Bailey's Payments

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Bailey's Payments (otherwise referred to as "Bailey's Punishments") is one of few repeatable quests within Degrees of Lewdity. The intro to the game will introduce this quest.


Bailey has instructed the PC to earn £100 by the end of the first week. It does not matter how the player achieves getting that amount, as long as they have it ready when Bailey comes to collect their payment. Otherwise they'll "extract value" from the player.

In the event the player unlocks Alex's Cottage and lives with them Bailey will visit every Friday to ask for payment like before.


This quest is unavoidable. It will be automatically given to the player upon starting a new game.


After the start of a new game, 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 around the Orphanage. In order to avoid punishment, you must pay rent.

Rent Sliders

You can control Bailey's rent via a slider in Settings. Be warned that setting it below 100% will count as enabling cheats and lock feats.

This setting allows players who already play with cheats or don't care about feats and find meetings Bailey's request difficult to pay. Or for players who find it to easy to gain money and want an increase in difficulty for their game.

  • 10% to 90% - Count as cheats, disabling feats..
  • 100% - Play the game as intended.
  • 110% to 300% - For harder difficulty.


If the player manages to scavenge together the required amount for the first week and successfully manages to pay Bailey, this will prove to be pointless as Bailey will demand even more the following week, before mocking the player by saying they thought it would become easier. At this point, the player quickly learns that Bailey is not interested in keeping their word at all, and instead wants to extract as much money as possible from the orphans (the player included) under their care.

Bailey's payments gradually increase each week as Bailey becomes more greedy and extorts the player for what they're worth.

The first payment on the 7th day will be £100. Naturally it will increase the more the player gives to Bailey.

  1. After paying £100, the second payment on the 14th day will require £300.
  2. The third payment on the 21st day will be £500.
  3. The fourth payment on the 28th day will be £700.
  4. The fifth payment on the 35th day will be £1000.
  5. The sixth payment on the 42nd day will be £1500.
  6. The seventh payment on the 49th day will be £2000. This amount is the capped final amount, after which the payment amount will stop increasing and remain indefinitely at this amount for the rest of the game.

While payments will eventually become capped at £2000, it will infinitely repeat. To sum things up, the player will now have to pay £2000 each week from that point onwards, rather than resetting back to the first payment of £100. This means that Bailey's payments do not stop, and will continue for the rest of the playthrough.

Bailey may also demand payment on other days than Sunday mornings, as this is due to the player being late on recent payments. If Bailey was avoided for a few days, they will set whatever day the player paid last to be the new due date from now on. Sunday may now become a Monday, for example.

If paying for Robin, the maximum amount required each week will be capped at £4000 instead. This is because the player is paying for them in addition to themselves. As an example, if the player is paying £500 for instance, Robin's payment is also that - meaning the player will have to pay a total of £1000.

For more information, visit this page: Robin's Quest

Meeting Bailey's Demands

While it may be very difficult to meet Bailey's demands, especially towards the latter stages of their payments, it still remains possible.

Be sure to think outside the box and use skills such as Dancing to gain an advantage in places like the Strip Club and Brothel. Alternatively, there are other ways to make money such as working at places like the Docks, find treasure within the Forest Lake Ruins, or use Skulduggery to engage in Crime.

Alternatively, the player may also choose to prostitute themselves and sell their "services" to others in exchange for cash.

All of this combined will net the player with the required amount by the end of the week, although it may take some extra effort.

Bailey's Punishments

If the player does not wish to pay Bailey at all or does not have enough money when they demand their payment, they learn that Bailey already has made arrangements with potential buyers. If they cannot pay with money, the player can pay with their "services" - their body.

In this case, Bailey is able to sell the player for more sinister purposes, punishing the player for not paying them.

The premise behind this is that Bailey sells the player to whoever pays the highest amount for them, regardless of who the buyer may be. Bailey ultimately does not seem to care for the player's well-being under the player's buyer, as long as they get their money - that's all that matters.

There are four unique punishments for the player to endure as a result of them not paying, each growing more difficult than the last:

  1. Sold to a fancy dinner party to be used as "pudding" for the rich attendees.
  2. Sold to Eden. If the player has the Stockholm Syndrome: Eden trait, it will be seen as a rescue instead.
  3. Sold to Remy, to be used as livestock on the Underground Farm.
  4. Sold into sex trafficking, more specifically the Underground Brothel.

A common misconception is that it is believed that if a week or more passes when the player is overdue on a payment, Bailey will skip to their next punishment. This is false. If the player is overdue on their first punishment for several weeks, it will not skip to the subsequent punishment, and instead have the dinner scene play out if the player returns to Bailey, rather than being sent to Eden.

This means that punishments will still happen in order, until the player actually goes through with the punishment they are overdue for.

If the player manages to go through with the final punishment and escape the underground brothel, the punishments will loop back around to the first one, allowing the player to experience each of the punishments again.

There is also a special punishment if the player refuse to pay while living in Alex's Cottage. In which case Bailey will support Remy's attacks on the farm. With their support Remy's encroachment will rise faster and their assaults will be reinforced with an additional group of elite thugs.

For more details see Farm Assault.

Fighting Back

It is possible to fight back against Bailey, but doing so is dangerously risky nonetheless.

The player can willingly refuse, or be forced into refusing automatically because the player lacks the funds required for the weekly payment. From there, the player is able to fight back. It should be noted that doing so will prove much more difficult than anticipated, as Bailey is one of few NPCs that is extremely tough to fight, the other being Eden. It is highly recommended to have a few charges of Pepper Spray on hand. A high English grade will allow the player to apologize more effectively during combat, lowering the pain inflicted upon player while Bailey's anger remains low.

Successfully managing to subdue Bailey will cancel out that week's payment and force them to give up their pursuit, retreating away embarrassed. A crowd of orphans gather as the fight continues, with them cheering at the player's defeat of the tyrant - with Bailey swearing revenge later on.

However, this proves to be it's own problem: They wisen up to the player's antics and the following week they will return with a bodyguard, making things much more difficult for the player to resist.

Alternatively, the player could try to (humorously) make them orgasm, allowing the player to skip the payment for that week as well, similarly to subduing them. Regardless, Bailey will still find a way of extracting value from the player. This leads into the next section.

Making Bailey orgasm will unlock the "Trouble at Home" feat.

Either way, subduing Bailey keeps your current payment for next week, so it is possible to never reach the maximum payment cap by never paying Bailey what they want.

Avoiding Payments

There are ways to avoid payments, but this is risky in of itself.

  • The sure-fire way is to make Bailey orgasm, bypassing the payment. This is only temporary as Bailey still punishes the player in some way.
    • They will prostitute the player out to anyone who wishes to purchase their "services", allowing them free access to the player's bedroom at any time. There is a good chance that a few days after the player successfully fights back against Bailey, they will wake up to someone molesting them as Bailey watches by the door, counting the money as they supervise the scene. Fighting this person off may prove tricky. If Robin or Kylar is in the player's bed at this time, they will wake up upon the player choosing the option to scream while in combat - they will then end the encounter by attacking the assailant, causing them to flee.
  • Another way of avoiding the payments is to live in the Forest or in the Moor indefinitely. Bailey will always wait until the player returns to the Orphanage to collect their payment, so it is entirely possible to avoid them altogether.
    • It should be noted that this comes at it's own cost of the player secluding themselves within the Forest or the Moor and choosing to live with Eden, in their Cabin, and/or the Wolf Pack, located at and the Wolf Cave deep within the Forest, or the Great Hawk, in the Hawk's Tower, deep inside the Moor. For more information on how to live with them, visit their pages respectively.
    • By doing this, the player will miss out on events that take place at the Orphanage, and any progress that can be made with Robin. Be sure not to pass out and wake up at the Hospital, as Bailey will be there waiting for the player. There eventually comes a point when in order to progress in the game, the player will have to return to the Town, and in one way or another having to cross paths with Bailey once again - making it impossible to avoid Bailey if the player wishes to progress.


Currently, there are no rewards for this quest as it will infinitely repeat. However, it will allow free access to the Orphanage without any trouble should the player continue to pay Bailey. Paying them will also avoid any punishments dealt the player's way, as well.


  • This quest is the only one that cannot be avoided in some way, as it is the basis for the game's plot.
  • It is completely unknown as to what Bailey does with the money, but it is best assumed the money is pocketed due to Bailey's corrupt nature.

Story Quests
Main Quests Bailey's PaymentsCafe CampaignFarm AssaultTemple Initiation
Personal Quests Blackmailing LeightonBlackmailed by LeightonDoren's ConcernsLeighton's InspectionsSabotaging RemyRite of PromiseRite of DefilementRobin's QuestTaking Flight
NPC Dismissals Dismissing AveryDismissing KylarDismissing Whitney
Repeatable Quests Chastity VowCharlie's JobsDanube Street BurglaryDanube Street JobsDocks InfiltrationDetentionLocker RaidSchool ExamsLandry's RequestCommunity ServicePilloryPolice InfiltrationSmugglersTrial by Fire
Special Events Moor AbductionNight MonsterStimulant KidnappingTenyclus
Annual Events Holiday Events Robin's HalloweenWhitney's HalloweenEden's HalloweenKylar's HalloweenRobin's ChristmasEden's Valentines
School Projects Maths CompetitionScience Fair

Main Mechanics Player Mechanics AttitudesBody FluidsBody Part SizesCurrent ConditionGenderPlayer CustomizationSubmissivenessTattoosTraitsTransformationsVirginities
Characteristics InsecurityLewdity StatsMain Skills (SkulduggeryTending) • School GradesSensitivitySexual Skills
Gameplay Mechanics Bailey's PaymentsCombatDifficulty SettingsFeats (Feat Boosters) • Minigames (BlackjackMasturbation) • Stalk EncountersTogglesSoft Bad-Endings
World Mechanics AntiquesBlood MoonDismissing NPCsFameLove InterestsMachinesSafehousesEnvironment (SeasonsTemperatureWarmth) • Unlockables
Clothing Clothing CatalogueClothing Mechanics
Miscellaneous Mechanics CheatsJournalScene ViewerStatisticsTips