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Sleeping with the Enemy

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Dean wakes up with a jolt, his hand immediately reaching out to where he always keeps a gun velcroed to the side of his bedside table. His fingers curl around it just as someone else's fingers curl around his wrist. “Boss. It’s me.” 


“Fucking hell, Benny.” Dean sits up in the bed, wiping a hand down his face. He looks over his shoulder at Castiel’s sleeping body. Something settles inside him at the confirmation that his boy is safe and okay. 


Putting his finger up to silence Benny, Dean slips out of the bed and drags on a discarded pair of sweatpants. Then he ducks into his walk-in closet, shutting the door before turning the light on. As Dean squints into the brightness, trying his best to get his damn eyes to adjust, Benny begins to brief him. “Two demons jumped Garth outside of a club about 40 minutes ago. He was able to fight them off, but he killed one of them.”


“Fuck.” Dean hangs his head. “Fuck. Okay. Who was it?”


“Just some low end idiot. No one of value.” 


“And the other one? The one that’s still alive?”


“Same. They both seemed new. Probably trying to prove themselves.” Benny tilts his head in the direction of the door. “We have the one that’s still kicking down in the dungeon.”


Dean sighs. “Alright. Does Crowley know about any of this yet?”


“If he does, he hasn’t made contact.”


“Anything from The Angels?”




Frowning, Dean turns to his rack of clothes and begins picking some out. He won’t be sleeping any more tonight. Might as well get dressed for the day. As he starts pulling dress pants up his legs, the ones for his favorite suit, Dean gives Benny his orders. “I want more info on these two demons, and someone needs to get me the whereabouts of Crowley right now. Check in with The Angels, I guess. Probably a good idea with the alliance. Give ‘em a heads up that Crowley might be stirring shit up.” 


“Yes, sir.”


“The one that’s still breathing, you said he’s in the dungeon?”


“Yes, sir.”


“Good. Strip him, spray him down, lower the temp, and hang him up by his wrists. I’ll deal with him later.”


Benny smirks. “Yes, sir.”


“Go on, now. Be quiet. I don’t want Cas to wake up yet.”


With a nod to show he understands, Benny opens the door just enough to slip out of it before quietly closing it again. He doesn’t make a sound as he leaves. 


Dean finishes getting dressed, then turns the light off in the closet and sneaks back into the bedroom. He pauses at the foot of the bed and gives himself 60 seconds to just appreciate the view of the boy he loves lying in his bed. In that single minute, he comes to a very important conclusion. 


He’s going to fuck Castiel tonight. 


They’ve waited long enough. 




Castiel wakes up slowly, the sunlight soft and welcoming as it pours in through the windows. He smiles at the view of the sun rising over the mountains in the distance. Then he turns on his side to look at an even better view. 


Except, Dean isn’t there. 


Castiel’s eyebrows pull in, making something on his forehead crinkle and pull at his skin. He slaps at it with a hand before yanking it off. The wrinkled sticky-note is bright yellow. Castiel grins like an idiot when he reads the words hastily scrawled across it. 


Good morning sleepy head,

Had to deal with some shit. 

Eat breakfast and lunch with Ellen.

Benny has your meds.

There are instructions for you in the playroom. 

Go read them.



Hoping Dean isn’t lurking around in the suite for any reason, Castiel drops all pretenses of acting cool and practically sprints to the playroom. His hand shakes as he reaches for the handle, and he has to remind himself twice that Dean gave him permission to go in. He can’t help but think of what happened last time he was in here, though. The things Dean did to him… god, the scene was mind blowing. More than mind blowing. It was fucking… cosmic. 


With a deep breath, Castiel pushes into the playroom, closing the door behind himself. Some of the lights are on, set to their lowest settings, including the lights around the platform of the bed. On the bed, in the center of the large mattress, is a black box with a red bow and what looks like a piece of paper. Castiel decides that it’s safer to read the letter first. He has a bad feeling about whatever is in the box. 



Be good for me today, and you’ll get that orgasm I kept from you last night. 

Be bad, and you’ll get your cock caged and your ass spanked. 

Either way, I’m fucking you tonight. Up to you if you enjoy it. 


Castiel moans, closing his eyes to try and get a hold of himself. It doesn’t help. All it does is make it easier for him to picture Dean fucking him. 


Snapping his eyes open, he rereads the first part of the letter before continuing on. 


It doesn’t get much easier to read. 


In the box is everything you need to make me happy today. 

I want you to come upstairs after lunch. Practice your music.

At 2 PM, you will shower. Clean yourself thoroughly. I want your ass clean enough to eat. 

Use the box to finish getting ready. 

Be naked and kneeling on the playroom cushion at 3 PM sharp. 

The bluetooth will be on. 

See you at 3, sweetheart. 

Be good. 



By the time he’s finished, Castiel’s face is bright red. 


He decides not to peek into the box yet. If he looks now, he’ll just obsess over the contents all day. Maybe this way, he’ll have a fighting chance of doing something other than thinking about what Dean might do to him. 




“P-please!” the man groans, a bubble of blood popping between his lips with the force of the one word. He gurgles a bit. Then he coughs. 


“Don’t choke on your fucking blood,” Dean growls, backhanding the piece of shit before grabbing a fistful of his hair and pulling so they’re looking into each other’s eyes. “I’m not finished with you yet.”


The man tries to speak again. Probably begging some more. Dean’s not interested. He just yanks on the chain he has gripped in his hand, raising the man until nothing but the very tips of his toes are touching the cement floor. The man screams. Dean just stares blankly at him until the man’s energy runs out. 


“Now,” Dean says quietly, starting to pace in front of the man. He checks his watch and frowns. “I only have 5 more hours until I need to be somewhere much nicer than this place, so tick-tock.”


The man chuckles, then spits a glob of red spit at Dean. It doesn’t even make it halfway to him. Dean just looks at the drop on his floor in boredom before slowly dragging his gaze back to the man. “Seriously, asshole. Let’s just get this shit over with.”


“Why? You’re gonna kill me either way!”


“Sure am. But you’re looking at a nice, clean bullet to the head, or me stabbing you and letting you hang like this, bleeding out like a stuck pig.” Dean walks up to the man and presses his hand against his stomach. He digs his nails in until the man is writhing and screaming, drops of blood pooling in the dents as he pulls it away. “It’s a simple question. Why did you want Garth?”


“I told you,” the man pants, tears falling down his cheeks, blood dripping down his stomach. “I - we - we,” his eyes start to flutter closed. 


Dean grabs a bucket of ice water and splashes it on him, glaring at him as he gasps and splutters. “I’m not done with you yet, remember?”


“Jus’ wan’ed scare ‘im.”


“Bullshit.” Dean grabs a knife, twirling it between his fingers. The man begins to violently heave and tremble, his chains rattling with each sharp movement. Dean rolls his eyes. “You look ready to piss yourself just at the sight of my blade. You don’t wanna die like this, man. I know you don’t. Let’s just make this quick and easy, yeah? You get put out of your misery, I get to go fuck my hot fiance. Win-win, right?”


The man sneers. “Fuck your fiance!”


Dean’s body goes perfectly still, the only movement being his eyes as they narrow. “Excuse me?”


“Said fuck your fiance.” The man chuckles, the sound raspy and choked. "Gotta say, 'm sad 'm not gonna be there when the demons get 'im. They're gonna fuck 'im 'till nothin's left."


"Shut. The. Fuck. Up," Dean orders in a cool, calm voice that means death for anyone in his presence. He presses the blade up against the man's soft cock and pushes down just enough to make him hiss. "Last chance. What did you want with Garth?" 


"Stupid, ya know that? Made one person valuable to two different organizations. You see how stupid that is, right man? Like… that's jus' a neon fuckin' sign for us. We destroy him, 'n it destroys you 'n The Angels. Two for one deal. You made Castiel-"


Dean stops him by shoving his knife into the man's gut and tugging upward, not caring as blood pours out over his own hand. The man stares at him with wide eyes, his mouth parted as he attempts to suck in a breath. "Shouldn't have said his name, fucker." 


Dean spits at him, then chucks the knife to the ground and turns his back on him. He looks over at Aaron and growls, "Let him bleed out. Make damn fucking sure he's dead before letting him down. Then clean this shit up and drop his body off on Crowley's fucking doorstep." 


Aaron nods. "Yes, sir. Anything else?"


"Yeah." Dean yanks at his tie, feeling the need to tear something apart. 


Because the piece of shit was right. Castiel is the holy grail to The Demons. He's perfect for them to target. And Dean won't survive. He could lose any of his men - even Benny - and figure out a way to keep going forward. But Castiel? Fuck, if they get a hold of Castiel… 


"I need you to get in touch with Ash and Charlie and schedule a meeting as soon as possible. We need to up Castiel's security." 


“Yes, sir.”


Dean takes the stairs two at a time until he reaches the main wing where his office is. He hurries down the hall and ducks into his office as quickly as he can in case Castel happens to be walking around. Considering the things Dean would like to do to him later, it’d probably not be the best thing if Castiel saw him drenched in blood and furious right now. 


Without bothering to wash up in his bathroom, Dean hits the button on his phone for Benny and puts it on speaker. It rings once before Benny picks up with a simple, “Yeah?” 


“Where’s Cas?”


“Uh - one sec.” There’s some shuffling around in the background of the call for a moment. Then Benny is back. “He’s in the kitchen with Ellen.”


“Okay. Yeah. Okay.” Dean rests his bloody hands on his hips, hangs his head, and closes his eyes. He tries to breathe, but he swears the oxygen isn’t reaching his lungs. Is this what Castiel feels like when he panics? It’s fucking awful. “I need you to keep your eyes on him, Ben. Like… keep them on him. No matter what. At least until he’s in the personal wing. And then I want you to be the one to guard the door. Okay?”


Benny hesitates. His voice is lowered when he speaks again, indicating that he’s probably already making his way to Castiel if he hasn’t reached him already. “Everything okay, boss?”


“Yes. Yeah. Fine. Just…” Dean takes a deep breath. He’s one of the most powerful men in the country. In the fucking world. He just murdered a man a few minutes ago. He murders men all the time. Tortures them. People fear him. Everyone fucking fears him. He’s Dean fucking Winchester for fucks sake. “I just need to know he’s safe today, okay? It’s irrational. There’s no reason for you to be panicking. Just… I just need to know, okay?”


“Of course, boss. Yes. I won’t let him out of my sight, and I’ll watch the door once he’s safe inside the wing.”


“Good. Yeah. Thanks. Good.” Dean sighs, scrubbing a hand down his face. He winces when he feels the blood. He had forgotten that was there. “Did he take his meds?”




“And he ate a good breakfast?”


Benny chuckles. “Yes. Scrambled eggs, two slices of bacon, a slice of toast, a bowl of fruit, a cup of coffee, and a glass of orange juice. Took his meds. Helped Ellen clean up. Watched a movie with Ash - half a movie, that is. He was unimpressed with it and went and played the piano in the foyer. Now he’s helping Ellen with lunch.”


“He - he played piano?”


“Yup. Fucking amazing.” 


Dean smiles to himself, feeling overwhelmingly better. He played piano. In front of people. That’s has to be a good fucking sign. Dean has to be doing something right at least. 


“I’ll keep him safe, boss. You just take care of you.”


Dean ends the call and nods to himself. He takes a deep breath. He refocuses. He vows that no matter what, no matter who, no matter how, no one will fucking lay a hand on Castiel. No one. No one but Dean. 


Dean will die before he allows anything otherwise.