Chapter Text
Sam's POV - The Past:
A small child knelt next to the basement door. He was never allowed down there. No matter what he heard, no matter how much he wanted to know what his father did down there. He was never allowed past the black tape by the basement door. He stared down the dark, old stairs that seemed so suffocating.
Walls closed around the stairs and came to a stop at a locked metal door; he couldn’t see anything if he wanted to. He never knew what happened down there. The six-year-old softly tugged at his sandals as he tried to adjust to the darkness. Pulling at the velcro on his shoes, keeping an eye on the darkness, the child lazily sat on the floor. His feet were dangling over the first step.
Why couldn’t he just go halfway down the stairs?
He wasn’t going down the stairs…if he was going halfway down them. Could he take a small peek without getting in trouble?
The child put his feet on the first step, and the step creaked. The kid tensed, but after looking around, found no one had come to smite him. Unaware of the trip wire, the child kept descending the stairs, dangerously close to setting it off. A shotgun was aimed at him from the darkness of the wall on the right side of the stairs, the trip wire ready to pull the trigger.
His sandal pushed against it as he slowly came down the stairs. He didn’t recognize the sound of a gun threatening to go off. The child didn’t have time to react as the gun was seconds away from going off into the side of his face when someone grabbed his overalls from the straps, yanking him roughly away from the trigger.
The child instantly started to cry, knowing he was caught as someone pulled him rather roughly up the stairs. The child was let go when he was back on the ground floor, his savior closing the door quickly and quietly. The six-year-old sobbed loudly as he took in the eyes of his big brother Dean, who panted in fear. Dean’s hands were on the basement door as he took in the danger his baby brother had missed.
“What were you thinking, Sam?!” His brother panted, upset, careful not to raise his voice.
“D-Don’t tell daddy. I-I won’t do it again.” Sam sobbed as his older brother turned to him. He was white as a ghost as he kneeled to him.
“Promise me.” Dean grabbed Sam’s shoulder, kneeling to him. “Never go down there again. Or I’ll tell daddy, you hear?!” Sam nodded in fear. His brother looked at him with fear despite all the anger in his voice before he pulled Sam into a hug. Sam melted into his touch as Dean closed his eyes, rocking him for comfort. He pulled back as Sam wiped his tears, sniffing. His brother got up, getting Sam a popsicle, which cheered Sam up. Sam reached for it, happily sucking at the sweetness while his hair was ruffled.
They both stopped hearing the sound of the heavy footsteps. Dean stood as they listened to the sound of someone coming up from the basement. They both tensed as the basement door creaked open. His brother stood up straight, placing his hand on Sam’s shoulders, keeping him grounded.
A bloody hand gripped the door, pushing it open with a loud whine. Their father stood in the doorway, half concealed in the darkness. Sam took a step back as Dean took a step forward. His brother kept a protective hand on Sam.
“...It’s time, Dean.” Their father spoke as Dean sucked in the air. Their father held out the end of the bloody knife to him, and he tensed, staring at the blood dripping on the floor. His brother slowly moved to their father, reaching a hand to take a knife. Dean took the bloody knife into his hand, glancing at it. The blood was still warm in his grip and slippery to a point. Slipping in his fingers slightly, making him grip it harder. “...Go watch TV, Sam.”
Sam didn’t say anything as he looked at the fear on his brother’s face. His father has been talking about bringing Dean into the basement…but both had hoped he wouldn’t. Sam never knew what happened in the basement…but he knew there was a reason to fear it. His brother sucked in the air, trying to look strong as he slowly moved towards the basement door.
Their father held it open as Dean moved past him. Down the stairs, he was careful to avoid the trip wire before he disappeared down the stairs and through the door. Sam followed them to the door, kneeling at the top of the stairs. Seeing his father turn to stare at him, their father said nothing, slamming the door.
Sam did not want to leave his brother when his brother was so scared. He sat on the top of the stairs, softly playing with his velcro straps. He paused, seeing the blood drops on the floor, he reached down, rubbing the blood between his fingers before he wiped the blood back on the floor, drawing a little smiling face. Waiting for his brother to come back…
_____________________________________________________________________
Now:
Highway to Hell played loudly in the house, echoing the house as hazel eyes prepared for surgery. Sliding on his gloves, he could hear the loud whining of the person on his operating table. They were gagged so they didn’t make much noise, but jolted with everything they could.
“Now, now,” Sam said, preparing his back for the surgery. “If you struggle, this will only make it worse. I just need a little piece to send to your dad.”
Sam outlined the tiger tattoo on the man’s back. The man jolted again in tears, his choking sobs behind the gag loud. He kept turning his head to look at Sam.
“Dean wants to send a couple of fingers, maybe an eyeball. I thought it made more sense to send a tattoo.” Sam grabbed the numbing agent, injecting it into his skin. “Tattoos are less of a mess, more identifiable. I am sure they can figure out the tattoo is yours, faster than if they had to match fingerprints or test blood.” Sam was nice enough to wait for the numbing to take effect. “Trust me, it’s a mercy.”
There was loud singing accompanied by the music, which made Sam sigh, leaning back against the table as he glanced up, hearing his brother most likely preparing their meal. This was a normal routine for the Winchester hitmen. They saw themselves as independent contractors. Working for whom they liked, when they liked.
They kept the Winchester legacy strong. Hitmen, assassins, whatever you called them. If you wanted something done, you called the Winchesters. Everyone wanted them for their own, offering them things like money, mansions, and vacation islands.
They never accepted, though.
Sam may be the brains behind the operation, but his brother called the shots. He was the more ruthless of the two. Dean was a skilled interrogator and torturer, able to make even the toughest spill their guts- Mentally and physically. He wasn’t easily won over or talked into things. Dean, as head of the family, made it perfect to make sure they weren’t easily manipulated.
Sam was the brains. He operated everything behind the scenes and advised his brother on the jobs or deals they should take. Though Dean seemed to be the face of the Winchesters, Sam liked being in the background. Gave him more freedom and less responsibility, giving Sam downtime, which he enjoyed. His brother’s…whole life is and will always be the family business.
“Can you feel this?” Sam asked, poking the skin. The man continued to cry, but Sam pinched him, and the man didn’t react. “...Sorry, this isn’t personal-”
“Sam!” Dean’s voice made Sam glance up as he grabbed the scalpel. “Did you want hashbrowns?”
“Do we have ketchup?” Sam yelled up the stairs.
“Do We GoT kEtChUp?” His brother playfully mocked. “Of course, we got ketchup. That’s all you eat is blended tomatoes.” Sam made a face. “You drink Bloody Marys unironically, bitch.”
“I’ll take some…!” Sam chuckled up to him. “Jerk.”
Sam moved the scalpel to the man’s back, using the scalpel to tear open the flesh. The man didn’t start to reach till he felt the blood pooling down his sides. The man screamed and thrashed in a panic as Sam sighed, annoyed.
“Thrashing is only going to make this worse. I’m trying to avoid cutting into your muscles, trust me. You want me to do this. Not my brother. If I mess this up by cutting any of the tattoo, it will be his turn…and you don’t want that…” Sam spoke, continuing, the man stilled, tears sliding down his face. Feeling the pressure of his skin being cut off. “...This is mercy.”
_____________________________________________________________________
Dean lazily chewed on bacon as he sat in the kitchen chair, hearing the slow sound of footsteps coming up the steps. Dean tilted his head, watching the door from the basement. He heard his brother miss the trip wire. Yep, that was Sam. Dean relaxed as Sam opened the door, running his fingers through his hair.
“Did you get it?” Dean asked as Sam lazily tossed a plastic Ziploc bag onto the table next to the breakfast. Dean frowned, grossed out, as he took in the tattoo. “Beautiful work, maybe a couple of grand.”
“The left eye is fucked up,” Sam mumbled as Dean tilted his head, realizing he was right.
“Shame,” Dean whistled as Sam grabbed the mailer and pushed the plastic bag inside before sealing it. Sam placed that into his bag to mail later today, pulled off his gloves, and tossed them into the trash. Sam took a seat next to him, grabbed the ketchup, and slathered it onto his hashbrowns. Dean reached over and poured Sam some orange juice, to which Sam didn’t react.
“Got school today, right?” Dean asked as Sam took a bite of the ketchup-covered hashbrowns. Sam nodded, chewing before he spoke. Despite being a hitman, Sam was also in school to become a surgeon. Sam had a life outside the family business, including a social life and friends. Sam’s eyes moved to Dean, who chewed his food in silence. Dean had shielded himself from this life as much as he could... but he was a Winchester; he couldn’t avoid it forever.
“Yeah.” Sam looked at his phone before standing. “I should get going if I want to make it to class on time and deliver this.” Sam grabbed his shoulder bag, patting it.
“Send my regards,” Dean mumbled, taking a sip of his coffee as he slid Sam’s lunch bag and thermos over to him. Sam beamed, taking the food before turning and walking away. “Don’t accidentally give them your lunch this time.”
“Yeah, yeah,” Sam said. “Later.” Sam left out the door, moving to his car in their long driveway. Backing up, he felt his phone vibrate. Glancing down, he noticed the text from Dean confirming the client meeting location. Sam turned up his music as he drove down the road, not in the mood to deal with the police if he were to get a speeding ticket. He had to admit that, as some of the best hitmen in the underworld, they had the benefit of working freelance.
No one held them accountable for what they were hired to do, because others would inevitably need them for revenge. This gave them a constant flow of work, which easily paid for everything they needed, including Sam’s college. It wasn’t honest work, but it was worth every penny.
Sam pulled into a strip club, noting the name: Finding Heaven. Sam scoffed to himself as he climbed out of the car, walking toward the entrance where a couple of security guards stood. Anyone else would have been patted down and searched.
Not Winchesters.
The Winchesters were the most neutral party around; even if they were hired to hurt another mob boss, they wouldn’t do it so obviously on their territory. Sam walked past, heading toward the office. This week, they were hired by a mafia boss named Castiel Novak, leader of the Angels. If Sam had to rate him, Castiel was among the top three most powerful and wealthy mafia bosses in the world. He was one of their regulars, coming to them with a job from time to time.
Sam walked toward the strip club office where two bodyguards stood ready. One casually opened the door for Sam to walk in. Sam’s hazel eyes slid over to the man in the room. Piercing blue eyes met his own, pulled lazily from the woman giving him a lap dance. He had his head in his palm, lying back in his chair. He seemed disinterested in her despite her efforts. Castiel turned his attention to Sam without hesitation. He said nothing, casually waving her away. She nodded in respect, turning and walking away. Her heels clicked on the floor as Castiel sighed. Sam couldn’t help but watch her go, noting her hips sway slightly as she walked. The bodyguards entered the room, closed the door behind them, and watched.
“Sam Winchester.” Castiel’s voice made Sam turn away from her. “I assume you are here with good news.” Sam reached into his bag, took out the mailer, and held it out to him. Castiel accepted it and opened it. Pulling the bag from the mailer, Castiel smirked at him. “Exceptional work, Winchester. You have a surgeon’s hand.”
Sam said nothing, but bowed his head in respect. Castiel waved one of the bodyguards closer to take the mailer and slide it in.
“Please release one of the ‘Prophet’s’ men and give them this,” Castiel spoke. “Tell them to tell Chuck his son says hi, and if he wants him back, he knows what I want.” Castiel lazily handed over the mailer before turning his attention to Sam. “...He is alive, isn’t he?”
“You said I can decide his fate,” Sam explained. Castiel eyed him, took the answer well, and poured them both a drink. Sam wasn’t going to drink it, but he took it politely. Castiel eyed him curiously as he crossed one leg over the other. “I figured him being alive and relatively in one piece would make the point.”
“Surprised your brother was tamed enough to hold back,” Castiel cooed as Sam eyed him. Of course, they were curious about his brother. They knew of Dean Winchester; however, he remained somewhat mysterious. He never met with these men. Most people unfortunate enough to run into Dean Winchester ended up in pieces. Sam was the diplomatic one; Dean dealt with the dirty work. “I heard him compared to a hound of hell with his prey.”
“He does what the job requires,” Sam spoke. “And as I said, you just wanted to make a point—death isn’t necessary. I took the lead.”
“ Hm. ” Castiel didn’t seem impressed, swirling the liquid in his drink. “...What does it take to have a meeting with the princes of hell?” (Dean’s and Sam’s nicknames.) Sam almost rolled his eyes at the title, but he wasn’t rude.
“We are meeting now,” Sam spoke, knowing what Castiel meant.
“I meant more with your brother,” Castiel stated, knowing Sam understood. Everyone wanted to meet Dean. Dean wasn’t someone people wanted to meet under normal circumstances, but if they could convince Sam of a meeting, they believed they could happen and ultimately convince the Winchesters to work for them.
“My brother doesn’t do meetings.” Sam frowned.
“Never?” Castiel tilted his head, unamused. “Not even with some convincing?”
“He’s not interested in being under any one boss,” Sam stated. “It’s unbeneficial to take sides.”
“But the one who owns the Winchesters owns them all,” Castiel commented, taking a sip of his drink. “Would I be wrong?”
He wasn’t wrong. They were the most desirable pieces on the chessboard.
“He’s not interested in being owned,” Sam spoke, getting up. “I would like what you owe.” Castiel looked at him coldly, meeting his eyes.
“What if I could give you both something no one else could give you?” Castiel asked. Sam had heard that before. “Something you desire more than anything.”
“Like?” Sam asked, trying not to laugh at the repeated offer. Castiel was quiet for a moment, thinking. Sam was amused to see how this would play out. Sam put his drink down next to Castiel. What would Castiel offer him? A mansion? An island? A tiger? What hadn’t he been offered at this point?
Castiel slowly pulled out a checkbook and held it out to Sam. Sam smirked to himself, almost disappointed that Castiel gave up that approach. Sam was still amused to see what Castiel would offer. Sam reached for the check, but Castiel pulled his hand back.
“You can take this check and go, and we will continue our arrangement as normal,” Castiel spoke as Sam tilted his head curiously. “...Or you can tell your brother I would like to pay him in person so I can discuss our arrangement for your employment under me.”
“And why would I do that?” Sam eyed him. He hadn’t meant to sound rude, but it did.
“...Because, Sam Winchester, you want to take my deal,” Castiel stated casually. “It’s something you’ve wanted for a long time.”
“And that would be?” Sam scoffed.
“...Your freedom.” Castiel downed his drink. Sam blinked in confusion, taking him in.
“...Freedom?” Sam asked, confused. Castiel must have noticed he hit the nail on the head because he smirked, putting his glass down.
“Sam Winchester, if you join under me, I will grant you your freedom from the Winchester family business,” Castiel spoke seriously. Sam’s breath hitched like he had been hit. “How…did he know?”
“...Wh—What?” Sam choked, taken aback.
“If you work under me, I will allow you to put the Winchester business on hold, live a normal life, and become a world-renowned surgeon,” Castiel explained. “Wouldn’t you love to no longer have to lie to your friends anymore...?”
“W-Why would you—” Sam choked, taking a step back.
“Because you still have a heart, Sam.” Castiel leaned back, putting a hand on his knee. “I gave you the freedom to do with that man what you wish, and you gave him mercy.”
“He shouldn’t have to die,” Sam breathed. Castiel could not make it out. “He’s not part of this life—just born to the wrong family.”
“You aren’t meant for the life of a grim reaper, Sam. You deserve to be a surgeon—to save lives.” Castiel nodded, making Sam glance up. “I did my research.”
“My brother—” Sam hesitated. He didn’t know why he was entertaining this.
“Your brother is this job,” Castiel said, leaning toward him. “I know you two take care of each other, but he will never leave this life. He thrives in it.” Sam said nothing. “So let me tend to your brother in your place,” Castiel stated. “He will be safe and taken care of under my care while you go live a normal life.”
“I don’t know if I can trust you,” Sam whispered. “Besides, I have no control over the decision—”
“I would offer you that check, but you’ve already taken the money, Sam,” Castiel said.
“W-What do you mean?” Sam asked, confused.
“Look at the check, Sam,” Castiel said. Sam glanced down at the check—a copy for Castiel’s records. It was made out to Sam’s school... Had he planned this? He had paid for the remainder of the semester. That would have taken him the whole year and then some. “All I ask is that you set up a meeting with your brother for me. I will pay him for the job as promised, collect the boy, pitch my offer, and I’ll drop it if he rejects me. Sounds fair?”
Sam studied the check with its zeros before nodding slowly. Castiel smiled softly as Sam reached over to grab the drink and down it. He then got up and moved to the door, hesitating in the doorway.
“Three thirty PM. You know the location.” Sam left without another word. Castiel smirked to himself, watching him go.
___________________________________________________________________________
Sam walked toward the school with quick strides. He didn’t believe Castiel’s words; there was no way Castiel paid them extra, especially this much. Sam moved to the front desk, where he saw a woman working.
“Excuse me?” Sam asked politely as the woman glanced up. “Can you tell me what my remaining balance is for this semester?”
“Name?” the woman asked.
“Sam Winchester. Student ID number 227813,” Sam replied as the woman pulled up the account.
“You’re all caught up as of yesterday,” the woman explained as Sam sat there stunned. He slowly moved away, heading to his class. As he walked, he put the phone to his ear. It rang, pausing only when he heard his brother answer.
“Yeah?” Dean asked as he cleaned up dinner.
“Get the house presentable before three. We have a guest coming over,” Sam said.
“Who?” Dean scoffed.
“One of the bosses wants to pitch himself to you,” Sam said. “I told him it was a lost cause.” Sam ruffled his hair. “But he’s going to pay us and collect the boy. I’m assuming he’ll be sending some of his men to talk to you.”
“Why are we entertaining this?” Dean asked, putting down the dishes he was cleaning.
“Because...let’s just say he is pretty persuasive,” Sam confessed. “I’ll be home at three. Be good.” He hung up before heading to class.
_______________________________________________________________________
Castiel’s POV:
3:29 PM.
Castiel pulled up to the Winchester house; everyone knew where they lived. The limo came to a stop at the door, making Castiel glance at his watch. He was a minute early, which was unacceptable for him. He was a stickler for his schedule and waited in the car until the exact time.
3:30 PM.
The limo door opened precisely on the dot. He walked up the stairs with his bodyguards following him. One of them knocked on the door while Castiel waited. Sam opened the door, his eyes lighting up in surprise to see Castiel. Sam opened the door without saying anything and moved aside to let them in. Castiel walked in, taking off his gloves, jacket, and scarf at the door, which he handed to one of his men.
“I-I’m surprised you’re here,” Sam spoke.
“Where’s the boy? His father would like him back,” Castiel stated. Sam ushered them toward the living room, where the man sat bound. Castiel nodded for his men to grab the bound man. The man whimpered as they took him out to the car before returning. Castiel handed Sam a check for what he owed, which Sam took gratefully. “Now that we are squared away, where’s your lovely brother?”
“Downstairs,” Sam commented. “Follow me.” Sam walked toward the kitchen and moved to the door on the right, opening it. Castiel peered down the dark staircase. “This way,” Sam whispered, starting down. Castiel followed carefully behind him. Sam pushed a hand back, stopping Castiel’s descent down the rickety stairs. “Careful of the trip wire.”
Castiel nodded, stepped over the wire, and carefully walked down to the second door. Sam opened it, and Castiel walked in. Dean turned to look at Sam and Castiel. Castiel’s eyes fell on the oldest Winchester. He was a handsome man, even though Castiel had only seen photos of him before, usually taken when he was taking out the trash or working on his car. The photos didn’t do him justice; they missed the freckles and the green eyes that seemed to captivate him.
“Dean,” Sam spoke as Dean eyed Castiel. “This is Castiel Novak. He’s here—”
“I’m not interested,” Dean spoke, raising an eyebrow at Castiel. Dean went back to cleaning and sterilizing the instruments of torture in a rather clean sink. Castiel took in the old brick walls of the perfected torture chamber. “Especially being pitched from some suck-up to the boss—”
“Dean, this is their leader,” Sam cut off. Dean’s eyes moved to Castiel, looking impressed as he took in Castiel’s polished shoes and expensive gray suit.
“No,” Dean answered again, going back to cleaning.
“Dean, I think this is something you should hear him out on,” Sam tried. That’s when Castiel knew he had won over Sam. Dean scowled at his brother, but Sam didn’t shy away from it. Castiel’s eyes moved over Sam; the man was now on his side. He figured paying off Sam’s student loans would work as a bonus, but he never imagined it would work this well. Now, Dean was the one he needed to gamble on—one wrong move, and he would lose him forever.
“Sam, would you mind giving us a moment?” Castiel asked as Sam hesitated to leave his brother with three men alone.
“It’s fine,” Dean stated. “They would be stupid to try anything.” Sam nodded, giving Castiel one last look before going upstairs and closing the door behind him.
“I think I can change your mind,” Castiel stated as Dean scoffed.
“Really?” Dean rolled his eyes. “You’re really that confident?”
“I’m so confident that I can promise you’ll be on your knees and submitting to me,” Castiel stated, as Dean frowned, taken aback by the cocky man.
“Oh, you think so?” Dean laughed mockingly, turning off the sink.
“I know so,” Castiel commented before turning to his men. “Leave.” The men nodded, leaving and closing the door without hesitation. Left alone, Castiel walked over slowly as Dean dried his hands.
What do you give a man who has everything?
Castiel had a hunch—it was a risk, but he decided to gamble.
Walking toward him, Dean eyed Castiel dismissively. Was Dean so convinced he was untouchable? Castiel smirked, deciding to break that cockiness. Dean couldn’t react in time as Castiel grabbed his hair from the back of his head, slamming Dean forward into the brick wall. Dean’s breath hitched at the idea of someone pinning him. Dean looked pissed, moving to speak, but Castiel pressed his bulge against Dean’s ass, making him tense and gasp at the touch.
Castiel held back a smirk. That reaction. Oh, that reaction. Dean didn’t know it, but Castiel’s hunch was right; he had just made the right move. Castiel slowly leaned forward, pulling Dean’s head back a bit by his hair as he hissed into his ear.
“Be a good boy and suck off your master,” Castiel hissed into his ear. “And I’ll reward you with my cock.”
Castiel let go, leaving Dean to react on his own. Dean took a moment to slowly turn and face him. Dean’s heart pounded in his chest, as did Castiel’s own. Castiel wouldn't normally expose himself like that; he was very private about that part of his life. However, to win the Winchesters, he would do anything. Dean’s face seemed conflicted when he looked into Castiel’s eyes. He held himself slightly. Castiel wondered if he had gone too far with Dean, pushed him too much.
Dean’s eyes moved from Castiel’s face, sliding down his body to his bulge. Dean took a step toward him. Castiel noticed Dean’s shaking fingers as he took hold of his belt. The touch made Dean drop onto his knees with a desperate breath of relief. His fingers struggled with the belt but eventually got it free. Dean swallowed, unbuttoned his pants, and pulled down the zipper. Castiel let out a small breath, feeling Dean pulling his hardening cock from his underwear.
Castiel watched Dean’s eagerness. Dean was excited. Dean licked his lips before glancing up at Castiel. Castiel watched him maintain eye contact as Dean leaned forward, sliding his lips over his mushroom tip. Castiel’s heart fluttered—he didn’t know why—at the feeling of Dean’s virgin lips sliding slowly over his pre-cum covered dick.
Dean let out a relieved breath as he slid Castiel’s cock into his mouth, keeping his lips tight around it. Castiel swallowed. Dean was new at this; he could tell. Castiel wasn’t sure if this was just his first time with a man or his first time having sex. Dean was in his late twenties or early thirties. Surely he had had sex before, hadn’t he?
Dean’s hands moved on Castiel’s base, gaining his attention as Dean looked into Castiel’s eyes for approval. Castiel’s hand moved down to grip his hair, nodding approvingly. Dean’s green eyes lit up at the affection. He worked Castiel's cock with his mouth, hungrily. Castiel gripped Dean’s hair harder, slowly starting to rock into Dean’s mouth. Dean gagged a bit, but he quickly got used to the movements.
Castiel was getting close, grabbing Dean’s face to rock in and out of his mouth. Castiel pulled back, knowing Dean couldn’t take him down his throat. Dean blinked in surprise as Castiel took his cock from him.
“Open your mouth and stick out your tongue,” Castiel panted through gritted teeth. Dean listened. He hesitantly opened his mouth, sticking out his tongue. Dean looked into Castiel’s eyes as Castiel stroked his cock. He had never felt this turned on before. Something about Dean just made him...
Castiel didn’t realize he was holding his breath until his release. A shudder went through his whole body as his cum spilled from his cock, landing on Dean’s nose, lips, and tongue. Castiel moaned, stroking himself through his orgasm. Dean sat there so willingly, closing one eye to protect himself from getting cum in it. Dean was being such a good boy.
Dean took Castiel’s cum on his face and tongue, waiting until the last bit spilled out. Castiel panted, looking down at Dean and cupping his face.
“Good boy,” Castiel cooed to Dean, which made him blush, slightly leaning into the touch. “Such a good boy.” Dean watched Castiel slide himself back into his underwear, cleaning himself up as if he hadn’t just been a mess under Dean’s tongue. Once fixed upright, Castiel moved to Dean, scooping the cum from his face and sliding it onto his tongue. Dean kept his tongue out as requested, tasting the salty cum. “Swallow.”
Dean slowly slid his tongue back into his mouth, nervously swallowing the cum. It took him a moment to get it down, mostly because of nerves, but he succeeded. Castiel took out a handkerchief, cleaning Dean’s face of anything else. Castiel’s hand on Dean’s face was soothing. Dean closed his eyes, melting into the touch as he came to terms with what he had just done. Castiel could tell Dean was becoming self-conscious; his happiness was falling away as shame set in.
“Stand,” Castiel commanded. Dean listened as Castiel cupped his face, looking Dean in the eyes. “Such a good boy.”
Castiel whispered so tenderly that it made Dean’s eyes water. Castiel watched him, trying to figure out a way to offer comfort. Castiel settled on a solution: leaning in, he pressed a loving kiss to Dean’s lips. Dean seemed surprised, pulling back and looking at Castiel in shock. Seeing the tears in Dean’s eyes, Castiel gave him a tender look and leaned in again. Dean leaned in as well. They kissed tenderly and with care. With a soft exchange, Dean pulled Castiel closer with a soft grip on his hips before Castiel pulled back again.
“My good boy,” Castiel whispered as Dean gave him a small smile, holding himself. Neither said anything as Castiel took his hand with care, giving it an affectionate squeeze. Dean needed this affection, especially after the intimacy they had just shared. “Thank you for trusting me.” Dean glanced up, blushing; his only reaction was a soft squeeze of Castiel’s hand in return. “Please think about my offer,” Castiel’s voice said, snapping Dean out of his thoughts. “You were such a good boy, I’ll let you take as long as you need to decide.”
Dean swallowed at that as Castiel cupped his face.
“Say it,” Castiel whispered. “Say you’re my good boy.” He didn’t expect Dean to do it.
“I’m your good boy,” Dean whispered, so softly that Castiel couldn’t help but kiss him in a quick, soft peck.
“Good boy,” Castiel whispered back, softly caressing his cheek before letting go of Dean. “I will be awaiting your answer.” Dean nodded, free of Castiel’s touch, holding himself. Castiel moved toward the stairs, with Dean following him.
Dean opened the door for Castiel, allowing him to ascend first. Castiel was halfway up the stairs when Dean slammed him roughly back against the side wall. Castiel blinked, taken aback. Dean stared coldly into his eyes. Had he pushed Dean too far? Had he done something wrong?
His thoughts were answered when Dean pulled out a flip knife. Castiel’s eyes moved to the weapon, but he didn’t react, refusing to let Dean sense his fear. Dean eyed Castiel’s face, taking in his reaction before slowly sliding down his body. Kneeling, Dean put the knife to the trip wire that Castiel had long forgotten. Dean sliced the wire with a quick motion. Castiel let out the breath he realized he was holding. Dean looked up at him.
That’s when he knew he won over Dean Winchester.
That’s when Dean Winchester became his.
Castiel reached a hand down, cupping Dean’s face as he mouthed the words to him, reminding Dean he was a good boy. Dean closed his eyes, enjoying the touch for a moment before standing and continuing up the stairs, moving away from Castiel’s touch. Castiel watched him go before taking a breath to relax and following him up.
Sam stood with the men in the living room, who were drinking tea. They stood when Castiel arrived, getting back to their jobs. The men thanked Sam before following Castiel to the door.
“I will await your answer, Dean,” Castiel spoke as his men handed him his gloves, scarf, and jacket. Dean watched Castiel intensely while Sam exchanged looks between them. “Thank you for your time.” Castiel walked out without another word, hearing the brothers exchange words.
“Well? Was I right?” Sam asked. “He’s persuasive.”
“Shut up,” Dean grumbled. Castiel smirked to himself as the door closed behind him.