#bailey the caretaker

[chaossuta]

Bailey, Lio (my PC) & Eden's relationship chart 😳

#dol #degrees of lewdity #bailey the caretaker #eden the hunter #dol pc #dol bailey #dol eden #fanart #I love them a normal amount #I think about them 24/7 lmao send help

[junjunjunko]

That one event in a nutshell.

#dol #degrees of lewdity #bailey the caretaker #kylar the loner #shitpost hours #my art

[maqui-chan]

i have a thing called reading too fast and it makes me prone to misreading texts. for a second i really thought 'whitney i know you're a whore but goddamn not my caretaker 😭'

#degrees of lewdity #bailey the caretaker #whitney the bully #dol #or did i misread it #since the pc doesnt have a phone does the library have yaoi #or the local bookstore

[ilovedarius666]

#bailey the caretaker #degrees of lewdity #dol pc #my art #avery the businessperson #eden the hunter

[blackbrass]

maybe it's good that PC doesn't have a phone...

#self care is finding and redrawing old memes #degrees of lewdity #dol #dol pc #avery the businessperson #kylar the loner #whitney the bully #alex the farmhand #bailey the caretaker #sydney the faithful

[nopecho]

IS NO ONE GONNA TALK ABOUT THIS?????

I feel like my mind is exploding.

Whitney?? A good father?? Sir????

#you'll make me fall for him harder Vrel STOP IT #WOULD WE GET WHOLESOME FATHER-KID INTERACTIONS??? #SIR #YOU CAN'T DROP THIS BOMB SHELL ON ME #i desperately want the pregnancy content to be complete now #I HATE YOU SIR I'M TRYING TO GET OUT OF MY DOL HYPERFIXATION #Whitney #whitney the bully #dol #degrees of lewdity #degrees of lewdity Whitney #avery the businessperson #degrees of lewdity avery #eden the hunter #degrees of lewdity eden #bailey the caretaker #degrees of lewdity bailey #kylar the loner #degrees of lewdity kylar #sydney the faithful #degrees of lewdity sydney

[hakusins]

cw // cigarettes, scars

some of my top DoL characters!!

#dol #degrees of lewdity #can u guys tell im down bad for bailey yet #the one character that probably would never become a love interest #hahahaha ;w; #fan art #art #mine #my fan art #my art #whitney the bully #bailey the caretaker #eden the hunter #sydney the faithful #sydney the fallen #i have an exam on monday but i wanna play dol....and i wanna draw more uweh

[shokujin-art]

After seeing Vrel's answer about Bailey, willing to be bought for a date in exchange of a good amount of money, my delulu ass had to draw something about it—

#dol #degrees of lewdity #dol bailey #bailey the caretaker #dol pc #myart #One day Bailey #One day-

[bound-tosydney]

Bailey removing pc's child teeth..😬

#dol fanart #bailey the caretaker #degrees of lewdity #robin the orphan #dol pc

[swpdz000]

they're like bugs

#degrees of lewdity #dol #shrimp is drawing #oh my god #too bad we can only have 10 villagers on one island #sadge #okay here comes the tags #help #harper the doctor #sydney the faithful #sydney the fallen #bailey the caretaker #kylar the loner #robin the orphan #remy the farmer #eden the hunter #avery the businessperson #whitney the bully #briar the brothel owner #alex the farmhand #wren the smuggler

[ashersanity]

- @princesstokyomoon, @bobsquatley :)

Sometimes your caretaker can’t help themselves around you.

YANDERE! BAILEY

asher, we’ve been over this.

content warning! very non-con, mentions of violence, murder, somnophilia, voyeurism spanking, gunplay, choking, bailey is a warning on its own, expect the worst.

pc and bailey are gender neutral as always unless explicitly stated otherwise

“Your body was always mine. Just like your first time.”

yandere type : sadistic, possessive, controlling, overprotective

Yan!Bailey who needs you by their side at all times. Doesn’t matter why, the shitty caretaker is somehow coming up with some sort of sick excuse to have you in their office. Starts off with simple things, gruff voice demanding you to come in here already, needing you to dust the floor, it’s dirty, they claim. No speck of dust in sight, but who are you to deny Bailey? You know what happens when you do. Escalates to having you now on their lap, comfortably seated on their thighs. It’s an order of theirs, they say. Right. Of course it is. if they have a cock, then they’re slipping their length into your hole, cock warming them for the entire day.

Yan!Bailey who gets that weird sinking feeling in the pit of their stomach at the sight of you chatting away, lips curling up into that damn smile of yours, softly laughing along to Robin’s jokes. Y’know like some weird school boy/girl who immediately gets jealous, seeing their crush talking to someone else. Familiar steps drawing closer until they’re looming right over you and the poor orphan, dark look on their face, assigning you both different chores to have you two separated for the day. Brushes it off after like it was nothing, doesn’t know why they got so heated up about it either.

Yan!Bailey who can’t possibly help themselves around you, wooden floor creaking under the weight of their heavy footsteps, slipping into your room at night without that pesky orphan being by your side for once. Well, not like it’s going to stop them from doing what they have to do. Disheveled, unkempt, dark hair that’s usually slicked back, breath reeking of booze as they draw closer to your sleeping form, tall frame towering over yours. Look at you. Blissfully ignorant, unaware of what they’re doing right now, how their tongue slicked with sweat and vodka trails over your pristine, perfect lips, untouched by any of the filthy bastards in this town. You don’t even get to know that your first kiss didn’t go to sweet, old Robin.. Bailey’s own lips pressing against yours instead, tongue slipping past between your teeth.

Yan!Bailey who has several cameras installed in your room, lens catching each and every movements that you make, including the much more.. private ones. Needing to know what you’re up to, what you’re doing, who you bring into your room, entangled bodies softly landing against the cushioned mattress. Forbids you from sneaking anyone into the orphanage after that, claiming it’s for whatever bullshit reason they gave you. Stores in the tape right onto their computer, dim light of the screen reflected in their eyes, fixated on the way you blush and pant, hands slowly circling around your sex. Always comes in handy after a long, stressful day, needing to let off some steam, a low groan reverberating in the office.

Yan!Bailey whose punishments only grow increasingly worse and worse by the day, catching you slacking off during your chores or entering their office a few too many times results in you bent over their lap, begging for mercy. Palm raised, unrelenting in their blows, smacking your bum till it turns red, as red at the blush on your face, squeaking voice and hiccuped sobs echoing through the desolate room. The caretaker who doesn’t stop just as that, needing you to fully regret your actions and repent for them. Finger slipping inside your hole, alternating between thrusting their digit in all the while spanking you. Thrust in, thrust out, spank. Thrust in, thrust out, spank. Makes you messily cum all over yourself like the whore that you are, dangling legs trembling over their lap. Ignore the wet patch that formed on their trouser/skirt once you leave, giving Bailey a last fleeting look over your shoulder.

Yan!Bailey who doesn’t hesitate to put a bullet through the eyes of any motherfucker who even dares to lay their dirty hands on you. Who do they think they are? Messing with their own property? The one in charge of this whole town? In their own presence? Don’t question what happened to that one thug that got a little too bold with you, shamelessly groping at your behind as you walked on, blindfolded and gagged, uselessly drooling away. Thought that would slip past the caretaker’s eyes? Idiot, nothing does. Never with Bailey. And they’re also making it your own problem too, grasping at the back of your head, forcing you down onto your knees once more. Time to apologize in the way you know best, whore.

Yan!Bailey who’s a bit too much into this whole gunplay thing. Cold steel of their gun pressed against your temple, finger hovering over the trigger, barrel loaded in. Servicing them on your knees like the slut that you are, knowing they can blow your brains out at any moment. Fat, wet tears rolling down your cheeks, struggling to swallow them all. Hissing lowly under their breath, taking in the image of your tear-stained face, flushed cheeks and parted lips. So goddamn pretty. Raping you with their shotgun right up your ass, taking in delight in the sounds of your choked up sobs as they slide the length in and out of your poor, abused hole. Presses an uncharacteristically soft and gentle kiss to your forehead to soothe your nerves. How cute.

Yan!Bailey who doesn’t feel a shred of guilt or remorse at having you locked up in the orphanage, forever theirs to stay. Didn’t want to pay up your debt? Fine by them. Now you’re paying the caretaker in a different way, gloved hands firmly gripped around your throat and applying pressure, tugging at the wrists tied behind your back, chest pressed up against the hard surface of their desk. This is what you wanted, isn’t it? Makes sure Robin is there to see by pure “chance”, by accident, walking in on you in this vulnerable state, legs limps from the other’s treatment, utterly helpless. That’s good. Show that orphan who you really belong to now, huh?

Yan!Bailey who’ll track you down no matter where you go, wherever you run off to, to the ends of the earth, dammit. Thought you could get away from them? From Bailey themselves? The one that practically raised you? Fucking arrogant brat, they’re here to put you back into your place once they find you. Taking advantage of the power, ressources and numerous connections that they have in this town, it’s only a matter of time before they find you. Once they do, it’s over. Utterly. Fucking. Over. You’re here to stay with them, chained up to their side, collar tightly locked around your bruised up neck, lettering of their own name visible over your skin. Bailey fucking owns you. And they’ll make sure you have that simple notion ingrained into your stupid little brain. Make ya learn because that’s what you’re good at. Right, brat?

[END OF POST]

Masterlist

#the fact that this isn’t all that different from their canon selves says a lot.. #fucking tsundere #I know you care for pc in your own way #a very weird way at that #dol #degrees of lewdity #bailey the caretaker #so this is the first thing I post about them huh.. #yandere #yandere x you #yandere x reader #character x reader #asher writes #badly at that

[tetradon]

some bailey sketches insp by kylar's kidnapping event

#i hate him #i also want him to breastfeed me #bailey the caretaker #degrees of lewdity #my art

[mellowwillowy]

DOL ft. Bastards Edition!

Alright, I really wish I could include at least Avery (too old) or Landry... But idk, I think these 5 would work~~ wdyt?

Remy and Eden are inspired by multiple artists!

#dol #degrees of lewdity #Briar the Brothel Owner #Bailey the Caretaker #Remy the Farmer #Eden the Hunter #XL the Capricious #Art Shelves

[kylarsobsession]

My friend Mari (friend mentioned in this post) drew this because of our friend @takkton making a joke about Bailey having to wear a fursuit to get money when PC is at the wolf cave lol

#talking doll #degrees of lewdity #bailey the caretaker #dol pc #PC

[ilovedarius666]

倫恩好可愛...

#degrees of lewdity bailey #degrees of lewdity wren #degrees of lewdity leighton #degrees of lewdity Remy #degrees of lewdity #my art #dol pc #wren the smuggler #bailey the caretaker #remy the farmer #leighton the headmaster

[blackbrass]

PC: "sowwy"

Bailey: "damn okay"

#funny how it works even on Bailey #bailey the caretaker #degrees of lewdity #dol #dol pc