You always wonder why, out of all the pretty and influential girls chasing after him, he chose you. It doesn't help how of a unit he is. Your typical perfect guy, popular, rich, and body that's comparable to a Greek God... and his voice— how you love his gentle and warm voice, there's just something about it that hypnotize you.
He always compliments you, shower you with affection, and be an absolute sweetheart. It gets you pissy. You don't know why you're always in a foul mood around him, he's not even doing anything that could trigger you. He takes a breath and you're already fuming. Grumbling profanities that he would laugh at wholeheartedly, like you didn't curse his entire being.
You hate how perfect he is. Hate how much you adore him. Hate how much you love him, and inside your mind you always question if he genuinely loves you. Maybe he's just playing with you? Waiting for the day he'd humiliate you, telling how you're too idiotic to even believe someone like him could ever love you.
That's probably why you're always cautious around him, you don't believe him enough to love an average girl like you.
***
He can't believe he's dating the cutest in the world. Everytime you scowl, show that adorable pout, he just wants to squish your cheeks together and kiss you plenty. Like a little kitty hissing when you sneer curses at him.
It's adorable really.
You'd say you didn't want to go to the movies he chose. Yet, you arrived earlier than expected, wearing a hint of makeup in that cute dress of yours. Makes him want to crush you. You put in the effort, took the time, even gave him the watch he'd been talking about—his favorite.
He really loves you. Really really loves you but why are you acting like he doesn't? He's confused. Hasn't he done enough to show you, tell how much he adores you? It makes him sad. Don't you know how much he's holding back? There's only so much he could take, you know. He could just take you everytime you run that cute foul mouth of you, shove his cock to make you shut up. But he's so patient with you because he loves you.
So don't push him too much, ok? Or else you might not like it when he finally show you his desire.
***
"You're late," you grumble, sending him a glare. Your arms are crossed, and your foot taps impatiently on the ground.
He chuckles, a soft, knowing smile playing on his lips. "I arrived just on time, sweetie," he says, stepping closer. "You're just too excited for our date, no?" His voice is teasing, but his eyes are warm, sparkling with affection.
You huff in response, but you can feel the corners of your mouth betraying you, tugging into a smile. He notices and takes your hand, his thumb brushing lightly over your knuckles.
"You're just so cute, you know? I really wanna crush— ow!" He hiss slightly as you swat his arm. He pouts a little, "You're strong, you're gonna leave a bruise."
You roll your eyes— as if that's gonna happen. Huffing you tug on his hand, "Let's go. I'm starving."
He smiles, looking at your back, "Ok, sweetie~."
Ah, you really are so cute.
He can't wait to fuck you.
***
"Why're you not eating, sweetie? Is the food not to your liking?"
Your appetite was gone the moment that waitress flirted with him, leaving you empty and bitter. This always happen. You're sick of it, sick of being jealous and feeling shitty for not looking like his girlfriend. Are you really worthless by his side? Do people not see you as his companion?
"Sweetie?"
You didn't want to lash out on him so you remained silent. Too bitter to talk. Even the food turned bitter, leaving you more upset.
He's such an idiot. But you're more of an idiot for being triggered by that stupid waitress, too much of a wuss to tell her he's taken, that he's yours. You're the idiot.
"I don't wanna eat anymore," you bitterly muttered, your face covered by the shadows of your hair, hiding that frown you wore he always seems to love on you.
He gets a sick twisted feeling in his guts, watching how jealous you get whenever some worthless wench tries to get his attention. It satisfies his urge, his sick thoughts hidden by his angelic face. You really love him, don't you? His lips curving into a sweet smile, eyes twinkling with desires. If only you know how much he gets off with you being jealous, you'd never doubted your pretty little self.
So… why are you saying such stupid things?
“Let’s break up.”
“Hm?”
“I said…” You take a breath, steadying your voice. “Let’s break up.”
For a moment, his smile wavers. Just a fraction. His right eye twitches ever so slightly, a crack in the carefully crafted mask he wears. But then, like a master of illusions, he recovers, his sweet facade sliding back into place, though something darker lingers beneath the surface.
“Now, now,” he says, his voice dripping with a saccharine softness that makes the hairs on your neck stand on end. “What’s the matter?” His tone is gentle, almost soothing, but there’s a sharp edge to it—a venomous undercurrent that cuts through the air.
You don’t answer immediately, your chest tightening under his unblinking stare. It’s as if he’s waiting, watching every little twitch of your expression, trying to peel you apart without lifting a finger.
“I just think…” you start, your voice faltering as his head tilts slightly, his smile remaining unnervingly intact. “I-I think we’re not… good for each other anymore.”
His smile widens, but it doesn’t reach his eyes. Instead, his gaze sharpens, a predator sizing up its prey. He takes a step closer, the air between you growing heavy. “Not good for each other?” he repeats, feigning confusion. “Sweetheart, where’s this nonsense coming from? Didn’t we promise forever?”
The sweetness in his tone sends a chill down your spine, but you hold your ground. “Forever shouldn’t feel like this,” you say, trying to steady your trembling hands.
It shouldn't make you feel bad about yourself, shouldn't make you anxious, shouldn't make feel... pressured.
For a moment, he says nothing, his eyes boring into yours. Then, his chuckle breaks the tension, soft and low. “Ah, I see,” he murmurs, leaning in just enough for you to feel the weight of his presence. “You’re upset. That’s all. We’ll talk this through, won’t we?”
But his words aren’t a question—they’re a command, wrapped in the guise of concern. And as his smile lingers, you realize leaving might not be as simple as you hoped.
***
Why is this happening?
You thought he would accept and move on.
"Mmm, that's it sweetie. Take it deeper." He coaxes, his grip on your hair tightening. He starts to push forward, forcing more of his thick length past your stretched lips.
So why?
Your eyes squeeze shut tighter as he pushes in deeper, your throat convulsing around his invading cock. He throws his head back with a guttural moan.
"That's a good girl. Mhm, your throat feels so good wrapped around my dick." He grunts, starting to set a steady pace. Fucking into your mouth, using your face like a cock sleeve.
It was gross. He never did that to you.
Lewd, wet sounds fill the office as he picks up speed, his heavy balls slapping against your chin with each rough thrust. Drool escapes the seal of your lips, dripping down your chin and onto your messed up clothes.
He looks down, taking in the debauched sight of you on your knees, choking on his cock. His dick is spit-shined and glistening, streaked with their drool. Shit. The sight makes him thrust harder, faster, chasing his pleasure.
"Look at me," He demands breathlessly, wanting to see the tears and desperation in their eyes as he uses their mouth ruthlessly. He's close, so fucking close already from the intense, vice-like grip of your inexperienced throat. He grunts and curses, slamming forward one last time before pulling out abruptly.
Thick ropes of cum paint your face and hair, marking you as his. Some of it even lands in your eyes, making them sting and water.
"You're so pretty... You look so pretty covered in my cum," he whispers lovingly, smearing the head of his cock across your messy face, pushing the hot seed into their skin like makeup. "The prettiest girl in the world."
You were supposed to break up with him...
How did it escalated to this?
***
It's not like he's losing a lot... you aren't that special. So why is he acting this way? There are a lot of better options for him, prettier, smarter, and richer girls. Someone who can actually match him, who doesn't embarrass him, worthier to stand beside him.
Why is he fucking you like his life depends on it?
Your eyes already hazy and unfocused, breathing hard as you couldn't count how many times you've already come.
One of his hands snakes up your trembling body, finding a soft breast. He squeezes the supple mound roughly, fingers sinking into the pliant flesh as he kneads and gropes. He finds a pert nipple and pinches it cruelly between his thumb and forefinger, rolling and tugging until it stands stiff and aching in the cool air of the room.
"Hm? Are you already tired? We're just starting," he coo, his hips slamming forward with renewed vigor. He leans down, his mouth finding your neck, sharp teeth sinking into the tender skin. He bites and sucks, determined to leave his mark on you, to claim you as his own. His. He can feel his orgasm building, his heavy balls tightening as he ruts into your abused cunt. The wet, obscene sounds of your coupling fill the room, punctuated by the creaking of the bed and your cries. He's close, so fucking close to filling your cunt with his seed.
"Gonna... hngh... fill this pussy..." He grunts between clenched teeth, slamming home one last time. His cock throbs and pulses as he starts to come, thick ropes of hot cum painting your inner walls. He grinds against them, making sure they take every last drop as he marks your womb with his essence.
Finally, with a last shuddering groan, he collapses on top of you, his softening cock still buried deep inside your tender, cream-filled pussy. He pants harshly against the shell of their ear, his hands still groping and fondling your sensitive body.
"Y-You're an idiot..." You sniffle, "Why me? There's a lot of—."
He cuts you off, "You know, I would never cheat on you, right?" He whispers tenderly, kissing your ears as if assuring. "No matter who comes to me, I would never pay attention to them. Never. You're the only one I want." His other hand comes up to grip your chin, forcing you to meet his intense, burning gaze.
It was the first time you ever heard his voice to be so... vulnerable.
"The only girl I want... So..." You can hear his voice shake, "Don't break up with me, ok?"
Your eyes glaze with tears, your heart tugging at his words. No, it wasn't supposed to end up like this. You made up your mind a few weeks ago, always nagging at the back of your mind. Ending your relationship would be the best for you two—.
He kisses you then, any doubts in your mind disappearing as his mouth claiming theirs in a brutal, dominating kiss. His tongue pushes past your lips, plundering the warm cavern as he grinds his hips forward, rubbing his throbbing erection against your thigh.
Ah, you don't care anymore.
"Don't think anymore, ok? Just let me do it for you."
He starts to rub the broad head of his cock along your slit, coating himself in your combined juices. "Tell you what, sweetheart. I'll be gentle like the usual... for now." He promises darkly, his voice rough with restrained lust. "I'll make this first part nice and slow, nice and easy for you."
"H-Huh?"
With that, he starts to push forward, the thick length of his cock slowly sinking into your tight, clutching heat. He has to fight the urge to slam forward, to bury himself to the hilt in one brutal thrust. But he resists, forcing himself to go slowly, to savor the exquisite feeling of your walls stretching around him.
"Ah, you're still so tight." He grits out through clenched teeth, his fingers flexing against your hips as he fights for control. "Such a perfect cunt."
"Too soon! I'm still... s-sensitive!" You cried out but he starts to move then, his hips rocking in a slow, sensual rhythm as he fucks into you with deep, deliberate strokes. Each thrust pushes him a little deeper, a little harder, until he's finally buried to the hilt inside you. He pauses for a moment, letting you feel the heavy weight of him, the way he's stretching you impossibly full.
"Hehe, sorry can't help it. Does that feel gentle enough for you, sweetie?" He asks, a small smirk playing at the corners of his mouth, yet his angelic face covers it. "Or do you need me to be even more... careful?" He punctuates the word with a sharp thrust of his hips, grinding his pelvis against your clit.
Your brain short circuit by the overstimulation, all you could think about was him, and his big cock, "A-Ah, you— ish... so good~!"
He snarls in feral pleasure as he feels your pussy clench and ripple around his pistoning cock. The way you are moaning and crying out, begging him not to stop... it's the headiest fucking thing he's ever heard. It makes him want to ruin you, to fuck you so hard and so deep that you'll never forget the feeling of his cock splitting you open.
You came in surprise, your eyes rolling in the back of your head, chest heaving, "C-Can't too much..!"
"You can do it," He growls, his voice a dark, distorted rumble. He can feel his own release building, his balls drawing up tight as he fucks into you with wild abandon, "A-ah~ clench this greedy cunt around my dick, dollface. Milk it for all it's worth.
You never saw this side of him before, a more vulgar side to him. Spouting dirty words that's the opposite of his facade. Maybe, you didn't know your boyfriend that well? He was always gentleman to you in bed, always going with your pace and being mindful about his words but now...
"N-No~ I really ah! Can't!" You shake your head frantically, having enough of the sensitivity.
"Yes, you can! You will, sweetie~!"
He buries his face in the crook of her neck, biting and sucking at the sensitive skin as he chases his pleasure. He wants to mark you, to leave his claim all over your body for everyone to see. He wants the whole world to know that you belong to him, that you're his to fuck and fill and love as he sees fit. The thought of another man putting his hand on you makes him mad, you're only his and he isn't afraid to take that way for you to be officially his.
"I'm gonna cum, sweetie." He grits out, his hips slamming forward with sharp, brutal thrusts. "I'm gonna pump this tight little pussy full of my seed, gonna breed this fucking cunt until it's dripping with my cum."
Breed?
He reaches down, his fingers finding your clit and rubbing mercilessly at the sensitive bundle of nerves. "I want to feel you cum on my cock, sweetheart. I want to feel you shake and quake as I fill you with my my child."
Wait...!
His other hand slides up, wrapping around your throat and squeezing lightly. It's enough to make you gasp for air, pulse jumping wildly beneath his touch. It's enough to make you even tighter, body instinctively clenching down around him as he fucks into you with short, vicious thrusts.
Too much!
"Now, sweetie~ cum. Now." He commands, his voice a dark and sinful. And with a final, brutal thrust, he buries himself balls deep inside her and starts to cum. His cock jerks and pulses as he paints your insides with thick ropes of his hot seed, filling you up just like he promised.
So full...
You gasp out, your skin flushed and damp with sweat. The room spins around you, his weight pressing you down into the mattress as you struggle to catch your breath. Body aches all over, especially between your legs. The feeling of his cum painting your insides is strange, unsettling.
Your vision having black spots, your consciousness fading as you hear him murmur promises to you.
"I'll take responsibility whether we have a child or not, we'll get married and have a cute child."
You feel a warm kiss on your forehead.
"I love you. I love you more than anyone else, I only love you."
Carlo "The Hammer" Santoro (Capofamiglia/ the Don)
Yandere Short Stories: Den of Wolves (Pt 1)
Yandere Mobsters x Waitress Fem Reader
A group of three mobsters sat in a dimly lit speakeasy as two of them conversed back and forth. Sonny remained bored as he nursed his drink while Tony and Nico went back and forth.
“No wonder you can’t get a girl, Tony. You’re fat as hell.” Nico loudly laughed as him and the boys all poked at Tony. “Probably haven’t seen Lil’ Tony in ages, huh pot-belly?”
“I’m not fat! Nonna says I’m husky.” Tony snapped as he gestured to his muscular yet bulkier frame. “I’m built strongly unlike you and your twig legs, Nico. You’re all skin and bones.”
“Tch. Whatever you say with your alderman.” Nico clicked his tongue as the two mobsters then became engaged in a heated back and forth exchange of insults.
The two stopped their squabble when the door swung open and a beaming Vinnie strolled in. The youngest mobster gave his group a big grin that screamed the cat finally caught the canary.
“Who got you smiling like that, Vinnie? Finally brought a broad back to your place?” Tony laughed at what Nico asked.
“Now you know I’m a picky man, Nico.” Vinnie adjusted his suit and pointed his nose up to the ceiling. “I got standards, unlike you.”
Tony loudly cackled when Nico’s face flushed in shame. Sonny only gave a smirk before he went back to his drink.
“Hey now. No need for friendly fire. It was just a question. You don’t usually smile like that.”
“If you must know, I asked that doll at the diner near the docks out. She’s a real pretty dame.” Vinnie told the boys who snickered.
“The one you’ve been ogling for months? We thought you were just gonna continue being a creep.” Sonny’s thick accent rung throughout the empty speakeasy. He reached into his jacket pocket to pull out a pack of cigarettes. “Didn’t think you knew how to talk to girls, Vinnie.”
“I do too know how to talk to girls, Sonny!” Vinnie spat as his face grew red from embarrassment. “She’s just… she’s different. I like her a lot.”
“You must if you’ve been after her this long and still haven’t lost interest. You’ve been stuck on her.” Sonny hummed. “Must be real pretty to keep you interested.”
“She’s my Bella and she’s the prettiest girl I’ve ever laid eyes on.” Vinnie sighed dreamily. “We’re dating now.”
Sonny gave his little brother a look. “Something tells me that you’re lyin.’ I don’t know any dame who’d willingly date a guy with your ugly mug. Did you flash her your gat?”
The other men laughed as Vinnie glared at Sonny. Everyone knew Vinnie’s scar on his cheeks was a sore spot for him.
“Sorry I’m not a pretty boy like you, Sonny.” Vinnie huffed. “But she’s still my girl.”
Sonny waved his hand to dismiss Vinnie’s claims. “Sure she is and pigs can fly too.”
“I’ll show you guys! I’ll take her out on the town.” Vinnie huffed, the tall mobster left the speakeasy in a hurry to go to the diner with (your name) worked.
.
.
.
(Your name) had just finished a shift when she heard the horn of a car honk at her. She turned to see Vinnie in his all black Cadillac town sedan as the monster gave her a goofy grin.
“My girl just got off work, how about I drive you to a restaurant, hm? My treat, sweetheart. I’m starvin’ and I know this spot down in little Italy you’ll love. The food’s to die for, I swear. ” Vinnie got out of the car to offer his arm to her. The scent of his aftershave was subtle along with the scent of tobacco. She smiled at how much effort Vinnie put into a dapper appearance.
“Thank you, Vinnie.” (Your name) smiled at the mobster. Despite the fact she didn’t give him an answer when he asked her to be his, Vinnie truly believed she was. It was almost as if she didn’t have a say in the matter. “You’re as sweet as pie.”
She smiled when he puffed out his chest a bit like a male bird did to impress a mate. Vinnie lead her over to the passenger side of his vehicle and he swatted her hand when she tried to open the door.
“Hey! No. I’ll open all the doors for you, dear. Especially to my can.” He huffed. “You’re my girl, so you’re gonna be cared for. No need to lift a finger.”
(Your name) smiled politely as he helped her into the Cadillac, his dark eyes filled with warmth. Maybe Vinnie Moretti wasn’t as bad of a man as the rest of Manhattan made him seem?
.
.
.
Vinnie took her to a nice restaurant and made sure to be the perfect gentleman. Yet she noticed the way the waiting staff seemed jumpy around him. Vinnie was not the boss by any means, but his rumored ruthlessness earned him the title of capo.
“This place swanky enough?” He gave her a grin. “This is one of the best spots in little Italy. It has the best cuisine. You like Italian food, sweetheart? I’ll give you some recommendations-“
A young waiter greeted the two with a polite smile and a bow. His gloved hands handed them both menus to start.
(Your name) gave a smile to the waiter when she was handed a menu. If she had looked up, she would have seen Vinnie’s face change green with envy. A terrifying expression was momentarily on Vinnie’s rugged face, his dark eyes now locked onto the waiter who went as cold as ice.
“W-would you like to hear the specials-“
“I don’t appreciate you interrupting me when I’m talkin to my girl. Scram.” Vinnie told the waiter who gave a bow and left with his tail between his legs. Vinnie then gave a smile to (your name) as if he hadn’t just expressed a thinly veiled threat to the waiter. “Anyways, doll. I recommend the meatballs.”
Vinnie began to ramble on and on, his hands moved as he spoke yet (your name) began to tune him out. Instead, she lost herself in her thoughts.
If she were to be involved with Vinnie, her life could become dangerous. The life of a mobster, especially one in the bootlegging industry, was not the brightest idea. No matter how charming Vinnie was, he was still a crook. She needed to end it before she got in too deep and drowned.
Vinnie grabbed (your name)‘s hand and kissed her knuckles to draw her attention back on him. His dark eyes studied her face.
“What’s got your attention that’s more important than me?” He had a teasing tone, yet she couldn’t see that little green monster that lurked behind those chocolate eyes. She didn’t want to be the one to find out if his rumored temper was true or not.
“I was just the inning about how lucky I am.” She gave him a warm smile and he instantly peppered her knuckles with more kisses. It seemed his ego was easy to satisfy.
“You know how to make a man’s heart race, sweetheart.” He smiled. “How ‘bout I take us somewhere to dance tonight?”
“Oh, but I’m not in dancing attire-“ Vinnie interrupted her with a wave of his hand.
“Nonsense. I’ll get ya a new dress and all that jazz. I’ll dress you to the nines. I’m sure a department store would bend over backwards to serve ya since you’re my girl.”
(Your name) just gave a smile to him while he ordered an assortment of different foods to try. Perhaps cutting things off would be much harder than she thought. Especially since Vinnie thought she belonged to him.
.
.
.
After the meal Vinnie dragged guided (your name) to the department store. The mobster was eager to show what colors and styles he’d like to see her in. His dark eyes watched her marvel at a set of gold jewelry in interest. Gold and red went well together in his eyes.
“This is real nice, don’t cha think? I’m thinkin’ ruby red. I think it’d suit you, sweetheart. I think it’ll make you look like a rose. What do ya think?” He beamed. “Sei carina in qualsiasi cosa.”
“What?” She softly asked as Vinnie laughed.
“You’d look pretty in anything.” He smiled warmly. Golly when he smiled like that, he didn’t look nearly as intimidating. “What do you think? Want to match my tie tonight?”
She gently touched the fabric in thought. This color was indeed pretty. Vinnie had good taste. “It’s lovely… how much?”
“Psh. All me.” Vinnie laughed and took out his wallet to flash his cheese. “I could probably buy every dress in this store if you wanted, sweetheart.”
“There’s no need for all that, Vinnie. I like this dress.” (Your name) then heard Vinnie call over the clerk.
“I’d like to pay for this dress her and my girl was eyeballing those jewels over there. I’ll take them too.” Vinnie put on a show for (your name) and the workers in the department store. “I want to spoil ya, sweetheart.”
“Thank you, Vinnie.” She smiled politely at the mobster who practically had hearts in his eyes. The young waitress still had no idea why he liked her so much.
Vinnie had the attendants dress her up to the nines as he searched around for a pair of shoes and a perfume. He wanted his girl to look her best so he could show her off to the boys. He’d show them that he indeed made her his squeeze.
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.
.
Vinnie paraded her around the speakeasy on his arm to his boys. His chest was puffed out and a smug expression was on his face.
“This is my lady, boys. I told you she was pretty.”
Sonny was the first to greet her. His tall form sauntered over like a cat. His dark eyes filled with mischief when he bent down to press a chaste kiss to the back of her hand that made her whole body shiver.
“It’s nice to know this twerp has good taste.” Vinnie scoffed at his handsome brother’s insult.
“Get the fuck outta here.” Vinnie gave him a little shove, his dark eyes narrowed at his brother. “Don’t listen to this cake-eater, sweetheart. He’s full of empty words that all the broads love.”
“Is he?” She asked in a soft tone, her lashes fluttered up at Vinnie. Vinnie was hooked, line and sinker.
“Think I don’t know my own brother? This guy would charm the pants off anything he can.” Vinnie jabbed his finger into Sonny’s chest. “This wise guy probably thinks he could steal you away but I won’t let him. You’re my girl.”
(Your name) just smiled as Vinnie lead her away from Sonny. But she couldn’t get rid of the way Sonny’s dark gaze made her feel like helpless prey spotted by a wolf. She gulped and tried to play it cool, but this speakeasy made her uncomfortable.
Even as the live jazz music continued on and Vinnie pulled her into an intimate slow dance, (your name) felt like she was trapped in a den of wolves. If only she knew she really was tangled in a mess she should have avoided like the plague.
tell me about all the fantasies you have about me. yes, no matter how gross they are. no, dont stop even when i look disgusted. i wanna hear all about it ♡
