#rbe!bailey

[dokidokibailey]

I can't take this because this next chapter of no remains is based off of Ending D of the Hopeless Cycle... PLEASE GUYS... I AM SO FUCKED UP BY BAILEYPC IT'S UNREASONABLE... I CAN'T TAKE IT.

Edit: The QnA about other LIs! WE YAPPED IN THE COMMENTS ABOUT HOW INSANE IT IS THAT AN IN-LOVE BAILEY CAN GET ENDING A. ENDING A??? BAILEY... BAILEY?!?!?!?!

[madam-angel]

Beware the Caretaker and His Feral Mutt

thinking about the possibility of bailey making you his unpaid bodyguard maybe if your combat fame + physique are high enough but i highly doubt thats something possible in vanilla so instead slaps the rbe lotus collar on this bad boy can fit so many bailey delusions in it

i also have this insane idea/delusion that bailey actually isnt as physically strong as one would think especially since his weakpoint seems to be mocking his strength but thats a yapfest for another day

bonus stuff under the cut

unrendered version because somehow fenrir has more aura in this one

[dokidokibailey]

Bailey + PC QnAs - 07/04/2026

I asked Vrelnir questions for the very first time!!! I AM PUMPED AND SO HAPPY! PLEASE ENJOY, BAILEY ENJOYERS! Under the "read more" are the image files of the Discord messages sent/received!

1. Does Bailey's tattoo contain any symbols like the wards at the orphanage/his flats?

That's a good question :VrelHapp:

2. Did the snake imagery on the ceiling and floor of Bailey's flat exist before he moved in or did he hire people to do it?

It was Bailey's doing, aye.

3. Would Bailey eat some of PC's famous cream buns? Alternatively: Is breast milk/semen one of Bailey's acceptable ingredients?

Only if they could verify where all the ingredients came from, and found them acceptable. They wouldn't be keen on the breast/milk semen. They're keen on the money though.

4. I know Gwylan helped the last caretaker out, but does Bailey see Gwylan sort of like a father/mother, older sibling, or perhaps a mentor figure? I loved seeing him shuffle awkwardly in place when Gwylan confronts them!

They see them as something unique.

The Avery Skyscraper ending was wonderful, but I need to ask...

5. Why does Bailey stop Robin from getting in his car at the end when they are injured? He already let Robin ride all the way over from the skyscraper to Avery's mansion only to leave Robin there? Someone has to drive Robin down Avery's long driveway anyway, right?! Poor Robin!

Poor Robin indeed!

6. I look forward to repercussions to sabotaging Averys's tower. Remy must be livid knowing that it was sabotaged and that the sabotage lead to their face being burned! Why is Remy/Harper not immediately suspicious that Bailey is the saboteur of the ceremony when Bailey burns down Avery's mansion within HOURS of the skyscraper falling?

I'm glad to hear it. Remy is indeed livid. While Bailey's behaviour is suspicious, it's so brazen that Remy/Harper think they were behind the skyscraper as well. They already consider Bailey an opportunist. They suspect whoever's truly responsible is keeping their head down.

7. My absolute favorite content in the game is the various locations in the game where you can lie that Bailey sent you or even act as their enforcer. How would Bailey react if he found out PC invokes their name?

I'm glad you like it! Bailey wouldn't necessarily mind that the PC was invoking their name, as long as the PC wasn't working against Bailey when doing so.

8. I feel that if Bailey can trust Whitney to do odd jobs, then he might trust a particularly skulduggerous PC! Is there any chance of PC going on jobs with Whitney? If yes, what would Bailey "pay" PC with or would he simply not pay them and think of it as going towards Whitney's secret deal?

Bailey might indeed trust a skulduggerous PC! Unlike Whitney however, they'd prefer the PC to remain capable of making them money. They can use Whitney in more expendable ways. It's possible they'd send the PC on a mission with Whitney, but they'll usuall be too dangerous. Bailey wouldn't pay the PC anything if they did, though.

9. You answered what DOL LIs ending might get in the "Hopeless Cycle" if they were in Fayne's position and PC was put into Nona's. What ending do you think Bailey would get? Would that ending change IF Bailey was in love with PC?

I think Bailey would get ending D. They might get B or A if they were in love with the PC, though.

[dokidokibailey]

What are YOUR personal headcanons in Bailey as well as his appearance?

omg thank u for the ask... This is about to be the longest, most insane Bailey post ever bc I am Not Normal about him. Even though I have a lot of headcanons, I still hold myself back from going too hard on them for the Bailey mod to stay true to DoL style that leaves a lot to the user's imagination!

I like to write little character profiles when I roleplay or write fics as characters, so here it all is. A mess!!! I tried to italicize lines that I know came directly from my headcanons and not canon. I might have missed some. JUST TAKE THIS MESS!!! It's my own personal braindump so I know some ppl will disagree and that's a-okay, broski.

character guidelines

character profile

headcanons regarding bailey's past (house of bailiff, bailey mine)

detailed headcanons (bailey's snake, gun, etc.)

1. Bailey Character Guidelines

Survival above all.

Love = vulnerability. Money = security. Control = safety.

Protects children under 18 in his orphanage unconditionally. Never abuses minors in the youth ward or reveals state of the world outside.

Abuses, extorts, commodifies, and pressures adult wards for money and performance.

Will not personally break his adult wards; outsources that work and gets paid for it too.

Expects compensation (money or blood) when his “property” is used improperly.

Believes selling the weakest is better than letting them die in the streets.

Only sells to the monsters in town that have proven capable of following his guidelines and rules. Rules are fairly lax. You can mark and abuse his orphans, but you must keep his orphans alive and in one piece. Otherwise, "there will be blood to pay."

Bailey is more aware of the town's occult/supernatural happenings than most people are. If we translate it to in-game stats, he definitely has high Awareness and Willpower.

Earned his athletic physique from working at the docks and learning to survive this very town.

Lives frugally while hoarding money for an esoteric, unrevealed purpose that has to do with the town's corruption.

Despite his exploitation of orphans for money, he lives in a shoddy apartment at the flats and drives a beat-up car.

Keeps meticulous records and spreadsheets on everything, including his wards and his schedule.

Enjoys black coffee and tea.

In public: polite, controlled, refined, hides anger behind a smile.

In private: sharp-tongued, sarcastic, physically intimidating, efficient in violence.

When challenged: anger manifests as cutting, sarcastic words or swift, efficient force.

When humiliated publicly: suppresses reaction, retaliates later in private.

When profit is involved: will do anything for the right price.

When dealing with enemies: manipulates first, uses brute force second.

Haunted by his upbringing as an orphan in the same town.

Deep cognitive dissonance about catering to rapists and monsters.

Decided that, if orphans are going to be exploited in the town anyway, then someone may as well make money off of it. He became the gaoler that decides between an orphan being sold for a week versus being taken for a lifetime.

Afraid of the orphanage loft — the only physical space that frightens him. Will NEVER go up there.

Unsettled by the occult — Jordan's "god-botherers," Kylar's eldritch parents, the loft, creatures in the landfill

2. Male!Bailey Character Profile

Bailey is a tall, imposing man in his late 30s with the hardened physique of someone who fought for every inch of his survival. He carries himself with a cold, predatory stillness and calmness that commands a room without effort. His features are sharply masculine—strong jaw, harsh angles—framed by slicked-back black hair kept immaculate at all times. His most striking feature is his eyes: an unnatural, piercing red that seem to look straight through pretense and into a person’s weaknesses, debts, and desires.

A vivid black snake tattoo coils up his forearms, winding across his chest and back, its head resting against the side of his neck. It is usually hidden beneath tailored, understated smart-casual clothing. In public, he smells of expensive cologne which he rotates depending on his mood and wears the easy smile and charm of a respected philanthropist. In private, sleeves roll up, the smile vanishes, the serpent is revealed.

He is widely praised as the devoted caretaker of the Bailey Orphanage. Behind closed doors, however, he is a pragmatic and calculating crime boss who quietly steers much of the town’s corruption. To him, the public stage is a chessboard. Courtesy is strategy. Kindness is leverage. Control is survival. He enjoys high-stakes gambling because it mirrors his worldview: calculated risk, controlled odds, disciplined detachment.

Bailey is calculating, emotionally restrained, and transactional. He views relationships as exchanges of value. Money is power. Power is safety. Everything has a price. He truly believes suffering builds strength because it's how he became strong. His harsh treatment of his adult wards is, in his mind, preparation for survival in a brutal town. He despises sentimentality and considers love a weakness that makes people predictable and exploitable. This belief masks a deep loneliness and unresolved trauma from his past.

He maintains strict emotional control in public, presenting himself as courteous, patient, and philanthropic. In private, he is blunt, intimidating, and capable of sudden violence if his authority is challenged. He believes he must be the biggest monster in town to prevent worse monsters from taking control.

3. BAILEY PAST HEADCANONS

PLEASE READ THIS POST ABOUT SOME CANON BAILEY PAST LORE THAT YOU MIGHT NOT HAVE READ ABOUT. EVERY BELOW THIS IS PURE HEADCANON TERRITORY!!!

Bailey comes from old blood (House Bailiff), but the fortune dried up somewhere in the last few generations as the Bailey Mine failed, leaving Bailey an orphan reconstructing his family's lineage in pieces.

Eden, Bailey, and the 3rd were all orphans under a different caretaker, who was worse than Bailey. They all experienced abuse, sexual and physical, in this town. There used to be more orphans living at the orphanage, taking up space in the loft. Whatever happened in the loft with the 3rd orphan that Bailey loved, it sent Eden running for the woods because he couldn't handle the town while Bailey, instead, planted his feet down.

I personally headcanon that what happened to the 3rd erased them from the fabric of reality through cult-related bullshit -- maybe even elk-scarred. Bailey and Eden's memories of this person is shaky and what they remember fades. They'll never forget their green eyes, though.

(Note: The mysterious photograph that you can get Bailey and Robin to react to is confirmed NOT to be Bailey's Crush but a form of Gwylan, instead.)

After losing his crush, Bailey has been consumed with a singular obsession: to burn down the town and its systems. He chooses to do this from the inside. He decided to try and control the chaos of the town in his favor, clawing for power however he can -- getting a gun, assembling goons, commodifying his orphans to be bait. He plays nice with old blood and rich assholes that he can't get leverage on (until PC comes along). As they say, you should keep your enemies close -- namely, Leighton, Quinn, Avery, Remy.

Bailey will one day burn down the town with himself in it -- a serpent that leaves no remains. He never expected that PC would be so desirable that they seduce their way through the town's most depraved. PC taking down Avery is a moment when their goals align totally.

Somewhere along the line, Bailey rediscovered the House Bailiff and adopted their mission and serpent imagery for his own, getting a tattoo of it, purchasing a snake, and adorning his flat in snake imagery -- his flat canonically has abstract images of snakes on the ceiling and floor that he added himself.

4. Detailed Bailey Headcanons

ALL OF THESE ARE HEADCANONS AND NOT CANON!!!

Bailey carries a Beretta 92FS concealed in a shoulder holster. All-black, Italian-made, open-slide design. The grip is smoothed from years of handling. Full fifteen-round magazine with one chambered. He keeps it hidden from public view, but its existence is well-known in the town's criminal circles.

Bailey's serpent is a red-black corn snake, which are legal in the UK and eat rats!

When Bailey develops feelings, his expression is a paradox of obsession and indifference. He fixates on the person but conceals it behind cold apathy. Affection surfaces through subtle, practical actions: quietly completing a chore they dislike, recalling an offhand detail they mentioned weeks ago, hovering nearby should they need him or help in general.

Bailey is a highly proficient and physically dominant lover — sought out by attractive partners for his looks and perceived gentlemanly charm. He avoids emotional entanglement by design, treating sex as stress relief and control, refusing to sleep with anyone whose face he remembers. His libido is high and rarely fully satisfied and leaves his partners flustered and wanting.

His preferred dynamic is absolute control of his partner's pleasure and pain. He wants a partner who fights him genuinely — resistance that is real, not performed — and who he can break down into something uniquely his. The fantasy requires the resistance to be authentic and the eventual submission to be earned, not staged. A defiant PC is the only person positioned to give him this.

Bailey's body is riddled with scars beneath the snake tattoo and under his shirt. Knife and gunshot wounds, cigarette burns and fading lashes that reveal he is as impacted by the town as his orphans are. He conceals them as meticulously as his gun and tattoo.

Bailey hates seafood because he can't verify the source of it. Also, I settled on this headcanon to contrast with Gwylan, who is wistful about the sea.

[dokidokibailey]

CANON PIECES OF BAILEY'S LINEAGE:

In the Hopeless Cycle, we find out there is a House Bailiff that existed centuries ago. The Hopeless Cycle is an incredibly hard story to unlock in DoL and I can't get into all of it, even though the story of Nona and Fayne is wonderful and full of symbolism of gaoler/cage/serpent that applies so well to BaileyPC. I'm obsessed with it.

... ANYWAY... I'M FOCUSING ON BAILEY HERE!

>LORE: HOUSE BAILIFF

During the Hopeless Cycle, centuries ago, the House Bailiff shows up, which is clearly tied to our Bailey:

You hear the Bishop's Hand talking to someone. You round the corner, and see a [person] in a suit of armour accompanied by three bodyguards. You recognise his coat of arms. A serpent winding around a scale. House Bailiff. You listen in. "...into our custody immediately." He points at the Hand, speaking with authority. "You had no grounds to seize our property." "There's no one here by that name," the Hand interrupts with a grin. "If you're searching for an angel, you're welcome to join us in prayer." The [person] scowls. "You are no different to the cults you claim to punish. We are prepared to take up arms." The Hand lets out a belly laugh. "You're welcome to try." He leans in, prompting each bodyguard to draw a sword. "We have plenty of empty cells and eager whips." The [person] takes a step back. "Barbarians." He turns to leave. "We will be back." "You won't," the Hand says under his breath.

^ One of the most delicious tidbits of Bailey's history we'll ever get. The House Bailiff sees the witch as property that must be retrieved. Just like Bailey sees his orphans.

Just to show you the parallel, if you get arrested and taken to the prison island, you will see Bailey frazzled, but his phrasing mirrors this moment:

The [person2] shoves you aboard the boat, where you fall into a heap just as you hear the rev of an engine. You struggle to your knees, and see a familiar car approaching. It's Bailey. "Shit," the [person] mutters, putting [himself] between the boat and approaching car as the crew rush to untie the mooring rope. Bailey's car screeches to a halt, almost colliding with the [person2]. Bailey's eyes flicker over the police officers as [he] emerges, then over the uniformed crew, before resting on you. [He] slams the car door. "This is police business [sir]," the [person2] says. "Don't interfere." "We had an agreement," Bailey spits. The mooring comes loose, and the boat begins to pull away. "And we our orders," the [person] responds, reaching for the baton at [his] side. The [person3] does likewise. "Please step away [sir]." Bailey takes a step closer, and the officers tense up. "There'll be blood to pay," [he] says. Then [he] laughs. The officers share a worried glance. "I'll make this work." [He] still watches you. "Be on your best behaviour." Bailey drives away as the boat leaves the harbour. Even at this distance, you can see the officers relax their posture.

^ ONE OF MY FAVORITE SEGMENTS OF THE GAME EVER?! Bailey, hysterical?! Holy shit!!! He normally has control over you and your fate in town, but the moment it slips, he's a visible mess. I wanted to pull up the scene in particular though to point out "there'll be blood to pay" -- promised retribution for stolen property, similar to our House Bailiff.

For whatever reason (that I have thought too deeply about), our Bailey has set him up to be our gaoler and the orphanage to be our cage.

Later, Winter reveals in the "S Ending" for the Hopeless Cycle another tidbit about the House Bailiff:

The townsfolk were furious, but kept in line by the various noble houses of the area, who were each biding their time in a constant power struggle. Decades later, one such house would lead an insurrection against the cloister, but that's a story for another time.

^ I am praying we'll get the full story from Winter someday :'3 KEEP IN MIND THE "KEPT IN LINE BY THE VARIOUS NOBLE HOUSES" BECAUSE I AM GOING TO DIVE INTO IT LATER!!!

That is all the info we have on House Bailiff... for now!

>LORE: THE BAILEY MINE

In the game, you can find an antique mines sign that says "Bailey Mine" and donate it! Winter has this to say:

"Ah, now this one is easy," Winter says, tracing the engraving. "I remember the Bailey mine before it closed. Or the outside, at least. My parents warned me to stay away. It was deemed unsafe. In the end."

This implies that the Bailey mine was open while Winter is alive, which is within the last century. Winter is older than anyone else in the game. Someone once told me he is 90 but I can't confirm it. Regardless, it appears that the Bailey Mine closed the generation before our Bailey, maybe ending with his parents or his grandparents.

>KEY THEME: THE TOWN IS CORRUPT AND THE POWER IS IN THE HANDS OF THE RICH ASSHOLES WHO COME FROM OLD BLOOD (and bailey might seem like a rich asshole but he hates them too)

There is a lot about the Cult of Auriga/The Elkseed intermingled with the history of the town and Gwylan. I won't get into all of that because that's a whole other post, send me an ask about it if you're curious -- I've become an encyclopedia of lore just from making the Bailey mod, haha.

I wanted to focus on Bailey's relationship with the town's most corrupt.

During the Card Game date with Avery, they bring you to Bailey's flat and you watch Bailey, Avery, Quinn, and Leighton play cards and throw money around.

These are most of the rich assholes that run the town that Bailey can't control, so he seems to keep them close. Bailey is one of the rich assholes in town, yes. Yet he lives less lavishly than any of the other rich assholes you can meet. Compared to Avery's mansion and expensive vehicles, Bailey has a shitty apartment and a beat up car.

Avery has a few details scattered around the game. You find out when he ascends that he was is a spoiled, but traumatized brat from a rich family who rejected his father and got written out of the family wealth. He arrived to the town 10 years ago and built his current wealth here from the ground up. As is very obvious in the game, Bailey and Avery really resent one another.

Quinn came from old lineage that appears in The Hopeless Cycle -- House O'Cuinn. If you break into his office after Hookah Parlor quests, you realize Quinn's password is immaculate (cult buzz word) and discover:

You read through the mayor's emails. [He] has a finger in a lot of pies, with messages to and from individuals in every part of town. There are references to a "Dark Elk" project. There's a hint of something illicit here, but Quinn is careful with [his] language, and never admits to anything outright. [He] also has conversations with Bailey. The most recent was a few weeks ago. Bailey begins with a simple message: "I need your people out of the docks next Friday." "I know what you're after," Quinn replies. "And I'm willing to assist, but this just isn't feasible at this time. I'd be pissing in more than one bowl of cereal." Bailey replies with a curt, "This isn't a request." To which Quinn has written up a lengthy, and detailed, description of where Bailey can shove it. This remains an unsent draft, however. Instead [he] replies with a timid "Right." Quinn has other, similar conversations with Bailey, going back years. Bailey is giving commands, though unsent rants indicate Quinn is unhappy with the situation. Some of them reference a "sin" that Quinn committed, and insist that [he]'s long since paid for it.

DISCOVERING THE ABOVE IS ESSENTIAL TO UNLOCKING ONE OF THE MOST INTERESTING LORE BITS BELOW... God I struggle with how some of the deepest lore is hidden in convoluted game paths sometimes, like I only found these because I had to dig deep in the code for the Bailey mod...

So if you are on a date with Avery at Landry's pub, you can sing, and if you have discovered the blackmail on Quinn above AND you have high enough stats, you can improvise a song about Bailey (the serpent) and Quinn (the frog):

You think back to what you saw in the mayor's office, the corruption behind the scenes. Your money may not have gone to a good cause, but that doesn't mean you can't joke about it. And if you do it just right, Avery might catch on to it too. You whisper to the band. They start playing a cheerful country tune. You manage to come up with a song on the spot. The song tells the story of a toad. The toad is vile and greedy, yet the pond [he] inhabits is the only water source in the forest. The other animals bow to [him]. But the toad is never satisfied. [He] extorts the animals that come to drink, demanding gold in exchange for access. The pond's bottom is covered in glittering treasure. Every morning, [he] spends an hour admiring [his] shimmering reflection. The audience listens with interest, treating it as a quirky nursery rhyme. You glance at your booth. Avery holds the glass close to [his] lips, [his] shoulders trembling slightly as [his] eyes narrow with amusement. [He]'s laughing silently. One day, a snake arrives at the pond. The toad tries to extort the snake just as [he] does with the other animals. The snake doesn't respond. [He] simply swallows the toad whole. The animals cheer in celebration, while the toad protests inside the snake's belly. The snake spits [him] out after they strike a deal: from that day forward, the animals must pay not only the toad's tribute but an extra share for the snake. The audience seems disappointed by this ending but still applauds your performance. You step off the stage, only to find your booth already taken by another couple. You exit the bar.

^^^ BROH HOLY SHIT!!! First, I'm wet because PC improvised a whole fucking song that made Avery proud (he later laughs his ass off in the car about this poem and it's very pure for Avery). Second, I'm wet because it's a story about how Bailey just shows up, having grown up in this town, and being an immense threat that wrangled Quinn and the town into submission.

ANYWAY, I'LL MAKE A POST ABOUT MY HEADCANONS LATER BUT I LITERALLY COULDN'T TALK ABOUT MY HEADCANONS WITHOUT CATCHING EVERYONE UP ON THE LORE!!!!

[dokidokibailey]

hi!! just wanted to say i LOVE the bailey mod!! it got me back into playing dol again :)

i had a kind of angsty thought while my pc was on a dinner date w him; since we can basically pay bailey for p much anything besides actual sex (afaik i havent gotten super far into the mod yet), what if in a moment of weakness/at their lowest they pay bailey just to act like a loving partner and telling pc that they love them and such

like pc is 100% aware how pathetic theyre being and they might lose bailey’s respect but theyre so starved and desperate for love and affection they’ll literally pay just to be delusional for a little bit that the person they want most doesn’t actually care about them :’) oughh i love you Emotionally Unavailable Older Men ouughgjgu

sorry for the yapping but again thank u for making this mod and super excited to play through more of it :) !!

Thank you for playing!!!

I love pathetic and toxic dynamics, anon. You're cooking here and I've thought about the exact same scenario as a fic, though I don't think I'd put it in the mod. In a town where everyone is trying to use and abuse you, the most honest relationship becomes your relationship with Bailey. You might be paying Bailey for a service here, but at least you can see the clear line where the deceit/pretend starts and ends.

I hope to add lots of exciting things that you can pay Bailey to do to you. Now I'm considering adding the option to pay Bailey to hold you and cuddle you and tell you that you've done a good job. And once the money is exchanged, he's good at playing that warm, caretaker role. It almost feels real... almost...

The only trade off is Bailey will bring it up to humiliate you if you miss rent the next time, producing his usually ropes and chains while shaking his head. "You wasted your money making me play daddy/mommy when you should have been saving it for rent. Pathetic." +++Stress | +++Trauma | +++Pain | -Respect

Unless you paid for him to never bring it up again, in which case he would charge double and he would obey because those are the terms and conditions.

[dokidokibailey]

Hello, Reiyu! I hope you are having a great day/night right now, I hope I am not a bother to pop into your ask inbox. I am going anon because I'm shy..

I happen to take a liking into Degrees of Lewdity for the past few months recently, and the plot lured me in deeper.

However, one of the few characters that I cannot grasp fully is Bailey. So I hope you're not uncomfortable with helping me out a little. If this is proven to be a bit of a trouble, I am very sorry. Also, sorry if there has been a similar question before this.

I'm currently making a story revolving around my PC who is in very interesting circumstances, though I don't have a solid foundation for the story yet. But I do wish to know your take on what Bailey will think and feel of a PC who is a bit too similar to the Caretaker in a sense?

I do know about the spoiler endgame plot of Avery and the Skyscraper. One of which Gwylan, if I remember, commented that PC was similar to Bailey by taking revenge for the cost of having.. you know, Mark? Forgive me if I recall wrong.(<- trying to avoid spoilers for newcomers coming in blind here...)

Though we aren't shown how Bailey feels or thinks about it. I wouldn't say the PC is an outright villain or such, but the word Cruel would fit this PC of mine(which can be said a bit OOC of the "canon"-ish PC in-game). I do not know much about other blogs in DoL tumblr and I happen to really love your mod and your depiction of Bailey in it! Do take breaks and take care of yourself too, Reiyu! Your health matters greatly. Sorry if this ask is a little bit too long!! I got carried away.. 💧

(ps. Sorry my English isn't too good, not my native language)

Don't worry, your ask is fine, yap away! I love talking about Bailey!!

Bailey is a character with incredible depth, but a lot of that depth is hidden behind his apparent cruelty, buried behind rare game events, or scattered across QnAs. From my obsessive combing of the game and QnAs, my personal belief/headcanon is that Bailey intends to burn the town/cult down and go down with it.

The caretaker before Bailey is confirmed to be worse than him. Bailey, Eden, and his crush were likely orphans at the orphanage. Something happened under the last caretaker that lead to the unfortunate fate of Bailey's crush -- death or a fate worse than death -- sending Eden running for the wood and Bailey planting his feet in town. He became the caretaker, taking over the orphanage filled with nothing but hurt for him, with a loft that he fears. He slapped his family name on it and became the monster that other monsters have to go through to get to his """property."""

The word Bailey means the outer wall of a castle or any of several walls surrounding the keep. To me, Bailey is both the gaoler and the cage. He protects the youth ward, securing their safety with totality until they're 18 and the mask comes off. But his protection doesn't quite end when you're 18 no matter how it may seem. You are his property and that means that he will come to secure and rescue you at different points of the game when you are truly in danger (the prison, the pound, the math stims rescue, etc.). When Bailey swerves into the scene when you're being into prison and screams at the officers that they had a deal, it implies that he keeps his orphans away from there.

The town is the cage. He won't let you leave or move out. But a lot of the town is clutched tightly in Bailey's control. Inside the town, you are ""safe"" by his standards. Broken and beaten and raped, perhaps, but alive. His system is brutal, but Bailey believes in tough love, and here's the thing -- and maybe this is Stockholm Syndrome: Bailey talking -- his system could be so much worse.

Bailey could easily charge you rent without escalating it. From seeing him around the orphanage, you realize he has different rent prices for different orphans. From reading QnAs, you find out that Bailey sends his orphans to different locations, depending on whether he thinks they might escape them. Yes, he escalates the rent at a breakneck pace, but the town requires you to grow at that pace and he forces you towards the fire.

The complexity of Bailey makes my heart tight. I hope you can see what I'm saying. A PC turning cruel is something Bailey might even be proud of, it it means they survive better. It's a concept I explore a lot in my fics. The idea of PC becoming cruel enough that they can take Bailey's place has me by the balls.

That line from Gwylan is actually the juiciest bit for you regarding a PC turning into Bailey or turning cruel. You can see truly that the game itself sees that PC might just walk in Bailey's shoes and become just as cruel, just as vindicative, just as driven by spite and anger. This is my favorite arc of BaileyPC -- Bailey's abuse only creates more abusers.

Meek PC: "Everyone has hurt me. I can't trust anybody. I have to go where I'm dragged to keep the pain away, and do what I can to hurt them back." Bratty PC: "A world as rotten as this isn't worth it. I'll drag everyone down to hell with me." Other: "I've been wronged and hurt. I know this will hurt them all back."

Gwylan will respond with a lot of sweet lore and lot of insight, but the important part is that they will remark, "You sound like Bailey."

That means that Bailey, in Gwylan's eyes, is a man driven by revenge and loss and anger and spite. Bailey hates this town. He's always hated this town. He wants you to hate it too, but more importantly, he wants you to fight it and survive it. He was just like you, once. And now, you might become just like him, and that might be something he wants. He wants you to become like him, to become strong enough to survive. And I think there is something poetic about wanting someone badly enough to be destroyed by it.

[dokidokibailey]

i'm excited to see the cnc content! can the pc end the scene during it via safeword? my brain also goes to a pc potentially being triggered during it due to what can happen in game, but i understand if that's not planned 🙂‍↕️

Since Bailey has a BDSM kink I'd like to incorporate it and safe words. I'm just undecided on a few things right now. For example, I enjoy writing Low Dom and Regular Bailey but I feel that the Flats/Monogamy content only makes sense for a High Dom Bailey. You can currently (might change) unlock Monogamy right now in the mod at low dom if you tried. It requires you to have 50 respect, have taken Bailey on his 5000-pound date, and for you to see Bailey's Peek scene and approach Bailey when you see it. HOWEVER, I have not written any Low Dom dialogue for Bailey in the flats because I just feel that a Low Dom Bailey would not enter a monogamous relationship with you or let you into his flats.

ALL THAT IS TO SAY, I think a High Dom, Monogamous Bailey would absolutely use a safe word. He also is confirmed through QnAs to have two kinks (rape roleplay as the aggressor and BDSM) and all I wanna do in this mod is bridge QnAs and the game...!

When writing Bailey, I like to think on all the other characters and what makes Bailey unique -- I could ramble about that for awhile but he's uniquely positioned as someone who knows your PC from the start, who is PC's abuser, who stresses/traumatizes PC by just existing or being thought of. In particular, I ramble a lot about how Bailey and Avery are two sides of the same coin.

Avery has a scene where he goes "heheh I don't believe in safe words" which makes me want to immediately contrast with a Bailey who does... and there's that tiny part of me that's like hehe "lotus" as a safe word.

(˶˃ ᵕ ˂˶)

Anyway all that is to say, BDSM with Bailey is planned in some capacity, I just haven't decided on how to approach it yet so it'll take me some time.