Rite of Defilement

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Sydney the Faithful
Sydney's CounterDatesEvents & InteractionsInter-NPC InteractionsPersonal Quests (Rite of DefilementRite of Promise)

Sydney might be willing to get his/her chastity device removed for someone completely pure, or if his/her mind was opened to lewdity. A very pure or very corrupt mindset, as well as a large amount of sinful lust, may be the key.
— In-game prompt

The Rite of Defilement is one of two personal quests involving Sydney. It offers the player a chance to open Sydney's mind to the idea of lewdity - something they deem as a sin - and go against the wishes of the Temple.

Unlike other NPCs, there are two paths to Sydney - pure and corrupt.

This page will cover the corrupt path. For the pure path, see the Rite of Promise. Note that these two quests are mutually exclusive - though Sydney can still be re-purified after the fact, completing the Rite of Defilement permanently prevents the completion of the Rite of Promise for that playthrough.


Having been fully exposed to the world of sex and debauchery, Sydney decides the only way to embrace their new self and show their devotion to the player is by through the sacrilegious act of removing their chastity belt. Once the player meets the appropriate requirements, Sydney will invite them to the Temple after dark to put their plan into motion.


Note: While this quest can be completed at any time of the year, actually starting the quest requires the player to chat with Sydney, which can only be done in the library while school is in session.

Before Sydney will suggest having their chastity device removed, their relationship with the player must have reached a certain, intimate point, as indicated by their stats.

  • Their Love must be at 83% or higher.
  • Their Corruption must be at 80% or higher.
  • Their Lust must be at 20% or higher.
  • They must have already removed their anal shield
  • The player must already be in a relationship with Sydney, as indicated by the ability to choose them as a Love Interest

Of the three required stats, Sydney's Love is the easiest to raise, as the player can meet the required level of Love simply by spending time with Sydney.

Sydney's Corruption and Lust go hand-in-hand. Most actions that raise Corruption/lower Purity also increase Lust; the player will likely have far surpassed the amount of Lust required by the time Sydney is corrupt enough to trigger the quest. Getting into sexual encounters with Sydney is also a reliable way to increase their Lust, regardless of whether they cum or the player asks them to stop.

Sydney's anal shield will be removed automatically once their Love and Lust reaches a certain point - specifically, 60% Love and 20% Lust. Also, the player must have already found out about Sydney's chastity belt beforehand; this usually happens during lewd encounters, but can also be acheived during certain scenes. Once the player meets the requirements, Sydney will mention the removal of their anal shield at random: "I was able to convince them to remove my anal shield, at least." Note that the player may have to wait a day after reaching the required levels of Love and Lust before Sydney has their anal shield removed.

Once the player has met the aforementioned conditions, they must get into a lewd encounter with Sydney. The most reliable ways to do so are as follows:

  • Crawl under the counter at the school library (Promiscuity 4)
  • Catch them peeping on the player in the changing room, then confront them and subsequently proposition them (Promiscuity 1)

Provided the other requirements have been met, the player will receive the following message after having sex with Sydney:

  • "That does it. We need to talk later. I'm getting this thing off of me, one way or another."

Upon hearing this, choosing to chat with Sydney the next time the option is available will begin the quest to remove their chastity belt.


Once Sydney has expressed their desire to have their chastity belt removed, chatting with them afterwards will lead to the following exchange.

You open your mouth to speak. Sydney cuts you off. "I want this belt off of me." He/She sounds determined, and his/her expression is serious.

"About time. Are you sure about this, though?"

He/She nods vigorously. "I've never been more sure of something." He/She begins to pace. "They won't just let me get my belt removed for no reason, but I'm not going to let that stop me. I've been an initiate for a long time. I've watched monks and nuns travel this way and that, and I know where they store all the chastity devices, along with some real kinky shit that I didn't understand until recently. Devices for punishment and purification." He/She makes a lewd gesture with her fingers as he/she speaks.

"We're going to sneak in at night, find the key to my belt, and then you're going to fuck me raw right then and there." He/She pays no mind to her volume level, and for a moment, you're worried someone will overhear. "I need this. I need you to defile me. It will bind us together forever." He/She gently takes you by the hands.

"The next time we're both at the temple, we can get started. I can't wait." Sydney releases you, and goes back to work.

After hearing this, the player must find Sydney at the Temple between 9:00 PM and 11:00 PM, where they can ask about Sydney's plan. If it's too early, Sydney will blush and say, "We'll need to wait for it to get dark, though. Meet me here once the sun's down."

  • Defiant: "Ready to break some vows?" you ask.
  • Neutral: "Are we ready to execute your plan?" you whisper to him/her.
  • Submissive: "So, are we ready to... do what you said?" you ask quiety.

Besides the timing, there are certain other factors that may throw a wrench in Sydney's plan, including:

  • If Sydney's Corruption goes below 10%, they'll lose their nerve. "About that... I..." he/she sighs. "Maybe I spoke too soon. We should really take some time to think about if this is what we want." In order to continue, the player must get Sydney's Corruption back up to at least 10%.
  • If the player is wearing a chastity belt they recieved from anywhere other than the temple (from Winter or the Forest Lake Ruins, for instance), Your belt... it's not from the temple, is it?" The player nods, causing Sydney to frown as they explain that the keys kept at the temple won't be able to unlock their belt. In order to continue, the player must remove their belt through other means - namely, letting it get destroyed during encounters.
  • If the player has yet to become an initiate at the temple, Sydney will frown, explaining "There's no way we'll be able to sneak back there, since you're not even an initiate. You'll have to talk to brother/sister Jordan and join the order before we can do this." In order to continue, the player must become an initiate at the temple.

If the requirements are met and the player visits Sydney at the correct time, Sydney takes a deep breath, telling the player they're ready before providing directions to the temple's back halls.

Sydney stops and turns back to the player. "Are you absolutely sure you're ready? Broken vows are taken very seriously here, and if we get caught..." The player is given one last chance to back out; should they do so, they'll still have the option to ask Sydney about their plan later, if they change their mind. Otherwise, the player can tell Sydney they're ready.

You nod. Sydney kisses you on the cheek for reassurance. "I love you," he/she says. "I'll finally be able to show you just how much I do."

Breaking In

With the player's confirmation, Sydney breaks from them and sneaks through a door. Per Sydney's instructions, the player waits two minutes before following.

The player navigates the halls without issue, the monks and nuns too preoccupied to notice the trespasser, until someone suddenly grabs the player, muffling their mouth and pulling them aside. The player struggles but relaxes upon realising it's only Sydney, shielding them from a passing monk/nun.

"That was close. Initiates aren't supposed to wander around this section, but the midnight vigils sometimes require us to anyways." They take the player's hand and lead them deeper into the temple.

The player follows along, quickly losing their sense of direction, though Sydney knows where they're going. "That room's where they store the incense. The strong stuff and the regular stuff for the thuribles. I don't know what's down that hallway. Or that one." He/She pauses. "This place always feels bigger on the inside. I wonder what else feels that way." | + Arousal

The player has two options to for getting past the door: pick the lock (0:05, Crime) or break the door down (- - - Grace).

  1. A Skulduggery skill of B or higher is needed to pick the lock, ensuring a quiet entry. If the player doesn't meet the requirement, they won't receive the option to pick the lock.
  2. Choosing the break the door down has two outcomes, depending on the player's Physique.
    • If the player has moderate/high Physique (around 5/6 for a small body, 4/6 for a normal body, or 3/6 for a large body), they'll smash the door off its hinges, breaking it open. "Someone will have heard that. We need to hurry," Sydney notes before grabbing a torch and leading the player into the room.
    • If the player has low Physique or a tiny body, the player only manages to kick a hole in the door and fall on their butt (+ Stress | + Pain). Sydney stifles their laughter as they reach through the hole, unlocking the door "Someone definitely would have heard that. We should hurry."

The Storage Room

Sydney and the player enter the room and begin their search. The player takes note of the various chastity devices and punitive equipment littered around the room, as well as a pile of pink canisters in the corner of the room.


If the player chose to break the door to the storage room down, regardless of whether they did so without injuring themselves, a voice will interrupt their search. "You're not supposed to be here. The player turns to find two black-robed figures. "You two have caused severe damage, and are trespassing. You must be purified." One grabs Sydney while the other advances towards the player, beginning an encounter.

As the player fights with one of the robed figures, they'll take note of how Sydney is faring against their attacker in the background, their state progressing each turn.

  1. Sydney struggles against his/her assailant.
  2. Sydney manages to push the monk/nun away from him/her.
  3. Sydney frantically looks around for something to fight the monk/nun off with. His/Her eyes settle on one of the pink canisters.
  4. Sydney picks up the canister and fumbles with it. A spray of pink mist hits the monk/nun right in the face. He/She stumbles, and looks disoriented.
  5. Sydney rushes towards you.
  6. Sydney points the canister at the monk/nun attacking you.

After the sixth turn of combat, Sydney will save the player if they haven't already subdued their attacker by making them cum or beating them. There is effectively no way to lose this encounter.

Regardless of how the fight ends, Sydney sprays the monk/nun with a pink mist, causing them to collapse in a pile with their colleague. They wipe the player's tears with their sleeve (- - Pain) before looking down at the monks/nuns scornfully, marker in hand. "I assaulted an innocent initiate, I need to be purified" has been written on both of their faces, with the words curving around the nose and mouth. Sydney smiles mischievously.

Sydney then begins to muse about why the "pink stuff" is being kept with the belts and paddles, before brushing it off. "Let's hurry up and find what we came for. I don't feel safe down here anymore."

If the player chose to pick the lock, this encounter will not occur, instead skipping straight to the search.


The player and Sydney begins searching the room. There are several spots for the player to search, each with a different outcome.

Aside from providing flavour text, these options do nothing, as Sydney will eventually find the key. The player cannot find it on their own. Regardless, the player's options are as follows:

  • Search by the chastity belts - The player searches the cabinets containing various chastity devices. Under one, they find a paper containing business jargon; if their Business Fame is at least Recognised, they'll identify it as an invoice, noting that someone spent a lot of money on these devices. Much of the page is inked out, but a "W" is signed at the end.
  • Search by the paddles - The player searches the paddles. They note that they at least seem to be cleaned after every use, judging by the wood cleaning solution and piles of dirty rags. They pick one up, noting its weight and shuddering at the thought of being struck by one. | + Stress
    • If the player has any of the Masochist Traits, they'll gain Arousal rather than Stress.
  • Search by the blindfolds - The player searches the blindfolds, finding little of interest, save for some small, pointy disciplinary devices.
  • Search by the gags - The player searches the gags, noticing that they're clean, as if new, before listing the various types of gags they find. Ball gags, ring gags, simple strips of cloth, tape...
  • Search by the pink canisters - The player investigates the canisters, of which there are few. They smell faintly familiar to the player.
  • Search the black robed figures - This option is only available if the player did not pick the lock earlier. The player finds a small brass key on one of the robed figures, but it doesn't fit Sydney's belt.

Eventually, after breaking into a locker drawer, Sydney finds what they're looking for: a silver key, the same silver as their chastity belt. If the player is also wearing a belt, they'll recognise the key, being the same type used to lock the player's own chastity belt. After some further rummaging, Sydney produces a second, similar key.

The player moves to unlock Sydney's belt, but they stop them. "I want to," he/she says. "I really, really want to. But not here. We need somewhere private." He/She stares into your eyes, his/her own full of intensity. "Somewhere soundproof. I know a spot." The take the player's hand and lead them back into the hallway.

The Prayer Room

Creeping down the corridor, Sydney searches the wall, grabbing one of the cracks. A hidden doors opens, and Sydney leads the player inside.

The pathway leads to a small, hexagonal room, lined with steps leading to nowhere and windows high above on each wall, with a single cushion in the center.

"This room is one of the temple's best kept secrets," Sydney whispers. "A prayer room that's said to be closer to heaven than anywhere else. Prayers tend to get intense here, so it's completely soundproof. For the sake of the people outside."

In the confines of the prayer room, Sydney shakily inserts the key into their belt. It clatters to the floor. If the player is wearing a chastity belt themselves, they'll do the same with the other key.

With their belt finally removed, Sydney approaches the player and pulls them onto the cushion, flipping on top of them.

"This is the most sacred place in town," he/she murmurs, his/her mouth just barely grazing yours. He/She grinds against you. "Won't you defile it with me?"

Defile Sacred Ground

The player proceeds to have sex with Sydney in the prayer room, initiating an encounter.

There are a few key differences separating this encounter from others, the most noteworthy being that Sydney's chastity belt is removed, allowing the player to take their virginity. The other unique aspect of this encounter is the fact that the player will be afflicted with a slight hallucinogen each turn, noting that the incense is making them feel light and dizzy. Otherwise, the encounter functions the same as any other.

Once Sydney cums, however, things start to go awry.

  • Sydney doesn't get up, and refuses to let you move. "You didn't defile me. What are you waiting for? I need you to ravage me!" He/She's on you again. The hallucinogens have driven him/her mad with lust!

At this point (and after every subsequent orgasm), the player is given two options, both inevitably leading to yet another encounter.

  • Allow it - Makes the encounter consensual. Recommended to avoid Stress from accumulating.
  • Try to resist - Makes the encounter nonconsensual.

In the ensuing encounter(s), things get even stranger.

  • Sydney's health will read "He/She looks love-drunk/sinful/crazed/wild with lust/rapturous," giving the player no idea of how much pain Sydney can take (not that it matters; see below).
  • At the start of the encounter, the player will receive one of three lines, depending on how far they've progressed.
    1. You feel as though some unseen force is pushing you and Sydney together. - The first of the three lines. Applies a slight hallucinogen to the player, altering their perception.
    2. You don't remember when it happened, but all of your clothes have vanished. Your mind feels fuzzy. - Repeats the hallucinogen effect, and completely strips the player of whatever clothing they were wearing.
    3. The room spirals out into nothingness, and only your lust remains. - Repeats the hallucinogen effect.
    4. From the fourth encounter onwards, the player will not receive any further prompts.
  • The line about the incense making the player feel dizzy is replaced, once again changing based on how many times Sydney came. Each of these lines applies a slight hallucinogen to the player, with the latter two being more potent than the first.
    1. The temple is melting away.
    2. The incense swirls around you both, binding you together.
    3. As one.
    4. From the fourth encounter onwards, the last line will repeat indefinitely.

Attempting to fight Sydney off in their love-drunk state is not recommended, as this will not progress the encounter at all, nor will it deter Sydney. "You better hit me twice as hard this time, lover. We're nowhere near done." | + Lust | + + Trauma

Asking Sydney to stop has a similar effect - that is, it has no effect at all. Sydney moves to get off of you, but it seems like something stops him/her. Before you can react, he/she's back on top of you. "Stop? No, no no no. I'll never stop. I've waited too long to stop now! We will both be defiled, my beloved!" | + + Trauma

At minimum, the player will be forced to endure four back-to-back encounters with Sydney. Each time the player brings Sydney to orgasm, they'll become more and more deranged, as reflected in their post-orgasm lines.

  • You and Sydney are both a mess. He/She looks at you through lust-crazed eyes. "Defile me! We must be as one! I won't let you go until you do!" The room begins to warp around you.
  • "You. You will make my body and yours as one. We will be bound forever. Just give in to me, and let me give in to you." Sydney pulls you back down again. There's nothing else in the world but you two.
  • Sydney pulls you back into his/her embrace each time. It seems he/she won't be satisfied until you are both defiled.

The fourth line - and the encounter as a whole - will repeat endlessly until the player takes Sydney's penile/vaginal virginity. Note that this will require the player to lose their own virginity, assuming they haven't lost it already. If they're an angel, they'll lose their transformation and become a fallen angel.

If Sydney and the player are both female (thus making them unable to lose their virginities to each other), the scene plays out somewhat differently. The encounter will end after making Sydney cum four times (i.e. after the As one, message appears), rather than stretching on indefinitely. Additionally, Sydney's lines when demanding the player to go another round will be slightly different.

  • Sydney doesn't get up, and refuses to let you move. A manic expression crosses his/her face. "Where are you going, my love? We've only just started!" He/She's on you again. The hallucinogens have driven him/her mad with lust!
  • You and Sydney are both a mess. He/She looks at you through lust-crazed eyes. "More," he/she demands simply. The room begins to warp around you.
  • "More!" Sydney pulls you back down again. There's nothing else in the world but you two.

These lines will also appear if the player manages to take Sydney's virginity before the fourth round of sex.

After the fourth round, if the player has fulfilled the aforementioned conditions (either taking Sydney's virginity or not being able to take their virginity in the first place), Sydney finally collapses atop the player, spent and satisfied (- - - Lust). Before long, the player begins to drift away, too.

A phantom howl fills the room as it comes back into focus around you. You feel your consciousness slipping, and your body gives in to exhaustion. Forever, as one...

As One

When the player awakens, they find themselves in Sydney's embrace, and half an hour has passed. Though they still feel dizzy from the incense, they feel refreshed. | - Fatigue | - - Trauma

Sydney stirs, stretches, and sits up, making no effort to conceal their naked body from the player. "I love you," he/she says as he/she drops back down to hug you. You sit in the afterglow, content to enjoy each other's touch. Eventually, Sydney and the player rise and return to the temple proper.

Sydney and the player attempt to return the way they came, only to find it blocked by a group of monks/nuns in black robes. "Shit. Alright, plan B, we can get out by going into the garden." The cool night air and smell of nature soothes the player's nerves as Sydney whisks them to the garden. | - Stress

Once in the garden, Sydney wistfully chatters about their life-changing experience. "I knew it would be good, but... why are they trying to keep that from us? Because we won't reach heaven? Bullshit! We just found heaven!" They tackle the player onto the grass, pinning them down and kissing their face as they begin to disrobe. "I wanna go again. You wanna go again? I want to feel you again."

Before they can take things any further, a voice interrupts from a nearby pathway as a figure in a white cowl emerges. It's Jordan. They smile gently as Sydney nervously greets them.

It doesn't take long for Jordan to notice Sydney's missing chastity belt, even as they hasten to cover themselves. Sydney frantically tries spinning a lie about their belt being broken, but this only further rouses Jordan's concerns. They give the player a suspicious glance before turning back to Sydney. "Would you mind if I inspected your virginity?"

Jordan's Inspection

Sydney whimpers at the prospect of a chastity exam. They begin to plead, but Jordan cuts them off with a firm voice. "I was caught off guard, as this is the first time in recent memory I've seen you without your chastity belt. I only wish to confirm your words. However, I'm sure you understand what you're admitting if you refuse an examination."

Cornered, Sydney can only lift their robes in compliance, allowing Jordan to inspect their genitals. Sydney tearfully mutters an apology as Jordan backs away, having finished their inspection.

"Sydney..." Jordan sighs, before giving a gentle smile. "What are you sorry for? You are unblemished, and may it stay that way. I'm sorry I doubted you."

Jordan goes on to tell Sydney they can have their chastity belt refitted tomorrow, then bids them and player farewell, leaving Sydney dumbfounded. "I... we did have sex, right? You- I know you took my virginity! We were as one! How..." The player postulates that Jordan was mistaken, but Sydney denies the notion, claiming Jordan "knows his/her stuff."

After a moment of thought, Sydney comes to a realisation: the prayer room had altered their perception, somehow preventing them from losing their virginity. "It... kinda sucks that you didn't actually defile me, but do you know what this means?" He/She leans his/her forehead against yours and lets out a breathless laugh. "We can have all the sex we want in that room, and the temple won't know! We can cheat the system!"

With this, both Sydney's and the player's virginities (if the player hadn't lost theirs elsewhere) are restored, though the stats tab will display Sydney's as being taken. If the player had become a fallen angel in the prayer room, they'll rush to a bond to look at their reflection. The feeling of loss quickly fades. You still look pure.

If Sydney and the player are both female, the scene is heavily cut down. Instead of worrying, Sydney is relieved when Jordan simply asks to inspect their virginity, and Jordan finds them to be pure. Once alone, Sydney simply states, "Good thing neither of us has a penis, right? I guess we never had anything to worry about," skipping the monologue about the prayer room and walking the player back to the main hall.

After the scene in the garden, Sydney and the player return to the main hall of the temple, until someone comes marching up to the pair. It's Sirris, fretting over how late Sydney had been staying. Their worrying dissipates when they notice how happy Sydney looks, however, and they place a hand on the player's shoulder. "Thanks for looking after him/her. Really. I hope you two had fun."

Sirris then offers to give the player a ride back to the Orphanage, to which the player can either accept or refuse. In any case, this signifies the end of the sequence.

Cheating the System

With their newfound knowledge, the player is now able to take Sydney to the prayer room when asking to go for a walk with them. They'll accept at any time of the day (except on Fridays), regardless of whether they're at school or the temple, provided they're still in their Corrupt state.

The encounter functions the same as it did the first time, with Sydney going mad with lust until the player manages to satisfy them, and the player and Sydney's virginities will still be protected within the confines of the prayer room. The player is also exempt from losing their angel transformation when having sex in the prayer room.

It's worth noting that the removal of Sydney's chastity belt is permanent; they will not get a replacement belt after the prayer room sequence. This means that if the player wishes, they can have sex with Sydney in a location besides the prayer room and take their virginity properly. This will have consequences, as Sydney and the player still have their chastity vows to uphold.


  • The removal of Sydney's chastity belt, and the player's if they were wearing one.
  • The ability to have sex with Sydney without taking their virginity, or the player's.


  • Both paths involve Sydney wanting to remove the belt "one way or another." However, the event that achieves this differs depending on the path.
  • It is theoretically possible to completely corrupt Sydney without having sex with them and/or going to the Temple. (and subsequently becoming an initiate there).
  • Despite Sydney's max corruption and personality change, they will maintain their positive relationship with their parent, Sirris. They will also continue working at the rental store in the school library. Additionally, they will also still blush out of embarrassment during certain events.
  • It is possible to re-purify Sydney after completing this quest. However, unlike with its pure alternative, part of its rewards will be rendered inaccessible (temporarily, should the player corrupt Sydney yet again). Although their belt will stay off, the player won't be able to invite Sydney to the prayer room if they're in their Pure or Neutral state.

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