#agent jack daniels | Explore Tumblr posts and blogs

duh-angel · 6 months ago

Text

Missing you

Jack Daniels ~ Agent Whiskey x afab!reader (wc: 2.6k)

“Wish you were here right now, all of the things I'd do. I wanna get freaky on camera” — Cybersex by Doja cat

SMUT ONE SHOT | MDNI | +18

backstory: You found yourself in a particularly tiresome mission in the city of Rome. Although the work kept you occupied, it didn’t stop Jack from constantly calling you and expressing how much he misses you. One day, he sends you a special gift.

You found yourself rocking back and forth in your comfortable hotel room chair, captivated by the glorious sight of Rome through the window. The vibrant cityscape, a fusion of modernity and historic charm, held your attention so thoroughly that you could spend hours just gazing at it, if not for the fact that you were currently on a video call with your “boyfriend”, Jack.

The conversation went smoothly, the two of you chatting about your trip and how much you missed each other's company. In the midst of the conversation, Jack's voice suddenly shifted, hinting at a surprise.

"Hey sweetheart, I've got something special for you. Take a peek inside your suitcase, would ya?"

You glanced at the leather suitcase bearing the renowned S logo, the company monogram gleaming in the center. With a hint of anticipation, you carefully opened it, revealing a box wrapped in blue. You looked back at the camera and gave him a sly smirk, silently inquiring about the mysterious gift. Your mind buzzed with curiosity, wondering what treasures lay hidden inside the deceptively small box.

"Go on, open it," Jack's voice cut through the silence, his tone dripping with mischief and anticipation.

Your heart skips a beat as you gaze at the vibrator nestled in the blue box, a blush spreading across your cheeks. The sleek, purple device seems to wink at you, promising an unforgettable evening. You could feel Jack’s eyes light up with mischief as he saw your reaction on the small screen. A roguish grin spreading across his face.

"Well beautiful, looks like Santa came early this year," he draws teasingly. "I thought you could use some company on your little trip. Why don't you give it a test run for me, hmm?" His voice drops, taking on a husky, seductive tone. "I wanna see you play with it, darlin'. Put on a little show for me."

He leans back in his chair, showcasing his bulge to your hungry eyes. One of his hands casually rested on it, making him groan softly. His brown eyes practically undressing you through the screen, making your body shiver. "Don't be shy now.” He whispers. "Turn it on, sweetheart. Nice and slow. Let's see how loud I can make you moan from all the way over here."

The heat of your blush intensified. Hell, you felt like you were about to pass out from how overwhelmed yet turned on you were. Slowly, tentatively, you reach for the vibrator, your heart racing as you switch it on. The soft hum fills the otherwise quiet room. Your eyes widened as you felt how your hand quivered from the power of the toy, and you can't help but imagine the sensation it might bring.

As the vibrations grow stronger in your trembling hand, Whiskey's grin widens. He watched your every move, drinking in the sight of you under his spell. "That's it, baby. Mmmm, you look so fuckin' hot right now," he groans.

"I wish I was there with you, watching those pretty pink lips of yours wrap around that toy... But I guess this will have to do for now." He palms himself through his jeans, clearly getting off on the show. His free hand reaches for a cigar, lighting it up as he settles in to enjoy the view.

"Go on now, sweetheart. Don't keep me waiting," Whiskey urges, his voice needy with that typical hint of demand. "Bury that toy nice and deep, just like you like it. Fuck, I can almost hear those sweet little moans..."

He takes a long drag of his cigar, blowing out a plume of smoke. His eyes never leave the screen, riveted by your every move.

You disregarded your pants and underwear in a clumsy manner, feeling almost idiotic to do this through a video call, but in a twisted way, it was filthy, raw. Jack licked his lips, his gaze smoldering with lust as your anticipating legs opened just for him. He's clearly enjoying putting you in this compromising position, eager to push your buttons and drive you wild with pleasure, even from a distance.

With a deep breath, you press the vibrator against your sex, biting your lip as the buzzing warmth sends tingles through your body. inevitably, your back arches and you let out a mix of a gasp and a moan. Your eyes quickly go to the man on the screen, enamored by the sight.

"You're so goddamn sexy when you let yourself go like this. I love seeing you lose control for me," he praises, voice thick with lust as he chortles. "Now why don't you slip that toy in and out of that tight little pussy of yours and ride it for me? I want you to cum over and over until you can't even remember your own name."

Whiskey pushes his chair back, legs spreading wider. The heat in his gaze burns through the screen as he waits for you to follow his filthy commands. Slowly, you grind against the toy, looking right into his brown eyes, putting on a show just for him.

“Ah goddammit.” A loud groan of frustration escaped Jack, followed by the sound of his laptop slamming down as he abruptly ended the call. Your heart skipped a beat, pounding fiercely against your chest as you stared at the suddenly blank screen of your laptop. The sudden disconnection left you feeling both puzzled and worried, a flood of anxiety washing over you.

The sinking feeling in your stomach grows as you process the implications of Jack's abrupt departure from the call, but before you can dwell on it further, a bright flash of light emanates from your smart glasses, momentarily blinding you. The urgent meeting notification blinks insistently, demanding your attention. In a panic, you instinctively nod, accepting the video conference without a second thought.

As the holographic display materializes before you, you realize the gravity of your oversight. In the heat of the moment, you had completely forgotten about your state of undress, the vibrator still nestled between your thighs. A wave of embarrassment washes over you as you pray that the hologram's limitations will spare you from any potential mortification.

Shifting uncomfortably in your seat, acutely aware of the toy's presence and the lingering warmth it has left on your sensitive skin. Your mind races with the possibilities of what might happen if anyone were to discover your compromising situation.

Your heart skips a beat as your gaze lands upon Jack, his flustered expression instantly setting your nerves on edge. You can practically feel his eyes boring into you from behind the holographic display, his presence both comforting and unnerving.

With a quick nod, you acknowledge his presence, trying to keep your voice steady and professional as you address him. "Agent Whiskey."

“Agent Wine.” His response, laced with a knowing smirk, makes your cheeks flush with equal parts embarrassment and excitement.

The way he says your codename, drawing out the 'Wine' with a playful inflection, sends a jolt of electricity through your body. It's as if he's relishing in his knowledge of your compromising position. You squirm in your seat, the vibrator still nestled between your thighs, a constant reminder of your shared secret.

The meeting drones on, a seemingly endless parade of statistics and strategic plans. Your mind struggles to keep pace, constantly drawn back to the throbbing between your thighs. You try to focus on the cold, clinical data presented, but your body betrays you, each movement a torturous reminder of the toy hidden beneath your body.

Your eyes dart around the holographic conference table, avoiding the temptation to glance down at the source of your distraction. You know that looking at Jack will only make matters worse, his mere presence a constant tease. But in a moment of weakness, your gaze drifts to his face, colliding with those piercing brown eyes and that infuriating smirk.

A chill runs down your spine as you raise an eyebrow questioningly. Before you can utter a word, Jack's finger presses to his lips, a silent command to keep quiet. Your heart races as he reaches into his pocket, retrieving a small remote control. Without a word, he presses a button, and the vibrator springs to life, humming softly against your most sensitive flesh.

A sharp gasp escapes your lips as the sudden stimulation sends shockwaves through your body. Your hands fly to the edges of your desk, gripping the wood so tightly your knuckles turn white. The vibrations pulse through you, each wave building upon the last, threatening to consume you entirely.

You bite your lip, trying desperately to stifle any further sounds. Your thighs tremble, the muscles quivering as you struggle to maintain control. The holograms flicker and dance around you, but all you can focus on is the relentless throb between your legs, the heat building steadily in your core.

“Is everything okay?” Ginger's eyes sparkled with concern and confusion as she addressed you.

You mustered a composed response, trying to maintain a steady tone. "Yes, I thought I saw a bug. Apologies."

At that moment, Tequila spoke up with a bemused smirk. "A bug? You're afraid of a tiny insect, Wine?" Whiskey chuckles darkly at Tequila's comment, his eyes never leaving yours. He leans back in his chair, a smug grin playing on his lips, clearly enjoying your struggle.

“Yes, a bug.” Your eyes narrowed, teeth gritting together as you shot a warning glare at Tequila. He quickly got the message, backing down with a knowing smile.

You let out a silent sigh of relief, turning your attention back to the meeting. But even as you try to focus on the discussion at hand, your mind keeps drifting to Jack, to the power he holds over you in this moment.

You are silently pleading for mercy. But his gaze remains fixed upon you, his expression one of pure, unadulterated lust. He revels in this, in the knowledge that he holds your pleasure, your very sanity, in the palm of his hand at this moment.

The minutes tick by agonizingly slowly, each second an eternity of sweet torture. You bite your lip hard enough to draw blood, the coppery taste mingling with the sweat beading on your brow. Your breath comes in short, sharp gasps, your chest heaving with the effort to maintain your composure.

Finally, the meeting draws to a close. The holographic displays flicker and vanish, leaving you alone with Jack and the lingering echo of the vibrator's hum. You slump back in your chair, your body trembling with the aftershocks of your denied release.

Jack's gaze locked onto you from across the room, a smug smile playing on his lips. "Sweetheart, you did great," he remarked before adding, "but I'm afraid we have some unfinished business to take care of."

Tossing the glasses into the bed, you called Jack again, slumping back in your chair, your body trembling with the effort of maintaining your composure.

As the video call connects, Whiskey's smirking face fills your screen, his eyes glinting with wicked delight. He leans back in his chair. "Well, hello there, darlin'," he drawls, his voice low and husky. "Looks like you're all alone now. No more prying eyes to worry about."

His gaze takes over your trembling form, taking in the sight of you sprawled out in your chair, cheeks flushed and chest heaving. You can practically feel the heat of his stare through the screen.

"I couldn't stop thinking about that little show you put on for me earlier," Whiskey continues, a predatory edge creeping into his tone. "The way you squirmed and bit your lip, trying so hard to hold back those sweet moans... Fuck, it was hot."

His free hand disappears from view for a moment, and when it reappears, it's wrapped around the thick length of his cock, stroking slowly. “You did so well" he purrs, his voice a low, seductive growl as looks at you. The way his rough voice turned into soft whimpers with each stroke sent a fresh wave of heat courses through your body.

His other hand actively looks for the controller, turning the vibrator a level more. It’s more loud, faster and intense, hitting all the right spots in your heat. “Fuck…” You cry out, thrusting your hips into the air as you look at him.

Your eyes drift downward, taking in the sight of his hand moving rhythmically, pumping his hardened length with slow, deliberate strokes. The knowledge that he is pleasuring himself while watching you only adds to the intensity of the moment, a heady mix of exhibitionism and voyeurism.

"Fuck yeah, just like that," he groans, palming himself harder. "You're so goddamn sexy, baby. The way you're movin' on that... Mmmm, makes me wanna bend you over and fuck you 'til you can't walk straight."

His gaze is intense, burning into you through the screen. "You like puttin' on a show for me, don't you darlin'?" Jack coos, voice low and rough with arousal. "Such a naughty thing, lettin' me watch you play with yourself. I bet you're drippin' wet right now, aren't you?"

Jack’s hand speeds up on his cock, stroking himself faster, getting off on the erotic display you're giving him. The other hand holds the controller, ready to push you over the edge at any moment.

“Just for you.” You utter, struggling to even talk as the level is torturing your pussy, barely able to keep your eyes on him.

“Damn right it's just for me," he growls, his voice thick with desire. "You're all mine, Agent. Every inch of that sexy body belongs to me." With that he turns one, then another cruel level more.

Your eyes roll back as the vibrations intensify, the toy mercilessly pounding into your sensitive flesh. Your body convulses, spasming uncontrollably. “Jack!” You cry out, begging him for something you’re not sure about. All you know is that the vibration is more than you can handle.

"Sorry sweetheart. I just wanna see you lose control. Fuck that pussy 'til you're screamin' my name. Show me how much you miss my cock."

His breathing grows ragged, chest heaving with each labored breath. He's completely entranced by the sight of you, lost in the fantasy of being there with you, taking you apart with his own hands and tongue. "Goddamn, you're so fuckin' hot," he praises breathlessly.

His words ignite something deep within you, a primal need that demands to be satiated. You arch your back, pressing the vibrator harder against your aching core as you ride the waves of sensation crashing over you. Your breath comes in short, sharp gasps, your chest heaving with the effort of holding back the impending release. The tension builds, coiling tighter and tighter in your belly until you can stand it no more.

With a cry of pure, unadulterated ecstasy, you let go, your body convulsing as the orgasm rips through you. The vibrator's hum seems to intensify, prolonging your climax, drawing out every last drop of pleasure. Through the haze of your own release, you see Jack's hand move faster, his breath coming in harsh pants as he chases his own end, whimpering your name like a prayer as he cums all over those strong, manly hands of his.

As the afterglow fades, his eyes meet yours, a wistful, almost vulnerable expression on his face. "God... Can we do this till you come back?" he asks, his voice tinged with a hint of uncertainty.

A playful smirk tugs at your lips as you lean, a mock pout forming on your face. "Someone's needy," you tease, enjoying the way his brow furrows at your words, making him look like a cute puppy.

Jack rolls his eyes, a familiar gesture that never fails to amuse you. "Yeah, yeah," he grumbles, but there's no heat behind his words, only a fond exasperation. “I just miss you.”

349 notes · View notes

magpiepills · 4 months ago

Text

Rope & Ride

Pairing: Jack Daniels x f!reader

Word count: 2.8k

Summary: Jack gets more than he bargained for when he gets too comfortable doing surveillance.

Warnings: SMUT Dub/non-con, NOT SSC/RACK compliant! Oral (f receiving), restraints, denied orgasms, stalking, breaking and entering, unprotected PIV, creampie, smoking, implied plot, but no substantial story,

A word from the author: Here is my very late entry in @wannab-urs ‘s The Dom That Middle Aged Man Campaign 2025 event. It’s been so much fun getting to share ideas and read stories written by the many wonderful writers involved and I’m so sorry that I’m past the deadline for posting. This is my first time writing Jack and I am so grateful to Gin for putting this whole thing together so that I could try something new.

Masterlist Turgid Members DMAMC25 Masterlist

He must be losing his edge.

You walked down the sidewalk toward your walk up, heels clicking against the concrete, and there he was, following along.

At the cafe drinking your coffee, at the library doing research, and as you shopped, there he was.

Maybe it wasn’t all his fault. A handsome man stands out, just naturally stands out, doesn’t he? Jack certainly does. He’s tall and slim waisted, but broad, broad, broad across his shoulders. He was neat, hair brushed into place, mustache trimmed, face sporting only the barest little scratch of whisker.

He might disguise himself, a suit, a leather jacket, dark aviators, a cowboy hat. Dark brown, never white. He knew he wasn’t a good guy deep down. A good guy wouldn’t follow a woman at all hours of the day and night. He wouldn’t peek in her windows or photograph her when she stopped to talk to someone. He wouldn’t tap her phone.

You wondered what he did with all the “evidence.” And you wondered how much longer you’d need to keep up the charade before he was finally done.

…

The day came one gray, drizzling evening three and a half weeks after you first spotted him. You’d received an urgent call from your sister in Dubuque, begging you to fly home right away, to take the first available flight and tend to an urgent family matter.

You hastily flung your suitcase onto your bed, threw in some clothes and took your coat and left. You hailed a cab beneath a lamp post, obscured by rain and your black umbrella, and disappeared into the night. A week, you’d said. He didn’t know if that included travel, but it was still plenty of time.

Jack got out of his car, a pale blue Mercury, nondescript, nothing flashy, and shut the door quietly. He crossed the street casually, with the confidence of someone who belonged right where they were. Your locked front door was little deterrent. Jack picked it easily, producing two slim tools from his jacket pocket and in less time than it would take to fumble with a key ring in the dark, he was inside.

He waited for his eyes to adjust to the darkness of your apartment, and tuned his ears to the sounds of your apartment. Silent, save for a table fan left on by accident, a ticking clock, and the rain that tapped gently against your windows.

After a few still minutes standing stone still, Jack relaxed. He was careful to be quiet, even though he was alone. A small flashlight was fished from the same pocket where he kept his lock picking tools. He held it in his mouth while he retrieved two gloves from another pocket and put them on, flexing his knuckles against the soft leather. Jack swept the first floor, moving fluidly through your sitting room, your kitchen, past the laundry nook.

Each room was neat, but lived in. You’d obviously left in a hurry, a newspaper was draped over the back of your sofa, stockings dried in the bathroom. He brought the fabric to his nose and breathed in the scent, but only detergent was there, nothing of you. In your medicine cabinet he found the usual things, bandaids, toothpaste, hair pins, ibuprofen. Nothing unsavory or incriminating there, not under your sink. A rummage through your linen closet was the same, revealing only a predilection for soft pinks and fuzzy blankets.

Finding nothing of note in your bathroom, Jack moved to your bedroom. He closed the door behind him and inhaled deeply. It was, like the rest of your apartment, tidy and pretty. Unlike the others, this room smelled like you. Light, sweet, it reminded him of candy and flowers and warm, bare skin. Your bedside table was the first target of his snooping. A small lamp, a book, a framed photo of two young girls and a dog, and your telephone. He held the flashlight in his mouth again, freeing his hands to inspect the book. He flipped the pages and found nothing but a bookmark.

“I know there’s something here. Give it up,” he complained to himself, voice deep and twangy. Your drawer, your dresser, your closet, under your bed, he found nothing he could use. He checked his watch. It had been close to an hour that he had spent exploring your home, violating your privacy, and he had nothing to show for it. Annoyed, he sat on your unmade bed to think. He sat on the edge. He sank into the plush mattress, then took off his hat to lay back. He sighed, relaxing further, and closed his eyes.

Your scent was stronger here, where you slept. With his searching concluded, Jack let himself revel in the sick pleasure of being in your bed. He turned his head and breathed in deeply. He pulled your pillow over his face, and grunted into it as he palmed his thickening cock.

He was never one to take a souvenir, but he made a quick decision. Jack got up from your queen size bed and went back to your dresser. He upended the top drawer and found a silky pair of panties, pink, like you like.

He was certainly losing his edge.

So absorbed in his own pleasure, Jack didn’t hear you come back in. He tilted his hips, bucking against the scrap of girly fabric in his big fist. His jean were shoved halfway down his thighs.

It amused you to watch him. After so many weeks of his stalking and spying, you got the chance to do the same. You were sure he’d seen you in moments of undress. You hadn’t changed your routine after you figured him out, free all. You carried on like normal.

Now, with him in your bed, jerking off with your panties, he was exposed and vulnerable for once. You didn’t feel any shame when you stared at his cock. You studied it, the veins of his thick shaft, the dark hair around the base, the blunt head, blushing and leaking precum that smeared onto your panties with each stroke.

The carpet muffled your footsteps and you were standing between his knees, pistol pointed at his handsome face. Your voice startled him.

“Don’t come.” Your voice was velvety and smooth, but he startled anyway. It made you smile. His hands flew to reach for his own weapon, but he couldn’t reach. How foolish of him.

“Is this what you wanted, Mr. Daniels? You’ve been following me for weeks, everywhere I go, everything I do, there you are. You’ve heard my telephone calls, you’ve got enough pictures for quite an album. If all you wanted was a pair of panties, you should have asked me to dinner like a gentleman.”

“You know what I want,” he spat back, "tell me where it is.”

You hummed thoughtfully, as if you were really considering his demand, then brought your knee to rest on the mattress between his legs.

“I really don’t know what you’re talking about, Jack. Right now you are in my apartment, uninvited, lying in my bed, and doing something very nasty with my panties. I think that it’s time to talk about what I want.” You brought your other knee onto the bed and leaned forward, letting the snub nose of your revolver press into the fabric of his white button up. He didn’t seem to breathe as you dragged it downward over his belly, only making a panicked little cry as the cold gunmetal reached his still hard cock.

You took your panties from his hand, “say ah.”

He obeyed, letting you poke the fabric into his mouth.

“Now, I’m going to get up for just a moment and you are not going to move.” You raised your eyebrows, and nudged him with the short barrel of the gun until he nodded.

Jack closed his eyes and dropped his head onto your bed with a weary sigh.

You returned with a length of pink fabric, the sash of your bathrobe and pulled your reading chair closer to the bed. As instructed, Jack didn’t move. He was still hard and leaking.

“Stand up and strip, Mr. Daniels. Nice and slow.”

The panties in his mouth muffled his hostile ranting, so you pulled them back out, laying the wet, delicate fabric on his chest.

“This isn’t a game,” he hissed, lifting up on his elbows. “You know why I’m here.”

“You’re handsome when you’re angry. Strip.” You wished you had a cocktail right now.

He stood and glared at you, cock bobbing between his legs as he unbuttoned his shirt.

“Slower.” He started to argue but held his tongue, tossing the shirt onto the bed. He pulled his belt from his dark jeans, but you stopped him, holding out your hand for his belt buckle flask.

Of course Jack “Whiskey” Daniels had a full flask. You sipped his bourbon, letting it warm you and nodded for him to continue.

His shirt was first. He unbuttoned it without flair, tossing it onto your bed. His pants were next, already around his thighs, along with his black boxers. He shoved them down and stepped out of them. It wasn’t as sexy as he could have made it if he tried. He’s got a nice body, and he may be unhappy with his predicament, but he’s still hard.

“Turn around for me Jack, give me a little show,” you say, eyes dancing with mischief.

He huffed and turned stiffly. Even if he was mad as a wet hen you were going to enjoy yourself. It wasn’t often you had a man in your bedroom. Not with Jack tailing you, anyway. You weren’t about to give him a free thrill. You tilted your head and drank him in. He was aging, scarred and a little worse for the wear. You liked it. You liked how he looked with a little gray beginning to thread through his hair. He was still lean and strong, fit despite the slight paunch of his belly.

His legs were gorgeous, not the skinny chicken legs a lot of men have, they were shapely, same as his arms. Not bulging with too much silly looking muscle, just right. Nice and toned. His back was the same, his chest, with its sparse hair, dark, tight nipples, skin that must taste salty.

His softening belly, his weak spot, bore a dark patch of hair that lead you gladly down between his legs where your real nemesis hung. That cock of his, long, thick, still hard, even as he scowled at you. It leaned slightly left, which you could have guessed from the bulge you often noticed in his very tight jeans.

Taking the robe belt in your hands, you reached out to wrap it around his cock. You wanted to tie a bow, but Jack’s hands blocked you, hiding himself. That earned him a smack, and a warning.

“Don’t move, Agent Whiskey. Not one move without my permission, do you understand?”

He raised his hands in surrender and muttered. You let the smooth fabric drag over his turgid member, but instead of the bow, you made him turn again.

“Hands behind your back. Turn around for me.”

He closed his eyes, not bothering to argue, and you heard him exhale when you tied his wrists together in a pretty, but very secure pink bow.

You fluffed your bow and turned him to face you once more.

“There. I bet that feels a lot nicer than some old piece of rope, doesn’t it?” You smiled at him.

Jack couldn’t believe his predicament. He had made sure you were gone, he had checked his time, he hadn’t left evidence behind. He was going to jerk himself off into your silky underthings and leave, the panties his only souvenir.he doubted you’d even miss them the way your drawer was full of so many lacy, silky, soft little things. He made a mistake somewhere, and now here he is, naked, hard, tied up in between your bed and your chiffarobe, while you bossed him around. He dare not acknowledge the throbbing erection. It was plain enough for you to see.

You put him on his knees, guiding him down with your dainty little manicured hand on his shoulder. His tired knees sank into the mercifully plush carpet, and he sighed.

He watched you walk back and forth in front of him, small steps in your tall heels. He wondered what you were thinking. He wondered if you really knew what he was looking for. His mind raced, all of his training leaving him woefully unprepared for a scenario like this, especially when your panties fell to your ankles.

You stepped out of them gingerly and swept them aside with the toe of your high heel.

You liked him on his knees. He was better behaved when he was at a disadvantage. His pretty lips pouted, his big dark eyes searched your face for a hint of your next move, widening when you raked your fingers through his hair and gripped it, holding him as you stood before him, balancing on one foot with the other pressing into the edge of the bed behind him.

Jack welcomed your bare pussy against his face. He took it like an offering and accepted your soft, damp lips against his tongue. You stayed still, letting him lap at your folds for a few moments, then began to roll your hips, using his face. His nose, lips, chin, even the scratch of his mustache felt heavenly against your achy center. You kept on, soaking his face until you came.

Jacks cock throbbed between his legs, untouched and rock hard. Droplets of precum dribbled from his tip. You caught your breath on the edge of the bed and watched him, chest expanding between his wide shoulders. You placed one ankle on his shoulder, and leaned back on your palms.

“That was a good start, don’t you think?”

Agent Whiskey licked his lips and nodded. “Yeah. Real good. Untie me and I’ll make it a good finish too.”

It made you laugh, his confidence. It preceded him, of course, but you hadn’t experienced it for yourself.

“Really, Daniels? I can’t untie you now. We’re just getting started.”

There was only your dainty watch on your bedside table to tell you that more than an hour had passed since you pulled Jack up and onto your bed. More than an hour of him gasping each time you touched him, lip quivering each time you denied him an orgasm.

“Please. Please!” He plead for your mercy as you held his body down with yours, hand around his cock, twisting around it, working upwards and back down tortuously slow. His hairline was damp with sweat.

Each time he got too close you stopped, plucked a cigarette from your case and smoked it, appraising his deconstructed state from a few feet away, then ashed it in a crystal dish.

When his breathing steadied and his whimpering quieted, you took your place on top of him again. This time with his cock situated beneath you, slipping back and forth between your wet folds, never taking him inside, just using his pulsing cock to bring yourself to orgasm once more.

Jack's eyes shone with unshed tears of frustration and he tried in vain to chase his own orgasm. He wondered if he would ever come again or if you’d always stop him. He was crazy with need, mind poisoned with unspent cum.

Not long before the two hour mark, you decided how you’d wrap up this meeting of minds.

You straightened your back, lifted your hips, and slowly sank onto his cock. Your pussy squeezed and pulled him in, making him groan and tug against his restraints.

He was thick and long, filling you, pressing against your body, a wonderful counterpressure to your clenching cunt.

“Fuck. Oh, fuck! Yes!” He babbled, thrusting, stomach tensing, hips pushing up as much as he could manage to meet your thrusts.

You sped up, riding him hard with quick up and down strokes intended to thoroughly drain him of every last drop of cum. His face was a study in surrender. Glassy eyes, mouth slack. You watched him closely and pumped his body with yours. Your own pleasure was undeniable, you’d used his body for countless orgasms since you first caught him in your web. You took another, the first he felt for himself and it was enough. Jack “Whiskey” Daniels flooded you with his milky white cum.

You left him, panting, used up, and wet, not yet aware of how fucked he truly is now, and returned with a Polaroid camera. You snapped shot after shot, his face, his body, his softening cock, and one last shot of yourself, smiling, satisfied, triumphant wearing his hat.

#dmamc 2025 #the dom that middle aged man campaign 2025 #jack whiskey daniels #jack daniels #agent whiskey #agent jack whiskey daniels #kingsmen golden circle #Jack whiskey Daniels smut #Jack Daniels smut #agent Jack whiskey Daniels smut #pedro pascal character fanfiction #pedro pascal #pedro pascal characters #bat writes #pedro pascal character smut #Jack whiskey Daniels x reader #agent whiskey smut #jack daniels x reader #jack daniels x you

211 notes · View notes

syd-djarin · 1 year ago

Text

private eyes - jack daniels x private investigator!f!reader (18+ MDNI)

You’re a PI hired to spy on Jack Daniels, by his ex-fiancé, who is believed to be a cheater. As time goes on, you don’t find any evidence of the sort, but what you do find is unexpectedly…erotic.

this is for @iamasaddie little lady kinky may challenge! congrats on 2.5k! <333 I was paired with Jack / Voyeurism.

banner by: @cafekitsune

tags: voyeurism (reader watches jack), masturbation (m & f), reader is a private investigator, gratuitous descriptions of my fav cowboy stroking his big cock, dub-con a little? reader masturbates in her car but there isn't anyone around so public but private

a/n: this is the first fic I've completed in months. it's short and to the point, idk how i feel about it but it pushed me out of my writing slump! kinda want to do a part 2 for this, what do y'all think 👀

wc: ~1.6k

smut below the cut

“I want you to catch that son of a bitch in the act.”

The visibly scorned woman, Camilla, sitting across from you asks through tears, ones that she hasn’t allowed to escape down her cheeks; catching them right at the waterline with an overused tissue.

This isn’t the first time a disgruntled, mistreated, or betrayed lover has sought out your services — no shortage of shitty men leaving trails of destruction while they pillage and greedily chase their own interests. She’s no different, seeking closure from the broken-off engagement from her now ex-fiancée, Jack Daniels. The pair had been together for a year, engaged for three months and one day, out of the blue, Jack broke it off. According to her, he didn’t give a concrete reason, something vague about being consumed with his job and that “she deserved a better life than that”.

Of course you get paid a pretty penny for your work, but you take great pleasure in catching a man in the act. Whether the woman needs proof for divorce settlements, custody battles, or to just have leverage. Whatever the case may be, you find a gratification you don’t get anywhere else; the upheaval of a man trying to have his cake and eat it too.

The conventionally attractive woman you couldn’t pick out of a line-up slides her homemade dossier across the coffee shop table, tacky & sticky from previous patrons. You flip through the information presented to you, taking mental notes as you go. You can’t deny the heat that rises up your face as you study the picture of your next target. The deep sable eyes resembling a baby calf’s are staring at you through the glossy photo paper. He’s sporting a mustache reminiscent of Burt Reynolds that is calling your name. His smirk is laced with a charming cockiness.

“He’s quite the looker, I know. Hell of a lay, too,” her words snap you out of your daydream. Her words feel hollow, his looks are the only attributes she’s mentioned during the duration of the consultation. You're not getting paid for moral judgements and you remind yourself you don’t know the whole story.

“Which is why I want to know who he’s fucking. I know there’s another woman, or maybe even a guy… he’d answer calls in the middle of the night and step into another room and I swear I could hear a woman’s voice on the other end, he’d tell me he’s going on work trips… he works at a whiskey distillery, why the hell does he need to go on all these trips?” She explains, putting air quotes around ‘trips’ with her dainty, well-manicured hands, “he’d stay late at work a few nights a week, and then it turned into a nightly thing… Anyways, you come highly recommended, so I’m trusting you won’t let me down,” she adds. You’re not a fan of the passive aggressive, back-handed compliment she gives you, but ultimately you give her an understanding smile as you both rise from the table.

“I’ll be in touch,” you tell her, as you exit. As cliche as that line is, you love saying it every time.

Days of following Jack around have proven to be fruitless. The man has a simple routine: wakes up at six, traipses to the bathroom to begin his morning regimen of a showering, shaving and grooming his beloved mustache, and to conclude, adorns his body in his tight denim jeans, a crisp button-down, a cowboy hat, and boots to match. You hate to admit it, and someone would have to waterboard this information out of you, but the hat is doing something for him.

Or you.

Whatever.

He shops weekly on Wednesdays (he always puts the cart back inside the store, not the cart returns in the parking lot), takes the same route home everyday, watches Jeopardy while he eats dinner – you caught on quickly that he cooks during Wheel of Fortune, it appears he isn’t a big fan of Pat and Vanna, dishes promptly following Final Jeopardy and bed by nine. In three weeks Jack hasn’t had a single visitor, of any gender, leaves work at five like everyone else, the man isn’t adding up to be a cheating womanizer like Camilla had set him out to be. Not to say that he isn’t, but you’re not finding any evidence to support that claim. You’ve actually found yourself developing a crush on the man. He’s undoubtedly handsome, seemingly laid back despite his strict routine, and there’s something mysterious that lies beneath that you’re itching to unearth.

You’re parked discreetly across the street from his house. It’s a nice quiet street, with only two lamps to illuminate the surrounding neighborhoods, allowing you to stay shrouded in the night.

You’re about to call it a night, exhaustion settling deep into your bones, when you notice a lamp turned on in the living room. Fortunately, the window faces the street, making your job that much easier for you. You pick up your binoculars to peer in, adjusting the focus for your prying eyes. Thank the universe he left his blinds open.

He sits on the couch with his back facing you. It looks like he’s reaching for the remote, like maybe he’s having trouble sleeping, but when he settles back into the couch, you notice he’s butt ass naked, in all his glory. Even through the binoculars, you can see how big his cock is. Your mouth salivates at the sight, wanting to feel the stretch of him in all your holes.

You’re not supposed to see this. Not at all. Usually in your assignments, you don’t get the full X-rated view, just the PG-13 suggestive one, and you are more than grateful for that.

But not now.

You’re getting your own private peep show from the man you’re getting paid to spy on. You’re feeling like a grade-A pervert right about now but the sight is too glorious to look away. He spits on his hand, and languidly begins stroking his cock. He runs his other hand through his hair, his toned arms flexing with his movements, his chest heaving.

It shouldn’t turn you on like it does. For one, it’s highly unprofessional. Secondly, he’s unaware he’s got an audience. Morally speaking, it’s definitely not your shining moment. But it’s the hottest thing you’ve ever seen, watching him tease and work himself up. You couldn’t pry your eyes away if you wanted to.

Jack’s not the only one getting worked up; your clit throbs so hard you feel like it’ll go numb. Your heartbeat echoes in your ears thump-thump thump-thump. You let out a whine when Jack massages his tip, precum dribbling out like a sweet nectar you’d like to feast on. He continues his slow movements, dragging out his pleasure at a delicious and excruciating pace. Somehow, this makes the whole scene that much hotter; the display of restraint and discipline. You wonder if he does that with his lovers. Teasing, teasing, teasing, giving just enough to drive you insane before slowing almost to a stop.

Possessed by desire, you haphazardly look for any lingering people outside before unbuttoning your pants to shove your hand to where it's needed most. You gasp at the cool air hitting your thinly clothed pussy, you can smell your own arousal seeped into your panties and it spurs you on further. You mirror Jack’s pace - teasing your lips with a featherlight touch, inching closer and closer to your needy clit, stopping just shy of it, to tease yourself more. It’s agonizing in the best way, taking your time like this. Normally, you like efficiency when making yourself come, rarely going the extra mile to turn the pleasure dial up, but this makes you question why you’re ever in a hurry.

You reach your clit, going in gentle circles to match Jack’s unhurried pace. You wish you could hear the sounds he’s making, all the grunts and whimpers escaping his plush lips.

He speeds up his strokes, now ravenous for his delayed release and so are you. Overtaken by the need to come, you drop the binoculars, letting them fall to the floorboard. You’re not even watching him anymore, having seen more than enough to commit to your spank bank. With your eyes closed and head pushing into the headrest, your mind is flooded with images of Jack fucking you slow, hard and deep, absolutely destroying your pussy – legs over his shoulders, hitting the spot that makes you scream and cry in euphoria. The image of him spilling into you, filling you up with his come is what tips you over the edge, your body shivers in bliss and you rock against your hand to ride out the high, feeling faint from the intensity.

After you’ve recovered and fumbled your chance of ever seeing The Pearly Gates, you dare to look back to his house, to find all the lights back off. It’s a bit of a relief, feeling less shameful of what you’ve done now that you can’t see him at the moment.

You button your pants backup and lean over to retrieve the forgotten binoculars from the floorboard, as your fingers grab them you hear a knock on the window. The sudden rap on the glass makes you flinch, feeling your skeleton attempt to flee from your corporeal body. Your heart drops to your stomach when you see Jack standing outside your car, leaning one forearm against the body so his face is level with yours. Fuck fuck fuck. You’ve been caught. Dizziness and nausea war within you as you roll down the window. You open your mouth to explain the situation, but words never escape your mouth.

“You like watchin’ people don’t ya?” he asks, his tone is dark, but not angry. No, it’s something else entirely.

“I–”

“‘S’alright. Caught onto ya pretty quick. A pretty face like yours ain’t hard to miss.”

“I– i’m sorry, um,” you scramble to find words, any words but Jack interjects again.

“You like watchin’, but darlin’ I want to know, do ya like bein’ watched?”

#snail trail alert 🚨#little lady kinky may #iamasaddie game #2.5ksaddies #jack daniels x you #jack daniels x female reader #jack daniels smut #agent whiskey x you #agent whiskey smut #agent whiskey fic #agent whiskey x reader #agent whiskey #jack daniels x reader #agent jack whiskey daniels #pedrostories #fanfic #smut

570 notes · View notes