#Dean Winchester x Deacon Kaylor

[javocjovian]

The Job - SPN Kink Bingo

Title: The Job Link: https://archiveofourown.org/works/24156748 Square Filled: Bondage Ship: Dean x Deacon (Folsom Prison Blues) Rating: E Tags: Bondage, Handcuffs, Prison Sex, Discipline, implied pre-series Dean x Deacon, Age gap, no underage, Consensual Summary: Dean’s decision to take a job in a prison had absolutely nothing to do with Dean’s crush on their dad’s old friend, Deacon. Nothing at all. Nope. Word Count: 1370

Created for @spnkinkbingo​ Beta-ed by @nickelkeep​

Quote:

After a short but explicit discussion, Deacon grabbed the keys to Dean’s cuffs. Dean flushed but muttered ‘leave them on’, and in five minutes Dean found himself cuffed to the bars of an unoccupied private cell and bent over with his pants around his ankles while Deacon made Dean swear that he’d died and gone to Heaven.

(x)

The Job

Dean had accepted the job so quickly that he hadn’t realized why. When Sam complained and looked at Dean like he was suicidal, Dean played it off: ‘He’s a friend of dad’s. He saved dad’s life. We’re Winchesters, that means we repay our debts. What, are you afraid of a little ghost, Sammy?’ All of those excuses were perfectly true, but it wasn’t until Sam and Dean were hauled into the Green River County Detention Center, cuffed and in prison rags, that Dean realized what extraneous factors might have been at play in his rash decision to take the job: Deacon.

 Dean hadn’t met Deacon until after Sam left for Stanford, but Dean had heard stories about him from John. John and Deacon had been old war buddies, and Deacon helped John out of quite a few sticky situations since then. Dean knew he was a prison guard, and he expected him to be like John—tough, unyielding, and even a little cold. Deacon certainly knew how to play the part. However, when he came to help them out with a case in Kentucky, Dean learned that he was also intelligent, intuitive, and surprisingly gentle. It took about two seconds for Dean to realize he had a crush. Luckily for Dean, the feeling was mutual.

 Dean didn’t know what he had expected when, seven years later, he found himself face to face with Deacon once more, as his prisoner. All Dean knew was that the libidinous thoughts that flooded him during that silent reunion were something he’d take with him to his grave. He also had no idea, although perhaps a foolish fantasy, that by the end of the night he’d have yet another secret to keep from Sam.

To no one’s surprise, Dean had found himself in a fistfight before lunch. It worked out because Sam and Dean were able to meet with Deacon in private to discuss the case. But Dean ended up in yet another fight not four hours later. That time he was hauled to Deacon’s private quarters, alone.

Once they were alone, Deacon was articulate and forthright as ever. Fleetingly, he reminded Dean of Sam, something that cemented Dean’s belief that he was on a bullet train to Hell, even more so after Deacon guessed the real reason Dean had let himself lose two fights that day.

After a short but explicit discussion, Deacon grabbed the keys to Dean’s cuffs. Dean flushed but muttered ‘leave them on’, and in five minutes Dean found himself cuffed to the bars of an unoccupied private cell and bent over with his pants around his ankles while Deacon made Dean swear that he’d died and gone to Heaven.

Dean was a shivering, sweating mess, and Deacon had only been working him over for ten minutes. He was pleasuring Dean experimentally with a metal baton, lubed up and buried in Dean’s ass.

“You know, Dean,” Deacon said smoothly, “I’ve seen a lot of ass come through this place, but none as exquisite as yours.”

Dean could feel his thighs shaking as Deacon pressed the baton into all the right places. He was overwhelmed, but it was ecstasy. Deacon played the imposing, dominator role so well, and it turned Dean to putty.

“You’re a glutton for punishment, aren’t you, Winchester?”

As per their discussion, Dean muttered out a firm, “Yes, sir…” his expression screwed up in concentration. His face fell a second later when Deacon found his prostate. Dean couldn’t help but buck his hips and strain at the cuffs locking him face-first into the bars. He heard Deacon chuckle.

“You’ve grown into quite the Adonis, Dean. Perfectly carved... strong... resilient...”

Dean bit back a groan. Deacon was doing things to his body that Dean had never felt before. Every press into his prostate had him dripping precum onto the cement floor. Right when Dean thought it would be too much, Deacon would stop and have Dean begging for more.

At last, Deacon slid the instrument out of Dean’s ass. Dean heard it clatter onto the floor and he trembled.

“Now then, I say getting into a fight in my prison deserves a more hands-on punishment. What do you think?”

It wasn’t a question. Dean’s head drooped as he heard the tear of a condom packet. His whole body shuddered. Somehow he managed to reply, “Yes, sir.”

“Good boy.” Deacon smiled. Then, knowing it would drive Dean wild, he added, “Your daddy would be proud.”

Deacon slid his cock into Dean’s ass, and there wasn’t enough air in the room for Dean to take a breath. He groaned shamelessly, grabbing the bars as Deacon pressed deeper and deeper. He could hear Deacon’s soft moan of pleasure as he slid all the way in.

When Deacon was standing flush against Dean’s ass, he reached over Dean’s shoulder and took hold of his face. Dean lifted his head up, his cheek pressed against the cool metal bars in front of him. His lips were glossy and red.

“You’ve earned this, Dean. I want to hear you enjoy it. Understand?”

“Yes...sir…”

Then Deacon began to move. He forced Dean to look at him as he ravaged him from behind, stroking Dean’s prostate over and over again. Dean trembled and moaned. He couldn’t stop himself. He made sounds he’d never admit to hearing, let alone producing. He lifted his ass of his own accord and outright begged for it, all the while Deacon took full advantage of him, fucking him into the prison bars, bent over, prone and defenseless. It was as good as the first time in that Kentucky motel. Hell, it was better.

When Deacon let go of Dean’s face Dean didn’t dare move it. He watched as Deacon moved his hand down Dean’s scrunched up orange prison shirt, down his heaving stomach and damp treasure trail. Dean’s expression opened up as Deacon touched his cock, swollen and throbbing past the point of endurance. When he began pumping it to the rhythm of his thrusts, Dean’s body spasmed and he dissolved into a series of curses and pleas.

“That’s good, Winchester. Real good. I want you to come, you hear me? I want to see it on your face. I’ll keep you here all night if I have to.”

Dean’s eyelashes fluttered dangerously. He could barely see. He could feel an orgasm tensing his every muscle, building powerfully and threatening to overtake him. Dean swallowed a whimper, but he couldn’t hide the expression on his face.

“That’s the Dean I remember… young... bold��� coming to see me in the room next door when your daddy went out...”

Dean’s expression opened up suddenly, and with one more thrust was coming harder than he had in years. He moaned gutturally, seizing up and listening to Deacon’s hurried breaths of approval. Deacon fucked Dean through his orgasm, not letting up until Dean’s stomach had dropped and his body turned to static. Then Deacon buried himself to the hilt and groaned. Dean felt the hand around his cock twitch as Deacon came.

Soon they were both motionless and panting, basking in their shared, post-orgasm bliss. Despite looking flushed and indecently roughed up, Dean managed an almost cocky grin at Deacon. Deacon chuckled.

Deacon pulled out and uncuffed Dean at last, then helped him get cleaned up with that surprising gentleness. It wasn’t often Dean felt taken care of, so he allowed himself to indulge in it. And when Deacon kissed him against the prison bars, Dean let his heart swoop into his stomach.

Dean saw Sam again the next morning, and just like that, they were back on the hunt. Dean never told him that he didn’t spend the entire night in solitary, or that he had the best night’s sleep in years and didn’t even look for the ghost. Although he did mention a few times that they should take more jobs in prisons, if only to see the incredulous look on Sam’s face. Dean had privately decided that prison wasn’t so bad, and if it weren’t for Agent Henriksen’s crusade to incarcerate the Winchesters for life, Dean might have decided to extend their stay at Green River County Detention Center just a little longer.

[coffee-obsessed-writer]

The Devil in Disguise Masterlist

Dean Winchester x Reader; Deacon Kaylor x Reader (Platonic); Derek (OMC); Preacher Steve (OMC)

Summary: Dean’s on the run from escaping a prison where a job went south. Sam is in the wind. With nowhere to go and an injured leg, Dean takes refuge in the only place he could find—an old remote cabin. Normally empty for long stretches, Dean happens to stumble in the same day that the cabin’s owner returns. After a rocky first encounter, Dean comes to believe that a distant connection they share could be the thing that saves his life and gets him back to Sam. But will it happen before Y/N’s finance, a prison guard at Green River, finds the secret she’s hiding in the woods?

A/N: The fic was inspired by the song “The Devil’s Backbone” by The Civil Wars. (Song lyrics below the cut).  Set around S2 (Folson Prison Blues).

Series Warnings: Language, Violence, Smut, Angst, Character Death

Part 1 | Part 2 | Part 3 | Part 4 [WIP] | Part 5

Oh Lord, Oh Lord, what have I done? I've fallen in love with a man on the run Oh Lord, Oh Lord, I'm begging you please Don't take that sinner from me Oh don't take that sinner from me

Oh Lord, Oh Lord, what do I do? I've fallen for someone who's nothing like you He's raised on the edge of the devil's backbone Oh I just wanna take him home Oh I just wanna take him home Ooooooooooo Ooooooooooo

Oh Lord, Oh Lord, he's somewhere between A hangman's knot, and three mouths to feed There wasn't a wrong or a right he could choose He did what he had to do Oh he did what he had to do Ooooooooooo Ooooooooooo

Give me the burden, give me the blame I'll shoulder the load, and I'll swallow the shame Give me the burden, give me the blame How many, how many Hail Marys is it gonna take?

Don't care if he's guilty, don't care if he's not He's good and he's bad and he's all that I've got Oh Lord, Oh Lord, I'm begging you please Don't take that sinner from me Oh don't take that sinner from me