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Sleeping with the Enemy

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“You’re trouble, you know that?” Dean asks Castiel about an hour after Castiel has fully come back to himself. They’re lying on the huge couch in the living room, cuddling and watching Netflix. Dean had suggested they watch in the little movie theatre he had but Castiel had rolled his eyes and told him that they were going to be normal people for a night and use a damn TV. 


Castiel isn’t sure what he did to make Dean say he's trouble, however. They haven’t spoken at all since they started the TV show they chose. They’re only a third of the way through episode one of Sex Education, and unless 3 teenagers talking in an abandoned bathroom about overdosing on Viagra speaks to Dean on a deeper level somehow, Castiel doesn’t know what brought it on. 


He knows how to answer, though. With a cheeky grin and an, “I disagree completely.”


“Yeah. Yeah, I bet you do. My little brat.”


Castiel blushes. “Is that a bad thing?”


“No. Surprisingly… I find it endearing.” Dean brushes one of Castiel’s curls off of his forehead. “I’ve never had one.”


“A brat?” Castiel turns in Dean’s arms so he can look at him better. “Wait, you’ve never had any sub I thought?”


“You’re right. I misspoke. I’ve never played with a brat.”


Castiel doesn't know what to make of that. Does Dean hate brats? Is he making an exception for Castiel? And, if he is, will he get tired of doing that?


“What’s going through this pretty head of yours?” Dean asks softly, tapping a finger against Castiel’s temple. As if he knows that Castiel doesn’t want to tell him, as if Castiel was already starting to formulate a lie, Dean adds, “Remember, Castiel, honesty is huge for a relationship between us.”


The reminder takes the air out of Castiel’s wings. He deflates against Dean, tucking his face into his neck so he doesn’t have to look him in the eye. “Why have you never played with a brat?” 


“Brats are…” Dean trails off and Castiel feels like shriveling up in a ball and disappearing. “Brats are long-game. One scene with them just isn’t - it isn’t enough, in my opinion at least. The thing about brats is how diverse the play is. Fluid. If I wanted to play with a sub, I’d talk terms with them beforehand. What they want from the scene, what I want, and negotiate from there. The scene starts, they obey the rules set up, you give them whatever was discussed, punish them if they fuck up, scenes over, you do aftercare, all is well.”


“But… not with a brat?”


“You can do that with a brat but I feel like it strips them of their personality. It’s - it’s safer to play within strict limitations when it’s a scene with a stranger or someone you aren’t very comfortable with. There’s less wiggle room of something going wrong, of something happening that they accidentally didn’t discuss, whatever.” Dean sighs, and Castiel can tell he’s worried he’s not making any sense. He is. A little. Castiel just can’t wrap his mind around it very well. “For a standard sub, strict limitations is usually fine. One night they want impact play. Another night they want suspension. Mix and match. Yada-yada. But a brat, usually, doesn’t want the scene to be planned at all. Not by them, at least. They like surprises, which usually works best if they’re in a long-term deal with a dom. And brats like being mischievous. Cheeky. They like to fight and wiggle and say no even though they don’t mean it. They like to be a good boy one scene and then naughty the next, and for both the sub and the dominant, it’s a thrill to get to experience both. To know that the man you’re kneeling for and obeying is the same man who whipped the shit out of you for biting him. To know that that boy on his knees being so damn good for you is the same boy who bit you last week and was a little shit that needed to be whipped until he sobbed. Both of them knowing that the other stuck around despite it all. It’s - it’s something I’d like, to be honest. I’m a sadist after all. But-”


“Wait, you are?”


Dean pauses and Castiel can feel how badly Dean wants to flinch. It’s rare for Dean to feel that way, which makes Castiel sad. Guilty. He shouldn’t have said anything about - “Yes. I am. Mild sadist, but… well - well, okay, I might be more than mild, I’ve never let myself explore it farther. I - I don’t know. But it’s only when it’s consensual though. Only when I’m paired with a masochist who fucking loves it. I don’t - I’m not the kind of sadist who wants a sub that hates pain. I don’t get off on them suffering for me, I get off on them suffering because of me but for themself. Does that make sense?”


“Yeah.” Castiel runs a hand along Dean’s bare ribcage, smiling when it makes him shiver. “Am I a masochist?” 


The pause is even longer this time. 


Then, very tentatively, Dean says, “I believe so.”




“Why are you a masochist?”


“Why do you think so?”


“Oh.” Dean chuckles. “Where do I begin? There’s the fact that you’re bratty in the first place, which means you have to like the punishment to some degree or you wouldn’t risk it. There’s the fact that your cock went from half-hard to leaking pathetically all over my floor after just a few hard slaps to your ass. Or we could talk about the fact that I honestly believe you could come if I did impact on you a certain why. Or would you prefer we focus on how you were humping the bench beneath you like a little slut as I paddled your ass raw?”


Castiel had tucked his face in the hollow of Dean’s throat about halfway through that and he remains there. “Oh.”


“Yes. Oh.” Dean kisses the top of his head. “It’s not shameful, Castiel. Not in the least.”


“I know.” And Castiel does. He knows. It’s just… “Is that why I cut myself? Because… because I like it?”


The way Dean’s breath hitches seems like a bad sign but his voice is surprisingly soft and understanding as he asks, “Do you like it?”


“I mean, obviously…”


“But-” Dean stops himself, seeming to be thinking his words through first. “What do you like about hurting yourself? Is it the pain itself or how the pain affects your anxiety and depression?” 


Castiel frowns. “I don’t know.”


“Can you maybe try to explain what you feel like when you cut.”


“I - it changes.” Castiel tries to think of how to explain it. He wants to. He wants to help Dean understand and he wants Dean to help him understand. “Sometimes it feels like I’m floating outside of my body. Detached. Usually that’s - usually that’s when I’m really depressed. I guess I sort of go - blank? Empty. It’s a scary feeling and I - I don’t like it.”


“So you hurt yourself, and it grounds you? It brings you back?”


There’s not an ounce of judgement in Dean’s voice. 


It’s amazing. 


“Yes. That’s - yes. It helps, at least. Not always a magic fix but - yes.” Castiel runs a finger along Dean’s collarbone. “Sometimes it’s the opposite. It feels - it feels like I’m trapped inside of my body. That’s usually the anxiety or the - the panic. Like I’m stuck inside my body and everything is caving in on me. It makes me want to scratch my skin off. Claw my way out. Cutting - cutting makes it all calm a bit, I guess? It’s something to focus on.”


“It grounds you, just differently.”




“But you don’t get off on either of those pains? They ground you, relieve you, but they don’t pleasure you.”




Dean’s hand presses against Castiel’s back, bringing him in tight. Almost painfully so. It’s not, though. It’s good. It’s so fucking good. 


“You like cutting yourself because it grounds you and it’s a way to escape whatever current state your mind is stuck in.” When he says it like that, it sounds so simple. “Then why do you like it when I hurt you in a scene?”


Isn’t that the million dollar question?


“I have no fucking idea.”


This makes Dean laugh. The sound is low and soft but full-bodied as well. It’s beautiful. “It’s okay not to know. What’s more important is that I can give you those two ways of grounding you in our playroom, plus give you the pleasure you need, all without you having to hurt yourself like that.”


Castiel’s heart skips. He pushes up onto his elbow to look Dean in the eye. “Really?”


“Yes. Well, I want to try at least. Suppose I shouldn’t be too cocky about it until I know it’ll work.” 


“But… how?”


“It’s a bit of a… hypothesis of sorts but,” Dean pauses, cupping Castiel’s cheek. His smile is nervous but hopeful. “When you’re out of your mind, I’ll bring you down. When you’re trapped, I’ll make you fly so high you forget your own fucking name.”


“But how?” 


“I don’t know yet.” Dean gives him an apologetic smile. “Think maybe it’ll take some testing out, though I have a few ideas.”




“Liiikkee,” Dean repeats, “You’ll find out when I show you.”


Before Castiel has a chance to pout too much, Dean’s moving into the next topic of conversation. “You want to do this full-time. What, exactly, does that mean to you?”


It feels like Castiel is given whiplash. He has to think for a minute, switching gears. Dean’s patient as he waits, just playing with Castiel’s curls and smiling a secret smile that makes Castiel feel bubbly inside. 


Castiel has thought a lot about this and at the same time he’s barely thought about it at all. He’s thought about the big picture quite a lot. The concept. But the details? Not so much. 


He’s still a virgin. Give him a break. 


“I just want… I don’t know.” Castiel sighs, already feeling frustrated. “Like, I don’t want to become your sex slave or shit like that. I think I already made it pretty clear how I feel about being locked in your ivory tower and controlled. I - I don’t want to feel like I’m living under my father again.”


“Okay.” Dean gives him an encouraging smile. “What do you want it to be, then.”


“Like - like that night, when you made me eat and I was good so you massaged me. I - I liked that you cared. That you made me do stuff to take care of myself when I didn’t want to do it myself. Sometimes it’s hard to - sometimes it’s overwhelming trying to take care of myself.” Immediately, Castiel wants to swallow the words back. Choke on them. He squeezes his eyes shut, feeling his face heat up. “That’s fucking stupid. I know that’s stupid. I’m not a fucking child-”


“Enough,” Dean snaps. It’s his dom voice. Angry. Authoritative. Leaves no fucking room for argument. Castiel obeys, falling silent, but he keeps his eyes closed. He shivers when he feels Dean’s fingertips on his cheek. “It is perfectly normal to feel overwhelmed by shit like that. Hell, Cas, I get overwhelmed with shit like that. Sometimes, waking up in the morning is all you can fucking do that day, and ya know what, babe? I’ll be so damn proud of you for that. I’ll take care of the rest. You just have to keep waking up. And on your good days - on your good days, you’ll have more freedom. Things will be relaxed. But every day, no matter what your head is like, I’m going to make sure your basic needs are met. You’ll eat three meals a day. You’ll shower or bathe. You’ll do your homework if you have some, or practice your instruments, or whatever other responsibilities you have that I think you’re fit to deal with that day. On the good days, you can do all that yourself, but on the bad ones, I’ll do it all for you. Feed you. Bathe you. The works.”


Castiel opens his eyes wide. “You’d - you’d do all of that?”


“Of course.”


“I don’t want to be a burden.” Castiel looks down at Dean’s chin, unable to meet his gaze. “I don't want you to get sick of dealing with me.”


“Cas, babe… can you look at me?” It takes him a second but after a deep breath Castiel meets Dean’s eyes. His expression is wide-open. Vulnerable, but sure. “Me taking care of you is what I want. What I need. I’m never going to get sick of you.”


Feeling incredibly exposed and afraid, Castiel whispers, “Promise?”


“I swear.” Dean drags his thumb along Castiel’s lip, lust flashing in his eyes. “What do you think of what I said so far? The standard rules?”


“I like ‘em.” Castiel’s eyes flutter closed as Dean’s thumb skates along his jaw and down the curve of his neck. He shivers as it passes over a sensitive spot. “When are you gonna want me to - to kneel and stuff?”


“I’ll always tell you. Always. You have no expectations from day to day, other than to trust me, be honest with me, and listen to me - unless you need to safeword.”


Castiel made a face. “Safeword? For stuff that isn’t sex?”


Absolutely. Cas, if I ask you to shut off the damn bedroom light you can safeword if it feels warranted. I won’t argue with you. I’ll want an explanation so I can understand and help you. So it doesn’t happen again. But your safewords never go away. Never. You - tell me you understand that, okay? Can you repeat that for me?”


“My safewords never go away.” Castiel feels incredibly powerful saying it. “Never.”


“Good boy. Now, just because I haven’t told you to kneel doesn’t mean you can’t. You are more than welcome to always kneel for me if you want to or you feel like you need to. Even if we’re in public. No place is off-limits when you need me to be your sir.” Dean smiles at that last part, as if he’s particularly fond of the idea. Castiel’s pretty damn fond of it himself. “The same goes with calling me sir. Even if you haven’t been told to, if you feel the need or desire to, you always can. I’ll feel honored. I like to feel as if I’ve earned the right to be called that. It pleases me to know you want me to be that for you. Okay?”


“Okay.” Castiel looks away, blushing. “Sir.”


Dean chuckles. “God do I love the sound of that on your tongue.”


“Maybe you just like my tongue.”


“Maybe I do.” Dean’s grip on him tightens, bordering on pain. “Maybe I’ll have to test it a bit more before I decide.”


“Please, sir.”


This just makes Dean laugh again. He’s clearly amused. He’s also clearly not going to give Castiel what he’s asking for, which is frustrating as all hell. 


“My little brat,” Dean muses, running a hand through Castiel’s hair and gently tugging. “Do you want more rules so you can be a brat?”


Castiel nods. Dean allows it, but he makes it so every jerk of his head is a fight, and that turns Castiel on way more than it fucking should. “I like the idea of getting rules that day, though. Or, like, scene by scene or whatever. It gives me anxiety to - to have to worry about remembering a bunch of stuff.”


“Yes. I know.” 


“You do?”


“Yes.” Dean smiles softly. “I realized it when you dropped. I understand you were having a lot of thoughts and were already on a downward spiral but you not knowing to call me sir, and then being unsure if I wanted you to kneel in the bathroom when I asked you to draw the bath. You need clear instructions and you need them to not be overwhelming.”


“And you’re just… okay with that?”


Dean’s smile turns into a grin. “Very much so. What would be the point otherwise, Cas? Like I said, I enjoy what we do because you enjoy it too. It has to go both ways. I like knowing I’m taking care of you. Knowing I’m giving you what you want - or sometimes what you need, because they can be different even if that frustrates you, which, trust me brat, it will. If I give you a set of rules that just make you more anxious or expect things from you that you won’t like, then I’m not doing that. I’m not taking care of you or giving you what you want and need. Does that make sense?”


Castiel nods. 


Then he’s blushing again, his thoughts drifting to earlier today. When he wanted to defy Dean. Push him. The thrill it gave him to see how far he could go. To know that someone dangerous like Dean would be punishing him. To see if he could take it. And he liked it. He hated it... But he liked it too. 


“What are you thinkin’ about, angel?”


His blush intensifies but when Castiel tries to look away, Dean traps him between two strong hands. He could close his eyes but he can’t get himself to. It’s like Dean has him in a trance. 


“Come on. You know you want to tell me.”


“I-” Castiel licks his lips, really wishing he could look away but also turned insanely on by the way Dean’s smirking at him. By how humiliating it is. “I was thinking about being a brat earlier, sir.”


Dean’s pupils dilate. “Tell me, boy, what is it that you like about being my little brat?


Castiel finally manages to close his eyes. It makes things worse. Now, he has no idea what Dean looks like. He could be laughing at Castiel. He could be angry. He could be turned on. He could look like he wants to eat him alive - which is Castiel’s personal favorite Dean Winchester expression as of late. 


“I’m waiting,” Dean teases. 


“Just - just how it - it-” Castiel squirms, embarrassingly aware of how his hard cock is pressing against Dean’s stomach. “It’s exciting.”




“Yes, sir.”


“It’s exciting to piss me off? To push my buttons?” When Castiel shivers, Dean laughs. He keeps his eyes closed so he doesn’t have to see the way the man is probably looking at him. It’s either bad and it’ll make Castiel feel stupid, or it’s good and it’ll make Castiel even hornier than he already is. 


Dean grabs a fistful of Castiel’s hair and yanks his head to the side so he’s growling in his ear, “Does it turn you on that I could do anything to you when you’re in there? I could keep you there for hours. Days. Forever. My perfect little sex slave. I could whore you out. Fuck you with machines. I could kill you, little angel. Does that turn you on?”


“Oh god,” Castiel whimpers, shuddering. It does. It does turn him on. What the fuck does that mean? What kind of sick person does that make him?


“Yeah, I knew it did. My dirty little brat.” Dean chuckles in his ear and it’s dark and ominous and nearly makes Castiel come in his damn pants. “Aren’t you afraid I’ll do those things to you? Surely you can’t want that.”


“No, sir. Don’t want it. Just - just hot that you - that you could.” Castiel gulps in air, desperate to explain himself. Desperate to understand it himself. “I trust you. I - I push you ‘cause I can.”


“Mmmm. Good answer.” Dean claims his mouth, taking him by surprise. Castiel gasps before melting into it, parting his lips and letting Dean plunder him. When he’s apparently had enough, Dean pulls away. His voice is husky when he asks, “And the punishments? Are they just a consequence of the thrill, or do you like those too?”


Castiel squirms. “I don’t - I don’t know, sir.”


“I think I know.” Dean palms him through his pants before squeezing him hard. It makes Castiel’s eyes fly open in shock. He’s immediately met with the sight of Dean looking at him in his favorite way - like he’s a meal and Dean’s planning to devour him. “I think you love it and you hate it, and I think you fucking love that you hate it.”


“Is that bad sir?”


Dean must be able to hear the slight fear in Castiel’s voice because his features soften and his voice smooths out. “Not at all, sweetheart.” Then he winks. “But I’m still gonna give you shit for it.”


“I’ll give it right back.”


“Oh, trust me. I’m counting on it.” Dean squeezes him through his pants again, laughing when Castiel cries out. "Someone's all hard and desperate again, isn't he?"


Blushing, Castiel nods. He takes a chance and grinds on Dean's thigh. It feels good enough for him to throw his head back and groan. 


"Look at you. Jesus christ." Dean grabs his hips and pushes him down harder. "That feel good, baby?"


"Fuck yes."


Dean grabs Castiel's throat in a sudden, tight grip. His eyes narrow and his demeanor shifts. Right before his eyes, Castiel sees sir step out of the shadows. He's not sure if it's that or the slight cutting off of his oxygen, but Castiel goes dizzy. 


"You have until dinner call to come." 


"I - wha?" 


"Dinner call should be any minute now, boy. If you can make yourself come before, go ahead. If you can't, then you'll just have to wait." 


"Wait until when, sir?"


Sir's smile is wicked. "Until I say otherwise."


"Okay. Yes. Yes, sir." 


Castiel's hands fly down to the button of his jeans, fingers working quickly to pop it free and pull down the zipper. Two strong hands stop him from going any further as sir grabs his wrists in a vice like grip. Castiel whines in frustration. They're wasting time. Cant sir see he's wasting time? It's not fair!


"Did I say you could touch yourself, boy?"


It takes Castiel a moment to process. Even then, he’s confused. "You - you said I could make myself come, sir. If - if I hurry?" 


Sir's lips twist in evil amusement. "Yes. So make yourself come."


Castiel just stares, dumbfounded. When he realizes sir isn't going to explain further, he looks down at his crotch and shakes his head. "Sir?" 


"On my thigh, boy." 


Castiel's eyes go wide. "But-"


"You said it felt good."


"I - well - yes…" Castiel looks away, his face turning red. 


"Then grind yourself on me. Show sir how desperate you are."


Tears sting Castiel's eyes at the humiliation. Surely sir cant be asking him to… to hump his leg. That’s - that’s how dogs get off. 


"Sir," Castiel whines, feeling dirty and horny and a breath away from giving in. 


A hand snakes up to grab Castiel's hair, yanking so hard Castiels breath catches. "Come on my thigh or not at all. Your choice, sweetheart."


The rough treatment and the husky, threatening tone of sir’s voice mixes with the 'sweetheart' to form an intoxicating need Castiel can't overcome. Before he's registered what's happening, he's tilting his weight forward and sliding himself across sir’s thigh. The shame from before still lingers beneath his skin but every thrust of denim against denim makes it fade. He feels like he's unraveling. Like he’s unhinged. This man has tied him up, spanked him, paddled him, fucked his face, turned him inside out until he was calling himself a slut, and yet here Castiel is, falling apart for him on his fucking thigh. 


The idea is thrilling. It sends sparks straight down his spine and through his cock and he cries out, hips bucking frantically as his orgasm lingers just out of reach. 


It's much less thrilling when Benny knocks harshly on the wing’s door and yells through it, "Dinner, boss."


Sir’s hands immediately anchor Castiel in place, pushing down hard enough where he can’t even budge. Castiel sobs out of frustration, his skin tingling from the denial while his chest throbs with dominated bliss. He doesn't care that Benny probably heard him. He doesn't care that sir chuckles. He just deflates against sir’s chest and trembles, denial thick and murky in his veins. 


"We'll be right there!" Sir yells in an amused voice that should piss Castiel off. It doesn't, though. Sir sounds pleased. Castiel pleased him. That's better than getting to please himself. He’d make that trade any day. 


If he could please sir AND himself though… that’d be nice. 


"Color, sweetheart?" Sir whispers in his ear, fingers carding through Castiel's hair in steady, calming strokes. 


"Green, sir." 


"Can you go down there to eat with everyone?"


Castiel tucks his face in sir’s neck, blushing. He's rock hard in his pants and feeling floaty. He's not sure how that’d go over downstairs. Then again, he’s already feeling himself coming down from that precipice. 


"I think so, sir.” Castiel takes a breath. “Can we - can we wait a minute, though? Please, sir?”


"That's perfectly okay, sweetheart. You go wash up. Take your time. Then we’ll go down to eat.”


Unable to help himself, Castiel squirms in sir’s lap. "And then I can come?" 


Sirs laugh is fond but Castiel recognizes a hint of cruelty beneath it that doesn't bode well. "Oh no, no, no. You won't be doing that at all tonight. Best not to dwell on it. We don't want a grumpy boy at dinner, do we?"


It takes everything in Castiel not to say "If we didn't want a grumpy boy then maybe we should let him come" but he doesn’t. As much as he thinks he'll like being bratty and pushing sir’s buttons, in this case his next orgasm is on the line, and Castiel’s not even sure how he'll survive the night as it is. He’s not going to make matters worse. 


So, in an incredibly forced polite voice that he's pretty sure sir can see straight through, Castiel says, "Yes sir," instead and goes to wash up like a good boy.