Seven Days of Valentines, (Diamonds and Daddies side story) Whiskey x F!Reader CH 2
A/N: Thanks to @talesfromtheguild for Beta reading and helping me with many ideas for this!
This will be a weekly series leading up to Valentines Day
I try to keep Readers physical appearance as open as possible for this story, but please note in these chapters shes going to become more of a ‘character’, some specific interests of hers are going to come into play.
This is canon to the main Diamonds and Daddies story, but i am uploading as its own thing. You do not need to have read Diamonds and Daddies to read this, just know its a fic about Jack ‘Whiskey’ Daniels being a Sugar Daddy and the reader is a professional Sugar Baby.
Fandom: Kingsman the golden circle
Ship: Jack ‘Whiskey’ Daniels x Cis F!reader
Warning/tags: established relationship, fluff, semi-public sex, sex against a window, P in V sex, fingering, Oral (M and F receiving) , multiple orgasms, slight over stimulation, dirty talk, choking, Daddy kink, DD/LG/BDSM style relationship, creampie,biting/marking, possessive language, aftercare, Jacks both a gentleman and a DIRTY BASTARD, Reader is 100% into it all
Word count: 6K +
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Summary: Whiskey whisks his Sugar baby away for a romantic Valentine’s getaway. Day two he takes her to see her favorite work of art.
Tuesday 9th of February
The second morning in Rome started with an early morning makeout session, soft, gentle kisses roused you from sleep, followed by a shower and a traditional Italian breakfast delivered to your suite as the two of you sat watching people make their way to the coliseum.
The coffee and crespelles were a perfect way to start the day, made all the more better by Jack’s large hand resting on your thigh, drawing gentle patterns with his thumb as you each sipped your mugs in comfortable silence.
By eight thirty AM the two of you were dressed in your warm clothes and out the door, ready to partake in whatever adventure Jack had planned.
You sat literally on the edge of your seat in excitement as you were driven around Rome to our destination for the day. Jack warmly chuckled beside you at your boundless enthusiasm, smiling wider to himself as you began snapping pictures along the way of the general beauty that was Rome.
Once you were dropped off Jack took your hand in his, leading the way up the road and round the corner. You practically hummed in excitement beside him, bouncing in glee as the large walls of Vatican City loomed over you.
“Jaaaacccckkkk!” you squealed delightedly, as he led you to the back of a growing queue. “Are we going where I think we’re going?”
He chuckled at your excitement again. “Couldn't take my girl to Rome without letting her see her favorite work of art could I?”
You bounced in place, trying to express your excitement and gratitude in any articulate way you could, you cupped his face and pulled him down for an expressive kiss on his cheek.
“You have no idea how excited I am Jack!” You elated, almost jumping for joy beside him.
He tried to calm you down and keep you still by resting his hands on your hips, pulling you to his front in a gentle embrace.
“I have a fair idea Sugar,” he hummed, kissing your brow affectionately. “I remember when you mentioned wanting to visit Rome, on our New Year's trip, just a passing comment, but your eyes lit up when you mentioned the Sistine Chapel, I just knew I had to take you one day Darlin.”
Your hands rested lightly on his chest, with your gaze cast down you smiled, tenderly remembering the brief exchange you had shared months prior. At the time you never took much note of your conversation, having forgotten all about it until Jack had surprised you with this trip, but clearly Jack had taken notice, and went through great pains to make your wish you had barely ever shared before a reality.
You had lost count of the amount of times he proved himself of how utterly perfect he was for you was incalculable.
He amazed you every day, outdoing himself with each little surprise or adoring words, each grand gesture or gentle peck, each casual touch or passionate kiss.
Jack Daniels, as cocky, ridiculous, and flirtatious as he was, was everything you had ever hoped for.
“I wish I knew, just how to show my gratitude to you Jack,” you whispered softly to him.
He gently pulled your gaze back up to meet his.
“Darlin, you don’t need to do anything other than stay with me. You’ve made this lonely heart feel something again for the first time in years, and that's more than enough for me.”
Your lower lip wobbled and your eyes threatened to spill, Jack preemptively stopped your sappy tears from spilling with a gentle kiss to your lips.
“Come on Darlin, lines moving.”
Jack walked arm in arm with you throughout the whole tour of Vatican city, your gaze was often fixed to the beautiful architecture or paintings, but everytime you glanced over at Jack, his eyes were fixed on you. You had his whole attention, not the paintings, not the tour guide, you.
“Jack?” You asked softly, concerned he was only humoring you and didn't actually care about anything you were seeing. “Aren't you interested in all this?”
“Oh I am Darlin,” he reassured. “But I love watching the way your eyes light up, better than any painting here.”
“You’re just trying to butter me up Cowboy,” you smiled up at him.
“Can’t help it Sugar, pretty thing like you on my arm? Who can blame me?”
“You flatter me Jack, You’ve been sweet talking me from the moment we met, I don't even think you would know how to stop,” you teased.
He chuckled and kissed your cheek.
“No Darlin, I don't think I would know how to either.”
It was impossible to express just how fantastical it felt to see some of the famous pieces found in the Vatican museum, Raphael’s ‘Transfiguration’, The statue of Laocoön and his sons, The Vision of St. Helen , Da Vinci's St. Jerome in Wilderness, masterpieces you had only ever seen photos of on the internet or in your meager collection of art History books. Completely indescribable. But these experiences paled in comparison to seeing Michelangelo’s Creation of Adam, photos could not compare to how breathtaking it was. It loomed above you, alongside dozens of other High Renaissance masterpieces, but your eyes were pulled back to that one each time.
You imagined Michelangelo, centuries ago, in his genius, laying on his back atop the precarious scaffolding as he painted it, how grueling it was, how long it took.
You never thought you would ever see it, not in person, it had been such a fantasy to you you had never really mentioned it before until Jack had asked you those months ago.
Daddies had taken you on vacations before, trips to sunny beaches and tropical getaways, when they wanted to impress you and have you show some skin, but not once had they ever asked you where you wanted to go, what you wanted to see.
There had been no desire to share your interests, to take you to experience culture and art over bikinis and parties. Jack had been right, you had been with some shit Daddies before you met him.
The picturesque beaches and clear oceans may have been pretty to look at, but it couldn't hold a candle to the beauty above you.
Standing there, with your neck strained up at the ceiling, your eyes began to water for the umpteenth time since you had landed in Italy, but you willed them away this time, focusing on the painting to burn the experience into your memory and refusing to let the tears fog your vision as emotions overwhelmed you once again.
“Baby?” Jack’s soft voice cut in, his arms wrapped around your middle as he came up behind you, kissing your forehead. “You good?”
“Perfect, Jack,” you whispered back, giving your neck a break by resting the back of your head on him.
“Everything you ever dreamed about?” He asked, following your gaze to the painting.
“Better,” you sighed, squeezing his arms around you.
You clung to Jack’s arm as you made your way out of Vatican city and back to the streets of Rome. He patted your hand affectionately, placing a kiss to your temple.
You had been so...so... moved, by Jack's surprise, by the artworks, by the experience and you knew you couldn’t express it to him. And you knew he knew.
You were beginning to understand the magnitude of his affections, he wasn’t just trying to impress you, to show off and boost his ego like many men before him.
No, Jack's masculinity wasn’t so fragile that he had to prove himself like that, he may flash his money for you, to buy you trinkets and clothes just as they all had before, but the way he went about it was so different.
Stuff wasn’t what he relied on to keep you with him, no, he kept you by his side by paying attention, by caring about you, for you.
He wanted to make you happy, truly, and he expected nothing from you in return apart from your companionship.
His words from earlier in the day were really starting to strike a chord with you.
“You’ve made this lonely heart feel something again for the first time in years.”
You looked up at him from the corner of your eye as he led you through the streets. He seems to know where he wanted to go, and you trusted him not to get you lost.
“Jack,” you whispered softly. “I-”
“Don’t need to say a thing Baby,” he interrupted. “I know.”
“But, I-” you sighed. “How?”
“How do I know?” he asked, amused. “Baby you thank me every damn time I do something for you, no matter how big or small, I've picked up on a few things. I can tell when you’re struggling to figure out how to thank me.”
He stopped in his tracks, guiding you to his front and pulling one of your hands up to his lips to kiss it.
“You tear up when something specially meaningful, those are the times you can’t figure out what to say,” he cupped your face in his large, warm hands. They felt nice against the chill that had clung to your cheeks. “But you don’t need to say anything Sugar, I can tell just by lookin at’cha you’re grateful. It made you happy, that's all I wanted. I don’t need a ‘thank you’, I just need you.”
Your lip wobbled and you pouted up at him, making him chuckle.
“See? Just like that, and I get yer waterworks running,” he teased, thumb wiping a tear that was threatening to spill.
You rolled your eyes and swatted his chest playfully.
“None of that Darlin” he laughed, ducking his head to kiss you. “My Baby gets all sappy for Daddy’s sweet words huh?”
“Don’t get cocky,” you giggled, trying to duck from him gleefully.
“Thought you liked me ‘cocky’,” he joked as you turned and tried to walk off, pulling you back into his grip, back flush against his front. “Specially when it’s inside-”
“Jack! People are watching!” you laughed, swatting at him over your shoulder, grateful at least your conversation wasn't too loud and probably not understood by the locals who rolled their eyes at the childish tourists as they passed.
He laughed merrily, letting you go and gently taking your hand.
“Such a killjoy,” he joked, leading the two of you again. “Come on then Sugar, lets get some lunch.”
Lunch turned out to be in this adorable local cafe hidden down many sidestreets.
Jack told him a work colleague told him about the hidden gem, unknown to most tourists, and had made a point to bring you there.
You sat inside, safe from the bitter cold as you sipped your hot drinks and shared croissants and muffins.
Silence passes between you, as you watch from your window the small trickle of locals walk by, trudging through the remaining snow slush, on their way to wherever it was they were going. It was a perfect way to relax after your tour, Jack told you to enjoy it while it lasted, because he had one more surprise for the day.
Jack’s second surprise was a tour of Castel sant'angelo.
It was originally built as a mausoleum, over the centuries it became a fortress and castle, in modern times, it had become a museum.
“Two museum tours in one day?” You asked, humming as the two of you walked over the beautifully sculpted bridge leading up to the impressive building hand in hand.
“Well with it being so close to the Vatican, I thought ‘Why not?’ , and I know how much my Baby appreciates her art and history,” he smiled.
Taking his words from earlier to hear, you thanked him with just a kiss on the cheek.
Jack insisted the two of you could walk back to your hotel by the time you were kicked out of the castle at closing time.
‘Just a forty minute walk’ he promised.
You pouted at him, shaking your head no.
“My feet are killing me Jack,” you whined.
“Won't it be romantic though Baby?” He asked, trying to convince you.“Walking through the streets of Rome at night? Just the two of us?”
It did sound nice, in theory, but the sky was clouded over, your feet hurt, the ground was covered in slush and it was starting to seep into your supposedly waterproof boots.
“My toes are going numb and it’s freezing Jack!”
“But Baby-”
“Daddy,” you sniveled, trying to appeal to his dominant, caring role over you. You wrapped your arms around yourself to block out the cold as the temperature dropped further. It was bearable in the day, sunlight and warm clothes enough to keep you reasonably warm. But you weren't dressed with the expectation of being outdoors too long, and as the snow began to fall you pulled yourself to his chest, snuggling into his warmth.
“Please Daddy, I don't want to walk like this.”
He sighed and wrapped an arm around you, caving to his instincts to care for you.
“Alright then, let me call a cab Honey Bee,” he relented, pulling out his phone.
You groaned when you made your way into the hotel room, throwing the keycard on the table and collapsing by the door , tearing off your boots and letting your soaked, numb toes free.
Jack chuckled at your dramatic behaviour, not removing any of his gear much to your confusion.
“There’s a few more presents on the bed for you,” he smiled, heat in his eyes and flashing his canines at you as he crouched down in front of you, stroking your cheek. “Want you to go in there and put them on-”
“Jack, my feet are too sore for any heels toni-”
“No heels, Honey Bee,” he said, his tone and use of your moniker a clear warning for you to fall in line. “You’ll like it, I promise. Now go open your presents and get dressed while I go pick up dinner.”
He stood up as you nodded and took his hand when he offered it, helping you up and grabbing the keycard from where you discarded it.
“Be back soon Baby,” he smiled as he opened the door and left.
Alone, you padded into the bedroom, your feet grateful for the plush carpet as you made your way over to the bed.
Laid out across the sheets was a beautiful little pair of pink and black satin sleep shorts, a matching bralette, a cute pair of pink fluffy bunny slippers, and a long fuzzy pink gown. You ran your fingers over the material of them all, amazed at how soft they all were.
Atop your outfit for the night was another folded up note. You picked it up carefully and opened it up, greeted by Jack’s familiar scrawl once again.
“Day two of seven, I know your feet must be real sore today Baby, I hope a relaxing evening with Daddy makes up for it. Get dressed and go pick out a movie out in the livin room for me.
Happy Valentine’s Week Sugar, Love Jack”
You softened, reading his words, again as you folded the note back up and began redressing.
The satin felt even smoother as it covered your skin, and the fuzzy robe and slippers helped warm you up after your cold trip back to your suite.
Once dressed you wandered out into the living area, delighted to see the couch covered in soft blankets and pillows, a gift hamper sat on the coffee table containing sweets, a bottle of wine, glasses and some foot lotion. Your heart warmed at the thoughtfulness of it all and how intimately comfortable it was.
As you snuggled under one of the blankets and flicked on the TV, scrolling through movie options you heard the keycard beep and the door unlock.
“Back Darlin!” Jack called from the entranceway , you heard him put something down and head to the bedroom.
He joined you a few minutes later, wearing nothing but a pair of sweatpants that hung low on his hips and his trademark stetson, carrying a large pizza box.
You smiled and bit your lip, admiring his little tummy that you loved so much.
He placed the box on the coffee table and snuggled under the blanket with you.
“Pick something out Baby?” He asked, one arm over the back of the couch and other hand wandering up your thigh under your robe and resting there.
“I think so,” you hummed, relaxing back into his embrace and warmth, head resting on his shoulder. “Sci-Fi movie by the looks of it.”
“Prospect?” Jack questioned. “Don’t usually sound like our kinda thing Darlin.”
“Yeah, but one of the actors caught my eye in the preview clips,” you giggled. “He looks like you Daddy.”
He quirked his eyebrow at you and gave you a shrug, letting you click play as he pulled the pizza and wine over for you to share.
You almost choked on your pizza when the actor showed up and Jack exclaimed in annoyance that he looked nothing like him.
“What are you talking about?” You laughed. “He could be your twin!”
“I know for a fact my Mamma only gave birth to one Daniels boy thank you very much!” He proclaimed.
You giggled hysterically, curling into him, trying not to knock the pizza box onto the floor.
“He’s just you with more scruff!” You gasped for breath between your laughter. “Listen to him he’s even got a southern accent too!”
“I resent being compared to a scruffy, sweaty, bastard space man who talks so damn weird Darlin!”
You covered your mouth, biting back a sassy comment about the ‘talks weird’ comment and tried to compose yourself.
“How can you not see it?” You asked when you finally calmed down. “The similarities are scary.”
The two of you eventually agreed to disagree as you finished your pizza and wine and moved on to a few after dinner chocolates from the hamper.
Jack rubbed your feet with the lotion as you lay on the couch sideways, easing the tension and soreness from your feet in his lap as the movie went on. You melted to his touch, unwinding from the long day on your feet.
You had taken quite a liking to the southern spaceman with the silver tongue, much to Jack's growing annoyance, he grumbled as you cooed at the man on screen.
But as irritated as he was, he pulled you to his side in comfort as you watched your little crush have his arm amputated, hiding your face in Jack’s chest throughout the difficult scene.
“Poor Ezra,” you murmured when the scene was over.
Jack rolled his eyes and kissed the crown of your head. “I don’t know what you see in him Darlin.”
“He’s your scoundrel, space-cowboy twin Jack. What’s not to like?”
“Think you need your eyes checked Darlin. I might actually be bothered ‘bout your little infatuation if you didn’t insist so damn hard that he looked like me.”
You giggled and settled down again against his bare chest.
“Hmm...”
“What are you hmming about over there?”
“You’d look good with a little blonde patch.”
“Shut up.”
When the credits rolled Jack switched off the TV, shrouding the room in darkness and stood up, gently pulling you up to your feet beside him. You were tired after such a long day, and the movie and snuggles afterwards only made you more tired.
He rested his hands on your hips and gave you a tender, soft kiss.
“You like your new jammies Baby?�� He asked, smiling when you nodded. “Yeah? You look so dang cute in them.”
He nuzzled his nose against yours.
“Is my Baby too tired tonight? Or do you want to have some playtime with Daddy before bed?”
You whined in response, resting your hands on his chest.
“I always want to play with you Daddy.”
“Oh I know you do Baby, but Daddy thinks you need your rest. Bed time for you I think.”
“I don’t want to go to bed Daddy.”
“Think you’re awake enough for it Honey Bee?” he asked, gently shoving your new robe off of your shoulders and onto the floor.
“Yes,” you nodded.
“Prove it,” he rasped, firmly pushing you to your knees in front of the couch and pulling his sweats down enough for his balls and hardening cock to hook over them.
You licked your lips and looked up at him, taking him in your hand at the base. His eyes burned into yours as you opened your mouth and began kitten licking at his tip, circling your tongue around him.
You kissed him, from base to tip, worshipping his cock.
He moaned at your teasing little touches and you felt him twitch in your hand, hardening slowly under your touch.
‘That's it Baby, Get Daddy nice and hard,” he sighed, closing his eyes and leaning his head back to lose himself to the feeling of you coaxing his cock.
You felt the crotch of your sleep shorts become wet, aroused by his raspy voice and lewd moans. But you kept your hands where they were, on his thigh and cock, knowing if you touched yourself without permission his ‘playtime’ with you would become a (delicious) punishment.
You relaxed your jaw and took him into your mouth, letting your tongue run along the underside of his length as you bobbed your head, taking him deeper into your mouth.
He let out a loud guttural moan, hands cupping your head to keep you in place.
“Hmmmmm fuck Baby!” He spat, looking back down at you and gently thrusting his hips into your face, careful not to choke you. “You’ve gotten so good at that! Can take me so well now can’t cha? Almost all the way!”
He rocked into you slowly, now fully erect in your mouth, you concentrated on breathing through your nose as he pushed himself deeper with each thrust.
You had succeeded in taking him easier than when you first had gotten together, but it was still a struggle to truly deepthroat him and supress your gag reflex, so far you had never managed to take him all in before you backed out. You kept your hand on his thigh, ready to tap out when needed.
Your eyes never left his face, and his never left your lips, watching as inch by inch his cock went further into your mouth.
“Breathe Baby,” he encouraged, hungrily watching his spit covered cock push and pull in and out of you. “If you can take me all the way in tonight Baby, I’ll give you a big reward.”
You mewled around him, excited by his promise of a reward. He always delivered on those promises in a spectacular way.
You took a deep breath through your nose and relaxed your throat as best you could, successfully taking him further, your jaw hurt and your throat protested as he pushed in even deeper.
Your eyes watered as your lips finally met the groomed hair at his base. You blinked up at him, waiting for approval and praise for having taken him all the way for the first time triumphantly.
“Hnnng! Fuck! Good girl! Good Girl!” he panted, watching you, transfixed on the way his cock looked shoved all the way down your throat. “Perfect, warm wet little mouth fuck!”
He reached down cautiously, fingers tracing over your neck gently, feeling the bulge in your throat. You whined, feeling light headed as he gripped your neck and squeezed lightly, he gave an experimental thrust, even with the awkward angle and groaned at the feeling of his own hand squeezing your throat tighter around him.
“Oh fuck Honey Bee I’m so deep,” he moaned, squeezing tighter, making you more light headed. “Doin such a good job, you need to tap out Sugar?”
You shook your head no as best you could, head swimming and body buzzing as he chokes you with his hand and cock.
“Can feel my fat cock moving inside you Baby, so damn hot, making me even fucking harder.”
He kept thrusting into your throat slowly, careful to not actually choke you. You were getting a little high from the lack of oxygen, far more aroused by it than you ever thought you could be. You only tapped out when black dots started to swim in your vision.
Jack pulled free without hesitation, crouching in front of you to check you were alright as the obstruction in your throat was gone and your lungs heaved in oxygen.
You gulped down air hungrily as Jack kissed your face in praise.
“Did so well baby, so proud of you, you took me all the way,” he murmured, nose nuzzling along your hairline. He waited for you to be ready to continue , and when your breathing had calmed and you gave him a nod to continue, he kissed your forehead, stood up and pulled you to your feet with him.
“As promised, my little girl deserves her reward,” he growled, nodding over to an armchair by the sliding door. “Go sit,” he ordered softly.
You scrambled to comply, anticipating your reward with glee.
He sauntered over, discarding his stetson on the coffee table before kneeling down in front of you, hooking his fingers into your sleep shorts.
“Up,” he gently instructed, pulling them down your legs as you lifted your hips for him.
He brought the shorts up to his face and inhaled your scent, licking up the crotch of them to taste the juices that soaked them.
“My baby tastes so good,” he praised, discarding the shorts over his shoulder. “Spread ‘em wide for me Sugar,” he said, gently coaxing your leg apart and licking his lips.
He didn’t tease, intent on giving you your much deserved reward as he drank you down and shoved his tongue deep into your dripping hole.
Your back arched, eyes closed and thighs shook, he pulled them over his shoulders to give himself more room, his strong arms wrapped around your thighs to hold them still.
You whimpered in delight, gripping his hair and pulling him deeper, his eyes cut up at you, letting you know that at any other time, an action would not be tolerated, and he would have you reprimanded for being greedy.
But this was your reward, you deserved it.
Jack did not hide his messy noises as he ate you out like a man starved, wet smacks of his lips on your lower lips, the sound of his skin coming into contact with your dripping thighs, his moans and your sounds of pleasure filled the room.
You gasped when you felt a thick finger prod at your hole, pushing up into you beside his tongue. Your head snapped down to watch as he slowly pumped his finger into you, his tongue began lapping up your folds until he reached your clit, suckling on it gently.
“Daddy!” You whimpered, pushing your hips up further into his face.
He gave you a cocky grin as a second finger joined the first, stretching you out so perfectly, his fingers were so much thicker than yours, fuck you loved his fingers so much, and he knew just where to stroke to make your body sing. In such a short time he had learnt your body better than you ever had.
“My Baby wants to cum?” He asked, running his tongue over your folds again.
“Yes, please Daddy,” you pleaded.
“Daddy prefers when you’re patient Baby. But you earned it tonight,” he growled, standing up with his fingers still inside you. Your legs dropped from his shoulders as he leant over you to nibble at your ear, you felt your juices that still coating his jaw as his skin met yours.
He abandoned his slow pumps of his hand, fucking you hard and fast with his skilled fingers. You keened under him, writhing at the sudden change.
“Look outside that window Baby,” he ordered in your ear hotly. “There's still people out and about, all they have to do is look up here, and they’d see you getting fucked by my hand.”
You felt your core clench around his fingers at his words, a wave of your arousal flooding out, soaking his hand.
“You like that idea Sugar? You like the idea of some stranger seeing my fingers buried in this pussy?”
You whimpered and tried to thrust up into his hand.
“Answer the question!” He growled.
“Y-Yes Daddy!” You cried, panting hard as you felt your pleasure building.
“Yeah? You get off on the idea of someone else seeing you? Seeing what’s mine?”
He sucked a mark into your neck, hoping it would show tomorrow, his secret little claim.
“Want everyone to see you? Like some kind of common whore? You’re mine Baby, don’t you forget that.”
“T-that's what i want them to see!” You whined, racing towards the edge, hoping he wouldn’t deny you as he often did to tease. “I want them to see who-who I belong to!”
He growled in approval.
“Yeah? What else Baby?” He asked, encouraging your line of thought.
“W-want them to see...That you’re- you’re the only one who can make me cum, that you’re the only one good enough!”
“Oh Baby you sure know what to say to stroke your Daddy’s ego,” he hummed in pride. “Go on then, show them, show anyone watching how hard Daddy makes you cum.”
You were already well on your way to your pleasure when he gave you permission to cum, but he helped you along by diving down and sucking hard on your clit.
Your back arched further as you screamed out his name, your walls clenching hard over his furious fingers, as they attacked that sweet deep spot inside you on a mission.
It hurt how powerful your orgasm was, how hard his fingers fucked you through it. And as it washed over you you were ready for him to pull out, for him to let you come down from your high, but his fingers did not slow.
You mewled, sensitive and sore from your first orgasm as you felt him forcing your body towards a second one already.
“D-Daddy, too- too much!” You whined, wriggling in his grasp.
“Yeah?” he asked, his teasing tone told you he didn’t believe you, he moved his head away from your clit to look you in the eyes, speeding up his fingers. “What’s your color then?”
Your hips began thrusting up to meet his hand again.
“Color Baby?” He reminded.
“Green,” bucking up hard now into his hand to chase your fast approaching second high.
“Thought so,” he hummed, taking your nipple into his mouth through your bralette, gently sucking on it and tugging it with his teeth.
When he had soaked the fabric and thoroughly teased you he released it.
“You’re going to cum again for me, that's your reward. Daddys going to make you cum so hard your pretty little pussy will be ruined tomorrow.”
You sobbed under him, anticipating how tantalizingly sore you would be with great delight.
“Come on, be a good little girl for me and cum,” he cooed, grabbing your jaw with his free hand to make you look at him, his face only inches away from yours.
“Cum for Daddy, and I’ll fuck you right up against that window for everyone to watch.”
Your stomach flipped at the thought and your core tightened around his fingers again.
“If it weren't so damn cold out there I’d fuck you right on that balcony, so the whole of Rome can hear your screams for me.”
He brushed your clit with his thumb as the words fell from his mouth, pushing you over the edge for a second time.
“That's it Baby, cum for Daddy,” he cooed softly, lips ghosting yours. “Squeezing my fingers so tight. Can't wait till my cocks all snug up in there, my favorite, perfect little hole.”
His words made your second orgasm just as powerful as the first, you shook hard in your chair and screamed loudly until your voice was hoarse. You tried to muffle the scream with your hands which, until now, had been gripping the armrest for dear life ever since Jack removed himself from between your legs.
He was having none of that however, grabbing your wrists in his hand and pulling them away from your face to hear your screams of pleasure.
He coaxed your orgasm as long as he could, slowing his fingers but still thrusting them hard inside you. Dragging it out.
You shook from the aftershocks each time his fingers shoved up against your cervix, whimpering as your breathing struggled to return to normal and body tried to unwind.
He pulled his fingers free from you, loving how your pussy tried to suck them back inside. You mewled at the loss despite how oversensitive you were.
He held up his hand to inspect it, proudly displaying how drenched it was in your cum.
“Look at that Baby, down past the wrist...You horny little thing,” he rasped, letting you watch as he wrapped his slick coated hand around his neglected cock, pumping it slowly, you could hear the wet pass of his hand with each pump.
“Stand up,” he ordered gently, not helping you as you stood up on shaky legs, struggling to comply as your legs threatened to give out underneath you.
“Top needs to go too Honey Bee,” he instructed, watching you with predatory eyes as you raised your arms, taking the sexy little Bralette off and discarding it somewhere behind you.
“Up against the window, arms up.”
You wobbled over slowly, sighing as your body touched the cool glass.
You felt so exposed up against the glass, despite the fact there was no one currently walking about outside, and there was no light in the living area now that the TV was off, the only light source being the lights outside, lighting up the coliseum.
You could see Jack's reflection in the glass as he came up behind you, stepping out of his sweats. You could hear him still pumping his cock with you slick.
Your back arched as he ran the tip of his cock over your dripping folds, making you gasp and shudder.
“Poor Baby, still so sensitive,” he teased, pushing you against the cold glass with his free hand, making your nipples tighten painfully at the chill. You wriggled slightly as he pushed his hips forward, tip entering your hole.
“Shhhh Baby, Daddy needs his fair share too, needs to fuck your pussy,” he sighed, your tight wet heat slowly enveloped him as he slowly inched his hips forward.
“Need to make you cum. One last time.” He emphasized the statement by snapping his hips forwards, filling you up completely as his hips slapped up against your ass.
He gave your oversensetive body only a moment to adjust to the stretch before wrapping an arm around you and fucking into you hard and fast. His free arm grasped your neck, lightly choking you again as his cock hammered into you.
“Fuck, so wet baby. Your cums soaking me, dripping down Daddys balls,” he rasped into your ear.
Slap. Slap. Slap. Slap. Slap, filled the room as you were shoved up against the glass with each thrust.
You cried at the delicious stretch, at how he made your tender, sore hole buzz with pleasure every time he shoved himself inside, at how your body stung from the cold glass, and at the filth he rambled into your ear.
“My perfect pussy, Daddy’s pretty little princess. Think about how anyone could walk past. Could see you,” he teased, turning you on more. “Stuffed full of my cock, wouldn’t be hard, this low down, just need to turn their head a lil bit, ‘s all it would take to see you.”
You moaned at his words, tightening around him.
“Fuck, squeezing me so tight,” he whispered in awe,thrusting harder into you.
You closed your eyes and lost yourself to the delirium of being fucked by him, trying hard not to cum around him until he gave you permission.
He didn’t like it when you came without his permission.
He chuckled darkly into your ear, slowing his thrusts down to teasing rolls of the hips. “There's someone now,” he rasped, watching someone walk by further down the street, you cracked your eyes open and could see just how close they were, close enough that if you called out with the window open, they would hear.
“I don’t think they’ve spotted us. Let’s see if we can change that shall we?” He suggested with another dark laugh, letting go of your neck to grip your hips with both hands, making it much easier to thrust inside you and leaving nothing to silence your noises as he slammed into you again with the same speed as before.
You shrieked, watching with wide eyes at the passer by, hoping he did not hear.
It was annoying just how arousing the idea of this stranger catching the two of you was.
Before you could even stop yourself, you came around Jack’s cock without warning. No build up, no tensing, it hit you so suddenly you couldn’t have stopped yourself if you had tried.
He growled angrily behind you, pausing his thrusts as you squeezed him hard, as your walls fluttered and tried to milk his cock.
There was no way you could hide what you just did, it may have snuck up on you fast but he felt it. Felt you squeeze him and shake in his grasp.
“Did you just fucking cum Baby?” He snarled. “Without Daddy’s permission?”
“I’m sorry!” you sobbed. “I didn’t mean to, it happened so fast!”
“You got off to the thought of some stranger seeing you, isn’t that right?”
“Yes, Daddy,” you whimpered pathetically, not wanting to anger him further by lying to him.
“Such a filthy little slut,” he berated, rocking back into you. “If Daddy didn’t need to cum so bad I'd punish you right now. Throw you over my knee and remind you that Daddy owns your orgasms.”
“I know Daddy! I’m sorry! So sorry!”
“I believe you Baby, but that don't change the rules. Doesn’t mean you get away without some sort of punishment.” He licked the shell of your ear, nibbling at you lightly.
“Tomorrow night, I really will destroy your pussy. I’ll hold you down and fuck you so hard, till you cum so many times you pass out, never letting up until you’re beggin me to. Daddy will choose how many times you cum, when you cum, and how hard you cum, to remind you your pleasure belongs to me.”
You sniveled, panting as your breath fogged up the glass.
“Y-Yes Daddy,” you agreed.
“Now stay still, Daddy gonna fill you up, get you nice and creamy.”
His rocks built back up to the harsh thrusts, reserving no gentleness for you as his grip would no doubt leave bruises on your hips the next day.
He growls, the steady slap of his thrusts, bumping of glass and the blood rushing in your ear was all you could hear.
And even though you had already cum three times, you could feel a fourth bubbling deep inside, warming you up.
He pounded you against the glass.
He cursed as his thrusts became frenzied, violent bucks up against your ass as he chased his release.
“Fuck, fuck, fuck, here it comes!” He bellowed, digging his teeth into your shoulder and marking you hard. He groaned against your skin as his hot cum flooded you. You felt it fill you and warm you up, even if he didn’t let you cum again, you adored the sensation of him filling you up each time.
His thrusts slowed as you felt his seed begin to leak out around his length.
You mewled at the loss of the orgasm you knew he wouldn’t have given you anyway.
He pulled out slowly, releasing your shoulder and watching as his softening length fell from you.
Your knees buckled, but Jack was quick to catch you before you fell and scoop you up into his arms.
“There we go Baby,” he murmured, gently nosing at your temple. “Let's get you sorted.”
As usual Jack’s aftercare consisted of his soft praises as he tended to your physical needs.
He washed you, tended to your marks, dressed you back into your new pajamas, and tucked you into bed. You drifted in and out of his care, only catching a few words here and there.
“Good girl”, “Did so well,” and “So proud,” were the familiar praises you heard.
He joined you under the warm blankets when he decided you had been thoroughly cared for, pulling you close to his chest to snuggle and murmur affections at you. You nuzzled deeper into his warmth, completely boneless and spent, listening to the gentle timbre of his voice as you drifted off.
That night you dream about old castles and handsome southern princes.
credit to @talesfromtheguild for this little bit
“Hmm...”
“What are you hmming about over there?”
“You’d look good with a little blonde patch.”
“Shut up.”
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@thats-one-tender-foot @luminescentlily @nuttybeardetective @ishqinbbc @ben-is-a-hoe @calamity-queen @phoenixhalliwell @talesfromtheguild @the-arctic-violet @jeeperky @mando-amando
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