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mellowwillowy · 5 months

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𝐃𝐞𝐭𝐞𝐧𝐭𝐢𝐨𝐧

⤷ Synopsis: An honor student was sent to detention, and to everyone's surprise, it was nothing out of the ordinary until the headmaster decided that he had enough and gave your beloved caretaker a call.

⤷ warnings — possessive behaviors, mention of past abuse and trauma, gn reader

"Seriously, your caretaker will be hearing this soon." The headmaster grumbled as he pinched the bridge of his nose, another trip to detention which you thought would just be another chance to laze inside the headmaster's room, sleeping on the couch while killing time.

"Didn't he tell you not to bother him over menial problems like this?"

"Considering how many times you have lazed in my room, I wouldn't say it's menial anymore. Besides, just what made you think that it was a great idea to pick a fight with Whitney?!"

You groaned at the headmaster's bickering, waiting for your beloved caretaker to just come and patch your wounded ass. Picking a fight with the head bully was never a great idea but you were somehow itching for a fight by the school's corridor out of nowhere!

"He should be here by now."

"And you will not be hearing the end from us."

The doors to the headmaster's room swung open, revealing your caretaker who was wearing an annoyed expression. "I supposed it's supposed to be something important, Leighton?" The man questioned your headmaster as he leaned toward the doorframe.

"Did you not learn the etiquette of referring to someone who is older than you too?"

"Oh I'm so sorry but we did not recall ever seeing you being a proper headmaster."

You and he both attended the same school, and the only thing that was surprising enough was that the uniform you two once wore hadn't changed much. Some may say that your uniform seemed a bit different but that was all, no further questions were asked about you. Especially your age.

"Your pretty little brat was causing trouble again, am I in the wrong to summon their beloved caretaker?" the headmaster spat as he drummed his fingers on the table, "Not the first, second nor tenth. But I couldn't just close my eyes anymore on this matter."

You tugged on your caretaker's suit, "Bailey, do you have bubblegum?" Surely you were defiant enough to not listen to the headmaster's bickering but he wouldn't do anything about it. He couldn't.

Bailey sighed as he handed you a pack of bubblegum, at the very least it kept you away from cigarettes. "And?"

"If I have to say, I am kind enough to give them preferential treatment, wouldn't you say so too? No photographs, no spanking, and no-"

"I think you are a bit too high over your head right now," Bailey growled at his remarks, "I too, am being nice to you. What do you think this school will do to a perverted headmaster like you if I leaked out all the blackmail materials you had against the students?"

You thought to yourself as you blew out a balloon, would the mayor do anything about this? Probably not unless a revolution started or the Mayor was edged by Bailey until he had no choice but to dismiss your headmaster.

"You are wasting my time, you know that right? And you," Bailey looked back at you, making you pop the balloon and chew the gum back.

"What?"

Bailey chewed back all the nasty words he was about to tell you as he scratched his head, "Get into the car. I'll have a chat with him first." You shrugged and left the room without looking back, shutting the dual doors tight.

"I'm not going to say much anymore," Bailey stood up from his seat and walked toward the door, "they could not feel how it's like to be a student and all you had to was turn a blind eye to everything they did, is that so hard?"

The headmaster's face contorted into a scowl, "Bastards, you two really have your caretaker's tendencies running thick in your blood, blackmailing just to obtain what you want."

"Whatever you are saying, if I see them troubled again, I won't be this lenient anymore." Bailey slammed the doors with a loud thud and thought to himself, just who was the brat that punched you so hard that it cut your left lip?

Bailey groaned at your sight and started to drive like a madman toward the orphanage, "Good, just make sure you can at the very least win."

"Did you win?"

"Hmm... I think so, considering how I'm the only one who could walk to detention." You shrugged as Bailey examined your bruises in the car, your uniform torn and stained with blood, your hair disheveled, and a cut on your left lip.

You cackled at his words and started to play the radio, bobbing your head to the tunes, "Reminiscing how hellish it was whenever you see me wounded?"

Bailey didn't respond but hell he knew what you meant. The two of you were not catered to as children and ironically enough, the boy you once remembered as someone kind and loving is now a ruthless extortionist called Caretaker, perhaps he was worse than your previous caretaker but he was nice enough to not do anything toward the children that were not considered as an adult yet.

Perhaps that was the only justification you could give him.

You pouted at his words, those who failed to pay will be sold but you knew he wouldn't do that. Besides, the others would be squirming happily should he ever sell you.

"Ah right, time to pay up brat."

"No preferential treatment for me?"

"You are still my orphans and I am nothing but a fair man."

"I think I'm short in money sir."

"What a coincidence, I need someone to clean my bedroom and make my bed," Bailey looked at you side-eyed, "and I need someone to keep me company for the night, I suppose you could cover up your debt with this much yeah?"

#DOL #Degrees of Lewdity #Bailey the Caretaker #Leighton the Headmaster #Whitney the Bully #Yandere x reader #x gn reader #this is a shitpost

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dollya-robinprotector · 10 months

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Also may I present to you: The teachers

#Yeah Winter you sus #Sirris is my papa #Doren and RIver remind me of Iskandar and Lord El Meloi #Mason is baby #And Leighton #ho ho ho oh beloved headmaster Leighton #degree of lewdity #degrees of lewdity #sirris the science teacher #winter the history teacher #river the maths teacher #doren the english teacher #mason the swimming teacher #leighton the headmaster #dollya art

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ashersanity · 6 months

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Eyes only on me, PC

This was just sitting in my drafts, don’t really know what else to do with it along with my other 7 unfinished works that we don’t talk about.

Pairings : (M!Whitney x sub GN!PC)

Summary : (Basically a possessive and jealous Whitney kidnaps high sex fame PC for slutting around. A spin on Whitney’s dismissal event except instead of selling you off, at high love, they fuck you.)

Content warning! : (kidnapping, dub-con at best, non-con at worst, Whitney is a warning on it’s own honestly)

This one’s really short. Don’t got the motivation to extend on it, but it has potential.

Whitney knew you were a slut. Everyone in town knew you were one. It didn’t bother him, in fact, he relished in seeing your needy mouth on his cock, slowly sucking away while his friends watched. Crowd jeering and cheering as you shamelessly bounced on his cock in public, at the pub.

It didn’t bother him. Until it did. Didn’t know when the hell it started, but when his friends snicker among themselves, passing around pictures of the notorious whore in town. It begins to feel weird for him, not so funny anymore. What the fuck is that feeling in his stomach, that made him grind his teeth and clench his fists?

Jealous. Whitney was jealous. And it was all your fucking fault.

The bully just brushed it off at first, thinking nothing of it. It was a stupid thing to get pissy about it, not like you guys really were a thing. You were just a hole he used for his own self-satisfaction, nothing more. It really started going downhill when he saw that video of you getting your ass fucked by the goddamn headmaster. Even Leighton, the old fuck had gotten a taste of you, messed with his property and filmed it too.

Didn’t know why, he just fucking snapped, ambushed you in an alleyway, snarling about how this was your fault and he didn’t have a choice. Nearly twisted your arm as he pinned you down and shoved a damp cloth against your face before you even managed to get a punch in.

There was nothing sweeter than seeing you awaken all disoriented and confused in his bed, that was surprisingly well-made too. Had you ingest a couple aphrodisiacs that he bought from a shady dealer, so you were all flushed up, panting and ready for him.

You wanted to be a whore? Well, then, fine. Whitney will indulge since he’s in a generous mood, cock already out of his pants to sink into that tight heat of yours. He’ll fuck your brain out till the only name that you’ll be whining will be his own, pound into you till you’re filled up to the brim with his cum and he’ll still be going. Fucking you so that the only thing you’ll be craving is his cock and his cock only, not some other bastard. Snarling that you’ll fucking take it and you’ll love it too.

Because you’re his slut.

#dol #degrees of lewdity #whitney the bully #dol whitney #degrees of lewdity whitney #leighton the headteacher #leighton the headmaster #asher writes #writing #what is this

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junjunjunko · 2 years

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More Degrees of Lewdity in a Nutshell.

A continuation of these shitposts! Part 1 Part 2

#shitpost hours #dol #degrees of lewdity #art #my art #kylar the loner #robin the orphan #whitney the bully #bailey the caretaker #leighton the headmaster #pc #sydney the faithful

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pip-n-chips · 6 days

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GODDD ffhgggnnvs teacher desk fucking

Sirris doing it in front of the class to demonstrate something for the lesson.. you're leaned across it on display n they do it slowly and carefully, explaining the steps and your reactions.. voice slowly gets less steady as it goes on. points out telltale signs when you're close to orgasm :)

Doren pinning you down against their desk after school.. they found you alone and vulnerable in the halls and they stayed late, anyways. might as well keep you company.. comfort turns into a kiss turns into you pinned against their desk and their papers scattered on the floor.

Leighton using a dildo on you because they decided just the paddle wasn't punishment enough.. you're already in so much pain you can barely scramble away when you feel the cold lube drip down to your hole and something prodding your entrance..

yehag

#sirris the science teacher #doren the english teacher #leighton the headmaster #leighton the headteacher #pippy rambles #degrees of lewdity #skajqoanakakqaa #thirsty

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limerencedisorder · 27 days

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i didnt feel like writing a comment so im jus making a post lolol

(theyre referring to this post)

first of all, its the scene where leighton punishes sydney. (to trigger this event, either you don’t return a library book you rented or RNG.) and if you want kylar involved, it just has to be raining or snowing. this can only be triggered during lunch break i think.

options to get this scene: 1 (intervene), 2 (offer to take part of the punishment), 3 (grope sydney while spanking), 1 or 2 (encourage sydney, wiggle your bottom), and 3 (thank sydney).

tags: @salty-muffin @kittiesandkillers and i think the other person turned off their @s lol

#dol #kylar the loner #sydney the fallen #leighton the headmaster #degrees of lewdity

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morgana-ren · 10 months

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Leighton, who knows your face but not your name once school is in session. He's never met you before, but you catch his attention in the hallway. You're laughing and giggling with friends, school folder squeezed to your chest and a sweet smile on your face. You walk right past him without a glance, too engrossed in your conversation to notice his leering.

Pretty thing, he thinks, wondering if he has any photos of you.

Surely not. He'd remember someone like you.

Leighton, who sends Sirris out to the cafe as he conducts his 'inspections.' Camera in hand, he lines the girls up and tells them to unbutton their shirts and flash their breasts— for health reasons, of course. He takes his photos as each girl strips and shifts uncomfortably before sending them back to their seats. His grin widens when he realizes you're at the end of the line.

Finally, he thinks.

You lower your blouse over your shoulders and ball your hands on either side of your torso, trying to hide the view from anyone but him, hard swallowing and trying not to meet his eyes. He stares for a moment before finally snapping a few photos, catching your quivering lip in the shot.

"Nice pair,' he says, licking his lips and imagining what it would feel like to jiggle the fat in his palms. You flush, shrinking back as he reaches forward and indulges, running a calloused thumb over the hardening peak. A quick squeeze and he realizes he's out of time.

She'll give me an excuse one day, he thinks, palming his hard cock beneath his desk. All students do at some point or another. You'll end up in his office. He's sure of it.

Leighton, who grows tired of waiting. You're a good girl, it seems. Well liked and behaved. A teacher favorite. So he takes things into his own hands.

He bribes two delinquents to frame you. He doesn't care how.

Just ensure she is sent to me, he tells them. They oblige gleefully. Thank God for this horrible town and the rotten fruit it bears.

Leighton, who is particularly careless with his car the next day. He drives through puddles and parks under trees; he doesn't take the tunnel to work, letting the rain wash over the paint job. Filthy, filthy, filthy.

It won't stay like this for long, he thinks.

You sit in his office after school, squirming and fingering anxiously at your skirt. You've never been here before. You're a good girl.

"I have something special for you today."

He takes you to the private lot, pointing to the sponge and bucket of soapy water sitting beside his car. You look at him and then the bucket incredulously. Surely he doesn't want—

"You'll want to take off your clothes for this," He grins, with far too many teeth. "No sense in getting your little uniform dirty."

You do as you're told. You strip down to your panties and get nice and wet and soapy cleaning his car. He watches attentively— very attentively, legs crossed to hide the throbbing length straining against his slacks.

"You missed a spot," he points, leaning in for a better view as you bend and buff out some dirt on his bumper. Your wet underwear clings to your ass, starting to ride up, and you don't dare pinch at it—

If only he had more time, he thinks.

Leighton, who raises a hand to Sydney in the Library. You rush to his aid, demanding an explanation.

"Supplies have gone missing under their watch," he tells you. "And they are responsible."

You claim equal responsibility, noble little thing that you are.

"Punish me too."

You don't have to tell him twice. Normally he'd have you both over the counter, but he can't pass up the opportunity. He empties the library, and tells Sydney to lock the door behind him. He won't hear any protestation from the little brat. None of it.

"I'm doing as she asked. Now get out."

You cling to the desk as he bends you over and flips your schoolgirl skirt, biting your lip to hide your shame. He takes a good, long look, committing it to memory before slapping the curve of your ass with his hand.

God, what he wouldn't give to—

Oh, wait. He's the headmaster. He can do as he pleases.

Your knees buckle as he crooks a finger in the waistband of your panties and gives them a firm tug down.

"This is a severe infraction, and thus begets a severe punishment. One you won't soon forget."

And one he won't either.

You yelp as he repeatedly cocks his hand back and slaps your bare bottom without mercy, your eyelashes wet and dewy as little silvery tears trail down your cheeks. Your cries border on obscene, and if he tries, he can imagine you're moaning for him like the naughty little thing he knows you are inside.

Your skin turns the most delicious shade, abuse leaving you already turning a cosmic shade of colors from the bruising. He almost pants harder than you do, hardly even needing to touch you to feel his peak approaching. He's horrified, but he can't stop. He's gone far past the 'deserved' punishment but the way you mewl and whimper has his mind obscured with hazy pink lust.

"H-headmaster!"

"Please let me go!"

"I'll be a good girl, I promise!"

He has to stop. He has to. If he doesn't, he's going to make a mess of his trousers.

A mess that should be on your teary little face and jiggling tits and all over your pretty cunt and deep in your bruising ass

With a final blow, he releases your arms, trying to catch his breath. You stay bent and sobbing long enough for him to catch a quick photo on his cell.

(Never the cell phone. Never ever the cell phone. Too traceable, too damning— but he can't bear to forget the sight in every marvelous detail. Before the shape of his hand disappears from your creamy skin and his handiwork heals over.)

Leighton, who leans over you as you sob, large hand grabbing a rough handful of your ass, snarling in your ear.

"You're a naughty little brat, and I'll be seeing you again soon. Mark my words."

He knows you feel his eagerness as he presses against you; there's no way you can't feel the hot, hard length practically ready to pop behind his zipper. His face is as red as your behind and he can tell if he doesn't pull away now, he'll have you here and now. He wouldn't be able to stop himself— couldn't control it.

Leighton, who turns without another word, leaving you heaving and weeping against the counter, bottom bared and practically bleeding.

Leighton, who beelines to his office, locking himself inside before making the mess he so longs to all over the printed pictures he has of your exposed tits and pouting lips.

It's not the same.

It's not the fucking same.

Leighton, who decides in that moment that he can't live if he can't defile you himself. He wants to feel those tight, wet walls constrict around his cock, velvety and hot. He wants to spread your legs and work you over until you're a panting, moaning mess, begging him to stop—

To keep going.

Leighton, the educator, who would be remiss in his position if he didn't teach you all about sexuality. About the dirty things humans do in the dark. About what a mouth is truly capable of and that your ass is used for more than just discipline.

Leighton, the headmaster, who announces to the school the very next day that he'll be rewarding all of his best students with private positions in his office for extra credit.

Leighton, your headmaster, who makes it mandatory.

#degrees of lewdity #leighton the headteacher #leighton the headmaster #Leighton dol #yeah this isnt the actual piece i was working on but its something small #enjoy the depraved filth #utterly gross right #why oh why do i love older men who abuse authority and clearly have a temper problem

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ihonestlycanttellyou · 7 months

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I thought only Doren had this scene omg, I'm lucky! :]

Tf was he doing though??? 🤨

#degrees of lewdity #dol #leighton the headteacher #leighton the headmaster #dol leighton #scene sharing #dol pc #dol pc: Onyx #Babygirl Leighton #<- my simp tag maybe idk

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angelgoeslewd · 2 years

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Kitty!PC is being SLEPT. ON.

Whitney pulling your tail to get their attention, stroking it to make you cum

Giving Kylar a tail job while you push him up against the bathroom wall and cuddle into his chest

Sleeping in Robin's lap. Period.

Sunbathing and falling asleep in the library, Sydney watches your kitty ear twich as you sleep and whisper-yells at anyone talking too loud so they don't wake you up

Bailey absolutely tries to get to to hunt mice around the orphanage. You won't do it. You prefer fish.

The dock workers love you. They feed you pieces of freshly caught fish in exchange to stroke your head.

Avery showers you in kitty themed objects, paw print socks, bows for your ears, stockings with lace and ribbon. You're his show-kitty.

Ok... you will hunt mice. But only for Alex. He's appreciative of you keeping his barn clean. Calls you his barncat.

Eden is kinda confused but is horny the minute you show him how sneaky you are and how well you can hunt.

You love to spend time in the bathroom, 'freshening up.' Bailey has bust down the door and dragged you out by your collar more times then you can count on one hand. You are the reason there is no lock on the bathroom door.

Also. Bailey sprays you with water when you're bad

Leighton is always finding ways to put his hand on your tail. He'll spank you with his hand to be able to touch it. Loves to watch it twitch. You might get detention just so he can fawn over you. Also loves the feeling of your rough tongue on his cock. Puts a bell on you.

Mason... has trouble getting you to swim. You have accidentally clawed him trying to get you out more than once. You make up for it by licking his wounds with your rough tongue.

If you get into trouble with Wren, be careful. He will keep you collared in his room and take pictures to sell. Takes you for walks. Ends with him fucking you when you try to sunbath.

You'd be Briar's house cat. You have a silk pillow to lay on by his side, the finest clothes, he'd take you every where... you are the shining star of his brothel. Miss Kitty's Mondays really draws in the crowd... breastmilk drinking is the main event 😉

#kitty!pc #dol #bailey the caretaker #DoL #degrees of lewdity #avery the businessperson #briar the brothel owner #mason the swimming teacher #whitney the bully #kylar the loner #eden the hunter #wren the smuggler #leighton the headteacher #leighton the headmaster #alex the farmhand #robin the orphan #sydney the fallen #☕ of dol #angelic songs

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shokujin-art · 5 months

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I hated him with such a normal amount that I wanted to try and design him. So I can draw more of him on my alt—

At least he made me learn how to draw beards and older characters 👌😳

#dol #degrees of lewdity #dol leighton #leighton the headmaster #myart #I love bullying that man

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thedarkonesposts · 9 months

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Let’s talk degrees of lewdity rare pairs. (REPLY WITH YOUR FAVES AND WHY… may sketch some for y’all 🥺)

Kylar pairings

This gets a whole section because most of my ships are just different Kylar ships

Kylar / Whitney

If Whitney can go from bullying pc to being soft why not do the same for Kylar? I love the idea of Kylar becoming fixated on Whitney against his will and obsessing over him despite how cruel he is to him- only for Whitney to catch on and take advantage (by fucking Kylar behind the scenes and still bullying him at school) I feel like Whitney can easily handle Kylar’s psychotic episodes. He’d just be like damn ok give me head if ur so obsessed with me, you’re the only one I fuck anymore anyways.

Kylar / Sydney

Wholesome? Sydney is so patient and understanding, loyal too, so I feel like he could manage Kylar well. Honestly just a fulfillment of them both being happy because I feel like they’d have a good relationship

Kylar / Sydney / Whitney

… the above but with the spice of Whitney making them realize they’re masochists.

Kylar / Harper

I just think Kylar needs to be in an asylum… getting groped and kissed by a hot doctor. They’re both insane and creepy.

Kylar / Eden

This may seem out of left field but let me break it down

- both possessive and jealous as fuck

- kidnappers

- Kylar has wife skills minus cleaning

- breeding kink

They’d be a shockingly healthy couple, Eden could keep his crazy ass in check and Kylar could be his personal fleshlight. Kylar would probably be in heaven if Eden kidnapped him and refused to let him leave- having someone be that possessive of him is like Kylar’s biggest dream.

Sydney/Leighton

headmasters pet, Leighton shows a weird interest and favoritism for Sydney that I think is gross… in a fun way. I feel like Leighton is trying so hard not to come on too strong but he’s clearly really interested in Sydney

Sydney/Harper

I swear I don’t just like authority figure / Sydney ships (I do.) I just think since they have a weird hinted at history it would be neat if that history was sexual and or weirdly romantic.

Sydney/Sydney

corrupt male Sydney and non corrupt female Sydney. It’s the ship to end all ships and I won’t take critiques

Whitney/Sirris

one sided, Whitney finds out that’s Sydney’s mom and flirts relentlessly, he gets turned down and takes it out on Sydney who does not care.

#tsefried rambles #degrees of lewdity #sydney the faithful #sydney the fallen #kylar the loner #whitney the bully #eden the hunter #harper the doctor #leighton the headmaster #is my Sydney and Kylar obsession obvious…

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whitneysboii · 10 months

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funniest(but also serious) thoughts i have for dol is just finding a way to get rid of encounters and all that sexual stuff

Because this game is so fucking interesting for a porn game how dare.

What is that tentacle room? Why is the wolf howl going to help? How does Black Alpha(i forgor their name) know and got into the room? Does this mean the room is actually physically present somewhere in the town/forest?

How dod Leighton manage to get to headmaster and no one realise anything about him for so long? Are they all actually aware of it? Do people who got used by him meet up?

Are there any townies who manage to move out? What the hell is up with Ivory Wraith? How did the town even get to normalizing everything?

What happened to Morgan? Does anybody else know Eden other than Bailey? How the hell does Bailey know Eden anyways?

I am so goddamn interested in every character, every part of this town, every little bit of story we get with characters and places it's silly

And perhaps my favourite question of all.

Why the hell does the town not bat a single eye to every single thing that happen but still require you to have an ID to get to the strip club bestie there are worse crimes that could be committed and there are. Very regularly. Townies really said "Your body may be grabbed, but god forbid you watch someone strip under the age of 18."

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Hello, anon! 👋

(I'm not sure if this is the same anon from before, but welcome, regardless!)

Firstly, any links that I post may contain spoilers, so use caution if you're trying to avoid them. Secondly, this post is probably definitely gonna be a long one, so strap in! (And hopefully this answers your questions, or inspires more!)

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I agree and I don't at the same time. (But I wholly agree that's it's too interesting for a porn game and how dare they lmao)

Getting Rid of Encounters / Sexual Aspects Completely?

A lot of the lore and characters that we love so much are based on the frequent encounters around town that they're fully aware are happening, but can't do anything about (partly due to the police literally not caring, and actually being part of the problem rather than the solution; the other part being if they truly want to or are capable of stepping in on PC's behalf or not). Obviously this changes things a bit if we remove the encounters or sexual aspects completely, although we might retain most story lines, quests, and characters if we still have the required ones (the Ivory Wraith* for example, and love interests such as Whitney, Avery, Alex, etc.). *If you're wondering why I included the Ivory Wraith, this has to do with their backstory. You can learn more about that here if you're interested. Again, beware of spoilers. I won't give anything away, but I was totally against the Ivory Wraith until I read that and now I'm just sad. Also, the tentacle room you mention - is it tentacle plains (accessible through the Hookah Parlour, or the mirror in your room at 3am)? I have suspicions that it's tied into the Ivory Wraith's story, but there's no solid evidence yet (aside from the tentacles, purple mist, the portal in the mirror, etc.).

Removing Only Unnecessary Encounters / Sexual Aspects?

If there was an option to toggle between "normal" and "required encounters", that would be ideal for people who want to play, but can't or won't for various reasons (I won't list them, as I'm sure people can draw their own conclusions if they've played this game). It might actually appeal to those who are asexual and/or repulsed by sex in general, too, which would be great for community building. (The only drawback I see are people becoming too aware of this game's existence and kink shaming, bullying, trying to cancel it, etc.) However, Vrel & team have done a wonderful job implementing something that's similar to that idea without removing the "core aspects" of the game (the point being to do whatever you have to in order to survive). Players can set their game mode to "soft mode" and limit their encounter rate, but this disables feats (if you're unsure of what feats are, they're basically achievements that earn you Vrelcoins; you can spend the coins into your next game to make it easier). Note that you can enable cheats at any point, too, though it has the same effects (no feats).

Soft Mode description:

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Black Wolf, The Alpha

As for the wolf howl and Black Wolf the Alpha, I actually haven't played as a wolfie in a while. I'll play through a save file and, should I find anything, I'll tag it here (it'll be under "mine", so it should be easier to find). I didn't know they could get into the tentacle room, so that's really interesting to know. Again, that makes me wonder if it has to do with the Ivory Wraith, although I'm not sure how Black Wolf would have gotten in if it does; the Wraith isn't specifically land-based as Black Wolf would be, so it's a bit strange. (Also, please send another ask if you find out anything - I love learning more about this game!)

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The Headmaster

Leighton is definitely hiding something, but I can't quite put a finger on it. I want to know who they're taking the pictures for, since they can easily go to the brothel (and do so regularly) and probably pick up any of the students there, too; there doesn't really seem to be a need for the pictures, at least not for Leighton. So, the next thing that comes to mind is that perhaps Leighton is selling them to someone underground. Someone who might have the upper hand within the school board, or maybe the town (Quinn the Mayor comes to mind, but I don't know enough about them to think they would be tied into that; however, there is an email about some sort of "sin" they committed and presumably "already paid for", but that comes into play with Bailey and has no mention of Leighton - both of them have positions of authority over students and/or (18+) "children", though, so maybe it's not so far fetched?). I don't think that the people who were used by Leighton meet up - however, it would be a unique quest line to follow. It could end with them being arrested (even if the PC has no involvement with the Landry & Mickey quest line, or it could occur after; could be a timed event), and Sirris, Doren, or one of the other teachers get promoted in Leighton's place for their hard work. Although, since Sirris has the Adult Shop and Winter runs the Museum, chances are that it would go to somebody else (i.e. Mason, Doren, or River). Honestly, I would prefer Doren, honestly, as they seem to be somebody that even Whitney hesitates around, so that would create a different kind of dynamic.

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Morgan, Eden, & Bailey

Not much is known about Morgan. I have a theory about their child, however, which is probably not anything new for this community. I'll pitch it anyway, because I personally haven't seen it posted anywhere. This is what the Miraheze blog states (which is not official as far as I know, but it does work and is accurate for most situations):

Morgan, upon meeting PC, calls them "Charles" or "Charlene." The dance teacher on Barb Street is named Charlie, which is a unisex nickname for the other two names above. I'm not sure what could have happened between the two of them, but something horrible must have left Morgan deranged in the sewers and Charlie on the surface, who potentially grew up by themselves. For all Morgan knows, or at least the PC, their child has/had passed away; if they were deranged before they lost Charlie, that would explain a lot, as they might not have been mentally stable (perhaps how they ended up in the sewers to begin with). If Morgan became that way after they fell into the sewer, they could be dealing with high trauma, severe hallucinations, and/or low control from multiple encounters (like what happens with PC).

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Eden probably wouldn't know Morgan since they pretty much never leave the Forest. They also probably don't know most of the other named NPCs (Whitney, Avery, Robin, Great Hawk, etc.) for the same reason. However, everyone there seems to know Bailey, regardless of where they've come from or been - Bailey has their hands in the pockets of nearly everyone in that town. Eden might know Bailey from buying the PC (to repay their debts), but there's a possibility they'd know one another outside of that. After all, Eden is a hunter - they face the things in the Forest that no one else dares to. This means that they probably come into town to sell the meat, fur, bones, and other bits of the wolves that try to attack them. Also, deer, foxes, and bears are shown to be out there, too, among other creatures (lizard-like beings in particular). Bailey may have found them at a butcher shop, grocery store, or a similar location (maybe even Connudatus Street, at the stalls), trying to sell their wares. Maybe they decided to cut a deal together, something where Bailey offered his "goods", too; a nice, new play toy for Eden and, in exchange, freshly caught food for the orphans.

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As for if anyone else would know Eden (outside of Bailey), there seems to be one other person. If you're dating Eden, then they'll come looking for you at Remy's (here's the farm scene, in case you want to read through it). It's unclear whether they know one another before Eden comes searching for the PC, however, so there's no solid evidence for either side yet.

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Misc. Questions

Are there townies that manage(d) to move out? While I don't know specifics, I think that there are a few people lucky enough to do so. Everybody talks about being "stuck in [this] town", but I think that Avery, for example, could totally leave if he wanted to. Maybe he doesn't for business reasons, or maybe the PC is his last reason for staying in town (could explain why he gets so angry when PC disobeys, because all he might want is someone to feel less lonely in this pitiful pit of a town, and he just needs one thing to go right and go his way for once). If you're someone like Robin, however, then you might be stuck there for a long time, assuming you do manage to find a way to leave. How did the town even get to normalizing everything? This is interesting to me because this had to have happened over several years, where it just became something that happened so frequently that people began to overlook it; we know this has been occurring since before the "Ivory Wraith" became known as that - so, at least since year 361. It may not have been something that happened often during that time, but it's probably been building up as people moved to or had families in the town. This might have been furthered by previous authority figures, such as other mayors, police forces, etc. I'd also suggest that Quinn might be involved, but it seems as though they'd rather scrub the town's image than let it be ruined (as it already seems to be, evidenced by PC getting asked about the town's rep while they work at the cafe); if they're not actively helping people get away from that, then they're allowing it to happen by not doing anything about it. Why does the town not bat an eye at everything else, but requires you to have an ID to enter the strip club? I've been wondering the same exact thing since I first started playing. I understand that the characters all have to be 18+ (for legal reasons, but also because... well... it would be weird if they weren't?), but I don't understand how you have to have an ID to get in considering there are other ways to "bend the rules." I'd love a side scene where you're forced to help Whitney + friends into the strip club (also maybe he makes you get on an empty stage and dance for him js), or maybe you run into Darryl at one of the parties that Charlie sends you to dance at. Either way, this offers different options for Darryl to see your potential; they could offer you a bar tending job first, then have you dance on the weekends for smaller crowds (of course, they'd have you perform more the better your dancing skills are).

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