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English
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Published:
2023-05-04
Updated:
2023-05-14
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2,046
Chapters:
3/?
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61
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Kendall Roy NSFW Headcanons

Summary:

A collection of various Kendall Roy NSFW Headcanons that i've had as requests through my tumblr.

Notes:

(See the end of the work for notes.)

Chapter 1: Kendall Roy + Dom/Sub

Chapter Text

Kendall Roy + Dom/Sub:

Sub:

- Kendall Roy is the stereotype of a man who craves power in his career but loves to be controlled at home.

- It would take a while to come to light, his performative smirk plastered across his face when you first start sleeping together, taking the lead as he thinks he should. But you'd notice the little twinkle in his eye when you tell him to wait for something, that he can't touch you quite yet, that he needs to ask before he spills himself inside you. Eventually you'd be straddling his hips, bouncing on his length, pinning his hands above his head until he promised to be good for you.

- This man will start to try negotiating (unsuccessfully) with more and more explicit words falling from his lips with each cutting hollow scoff you give in response, making him wait just that little bit longer for release because he dared to speak out of turn while you're in control.

- You have complete control over Kendall when you sink to knees and make him beg for you to taste him, the poor boy's self control being tested to its absolute limits as he sings your praises and tells you how much 'he doesn't fucking deserve you' until finally you take mercy on him and run your tongue over his length, a steady stream of thank you's cascading down from above.

Dom:

- When Kendall's in the mood to take control you can tell straight away from the almost threatening look in his eye. The sly smile telling you he's about to find your limits and toy with that line until you beg him to cross it.

- He'd love seeing you completely helpless, tied to the bed and entirely exposed to him, just a plaything for him to use in whatever way will bring him the most fun and satisfaction.

- Dom Kendall is painfully into teasing you, taking his sweet time before he ever even touches you, and then only the slightest brushes to get you frustrated; a little pinch of your nipple so you flinch against your constraints, spitting on your throbbing clit but never quite bringing his tongue to touch it, stroking himself just next to your opening without making any of the contact you desperately crave.

- While you're at his mercy, Kendall would mark you as his, hickeys across your chest and up your thighs, making sure if anyone was looking at you in a way they shouldn't, you would be unmistakably his. He'd make you chant over and over again how 'you're all his' and 'how badly you need him', rewarding your devotion by finally bringing his fingers to your clit, rubbing soft circles on the sensitive bud until he can see your pussy clenching around nothing, your thighs starting to tremble, snatching his fingers away before you reach your much needed release.

- Ken would laugh darkly as your hips buck of their own accord, desperate for friction but unable to give yourself any relief, every nerve in your body at Kendall's will. He'd see how many times you could bring you to the edge before he had you in tears, mocking your desperation when he asks if you're crying because you don't like the feeling of his fingers deep inside of you, his tongue tracing over your nipples and if he should stop, and you frantically shake your head and beg him to keep going, to make you feel good.

- When his own aching need grows intense enough he'd finally settle between your pinned legs, fucking into your leaking entrance with rough, heavy slams until you can almost taste the sweet relief of your built-up orgasm. Kendall would pull out at the final second, letting himself shoot all over your chest instead, watching his sticky seed pooling between your breasts and across your stomach, your whole core straining with how close you finally came to release only to have to cruelly snatched away again. Kendall would watch you struggle against the bings on your hands and legs, makeup smudged with your trickling tears and body covering in his hot white load, and decide you had been good enough for him.

- With a vibrator pulled quickly from a bedside drawer your first orgasm would come rapidly, overwhelming sensation running through you as your body finally released all its build up tension in a wave of pleasure that would have your head spinning and you thanking your sweet Kendall for letting you cum, the sheets beneath you half-drenched. And he'd laugh and keep the vibrator firmly fixed to your throbbing clit, turning it up a speed and watching how quickly your grateful expression grew concerned, knowing your teasing was far from over. Kendall would keep you tied up there for the rest of the night, making you count out each orgasm he generously gave you, fucking your dripping hole whenever you begged him to give you a break, reminding you how desperate you've been to cum all day.

- Afterwards Kendall would be a genuine gentleman of aftercare, checking he didn't go too far, that you have everything you need and reminding you that above all he loves you very much.