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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 βbabysittingβ reader without reader knowing heβs a demon now and readers dad isnβt 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 π??" 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 dayβ the days where, when you ask about them, your dad goes all quiet and his eyes go lifeless; gives you just some utterance about βmonsters,ββ and maybe he attended a family barbecue or two, youβre not quite sure. you never paid attention to him, and he never paid attention to you. but, if you had to be specific, you havenβt seen him since you returned from college last year on a brief trip home.Β
and now, youβre here. with him. in your family home. because your dad decided you needed a babysitterβ at the grand old age of twenty-two.Β
naturally, youβre 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 heβs out for the weekend because livestock are suddenly turning up dead. and, most magically and importantly, deanβs a whole lot different than he was.
of course you avoid him. who wouldnβt? youβre not exactly desperate for one of the myriad of stdβs that man probably carries. itβs not like youβve ever thought about him or anything, itβs just.. well. ifβ and thatβs a big ifβ you could end up sleeping with him, you wouldnβt be fighting to say βnoβ. and besides, from the fleeting, sexually charged glances that heβs snuck your way, to the way he seems to linger in the doorway to your room when he thinks youβre not around (spoiler; you are), thereβs something off about dean.Β
now, youβre in your room, towel wrapped around you as you absent-mindedly scroll through your phone. you donβt know where dean is within the house, donβt care to know; all you want is to get through this weekend without him being around you. youβve managed to make it to sunday, with now just a few hours to go. and then, once your dad returns, youβll be free.
βgood there, sweetheart?β
you freeze. turn around slowly from where you are on your bed to find himβ deanβ leaning against the doorframe like itβs where heβs supposed to be. like itβs nothing. arms crossed over his chest as his eyes look you over. no, revise that; his eyes ravage you. βwas wonderinβ where you got off to. thought you decided to go be a, what is it? ohβ a lamb to the slaughter.β
heβs poking fun at the recent streak of livestock deaths, but hidden under his words, thereβs a layer of innuendo heavy enough to bury you. something in your stomach turns and twists, and you pull the towel tighter around yourself.Β
βnot my thing,β is your short, bitter, reply. no niceties for him. nothing for the man who hasnβt stopped looking at you like youβre his next lay since he got here. and, if truth be told, you donβt think he needs anything, not when thereβs something really different about him. heβs moving from the frame now, advancing into your room and over to you.Β
βhuh, thought it would be,β he commentsβ to not you in particular though. just marches into your room, taking in the sight; the pink-and-white theme youβve 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 βrebelliousβ phase), stuffies you canβt seem to part with because they always remind you of when your dad came home from βfishing tripsβ, coincidentally with dean and his brother. βnice room. pretty things for a pretty girl. cute.. toys.β
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 faceβ
βiβm just trying to get dressed. um, soβ could you go now, orββ
needless to say, you shouldnβt have asked.Β
hell, you shouldnβt have come home at all.
because the next thing that you knowβ or donβt know, reallyβ is that deanβs 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 heβs gotten the wrong impression, but he just grabs your wrists in a bone-crushing bind and holds them above your head, baring his teeth.Β
heβs quicker than you, stronger than youβ in all ways, better than youβ 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, youβre still under him, muttering soft apologies for whatever it is thatβs caused him to clearly lose his fucking mind.. and feeling your cunt getting wetter by the millisecond.Β
βheyβ hey, now. donβt fight it.β 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. βcβmon, lamb, you know how much you want it. me. sheβs so fuckinβ wet fβme, i can feel it. and we canβt jusβ leave her achinβ and hurtinβ like that, can we?β
you swallow uncomfortably. okay, sureβ maybe you had been looking at him in a different way as of late, but it had been nothing as to the way heβs been looking at you. all hungry eyes and furrowed brows, as if heβs 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.Β
but back to what matters. maybe you did want deanβ when you were younger, and thought he was pretty, and fun, and had all these silly stories about your dad and βgankinββ things. when you thought all other boys were gross, unlike dean, who in your eyes was the epitome of a man. however, now youβre 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 couldnβt do for your mom.Β
dean is anything but.Β
βi know youβve been thinkinβ of me.β he says it with such authority that it almost scares you; mainly because of how right he is. βwere you fuckinβ yourself to the thought of me whilst you were at that fancy school? pretendinβ all those other boys you let have this sweet pussy were me? god, look at youβ βcourse you were. too shy and innocent to ask for the real thing, arenβt you?β
you give him a weak nod, not trusting your voice right now.
βfuckinβ thought so.β the grin on his face right now is feral, prideful; to the point where itβs almost disturbing. true, you know dean to be cocky, a βselfish and arrogant cunt,β if your dadβs words are anything to go off of, but not like this. and all the while, you can feel him push into youβ inch by inch, little by littleβ his taunting distracting you enough from the ache and burn you feel from him stretching around your tight cunt. βbeen wonderinβ myself what itβd be like to do this. to do you. always thought youβd be a decent fuck, if any of your dadβs complaininβ βbout the noise you and the boys youβd bring home would make,β he practically snarls this out, jealously stabbing at the edges of each word, dripping from his mouth off of a vitrolic-laced tongue.Β
heβs 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. βgotta say, youβre fuckinβ tight, lamb. donβt know where how iβm gonna fill all of her, but weβll find a way, wonβt we? jusβ as long as you donβt throw a fit, then itβll all be good.. got it?β to which, you donβt answer; because youβre too busy wincing when you feel his thumb press against your ass. βyβknow, i could tongue your hole if i get bored of your pretty cunt,β he comments. you realised that heβs buried in you now, his hips pressing up against your ass. βput you in a cage and take you home with me. ohβ youβd like that, wouldnβt you? be my little pup for whenever i wanna use you? can tell you doβ sheβs gettinβ wetter by the minute fβme.βΒ
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. heβs going to kill you.Β
your face is inches away from his, your noses almost touching. thereβs a heady, almost hypnotising, smell to him; whiskey, cologne that youβve 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. βjusβ gotta ask for it, sweetheart,β he tells you. βiβll do whatever you want. want me to fill you so much you canβt fuckinβ walk, leave all your holes so sore and gapinβ that i might as well split you in half? shitβ i can even put a fuckinβ baby in you, if you want. donβt think for a second that i havenβt been near your birth control. that was the first thing i sorted out for you when i got here. oh, iβll fuckinβ do it all.β
thereβs a pause, as you finally decide to trust your voice again.
βiwantyoutofuckme,β is what leaves your mouth.
dean scoffs. βwhat was that, sweetheart? didnβt catch any of thatβ not with the way youβve got yourself wrapped around me right now.β
βi want,β 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. βi want you to fuck me.β
βyeah? yeah?β as he mocks you, you can feel dean pulling out, until just the thick tip of his cock is left between your folds. ββs that what you want? well.βΒ
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 heβs used to bury himself to the hilt again. heβs 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.Β
thereβs 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 shouldβve been much more romantic, intimate.Β
then again, isnβt this what you wanted? hadnβt you asked him to fuck you? all thisβ all of this is all youβve 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 heβs a pavlov dog or something. sinking his teeth into your warm, spit-soaked flesh each time he bottoms out.Β
a mistaken reward for a misbehaved animal.Β
βtakinβ me so well, arenβt you, lamb?β 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. βbet i could make you further, yeah? donβt wanna tire her out of anythinβ, not when youβve got more than one hole..β
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.Β
however, heβs fucking you so good that you canβt acknowledge his perversions. let alone think about another boy having you again.Β
your back arches off the bed at the feelingβ 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.Β
and with two of your holes now filled, you canβt help but to cum. itβs been building for a while; heβs more than good, filling you up and finding all the spots that no boy has ever done before. itβs hard to chose which pleasure to focus onβ the cock thatβs being rammed in an out of your wet cunt, or the fingers that keep you distracted, keep you tense. if anything, youβre more focused on the humiliation of having to lie still and take it. youβve used toys on yourself before, but they were staticβ a general sense of pleasant fullness. the movement, the fullness and then the emptiness, makes you all so hyper-aware of where heβs touching you. where heβs fucking you. yes, you need, more than anything, to cum.
of course, dean picks up on this. βhuh, dβyou needβ you need to cum? yeah? βs that what you wanna do?β he asks, grin all wolfish and pridefulβ just like before, but less disturbing this time and more possessiveβ as he manages to work another finger into your ass, still keeping that frantic, steady pace as he fucks you. βyou gonna do it? do it fβme? cum around me like the cockdrunk whore you are, then let me fill you with my cum and knock you up? youβd fuckinβ love that, wouldnβt you? you greedy girl..β
βpleaseβ wannaβ need toββ your words are all broken syllables and whorish pleas, like youβre begging for your life. you take no notice of the degradation, the threats. βplease, sir!β
and all this, just to be able to bathe in the sick, slightly gleeful joy of knowing that youβve had your brains fucked out by dean winchester.
(then again, youβre probably in a long line of many).Β
βwell, go on then,β 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. βfeelinβ me up in there? see how nice iβm beinβ to you, lamb? now, you gotta make sure it all takes now, okay?β and you simply nod, hiccup and cry a little. too busy playing some twisted, adult game because your dadβs out and you can finally fulfil your biggest fantasy.Β
youβre 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 deanβs teeth buried in your collarbone, and your cunt spasming around him.Β
when he cums, though, itβs hard and long. groans that reverberate against your sore and bleeding skin, felt right down to your shaken core. heβs 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 youβ your cunt making uncomfortable, wet noises, and slick beginning to seep out and soak the sheets beneath youβ as if heβs trying to make sure it sticks. as if heβs trying to knock you up, give him an excuse to keep coming back to you.Β
and you think he mentioned something about your birth control. you canβt rememberβ not when youβre like this.Β
but itβs not the end.Β
βhands and knees,β dean pants into your neck, like a dog overheating in the sun, before pulling away and staring down at you with hardened, dark eyes. βnow.β
you oblige, obviously, but it takes you a minute or so; you get to your hands and kneesβ barelyβ 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 falterβ 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 itβs quickly forgotten about when you feel him align yourself up with your hole.
itβs just that this time, itβs your ass.
naturally, you tense up. βdean, i canβtβ noββ youβve never taken anything up the ass. well, nothing, except for deanβs fingers. βseriously, pleaseββ
he slips in so easy, your slick having dripped down to your hole and allowing him to just push the tip in without effortβ without care. he hasnβt 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. βthatβs not what youβre meant to call me now, is it, sweetheart? better behave now, or iβll make this harder than it needs to be. got it?β
even in your cockdrunk state, you know what he means. βplease.. sir.β it almost comes out in a whisper; all avoidant eyes and pouting lips. because itβs dirty. because itβs shameful. youβve heard all about your girlfriends and their partners and/or hook-ups, calling them that, βdaddyβ and βsirβ, and you, looking down on them for being so perverse.Β
βi want you there.β
oh, how the mighty fall.
βatta girl.β
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 heβs already pulling back and pushing into youβ just as hard and mean and brutal as he did with your cunt.Β
heβs got the belt wrapped around his hand again, pulling every now and thenβ basically, any time that you donβt sing your praises for him with slurring moans and pathetic mewlingβ making you arch your back and press your ass up against his pelvis. if anything, itβs giving him a better chance at making you cum again, letting him find all these untouched, virginal, places inside your ass thatβs no oneβs ever had. until now.Β
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 youβre surprised youβre still conscious.Β
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.Β
just like your dad has always said, βmonstersβ.
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.Β
itβs like youβve come back to life. suddenly, everything about this is too much; too real. youβre trying to push back against dean, get him off of you, but he doesnβt budge. just keeps fucking youβ that is, until he lets out such an inhuman sound that it has to be demonic.Β
βwhereβreβ where are you tryinβ to go?β dean snarls, letting go of the belt entirelyβ letting you breathe again, finallyβ 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. βainβt goinβ anywhere, lamb. weβre not done playinβ.β
youβve already debased yourself for this man monster, so thereβs 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 thatβll 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 heβs some mad surgeon, and your body so strung out and defeated, as you lay on your stomach,Β as he rams himself into you, again and again and againβ
and with this new position youβre in, the pressure on your body is overwhelming. more specifically, the pressure on your bladder. you need to pee. badly. but you canβt do anything, canβt tell dean because anything out of your mouth at this point is some garbled version of βsir, please!β or some angelic praise that you donβt even hear yourself say. any time you get close, he pushes your face back into the sheets, tells you that βdonβt need to hear the complaints, sweetheart; iβll get you cleaned up soon enough,β and goes back to making a mess of your ass.Β
so itβs 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 thatβs already there. the tearsβ the ones that have been free-falling and numbing your face for a while nowβ seem to stop for a moment, as if youβre frozen out of horror. because you pissed yourself whilst having your ass fucked raw.Β
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. βcβmon, sweetheart, i know you can do it,β 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 heβs also so fucked right now that he never even noticed. just thought you squirted or something. heβs still pumping away in your ass, the unforgettable feeling of cum being pushed against your tight walls, like itβs a compact space because thereβs simply nowhere else for it to go. βyou gotta cum fβme, lamb.. ainβt good to hold it in her fβtoo long..β
you do cum; although, itβs after heβs pumped two loads of cum into your ass, and some heavy fingeringβ which really borders on fistingβ in your numb cunt.Β
your orgasm this time is more painful and exhausting than any youβve ever had before. your muscles exhausted and cunt clenching around nothing, and for a second, you think youβve died. every hole of yours feels broken, all gaped and full, as your breathing falters and stutters. thereβs 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.Β
and when you look downβ when you finally muster up enough energy to moveβ it really is blood. small spatters of the stuff on your pretty pink bedding. heβs fucked you so hard that youβre bleeding.Β
when he pulls awayβ as in, leaving you in a crumpled heap on your bed whilst he wipes himself down with one of your t-shirts nearbyβ dean clicks his tongue like youβve done something wrong, shaking his head. youβre not sure what exactly, but when you notice how intently he stares at your lower half, you realise whatβs wrong. heβs watching everything all pathetically leak out of you. βfuckinβ wasteful is what you are,β 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. βtold you to take it, lamb. canβt be wastinβ it like if you want to see me again.β
he says it like he will be coming backβ no matter what.
and then, heβs between your legs, licking up the blood thatβs gathered in your bush. along with.. everything else. from hole to hole, his tongue is relentless. heβs lapping up his own cum from your holes, fucking it back into you occasionally, but mostly holding it in his mouth.
heβs not eating you out exactly, but you can sense that as soon as you start whimperingβ hell, even the slightest of movementβ will do him in. and heβll 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. βopen up,β he demands, and you do. you open your mouth, feeling dreaded anticipation line your stomach like a barrier. but itβll do nothing against what he does.Β
he spits in your mouth.
then, heβs 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. itβs all of you. all of him. the both of you. but itβs not enough. not even close. you try to keep him there, on your lips, even when you pulls awayβ even going as far as to dig his blunt nails into your sore tit. and only then do you give him. truth be told, youβre 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.Β
you want dean winchester. every single part of him. even the rotten, monstrous parts.
youβre ready to slip into sleep after all of thatβ what, with your body already giving into that twilight where youβre safe and untouched.. even with blood and cum between your thighs, and your chest littered with bites and salivaβ but then you feel something, someone, between your thighs, and you weakly raise your head.
βweβre not done, though, sweetheart. i gotta get my sweet fix.β deanβs back between your legs now, ignoring your pathetic mewls, his pupils blown as he licks his lips. heβs staring at your cunt, ready to devour it. βsex always makes me fuckinβ ravenous..β
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goddddd and i just UGH but also UGHHHHH and aughhhh.... oughhhhhhhhh...... ACK !!! and.... aghhhhhhhh. ughhhhh ! UGH !!!!! and i can't even because AGHHHHHHH. UGHHH
Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
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