#tony caito x reader

[deborahmessingsfingers]

z’s masterlist

hands

(bo burnham x reader)

you knew he’d be mad, that was the point.

teeth

(demon!bo x reader smut)

there was something about him, each time you saw him, it was like he set off fireworks in your belly, smiling widely with a lit match in his hand.

hair

(bo burnham x reader smut)

it wasn’t often that Bo broke the rules.

mouth

(bo burnham x reader smut)

Bo’s had a long day.

prove it - multichapter

chapter 1

(horror!bo x reader) (unfinished)

at first, it frightened you to think of how such a meek, diffident character could become the very thing they feared in the blink of an eye. but as the days passed by and your persecution and misery continued to worsen in nature, you slowly began to understand just why a kid like Robert, a kid not unlike yourself, would eventually snap.

i’m tired

(bo burnham x reader)

your eyes instinctively closed shut as you felt a wave of dizziness hit you. his avoidant nature and impatience all but confirmed it; he was not doing well.

you know…

(tony caito x reader)

you finally get to meet Tony’s softer side

[pseudonympls]

Might post a short Tony Caito drabble I wrote the other night on like four hours sleep hyped up on caffeine 🥴

Been feeling a bit emotionally weighed down by the Bo manor fic so needed a short reprieve with some quick and dirty dickhead Tony smut 🙃

[pseudonympls]

IT’S HERE!!!

Besties, despite how ready you think you are for this, there is no preparing, just dive in.

If ever there has been a fic recommendation, this is it. Read it, weep, and then go leave her some praise because it’s fucking INSANELY GOOD!

it literally has everything:

Sin bin dialogue CHECK

Absolute filth CHECK

Tony being a little bastard CHECK

Actual reader character development CHECK

Polaroids CHECK

Ridiculous charm and style CHECK

Seriously, put everything aside for a minute and read it, you won’t regret it.

FFMW PART I

Friends, after some delay and much hair-pulling, the first installment of my Tony Caito/Reader fic is up on Ao3

[deborahmessingsfingers]

You Know…

pairings: tony caito x reader

word count: 1097

tags/warnings: explicit language, implied sexual content, anxiety, panic attacks, reader is gender neutral, comfort

also on ao3

Your entire being was vibrating, it felt like you were floating off the ground, held up by a chokehold of anxiety and doubt.

You’d cornered yourself away in the locker rooms during lunch. People were still passing by here and there but it was the quietest place in the school you could think of to hide away and let it out.

It was all just too much. The pressure had engulfed you entirely; gobbled you up as a young, promising, spritely student and spat you out as a babbling mess of deadlines and dread.

You could hardly breathe, your nose long rendered useless by the constant stream of tears and snot. You sat gasping and dry mouthed, quiet sobs escaping your throat each time you banged your head back against the red locker doors, eyes winced shut.

The sound of footsteps fast approaching beckoned your eyes to fly open, your body freezing up entirely, as if you wouldn’t be seen if you just stayed still. The shiny, brown leather shoes that entered your field of vision coaxed a dichotomous sense of relief and dread from the depths of your stomach.

“What’re you doing, honeybun?” the voice asked, laced with a cold, indifferent tone. You looked up to see Tony Caito, the school’s student liaison (and secondarily, your boyfriend) looming over you. You looked up at him, blinking rapidly as you wiped your face clean as best as you could. He simply stood there, taking one of his hands from his pocket with a flick of his wrist to check his watch, as if he had other, more important places to be.

“I-I just,” you started. You’d never talked about this to Tony, or anyone for that matter, you were struggling to find the right words to articulate just what was going on in your mind, “it’s just all too much, Tony.”

He sighed. Tony rolled his neck before grabbing the legs of his pants, lifting them slightly to accommodate his long legs as he crouched down to sit next to you, leaning against the lockers with a muffled bang.

“What’s too much, pumpkin?” he asked. Again, his tone was dispassionate, calloused, as it often was. It made you uncomfortable and confused, wriggling around in your spot as you tried to figure out whether he really wanted to know, or whether he was only asking out of a feeling of obligation.

“All this.” you answered vaguely, hands gesturing to the world around you and your state on the floor.

“Scholarships and deadlines and-and grades and… friends and reputations a-and…” you could feel yourself choking up again, the freefall of words so quick to stop and start.

You looked over at Tony to see his eyes darting between the cracks of the concrete floor, biting his lip in thought as he often did. Waiting for his response only further heightened your anxiety, the little voice in the back of your head berating you for opening up; to him of all people.

In that moment, you weren’t quite sure why you let Tony into your life. He was bossy and judgemental, aloof and haughty. You supposed it was his charm. His neatly slicked hair, his creaseless suits, the way he so effortlessly wooed you with a wink and the promise of a good time.

You were brought back to reality as he inhaled deeply, your stomach dropping with dread as you waited for his beratement.

“You shouldn’t worry about that shit.”

His words rendered you speechless. You expected harsh criticism, for him to take the harsh reality of life and slap you across the face with it. Instead, he looked up at you with a somewhat soft expression - softer than anything you’d seen before anyway.

Usually his stare was gelid and demeaning, the closest thing you’d seen to vulnerability was when he was coming undone on top of you with gasps and empty praise. But there was a certain, unfamiliar whisper of concern behind his eyes now that you’d never seen before. You continued to stare, your open mouth silently begging him to elaborate.

“You’re gonna be okay,” he continued, your brow crinkling in disbelief at the encouraging words escaping his mouth, “you have one of the highest GPAs in the school. You run laps around everybody else when it comes to extra credit. You’re smart… and you’re kind, and you’re funny,” you felt your heart threaten to burst as he continued, your quiet sob session now long forgotten,

“And you managed to bag me, and you know what my standards are like.” Tony laughed awkwardly, wresting a laugh from the back of your throat. You could see his face change to a light hue of pink, his hand wrapping around the back of his neck to scratch it awkwardly.

You watched on in a slight state of disbelief, not truly able to wrap your head around getting to see Tony let his walls down. It wasn’t much, but it was the first time you’d ever seen proof that he cares.

Granted, it wasn’t much, and when he snaked his arm around your shoulder you knew the fleeting moment of vulnerability was soon to be over, but that slight display of genuine affection would have you soaring for weeks.

One of his large hands drifted up to cradle your face, his thumb swiping underneath your eye to dry the last of your tears. As your eyes locked, you felt the bubble of pent up apprehension and unease burst into an enthralling display of denotative fireworks.

For one more brief moment, Tony’s facade remained softened. His eyes darted around the room to confirm your solitude, not wanting another soul to hear his next words as not to expose his unguarded self to his peers. He softly and slightly opened mouth to whisper to you,

“You know I love you.”

Your mouth instantly widened into the biggest grin, your cheeks quick to start aching as you processed his confession.

“I love you too, Tony” you whispered back, milking the intimate moment for all you could.

Tony was quick to snap back to his usual indifferent facade, the arm Round your shoulder pulling you closer to his body as his other hand left your face to meet the soft flesh of your thigh, burying his face in the crook of your neck. You rolled your eyes as you felt him nip and peck away at the peach fuzz behind your ear, shivering as his teeth gently met your earlobe.

“Y’know, I always say the best pick-me-up is a good, hard fuck”

[tony-caito]

Fix Fuck Make Worse- Part III

Tony Caito x Reader: 18+ only

Tags: explicit sexual content, kink heavy,foul language, recreational drug use, underage drinking, angst, hurt/comfort.

[tony-caito]

Fix, Fuck, Make Worse: a Tony Caito x Reader fic in four parts (and an Epilogue)

Graphic by the incomparable @oh-bo

Explicit Sexual Content 18+ ONLY

Tony Caito x AFAB Reader, Tony Caito x Original Female Character, She/Her Pronouns.

A/N: Please see Ao3 tags for content warnings

Summary: Tony Caito is perpetually, preternaturally in the know. From trips to the nurses office to detention assignments, to who’s diddling who under the bleachers during lunch block, no student at Pinkerton Academy can so much as sneeze without the Student Liaison catching wind of it. Wondering how you scored on your standardized tests? He’s liable to know the answer to that before you do. It goes without saying then, that when a new student enrolls at the prestigious PA, Tony will be keeping tabs on them. If that new student happens to be a pretty girl, well- all the more reason for him to make it his business.

Part I

Part II

Part III

[pseudonympls]

Smart Girl

Tony Caito x Reader. AFAB Reader. She/her pronouns.

Rating: Explicit

Unsafe sex. Infidelity. Slight degradation. Semi public sex. Hate fucking

Word Count: 3.2k

Stamping your clock-in card you sighed. Another day at the diner. Readjusting your pepto bismol coloured polka dot dress - the unfortunate uniform all the girls at the diner were required to wear - you ascended the stairs to the diner.

Your shift went by mostly without incident, a few oldies who insisted their coffee wasn’t hot enough, and a couple you’d seen at high school making out in the far booth - you pretended not to see the guy’s hand travelling up the girl's leg, ignorance is bliss, they say.

It had been a month since you graduated Pinkerton Academy, and what a drag the summer was turning out to be. You couldn’t wait to leave high school, spend the summer working part time to save money and then head off to college, Yale, to be precise. But the waiting in between the oncoming storm of excitement and change was long and drawn out….that was until he walked through that swinging door.

Impossibly tall, dark blonde hair parted severely to the side, he swaggered into the diner, and you scoffed. His body encased in a burgundy velvet suit, his expression pointed and arrogant, he spotted you at the bar - you swiftly turned around, busying yourself with polishing glassware, as you heard his brogues travel toward you.

Tony fucking Caito. Otherwise known as the school manwhore - celebrated for it, of course, because it was cool to fuck around as a guy - as a girl, not so much. Otherwise known as senior student liaison. Otherwise known as the guy who saw through you as if you were transparent, for four solid years.

“Hey, I know you, don’t I?” you hear his voice chime over the cheesy eighties music blaring over the speakers.

Your stomach drops - you could have got away with him not seeing you, had you only turned around faster.

Your manager nowhere to be found, you decided you could afford to be a bit cheeky.

You spin around, look him dead in the eye and say “No, I don’t think so?” raising your eyebrows at him, continuing to polish the glass in your hand.

He looks briefly taken aback, clearly not used to people speaking to him in this manner, and says “You...you went to Pinkerton, right?” - suddenly looking unsure of himself. Huh, a small flutter in your chest, you liked that.

“Mmhm” you nod, looking around the virtually empty restaurant, wishing for a four top to come in the door any second, to take you away from this stupid situation.

“Yeah, I knew it,” he clicks his fingers, and says your name, pointing at you “right?”

He...remembered your name? A little taken aback you nodded silently, seeing a small smirk of satisfaction curl around his lips. 

“Yeah, couldn’t forget a face like that” he knelt on the bar with both elbows - towering above you even while slouching, what a fucking bastard.

You left the silence to hang in the air - hoping a little that if you just didn’t speak anymore, he’d leave.

No such luck.

“So, can I get a drink in here or what?” he smirks, glancing down to your hands which had neglected to move for a moment, your fingers gripping the glass tight.

“Sure” you managed to get out, taking on the challenge of staring him down. 

“Root beer” he said, his eyes not once wavering from yours. Exhaling out of your nose you admitted temporary defeat, as you looked away to grab his damn root beer.

Popping the cap and setting it down in front of him, you plastered a grimace over your face as you took his money and put it in the register.

One of the slow days at work you actually wished for it to be busier, but the universe didn’t seem to be in the business of granting wishes, today.

“So, why are you working in this place?” he asked, somewhat innocently, but his tone was classic Tony.

“Well, Tony, some of us weren’t born with a silver spoon in our mouths, and have to work to save money for college in a couple months” You snapped back, arms crossed defensively, cloth hanging limply from your tightly balled up fist. Hot rage seethed beneath your mildly irritated demeanour. 

“Oh shit yeah, you’re going to Yale, aren’t you?” he smirked “Smart girl” he nodded, taking a swig of his root beer.

He seemed utterly unflappable, which only irked you further.

“Mmhm” you nodded. Praying, begging for someone else to walk through that door and save you from this god awful situation.

The universe was listening now, as suddenly a rowdy group of five kids rolled into the restaurant, pursing your lips at Tony. You gladly took your leave, utterly relieved at the distraction. 

While you were taking the kids drink orders, you heard Tony about to leave, when he hollered “Bye, smart girl, seeya round” - you just about turned to see his smarmy face leave through the door. 

You felt an unfamiliar twang in your chest as you continued on taking orders. Heading back up to the bar, you were taken aback to see a crisp twenty dollar bill underneath the empty root beer bottle. He might be an asshole but at least he paid you for the time you had to endure him - you thought, smiling, slipping the twenty into your apron.

Agreeing to work all day probably hadn’t been your best decision ever, downing your fourth cup of shitty diner coffee you were thankful that two other waitresses had turned up to lighten the load. Splashing some water on your face you hastily reapplied your red lipstick and began to climb the stairs to the restaurant. 

The dinner rush was well underway, the hubbub of the evening drowning out the eighties music on a loop, blenders whirring and the shouts from the kitchen were all assaulting your senses. But you put on a brave face and simply got on with it.

Eventually the tables left, one by one, then all at once. Only a few more hours to go until closing, you thought.

You thought you were having deja vu when you saw that exact same shade of burgundy come through the door, only this time it was followed by something else. A tall blonde girl followed Tony in, simpering next to him like a puppy. That’s right - Tony had a girlfriend, Erica. Beautiful, elegant, if not a little dumb. 

She also could have passed through you as if you were a ghost - such was not being a part of Pinkerton’s special select few: the elite. If you weren’t part of their group - you weren’t anybody.

Having their pick of booths across the restaurant, you saw Tony choose one where he was in direct eye line with you. As his eyes caught yours you swallowed hard. Was he back to pick up the twenty he left in error? Was he...fucking with you?

They ordered with one of your colleagues and as you kept busy with small tasks you could feel his eyes on you. Boring into the back of your skull when you turned your back, following you around the restaurant when you had to pass their table. 

After ten minutes of avoiding looking at them, the anxiety clawing your insides was too much - you decided to steal a glance. Only you wished you hadn’t, because you saw Erica at their table, mindlessly scrolling on her phone, occasionally sipping her diet coke, and Tony’s piercing blue eyes, right on you.

You were so taken aback you almost dropped the couple of plates you were balancing, luckily you regained composure to slip behind the door that led downstairs. 

Taking a few deep breaths, and goading yourself to carry on, you were just about to push on the door when Tony came through the doors.

“There you are, I wondered where you’d got to, smart girl” he chides, backing you up against the wall as he nears you, his height seeming very intimidating all of a sudden. 

“Wh...what do you mean” you stutter, your nerves showing through your words more than you’d like.

He glances out the porthole window to his table, Erica still absorbed in her phone.

“Look, meet me in the staff bathroom in ten minutes” his tone gets dark, and you’re not quite sure what he’s implying.

“H...how are you gonna get in there?” you ask, bewildered.

“You’re gonna let me in, silly,” he smiles, seeing his slightly snaggletoothed smile you relax a little.

“Um….uhhh” you flounder, looking for the words but they don’t come to you.

“Now now, you know you've wanted this, ever since high school, right? Well, it’s never too late, y’know” he brushes his fingers up against your cheek, just enough to tickle but not enough, you want more.

“Ten minutes” he repeats as he spins around and retreats through the door.

You remain flabbergasted for a few moments before standing up straight and following Tony out the door into the restaurant. Trying desperately to ignore his gaze as you return to the bar, tuning into your colleague's particular brand of drivel that night, whatever gossip was being had - you had to pretend to be present. 

The ten minutes were almost up - and you hastily told your colleague you were going for a break. Your heart hammering in your chest, fit to burst, you descended the stairs to the bathrooms, and the staff area.

Hearing heavy footfalls on the stairs behind you, you grasped at your key card in your hand, waiting to see the man in burgundy velvet...but instead you were greeted with the black and white chequered trousers of one of the chefs - looking at you with a face like thunder. Storming past you, scanning his own keycard to the staff room you felt all of a sudden, embarrassed. 

What if Tony was fucking with you? It wasn’t beyond him - all the years you hadn’t exactly known him but heard of his antics all over school, he was prolific for taking what he wanted when he wanted it. 

In this particular instance he seemed insistent on taking your pride...what was left of it anyway.

Feeling ashamed for falling for such a trick, you began ascending the stairs, only to be almost bowled over by Tony.

“Having second thoughts, smart girl?” he asked, although his face seemed serious this time.

Struck dumb by his presence, you shook your head, turning around to swipe your key card, allowing you entrance to the staff area. Holding your hand out to Tony for a second, just to look down each corridor to ensure the coast was clear, you waved him on, leading the way to the bathroom. Each step sealing your fate further.

Once inside, Tony hones in on you, pulling slightly on one of his lapels, pursing his lips as he stands in front of you - eyes scanning up and down your body.

“You’re pretty fucking cute, you know that? Trying to pretend you hate me, gorgeous” his eyes narrow as he speaks, making you gulp instinctively. 

“I..I don’t hate you, you were just…” you start “An asshole in highschool, let me guess?” he finishes for you, placing his hands in his velvet pockets.

Him being this close to you - you can smell his aftershave, something deep and masculine. You take a sharp intake of breath as you feel want pool in your underwear, your body sure picks its assholes to be attracted to.

He walks toward you - slow and steady but absolutely in pursuit of one thing. Your back hits the cold tile of the bathroom wall and you grimace, he has you right where he wants you - and also, where you want to be.

Pressing his body into yours, you’re aware of how much taller he is - he brings his face down to meet yours and smiles that genuine smile again, before melting his mouth to yours in the most exquisite way.

His lips are soft and well moisturised, molding to yours like they were made for your lips. You feel his hand come to your jaw and he slowly opens your mouth with his tongue. What’s that taste? Something...spicy, cinnamon is it? 

His mouth is fiery in more ways than one as he deepens the kiss, licking your lip with his tongue and lightly massaging the skin of your collar bone with his fingers.

Your hands instinctively grip his forearms, clad in the luxurious velvet. One arm snakes around your waist, pulling you ever closer to him - so close you can feel him pressed up against your hip bone, you let out a squeak of surprise.

He pauses, and begins to kiss along your jaw, threading his fingers into the hair at the nape of your neck he continues, placing gentle kisses down your throat, occasionally offering a sweet suck to the skin.

Palming your breast through your dress you let your head sink back to the cold tile as you let him suck and kiss the flesh on your neck, feeling yourself getting wetter every second.

“Haven’t got time for any of the good stuff today, honey, Erica’s an idiot but she’ll notice I’m gone soon enough - gotta get to the main event I’m afraid” - your stomach lurched at her name, you were distracted for a few seconds enough to not notice Tony’s hand slip up your dress and press into your panties.

Jolted back to reality, you saw the shit eating grin on Tony’s face as his fingers slipped inside your underwear, and he began sliding his fingers against your clit in circular motions.

A small moan erupted from your throat as he pressed into you, digging his teeth into his bottom lip as he watched you below him. His hips bucked into your stomach and you took the opportunity to feel him through his velvet trousers, his hard cock pushing through the fabric on to your hand - you could practically feel him pulsing already. 

You tried not to notice how incredibly large the bulge was...you had heard the rumours going around at school: that Tony was hung like a horse. Of course such rumours while at school were bound to be bounced around - you’d sooner ignored them.

Ceasing his movements on you he brought his fingers up to his face, sinking them deep into his mouth, sucking them clean and releasing them with a pop.

Taking his arm from around you to undo his trousers, letting them fall by his feet, you saw now that the rumours must have been true. The stark outline of Tony’s cock through his pants was...the largest you’d ever seen.

“What’s wrong, sweetheart?” he asks, bringing his hand down to play with himself, staring you in the eye. “Never seen one this big, before?” he smirks, hissing gently as he continues to rub his cock.

Pushing the waistband of his underpants down you were shown the full view of what was to be shortly destroying you. 

“You’re on birth control, aren’t you?” he whispers, seemingly disappearing into his own bliss as he strokes himself.

“Mmhm” you answer, almost unable to peel your eyes away from his cock.

“Good girl” he says, pressing his hips into you as he lifts your dress around your legs, prompting you to wrap your legs around his waist. He grabs your lower body and presses you further up against the wall - so that your aching centers have some chance of aligning. 

The tip of his cock presses against you - and for a moment you can’t believe you’re here, about to fuck Tony Caito in your work bathroom. 

But Tony pauses, leaving much to be desired.

“Tell me you want it” he whispers deeply, his lips next to your ear, his breath sending tingles up and down your spine.

“I want you, Tony” you breathe back, and at his cue, he slowly presses his gigantic length into you, your voice involuntarily moaning and squealing as he fills you, your legs shaking with overstimulation as he presses against every inch of your insides. Feeling like there’s more him than you in your body at this point.

Pulling back out of you slowly, he slams back in, sandwiching your body between his soft velvet clad torso and the cold hard tile. He begins thrusting, each delicious thrust pressing against your clit roughly bringing you ever closer to your peak. The soft grunts leaving Tony’s lips and the vulgar wet slapping noises your bodies make are the only sounds that fill the bathroom, because one of Tony’s hands came up to clamp around your mouth to quieten your squeals. 

The pure concentration on Tony’s face, the way his eyebrows knit together, makes your core light on fire as he pounds into you, your eyes rolling back inside your head in pleasure as he fucks you.

“You gonna come for me? Huh?” Tony pants between placing wet kisses on your neck. “You need to come for me, you smart...whore” - the way that word rolls off his tongue, sweet like honey, sharp like poison, tips you over the edge into blinding, all encompassing bliss. Your pussy convulses atop his cock, and you feel him shudder beneath you, shooting his load deep inside you as he attains his own peak.

Coming back to reality, you’re reminded that you’re at work, having just had sex with Tony fucking Caito in the bathroom...he clearly sees the horror dawn on your face, as he grabs some toilet paper and places it between your legs, relinquishing his harsh hold on your body.

He makes short work of dressing his lower half, straightening up, and pressing his fingers into your jaw as he says “Clean yourself up, honey, you’re a mess” with a devilish smile.

As he unlocks the door to leave, he says “seeya, smart girl” - that genuine smile is back, erupting an explosion of butterflies in your stomach.

Before you realise, he’s gone, and you’re a quivering mess against the bathroom wall.

You take some time getting composed - turns out you look like you’ve had the shit fucked out of you. Cleaning up some of your smudged makeup and re-doing your hair, you’re reminded that you only have an hour left of work.

Leaping up the stairs, fully expecting Tony to be still sat at his table, you stare in dismay as you see their table empty and cleared.

You shook your head, and told yourself that even if he were still here, it would be with his girlfriend and he wouldn’t be waiting for you - you, the girl he just fucked unceremoniously in the bathroom.

Still in your own head, you didn’t notice one of your colleagues run up to you. 

“Hey, um, the guy on table eight told me to give you this?” she said, shoving an envelope into your hand, and walking away quickly.

A little flabbergasted, you opened the envelope, to see a fifty dollar bill peeking out, and a napkin with a phone number on, simply saying “Call me, smart girl”.

Maybe you’d found something more interesting to do over the summer after all.

[tony-caito]

For any of my fellow Sin Bin fans who give a noodle, my upcoming fic will be a multi chapter Tony Caito x Reader story. So uh, buckle up.