From Degrees of Lewdity Wiki

Bailey the caretaker is the one in charge of the Orphanage on Domus Street where the Player Character (PC) currently resides.


Bailey's description will remain consistent, regardless of what sex they are determined as. They are described as having dark hair.

First Meeting

The first meeting with Bailey is the intro of the game.

As the player enters Bailey's office, they already know why they are there, and further explain by saying they want to make the player an independent citizen and to release them from their protection. There's a catch, however - the player has been living under their roof without giving anything in return, and they owe them. Until then, they refuse to let the player go free. They explain how £100 should do to begin with, and it doesn't matter how the player achieves getting that amount, as long as they have it a week from now.

Otherwise they'll "extract value" from them.


Between 7 AM to 9 AM, Bailey can be visited in their office. They are not to be disturbed, as they will become hostile to the player should they enter and re-enter.

If the player tries to sleep in on a school day, Bailey will bang on the player's door at 7AM and demand that they get up, though the player can go back to sleep afterwards with no repercussions.

In the event the player unlocks Alex's Cottage and lives with them Bailey will visit the cottage every Friday or Saturday morning to ask for payment.


Bailey acts very antagonistic towards the player, and serves as the closest thing the game has to an antagonist. They have an overarching role in the game's narrative, meaning that the player's motivation is based around defying Bailey's requests. As such Bailey will make numerous cameos in various scenes, such as:

  • Bailey may try to bully the other orphans into submission, such as removing motivational posters or punishing them in similar ways to the player.
  • If the player hears an orphan being attacked, they have the option to tell Bailey. Doing so has Bailey deal with the attacker personally.

Additionally, Bailey will also drive the player back from the Hospital for the first couple of times but eventually stops coddling the player, letting them deal with their own problems. However, interestingly, Bailey will try and interject if the player ends up being taken to the Asylum.

It is more or less considered impossible to improve Bailey's relationship, as they will intentionally always act antagonistic towards the player, due to them being the main antagonistic driving force behind the player's misfortune dealt their way. While the player can "seduce" Bailey, this is more or less considered as a "one-off" in Bailey's eyes, and Bailey will return to demanding payment as usual after some time has passed.

The player cannot remove them from the game in any way, through dismissing them and/or finding a new place to live. It is important to know that Bailey has strong connections in the town, and will not be shaken off so easily by the player - especially regarding missed payments.

Seducing Bailey

Part 1

With Promiscuity 2 or higher, the player can attempt to seduce Bailey (+ Trauma) when they come to collect their payment.

"You can pay me," he/she sneers. "With money. £ (Amount). That's what your body's worth."

The player is then given their usual options of paying or fighting Bailey. If Bailey has a bodyguard with them as a result of the player's defiance, the guard will offer to take the player as payment, earning a glare from Bailey.

The player can only try seducing Bailey once, after which the option will be gone from all subsequent encounters. Note that the player's Seduction skill does not factor into this interaction at all, but comes into play for another sequence that goes much further.

Part 2

If the player has Promiscuity 3 or greater and a S in both Seduction and Attractiveness (Beauty will contribute to Attractiveness, but things like hair length, the lewdness of clothing, make up, and transformations can help push it to S), the player has the option to successfully seduce Bailey. Enter Bailey's office while they are in it (between 7AM and 9AM) the day before the player's rent is due (the player can check in their Journal when rent is due if they are not sure) and the player will be able to ask Bailey for more time, claiming Bailey doesn't want to see them go away. As Bailey agrees with the statement, they will knock the player over and begin a nonconsensual encounter (+ Trauma).

In this encounter Bailey's trust will nearly always be at its lowest value, even if a player with S rank English apologises, so the player will very unlikely be direct Bailey in any way or ask Bailey to do anything as all checks will usually be Very Hard or Impossible. If the player makes Bailey orgasm, Bailey seems horrified afterwards, immediately covering their horror with fury and throwing the player out of the office. The player will then get one extra day to make their payment, permanently changing the day rent is due. If the player instead reduces Bailey's health to 0, they will be thrown out of the office with no extension given. The player can only attempt this once per pay cycle.

"Shit... Shit! What the fuck did I just do?"
— Bailey, upon realizing their mistake

Note that it can be very difficult to obtain what is required for the event in a normal playthrough, but it is possible nonetheless. It is a scene purposefully designed to be very difficult to obtain normally due to the circumstances it entails.

Player's Demands

If the player uses the "Demand" option when trying to fight off Bailey, unique lines are said. A list is provided below.

  • "I'm not letting you auction us off like whores!" (if the player has high Awareness)
  • "What do you want from me?" (if the player has low Awareness)

If Robin is affected in some way by Bailey:

  • "What the fuck did you do to Robin?" (if Robin is missing)
  • "It's your fault Robin is hurt!" (Robin's Trauma > 60)
  • "No more extortion!" (the player knows about Robin's debt)
  • "You're a monster!" (default)

Otherwise, they will say the following:

  • "You're worse than the rapists you cater to."
  • "You're a shit caretaker."
  • "You're going to pay for what you've done."
  • "You abusive, vindictive fuck!"
  • "I'm not going without a fight!"

Combat Dialogue

When choosing to fight, Bailey will start with "You think I won't be beat it out of you?". They will then say some of the following lines during combat.

Depending on Bailey's anger:

  • "It's no wonder everyone wants a piece of your orphan ass."
  • "You're so valuable!"
  • "Just relax. I'll handle everything like always."
  • "You were always the best looking little bastard/shit."
  • "It's easier this way. Trust me."
  • "Maybe I should inspect you before we go."
  • "Why do you shits have to make it harder on yourselves"
  • "I told you to hold still"
  • "You're making it harder on both of us"
  • "You chose to let this happen"
  • "Are you going to listen to me now?"
  • "You're going to a bu..."
  • "You're coming with me and that's that"

Depending on the player appearance:

  • If the player hair is longer than 600 (reaches navel at 600)
    • "Kept your hair long? I know someone who will like that."
  • If the player dick is larger than 4 (must be either Large or Enormous) or breasts larger than 6 (must be either Full, Large, Ample, Massive, Huge, Gigantic or Enormous)
    • "Cows fetch a high price these days, you know."
  • If the player athletics is > 750
    • "You've taken care of yourself. Good.

When the player is cumming:

  • "Nice look. Some people would pay big to see you hot and bothered like this."
  • "Should've brought a camera. Your profile would look great with this expression."

The following lines would appear if the player were to have sex with Bailey, via seduction:

  • If the player lost their virginity to Bailey
    • "Your body was always mine. Like your first time."
  • If the player lost their anal virginity to Bailey
    • "You should be putting out more if you're this tight. What do you think you're good for?"
  • If the player lost their oral virginity to Bailey
    • "Don't get any funny ideas. Just take it."
  • If the player lost their first kiss to Bailey
    • "Surprised are you? You'll learn to kiss better soon."
  • If the player cums or get cummed inside Bailey
    • "I hope you appreciate that."
    • "Just something to remember me by."
    • "We'll call that your going away gift."


Note: The following events are not to be considered as a full, comprehensive list of Bailey's interactions in the game - but more rather their most notable interactions. As such, minor events may not be listed below. However, more interactions will be listed below as the character remains in development.

Bailey's involvement with the player allows them to have unique interactions with each other. It is implied that the player detests Bailey for what they put them through, constantly mentioning them in passing - and not in a positive way.

Bailey's Office

Going to Bailey's office normally Bailey will just tell the player to not waste their time. However certain things can affect what Bailey would say to the player. If the player is crying, Bailey will tell the player that there's bandages in the bathroom.

If the player is flustered, Bailey will tell the player to get someone to take care of that for them, even hinting at prostitution. If the player is visibly disturbed, Bailey will grimace and will say that someone is probably into that. If the player is drenched in lewd fluids, Bailey will tell them to get themselves cleaned up.

Going to Bailey's office for about 6 times will make a prompt to seduce Bailey to appear.

Annoying Bailey

Going inside Bailey's office for 4 times without any particular reason at the same day will cause Bailey to spank the player, initiating a nonconsensual encounter. Apologising to Bailey because of this, or after 14 turns, they will release the player and tell them not to waste their time before gesturing them to leave. Beating Bailey out will cause them to shout it.

However successfully making them cum will leave them dazed for a bit, before shaking their head and telling the player to leave. After this, Bailey will just ignore the player for the rest of the day.

Bailey's Payments

The game's premise is centered around Bailey. The PC wants to become an independent citizen, but throughout their time at the Orphanage they haven't given anything back to them, so Bailey tasks them with finding £100 to begin with - they don't care how they do it as long as they have it ready by next week - or else they'll "extract value" from them.

From then on out, Bailey will demand money from the player at the end of each week, more specifically every seven days on a Sunday. They will track the player down and demand payment from them. In order to avoid punishments, the player must pay as prompted.

If the player refuses to pay Bailey, through submitting or losing combat, they will learn that Bailey already has made arrangements with potential buyers for their "services" - if the player cannot pay with money, they will find another use for them, selling the player for much more sinister purposes.

There are four unique punishments for the player to endure as a result of them not paying, each growing more difficult than the last. The last punishment will repeat. And a fifth if the player lives in Alex's Cottage.

Visit this quest page for more information: Bailey's Payments

Bailey plays a central role in Robin's story. The player is not the only victim of Bailey's extortion. For more information, see here: Robin's Quest

Mentions of Bailey

Bailey's overarching, intimidating presence is felt across the town, and they can be brought up by numerous NPCs.

  • Bailey may be mentioned in passing when talking about keeping an orphanage dog with the other orphans or examining what is available at the Shopping Centre's Pet Shop. In both cases, the player is unsure whether or not Bailey will let them keep a pet.
  • Bailey will be mentioned by Landry during the "Police Infiltration" sidequest - calling them a "nasty piece of work" and even comparing them to Briar by saying it makes Briar look like a "bleeding-heart humanitarian."
  • Bailey will be mentioned by Alex if the player ask them what they know about Bailey after Alex fields got burnt by Remy. And responds that they heard rumours of them, and after seeing what happened notes that some of those rumours may be true.
  • Bailey will be mentioned by Wren in their Docks event if the player already met them. They'd ask if Bailey sent them and say that they won't interfere either way.
  • Telling the person inside the stone building that Bailey sent the player after knocking the vials will cause them to hesitate before releasing the player, saying that they didn't know they had business with that sort.

Bailey in the Park

Several characters can show up in the park at night when the player is running around naked, and one of these NPCs is Bailey. They will be seen making a deal with someone, who thanks Bailey and say they'll be gentle even though "this one's feisty". The player then has the choice to stay hidden or show themselves (Exhibitionism 2). If the player stays hidden, they will stay out of sight, but close enough to watch, Bailey having no idea the player is in such a state so nearby. If they show themselves, the worst thing that may happen to the player is that Bailey will shout at them if a payment is due. This has Bailey say "I've been looking for you. Time to pay-" before they are interrupted by the player dashing swiftly away from them.

Cafe Grand Re-Opening

Bailey is a central part of this event. The event in question triggers once the player has become renowned for their cream buns. During the event, Bailey will actively try to stop the player from telling the world about their tyranny.

For more information on how to achieve this, visit this page: Cafe Bun Chef Sequence

Bailey makes an appearance as the player steps through the cafe's doors. They grasp the player's arm while giving them their "best smile" - it's noted it does not look sincere. They tell the player they have done well through their teeth, but not to "fuck it up." If Avery is with the player, they grasp Bailey's hand, forcefully shaking it. They introduce themselves with Avery, with a hint of anger in their voice. The player's heart skips a beat as Bailey reaches into their jacket, but they instead pull out a handkerchief from their pocket. They tell Avery it's a pleasure to meet them, but they were just talking to their ward. They ask for a moment's privacy away from Avery, with Avery saying they have old friends to catch up with, while stating they are sure there are also many others who want some time with the player. While Bailey watches Avery leave, the player has three options:

  • Slap Bailey. Reduces Trauma. Has the player slap them across the cheek, with Bailey barely flinching. The room quiets for a moment before breaking into laughter. Bailey leans in closer with a fake smile. They whisper to the player that they'd "best not try that when we're alone" before telling them they are worth more with both hands attached.
  • Thank Bailey. Has the player sincerely thank Bailey driving Avery away. Bailey will then lean in closer, whispering to the player that when they deliver their speech, they should not say anything they will regret later on.
    • Defiant: "Thanks," you say. "You've made my evening slightly less unpleasant."
    • Neutral: "Thank you," you say. "I needed some space."
    • Submissive: "Thank you," you say. "Avery can be scary."
  • Remain Silent. Has the player simply glare at Bailey, not saying anything. They look away from the player.

Regardless of the player's choice, Bailey will pull away as the player is realising that for the first time since they arrived they are no longer the centre of attention. The attention turns toward the new arrival of the town's mayor, Quinn. Bailey will then lean in, whispering something to Quinn. They seem to dismiss it as "nonsense" however, laughing. A speech by the player will still go ahead. Bailey's acts of protest will be ignored by Quinn, as the mayor will take the player's arm and rejoice in their celebration. Bailey takes Quinn to one side and whispers something else, with Quinn frowning in response. They excuse themselves from the scene before walking away with Bailey. It's noted that the player cannot make out what they are saying. The player will then look over at Bailey and Quinn as people find their seats for the big event, with Bailey seeming agitated while Quinn acts more jovial, chuckling while pulling themselves away from the conversation.

During the speech, Quinn takes the time to bring attention to Bailey, stating they'd like to thank the player's guardian, while gesturing over to Bailey perching at the edge of their room - their hard work protecting and caring for the town's "most vulnerable" has allowed the young prodigy to flourish, with applause filling the room.

When it's time for the player to have their say, they have five options on what they can do. One such option is the ability to tell the world of Bailey's tyranny.

Doing this has Bailey stare back as the player looks around the room. They take a deep breath, talking about life at the orphanage - more specifically the lack of food, what Bailey makes the player and the other orphans do, and the punishment for failure. It's noted that at some point the player's fingers start to hurt from gripping the sides of the podium. The audience listens in silence, with some smiling, others in disgust. The orphan employee seen before is in tears. Bailey refuses to look at the player, glaring at the mayor instead. Quinn will intervene, interrupting the player's speech by pushing them off the podium. They claim that the player is "such a joker" and that their friends put them up to it. They go on to state that Bailey's orphanage is one of the town's oldest and "most esteemed" institutions, and that any abuses of power are taken seriously. The player isn't sure if their words got through, with many of the locals nodding along with the mayor's words. However, it's noted that some still don't look so convinced, believing the player's words to be true.

During the after-party, the player has the option to socialise with the cafe's visitors. If the player has told them about Bailey's tyranny, a concerned-looking man/woman will ask for more details regarding the orphanage. Their friend shushes them in response.

As the party winds down, the player will start to head towards the exit, but not before they are intercepted by Bailey. They call the player a "brave little shit" before grasping their shoulders and turning the player to face the now drunken guests stumbling out of the cafe. They state that they all want a piece of "orphan ass" now that the player has screamed about it, saying that it's made things difficult. They release the player before walking away.

At the Flats

While doing work at the flats, the player is warned about a flat with a lotus knob. There's a random chance that the player will find the flat, and if the player chooses to open it anyway, they will learn that Bailey lives there. Bailey will notice that the player didn't expect them and immediately slam the door.

Once the player owns the Hookah Parlor and then cleans it, Bailey will come in and claim 50% of all profits made on the parlor, specifically saying that it isn't negotiable. The player can get mad at this or just nod, but it doesn't make any meaningful change. Bailey will suggest going to the Farmlands for material and then leave.


  • Bailey is one of several people of interest to exist since the initial release of the game. A full list is provided on the Named Non-Playable Characters page.
  • Bailey is the only named NPC to have an overarching role in the game's narrative, and will be consistently mentioned by the player on numerous occasions.
  • Bailey is the only NPC that cannot be avoided whatsoever - there is no way to skip Bailey's introduction.
  • Unlike many other NPCs within the game, Bailey is one of few named NPCs to know of the player's true identity before the game begins, with the other person being Robin. A hidden variable such as $genderknown is set to these two named NPCs.
  • In earlier days of the game, Bailey's introduction was different. They were originally intended to be nicer. Their original introduction can still be found in the game's files.
  • Bailey's name is a reference to the term "Bailiff". Merriam-Webster defines this term as such:
  1. a: an official employed by a British sheriff to serve writs and make arrests and executions b: a minor officer of some U.S. courts usually serving as a messenger or usher
  2. chiefly British: one who manages an estate or farm[1]
  • Numerous requests for ways to remove/kill Bailey by the community have been made - however, this has been denied:
    • There are multiple reasons for why this is the case, as listed below:
      1. Bailey acts as the main means of progression and pressure within the game. They are purposefully designed to motivate the player to make money each week in order to avoid trouble. Removing them from the equation will effectively remove the player's reason to walk out of the orphanage.
      2. Additionally, it robs the game of an antagonist, as no other NPC has much of an impact on the player as Bailey does. Without Bailey, there is no consistent, overarching presence looming over the player's head.
  • It is implied that Bailey has the mayor, Quinn in their pocket, to an extent.
    • Any attempts to defame Bailey by the player will be dismissed by Quinn.
    • Whether the mayor knows about Bailey's abuse towards the player remains to be seen. Quinn may be blissfully unaware, or fully aware of the situation but wishes to avoid controversy.
    • Quinn's emails with Bailey seem to confirm this, with Quinn begrudgingly going with whatever Bailey tells them to, though not before Quinn's types up a rant that they never send. Quinn's rants mention a "sin" that, according to Quinn, they have already paid for.
  • Bailey is one of very few NPCs to stay firm to their demands and not be won over by the player's body - to an extent.
    • While it is true that they can be seduced - to Bailey's begrudgement - this requires a max rank in Seduction, and cannot be pulled off easily. Bailey will be in shock afterwards, contemplating what they have just done, but ultimately allows the player one extra day to get the money to pay them. Bailey consistently affirms that they are more interested in the money the player brings in, regardless of the methods they will take to retrieve it. They will only concede, begrudgingly as stated prior, under specific circumstances - but it should be stated that ultimately they are not interested in the player as a person nor as a potential love interest either.
    • The player thinks of Bailey as a threat, more or less. As such, doing things that would humiliate Bailey in some way such as making them orgasm or telling the truth about the orphanage in specific scenarios will anger them.


"The following images showcased below are fan interpretations of what this character looks like in-game. Despite canon descriptions existing within the game itself, visual depictions of the character akin to the player sprite are best left to the player's own interpretation."


  1. “bailiff,” Dictionary, Accessed 7/15/2020.

Named NPCs
Love Interests RobinWhitneyEdenKylarAveryBlack WolfGreat HawkAlexSydney
People of Interest BaileyCharlieDarrylHarperJordanBriarSamLandryLeightonSirrisRiverDorenWinterMasonMorganGwylanNikiRemyWrenIvory WraithMickeyZephyr
Special NPCs Quinn
Persistent NPCs Black DogPrison GuardsPrison InmatesWatchtower Guard