#agent whiskey imagine

[fuckyeahdindjarin]

Pressing

Jack Daniels x F!Reader, dude ranch AU

A Palomino oneshot, but can be read on its own

{ Series Masterlist | Main Masterlist }

Rating: E

Summary: Jack marks you as his in an unexpected way.

Warnings: PWP, Jack's belt leaves an impression on reader's skin, unintentional branding, unprotected sex, long-distance relationship, desperate and feral cowboy, no physical descriptions of Reader, very lightly edited, written as part of the Palomino universe, set after the end of the series, but can be read as a oneshot on its own

Word count: 1.4k

Notes: This little story came from an ask sent in by 🐴 anon in December 2022, which I have long lost, about a song that mentions a guy’s belt buckle leaving marks on his girlfriend's inner thigh while fucking. Naturally, they thought of Jack’s belt. 🐴 anon, if you’re still here, thank you for the inspo and for your patience ❤️

Also thank you to @lola-lola-lola for getting me horn knee about our cowboy again 😘 Writing Palomino smut first thing in the year was not on my 2024 bingo card, and I’m not mad about it!

Cutest dividers by @firefly-graphics.

It’s been two and a half months. Week after wretched week of phone calls on stolen time. Day after day of aching to reach through the phone screen and the distance between you to touch him.

It’s hard being hundreds and hundreds of miles apart. It’s even harder on weeks when he’s in the mountains with no reception. Harder to find time to call when you have to work late and he has to get up at dawn.

But you endure it all - for days like this. 

It’s a rare weekend off in the high season, with Teak pulling back-to-back pack trips to cover for him, joking that he can’t take all his sighing and pining for his Darlin’ anymore.

Jack takes the last flight out on Friday night, arriving first thing on Saturday morning, before the city - or you - wake up. You’re half-buried under the duvet when the jingle of the key in the door jolts you from shallow slumber.

On unsteady feet, you wobble out into the hallway, crashing into the walls as you go, balance off-kilter from sleep.

But it’s ok - he catches you, all white t-shirt and tight blue jeans. Incognito, if you will, in casual sneakers, but the cowboy hat is on as always. You knock it off post-haste, burying your face in the side of his neck in a desperate need for contact, his warmth seeping into your skin and wrapping you up in the deepest of comforts.

His hair is longer than he usually keeps it, and your fingers twist into his tousled curls when you pull back, taking in the stubble on his sharp jawline, and his tired eyes. But before you can say anything, he leans in and slants his lips over yours.

The taste of airplane coffee is sharp and bitter on his tongue as he kisses you deep and messy. You startle when he suddenly slams the door shut behind him, not realising it was still open, and his beat-up weekend bag is tossed carelessly behind him somewhere in the doorway. 

The legs of the kitchen table scrape jarringly against the floor as he crowds you onto it, big hands cupping your ass and pulling you against his straining erection through his jeans.

‘Fuck, it’s been too long, darlin’.’ His voice is gravelly from an apparently sleepless overnight flight, and hearing his voice finally on the shell of your ear has you whimpering needily.

‘Can’t wait any more,’ he growls, desperation thick in his voice.

With a flick of his wrists, he shucks off your ratty sleep shirt, eyes hooded as he gazes down at your tits, like he can’t believe he’s actually touching you. Cupping them, soft and heavy, with reverent, rope-worn palms, he sucks one nipple after the other between his lips, making you squirm against him and leak wet and sticky between your thighs.

Strong hands hold you in place easily as you buck, the scrape of his moustache almost painful on your over-sensitive skin, nerve endings on fire after being deprived for long weeks. 

Too impatient to wait, you tug your pyjamas shorts down your hips and kick them off clumsily, panties tangled in your damp folds as you writhe under him. 

You feel the breath catch in his broad chest at the peek of your pussy, a rapidly growing damp spot darkening your cotton underwear. Hooking his thumb under the fabric, he tugs it unceremoniously to the side, baring you to him. 

‘Look at all this,’ he marvels, tracing the fleshy pad of his thumb through your folds, making you arch clean off the table. ‘So wet for me and you’ve barely woken up.’

‘Been thinking about you the while night,’ you admit, hips twitching as you chase his touch. ‘Couldn’t sleep.’

‘Did you touch yourself, darlin’?’

You shake your head vehemently. ‘No. Wanted your fingers. Your cock.’

His nostrils flare at your answer, unabashedly possessive in the way he looms over you. 

‘Good girl,’ he murmurs into your throat, nosing the side of your neck while thick fingers thrum against your clit. ‘I was so hard for you the whole fuckin’ flight.’ 

As if to prove it to you - not that you need it - he rolls his hips into your inner thigh, the hard bulge undeniable.

You mewl, hooking your ankles around his waist. ‘Fuck me now, Jack - please.’

There’s a wordless fumble for the solid sterling flask bottle of his belt buckle, his usual level-headed composure nowhere to be found as he pushes down his jeans with shaking hands, just enough to pull his cock out of its denim confines - 

And then he thrusts home inside you.

After months of only your fingers, it’s a stretch. But what a delicious stretch it is.

You feel him throb deep inside you, feel the thunder of a pained groan in his chest, pressed up against yours. Your cunt is all slick and give to his determined strokes as he begins to move. 

There’s no finesse, hardly any awareness, when he fucks frantically into you. His solid weight pins you to the table, and it rattles precariously under your back.

Your legs are splayed obscenely wide and bent at the knees while Jack pounds into your wet heat, eyes wild and mouth hanging open, watching your tits bounce as you take him, your nails digging into the cotton of his white t-shirt. He never did take off your panties, and the fabric rubs your clit just so with every one of his thrusts, rapidly sending you to the edge.

In the back of your mind, you’re aware of the coarse scrape of his jeans against your inner thighs, and something digs hard into the tender skin, the repeated motion dulling the sensation to an almost numb pressure. 

When you cum, you’re crying out before your head catches up, your body convulsing with blind bliss as your pussy clenches around him in a hot rush. The blood pounding in your ears is drowned out by your chants of his name, and then his hips start to stutter and his whole body tenses, frantic eyes on yours as he teeters on the edge. 

‘Where, darlin’?’

‘Inside me.’

The words have barely left you and he’s coming, broken pants against your lips as he comes and comes and comes - spilling inside you, filling you to the brim until he’s empty, turned inside out.

Slumped, boneless on top of you, humid pants pressed into your shoulder, his fingers tangle with yours, squeezing as if to let you know that he’s here.

You almost doze off, the gradually slowing rise and fall of the cowboy’s broad chest a comforting anchor, when he rouses you with gentle lips along your jaw. You giggle, feeling him softening and sliding out of you, making a mess of your kitchen table. 

‘Mornin’ darlin’,’ he says somewhat belatedly, warm eyes crinkling as he smiles at you.

‘Morning,’ you grin back, and when he shifts, you wince at the ache in your joints from being pinned to one spot for this very vigorous wake up call. His hands smooth over your legs in apology, and you jump when his fingertips brush over somewhere at the juncture of your upper thigh that is surprisingly sore.

‘What’s that?’ you ask, puzzled.

Jack doesn’t answer, curiously quiet. You look down to where he’s bracketed between your legs, watching him trace his index finger over the unmistakable imprint of his distinct belt buckle on the inside of your thigh, where it’s been digging into your skin the whole time. 

He glances at you. ‘I’m sorry. Did I hurt you?’

‘No, you didn’t,’ you give him a knowing grin. ‘And are you really sorry, cowboy?’

He doesn’t even have the decency to look sheepish. Gently pinching your swollen folds together, he groans when a milky bead of his cum dribbles out of you, running down the inside of your leg and smearing onto the flask-shaped impression.

‘Ain’t sorry about somethin’ that looks this good on you, darlin’.’

‘Could’ve asked me before you branded me, you know,’ you half-joke, running your own finger along the deep lines carved into your skin, for now.

‘Beggin’ your pardon, I tend to forget my manners when I’m balls deep in a pussy as sweet as yours,’ he retorts, one eyebrow arching when he feels you shiver at his words.

You huff in jest, ‘Doesn’t sound like much of an apology if you asked me.’

‘Whatcha want, darlin’? Me on my hands and knees for you?’

Heat flashes under your skin, from your cheeks down to your toes, and Jack’s eyes darken as his tongue wets his bottom lip. ‘Alright. I hear you loud and clear, ma’am.’

Slowly, he sinks onto his knees in front of you, his joints creaking endearingly as he goes, and you can’t help but tease, ‘Easy there, cowboy.’

The wicked tip of his tongue peeks out, and you bite your lip in a moan when it cleverly traces the outline of the belt buckle on your skin, ending in a playful nip that pulls a gasp from you.

With an unapologetically smug grin, Jack winks. ‘I’m only just gettin’ started, darlin’.’

Note: Thank you for reading ❤️ I’ve missed these two, and if you’re new to Palomino, I hope you’ll give the series a chance!

[absurdthirst]

Kinktober 2024: October 7th

Day 7: Bruising or Bitemarks // Virgin // Ice Play

Agent Whiskey x F!Reader

Rating: Explicit

Word Count: 1.1k

Warnings: Vaginal sex, cock riding, biting, hickies, begging, submissive Whiskey, teasing

|| Kinktober List || MasterList ||

Click Keep Reading only if you have read the Rating and Warnings and understand the warnings may not be complete to avoid listing spoilers. As AO3 says 'creator chooses not to use warnings'. You also agree that you're the right age to be consuming anything here.

“Uh, Whiskey?” Jack looks up from examining the amber tone of the newest batch of Statesman that had been un-barrelled and bottled, sniffing the oaky rich notes and was satisfied with the hint of cloves and honey. It will be a good vintage, one that he had personally crafted and he was just about to put it to his lips to taste when he’s interrupted. 

Looking up, he finds Champ, aka Agent Champagne, his boss - staring at his neck. Making him frown at the bewildered and slightly bemused expression on the older man’s face. “What is it?” He asks, setting down the glass and reaching up, his brows pulling together even more when he feels a tender abrasion that has been exposed as his collar moved down, pulled tighter as he had sat. Making his own embarrassment bloom on his face as he realizes what Champ is staring at. 

****

“Fuuuuuuuck, sugar.” It’s hotter than fucking Satan’s ass in the middle of July, but he’s not going to even fucking complain. Your sweat slick body writhing on top of him, your cunt wrapped around his cock, bouncing on it so expertly that it makes his toes curl every time you settle on him. His head tips back, eyes closed as you kiss down his jaw. 

You hum, the sound almost a growl as you reach up and start to tangle your fingers into his sweaty hair, holding onto him like you are riding a bull. Putting a little more roll into your hips as your teeth come out and you scrap them over his skin. 

“Oh shit.” Jack hisses, his cock twitching in an instinctive reaction to your little nip and making you giggle. 

“You like that, baby?” You coo, your voice dripping with sex and honey, just the way he likes it. You nibble at his throat again and he moans softly, his cock jolting inside your walls again. Even if he denies it, his body is telling you that he loves what you’re doing. 

“Hmmmmm.” You smirk and open your mouth wider, letting your teeth sink into the sensitive flesh of his neck, right above the pulse and dig in. 

Your name falls as a whimper from his lips, his own fingers digging impossibly tight into your hips. Holding you there rather than trying to push you away. You know Jack is stronger than you are, you have seen him in action. If he didn’t want this, he could easily stop it. 

The fact that he doesn’t makes you feral. Sucking and biting more and more. The same spot over and over again until he is wearing an impression of your teeth in the smooth, tanned skin of his vulnerable throat. A bruise is already starting to bloom under the surface from where the pressure of your mouth has broken capillaries. 

“Goddamn.” He pants, rocking his hips up into you, needing and wanting more of your cunt while you lose yourself in the taste of his sweat and the beauty of marking his body as your own. “Sugar, you gotta- I need-” 

He whines again when your tongue presses at the hollow of his throat, your teeth scraping over his Adam’s apple. He’s never been one to give up too much control, but right now, it’s like you’ve lassoed him to the bed and he can do nothing more than bed for you. Chills racing up his spin every time your teeth bite into his flesh and his body pulls tight in pleasure. 

“I know what you need.” You tease, lapping at the latest mark and then deciding to suck on it again. Enjoying the tightening of his core and the melting of his limbs as you put another set of bitemarks to his shoulder after you’re satisfied with one right above his collarbone. 

His chest becomes your canvas, your mouth the paintbrush. Bruises and impressions start to form a pattern over his skin. Making him whine and squirm ever more, groaning in protest when you actually pull off his cock so you can move down his body. 

Another bruise on his hip bone, making sure that it will be vivid when it fully forms, imagining the way it will look when his low slung jeans rest right below it. It makes your now empty cunt clench around nothing and you moan before you move to give him a matching mark on the right side. 

Jack Daniel whines when you bite right next to the base of his cock. You don’t apply as much pressure as you do on the less sensitive areas, but the shudder of his thighs and lovely little spurt of pre-cum that beads up against his belly and slides down his stomach gives away how much he likes this. 

Your tongue teases his balls, making him gasp and they draw tight, as if he is about to cum, but you move away and his groan is heavy with disappointment. 

Focusing on his thighs. You always love how thick and strong they are. Able to ride a bull and hold tight, they are tight with need and anticipation as you smirk up at him, your face planted right at the most sensitive inner portion. 

“Cock tease.” He blows out a half breath, half laugh as he looks down at you. “You might as well make your mark there, too.” He pants, making your smirk at the way he makes begging seem like he’s going you a favor. He wants this just as much as you do, maybe even more. 

You blow on his skin, making him hiss before you finally give him what he wants. Your mouth suctioned to his skin, pulling it harshly before you pull away and bite around the mark. Only to do it all over again under there is a change in the skin. The slight puffiness of where it has been sucked on, the discoloration and then the indentions that are so close to breaking the skin that they are bruising as well. 

Jack looks drunk, his eyes heavy and his chest heaving, so close to just giving in and cumming untouched from the attention of your mouth. “Sugar.” He slurs the soft praise. “Goddamn, c’mere.” He reaches down and urges you back up his body. “I fucking need to be inside you when I blow my load.” 

You nip his hip again and giggle when he moans, your teeth carving the path back up his body. 

****

“Jack?” He doesn’t hear him say his name the first time. “Earth to Jack.” 

Jack squirms slightly, pulling his collar and covering up the bruises and bitemarks that could be seen and shooting Champ an innocent look. “Training injury.” He lies, knowing that the man would never believe that for a second. 

Champagne snorts and shakes his head, turning back to the bar cart with a chuckle. “I’ll have to get Ginger to get the nanites to get rid of it for you.” He offers, smirking to himself. 

“No.” Jack shakes his head quickly, picking up his whiskey glass to lips to hide his grin. “I’m good.” 

[creedslove]

HEARTLESS 💔

Agent Whiskey (Jack Daniels) x f!reader

Summary: he was ready to give you the world, except one thing: be the father of your baby

Warnings: angst, hurt, angst, agent whiskey (because he is a trigger warning himself), asshole!agent whiskey, pregnancy, mom!reader

A/N: YAY, finally my first Agent Whiskey story!!! Came up with this idea last night and I was so excited about it. I love angst and he is such a handsome angsty asshole! I hope you guys like it ❤️

2.2k words

The moment Jack lay his eyes on you, he felt different.

He didn't understand it at first, it felt so odd, so foreign, so unexpected. Something he hadn't felt in years and years, not after his beautiful, little family was ripped away from him.

He tried fighting it off, it was his first instinct, he couldn't do that, not after all those years, not after having his heart broken the cruel way it was. But at the same time, everytime you smiled at him, asked him about his day, called his name, something as simple as that, it made him weak on his knees.

That cowboy had it bad. And he had it bad for you.

So he made his first move and invited you out. You accepted.

Three years later, Jack was the happiest man on earth. He had a woman he loved very much by his side, you were gorgeous, so perfect for him, you made him feel so good, so worthy of love, and he treated you like a goddamn princess.

You spent more time in his apartment than anywhere else, he wanted to ask you to move in with him, but it didn't feel quite right yet. One of the reasons was because he didn't actually like living in that apartment, he thought maybe taking you to his ranch would be a lot better. You wouldn't be so busy all the time, the daily routine stress wouldn't be as bad as New York, you would be all the time around nature and things would be fine between the two of you.

But you guys weren't married.

And Jack didn't know what to do with himself when that particular thought crossed his mind. He had never, even considered marrying someone new after he lost his sweetheart. He just couldn't, it would be impossible, he could never replace her.

But then again, whenever he saw you, his heart fluttered and he couldn't help daydream about watching you walking down the aisle with a pretty white dress all for him.

Whenever he was out, he would check jewelry store's windows and picture which ring you would like the best.

Until he finally got the balls and bought one for you. He hadn't proposed yet, he still didn't know how he could do it, but he had made up his mind. He was going to make you his, you would become his sweet, beautiful Mrs.Daniels, his world and nothing could ever come between the two of you.

The night Jack proposed to you, you were both lying on the grass, spending a summer weekend at the ranch, where you two stargazed and made love for what it seemed like hours, and when you felt him move, you turned around just to see him on his knee, a ring box in hands and his pleading eyes, asking you to become his.

And you said yes. You were Jack's and he was yours.

And you would continue to do so, until you began feeling sick. You were sure it wasn't nothing more than just a stomach bug, maybe you were coming down with the flu or something like that as you also felt light headed. You insisted Jack didn't have to take you to the doctor, but he was overly protective and quite stubborn too, so it was better just to let him, instead of trying to talk him out of it.

He held your hand the entire time, as you two waited at the reception and the only reason why he didn't go inside with you was because the doctor insisted you had your appointment on your own.

A few questions asked and a blood exam later, the doctor called you and Jack into the office.

They had the results that neither of you expected: you were pregnant.

Jack's world crashed and collided at that very moment. He felt the ground disappearing from under his feet and his heart dropped to the pit of his stomach. He couldn't do it again, he wasn't ready to lose everything that mattered to him.

He couldn't believe you, out of all the people in the world, you couldn't do that to him.

He had lost a wife and a baby before, and he wasn't going to go through that again. He had said many times he didn't want to be a father, he didn't want to have a baby and he thought he found someone he could rely on, he could trust.

But he hadn't.

No matter how many times you had tried to explain to him you were on birth control and that they could all fail, Jack wouldn't listen to you.

You argued, yelled at each other, he told you so many horrible things to which you replied even more horrible ones.

But the end of the line was when he suggested you get rid of the baby.

You couldn't and you wouldn't.

You had never thought of yourself as a mom, you didn't even think you had the maternity bug in you, but the moment you learned the news you were carrying a little someone inside, someone who would grow to become a baby, and then a beautiful child, you just couldn't bring yourself to do it.

Jack even offered you money, so you would interrupt it. But you didn't even bother answering him. You took off the ring he had given you, placed it back in the box and left it on his pillow and you walked out of the ranch you had called a house once and never returned.

You hadn't seen Jack anymore. But you still felt him around sometimes, you just couldn't tell if it was real or just a product of your imagination. You would catch whiffs of his cologne, or you would glance at a man that looked like him and would simply disappear in the blink of an eye. As your bump grew, the loneliness and the heartbreak were visible. You would smile, but the smile wouldn't meet the eyes.

Still, a small part of you thought and maybe hoped he cared for you, but he never came after you, he had nine months to do so and you had no news.

When you learned you were having a baby boy, you felt a pang in your chest and for a moment you actually worried about what he and other people would think. You didn't want to compete with her, you weren't a replacement of his family, you knew he had lost a wife and a baby boy, and life had given him a bride and a baby boy and he chose to walk away from that. You realize then, you weren't competing with anyone, you were living your life and it was not your fault if someone else lost theirs in such a tragic way. Then, after that realization, your heart filled with nothing but love and pride of you beautiful baby boy. If his dad chose not to be around, he was still a tiny piece of Jack you would keep, to remind you of all the good times you had spent together and the moments you were happy.

When you gave birth to your beautiful baby Wyatt, you thought you had seen Jack. You were almost sure you woke up in the middle of the night and found him in the room. He was dressed exactly the way you saw him for the last time, dark clothes and cowboy hat, and he eyed you and the baby.

You didn't have the strength to say anything to him and you just closed your eyes when you saw him picking up Wyatt so carefully into his arms.

In the morning, the doctors said you had experienced a fever peak through the night, so if it was actually Jack or just a cruel feverish dream, you couldn't tell. You even asked around, but no nurse had seen a cowboy over the nightshift.

Time flew, you never actually believed in that whenever you heard people saying, until you realized the tiny newborn became a bigger baby and that baby turned into a toddler in the blink of an eye.

Life was hard without Jack's financial support, you had to admit that, but you lived a happy life with your son, who painfully reminded you of his daddy. The sweet warm pool of brown chocolate eyes, to the cute curls that grew wide if you didn't give him a haircut every two months, to the smartness in him and his fascination with farm animals.

It was actually kind of funny, Wyatt had never met his daddy, he had barely acknowledged the fact other kids had a father and he didn't have one, and yet, he was just the spitting image of his. Sometimes you wonder what Jack would think of him, if he would be proud, happy or pleased to see his boy and himself were so alike. You still had that feeling Jack was around at times, when you took your son to play dates at the park, when you were out shopping and he waved at someone behind you you couldn't never actually see.

And also the times a mysterious amount of money came in handy whenever you found yourself struggling with some bill.

A tip or a bonus in cash your boss didn't actually know how to explain where that came from or when some of your debts simply had disappeared, but you couldn't track the source of the money. However, you only knew one person who had enough money to actually be able to do such things.

You just didn't understand why Jack did all that, if he was so clear about not wanting you nor your baby you didn't get why he still took some of his time to go after the two of you and not only that, he was also putting money into you. Not every month, like child support but enough so you could be comfortable.

On the weekend, you decided to take Wyatt upstate. He was so excited to go to the small farm, a nice ranch where families could spend the day and see all kinds of animals. Your heart ached as you thought about the time you lived with Jack, if you hadn't gone separate ways, Wyatt would love to live there, play with the animals all day and interact with them. It could have been a different story, for the two of you and also Jack, but it was his choice after all.

The little toddler was so excited as you walked around the entire place with him, you were so patient with your son, holding his little hand and showing him all the animals he wanted to see.

He liked the chickens, the horses, the baby pigs and was so excited, but his little heart raced when he saw a man standing a few feet away.

"Mommy, wook! A cowboy!!!" He squealed excitedly as he still struggled in pronouncing the Rs and let go of your hand, running freely towards the man.

You called his name, but knew it was no use at all, so you forced yourself to run after him. You fastened your pace, worried about losing your little boy in the crowd and froze as you saw your son standing next to a man you could recognize miles away. He was in his typical cowboy clothes and he had one arm wrapped around Wyatt's small body.

He smiled at the little boy, nodding gently at whatever he was saying to him. You looked at them in horror, shaking your head and not understanding why that could be possibly happening.

You took some steps closer and whispered your son's name. Jack immediately looked up at you and smiled softly

"Here's your mama, little one" he said in his thick accent "looking pretty as ever" Jack added and got up, lifting his son up and felt his heart clenched at how tiny arms wrapped around his neck. He trusted him so easily, as he was so sweet and affectionate, without even knowing him, without having a clue he was his dad. Of course that sweetness was all you.

You teared up and swallowed hard, extending your arm to Wyatt who was still mesmerized at the big boy.

"Hat, mama!!" He pointed excitedly at Jack's head and made the older man chuckle.

"I see you are a little cowboy yourself, aren't ya?" He asked and took his hat off, handing it to the little boy and placing it on his head.

He kicked his little legs in excitement and finally agreed to go with you, holding your hand and twirling around in pure happiness.

You didn't have any words to say, you wanted to stay away from Jack, and keep him away from your son, he had rejected you, and now he had no right to claim either of you.

You immediately took Wyatt's hat off and shoved it back to Jack. He only stood there, disappointment in his eyes but he understood it.

"It was nice seeing you, sugar. You're looking gorgeous as ever" he said but you only gave him your back and walked away from him.

Jack had lost his first family and out of fear, he lost his second one too, because he was a coward, he was a bad man and he would have to live with that guilt for the rest of his life.

_____

A/N: of course my first Agent Whiskey piece had to be an angst one. I hope it was alright ❤️

[eudaimaniacs]

agent whiskey smut headcanons

character/universe: agent jack "whiskey" daniels (kingsman: the golden circle) warning/s: full-on smut, read at your own caution notes: first time writing smut, so i'm not yet comfortable writing a full fanfic/imagine about smut, but this definitely helped me to write more. hope you enjoy reading!

Agent Whiskey is one heck of a man and lover. He can be rowdy and rough but shows his romantic and passionate side.

Jack loves putting on his cowboy hat whenever you have sex. Quickie or not, this man won't let go of his hat. (Save a horse, ride a cowboy).

His favorite position is cowgirl because it fits the cowboy aesthetic he's known for. Jack prefers positions that let you ride him but also loves when he sees and kisses you.

Jack is vocal during sex and loves complimenting you in that thick accent. He also lets out beautiful and deep grunts and moans that are music to your ears.

Location can vary for this man, but the bedroom is the best (of course). He wants privacy when you have sex with him but takes risks when he feels to. One time, you two were almost caught by a co-worker, and it was awkward brushing it off.

Jack also loves car sex, especially in his Ford Bronco. It can vary from Jack fingering, giving him head to fucking you. It's uncomfortable to have car sex, but Jack makes it the best.

This man has a heavy breeding kink. Jack wants to start a family with you, and it shows when he hasn't seen you in a long time. He loves dumping his warm load inside your pussy.

Jack is the dominant one when it comes to bed. He takes control and gives you the most head-spinning and fantastic sex.

Jack is a major tease and lets out a hearty laugh when he does it.

Whenever you tease this man, it's another story. Jack becomes possessive and marks you to remind everyone that you belong with him.

He doesn't like to admit it, but sometimes Jack loves when you switch and take control instead. It turns him on when you become dominant and shows confidence.

Going back to one headcanon, Jack is a worshipper and takes his time to admire every detail and curve on your body. You shiver when he touches those sensitive spots while complimenting your figure on that sexy, thick accent.

Whenever you have passionate sex with Jack, he takes his time indulging and taking care of you. He whispers compliments and makes the atmosphere romantic.

Lastly, aftercare with Jack is the best, rough, or most passionate sex. He cleans you up and makes sure that you feel okay. Jack kisses and hugs you after sex when you two lay on the bed. 

eudaimaniacs © 2023

[wildemaven]

Jack’s determined to sweep you off your feet for Valentine’s Day

[infinity-mars]

Play With Me

Pairing: Jack "Whiskey" Daniels x f!reader 

Word Count: 8.5k+

Rating: Explicit Smut (18+ only) 

Summary: You go out for a night of fun and encounter an alluring cowboy that does everything he can to capture your attention.

Also posted on my AO3 !

You loved to dance. Those moments when your heart fluttered in your chest made you move like you could fly, relishing in the feeling of power it gave you. You weren’t particularly graceful or always on time, but there was a certain magnetic thrum in the air that bent you to its will all the same. 

From outdoor dance clubs to private velvet-roped lounges, discothèques, raves and rooftop bars, you’ve tried to see it all with your friend Kate by your side. 

The cool air nipped at you both as you finally walked inside the club, the heat of passing bodies a welcome feeling. The lit room had a hushed glow as people made their home for the night in plush seats off against the far walls. 

You imagined that the venue was similar to what Alice saw when she went down the rabbit hole and found herself in Wonderland. The bar certainly had the right name, you thought, the people walking around just as colorful as the children’s story. 

The bartender was quick and you were thankful, even though the drink he made was weaker than you preferred. Vodka burned as it hit the back of your throat, aided by the scoff that found you at the man chatting up your friend. 

Kate always had a thing for slightly pathetic men, like she could eat them alive. You were used to her routine by now, her colorful storytelling one of your favorite things to listen to over your morning coffee.

Honestly, you were both horrible together: you pitied the unsuspecting bystanders that listened in. Laughing at an old story she loved to tell at your expense, you didn’t see him at first. 

You wish you could go back to the moment he came crashing into your orbit, not noticing the person on your left until he made himself known. 

“Now what is a pretty bee like you lookin’ so bored all the way over here?” a gravelly voice spoke, the man’s lips tantalizingly close to the shell of your ear. 

Your eyes looked over before your brain could catch up, and what you saw certainly sidetracked whatever thoughts had possessed you before. Wearing a black leather jacket that swam in the neon light of the bar, he almost seemed to glow in a classic white shirt that tapered on his slim waist.

“I’m enjoying myself just fine thank you,” you retorted, taking a generous swig of your watered down drink to hide the rush of nervous energy that possessed you. You were used to beginning the chase, and it caught you off guard to be taken by surprise. 

How refreshing.

 A small grin flickered across his face at your answer. His dark hair and broad shoulders only made him more mysterious, the lolling drawl of his voice making you curious despite yourself. 

Men would approach you with the fashionable audacity they all liked to carry around with careless hands hoping for a quick fuck. Sometimes you’d indulge yourself, but the enjoyable heat of another person wasn’t worth it if they never shut their mouths. 

Your vibrator and weighted blanket made sure of that.

You were undecided if this man fit into that category though.

“That’s not what I see.”

“Hmm, what do you see then, if you know me so well?”

The man shifted his foot and leaned in closer, the subtle spice of his cologne clinging to his suede collar. The way he wore it was effortless, and you wanted to grab onto his jacket to either bring him closer or shove him back, depending on what he said next.

“I see a woman that’s bored out of her mind trying to convince herself she’s not, drinking alcohol not worth the proof on the bottle,” he explained, voice dipping lower as you turned to fully face him, finally meeting eyes that never strayed from you.”You want more than whatever junior over there could ever offer someone like you.”

“Someone like me?”

“Oh honey, I know I walked into that one with both feet. You’re just fishing for compliments now, aren’t ya?”

“Mmm, are you going to tell me what I wanna hear or are you going to buy me a drink?”

“The shit they mix here ain’t what you deserve, I saw that bartender mixing those drinks. Take a sip of this darlin’, and tell me I’m not wrong,” the man tempted, readily extending a sleek silver flask to you that was attached to his belt buckle. How scandalous .

The promise in his expression emboldened you. He had taken a drink from the flask himself before offering it to you in invitation.

“What’s life without a little risk?” His eyes seemed to ask.

You took the chance, the warmth from his hands lingering on your fingers as you took the flask from him.The delicate gold choker on your neck glinted in the light as you swallowed.

Taking a swig, you absorb the flavor. He knew his alcohol, and from the confidence of his statement nothing less than top shelf mattered. You could certainly respect that, wondering if his lips would have the same taste if he kissed you.

“You’re not wrong, it’s very good. I’ve always been partial to whiskey myself.”

“Just good? What you have in your hand is a rare share of Statesman Whiskey, made straight from the source in Kentucky,” he retorted, almost offended if not for the mischievous twinkle in his eye. Something you had said passed a test you weren’t yet aware of.“Even as a Yankee you must understand the quality of that. I knew you would.”

“You caught that, did you?” 

“I don’t miss a thing, and you have most certainly caught my undivided attention.” 

You shifted completely to turn your back on your friend and her man of the hour, uninterested in the conversation that no longer included you. 

This man was right about one thing: you had been bored, and hopefully he would measure up for the evening. He didn’t shrink at your gaze.

It was nice to be approached for once with an interest that could mirror your own. 

“I don’t know how you fit that ego of yours inside this place. This doesn’t exactly look like your scene if I’m being honest.”

He chuckles at that without taking offense and coyly tips the brim of his hat in your direction, smiling with a flash of tongue at your choked laugh that's just for him. 

“Let’s just say I’ve gotten a lot of practice over the years. Even more talking to gorgeous girls like you. A buddy of mine wanted me to check out this new place to meet up sometime for work .”

The queer way he said that wasn’t lost on you, but you figured it was just an inside joke of some kind. 

“You know that a honey bee can sting when it's threatened right?” 

The way he widened his stance in victory as you focused on him was intentional, the insufferable action the kind of cockiness you usually wanted to smother with your own if not for the way it oddly suited him. 

“Oh, that doesn’t deter me one bit. I’m sure your sting is just as sweet. I happen to like that.”

The grin peeking out from beneath his mustache looks genuine. You’re intrigued, looking at him now in consideration. As you checked him out from head to toe, one thing stood out rather prominently. 

“Is that a gun in your pocket or are you just really happy to see me right now?” 

New York might be a concealed carry state but he looked like one of the only men on the premises actually packing heat in all of the ways that matter. The well fitted dark blue denim hugging his thighs left very little to the imagination. 

He was tailored to torture you inch-by-fucking-inch.

“Why don’t you come dance with me for the next song and find out?”

Oh you definitely wanted to shut him up. Preferably with something else to keep that mouth of his busy. 

“No.”

“No? Give me one reason why not and I’ll leave you alone. You can take someone else home tonight and leave ol’ Jack behind.”

“So that’s your name then? Jack,” you reply. His eyes droop at the sound, half lidded and unhurried in the way he examines the way you say his name. 

You finally introduce yourself, like you hadn’t been bantering with the man for a while now. 

Like you hadn’t been imagining what he would look like after spending a night with you, scratch marks down his back a parting gift that'll make him think of you every time he moves.

“If you are so obliged, it’ll be the name you’ll be screaming later and that’s a promise,” he vowed, chewing on a mint he popped in with a cheeky wink thrown in your direction. On any other man that would be a turn-off, but you looked down and saw the way his hands clenched around nothing as you observed him. 

Jack was his own harbinger of surprises it seems. 

The second of silence that follows sears under your skin, charged and frantic for more friction. A quick reply caught on your tongue that you held in, keeping it for later: never let it be said that you didn't like flirting with delayed gratification every once in a while.

“How do you know that I don’t have someone already waiting in my bed for me?” You asked. Jack’s eyes were arresting, lingering lower on your chest for a few moments before looking into your own to answer you.

 He gave a satisfied hum when he found whatever he was searching for.

“I think the way you’re staring at me is all the answer I need.”

You’ll give him credit, he was saying all of the right things. Or at this point, you wanted them to be, your attraction only tipping in his favor.

“Now what is a Southern boy like you doing here? Not to be a cliche, but you’re a long way from home.”

“Oh, I’m just like anyone else. I work at the Statesman New York office, traveling a lot when I’m needed elsewhere. What do you do when you’re not talking to vagrants like me in strange bars?”

“I’m a romance novelist, dabbling in a lot of things really, you know how it is.”

“Hmm, now that sounds interesting. What words must form on that clever tongue of yours?”

“Wouldn’t you like to know,” you flirted back. 

He began speaking again, the story he launched into exotic and altogether hard to believe, but it wasn’t the words that reeled you in. It was his large hands waving temptingly close that distracted you. You could care less about the time he almost died in Marrakesh after offending someone’s wife.

You’d commit the story to your memory later when the pleasant haze of him faded away.

His tale came to a close as you glanced down and laughed at the stereotype that for some reason didn’t surprise you.

“Can you even dance in those boots for anything other than a two step?”

“I can do a lot more than that.”

“With your shiny belt buckle and Stetson I’d almost think you’re compensating for something,” you teased. A flash of delight lit up his face at your observation, the smirk he sent your way something just north of sinful.

“Everything is bigger in the south darlin' and besides,” he trailed off, hands coming to slowly cage you in against the bar but not quite touching you. “Let’s be honest here, we both know you like what I’ve got underneath.”

You lean forward, a breath of air suspended between you as your mouth almost ghosts over his. Maneuvering out of Jack’s reach, you reach up and take the hat off his head.

You had no doubt he would have stopped you if he had actually wanted to, those large hands of his able to easily overpower and hold you down. 

You suppress a grin at the thought.

Putting the large hat on your head, you brushed out your unruly hair to make it stay firmly in place. His eyes unfocused for a moment before looking at you with renewed intensity, his jaw ticking to the side as he takes you all in. 

You loved the chase, but at that moment you were tempted to end the flirtation and leave the bar to see if those fingers would fill you up as well as they promised. 

“Come on, show me your moves," you dared, steeling yourself as you joined the growing crowd beginning to take over the dance floor. He convinced you. "Do your worst, Jack.”

A remix of one of your favorite songs set the pace as it moved through you. The bass was rich and dark in your veins as you danced, Wonderland falling away in the fury of bodies all around you. The charge that flitted low in your abdomen was one that threatened to crack you in two as Jack brought you back, your ass grinding into him after each beat.

It would be so easy to turn around and let yourself melt into the heat of him.

 But riling him up sounded like a lot more fun. So when the beat shifted so did you, one hand removing the hat from your head as the other reached behind you to bring him down to your level. 

“You know, there’s a saying I heard before that if you steal a cowboy’s hat you’re either fuckin’ or fighting, and darlin’ I don’t have any weapons on me right now. So what’ll it be?” He asked, his voice against your ear making you lean into his palms. 

You felt like smoke, weaving around him as you continued to dance.

“Mmmm, doesn’t a combination of both sound just as good?”

The reactive tightening of his fingers on your hips was just what you needed. The both of you were lost, the music loud enough to cover up how hard your heart was beating.

Jack runs his nose along your neck and jaw until he nips at the vein, the heat of his breath making your own decision for you.

Turning, you reach up and finally kiss him. It wasn’t a quick affair, the push and pull between you both a fight to see who would give in first. You wanted to memorize the feeling, imagining the burn of his facial hair on your thighs as you rode his face. 

You’d even wear his hat while you did it if he asked nicely. 

He tasted like mint and mussed hair dangled in front of his eyes, lightly brushing your forehead as you mingled together. 

You were both insulated in the crowd, kissing each other until you were hardly even dancing anymore. 

Ready to leave the liquor and low lighting behind, you stopped Jack in his tracks. Backing him into the wall of the hallway you ventured into, you did so firmly, hands holding him hostage as you clung to the lapels of his leather jacket. 

The hunger he saw reflected in your eyes pinned him in place, and that alone made him want to ruin you. 

Leaning up in your high heeled boots so that you could kiss his cheek, the remaining lipstick you wore smeared onto his skin like a brand, the red lip print left near his opened mouth telling him that you were dangerous.

Better yet, his favorite kind.

“Follow me cowboy,” you rasped, leaving goosebumps in your wake as you lightly skimmed over his skin with your teeth. The fever consuming from now was one he hadn’t felt bubbling in his blood ever since his last mission months ago.

 He craved it.

Jack vaguely connected that you were an unstoppable force to his immovable object, ready to crash into him like the paradox you were presenting yourself to be. 

When he had clocked you from across the bar earlier he had admitted to himself that you weren’t the usual type of woman he jumped to charm into his bed. You had looked wholly unimpressed with your surroundings before, swirling the ice in your drink as the yuppie next to you preened like a toddler with a captive audience. 

The oncoming storm he’d read in the lines of your body told him another story, however, one that swept him into you and past the redhead that had been trying to catch his attention since he’d walked in. 

The shadow of something wicked had made Jack eager to align your passions with his own.

Impatient at his composure as he thought of this, you hooked two fingers into his belt loops and tugged him off the wall and into you, that jolt he felt from before electrifying below his skin as you pressed against him. 

Reaching down and lightly cupping one of your hands over the denim of his jeans, you felt him squirm the longer you dared. 

 His dark brows furrowed at your forwardness, wanting to taste you again.

Your hands were firm on him, brokering no argument for the sly agent to persuade you with. He admired your drive, easily taking the momentum from him and twisting it to your desires. You kept surprising him, and by the way you delved into his mouth you weren’t afraid of showing him this side of you.

You wanted him to say something, anything, so this time you squeezed with intent, the hiss in your ear headier than the alcohol on his breath.

His cock twitched under your hand, and god it was power . 

You enjoyed him like this: slightly wild but contained, a groan threatening to break through clenched teeth as you felt him up in public so casually. 

You kiss him possessively in that dark room, drinking him up and daring him to consume you in turn like he promised. He might have approached you first, but you were going to finish what you both started.

It was desperate and messy and loud but neither of you cared.

A couple walked close to the both of you, forcing you to break from him in the narrow hallway to let them pass. Your absence made Jack swiftly reconnect himself with your body, his large hand sliding down into the pocket of your jeans to roughly squeeze your ass that had been grinding on him only moments before. 

Leaving his hand where it was, he used it to direct you outside into the street. The nighttime air filled your lungs with relief, cooling the sweat that dampened your neck.

“You're positive you don’t wanna go back to my place? I can assure you the view from my floor is nothing to scoff at.”

“While that might ordinarily be tempting, Jack, your apartment doesn’t have any of the toys that I like to use,” you retorted. 

You could already imagine flashes of the night ahead of you at your apartment. 

“A pity then, I just know that you pressed against my floor to ceiling windows when the sun rises would be a pretty sight indeed.”

“Let’s enjoy tonight and plan on that for next time.”

Shame was not an emotion that Jack entertained often and he wasn’t about to start now, leaving your lipstick where it sat proudly on his face. A few people stared at him in the street, but no one stopped your brisk pace. 

At the last crosswalk he pinched your ass in retaliation when you turned to kiss him harshly, nipping his chin as you leaned back onto your heels. As if you were dry kindling struck by lightning, his hands trailed flames in their wake, each touch only hastening your steps forward.  

Exposed brick, industrial lighting, and high ceilings were what attracted you to your building when you first moved to the area. Your small loft on the upper floor gave you the privacy you craved, the cityscape around you comforting in the way it always kept moving. 

While waiting for the elevator Jack untangled himself from you to lean against the wall on your right. He stood there appreciating you as a few of your neighbors walked around the lobby, Jack tipping his hat to them as they passed.

You didn’t even realize you’d dropped it at some point to kiss him earlier.

“Prettier than a peach,” he murmured, his hand reaching to smooth over his mustache in thought. He was earnest, the mood shifting into something unnamed as the elevator dinged. You huddled into him as people came and went.

"You know," you began, "I'd look even prettier with your hands wrapped around my throat."

 He coughed into his hand, not wanting everyone else in the lobby to see how tight his jeans suddenly felt. You laughed.

You both stumble into your apartment, the size of Jack overwhelming as he backs you into the closed door. His mouth was persuasive, like a switch was flipped now that you were both away from everyone else. 

He left bruising kisses on your neck, completely unyielding in his quest to mark you wherever he could reach. His hands were on the back of your head, holding you in place as he gripped your neck just so. 

For a long suspended moment you were frozen, wanting to regain the ground you refused to lose. But hell, could this man kiss the thoughts from your head. 

Then, all at once, heat spreads through you, thawing you into action. 

Holding onto his jacket with your fingers you tilt your head back with a breathless chuckle, making Jack look into your eyes. You take up one hand and grip his chin, the other drifting to caress the lipstick mark you shamelessly left on his cheek. Pressing down on it with more pressure to show you meant your next words, you wanted him to listen. 

He smirked into your touch, a cocky sort of grin showcasing his dimple that felt entirely warranted as your breath stuttered in your chest. 

“Go sit on the couch,” you ordered. Kissing you once more before moving away, a filthy moan left you as his tongue darted out for a taste. His eyes didn’t look away until you turned your back, shedding clothes in your wake until all you had left on was the lace you were wearing.

“Would you like a drink?”

“Sure thing baby, pour me a bit of whatever you’re having.”

You didn’t leave him for long, reappearing with strong liquor and the type of lingerie that made you feel like you could eat a man’s heart in the marketplace like Beatrice once said.

The warmth from the drink you’d sipped in the kitchen enveloped you as it licked up your chest— you were in your element now.

Grounded in your body, you took a deep breath. 

Emerald lace and satin embrace you, assured in the sway of your hips as you walked over to your cowboy. Handing him his drink and swiftly straddling his parted thighs, you let him take you in.

 You don’t know when he became “your cowboy,” but it sounded right, for the night at least.

Say what you will, but Jack was flexible with a change in plan. He just had to bide his time, finishing the finger of bourbon left in his glass before setting it aside.

The way you spilled out of your lingerie had him drowning in you. Champ once told him that he was an adrenaline addict, chasing every mission that got his heart racing. He wasn’t wrong—you couldn’t function as a successful Statesman agent without a dash of daredevil in you.

And he just loved the way you moved.

His mouth descends on you again, leaving you once to gulp in a desperate breath before attacking with renewed vigor. 

He hoarsely spoke your name, and it was the best thing that had left his lips all night. You wanted him to say it again but this time underneath you, unbidden and desperate at the way you pulled it out of him. You slid your tongue into his mouth and brought up a hand to roughly yank at the hair on the sides of his head, until he bowed his back and leaned into you for a moment.

“Is this what you want?” You asked, snaking your hand underneath the cup of your brassiere to shove it aside and caress your breast, a groan breaking through your composure at the way Jack bucked into you. Though his breathing was measured and even, his lips parted at the sight of your nipples pebbling in the cool air. 

“You know, when I saw you at the bar I knew I had to talk to you, take you with me when I left,” he murmured, quiet in his admission as it rang true on his face. 

“Mmmm, honey, I don’t know if you’ve noticed but...you’re in my apartment at the moment, on my couch no less, drinking my bourbon,” you answer just as quietly into his ear. You graze over it teasingly with your teeth just to see him shiver. “And I’m wearing a matching set right now. So who really took initiative tonight, hm?”

Jack laughed almost in disbelief at your words, his body responding for him. It’s an honest sound, one that makes you kiss him deep enough to taste his tongue in the back of your throat.

Ultimately what you saw in his eyes was patience. And that was hotter than anything else he could have done. 

 You sigh his name, letting your head fall forward as he seeks out another kiss from you. 

“This is just the preview. I want it all, and I know you do too,” he breathed against your lips. “Now are you going to let me touch you, or do I have to watch you fuck yourself on my thigh before I can taste you? You can only tempt a man so far.”

“Is that a threat or a challenge I hear?”

“I did promise that you’d be screaming my name, and I take that job very seriously. You'll hear no arguments from me.”

“You sure you can handle me like that, cowboy?”

Jack was wavering somewhere between wholly aroused and perversely indignant. No one questioned him like this, in the bedroom or otherwise if he could help it.

 He hated how it turned him on like this. 

You’re not sure what emboldens you to tease him; your resolve only heightens the longer he looks at you, as if you could spill over into him and it still wouldn’t be enough. 

“I have never been more sure than I am right now.”

He knew how to fire you up. In many ways, you were both quite similar.

Restless and insatiable. 

Purposefully running your hands down his chest only to stop your exploration at his belt, the rumble in his chest was one of approval as you scratched at his abdomen through his shirt. 

You enjoyed yourself when pleasure could mix with a bit of pain, and you had an inkling that Jack did too. You wanted to deny him, reduce this enigma of a man into a begging mess before the sun came up. But your own need to be touched by him won out, and damn him for kissing you like that—as if you were the antidote to a fatal poison he had drunk in an effort to forget you. 

“You can touch me, Jack, but there’s something I want to do first.”

You meet his gaze for a brief moment as you pause in this position on top of him, being perfectly still when all you wanted was to hold him close until there was no space for questions or distractions.

An understanding passes between you both. Your body buzzes with nerves, synapses firing as all thoughts focus on the man holding you.

He grabs at your hips, whispering encouragement in your ear as he guides you to settle flush against his lap with your legs on either side of him. The zipper of his jeans and his belt buckle rubbed into your clit hard enough to make you shiver.

“ Fuck… ”  

Jack  scrapes his teeth over your jaw. Barely there. More of a breath across your cheek than anything. 

You reach back and unlatch your bra, throwing it away as he cups each breast in his calloused hands. Arching into his attentive mouth as it reached your skin, you threaded your fingers in his hair, messing up the hat flattened strands and tugging on them harder when he bit down teasingly. 

Letting your nipple go with a wet plop, he leaned back into your hands on his head.

“God, I am so fucking hard thinking about licking into that pretty pussy of yours, bet you taste real good,” Jack groaned. You answered in kind, kissing him again to swallow his words.

This was just the warm-up.

“I’m going to cum just like this against you, but if you move any more then I won’t be quite so kind later. Wanna make you earn it. I’m a generous lover, Jack, but a fair one,” you simpered, grinding almost cruelly against the hardness of him that you could feel throbbing through his pants. “You want me to be nice, don’t you?”

“Oh darlin’, I’m sure you’re sweeter than a saint,” he grunted, words stuttering as you brought his head up closer to yours, lips touching but not quite. Rotating your hips, you sigh into his mouth as you move against him. 

True to his restraint so far, he kept himself in place, his breath hot against your cheeks as your pace quickened. 

“Mmmm, can’t wait to have you inside me,” you sighed, his muscles straining beneath your fingers. Shuddering at the feeling of him under you, your first orgasm was creeping closer as it began trickling down from the tips of your fingertips. “D-don’t want you to cum until I’m done with you.”

Jack’s mouth opened partly in awe as you grinded on him with even more force. 

He had a hidden strength to him, and by the way his arms flexed around you he could have easily moved you under him at any time. The fact that he didn't demand it was arousing.

Fuck you were wet.

Tilting his head slightly, he enjoys the view of you on his lap using him for your own pleasure. Your tits bounce as you move, and he’s torn between telling you how perfect they are and moving just slightly to bury his face in your softness. He whimpered silently as you pulsed around him, able to feel it over his clothes as you threatened to unravel.

“Oh, look at you,” he exclaimed, voice a low rumble that stokes the fire in your belly. “Just like that, baby. Fuck, come on. Take what you need from me.”

He says your name once, fervent and taut, barely able to keep himself in check. The fact that he was still almost fully clothed made him need more . You were all warm skin and curves and he wanted to feel every second of you wrapped around him.

He tensed his thigh and shifted slightly but you didn’t notice as you rode out the waves of pleasure rolling over your clit.

It was exquisite and hurried and not the end goal but you didn’t mind. You had wanted to see if he would listen to you. If he could take what direction you gave him. It was an entirely different high you’d surprisingly discovered in your twenties, having a man in your control, making him beg with just your body. 

And yet, Jack did not beg for himself. The look in his eyes was expressive enough. Still he didn’t move, and that was what finally pushed you over. 

Gasping in shock, your orgasm softly washed over your skin. He eagerly watched, memorizing the way your mouth hung open at the feeling of him grabbing your hips with bruising force to drag you over him once again.

When you finally opened your eyes Jack was already looking at you, and you did not shy away. His hair was tousled from your hands, lips swollen, eyes bright—you savored him like the Kentucky whiskey on his breath. 

“Mmmm, you were so good for me,” you praised, voice heavy in your mouth as you recalled how to speak.

As you came back down he chased your lips, taking his time to touch you the way he could now that you’d fallen into his chest. His mouth was a wanting, wretched thing, tracing a path from your lips to your chest. 

You pulled back for a moment. “Do you want to switch to the–”

“I’m not done yet,” he interrupted, bringing you back into a heated kiss that had you whining into his hold on you. He slips his tongue in your mouth and seems to slow time licking into you just so, making you shiver. 

His hands were frenzied in the way they glided over all the flesh he could reach. 

You would torture him no longer.

His blunt nails traced over your spine, and you wanted to ask him to do that again. 

“Now you are a rare gift, my dear,” he hummed into your mouth. “I would hate for you to be tired already.”

“Oh, you don’t have to question my stamina,” you slyly answered. Even now you are still hazy in your bones, tethering yourself to his firm grip on your ass. “Worry about your own.”

The chuckle that leaves him is telling, and you clearly feel his frustration rolling off him now that you can think in complete sentences.

You kiss the corner of his mouth and swiftly hop off of his lap, trembling for a moment as you right yourself. There’s a slight damp spot from where you were sitting on his white shirt that had been hanging over half untucked from his jeans, but you’re too drunk on endorphins to feel embarrassed. 

You did that .

Your heart stuttered for a moment at the raw ache you saw in his face. Hooking your fingers in the slim waistband of your panties, you then cast them aside. 

It felt like an afterthought after what you had both just done, but the way Jack looked at you was anything but unappreciative. 

What you inspire in him is so erotically charged that he is momentarily struck dumb by what you do next.

Falling onto your knees you look up at him through your lashes, taking the flask attached to his belt buckle, the surface slightly wet from your release making it slick in your hands. It was silent in the apartment, the only sound Jack’s breathing as he watched you drink from the flask that he favored so much. 

You could taste yourself around the metal and lipstick and whiskey. A theme of the night it seemed.

Awareness flows down your spine at Jack’s gaze. As you take one more pull, his hands reach up to card through your hair, holding it in a makeshift ponytail, reaching for you with a finality that has you arching into him.  

You lead him into your room, wishing you had cleaned up a bit before tripping on the rug, laughing as you both stumble into your metal bed frame. 

“Now Jack,” you begin, bracing yourself for the next conversation you rarely walked into without some gut feeling bracing you up. “Do you have a safe word?”

He didn’t answer immediately, but when he did he was entirely focused on you. 

“I do, pretty girl. It’s sweet tea.”

The way his mouth caressed each syllable with that slow southern drawl shouldn’t have been as damning as it was.

“How do you feel about ropes?”

The way he lit up was thrilling. He looked away with unfocused eyes, enjoying a private joke that only he knew. It was the expression of a man that delighted in his own mystery. 

You couldn’t deny that a part of you was burning to know what he locked away. He prowled with that hidden energy, and knowing what you’d experienced of him so far, you would have to work for a proper taste.

“I happen to be quite gifted with whips and a lasso if I do say so myself. I’m rather versatile in that regard. Rest assured it is not my first rodeo.” 

“In that case cowboy, I want you...to tie me up,” you said before grazing your thumb across his bottom lip. He nodded slightly surprised, with the way you had directed him earlier he had thought you’d wanted to tie him up instead.

 It wasn’t like he couldn’t escape from some ropes if he really needed to.

He had been amazing under you before, but you wanted more. You wanted him to take your body and make your need dissolve on your tongue as you cry. You wanted it to hurt.

Jack felt like you could read his mind, look into the very heart of him and learn all of his desires. Palming himself over his jeans, he imagined the warmth of your mouth and had to stop from outpacing himself.

You walked into your closet with purpose, toeing on your favorite pair of stiletto heels as you grabbed your selection of ropes from where they’re hidden.

His eyebrow ticks up at the sight of you naked with only your Louboutins on, the black ropes in your hands are just as daring. He waits for you to settle onto the pillows of your bed before methodically tying your hands to hooks in the wall on either side of your headboard.

 It took him a few moments but his knots were sound, loose enough but tight on your wrists so you couldn’t break free. You were grudgingly impressed with how fast Jack could work when he was motivated, filing it away where you could exploit later.

He throbs at the salacious painting you rendered, spread out and glowing in the warm lighting of the room. With your opened legs you were vulnerable and slick and soft. 

Jack didn’t want to wait any longer before losing himself in you.

He shifted down to lay himself between your parted legs. You swiftly stopped him with your left leg extended fully out, the stiletto of your heel digging into his lowered shoulder as he kneeled on the bed. The startled look on his face made you tease him, grinding it in a little further before moving it down his chest to stop at the length of his cock straining for freedom. 

Pressing down.

The choked groan that he involuntarily let out was painfully erotic. You wish you could record it and hit rewind.

“Hold your horses, Jack. You have far too many clothes on. Strip for me first before you get what you want.”

To his credit he didn’t jump up and frantically discard the remainder of his clothing. Like you before his expression turned calculating, methodically shifting off the bed and taking off his shirt and discarding his pants along with his underwear. All are then folded on your nightstand, neat and pricise to minimize wrinkles.  

You swallow at the way he ignores your anticipation, but it brings no relief. 

His skin is tan like the rest of him, belly soft and strong before a small trail of dark hair leads down to the base of his cock sitting heavy against his stomach. 

You imagine tracing your tongue over every inch of him seeing where he’d fracture and break in your hold, only to put him back together again when he asked.

He was incredibly distracting like that when he wanted to be.

Captivated, your eyes stop back at his chest, small faded scars criss-crossing his skin, one worryingly close to his heart that had you straining for a closer look. His muscles ripple as he moves, the veins of his arms as formidable as the rest of him. 

Jack was focused as he finally settled low on the bed, fingers ghosting over skin as he hitched your legs over his shoulders. Kissing and nipping at the inside of your thigh, he took in a deep breath and let out a little hum, puffs of air hitting your pussy as he adjusted.

He leaned his head on your left thigh and looked up at you briefly.

“You remember the safe word, sweetheart?” He asked. You nodded, almost drunk at the heat of him crowding you. “I need to hear you say it.”

“Yes Jack, I remember it’s sweet tea. Now are you going to eat my pussy like you mean it or do I need to get myself off again?” You answered, tapping your leg down on his back knowing fully well how it would rile him up.

He grins at you savagely, leaning down the remaining space to lick a long stripe all the way up your folds. 

You buck into his mouth, your already sensitive clit coming alive again. He moves his arms to cage your hips in his hold, bringing you flush to his tongue by grabbing onto your ass. 

He was nestled between your legs, mapping your body with licks and handprints. Your half-formed praises and keening whine made Jack a mess of a man, grinding into the mattress as he drank up everything you could give him.

He loved your voice and the way it scattered into nothing when he sucked your clit into his mouth. He made no pretense at staying quiet, noisy and whole in his destruction of you.

Coming up for air, his mustache glistened, cheeks red from his own harsh breathing against your cunt. His lips were wet and you wanted to taste yourself when he kissed you. He reaches down for a moment and pumps himself harshly, tightly fisted and the sound he lets out...you feel it like a pulse.

His nose brushes you as he dives back in. If he could sink underneath your skin you would burst. 

He slides two fingers inside, your muscles clenching around him as far as he could go. Curling his fingers upward and holding them there, a hot fusion of unnamed pleasure and painful awareness zips through you. You can't help but squirm underneath him.

There it was.

Jack wanted you to call his name until he no longer connected it with himself, an uncontained force that compelled him to do whatever you wanted if only you'd say his name like that again. 

Wanting. 

“Fuck, when you say my name like that I just burn all over,” he murmured. “You gonna cum now, baby?”

You hum distractedly, the coiled tether in your abdomen snapping when he doubles down just right. He eagerly laps at you as your pussy flutters, climbing higher and higher until plunging you into nameless bliss. Each limb feels liquid as you touch down.

Jack keeps sucking and licking you without stopping and you can’t cover your mouth to muffle the whimpers that slip through. He adds a third finger and continues to move through each aftershock that bounces through your body.

“Come on. Lord—when you sound like that I don’t want you to stop. You’re not done yet, I know you can give me another one. Look at the way you take me in.”

You wanted to dodge his mouth as he sucked on you again, even the gentle way he prodded at you felt like too much. You weren’t going to beg yet, even for a man like Jack. Despite your discomfort you felt yourself stir again, weaker but no less corporeal, as he pressed down hard on your clit with a pressure that made your breathing pick up.

With effort you rocked into him once more and strained to lock your legs around his head, squeezing when he nipped at you. A handful of minutes later you were boneless and spent, legs trembling as he drew your pleasure out.

 He moaned at the feeling of being utterly surrounded, desperately sending you over again so that he could breathe. 

You couldn't think past the wall of sensation you were being held against without mercy.

This orgasm was harder than the last, a juggernaut that only built on the first. A few silent tears trailed down your face, so overcome that his facial hair burned similar to the hand shaped bruise already forming on your hip. 

You close your eyes so tightly that sunbursts bloom behind your eyes as you breathe through it.

Standing up to catch his breath, he used some of the slick on his fingers to slowly cover his shaft, aching from being hard for so long already. From the sheer size and weight of him that you can see, you’re glad for the bottle of lube on your bedside table, though you’re so wet it probably didn’t matter.

Jack settles himself over you, tugging you up into a fierce, messy kiss, teeth and tongues and harsh breaths traveling from his mouth into yours. 

You were so relaxed that the stretch of him affected you only for a moment as he buried himself inside you. The gasp when he moves catches in your throat, a ghost of all the pleasure he had given you just moments before leaving your body.  

 His voice stutters as he slowly thrusts inside of you, setting a steady pace. “Should keep you right here just like this, make you cum until you forget your own name. Would you like that? Take care of you like no one else will?”

You swear, picturing his words as they traced themselves down your body. As heavy as the feeling of Jack resting his weight on you was, you thrived on it. Your arms felt strained from being tied, but he curled around you just so, keeping you both connected for as long as possible.

Jack’s arms flexed as he adjusted to reach for you, extending his fingers until they pressed into your parted lips.

Swirling your tongue around his two fingers, you could taste yourself on his skin. He then leaned down and used them to press into your clit. It had you closing your eyes, too overwhelmed to speak through it. 

You didn't have any smart comebacks in you now.

His unrelenting tempo jostled the bed against the wall. Moving back to lean on his heels, Jack pistoning into you at this new angle was overwhelming but you simply didn’t care. He yelled out in a voice you almost didn't recognize, hoarse and wet as it ripped from his chest.

“Come on Jack, cum in me,” you panted. “ Fuck , I know you’re close. Can feel you aching for it. You’ve been so patient. So good . ”

You intentionally clench around him like a vice, and it has him tumbling into his own release moments later with a startled shout.

Satisfaction seizes his veins in a chokehold.

He collapses into your chest, the both of you covered in a slight sheen of sweat that was beginning to dry in the cool air.

Whimpering slightly as he pulled out, he worked through his own lethargy to take care of you.

He leaned up and undid the knots holding you hostage. Immediately your arms flop onto the mattress, the burn of your muscles just adding to the mental catalog of sensations you take stock of. With Jack resting on your chest you card your fingers through his hair, the both of you too out of breath to say anything for a few moments. 

The weight of him on top of you kept you grounded.

Warm. Languid. Eyes drifting closed at how heavy you feel. 

“You are gonna be the death of me, woman.” 

“Mhmmm, if that’s the case then I’ll wait to tell you my proposal then. Wouldn’t wanna kill you before another round, Whiskey.”

He lifts his head from your chest at that.

“What did you just call me?” He asked, eyes unreadable as they scan your face. You didn’t care, the words light in your mouth as they leave you.

“Whiskey. You taste like it. And if you think this is the only time I take you to bed, then let me inform you: I still need to drink my fill of you.”

He scratched at his mustache for a moment in thought before he smiles, the most genuine of the night that makes his eyes crinkle with laughter. There it was again, that secret in his expression that has you eager to ask what he’s hiding.

“You’re a very perceptive person, honey. I am thoroughly surprised by you. Tell me what you have in mind when I come back.”

He jumps out of bed to walk into your en suite bathroom, his ass distracting as you watch him fumble around before returning with a warm washcloth to clean you up.  Each brush of his hands on your body is gentle, reverent even as it glides over you. He kisses where your hands had been bound, asking if he was too rough.

You almost laughed. 

You liked it that way. 

Something inside you wanted to stay in the moment, gazing at each other in the dimly lit room. Not forever, just a little longer. You imagine him walking away from you out the door, and it puts an unpleasant feeling in your gut, like you wouldn’t see him again.

You had the sneaking suspicion that if Jack didn’t want to be found he’d disappear.

“So I was thinking,” you began, finally tossing your stilettos off the bed to lay under your quilt. “I have an ungodly expensive espresso machine that makes a decent latte and fresh beans in the kitchen. How about we take a quick nap and then fire it up before round two? I heard once that drinking coffee makes the sex even better.”

“Don’t you mean rounds three and four?” He teased, that ego of his purring at the thought of how much you spasmed and shook around him.

If you weren’t so relaxed you would have probably grabbed onto his balls in response, made him swear around that crooked smile of his.

You'd learn how he liked it and edge him until he melted out of his damn cowboy boots. The thrill of him was delicious, and you hadn't gotten to take a true bite out of him yet.  

“You think you can go another round later and finally ride this prize stallion?” 

That makes you slap at his shoulder. His laugh diffused whatever seriousness lingered and you readily agreed, the both of you winding down as exhaustion hits.

 As his arms settle around you, you imagine the potential of a future with this man of mystery.

 He had barely scratched the surface of what made you wild, and you wanted to change that. Leaving Wonderland with him tonight was an event you were eager to repeat. 

[minniemoo2002]

A Tired Wife (Jack Daniels x Pregnant!Reader)

Warnings: Fem!Reader, pregnancy, fluff

Is this vaguely inspired by that one scene in knocked up? Maybe. Honestly can't believe I'm writing fanfics again I'm so excited

Jack always had a pit of guilt in his stomach when he came back this late. He crept up the stairs as silently as possible, avoiding the creaky one in the middle. The house was completely still so any noise would probably wake you, which was something he was desperately avoiding. Hell hath no fury like a tired wife being woken in the wee hours.

When he entered the bedroom and saw a perfectly untouched bed, the guilt in his stomach was replaced with pure panic. His bag was dropped to the ground without a second thought and his hand rested on the gun still in his holster.

"Y/n?" He called out

"In here" Your voice replied quietly from the en-suite bathroom. He hadn't even noticed the light leaking from the door. His panic melted away as he moved to meet you.

He wasn't quite sure what he was expecting to see. He was taken aback to find you in the bath, neck deep in bubbles with a few candles lit. You smiled weakly at him, he noticed the dark bags under your eyes, you looked exhausted.

"Honey, why are you in the bath at two in the morning?" He asked gently

"Your baby has decided that we don't sleep at night" You replied quietly

He knelt down next to the tub, a careful hand cradled the back of your head as he pressed his lips to your forehead. You let out a contented sigh. He knows how you worry when he's gone. His other hand dipped into the water to caress your swollen belly.

"Why don't we get Mama to bed, huh little one?"

Jack helped you out of the tub and into a nice fluffy towel before ushering you off to bed. He quickly put out the candles and then followed you, only to find you mostly asleep already. He chuckled to himself before sliding into bed next to you. His arm was slung around you, his face buried into your hair.

Jack always felt guilty coming home this late, but you were always glad to fall asleep in his arms again.

[replaytech]

I’m not saying that I could fix him but yes I am saying that I could fix him

[moonpascaltoo]

JACK DANIELS / AGENT WHISKEY

╰┈➤18+ none of these stories belong to me! this is a masterlist of all agent whiskey stories i’ve read and reblogged! just thought it would be nice to have them all in one spot! (if your fic is on here and you wish not to be, please let me know!) some will have summaries if provided <3

MASTERLIST • PEDRO PASCAL CHARACTERS • 06/24/28

@fuckyeahdindjarin ✰ Palomino Unable to get a refund for a week-long horse-riding pack trip you'd booked with your ex, you decide to go solo. As it turns out, a rebound with a cowboy named Jack while traversing the wild landscapes of Wyoming might just be what you need. (literally can not stop thinking of this series)

@iamskyereads ✰ salty caramel You hate him, you really do. During a mission Agent Whiskey eats a candy laced with a dangerous poison, and you’re the only one who can save him.

@ezrasbirdie ✰ cupcake Jack Daniels, lead used car salesman at his dealership, has a crush on you, the pretty receptionist. It's too bad he can't get out of his own way. Luckily for him, you have patience and a soft spot for shy cowboys.

@bubble-tea-bunny ✰ hello, nurse

@wardenparker ✰ angst request

@fooled-around-and-fell ✰ social cues

@creedslove ✰ heartless he was ready to give you the world, except one thing: be the father of your baby

@freelancearsonist ✰ in our ivory tower You enjoy the view from the top with your boss.

@haylzcyon ✰ picking locks part 2 A rough day ends with a broken key inside your front door. Local locksmith and acquaintance Jack Daniels comes to your aid - assisting in more than just picking the lock. 

@punkshort ✰ hot chocolate You lead a quiet, boring life in a podunk town, but when a certain secret agent stumbles into your world needing your help to catch a criminal at the local carnival, your quiet little life changes forever.

[backtothefanfiction]

Please Don't Leave Me | Agent Whiskey x Reader

Summary: The mission goes very wrong.

Warnings: Injuries and angst

Word Count: 1K

A/N: just a quick writing challenge for myself based around the prompt please don't leave me. I put a bunch of characters into a generator and Jack came out and it was honestly the easiest little story to create in 20 minutes. Enjoy.

There’s a reason you should never mix business with pleasure and it’s because of moments like this that actually remind you why.

It was supposed to be a simple mission. In and out with time for a good night at the hotel after. Just you and Jack doing what you do best. You had been working on and off together for five years now. Screwing each other after missions to let off steam for almost equally as long. Everyone told you not to do it. All the other girls in the office who had ever been seduced by him and left flapping on the shore when the tide went back out; warned you to stay away. But you were sure you could handle it. Told yourself it was just sex and that you wouldn’t fall in love. But he knew how to play the game. Knew how to win you over every time and lull you into a false sense of security to the point you thought, maybe he did care. Maybe he did love you back. But that look in his eye right now as he stood in the doorway, flash drive in hand ready to make a run for it whilst these brutes did everything they could to keep you down.

You hadn’t worried at first, but then you took a bullet to the shoulder and god damn if that didn’t hurt to the point you just wanted to hide in the corner and cry; but you couldn’t. You were a tough badass woman who had trained and worked too damn hard for this job to not keep fighting for the sake of the mission.

You really couldn’t blame him when he gave you that apologetic look and said, “Sorry Darlin’, it’s nothing personal.”

“Don’t leave me!” you had called out desperately. He was your back up after all. Without him there was no barrier between these men and yourself. Who knew what they would do to you. Kill you most likely, but when- and after what torture. “Jack! Please don’t leave me!” But he was gone.

Fuck! Fuck! Fuck! Fuck! Fuck! 

Your arm smarted, but you continued to try and punch your way out. 

It was no good. Although some of them had run after Whiskey, many of them continued to gang up on you. You were on the floor now, arms held up protectively to your head, body curled tightly in an attempt to protect your vital organs; but it was no use. They kicked and they kicked- one thud after the other against your body. You should have been focusing, but what was the use. So your mind wandered- back to him. Every tender soft word said between crisp white hotel bed sheets. Every tender kiss. Every “it’s only you kiddo.” And he still left you behind.

There was a resounding bang! Followed by another and another. The kicking stopped. Your body started to relax as you opened your eyes to see him there in the doorway, a smoking gun in each hand. “Now fellas!” He called out into the room and you looked around the room at the men in their shitty black suits, all lying on the floor nursing various shot wounds. None of them instantly fatal, but still deadly enough. All hitting vital organs that would bleed out quickly, but not enough that they wouldn’t be able to listen to his lesson first. “Is that any way to treat a lady?”

You glowered at him when he finally locked his eyes on yours. He quickly holstered his pistols before rushing over to you. “Now you didn’t think I was actually gonna leave ya, did you?” You groaned as his arms reached around your body and lifted you from the floor.

“The drive?” you asked, your voice raspy.

“I handed it off to Ginger.” He said as he carried you from the room.

“Wait? Ginger’s here?” you groaned.

“Hey, rest now. Don’t worry, I’m gonna get you out of here.”

That was the last thing you remembered before your vision went black and you went limp in his arms.

—---

“What happened?” You asked as you woke up in the medical bay two days later. To your surprise, Jack was sat in a chair beside your bed reading some rodeo magazine. 

He quickly closed it, putting it down in his lap, before leaning across the bed, reaching for your hand.

“I’m sorry,” he said earnestly. “I thought I would lead them away, but clearly not enough of them.” You remained quiet, both slowly recalling the events that left you feeling black and blue, but also analyzing the pain in his eyes. “I called for evac the moment I left the room. Ginger said she’d seen everything through the glasses and was already on the way. Champ told me to get the drive out first. I had to do it. I couldn’t let on…” his voice trailed off.

“You couldn’t let on what?”

“I know I’m not supposed to do shit like this. You know. I told Champ I wouldn’t- fuck!” he hung his head in shame. “I didn’t think…”

“You didn’t think what? Didn’t think what Jack?!” you pressed him.

“That I’d actually care about you!” He snapped. “That I’d fall in love with you.” His words stunned you. “I compromised the mission today.” he said with shame.

“Yeah, but you got it out. You did the right thing in the end.”

“Yeah, but it should never had come to that.” He grunted. “I saw you in that dress and I just became distracted. It should never have come to that.” He repeated himself. 

In the silence that fell, you finally realised what he had said. “You love me?” you questioned tentatively.

He looked at you confused. “After all that, that’s the thing that you take away.” He paused for a moment, if only to gauge your reaction. “Of course I do. Knew it the first moment I met you. All smart mouth and attitude and…” his voice trailed off as he got lost in you. You squeezed his hand encouragingly. “I promise I’ll never actually leave you, okay? I’ll always come back for you.”

And he always did. Until the Poppy Adams case. Until he would never come back to you again.

[shots-of-whiskey-and-wilson]

a conversation with jack

a fluffy agent whiskey x gn!reader imagine

SUMMARY: jack's reaction to you talking about something you love :)

WARNINGS: none! literally just pure fluff here.

WORD COUNT: 126

being extra excited while you’re telling jack about something, maybe about your day or something you just really really like while he listens intently and makes heart eyes and smiles at you the whole time

mid-sentence he leans forward and gives you a kiss on the forehead and it catches you off guard and you freeze mid-sentence as your heart rate spikes

he looks at you expectantly as if to say “keep talking, i’m listening”

you tell him you can’t remember what you were saying and he chuckles and just thinks it’s so unbelievably cute

he politely reminds you where you were and it takes you a few seconds to recollect your thoughts and you’re blushing and smiling your way through the rest of your speech

that's all :)

@iamthatonefangirl

[iiconicxpersona]

National Anthem

retired!Agent Whiskey x latina!Reader

"Red, white and blue is in the sky.

Summer's in the air, baby, heaven's in your eyes."

Summary: it's the fourth of July and Jack is enjoying the holiday with reader and their fraternal twins at his ranch house.

Warnings: fluff, mentions of smut towards the end (18+, minors dni), age gap (reader is 30, Jack is 48), no use of Y/N, y'all just prepare yourselves for papi Daniels.

Word count: 2.7k

“Jack! Jimmy! The hot dogs are ready!” You called out while carrying the large plastic Tupperware full of freshly grilled hot dog links to the picnic table.

Just a couple of steps behind you was your daughter Rosé counting her steps as she skipped cheerfully to the table with the plate of warm hot dog buns in her tiny, yet firm, grasp.

Meanwhile on the other side of the ranch, Jack stayed knelt next to his young spawn and continued working on the mechanics to the pyro machine. “Jimbo, how ‘bout you go make us a couple of hot dogs while I finish setting up the fireworks?” Jack smiled lovingly at his son.

“Okay papa! Can we watch them on the trampoline like last year?”

“O’course son. Now go on and tell your momma and sister I’ll be there in a sec.”

Once Jimmy sprinted in your direction off in the distance, Jack took a moment to watch his family join together with smiles on their faces and love in their eyes.

Never in a million years did he think he would be given a second shot at having a family. After losing his sweetheart and their unborn son a few years prior to meeting you, Jack was sure that was it for him. Despite being involved in random one-night stands for a mission or to just fill a lonely night, life just wasn’t worth living without her. Jack would often find himself wishing the next mission would be his last just so he could be reunited with his family again, until you came along.

---

Both Jack and Agent Tequila were on their next mission of tracking down another famous musician at a rock concert. The two separated into the crowd and Jack bumped into you by accident, spilling your beer all over your new outfit.

“¡Ay qué chingas! Thanks a lot, bud.” You groaned and furiously wiped what was left of the beer off your blouse. 

“My apologies, sugar. Didn’t see you there.” Jack pulled out a napkin from a hidden pocket inside his leather jacket and handed it to you.

You reached to snatch the napkin from his hand but the sudden little static shock you felt when your skin touched his own made you finally look at his face. Your anger immediately melted away only to be replaced with sudden nervousness and a smile that couldn’t disappear no matter how hard you tried.

“No, i-it’s fine. Accidents happen, right?” You giggled.

“Right.” Jack chuckled nervously. ‘My god, she’s beautiful.’ He thought to himself.

In that moment it seemed time itself had frozen because neither you nor Jack felt the strength to move. Your hands were still connected with only the napkin in between. The rest of the arena that was still filled with people fell silent. Even Agent Tequila practically screaming in Jack’s hidden earpiece couldn’t break his trance from you. The friends you arrived at the concert with had disappeared to their seats the moment Jack bumped into you, knowing damn well he was exactly your type.

“My name’s Jack.” He finally cleared his throat, bringing you both back to reality. “Can I buy you a drink, sugar?”

---

Five years, one marriage and a set of fraternal twins later, Jack had a life worth living for again.

“Como la flooooorr. Con tanto amoooooorrr. Me diste túúúúúú. Se marchitóóóóó. Me marcho hoy. Yo sé perdeeeerrrr;” You and Rosé sang along to the music dramatically as she stood on top of the picnic table to give her best Selena impression. Once the music started and Jimmy joined in on the fun, you put Rosé back down safely on the soft grass before the three of you began dancing Selena’s dance moves.

Jack couldn’t hold back a smile if his life depended on it. He cherished these family moments more than anything in the world. To think he would’ve missed out on this if he had chosen not to retire the moment you found out you were pregnant with the twins four years ago. There’s no telling where he would be right now, but he was certain every day that you, Jimmy and Rosé saved his life.

Once he had set up the last firework, Jack leaped to his feet and turned to anxiously meet his small family on the other side of the ranch. Jimmy was already sitting down and stuffing his face with a hamburger while you and Rosé were too occupied dancing to the music until her eyes met Jack coming from a distance. “¡Papi!”

You watched with a smile as she ran as fast as possible into Jack’s embrace, leaping into his arms before he picked her up and spun her around. “Hey there princess! Looks like you and your momma were havin’ fun.”

Rosé quickly nodded. “Uh-huh. Are we gonna watch the fireworks now?”

The sun had set enough to where the sky turned a bright shade of orange-ish pink, still too bright for a firework display.

“Not yet, moonshine, we gotta wait for the sky to get just a lil' bit darker. Maybe once we’re done eatin’.”

“Okay papi.”

Jack kissed her temple making an audible smooching sound and she giggled in his arms as his mustache tickled her skin.

“Mami, I’m thirsty.” Jimmy mumbled with a mouth full of his hamburger. Mustard and ketchup smeared on either side of his mouth.

You chuckled and reached deep in the bottom of the cooler to get him a bottle of root beer. Just like his daddy with an actual beer, Jimmy refused to drink his root beer if it wasn’t ice cold.

“Here you go, mijo.” You placed the bottle beside his plate and grabbed his napkin to wipe the condiments off his cheeks. “And remember don’t talk with your mouth full. It’s dangerous and bad manners.”

Jimmy nods while swallowing his food. “Yes ma’am. Gracias, mama.”

 “De nada, mi amor.” You smiled at your son and kissed his now clean cheek. Gently ruffling his dark hair and turning to meet Jack by the cooler once he sat Rosé down.

“No kiss for me, sugar?” He smiled at you.

“There’s always a kiss for you.”

Jack gently grabs your hand to pull you into his arms with your own snaking around his neck, closing the gap between you two as much as possible until your lips met in a tender kiss. You couldn’t help but giggle at the feel of his facial hair scratching at your skin, but even that couldn’t distract you from feeling his hands slowly slide down and grasp at your behind over your red sundress.

A slight gasp turned chuckle escaped your mouth at his grip only for Jack to instantly swallow the sound with a deeper kiss.

“Jack,” you teased in between kisses. “The kids are watching.”

Both you and Jack opened one eye and turned your heads slightly to see the twins looking at you two in disgust, turning to each other to point their fingers to their throats and make gaging noises.

“Ew! Dad’s touching mama’s butt!” Jimmy gagged.

You and Jack stood there laughing at the reaction of holding each other. “Son, one day when you’re older you’re gonna love someone like I love your momma and you’ll understand.” Jack said.

“What about me, papi? Will I understand when I grow up?” Rosé chimed in.

You raised your eyebrows and looked directly at Jack, trying so hard to hold back a laugh when you felt his hands slide to your upper back while shaking his head at his daughter’s question.

“No, moonshine, you won’t. Daddy’s not letting any boys touch you, ever.”

-

The twins had finished their dinner before you and Jack could even sit down to enjoy your first plate of freshly grilled food. Their anticipation to watch the firework display became so thin that Jack resorted to giving the twins each a sparkler to keep them entertained for the time being. Once you finished eating, you and Jack cuddled next to each other on the picnic table bench and watched both the children and the sunset while drinking a beer.

Tennessee Whiskey began playing on the speaker, making your heart melt at the memory of your wedding night. It was the song that played during your first dance with Jack as husband and wife.

“May I have this dance, sugar?” Jack stood up and held his hand out for you to take.

“Anytime, cowboy.”

Once your hand slid in his, Jack slowly raised it up to peck the back of your hand, keeping eye contact with you and making you blush. It amazed you how even after five years Jack still knew how to make you feel like a teenage girl in love. A mutual feeling for him as well. For a man pushing fifty-years-old, you made him feel young. Hell, in his mind you’re still young at pushing thirty-one. To this day he can’t seem to figure out exactly what you saw in him the night you met. A pretty young thing like you deserves to be with someone like his former partner, Agent Tequila, or someone closer to your age like Eggsy. No. Instead, you fell for him: the whiskey drinkin’, pussy eatin’, southern playboy spy Jack Daniels. God only knows what he did right in his life to deserve you, you’re far too good for him, but he thanks the man up above every day for his little family.

“You’re as smooth as Tennessee whiskey. You’re as sweet as strawberry wine. You’re as warm as a glass of brandy, and honey I stay stoned on your love all the time.” You and Jack sang along while swaying to the music and staring lovingly into each other’s eyes.

“Can you believe it’s been four years since we got married?” He asked.

“I know.” You turned your head to look at the children playing off in the distance. “Ay, how time flies.”

“And you’re still just as beautiful.” Jack smiled, never taking his eyes off you.

“Oh Jack.” You blushed and smiled back at him.

“Papi! Papi! It’s time for fireworks!” Rosé called as she and Jimmy ran as fast as their little feet would allow towards the trampoline.

Time really does fly fast when you’re having fun. The fireflies were already making their presence known off in the distance and the once orange-pink sky had turned a darker shade of blue.

“We’re coming, moonshine!” Jack intertwined his fingers with yours, picking your hand back up to connect with his lips once more.

As you two walked hand in hand to the trampoline, you rested your head on his shoulder and smiled while you watched Jimmy and Rosé jump and laugh amongst each other. At the same time, you were being careful not to smudge any makeup on Jack’s white button-up shirt.

Even in retirement Jack always wanted to look his best, mostly for you. He was almost never just a t-shirt and sweatpants kind of guy unless it was for bed. Before Jimmy and Rosé were born, Jack preferred to sleep naked or at least in boxer briefs, but that all changed a few months back when thunder scared the kids awake. Just as you and Jack were about to start making love, the kids had burst into your room and forced their way to sleep in between the two of you while you both desperately tried to keep yourselves covered and awkwardly stared at the ceiling all night. After that, you both agreed to start locking the door and not sleeping naked anymore on the nights you weren't 'busy'.

You chuckled out loud at the memory.

“What’s so funny sugar?”

“I was just remembering what happened on Valentine's Day. That’s all.”

Jack chuckled, needing no further details. “Crazy kids. Next time we’ll get your momma to babysit.”

-

“Mama, I wanna sit with you.” Jimmy said as he waited patiently for you to settle yourself on the trampoline.

“Okay mijo. C’mon.” You smiled and patted your lap.

He carefully made his way over to sit on top of your lap while Rosé jumped in the middle as Jack was trying to get comfortable.

“Careful moonshine. Daddy ain’t young anymore.” He chuckled before finally sitting upright.

“Sorry papi.” She giggled before landing her last jump with her whole body and rolling next to her father. He didn’t hesitate to let her sit on his lap and placed the large remote down in front of them.

The four of you took turns pressing the buttons for each firework until the kids became too distracted and watched while Jack took over the controls with one hand. The other snuck up behind you and gently caressed your back and exposed shoulders.

“¡Mami, mira los fireworks!” Jimmy smiled and pointed up at the display.

“Sí mijo. They’re beautiful, right?”

“Just like you, mami.” Jimmy looked up at you and smiled.

You looked down at him and gasped as your heart melted. Smiling and hugging him tighter while you placed multiple kisses to his temple. He giggled and squirmed in your arms. “Eres el hijo de tu padre.”

You both looked at Jack with big smiles. He winked and returned the smile to his son. “Attaboy, Jimmy.”

-

The rest of the display was spent staring up in awe and comfortable silence. It didn’t take much longer before the fun finally caught up with the twins as they yawned and rubbed their eyes to stay awake for a little longer, but it seemed like the more they tried to fight it, the sooner they fell asleep.

Once the display was completely over, Jack carefully slid off the trampoline and helped you down from the other side. He handed you Rosé gently before picking up Jimmy in his arms and letting you lead the way back into the ranch house. You both changed the kids into their pajamas before tucking them into bed, giving them one last peck on the forehead and turning on their nightlight.

“¿Papi?” Rosé mumbled, her eyes trying to open as she looked for Jack.

“Yes moonshine?” He smiled at her.

“Can we go horseback riding tomorrow?”

Jack chuckled and sat down next to his daughter, gently rubbing the top of her head. “We’ll see, moonshine. Okay? For now, just get some sleep.”

Rosé smiled and nodded in his direction. Jack kissed her once more on her forehead as she yawned with her eyes fluttering closed.

“G’night, baby girl.”

“Night papi.” She mumbled before finally drifting into a deep sleep.

-

You were brushing your long dark hair over one shoulder in the master bathroom when you felt Jack snake his arms around your waist and attack your neck and exposed shoulder with light nibbles and kisses.

“Are the kids asleep?” You chuckled as you fell back into his embrace, tilting your head to the side to expose more of your neck.

“They sure are, and I already locked the door.” He whispered seductively in your ear.

“Well, what should we do now, cowboy? I’m not the least bit tired.” You teased.

Jack growled and sunk his teeth into your shoulder causing you to moan. His hands claiming your body with one hand pushing down the top of your sundress to massage your bare breast while the other gently teased your clit over your clothes.

“Whaddya say we make another baby?”

You couldn’t hold back your smile at his suggestion. He didn’t know this yet, but you had been thinking about having another baby lately. The only reason you kept that to yourself is because you weren’t even sure he wanted more kids, so to hear him say this made you excited in more ways than one.

“You want another baby?”

“I do. Seeing you with the twins today got me thinkin’ about it.”

You grasped at his hair and pulled his head back far enough to where your lips connected with his in a passionate kiss.

“So whaddya say, sugar? Wanna ride into the sunrise on a real cowboy?”

“As long as I get to name the baby this time.” You teased.

Given Jack’s history, you thought it would be nice to give him the opportunity to name the twins. However, with his obvious sense of humor that you adored so much, you should’ve known he would pick alcoholic beverages to name them after.

You shrieked and giggled uncontrollably as Jack spun you around and picked you up, wrapping your legs around his waist and holding yourself up. Kissing each other passionately as he carried you to bed.

--------

Spanish translations:

¡Ay qué chingas! - Oh what the fuck!

“Eres el hijo de tu padre.” - You are your father's son.

A/N:

I hope you guys enjoyed this! It's my first time writing for Agent Whiskey Jack Daniels. I was planning to have this out sooner but I literally got the inspiration while listening to Lana Del Rey and watching the firework display on the fourth lol. It's still July so it still counts.

[creedslove]

HEARTLESS 💔 - PART TWO

Agent Whiskey (Jack Daniels) x f!reader

Summary: much to your horror, Jack shows up again and asks you to see his son one more time

(This is the second part of the one shot HEARTLESS 💔)

Warnings: angst, hurt, a little bit of fluff because Wyatt is super cute, mom!reader, asshole!jack, mentions of abortion

A/N: besties honestly i don't even know why I am doing this, while i was writing, i realized i don't like this suffering at all 😭 i think agent whiskey is such a dad and husband material and he's so handsome and sexy and he would be so affectionate and would give the best orgasms and cuddles in the world but i can't stop myself from pouring angst into people's lives 😭

1.7k words

Wyatt whimpered as you sent him to bed. He wasn't sleepy at all and he wanted to talk about all the fun things he'd seen during the day. He loved to run freely through the green fields, he liked scaring away the chickens, petting the horses and watching the baby pigs. 

But his favorite part of the trip was the cowboy. He was so cool, Wyatt spent the rest of the day blabbering about him and asking you all kinds of questions. He was so innocent and pure, your heart shattered each time he would look at you with his little curious eyes and shoot you another question about the mysterious figure. 

Though he wasn't mysterious at all. It was his dad, not that Wyatt knew about it, you figured he was just too little for that, he was still your baby. He wasn't even four yet and he had to live his little life with only his mama as he'd been rejected by his dad since he was just a small little bean in your womb. 

You saw his begging, pleading eyes, just like Jack's and felt your heart clench, there was nothing he would ask you and you would say no. You sighed and pulled Wyatt into your lap "fine baby boy, if you don't wanna sleep now, then come cuddle mama!!!" You tickled his tummy and made him squeal and snuggle you. 

You sat comfortably in his small bed and let him sprawl over you, loving how happy he got. You ran your fingers through his soft curls and pecked the top of his head. He was waiting for a bedtime story as you always told him one, but this time, he wanted a cowboy story. You swallowed and took his tiny little hand into yours, stroking it gently 

"You really liked that cowboy, didn't you?" You asked your son and earned an excited nod "alright… let mama think…" you closed your eyes and thought of any story you could tell him, however, you didn't know any cowboy stories… the only cowboy story you knew was your cowboy… but that was a long time ago, when he was yours and you were his. 

Still, Wyatt looked up curiously, waiting to know what you had to tell him. 

You swallowed and began telling him the story about your cowboy. 

With a few modifications, some sugar coating and softness you told your son about your first encounter with the cowboy and how it made your heart melt. You told him how you two hit off and how the cowboy had a real nice job of fighting bad guys and saving the world, you couldn't control the pride in your chest as you saw the joy in Wyatt's eyes, loving that storytelling so much he often gasped and giggled.

And going down the memory lane, you managed to make your son sleepy, as he blinked his tired eyes and yawned "night night mama" he whispered before falling asleep.

You smiled at yourself and covered him up, silently walking out the bedroom and walked around your dark, empty apartment. Your mind wouldn't stop replaying the images of your day, your sudden encounter with Jack, something you really thought wouldn't happen soon. He looked handsome, like he always did, smelling great and if you didn't know any better, you would probably fall for his trap again, if he flashed you those beautiful eyes, gave you a grin and said any dumb pickup line with his accent. There was just something so attractive about him, and you had fallen for him once, but you wouldn't make the same mistake twice. 

You thought about how he hugged Wyatt, it didn't even seem the same man who rejected him, who simply broke things up with you once you found out you were pregnant. One day you were deeply in love with each other, and the next he was suggesting you get an abortion. It was something you just couldn't handle, you couldn't accept and just like you were alone in the world with your baby. 

When the doorbell rang, your heart clenched once more, you didn't even need to check, you just knew it was Jack. 

You dried your eyes and sighed, walking to the door and opening it for him. 

Jack stood there, looking almost as unsure as you did. He was holding his hat in hands and watched you hesitantly. You could tell he was looking for words to say, but nothing came out. 

"Come on in, Jack" you said and let him step inside, closing the door behind him and letting him get familiar with the place. 

Jack looked all over the place, he had never been inside your home and it hurt him how it looked homey and cozy. No matter how much he spent on decoration at his own place, he could never get it like that. 

He carefully watched the picture frames, so many photos of a life that could have been his as well, but he chose not to be a part of it, it didn't even matter his reasons now, the result was there: pictures of you on your baby shower, pictures of the first time you held Wyatt in your arms, his first birthday, his first day at daycare, mother's day… all those precious, beautiful moments, and absolutely no trace of Jack. 

"It's good seeing you again, Y/N… you look even prettier than before, sugar" the man turned to you, his voice was small and though his cocky way of speaking wasn't there, you couldn't believe the first thing he told you in years was a cheap attempt of charming you.

"What do you want Jack?" You folded your arms and stared at him, you didn't want to play games nor beat around the bush.

"I wanna be around my boy" he replied to which you scoffed and shook your head 

"Your boy? The same one that you rejected when he was nothing but a tiny little bean in my womb? The one you insisted on me getting rid of? I don't think so, Jack" 

He sighed ashamed of his past and took a step closer, to which you immediately took a step back, showing him you wanted nothing but distance from him. 

"I know what I did, and I know how awful it was, but after I saw him today… I realized I can't get away… please Y/N" 

"You think you can just walk in and demand to see my son? After you abandoned us? He isn't a cute puppy, Jack! You can't just find him sweet because you spent five minutes with him and think you can bring your shit storm into our lives. That's not how it works. I don't want him around you, because you are a mess and you will break his heart just like you broke mine!" 

"I didn't abandon you, Y/N. Don't be unfair with me!!! All these years, I followed the two of you from afar, I provided you with money and other things you needed.. hell, who do you think managed to get you this apartment lease?" He raised his eyebrow getting on the defensive "I wanna do it the right way, but if you make things hard, I'll get a damn lawyer and you will have to fight your cut ass off to pay for one yourself because I won't rest until I have my boy with me!!!" 

You knew Jack, he wasn't bluffing. He was the kind of man who got everything he wanted, but you just couldn't accept he could walk into your home and have a claim on your son after everything that happened, even threatening you to find an attorney. 

"It's not the same… money helps but it is not everything, where were you when I was pregnant and alone? When I needed someone to hold my hand and tell me things were fine? Where were you, Jack? When Wyatt had his first fever and I didn't know how I could help him calm down? When he said his first words? When he took his first step? You missed it all out, even if you had given me your whole fortune, nothing pays the memories you lost!" 

"I just want to see my son, nothing else Y/N… I don't want you, I don't want our relationship back" he said knowing it would sting you, he couldn't help but make his intentions clear. You two would never be together again, he knew that because you would never take him back, so he thought it was easier to just convince himself of it beforehand. 

You, on the other hand, could never be with him again, even if he hadn't done the things he did, there was still no way you could compete with a ghost, you just thought it was easier to convince yourself Jack never stopped loving his first wife and he never would, so your relationship was nothing but an adventure. 

You didn't want him to see the tears in your eyes, you didn't want to show how weak you felt at that moment. 

Before any of you could say anything else, tiny footsteps interrupted the argument that was about to explode. 

"Cowboy!!!" Wyatt said excitedly as he still rubbed his tired eyes but ran to Jack, giggling as he was so easily lifted up into his arms. The toddler was so affectionate, he just wrapped his small arms around his neck once more and rested his head against Jack's shoulder "miss you cowboy!" he giggled happily and snuggled.

You bit your lips and did your best not to cry, but it was pretty much impossible, you couldn't understand why your son liked that man so much without even knowing him. It wasn't fair to you, and you were ashamed to realize you felt jealous. 

Jack, on the other hand, felt his heart fill with pure joy for the first time in ages. He quickly kept Wyatt in a warm embrace, loving the smell of his baby shampoo and how cute his PJs were. 

His hand rubbed up and down his back as he sat on the couch, letting him relax completely and in a matter of minutes, Wyatt was back in dreamland.

You hated how easy it was for Jack to make your son fall asleep, and how much they already liked each other, it hurt you so much, but you were determined not to let that man get near you again.

_____

A/N: ¿Malparido, no?

[atinylittlepain]

Ginny my love I have an “I got love in my tummy and a tiny little pain” request - Whiskey au where he teaches his little boy how to lasso 🥹

aw, my first whiskey fic, and it's a sweet one :')

Like Father, Like Son

agent whiskey x f!reader (& their boy)

no warnings on this one, but like, be 18 or older pls

............................

“I’m telling mom.”

“You tellin’ me you don’t wanna learn how to do this?”

“...no.”

“Well then, what your mama don’t know ain’t gonna hurt her. But that don’t mean you can start swearing up and down the streets either, she’d probably have my ba– my head if you did, understand, son?” 

“Yeah, dad, I understand.” His boy rolls his eyes, eight going on eighteen already, and Jack can’t help but ruffle his hair a little bit.

“Atta boy, now why don’t you watch me for a turn and I’ll talk you through it, and then we’ll have you give it a go, that sound good?” His boy nods, taking a few steps back as Jack unfurls the lasso in his hands. 

“Now, the thing about lassoing is, it ain’t about throwing it. This ain’t like baseball, ok? You wanna deliver the loop to your target.” Jack lets his loop up, starting to let it swing over his head.

“It’s all about waiting, son. You’ll feel it after working up some momentum and that loop is tugging out of your hand, and that’s when you wanna release, like so.” He lets the lasso go, circling it around the old milk pail he set up for target practice and pulling the slack tight, his son letting out a little sound of wonder that makes him grin. 

“Alright, you wanna give it a go now?” 

It takes him a few false starts, getting tangled up in the lasso before he can really get the loop swinging over his mop-haired head, but when his son does let the loop go and snares his target just right, Jack can’t help the whoop he lets out, pumping his fist in the air before gathering him up in a tight hug, much to his son’s jaded dismay.

“Hell yeah! That’s what I’m talkin’ about! Gonna have you wrangling longhorns in no time.” 

“Dad, you’re smushing me.” He lets his boy go with a chuckle, holding him by his shoulders to get a good look at him.

“Too cool for your ol’ dad already, huh? S’okay, son, reckon I was the same way when I was your age. But I’m so proud of you, my boy. You wanna give it another go?” His boy grins at that with an enthusiastic nod.

“Hell yeah!”

“I better not be hearing what I think I’m hearing out there!” Her call has both their heads whipping around to the house, and sure enough, she’s leaning in the doorway, the crooked smile on her lips telling him that she’s only half serious.

“Well I have no clue what you’re talking about, sugar. Just having some good ol’ fashioned fun out here.” She pads out to them, barefoot in the grass, and Jack’s heart is fit to burst watching her lick her thumb before swiping it over their boy’s cheek, wiping away a smudge of dirt despite his protests. Jack pulls her into him by a belt loop, stealing a smacking kiss that has her laughing and their boy gagging dramatically. 

“Hey now, none of that. You wanna show your mama what I taught you?” 

“He– I mean, yeah.” With that, their boy jogs over to the old milk pail to collect the lasso. She meanwhile fixes Jack with what is an attempt at a stern look, though she can barely get her words out around a disbelieving laugh.

“If he ends up talking like a truck driver, I’m blaming you.” That makes him laugh, pulling her a little closer and landing another kiss to her pursed lips.

“Don’t worry about that, sugar. Our boy’s gonna turn out just fine.”

[wildemaven]

Enjoying Christmas with Jack on the ranch

[illfoandillfie]

farmer!Jack au where when he has to get up super early sometimes (like 4am) to help him wake up he likes to fuck you, but you don’t want to get up that early so he has permission to do it anyway…

Blurb Advent 2023: Day 22

😈😈😈

Warnings: somnophilia, p in v sex, unprotected sex, reference to oral and anal as well

You’d never imagined yourself dating a farmer. Not that you’d have ever totally ruled it out but rural romances were your least favourite sort and you preferred working behind a desk to out in a field. And the thought of having to do anything at the crack of dawn was, frankly, against human nature. You simply weren’t a morning person and couldn’t picture yourself on a farm. But then, you’d met Jack and somehow you’d fallen in love with one. He loved fresh air and the satisfaction of fixing things with his own two hands. And while he said he liked sleeping in too, for him that meant still being abed at 6.30 in the morning. It was something of a miracle that you worked so well together but it was undeniable that you did. Of course, it helped that he only rarely expected you to join him when he rose before the sun. He had a couple of hired farm hands that helped him get through the work, and you had your own job in town to worry about. So it was only on very special occasions that he asked you to rise with him.  

Earlier in your relationship, just after you’d moved into his ranch, he had tried to convert you to the wonders of a 4 AM start. He’d tried to play up the romance of it, providing a thermos of coffee as you watched the sun rise and things like that, but it was hard for you to feel the same. It was still 4 AM. Then, when romance didn’t work, he tried bribing you with sex. Not the worst idea in theory, but in practice sex just made you sleepy. You’d just roll over right after and drop off again. And it was the same story no matter what position or form the sex took. So, rather than a good start to the morning, he was just momentarily interrupting your sleep and tiring you further. And, eventually, he had to accept you would never feel the same about early starts as he did, which would have been easier if he hadn’t conditioned himself a little.  

In the weeks he’d tried his sex tactic, he’d discovered he quite liked starting the day with a good fuck. Getting off put him in a good mood. Sex helped shake off sleep and get his blood pumping and his heart racing and by the time he’d cum he was ready to get into the day. Better than coffee he’d said to you whilst trying to make you see things his way. Of course, it became clear you disagreed and he lost his newly discovered favourite ritual. Mornings became harder than they ever had been after that. It just wasn’t the same waking up on his own. His arguments became less about you joining him in his work and more about convincing you that a brief interruption to your sleep, just long enough for a good fuck, was good for the relationship and good for you.  

In the end, you’d given in. Not entirely - there was no way in hell you’d get up that early without a very good reason. But you’d come to an arrangement that suited you both. As long as he didn’t expect you to wake, Jack could fuck you at whatever time he wanted. He’d been unsure at first. He was a gentleman for one thing, he’d been raised not to touch a woman who wasn’t conscious enough to ask for it. And, once you’d gotten him over that hurdle, he’d become concerned that it wouldn’t be as good if you weren’t actively participating. But he’d agreed to try. So, you went to bed without underwear on to make it easier on him, and he’d discovered so as he gently parted your legs, very mindful of what might wake you. He soon found out you were responsive even while asleep. You made little sighing sounds and small moans as he touched you. You got wet as easily, if not easier, than when you were awake. And your body seemed to react innately to his touch, legs falling open with minimal guidance, pussy clenching as he pressed into you. He came fast that first time, mind blown by how easy it had been to do. How well you’d taken him without even thinking about it, how he’d still been able to make you cum, how the risk of waking you made him feel naughty and dirty and so very hard.  

He experimented a bit – tested out how much you could handle before you woke, tested out how you reacted to being eaten out and having your ass fucked. The first was fun but he preferred doing that when you were able to fully appreciate it, the second was also enjoyable but so much more effort and harder on you. In the end he decided it was easiest and best if he just stuck to using your cunt. Which suited you perfectly. Occasionally you’d wake up with him thrusting into you, groping your tits, shamelessly and somewhat possessively staring at you. Sometimes you’d wake alone with a mess of his cum between your thighs. It was hard to decide which was hotter. You loved seeing him of course and being fully aware of what he did to you, but there was something very arousing about knowing he’d used you like some sort of sex toy, masturbated with your body while you’d been asleep. That he found you so irresistible he couldn’t keep himself from taking you. Sometimes waking with cum stuck to your skin and your cunt still wet from his touch, you couldn’t resist getting yourself off. Though waking in such a state was also a good extra push to get you out of bed each morning before you looked at your phone.  

And then there was the unforeseen side effect. There was one hole Jack wasn’t game to use while you slept, and frankly you were a little glad for that. But, because he couldn’t use your mouth in the mornings, he became extra excited by the idea of a blowjob at every other moment of the day. In fact, the routine somnophilia had only seemed to increase the amount of sex you were otherwise having. It was understandable for you since you didn’t always get off when he did, and even when it happened you had no memory of it. For Jack though it was obscene. He’d would wrap up his morning’s work and return to the house in time to meet you while you were getting ready. He’d invariably catch sight of the unmade bed, be reminded of how completely you’d given yourself to him, and be ready to go again. You’d have just washed one load off when he’d hop in the shower to give you another, or else you’d end up kneeling on the kitchen floor, licking the sweat from his cock while he groaned about how good you were to him. In the evenings he was more interested in using your ass since it was easier to do while you were awake, or else he’d want you to ride him and do some of the work for a change. You laughed the first time he said it but he’d meant it, laying back with his arms behind his head while you bounced on his cock. He’d eaten you out after though, until you were begging him to stop, as repayment for everything. 

Because he woke so early, Jack usually went to bed before you but even so, there were nights he still managed to convince you to warm him through the night. You’d go to sleep full of him, his hand resting over your cunt like he owned it. You’d cum like that a few times when the heel of his palm touched your clit just right. And you were never quite sure if it was accidental or intentionally to keep you wet and make you easier to fuck when he woke.