glued to the horse’s back. It fills him with awe and pride every time.

After lunch, Dean and Benny tend to the broken down tractor. The head wrangler has shed his plaid shirt, the white singlet he’s wearing already stained with gearbox fluid and grease. He’s on his back under the John Deere, unscrewing one of the bolts that is keeping the broken piece of machinery in place. The engine hood has been removed, his friend sitting on his haunches by the tractor as he disconnects the crankshaft and the flywheel from the side. The two mechanics are surrounded by bits and pieces, containers of oil, toolboxes and more.

“How’s it comin’ over there, Chief?” the Southerner asks, placing the removed parts on a cloth on the ground next to him, careful not to lose any essential components. “Gettin’ there,” he mutters through gritted teeth, using all his might to loosen the nut that doesn’t want to give, years of sand and rust making it difficult to unwind.

The gravel is sticking to the fabric of his shirt and his exposed skin, sweat causing the particles to cling to his shoulders and back. His muscles work and roll, veins laying thick on his forearms as he puts pressure on the wrench. Finally the nut gives and the gearbox is detached. The cowboy slides from under the John Deere skillfully, holding the heavy chunk of metal up with one hand.

“It’s loose. Can you help me out on this side?” he requests, whipping the moisture off his forehead with his free wrist. His friend from the south switches positions, helping Dean haul the heavy load away from the tractor. After struggling for a bit to remove the rusty screws that hold the heat shield in place, they begin stripping the transmission. The torque converter seems fine, and so does the oil pump, but when the two men get to the planetary gearset, the problem is soon revealed. The worn wheels obviously have seen better days.

“Well, shit. No wonder the pan was swimming with metal,” Benny comments, stretching his back while looking down on the carnage. “Yeah, we’re gonna need to replace that. We might be able to salvage the clutch packs, though.” The cowboy gets up, wiping his grimy hands with a cloth. “I’m gonna call the John Deere dealer in Phoenix, maybe they have one in stock. I’ll order a new oil pan too.”

Leaving the farrier to the job of checking the clutch, the head wrangler heads to the Singer’s home. He hopes that if he can arrange the parts before 3 PM, he will be able to head to town and pick them up so that the ranch will have a running tractor in the morning. Humming, he kicks off his boots and heads to Bobby’s office, a little surprised to hear country tunes coming from the room. His uncle must have forgotten to turn off the radio, but as he opens the door and sets foot inside, he’s surprised to find Y/N in the ranch owner’s spot.

“Hey,” she greets, looking up with a kind smile on her face.

Once again, the cowboy is taken aback by her appearance. She must have changed clothes after the midday break, because instead of the usual pair of jeans, cowboy boots and a long sleeved button up shirt, she’s dressed much more appropriate for the warm weather. The gorgeous woman is wearing shorts, her bare legs coming out from under the desk, crossed at her ankles with a set of Allstars on her feet. The crepe colored cuffed T-shirt is cut lower than what she usually wears when she’s at work and Dean kicks himself internally when his eyes drop to her cleavage for a split second. Thankfully, she doesn’t seem to notice, her focus already back on the laptop in front of her.

“Hey. Sorry, I uh -” he stammers. “I didn’t know you were in here.” “Yeah, Bobby said it’d be okay if I look at the finances, now that he’s out of town,” she explains, pretending she didn’t feel his eyes on her, and somewhat apologetically gesturing at the piles of paperwork, opened folders and receipts surrounding her. “Hence the mess.” “Right, that’s - that’s great. I hope you can make sense of his handwriting,” he chuckles, moving closer to the desk while rubbing his neck nervously.

The intern glances over the screen, a huff passing her lips. She feels like she has been trying to decipher a military code for the past hour, so she gets what he’s saying. Thankfully, she’s beginning to get the hang of it, though. Despite that she would rather be working with horses, this is a field she’s familiar with. Numbers, balances, filing, thinking about business plans and coming up with marketing ideas; she used to do this nonstop. The handsome greasemonkey who just entered her calm and safe confinement, however, is bringing more distraction than she can handle.

His white undershirt is damp, the ranch hand’s broad shoulders on full display. He’s covered in black smears, and by ‘covered’ she means his strong arms and hands, even his face. The emerald green eyes she fell in love with the moment he first looked at her seem even brighter, now that they are surrounded by strokes of grime on his cheek and nose. Perspiration making his skin shimmer, beads of sweat gathering in the dip above his collarbone. Sand is sticking to his light brown hair, the particles peppering his chest as well. God, if they would have been together still, she wouldn’t think twice about jumping him. Considering they are not, she clears her throat and swallows with difficulty, hoping he’s not aware of her ogling.

“It’s a challenge,” she replies to his previous comment, but secretly the answer covers so much more ground. Trying to distract herself, she focuses on her work again. “I’ll bet,” he acknowledges, unable to take his eyes off of her.

She might be typing furiously on her keyboard, but the wrangler noticed her gaze, alright. Struggling to keep his head cool, he tries to think of something to say to break the sexual tension that is fogging up the office.

“Any bright ideas on how to get a bit more profit out of this joint?” he wonders, figuring that talking business might extinguish the sparks that are flying between them.

“Actually, yes. I have a few,” Y/N says, glad to be able to shift her mind to something else than Dean’s muscular body. “I’m just trying to get a basic overview of the liabilities and the assets, but I’ve already spotted a few things that need improving. I believe that right now, focusing on tourism might not be the best idea, since that target audience will be affected by the economic depression more than owners of expensive horses will. The rich rarely get poor when times are hard for the country, so that’s the segment the ranch should be aiming for.”

As she offers her insight, Bobby’s right hand takes her in. She clearly knows what she’s talking about, and once again he's impressed with her intelligence. When she suggested giving the books a once-over, he was worried his stubborn uncle might not accept help from the intern, certainly not in that department, but she managed to talk him around. Not once did Dean doubt that she would deliver, though.

“I found the GCR website, but it looks like it was built in the nineties and hasn’t been updated in years,” she remarks without holding herself back, knowing that she can speak freely. “Who maintains it?” “That would have been Ash,” the wrangler admits, seeing how that could be a problem. “Right…” Y/N ponders. “Do you know if Bobby ever had a marketing plan made?” “A what now?” the cowboy says, puzzled. “You mean, advertising?” She tilts her head to the side, half nodding, but not entirely settling on his answer. “A marketing plan is a bit more advanced than that, but yeah, ads are part of it.”

Dean thinks for a second, pulling at his lip with his front teeth. “The ranch was listed in that magazine JQurnal a couple times, but that was years ago. It’s just too expensive. Bobby always says we should let the ridin’ do the talkin’ at the shows.” “He’s right, but if people have trouble finding the ranch online and aren’t familiar with the brand, a good run isn’t going to be enough,” Y/N brings to mind. “For instance: I couldn’t even find you on Google. I only found a few show results with your name at the top.”

The cowboy does a double-take, crossing his arms in front of his chest, a grin plastered on his face. “You googled me?” “Oh, don’t flatter yourself.” She shoots him down, trying to hide a playful smile. “My point is; this ranch needs a good website that tells the potential customer about its vision, the offered services and good references. We also need to create an account on Facebook and make sure it’s interactive, post nice photos on there to attract people. It’s free air-time, basically. Social media is going to be the way to put a company out there.”

“I’ll message Ash. I’m sure he still has the account information,” Dean assures. “Great!” Y/N says, content, glad that they are getting somewhere. “I’ll ask my brother to look at the design and programming. He’s in IT, so he can help us out. Meanwhile, I’ll see if I can organize all this, list the overhead and operating expenses and prioritize what Bobby needs to take care of first. Oh! And I can start on the marketing strategy, maybe write texts for the web page--”

“Y/N?” The intern behind the desk looks up, met by the head wrangler’s warm eyes which are filled with appreciation. It stops her waterfall of words instantly. “What?” she returns softly. He holds her gaze, a smile tucking at the corner of his mouth. “Thank you for doing this,” he says, sincere. “No worries,” she returns, somewhat shy. “Glad to help.”

A comfortable silence falls over them as the head wrangler watches her leave through a stack of invoices, before he steps back to the door. Y/N stops him, however. “Dean?” The cowboy turns around. “M-hm?” “What did you come here for in the first place?” she wonders. “Do you need anything?”

For a second, he’s not sure how to answer that, confused by the question, but then the lightbulb in his head switches on. Jesus, I’m so lovestruck that I can’t even think straight. “Oh! Right. I need the number of the John Deere dealer in Phoenix. We figured out what’s wrong with the tractor,” he explains. “Bobby probably has the number scribbled somewhere on a post-it or somethin’.” Her eyes roam over the mess of yellow notes, detecting the one she’s looking for and pulling it off the small memo board next to the desk. “Here you go.” Dean takes the piece of paper from her, waving it in the air as he moves towards the doorway. “Thanks.”

As the cowboy pulls the door shut, he holds on to the handle for a second, blowing out a breath. The current that was coursing through him and had his muscles stiffen, begins to ooze away. He really needs to get his act together, because no matter how badly he wants to be with Y/N, he simply can’t have her. But now that they are hanging out as friends again and don’t avoid each other anymore, denying the obvious pull is going to be anything but easy.

He draws his phone out of his back pocket, holding the note next to it as he types the digits into the device while walking to the front porch. Maybe if he stays busy, he can keep his mind off the woman he’s in love with.

The pot roast Ellen made before leaving is absolutely delicious, filling the stomachs of the hungry crew beyond capacity. Benny leans back in his chair, the brawny farrier rubbing his hands over his round belly. One would expect the lack of table manners from him and from Dean, but it’s Garth who lets out a burp, having the others in stitches.

Y/N shakes her head disapprovingly, glaring at Jo over her glass of water when the petite woman manages to outdo the stable boy, triggering more laughter. The whole lot are a bunch of savages, but she wouldn’t have it any other way.

After dinner, it’s finally time for some quality time with the intern’s favorite being on earth. After changing her sneakers for her boots, she heads to the stables, where the horse with the pretty white face and Bambi eyes is waiting for her. The mare neighs softly when she notices her owner, kicking her door with her front feet, impatiently telling Y/N to hurry up.

“Alright, alright.” she chuckles, taking Meadow’s halter from the hook before she unlocks the stable. “What do you want first? Playtime in the paddock or a grooming session?”

The Quarter stretches her neck and tilts her head, begging for a good scratch. With a wide grin on her face, Y/N rubs the horse’s withers, watching how the Meadow wiggles her upper lip in delight, clearly enjoying the backrub. Chuckling, the cowgirl rustles her black mane. “Grooming it is then.”

Meadow seems to disapprove when her human stops the massage and pulls the pole piece over the horse’s ears. The animal ushers Y/N to continue, invading her private space, and even though she should correct the mare for such behavior, she laughs at the persistence. Meadow wishes to be treated as the princess that she is and knows very well she can get away with it.

In a way, it’s what makes their bond so much stronger. The mare isn’t suppressed by a strict regime or compelled to show obedience. Some trainers will claim that if a thousand pound animal doesn’t want to do something, it won’t. Y/N doesn’t agree. She has seen plenty of horses on shows in the warm-up area who obeyed, not because they were asked a question, but because they were ordered, knowing very well what the consequence would be if they didn’t listen. Those animals don’t respect their riders. They fear them.

Y/N has always allowed her horse’s true character to shine, rarely having to stand her ground, because somehow, the smart animal knows exactly when there’s room for a little fun and when there isn’t. Like that evening in Flagstaff, when Meadow was the only thing that kept Y/N on her feet after Dean broke her heart. Time after time, it amazes her how good these creatures are in picking up on emotion and energy. They are so sensitive, so willing, so kind. Why would anyone want to force respect, when you can so easily earn it?

Meadow follows her owner though the stable alley to the tack up area, her shoes clicking on the pavement. The horse girl sets the grooming bag down on the ground and chooses the mare’s favorite brush that will help her loosen her summer coat. She’s beginning to shed, and Y/N makes a mental note to put on a thicker rug tonight before her coat gets too long. Little hairs and dust particles dance in the evening sunlight, floating towards the ground like leaves in autumn. Once again, Meadow’s enjoyment spreads a smile to the young woman’s lips. It’s therapy for both of them.

After the extensive grooming session, Y/N straps a pair of bell boots over her horse’s hooves, which will make sure she doesn’t lose an iron shoe while running around in the paddock. The equestrian leads the enthusiastically dribbling Quarter. After turning her around and closing the fence, Y/N unclasps the leash, causing the feisty mare to turn on her hind legs and sprint away, bucking happily as she circles around. She then drops her head to the ground, sniffing the sand while looking for a good spot to take a sand bath. With a satisfied groan, Meadow drops to her knees and softly lands on her side, rolling in the dirt and enjoying every second of it. Her owner chuckles; so much for brushing her clean.

The dusty horse gets up and shakes out the sand like a dog would after having a swim and groans, satisfied. She then continues to explore the paddock, swishing her tail and looking around curiously.

Y/N climbs the bars of the steel fence, taking a seat on the top one. Now that she has a higher perspective, her gaze roams over the fields. Cain is still in his pasture, which is the furthest away. He has taken notice of Meadow, but doesn’t seem interested, which is quite odd, since he’s a stallion. The poor horse has barely moved from his spot since he arrived earlier this week, but thankfully started eating and drinking two days ago. For now, Dean is letting him be, giving the traumatized animal the time to adjust to his new surroundings. He can’t start any kind of training without the horse being comfortable in his environment anyway.

“Hey.” Breaking away from her wandering thoughts, Y/N looks over her shoulder as the man who she was just thinking about approaches the fence. He has freshened up and replaced his strained shirt for a clean grey Henley, the sleeves of the clothing piece rolled up.

“Hey,” she greets back, swaying her legs a little and looking down at her boots. “Beautiful sight, ain’t it?” he comments while laying his arms over the top rail, elbows out with his chin resting on the back of his hands. Clearly enjoying the view, he looks out over the property.

She lifts her head again and straightens herself, squinting against the sinking sun. The desert land is set alight by golden rays coming from the west, the hills in the backdrop transitioning into mountains on the horizon. Little bugs twirl above the surface, the absence of the wind allowing them to dance in the air freely as they are illuminated by the warm light. The working horses are grazing up ahead between the cacti, peaceful, and adding to the serenic scene. “It is,” Y/N agrees, smiling in contentment.

For a moment, she allows her eyes to fall on the cowboy by her side. He can’t see her, his hat shielding her subtle glance, which gives her the opportunity to linger in a daydream of what could have been. The scent that she remembers from the times he held her close floods her senses, a mixture of leather, his usual shower gel, and a subtle musk that is so unmistakably his. The things that she would give to still call him her man, to be able to kiss him and find comfort in his loving arms.

Somewhere along the line, life took a turn she never saw coming. Maybe it was the speed at which they traveled the treacherous road that caused them to go over the edge and tumble down the slopes. Maybe it was the altitude they reached that made the fall so long and painful. Whatever the reason, she will never know, not as long as he won’t talk to her. Y/N isn’t exactly sure if she is looking for hope or closure, but the question that has been ringing in her ears since they broke up suddenly comes crashing through the surface.

“What happened between us?”

The four words that are pronounced with deject catch Dean off guard, and he gazes aside, mystified. The way they have been around each other over the past few days and how she seemed so much more comfortable in her skin had him think all was said and done. But that dreadful conversation he hoped he never had to have has just been kicked off with her seemingly simple question. It’s one only he can answer, and he owes her that much.

Y/N half expects her ex boyfriend to turn around and walk away, since he preferably avoids a heart-to-heart like the one she just initiated. Instead, he lets out a sigh, not one of annoyance, but to ready himself for what’s to come. After contemplating for a moment longer, Dean places his foot on the bottom rail, hoists himself on the fence and takes a seat next to her. He’s cooperating, which has to count for something, and yet he doesn’t seem to know what to say, causing the girl by his side to fill the dreadful silence.

“I just… I can’t wrap my head around how we went from being absolutely fine in the afternoon and then having that huge fight hours later,” she expresses hesitatingly. “I know I was acting like a jealous control freak, and - and I got so confused by the way you labeled me when your father was there. I never meant to give you the feeling that I don’t trust--” “Whoa, wait,” Dean interrupts, staring at her in shock. “You think this is on you?”

Placing her hands on each side of her and gripping the cold bar, she shrugs. “I mean, mostly, yeah. I realize I said and did a few things that caused you to blow up on me like that and had you running for the hills.”

Dean’s gaze unfocuses, then he tilts his head back and closes his eyes before he tucks his chin down again. Regret has his heart in a tight grip while guilt settles in his stomach like a heavy chunk of concrete.

He should have known how her mind works, how her insecurities would instantly take the angry words he shouted at her and twist them into a scenario where she is the villain. A scenario in which she’s not good enough, not pretty enough, has too many vices and is too complicated. A scenario in which he lost interest because of those very reasons. None of it is true.

The cowboy wanted her to be angry at him after that night, figuring it would be easier for her, but now that he has found out that she has been blaming herself for their split all along, he almost buckles under the weight of his remorse. She deserves to know his intentions, no matter how difficult it is to open that bear cage in which he has locked away his feelings. And so he looks at her, hoping that he can offer her some consolation.

“Yankee... You did nothing wrong, you hear?” he presses, his sincere, shamrock green eyes adding to his message. “If anything, you’ve been absolutely perfect.”

It’s the first time Dean calls Y/N by her nickname again, an alias that he reserved soon after the intern arrived at the ranch. It became a sobriquet only he used, one he always said with such endearment. Today it’s no different, and the fondness adds so much sentiment to his message, that it begins to overwhelm the woman it’s meant for. She holds his gaze, however, tears brimming on her lashes.

“Then why don’t you want to be with me?” she asks, her voice fragile.

The fist of contrition that has enveloped Dean’s heart squeezes closed, barely allowing it to beat. You stupid idiot, he thinks to himself, what have you done to her? He gave in to his feelings, deep down knowing their relationship was going to end in destruction, and he still let it sail its course. He should have never allowed Y/N to get so close and yet he did, because he never took into consideration that a woman would want to stick around. Just like he never considered it a possibility that he would fall in love himself, yet here they are.

God, he wants to tell her the truth, but at this point the cowboy isn’t sure if it will make matters better or worse. He averts his eyes for a second, biting the inside of his cheek, before returning his gaze and meeting the one of the girl he would move mountains for. He has to be brave now, he owes her that much. So he takes a deep breath while he searches for words, eventually choosing the ones that come from deep within his soul.

“I do. I do wanna be with you. Breakin’ it off, it was never because I didn't care enough. On the contrary, I care about you, so much,” he admits, a sad smile spreading across his lips. “That’s why I can’t be selfish here.”

Stunned, Y/N’s shimmering eyes enlarge. She never expected a revelation as such, convinced that Dean felt like they weren't a good match. He was so frustrated, so angry. His bitterness that evening at the showgrounds truly convinced the cowgirl that he didn’t want to be with her, but now he claims that does? “What - what are you talking about?” she stammers in confusion.

Dean hooks the heels of his boots on one the rail below, shifting slightly and placing his hand around the top bar, only an inch away from hers.

“You deserve the world. That and so much more,” he states. “You deserve a life that’s stable, without complications, without worry and uncertainty. To be with someone who treats you well and can provide for you--” “This isn’t the 1950’s, Dean. I can handle myself,” she interrupts. The wrangler chuckles softly, appreciating her feist in the midst of the tragedy. “I know. But sharing your life with someone who can’t be upfront and holds back secrets; it’s not what I want for you.”

Y/N ponders, her eyes fixed on her horse in the field. She has heard this song before, but she didn’t realize its meaning, simply because it was sung in a different language. When Dean spewed out all that fury during the argument, all she took from the string of vexed words was that he was convinced she couldn’t deal with him on his bad days. Yet all this time, all he has been thinking about is saving her from himself. Can’t he see how much he has to offer?

“What about someone who makes me happy, makes me laugh, makes me feel appreciated?” the cowgirl brings to mind, studying the man next to her on the fence. Dean sighs dejectedly. “Well, if you’ve been thinking that this was all your fault, I clearly failed you in more ways than one.”

She’s studying him, he can feel her eyes burning like the sun on a blistering hot summer day. He tips his hat downward and stares at the chunks of dirt below, wishing he could time-travel and do her justice by keeping a safe distance. He can’t, though. He can’t make this right. It was never right to begin with.

Y/N exhales while the handsome man mulls over his mistakes. Her fingers, which are wrapped around the cold steel, itch to move over her ex boyfriend’s hand, but she doesn’t give in to the temptation. He’s hurting enough as it is. They both are.

“Dean, whatever is holding you back, it will never change how much I…” she pauses, the word ‘love’ on the tip of her tongue, but she decides not to drop that bomb, “how much I care about you.”

The persistent fire of hope inside of her might have decreased to a small flickering flame that barely stays lit in this storm, but it hasn’t died yet. Maybe one day she will be able to tell him. Maybe one day he will be able to accept it, and who knows, even say it back. The cowboy restores eye contact, having picked up on the short cease. I’m seeing things, right? Was she really about to say that she…?

Chasing the thought from his mind, he focuses on the mountaintops ahead, the last light catching the volcanic formation. “You don’t know that. And I… I can’t bring myself to open up about what happened. I just can’t,” he returns, his voice breaking on the last word. “That has nothing to do with you, I swear. No one knows, no one but my father.” “What, not even Ellen and Bobby?” Y/N asks, perplexed. Shaking his head, the wrangler pulls at his bottom lip while wondering if he has already said too much. Empathy begins to build, the urge to offer him any kind of alleviation growing. “Dean, you can’t keep this in.” “I have to. My family, my friends, you… No one will look at me the same if they know what kind of person I really am. The things I did…” He sighs. Admitting how the shame he can’t quite explain is incredibly difficult on him. “I’m a monster.”

“You are not a monster.” She reaches for him, breaking the constraints that held her back. Her delicate hand cups his face, his stubble brushing against the pad of her thumb as she gently strokes it over his cheekbone. “I don’t believe that, and neither do I believe that the people who hold you dear will dispose of you when the secret does come out.”

Dean breathes out a shuddering breath and leans into her touch. He doesn’t want to discourage her, but he’s convinced that when push comes to shove, the outcome will be different. Nevertheless, he cannot force himself to move away right now. The connection affects him beyond what he’s capable of handling and he squeezes his eyes shut, struggling to collect himself.

“I’m so sorry,” he says, his voice soft and cracked. He glances aside at her again, remorse evident on his features. “I’m sorry that I hurt you the way I did, that I made you feel like you aren’t enough, because you are,” the cowboy assures, genuine. “But it’s better this way.”

The emotion that the conversation reveals is contagious, evidence of it threatening to overflow and come down her cheeks. “For whom exactly? Because it isn’t for me.” “In the long run, it will be,” Dean guarantees.

Y/N reluctantly allows her hand to slip away from him and straightens herself, resting her elbows on her knees and clasping her hands over each other as if she’s praying for a different outcome. “I can’t change your mind, can I?”

She won’t be able to, both know that by now. Severe self-esteem issues and crippling trauma disable the blind and broken man from having a clear view of the road to happiness. All he cares about is her journey, and he will be nothing but a burden if he hitches a ride. “How can I change my mind about wanting what’s best for you?” he returns.

There is something very final about his reply, and after a few seconds, Y/N admits her defeat. As she tries to not get lost in the intensity of the heartbreak, she takes in Meadow, who watches her owner from a few yards away. Tears begin to roll down her face nonetheless as she squeezes her lips together in a tight line.

Dean swallows hard at the sight of the girl next to him. The evident pain she’s suffering from almost makes him cave, but he keeps thinking about the bigger picture and how he doesn’t fit into it.

“Hey…” he whispers, nudging her shoulder. “Know that I’m always gonna be there for you, if you want me to, at least. That will never change.” “Really?” she says, the idea of his support offering some solace. “Promise,” he pleads.

A soft smile pulls the corners of her mouth upward as she holds his gaze, the truthfulness of his oath sinking in. At least they still have this. A strong friendship, an unbreakable bond, one that survived the toughest breakup she has ever lived through. Appreciating that treasure, she sniffles, wiping her cheeks dry before she lays her head on his shoulder.

There isn’t a hint of hesitation when he lets go of the bar, wraps his arm around her waist and rests his chin on top of her hair. Counting his blessings, Dean shuts his eyes; he hasn’t lost her completely. They sigh simultaneously, the heaviness of the much needed talk leaving the pair.

The moment is interrupted when Y/N senses someone approaching, hoofbeats falling on the sandy soil. A curious horse halts in front of them, only a few feet away, observing her owner with wonder. Meadow seems somewhat confused, worried even, picking up on the distress. Gently, the mare pushes her soft nose against her human’s knee, her lip twitching to get her attention.

Y/N huffs a laugh, stroking the Quarter’s neck sweetly. How does she always seem to know how to cheer her up, just by taking notice and seeking her out? Meadow has the ability to offer comfort and show empathy, a trait of these gentle giants that she admires greatly. Whoever claims horses can’t talk, refuses to listen.

The head wrangler smiles warmly at the connection between animal and human, glad that the kind creature is able to spark joy within the girl next to him. Two souls entwined, speaking a language of their own, an endearment for one and other that will last a lifetime. Her presence doesn’t just heal Y/N, in a way it eases the cowboy as well. The pair has something very special, and he’s thankful they do.

“Are you still coming with us to Congress?” the cowgirl wonders, scratching behind Meadow’s ear, one of her favorite places. Raising his eyebrows at that question, Dean takes her in. He didn’t consider that her offer still stands. He retreats his hand that was resting on her hip and steadies himself on the rail. Not to put distance between them, but because he uses the other to ruffle Meadow’s mane, who has now taken an interest in him.

“Are you sure? I mean, if that’s what you want,” he returns, stumbling a little. “It’s the biggest competition we’ve ever ridden; of course I want my trainer there,” Y/N states matter-of-factly. Humbled, Dean huffs, amazed by the woman’s resilience and capability to forgive. No wonder she’s so good at everything she does, because no matter the hurdle, she always bounces back. “Well, in that case, I wouldn’t miss it for the world,” he agrees.

The cowgirl beams at him, sentiment still apparent in her glossy eyes and slightly contradicting her facial expression. The story of her and Dean has become a bittersweet memoir, but they haven’t reached the final chapter yet. There is more to be written, and it might not be the romantic novel she hoped it would be, but it’s still a tale worth telling. She wants Dean there to cheer her on when she enters that enormous arena. She wants him there to catch her when she has finished her test. In her heart, she knows that he will keep his promise; he will always be there for her. And who knows? Maybe there will be an unexpected twist at the end of this book.

“You’re gonna pick up training tomorrow?” the horseman assumes. Y/N nods. “Yeah. I gave her a few days off to recover from Flagstaff. I didn’t want to overwork her right before the big show.”

It’s a smart approach to a big event, one that takes confidence and Dean approves of. A lot of riders would have trained hard every day up to that pinnacle moment, with the risk of tiring their horse and reaching that peak too soon. Meadow doesn’t have to learn anything new, though. Her run at the horse fair was spectacular. All that’s left to be done is light training to build her up and get Meadow to Columbus fit and fresh, so that the little mare can ace another solid performance.

“6.30 AM, then?” Dean checks. “Alright, 6.30.” The agile cowgirl swings her legs over the top rail, facing the other way before she hops down. “I’m gonna clean my tack and start packing,” she announces, making her way to the barn. Dean chuckles, twisting his body to watch her go. “Already? We’re leaving in five days.” “Exactly!” Y/N returns, as if he has just proved her point.

She disappears into the stables, leaving the wrangler shaking his head, grinning. She’s such an lively light. Nothing can stop her, not even his bad-decision-making. Her request for him to travel to Ohio with her took Dean by surprise, but he’s glad that they are at that stage. The professional partnership they have works incredibly well, Y/N and Meadow’s results in Flagstaff speaking volumes. Maybe if his contribution to the equestrian’s success helps kick off a promising career, he will be able to come to terms with the many times he fell short.

Meadow still stands before him, apparently enjoying the cowboy’s company. Y/N has mentioned before that the strong-willed mare isn’t a fan of men, but somehow she doesn’t mind it when Dean runs his hand down her neck, her coat feeling like satin under his touch. “I figured you’d be pissed as hell at me,” the horseman begins to talk, “for hurting her so much.” But the Quarter seems anything but annoyed with the wrangler, twitching her lip against his jeans, hoping he has a treat stored in one of his pockets. It makes Dean chuckle.

“I just want her to be happy, y’know? For her to fulfill her dreams. I know you do, too.” He runs his fingers through the horse’s dark mane. She perks her ears forward at the man on the fence, listening to his voice. He’s aware she can’t fully understand what he’s saying, but she does sense that he has a broken heart. Affectionate, Meadow softly presses her nose against his cheek, blowing warm air against his rough skin. It always amazes him how careful and gentle these large animals can be, and appreciates the kind gesture.

“I’ll let you in on a little secret,” Dean says softly, caressing the horse’s beautiful sculpted face. “I love her.”

It’s painful to say it out loud, and yet he smiles. There’s something liberating about letting the three word sentence that holds so much meaning fall off his tongue. Meadow will not be able to pass it on, so the revelation is safe with her. Dean sets his jaw, fighting the sentiment that ambushes him unexpectedly, before he continues. “But sometimes when you love someone, you gotta let them go.”

The bay horse purrs, blowing out a breath while her dark brown eyes take the cowboy in. She then lays her heavy head against his chest, an act of kindness usually preserved for her human, comforting the man who has earned her trust with one glance into his soul.

They stay like that for a moment in time, and eventually when there’s nothing left to be done, Meadow strolls away, letting the horseman be. Dean folds his hands together, resting his forearms on his knees, needing a minute before he joins Y/N in the tackroom. Throughout the tough conversation he stood strong, able to keep the tears at bay surprisingly well. Now, though, he wipes his eyes.

He’s not sure when this happened, when ‘liking’ her became something more. Maybe it was when he first kissed her by the fire, maybe when they laid together under the stars or when she fell into his arms after winning her freestyle debut. It doesn’t really matter how he got here, because it’s crystal clear to him that he loves her. He has let her go, and that’s how he knows.

A soft thud behind him breaks Dean away from his epiphany. He turns around, finding a fluttering bundle of red laying beneath one of the barn windows. It’s a Northern Cardinal who has mistaken the glass for an open passage, the bird rustling its fiery red feathers as the tiny animal gets back on its feet, needing a moment to recover from impact. Dean has seen them here before, but they are quite rare this far south. When it remains on its spot, the wrangler lowers himself from the fence to see if the poor fellow needs help, but when he’s within a few feet of the bird, it flies away.

Both intrigued and concerned, he keeps track of the feathered creature, which isn’t difficult thanks to its bright color. Dean isn’t necessarily superstitious, but his aunt used to tell him that this species of birds are messengers from God. Cardinals appear when an angel is near, he remembers her saying. When one flies into a window, however, it’s believed to be a bad omen.

The bird floats over the pasture while chirping, landing on a fence-pole. Meadow notices it, approaching cautiously until the cardinal flees, spooking the Quarter. The bay horse makes a funny sound similar to a squeal, showing off her neck as she bucks like a young foal. Dean smiles at the sight of the fresh mare, who clearly took the opportunity of the small animal's sudden movements to overreact and make a scene. She doesn’t seize her sprint, though. When she continues to run in circles, Dean decides to turn her in. It’s clear that the characteristic horse wishes to be escorted to her stable.

When he can’t find the leadrope, he enters the barn, remembering Y/N took it with her to the tackroom. Met by the smell of leather and oil when he enters the storage space, he finds the cowgirl on a stool, rubbing her saddle clean with a cloth.

“Meadow’s getting restless. Want me to bring her in?” he offers. She lifts her attention from her task for a second. “Yeah, sure. Thanks.” The wrangler takes the rope off the hook by the door and moves out of sight again, leaving Y/N to work in a blissful silence. Plenty of horse people detest this chore, neglect it even, but taking care of her tack has always soothed her. The step by step routine is something she can focus on when her head is too restless with processing information. Today is no different, although the meaningful and much-needed conversation with Dean already offers the relief she was hoping to find. She feels lighter, despite the difficult and draining exchange they just had. It’s out of the way now, the last remaining remnants of incomprehension cleared up. The fog has lifted, now she can focus on what’s ahead.

There have been times during the past week that the All American Quarter Horse Congress was the last thing on her mind. She stared at the booking website on her laptop screen for hours, her information already typed in, ready to book a flight home and leave it all behind. Thank God, she didn’t. It would have been a waste of a once in a lifetime opportunity, one that she is going to take with both hands. Y/N can’t wait to dance with Meadow again, the grand stadium their stage, the music their melody. It’s going to be an unforgettable r--

Her contentment is suddenly disrupted by a distant scream. The cowgirl perks up, her sense of hearing heightened. It sounded like the way a stallion roars, the high-pitched neighs Cain made in the trailer when he tried to fight his way out are forever edged on her eardrums.

Uneasy, she gets up from the seat, picking up on the running footfalls in the gravel, every rushed step sounding further away. The commotion has her haste towards the doorway while a bad feeling takes hold of her. Before she can step into the alley, Dean’s bone-chilling voice reverberates under the high roof, calling out her name at the top of his lungs.

“Y/N!!!”

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#Ride With Me #Dean x Reader #Cowboy!Dean #Dean angst #Dean series #Dean Winchester series #Cowboy!Dean AU #cowboy!dean x reader #Dean Winchester

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