Writing Prompt

WRITING OBSTACLE

Write a story about a morally grey character.

A morally grey character is someone who is neither outright good nor completely evil - but they don't have to be boring! Give your character motivations for both their good and bad behaviours.

Writings

Blood For The Beautiful 🌹

Leona Castiel walked a fine line between duty and pleasure.

He didn’t exactly enjoy his job. It was messy, dark, and undeniably dangerous.

Yet, part of him thrived in it. He cleaned the streets of filth that dared to step out of line. The screams of agony that echoed through the empty basement halls were like music to his ears.

All so she could stay safe.

Georgina Floyd.

The most beautiful girl he’d ever laid eyes on, with soft jade eyes and sunkissed skin. She worked at the cafe down the street, brewing coffee behind the counter, taking orders from excited customers. Many times, he watched her from the shadows, tucking her caramel-blond hair into a messy ponytail, nervously chewing on her lower lip as she cleaned spills and prepped dishes for the constant flow of customers.

He enjoyed watching her work. It was one of his favorite pastimes. He liked to imagine her in his own kitchen, swaying her seductive hips to some obnoxious pop song, working at the marble island. Not that she knew he existed— she didn’t even know his name. But Leona knew everything about her.

Her favorite movie. Her favorite food. Her address. Even the exact name of the hair product she used—the one that left a sweet vanilla and cinnamon scent…

A loud scream interrupted his blissful daydreaming, the unwelcome sound emitting from the tortured man had been working on for the past hour or so. Leona didn’t mind. His mind had wandered before, and this was an opportunity to meet a new…acquaintance.

The man, Mr. Wickhamm, was older—late forties, possibly early fifties. His once pristine suit was now drenched in sweat and blood, the fabric torn and disheveled. He’d been sitting in the chair for far too long, bound, gagged, and on the edge of madness. His eyes were wide with fear, and his panting breaths echoed in the otherwise silent room.

Leona leaned forward, making eye contact with the terrified man, and let out a slow, deliberate sigh. “Mr. Wickhamm,” he purred, his voice low but striking with an unspoken command. “I do hope this is worth your time.”

Wickhamm’s breathing hitched as he trembled in his restraints. His desperation hung in the air, thick as the blood pooling around him. Leona’s gaze wandered, inspecting the man in front of him with clinical detachment. His appearance was no longer that of a respectable businessman, but a wretched, broken soul who had long lost his dignity.

“Tell me, Mr. Wickhamm,” Leona murmured, “What brings a man like you to these depths?”

The man whimpered but said nothing, his eyes flicking from Leona’s icy gaze to the tools scattered around the room. There was no escape. He knew that now.

Leona picked up a knife, admiring its sharpness as he ran his finger along its edge. “The thing about men like you, Mr. Wickhamm,” he continued, his voice dropping an octave, “is that you think you’re untouchable. But everyone has a weakness. Some people have wives, some have children, and others…” He paused, taking a slow step toward the trembling man. “Others have greed.”

Wickhamm’s eyes flickered with recognition.

“You were hired, weren’t you?” Leona asked, his voice softening as he leaned closer. “To hurt someone. A girl, actually. Georgina Floyd.” He let the name hang in the air like a toxin, waiting for the man’s reaction.

Mr. Wickhamm’s face went pale, his lips parting in an unspoken plea. “I—I didn’t have a choice,” he stammered, but Leona silenced him with a raised hand.

“I know,” Leona said, his voice calm as ever. “That’s what makes this so… tedious. People like you always think they have no choice, don’t they?”

The man’s eyes darted around the room, looking for any escape, but there was none. Not here.

Leona stepped back, tilting his head in thought. “You see, I have this little problem,” he murmured, half to himself. “There’s a girl I care about—a soft and sweet thing, like summer.” His eyes narrowed slightly as he stared at Wickhamm. “And you… you tried to bring the filth of my world too close to hers.”

Wickhamm shuddered, his breath coming in shallow gasps.

“I clean up messes, Wickhamm,” Leona said, his voice suddenly sharp. “And you? You’re just another stain.”

He gripped the older man’s hair, yanking his head back, exposing the pale skin of his neck. The light overhead flickered once, casting an eerie glow over the grim scene.

Leona’s hand was steady as he brought the blade to the man’s throat, his fingers warm against the cool steel. “Tell me, Mr. Wickhamm,” he drawled, his tone velvet-soft, “Was the money worth it? Did the few miserable bills they stuffed into your pocket justify the hell you’ve landed yourself in?”

Wickhamm’s lips trembled, his breath hitching, but no answer came.

Leona sighed with palpable disappointment. He wiped the blade clean with a pristine white handkerchief, now streaked with crimson. “And here I thought we were building a rapport.”

Stepping back, he surveyed his work—the blood, the tension, the despair. But in the end, it all had a purpose. A purpose he was about to fulfill.

He could almost hear her voice now, Georgina’s sweet laughter drifting through his mind. The thought of her, warm and innocent, kept him grounded even as he dealt with the filth of the world.

With a final glance at Wickhamm, Leona moved forward again, a cold smile curving on his lips. “Now… Let’s see if you can be of any use to me.”

The room was still, save for the soft drip of blood from the body at Leona,s feet. The silence stretched on, interrupted only by the faint hum of Leona’s breathing as he cleaned his blade. His eyes flickered briefly to the shadows in the corner of the room.

A dark figure hovered there, barely more than a silhouette.

Leona let out an exasperated sigh, his voice low but sharp. “You know, it’s getting old, Cassien. Stop lurking in the damn corner.”

The figure shifted, a quiet chuckle escaping from the shadows. The outline of a man stepped forward into the weak light. Cassien. His shoulder-length curly brown hair framed a face that was both striking and unsettling, with obsidian eyes that seemed to swallow the light around them.

“Couldn’t resist,” Cassien smirked, his voice dripping with a mix of cynicism and amusement. “It’s the only time I get to enjoy the show. You should make it longer, Leona. Really drag it out next time.”

Leona didn’t respond immediately, simply wiping the last of the blood off his knife before sheathing it.  “You’re always here for the ‘entertainment’, aren’t you?”

Cassien shrugged with a lazy smile, his eyes gleaming with a mischievous spark. “What can I say? It’s better than watching those damn politicians play their little power games. At least you get to do something.”

Leona gave a half-smile, clearly unbothered by the comment. “I’m sure I’ll find more entertainment at ‘The Den.’”

Cassien’s expression shifted slightly, no longer playful. “Right, the meeting with the bosses. Let me guess: more promises, more negotiations? Same old dance.”

Leona shot him a quick look, his gaze sharp. “Exactly. And while I’m there, you’ll be dealing with the mess here.”

Cassien’s lips curled upward again, and he cracked his knuckles nonchalantly. “Leave it to me. I’ll clean up the body. No one will ever know he was here.”

Leona gave a nod of approval, pushing a loose lock of chestnut hair back into place as he moved toward the door. “Good. No trace. The last thing I need is complications.”

Cassien tilted his head, the faintest of smiles tugging at his lips. “Always a pleasure watching you work. But I’ll take care of the rest. Go handle your little meeting.”

Leona paused at the door, his hand on the handle. “Don’t make a mess of it. Remember what happens when things aren’t clean.”

With that, Leona left, his footsteps fading as he descended into the night. The sound of the door clicking shut was the final note before Cassien moved swiftly into action, already planning how to erase every trace of the night’s grim work.

Leona slid into the plush leather seat of the Aston Martin DB11, the engine purring to life with a satisfying roar. The night was still young, but his mind was already racing ahead. The meeting with the neighboring bosses was essential—there was power to be claimed, alliances to be secured. But none of it mattered if it didn’t protect her.

As the tires gripped the asphalt, Leona’s gaze flickered to the rearview mirror, his mind briefly drifting back to Georgina. He had seen her earlier, lost in the world of her little cafe, unaware of the darkness that encroached on her life. She would never know the extent of his actions, the depths of the darkness he navigated just to keep her safe. She didn’t need to.

His eyes hardened as he navigated the streets, his thoughts already turning to the meeting ahead. Deals would be made, power shifted, but all of it would serve one purpose.

Georgina.

No one else could stand in his way. She would be his, and anyone who thought otherwise would soon regret it.

Paint

y can still picture himself a couple of years ago, absolutely livid because Hope got away again, let himself be caught only to laugh in Y's face, and run away later. He was ridiculing him, trying to make him and his men a laughing stock.

So when they caught him again, Y was the first to visit, demanding everyone to leave them alone, gun so tempting where he twirled it in his hand. Oh, but when he walked in, he wasn't expecting a man his age, had expected a dirty, old bastard like they all seemed to fucking be.

But Hope was a complete change of scene, giggling where he was sitting on the floor, a cute little hat atop his head and Y didn't know what to think.

This was the feared Hope everyone warned him about? The same man that could escape in mere seconds?

Who was staring up at Y with a glittering smile and painted nails.

Painted nails-

It was too late when Y realized Hope was free, the younger bouncing toward him with quick, happy steps.

Y couldn't move- couldn't even bring himself to lift his gun and shoot, hated himself for it.

Hope looked so sweet when he stopped in front of Y, grin bright, heart-shaped. Y couldn't even be angry anymore- took an enormous risk, letting Hope near him so easily, letting the other touch him.

But Hk pranced around him, giggled, "I was waiting to see when you'd meet me~"

Y didn't reply, knew it was best to keep his mouth shut, even when Hope's hand crawled up his neck, fingers running softly through the hair on his nape.

"You're very pretty, Agust," grimaced because this wasn't okay, knew he was being stupid.

Hope stopped in front of him again, warm hand still on his nape, drawing circles against his skin.

"I'm J Hk," Y... didn't know that, didn't believe him either. "Call me Hobi, yeah?"

He knew Hk didn't hold a special position, their leader was Sj, and Y never had a problem with him- he kept his distance. Never crossed paths with the other and preferred to keep it that way.

So he was definitely surprised when N called one night, telling him that they caught someone on their side of the woods, someone who looked a lot like one of Sj's men.

Things were somewhat calm, nothing was happening out of the ordinary- why would one of sj's men be watching him? He probably stumbled into the woods by accident. So Y told them to bring him in, rough him up a bit maybe and let him go. But he'd escaped before they could even speak to him, and Y was starting to get on edge, nearly daily occurrences now- white ears peeking from behind cars, flashes of white when Y was making rounds.

And it was the same thing, over and over and over again. Hope getting caught only to escape in minutes, and Y-Y didn't want to hurt him- didn't want to start a war over something so meek-

"I'll see you later," He left, and Y let him go. Watched, still silent, as Hk walked out of the back door, turned to wave for the last time.

He stood there, long after Hk left, frustrated for being so weak, slamming the gun against the floor with a tug at his hair.

Fuck, fuck-

he's fucked.

He was marching out soon, barging into N's room to huff out a sharp, "J Hk. Bring me all the J Hk in this fucking country," N nodded with a frown but still brought in piles of folders the next day, and Y apologized, letting him have the rest of the week off because he knew he was maybe a bit unfair, knew N spent the entire night up researching.

N was more than happy to accept and Y got to work quickly, flipping through pages worth of information at light speed.

By the next day, he was starting to give up, disgruntled, maybe even a little angry at himself because he took Hope's words to heart. Why wouldn't the other lie? And now, he's making Y look like a complete idiot.

But he was almost at the end when a little picture tag caught his attention. He paused, brought the folder closer, nearly smiled.

It's him.

Younger, hair matted on his forehead, an awkward smile pulled on his face- but it was him no doubt; same sharp nose and high cheekbones, heart lips, and perfect denture.

J Hk of xyz.

Hk didn't show up for a while, and Y nearly forgot about him.

nearly.

maybe not that morally grey but still if you recognize the names NO YOU DONT thank you for reading this far uhuehueheuheuh

Insanity Plea

The officer opens the door and gestures me inside. Files in hand I adjust my collar and walk in. The door shuts with a loud pop, the stuffy air feeling almost oppressive.

The small room is lit with overhead light, it gives off a sterile glow, washing out all the color. The man handcuffed to the metal table in the middle of the room looks up, his orange jumpsuit almost looking sickly green. He straightens up, although he can’t shake away the worry lines etched into his pale forehead.

“Mr Gable?” I ask as I pull out the opposing chair. He gives a curt nod, a quiver in his lip. “I’m James Becker, your court appointed attorney.” I place down my stack of files and open the one at the top. I skim a few lines, my fingers drum against the table. Gable shifts nervously, his cuffs clinking. “I’m gonna be honest Mr Gable, this isn’t gonna be easy,” I say as I glance back at him. “Lots of evidence, cameras, witnesses, dna…All points to you.”

His sweaty hands clench. “It was an accident-“ He starts, his voice high and breathless.

I raise my hand and stop him. “That right there is gonna get you 50 to life, Peter. Can I call you Peter? Listen, we got a good chance here. If… we play our cards right.”

“Got any history of mental illness? Voices, hallucinations?” I ask, a brow raised.

He looks down at his hands, and shakes his head. His knee bouncing up and down.

I rub my temple, a sigh escaping my lips.

“They…they said I’d get a lesser sentence if I plead guilty.” He says softly, his wide eyes raising to meet mine.”

“Jesus Christ, Peter, that’s how they get you,” I say, my voice rising with exasperation. “You might get the chance of parole after 30 years, bud.”

He looks down again, taking in a shuttering breath.

I stare at him, my fingers drumming against the table once more. “Listen bud, there’s…well maybe another option, but it’s not free.”

He looks up enthusiastically. “S-shit I’ll take anything at this point”

I smile and grab the little black book from my inner breast pocket. “It just requireds your signature, and I promise, you won’t be going to jail.”

“Just…just like that?”

“Yep, just gonna make a deal.”

           ………………

I close the door loudly, muffling the screaming voice of Peter and the officers attempting to sedate him. I hum as I walk down the hall and out of the holding area.

“Mr Becker?” A soft feminine voice calls from behind me. I turn, seeing an elder woman with tired eyes.

“I’m Sarah Lee, I believe you’re representing…Gable..?” Tears well up in her eyes, her voice shaking. “Ah Ms Lee, my condolences,” I say sorrowfully. “Yes I’m representing Mr Gable.”

“Please Mr Becker, if you are a decent man of any kind, please I beg you,” She chokes back a sob, she moves her hands in front of her, pleading. “Please don’t let that monster go free.” Her voice turns bitter.

I smile, my fingers thrumming against my black book. “Let’s make a deal.”

The Monster in the Tiny House

Snuggled into a calm residential neighborhood lived a young man, John. Of all the magnificent two-story houses that surrounded him, he lived in the tiniest one. With barely enough money to make a living, he still called this place home. In the backyard was a vibrant, thriving garden. Flowers from all colors of the rainbow filled the sight. Beneath the flowers were fruits which grew to perfection and vegetables that were grown for the most mouth watering meals. The lively garden had been in tact ever since John's mother sadly passed. He made it his life's goal to keep the garden alive in order to also keep his mother's spirit's alive. Every morning at exactly 6 AM before work, John watered the garden. And every night at exactly 9 PM before bed, John watered the garden. But even as water hydrated the garden day in and day out, it always stayed exactly the same. Underneath the house, however were bugs that would attack in the night. They would slurp all the water that had been provided during the day and hide when John would awake. John was repeating what he had done the day before with not a sliver of progression. But the bugs never used to be there. For they were born from the monster within the house. There were clothes covered in dirt scattered throughout the living space. Dishes and trash piled up to the height of the ceiling. Food scraps covered the floor becoming the new carpet. And the stench that flowed inside could kill someone the instant they opened the door. While John thinks he is keeping his garden alive, he is killing it all the same. His mother would be proud, but not at this. For, John is the real monster living in the tiny house.

120 Alice Court

Mr. Rhinehardt was the kind of person one noticed. 120 Alice Court was a charming Queen Anne three story manse that had been transformed into flats right after WWII. It was advertised as full of character, which meant drafty original windows, gingerbread turrets, pipes that banged, and a sunny wraparound porch. Mr. Rhinehardt lived on the top floor.

In the winter 120 Alice Court put on a good face. Stella Lampfear the artist who lived in the basement/ garden apartment thought the snow frosted old place looked like a lopsided birthday cake. Whenever it snowed she caught Mr. Rhinehardt in his St. John’s sweatshirt shoveling their walkway and vehicles.

The Small-Martinis with their little girl Clarissa and another on the way moved into Old Lady Green’s flat last autumn. Between work and Clarissa, they barely noticed Mr. Rhinehardt. They passed in the foyer with a polite nod. Or he held the door open when they were carrying in groceries and the stroller. They never knew when they lost SugarPants it was Mr Rhinehardt who found it in the recycling, washed and returned the toy cat with a stuffed toy kitten.

During the sticky summer nights every window in 120 Alice Court was wedged open in the hope of a breeze. Maybe that was why Mr. Rhinehardt stood on Miss Feathergill’s last nerve. He was partial to German Thrash Metal and bottles of katzenshiegal on occasion. The summer soundtrack was Miss Feathergill banging her second floor ceiling as Mr. Rhinehardt danced.

While spring cleaning Stella Lampfear noticed the top floor tenant weaving drunkenly up the front stairs. It wasn’t the first time. In fact she noticed his stumbling home more and more. Then there were the familiar long blue bottles tucked in the recycling bins. And of course there was the switch from the pounding beat of Accept to moody requiems.

Having gone through her own blue period Stella recognized all the signs. Her hands clenched and unclenched helplessly. There was no salvation from sadness were hard work and perhaps Zoloft. Stella reclaimed the bottles and sparked her welding torch.

By his laptop Karl aka Mr. Rhinehardt scrubbed at his face and reached for his glass. He was distracted by the tinkling of glass in the backyard. For months he had been smashed between writer’s block and anxiety. He watched the artist in the fading blue light lit by a flame working metal and swaying bottles. Karl set down his glass captivated.

Obsessed

It was never about being my own person. I just wanted to help someone asking for it. Whether or not she got it, I was cruel.

From the first day we met, she clung onto me for dear life. To her, I was so strong and perfect, confident and everything she wished she was. I didn’t ask for anything from her because in reality she couldn’t offer me much, but at the very least she was a loyal and dear friend. I wanted to get her out of her shell.

Slowly she started to worm her way into my life. Texting pestering questions, researching how I did my hair and makeup, calling when she was feeling sad. There would always be some emergency, some trauma resurfaced. And I would answer to do the right thing. I was her rock.

Pretty soon she would startle me with her long stares - eyes always watching me, dissecting every physical part of me, burrowing into my movements to figure out what made me “me.” Out on the dance floors she would, when she thought I wasn’t noticing, study my body as it swayed and she would move like my shadow.

Over the next year, I found myself snappy, shortening my replies. I felt like hiding. Eventually I started making comments in rebuttal to her voice. The very memory of her voice grated my skull. I could not at the time remove myself because I was her everything, her symbol of rebirth.

One day I snapped and never replied. It was my first crisp breath after years of being smothered, of feeling exploited by her desperate gaze, of my space being violated. To this day I’m not sure if I was the bad one, but I am thankful to have been freed.

Navigating Murky Waters

The first thing you should know is that I'm not some sort of angel who strives to always be a do-gooder. I don't care that my parents named me Veronica after the Saint of Kindness. That's on them. They were practically begging for the universe to make me the way I am by naming me after a saint.

Now, I'm no Satan either, let's be clear. I like to think I land somewhere in the middle in terms of my character. A nice, warm grey area. Not to be confused with Gray, my last name. Yes, I know. Notice the irony and move past it, please.

We have far more important things to deal with.

The next thing I need you to know - and this is where you should start taking notes - is that you must contact Evelyn Harper in the case that I don't return at any point during the mission. She knows everything I know and can help you if something goes amiss.

You'll also want to note that it's only the fourth floor we're targeting today. Don't ask questions. Don't ask about names or what they do. Don't ask anything humanizes them. The less emotions and humanity involved, the better. All you need to know is that you're going into the fourth floor as an IT specialist, but instead of updating the software, you'll download our tracking software and bug the office.

We'll use the information we collect over the course of 10 days in order to carry out the next part of the attack. That's where things get a bit bloody. By which I mean we eliminate them all.

I know what you're thinking. How cold; how callous. Take a step back with me, though. If we successfully see this through, we free all of the Chicago Bay hostages. We can save their lives just like that. And you know what else it'll accomplish? It'll shake up the job market like never before. Thousands of jobs will open up in the aftermath of all of this. Full time jobs available for my brother, your best friend, my niece, and your cousin.

Not so black and white now is it? It's the age old question of which is the lesser evil: The lives of a few or the livelihood of many? We're just the unlucky bastards who got tasked with the follow through this time.

Now don't get me wrong. It's not like I enjoy killing just to kill, but I can get behind a legit reason. There is no price too large to pay for the joy of reuniting families torn apart by monsters. Anything is worth the truly good people in this world succeed. We're helping a greater good here, and I promise that you'll see it that way one day.

Now that we've gotten all of that out of the way, are you ready to get started?

Henry

Henry wasn’t sure if he was Henry anymore.

He felt like Henry some days. Well, what he remembered Henry feeling like.

He felt like Henry when he was working in the forge, sweating like a pig and beating the shit out of molten metal. He felt like Henry when Islwyn clapped him on the back and shoved a tankard of ale in his hand. He felt like Henry when a little girl, blonde and filthy, tugged on his cloak and asked for a copper.

He gave her a silver and fought the urge to puke.

It was easier when he didn’t feel like Henry. Worse, a thousand times worse, but still somehow easier. When that dark feeling started twisting inside him, snapping at his heels and clawing up his throat, it was so much easier to remember who he was. Where he was. When he was.

Dugal gave him orders and he carried them out. If he was feeling like Henry they made his stomach turn, but if he was feeling like Not-Henry he barely thought about it.

Seeing Clara nearly broke him. His baby sister, too tall, too old, too strong. He remembered her barely reaching his waist, all big grey eyes and shiny blonde hair he painstakingly braided each morning. But now when he saw her she reached his chin and carried a sword.

Without fail, whenever he saw her, the two beings inside him started tearing into each other. Henry begged and begged to hold her for just a second more. Not-Henry seethed at the indignant girl standing against Dugal. Henry was horrified, horrified his baby sister was grown and had blood on her hands and scars on her body. Not-Henry didn’t even notice.

Henry knew that even if he could decide which one was really him, or maybe even just which one he wanted to be, it wouldn’t really matter. He’d never get Clara back, his Clara back. Something had broken fifteen years earlier, when that blade had sunk into his throat and everything went black. Or maybe it had broken when Dugal had dragged him back, kicking and screaming and clawing from—from wherever he’d been.

He was pathetic. He hated every inch of himself, Henry and Not-Henry alike.