Y/N gets dragged to a boxing match by her friends where she meets Dean “Raisin’ Cain” Winchester. When asked out on a date, she says she’ll only go if he wins. Which is a serious problem.
Pairing: Boxer!Dean x Reader
Warnings: violence in the form of boxing
Word Count: 3100+
Note: I’m not a boxing expert, but I have watched a lot of fights from the greats to make this series. Find any Sugar Ray Robinson fight on YouTube and use it for background music if you’d like. I certainly used some to get in the zone. Feel free to leave comments on how you like or dislike it (with reasons why you dislike it) and guess where the story is going.
The den didn’t look like much from the outside. The brick was chipping on the corners and several of the windows were boarded up. If there hadn’t been a line of patrons waiting at the door, Y/N would have thought it was abandoned.
She looked at her ticket stub again. Admit One: Winter Chicago Amateur Semi-Finals.
“Why are we here?” she asked Jo, her roommate.
“Because Claire got tickets from her friend who works concessions. She’s already inside and said to meet at the seats on the second row.” Jo spun, flaring her skirt and drawing the eye of several men standing around them.
“I feel overdressed.” Y/N looked down at her little black dress, wincing at the grand amount of tulle under the skirt. In reality, it was only a notch above what she wore around town, but she would have preferred to save this dress for a Sunday. “It’s just going to be a bunch of sweaty guys beating each other up. We could watch that any night at your mom’s bar.”
“Y/N,” Jo sighed, “try to enjoy this. The guys fighting tonight are going to look a lot better than the ones at the bar.” Jo leaned close and whispered, “and they’ll be wearing considerably less clothing.”
“Jo!”
A quick cheer resounded from the front of the line as the doors opened. Light poured out into the street, followed quickly by lively music. Barely twenty people had walked through the doors when the bet collectors were yelling the stats. Y/N and Jo showed their ticket to the bouncer and were nearly drowned in the rush to get in. They were separated, but Y/N walked over to a less populated part of the arena to catch her breath.
“You alright, sweetheart?” a voiced asked.
She turned and found herself face to chest with a man in a suit. Taking a step away, she looked up into the greenest eyes she’d ever seen. He watched her with concern, but something about him made him feel dangerous. Like he could easily overpower her in more ways than one.
“Yes. Thank you. Now if you’ll excuse me, I need to get to my seat.” She turned to walk away.
“You might want to wait a few more minutes till the crowd dies down or you’ll get swamped again.” Y/N stopped to listen. It was still crowded. “And I would take a moment to breathe. Once you’re sitting down, it’s probably not going to smell good.”
“Wonderful,” she muttered under her breath. But she stayed all the same. If the smell of sweaty men could reach her up here, then it was going to be unbearable down there.
“I’m Dean. What’s your name?” he asked, holding out a hand. She shook it with her fingertips.
“Y/N. Pleased to meet you.” She turned to watch people find their seat, reminded of the movements of ants.
“Have you ever been to a fight before?” Dean asked.
“Are you writing a book?”
He raised his hands in defense. “Just wanted to get to know you, sweetheart.”
Y/N snickered, “I hope you don’t think you’ll get anything out of it.”
“Well now that you mention it…” Y/N turned to gape at him. He was serious. If he wasn’t so big she would have thought his boyish movements would have been cute. She almost missed his question while watching his tongue dart out to wet his lips. “Did you hear me?”
“Please?”
“What are your plans after the fight?”
“As far as I can see, nothing with you.” Y/N turned to walk away, she could handle the second-row problems better than this.
“Come on, princess. Being one of the boxers should get me somewhere.”
Y/N took a deep breath. He was big enough to be a boxer but didn’t seem to fully fit the type. Not to mention he wasn’t dressed for a fight.
“I’ll tell you what. You win your fight tonight and I might meet you after the prizefight. Otherwise, forget it.”
Y/N walked away from his grinning face and into the pit. Jo and Claire didn’t have time to ask questions as the first opponents arrived at the ring. Y/N was ready to forget Dean.
“Dean! Where’ve you been, boy?” Bobby Singer grabbed Dean by the lapels and tugged him into the prep room. “You need to get dressed before Uriel gets here.” They froze as someone knocked on the door. “Balls.”
Bobby opened the door for Uriel. Dean hated his sneering face, but he was second in command for the match-fixing ring.
“Take a dive in the fifth, Winchester, and stay there. Feel free to do what you want till then as long as it doesn’t keep Cole from taking you out.”
“That’s not what we agreed, Uriel,” Bobby snarled, “Dean’s supposed to go to the big prize match in March.”
“He will. We had to add a week into the schedule so a special guest could meet you there. You’ll get a rematch next week, and then you’ll be on your way as planned.” Uriel laughed, a sound everyone found akin to nails on a chalkboard.
“You’d better not screw me. Not like you did to Cas with Bartholomew.” Dean stayed back, but his fists were tight enough to turn his knuckles white.
“Yeah, wasn’t that a bite? He made the distance till the tenth, though.” Uriel chuckled.
“It was torture,” Bobby spat.
Uriel stepped forward till he loomed over Bobby. “I wouldn’t focus on the past if I were you. Those who look back too much tend to get lost in the future.” He nodded at Dean and walked out, shouting over his shoulder, “the fifth, Winchester.”
They stood in silence, both seething. But it was the life they were in, one that they more or less chose. Sometimes they joked that God himself couldn’t stop them from deciding who lived and who died. They saved that for nights even darker than this.
“One of these days someone’s going to feed him a knuckle sandwich,” Dean growled.
Bobby nodded in agreement. “But it’s not gonna be you. And it’s not gonna be tonight. You’ve got too much riding on your family for you to rebel. It’d take the whole house of players to end this.”
“Or getting caught,” Dean mumbled.
“Bite your tongue boy! If they get caught, we get caught. And then all their attack dogs will get stuck in the same cage as us. We wouldn’t last the night.” Bobby sighed. Dean looked at him from the corner of his eyes. He was getting old, and the stress of the maintaining the fixes was taking its toll. Bobby shook himself with a grunt. “You need to change quick if you want to catch Sam before his fight.”
Dean shed his jackets while Bobby hunted out the shorts and gloves. He’d signed on to do whatever Uriel told him, but the image of the pretty girl from earlier mixed with the shame of being a fixed boxer made him question how tonight was really going to turn out.
Y/N jumped as the bell rang, ending the match. The ref announced the scores, awarding the win to the tall man with long hair. She halfway wondered how he could see his opponent.
“Ladies and gentlemen,” the announcer started, “these ring officials have been appointed by the Illinois State Boxing Commission.” He rattled off several names, she couldn’t remember if they were different from the match before, but they did look a little grimmer. “This is the feature presentation of the light heavyweight not exceeding 175 pounds. From Fort Benning, Georgia, wearing the black trunks with the white stripe and weighing 170 pounds: Cole “Avenger” Trenton.”
A quick cheer rang through the arena. The announcer waited for it to die down before continuing.
“And from Lawrence, Kansas, wearing the white trunks with the black stripes and weighing 175 pounds: Dean “Raisin’ Cain” Winchester.”
Y/N nearly fell out of her seat. It was the man she’d met earlier. And he was the title fight! She covered her face with her hands as Dean looked around the crowd before finding her. He smiled and winked, making her blush. She hoped he was too far away to see it.
“And ladies and gentlemen here is referee Balthazar Smith with instructions for both contestants. And ladies and gentlemen, no smoking, please.”
The referee stepped up to the mike and waited for Dean and Cole to meet. Their coaches stayed close, massaging their shoulders, and probably holding them back based on the daggers they were shooting. “You boys received your instruction from the Illinois Boxing Commission. I want a clean break at all times; careful of your kidney punches and your rabbit punches. In case of a knock-down, I want you to go to your furthest corner and stay there ‘til I tell you to come out fighting. Also, in case of a knock-down, you must take an eight-count. It that understood?” Dean a Cole nodded. “Shake hands and come out fighting.”
The boxers separated and went to their respective corners. Their managers took their robes and gave them mouth guards. The row in front of the girls was filled with men from the press. Y/N had been listening to the man directly in front of her all night as he announced the fight for a small radio program. He kept using terms she didn’t always recognize, but sometimes he’d clarify for visiting listeners. She hoped Dean wouldn’t get hurt.
Bobby held Dean back as he bounced and shadow boxed. “I know you don’t want to, but do what Uriel says. Next week you’ll get the rematch, and then we’ll be onto the big time.” Dean nodded and danced towards the center as the bell rang.
“Ladies and gentlemen, that was the opening bell for this scheduled ten rounder, and Raisin’ Cain Winchester, who won the championship last year, is on his way to defend his title against a younger opponent in the semi-finals. Cole the Avenger is fighting in memory of his father, who died due to boxing injuries.”
He labeled several punches and moves as the men started to swing at one another. “Trenton, who is very effective inside, very good at body punching, and Winchester who is obviously good at long range… with that snappy left jab… and the right cross.”
Dean cinched Cole’s arms to his sides, preventing further body punches. Already they were both sweating, and Dean’s grip was slipping. The referee came over and broke them apart. They separated, but Cole chased Dean into a retreat. Dean fired out a jab, which Cole returned. They traded punches, uppercuts, and several different types of blows that Y/N had learned that night.
“That right hand to Winchester was just a trifle short. If Winchester keeps dancing around the ring like he is, he might tire before he can knock some wind out of Trenton. But there can be no doubt that both men came here tonight to fight. A short minute remaining in round one.”
To Y/N, the minute felt like ten as the men quickly exchanged blows faster than the reporter could call them. Cole landed a solid punch to Dean’s face, making him stagger back into the ropes.
“A little trickle from Winchester. Trenton is scoring repeatedly!”
The bell sounded as Dean pushed off. They ignored one another and went to their corners.
“And round one is over! Raisin’ Cain Winchester taking about as much punishment as I’ve ever seen him take in round one except for last year when Castiel Novak nearly punched him out of the ring. Winchester came back to win that fight. Novak fought and lost to Bartholomew in his next bout in a nearly murderous display. Winchester has had a total of 130 bouts, losing seven, two draws, and one technical knock-out trying to win the middleweight championship when he first started.”
The reporter continued to pass along Dean’s stats and Y/N couldn’t help but be slightly impressed. He was actually a good fighter. But she wasn’t sure she wanted to date a boxer. Not yet. There were still nine rounds to go to see if he could hold up his end of the bargain.
Rounds two, three, and four came and went with similar displays of prowess. Dean’s cut on his brow kept bleeding into his eye. Bobby kept patching it up and cleaning it the best that he could. Y/N learned that he had been a boxer back in the day, but an unsportsmanlike hit to his spine kept him out for several years. When he came back, he stuck to training others and found the Winchesters: Dean and Sam. He was a coach for both of them. Y/N wondered how his heart stayed in his chest on nights when they both fought.
“Trenton talking to Winchester constantly. And the eye of Dean Winchester is starting to smear a bit. Right on the right eyebrow.”
Cole swung out, catching Dean in the ribs, making him double over.
“Probably the best blow of the fight! Avenger Trenton overhand right swinging below to catch Winchester in the ribs.”
Dean swung wildly, missing Cole completely as he ducked. Dean backed away and tried to wipe the blood out of his eye, but missed seeing Cole’s left hook. He dropped like a stone, his head bouncing painfully against the canvas.
The world slowed down to single heartbeats. Patrons leaped to their feet like rocks in molasses. Bobby shook his head, refusing to watch. Y/N looked for his eyes, begging whoever would hear her to see the brilliant green instead of the blood over his closed lids. She gasped as they fluttered.
He found hers as well, latching onto them like a ship to a lighthouse during a storm.
The referee started to count.
One.
Two.
Three.
“To hell with this,” Dean mumbled.
Four.
He reached for a rope, using it to pull himself up. But knees don’t count. He knew he had to get to his feet.
Five.
Cole shouted at him, “stay down! Or you’ll be worse than done, Winchester.”
Six.
Dean managed to get one leg under him, but it wobbled too much to support him.
Seven.
Dean pulled again, straining against his bruised ribs to stand on his feet.
The crowd roared with delight.
“Dean Winchester was not down for the count yet, ladies and gentlemen! We’ve still got a match as long as he’s got any fight left in him.”
The bell rang, ending the fifth round. Cole looked pale and a little green around the gills. Dean nodded to him, taking the blame for the manager storm that was going to hit later.
They met again, but Cole let Dean do all the hitting, feigning exhaustion. Dean knew Cole’s fighting and his style. Cole was tired, especially now that Dean wasn’t pulling his punches.
“A slowly tiring Winchester, but Trenton slows as well. Not punching cleanly going into this round, missing. Winchester’s left hook was low, giving him a warning from ref Balthazar.”
Dean gave Cole four quick jabs to the torso, sending him stumbling into the ropes amid a chorus of cheers. He followed with three more to the head and face.
“Come on Dean! You’ve got ‘im!” Y/N screamed.
“Four clean blows into Trenton, and then three more. Winchester was hurting Trenton. He’s hurting him now. Jabs to the ribs and the face. Now a bolo. Trenton is round housing, missing Raisin’ Cain Winchester by a mile. Trenton’s left eye is swollen. Closing gradually. Damn! Pardon my language, ladies and gentlemen, Dean Winchester has spun Trenton around. He’s still standing, but blocking drunk. Ref Balthazar separates them again as Trenton leans on Winchester. Half a minute to go in the sixth round. Winchester set him up with those body blows, damaged his nose. He has Trenton on his feet asleep, holding on. The audience is standing and cheering.”
Dean kept jabbing. Cole wasn’t fighting back and he was a fellow pawn, but Dean was punching red. All those times when he had a win in the bag and Uriel told him to fall, or every time they promised him the prize fight, like tonight, but then took it away. He could hold himself up. They could take their schemes and schedules with them to hell.
“Trenton punching drunk as the bell rings, ending round six. The ringside doctor checking him out. If he doesn’t respond to the bell, the fight will be over. No! He’s up and ready to go. This is round seven, ladies and gentlemen. And Winchester is not holding back, not with the end so close.”
Y/N notices a flurry of movement to one side of the ring. The doctor is waving his arms till a large man nods. The bell rings, but Dean keeps going.
“Winchester doesn’t hear the bell. Ref Balthazar has to break them apart. But it’s too late! Down goes Trenton. The ref counts… and Dean Winchester has won by a knockout, ladies and gentlemen. For six rounds, Trenton gave better than he took. Then Winchester unleashed all of his best guns for the last round. Our score cards showing that Winchester was ahead sixty-three points to fifty-seven.”
The ref pulled Dean towards the middle as Cole’s coach and attendees pulled Cole’s body off the canvas. The announcer stepped on stage and grabbed the mic. “Attention ladies and gentlemen, the winner by knockout, in two minutes and fifteen seconds of the seventh round, and the defending winner of the Winter Chicago Amateur Semi-finals is Dean “Raisin’ Cain” Winchester. He will face his last opponent to defend his title for another year once dates have been determined.”
He raised Dean’s arm above their heads. Y/N joined the rest of the crowd with a standing applause and cheering.
“See! You enjoyed yourself.” Jo yelled above the din.
“Yeah. I guess I did. Thanks, Claire, for the tickets.”
Claire continued cheering, stopping for a split second to gasp out, “he’s coming this way.”
Y/N looked back at the ring to see Dean pushing his way through the managers. Aiming to meet him halfway, she headed to the chaos surrounding the canvas.
Bobby was shaking Dean. “What were you thinking?”
“Nothing,” Uriel’s voice said, breaking into the circle. “He wasn’t thinking at all.”
Dean stopped his struggle to face Uriel. “You want to duke it out here?” he challenged.
Uriel shook his head with a smirk. “No. But we will discuss this Winchester. Enjoy the light… while it lasts. And get that brow checked out; we wouldn’t want it to turn into something serious.”
Dean broke away, surging through the crowd. He bumped into the person he wanted to see most.
“Heya, sweetheart. You got plans?”
“I’m open to suggestions.”
Part 2: Caution
Our Deepest Desires 