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Sleeping with the Enemy

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Castiel follows his instructions to the T, refusing to be even slightly bratty or disobedient. Not when his orgasm is on the line. Ever since he was edged - or, more accurately, and humiliatingly, edged himself - on Dean’s thigh, he’s been going a little crazy. He swears that he can feel the barely-contained electricity beneath his skin, just begging to be released. 


Once he’s squeaky clean, Castiel walks into the playroom with a towel wrapped around his waist and approaches the bed. The box is even more intimidating than before, but there’s an underlying excitement to it now. Adrenaline. He’s so close to 3 PM. And then Dean’s going to fuck him. 


Castiel is going to lose his virginity. 




To Dean. 


In less than 2 hours. 


Goosebumps crawl along Castiel’s skin as he picks up the box and carefully pulls at the ribbon. The silk unravels gracefully, falling off to each side of the box. All that’s left is the lid. 


Castiel’s breath hitches when he gets his first glimpse of what’s inside. The silky black cushion has three things nestled on it. 


The first is a collar. It’s black, leather, and about as thick as his finger. In the center of it is a tiny silver loop with a silver dog tag hanging from it. The tag is engraved with one word in elegant script: Brat


The second is a black silicone anal plug that Castiel swears he’s not going to be able to fit into his hole. Its neck is thin, but the end of it is round and… big. Castiel blushes as he realizes it’s probably not actually that big. Especially compared to Dean’s cock. 


The third is a small bottle of lube. 


Castiel groans as he realizes what Dean wants him to do. He wants Castiel to finger himself. To… stretch himself. To put this in himself. The collar isn’t so bad, it’s not like anyone but Dean will see it, but the plug? The thought of having to lie on his back and work himself open is awful and humiliating and his cock is so painfully hard just at the thought that he thinks he could burst. 


It’s at that moment that he realizes there’s a tiny slip of paper tied to the cap of the lube. He nearly laughs when he reads it. He swears, Dean knows him far too well. 


Don’t you dare touch your cock. It’s mine.


Castiel squeezes his eyes shut and groans in frustration. 


He’s doomed. 




At 3:01, Dean steps into the playroom. He smirks when he sees his boy kneeling ever so slightly in a different position than he was taught. The usual position would press the end of his plug against the balls of his feet, making it more intense for him. One of these days, Dean will tell him he’s not allowed to adjust. Today, though, he plans on putting the boy through enough as it is. Dean can let this one slide for now. 


“Look at that. Such a beautiful good boy for me.” The praise sends a shudder through Castiel’s body, the tiniest, most adorable sound escaping him as it happens. Smiling, Dean walks until the toes of his boots are a foot away from Castiel’s bare knees and then stops. He drops the stack of clothes he was holding in his hands before moving his attention to his belt. The hunger in Castiel's eyes as the boy watches Dean free his cock is intoxicating. It's even better knowing that hunger isn't going to be satisfied any time soon. Not in the way Castiel will want it to be. 


Dean takes his cock out of his jeans and fists it with one hand. He reaches out with his free hand and grabs Castiel’s hair, yanking the boy up onto his knees and slightly forward. Castiel moans, his lips parting immediately. 


"Does my boy want to suck sir's cock?" Dean teases.


Blushing, Castiel nods.


"Use your words, sweetheart."


"Yes, sir."


"Yes what?" 


Castiel ducks his head, but he can't hide the way his face gets even darker as his blush spreads all the way down his neck and to his chest. "I wanna suck your cock, sir."


"Be polite, boy. Look at me." Castiel obeys immediately. The blue of his eyes is barely visible with how blown his pupils are. "Now, look me in the eye and beg me for it." 


"Please, sir…" Castiel starts to look away, but corrects himself before Dean has to. It earns him a genuine smile from Dean. He swears the boy lights up like a fucking firework when he sees it. His reservations melt away after that. "Please sir, let me suck your cock."


"Since you asked so nicely…" Dean sighs as if this is a chore for him. "I suppose you can suck it, then."


"Thank you, sir."


"Mmm." Dean smirks. Then he tightens his hold on Castiel's hair and presses his cock against the boy's lips. When they part, he slowly drags the tip around to trace the outline of his mouth, precum acting like lip gloss to make the boy’s lips shiny. Then, without any warning, Dean shoves into Castiel’s mouth and towards his throat until he's gagging. He eases up for a few seconds before pushing forward again. Castiel whimpers and tries to pull away, but Dean doesn't let him. "Grip my thighs. Tap me with one hand for yellow. Two hands for red. Okay?"


Dean jerks Castiel’s head back until his cock is only pressing against his spit-slick lips. "Yes, sir," Castiel pants. Before he has the last syllable out, Dean is shoving back into his throat. 


Then, for the first time, Dean lets himself go and fucks Castiel’s face. The boy's eyes go impossibly wide, the little bit of blue that's visible brighter than usual. Fat tears start to roll down his face as he chokes and gags. Spit goes everywhere, running down his chin, flying out the sides of his mouth, and soaking Dean's cock. His lips start getting puffy and red as they spend time stretched around his girth. It's a beautiful fucking sight. Dean finds himself mesmerized by it, barely able to focus on how good it feels. 


Okay, that's a lie. He's an excellent multi-tasker. Dean can definitely appreciate how good it feels.


It feels fucking phenomenal. 


"You're doing so well, sweetheart," Dean gasps, speeding up the snap of his hips. "Such a good little cocksucker for me. Perfect. So fucking perfect."


Castiel moans, his eyes fluttering closed and his body relaxing under the praise. Dean grins. He doesn't think he'll ever get sick of witnessing that reaction.


It's only a minute or so later that Dean's already nearing his orgasm. He decides to test his boy a little further than planned by pulling him in close and holding his head in place, Dean's cock nestled in his panicking throat. He groans at the sensation of the muscles contracting around him as Castiel tries to figure out what to do.


"Shhh," Dean whispers, using his free hand to stroke the side of Castiel's hair that isn't being pulled at the moment. "Don't try to breathe. You can't. Just relax. Give into it. Sir will decide when you need air."


Castiel makes a sound of protest and tries to get his head away from Dean's crotch. The boy's hands stay firmly in place on his thigh though. Tightening his grip, Dean takes the hand that was being gentle a moment ago and uses it to cup the back of Castiel's head. The boy whimpers as Dean uses the new leverage to push deeper. He stares up at Dean with tear-filled eyes, his pretty dark eyelashes soaked and glistening. 


"You look fucking wrecked," Dean whispers. "You're gorgeous like this, Castiel." 


He pulls the boy's head back long enough for him to suck in air through his nose, then shoves him down again. More tears fall down his cheeks, but Castiel continues to stare up at Dean like he's the greatest thing in the fucking world.


Dean grins. 


"So good for me, sweetheart. Come now. Take another breath." Dean guides Castiel back, letting him fill his lungs again. Then Dean starts to fuck his face like before. Within seconds, he's feeling his balls tighten and his stomach twist. "Fuck. Gonna come. Swallow it all, understood? Show me how much of a cum slut you are." 


Castiel moans, nodding the best he can as his face gets fucked, and Dean loses it. He pushes in deep and spills down the boy's throat until he's emptied. 


Panting, Dean pulls back and wipes his cock clean against Castiel's cheek. The boy shudders, his eyes darting away in shame. His poor cock is bright red and standing at attention, begging to be noticed. Dean ignores it, tucking his satisfied cock into his jeans and fixing his belt. He steps away and taps the toe of his boot against the clothes he brought in earlier. “Get dressed. Don't wipe your face clean.” 


Castiel sways forward before his eyes flick up to Dean. “Sir?” he asks, his voice scratchy from his throat getting fucked. 


“Get dressed.” Dean gestures at the clothes. “Not a hard command, is it?”


“N-no, sir.” Castiel frowns, but he reaches for the clothes and pushes to his feet. When he sees that Dean included one of the lace panties that they bought at the store, his cheeks turn red again. He ducks his head and pulls the panties on with trembling hands. Then the tight dark wash jeans. Then the cream colored sweater. 


“Come on.” Dean says in a clipped voice, fighting a smile. “Your boots and coat will be at the front door. Let’s go.”


Castiel just stares at Dean, clearly convinced he’s misunderstanding. 


“Do I need to throw you over my shoulder and carry you? Because that would fall under misbehaving. Do you want to misbehave today, boy? Is that the choice you’re making?”


“No, sir!” Castiel all but shouts, shaking his head violently. “No. I wanna be good, sir.”


“Then let’s go.”


“I - but - “ Castiel’s right hand flutters up to his throat, his face once again filling with color. “Sir?”


Dean steps forward, reaching up and stroking his knuckles along the boy’s cheek. He wants to enjoy this, to fuck with his boy a bit, but he wants Castiel to enjoy it in his own way as well. That means the boy needs to relax. “Do you trust sir?”


“Yes,” Castiel whispers, leaning into the touch. “More than anything, sir.”


“Then trust that I would never put you in a situation that would make you unsafe or uncomfortable.” Dean winks. “Uncomfortable in a bad way, of course. Considering your cock is hard as a rock right now,” Dean pauses, running his hand along the ridge of Castiel’s cock. He chuckles when Castiel moans. “I think you like when you’re uncomfortable in a good way. You want to go out with this collar on, your cheek streaked with spit and cum, don’t you slut? You want everyone to see you. To know that you belong to me. That you’re nothing but a slutty little brat.”


Castiel stares down at the floor, saying nothing. His deep blush says enough. Dean laughs again. 


“And if they knew you had a plug in your needy little hole?” he whistles, shaking his head. “Yeah. Yeah, I think you’d like that, wouldn’t you? Should we tell everyone we see that you’re stuffed full for me? Hmmm?”


The look Castiel gives him is half-pleading for mercy and half-pleading for more. “W-whatever you, uh… you want sir.”


“Exactly. Now you get it. Whatever I want. You aren’t important.” Dean walks forward, backing Castiel up until the boy is pinned against the wall. He presses his thigh against Castiel’s denim-clad erection. His brat throws his head back and whines. “Now, we’re going to go do something very important today. You’ll need to be on your best behavior, and you’ll need to pay attention. Understood?" 


After gaping at Dean for a few seconds, Castiel carefully nods. "Yes, sir."


"Good. Let's go, then."




By the time they get to the shooting range, a separate building on Dean's property that Castiel had no idea existed, Castiel's heart is beating so hard he can barely hear the gunshots through the exterior walls. Dean presses a red button beside the door and a buzzer sounds. Within seconds, the building goes silent. Castiel sees why when they enter, Dean's hand on the small of his back to push him forward. Red lights are lit up above each aisle in the building, and everyone in there has put their guns down on the metal tables in front of them. 


As they walk by each hunter, Dean takes time to stop and say hello. Castiel knows why he's doing it. Even though Dean and everyone else never acknowledges him, he understands that he's being noticed. He's caught more than one hunter staring at him when Dean is distracted. It's humiliating. He had thought that his saving grace would be that the engraved tag is too subtle to read from far away, but Dean fixed that by making sure every single person in the building saw his collar up close. There's no way any of them didn't see the Brat written there, labeling Castiel. 


Add in that his lips feel puffy, his cheek is streaked with dry spit and cum, his ass is stuffed full of a plug that loves to tease his prostate, his throat feels raw, and his cock is so hard it’s nearly bringing tears to his eyes, and Castiel is having the worst-best day ever. 


Then Dean sets him in front of a metal table and offers him a gun. 


A gun.


Castiel doesn't take it, instead just staring at the thing like it might bite him. "I've never…"


"Yeah. I figured." Dean smiles at him, thankfully not upset at Castiel's hesitation. "You need to be able to protect yourself, just in case. I don't plan on you ever needing to, but I'd feel better knowing you could if you had to." 


Figuring that's fair, and thinking that he’d probably feel better too, Castiel nods and reaches for the gun. It’s much lighter than he expected. Dean explains why before he even asks. "There's no magazine in it yet, and the barrels empty. I'm going to show you how to hold it and handle it first, okay?"


"Yes, sir."


“Here, hold it like this with your hands here and here.” Dean arranges Castiel’s hands until Castiel is holding the gun how Dean wants him to be. “This is the safety, this is the trigger, this is the rack. You’re going to pull this back to rack it, which will get a bullet in the chamber. It’s a little hard, you need to put some effort in, but you’ll get used to it. After you have a bullet in the chamber, all you have to do is switch the safety off with your thumb just like this, and pull the trigger. This gun empties the magazine without needing to be racked each time, so once that first bullet is in the chamber, you can keep squeezing the trigger without worrying about doing it again. Make sense?”


“I… think so?”


Dean’s lips curve into a smile Castiel can’t quite interpret. “Want to see me do it?”


“Please, sir.”


Dean pulls on a pair of ear protection before placing another on Castiel’s ears. Castiel can’t help but smirk at the Winchester on it. It’s the brand of the gear, not Dean’s last name, but he knows that’s probably why Dean bought them. 


“Okay. So, this is the magazine.” Dean says loudly as he holds up a rectangular hunk of metal that has bullets stacked inside it. He places the magazine at the bottom of the gun and shoves it in hard until it clicks into place. With his left hand, he grabs the top of the gun and pulls it back - racking it, as Castiel remembers him saying. Dean looks at Castiel, making sure he’s watching, then arranges his hands exactly as he had with Castiel’s and flips the safety off with his thumb. 


After a moment's hesitation where he once again looks at Castiel to make sure he’s paying attention, Dean lifts his arms and aims. He pulls the trigger and begins to empty the magazine into the target that’s too far away for Castiel to see clearly. Then he places the gun on the metal table and takes his ear muffs off. Castiel does the same, watching as Dean presses a button that brings the target closer to them. Every bullet hit in the exact same spot, the center of the target’s forehead. It looks like just one big bullet since they all blend together. 


“Wow,” Castiel whispers. He shivers as he realizes the man who did that is the man who is going to fuck him tonight. The plug in his ass suddenly feels larger and heavier. His cock throbs. He feels his cheeks heat up and hopes Dean is too distracted to notice. 


“You ready to try?”


“Ummm… sure?”


“Just aim for his belly. Anywhere in this area,” Dean says, pointing his finger at the torso and moving it to gesture at the whole thing. “Anywhere in there will make me happy. Can you try for me, sweetheart?”


Castiel looks at the target with wide eyes. “I can try.”


“I think you’re forgetting what context you’re here in.” 




Dean grabs Castiel’s cheeks with one hand and squeezes, making him gasp. “You’re still my sub right now. We haven’t stopped our scene. You’re wearing my collar. Your ass is stuffed with my plug. Your cock is poking out of your jeans right now because of me. Show me some fucking respect, brat, and address me properly.”


“I’m sorry, sir!” Castiel whimpers, looking down at the ground. “I didn’t mean to misbehave, I promise. I swear, sir.”


“You’re okay. I forgive you, sweetheart. This once. Don’t forget again. Understood?”


A tingling sensation travels up Castiel’s spine as he nods. “Yes, sir.”


“Now, here’s another magazine. Load the gun and hit the target. You’ll look through this right here to aim. Line up the dot with where you want the bullet to go, keep your arms steady, and prepare yourself for the kick. Don’t let it toss you back.” 


He puts Castiel’s ear protection on again and hits the button to put the target back in place. Then he nods to show Castiel he can begin. 


The gun is so much heavier than he thought it would be now that it's full of bullets. He has to adjust his hands a few times before he feels confident enough to raise the gun and aim. His arms shake as he tries to steady himself. Sir steps up behind him and curls his hands around Castiel’s, adding stability and strength. Castiel breathes a sigh of relief. Feeling more confident now, he takes a final breath and squeezes the trigger. 


The weapon kicks back like sir had warned, but with sir standing behind him and holding the gun with him, it barely affects Castiel. He hears a loud, “Keep going,” through his ear muffs and starts again. He goes until the entire magazine is emptied. 


When they bring the target back, Castiel sags. Only two bullets even hit the paper, one in the groin, the other in the shoulder. He pouts and looks at sir. “Hey, you got his penis. I’ll say this - that’d bring me down.” 


Castiel laughs. 


Another magazine is given to him and they start over. 


After going through 4 more magazines, Castiel finally manages to get all of his bullets at least somewhere on the paper, and two shots in the torso like he was told. 


With the 5th magazine comes a new challenge. 


Just as Castiel is raising the gun to aim, no longer needing sir’s help, his plug begins vibrating. He falls forward, gasping in surprise. Sir gets a hand on the gun to make sure it stays pointed towards the target and wraps one arm around Castiel’s torso to force him to stand back up. The buzzing in his ass grows more intense as one of his ear muffs is lifted for sir to murmur in his ear, “You’ll sometimes be distracted when you have to defend yourself. Let’s practice.”


Castiel whimpers and shakes his head, knowing he can’t do it. “Too hard,” he pants, squirming as if he can escape the buzzing on his prostate. 


Sir bites his earlobe hard and growls, “Complain again and I’ll yank your pants down and smack your ass raw in front of every man here.”


Groaning, Castiel adjusts his grip on his gun and forces himself to do as told. 


Not a single bullet hits the paper. 


They try again. The plug is at the same level, but now sir is reaching around and groping him through the front of his pants, Castiel able to feel how the front of his panties are getting soaked in precum. 


Not a single bullet hits the paper.


“We won’t be leaving here until you can prove to me you can keep yourself safe, boy. Better get your shit together.”


Sir nudges his arms until they’re back in place to shoot. Then the plug in Castiel’s ass is turned up at least another notch, if not more. Sir continues rubbing his cock through his jeans as he trails sloppy kisses and nibbles along the side of Castiel’s throat. 


Castiel whines. It’s not fair. 


He accidentally says that. He says it’s not fair. He didn’t fucking mean to, but it falls from his mouth anyway. 


Sir’s hand tightens painfully against his cock, making him cry out. “Did you just complain?”


Castiel locks up. “No! No, sir-”


“Don’t lie. Lying will make it worse, boy.”


Panting in fear and arousal, Castiel squeezes his eyes shut and whispers, “I’m so sorry, sir.”


“Not yet.” Sir takes the gun from him and unloads it easily. Then he rips his ear protection off and clears the metal table in front of them so it’s empty. Castiel gasps when he's shoved onto it, his chest against the cool metal, his body bent over to present his ass. “You will be.”


“Sir-” One of the rags used to clean the guns is stuffed into Castiel’s mouth before he can say anything else. Something cool and hard is pressed against his palm next. 


“Drop the bullet to safeword,” sir orders in his ear, his tone evil and distant. 


Castiel whines, humiliated and anxious and turned on beyond belief. It gets worse when sir yanks his pants down in one quick jerk, exposing his barely-there lace panties and plugged ass to the rest of the facility. He knows logically that the men here can’t see him very well. There are little half-walls between each table. Still, a good portion of his ass dangling off of the edge can be seen, and he knows for sure that sir is in full view as he stands back. 


Castiel starts to bury his face in his hands but sir grabs his wrists and ties them with the leash he had used for his collar. 


“Oh, is my little brat embarrassed?” sir coos loudly. It earns a few laughs from the men nearby. Others far away are still shooting like nothing is happening. Maybe they know, maybe they don’t. Either way, they’re here to practice shooting, and that’s what they’re doing. The mere thought is humiliating. Castiel can feel how hot his face is, knowing it must be bright red. 


It gets worse when he hears the distinct sound of leather being pulled through belt loops. 


The first hit catches Castiel by surprise. It comes without warning, and it’s much harder than he expected. Castiel writhes pathetically against the table and cries into his gag. He’s hit again. And again. And again. Sir is moving fast, barely leaving him time to recover between hits. Castiel swears he can feel every pair of eyes on him now, even if he can’t see anything but the targets ahead of him and the walls on either side of his head. 


The plug speeds up until Castiel is gurgling against the cloth in his mouth. God, he needs to come. He needs to come so bad. 


As if sir knows - which he probably does because sir always knows - he grabs Castiel’s balls tight and yanks them back through his underwear. The pain is enough to pull him back from the edge. Hot tears fall down his cheeks as he sobs. 


It takes a second for Castiel to realize the spanking stopped. His wrists are gently freed. Then his mouth. The plug turns off. His pants are pulled up. He’s brought back to his feet, sir’s hands resting on his shoulders to make sure he doesn’t fall. The bullet is taken from his hand. 


“Such a good boy for me,” sir whispers as he turns Castiel to face him and begins brushing his thumbs over his cheeks to collect his tears. “My good sweet boy.”


Castiel just sniffles, feeling dazed and horny and torn between coming and sobbing. 


“You want to get fucked now? Want me to make you come?” When Castiel’s eyes go wide, sir chuckles and shakes his head. “Not here. Back in the playroom. Just us, sweetheart. You want that?”


“Yes, sir,” Castiel says with a frantic nodding of his head. 


He’s being led out of the facility. Eyes fall on him, he can feel them, but Castiel is far too out of it to care anymore. He thinks he hears sir tell someone to clean up their station. All that matters is that he’s hearing sir, and that he’s feeling sir’s hands guiding him. Castiel swears all he does is blink once and they’re in their personal wing. He blinks again and they’re in the playroom. 


Sir leads him to the bed, his movements gentle, the skin of his hands rough even as his touches are soft. 


Castiel watches in a daze as sir ties him with the same pretty red rope they used last time. It’s a similar pattern, though slightly less constricting and it’s not attached to the ring above to keep him in place. 


“I’m going to edge you,” sir announces in that raspy, low voice of his. Castiel whines. That’s the last thing he wants after all of this teasing. The very last thing. His reaction makes sir chuckle. “Oh, you don’t like that, do you sweetheart?”


“Please, sir,” he begs, wiggling his ass the best he can. The rope fights him as he moves. It’s a distraction, drawing Castiel’s mind to his body instead of the teasing that’s about to occur. The rope against his skin, pretty and red and tight, makes him feel safe and secure. Every time he moves - every time he even breathes - the rope constricts him and he’s reminded of Dean. He likes it an awful lot. 


“This is a cock and ball ring.” Dean sits in front of Castiel and shows him what looks to be a black infinity sign. “I’ll put this at the base of your cock and around your balls, and it will keep you from being able to come. Then I’m going to explore you, just like I promised. I’m going to lick you. Suck you. Maybe bite here or there. I’m going to drive you wild. Tease you until you can barely breathe. Until all you can do is beg helplessly for my cock. And then, I’m going to fuck you.”


Castiel just stares at him with wide blue eyes, his lips parted as he takes in shallow breaths.


“I’ll use my cock to push you to the edge. Over and over and over. That’s why it’s called edging. But you won’t tip over that edge, will you boy? Not until I give you permission. Isn’t that right?”


“Yes, sir. I’ll - I’ll be good. Won’t come.”


“Good. That’s good.” Dean begins to secure the cock and ball ring around him, making Castiel gasp from the slight contact of skin against skin. It feels phenomenal. He’s already so turned on, everything heightened and overwhelming, that just the slightest touch is enough to make his whole body quiver. “Because I’d be very disappointed if you come before I say you can.”


Disappointing Dean.


Wow. That’s… that’s the last damn thing Castiel wants to do. He wants to be good. So good for him. He wants to make him happy, not disappointed.


“I’ll be good,” Castiel promises. “I’ll be good, sir.”


“I know you will. Always so good.” Dean leans forward, locking their lips in a kiss that takes Castiel’s breath away. He’s already panting by the time Dean pulls back and stands up. “Say yellow if you’re going to come, but I want you to be close, boy. Very close. Let yourself come to that edge. Don’t run from it.”


Feeling anxious about whether or not he can actually do this, Castiel just bites his bottom lip and nods.


"Let the pleasure happen to you, but don’t let yourself be enslaved by it. Remember that you don’t belong to it—you belong to me. Your orgasm, your pleasure, belongs to me. I’m the one with all the power. Remember that.”


“Yes, sir.” 


A pillow is slipped in front of him, then Dean gently pushes him forward so his ass is up in the air. The pillow makes the position slightly more comfortable, but it’s still an awkward position to be in. He’s not sure if he’ll be able to stay in it for long.


Then Dean begins kissing along his bare skin, and Castiel forgets about everything other than sir




Dean’s a sadist. 


A total fucking sadist.


In his defense, he warned the boy. 


“Please!” Castiel sobs, his breaths water-logged as he writhes against the pillow beneath him. He’s been humping the thing like a dog in heat and still hasn’t managed to come with that cock and ball ring tight around him. It’s adorable and sexy as fuck and every time Dean chuckles, it makes his boy whine in humiliation. Dean’s always loved edging, but this is a whole new level. Edging Castiel specifically is like stepping one foot into fucking heaven - probably the only time that’ll happen, considering Dean’s lifestyle. “Please, sir!”


Ignoring the desperate little slut, Dean pulls out his two fingers from Castiel’s hole and replaces them with a dildo that’s two inches shorter than his cock and much slimmer. Castiel cants his hips and keens when it’s shoved into him, his hole barely resisting. 


Castiel tries his best to fuck himself back against the toy with the little amount of wiggle room available with his rope, letting loose tiny helpless gasps as he moves. Dean has to reach down and grip the base of his cock tight just to soothe the massive ache the sight brings on. That’s the worst part about edging Castiel, apparently. Other subs, Dean could edge them for hours and just be turned on by it. With Castiel, however, it feels like Dean’s fucking edging himself. He’s pretty damn sure he won’t make it much longer. Not that he thinks Castiel will complain about that. 


Whining pathetically, Castiel looks over his shoulder the best he can and begs, “Please fuck me, sir! Please, please, please!” 


“Fuck.” Dean takes a deep breath, feeling his control slipping through his fingers. He twists the fake cock in his boy’s hole and tries to assess. “You’re not ready, baby. You need more prep.”


“Noooo,” he half-begs, half-sobs, fat tears running down his cheeks as he keeps staring back at Dean. “Please, sir.”




“Please. Please. Please please please please fuck me. Need it. I need it. Need you so bad, sir. Please. God, sir, please! Need - I need-”


“Okay,” Dean says with a soft chuckle, brushing his fingertips along his boy’s red ass cheeks. “Shhh, shhh, shhh. Okay. You’re okay. Just breathe. Sir has you. Sir’s right here, sweetheart.”


Castiel’s head falls forward in clear relief, his breaths coming slightly steadier now. His whole body shakes and shivers and jerks in anticipation. 


Continuing to hush his sweet, gorgeous, sexy as fuck boy, Dean pulls his knife out and easily frees Castiel from his rope. He takes the time to rub each mark left behind, partly because it will help them not bruise as badly, and partly because Castiel still needs a bit more time to calm down in order for him to be able to fully enjoy this. 


When Dean gently guides Castiel onto his back, tossing the pillow to the floor, he finds the boy staring up at him in awe. He’s flushed and breathless, big blue eyes wide as they take in every inch of Dean’s naked body. It’s the first time Castiel has seen him without a trace of clothing on. It doesn’t take a genius to figure out that the boy likes what he sees. 


Dean pours lube into his palm and begins to slowly stroke his cock with it, wanting to be dripping wet to help his boy feel the best he can. Castiel starts to reach out for him now that his hands are free but stops himself. Dean quickly helps him out by taking his right hand and bringing it to rest on his chest, right over Dean’s racing heart. It’s such a small thing, but it makes Castiel gasp.


“I love you,” Dean whispers without meaning to. He can’t get himself to regret it, though. Not in the least. 


Castiel’s breath catches in his throat, the boy blinking quickly like he’s trying to see better. He takes a moment before slowly, cautiously, whispering back, “I love you, too.”


Something transforms inside of Dean’s chest. Something impossible to explain. Something profound. It’s like he finally steps into himself. Finally fits in his skin. 


“Really?” Dean asks, unable to help himself. He has to be sure. This is too good to be true. Way too fucking good to be true. Why would someone as beautiful and kind and innocent as Castiel love someone like him?


“Really.” Castiel’s fingers flex gently against Dean’s bare chest as if he can reach inside and touch his heart. “I love you.”


Dean sighs happily. “Say it again.”


“I love you, Dean Winchester.” Castiel grins. “I really fucking love you.”


Dean’s head hangs down and his eyes flutter closed. Both hands come to rest on Castiel’s slim hips, holding him in place. Then Dean pushes forward and begins to press into Castiel. When Dean looks up at Castiel again, his blue eyes are blazing. “Color?”


“Keep going,” Castiel begs before adding a breathy, “Green, sir.”


After pressing a soft kiss to Castiel’s lips, Dean shifts his body and continues pressing forward in small, smooth strokes that bring him deeper and deeper inside the boy each time. Dean sighs when he’s nearly all the way inside him, his hands trembling slightly where they hold Castiel. “You good, sweetheart?”


Castiel blinks up at him with tear-filled blue eyes, looking almost shocked. He opens and closes his mouth a few times like he can’t figure out what to say. Dean chuckles softly. The boy doesn’t look upset or in pain, just mesmerized. Dean can handle mesmerized. 


“Come back to me, sweetheart,” Dean whispers, running gentle hands along the boy’s soft skin. 


The touch seems to help bring Castiel back to the moment. His ass clenches, his eyes widening. With pink cheeks, and a dazed look in his eyes, he whispers, “Oh.”


Dean raises an eyebrow. “Oh?”


“Oh god,” the boy breathes, his hands moving so he can cling to Dean. “Oh god that’s good.”


Chuckling darkly, Dean grabs the boy’s wrists and presses them together. He uses some of the scrap of rope from the bed and ties his wrists before placing them above Castiel’s head on the mattress. “Keep those there, or you’ll be in trouble. After all of this work, you still won’t get to come.”


“Yes, sir.”


“Good boy.” Dean grabs one of Castiel’s ass cheeks and lifts, then pushes his weight forward so he’s hovering over him. The movement sends Dean in the final inch so he’s bottoming out. Dean hangs his head between his shoulders, trying to keep control of himself. Trying to remember this is a virgin beneath him. A nervous, innocent, beautiful virgin that he loves. That loves him. “Color sweetheart?”


"Mmmm." Castiel peeks up at him through his lashes, nibbling on his bottom lip. It doesn't go unnoticed by Dean that he's tentatively rolling his hips to get Dean’s cock to move inside him. When he catches Dean watching with a raised eyebrow and a cocky smirk, Castiel’s face goes red and he stills. "G-green, sir."


"Very green, aren't you?" Dean taunts.


"Sooooo green. So green, sir."


Dean growls as his final shreds of self-control dissolve. He digs his fingers into Castiel's slim hips and begins to fuck into him, doing his best to stay at a steady pace until the boy adjusts. He could watch the sight beneath him forever. His sexy boy getting all worked up, needy cock trying to spill but unable to, cheeks flushed, chest rising and falling erratically, blue eyes wide and locked onto him. 


"Fuck, you already take my cock so well, sweetheart." Dean grins down at his boy. "Your body already knows exactly who it belongs to, doesn't it?"


Castiel mumbles something unintelligible and nods. 


Gripping one of Castiel’s ankles, Dean presses the boy's slim leg back until he’s fucking straight into his prostate. Castiel shrieks and tries to pull away. When he realizes he's not going anywhere, he looks up at Dean with pleading eyes. "P-pleeeease!"


"Please what?" 


"Please, sir! Pleee - please - oh - oh - oh God- sir!"


Dean chuckles and fucks him harder. Faster. He wants to fucking ruin Castiel. He wants him sobbing and drooling and unaware of anything else in the world but Dean


"Feel good?" Dean asks as he watches Castiel’s pretty blue eyes roll into the back of his head. 


All the boy manages is a high-pitched, "Siiiiiiir!"


"What's wrong, baby boy?" Dean asks with a fake pout. "Whats the matter, hmmm?" 


"P-pleeeease sir, needa - nee - commmmmmme!"


"Oh is that the problem? Do you need to come sweetheart?"


Castiel looks up at him in relief, nodding quickly. "Y-yes. So bad. Ga - siiiirrrr."


"You wanna come for me, sweetheart?"


"Yeeees, sir!"


Dean reaches down, toying with the cock and balls ring without actually removing it. "You wanna come on sir's cock?"


"Yes! Yes, sir, pleeeaasee!" 




"I - but -" Castiel shakes his head like he's clearing it and blinks a few times. "Wha-?"


"I said no. You don't get to come. Not yet."


Castiel shudders violently. "Sir, noooooo!" 


"You feel so fucking good around my cock, sweetheart. Such a perfect little slut hole for me to use." Castiel sobs harder, barely able to breathe. Dean ignores him. "Does this feel better than my fingers, sweetheart? Than the toys? The plug? Is sir’s cock the best you’ve had?”


Castiel whines and thrashes. “Siiiiiirr!” 


“What do you say?” Dean growls, tightening his grip until he knows there will be bruises on his boy’s skin. Marks. Claims. “What do you say to sir for making you feel better than ever before?”


“Th - th-” Castiel pauses to release a wrecked sob. “Than’ y’. Thank y’. Th-” 


“That’s it. That’s my grateful little slut. You’re doin’ so well, sweetheart. You take my cock so well already. Like you were fucking made for it. Were you made for my cock, sweetheart?”


“Than’ you,” Castiel says again, probably unaware that the topic has shifted. “Thank - thanks’y - th - than’ - thank y’ - ooooo - than’ you - thank-”


“You wanna know why your hole takes my cock so good?” 




“Because your body already knows who it belongs to, Castiel. Your hole knows who it belongs to. It’s already mine, isn’t it? Why wouldn’t you take my cock when you’re mine, right sweetheart?”


“Yeeeesss, sssssir!” Castiel starts to raise his hands before dropping them back on the bed again. His face and chest are flushed. His eyes are continuously spilling tears. His poor cock is leaking like a fucking faucet despite the restraints on it. His whole body is trembling and shuddering. He starts whimpering, “Thank you,” again, over and over and fucking over again. 


He’s ruined. 


He’s wrecked. 


He’s Dean’s.


“Alright, sweetheart,” Dean coos, reaching a hand down to his sweet boy’s cock and ball ring. “Alright, you can come. Sir wants you to come. Can you do that for sir? When sir frees your little cock and balls, are you gonna come for sir? Are you gonna show him how good he’s making you feel?”


Castiel is nodding frantically, saying, “Yes, yes, yes, yes, sir. Yes, yes, yes, yes, yes, please, please, sir, needa’come, sir, god, sir, please, thank you, sir, sir, sir-”


Chuckling, Dean ignores the boy’s desperate pleas and focuses on gently sliding the latch on the toy so nothing is caught or hurt as the rings around his cock and balls open. The moment the toy falls, forgotten against Castiel’s hip, Castiel shoots his load. 


“Goooood boy,” Dean coos. “That’s a good boy.”


Mewling, eyes falling shut, body going lax, Castiel shoots a second time. It’s just one more strip of cum but it does wild things to Dean. He grips the boy tight and jerks into him twice more before holding as deep as he can and spilling into Castiel’s fluttering hole. His body shakes and trembles with the orgasm, his mind going foggy. He’s never experienced anything like it. For just a moment, he reaches a different space. Like fucking subspace but not. When he blinks back into focus, he finds Castiel lying still, his breathing calm and slow. His pretty long eyelashes flutter on his cheeks. 


“God, you’re beautiful,” Dean whispers, not sure if the boy is even awake. He doesn’t care. He can’t help it. “So perfect, sweetheart. I love you so fucking much.”


Dean continues murmuring praise and declarations of love as he draws the scene to a close. He gently unties Castiel’s wrists and rubs them for a minute. Then he pulls out and cleans himself up with a towel nearby before getting a warm, wet cloth to use on Castiel. 


Once Castiel is all clean, Dean tucks his bunny into his arms and scoops him up so they can go to their bedroom. The boy nuzzles his neck before murmuring, “W’ goin’, sir?”


“To bed, sweetheart.”


“Bed in’there.”


“I like our bed better.”


“Mmm.” He hugs his bunny tight and makes a little noise as if he’s just discovered it. “Bun.”


“Of course I brought your bunny. He’s your favorite.”


“You my fav’or.”


Dean smiles, nudging the bedroom door open with his foot and slipping inside. “Thank you, sweetheart. You’re my favorite too.”


“No juice,” the little shit says with a satisfied tone. “No food.”


“Ooooh, you think you got out of that, huh?”




“Good thing I made sure a little cooler of juice and some snacks were put in our room tonight, hey?”


Castiel slumps in his arms. Even though Dean can’t see him, he can tell he’s pouting. He’s pouting very hard. 


Chuckling, Dean lays his boy down on the mattress and props him up on the pillows. He kisses his forehead before grabbing a capri-sun and some chocolate out of the cooler. His sweet boy makes faces at him for the few minutes it takes for Dean to be satisfied, but then he’s definitely happy as Dean finally gives in and crawls into bed beside him. 


“Love you,” Castiel whispers the moment his arms and legs are wound around Dean. “We said that, right?”


“Right. We said that.” Dean kisses the crown of his head. “I love you, Cas. So fucking much.”


“Mmmm.” Castiel perks, looking around with a frown. 


Dean’s heart skips. “What’s wrong?”




“Oh.” Dean rolls them over and reaches to the floor where Castiel had accidentally dropped his bunny while being cruelly force-fed. He presses the stuffed animal between their naked bodies, grinning when Castiel does an adorable little wiggle of joy. “Better?”


“The best,” Castiel slurs, eyes closing as he sinks into Dean’s hold and the mattress. “Love you.”


“I love you too, sweetheart. Get some rest.”


“Love you.”


Dean smirks. “Love you too.”






“Hmmmm.” Castiel giggles under his breath before sighing happily. “Love you.”


Realizing this is going to be how they fall asleep today, Dean closes his eyes and obliges his boy. “Love you too.” 


They go three more rounds before Castiel slurs a final, “Love’y,” and falls fast asleep in his arms. 


Dean joins him just seconds later, one final thought flitting through his mind just before slipping under. He had no fucking idea it was humanly possible to be this happy.