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bowieandqueen11 · 1 year

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Kissing Kendall Roy Would Include...

Request: idk if the Kendall Roy request is still open but like; i know it sounds silly but just kissing him. Just always kissing him whenever you can reach at the time. his hands while he hands you a glass of wine while youre sittin on the couch? sure. top of his head from behind? you got it. his eyelids when hes slowly waking up? amazing. under the jaw after straightening up his collar? lovely. on the chest after the shower? hot. cheeks so he doesnt cry? the cutest. just how can you stop when its HIM-

BABE I am YEARING god you are so real for this I want to cry I- Also ty ty for doing my job for me and giving me legit all the amazing headcanons inspo ily fr <3

NOT ME WRITING 4.1K OF KISSING KENDALL HEADCANONS LMAOO anyway I went a bit overboard and this took quite a while to write, so please please let me know if you enjoy! :) Thank you!

Warning: Kissing, racy kissing, some heavily implied NSFW, mentions of drinking and smoking and a little strong language! Although not explicit, I’m going to go with 18+ on this one please!

(I do not own Succession or its characters, all rights go to creators. Gif credit goes to @technicolourtelevision.)

☆.。.:・°☆.。.:・°

Hngghhhh I want to kiss Kendall Roy so bad like?? His little dopey eyes and his sweet as seduction smile and his perfectly squidgy cheeks and those sad plump lips like frick Logan and the cycle of abuse Kendall Roy was invented for kissing pls-

Your first kiss happened when the two of you were sixteen: Shiv and Roman had been shipped off for the day to some yacht event their mother was hosting in England, and so the usually imposing mansion seemed all the more eerie when you slipped into its hall. Trawling through the rooms, you peered through ornate doorway after empty doorway to find nothing other than freshly beaten rugs and expensive looking vases crowding the place. Little did you know, as you snuck into one of the Roy’s ‘entertainment rooms’ in the west wing of the second floor, that Kendall was similarly as bored as you were; finally being given a break from listening in to his father’s conference calls, it wasn’t long until Ken decided to investigate the weird sound of talking coming from down a couple of corridors. He came trawling in to see you looking surprised, sitting hunched up on the floor and watching some kind of 00s looking rom-com on the flat screen television. He smiled fondly, not surprised to see you, and came dawdling over until he was perched politely down in front of the settee beside you. His freshly pressed brown trousers brushed against your own as his knee came to rest against your own, and he didn’t even hesitate to reach into your open backpack and pull out a couple of sweets you had smuggled into the Roy residence.

There had always been something between the two of you, ever since you had met as neighbouring children almost ten years ago now. A stolen glance. A kiss on the cheek when the two of you departed to plod sadly back home. A missed bite on the lip when the two of you waved and ran over to hug each other after only a few days apart. Kendall cradling himself and always beelining straight for your arms when his father had yelled at him again. Even so, while the two of you sat staring at the television screen without even really seeing it, it took Ken quite a lot of courage to try and make his feelings a little better known. Taking inspiration from the way the character flashing before his tired eyes had grasped onto the protagonist’s hand in some desperate plea of true love, Kendall tentatively spread his fingers out like a sprouting vine until they bumped against your own. He didn’t even turn his head when he planted them gingerly down on top of your own, but his fingertips shook nonetheless. It took you a great deal of bravery as well to rest your elbow back on the cushion as if you were going for a yawn, before letting your own fingers fall back down against the nape of his neck. Uncertainly, you hold your breath, and hear Kendall’s hitch as you play with a few strands of the hair poking out just above his cream cable-knit jumper. Out of the corner of your eye, you can see his hand claw where it’s resting on his inner thigh.

Before you can even register your shock, Ken’s torso has turned and he’s leapt at you, clumsily knocking you backwards. Luckily his hands have already shot out to grasp behind your back, so you manage not to bruise yourself against his ferocity, but it doesn’t stop you from gasping as Kendall clambers over your body like a shoot reaching for the sunlight. The overwhelming rush of love gushed through him like the course of a river as he overtook you, his lips frantically latching and smothering and pulling against your own until you couldn’t breathe. Couldn’t feel. All there was in that moment was Kendall, his legs sliding between your own and the throb of his plump lips as they graced over every inch of your mouth they could latch onto.

He only pulled away, most unfortunately in a state of fear driven panic when the door pounded open and the scowl of his father thundered across the doorway. It was the first time Logan had ever caught him in the act of showing true, unforced, fully felt love, and so for a while after that Kendall retreats back into himself. Feeling the lash, feeling the sting of his father’s disdain, he becomes more cautious about allowing himself to indulge in the one thing he’s ever truly wanted in his life.

He tries his best to pull himself away from you - but it’s like an invisible tide, slowly swallowing him whole again until he’s lost in the warm tides, the glimmers of you breaking through the blue bounds like shards of sunlight and free air. He tries his best to smother it, or to drink and smoke the hole in his chest away, but even then it doesn’t do the trick: he has to steal one more kiss from you before he goes away to college, and then he can release you from the hell scape that is his life. A few hours before he’s due to head off for his first term, you enter his bedroom to find Roman rummaging through the last few half-packed boxes, searching for technology he can steal from his brother. You ask him where Ken is, and he gives you a ‘I wouldn’t even fucking bother, I’ve already tried to talk to him’ raise of his eyebrow and shrugs, titling his head slightly towards the bedroom’s balcony. That’s all the invitation you need to slide open the gliding doors and step out into the cold breeze, shivering as a few drops of rain brush off from the drooping trees that dance over the railings.

Kendall’s sitting on one of the lounge chairs: his legs are pulled up to his chest, and his arms are tightly clasped around them. He has headphones on, and as you come to sit beside him, you realise that his chin is tucked into the gap between the legs and he’s crying quietly to himself. He startles when he feels your pressure against his side, but neither of you say a word. You just already know that his heart is broken. And he knows there’s nothing he can do, nothing he can say that will stop him from being the shadow latched onto his father’s shoe. He’s tired. Of his father. Of his life. Of being a Roy. Of not being able to be with you in the way he so desperately begs for at night. So, before he gets into the limo you can see rambling down the stone-spitting drive, Kendall Roy kisses you for the second time. And in his mind, he believes it to be the last. You can taste his salty tears as he tenderly leans his head over, the slight pressure against your mouth making the lines on your forehead deepen. For a moment, your mouth opens in a gasp and Ken takes the opportunity to brush the front of his tongue against your own. But then the limo pulls up outside the front door and honks its horn, and Ken pulls away with a sigh. Before he leaves, he sorrowfully lets his forehead fall against the top of your own, and he sniffles for a few seconds as he desperately tries not to choke on his tears.

Then he just gets up and leaves. He can’t even bear to look backwards. It just hurts too much, even though he feels his heart being bruised and broken with each step away from you he takes.

Thankfully for Kendall, you’re not going to give up on him. You’ll stay by his side through thick and thin, keeping as his best friend throughout his adult years. If he can’t allow himself to love fully, and freely at the moment, that’s fine. The time will come for the two of you. The time will come when he’s no longer scrambling for that knife in the mud. The time will come when he’s the victor, and he can bend and snap the rules at his own will and fancy.

Besides, soulmates always found their way back to each other in the end.

It takes quite a few years for Ken to finally admit you’re the love of life. Until his mother’s wedding in a beautiful, if slightly dusty, hamlet in Southern Tuscany. Like a flower blossoming out of the cracks of a dull grave, he breaks down in front of his siblings on that sun-dried street. How much he ‘fucking loves you’ and ‘fucking misses you’, and that he’s a ‘coward’, so it’s no surprise that when you come wandering past one of the orange backhouses trying to find Ken, Roman and Shiv give each other a look and decide to give the two of you a moment alone before calling for a car. When you spot him sitting alone, shivering, looking as if life had just stomped on him and left him a quivering mess by the bins, your heart just crumbles.

He barely moves when you come to settle down on the dirt beside him. He just stays flopped like a ragdoll, his hands shaking where they rest over his knees. After a moment or two of you just allowing him to settle into a safe silence, he begins to wrangle his hands together nervously: a sure sign that he’s about to start sobbing. So you do the only thing you can think of in that moment, without breaking him into a million pieces. You lean sideways, and press a gentle kiss against the top of his stubble line, the skin warm and scratchy under your touch. He finally musters the courage to take a glance at you then, and from the sheer emotion that wallows in the pained look he gives you, you just know. He can’t hide it anymore. It has to come out, whether he can admit to it or not. Ken opens his mouth, a gasp rushing in as if his whole lungs are about to tumble out, and you jump at the opportunity. Before he can drown you lunge forward and latch onto his lips, right where a stray beam of sunlight is resting. He’s quick to reach up and cup your face, turning his head sideways so he could better wipe his bottom lip against the edge of your mouth. He cinched you to him, a shiver rolling down his spine as a few stray tears rolled their way down the bridge of his nose. The heat of the sun starts to burn against the back of your head but you couldn’t care less, because Ken has started laughing breathlessly, hysterically against your open mouth. It’s almost as if strangled devotions are about to choking their way up his throat, but you quickly silence him once more, and he falls, for the first time in his life, easily against you.

Thankfully, kisses after that afternoon come much more freely - especially the languished ones on your wedding night. I mean, he’s waited far too many years for this moment, so Ken manages to sneak you away from the party and bridal carries you up the staircase and into the newlywed suite of the fancy estate. You bite the edge of his bottom lip as he places you down on the bed, his chest already heaving just from the slightest dance of your hands as they slide under his shoulders and shove the suit jacket off of his shoulders. Messily, hungrily, fervently, he crawls over the duvet and clinks his teeth desperately against your own. Once he’s above you, he uses a free hand to rustle underneath the rustled layers of your dress until he finds the square of bare skin where your upper thigh meets your buttocks. He scratches his fingernails teasingly underneath your panty line and squeezes firmly, making you groan into his awaiting mouth. He smiles, both fondly but with a hint of smugness, as takes your free hands and lifts them up towards his shirt buttons, guiding you to undo them with a heavenly pop after pop. He swears in that moment, as your hands glide out over his abdomen and massages the sides of his pecs, he would be content to die in your arms right there and then.

Kissing to wake him up every morning is literally what bliss must feel like. At six on the dot, you lean over on your side and gently kiss the top of his eyelids until they sleepily flutter awake. Bless his heart, the first thing he does every morning now is automatically smile; his arm reaches out onto your side of the bed before he’s even fully awake, seeking you out. It always makes you laugh, when his hand finally grips onto the side of your waist and tugs you further against him, because it was a little habit that had grown since your childhood years. When Kendall managed to sneak you in through his bedroom window, unable to sleep soundly by himself in his own bed, he would always start out feeling so self-conscious. Lying on his side, he faced out towards the open opaqueness and gilded shadows of his hollow room, his hands bunched up under his pillow. Even though he used to leave nearly a mile between the two of you on the silk sheets, he was so hyper-aware of making you uncomfortable: of scaring you off, if any part of him touched you. By the morning though, he always managed to kick and crawl and scrabble across the bed in his sleep. Although he was still to conscious to hold you fully, you would wake up to feel an intense pressure against the top of your back. Kendall’s head would be stoutly impressed upon your shoulder blade, his hands curled up and tucked against the small of your back and his legs raised against your hips as if he were a child curling up against his mother.

Now, though, Kendall’s finally content. He’s finally able to open up, to indulge himself in the only thing he’s ever truly wanted. He allows his cheeky side, his Roman-esque side to shine through by lulling you into a false sense of security. After a few minutes of you cradling his head against your bosoms and pressing kiss after kiss against the expanse of his head, he’ll jump up and pounce at you. You squeal as you scramble for an escape, trying to kick him off as you throw your hands to the floor and try to run your way towards the kitchen. He’s quicker though: not even a second passes before his arms tighten like a vice around your abdomen and he’s blowing wet raspberries against your throat. So infantile, so uninhibited, he drags you kicking and giggling back towards him so he can latch onto your bag and spoon you for a little while longer. You don’t complain when you feel him settle behind him, the heaviness of his leg as it reaches up and clambers against your own a welcome comfort. So is the feeling of his loving lips wiping a fond kiss against the nape of your neck.

Mhhh you bet those domestic kisses are godlike baby! The whole time you’re sliding around the kitchen trying to dump the takeout the two of you had decided to order on a tired whim onto plates, he’s holding you. His hands are thrumming against your waist as he presses against you from behind, singing into your ear a song the two of used to dance around to when you were younger. Every time you think he’s finally pulling away to maybe, you know, help by getting some cutlery or dumping the empty boxes in the recycling, he appears again to tickle you by licking gently behind your ear. You try to swat him off with a laugh, but that only seems to spur him on; the man is literally so deliriously happy he could cry. This. This domesticity. This fondness. This trust. You. It’s all he’s ever yearned for. Spent his younger years dreaming about. So you bet your ass he’s going to come sneaking up back behind you so he can tremble against your back as he pulls down the back of your shirt and leaves a few hickies proudly littered behind along your shoulder.

When the two of you finally settle at the dining room table to eat, to talk naturally like you’ve done a million times before over the years, you actually manage to surprise Kendall. Using your foot, you catch the edge of his sleek charcoal chair and pull him closer to you until he’s sitting by your side. It makes it far easier to grasp onto him when he shakily pours you a glace of wine and hands it to you, and definitely is a far more satisfying viewpoint to see how his tears well up when you take the wine glass from him and place it passively on the table. Unclenching his hand, you slowly kiss each knuckle one by one, raising them up to your mouth in the way someone may kiss royalty. He’s giddily smiling when you rub your thumb over the back of his hand, and he refuses to let go of you, even while he’s eating. As he turns back to try and cut up his noodles with the edge of his fork, you compassionately pretend you don’t notice him turn his head away from you for a moment, so he may sneakily try and wipe his eyes on the corner of his shirt.

On tougher days: when things haven’t been going well at Waystar, or his siblings have decided to barge in and try to stir up some new unwanted drama in his life, the sweetness and tentativeness of shower kisses are Kendall’s favourite. He will actually melt into a puddle of goo if you hold onto him, allowing him a moment to feel safe as the water cascades down and burns against his clenched eyes. He finds it difficult to be around water, so he may be a little panicky, but the feel of you wrapping yourself around his naked torso always manages to calm him straight down again. That is, until he gulps heavily at the feel of your lips kissing a trail up his inner chest to come tease with soft bites against his pulse point. He’ll wrap his arms around the curve of your spine, running them gingerly up and down as if he can’t believe this is still really happening.

When you rinse out his hair, he finally comes back to himself and blinks in amusement when you try to wipe away a few of the leftover suds from the tip of his nose with a short kiss.

Bro I mean- it also helps him immensely when he finally just like... snaps. When he can no longer hold back the growing pounding against the dam of his heart, and the desire that’s been eating him alive ever since he was a teenager comes cascading out. In a split second, your hands have been removed from where they were running soapy circles against his oblique muscles, and he’s pinned them harshly above your head. Taking a step towards you, he traps you against the steaming glass of the shower while his tongue explores the inside of your mouth. He pulls away, panting, before lowering himself onto his knees and kissing the inside of your thighs as he lifts one of your legs over his shoulder.

Sometimes you make him jump with your kisses, no matter how well intentioned they are. Kendall hates having to work inside his dad’s old office: suffocated by the smells, the sights, the overwhelming life that still bursts forth from the space and haunts Kendall, even in death. To try and help him relax, you’ll come sneaking in to kiss the back of his head, making him jump a country mile. With a smirk, he drops his phone down onto the desk and leans backwards slowly, raising his arm up until it latches onto the back of your head. Langurous, he leans his head back against the headrest until you fall down and softly press your mouth against his. Even though he can see Gerri and Karl give each other an unimpressed side-eye glance, he honestly couldn’t care less. In the end, Kendall would give all this up: everything he’s worked his whole life to accomplish. In the end, he couldn’t give a fuck if he made his father proud, if he was competent enough to earn being a Roy, if he lived up to the mantle of being the second-born eldest son. Of being the favourite. Because in the end, all Kendall Roy actually wants is you.

Being CEO also comes with its perks, though, like you being able to straddle Kendall’s waist and sit on his lap, the two of you squeezed into Logan’s old chair. His groans can reverberate hoarsely throughout the empty floor after ‘lights out’, only the poor cleaners being left to see the blinds to his office shake as something hits against them. With an unceremonious thump, the tie you had loosened and thrown falls onto a shelf full of open binders, soon followed by Ken’s shirt. He fidgets underneath you, bucking his legs up when you begin sucking against the bottom of his jaw, and it fills you with great pleasure to feel his hands clutching desperately into the meat of your hips.

The sweetest kisses shared are up on the company’s roof. Sometimes Ken is just having an off day, mentally, and needs some time to decompress away from everyone else. No matter where you may be in the building: no matter if you may be in a meeting, or at your desk, or just hanging around the breakroom listening to Tom and Cousin Greg discussing something with heated whispers in the corner, Kendall comes lumbering in looking crestfallen and immediately dismisses everyone in the immediate vicinity. They all scramble off like cockroaches, and Ken reaches out to take your hand. You offer it willingly, knowing what’s going on when he starts fiddling with the edges of your fingers. He folds into you in the elevator, clasping onto you and tucking into your side as you hold him against you, stroking back his hair. When the two of you finally arrive on the wide stretch of beige concrete, and no one can see him be weak, Kendall allows you to guide him down until he’s sitting between your legs. He leans back against your chest, squeezing his eyes shut and gripping onto your legs as he simultaneously feels the sharp sting of the wind and the feel of your lips against his temples.

Kisses at events are actually the best no joke like those married life vibes are off the chart. When Connor and Willa decide to have another, smaller vow ceremony in front of immediate family, everyone (even Shiv finally relents) thinks the two of you look so cute. Holding each other close at the edge of the country estate’s freshly manicured lawn, the fresh crunch of the dewy grass underneath your shoes is a welcome relief against the burn of Kendall’s hand as it caresses your own, holding it up by his side. The two of you can barely make each other’s eyes, falling into a fit of euphoric, infantile giggles that makes the other wedding guests stop and stare confusedly at the two of you. The kind glow of the varnished barn lanterns brushes over you and Kendall’s blushing cheeks, the lace-like wood work that winds up their edges illuminating over your bodies and making the two of you glow like you were sublime. Like a fool madly in love, he keeps snatching looks at you with that big, soppy smile of his, before pressing a kiss against your forehead. He leaves his chin there, sighing in contentment as he pulls your shared hand over till it’s resting against his heart, and continues swaying the two of you back and forth.

Ken has adopted this adorable little habit of letting you know when he wants kisses. He dips his head and looks at you like a forgotten puppy, taking your jaw in his hands and stroking his thumbs over your bottom lip and man does it just make you melt and indulge him straight away.

I mean my man has a literal lifetimes of kisses to make up for, and I’ll be damned if he isn’t going to grab onto every opportunity he can. Every touch, every caress feels like a fresh spring breeze, like sunlight caressing the curling corners of a brand new flower, like the cascading glimmers of light falling through the vastness of an unsurmountable ocean. It’s a renewal of life. Of hope. And in all honesty, it’s the main thing keeping the real Kendall Roy alive.

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