#dol winter

[dollya-robinprotector]

Archeology field event or something after that-

PLEASE GIVE ME MORE WREN AND ROBIN INTERACTION RAHHHHHHHHHHHHHHHH anw Wren redesign yall hehehe gotta give him the "bird wings" treatment.

[the-real-lordrisley]

What I find absolutely hilarious is that DOL, a game with some absolutely horrendous things in it, has one of the sweetest, non toxic, friendly fandoms I have ever been in 😭🙏

[nopecho]

CREAM HEADCANONS

Based on a series of reblogs between me, @propertyofkylar and @propertyofwhitney67 !

Censored in fear of the tumblr rules (sorry guys I'm a coward)

I'm open with recieving other headcanons and suggestions!

[visualnovellover]

WINTER PLEASE JUST ONE CHANCE PLEASE FOR THE LOVE OF GODDDDDD

Forgive

Repent

[kittiesandkillers]

My interest is peaked.

[propertyofkylar]

kinktober day five: immobilized (m!winter x gn!pc)

word count: 806

tags/warnings: pillory usage, bdsm, spanking, teacher/student relationship, no genitals for reader but they are wearing a skirt

“So it goes like this?” You put on your most innocent voice as you leaned forward, placing your head in the divot of your teacher’s own pillory. 

“Yes, exactly,” the gruff teacher’s voice came from behind you. It made you smile as he moved the top part of the pillory down, effectively trapping you in the wooden contraption. 

“Oh, I see,” you wiggled your fingers experimentally. “I often see criminals in this in town. It must be uncomfortable to be here for hours.”

Winter sighed. “Yes, well, it’s not intended to be anything pleasant. I would recommend against doing anything that would get you placed in one of these by police.”

You could tell he was still behind you. Soon, it would be your time to strike. You continued speaking in that super-sweet voice. “But it’s okay for you to put me in here, right?”

Winter cleared his throat. “This is a controlled environment and it’s for educational purposes. So it’s okay.”

“Mm,” you said, wiggling your ass and feeling your skirt fly up, exposing your thong. You thought you heard Winter’s breath catch in his throat. “No wonder people are always doing things to the criminals in the pillory. It must be easy, since I can’t go anywhere.” 

“Yes,” Winter said quietly in response. You grinned widely, knowing he couldn’t see the mischievous look on your face. 

“Oh Winter,” you said sweetly. “Can you teach me more?”

“What would you like to learn?” He asked. 

You let out an innocent sigh. “Well, sometimes I see the people in the pillory getting things thrown at them. Can you tell me what other sorts of punishments go along with being in the pillory?”

This time, you were sure you heard his breath catch. “Ahem,” Winter said softly. “Well, you may have figured out that the purpose of the pillory is public humiliation. So, those watching the criminal may try to expose them.”

“Expose them? Oh, like this?” You shook your ass again and heard Winter groan in response. 

“Yes…” he breathed. 

“Winter, I’m a hands-on learner,” you said. “Can’t you show me what they would do?”

He swallowed loudly, but he stepped closer to you, and you could practically feel the heat radiating off of him. Winter flipped your skirt up and tucked it into its own waistband. His hand skimmed against your skin, making you shiver. 

“Oh, I’ve been so naughty,” you said with a sigh. “Someone should punish me for being so bad…”

“You certainly have been bad,” Winter said in a low voice. Then, a hard smack was delivered to your ass. 

The strength of it propelled you forward slightly, the hard wood of the pillory scraping your wrists and neck. “Ngh,” you sucked in a breath. “Is that common?”

“You’ve seen it for yourself, surely,” Winter said, before delivering another hearty spank. You cried out. “When someone is immobilized, it’s easy to do whatever you want.”

“Whatever you - fuck - want, huh?” You were breathing heavily now after just a few smacks. Winter was surprisingly strong. And it was turning you on more than anything. 

“No cursing,” Winter said, deftly bringing his hand down to your bare skin again and again. “You are a naughty one. Indecent, I would say.”

“Yes…” you said quietly. You could feel wetness running down your inner thighs. And you could tell Winter saw it too, because he tried to hide his gasp, but failed. This only seemed to motivate him more. 

Smack. Smack. Smack. One after another, Winter spanked your increasingly sore bare ass. You could only imagine how flushed your skin was now, imagine the look on Winter’s face as he repeatedly slapped you. Was he focused, with an intent, serious look? Was he having fun?

It was at this point that it really started to hurt. Your skin was stinging. Sitting in class tomorrow wouldn’t be fun. Though, you made a mental note to be extra squirmy and uncomfortable in Winter’s class. 

Tears sprung at the corners of your eyes, uncontrollably. “P-please,” you gasped. “I’m so sorry for being bad.”

“Hmph,” was Winter’s reply. He delivered several more stinging blows to your aching rear. Then, his hand withdrew. You let out a whimper. 

“I suppose this should be enough of a lesson,” he said, and then undid the pillory. You stood up, rubbing your aching wrists. But with how long you were in there, and the amount of abuse your butt had taken, your legs were weak. You stumbled - right into Winter’s arms. 

You took the opportunity to gaze up at him. His eyes were serious, but his pupils were blown out. You could feel a bulge in his pants rubbing against your midsection. So, you offered Winter your brightest smile.

“Now that the punishment is done, can you show me what happens when you’re good?”

[riwooga]

Forever thinking about Winter being in love with the PC…

Winter slowly realizing he’s falling for the PC, not only someone so much younger than him, but one of his own students no less.

The probable months of denial, of forcing his gaze away, of suppressing the fond smiles, but for every new interaction, every time the PC shows up with a smile and some new mysteriously procured artifact, nodding along in interest when he explains its origin… for every time the PC helps promote the museum, every time he hears them play along in the historic role play so fervently, goodness especially if the PC helped Winter not only restore the museum but helped him get his dreamed of field office too?

Regardless of how wrong it is, Winter feeling his heart stir for the first time in probably so long.. But he knows he’s too old for the PC, the dynamic would be beyond improper, and he knows he can’t let those emotions actually take root. All rationality in his mind probably berating him, of how he has children older than the PC, he’s past the years of his prime, not to mention again the severe taboo such a relation would have.

.. but I can’t help but imagine him sometimes wistfully thinking about if he was young again, letting his mind indulge in thoughts of what could be in another lifetime. Something he wouldn’t dare fully allow himself in this one. How he’d probably love to turn into a full on little archeological duo, exploring all the unturned nooks and crannies of the town, and even beyond.. but he’s not young and spry anymore, and him indulging, would almost feel like robbing the PC of that youth for themselves.

Maybe him going to the temple is half an attempt at also getting someone else to tell him that his actions are right, that he’s right to shut those emotions down, shouldn’t indulge. But even if encouraged to pursue, he knows deep down he can’t, no matter how much his mind and heart might disagree, he’s holding his morals tight, because what else can you really do in a situation so doomed to fall empty?

[getinthefuckingcarkitten]

Foxglove villain origin story

[digenerate-trash]

More head cannons that I have but for non-love interests. mostly teachers and Bailey and Harper. 

Bailey used to be a normal person who cared if the orphans got hurt but over time in order to keep the younger kids safe from the town he needed to start charging the older ones rent to keep this rinky-dink shack above water eventually it became too much for him to care about every victim he sent out onto the street to make rent so he stopped. Either by dissociation or worse. now he's just a heartless asshole who protects only the kids in the youth ward and even that is hard for him to do. The road to hell is paved with good intentions after all. 

Harper is afraid of blood. Straight up. He’ll faint if he catches sight of it that's why he prefers needles and brainwashing no blood is involved if you do it right. He's giving some real “I never got my doctorate” energy and I don't think this town cares because he's the best they have. He's definitely jacked off over an unaware patient. Has a kink for making patients cum hands-free (it's a power thing). Almost agreed to work for Remmy for free because he got too excited about brainwashing people into mindless cow hybrids. moral compass? Whos she? 

Leighton is such a fucking freak of nature. Would not be surprised if he went from teacher’s aid to head teacher solely through blackmail and other underhanded means this dud has always been a straight-up freak. Like Kylar but instead of being obsessed with one person, his passion is corrupting innocent people and once he's done and he's gotten off it's off to the next unsuspecting victim. This dude probably doesn’t know how to use a modern cellphone though so thank god for that. 

Sirris. Mommy? sorry. Mommy? sorry. I mean Mommy? Sorry. For real though giving milf energy. Probably really loved her dead husband to the point where she's not getting married again. (which is the real crime) but deeply cares for her kid, and even though she has no idea the extent of  Leighton’s abuse she has threatened to kill him and go to church the next day if he even breathes near her kid. Owns a sex shop purely to exploit this town's obvious sex addiction issue and is probably saving for Sydney's future as well. The only good parent I’ve seen in this game.  

River is a virgin for life. my man has never seen a pussy and is physically afraid of it. (same goes for cock but a little bit less so) has an avid believer of the church's teachings and he has a kind of friendship with Sydney but refuses to give them any special treatment because it wouldn't be fair (although Sydney is his favorite). Prob wear’s a chastity belt since he was 18 and has absolutely refused to take it off its like a security blanket now. No one is getting their filthy hands on this dick.

Doren is one of those freaks who has crushes on his students and sees nothing wrong with it, he cares about them and wants the best for his students but the power dynamic is hard to ignore for his students and even though he wants to be kind and a friend to all of them most students will avoid getting too friendly with him. He does his best to protect the students he likes best giving them snacks at lunch being extra patient with them during lessons helping them out or bumping up their grades just because they asked but if you’re a nuisance he lets you fall by the wayside because his love and care are conditional. 

Winter is heavy into costumes and BDSM but that's not a surprise super into weird sexual history and also has a huge denial/edging kink. Surprisingly the teacher she gets along best with is River. They hang out in the teacher's lounge and bitch about students. Leighton has absolutely harassed her for information on her students like which ones squirm during her unorthodox lessons but she refuses to play into his antics. When she's working at the museum she is the most content. It's her real passion but it doesn't pay the bills. Probably got hired because Leighton thought she would be an easy mark but it turns out she's a total dom and now he's afraid to fire her. 

Mason is the guy Dorent wishes he was. Students are always trying to feel him up during lesions and asking if he's single. But he really just wants to be left alone. At one point he was good enough to be on a national swim team but for one reason or another, his life fell apart and now he's burnt out and living in the worst town in Britain at the ripe age of 25. The dude probably wouldn't hurt a fly unless he had to and even then he would be crying for a week afterward. Bottom energy.

[degrees-of-lili]

The rest of the teachers and I'll copy the designs I did for the other teachers into this for completions sake and so I don't have to link them all from my Otome blog. Leighton, Sirrus (+Syd) and Mason.

[c0baltcat]

DoL PADORU vol.1!

=School Collection=

I’d include Leighton in another section due to image limitations

[yaelibex]

me sliding in @ Winter's history class

[kittiesandkillers]

I wonder what vrel means when he says that Winter has deep ties to the town.

Side note, Kylar has pinchable cheeks.

[propertyofkylar]

2 & 16 for Winter…do with that what you will. I want to see where you take it :)

teacher's pet - m!winter x f!pc

haha no this ask isn't exactly one month old today what do u me--*gunshots*

word count: 1196

tags: 2. jealousy/possessiveness, 16. student/teacher, age gap, lil bit of finger but mostly penetrative sex

You were in the locker room practically as soon as the bell rang, eager to have completed another day of school. You got dressed as quickly as you could with the words of your teacher earlier still echoing in your head. 

“See me after school today.”

Just thinking about it sent a shiver through your body. When he said it, Winter’s tone had your fellow students giggling. “Ooh, she’s in trouble…” but you didn’t mind. You brushed it off to your classmates. They didn’t understand. You did. 

Almost skipping down the halls, you made it to Winter’s classroom, where he was sat at his desk grading papers. You instinctively locked the door behind you and Winter lifted his head up to gaze at you, one eyebrow lifted. 

“Come here.”

His tone was firm and stern, and it sent a shockwave straight to your core. You tentatively took several steps forward. Winter let you stay in the uncomfortable silence for several beats before continuing with a sigh. 

“Flip up your skirt and put your hands on the desk,” he commanded, and you quickly did as he said. You could feel yourself growing wetter as your teacher stood up and stared at your bare ass. 

“W-Winter—” you began, but you were silenced by a smack to your ass. 

“No panties,” he tutted. “Really? Who are you trying to show off for?” He leaned back and crossed his arms against his chest. 

You suddenly felt quite embarrassed. “Nobody…” you mumbled. 

“What was that? I didn’t hear you.”

“I said nobody,” you repeated, barely louder than the first time. “It was only meant for you to see…”

“Is that so?” Winter said with a cocked eyebrow, though a hint of blush on his face indicated that his composure was struggling. 

“Yes!” You huffed, feeling slightly indignant. “Who else would I be doing it for?”

Who? That word seemed to grab Winter’s attention. Something shifted in his face and you had a realization. 

“You’re jealous!” You gasped, standing up straight, ignoring that your skirt was still tucked into your waistband, making you half-naked. Winter struggled to stay composed again. The mood had suddenly changed upon this moment, and you now were feeling quite giddy. “You’re jealous. Seriously? That’s so funny. I don’t get it.”

Winter sighed, looking away. “You’re so young,” he admitted. “You fit better with someone your age. Or even one of the younger teachers. Not me. So yes, I get jealous seeing you having fun with your fellow students. You should be with someone more like you. Not me.”

His surprisingly earnest speech tugged at your heartstrings. You stepped closer to him, gently taking his hands in yours. “Forget all about that. You’re my favorite teacher. I’d much rather be with you. Besides…” you subconsciously licked your lips. “I prefer my men a little more experienced than these boys.”

You stood on your toes and pressed a kiss to his mouth, which quickly grew heated. You threw your arms around his neck as he pushed your back against his desk, where he had already moved everything out of the way of the center. How thoughtful. The bulge in his pants pressed against your bare pussy and you groaned into his mouth. It never failed to surprise you just how virile he was for his age - which you didn’t actually know, as you were afraid to ask.

Winter’s wrinkled hands gripped your bare thighs and you smiled. The old man may have been jealous. He might have felt insecure compared to the people you hung around with in school. But the way he behaved when the two of you were alone couldn’t compare to anyone else. He was stern but soft, and always took great care of you. Just as he was doing right now, as his thick fingers stroked your clit, two slipping inside your cunt, which was practically dripping.

“Fuck!” You gasped at the feeling of his fingers stretching you out. He bristled at your curse. Stodgy old man wouldn’t change, even during sex.

“Behave yourself,” Winter scolded, but it honestly only made you hornier. You reached in front of you and undid his pants, opening his boxers to take out his thick cock, which was already red. The sight made you lick your lips again. Another reason why you chose to be with Winter.

Winter’s breathing got heavy as you began stroking his shaft, enjoying the feel of his skin beneath your fingers. “Winter,” you said, looking him in the eyes. “I want you.”

You needed to say nothing further. The tip of his dick slid against your folds, and once it was properly lubricated, he slipped it inside of you. Both of you gasped sharply at the feeling.

“Feels so good,” you mumbled as you rested your head on his shoulder. Winter let out a low moan as he began to thrust inside of you. To you, it didn’t matter how old he was. He was a skilled lover and took the time to figure out exactly what felt good for you. Which was a lot more than you could say for some other people you had slept with.

Whimpering with every thrust, you wrapped your legs around Winter’s waist, the two of you practically becoming one body. Winter steadied his hands on the edge of his desk, his breath hot and heavy in your ear.

“Oh–I’m gonna–” you felt your legs trembling and gripped Winter harder as your climax hit. You could feel your own wetness dripping down the inside of your legs as you came, shuddering and digging your nails into Winter’s back.

He, in turn, moaned your name, which made your body feel a way it had never felt before. The only sounds in the room were the wet slapping of skin on skin and the two of you panting.

You tried to meet his thrusts with your own, which was difficult with the way you were sort of perched on the edge of the desk. You pulled your head back and Winter’s eyes met yours. His were dark and heavy with lust. “Winter,” you whispered, and watched as those eyes opened wide.

“Fuck,” he mumbled, and if the pleasure wasn’t overtaking you at the moment, you would have scolded him right back. But you could tell his own peak was soon arriving, and you again tightened your legs around him, giving him no chance of escape. 

Winter moaned your name again as he came inside of you, filling you up with his hot cum. After a brief moment he looked at you curiously, as you usually didn’t do that.

“Marking me,” you said simply. “How can you get jealous when I’m carrying your cum inside of me?”

His face turned red, and he buried it in your shoulder. “I don’t know what to do with you,” he sounded exasperated, but warm. The two of you stayed like that for a bit longer before he spoke your name softly.

“Yes?” You said in response.

“Wear your underwear tomorrow. I don’t want to chance anyone else seeing you like that.”

You giggled. “Absolutely, sir.”

Winter nodded and patted your head obediently. “Good girl.”

[riwooga]

DOL npcs part 3, the teachers! ✨

Frankly it’s an injustice how little lewd we have with them 🤧 (what I wouldn’t give….for lewdness with Winter… or Doren..😩) I honestly also wonder if one of them will ever end up romancable? ..hm 👀✨

Anyway here’s the close-ups~

[whitneystoy]

I’m thinking of drawing each of the school recurring NPCs (the LI’s and teachers) as their yearbook photos, but that might take awhile so…. In the meantime I’ll work on either the gh scenes from the brothel or the janitor scene from the school

Also! Uncensored versions of my art are posted in the r/Degrees of Lewdity subreddit