So this took me forever to write but it is loosely based on a prompt I wrote a while ago. Enjoy :)
Warnings: Warden Castiel, Prisoner Dean, Alternate Universe - Prison, Bottom Castiel, Rimming, Rough Sex, Spanking, Sex Toys, Dirty Talk, Slurs, Light Dom/sub, Submissive Castiel, Dominant Dean
As the man crumbled forward after a knee to the groin, an uppercut was thrown sending the man's head backwards at lightning speed before he fell to the floor like a log. With instincts surprisingly similar to Batman (or so he though), Dean Winchester ducked the incoming punch from his rear as he crouched to the ground swung his leg out in the process, which took the man's legs from under him and sent him to the ground knocking his head hard on the smooth concrete with a groan. Dean smirked down at the bodies around him, five of them to be exact, either groaning in pain or knocked out cold and only a bloody lip on him to show for it.
"Winchester!" the head guard, Balthazar, called, "Warden's office now!" Dean smirked up at the guard where he was stood on the metal grate pathway that overlooked the dining hall before the surrounding guards approached him and led him by the arm to the door that led to the Warden.
Before he entered the familiar office, Balthazar had handcuffed him. If he needed to, Dean could easily slip them with the handy lock pick he kept on his person at all times that had managed to slip the guards' notice the entire three years he had been incarcerated. As he was only going to see the Warden, Dean knew he'd be safe and there was no need to slip them.
"He's not happy," Balthazar whispered to him and Dean simply smirked at him in reply.
"Is he ever happy? Dude's got a stick so far up his ass I'm surprised he can still walk." The remark earned him a jolt to his abdomen from Balthazar's batten causing Dean to hunch over with a wince.
"Respect the Warden!" Balthazar growled, "He's the only reason your ass isn't in high security. God only knows why. Save us a lot of trouble. He seems fond of you though so it would be in your best interest to do as he says."
"What can I say Balth, no one can resist the Winchester charm," he replied with a wink which earned him a roll of the eyes and a shove towards the door.
"Hurry up," Balthazar replied exasperated, "He's waiting."
Dean stumbled through the door glaring over his shoulder at Balthazar who had shoved him once again. When he turned, it was to see the back of the Warden who had his hands folded behind his back as he looked out the large window that overlooked the yard where a few prisoners were milling about on their recreation time.
"How many times Winchester?" the Warden growled his voice low and demanding. "How many times are you going to go about wreaking havoc in my dining hall, destroying my property and injuring my inmates?"
"What can I say boss, I just like hanging out with you," Dean replied smooth as ever. Of course as soon as the Warden turned around to finally face Dean, he knew it was mistake.
He stormed over to Dean his face screwed up in anger as he pushed right up into Dean's personal space. As he spoke, Dean could feel the spit on his face from his words, "You think this is a joke Winchester? You think you can just beat up whoever you like wherever and whenever you like? I should send you straight to the hole for a month for the damages you've caused and then when you're out I'll ship you off to the highest maximum security prison where the only human interaction you'll have is when they bring you your meals!"
Dean swallowed as he looked into the Warden's eyes knowing he meant every single word but Dean didn't let it show how afraid he was that he would follow through because he knew how to twist him to get what he wanted. The inmate's face broke into a smug grin as he eyed the man before him taking in his clenched fists and his tight shoulders before he finally broke the tension in the room by leaning forward so he was whispering directly into the Warden's ear.
"You and I both know you aren't going to do that Warden," Dean purred. He pulled back just enough to see his reaction and even though it was minimal, he could see the resolve breaking.
"And why would I do that?" the Warden replied his fist unclenching and clenching as he spoke.
"Because," Dean drawled in his ear, "You love it too much when I'm in here with you." With that, Dean raised his hands twisting the Warden around and bent him over his desk his hands forcing his head into the mahogany while he braced his body across his back holding him in place as he struggled. "Don't try and deny it, I see you watching me from up here when I'm in the yard as if you're just trying to figure out how to get me up here. There's no way you're going to ship me off." Dean accompanied his words with a grind of his groin against the Warden's ass earning an audible gasp and the tiniest whimper. Dean grinned at his victory leaning down so he was once again whispering into the Warden's ear, "Tell me you don't watch me and think about me up here with you just like we are now and I'll let you go."
There was an inaudible whine that Dean knew was what he wanted to hear. With his fingers wrapped in the locks of the Warden's raven hair, he pulled him back earning a hiss from the man. "What was that?" He asked cockily.
"Please," he whined. Dean grinned predatorily as he shoved the man back down onto his desk pressing his elbows into his back which would have no doubt been uncomfortable but the man was in no position to complain as he pushed back against Dean grinding his ass against Dean's crotch.
"Just what I thought," Dean cooed. "You're a needy little slut who would bend over for anyone who showed you just the littlest bit of defiance wouldn't you Cas," the nickname rolled off his tongue with familiarity earning another whimper. "Mister high and mighty up here in his office with a stick up his ass the size of a tree, I wonder if you'd be so feared down there if they saw you like this, begging to be fucked by Dean Winchester." Dean looked around the room and out the window before a grin broke across his face as an idea entered his mind, "Well there's always one way to find out."
The inmate pulled on Cas' hair once again forcing him upright and pushing him towards the window with a solid push that had the man stumbling over his feet. Dean took the opportunity to slip his cuffs and step up behind the other man once again pushing him against the glass. Cas' hands pressed against the glass and Dean could see the man had his eyes closed as he panted hard.
"Drop you pants," Dean demanded.
Cas' head turned to look over his shoulder at Dean his face clearly asking if he was being serious but Dean simply raised his eyebrows in response to which Cas quickly complied fumbling with the belt buckle as he tried to obey in haste. As soon as it was free of its loops, Cas dropped it to the floor, his pants following suit.
"Boxers too, Cas," Dean instructed. There was fear in the Warden's eyes this time as he turned to look at Dean before looking out the window at the few inmates who were still wandering around the yard. "Trust me when I say, they don't look up here and even if they did, you can't make out anything." Dean soothed. There was a slight nod to Cas' head before his hands gripped the waistband of his underwear and pushed them to the floor, kicking his pants and boxers off in the process. With the Warden's bottom half naked, Dean couldn't help but stare.
"Perfect," Dean praised as he stepped behind the other man bringing his arms around and lightly grazing his fingers along the man's thighs, peering over his shoulder as he did so. He smirked down at the erection that was present while the man in his arms shivered at the slightest of touches. "You been thinking about this all week? Thinking about how last time I left you such a mess that no one heard from you in two days? Hmm Cas? Am I that good?" He asked as his fingers worked the buttons of his shirt before he slipped it off the Warden's shoulders.
"Please," the Warden breathed so quietly that Dean strained to hear him.
Dean nosed along Cas' neck trailing up to his ear as the other man craned his neck to grant better access. When he reached his ear, Dean took the lobe between his teeth working it over teasing the other man while his hands continued their light touches. The man before him was trembling so hard as Dean worked him over that he started to take pity on the man. Dean removed his right hand from the man's body and moved it up to Cas' mouth who instantly opened wide allowing the prisoner to slide two fingers inside. The Warden eagerly sucked on the digits while Dean's free hand moved to lightly wrap around the man's dripping cock tight enough for him to feel it but not nearly enough to cause any pleasure.
"So wet for me aren't you baby," Dean cooed. "Bet if you could, your ass would be dripping right now. All wet and ready for me to just slide in and fuck you like you've been begging for since I came in here." His words earned a muffled groan causing a dark chuckle to escape Dean's lips, "But we can't have that can we? Better get those fingers nice and wet, don't want to hurt you baby."
When Cas' tongue tracing his fingers became too much, Dean pulled his hand free earning a desperate whine from the Warden. Dean kissed his neck to soothe him, silently promising him he would get what he needed soon enough. With his hand now free, Dean trailed his fingers down to the Warden's ass pressing between his cheeks and slowly traced his rim. The touch had the man's body shiver before his hips bucked back onto the finger begging for it to slip inside. In response, Dean squeezed the Warden's cock painfully earning a sharp yelp.
"Stop being such a whore and take what you're given," Dean growled unrelenting on his grip to the man's cock. The other man's whole body tensed before he nodded and let himself go slack. "Good boy," Dean praised before he relented his grip which earned a relieved sigh. Dean chuckled as his fingers once again found Cas' entrance and slid a finger inside. The hitch in the Warden's breath was what kept Dean sane at night. "So perfect for me baby," Dean whispered into Cas' neck as he pressed butterfly kisses to his heated skin. "You think you can handle more?" He asked as his finger continued to thrust inside the Warden's tight ass wriggling about stretching him wider. At the Warden's nod, Dean slipped a second finger inside and earned a strangled hissed. "I know baby, I know," Dean soothed his free hand moving up Cas' torso feeling his muscles flutter under the touch while his fingers continued to work inside him. "You want me to use my tongue? Get you nice and wet for me?"
Cas' whole body shuddered his forehead dropping against the glass with a thud before he breathed out, "Please." Dean was on his knees in an instant trailing his hands softly down Cas' sides leaving goosebumps in their wake. When his hands reached the muscle of the Warden's ass, he squeezed the pert muscle working both cheeks over before spreading them. A small whine escaped Cas' lips as Dean licked over Cas' entrance tracing the rim for a moment before pulling away and sliding his finger back inside.
"You're so fucking perfect, Cas," Dean breathed as he worked his second finger inside searching them deeper inside the other man before he leant forward once again working him over with both tongue and fingers. Dean's spare hand rested on Cas' hip feeling him quiver under the ministrations trying with all his might to not thrust back.
When a third finger slipped inside easily, Dean stood back to his feet his arm wrapped around Cas' torso holding him against his chest. Dean looked over Cas' shoulder seeing the Warden's face reflected back in the glass in front of them smirking at how debauched he looked. His eyes were closed with his cheeks flushed red and teeth biting down on his lower lip to keep the noises at bay. He was absolutely beautiful. Dean kissed his cheek in appreciation smiling when Cas leaned into the touch.
"Dean," Cas whined, "Please."
"You think you're ready?" Dean chuckled at the cry Cas' let out as he pulled his fingers free.
A second later, Dean was pulling his orange jumpsuit down letting it pool at his feet along with his boxers. He spat into his hand before he wrapped a hand around himself and spread it over his cock along with the pre-cum that was leaking from the slit. His eyes rolled back into his head at the sensation after denying himself for so long but before things could get too far, Dean stopped his movement. He stepped up behind the other man again with one hand on his cock, the other resting on Cas' hip holding him in place while he guided himself to Cas' entrance.
With the head of his cock pressed up against Cas, he buried his nose into the nape of the other man's neck before he slid inside in one slow, long thrust. The Warden's head dropped against the glass once again panting as he shook where he stood. Dean's other hand came to rest on Cas' other hip holding him in place as they both adjusted.
"Fucking hell, Cas," Dean panted. "Never going to get used to this. So good for me baby," he purred.
Without another second to waste, Dean pulled back and thrust back inside relishing in the broken sound Cas let out. His grip tightened on the other man's waist as he pulled back once again thrusting in harder than the previous thrust. His pace quickened, his thrusts more brutal as he continued to move inside the Warden earning delicious moans and grunts from the man in front of him.
"You like that, Cas?" Dean asked as his thrusts gained further momentum. "Tell me how much," he demanded while one of his hands slipped up his torso and started to play with one of his nipples.
"Y-You," Cas stuttered, "You feel so good."
Dean chuckled as he continued to work over the bud grinning as Cas' head fell back against his shoulder at the sensation.
"Come on, Cas. You can do better than that."
"I-I like how big you feel, stretch me, uh, so wide. Leave me sore for days," the Warden panted between cries and whines. "God Dean, fuck me harder," he begged no longer worried about the people milling about below and he succumbed to the pleasure Dean was giving him. Dean decided to tease him a little longer not giving in to Cas' demands grinding against his ass in slow circles until Cas was near tears. "Dean," he whined, "please."
Dean smirked against Cas' neck before he pulled out completely and spun them around. Before Cas could complain, he had him bent over his desk, face pressed into the wood thanks to Dean's hand on the back of his head and thrust back inside.
"Of fuck yes," Cas cried out as Dean slammed into him over and over, one hand still gripped tightly to his hip to pull him back into each thrust. Dean was so overwhelmed with how Cas felt around him, so hot and tight that he knew he wasn't going to last much longer. He knew how Cas loved it rough and wanted him right on the edge there with him so with one last ditched effort, he wrapped his hand in Cas' hair pulling back painfully until Cas cried out. His hips didn't slow their punishing pace as he pounded into the Warden's prostate over and over so he was a mess of 'uh, uh, uh's and 'Dean's.
"You love it like this don't you baby?" Dean grunted. "You going to come all over your desk like a good boy Cas? Bet I don't even need to touch that cock of yours for you to come." When all Dean got in reply was another string of curses, Dean knew that the Warden was close to the edge and only needed just a little more to get him there. "What would you do if someone walked in right now? See you hanging off my cock crying out like a two dollar whore and better yet, hanging off your prisoner's cock. Huh Warden, what would you do?"
Suddenly, Cas was crying out, clenching down hard on Dean's cock as he came hard all over the desk beneath him. His whole body convulsed as Dean continued to thrust until he simply went limp panting to recapture his breath. Dean let go of his head to grip onto his hips tight enough to leave bruises as he picked up the pace, thrusting inside the limp warm body with abandon, pulling him back into his thrusts. It was only a handful more thrusts before Dean hit the edge himself pushing inside as deep as he could as he came with a groan. He collapsed over the Warden's back as he recovered savouring the satisfied sigh that fell from Cas' lips.
With their heartbeats back to normal, Dean raised himself up on shaky arms and stood upright pulling himself free of the other man's body as he did so. Cas winced at the sensation and Dean slapped his rear to shut him up.
"Don't let anything fall out," Dean commanded before he leant down to open the bottom drawer of Cas' desk. He pulled out the black plug he found inside that he knew was in there before he pressed it to Cas' entrance and slipped it in his sloppy, fucked out hole. Once it sat snug inside, Dean slapped him once again on the other cheek which earned a chocked moan from the Warden. "God, you're such a fucking slut," Dean laughed.
"Mmm, only for you Winchester," Castiel retorted a lazily smile on his lips as he stood and turned to face Dean. Dean couldn't help but smirk at how fucked out he looked. His hair was a shambles, his lips bitten completely raw and his cheeks and chest covered in a blush. Before Dean knew what was happening, he was lifting Cas back onto the desk and kissing him sloppy but passionately. Cas was completely pliant in his arms kissing back with as much desire before he pushed him away with a hand to his shoulder. "We should probably clean up," Cas reasoned, "You've been in here a while now."
Dean's head dropped to Cas' shoulder and wrapped his arms around the other man. "I don't want to go," he whispered barely loud enough for Cas to hear him, but somehow he did and it earned him a kiss to the top of his head.
"As much I don't want you to, you do have to go. Now get off me."
Dean grumbled the whole time but he did as he was told and unravelled himself from Cas' body. He smirked as Cas stood with a wince, grimacing at the fact he had been sitting in a pool of his own cum. When Cas noticed, Dean schooled his expression with the glare he was receiving.
They dressed in silence before Dean picked up the handcuffs and gave them to Cas to put back on him. Dean watched as Cas' head dropped and his expression grew dark as he took the cuffs from him. Before he could put them on, Dean raised his hands to grip Cas' chin forcing him to look him in the eyes. Dean searched the other man's face for some kind of clue as to what was going on before he noticed the bags under his eyes, the exhausted look in his stare.
"What's wrong?" Dean asked sincerely.
Cas sighed and tried to pull away but Dean held him firm forcing him to keep their gazes locked. After a few moments of silence, Cas' resolve broke.
"I can't deal with this, Dean," he began. "The guards, they're getting suspicious as to why I'm not putting you into higher security and I can only hold them back for so much longer before someone goes over my head and they come to ask questions I can't answer."
Dean reacted without a second thought and pulled him in for a hug. Cas clung to him as if Dean was the only thing holding him up and it broke Dean's heart to know that this man was in so much pain and he hadn't even known.
"I'm sorry," Dean breathed into his hair kissing the top of his head. "I know I'm not making it easy but they attacked me not the other way round. I just defended myself. Come on Cas, it was five on one you know I'm not that reckless."
Cas pulled away from his slightly only enough so that he could look Dean in the eyes as he spoke, "I know. I know you're not. It's just-" he hesitated looking away for a moment before he locked eyes with him once again, "I'm not cut out for this Dean. I can't deal with the fact that when I go home it's cold and empty while you're in here locked away and the only way I can see you is if you go and beat people up."
"Cas, Sweetheart," Dean calmed with a hand to his cheek. "I know it's not ideal but I'll be out soon."
Cas' eyes blew wide as he stared back at Dean, "Wh-What?" he stuttered his face full of confusion. "You're serving two life sentences back to back. How are you going to be out soon?"
"Shh Sweetheart. The less you know, the better." Dean kissed his forehead and stepped away holding his hands out.
Before long, Dean was back in his cell with his job in the kitchens revoked and reassigned to bathroom cleaning duty. But he had a smile on his face as he recounted the events of earlier while he went over his plan one more time.
There is a possibility of more but that depends on you guys ;)