#rbe!bailey

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! So this is just me yapping into the void.

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 happenings than most people are. If we translate it to in-game stats, he definitely has high Awareness and Willpower.

Earned his 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, 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 of thirty-five 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.

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 hate how convoluted the game paths are, 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.

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

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."

also idk if this is a "they would not fucking do that" situation but consider: pc taking care of bailey after he/she gets hurt somehow 😏

RBE!Bailey Abduction where he confines you in his Flats for sometime is unlocked either by getting pregnant with Bailey's kid, knocking Bailey up, or getting hurt for Bailey (when Respect is sufficiently high enough). I am not quite sure yet if I want Abduction to be an event you can trigger more than once but I think it can be done... the vanilla game doesn't usually add alternative dialogue when you repeat something, so you kind of cycle through some of the same events and the characters say the exact same thing -- that persistent doltown amnesia. I would feel inclined to write at least one line from Bailey if he abducts you again that is like "yep, we're really fucking doing this again, you clearly can't be trusted on your own."

According to qna, Bailey is into CNC, and that is stuck in my brain. Like you don't force yourself on people but you still want it sort of ? Now, i'm imagining a scene of Bailey asking PC to roleplay. And clueless PC, orphan in Doltown, victim of multiple assaults, is very confused ("you want to rape me... consensually ??? That's a thing ? You are actually giving me a safeword ?").

Bailey is also into bondage and would apparently be a good dom. We do have a very bad bitch dom in the game (Avery) so now imagine PC comparing the two, the contrast.

Do you have any plans to integrate these kinks in your mod (or fics) ?

Thank you for playing! I love how terrible Bailey is. The toxicity is 90% of why I am so compelled by him and want to write him more. If BaileyPC was a healthy relationship, I would not have made the Bailey Expansion Mod! LMAO

I LOVE THAT BAILEY IS INTO BONDAGE AND RAPE ROLEPLAY SPECIFICALLY. IT'S ONE OF MY FAVORITE DETAILS ABOUT HIM. The delicious cognitive dissonance of Bailey catering to the town's most depraved rapists and he has the same desires as them, but he needs it to be consensual. It fucks me up so bad. IT'S SO SPICY.

I personally feel this sets BaileyPC up so well -- who else can give him the rape roleplay act but also make it convincing? The brat that drives him up the wall, that's who.

Bailey being a better dom than Avery is a given. In my headcanons, as the caretaker, Bailey actually gives a shit about aftercare.

Also, did you know that when Avery whips you with the cat o' nine tails, PC can mock Avery and regular PC (not bratty/meek) says: "Is that all you can do?" you ask. "Bailey would eat you for breakfast."

PC JUST SAYS THAT SHIT OUTTA POCKET. Now imagine PC actually getting the whipping from Bailey that they so obviously crave. :'3

I will be exploring at least bondage in the mod, but I'm not sure about CNC yet. I'll think on how to do it best!

I will definitely be exploring both in fics because I am weak for the concept and I actually already have something written regarding CNC, I just haven't posted it yet because I worry Bailey is too OOC. In my drafted fic, Bailey pays f!PC for their services and demands that they run and fight and make it seem real -- to fight him like she fights him in the hallways of the orphanage over rent. She obliges and the act and reality bleed together.

What if bailey gets so possesive of pc he puts a chastity belt on them to keep them all to himself and sometimes just to be an asshole doesnt fuck them when they ask or even beg and watch them desperately grind against the chastity belt for any sort of friction or pleasure

Mean dom bailey come home

MEAN DOM BAILEY IS MY FAVORITE FLAVOR OF BAILEY!

I adore the idea, anon. Chastity cages get me going and I was really delighted to discover they are a focus in Degrees of Lewdity.

Bailey as a key keeper would be so, so cruel. They would unlock you only for cleaning and only when they believes you deserve it -- which is almost never. You don't get unlocked just for clearing rent. Maybe if you pay extra, they'll think about it.

As punishment, they would unlock you just to give you a ruined orgasm or to deny your orgasm until you're begging. Then they would lock you up again before you find any release. A reminder of who holds your key and all the power in this dynamic.

As a small reward, they might unlock you and grind you down with their foot. Dress shoe digging into your cock/clit, all while mocking you for being so sensitive. Of course you're sensitive -- they locked you up for weeks.

Then when they finally, finally unlock you and use your properly, it'll be mindblowing. Multiple orgasms drawn out one after the other. Bailey would take their time with you and finish you off with proper aftercare. But this is only after weeks/months of leaving you wanting. Then the miserable cycle continues.

Bailey making PC pay for each orgasm they are given. Stopping right before climax and making them beg until they get a satisfactory fee. And if they do manage to come before then, adding it to their weekly paiement. Pleasure doesn't come for free.

Spa worker PC getting a taste of their own medicine. Paying for a "happy ending", but Bailey pins them down and start edging them. They are getting their orgasm, just... not now. Maybe a tip could motivate them to be... faster. PC shouting higher and higher prices, but Bailey knows they earn more than that per week. Surely they can give more.

You know that one qna about Bailey imprisoning Quinn if kissing them meant getting 1000£ every time ? Bailey tying up PC in ropes and edging them over and over. Making them cum until they are bled dry of their money. Only relenting when they scream that they really don't have anymore to pay them. Or maybe they don't stop. It can always be added to their debt after all.

Don't misunderstand though. PC is just a convenient source of wealth. Bailey certainly didn't enjoy seeing them in bondage or making them a overstimulated mess. Nope.