Y/N’s past hunts her down, and she finds out some of Dean’s secrets as well. Dean has to choose whether to fall or to fight.

Characters: Reader (Y/N), Boss Mr. Shurley, former ex, Sam Winchester, Dean Winchester, Uriel, Cole Trenton, Raphael, Virgil, Castiel

Warnings: Boxing violence, abuse mention

Word Count: 3500+

Notes: I’m sorry I couldn’t finish the series in time for the Supernatural Fic Apocalypse, but I hope you like it and will look for it in the next few weeks. Tag lists, requests, and feedback comments are open. Enjoy!

Part 1: Ringside       Part 2: Caution

Y/N aligned her pens and pencils for the day. It didn’t wasn’t much, but being a secretary paid the bills well enough. She pulled the weekend cover off the typewriter and ran her fingers over the keys. One day she would buy one for herself; then she could create magic.

Mr. Chuck Shurley waved at her as he entered his office. He hung his hat on the doorknob, a sign he didn’t want to be disturbed, and Y/N heard the door click as he locked it. She assumed it meant he had several submissions to look over. Being the boss of a small publication company meant he had final say over what they published. Y/N hoped that being secretary would help her out when she wrote her first piece.

Y/N, deep in thought over that dream, didn’t pay much attention to the suited man who walked up to her desk, hat in hand.

“Excuse me miss, does Y/N Y/L/N work here?”

His voice made her blood run cold. Y/N looked up and almost screamed. He was smartly dressed, but she knew what lived underneath. She reached for the button that would call security, but…

“Please don’t. I’m in, I’m out, I’m gone. Just hear me out.”

Her heart thundered in her chest as her finger hovered over her salvation. He walked around and took that hand in his. Y/N gasped in defeat. Maybe she could scream?

“When you left… I thought I would die. I got drunk every night till my mind cleared. It’s all my fault; I hurt you. I shouldn’t have.” He sank to one knee, “can you… will you forgive me?” The crouch pulled back his coat to reveal a vest holster. Words died on her lips. He chuckled nervously, “say something. Anything.” He let go of her hand to pull his jacket over the holster.

She took her chance. And pushed the security button. Mr. Shurley yanked his door open as your ex stood and pulled back his hand. Mr. Shurley saw you flinch and pushed him out of the way. She leapt to her feet and stood behind Mr. Shurley. ‘He’s got a gun,” She whispered as the guards ran in. They took him by the arms and led him out.

“I’m sorry, Y/N! Bitch! I said I was sorry!” His crying and cursing faded away, leaving Y/N shivering against the wall.

When Mr. Shurley turned, she burst into tears. “I’m sorry, sir. I thought I was far enough away. I didn’t mean to put anyone in danger. I…”

“It’s alright, Y/N. Is there anyone you can call to take you home? Preferably a man?”

“No… yes.”

“Hey, Winchester, some girl’s calling for you.”

Dean nearly ran to the training gym’s receiver, grinning through the whistling from the other guys. “Y/N. What I can I do for you?”

His face fell as he heard her broken voice on the other line. “Dean, can you come get me from work?”

“What’s wrong? I can be there in…”

“Winchester!” Uriel called out, motioning him to come to the ring.

Dean cursed under his breath. “I can send my brother. You know Sam, right? Will he be an okay second till I can get there?” Dean waited with baited breath till she answered.

“Yes.”

“I’ll send him your way and come as soon as I can get away. I promise.” Dean got her work and home address and sent Sam with a cab. He walked to the ring and said to Uriel, “say it quick. I’ve gotta leave.”

“Don’t rush me; We’ve got important matters to discuss.”

“Yeah, I know. Do what you say and everything will be peaches. I got that.” Dean stepped to walk away, but Uriel grabbed him by the collar. He spun him around to the row of seats surrounding the practice ring.

“Have a seat. There’s more to it.” He leaned against the apron, towering over seated Dean. “Raphael seems to be under the impression that you will follow orders better in the future if we give you this win.”

“Fantastic. Can I go now?”

“No. Cole, on the other hand, wants to beat you fair and square. While I am inclined to agree with him, there is a bit of a time constraint considering your fight is the undercard to Sam’s. So he’ll go down quick enough.”

“Great. I’ll be seeing you…” Dean tried to stand, but Uriel forced him back into the chair. Dean snarled, arms tensed and ready to share a few blows. From the corners of his eyes, he saw the other fighters in the gym look away.

Uriel chuckled and patted Dean’s shoulder. “Don’t think we don’t know where you’re running off to. We saw that sweet little miss you ran to the night this all went sideways. Your Sophie[1] can wait a few minutes. If you don’t think so, I can talk on the way over and explain personally why you’re late.”

“She doesn’t know anything. She doesn’t need to know.” Dean pushed Uriel’s hand off his shoulder, “and I am not just going to sit here while you threaten her. I’ll do your bidding, for Sam, but you’ll leave her out of this.” He turned and stalked away, grabbing his leather jacket off the hook next to the door.

“If you walk out that door now, Winchester, your career here or in any other boxing circle is finished.”

Dean looked over his shoulder at Uriel’s fuming face. “Then I guess after Cole’s rematch I’m done.” He slammed the door behind him.

Uriel punched the corner of the ring, making the rope post splinter around the edge. He scanned around, then found him. “Trenton! Get over here; we need to talk.”

“Thank you for bringing me home,” Y/N said from the couch. Jo and Claire were out at their own jobs, so Sam had taken it upon himself to make coffee. He brought her a cup, which she nearly dropped from her shaking hands. He took it back and sat it on the end table before sitting next to her.

“You’re going to be alright. Dean’s not going to let that creep anywhere near you. I wouldn’t be surprised if he’s hunting down that bast-… the guy right now.” He glanced at his watch again, wondering what Uriel was holding him for.

“Why do you look worried?” Y/N asked with a nervous chuckle. “My ex is the one in danger.”

Sam shook his watch back under his sleeve. “Nothing. The boss was talking to him, and it didn’t look good.” Sam coughed, “not that you need to think about it too much. Probably a pep talk that couldn’t happen any later.” He handed her back the coffee mug, relieved it didn’t shake as much.

Y/N was thinking too hard for her hands to shake. Connections broke past her terrifying memories. “Are the fights rigged?” she blurted out.

Sam almost fell off the couch. “What? Why would you think that?”

“The guy at the dinner. He said the fights were faked.” Y/N nibbled her bottom lip. She handed the forgotten coffee back to Sam. In the contest, Dean was almost counted out, then he looked at her. She remembered the way his eyes gleamed, she thought in defiance of defeat. Maybe there was more to it. “Was he supposed to lose the fight I met him at?” She looked up at Sam when he didn’t answer. He tried to stand up, but she placed her hand on his thigh, freezing him in place. “Tell me the truth. Is it rigged?”

The front door clicked shut as Dean walked in. “Is what rigged?” He glanced at Sam, who was staring into the coffee mug. “You told her?” Dean shouted.

“I didn’t say anything!”

Y/N stood and walked over to Dean. At first, he looked down at her in shock, then glanced away before grabbing the door knob to leave.

“No. You’re not going anywhere till you tell me what’s going on.”

“Y/N…”

“Is this what you couldn’t tell me at the dinner?”

Dean met her gaze. His eyes darted between hers. With a sigh, he took off his hat and coat. “This is going to take a while.”

Y/N had no idea there was such thing as a family business in boxing. When their Dad died, the ring they owned would have gone under had it not been for Raphael. But he changed things. Everything. The easy thing about bribing the boys was he could always threaten to hurt the other if they stepped out of line.

“That’s why I don’t want to get you involved. I didn’t want to put you in danger.”

“I’m already in danger! But I would much rather have you on my side than have to battle anyone alone.”

Dean growled, “did they threaten you already? Is that why you called me?” He stood up and paced around the room. “That son of a… I’m going to rip his throat out.”

“No. It was my ex.”

Dean stopped. “The one you told me about?”

She nodded and told him about her morning. She couldn’t say his name. It withered and evaporated before it could reach her lips, frightened to summon the ghost into reality. Then the rest of her story spilled out. She told it like it was a common thing. Small town, no chance of escape. He was the better of the prospects. But the local bar made good money off men like him. The town rebuilt the police station next to it for easy access, it was so popular with guys quick to their fists. Y/N wasn’t sure how many people took the fights home with them. They’d been engaged. He almost lived in her parent’s house, but just short of paying rent. Their attic always seemed to smell of cheap whiskey. She left after just one episode, penniless and only possessing the clothes on her back, refusing to live in a place where denying to buy him a refill made him… she didn’t, couldn’t finish.

“I’m gonna rip his throat out too.”

“Please don’t do that. He’s just a leech of a bum who happens to own a handgun. You’ve got bigger fish to fry.”

Dean sighed and sat back down. “Sounds like equal Jonah swallowers to me.” He sat in silence for a moment. “So that’s where your ‘don’t be a polite doormat’ worldview comes from. I wish I had your strength to fight my demons.”

“You do,” Sam said. “I’ve seen how you’ve undermined them for years. You’ve got the chin to fight them.” He spoke over Dean’s protests, “don’t worry about me. They won’t touch me before the fight, and afterwards, I’ll be with you and Bobby. Then we can both leave.”

“What about during the fight?” Y/N asked. “Does Raphael control him too?”

“No, my opponent is from the other side of town. Virgil-something. Bobby did a little digging to check that, said all he found out was the guy had weapons for fists.”

Dean sniggered, “wait till he meets your armory.” He was smiling again. He wrapped Y/N’s fingers in his own and kissed her hand. “Do you think we can do this?”

“Yes. But why don’t we call the cops?”

“They probably already know,” Sam snorted. “They’ve got as much of a hold on the underworld as Raphael has in the local boxing. Besides, we’d go to jail and get stuck with Uriel’s cronies.”

“We wouldn’t last the night,” Dean mumbled. “You can’t go to the heat, Y/N. They’d nab us all, whether we’ve been blackmailed or not. Promise me you won’t go to the police.”

“I promise.”

Sam checked his watch. “We’d better get going if we want to be on time for call.”

“I’m just the undercard, so I’m going to stay a minute and come over with Y/N.” Dean looked at her, “if that’s alright?”

“Yes. It won’t take me but a minute to get ready.” Y/N stood and walked Sam to the door. When he was gone, Dean was there to kiss her. At first it surprised her, but the way his lips matched hers tilt for tilt, they felt like puzzle pieces completing one another. She gasped when Dean broke away suddenly.

“Sorry, I didn’t mean…”

“Dean, it’s okay.” Y/N tried not to blush, but her breath wasn’t coming out right. It staggered and spun till she could gather her thoughts. “Does that make this next evening date number two?” she asked with a giggle.

Dean grinned, “hell yes.”

When they got to the ring, it was already packed. Dean introduced her to Castiel, close friends since before and after his last big fight with Bartholomew. “He’s your bodyguard till I get back.”

“Fine,” Y/N huffed, “but give Trenton an extra uppercut from me, okay?” Dean chuckled and kissed her cheek before leaving. There were a few small fights, Y/N realized she was sitting behind the same radio host as before, then the arena went silent as Dean and Cole walked to the ring. The announcer did his thing and jazzed up Sam’s top billing fight to follow. The crowd roared as the first bell rang.

“Winchester starts this first round, as he does every round, with a series of jabs,” the radio man said. “Trenton sets a pattern too. Weaving, crouching, trying to get under. The third man in the ring is our referee Balthazar Smith. The opponents stay in the middle, spinning the center to stay focused and close. They’re going at it now. Trenton is jabbing quick, but Winchester gives him a few solid blows to the head. And that’s the bell, ladies and gentlemen. Round one is at a close.”

Y/N and Castiel cheered with the rest of the crowd. Trenton had a few fans, but Dean had several more. Y/N watched the judges almost as much as she watched the fight and liked how they nodded when Dean landed a hit. The bell rang to start the next round.

“They start up again, moving faster at one another. Much different than the slow build of last round. Already you can sense what a perfect match this is. These two men are masters at their trade, but only one will move… and Winchester lands a blow to Trenton’s stomach! Trenton staggers back but launches himself at Winchester. He gets in a few hits… but now Winchester gives him the one-two. Winchester’s got the speed in him tonight. Trenton is stunned. Winchester stinging in those jabs, Trenton trying to get in close with those wicked hooks. The referee has to separate them as the bell rings.”

Dean was looking ragged by round eight. Cole wasn’t falling like Uriel had said. From their corners, Dean shot Cole a look. Cole nodded back, confirming Dean’s thoughts. Dean nodded at Bobby, who was fixing his eyebrow, still open from their first bout. Dean sighed and stood as the bell rang.

“Rolling into round nine, the audience feels like they’re ready for an explosion. They meet quick. Both men dishing it out and still staying in there, though a quick series of hits could make the bout. Oh! Did you hear that thump? That was a Winchester glove colliding with Trenton’s ribs. Winchester still has that patch over his eye, but he’s still forcing the fight, although just a little bit slower. And Trenton watching like a hawk, always looking for that split second of an opening, always eager to unload his combinations.”

Y/N flinched with each hit. They were harder now and audible above the din of the audience. Even Castiel’s brow was knit with worry.

“Trenton upper cutting Winchester, sending him to retreat along the ropes. Trenton lands one to Winchester’s face. That can’t feel good on his patch. Winchester pulls him close, cinching Trenton’s arms. But they’re still able to reach up to hit him in the back of the head. They are separated with much struggle from the ref. Trenton chases Winchester around the ring, jabbing an upper cutting. Winchester blocks his face and sends out jabs that land on Trenton.”

“Round eleven, thirty minutes of actual fighting have gone by. Neither man has really taken over, but this could be the fiercest of them all. They’re starting out close and hard, ladies and gentlemen, and it doesn’t look like they’re going to let up. Winchester twists under Trenton’s punch, then pulls up to land on Trenton’s face. Winchester uppercuts, but misses him by a mile. Trenton pulls in close, one-two into Winchester’s chest with a little bit of elbow into his cheek. Ref and judges on the wrong side of the ring to see it. Now you can hear the audience as Winchester starts raining down on Trenton. This is what they’ve been waiting for. Trenton fights back, but the blows keep coming. Trenton gets Winchester on the ropes, thirty seconds left in the round. He uses them to land body blows, but Winchester pushes him back, cinching Trenton’s arms again. They’re both haymaking as the bell rings.”

“Round number twelve, and again those opening jabs by Winchester. “Raisin’ Cain” just a little bit slower, but he’s shaking off that battering he took in the previous rounds. Trenton, weaving, crouching, always aggressive. He’s loaded with confidence after that last round. But Winchester is showing his dynamite. One, two, three jabs to Trenton, snapping his head back with each. Winchester’s stance spread out as Trenton backs away from another combination. If you can hear that static, ladies and gentlemen, that’s the full audience spurring on their favorite. Trenton tries to bob down, but Winchester’s uppercut is waiting for him. Even with the patching, Winchester’s red is flowing; I can smell the iron from here.”

Dean’s lips looked more swollen than they were stretched over his mouth guard, but his hurt eye was starting to close. His left arm hung lower, giving him less protection.

“Here we go for the final round. Through it all Trenton and Winchester have dueled like champions. With just three minutes left, Trenton is still the aggressor. Winchester, who’s probably thinking he’s never had it rougher, is gamely hanging on, mouth open, jabbing all the time and tying Trenton up in the clinches. Winchester dances Trenton over to the ropes, his restraints looking more like support as Trenton leans on him. It’s been a rough night for him too. They back away from each other before the ref has to separate them. Their arms reach out at the same time, while they receive a punch like the one their dishing out. Trenton keeps trying to bob below Winchester’s hits but keeps finding uppercuts before being beaten down by roundhouses. Thirty seconds to go. Winchester cinches Trenton, but Trenton keeps catching him in the ribs. There’s the bell, and the big fight is over. Both Cole Trenton and Dean Winchester deserve tremendous credit. But now it’s up to the judges appointed by the Chicago City Commission. Here’s announcer Johnny Addie with their decision.”

The announcer stepped into the center, dragging the mic chord behind him. He flipped through the judges’ cards, then pulled the mic to his mouth.

“Judge Aidie Idella scores it nine five one even, Trenton. Referee Al Burr scores it nine two six, Winchester.”

The crowd booed. Y/N couldn’t tell if it was for or against Dean.

“The other judge, Bill Wrecked, scores it eight six one even, the winner and official semi-finalist of the Light Heavyweight of Chicago, Dean Winchester.” The announcer lifted Dean’s arm above his head as the crowd cheered. The announcer marked the place and time for the final match, then led Dean out of the ring. He and Bobby went to the back to change out so he could watch Sam’s fight.

Uriel got up from his seat in the third row behind the judges and motioned for the ref to follow him. They ended up in Raphael’s office, where he was entertaining a visitor with the best view of the ring, and his aged drinks.

Raphael didn’t turn from the window but addressed the men as they entered. “Uriel, you haven’t met him yet, but this is Virgil Akins. He’s put on a lot of weight to fight Sam tonight, make sure it’s memorable to all the right people. And Balthazar,” he turned and faced him, “don’t screw this up with a bad call.”

“Yes, sir.”

Balthazar Smith kept a strong face, but Uriel smiled to see him wipe his hands on his pants. Uriel led him and Virgil out into the hallway, cornering them to one side. He shook Virgil’s hand.

“Dean Winchester has already said he’s finished. We’ll invite him nicely to the box to watch his brother’s fight, then you can have him. He’ll think it’s a real fight, so hold nothing back. You know how to end it. Balthazar, when Virgil uses his rabbit punch, make sure you’re looking the other way, and do something to make sure the judges are looking away too.”

“But sir, those punches can kill.”

“I know. There’s no way Dean did this without talking to his brother, so Sam’s in on it. Don’t worry too much about it. Virgil’s got it handled. Understand?”

Balthazar moved to give a retort but swallowed it. “Yes, sir.”

“Good. Now get out there before anyone misses you. Soon the Winchesters will be finished.”

[1] Sophie: 50’s slang for “girlfriend”

Part 4: Rabbit Punch 

Tag list:

@sassy-losechester, @mysteriouslyme81, @theriumking, @kittenofdoomage, @supernatural-jackles, @bringmesomepie56, @jpadjackles, @ilostmyshoe-79