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baronessvonglitter · 3 months

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All Through the Night

Agent Whiskey x f! junior agent!reader

Word count: 4.4K

Summary: after it's made clear that you're not welcome as a Junior Agent for the Statesman organization, Whiskey takes you under his protection for an unforgettable night

WARNINGS: 18+ Only! Mature and Explicit, mentor/mentee relationship, forbidden relationship, vandalism, nightmares, 'only one bed', first time, oral sex (f receiving), unprotected p in v sex, no use of y/n

JACK DANIELS MASTERLIST | FULL MASTERLIST

When you're first introduced to your mentor Agent Whiskey, you're not sure if you'll get along with him. With others he seems friendly, casual, laid-back, flirtatious even. But with you he takes on a sterner tone, as if he's closed off, and from the moment you're paired up as mentor and mentee, he treats you with nothing more than solemnity. Throughout your training he doesn't praise you as you honestly wish he would, just gives a curt nod, arms crossed, mouth set in a firm line, eyes giving nothing away.

It doesn't really help that you come from a rival agency, igniting all kinds of rumors. None of the other trainees get close to you. You find it pointless to try to change their minds. You've been alone most of your life, so why try to make friends now? Especially when you're in competition with each other.

You rise through the ranks quickly, an apt pupil and adroit agent. With each test you pass with flying colors, you expect something more from Jack Daniels himself to show he's proud of your progress, even just a smile, a pat on the shoulder, but he remains as unmoved as ever.

The day comes when you're given your official agent name, and in a flurry of excitement you rush to claim yours, only for your expression to turn quizzical when you hear what your new alias is. "What the hell is a Gimlet?" you finally ask as you burst into your mentor's office.

Jack glances up at you quickly, obviously in the middle of an important call, and tells the other line he'll call them back. You pick up on the ghost of a smile that passes his lips before he catches himself and turns serious again.

"Sorry," you tell him. "Is everything okay?"

He nods. "Classified information," is all he says. But you see the look of worry in his eyes, the way he casts his gaze upon you, you can't tell if he wants you to stay or needs you to leave.

"Was Gimlet your idea?" you accuse him, trying to lighten the mood.

"Nope. Wasn't my idea." As usual your heart does a triple beat at the sound of his deep voice, the Southern twang. Lately you've realized you've developed a little crush on him, but your education and your training are paramount at this point in your life. You can't be thinking about him this way, even though it's a hard feeling to suppress.

Uninvited, you sit on the edge of his desk, waiting for him to command you to get off. He doesn't. "Sounds like a Lord of the Rings character.. Gimlet.." you do a raspy little monster voice, and Jack crooks his eyebrow, looking like he wants to explode in laughter. "Sorry we can't all be as cool as Whiskey," you grin. "Oh, see that frown? Now that's what I call a Whiskey Sour."

He glares at you with mock severity and you take this moment to try to mess with him a little, to get him to open up.

"No-go on the Whiskey Sour, got it. How about 'Ten Gallon'? 'Billy the Kid'? 'Butch Cassidy?'" Teasing him is so much fun simply because you know he's an easy target, and it's as close as you've come to flirting with him.

He sighs in defeat. "You're thinking of 'Gimli.' From Lord of the Rings."

You shake your head, a smile bursting onto your lips. "Nerd."

"You really want me to lose this fight, don't you?"

"You've already lost, Roy Rogers." You playfully flick the brim of his hat.

A noticeable blush shows on his face as he straightens his hat, and as he clears his throat he adjusts himself in his chair. "So. You're using all the western ones, huh?"

"It's on theme, wouldn't you agree?"

He holds back a smirk. "Don't you have a codebreaking class to be in soon?" He stands up from his chair, adjusting his the waistband of his jeans, inadvertently drawing your attention to that area. Maybe you're imagining it, but it looks as though he's trying to hide the bulge evidencing his excitement.

Reluctantly you take the hint, getting off his desk. "So you're not going to tell me what that call was about? Shouldn't I be in the loop?"

Jack looks like he wants to spill the beans, his lips part as if to speak, and you can't help but imagine how soft those lips would feel against yours, what the slide of his tongue into your mouth would taste like. "All I can tell you is we're bumping up security on you. It's one of those 'the less you know, the better' type of deals, sweetheart."

It's the first time he's ever used a pet name for you and it sends the butterflies in your stomach in a frenzy. "Are you sure?" you ask, taking one more step towards him.

You hear him exhale, his dark brown eyes flickering with doubt. The moment between you feels like it could change everything. "I'm sure," he says at last.

You nod and start to leave, glad that at least a little progress had been made in that you got him to crack a smile.

"It's a cocktail," he says, and you turn back to look at him. "A gimlet.. it's made with gin, lime juice, and sugar."

A smile grows on your lips. "Sounds delicious.. but I really would prefer something cooler like 'French 75' or 'Absinthe.'"

"Adios, Junior Agent Gimlet.." Arms crossed, he signals it's time for you to skedaddle.

As you leave he can't help looking at your ass, the gentle sway of your hips. He's imagined all kinds of things since the day you were partnered with him, and he's managed to sequester those feelings from the way he's supposed to treat you. Times when you sought him out for his esteem, his recognition, he only fractioned it, hoping to keep the boundaries between you, make it easier on him to deny what he feels, but it's only made it worse.

Truth is, he's not only proud of you, but you've managed to get to him like no one has before. It's not just a protectiveness he feels towards you, but something deeper has grown. He hates to admit this to himself. And now, just before you made your animated entrance into his office, he was informed about a problem the agency was facing, one he couldn't share with you, at least not yet. Hell, even telling you to be careful would just set you on alarm, so he has to pretend everything is fine while you're unaware. While he's well aware you can handle your own, he just wants to keep you out of harm's way.

The rest of the day you can't help noticing that he's there, nearby. He's there when you're at lunch in the dining area, when you're studying in the library, when you're at weapons training. Not that you mind at all. You approach him towards the end of the day as you're headed back towards your dorm. "You're my security detail, aren't you?"

"You figured that out pretty quick."

"You're not exactly stealthy," you smirk.

"That stings, darlin'. But I'm not supposed to be stealthy. Just need to keep you safe."

"You're still not going to tell me why?"

He just shakes his head as he walks you to your room.

You sigh. "Are you going to stay out here all night? Like a guard or something?"

"If that's what I have to do."

It should bother you that you don't have much privacy, that your every move is going to be monitored. You assume it has something to do with your previous agency, but there's a small part of you that lacks the courage to address it. Looking at Jack, you wonder if he suspects you of wrongdoing, or if he's simply following orders.

"Good night then," you shrug. "Just remember: you'd be bored without me." Playfully sticking your tongue at him you slip inside your room.

"I'd go insane without you," he whispers just as your door clicks shut.

Not a few seconds later, he hears you calling his name, and he rushes inside to find you frozen, staring at your ransacked room. Upended furniture, your personal belongings thrown and scattered around. Drawers emptied and tossed aside. Your bed torn apart, your mirrors broken.

Questions form in your mouth but die on your lips. You have no idea who and even less idea of why. Jack immediately jumps into action, calling for a full sweep of the room for any evidence the intruder or intruders may have left behind. Meanwhile, feeling helpless, you stand out in the hallway, arms folded over your chest as the security team hurries in to investigate. You're asked to come in to check if anything was stolen, but seeing the few precious items you have still intact in your hiding place, you come to the conclusion that whoever did this was just out to scare you.

"Do they usually do things like this?" you mumble as Jack waits with you in the hallway. Some of the other junior agents are peeking out to see what's going on, and upon seeing your death glare they go back inside their dorms. "Seems petty to initiate someone by doing something so cruel."

"Sweetheart, I don't think it was no initiation," he says. "I'm pretty sure you don't think that either."

It finally catches up to you, the loneliness you've suppressed, the emotions you've had to swallow because you wanted your work to be your life. The friends you didn't make have now all turned to possible enemies. It's the loneliest feeling you've ever had.

"I'm not gonna let anything happen to you," Jack tells you, and to your surprise he kisses your forehead. "I'm here. And I'm not letting you out of my sight."

You nod, grateful for his assuring words. "I thought I didn't care, but I just hate feeling so unwanted here," you swallow the tears that threaten to fall, having kept strong for so long.

Watching you like this is a dagger to his heart. You're usually so upbeat, so full of sass, and this incident bringing you this low really breaks him. He wipes your tears away. Your fear is normal, and even though he can't promise to remove it completely, he wants to at least make you feel a little better. "This is why I don't want.. just the thought of you being in danger.."

Your eyes grow wide as you stamp down the hope that he's speaking from anything more than a mentor standpoint. "Danger is what you're training me for.. why don't you want me near it?"

Jack clenches his jaw. He doesn't want to admit what goes against all rational thought, against all logic. He's protective because of how he feels about you. When did he become such a weak fool? He inhales and exhales slowly, hardening his features to hide his emotions. "I just don't like the thought of you getting hurt."

All you can do is absorb this information and store it away to think about another day. "I don't want to stay in there. The whole room feels.. violated." You cross your arms, shivering.

His mouth is dry as he asks, "Do you want to come spend the night in my room? It's safe, no one's getting in there. I'll keep watch the entire night."

Blinking, you grasp what he's offering. "Only if it's really okay with you."

"Your room is so you," you compliment, looking at the decor as Jack brings you inside his room. "Very masculine. Very John Wayne." The walls are decorated with buffalo prints and mounted longhorn steer antlers, and above you there are wooden ceiling beams, which draw your attention to the adobe fireplace in the corner of the room. Both woven and cowhide rugs lay at various places on the floor. You take from him the bundle of clothing and hygienic necessities you brought from your room and go into his restroom to quickly change and wash up for the night.

"So, where should I sleep?" you ask, emerging from the restroom.

"You take the bed," he says gruffly. "I'll take the sofa," he says, already making himself comfortable.

"You're sure?" You start to feel bad for disrupting his peace.

"Of course I'm sure. Where else you gonna sleep? The closet?"

You laugh a little, starting to feel more at ease. "In that case.." you tentatively climb into his bed, done in western prints, the headboard made of brown leather.

He watches you get into his bed. There's a certain gracefulness to the everyday action. Damn if everything about you doesn't arouse him. He has to take a deep breath to keep himself grounded. But it's his bed you're getting into, your skin touching his sheets, your head resting on his pillow. He clenches his jaw.

"Aren't you going to sleep?" you ask.

"I can stay awake all night if I have to. Make sure you're safe."

"Whiskey, you don't have to do that.."

A little smile crosses his lips. "Then I'll sleep once you're asleep."

"Once I'm asleep just get in with me. This is your room and I'm not going to kick you out of your own bed."

His heart beats double-time at your suggestion. There's no way she can possibly mean that he tells himself. "I'm fine here," he says, nearly choking on his words.

You nod against his pillow, which has his scent. "Well if you change your mind.. this mattress is heavenly." You close your eyes and shift your hips so you can lay on your side.

Damn it. That isn't something he needs to hear. He doesn't need your voice to sound so damn alluring like that. The way your hips roll as you shift position is sending his mind to places he doesn't need to go right now. He takes his eyes off you just to alleviate the flow of blood to his dick, which is already pretty hard.

It's late when he realizes you're finally deeply asleep. From where he rests on the sofa he watches you sleep, admires your beauty in the dim light of the room. He doesn't realize he's also fallen asleep until he hears you cry out in your sleep, your body tossing about. He jolts awake and goes to you, wraps his arms around you as if to shield you from your nightmares. "Sweetheart, wake up," he says gently. "I've got you."

You wake, shivering, your nightmare still looming large in your mind's eye until Jack's soothing embrace eases you back to reality. "It was so real," you mutter, taking a gulp of water from a glass that he offers you. "Would you.. would you get in with me? I just need to be held right now."

He hesitates only a moment before getting in on the other side of the bed. You slide over to make room, then scoot back towards him, allowing him to pull you close with his arm around you.

And damn it if he doesn't love the way you feel against him.

Not asleep yet, you let your body get into a comfortable place, basking in the warmth of his body, your hands resting on his, settled just below your chest. Without thinking about it, you trace the outlines of his fingers, his hands much larger than yours. His other hand is just above your hip, warm, pleasant.

Actually, 'pleasant' is too gentle a word to describe it. It's an intimate touch without being too forward. So many intrusive thoughts come to your mind. And in this rare moment of closeness, you let them win.

Closing your eyes you take a deep, silent breath as you take his hand from your hip and lead it lower, beneath the hem of your pajama shorts. Jack gives a little growl, indulging in the feel of your soft, smooth skin against his fingertips. "We shouldn't be doin' this," he whispers as his hand stills. You can feel the thumping of his heartbeat against your back. "We're breaking a lot of rules right now, just bein' here like this."

You can't help feeling a little guilty. You got yourself into this mess and all he did was try to pull you out. And now you were just a huge inconvenience, apart from also being a huge temptation. "No one would know but us," you tell him, turning on your side to face him. "I know you're my mentor, but I'm not a child. I want this."

He's quiet a moment, looking into your eyes, and for a moment you fear he will reprimand you, turn you down. It would be the worst embarrassment you can imagine. But then he leans in and kisses you, softly at first then with more pressure, and your lips part for his tongue as yours presses against his.

His hands make their way down your body, trailing across your skin as if you're the most delicate thing he's ever seen. Your hips rise up, inviting his touch, and damn it if he isn't ready to just rip your clothes off. Your body buzzes with exhilaration as Jack presses kisses down your neck, your chest, all the way down to give a kiss on your hip. "Is this okay?" he asks, breath shallow as his eyes search yours.

"Yes," comes your whimpering reply, and your breath hitches in your throat when he traces the border where your pajama shorts meet your thigh, and he slowly pulls them down. You arch your back, lifting your hips to help him, and your panties and shorts come off in one go as he slides them down your thighs until he removes them completely.

"I want to see all of you," he whispers, and you nod, pulling up your top, completely exposed to him. You watch him with wide eyes, awaiting his reaction.

Jack licks his lips, looking as though he could devour you. But he takes his time, his fingers slowly tracing up your torso, gently cupping your breasts and grazing his thumb across your nipples. Your sweet little gasp sends sparks firing in his eyes. "You're so sensitive to my touch," he whispers, as if witnessing a miracle. He laps his tongue over each bud, pursing his lips around it and groaning in need as you moan, lifting your hips to his. Even through his night clothes he can feel your heat, your moisture. "I need to taste you," he growls.

"Wait," you whisper. "I need to tell you.. I've never done this before."

This is something he doesn't expect. You always seem so sure of yourself, so direct in what you want, that he never would have thought you'd be inexperienced. "You really want me to be your first?" he asks, growing excited at the prospect of being with you.

"I want this.. with you," you assure him. "There's no one I trust more."

That's all he needs to hear from you. You're giving yourself to him, trusting him. "That means the world to me," he tells you. And with that, he doesn't hesitate. His hands move down your waist, across your hips and between your thighs. Spurred on by your shuddering sigh, he traces your slick folds with his fingertips until you beg him to finally touch you deeper. He eases two fingers in and out, his thumb tracing circular motions over you clit, barely restraining a growl as you eagerly clamp down on his digits. He watches, rapt, as you bite your lip to keep from moaning. He wants to give you more, to make you see stars while he's showing you what it can be like between lovers.

You feel like a god damn queen the moment he slips further down between your legs, gently raising them and getting himself settled. Heart hammering wildly, you gasp as you feel his tongue on your clit, gently sweeping over the sensitive flesh as he continues to work his fingers in and out. On a gasp your fingers grab his hair, causing him to growl and cup your butt with both hands as he resumes his attention on you, tongue flicking over your clit, along your folds, dipping into your crease, lapping up your sweet honey as if he's never going to have another meal ever again. Your blood grows hot and you're unable to even think of anything else but the burgeoning pleasure, and just when you think you might explode from need, the sweet, pulsing feeling takes over. You cry out loud, quivering as Jack makes you come.

He pulls away slowly once you're done, pressing gentle kisses on the insides of your thighs, working his way back up your body with his lips. "You okay there, darlin'? Need a minute to collect yourself?"

You nod, laughing a little, on the verge of giggles because your body has just experienced something so wonderful. "I'm good.. I'm perfect.." you manage to say, and there's a light in your eyes that affirms this.

"You are perfect, we are in agreement on that," he smiles, tucking a stray strand of hair away from your face, still flushed from your orgasm.

"Jack," you whisper, using his given name for the first time. "I'm ready.. I want you."

There's a delicious urgency as you help him remove his night clothes. His masculine build exceeds anything you have fantasized about him. His chest is broad with a sprinkling of light brown hair on his chest, and more of that curly hair leads from his navel down to his cock, which he encourages you to touch. It's thick, warm, heavy in your hand, growing more firm with each little stroke you give him.

You both have a need required to be met, but Jack wants to do this slowly, to build it up and make it the best possible experience for you. He has a strong desire to tear into you but he restrains himself, opting instead to kiss you softly, pressing himself to your warmth. He wants you to be a complete puddle for him to take care of once he's finished with you.

As he explores your body you explore his, running your hands over his muscled arms and back, savoring every part. You whimper as he pulls you closer, and your heart gallops. Before he loses himself in the moment, Jack reaches into his bedside drawer for a condom and carefully puts it on, then goes back to kissing you, gently nudging your thighs apart to make room for him. "If you want to stop, tell me," he says to you, and you reply with a kiss, eagerly bringing your body to his and he has no other thought in his head than to make you his once and for all.

Your eyes lock with his as he presses forward, easing himself in just a little at a time. Jesus, the pressure is so sweet, he's only an inch or so in and already he's stretching you. "I'm gonna take it easy with ya, cowgirl," he whispers, pulling out then easing back in, wanting you to be as wet as possible so you can take all of him. Your sweet, sharp little intakes of breath let him know you're feeling good, that you need more, and with each stroke he goes in deeper, until you're completely filled with him, as if you've needed him this way forever, as if you'd been born just to be his.

"You feel so good," you tell him, placing a kiss upon his neck, the skin of his throat rosy with the labor of holding back.

He sighs. eyes closed then open again because he wants to see you laid out beneath him this way. "God, you feel so right.." He moves his hips against you in slow, fluid movements, and in turn you take more of him into you, giving him a home within you. Jack's lips move over yours, then nuzzle your neck, tracing circular patterns over your breasts and back again, while your hands explore his broad shoulders, his brawny arms and the steady pacing of the pistoning of his hips driving against yours as the euphoria within your heart swells. "There's my good girl.. ah, such a tight fit.. but you're so nice and wet for me.."

"More," you gasp, nails lightly scratching on his back, and he gives you just that, taking your breath away as your bodies move together, quickly, towards your common goal. The electricity grows between you, the sweet, sweet friction doubles in your efforts, eliciting desperate moans and sweet gasps. Jack can feel the tension growing within you, the excitement building up to its greatest height. Jack whispers, "That's it, my sweet darlin', come for me.. oh I can feel you squeezin' all around me.." You whisper his name in a frenzy of desire, whisper it like a prayer as you feel the pleasure climb higher and higher. Without warning you shatter beneath him, crying out as you come.

Your sounds are the most divine music ever played. He can no longer hold back, gaining momentum as he brings himself to the tipping point, burying his face in your neck when he comes, releasing with a satiated exhale. You hold onto him, both of you trying to catch your breath, and you press a kiss to his shoulder. He looks up and smiles at you. "You doin' okay, darlin'?" he asks. His body is still but he remains inside of you, wanting to keep the feeling a little longer.

"I think I can die happy having experienced that with you," you sigh, tracing the outline of his jaw.

"You're too sweet," he shakes his head, grinning like a fool as he kisses your lips. "And I'd be more than happy to do that again and again.."

"Oh?" Your heart jumps for joy. "I suppose I could find time for that to happen," you tease him.

Jack smiles and nibbles on your neck. "Good, because I can think up a few other things to try."

You blush, despite still being naked and entangled with him. "What kinds of things?"

"Things like new positions, new places.. maybe once you're comfortable you'll let me tie you down and give you a little tease.." he smirks. "You know, just a few thoughts," he says casually with a gleam in his eye before kissing you gently.

"Holy hell," you whisper, utterly turned on again as you return his kiss. "I can't wait.."

dividers by @saradika-graphics 👑

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