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give until there's nothing left | dean winchester/reader

summary; you know of dean winchester. sort of. just a family friend of your dad's; nothing special. but when you dad goes on a "business trip" and decides you need a babysitter.. well. enter dean winchester. just a whole lot different (and darker) since the last time you saw him. 4.7k words.

content; heavy smut. vaginal/anal sex. DEAD DOVE. age difference (about fifteen years. lol). dad's best friend!dean. non-con elements (but no rape). demon!dean. cum-eating. manipulation. dacryphilia. innocence/corruption/degradation kink. use of pet names ("sweetheart"/"lamb"/"sir"). double penetration. biting/breeding/piss kink. asphyxiation. perv!dean. contraception sabotage. open ending.

any notes? demon!dean i love you. also for the anons who asked (to quote), "Could you do demon dean “babysitting” reader without reader knowing he’s a demon now and readers dad isn’t aware either so he asks an old friend because reader Isnt trusted enough even as an adult to stay alone and demon dean does all shorts of horriblr things 👀??" and "I NEED DBF!DEAN AS A SERIES BRUH THAT WAS SO SAD AND I NEED MORE PLEAEE PAPA".. and anyone else who likes my depravity; whilst this isn't part two to my dbf!dean, it's as nasty as i could possibly make it.. maybe even more-so. that being said, please read the content warnings. other than that, enjoy..

you know of dean. sort of.

some family friend of your dad from back in the day– the days where, when you ask about them, your dad goes all quiet and his eyes go lifeless; gives you just some utterance about “monsters,”– and maybe he attended a family barbecue or two, you’re not quite sure. you never paid attention to him, and he never paid attention to you. but, if you had to be specific, you haven’t seen him since you returned from college last year on a brief trip home.

and now, you’re here. with him. in your family home. because your dad decided you needed a babysitter– at the grand old age of twenty-two.

naturally, you’re pissed. whatever possessed your dad to do such a thing is beyond you; and you find it funny how dean just magically was in town when you showed up, and magically was available when your dad decided someone should look after you whilst he’s out for the weekend because livestock are suddenly turning up dead. and, most magically and importantly, dean’s a whole lot different than he was.

of course you avoid him. who wouldn’t? you’re not exactly desperate for one of the myriad of std’s that man probably carries. it’s not like you’ve ever thought about him or anything, it’s just.. well. if– and that’s a big if– you could end up sleeping with him, you wouldn’t be fighting to say “no”. and besides, from the fleeting, sexually charged glances that he’s snuck your way, to the way he seems to linger in the doorway to your room when he thinks you’re not around (spoiler; you are), there’s something off about dean.

now, you’re in your room, towel wrapped around you as you absent-mindedly scroll through your phone. you don’t know where dean is within the house, don’t care to know; all you want is to get through this weekend without him being around you. you’ve managed to make it to sunday, with now just a few hours to go. and then, once your dad returns, you’ll be free.

“good there, sweetheart?”

you freeze. turn around slowly from where you are on your bed to find him– dean– leaning against the doorframe like it’s where he’s supposed to be. like it’s nothing. arms crossed over his chest as his eyes look you over. no, revise that; his eyes ravage you. “was wonderin’ where you got off to. thought you decided to go be a, what is it? oh– a lamb to the slaughter.”

he’s poking fun at the recent streak of livestock deaths, but hidden under his words, there’s a layer of innuendo heavy enough to bury you. something in your stomach turns and twists, and you pull the towel tighter around yourself.

“not my thing,” is your short, bitter, reply. no niceties for him. nothing for the man who hasn’t stopped looking at you like you’re his next lay since he got here. and, if truth be told, you don’t think he needs anything, not when there’s something really different about him. he’s moving from the frame now, advancing into your room and over to you.

“huh, thought it would be,” he comments– to not you in particular though. just marches into your room, taking in the sight; the pink-and-white theme you’ve had since you were just a babe, a few posters here and there of artists and shows you favoured in your teen years (when you cut off all your hair, started hanging around with kids almost four years your senior; the typical “rebellious” phase), stuffies you can’t seem to part with because they always remind you of when your dad came home from “fishing trips”, coincidentally with dean and his brother. “nice room. pretty things for a pretty girl. cute.. toys.”

you wonder if dean helped pick any of them out, chose them for a specific reason, fantasised about you grinding on them, just like how you want to ride his face–

“i’m just trying to get dressed. um, so– could you go now, or–”

needless to say, you shouldn’t have asked.

hell, you shouldn’t have come home at all.

because the next thing that you know– or don’t know, really– is that dean’s pushing you back against the bed, straddling your naked body as the towel gets ripped from your hands. you try to push him away, maybe try and tell him he’s gotten the wrong impression, but he just grabs your wrists in a bone-crushing bind and holds them above your head, baring his teeth.

he’s quicker than you, stronger than you– in all ways, better than you– as he strips and ties his belt around your neck tightly. just like a leash. just like you might get away. and all the while, you’re still under him, muttering soft apologies for whatever it is that’s caused him to clearly lose his fucking mind.. and feeling your cunt getting wetter by the millisecond.

“hey– hey, now. don’t fight it.” he pulls on the belt, making your head jolt. the fat tip of his cock rubs up against your wetness. you bite back a moan. “c’mon, lamb, you know how much you want it. me. she’s so fuckin’ wet f’me, i can feel it. and we can’t jus’ leave her achin’ and hurtin’ like that, can we?”

you swallow uncomfortably. okay, sure– maybe you had been looking at him in a different way as of late, but it had been nothing as to the way he’s been looking at you. all hungry eyes and furrowed brows, as if he’s trying to work out all the ways he can make you cum, hand resting way too close for comfort near his dick. and you only know that last tid-bit from how he sits on the couch; spread legs, clear boner that comes on when you enter the room.

but back to what matters. maybe you did want dean– when you were younger, and thought he was pretty, and fun, and had all these silly stories about your dad and “gankin’” things. when you thought all other boys were gross, unlike dean, who in your eyes was the epitome of a man. however, now you’re older; you want someone who will hold your hand on a date, buy you flowers out of the blue because you deserve them. will give you anything and everything you want. what you want is everything your dad couldn’t do for your mom.

dean is anything but.

“i know you’ve been thinkin’ of me.” he says it with such authority that it almost scares you; mainly because of how right he is. “were you fuckin’ yourself to the thought of me whilst you were at that fancy school? pretendin’ all those other boys you let have this sweet pussy were me? god, look at you– ‘course you were. too shy and innocent to ask for the real thing, aren’t you?”

you give him a weak nod, not trusting your voice right now.

“fuckin’ thought so.” the grin on his face right now is feral, prideful; to the point where it’s almost disturbing. true, you know dean to be cocky, a “selfish and arrogant cunt,” if your dad’s words are anything to go off of, but not like this. and all the while, you can feel him push into you– inch by inch, little by little– his taunting distracting you enough from the ache and burn you feel from him stretching around your tight cunt. “been wonderin’ myself what it’d be like to do this. to do you. always thought you’d be a decent fuck, if any of your dad’s complainin’ ‘bout the noise you and the boys you’d bring home would make,” he practically snarls this out, jealously stabbing at the edges of each word, dripping from his mouth off of a vitrolic-laced tongue.

he’s barely got half of his fact cock inside, when you suddenly feel him push one hand under your side, cupping your ass. your breath catches as he gently tugs the belt around your neck. “gotta say, you’re fuckin’ tight, lamb. don’t know where how i’m gonna fill all of her, but we’ll find a way, won’t we? jus’ as long as you don’t throw a fit, then it’ll all be good.. got it?” to which, you don’t answer; because you’re too busy wincing when you feel his thumb press against your ass. “y’know, i could tongue your hole if i get bored of your pretty cunt,” he comments. you realised that he’s buried in you now, his hips pressing up against your ass. “put you in a cage and take you home with me. oh– you’d like that, wouldn’t you? be my little pup for whenever i wanna use you? can tell you do– she’s gettin’ wetter by the minute f’me.”

his hand around the end of the belt suddenly pulls, the knot playing by your neck tightening. you choke a little, a moan coming out all breathy and gasp-like. he’s going to kill you.

your face is inches away from his, your noses almost touching. there’s a heady, almost hypnotising, smell to him; whiskey, cologne that you’ve smelt on at least a dozen other boys (and yet, none of them smell the way dean does right now), and strangely, sulphur. and here you are, breathing it in like a volatile aphrodisiac, all polluted and rotten, letting it coagulate in your lungs and choke you.

he moves in closer, like he might kiss you. “jus’ gotta ask for it, sweetheart,” he tells you. “i’ll do whatever you want. want me to fill you so much you can’t fuckin’ walk, leave all your holes so sore and gapin’ that i might as well split you in half? shit– i can even put a fuckin’ baby in you, if you want. don’t think for a second that i haven’t been near your birth control. that was the first thing i sorted out for you when i got here. oh, i’ll fuckin’ do it all.”

there’s a pause, as you finally decide to trust your voice again.

“iwantyoutofuckme,” is what leaves your mouth.

dean scoffs. “what was that, sweetheart? didn’t catch any of that– not with the way you’ve got yourself wrapped around me right now.”

“i want,” you breathe, cutting yourself off when he pulls himself back a little. the inch or so lost from your cunt is enough to make you cry. “i want you to fuck me.”

“yeah? yeah?” as he mocks you, you can feel dean pulling out, until just the thick tip of his cock is left between your folds. “‘s that what you want? well.”

and with that, dean slams himself back into you.

it feels like life itself has been pulled and ripped violently from your body. your back arches off the bed, the belt constricting around your neck even tighter, as you cry out from the sheer force that he’s used to bury himself to the hilt again. he’s still got the belt wrapped around one hand, whilst the other holds onto your waist, keeping you in place as he fucks into you, over and over.

there’s something animalistic about it, you realise, as you mind is subdued to his heavy-hitting thrusting and sadistic behaviour. how easy it is for him to push himself, deeper, faster, harder, into you, never once giving thought to how you feel. with each passing second, as you become numb to such brutality, you feel so detached from the position you find yourself in; like your fantasised first time with dean winchester should’ve been much more romantic, intimate.

then again, isn’t this what you wanted? hadn’t you asked him to fuck you? all this– all of this is all you’ve ever wanted. just maybe not so violent.

but this is easily forgotten with his mouth all over you; your jawline, your throat, your collarbones, your tits. oh, especially your tits. tongue pressed firmly against your nipple, sucking and salivating like he’s a pavlov dog or something. sinking his teeth into your warm, spit-soaked flesh each time he bottoms out.

a mistaken reward for a misbehaved animal.

“takin’ me so well, aren’t you, lamb?” his words come out with more bite than they should, all pestilence bleeding in from the edges of them and seeping deep down into your mind. “bet i could make you further, yeah? don’t wanna tire her out of anythin’, not when you’ve got more than one hole..”

you whine when you feel his hand against the curve of your ass again, having left the belt around your neck and oxygen now returning to your cockdrunk brain. you can feel him press his thumb against your hole once more, and then, slipping in.

however, he’s fucking you so good that you can’t acknowledge his perversions. let alone think about another boy having you again.

your back arches off the bed at the feeling– the feeling of him practically shoving his finger into your ass, all the while still nothing himself deep in your gaping cunt. your obscene noises of a strange blend of pain and pleasure get lost in his own noises, all animalistic, albeit hypnotising, as well as the vulgar squelching from how wet you are. occasionally, you squirm a little, feel your face heat up at how pornographic your own hole sounds.

and with two of your holes now filled, you can’t help but to cum. it’s been building for a while; he’s more than good, filling you up and finding all the spots that no boy has ever done before. it’s hard to chose which pleasure to focus on– the cock that’s being rammed in an out of your wet cunt, or the fingers that keep you distracted, keep you tense. if anything, you’re more focused on the humiliation of having to lie still and take it. you’ve used toys on yourself before, but they were static– a general sense of pleasant fullness. the movement, the fullness and then the emptiness, makes you all so hyper-aware of where he’s touching you. where he’s fucking you. yes, you need, more than anything, to cum.

of course, dean picks up on this. “huh, d’you need– you need to cum? yeah? ‘s that what you wanna do?” he asks, grin all wolfish and prideful– just like before, but less disturbing this time and more possessive– as he manages to work another finger into your ass, still keeping that frantic, steady pace as he fucks you. “you gonna do it? do it f’me? cum around me like the cockdrunk whore you are, then let me fill you with my cum and knock you up? you’d fuckin’ love that, wouldn’t you? you greedy girl..”

“please– wanna– need to–“ your words are all broken syllables and whorish pleas, like you’re begging for your life. you take no notice of the degradation, the threats. “please, sir!”

and all this, just to be able to bathe in the sick, slightly gleeful joy of knowing that you’ve had your brains fucked out by dean winchester.

(then again, you’re probably in a long line of many).

“well, go on then,” dean huffs, one of his rough hands finding your clit and rubbing it harshly. just more stimulation, to add to the mountainous overstimulation you currently are objected to. feeling dread, feeling fear; feeling an undeniable warmth when he moves from your clit and pressed down firmly on your lower abdomen. feeling for himself. “feelin’ me up in there? see how nice i’m bein’ to you, lamb? now, you gotta make sure it all takes now, okay?” and you simply nod, hiccup and cry a little. too busy playing some twisted, adult game because your dad’s out and you can finally fulfil your biggest fantasy.

you’re crying even more when he bites down, hard, into your collarbone, sinking his teeth in deeper whilst you writhe under him. and somehow, this is how you cum; with dean’s teeth buried in your collarbone, and your cunt spasming around him.

when he cums, though, it’s hard and long. groans that reverberate against your sore and bleeding skin, felt right down to your shaken core. he’s deep when he does it, so you feel it all- and especially when he begins to slowly, a little weakly, push it further and further into you– your cunt making uncomfortable, wet noises, and slick beginning to seep out and soak the sheets beneath you– as if he’s trying to make sure it sticks. as if he’s trying to knock you up, give him an excuse to keep coming back to you.

and you think he mentioned something about your birth control. you can’t remember– not when you’re like this.

but it’s not the end.

“hands and knees,” dean pants into your neck, like a dog overheating in the sun, before pulling away and staring down at you with hardened, dark eyes. “now.”

you oblige, obviously, but it takes you a minute or so; you get to your hands and knees– barely– body trembling and weak from the first round. your hands are wet against the sheets, barely able to hold yourself up, your sweat mixing with slick and cum. you feel your breath falter– both from the slight sickness that is born and bred in your stomach at this moment (allowing yourself to do something so disturbingly nasty, allowing yourself to be ravaged in such a manner), but it’s quickly forgotten about when you feel him align yourself up with your hole.

it’s just that this time, it’s your ass.

naturally, you tense up. “dean, i can’t– no–” you’ve never taken anything up the ass. well, nothing, except for dean’s fingers. “seriously, please–”

he slips in so easy, your slick having dripped down to your hole and allowing him to just push the tip in without effort– without care. he hasn’t gone any further, one hand clamping down on your waist as you arch your back a little, whimper from the searing heat that blooms throughout your body. his fingers were one thing, but his cock is another; and even just him entering the tip is enough to make you want to cum again. you buck back against him, almost fucking yourself onto his cock. the hand on your waist tightens. “that’s not what you’re meant to call me now, is it, sweetheart? better behave now, or i’ll make this harder than it needs to be. got it?”

even in your cockdrunk state, you know what he means. “please.. sir.” it almost comes out in a whisper; all avoidant eyes and pouting lips. because it’s dirty. because it’s shameful. you’ve heard all about your girlfriends and their partners and/or hook-ups, calling them that, “daddy” and “sir”, and you, looking down on them for being so perverse.

“i want you there.”

oh, how the mighty fall.

“atta girl.”

in one swift movement, dean pushes himself entirely into your ass, a strained groan escaping him when you cry out from the stretch, and your arms finally give up. you fall forwards into the sheets, the taste of cum and sweat meeting your wet lips, and you have no time to react because he’s already pulling back and pushing into you– just as hard and mean and brutal as he did with your cunt.

he’s got the belt wrapped around his hand again, pulling every now and then– basically, any time that you don’t sing your praises for him with slurring moans and pathetic mewling– making you arch your back and press your ass up against his pelvis. if anything, it’s giving him a better chance at making you cum again, letting him find all these untouched, virginal, places inside your ass that’s no one’s ever had. until now.

his other hand has reached around to find your clit, all puffy and sore, rubbing it in teasing circles as he continues to rearrange your insides once more. his balls slapping up against your clit each time he goes balls-deep in your ass, the cum that slowly drips down your thighs making contact. everything is so distorted and so overwhelming and so wet, that you’re surprised you’re still conscious.

but you know that you are still conscious, because you catch his face in the mirror on the vanity, and everything stops. and you feel sick. because his eyes are black. not just blown-out pupils, or shadows from the lighting. pure black.

just like your dad has always said, “monsters”.

dean is one of them. maybe not always, but he is now. and now is where you are, where you get fucked to death (a very probable chance, it now seems) by something not-so human.

it’s like you’ve come back to life. suddenly, everything about this is too much; too real. you’re trying to push back against dean, get him off of you, but he doesn’t budge. just keeps fucking you– that is, until he lets out such an inhuman sound that it has to be demonic.

“where’re– where are you tryin’ to go?” dean snarls, letting go of the belt entirely– letting you breathe again, finally– and shoving your head into the sheets. his large hand is holding the back of your neck, all of his strength going into it as he bends over you, like he needs to keep you there. like he might will snap your neck. “ain’t goin’ anywhere, lamb. we’re not done playin’.”

you’ve already debased yourself for this man monster, so there’s no reason to voice your pitiful praises or slurring apologies (mainly because your face is smushed into the sheets), so you simply moan and whine, cry fat tears that’ll leave your skin dry. bucking your ass backwards to meet the entirety of his fat length is just one step further. feeling good is just one step further. climaxing is just one step further. you can hear him laugh, something dark and perilous; feel him tracing your walls, the tip kissing something in you, fucking rearranging your guts like he’s some mad surgeon, and your body so strung out and defeated, as you lay on your stomach, as he rams himself into you, again and again and again–

and with this new position you’re in, the pressure on your body is overwhelming. more specifically, the pressure on your bladder. you need to pee. badly. but you can’t do anything, can’t tell dean because anything out of your mouth at this point is some garbled version of “sir, please!” or some angelic praise that you don’t even hear yourself say. any time you get close, he pushes your face back into the sheets, tells you that “don’t need to hear the complaints, sweetheart; i’ll get you cleaned up soon enough,” and goes back to making a mess of your ass.

so it’s no surprise that the inevitable.. happens.

you feel yourself pee before you can properly register it. feel the warmth seep out of your gaping cunt and onto the sheets, mingling with the disgusting mess that’s already there. the tears– the ones that have been free-falling and numbing your face for a while now– seem to stop for a moment, as if you’re frozen out of horror. because you pissed yourself whilst having your ass fucked raw.

and somehow, this is what makes dean cum. his chest pressed firmly to your back, your sweat (and other bodily fluids) mingling and probably creating a new chemical reaction or something, as he pants heavily in your ear. “c’mon, sweetheart, i know you can do it,” he coos, hand rubbing lazily against your sore clit, occasionally wiping through your disgustingly wet folds. either he knows that you peed and will find some other way to bring it up and humiliate you with, or he’s also so fucked right now that he never even noticed. just thought you squirted or something. he’s still pumping away in your ass, the unforgettable feeling of cum being pushed against your tight walls, like it’s a compact space because there’s simply nowhere else for it to go. “you gotta cum f’me, lamb.. ain’t good to hold it in her f’too long..”

you do cum; although, it’s after he’s pumped two loads of cum into your ass, and some heavy fingering– which really borders on fisting– in your numb cunt.

your orgasm this time is more painful and exhausting than any you’ve ever had before. your muscles exhausted and cunt clenching around nothing, and for a second, you think you’ve died. every hole of yours feels broken, all gaped and full, as your breathing falters and stutters. there’s absolutely nothing on your mind, aside from masochistic euphoria. something breaks inside of you; all sinew and blood and bone that slowly drips from your body. along with your now-shattered dignity.

and when you look down– when you finally muster up enough energy to move– it really is blood. small spatters of the stuff on your pretty pink bedding. he’s fucked you so hard that you’re bleeding.

when he pulls away– as in, leaving you in a crumpled heap on your bed whilst he wipes himself down with one of your t-shirts nearby– dean clicks his tongue like you’ve done something wrong, shaking his head. you’re not sure what exactly, but when you notice how intently he stares at your lower half, you realise what’s wrong. he’s watching everything all pathetically leak out of you. “fuckin’ wasteful is what you are,” dean sighs, then presses meanly down on your lower abdomen to force more out. you writhe under his firm hand, feeling your face grow hot at the uncomfortable sensation of something oozing out of both of your holes like that. “told you to take it, lamb. can’t be wastin’ it like if you want to see me again.”

he says it like he will be coming back– no matter what.

and then, he’s between your legs, licking up the blood that’s gathered in your bush. along with.. everything else. from hole to hole, his tongue is relentless. he’s lapping up his own cum from your holes, fucking it back into you occasionally, but mostly holding it in his mouth.

he’s not eating you out exactly, but you can sense that as soon as you start whimpering– hell, even the slightest of movement– will do him in. and he’ll feast on your cunt like an animal starved. the prized apex predator finally getting the sweet prey that everyone else wants.

dean manages to pull himself away from your cunt, grabbing the end of the belt and yanking your head towards him. “open up,” he demands, and you do. you open your mouth, feeling dreaded anticipation line your stomach like a barrier. but it’ll do nothing against what he does.

he spits in your mouth.

then, he’s kissing you; all filthy and demanding, tongue shoving past your lips. you can taste yourself, bitter and thick, mixed with the sharpness of his spit. though, you gag and wretch a little at the taste on your tongue, that taste of cum and blood. it’s all of you. all of him. the both of you. but it’s not enough. not even close. you try to keep him there, on your lips, even when you pulls away– even going as far as to dig his blunt nails into your sore tit. and only then do you give him. truth be told, you’re nothing but greedy for him at this point; greedy for someone born and bred for violence and debauchery, but tenderised to know and care for you. well, enough to know your body.

you want dean winchester. every single part of him. even the rotten, monstrous parts.

you’re ready to slip into sleep after all of that– what, with your body already giving into that twilight where you’re safe and untouched.. even with blood and cum between your thighs, and your chest littered with bites and saliva– but then you feel something, someone, between your thighs, and you weakly raise your head.

“we’re not done, though, sweetheart. i gotta get my sweet fix.” dean’s back between your legs now, ignoring your pathetic mewls, his pupils blown as he licks his lips. he’s staring at your cunt, ready to devour it. “sex always makes me fuckin’ ravenous..”

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