Hiya, this is my blog where I post and reblog things for 18+ fandoms I can't post on my main or my art blog lol. I'm mainly into degrees of lewdity but may post other 18+ fandoms as well. Mdni obviously.
I'm the Gwylan specialist *fixes my nonexistent glasses*
Basically, you need to raise his interest first! You do so by unlocking clothes in his shop - like going to ufarm unlocks cow set and by telling Gwylan stories about your adventures you raise his interest
There's special sets - Halloween, Christmas and Valentine's - that can be unlocked by simply reaching specific dates. BUT while those raise interest those won't count towards unlocking him as a li, so I highly recommend to unlock them the hard way
At about 50-55% you'll unlock the beast ritual which is first crucial step. AND at >65% you'll unlock the intimate ritual.
During the intimate ritual you have the option to get on top and kiss him. That requires high physique and willpower and at least 40% lust.
He'll kick you out for a week and after that his social menu will include new stat - yearning.
The most effective way to raise yearning is to perform successful rituals and to offer to drink half of the poison during beast rituals.
At >81% interest and >50% yearning you'll claim him as a li! BUT!! You must eat breakfast at the cafe with him several time otherwise yearning will get stuck at 50%
That's reall brief and simple guide. I haven't tackled the hypnosis or transformation here but feel free to ask if you need clarifications!
I finally had another dol related dream. In the dream I left a house (unsure of whose it was) and then started getting chased by Eden through the woods. But I stopped because I saw a hurt looking dog. The dream ended there but I'm pretty sure it would have involved me getting caught or stopping and asking him for help.
I finally had another dol related dream. In the dream I left a house (unsure of whose it was) and then started getting chased by Eden through the woods. But I stopped because I saw a hurt looking dog. The dream ended there but I'm pretty sure it would have involved me getting caught or stopping and asking him for help.
*BANGING POTS AND PANS TOGETHER* APPARENTLY VREL SAID HARPER'S FAVOURITE POSITION IS THE STAND AND CARRY!!!!!!!!!!!11111111!!!!!!!11!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
HARPER'S FAVOURITE POSITION IS LIFTING UP THEIR PARTNER AND FUCKING THEM (WHILE FACING EACH OTHER) DO YOU HEAR ME!!!!!!!!!!!!!!!!!!!!!!!!!! IM GOING FAWKKING INSANEEEEE WAUUUUUUUGHGHGHGHHHHHHHHHHHHHHHHHHHHH
Pairing: Yandere!Harper x Reader (Degrees of Lewdity).
Written for a very lovely anonymous commissioner.
Word Count: 7.0k.
TW: AFAB!Reader, Non/Con, Extremely Unbalanced Power Dynamics, Mind Control/Hypnosis, Oral Sex (M. Receiving), Forced Masturbation, Medical Malpractice, Emotional Manipulation, and Nonconsensual Drug Use. Dead Dove: Do Not Eat.
Harper’s office was the warmest place in the asylum.
It might’ve been more accurate to say that it was the only warm place in the asylum, really. The communal rooms were inhospitable - too much plastic and too little body heat. The dorms were drafty in a way your cheap, tear-away blankets couldn’t keep out. Even the courtyard was freezing more often than not, any sunlight that might’ve trickled through the forest’s dense canopy immediately smothered by stone walls and wrought-iron gates long before it had a chance to reach the ground. You got used to going about your day half-frozen. It was the seeping kind of cold, the type that soaked under your skin and left you too numb even to shiver. Some days, you even found yourself envying the patients in straitjackets. At least they had something thicker than sheer cotton scrubs between them and the cold.
Harper’s office was a respite, in comparison. You spent the bulk of your free time curled up on his velvet-lined sofa, buried underneath a well-padded quilt with one of his less boring coffee table books in your hands. He was at his desk, an old-fashioned tape-recorder to his left and a laptop open in front of him, his hands moving gracefully over the keys as he jotted down notes from his last session. Whether he was in the room or not didn’t really impact your enjoyment of his hide-away, but the company was nice. The other patients weren’t much for conversation, and the staff— Well, there was a reason you liked Harper so much. That everyone liked Harper, really.
Thankfully, he was nice enough to pretend he liked you, too. At least enough to let you whittle away the hours until your release on his couch.
You were just beginning to nod off to the steady sounds of keyboard clacking and tape-recorder whirring when he called your name. Begrudgingly, you raised your head and found Harper smiling toward you as he nudged a small stack of documents to the edge of his desk with a pen. “Walk these to the archive for me, would you?”
You frowned, but sat up. “Don’t shove your work off on me, old man.”
“You don’t seem to be terribly busy with your own.”
“I’m a patient. I’m supposed to be resting.”
“Technically, according to the schedule our orderlies so lovingly put together, you’re supposed to be in the middle of a group session at the moment.” He cocked his head to the side. “Would you prefer it if I asked you to make your way down to the rec room, instead?”
A chill ran up your spine at the thought of sitting through another group therapy session. They weren’t worth the effort it took to attend. Most of the patients were so heavily sedated, they couldn’t remember their own names, let alone why they were here. Those who’d escaped their introductory appointment with minimal medication, like you, were similarly unhelpful. The questions posed were meaningless, the responses a never-ending onslaught of violence and rape and trauma retold in disjointed, half-remembered bits and pieces. You wanted to be sympathetic, to nod and coo and heal, but you couldn't take it. You’d all come from the same miserable town. You didn’t need more suffering. You had plenty of your own.
And so, you pushed yourself to your feet, marching over to Harper’s desk and snatching the documents away. He leaned back, his grin cat-like in its utter and complete self-satisfaction. “See?” he asked, in the same tone he used during your private sessions, when you finally divulged the intrusive thought or traumatic experience he’d been attempting to pry out of you for the better part of a week. “Was that so hard?”
“You’re a tyrant.”
“I am a doctor merely trying to see that my charge stays active.” And then, almost purring, “Would you have me do less for my favorite patient?”
The praise was half-hearted. Worse than that, it was cheap. The same kind of flattery that you’d employed across a hundred odd-jobs to milk marginally bigger tips out of a thousand love-starved clients. You knew that, and yet, heat rushed to your face all the same, the inside of your mouth going dry and cottony. You rushed to turn away from him, muttering an excuse as you made a run for the door. It wasn’t until you were safely across the threshold that you stopped, sucked in a deep breath, and allowed yourself the smallest, faintest possible smile.
You didn’t like it here. You hated the people, the staff, the chill. You couldn’t wait to leave.
But a tiny, guilty part of you was thankful that, if nothing else, you had Harper to make it all just a little bit easier.
~
You never had night-terrors before the asylum.
You hadn’t really dreamed at all. You hadn’t slept enough. Robin used to find you curled up in empty classrooms, trying to get a few minutes of shut-eye in before a semester-defining exam. Bailey would have to pick you up from one of your many part-time jobs at least once a month because you’d passed out from sheer exhaustion in the middle of your shift. In the asylum, you couldn’t work yourself to the brink. You were never sleep-deprived enough to lull yourself into that dreamless, pitch black, death-like sleep. Most nights, you didn’t have anything better to do than to sleep. It was awful. It was a waste of time. It wasn’t like you.
Worst of all, it meant you dreamed. They were awful, vicious things; all shifting colors and whispering voices and grabbing hands. Sometimes, you’d get lucky, be able to enjoy a couple minutes of some half-remembered schoolyard scene or a pleasantly ungrounded fantasy before things devolved and you found yourself pinned to a tile floor, fingertips biting into your hips as some heavy, amorphous mass with molten gold hair and acid pink eyes. It was an unfortunate coincidence that the monster in your worst dreams resembled Doctor Harper. It wasn’t his fault you were here. You only had yourself to blame, for that.
Not-Harper’s unoccupied hand found its way to your neck, the heel of its palm biting into your nape. The floor was so, so cold and the thing on top of you was so, so hot. There was a voice whispering in your ear - detached and disorienting - and below that, another sound, more melodic, more predictable. Something harsh and solid ground against you from behind. In the corner of your eye, the needle of a syringe caught the light, its tapered point angled toward your neck. You tried to squirm away, but the tile was slippery and the mass was so heavy and it was all so, so hopeless. The needle plunged down, down, piercing the side of your throat and—
And you woke up screaming. Your voice echoed off of the bare cement walls of your room, unswallowed and unanswered. You bolted upright, clinging to your paper-thin blanket. Pathetic. This was all so pathetic. You were alone in an insane asylum miles and miles outside of town. The orderlies weren’t on patrol and the nurses didn’t care. No one was coming to—
Three sharp knocks against your door, evenly paced and just short of forceful. A voice called your name, soft and masculine and achingly familiar.
Harper.
“Come in,” you managed, after a long beat. A latch slid out of place and your door swung open.
He must’ve been working late. It had to be closer to sunrise than sunset and he had the look of a man who’d spent the night burning the candle at both ends. His lab coat was missing and his shirt had been unbuttoned two degrees past the collar, the sleeves rolled up to his elbows. The fact that he was still in the building at all surprised you. You’d assumed he lived in town.
Your confusion must’ve been obvious. In place of a greeting, he offered an explanation. “I was passing by and heard the commotion. Are you alright?”
You nodded hastily. “Just a bad dream.”
“Ah.” And just like that, he was a man of science again, latching onto the first scrap of evidence you provided and jumping to the most rational conclusion. Pulling your door shut, he crossed the room and fell onto the foot of your bed. There was no hesitation, no pause to seek permission. He was acting like he owned the place - which, to be fair, you were pretty sure he did. “You know,” he started, adjusting his glasses. “Dreams can often signal to areas of tension within in the subconscious. Your brain might be drawing your attention towards, say, fresh trauma you haven’t allowed yourself to process.”
You grimaced. You knew what he was dancing around. Lately, Harper had lost interest in your miserable upbringing, pitiful social life, and self-destructive coping mechanisms. Rather, he’d taken to asking after the reasons behind your interment incessantly. And, if you’d been able to, you would’ve given him what he wanted gladly. You would’ve laid out every thought, every feeling, every factor that left you stranded in his care. But you couldn’t. You wanted to, but every time you opened your mouth, you just—
You couldn’t.
You shrank into yourself, dropping your eyes to the sheets. “I… I’d rather not talk about that, right now.”
“I see.” Immediately, the softness in his voice was gone, replaced by cool professionalism and the slightest trace of disappointment. He stood, starting for the door. “I suppose we’ll see how you’re feeling in the—”
You acted on reflex — lashing out and catching his wrist. To his credit, Harper didn’t flinch. He didn’t even seem all that surprised.
“Can you stay?” The question was a slurred rush, too embarrassing to properly separate into distinct words. “I mean, just for a few minutes. I don’t want to— I can’t—” You forced yourself to pause, to breathe. “I don’t know if I should be alone, right now.”
Harper regarded you for a long moment. In the darkness, he was more shadow than not. A stock silhouette in place of anything more recognizable, anything more welcoming. “You understand that I’m not on duty.”
“I know. I’m sorry.”
“And I really ought to be using this time to tend to personal needs. For my patients’ sake as well as my own.”
“Right. Of course.”
“Then again, if there was some way you could help me…” He trailed off, clicking his tongue. “I might be able to make an exception.”
Your mind was a blank expanse. You knew he was alluding to something, but you couldn’t begin to guess what.
“Help with… paperwork?”
A breath of a laugh, thin and sardonic. His eyes fell to your lips, then his belt. Understanding dawned on you immediately.
A bottomless pit opened up in your stomach. You couldn’t help it. You laughed. “That’s a little unprofessional, doctor. Even for you.”
He shrugged. “It’s perfectly natural. Most practitioners end up leaning on their favorite patients more than they should, in times of stress.”
Again, there was that rush of warmth, that bone-deep satisfaction. The word played over in your head, again and again. Favorite. Favorite. Favorite. Your hands were on his belt by the time you thought of a decent justification. You’d done more for worse men. He wasn’t forcing you, or blackmailing you, or even really pushing. You didn’t want to do this, but you wanted him to stay. You’d do whatever you had to, if it meant not having to spend the rest of the night alone.
You moved swiftly, mechanically. Unbuckle his belt, undo his fly, ease his pants down just far enough to free his cock. He was already hard enough to wrap your hand around. Rather than consider the implication, you decided just to be thankful he’d made your job that much easier.
And, for what it was worth, he had a pretty dick. Longer than average, too thick to be considered lean but not bloated enough to make you massage your jaw on reflex. No prominent veins, thankfully — those had always left your throat sore. The tip was a nice, rosy pink. You might’ve appreciated the color, had you been in a state to appreciate anything.
You made a point not to look at him as you brought your lips to his head. This would be easier if you were clinical about it, so that was what you tried to be. You divided your work into neat, impersonal steps. Lap the flat of your tongue over his tip then take him into your mouth. Wrap your hand around his base and pump. Try (and fail) not to cringe at the taste of his bitter pre-cum. All perfectly doable. All perfectly normal.
You were just starting to bob your head when you felt his palm against the back of your skull, urging you lower, deeper. You obeyed as much as you could — swallowing him down until he hit the back of your throat. Your gag reflex had been trained away years ago, but still, there was only so much you could do to suppress biology. Tears formed in the corners of your eyes, a low whine bubbling up from your chest. All to be expected. You were at your limit. Harper was smart. Harper would see that.
Except, he didn’t. He pushed harder, and you felt his cock nudge into your throat. Immediately, you floundered, your hands lashing out to catch his dress pants. You glanced up before you could stop yourself, finding Harper’s face. His expression was impassive, bordering on curios. His lips were curved into a smile, the same one he wore during your appointments, all gentle compassion and tender patience. But his eyes—
It might not have been so bad, had they not been so intently focused on you.
"Breathe, love.” His voice was enough to pull you back into reality. Again, his admission echoed in the back of your mind. Favorite, favorite, favorite. “Almost there, just—”
His hips jutted forward and you choked around him. His cock twitched in response, an airy groan slipping past his lips. You wanted to do this right. You wanted to make him happy, to make him proud of you. Your tongue swirled where it was trapped underneath his shaft, your throat convulsing as you forced yourself to take him that much deeper. You were fully crying, now, tears dripping from your chin onto your thighs. Harper shut his eyes, his nails biting into your scalp. That meant you were doing a good job. That meant you were his—
Cum flooded down your throat, hot and searing. You could feel it moving through your chest, burning a hole in your stomach. Harper didn’t thrust, or jerk, or move in any way. He just held you there — close and safe and loved.
That night, you fell asleep to the feeling of his hands petting over your hair.
Somehow, it wasn’t quite the comfort you thought it would be.
~
For whatever reason, you expected sucking his dick would be enough for Harper to stop asking the only question you wouldn’t answer.
It was not.
You were exposed to all of his tried-and-true methods, first. Writing in private journals that he always found an excuse to read, reacting to increasingly bizarre prompts all vaguely reminiscent to your life outside of the asylum, answering prying questions for hours after your session was supposed to end. Eventually, Harper got frustrated. He scowled more often, spoke to you more coldly, withheld praise he used to dull out like medication. Then, when you failed to meet his agitation with compliance, he got creative.
“I wanted to try something new, today.”
Your heart dropped into your stomach. You had to fight not to bolt from the chaise lounge you were currently laid across. You understood why you couldn’t see him in his personal office for your actual appointments, but awareness did little to endear you to the counseling room. It was too big. The lights were too bright. You always seemed to be freezing.
“Do I get to say no?”
He laughed and stood, neglecting to answer.
You focused on the ceiling. You could hear him approaching you, feel his shadow block the light. The cushion below you dipped as he propped a knee next to your hip. “It’s called recovered-memory therapy, with the added help of tactile stimuli.”
“Tactile stimuli…” You blinked slowly. “Like a therapy dog?”
“Close, dear.” You weren’t looking at him, but you didn’t have to. His smile was more than audible. “Can you roll over for me?”
You couldn’t. You didn’t want to. You started to sit up, but Harper only took it as a sign that further assistance was needed. He caught you by the waist, turning you over and forcing your stomach flat against the lounge. Your breathing picked up, teetering on the edge of hyperventilation. You did your best to wrangle it back to a steady pace.
“This was the position you described in your dreams, yes?” He straddled your thighs. His chest pressed into your back, too close. Too warm. “How did you say your attacker was touching you, again?”
You hadn’t. You wouldn’t. But Harper sighed and frowned and looked so, so disappointed and you couldn’t stop yourself, the words spilling out before you had a chance to patch the leak. “They were holding my— my neck, and their hand was on my— my—”
“Right. Of course.” His hand fell to your hip, then hesitated. “If you’d feel more comfortable touching yourself, I’d understand. If not…”
You shook your head vehemently. You would do whatever you had to so long as it meant he wouldn’t put his hands on you. You couldn’t take that. Not again.
He helped you onto your knees. Slowly, mechanically, you worked a hand between your thighs and began to rub circles into your clit through the thin material of your uniform. The action was without sensation. You might as well have been brushing your teeth.
He rested a hand on the back of your neck. He wasn’t cruel enough to choke you, but he wasn’t kind enough to give you space, either. “Good. Very good. Now, tell me about the day you realized you needed my help. Start from the beginning.”
It felt as if you’d swallowed a needle. You did your best to speak around the obstruction. “I was— I had to visit you. Something happened at school, but that’s not important. You gave me a shot, and it made my head a little fuzzy, so you left me—” Your wrist slipped, and you applied a little more friction than you meant to. Something dull and electric ran up your spine — just strong enough to be mistaken for pleasure. “So you left me alone to wait it out. Just for a few minutes. You said you’d be back in a few minutes.”
“And I was.” He knew this part as well as you did. This retelling was not for his sake. “But, what got to you first?”
“A nurse, I think.” Someone in a uniform. Someone who worked at the hospital. Someone who meant to do you harm. “I don’t know. I can’t remember his face. I just— I was on the ground, and he was holding this— this thing up to my neck, and he must’ve gotten me because—”
Your voice hitched. Harper bowed his head, pressing his lips into your temple. “It’s alright. You’re safe, here. You can tell me anything.”
It would’ve been easier to believe that if he hadn’t literally been pinning you down.
“I don’t know what happened,” you said, sincerely. “I blacked out. When I woke up, the body was gone, the cops were there, and I was covered in blood.”
“A psychotic break.” He’d never sounded so pleased. “Do you know what that means?”
You shook your head. You didn’t want to know, either, but he told you anyway.
“It means that you need much, much more care than we initially anticipated.”
You tried to pull away, to go slack, but his hand slipped between your thighs, cupping your own. He pressed your middle and ring fingers into your clit, guiding you into an awkward, vertical motion. You let out a distressed whine, squirming underneath him. “But— We’re fin—”
“I know.” Another kiss, this one to the corner of your jaw. “This is a reward. You did so well.”
You wanted to argue, but he applied more pressure and suddenly, you were too busy melting underneath him to do much of anything.
It was humiliating — how quickly you came. You hadn’t been touched in months. You were sensitive, and deprived, and so, so afraid. Harper hummed as you jerked and twitched underneath him, only letting go of your hand once the last of your spasms had died out and you were no more fun to play with than a toy after its batteries had been drained. Even then, he held you there, his grin biting into your cheek.
Your nightmares were immediately forgotten. Whatever landed you here in the first place, no more than a distant concern.
You had to get out.
~
Surprisingly, as your release date approached, Harper retreated. He reverted back to the way he’d always been — calm, collected, careful not to push the boundaries of your patient-doctor relationship. Sometimes, you’d wake up to his silhouette in your doorway, but there were no more late-night requests, no more innovative new strategies to your care. When you began to skip your appointments with him, he didn’t say anything. When you stopped coming to his office in your downtime, his only response was to give you a wide berth, in return.
On the morning of your release, he came to fetch you himself. You were already wearing — had been since the night you before — the sundress you’d arrived in. It fit poorly, which made sense. It’d been months. Hospital food and a largely sedentary lifestyle meant your body had changed, lost definition, gained new curves. Still, you felt safer in the remnants of your old life, your real life, than you ever had in your stale uniform. Harper regarded with narrow eyes and a pleasant smile before turning on his heel and signaling for you to follow.
You expected to be taken to the front gates. That was how you saw the other patients leaving, as rare as it was for the asylum to actually let one of its patients go. Instead, Harper led you down the familiar route to his office, pausing outside the shut door. '“You know,” he started, slowly, adjusting his glasses. “I do mourn that our time together has ended so quickly.”
You forced yourself to shrink, to simper. “I’m sorry, doctor.”
“There’s no need to apologize. It’s really very selfish of me.” And then, leaning down, lowering his voice into a conspiratorial murmur, “Can I tell you a secret?”
You wanted to cover your ears. You wanted to say no. You wanted to run.
You nodded.
“I’m afraid it’s rather selfish, but—” He paused, his grin widening. “No doctor has ever truly wanted to let their favorite patient go.”
Immediately, you relaxed. Honestly, it felt a little silly to have ever been scared at all. What else did you think he was going to say? Of course you were his favorite patient.
He’d always been your favorite doctor.
Without another word, Harper opened the door and ushered you inside. Bailey sat on one end of the well-worn sofa, elbows braced on his knees and mouth twisted into a distinct grimace. You perched on the other end, pulling your legs up and tucking them underneath you. You’d always been so comfortable here, so warm. It was difficult to remember why you’d stopped coming by.
Bailey shot you a frown. “Don’t get comfortable, brat. We’re leaving as soon as the doctor signs your paperwork.”
“About that,” Harper said, leaning against his desk. “I believe my patient has something to say to you.”
You did? Oh, of course you did. How could you be so absent-minded?
“I don’t want to go.”
Your voice was bright and clear. This was the most sure of yourself you’d been in months.
Bailey seemed less convinced. “Run that by me again?
It was hard to imagine how you could’ve been more clear. “I don’t want to leave.”
He looked to Harper. “Get out.”
Harper didn’t move. “Please, Bailey. We’re all friends here.”
Bailey didn’t respond. He held his ground until, with a sigh, Harper rolled his eyes and left the room. Once the two of you were alone, Bailey went on. “Look, kid.” He sounded exasperated, as if this was chore that had already run long. “Whatever he told you, don’t believe it. Harper’s full of shit. Whether it was about new treatments or hallucinations — just forget about it. There’s nothing he can do for you in here that he wouldn’t have already done out there.”
“I don’t want to leave.”
He groaned. “Yes, you do. I didn’t drive my ass all the way out here just for you to—” He broke off, running a hand over his face. “Robin misses you.”
Oh, god.
Robin.
Several things became undeniable at the same time. You didn’t want to leave. You had to go. You hated the asylum. The asylum was good for you. You’d been kept here for months with no progress. Your treatment wasn’t over, yet. Harper was a good doctor. The best doctor. You were so, so scared of him. He hated you. He was bad to you. He hurt you. You were his favorite—
There was no good way to describe the feeling of being suddenly aware that half your thoughts were not your own. It was a little like believing, firmly and undoubtedly, that your head was above water, only to blink and find that you were already drowning.
You took a deep breath. You were fine. You were in control of yourself. You wanted to leave. All you had to do was tell Bailey that. All you had to do was say the only thing you’d been able to think for weeks, now.
“I don’t want to go.”
Your tongue tasted like sulfur. You could feel the blood boiling underneath your skin. You tried again.
“I don’t want to go.”
Bailey sat up. You pressed your thighs together. Again.
“I don’t want to go.”
Again.
“I don’t want to go.”
Again.
“I don’t want to—”
“Alright, kid, I get it.” He gestured dismissively, then called for Harper. “You can come back now, freak.”
Immediately, the door swung open and Harper sauntered across the threshold. His grin was wide and fanged, dripping with fresh venom. “I believe my patient has made the necessity of our work clear.”
“Crystal.” Bailey stood, but hesitated before exiting. He fished something out of his front pocket - a business card for the orphanage, its edges soft and its corners bent. A phone number was printed neatly along the bottom. His office landline.
Wordlessly, he held the card out to you. You stared at it blankly for a second, then another, before reaching up with shaking hands and grabbing his wrist as tightly as you could. Bailey jerked back on reflex, but you held on, letting him drag you to the floor. The business card was gone - no longer a matter of concern. You wouldn’t let go. No matter what happened, you wouldn’t let go. Not until you were home. Not until you were far, far away from Har—
“That’s enough, dear.” Instantly, your body went slack, your hands falling to your sides and your arms going slack. Bailey stumbled back as Harper cocked his head to the side, feigning a pout. “I’m afraid you might have to leave. Your presence seems to be causing quite a bit of agitation.
There was a sneer, the beginning of a snarl, but Bailey caught himself before things went further. With no emotion more apparent than schooled apathy, he turned and left — slamming the office door behind him. Leaving you alone.
Harper let out a low, breathy sigh. “Good riddance,” he said. He bent down, picking up the card Bailey had dropped. His eyes skimmed over it before, with no small amount of delight, tearing into pieces and letting them flutter back to the ground. “Never did like that one. He can be awfully possessive with his toys for a man who casts them into the world so carelessly.” And then, to you, “It’s a good thing that you landed in my care, isn’t it?”
You didn’t respond. You couldn’t. The only words you seemed capable of saying were still heavy on your tongue, and you wouldn’t give him the satisfaction of repeating them again. Harper didn’t seem to mind. With no great urgency, he gathered you up in his arms and set you down on the edge of his desk. Your body, still limp, collapsed against his, but he only laughed and wrapped an arm around your midriff, holding you that much closer to his chest. For lack of an ability to speak your mind, you groaned — the sound throaty and thoroughly miserable. Harper’s smile bit into the side of your skull.
“Something on your mind?”
“I hate you.”
“I thought you might say that. It’s an occupational hazard, you know — something they warn you about in school.” His fingertips skirted up your back, following the curve of your spine. “I hope you appreciate that hatred is something I’m still allowing you to feel.”
Allowing. Like he had total control over you. Like your free will was a privilege you ought to be thankful not to have been stripped of. You thought about shoving him away, but every time you tried to move, your vision blurred and your body grew heavier, as if you were suddenly on the verge of falling asleep. As if you were back on the hospital floor, dead weight on top of you and a needle in your—
The realization was sudden and jagged, as obvious as it was sickening.
“You’re the reason I’m here.”
“Of course.” He made no attempt to deny it. If anything, he sounded a little smug. “It’s clever, isn’t it? Hypnotism is so finicky, and no matter what I do, it always seems to wear off sooner than I’d like. This, though—” He bowed his head, burying his face in the crook of your neck and inhaling deeply. “This works. One injection, a compelling trigger phrase, and you’re as suggestible as a newborn lamb.”
“But— But I hurt someone. All the blood, and the—”
“There was blood, certainly. Compliments of our generous donors. And you worked yourself into such a frenzy, I doubt the powers-that-be would’ve questioned it if I’d asked to have you locked away for the next, oh, twenty-five years?” He paused to chuckle. The sound was thin and airy and cruel. “It lasts, too. You’ll be able to go months between doses. Just think of the applications. No need to break-in cattle, not when two shots a year will have them so wonderfully obedient. And the brothels, Briar’s been complaining about worker retention for—”
You cut him off with a low, warbling sob. You didn’t want to cry in front of Harper. No part of you wanted to give him the satisfaction. You’d managed to hold it in for weeks — through probing and prying and late-night check-ins. But there was something about his tone, so eager to strip away your free will and sell you off to the highest bidder. It was the happiest you’d ever seen him. It was the proudest you’d ever made him.
The dam broke open. Tears streamed down your cheeks, hot and humiliating. You clenched your jaw, grit your teeth, but you couldn’t seem to bite back the pitchy whines and miserable whimpers that bubbled up from some deep, primal cavity. You couldn’t cover your mouth. You couldn’t even raise your hands to try.
Harper’s expression dropped. He pulled back, already cooing, already peppering kisses over your cheeks. “Now, now, there’s really no need for that. You, my dear, are far too precious to give away.” He pulled you into his arms, letting your body slump lifeless against his chest. Rounding the desk, he fell into his chair and arranged you to straddle his lap, a knee on either side of his hips. “What would I ever do without my favorite patient?”
Sudden, searing agony. The room went blurry. Your vision flashed white. You collapsed against him willingly, now, burying your face in his lab coat just to block out the world as it spun around you. Harper sighed, pressing a long kiss into the top of your head. His hands found their way to the back of your sundress. Fabric shifted, a button falling out of place, and you felt the bodice go slack.
“Raise your arms for me, love?”
With all the obedience of a programmed machine, you raised your arms above your head. Your dress pooled at your waist, as limp and as useless as the body that was no longer under your control.
There was no attempt to undress you properly. He worked efficiently, slipping his hand underneath your skirt and cupping your cunt. The pad of his thumb circled your clit once, twice before his interest drifted and he pulled your panties to the side. The insertion was abrupt — bordering on painful. Three fingers at once with minimal prep. You’d had things shoved into you before, often roughly and never with your permission, but you’d never had it done so slowly or with so much care to soak in each little pained sound you offered by way of response.
It would’ve been better, had he been a little more rushed. Unfortunately, even at his most monstrous, Harper was still a man of science. He moved at a languid pace, pumping his wrist lethargically, pausing often to stretch or curl or grind against the walls of your cunt. It should’ve stayed that way — dry and harsh and uncomfortable — but despite the lack of pleasure, you could feel yourself getting wet, hear the slick squelching as he moved inside of you. “So resilient,” Harper praised. “It’s impressive, really. Even trapped, you try to make the best of things.”
Not that he was helping. The heel of his palm came up, grating against your clit. The room suddenly seemed too hot. Your face wouldn’t cool down. You felt sticky all over. How you’d ever taken comfort in this was a mystery. You would’ve preferred to be left out in the cold forever, if it meant not having to bear another second of his warmth.
And your stupid arms were still stuck above your stupid head. You whined, clenching and unclenching your fists, and Harper took pity on you. “Around my neck, now.” And then, when your hands moved to wrap around his throat, “Nicely, please. The way you know you should.”
Glowering, you draped your arms around his neck. The closeness was terrible. The fabric of his dress shirt was coarse against your bare chest. He spread his fingers apart and you lurched into him, attempting to seek shelter in the source of your agony. It was awful, but bearable. You’d survived worse. You’d even come out the other side with your dignity more or less in-tact. You just had to stay calm. You weren’t here. You were somewhere else. You’d left the asylum. You were with Bailey, back at the orphanage. You were going to see—
“It’s alright, dear.” Harper’s voice was a hook, piercing your mind and dragging you back into reality. “You deserve it. You can let go.”
He was so fucking calm. That was the worst part. He was so calm, so put-together, so unaffected, and you weren’t allowed to be. The moment the words left his tongue, your body was on fire. There was no bliss to it. The pleasure was scalding and invasive. The physical symptoms, ungraceful and involuntary. Your mouth fell open, but any sound you might’ve made was cancelled out by your sudden inability to breathe. Your hips rocked against his hand, trying in vain to prolong the intolerable. Your thighs snapped together, pressing into his sides with enough force to make your muscles ache. He watched you all the while, eyes half-lidded and head cocked to the side. The same way he might’ve looked at an especially endearing lab rat, or a patient report that was just a touch more interesting than he’d expected it to be.
Eventually, thankfully, the last embers of your involuntary climax burnt themselves out. You slumped against him — too exhausted to need mind-control as a pretense for your reliance. For a long time, Harper let you stay like that. Unmoving and unthinking. Even that mercy, though, was eventually withdrawn. His hands found their way to your sides, his fingertips massaging circles into your back. You whimpered at the contact, but he only hummed.
Slowly, his touch drifted north. Untangling you from him, he eased you away from his chest. “You didn’t think we were done, did you?” His gaze fell to his belt, lingering for a moment before darting back up to meet yours. “Whenever you’re ready, dear.”
You might’ve laughed, if there had been any part of you left in a state to appreciate the irony.
It was a small kindness that you didn’t have to think about what you were doing. You watched from a measured distance as your hands undid his belt, as a fist mechanically pumped over his cock until he was leaking onto your knuckles. There was no reluctance, no emotion to it, only a dull understanding of the steps that needed to be taken and the awareness that with or without your mind, your body would see the task through. Harper’s hands fell away from you entirely as you shifted onto your knees, aligning the head of his cock with your abused entrance. He leaned back in his seat, putting that much more distance between you and him. Giving himself a better view.
Even if you’d had more control, you doubted you would’ve been more gentle with yourself. You bottomed out in the first stroke, your hips settling against his as his cock filled you to bursting. Adjustment was unnecessary. Discomfort was a part of the treatment, not a symptom of your condition. It didn’t fade as you rocked and ground against him, only sharpening into other, more acidic byproducts. Pain. Overstimulation. Pure and utter loathing.
Harper made no attempt to help. He seemed more than satisfied to let his experiment run its course untampered with. His hands kneaded at the arms of his chair, curling and flexing in-time with your mechanical bouncing. A blistering red spread over his cheeks, although you couldn’t be sure if he was getting off on what you were doing or the fact that you were doing it at all. He was moaning unabashedly — little, breathy, lilting noises that would’ve had you assuming he was the one being tortured. Worst of all, there was this look in his eyes. Not love, not really, but something tangential. Adoration. Fascination.
Sickness.
Sick and desperate. You rolled your hips and he buckled into himself, letting out a rough groan. Immediately, his hands were on your hips, guiding your ministrations, forcing you to move faster, to take him deeper, to somehow bend even further to his whims. You felt him twitch. A moment later, Harper lurched against you, his mouth finding your throat. You could feel his breath, hot and humid, then his drool as he lapped over your skin. It was disgusting. It was horrible. It was—
“Cum,” he ordered, his eloquence lost to pleasure. “Like you want this. Like you love me.”
And you did. Holding him tight, crying his name, making it seem like there wasn’t anywhere in the world you’d rather be. Harper followed shortly — desperate in spite of his composure. There was no attempt made to pull out. He dragged you flush against him, keeping his cock buried inside of you as he came undone, leaving you full and heavy and tainted. Claiming your mind wasn’t enough, apparently. He had to leave his mark on your body, too.
He didn’t let you go, after he finished. Part of you hoped that he would — that you’d be allowed to steal an unsupervised shower and slink off to your cell to sleep away the misery. Instead, he clung to you, draping himself over your rigid body as he panted and trembled. Eventually, he seemed to pull himself together, regaining just enough of his composure to grin and reach for something behind you.
You heard a drawer slide open, metal clack against wood as he removed a long, rectangular box. “…I have something for you,” he started, the words slurring into one another. “I thought I ought to give it to you later on, in a more controlled environment, but—” A pause, a laugh. “I suppose I’ve gotten rather sentimental, haven’t I?”
He placed the box on the arm of his chair and, with a single hand, pulled the lid off. You recognized the contents at a glance. A syringe — its needle infinitely long and the fluid in its barrel an acidic shade of pink. He took it up gingerly, resting his thumb over the trigger and holding it up to the light. You didn’t ask, but he told you anyway. Still playing doctor, even now. “Your current dose should last another month, but I thought it best to re-up now. To ensure that our relationship remains as productive as it has been, so far.”
He brought the needle to your neck, aiming for the patch of skin his mouth had sought out time and time again. You were shaking, in spite of your paralysis. It took everything you had to speak, and even then, you could only manage a few pathetic little words.
I have NO CLUE if anybody's done this but the past week has been hell trying to unlock every piece of content so I can wife up Gwylan (my newest obsession—sorry Wren 🥀) and some of the 'requirements' are kind of vague SO... after draining every drop of Gwylan content dry and getting my yearning to 100% with this bitch, here's a clothes guide to help you all get those interest points with Gwylan! It requires SCRUBBING through the game and getting every piece of content, so if you're not doing it with cheats... Good luck soldiers 🫡
As a side note: especially with Temple clothing, I am not positive on how to unlock some things so if anybody has any corrections/advice please let me know so I can fix it :)
ADDED/FINISHED the list thanks to the lovely anons in my DMs as well as Tumblr users helirubys, waxanatomy, and ambicutiebutt (not sure if y'all wanna be tagged but I sososo appreciate the help!).
What's so special about the forest shop?
Unlocking clothing is the ONE way to gain interest with Gwylan. If you want to romance them, it's a long process that involves unlocking every piece of in-game content there is. Once you unlock clothing, you can talk to Gwylan about how you obtained it. PLEASE NOTE you can NOT cheat unlock the clothing! Gwylan will know you used cheats and you will not gain any interest points! You can bypass some of this by editing the save file if you are truly that desperate, but seasonal clothing (Halloween, Christmas, Valentine's) cannot be unlocked this way.
With any of the holiday clothing, they automatically unlock, BUT you won't get special Gwylan dialogue or the interest points so I do highly recommend you unlock them before they're released for the season!
SEASONAL OUTFITS
Witch Set (includes Witch Dress, Broomstick, Witch Hat, and Witch Shoes): "In stock from the 21st of October, or get accustomed to tentacles."
Another holiday set. For this, you'll need to have multiple tentacle encounters until you get the 'prey' and 'witch' trait. The easiest way to do this (in my opinion) is to go out to see while hallucinating. You'll need tentacles enabled for this—obviously. Same with the other holiday outfits, you'll lose out on dialogue if you try to cheat this unlock in any way.
Pumpkin Set (includes Pumpkin Dress and Mini Pumpkin): "In stock from the 21st of October, or learn 15 recipes."
Very self-explanatory. You can learn recipes through housekeeping lessons at school. I did figure out if you edit the save to NOT unlock the dress but instead to add the recipes into your list (by editing "recipes": true), you can unlock the set and still get the special dialogue/interest. Alternatively, you can also learn recipes once you unlock Avery's mansion but that will happen way after Halloween I think, and it's not completely foolproof.
Skeleton Set (includes Skeleton Outfit and Skeleton Mask): "In stock from the 21st of October, or discover a crypt."
This one's pretty easy—you need to enter the catacombs. To do that, you'll enter the forest, go further about 2 or 3 clicks until you reach the Old Graveyard. You'll enter the graveyard, do a skullduggery check, and voila! You're in the catacombs. You'll want to be in the catacombs for the Mummy set too.
Mummy Set (includes Mummy Top, Mummy Skirt, and Mummy Face Wrap): "In stock from the 21st of October, or be wrapped up in spider's silk."
You'll need to enable Spiders and Swarms for this one if they aren't enabled already. Once you're in the crypts, keep traveling west and eventually you'll encounter spiders. This took me a bit to get to, but eventually you'll be completely cocooned in spider webs. I think you can ALSO get this by cleaning attics on Danube Street, but I haven't tried that route and I feel like that might take even longer.
Scarecrow Set (includes Scarecrow Shirt and Scarecrow Hat): "In stock from the 21st of October, or flawlessly defend a multitude of fields from assault."
I HATED THIS ONE SO MUCH. I love Alex, I really do, but what the fuck! To unlock this, you have to unlock all 9 fields of the farm and defend them all from Remy without losing a single one. This made me crash out.
Futuristic Set (includes Futuristic Bodysuit and Futuristic Shades): "In stock from the 21st of October, or become too invested in a strange arcade game."
So for this, I think you can only encounter the game while hallucinating. Go into the arcade, and there SHOULD be a 'lone, mysterious cabinet' you can investigate. You can only play it once a day; eventually you'll get encounters through it, although I think they're randomized because I did this on three different saves and had different encounters among them. After the second encounter, you SHOULD have unlocked the suit and the arcade game will disappear.
Vampire Set (includes Vampire Jacket and Classy Vampire Jacket): "In stock from the 21st of October, or succumb to a jealous lover's longing."
This is one of the TWO sets you unlock through Kylar (the other being the Rose Wedding set). To unlock this, you'll need to have a couple of things set up: You'll need to have gotten a stuffed owl plush from Kylar, and have their jealousy up high. Then, you get to piss him off. I did this by sleeping with Robin in the orphanage room, in which I got a "Something is watching" or something like that after the encounter, although I've heard you can sleep with Whitney as well as long as it's IN your room and the owl is already in there. After this, walk around outside a bit and eventually Kylar will kidnap you. After that, you just need to get the "Stockholm Syndrome: Kylar" trait and it'll unlock the vampire set. You can manipulate NPCs feelings with cheats if you want to speed up this process.
Christmas Set (includes Christmas Dress, Jingle Bell Dress, Christmas Shirt, Christmas Trousers, Christmas Hat, Mini Snowman, Christmas Leg Warmers, Candy Cane, Reindeer Slippers, and Christmas Boots): "In stock from the 18th of December, or leave a generous gift to a family in need."
The 'generous gift' will be left on Domas Street. When you break into people's homes to steal, you'll eventually come across a home where you are given the option to leave money for them because the home is destitute. I left 1,000 just to be certain, I'm not sure if you can get away with less. If you edit the save to unlock this, you will NOT be able to get this dialogue with Gwylan, so the only way to get this is to start thieving homes on Domas.
Gift Set (includes Gift Wrappings and Gift Bow): "In stock from the 7th of February, or face a unique punishment for stealing clothes."
So you'll need to steal from Gwylan's shop twice for this. Just walk out with clothes—the first time you come in, the shop will attack you and steal all your clothes (so don't wear anything you don't want to lose!). Walk back out and steal more clothes, come back in, the shop will once again steal your clothes and wrap you up in gift wrappings. You'll also be banned from the shop for a day as a heads up.
ADDENDUM: Gwylan HAS to be there when you steal, otherwise you'll just get assaulted by the shop over and over again.
Rose Wedding Set (includes Rose Wedding Dress, Mini Rose Wedding Dress, Rose Wedding Suit, Frilly Rose Wedding Suit, and Rose Wedding Veil): "In stock from the 7th of February, or escape a forced wedding."
The other Kylar outfit, and probably one of my FAVE unlockable clothing besides the butterfly dress. For this, you'll need Kylar to be hysterical—to get that, have high love, lust, and jealousy. Then, just have lunch with Kylar. They'll drug your food and try to force you to marry them. This is also Kylar's dismissal quest: if you let the police arrest Kylar, you won't see them again in the game unless you go to prison, in which case you can break them out if you really want to.
TEMPLE SPECIFIC
Initiate's Robe: "Prove your purity."
Join the temple. EZ-PZ. I don't like the temple, but you'll want to join to both earn feats and unlock a bunch of clothing.
Holy Pendant: "Discover the soup kitchen."
To discover the soup kitchen, you'll just need to continuously pray at the temple. Eventually you'll trigger an encounter where a nun is going around, asking for donations. After you generously donate, they'll inform you of the soup kitchen.
ADDITION: You can also discover the soup kitchen through a task of Mickey's in which they'll ask you to deliver a note to River, OR by passing a S-rank seduction check to squeeze more out of a polite client at the spa. A note about the spa, though—you'll need a high hand skill and beauty to get employed there.
Nun's Habit Set (includes Nun's Habit and Monk's Habit): "Advance in rank at the temple."
This one's self-explanatory—join the temple. Once your grace is high enough, you'll talk to Jordan about advancing in rank. This can be unlocked through a save file edit if you don't want to go through all of that and will still get you the points but it is not recommended. If you're using cheats and want to speed run this, just manipulate your grace and talk to Jordan.
Sexy Nun Set (includes Sexy Nun's Habit, Sexy Priest's Vestments, Sexy Nun's Gloves and Sexy Nun's Stockings): "Purge enough corruption."
Lower the soft world corruption by at least 30 points. You can look at the wiki here to see how to do that exactly.
Confessor's Robe: "Be introduced to the temple's most exalted."
Meet the Bishop's hands! You'll need to be a second-tier monk/nun, and this is automatically unlocked after you complete your first successful purge at the confessional booth.
Exorcist's Garments (includes Exorcist's Cassock and and Exorcist's Habit): "Interrupt a heretical ritual."
You'll need to do a couple of things to get to this. First, you'll need to have unlocked dance shows from Charlie. You do this by getting your dance skill and Charlie's respect high enough for them to offer shows to you. Then, if you haven't already joined the temple, you'll want to do so (you may need to advance in rank, I can't remember if you have to). This trigger's a quest where Jordan asks you to 'keep an eye out' for a missing initiate during a dance show. Go perform at a party on Danube, and after saving the initiate you should unlock these.
Temple Sparring Garments (includes Monk's Sparring Habit and Nun's Sparring Habit): "Become proficient with one of the temple's holy tools."
Also only available to monks/nuns. Just reach at least B-rank in either the baton or whip by sparring in the cloister daily.
Evangelist's Uniform: "Successfully solicit a donation for the temple."
When asked to solicit donations for the temple, pull up an initiate's skirt. You'll need level 3 promiscuity.
Stone Pendant: "Find beneath a loose stone at the temple."
You'll need to be in the temple (obviously) to find this. Just snoop around and be nosy and you'll eventually get it.
Holy Stole: "Requires sufficient devotion."
Max out your grace! You'll know you have it when the bar is gold and glowing.
JOB SPECIFIC
Belly Dancer Set (includes Belly Dancer's Top, Harem Vest, Harem Pants, Belly Dancer's Veil, and Belly Dancer's Shoes): "Be offered the star role in a show at the brothel."
You'll need to have the brothel unlocked for this one. To do that, you'll need to go to the night club and be denied entry for not having an I.D. This should unlock Briar's brothel, where you can get your fake I.D. and also work at the brothel. Continue working there until you max everything out basically (but be careful to NOT piss Briar off).
Swan Lake Set (includes Swan Lake Dress, Fancy Swan Lake Dress, Swan Tiara, Swan Feathers, and Ballet Shoes): "Be offered special dancing jobs."
Go to the studio and take dance lessons from Charlie! Once your dance skill and Charlie's respect is high enough, he should offer the job to you. You'll need to do this all to unlock one of the temple outfits, as well.
Chef Set (includes Chef Jacket and Chef Hat): "Become famous for your cream buns."
To get this, you'll need to work at Sam's cafe. It takes a while, but eventually you can work as a chef and get to work on the cream buns' "special" ingredient. Just keep up at it and eventually you'll unlock this.
Fedora: "Eavesdrop as a bartender and learn about a criminal undertaking."
You'll get this at Darryl's club by working as a bartender. You'll need a fake I.D. from Briar first, though, which costs about $500 as a heads up.
MISC. ITEMS
Catsuit: "Pillage a shipment."
You'll want to have high skullduggery and athletics for this one. Just go to the docks and break into shipments until you find the catsuit (and, consequently, my fave NPC, Wren). It might take a couple nights to find it depending on if the RNG likes you or not.
Flower Crown: "Make one with someone special to you."
Have Robin as a love interest and go to the garden while they're at the orphanage. They should come out and ask if you want help with the garden, in which you're given the option to make them a flower crown!
Daisy: "Find daisy seeds."
Unlock the ability to plant daisies. If you somehow haven't gotten this, it just means you have to go out to the orphanage garden and search for seeds.
Rose: "In stock from the 7th of February, or get kissed by a rose."
WOW thank you guys for the correction on this one because I was SO wrong. You'll need to have unlocked rituals with Gwylan for this one. You'll need high yearning + high lust, and during the ritual a rose will bloom from their mouth and they'll kiss you.
Dark Pendant: "Discover Bailey's fear."
Unlock the orphanage loft! This will happen eventually throughout the game, and I'm not sure if it's dependent on rebelliousness/hope. The pendant will unlock once you discover the loft, though.
ADDITION: Looks like discovering the loft is pure RNG.
Jasper Pendant: "Get an impromptu science lesson."
This will unlock through Gwylan's quests for you. Eventually, Gwylan will ask you to bring them a gold choker, gold bracelets, and gold anklets—you'll need Sirris' adult shop unlocked for this quest, though. Once you bring back the jewelry, Gwylan will give you a science lesson on the properties of gold, and that will unlock the jasper pendant.
Feather Accessories (includes Feather Necklace and Feathered Hair Clip): "Romance an avian."
You'll need to romance Great Hawk and make them a love interest. I have that content disabled and was able to unlock it through a save file edit and still get the unique dialogue/points, BUT from then on Gwylan might ask you to bring back hawk feathers.
Loincloth: "Befriend a lonely hunter, or join a pack of wolves."
Self-explanatory—go deep enough into the woods until you are hunted down by either Eden or Black Wolf. I don't know the requirements on BW's side since I have them disabled as well, but for Eden you'll need to gain the "Stockholm Syndrome: Eden" trait before unlocking the loincloth.
ADDITION: Confirmed that you'll need the "Stockholm Syndrome: Wolves" trait if you go the BW route.
Shrine Maiden Set (includes Shrine Maiden Robes and Spirit Mask): "Become sufficiently foxy."
Gain the fox transformation. Since I have all bestiality content disabled, I was only able to get this through using cheats to give myself the TF. Not only will this unlock special dialogue with Gwylan, but it also opens up the opportunity to have 'hypnosis' sessions with Gwylan to help with acceptance.
ADDITION: You can also unlock this by praying to a shrine in the moors!
Fox Mask: "Attend an exclusive party."
You'll need to be on Avery's quest line and go on dates with him. Eventually, you'll go to a game night between Avery, Quinn, Leighton, and Bailey—you want Avery to win this game night. After he wins, he'll take you to the exclusive party where you'll unlock the mask.
Vintage Set (includes Vintage Pantsuit, Vintage Skirtsuit, Bowler Hat, and Military Beret): "Help an old fossil remember."
You unlock this through Winter and the history museum. Very specifically, you'll need the Bleeding Ward painting. You get this through doing a heist with Wren—you can unlock this quest by getting Wren to approach you in the pub. You'll want a high skullduggery for this (and I recommend a high dance skill, too!).
Rag Set (includes Rag Top and Rag Skirt): "Demonstrate historical torture devices to completion."
Also earned through Winter. I want to say it's through their classes but I'm not entirely sure, unfortunately.
Butterfly Set (includes Butterfly Dress and Butterfly Bow): "Become addicted to nectar."
OUGH This set is SO cute. To unlock it, you'll need plantpeople enabled. Go DEEP into the forest or moors while hallucinating and you'll encounter plantpeople. I think you have to unlock the trait 'nectar addict' or 'dendrophile' to obtain this, I think I got it in about 3 or 4 encounters. For the forest, you won't encounter plantpeople until you're past the lake so be careful about Black Wolf and Eden who might try to start hunting you.
School Set (includes Classic Serafuku, Serafuku, Gakuran, Serafuku Dress, and Sailor Ribbon): "Discover the headteacher's secret."
Pay attention in math class! Eventually, River will ask you to deliver a letter—open the letter. You'll get detention for it, but it will give you the login information to Leighton's computer. Later on when school is closed and locked up, you'll need to break in and get into Leighton's computer. Not only do you unlock the outfit, but you're given the chance to blackmail Leighton into never giving you detention. (Alternatively, you can report Leighton to the police with the information, OR do both like I did lol.)
Chain Set (includes Chain Tunic, Chain Leggings, and Chain Boots): "Learn the many tales of a witch and her gaoler."
You'll need to deliver the Hopeless Cycle painting to Winter. You'll get this painting through accepting a job from a shifty stranger on Domus Street, let them film you, and then turn the tables on them and get the key to the Serpent's Maze in the Farmlands.
Esoteric Spectacles: "Succeed a master."
Explore the flats on Barb Street! Eventually, you'll find the hookah parlor. Once unlocked, keep progressing the tentacle parlor/town upgrades and eventually you'll inherit the hookah parlor.
Succubus Set (includes Succubus Top, Succubus Lower Back Wings, Succubus Gloves, and Succubus Heels): "Become sufficiently impure, or take 15 virginities."
Not sure what the requirements for "sufficiently impure" is because my purity was at a 1 and it STILL didn't unlock, so I had to take 15 virginities. Annoying, but manageable, especially if you adjust the settings at the beginning so you're more likely to encounter virgins. Among named NPCS, though, Robin, Kylar, Sydney, and Great Hawk are all virgins (and Eden has a handholding virginity but I'm not sure if that counted towards this set).
ADDITION: I've been told you need to get the demon transformation which is acquired by KEEPING your purity at 0 for 30 days.
Janet Dress: "Lose yourself in a classic romance tale."
Go to school and read the story of "Janet and Raul" in the library until you're given the option to imagine yourself as Janet. The dress should unlock after.
Sage Witch Hat: "Take part in an intimate concord."
I don't think this unlocks until you do a ritual with Gwylan. For the sake of spoilers, I won't head into specifics but this will probably be one of the last things you unlock.
Familiar Collar: "At last, yours to keep."
Another thing unlocked through Gwylan's storyline and probably the VERY last thing you'll unlock. You'll need to have unlocked them as a love interest to get this, which means unlocking every other piece of clothing first.
"SOFT" BAD ENDS (recommend saving these for last if you plan on unlocking without cheats)
Slut Shirt: "Survive slavery in an underground brothel."
There are a couple of ways to get to the underground brothel. Refusing to pay Bailey might get you there, but it's not a surefire way (I found he's more likely to sell me off to Eden. Sigh.). Pissing Briar off is another way, I think—start working at the brothel, and then start prostituting yourself out instead. There might be other ways, but I'm not sure. Either way, you'll need to escape the underground brothel, which will take a while, so I suggest doing this as one of the last ones.
ADDITION: The easiest way to get to the underground brothel is to do Mickey's favor in uploading a USB to Briar's computer and not bother with a distraction or escape route.
Prison Set (includes Prison Shirt, Prison Trousers, and Prison Jumpsuit): "Get sent to prison."
You'll need to basically have all of your crime stats maxed. Maybe evade arrest a few times before turning yourself in at the police station—eventually, they should send you to prison. It was such a PAIN breaking out as a heads up—apparently if you have the harpy TF it's easier, but I not only didn't have the harpy transformation but was also trying to break Kylar out. Wouldn't recommend. Easiest way to max your crime stats are through assault, thieving, and evading arrest. If you blackmail Leighton, your coercion should get pretty high in one go, as well.
Cow Set (includes Cow Bra, Cow Panties, Cow Bell, Cow Socks, and Cow Sleeves): "Become livestock."
You need to access Remy's underground farm. There are a couple ways to do this, but the easiest I've found is by passing out in the moors by Remy's estate. There is also a LOW chance that you can get kidnapped while helping somebody move boxes on the street (in where they'll throw you into the van), but the easiest for sure is to just pass out on the moors.
ADDENDUM: You do NOT need the cow transformation to unlock this! Just wind up on Remy's farm—you can escape right after and have this set unlocked still.
Unbound Straightjacket: "Escape the asylum."
Unlocking the asylum is kind of annoying in that you have to pass out multiple times on the street from stress. Eventually, Doctor Harper will take you to the asylum instead of sending you back with Bailey—then, all you have to do is escape. Out of all of the soft bad ends, I think this one is the easiest to escape from.
ADDITION: If you've unlocked weekly appointments with Harper, get your trauma up and eventually you'll get a message saying Harper will have to intervene if they see you in this state. Go see them and they'll take you to the asylum.
Islander Mask: "Build with foreign wood."
Reaching the island is probably the most annoying thing ever. I HATE the island. To do this, you need to pass out at sea and HOPE you get picked up by Zephyr the Pirate. Eventually, their crew will dump you overboard and you'll end up at the island. Getting to the island is annoying enough—being on there just sucks, especially if you're doing a save without cheats. You'll need to build shelter on the island and befriend the islanders before you're finally able to unlock the mask. And good luck getting off!!!! Island is my least favorite part of this whole game and I'm so tired of hunting for food on there only to come up with fucking walnuts every time! Make me crash out!
ADDITION: You can also go to the island directly through Jordan. With maxed grace as a nun/monk, they'll request the player to retrieve a holy spear from the island. Then, you'll ask Winter about it and explore the old sewers until you find the Smuggler's Pub, where you can directly ask Zephyr to take you there!