#schlossberger

[oceancentury]

John ‘Jack’ Bouvier Kennedy Schlossberg (only grandson of John F. Kennedy and Jacqueline Bouvier) is Vogues new political correspondent.

[melancholicstation]

HUSBAND JACK SCHLOSSBERG HEADCANONS 𓍼 𓇢𓆸

taglist: @remotewatch @bloxholden35 @kennediva @h-l-vlovesvintage @absurdlyvintage @chemicalw0rld @fortheloveofjos @kimcrystal123 @astro-vibes-bro @tsloverr-13

might make this into a couple of one-shots??

imagining WIFE!READER as an orion carloto type, who balances modelling and writing, and makes tiktoks in the same vain of alanabananaxox on tiktok (she's been my no.1 tiktoker since 2021) and sotce.

met wife!reader at a runway after party of an up and coming new york indie brand ( sandy liang, khaite, bode etc. )

proposes to you with the blythe doll you had been obsessing over, dressed in a wedding dress and hand-customised by a popular etsy dealer with quite a high rate like this girl on tt

encouraged by jack to do a ‘what’s in my ( miu miu joie leather ) bag’ video on tiktok to help campaign for kamala akin to this video of anne hathaway but with a different vibe.

jack is ultimate embarrassing hard launcher bofy, leaving in all his girlfriends giggles that come from his chaotic antics when filming his videos.

wife!reader loves to slather jack’s face in biologique recherche’s “masque vivant”, he complains that it smells like rotting meat😹😹😹😹😹.

jack would be always on that damn phone during your runway shows, recording each time you pass him by in the catwalk.

would be the absolute opposite of marriage-shy.

unpopular opinion this man would be asking about marriage, a solid 3 months in ( jfk and jackie married in a YEAR )

fucks UP a rotisserie chicken.

forwards you his tweets before and asks if they’re good enough to post.

smells like aesop musk and of herbal deodorant.

wife!reader buys rick owen’s black and white t-shirts and slacks for jack, and jack’s absolutely baffled when he learns the price tag.

love language is buying wife!reader drinks whenever and wherever they are: hot chocolate in central park, home-delivers you a sab benedetto sparkling water because he had a meeting at cipriani downtown, and always orders a polo bar punch for you prior to your arrival to your shared weekly dinner date at the polo bar on 55th st.

instigates a24 marathons on friday nights, much to the dismay of your prior night plans ( you are more of a criterion collection girl and have held a subscription since you were a freshman in college )

( clumsily ) slips lana del rey lyrics into sexting and dirty talk.

husband!jack and wife!reader texts go like this:

jack is horrific at low impact pilates, he needs to be near a body of water.

he wears your prized doublesoul x orion caroloto ‘lamb’ socks around your woodfloored high-rise despite your varied attempts at hiding them from him.

constantly frets over you during society galas, which is quite convenient due to your tempered social anxiety and your forgetful memory of high society etiquette.

immediately brings you to meet the family, for which you were completely unprepared for ( i’m imagining something reminder of that one story of meghan markle meeting princess kate middleton in ripped jeans and bare feet )

jack loves to wear your 100% cotton brandy melville pointelle tanks despite them being comically tiny for his frame.

would have an innocence kink.

he gets intensely flushed when called his proper full name: john bouvier kennedy schlossberg, wife!reader abuses this to the HIGHEST degree!!!

the first time he entered you apartment he was constantly paranoid of breaking anything because your house was littered with ceramics from brooklyn under-ground designers and clay lamb figurines.

he NEEDS his beauty Zzzzzzz or else.

plays with your very expensive westman atelier blushes like a toddler.

sickly devoted to you.

you both want to adopt a lamb despite living in a HIGH-RISE apartment.

sends pics captioned with anaïs nin lewd quotes.

he would think whole foods was stupidly over priced but would purchase his groceries there in spite of his opinions.

has hyperfixations on old-hollywood women which causes you to be snippy at him for exactly 2-3 hours ex. jack’s current hyper fixation on audrey hepburn being his doppelgänger.

wife!reader definitely participated in that egg cracking trend where girls would crack an egg on their boyfriends head.

would love caring for your hair and doing your curly girl hair routine if you had one.

wife!reader does small yet viral shoots for brands like mirror palais, the row, and loewe.

manhandles you ( lovingly ) without even trying.

mans is a chronic diptyque candle lighter.

loves to be coddled and cradled as a grown man…

plays with your van cleef stack before stage when he’s nervous about his speech landing correctly

uses his family connections to get his girl courted by the high-ticket fashion brands: schiaparelli, chanel, dior, yves saint laurent etc.

[politicalchange]

jack schlossberg talking you through it.

only for your pleasure of course. he loves making his girl feel good. you’d be bouncing on his girthy cock, wet sounds filling the room along with you loud moans & whimpers, while jack just looks up and watches you, while his hands gripping your hips and occasionally grabbing your tits. he can tell your close just by the laziness of your movements and the constantly throwing your head back while you rolled your hips on his. “fuck jack baby please.” you whimpered and put your hands on his chest, all tired and fucked out.

“cmere baby.” he said in a low, raspy morning voice. he pulled you down onto him and crashed his lips onto yours, slipping in his tongue and running his long, veiny hand through your hair, while his other hand caressed and squeezed your ass. “you like makin a mess on my cock huh pretty girl.” he smirked at you and you nodded, you started grinding your hips back and forth against his again until he stopped your movements and started fucking up into you.

you moaned loudly and threw your head back, one of your hands gripping onto the headboard and the other onto the pillows. “cmon baby i know you got one more in you. do you pretty girl?” you nodded and buried your head into his neck and continued moaning. “no say it y/n. say you’ll cum for me again baby.”

“fuck yes jack i’ll cum for you.” he laughed in your ear as he continued fucking up into you, keeping up his pace and occasionally smacking your ass. he grunted as he felt you clench around him and threw his head back into the pillows. you whimper his name and throw your ass down on him, matching his rhythm as you both try to chase your highs together.

he feels your body tense up and you start to tremble and he wraps his big, buff, veiny arms around you to hold you close so you don’t try to run away. he knows your close. he was forcing you to take every inch of his cock while he whispered dirty things into your ear. “you like when i fuck you like this princess? you gonna squirt all over my cock?” all you could do was cry out and squeal from the pleasure.

“give it to me baby. cum all over this dick.”. you squeezed your eyes shut and continued to rock back and forth against his cock while you came. you whimpered against him and gripped onto his hair, looking for support in something. a few moments after, jack grunted into your ear and came himself. he always made sure you came first. “oh fuck baby this pussy feels so good.”

he rubbed on your back and tried his best not to ruin your high, “calm down baby i know.” he continued to let you rock back and forth.

“look at you princess you did it for me, didn’t you.”

[reminiscing4ever]

[uniicorns-arereall]

are you guys ever reading some absolutely FILTHY smut and you just think to yourself:

like why are we bringing crazy plot points into this… and why do i kinda like it ?? JK JK

[kennedyformee]

😩😩😩😩

[velunas]

summers in the air, heavens in your eyes

pairing: jack schlossberg x reader

summary: sex on the beach with your boyfriend jack

wc: 1.3k

warnings: smut!!! oral (f receiving), swearing, p in v sex, kinda public sex (pls do not have sex in public or on the beach u will get sand in ur vajayjay), terrible ending

a/n: WELL... listen i've been in love with jack schlossberg since like 2016 and everyone is finally realizing he's hot as fuck so here we are and i have no regrets. enjoy sinners <3

minors do not interract plz! xoxo

the air was thick and warm, the humidity making your hair stick to the back of your neck. your boyfriend jack lay beside you on his back. his eyes are shut as he basks in the sunlight. there are streaks of white on his cheeks from the sunscreen you slathered on him before he ran out to the ocean, eager to surf. a headband you lent him pushed his dark hair back, and his soft skin was now slightly darker than when you arrived that morning. 

“i can feel you staring at me, y’know.” 

he says, reaching a hand over to pinch your soft thigh. you giggle and playfully smack his arm. “didn’t realize it was weird to stare at my boyfriend.” you retort. he cracks his eyes open and turns his head to look at you. he smiles softly and opens his arms, beckoning you to sit on top of him. you comply, moving so you’re now straddling him. his large hands find home on your hips, his thumbs rubbing circles into the skin there. 

“hi, pretty girl.” he moves a hand to cup your cheek and tugs you down to kiss him. your mouths meet gently, moving in tandem. his tongue prods at the seam of your lips and you open them for him. he explores the inside of your mouth, groaning at your taste. “tastes like strawberry.” he mumbles between kisses.

the hand lying stagnant on your hip moves to the tie holding your bikini bottoms together, twirling the strands between his fingers. you pull away and his head chases you, silently asking for more. “jack, we’re technically in public, anyone could see us like this…” you tell him and he rolls his eyes. jack sits up and you shift down on his lap. he brings his mouth to the shell of your ear, licking it before whispering to you “seems pretty empty to me, baby.”

you look around, doing a sweep of the area to make sure it is truly empty. the beach was mostly private, a secluded location in front of the beach house that jack had rented for the weekend for the both of you. there was no one as far as your eyes could see. technically, you were on private property. if anyone saw you two together, it was practically trespassing. throwing all of your worries away, you lean back into him, connecting your mouths once more. 

he smiles into the kiss, pulling you as close to him as possible. his strong arms wrap around your waist, pulling you directly on top of his arousal. you groan at the feeling and grind your hips further into him. before you can protest, he flips the both of you, lying you on your back. he moves his mouth to your neck, lathering hot and wet kisses and leaving purple blemishes in his wake. he shifts down slightly, pressing kisses into your collarbones and between the valley of your breasts. 

his hands again reach for your bottoms, and jack looks up at you for permission. as soon as you nod, he slides them down your hips and slips them off, throwing them onto your towel. his hand slides up the length of your thigh, stopping at the innermost part. he hums and leans down, pressing a kiss to your pubic bone. “so pretty down here, honey.” he mutters to himself. 

with that, he devours you. his tongue snakes out to caress your clit. one hand holds your hips steady, while the other slithers down to your slit, slipping his middle finger inside of you. the pleasure you feel is burning hot, a fire that begins to burn in the pit of your stomach. a strangled cry wrings its way from your lips as jack adds a second finger. his fingers move earnestly, knowing exactly what you like and how to drag you to your peak. 

“please, jack. it’s so good. i’m so close” you whine, pushing your hips into his warm mouth. he doubles his efforts at that, sucking your clit into his mouth and quickening his fingers. you bring a hand down to his soft hair, pushing his headband off. his dark locks fall into his eyes, but you’re quick to hold them back yourself. he moans into you as you tug at the strands. 

“c’mon, sweet girl. cum for me, lemme taste it.” 

and you do. your orgasm rips through you almost violently. your hips twitch and your moans are unrestrained. his mouth relaxes and instead presses soft kisses against you as you float back to earth. he travels up the length of your body until he reaches your face, kissing your temple, cheek, and the corner of your mouth before kissing your lips. you could taste yourself on his tongue. 

his hips press into you, grinding into your naked body. he brings a hand down to quickly pull off his bottoms, jerking himself off quickly before spreading your legs. aligning himself with your hole, he pushes into you slowly, allowing you time to get used to his impressive girth. it was no secret that jack was extremely well-endowed, and no matter how many times you had sex with him, it was always an adjustment in the beginning. 

he eases into you slowly until his pubic bone is flush with your ass. he pulls back steadily, rocking back into you with restraint. “s’good, baby?” he asks. his accent is thick and his words are slurred slightly as he loses himself in pleasure. you nod, wrapping your arms around his neck. “it’s so good, you’re so big.”

jack speeds up his movements, slamming into you. his breathy moans invade your ears and you can feel him twitching inside of you. he pulls out of you and taps your thigh, signaling you to change positions. he lays on his back as you throw your thighs over his hips, pushing yourself down onto him again. 

he throws his head back, gripping your hips with a bruising force. if you weren’t so fucked out, you’d tell him to ease up so as not to leave finger-shaped bruises in your skin that could be so easily spotted. but the only thing that was on your mind was bringing the both of you to your orgasms, so you got to work. planting your feet, you begin to bounce on him. he thrusts his hips in time with your movements, pushing into the soft spot hidden inside of your walls. 

“god, baby. you’re so good at this. just made for me, huh? perfect little pussy that only i get to fuck.” 

you clench your thighs around his waist as you feel your climax approaching. “yeah, i’m made for you, jack. m’your girl forever.” you gasp. as if he can sense how close you are, he brings a hand up to your clit, rubbing it in quick and tight circles. he pounds his hips furiously in time with your movements. you feel him spasm inside of you, warm spurts of his spend painting your walls. that brings you to your second orgasm, convulsing above him. 

you collapse onto his chest, attempting to catch your breath. he wraps a weak arm around you, breathing heavily into your ear. the two of you come down in silence. as your breathing evens out, he presses a loving kiss on the crown of your head. “you ok, baby?” he whispers into your neck. “tired” you mumble, nestling farther into him. he tightens his hold on you before shifting to sit up, still inside of you. 

“let’s get you inside, sleepy head. we can take a nap together.” 

he lifts you off of him, and you whine at the sudden emptiness you feel. he pulls up his swim trunks and stands, grabbing your towel and wrapping you in it, guiding you back into the house to lay down and enjoy the rest of your peaceful evening together.

[reidtina]

Mr. President

Pairing: jack schlossberg x fem!reader

Content warning: +18 MDI semi-public sex (I think it's considered), oral sex (reader receiving), pet name calling (honey, darling, baby, babe), vaginal fingering, orgasm, office sex, smut, mentions of sex, established relationship, I think that's it

Word count: 1.9k

Summary: Jack Kennedy Schlossberg is the grandson of the Former President John F. Kennedy, and now he's the one to assume the role of president of the USA, he's a serious politician, but when it comes to his girlfriend Y/N, he's also a little horny, which sometimes leads to situations like eating her pussy in his office at the white house.

A/n: i wrote it because I didnt find many fics of him, but it's my first ever, I posted it on ao3 too

You’ve been dating Jack for over 3 years now, you lived in New York City, and since he moved to the White House in Washington you didn’t get to see each other as often as you’d want, but you had a few free days this week, so you decided to spend them in DC with him. The guards already knew you, so they let you in and you went straight to your boyfriend’s office on the west wing.

When he hears your knock on the door, he yells a little “come on in” and as you open the door, he looks up from the paperwork he was doing and smiles at you.

“Hey, darling” he says standing up from his chair and making his way to you and wrapping his arms around you in a tight hug. “I’ve missed you” he sighs, placing a kiss on your forehead.

“I’ve missed you too, babe, I wish we could spend more time together” you say

“I know” he replies, sliding his hands to your hips, pulling you over to sit down on the edge of his desk. “But I want to make up for the lost time” he stands between your legs, running his hands up and down your thighs. “I was about to go crazy having to work without seeing you all day” he says kissing your neck. His fingers move just under the hem of the tight black dress you are wearing.

“God, how I love this dress” he mumbles, his hands moving from your hips to slowly run up and down your back, feeling the soft lace on your skin through the fabric.

“Does that mean you don’t want to take it off?” you ask in a teasingly tone with a grin on your face.

He chuckles and is fast to reply “Oh, no, honey, I may love it, but there’s nothing you can wear that I’d like more than the sight of your bare skin”. He bites your shoulder lightly and runs his tongue over the spot he just bit.

Jack nips at your neck, planting a trail of kisses all the way down from your neck to your collarbone. “It’s not even fair how beautiful you are” he mumbles against your skin, his large, warm hands sliding under the dress to grab your thighs. He pulls back to look at you and his eyes roam your body, admiring every curve and dip of your figure under the form-fitting dress. “God, I need you” he groans.

“You have me, I’m yours” you say looking deep into his eyes and your hand cupping his face, pulling him in for a kiss.

When you break the kiss, he says “No, I need you right now” gripping at your waist to pull your body closer to his, pressing his hips into yours. His eyes are darkened with lust, his breathing heavy. “Can you lock the door?” he asks, his voice low and gravelly.

You get up from the desk and make your way to the door and while he closes the curtains you turn the key on the door, locking it and as soon as he hears the click of the door locking echoing through the office and you go back to where he’s standing, he pounces. He grabs your hips again and pins you to the edge of his desk, his mouth crashing into yours in a messy kiss. The kiss is hot, desperate, his tongue invades your mouth, tangling with yours.

“Hooking up with the president in the white house, that’s kinky” you mutter through the kiss, running one hand through his hair and the other lightly scratching his chest. “God, that mouth of yours” he mutters back, then running his tongue slowly over yours, before pulling away slightly. “Maybe I’ll have to put it to good use for me” he says, nipping your bottom lip and pinning you harder to the desk with his hips. His hands grip your thighs, slowly sliding up your dress. He plants a trail of kisses down your neck, biting softly at the skin, his warm breath fanning across your chest through the fabric of your dress. His hands continue to slide up your thighs, and he moves to push your legs apart.

He lifts you up and sets you gently on the desk, his body now between your legs, his lips are on your neck, slowly sucking in the soft skin and marking you as his own. His hands are on your hips, holding you against him as he continues to kiss and bite every bit of skin he can find, sometimes getting a moan out of you.

“God, you’re delicious” he mutters against your skin, his hands moving to your thighs as he pushes your dress up, slowly running his hands up your bare legs, his lips find their way to your collarbone, and he kisses, nips and sucks, masking your skin as he goes. “So soft” he breaths heavily, placing a kiss right over your chest before moving down to your bare thighs, his hands grip on them, as he slowly spread your legs wider “I need more” he groans and you moan to the feeling of his mouth on your thighs. “Take it” you say softly and low.

His lips move to your knee, where he bites down gently “Careful what you say to me” he mutters, his hands slowly tracing up your inner thigh “I’ll take everything I can”, his words send shivers up your spine. “It’s yours to take” you whisper as he pushes your legs open even further, biting gently at your inner thigh, his lips moving over your skin “you’re mine” he says, his hot breath washing over you. “I am” you confirm, nodding and caressing his hair as his lips find their way higher and higher, until you feel them press against your core through your underwear, he gently bites and sucks at the skin and then pauses to say: “and no one else’s”

“No one else’s, only yours” you confirm again, eager to feel his mouth on your skin again and then his tongue darts out, licking over the fabric of your underwear once again. He looks up at you through black eyelashes and whispers “I’m going to show you exactly who you belong to”, his fingers running over the lace of your panties. “Show me, babe” you ask.

He grins at you, and in one swift movement, he hooks his fingers into your panties and pulls the lace off, tossing them somewhere on the floor, before quickly getting back on his knees in front of you. He runs his hands up your legs again, his fingers slowly running over the sensitive skin of your center. “I’m gonna make you say my name” he says in a seductive tone. “Oh, fuck” you let out a moan when one of his fingers enters you.

He moves his other hand up to grip your thigh, pulling you closer to him “That’s not it, darling” he teases, his breath hot on your skin and now two fingers moving inside of you. “Say it” he demands, his lips trailing up your thighs, moving closer to where his fingers are, his lips move up and down, not quite where you need them yet. “Jack, please” you beg, your voice shaking in lust and need. He runs his tongue over the sensitive skin of your thighs, teasing you “please what, honey?” he asks, looking up at you, his brown eyes darkened with lust, burning through your skin. “Please eat my pussy” you ask, barely able to let out the words through your desperation. “That’s all you had to say, darling” he mutters, and wasting no more time his tongue dives into you, his mouth and fingers working over you. He sucks and licks at your skin, tasting every bit of you as he devours you, his tongue moves rapidly.

He pulls back for a moment, running his tongue over his lips, the corners of which turn up in a sly grin “I’ve been wanting this all that, baby” he says and you grin down at him and teasingly say “You love the way I taste, don’t you?” He hums against you, his tongue running up and down again “Yeah, I do. I’m addicted to you” he says, his eyes flickering up, watching your facial expressions, admiring your moans and the way you tilt your head back in pleasure, loving every second of it. “You know I love when you sound like that” he mutters, his eyes never leaving you. “Jack” you moan his name, the sound of it sending blood down his cock, he loves the sounds you make, loves the fact that he’s able to get you this worked up “Say it again” he asks and you obey, moaning his name again as you bite your lower lip “I’m almost cumming, Jack” you groan. “Yeah, baby?” he smirks onto your skin, keeping his fingers movements at the same pace and asks you “Tell me what you want”

“Just keep doing it like this” you say grabbing his hair and he groans against you, loving the feeling of your fingers in his hair, he obliges, continuing to move his tongue and fingers in just the way he knows you love. “Just like this, baby? You like that”

“Uhm, yeah, just like that” you moan, his mouth working to get you just where you need to be, you feel your legs shaking and your breath getting heavier when you finally cum on his fingers and mouth, he laps up your release, pulling out his fingers and running his tongue over your core and sucking his fingers before standing up and grabbing you to hold your body against his. He kisses you, giving you a taste of your own pussy, “You’re so perfect” he says, cupping your face and holding your body against his. “I love you, Jack” you reply, he smiles, a soft, love-filled smile as he lifts you into his arms and walks over to his chair, sitting down and pulling your body into his lap, he wraps his arms around your waist, nuzzling his head into the crook of your neck and whispers “I love you too, y/n”

“Where are my panties? I can’t be caught sitting here on your lap wearing nothing but a dress” you say and he grins against your skin “They’re on the floor somewhere, let’s hope no one walks in” he says, pressing a gentle kiss on your neck and running one hand up and down your bare leg. “Let me just grab them” you ask, grinning too and attempting to stand up, but he holds you in his lap “Oh, no, you’re not going anywhere, not when you’re sitting on my lap with nothing but a dress”.

You chuckle and say “You’re so naughty, Mr. President”, he grins and says “Only for you, you menace. You make it so easy when you wear a dress like this”. So you tease him and say “Even easier when I don’t wear anything”. He groans and bites your neck “Don’t tease me like this, you know I’ll have you again” he says, running his hands on your bare thighs. “I’d be happy to let you have me as many times as you want to” you say, smirking. “I need to go through a few meetings and then I’ll take you back to my room” he promises, making even more eager to have him all to yourself all night long. “I can’t wait for that” you grin.

“Oh, I have so many ideas” he says, his lips moving to your shoulder “and you’ll have to follow every single one of them” he teasingly whispers, nipping at your skin and making you smile to the thought of the night you’ll have.

[guy60660]

Jack Schlossberg | Vogue

[remotewatch]

some call it arrogance

Jack Schlossberg x reader | 2.5k wc

summary: Let’s face it: you kind of suck at paddleboarding. Thankfully, your boyfriend is an eager instructor with a trick up his sleeve!

cw: shameless smut, outdoor recreation, questionable teaching, peppy upbeat softdom jack (good lord), fingering, unprotected sex, if you want to keep your plan b go VOTE ‼️‼️, play fighting, jd is catching strays, this is somewhat a comedy

minors dni and stay out!!!!

Time and time again, you realize that you and Jack have very different definitions of what constitutes a short paddle. You could pass out right here on your little break, sun hat plopped over your face and one leg dangling in the pleasantly cool water. He tugs you closer to his board to drum a few fingers on your knee and ask “You asleep?” just as you’re drifting off.

A barely audible “mhm” is all you care to let out. Jack’s hand slides to your inner thigh, a polite veneer of concern slapped onto his more crude interests.

“Do you need something?” When you lift your hat to squint over at him for being so euphemistic, he’s already zapping you with those doe eyes you struggle to resist.

“Diva, the telephotos,” you mumble as you flop back down. There’s almost certainly no one hiding out in the mangroves waiting to catch you two, but the press had noted the extension of your Japan trip to stop at Iriomote. Your growing collection of condemning paparazzi pics is already nudging at the edge of your mind, and you have no desire to add to it today.

“They can’t get a good shot this far out.” His hand stills when you don’t murmur back how much of a whore he’d have to be to know that so definitively.

“Here, let’s get out of the sun for a bit. Get you a honey stick or something.” A grateful thumbs up is the most movement you care to make.

As much as you like getting into Jack’s hobbies with him, it’s undeniably more fun to have him tow you around whistling Elvis tunes like your little chauffeur. It would be so easy to fall asleep to the sound of it paired with the waves crashing in the distance; maybe you do; it’s really none of your business.

The temperature suddenly drops, and you briefly tilt your hat up to see he’s steered you into a particularly thick mangle. It’s a straight, narrow shot from it up to the shore; exactly the type of hidden launch he’d know about.

He turns around from rooting in the supply bag and waggles a fanned out selection of power bars, honey straws, and glucose gels at you.

“What’re we having today, huh?” Still hiding under your hat, you grasp blindly until you find a few straws and tear one open with your teeth, shoving your dentist’s exasperation to the back of your mind. Jack knows better than to pester you until your temperature and blood sugar level out a bit. Eventually, you rise from the dead and get a better look at your spot.

The mangrove roots here are as thick as you’ve ever seen and rise far enough out of the water that you could set up a hammock under them. Schools of diminutive silver fish swirl beneath the surface, bouncing light back up to paint the underside of the overhead foliage. The two of you are technically visible from open water, but a pap would have to drop anchor at the perfect angle to get more than a glimpse. You remind yourself that you’re on the west side of the island anyway; surely there’s more exciting things to report on than America’s most notorious SUP proficiency gap relationship.

“You’re getting better, you know.” You gnaw at a second honey straw and scrunch up your nose.

“Am I?”

“For sure. Remember Lake Superior?”

“God, must I?” you groan, wincing at the mere thought.

“Gotta appreciate where you started!” Jack is laid out on his board doing alternate toe touches, and the fact that it’s more of an unconscious ritual than a way of showing off his balance makes it all the more annoying.

He’s truly so pretty, even after putting your legs through hell on the way out. The little gaps in the mangrove canopy cover him in spots of sunlight, and he still refuses to buy a smaller pair of shorts, just rolling down the hem of those ratty old ones until they’re shorter than any of yours. You’re too busy watching them fall further down his thighs with every leg raise to notice he’s still talking.

“Sorry, what?”

“I said-,” Jack finishes the last of his coconut water and smacks his lips. “Why don’t you stretch a bit before we head back?” You press your hands flat as if to push yourself up, and he notes your hesitation.

“What is it?”

“…Can you spot me?” His smile cracks his whole face open like a fresh daffodil, clearly thrilled to be needed.

“Why, certainly.”

You brace yourself as he slides onto your board as easily as scooting closer on the couch, quads flexing delectably while he helps you stand up.

“Do a forward bend for me,” Jack effortlessly slips back into his instructor cadence, to the point that you could forget he’s your boyfriend aside from his hands feeling far more than professionally comfortable on your hips. He leans up against your backside to peer over you as you place your palms flat on the deck, not bothering to conceal how much it excites him. After the tension of the paddle out and stiffening up during your nap, the stretch in your hamstrings is virtually orgasmic. Jack doesn’t miss the little sigh of relief you let out, nor do you the the smugness that spills into his voice.

“And walk it out, just like that,” you can feel him staring at your ass and can’t even kick his shin without knocking you both over.

“Can you at least pretend to enjoy this a little less?” it doesn’t sound very commanding with his dick pressed right up against you before you shift into downward dog. Even less so when he knows how much you love a good calf stretch, knows exactly how far to push you into it to make you melt in his hands.

“If I’m not happy to be here, how can I expect you to have any fun?” There’s a brief wobble as he reaches to grab your ankles and help you move to a headstand, but one shift of his heel and you might as well be back on dry land.

“That’s why I said pretend.”

“That’s why I’m not an actor. And, push yourself up!” If nothing else, you’re decent at handstands, at least with Jack ready to catch your legs. Decent on a good day, that is, when the humidity isn’t bleeding your energy like a stuck pig. Your right palm slips into the water, and you screw your eyes shut in anticipation of a face full of board and a few tree bark scrapes.

“Fuck!” you hiss, but his grip instantly locks down on your ankles and lifts you out of the line of fire. Jack’s obliques ripple as he rights the board, and he’s very clearly pleased to catch your notice of it.

“That’s alright, you had a few good seconds there.” He lets you swing a few moments longer than necessary before lowering you back down and piping up again. Ever the show-off.

“It’s always…,” he hesitates as if he’s searching for the right words. “-been my understanding that if you can balance on all fours in unfavorable circumstances, you can stay standing just fine.”

“And what kind of unfavorable circumstances would you be talking about?” it’s obvious, though you’d rather hear him say it. He knows you too well to take the bait and cheekily rolls his eyes.

“You know, the favorable ones.”

“Is that what they teach you at surf instructor school?” Your hands are back on the board now, and you kick one foot free to slide it down his chest under his shorts.

“Oh yeah, the first thing,” he chuckles, fishing it out before helping you down into a plank.

Jack somehow wriggles his way under you without causing any major upheaval, claiming it’s the easiest way to check your form. He’s talking like this is your first time on a board just to wind you up and making no attempt to hide how much he enjoys doing so.

“Now, there’s nothing to it, just gotta make sure you’re not leaning too far to the left-“ he tugs at one of your bikini ties.

“Or the right,” he twists the other between his fingers, not quite loose enough to fall off, but certainly plenty of room for him to slide his fingers below your waistband. His smile grows wider when he pulls them back out to observe their newfound shine. You have a halfhearted go at defending your reactivity.

“That has nothing to do with you.”

“Oh yeah? You’re pulling a JD, getting riled up by the dolphins?” If your balance or endurance were half as good as his, you’d shove him off your board and ditch him right there. The best you can do is double down; a bit pitiful, but better than giving him any satisfaction right after that bullshit.

“And these are the unfavorable circumstances? Seriously?” It’s more the stupid fucking grin on his face than the controlled circles he’s tracing on your clit that’s disrupting your concentration. You’re hoping that focusing on the space between Jack’s eyebrows will keep your mind blank, but his fingers feel better and better the more you try to ignore them sliding around like he’s trying to memorize every cell you’ve got down there.

“It would be deeply irresponsible of me to throw you right into the deep end. Safety first, after all.”

“So irresponsible,” the mocking tone you’re going for doesn’t really work when your pitch is stuttering in perfect response to his movements.

Your eyes slip closed out of habit, but he’s right there playfully pinching your nipple to bring you back to reality.

“Hey, now! No daydreaming during your lesson! That’s not very considerate to your instructor,” he’s trying to pout up at you, hit you right in your weak spot, but he looks far too pleased with himself for the illusion to work.

“What if he deserves it for comparing me to a bloated couch fucker?” Again, the conviction isn’t really there when you’re bending your knees into terrible form trying to chase his touch every time they recede.

Jack yanks his fingers away, sucks them clean with a slippery pop, and kisses you on the point of your chin before shuffling out from under you.

“Clearly you’re not being challenged enough if you can complain like that!”

This time, you do try to kick him off the board, but you have no range at all to put some power into it. That’s what you tell yourself, at least.

“Look at you! You wouldn’t have been able to do that at Lake Superior. Told you you’re getting better!” He’s tugged his shorts down and your swimsuit to the side before you can snap at him, and he actually cackles when he sees how much your lats twitch when he first slides in.

“You’re unbelievable.” The way your voice shakes makes it sound more like a compliment than a last ditch effort to compose yourself.

“That’s what I’ve heard! There you go, arch for me.” He’s not causing much motion yet, only waves big enough to scatter the fish, but you’re wound so tight he might as well be putting you straight through the deck. Your arms are already shaking, and of course Jack notices; how could he not?

“Keep your arms steady. No, don’t lock them up, lean into it,” he’s saying like they’re not on fire, like you can’t feel yourself clamping down on him in some sort of weird unified muscular system effort to keep you from falling on your face.

“Can’t believe y-“

“How fast you’re progressing? I know, right! You must have a pretty good teacher!” He’s absolutely insufferable. You’ve been moving nonstop since dawn, he’s got your ass locking up like an NDA, and his voice is still perfectly fucking steady.

Jack’s middle finger just barely trails along your side, feather-light enough to raise goosebumps on your skin.

“You’re holding too much tension here.” Thank god, he mercifully spares you the lecture about proper abdominal engagement.

“Jack, I can’t- I’m gonna fall!” The wavering in your voice is so unbelievably humiliating when he’s barely breaking a sweat. Your arms buckle, threatening collapse, and there he is seamlessly shifting his hands from your hips to swing under your torso and support you when they finally give out, the other splaying flat across the deck.

“Noooo you’re not, you’re fine. You can have a little break, and then we’ll try again, okay?” All while his thrusts remain infuriatingly consistent. The board barely even moves when he catches you. Your nails scrabble at the deck pad, then the limb supporting you, trying to regain your balance, ground yourself, Jesus, something, but he’s got a better angle now and can haul you back onto his dick as hard as he likes without worrying about your arms giving out.

“You’re such an asshole!” you sob as you claw at his forearm.

“Tell me to stop then! Be silly and turn down a free lesson, why dontcha?” Any attempts you make to thrash your way out of Jack’s grasp just stimulate you more, and he’s suppressing a fit of laughter watching you jolt like you’re stuck in a bear trap. When all that’s left for him to knock out of you are little stilted squeals, his resolve softens, and he leans down to kiss your ear.

“I know you can do it. Push yourself up for me.”

The only way out is through. This time, your arms do lock up; blame the unfavorable circumstances. The world narrows to tunnel vision as you watch the board tilt left, then right, with the ringing in your ears making the whole spectacle feel a tinge nightmarish.

Your orgasm hits you hard enough to have Jack choking out an “oh, fuck” that sounds just as strangled as his dick must feel. You can hardly enjoy it over both of your triceps cramping terribly, though you can’t help but feel a little proud of yourself for staying dry when you slump to your elbows halfway through.

As unceremoniously as Jack thuds down at your side, he still instinctively spreads out enough to keep the board steady. He looks about ready to fall asleep, so of course you roll over to bother him.

“Is that how you taught people to surf?”

“Nah, they were way more advanced.”

“Fuck you!” He’s back on his board and paddling out of the inlet in a flash, somehow not flipping yours in the process.

“Sounds like someone doesn’t need any breaks on the return trip!” By some miracle, you manage to grab his leash before he flies past you.

“You’ll tow me back.” Jack spares you a full glance over his shoulder, and there’s an unmistakable streak of you remaining on the left side of his mouth.

“Oh, yeah? Why’s that?”

“I’m pretty sure I’m your favorite student.”

[melancholicstation]

robert f kennedy after interrupting his own indiana campaign schedule—humours a very smitten young girl @ an indianapolis daycare in 1968. 😢

“Bye-bye I’ve gotta go now”

“Where are you going?”

“Oh I don’t know, going to speak to some grown ups I think. That’s not nearly as much fun.”

[politicalchange]

you being jack’s scandal.

jack had been married, but his marriage was in shambles. ever since he started running as a presidential candidate up until the moment he became president. he had no one to go to for support, his wife distanced herself, taking their daughter alone and letting jack go through things by himself. then he met you.

he told you about his problems, talked on the phone, took you for late night walks in the white house garden, it was all so nice. it started off as something small, you both met at a bar, jack resorting to the strongest liquor as a way to cope with the stress of his wife potentially leaving, and you being the most sober person in the bar, making sure he makes it out alive. his wife never left him though. and she still doesn’t know what’s happening between the two of you.

anyway that’s how you ended up a month later, late night in the oval office, jacks button up white shirt sliding off your shoulder while you bounced on his cock in his president’s chair. jack continued to unbutton his shirt that was clad around your body and began to suck on your tits, leaving you in pleasure as you threw your head back.

“get up.” you quickly obeyed and stood on your feet, jack turned you around and bent you over his desk, quickly shoving his cock back into you and thrusting hard, his strong hands grabbed your waist and one hand was used to smack your ass, leaving a mark.

“you love being bent over my desk like a dirty fucking slut don’t you.” you whimpered and nodded, but jack gripped onto your hair and brung your back to meet his chest, you squealed loudly as he continued thrusting. “say it. say you like being a dirty slut. my dirty slut.”

you gasped as he gripped your throat. “i love being your dirty slut.” you cried and he had the audacity to laugh and force your head back onto his desk. he grunted as he gave you a few more hard thrusts, until he pulled out and you cried out at the loss of contact. he turned you around and gripped your face, “shut the fuck up.” then he crashed his mouth onto yours.

the makeout was quick and hot, jacks tongue fought for dominance against yours and you could feel the saliva swapping, that just make it even more hotter. jack pulled away and forced your mouth open, then he spit in it. “swallow.” you obeyed and jack smirked, caressing your face.

“you wanna get fucked more, huh baby? one orgasm wasn’t enough for you?” you shook your head and jack picked you up, shoving you against his window as he forced his cock back into you. “i’ll fuck you till you had enough don’t worry baby.”

you moaned out loud and began scratching at his back as his big arms wrapped around you and bounced your tiny figure up and down, all the pleasure becoming too overwhelming for you to handle. jack laughed in your ear, “don’t worry baby i got you. i won’t let you fall.”

after a few more thrusts, you came. but jack had other plans. “get on your knees.” you quickly got on your knees and jack forced his cock into your mouth, making you gag around it.

he groaned and threw his head back, gripping onto your hair for more support as you continued sucking the life out of him. you bobbed your head back and forth and gathered saliva into your mouth, letting his cock fall out so you can spit on it. you giggled as you slapped it against your face and pouted your lips up at him. he looked down at you, “fuck baby your so pretty.” you nodded and became stroking his cock, making sure to look up at him with low and seductive eyes at the same time.

“fuck i’m gonna come.” jack shot out spurts of cum onto your face, covering it all. you rubbed his cock all over you and licked his tip to collect any leftover cum, before using your fingers to lick his cum off your face.

jack pulled you up by your neck and sloppily kissed you, picking you up and bringing him into his bedroom. “my dirty fucking girl.” you giggled and wrapped your legs around him.

little did he know, his wife was on his way to speak with him about marriage counseling. yikes, that’s scandalous.

[endless-ineffabilities]

my husband's a slut I fear

[murdrdocs]

been having a thought lately … concerning brooklyn baby and jack …

you stumble upon it in the middle of the night.

you're laying on your side, jack's arm limply thrown over your waist, his breaths as steady as your thumb as it scrolls through the comment section of yet another video. you should be like him at this time of night, knocked out and having been so for at least a couple of hours. you should be curled into his side, greedily sharing as much warmth from his body as you could.

but every video is more entertaining than the last, each comment leads you down yet another trail. you said you would stop when jack clicked his lamp off and pulled you into him. but he's since rolled onto his back, a sign that he's out for the night, and you're still in the position you started in.

you reason with yourself; one final video and you'll plug your phone up and go to sleep. it just happens to be some sick form of fate that makes the next video on your page be one of you and jack. it's a clip of the two of you walking through the street a few days ago, jack leading the way with your hand in his. the two of you are walking in slo-mo, making it more dramatic when jack appears into the frame first, and then you second. video-jack turns his head to look at you, grinning in a way that is almost coquette-ish when you smile back. the video then cuts to you and jack stood outside of a restaurant, his arms wrapped around your shoulders and his body slumped against yours. the two of you look picturesque in that moment. you understand why someone would have filmed the casual intimacy.

to top it all off, the creator set the candid moment to lyrics that allude to jack being cool, but not nearly as cool as you.

instinctively, you double tap the video and then click on the comments. the top one makes you laugh.

i know she bosses him around.

and the comment right beneath it, added by the creator of the video, says: and he likes it, too.

and the thing is, they're right.

eventually, you own up to your word, clicking your phone off after taking a screenshot of the comments. you roll into jack's side, making a mental note to show him what you've found in the morning.

[eppysboys]

JFK's grandson 😌

[velunas]

please please pleaseee write jack schlossberg relationship headcanons 😩🙏 i love your fics!!

YEAA MORE JACK LETS GOOOOO

dating jack schlossberg headcanons ——

cw: idk man but it’s pg i swear (maybe pg-13 at worst)

takes pictures and videos of everything and i mean everything

just woke up and your hair is crazy? he’s taking a picture. you’re singing in the car? he’s recording it. mid hair wash in the shower? he’s taking a picture.

somewhat affectionate in public but extremely affectionate in private

if you’re out on a walk or going shopping with him, he’s got your hand in his and you’re walking on the inside of the sidewalk and he’s keeping you as close to him as he can

at home he basically lives inside of your clothes with you. will sit next to you in your couch and pull your legs on top of his and rub your calves because he just loves to touch you

showers together!!! he loves the domesticity of it. you have to buy double of all of your hair care items bc he’s using them all. your conditioner doesn’t last more than a month with him staying with you

begs you to wash his hair all the time. he just loves when you play with it tbh

will happily pay for you to get your nails done just to feel them scratch his scalp

kisses all over your face when you wake up together in the morning

or he will sneak out if he wakes up before you to grab you both breakfast and coffee

loves watching you get ready for dates. he’ll sit on the edge of your bed and just admire you as you do your hair and makeup

goes to you for fashion advice all the time. he also secretly loves coordinating outfits with you

makes sure to tell you he loves you before you both go to sleep, even if you’re upset with eachother

sends you random videos of what he’s doing throughout the day

makes you playlists of songs that remind him of you

i feel like he’s just such a classic gentleman and does all the ‘gentlemanly’ things like open doors for you, pull out your chair, doesn’t let you pay for anything, all that kinda stuff

he’s really just the sweetest boyfriend ever like u cannot get any luckier