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Jack loves watching you get ready. He always makes sure to bring you to his place before any date nights or cook outs or any sort of event the two of you might have to attend— He swears it’s because his bathroom is bigger, the water pressure on his shower a hell of a lot better than that dingy thing in your apartment, but the truth is that he loves to sit at the end of his bed and watch you fleet around his room.
There’s some boppy pop music coming from your phone — It’s a Sabrina Carpenter song, which he knows because you keep belting out in his car but still pretends that he has no idea who she is because he loves how offended you get — and you’re wrapped around in a soft baby pink robe, sitting by the dresser as you lather up your silky smooth legs in the lychee scented body butter he got for you. You’d been very specific about it being butter not lotion and, while Jack still couldn’t figure out the fucking difference, he’d swiped the card with a smile on his face. It’s the best thing he’s ever smelled before, mouth watering in a way that can only be described as Pavlovian whenever he smells in— It’s soft and sweet and so you that Jack thinks he might mourn the day you decide to change it.
You have a different cream for your neck, and a different one for your face and a third one for the ‘under eye area’, as you call it. Jack thinks the under eye one is his favorite— Mainly because, after applying on yourself, you often sit on his lap and apply it on him too, tiny quick dabs of your pinkie on the crow's feet by his eyes that you swear you love. ‘Just keeping you hydrated, Jackie.’ you say whenever he jokes about you trying to get rid of his wrinkles; he doesn’t care, he’ll let you do whatever you want to as long as you keep sitting on his thighs.
You get dressed before doing your make up, which you tell him a lot of people don’t do — ‘You get one foundation stain while trying to put on a shirt, Jackie, and you learn your lesson.’ — and Jack almost wishes you’d do that too just so he could stare at the opening of your robe for a little longer. He thinks you know what you do to him by the way you slowly remove your robe, sliding into your underwear — flimsy and lacy and expensive, which Jack would know, since he’s the one footing the Agent Provocateur bill — before you stand in front of your section of Jack’s closet while you decide what to wear.
Jack lied before. This is his favorite part. He sits by the bed, half hard on the days his dick cooperates, dry mouthed on the days that it doesn’t, and watches as you shift from one foot to the other, browsing through drawers and hangers as if the closet is your own, private boutique. You go back and forth between two dresses and, although Jack has a favorite, he knows better than to intervene— This is your moment, your little routine of self-care and making sure you look good for yourself. You end up going with the dress he likes best even without his input, a dusty rosé shade that compliments your skin even though that’s not the only reason Jack likes it: It’s laced up in the back like a corset, which means you need his help to put it on and off.
There are very few things in the world that Jack enjoys more than being useful to you. He laces the bodice carefully; his deft fingers, so used to saving lives and taking them, clip every single clasp in place before he tugs the strings, making sure the dress is cinched but still comfortable: He has learned that one the hard way after you got lightheaded during a work dinner because you’d ordered him to tug it a little too tight. It accentuates your waist perfectly, showing off all of the curves that Jack likes to trace with his tongue and you giggle when he presses a kiss between your shoulderblades.
“You’re going to make us late.” You tell him but, despite your words, you lean back against him, Jack’s gripping your hips as he trails his mouth to your neck.
“We got time.” He whispers against your ear. And it’s true— Jack knows you take your time getting ready, and he certainly doesn’t want to make the same mistake he always made with his first wife and keep hurrying you up, so instead he lies to you about the arrival time; the reservation is at 8pm on your favorite restaurant, but Jack marked 7:20 on your shared calendar.
He doesn’t mind lying a little if it means he gets to watch you readying yourself up. He circles his arms around you and then runs his hands up your body, cupping your breasts; it makes you sigh, head lolling on his shoulder and, if this dinner wasn’t so important, Jack might’ve told you to skip it all together.
But he can’t, because he has a diamond ring in his pocket and he’s been practicing getting down on his knee with his prosthetic leg for over a month now.
“You can’t kiss me.” You say, voice just a little bossy. “It’ll ruin my make up.”
“You’re not wearing any.” He grins. “You never put it on before your clothes.”
Your body goes rigid for a second before melting against him— It pains him how surprised you always get when Jack shows interest in your habits, how you’ve never been known like he knows you.
“I already put on my moisturizer and my lip balm. It takes a moment to penetrate.”
He bites down against your skin, fighting very hard to swallow down the joke he wants to make.
“And you can’t lie down.” Jack states, smiling cheekily against your neck because he already knows the answer.
“Nope.” You pop the ‘p’ and Jack can hear the smile on your voice. “It’ll ruin my hair.”
“Hands on the dresser.”
Your body shivers in front of his but you obey nonetheless, bracing yourself on the dresser, ass rubbing against his crotch when you arch your spine. Even though he already knows what he’s going to find underneath the skirt of your dress, Jack’s mouth still runs dry at the sight of the baby pink underwear that frames your asscheeks; same color as the dress, a delicate mixture of satin and see-through mesh that he simply cannot stop and appreciate. The pad of his thumb runs over the fabric, chuckling when you wiggle and push back against him. He kneads the fat of your ass, the tip of his thumb barely teasing the gusset of your underwear— It’s already dampening, the satin just a little darker there.
“I didn’t even touch you and you’re already this wet?” He tuts.
“I’ve been wet since I got in the shower.” You admit, head turning just a little to look back at him, eyes blown with need. “Thought you were going to join me.”
Desire curls down his spine at your words; Jack had a long time to make peace with the loss of his leg, at this point in his life having lived longer without it than with it, but he’d still been self-conscious around you at first— He refused to shower together, a lot of the times even refused to take off the prosthesis around you even in his own home no matter how painful it got. He had felt like half a man at first, afraid that you’d see him for what he really is: An old, ptsd-riddled war veteran with half a missing limb and your entire life’s worth of trauma.
But then you pushed him down onto the built-in bench in his shower, rode him until your body gave out, and that was that— Jack never felt like half a man anymore. You treated him the same, perhaps even better; he’d tense at first, whenever you decided you wanted to massage his leg after a brutal shift, but you never made a big deal out of it. It’s just a part of who he is, like his grey hair and the wrinkles on his neck, and you love him all the same.
“Jackie—” You breathe out and Jack immediately knows he’s taking far too long, your hips pushing backwards, trying to find him. All he wants is to crouch down and lick you until you’re screaming for him, but Jack needs the two of you to get to the restaurant on time. He pushes your dress up, tucking it on itself so it doesn’t keep sliding down your body.
“Patience, sweetheart.” Jack pulls down your underwear slowly, mouth watering as he watches it stick to your cunt for a second before finally letting it fall down your legs. “I’ll give you what you need.”
The tip of his finger runs through your folds, not really pushing in, just feeling you. He sees the way your body shivers, your breathing cutting off for just a second, waiting. Jack gathers your slick, brushing it towards your clit and you shift, spreading your legs a little more.
“Jack—” You try again, but he cuts you off again, giving firm, long circles around your clit; toying with it, giving you just enough to make you as needy as he wants you.
“Did I ever tell you how pretty this pussy is?” His fingers pull the hood of your clit back just enough to run his thumb over the most sensitive part, the one that has you keening and bucking away with barely a touch. “Prettiest pussy I’ve ever seen.”
“Yeah?” You ask, a little breathless, but there is a special kind of fire when you look at him over your shoulder. “Does that mean you’re thinking of someone else’s pussy right now?”
Jack laughs, leaning forward to pull you back against him, his mouth finding yours when you crane your head back just enough. You bite down on his bottom lip, a little sharper than usual, and Jack’s finger finds your entrance. “Never.”
“Good.” You respond just as he sinks his middle finger into you. You clench down on him instantly and Jack has half a mind to replace his finger with his cock; he holds himself still, though, dragging his finger in and out, slowly. You whine, and Jack knows you’re trying not to fuck yourself on his hand. “Another.”
Jack hums, palming himself through his slacks. “Gotta be more polite, baby.”
“Please, Jack.” You say it through clenched teeth. “Give me another finger.”
You can do better than that, he knows you can. He could probably drag this on for a lot longer, teasing you until you’re begging so prettily, but he gives his watch a single glance before plunging his ring finger inside of you.
“There you go.” He coos, watching as his fingers disappear inside of you. It’s a stretch even with just two fingers, your slick heat trapping him inside like a vice; he scissors his fingers slightly, feeling you give a little around him, his entire body set aflame at the needy noises you’re making. “That’s enough for you, baby?”
“No.” You shake your head, body jolting when he twists his fingers just right. “Need more. Need your cock—” You pause, just for a moment, before adding in the most saccharine tone Jack has ever heard. “Please, I need you to fuck me.”
And who is he to deny any of his baby’s requests?
Jack plants his feet on the ground, steadying his posture before freeing himself from the confines of his slacks; you bend your spine at the noise of his zipper opening up, leaning forward and jutting your ass further in the air. He uses the hand that had been inside you to slick himself up, pumping his length just a couple of times before notching it to your entrance. You clench around his leaking tip, almost pushing him out; the sensation makes Jack dive his hips forward, sheathing himself entirely inside of you with just one thrust.
You moan, loud and unabashedly, reaching behind to hold Jack’s hand. He waits for you to adjust, knowing that the thickness of his fingers is nothing compared to his cock, but the clock is ticking— Jack moves his hips slowly at first, languidly, pulling out just halfway before pushing into you again. Your hand tightens on his, long fingernails digging into whatever bit of his fingers that you can reach: It leaves a mark behind, deep red scratches, and Jack gathers both of your hands behind your back, holding them at the small of your back before he picks up the pace.
You’re like a ragdoll in his hands, pliant and welcoming, letting him fuck you as hard and as fast as he wants to— Your body moves when he makes it so, and you moan so loud it nearly drowns out the filthy, squelching sound as your cunt swallows him whole again and again.
“This is what this pretty little cunt needed, isn’t it?” Jack asks, almost out of breath as he dives into your warmth. “Teasing me like that, getting all dolled up for me.”
“Who— Who says I was doing it for you?” You ask and, even though Jack can’t see your face, he can hear the grin in your voice. “I look pretty for myself.”
Jack’s open palm slices through the air, connecting with your asscheek hard enough to make you yelp. You clench down on him so tight that he almost comes right there, teeth clacking against each other in an effort to keep himself from coming before you.
“If you can still be a brat, that means I’m not fucking you hard enough.”
“Maybe you should try harder, then— Fuck, Jackie.” The cheeky sentence turns into a mewl when Jack moves just enough to hit a different spot inside of you, the one has your eyes rolling back into its sockets, the one you’ve told him no other man has ever been able to reach; he sneaks the hand not holding your wrists down your front, finding your clit with fast, jerky movements.
“There you go.” He says when he feels you melting in front of him, forgetting yourself in the midst of pleasure. Jack likes when you talk back, thrives on it in fact, but there is something to be said about watching you drop all pretense and just enjoy him and the things he does to you.
Your orgasm comes without warning, Jack’s name on your tongue like a prayer before you go completely silent, cunt spasming around him so violent that his hips stutters; Jack doesn’t stop but he slows down his thrusts, letting you enjoy the moment, lost in how long it takes before you relax again.
“Cum in me.” You say, breathless, body limp against the dresser. Jack lets go of your arms, then, and you rotate your shoulders for a moment before bracing yourself again. “Please, Jackie. I wanna feel you dripping out of me all night.”
It’s the image of you sitting in a fancy restaurant, leaking his come through the expensive underwear he paid for that drives him over the edge. Jack buries himself as deep as he can, hands on your hips and forehead between your shoulderblades as he comes.
“Jesus.” He breathes out, still leaning against you. “Can’t go around saying shit like that, sweet girl.”
You giggle, reaching back to run your fingers over his forearm. “You seem to like it.”
Jack chuckles, but he doesn’t confirm it— Doesn’t need to. He presses a kiss to your shoulder blade, asking instead:
“Are you alright? Does anything hurt?”
“Just peachy.” You turn around when Jack pulls out, wrapping your arms on his shoulders and tugging him close, your concern with your moisturizer and hair entirely forgotten as you press your lips to his. “We’re going to be late, though.”
Jack checks his watch, giving you a tiny, shameful grin. “It’s fine. We don’t gotta be there until 8.”
The confession makes you gasp, untangling yourself from him; Jack occupies himself with tucking his cock back into his slacks, trying to avoid the offended look on your face. But to his surprise you just coo, taking his jaw into your hands, a loving smile on your face, your eyes soft and smudged with dark mascara.
“You know me so well, Jackie.” Your thumbs brush his cheekbones. “Take off your shoes and your leg, I’ll be ready in a second.”
It takes you fifty-seven minutes to get ready, deciding to change your outfit because he wrinkled your dress and then also deciding to change the styling of your hair because ‘it doesn’t go with the dress’, and Jack takes the time to nap even when he swears he’s just resting his eyes— By the time you two arrive at the restaurant you’re too late for your reservation but you look so pretty and so happy that Jack doesn’t mind waiting another forty minutes for a free table.