Maybe you could do a Connor Roy Smut Headcanon??💗 Really been living your work
Currently rewatching and I forgot how much of a genuinely sweetheart he is!
Sweet Connor who is always buying you insanely expensive gifts imported from all over the world but hidden in each item would be a page long handwritten love letter explaining every detail of why he chose it for you.
Despite claiming to be an old fashion type of guy, I think he would loveeee sexting! Send him a random picture of your ass, and you would get a 2 min long voice message back from him describing how hard you make him and how lucky he feels.
His lap is actually the comfiest place to sit.
Wants you to sit in his lap while he sucks and teases your nipples and you play with his hair.
Innocently sitting on his hips right below his lil squishy tummy as you two chat about your day. But would quickly becoming your grinding on him as he squeezes your hips pulling your tighter to him
I believe with my whole heart he is amazing at foreplay. He spent year fucking girls just for his own pleasure, now he really likes to take his time. Covering your face and neck with kisses before he was even trying to get your shirt off.
This would occasionally lead to him almost ruining the moment. You would be begging him to put it in already, and he would dramatically respond something like “I have to take my time…i don't know how much i have left”
Really Really likes lingerie! Especially if it's super feminine, anything with lots of lace, flowers, and pink
Always coming home to some lacy set placed on the bed with a little card :,)
Please give this man some praise. Tell him how good he feels inside of you, how nobody can fuck you like him, and as basic as it is, pleaseee tell him he's the best you've ever had. He won’t be able to stop blushing and will hide his face in your neck but you can tell how much he loves it as he starts pounding you harder.
Gentle loving sex 70% of the time
Intense passionate pounding the rest
I think he would probably want you on top a lot. Of course he has no problem being on top but loves watching you ride him as you use his cock to make yourself cum, his large hands squeezing your ass helping to guide you up and down
Also loves doggystyle!
Wouldn't get rough with you too often but when he did, he was usually taking you from behind one hand pulling your hair as the other wraps around your neck. Not squeezing just using it as leverage to fuck into you harder
Shutting him up from conspiracy theory rambling by unzipping his pants and pulling his dick out
Would get a vasectomy just to cum in you as much as he wants
I don’t think he would be a big fan of degradation, calling you his little slut would make him feel “like your pimp” he would state
Aftercare would sometimes be you holding him in your arms reassuring him how much you love him and how happy he makes you as you lightly scratch you back with your nails. He just gets so worried that he doesn’t truly please you so your soothing voice reminding him would almost make him cry T_T ugh he's so cute
Description: When you started your new job as Roman Roy's new assistant, you expected coffee runs and sending fax. This expectation is quickly thrown out the window as you find yourself falling in love with your boss and his older brother.
Pairing: Kendall Roy x Reader, Roman Roy x Reader
“Roman, you’ve got to be fucking joking? What is this about?” You grumbled to yourself, looking back down at your phone displaying the 2am texts you had received from your boss.
Two months ago when you had first applied to be the assistant to the son of Media Mogul Logan Roy, it was simply a passing thought. You were broke and needed some kind of real job to support yourself as you tried transforming this whole ‘starving artist’ gig, into an actual career as a painter. Now it seemed you had fully dove into his traumatic but extravagantly packaged world. You rarely went a day without him giving you something absurd to do, tasks that definitely were not in your job description. Just last week he made you fly to California so you could bring him back dessert from his favorite restaurant. Then complained that “it didn’t taste fresh” and “could be compared to what they’re served in Guantanamo”.
Although Roman was difficult and had zero filter when it came to expressing himself, you two had an understanding. Despite only working for the youngest Roy for about 2 months, since the beginning he always felt more like an older brother telling you what to do then your boss.
The boss/employee relationship quickly turned into a real friendship after only a month of working for him. He had invited you to your first charity gala. Bringing you along to gain experience with helping him win over new investors. However, you two quickly turned the night into a drinking game of ‘you must take a drink of champagne every racist or sexist comment you hear’. You both stumbled out of the gala that night as a new pair of drunk best friends.
While waiting for Roman to answer your questions about the Elon situation, your mind began to drift back to the first time you met Roman Roy.
“What the fuck am I doing?” You asked yourself harshly, your hands shaking as you cautiously walked through the spinning doors of the glistening Waystar Co. skyscraper.
“I’m here for an interview with Roman Roy” you say to the front desk receptionist, giving a light smile you hoped covered the fear you know is seeping from your eyes. “God, do you think she can tell how nervous I am?” You questioned anxiously in your head, already beginning to fidget with the seam of your pencil skirt. Your paranoid thinking quickly interrupted by the receptionist.
“Mr. Roy’s office is located on the top floor. Please head up and someone will be waiting for you there.”
You had always thought of yourself as outgoing, adventurous, maybe even a little fearless. However, as you walked into the office of the son of one of the richest men in the world, all of the courage slipped from your body.
“Hello!”
A voice yelled as the grandiose office chair in front of you spun around slowly to reveal a least intimidating looking small man.
“I’m Roman Roy.”
“Did you like that introduction? I was going for kinda like an evil villain vibe” He said dramatically, letting out a chuckle at his own joke
You were at a loss for words. 15 seconds into the interview and it was already weird, but in the opposite way from what you had expected. Shouldn't he be wearing a tie? Why is he making jokes? Is now a good time to shake his hand? Were all questions you asked yourself before responding.
“Uhh yeah, it was great. I mean… I was intimidated” you stumbled letting out a light giggle. Hoping he would respond positively to your attempt at joking back.
“Ahh and that brings me to my first point, possible future assistant” he stated loudly. “I don’t just want someone here to follow me around and suck my dick. I need an assistant just as driven and blood thirsty as me. Someone with opinions and fucking I don’t know good ideas!”
“Blood thirsty?”
You thought to yourself. You were under the assumption being an assistant meant getting coffee, making copies, sending faxes. You know, office stuff!
You watched as Roman paced the room, loudly rambling about “becoming CEO” and “burning alive anyone who fucks with him” As you listened you realized your nerves had disappeared. Something about his brashness, the constant swearing, or maybe the endless sexual comments made him feel… human. Despite being well worth over a billion dollars.
“Well” you stated, finally finding a brief pause to interrupt his cadence.
“Although I don’t exactly come from this high executive world, maybe that could be of benefit to you.”
You weren’t exactly sure where you were going with this, but you knew he had likely been interviewing highly qualified Yale graduates all day and you had to stand out. You let your poised interview personality fall away and began to speak honestly.
“All these Ivy League guys that have walked in here will say anything to make you happy. Do anything to increase their position in the company, and honestly, Mr. Roy…I have no interest in climbing the corporate ladder.”
This was true. You honestly didn’t care enough about money to try and use the Roy family. You just needed a job to pay for rent, buy weed, and go out every once and awhile.
“However” you continued “I am the only one who will be honest with you even if it’s not what you want to hear. And I understand the average person. I can provide you with real insight into how to gain leverage with the public.” You said confidently attempting to convince Roman but also yourself.
Roman finally stopped his pacing and sat back down in his large office chair. Saying nothing, hands in front of his face with his fingertips touching. The stern look he had on his face made you begin to panic again. Maybe the overly honest approach was too passé, not “blood thirsty” enough.
Roman breathed in deeply and began listing your flaws. “Well you’re highly under qualified, clearly lacking in professionalism and have zero genuine interest in the company”
You looked down at your hands ashamed. Fuck, he was right. Why did you even walk into this building? Why did you try to play it cool?
“But” Roman drew the word out longly while spinning childishly in his office chair. “I think that’s…exactly what I’m looking for!” turning his frown into a devilish grin and jumping up. “You’re hired!” He stated placing his hand out
“What?” You gasped leaving your mouth hanging open slightly.
“Yes! You! You’re hired! I am hiring you.” He said sarcastically annoyed “Now shake my hand before I change my mind or something”
You shook Romans hand more aggressively than you had intended as your excitement grew, while expressing repeatedly “Thank you, thank you Mr. Roy”
Summary: To the point office sex with soft dom!Kendall
“What’s on your mind?” Kendall questioned as his eyes studied you laying out various fast food items across his desk.
Today was one of the rare moments when Kendall had asked you to bring him lunch, instead of just completely skipping it or having Jess throw him a protein bar.
“Oh hmm nothing, just happy to spend time with you.” you hummed, returning a sweet smile to his gaze. You always cherished these little moments when kendall let you completely into his life. It was also nice when he needed you for something. He could probably have lunch delivered from anywhere on the planet, and yet… he chose you.
“Come here” Kendall's face beamed instantly, flashing you his typically toothy grin as he gestured to his lap.
You swiftly moved from around his desk, easily settling into his lap with your ass on his thigh as he cradled you. Your hand reached up to stroke the rough stubble forming on his cheek with your thumb. He leaves a light kiss on your palm and whispers “missed you.” before attaching his lips to your chest leaving wet kisses across your collarbone.
“Babe you haven’t even eaten yet,” you exclaimed, reaching for a french fry from his desk. “You’re not gonna have any time” you pout, placing the fry in his mouth.
“You’re probably right.” Kendall says sternly, slowly standing and easing you gently from his lap back onto your feet.
“But you can’t just walk in here. Sit in my lap. And not expect to get fucked”
His hands waist no time in reaching for your hips. His tight grip turning you around and his fingers working to push your skirt up around your waist, exposing your ass. You gasp as the cold air and rough feel of his fingers brushing against your thong, while he spreads your thighs. The empty space between your legs, warm, already yearning to be filled. His hands smoothed over your ass, grabbing a handful and massaging roughly, before leaving a light slap.
“Ken!” you yelp as his hand runs over the red flesh.
“Shhh..” he is hushing as he presses his chest against your back, grinding his covered bulge into your ass. “Don’t want anyone to hear.”
Your waist is quickly bent over his desk as he uses his weight to push you forward. The clinking sound of his belt and his hot breath hitting your ear is more than enough to have your pussy dripping and Kendall can instantly tell when he rubs the head of his cock along your slick folds.
“Always so fucking wet for me.” He groaned out. Shuffling his feet between yours to spread your legs further for him. You stifled the loud moans desperate to leave your mouth. Letting out a breathy “just for you”. You could hear the pornographic sounds of his dick spreading your wetness, while his tip continued teasing your slit.
Kendall breathed out a soft “love you” as he finally pushed himself into you. He always had a habit of letting his emotional side slip, but those simple words caused you to completely relax into him. Pushing your ass back and further onto his cock, stopping briefly as he bottomed out. He thrust his hips into your ass as his hands held tightly to your hips, forcing you to feel every inch of him inside your walls as his head twitched at your cervix. His slow yet deep pace leaving you breathless and searching for something to grasp as the burning sensation of stretching for his large cock turned to pure pleasure. He quickly moved his arms to wrap his hands around your fingers, placing them together behind your back. The loss of control forcing you to fully submit to his brutal thrusts.
“Oh god, oh fuck, feels so good” you whimper as his swollen balls slapping against your skin, stimulating your pussy even more. Your eyes roll back as you feel yourself tightening around his cock, feeling like you could cum at any second. “I’m so close Ken, I’m gonna.”
“Cum baby, cum for me” he mewls in your ear maintaining his pace, as his hands finally leave yours. One moving to rub rough circles on your clit, while the other grips your thigh tightly. Making sure your legs stay open wide for him as your pleasure builds and they begin to shake.
Your orgasm floods through your body as your pussy pulses around Kendall. Despite your efforts to suppress your moans, loud yelps leave your lips as your repeat “fuck” unable to form any other thoughts from the cock high buzzing in your brain.
“Good girl, it's okay, I got you baby” he cooed, talking you through your orgasm.
You can feel your overstimulated pussy attempting to push Kendalls cock out along with more wetness. However, he continues fucking into you pushing his body against you as close as he can, chasing his own high. You felt your knees beginning buckle and your brain going numb. The sharp desk meeting your hips as you quivered beneath him.
"You can take. Just a little more." His rough groans switching to gentle whimpers as his cock twitched against your walls, releasing his cum deeply inside. His weight collapsed onto you, your cheek met with the cold wood of the desk as you both breathed out your high.
I have a request for Kendall!!!! I imagine him and the reader being on the verge of divorce and him being a possessive almost ex husband and making a scene every time a man breaths near the reader and them fighting and screaming at each other and then having the best make up angry sex of their lives.
Your mind is phenomenal, I hope you like it!
Marriage Make Up
Kendall Roy x f!reader smut 4.1k word count
You tried with Kendall. You really tried. It started with the coke. Which you could look past for awhile. Occasionally, suggesting various detoxes and rehab facilities, always trying to let him know you were there for him. Free from judgment. You knew who Kendall was when you married him, the addictions he struggled with. The trauma. However, the day you stood in front of him, your handmade white dress flowing, a traditional veil being lifted from your eyes to kiss him. You promised yourself you were going to be there for him. No matter what happened.
That was until the coke turned into ignoring all phone calls, never coming home, forgetting birthdays, and daily drunk 3am texts that clearly weren’t intended for you. You threatened Kendall that if this is how the marriage was going to be, you couldn’t be a part of it. But honestly they were empty threats. When you had made that initial promise, you meant it.
That was until the escorts.
You were awoken one morning by the ringtone of your phone, slowly blinking your eyes open as the sound grew louder. You threw your arm over searching to find the warmth of your husband's body sleeping next to you. Instead, being greeted by the now too common fabric of the cold sheets. You began rummaging through the pile of king size blankets searching your buzzing phone, eventually answering right before a call from Roman Roy went to voicemail.
“Hey! Seen your husband lately?” Roman questioned. Never beginning conversations with any kind of small talk.
“Oh yeah…Kendall, my husband” you scoffed. “At this point I have no idea if he is even still alive.”
“Oh he’s alive alright. All over the news actually… Billionaire Logan Roy's son, Kendall Roy seen leaving NYC restaurant with instagram model Claire Hane.”
Roman read aloud the headline cackling after almost every word.
“That girl is like, known to be an escort! What? Did you stop putting out?” He continued joking.
As soon as Roman had begun reading the headline your heart was pounding. Kendall in the news was rarely a good thing, and with every word out of Roman’s mouth you could feel heat rushing to your face as tears filled your eyes.
Choking on the lump in your throat you struggled to come up with a respond to Romans teasing. You wanted to act unbothered, like you were as heartless as any Roy sibling, unphased. But the tears already streaming down your face clearly proved otherwise.
“I…Fuck” you huffed finally managing to get something out of your quivering mouth. Everyone had warned you with patronizing eyes and scolding fingers when you married Kendall that he was inconsistent, unthoughtful, and “occasionally psychotic” his ex-wife even mentioned. However, you always waved their comments off with a smile. “Yeah, I know he has a lot going on, but I’m in love. And he can be really empathetic! I’ve never had someone take care of me the way that Kendall does. And not just with his wallet!” You explained over and over. Now all of your illusions were quickly shattering. Of anything he could do, cheating was not one you expected. Your sex life was great! At least, you thought. Maybe a little lacking lately, but that was hardly your fault seeing as though he was rarely home. Did he honestly need to pay for sex? Your confidence in him and your confidence in yourself were crashing down right in front of you.
“Look y/n, I’m sure it's not you. My brother is an asshole. This wouldn’t be the first time he’s been a shitty husband.”
Nearly forgetting Roman was on the other line you groaned at what you knew was his attempt to cheer you up. “Thanks Rome, I’m gonna go drink over my failed marriage. Bye.” you mumbled quickly hanging up before Roman got another chance to throw in a heartless joke.
Time appeared to be moving painfully slow after the disheartening events of this morning. After laying in bed clutching your chest and sobbing for what felt like weeks, you eventually pulled yourself into the bathroom. Confronted by your gloomy reflection of swollen eyes, still in shock this was all really happening. That Kendall would really be hiring escorts, and that you would find out from his brother! You decided the only way to distract your distressing mind would be a hot shower. Taking your time to delicately wash your hair and lather every inch of your body with the expensive body soap. Even though Kendall was richer than you could comprehend, you still had a habit of trying to preserve those things, never using too much. However, now all those little things were out the window. Who cares anymore if I’m just using him, you thought to yourself. Obviously he doesn’t.
You dried yourself off slowly taking the time to apply a sweet smelling lotion and your face moisturizer. Taking one last glance at your figure in the mirror and letting out a deep sigh. “Fuck him, I’m still sexy” you exclaim aloud at your reflection.
“Fuck yeah, you are!” You hear Kendall reply slyly behind you, looking back to see his suited figure leaning against the door frame. His eyes scanned your body from head to toe. You have no problem brushing off his remarks rushing to grab your white silk robe, covering your exposed body from him. Kendall was quick to pick up on your agitated reaction as you brushed past him.
“Okay. Yeah great what the fuck did I do now? Cause I know I didn’t leave any fucking drugs around the house.” he huffed, naturally jumping to defend his actions.
“Yeah, probably because you’re never here.” You mumbled quietly. You weren’t ready to fight about it. Not yet at least. You still felt too heartbroken to even scream at him, simply just wanting him to disappear until you were ready to confront the reality.
“I know I’ve been gone a lot y/n, but with my dad gone things at the office are just really starting to pick up and everything with Mattson, I mean…” his voice trailed off as you wandered around the room putting together a comfortable outfit. His rambling excuses eventually stopped when he looked at you and questioned,
“Uh babe the fuck are you wearing?”.
“God Ken, why do you even care? You’re leaving again tonight right?” you sneered. He’s never home, and then when he is home all he has is work excuses and a problem with your outfit, seriously?
“Um, we're leaving tonight. Waystar Charity Gala. One of my biggest opportunities to make a good impression as CEO. What, did you fucking forget?” He exclaimed.
“Fuck” you whined holding a finger to rub your temple.
You had totally forgotten tonight was the charity event, explaining why Kendall was home and finally paying any attention to you. Part of being married to Kendall Roy was putting on a play. Attending various events and red carpets draped over your husband's side performing as his beautiful, dotting wife. Although, honestly you never had to fake it. You genuinely did adore Kendall and it made you happy to make him look good, and brag about his accomplishments to his peers. And you were good at it! Always leaving every man in the room jealous of how happy you made Kendall, and every woman dying to take your place. But tonight you weren’t sure if you could handle that job. You couldn’t even make eye contact with him right now, let alone appear like you’re obsessed with him.
Kendall walked over to where you were sitting on the edge of the bed, looking down at you. You resisted every urge to begin crying again, screaming at him about this morning's headlines. Although it was eating you alive, you knew that sobbing to him wouldn’t work on Kendall. The Roy’s were a different breed, and if you wanted to get to him, you really had to make him feel something. You looked up at his figure towering above you. Giving him soft eyes but maintaining the displeased frown on your face.
“Are you seriously this upset over me being busy? God I know, I’m sorry for being the world shittiest fucking husband!” he scoffed “ But I’m trying to take over a fucking company here y/n. Now, you knew what you signed up for when you married me, so we’re going to this fucking gala. And you’re going to be my loving wife, okay? You’re going to look beautiful, and you’re going to make me look good. Can you do that? Can you be a good girl for me?” his patronizing tone sinking deep into your chest. You knew he was half serious, half just attempting to intimidate you, and the good girl he had to throw in hoping it would finally get to you. And it did. Sending heat straight to your center. You gave a slow nod in response, not breaking eye contact. Although, this response was not enough for kendall as he roughly brought a hand under your chin “Say yes Kendall, thank you Kendall”. You repeated his words gently and even turned your head to leave a gentle kiss on his palm. His entire demeanor softened, you could easily play into his game now but you were already planning ways to get back at him throughout the night.
Your dress for the night was a striking dark blue, a slight shimmer radiating from the bottom, drawing all eyes down the velvet fabric that formed around your body nicely. The plunging neckline, a lower cut then you would usually wear. You nearly forget about Kendall as every head in the crowd turned in awe at yours and Kendall's arrival. Your beauty quickly becoming the topic of the event.
As you made your way through the party, Kendall snaked his arm around your waist breathing deeply into your neck, recognizing his favorite perfume of yours. Smirking as he whispered “You’re so good to me.” His words sent a chill down your spine. How could he so easily say things like that while he had another life going on? Your brain jumped between wanting to slap him, and completely surrendering to his touch. You wanted nothing more than to leave a soft kiss on his lips, lean your head into his shoulder and mean it. But you refused to give in so easily, letting his hands wander your body without returning any of the attention.
It seemed as though you had a spotlight on you, the way your dress glistened softly, your light smile drawing in awestruck gazes from every direction. Kendall analyzed every man who let their eyes linger on you as you passed by, his grip around your waist growing tighter with the minute. Although, he wasn’t saying anything you knew the increased attention surrounding you was driving him insane. Of course, Kendall's ideal night consisted of having the most desired woman in the room but tonight felt excessive. With men who had never spoken to him in his life stopping to shake his hand, clearly only for a chance to gain proximity to you.
You grabbed a champagne glass from a waiter before turning on your heel away from Kendall commenting “I’m going to go mingle.”
“What are you-” his question, cut off by quick disappearance into the crowd.
It was easy to charm the kind of men you find at these events. Whether they were married or single, younger or older all you had to do was act interested in their lives. Listen to them talk about how much money they make, throw in an innocent giggle and they’re easily under your control. Which made it easy to flirt with random billionaires throughout the room, but made for little true entertainment. Reminding you what you had first admired about Kendall. Although others rarely saw it, Kendall had depth. You two often would stay up till early hours in the morning pouring out endless streams of emotions to each other. He enjoyed deep conversations and sharing his daydreams. Kendall was made of much more than just Waystar inheritance money. Every other man in the room felt so…simple, so facile compared to Ken.
It wasn’t long until Kendall found you in the crowd again, eyes locked on some investor as he did his best to swoon you. He watched as you threw your head back in laughter, lightly letting your hand graze the man's bicep.
Kendall formed a tight fist as he felt a trigger go off in his head. Kendall spent his whole life competing. He definitely wasn’t going to let your attention be stolen by anybody else. In his mind when he put a ring on it, he won you. Besides you hardly paid attention to the people at these things, why tonight did you decide to put on such a performance while brushing off all of his advances? The jealousy of your lack of attention was piling on him like a ton of bricks. He knew he had been extremely negligent in the marriage department lately, and as much as he probably deserved to be cheated on after everything he’s done in his life, he didn’t think you would be so quick to throw yourself at other men.
He made his way over to you and the man stood in front of you, quickly sliding in closely next to you. “Thanks for keeping her company, man. Keep up the good work.” Kendall joked aggressively.
“Ah anytime, we’ve all seen what a busy guy you are, hate to see you leave this beautiful thing all alone.” The man scoffed back lightly, referencing today's news. You were always impressed by rich men's ability to be mean to each other without actually fighting, it was as if cryptic trash talk was their second language.
“Oh, I guarantee I can keep my wife very entertained” Kendall asserted.
You observed the two men wind each other up, pleased that your simple yet effective plan of making Kendall jealous was working. Eventually, the other man let up, leaving you two standing alone. Kendall’s chest was heaving in front of you, his large eyes scanning the room, and you could sense that he was trying to calm himself down. Resisting from making a scene. He knew he needed to stay longer, that he should spend the entire night networking with strangers, gaining the trust of possible donors, anything to earn respect as CEO. But as his anxieties regarding your displeased attitude began growing more unignorable, he wanted nothing more than to drag you out of the venue. Away from everybody's eyes, and against only his. Protected.
Kendall wasn’t saying a word to you, and you took your opportunity to wander off again to search for anyone semi handsome you could pretend to care about. However, your first step away from him was interrupted by a rough grip on your hand. You turned hesitantly, knowing you will be met with his distressed eyes, “I’m done with this fucking game. We’re leaving.”
The fighting began the second you walked into the apartment building. Not even making it past the lobby before Kendall was yelling out “So are we gonna fucking talk about this?”
“What is there to talk about Kendall? How you clearly have no desire to even be married to me? Why don't we start there!” You explained only to be met with a stunned
“What?”.
“You’re never fucking here Kendall! And if you are here you’re high, mad at me for being upset that my husband only ever sees me when he's coked out of his mind!”. You had never yelled at him like this, shocked at the amount of anger you could feel swelling in your chest.
“Oh and now you don’t even want to have sex right? You can just hire someone for that too! I hope eventually you can spend enough money on pussy and drugs to actually be happy Kendall!”. It was harsh, yes. You wanted to hurt him. Hoping maybe your words could compare to how it felt reading the headline.
“Fuck you. Okay, what the fuck are you talking about y/n?”
“The news, Kendall! I’m not fucking stupid! Everyone has seen your recent little public affair. Obviously, I don’t make you happy so please lets just do whatever the fuck we have to do to end this! I don't want anything from you, I don't care, I just don't fucking care anymore” you aggressively stammered on, raising your hands in defeat.
Kendall was sitting on the bed watching you pace the room. He didn’t realize that his dinner last night had made so many news articles, but they weren’t lying. He did meet up with an escort, thinking that fucking someone he didn’t care about might actually help him blow off some steam. But by halfway through dinner he had already made up his mind that he couldn’t follow through with it. Sure, she was beautiful and listened to him rant about work and his ex-wife. Nonetheless, his interest faltered with every coy giggle she let out. She wasn’t sarcastic like you, she didn’t push back or tease him. It was as if you were the only one bold enough to treat him like a real person, not just a possible paycheck. He left the restaurant with her but only to have her dropped back off at her apartment, giving a soft apology while still paying her the originally intended amount. He thought he could be like his dad, not give a fuck about anyone, use anything for his own pleasure. But he was positive his dick wouldn’t have been able to get hard all night, and trying only would have made it miserable for her and him.
“I didn’t fuck her.” Kendall finally huffed in response pushing himself to stand in front of you “I couldn’t fuck her! I’ll be honest with you y/n, I wanted to. But we never even made it past the fucking restaurant! I couldn’t stop thinking about you. You never leave me side y/n and I know I fucking put you through hell and back! I’m really fucked up, but I didn’t fuck anyone else!”
You weren’t sure whether to believe him. Regardless you would still be upset that he considered it. But there was something oddly sweet about a man who could buy any woman not being able to go through with it because of you. Kendall had slowly been stepping towards, and your hands laid gently at your side, unsure of what to do with all the information in your head, only to be met with a rough kiss from Kendall. You pushed him away exclaiming “Kendall, what the fuck? I’m so fucking pissed!” yet you were met again by his tight grasp around your waist and his lips returning deeply to yours. This time unable to resist the urge to give in and kiss him back.
“I know. You should be pissed. But I love you, I love you y/n.” he muttered in response against your lips. The sound of your shared panting filling the room as the passionate kiss continued. Kendall walked you backwards until you collided with the wall behind you.
“So fucking mad at you Ken!” you growled into his mouth as you both clawed each other's clothes, his arms raking down your backside squeezing your ass roughly and brushing the sleeves of your dress off your shoulders. Letting the fabric pool around your waist his mouth was quick to begin leaving a trail of sloppy kisses down your neck, stopping to nibble gently on the skin between your neck and shoulder. You threw your head back as his mouth made contact with your nipple, he sucked harshly, pulling the skin lightly with his lips, and then soothing the sensitive bud by tracing circles with his tongue. His other hand working to undo the zipper holding up the remainder of your dress. You attempted to steady your shaking hands and loosen his belt and dress shirt but the feeling spreading from your nipples to your pussy was already causing you to struggle. When your dress pooled around your ankles, Kendall wasted no time in lifting you into his arms, legs instinctively wrapping around him as he sucked on your bottom lip. You could feel his bulge pressing firmly into your center as he trapped you tightly between him and the wall. His hips grinding, desperate to buck into you, causing a yelp to leave your mouth every time.
He moved his hands swiftly, lowering his dress pants enough to pull his cock out, rubbing the large bead of precum that was forming on his head between your folds.
“Fuck Ken!” You exclaimed as you felt his head pressing firmly against your slit. Kendall usually enjoyed taking his time, slowly working his cock into you, trying to make you as wet as possible before bottoming out. However, now you could feel him pushing in with no hesitation. Grunting as your lips squeezed tightly around him, giving you no time to adjust, only pulse as he pushed deeper. His cock had never felt so swollen inside you before. You weren’t sure if it was the time apart or the passionate argument but your pussy was yearning for every inch of him inside you, and to completely submit to his hold. But your brain still had the lingering thoughts of his actions.
“Why Ken? Fuck- why do you have to be like that? Why can’t we just talk?” You managed to moan out
“I don’t know why I’m so fucked up y/n” he grunted into your ear pushing the final inch of his length all the way inside of you. Both of you let out a sigh in unison as your bodies aligned perfectly together. Your legs spread wide for him as he held your ass in his palms, grinding deeply into you. With each thrust his pelvis softly nudging your clit driving your pleasure further.
Backing away from the wall, while maintaining his tight hold around you, Kendall walked your conjoined bodies over to the bed. Laying you down harshly against the edge of the mattress, pulling your hips quickly to meet his, pushing his dick deep back inside you. He collapsed into your shoulder, his arms wrapping around your chest. He fucked into you at a brutal pace, you were unable to controls the cries that left you lips each time his thick head brushed against the sensitive spot along your walls.
“Ken please- I need you” you whined scratching your nails down his back searching for anything to hold onto while the knot in your stomach tightened.
“I want to be better, baby. I can be better for you. I promise” He groaned deeply into your neck, his words so easily seducing you back into completely trusting him again.
“I want you home Ken, I want- ughh you” you managed to moan out breathlessly. As your orgasm drew closer, so did your thoughts about missing Kendall. You just wanted to tell him how much you loved him, how much you needed him but all that left your lips was a loud cry as you felt your pussy finally release on his cock.
“You’re making me cum! Fuck Ken oh my god, wait wait I-…” you yelped.
Your hand reached between your legs pressing your palm to his stomach as your overstimulated pussy throbbed harshly around him. He maintained his brutal pace, holding your hips in place as you squirmed against him.
“Just a little more baby, you can take me. That’s my girl” he cooed, his hands straightening your legs over his shoulder. His hips snapping against your ass, eyes never leaving yours. Watching in adoration as your eyes shut closed, but your mouth remaining open, drool falling down your chin as the pleasure slowly became too much.
With a few more powerful thrusts Kendall was releasing deep inside you. Allowing himself to collapse completely into your warm body. Shallowly grinding his hips to ride out his passionate high. Waiting until he felt your walls stop throbbing around him. Allowing both of your breathing to relax before he eventually pulled out with a long sigh. Kendall looked down at you fucked out face. His thumb brushed your cheek gently, then ran it along your bottom lip. He thought you always looked so beautiful with your cheeks flushed pink, hair wildly flying around your face. Arms reaching up searching for his protection. He wasn’t ready to give up on another marriage, not when the make up sex was like this, he laughed to himself. He gathered you in his arms scooting your bodies up the bed, until he was comfortably holding you.
Ah little Romey…We ALL know Roman is the type to catch feelings for someone after they’ve been friends for a while. Slowly increasing the amount of sexual jokes he makes towards them
One day he would call you one day while you were at work, joking about how hard his dick was. You would respond something like “Eww gross Rome, why are you telling me this?” and instantly hear him gulp on the other end
He was speechless, your harsh reaction turning him on. That's when he would really start to see you as more than a friend
You know that scene from Wolf of Wall Street, when Margot Robbie spreads her legs and puts her heel on his head to stop him from getting closer. That's the kind of thing Roman would fantasize about, eventually letting it slip out
So of course once you finally put the pieces together of his little kink, you had to take advantage…
He showed up at your apartment to find you in bed with your legs spread playing with your clit, you were shocked he actually tried to make a move. But when you stopped him and instead told him he could only watch, he was hooked. Now he had to have you
He's had so much in his life handed to him, he liked that you made him work for you
Things would start with mutual masturbation, he loved watching you touch yourself while he jerked off. Teasing him the whole time “Are you going to cum for me already? God so needy for my pussy”
Obviously this boy wants you to degrade him pretty intensely. He doesn’t know why he likes it but when you make him get on his knees for you, and taunt him about how he can’t fuck you, his pants instantly get tighter
Would try to fix any fights, arguments or even little disagreements with sex.
“Will you just sit on my fucking face!” Wants you grinding down on him while you pull his hair, moving his head where you want him. Suffocate him a little…
But I think he would also loveeeee if you were really gentle with him. Calling him a “good boy” and holding his head stroking his hair while he sucks your nipples eeeee
Okayy I think Roman would be super anxious at the thought of accidentally cumming in you and getting you pregnant. Usually pulling out to cum all over your stomach or face
But one day while he was fucking you harder then usual you couldn’t stop yourself from wrapping your legs around him, trapping him in deeper. Instantly he would be whining into your ear, repeating “fuck” under his breath as he came harder then ever
From that moment he would be obsessed with cumming inside you. Still terrified, but it was that thrill that turned him. Especially when it felt like you almost made him do it. By wrapping your legs around him, or not stopping when you're riding him
I think you could get some gooood praise out of Roman while teasing him
You had been straddling his waist, grinding your wet fold along his dick, stopping every time he got close. Eventually he would be panting “Please let me have your pussy, ugh need to be inside of you” and “You’re so good to me, I love you, I love you”
Don't think he would be a fan of wanting to take baths or showers together however, would want to watch you take a bath. Sometimes making it sexual, jerking off while he watches you lather soap everywhere. But most of the time just wanted to vent and ramble to you about whatever’s on his mind
Summary: Soft mornings with Kendall escalate to him making you squirt for the first time
Ashtrays full of cigarettes, half full champagne glasses, and last night's clothes were thrown across the floor. Ruins of the party that had ended only hours earlier, were illuminated as the orange sunrise flooded Kendalls high rise apartment. Mornings when Kendall could smell your vanilla perfume, hear your soft breaths, and reach over to find you seemed to have been making his entire life feel easier. He didn’t wake up in a panic thinking about mergers or acquisitions, everything was lighter.
Kendall leaned over, hovering above you as you slept on your stomach, tracing his fingertips lightly over your spine. He could have spent hours studying every part of your body. Caressing you, leaving light kisses on every freckle. You hummed lightly at the familiar feeling of Kendalls soft fingertips embracing you. He had a routine of waking you up by leaving light pecks from your shoulder, up your neck, and to your ear before whispering “Good morning” followed by an ever changing list of pet names. You would throw out a soft “morning love” before he was already getting up to get ready for the office.
However, today your boyfriend's touch lingered a little longer, and instead of his usual brief “good morning” he stopped to cuddle into you.
“Mm Ken, don’t you have to go into the office?” you murmured, leaning back into his touch. Moving yourself closer until your ass was perfectly situated against his slowly growing bulge.
“I have some time” he whispered. “You know, I would spend every morning like this if I could. Fuck Waystar, this is all i want.”
Ken had been increasingly more affectionate lately. Sending flowers to your apartment, scheduling surprise dates. He knew if things went well with taking over Mattson, Waystar would take over his life even more. Maybe even as sole CEO. Until then he was making sure to spend every second with you.
As you laid comfortably in Kendall's arms still half asleep, you couldn’t help the small sighs that began leaving your lips. Kendall trailing light kisses up your neck, his hands brushing softly from around your waist to the small mound above your pussy. You could feel his now painfully hard bulge grinding slowly into you. Your brain was silently begging for Kendall to move his fingers further down. However, he continued his almost innocent movement of rubbing soft circles and leaving light taps above your center. You turned your body towards Kendall, staring into his eyes briefly before moving to kiss him. Before you could catch his lips, his hand that was previously teasing you was softly cradling your face as Kendall brushed his thumb against your check. You watched his eyes flutter from yours to your mouth and back to meet your eyes again. Your heart aching with butterflies as he peppered your face with warm pecks, his morning stubble lightly scraping your chin.
Yours and Kendall’s lips finally met in a sloppy, half asleep kiss. His hand quickly returned to where it had been previously, this time pushing your thighs apart, and letting his fingers gently rest on your folds. Kendall could feel how soaked you were. Your pussy, already aching at the thought of his large cock stretching inside you. The light pressure and small circles he was rubbing into your clit, causing you to moan into his kiss.
“God, I love how you sound for me. Already so wet and ready for my cock.” He said as his fingers slowly began to spread your lips apart. He tapped lightly against your slit encouraging a small yelp from you as you moaned “Feels so good Ken.” He dragged your wetness from your slit up to your swollen clit in a long stripe before slowly dipping two fingers into you deeply. Giving you no time to adjust to the satisfying full feeling. Kendall sucked tenderly on your bottom lip as you attempted to kiss him back deeply. But with every movement it became more difficult to ignore the pleasant tension building in your pussy. He pumped his two fingers in steadily, curling them slightly as he dragged them back out, hitting the sensitive spot in your walls everytime. You couldn’t control your squirming as you began grinding your hips into Kendalls hand desperate to feel him deeper. He removed his fingers slowly from inside and you quickly whined at the loss of contact. He pushed himself up so that his back was against the headboard, swiftly dragging you with him so that he was holding you in his lap. You felt like his toy, and you loved it. Legs spread wide open, completely vulnerable to his touch.
His fingers eagerly returned to stroking inside your walls. The intensity at which he was pumping his fingers into you quickly increased, and everytime he curled his digits to make contact with the sensitive ridge inside your walls, the overwhelming sensation urged you to close your legs. His tight grip held your legs open, his free hand holding your face as he sweetly cooed in your ear “such a good girl. You look so pretty spread out for me.”
“Please Ken- don’t stop, don’t stop” you were so close, and you could feel your eyes rolling back into your head. The room filled with the sounds of your breathy moans, and the wet slap of kendall palm making contact with your clit drawing more liquid out of you and around his fingers.
“Yeah?” Kendall questioned “You want to cum baby? I want you to cum all over my fucking fingers.” His dick was straining painfully hard, pressed against your ass and he was fighting himself from roughly flipping you over and pounding into you until you begged for his cum. But he was loving watching your eyes roll back, seeing the sweat build on your forehead as you desperately pushed your hips forward into his hand. So needy for him.
“Omg, I’m- I’m gonna cum” you breathed out. Feeling you tighten and squirm against him, Kendall tightened his grip on your thighs pleading into your ear “cum for me baby. That’s it, good girl.” Your orgasm flooded your body harder than expected as you threw your head back into Kendall's chest, clenching around his fingers and screaming his name. “Shsh it's okay, it’s okay. I got you, pretty girl” Kendall hushed, leaving kisses on your forehead as you rode out your high.
When he finally removed his fingers they were practically dripping. You looked down shyly to find a small wet circle on the sheets directly beneath you. “Oh my god…did I? Did you make me?” you stammered slightly embarrassed at the thought of what your boyfriend made you do.
“Did you think your boyfriend, who is… the man, couldn't make you squirt?” he exclaimed confidently.
AN: I have had so many request for Greg smut hehe here is some headcanons about tall boy :)
You would have so much fun teasing him! Before every blowjob you would take your time pressing gently sloppy kisses along the head and down his shaft. It drove him wild watching your big eyes innocently staring up at him as you drooled on his cock. He couldn’t stop himself from pleading everytime “oh babe, you feel so good. Please- please take it all.” His hands involuntarily grabbing your head pushing down and pulling your hair slightly.
Greg never intended to be rough with you, but it always turned you on when your inexperienced boyfriend lost control of his actions and pulled your hair lightly, or made you gag around him. You loved being on your knees for him, knowing it always gave him a little sense of power.
We have all seen Greg's little encounter with having sex in risky places and I think despite Logan's reaction, that idea would continue to excite him. He would suggest ideas like having sex on the balcony of his new apartment, or at least pounding you from behind as he pressed your body against the glass.
Once during a night out with Kendall, Tom, and Roman, Greg even tried to convince you to let him go down on you in the women's bathroom. “Babe, I love your enthusiasm about having sex anywhere, but don’t you think you're a little too tall for that?” “Well no, you see because, I’ll just kneel down like this, and you're wearing a dress so you know, easy access…” he stammered as he demonstrated. Even when trying to be sexy he always made you laugh.
I think Greg would turn to Kendall for sex advice. Asking him questions like “So can I make y/n actually like… squirt? Or is that just in the movies”
But honestly you didn’t want Greg to change a thing! He was better than he thought and even though he always seemed insecure about his size, he was one of the biggest you had ever seen.
You remember the way it slapped against his stomach the first time he pulled it out of his boxers, already leaking precum from his swollen tip. His hands were shaking as you slowly kissed down his stomach. He finished quickly inside your mouth, unable to hold back his orgasm, but within minutes was ready to go again. Swiftly picking you up with both arms, kissing you deeply as you wrapped your legs around him.
He definitely struggled to put on the condom the first time you guys ever had sex.
You took this as a cue to slowly slide it onto him as you looked into his eyes. In that moment he knew he would do anything to keep you around. He never has anyone make him feel so comfortable with himself.
After the first time Greg would be so excited about the thought of trying new things with you. You would be cooking dinner and Greg would slide next to you casually mentioning “So…I’ve been reading about the art of Kama Sutra” you couldn't hold back your laughter with Greg instantly working to defend himself “what? Babe, it says it's a really great way for couples to bond and brighten their sex life!”
He would make you laugh during sex. Not in a bad way! But I just think he would say silly things that would make you laugh as you're moaning.
Can’t you just see yourself saying “Greg stop making me laugh, I was about cum!” As his face is buried between your legs.
Would slowly get better at the dirty talk but eventually he was saying this like “oh, you take me so well” maybe occasionally a “good girl” in there ;)
Most nights with Greg would be fairly soft and vanilla. He loved missionary and being able to watch the expressions on your face as he slowly pushed into you. Enamored by your moans and the fact that he was the one causing them.
I think the first time Greg said I love you would be during sex. It would just flow out of him as he was pounding into you harder than usual. His face buried deep in your neck, letting the words slip into your ear.
Cuddling would be essential for him after sex. Not shy about wanting to be the little spoon.
Even if it was just a quickie he would spend minutes after just holding you.
As opposed to wanting to be rough with you after a hard day in the office I think Greg instead would appreciate you taking control. Straddled his waist slowly grinding down onto his hips. Whispering in his ear how much you needed him as you gently lowered yourself onto him.
such an affectionate boy in the bedroom. Would constantly be checking that you were okay. “Is this okay?” or “Want me to slow down?”
Summary: After spending the day with Kendall and his two kids, Kendall admits he frequently fantasizes about having another baby with you. This conversation quickly leads to an intimate night of him trying to make that happen.
“I mean, is this all my life is y/n? Forty years of fucking up”.
“Ken, your life is forty years of being an amazing older brother, a hardworking son, and a great dad! Maybe with a few hiccups along the way but…who's counting?” you exclaimed as you placed a fresh cup of coffee in front of your emotionless boyfriend. His large eyes staring back at his reflection in the black liquid.
“The press is counting, my family is fucking counting. And you don’t have to lie y/n, I know I am neglectful in all those relationships. Especially with my kids” he roughly remarked.
For weeks you had been pushing the idea of Kendall spending more time with his kids. Whenever he had a day off you would throw out suggestions like, “Hey Ken, the weathers great! Maybe we should bring Sophia and Iverson to Central Park.” Or “NYC has so many museums, we should take Sophia to the ballet, and Iverson to the Hall of Science”. Never intending to make Kendall feel like a deadbeat dad. You knew how he admired his kids. Occasionally he just needed a little push to be there for them.
Due to Kendall’s lackluster attitude you figured today wasn’t the day to ask kendall if he wanted to make plans with his kids. Maybe it was the warm Saturday morning air flooding the usually chilling apartment, or the fact that Kendall was finally not in the office on a weekend but you just had to throw out the idea one more time. “Ken, I know you're having a rough day” you said softly as you reached out to squeeze his open hand. “But maybe not being cooped up in the office or your apartment will make you feel better-”
“Look, I know where you're going with this y/n and I’m not going to another one of your fucking pilates classes.” Kendall directly cutting off your sentence before you could finish. You couldn’t help but laugh at your boyfriend's consistent apathy.
“Damn, but I just love seeing you so worked up and sweaty” you retort. “No Ken, I was going to say, why don't we take Sophia and Iverson to the zoo today?” you cheerfully presented. To your surprise Kendalls eyes nearly seemed to light up at the word “zoo” as if something clicked inside of him, almost breaking his depressive state. Kendall responded with a quick “let me call Rava”.
You watched the rows of skyscrapers pass as you and Kendall sat in suffocating silence on the way to Rava’s apartment. Kendall fidgeted in his seat, pulling on his t-shirt, mindlessly switching between apps on his phone before eventually letting out a quiet “you know, you don't have to come if you don't want to y/n, I can pick them up by myself if it makes you more comfortable.” You placed your hand gently on his upper thigh giving a light squeeze as you explained. “Ken, it's really okay. I mean she's the mother of your children! We can't exactly avoid each other forever.” you said, showing a soft smile to assure Kendall of your confidence. Honestly, you and Rava got along fine. Although she was slow to warm up to you, you never took it personally. Who wouldn't be cautious of their drug addict, ex husbands, new girlfriend. Over time her cold demeanor shifted as you two began having small conversations whenever she would pick the kids up. You almost admired Rava in a way. She was beautiful, always looked elegantly put together, successful in her career, and she was an amazing mother. Everything you secretly hoped to one day be for Kendall.
As the car pulled up to Rava’s apartment you mind began to picture how your future might look with Kendall if things continued at the pace they were. Of course, Kendall had joked many times about getting you pregnant and running away together to get married. But you two never had a real discussion about what you saw for your future. You couldn't help but occasionally daydream of you and Kendall standing in an empty room deciding between sage green or soft peach, paint swatches for a nursery. Or rocking your baby to sleep as Kendall softly wrapped his arms around your waist, humming gently in your ear.
Your mind wandered further into your maternal daydream as your day at the zoo went on. Observing how patient and gentle Kendall was Iverson and how lovingly he doted on Sophia, had your heart skipping beats every minute. Making sure to capture hundreds of photos of all the adorable moments. Kendall typically only showed his love in undisclosed ways but with his children it was on full display.
As you and Iverson stared into a tank of swimming otters counting each one that passed, Kendall realized for the first time in weeks he didn’t feel like the world was collapsing in on him. There was something reassuring about watching you point out different frog species with Iverson and hold hands with Sophia, skipping together to each animal. Everytime he heard one of his kids yell “Dad, come look!” served as a reminder that he still had people in his life who cared about him. Who needed him.
Kendalls wandering thoughts were interrupted by a small tug on his sleeve and he looked down to find his daughter sweetly beaming up at him.
“What's up Princess? Are you having a good time?”
“Dad! y/n is so cool and you’re always happier when you're with her!” The young girl exclaimed.
Kendalls entire demeanor softened, and he kneeled down to wrap his arms around Sophia. Hearing those words nearly broke his heart. He was highly aware he wasn’t always at his best when around his kids, but he always tried to fake it for Sophia and Iverson. The fact that his kids could see past the facade made him sick. Just another reminder of the ways he was becoming like his father.
Kendall attempted to hide his shame from Sophia, responding smoothly “Yeah Soph, I guess you’re right about that. Lucky for us, I think y/n is here to stay.” In spite of her fathers hopefully tone, Sophia was hardly a young kid anymore and she could still see the fragment of sadness Kendall felt. She pleaded further “Please dad! y/n is the best! I want her around forever!”. After his divorce Kendall decided remarrying was out of the question for him. The thought of being like his dad; multiple wives with kids he ignored from each, practically gave him nightmares. However, Kendall couldn’t deny that when he met you, his mindset instantly changed. Within only a few months the thought of you having his child definitely crossed his mind more than once. He would catch himself picturing moments like you handing him a pregnancy test with a bright ‘+’ result. Staring up at him with your soft eyes anticipating his reaction. How he would scoop you up in his arms and yell “we're having a baby!” kissing you all over and reminding you how he would take care of you forever. Nonetheless, he always pushed those thoughts aside and never revealed how he really dreamed of you two ending up. The press already had a field day with your age gap, you were really starting to build momentum in your career and the last thing he ever wanted to do was make you feel trapped.
That night you and Kendall sat snuggling on the couch, scrolling through all of the silly photos taken throughout the day. You felt especially safe wrapped in Kendall's arms tonight. Assuming it was just the effects of getting to see Kendalls paternal instincts. He left gentle pecks along your forehead while giggling at every photo of Iverson and Sophia posing with the animals. The effortless time with his kids paired now with your warm body cuddled on top of him reliving the memories was already filling him with a mellow nostalgia.
As you scrolled past a selfie of you kissing Kendall on the cheek you giggled “we would make such cute babies.” Instantly Kendalls ears perked up seeing as he was the one usually joking about making babies.
“Are you kidding? Our kids would be like the next super model, techno DJ, fucking ultra geniuses!”
You expected Kendall to have to have such a teasing reaction but honestly you were being serious.
“Fuck yeah they would!” you joked back, pressing a peck to your boyfriend's lips. Kendall quickly deepened the kiss before pulling back to look at you.
“Did I ever tell you how sexy I think you would look pregnant?” Kendall whispered. “What? Omg Kendall no! You have never told me that” you laughed.
“Come on. What do you think… I think about after I cum in you?” he said with a large grin.
“Ken I- are you serious? Do you really think about you?”
Despite the giggle you let out as you asked, you knew Kendall caught on to the trace of hopefulness behind your question.
“Uh of course, I think about how fucking beautiful my girlfriend would be with my child, yeah.” Kendall assured.
Your heart was nearly pounding out of your chest. Despite being unsure if Kendall was being honest or simply pulling your heartstrings hearing him say those words was making you melt deeper into his arms.
“Mm really? How often?” you teased, hoping to gather more confirmation that Kendall wasn’t just joking.
“Um okay, you want me to be honest?” he asked.
“One hundred percent.” you said.
“Like. Everyday.”
Stunned by his answer, your mouth fell open and stumbled to come up with a response.
“Seeing you with Sophia and Iverson, waking up to you every morning, fuck y/n, you have no idea how bad I want to come home to you and our family.” Kendall continued.
“Our family?” you questioned.
You could sense Kendalls discomfort with your reaction. You hadn’t intended to say that thought aloud but you were speechless. It felt as if the delusional world in your head and reality were swapping places.
Kendalls large eyes were staring into your eyes, anxiety flooding his body, praying you say something else.
“Ken I-” you began, before being interrupted by a distressing Kendall.
“Look y/n its just a thought, I mean I’m definitely not trying to push for something you’re not ready for, like I know your young and-”
Crashing your lips into Kendalls was the only way you knew to shut him up from his fearful rambling.
“But…I want you, Kendall.” you said.
Your hands holding his face to look directly into his dark eyes. “I want all of you. All of your bad habits. All of your ex-wife, Roy family drama baggage. And especially…to have your babies.” you drew out slowly, letting a devilish smile creep onto your face.
That was all the reassurance Kendall needed before he was kissing you deeply , moving to positioning himself in between your thighs, hovering above you.
“Is that really what you want y/n? You want me to make you mine?” His previously trembling voice was now confident and nearly patronizing.
“Mhm baby, only yours” you replied sweetly while attempting to grind your hips up to Kendalls. That slight bit of friction was met with a repressed grunt from Kendall, his hands moving to tightly grip your hips, halting any movement. You could tell Kendall was already craving you. You could feel his dick growing harder as it pressed firmly against your clothed center. The truth was Kendall was hard since the conversation had begun. Even when you had simply joked earlier about making cute babies Kendall couldn’t help the blood that instantly rushed to his cock, causing it to throb against his sweats.
Kendall moved slowly to remove the soft sweater you were wearing, gently helping you to pull out each arm before lifting it over your head. His lips softly connected to your neck. Leaving light pecks, stopping occasionally to gently suck on the skin and admire the small blemishes he was leaving behind. His large hands softly massaging your breasts before his tongue swiftly moved to draw light circles around your nipples. Taking the small bud between his lips and sucking tenderly, making sure to give each nipple equal attention. Your body pushed your chest forward desperately giving in to his delicate touch. His ability to instantly turn you into a moaning mess never failed.
You squirmed beneath him searching for something to grind against, desperate to stimulate the area he was ignoring.
“This is what you’ve been waiting for isn’t it? For me to fuck you and make you mine? Already so eager for my fucking cum in you. My pretty girl” Kendall taunted softy. Watching you gasp as your back arched into him.
“Please Ken” you pleaded.
His fingers trace slowly down your body, finally making contact with your touch deprived center. Using two fingers to rub soft circles on your clit and slide them through your slick folds pressing firmly against your slit. His fingers were instantly covered in your wetness before he even dipped them into your pussy.
Kendall stared into your eyes as he brought the first finger he used to spread your pussy to his lips. Sliding the digit slowly into his mouth, “Fuck! You taste so good”. Bringing his second finger to your mouth with a commanding “suck”. You gladly accepted and softly sucked on the flesh tasting yourself before Kendall removed the finger with a loud popping sound.
He quickly moved from between your thighs to kneeling at the edge of the bed, wrapping his arms firmly around your thighs and pulling your dripping pussy level to his mouth. You cried out as his lips connected directly to your exposed clit. Kendall hummed into your pussy as he tongued the sensitive bundle of nerves. Your hands grasped desperately searching for something to hold onto as you felt your orgasm building in your stomach. Kendall removed his firm grasp from around your hips and found your hands, interlocking his fingers with yours. “Fuck Ken! You’re gonna- make me cum! Please- please don't stop!” You cried out, squeezing his hands harder feeling your eyes close shut. On nights when Kendall was feeling especially dominating, now is when he would completely pull away. Always trying to see how many times he could bring you to the edge before he finally gave you permission to cum. However, tonight was different. Kendall was on a mission to prove just how good he could make you feel, how bad he wanted to give you everything, that he would truly take care of you. His cock was leaking with precum appreciating every sound that left your body as he continued working your pussy. Rapidly licking at your slit and sucking on your clit until finally the knot building in your stomach released. You couldn't stop the dramatic stream of moans that left your body.
“Oh my God Ken!”
“Good girl” Kendall hummed as you attempted to catch your breath feeling your sensitive pussy throbbing inside.
You yelped, as you felt Kendalls mouth return to your overstimulated clit leaving light kisses while he worked to remove his sweatpants and boxers.
Kendall gently lifted you in both arms and softly laid you back down in the center of the bed. Taking his time to kiss you deeply as he wrapped his arms tightly around you. His chest heaving against yours as he lowered his waist. His dick finally making contact where you had been craving it most, smoothly grinding his tip in between your folds.
He buried his head in the crook of your neck, his dark voice whispering lowly into your ear “You’re my fucking girl.”
“I’m all yours Ken.”
“And this.” Kendall moved his hands to lightly slap his dripping head against your clit, “is my fucking pussy.” His aggressive words muttered with affection and tenderness.
“It’s your pussy Kendall. Forever”
Gradually Kendall began pushing his tip into your soaking entrance, taking his time to guide his cock deeper. Halting his movements frequently to feel you stretch around him.
“Fuck! I love you.” He grunted when his cock finally bottomed out. Dropping all his weight onto your hips, rocking deeply into you. His body was pressed so tightly against yours making you feel especially small and protected. His pelvic bone brushing against your clit with every thrust as he smoothly gained aggression.
Breathy mumbles of “I love you too Kendall, I love you so much” left your lips. His powerful thrust sending electricity straight from your brain to your pussy and through every inch of your body. The sound of your wet pussy dripping around Kendalls cock, his warm breath brushing your neck as he moaned deeply instinctively made you wrap your legs tightly around his hips. Although Kendall had intended to be soft with you tonight he couldn't stop himself from pounding into you ruthlessly. He could feel your pussy tightening around his cock with each thrust signaling you were close to cumming once again.
“Fuck baby! Why are you so fucking wet for me huh? Does it turn you on knowing I’m gonna cum in that fucking pussy? My pretty girl, gonna have my baby?”
He wasn’t expecting a real answer, only seeking to push you closer to cumming on his cock. He was using everything in him not to cum before you and you could feel his smooth pace become more erratic as he snapped his hips harshly against yours.
Letting go of his tight grasp around your body to balance with his forearms on either side of your head. Holding your face with his hands, pressing his forehead lightly atop yours.
“You want my fucking cum?” He questioned, doing his best to maintain a firm tone as he held back his orgasm.
“Yes Ken! I want your cum, baby! Please!” you cried out.
“Tell me where you want it. Tell me where you want me to cum baby”. He was fucking into you at a brutual pace watching as tears began forming in the corners of your eyes.
“Fuck! In my pussy Ken, please cum inside me!” you pleaded as his words drew you to your second orgasm. That was all Kendall needed to hear before he was releasing deep inside you with a powerful thrust. It felt as if you could feel his cum hitting your cervix as he maintained his rough pace, fucking his cum deeper into you. Kendall could feel his orgasm rushing through his entire body, his cock throbbing inside of you, twitching, as he felt your nails drag down his back and your pussy squeezing around him. Milking every ounce of pleasure.
Kendall slowly pulled out you with a deep sigh. The loss of contact, already causing you to feel empty. You were yearning for him to reach out his arms again and pull you into a deep hug. Kendall traced his fingers lightly over your stomach, remaining silent as he studied every inch of your body before dropping to lay down on his back next to you. “Is he already regretting this?” You thought to yourself as Kendall laid silently staring up at the ceiling. You could feel you heart slowly sinking, letting out a soft sigh as you sat up and began shuffling off the bed. Your movements, quickly interrupted by Kendall reaching to pull your body into his lap. Straddling him, his toned arms pulled you into him tightly. Your chests rose and fell in sync as you both breathe in deeply. You feel Kendalls chests begin to vibrate beneath you and he lets out a loud chuckle, brightly exclaiming “We’re gonna have a fucking baby!”
Okay sooo starting strong and maybe controversial but i think Kendall might umm cum kinda fast. But, even if did last a normal/good amount of time I think he would always be insecure that he finished too quickly.
Sooo because of that little insecurity I think he would always! try to go down on you after he came. Like, even if he just made you cum 3x on his dick he would still be like “come on baby just one more” as he's kissing your clit because he's just so worried about making you feel good!
Kendall being into toys just makes sense to me. Like he definitely would want to try handcuffs. Mostly on you, but I can see him wanting to be handcuffed while you suck his dick or ride him.
He would loveeee to hold a vibrator on your clit until you push him away or literal tears start falling and your screaming “Kendall please oh my god, I- cant-”
I think Kendalls main kink would just be trying to make you cum as much as he can! It would be so reassuring for him that even if he was a fuck up in other ways at least he could make you cum 5x in one night.
That would keep him going on hard days haha just picturing you waiting for him naked at home.
We ALL know Kendall would be a huge fan of car sex. Gently stroking and squeezing your thigh while you're on your way to some fancy event. Slowly inching his fingers higher, until he starts lightly brushing his fingers tips against your clit.
He wouldn’t even look at you while he teased you, keeping his focus straight ahead. Would probably do it while he was on the phone. Slowly making you come undone while he talked to Stewy or a possible new investor.
On the drive home he would purposefully make you moan as loud as possible. Secretly, hoping the driver could hear everything he was doing to you.
I think he would be into taking a shower together after you guys have sex. He just wants to hold you in his arms under the hot water for at least 20 minutes straight.
“Ken maybe we shouldn’t use all the hot water”
“Babe, I don't know if you know this but I’m fucking rich. I’ll have hot water flown in from fucking underwater volcanoes if it means i can hold you longer.”
Then he would wash every single part of your body so gently and soft with soap that probably costs the same as your rent in NYC. Definitely stopping to suck on your nipples, and squeeze your ass
Since a relationship with Kendall might be a bit on/off, make up sex might be a frequent occurrence. Sometimes it would feel like he was trying to start a fight just so you could have rough sex after.
But once you figured out his little game you started teasing him and not giving in so easily. At first Kendall was pissed. I mean, the poor man already feels so out of control in his life he at least liked getting to be dominant in the bedroom. However, that was until the first time you actually got him to beg to cum.
You were on top riding him and every time he got close to the edge you would stop.
“fuck baby don't stop I’m gonna cum”
as soon as he said that your hips halted. Teasing in his ear “aww baby did you wanna cum in me? Not yet” you did that 3x more times until eventually Kendalls eyes were rolling back and he couldn't stop himself from grabbing your hips and holding you while he fucked up into you, cumming sooo deep inside.
Ever since that moment occasionally he would let you take control but usually he was the dominate one
Kendall has fantasies of you waking him up with head, and would drop not so subtle hints about it. “Yeah, I think I could just increase my performance if I started everyday with like an orgasm”
His favorite thing in the world is to receive a random nude from you while he's at work but would want it to be kinda special. Like you have on fancy lingerie or you’re taking a bath. Something more than just a mirror pic, but he would gladly take that too!
My brain is just a montage of Radiohead Mitski Kendall edits right now, I could keep going forever!
Enjoy♡
AN: this is my first story ya'll go easy, but its simple soft dom Kendall stuff so I hope you all enjoy♡
Lately it had felt like every weekend with your boyfriend Kendall Roy meant you spent the night walking into some abandoned looking warehouse in Queens. Or occasionally a glamorous but to be honest, boring night club in Soho.
Where did he even find these parties? You thought to yourself as you strapped on your high heels, mentally preparing for another night of being Kendall’s arm candy.
Kendall wasn’t always like this though. Of course, you were well aware of your boyfriend’s heavy partying “habits”. In your first month of dating, he showed up to your apartment three times in the middle of the night. High off of a combination of god knows what, reciting Harvard level love poems at your window. You soon realized the parties were just a part of the Kendall package.
However, it felt like for a minute you two had started to get truly…close! He began taking you to five star restaurants as opposed to the typical nightclub. Updating you about his schedule, sending “I miss you texts”. You two even had a weekly ritual of falling asleep to 90s cartoons! He had been working out more and doing cocaine less. Why the sudden shift backwards? Was it all in your head? Is he really just a rich, party addicted, man child? Your anxious thoughts began to spiral as you stared at your reflection in his grandiose bathroom mirror.
“Fucking Beautiful” your mental spiral was interrupted by the grasp of Kendall’s arms squeezing tightly around your waist while placing soft kisses down your neck.
He seemed to instantly notice the fake smile you put on and the slight sigh that left your lips. Kendall could always tell when you were upset. It was like he was an expert at reading your body language after years of navigating his complex family.
The Tom Ford suited man turned you around to face him and his soft hands lifted your chin up to meet his eyes. “What’s up? What are you thinking?” He expressed flatly.
“Nothing Ken, I just-“ his lips instantly, forming into a frown. While his almost angelic eyes remained softly looking down at you.
God, he looks so hot when he pouts, you thought. You considered for a moment just forgetting everything. Saying fuck it and just going out. But you were genuinely starting to fall for Kendall and it seemed important at that moment to tell him how you felt.
“I just don’t think I feel like going out tonight” you said, doing your best to sound sweet as opposed to disappointing.
“Oh uhh yeah well” Kendall stumbled.
“I was hoping to maybe spend time with just you Ken…” you smiled up at him, reaching for his tie to pull him closer for a soft peck. Kendall quickly deepened the peck wrapping his arms lower around your body and stepping closer to trap you between him and the bathroom counter.
“Mm look at you, so cute and needy for me” Kendall said, as his hand moved up your back, grabbing a handful of your hair and gently tilting your head back to leave soft kisses on your neck. “You know… if you want me. You should be a good girl and just tell me.” Kendall whispered in your ear. His harsh kisses along your collarbone paired with his words cause a soft moan to slip from your mouth.
Kendall took a slight step back holding your face in his hands. Your lips both parted and nearly brushing against each others as he looked down at you.
“Tell me what you want y/n.”
A soft breath left your mouth before you stumbled to get the words out.
“I..mm. I want you Kendall. Right now” This wasn’t exactly how you intended for this conversation to go but you definitely weren’t upset at his reaction.
“Good girl” Kendall softly drew the words out in response.
Pulling you closer yet again into another deep kiss. The intensity of his lips against yours increased along with the butterflies in your stomach. The way he seamlessly switched between gently caressing you, as if he was too rough you would break. To devouring every inch of your body with kisses and love bites. Squeezing your ass, gripping your hips and thighs, his hands were everywhere. Before they eventually landed on your dress zipper. The room filled with heavy breaths and sighs, your clothes feeling more like a barrier every second.
As Kendall began roughly pulling your dress down your body, your hands swiftly reached up to begin loosening his tie. His large hands quickly interrupted yours, enclosing around your fingers, roughly bringing your hands back to your side and behind your back as he spun you around. Faced again with your own reflection in the mirror. Although, this time instead of negative thoughts of Kendall, only the thought of his tongue carelessly licking your clit filled your mind. Kendalls dark eyes stared into your reflection as his hands journeyed down your body. His rough finger brushing over your clit, stopping to draw light circles as he toyed with the hem of your lace thong.
His hands slowly slipping underneath the fabric made you gasp and drop your head down. Kendall was quick to object to that reaction, roughly grabbing your face with one hand, returning your eyes to his hard gaze.
“I want you to watch yourself cum for me” “okay?” Kendall firmly demanded while slipping your thong down your thighs.
“Yes..please.. I want to cum for you” you managed to get out as you felt Kendall's middle finger begin to slowly slip into your pussy. His solo finger easily slid in and out and Kendall quickly added in a second. You could feel your wetness spreading as it slowly began to coat the inside of your thighs.
Kendall was nearly shocked by how quickly you were ready for him. Your soft walls were already beginning to tighten around his fingers, and the lewd echo of your dripping cunt was almost too much for him as his growing cock strained against his pants. But he couldn’t help but tease you a little more.
“God this little pussy is so fucking wet for me. Do you really need my cock that bad?”
“Mm- yes Ken..please” You pleaded with him. One of Ken’s biggest turn ons was begging, and at this point you wanted to rile him up. His aggressive yet tender tone behind all his words was driving you crazy. You could feel your pussy throbbing, needing more than just his fingers inside you.
“I want to cum all over your cock! God, please ken… fuck me!”
Kendalls hands withdrew from your body as he began undoing his belt, and lowering his dress pants.
“Sh sh sh” Kendall hushed into your ear before leaning down to spit on your pussy. Rubbing the head of his dick in between your folds.
“How do you still sound so fucking innocent while your begging me to fuck your little pussy?”
Kendall couldn't hold back his moans as looked down at his dick spreading your wetness, from your slit to your sensitive clit. His teasing was growing unbearable and you couldn’t stop yourself from pushing your ass further back, closer to Kendall. This was quickly met with a hard slap on your ass. The whimper that left your mouth nearly sounded pathetic.
Kendall began pushing the thick tip of his dick painfully slowly into your pussy. His head dropped to fall against your shoulder and you could feel deep breaths leave his body as he tried not to already cum in your tight pussy. God, the way you stretched around his length slowly squeezing every inch of his dick made him feel like your pussy was made for him. Like you were made just for him. To hold, and kiss and fuck however he wanted.
Kendall pulled out slowly before roughly snapping his hips forward slamming against your ass. He kept this slow yet aggressive pace as his hands made their way up your body and to your tits. He gently pinched your nipples, squeezing the small buds between his fingers. Earning multiple high pitched squeals from you encouraging him to quicken the rate at which he was thrusting into you.
“Omg Kendall, your cock feels so good inside me, so fucking good” you moan.
“Oh look at you. You take my cock so fucking good baby don’t you? Mm fuck, look at how pretty you look while you get fucked. God, you make me so fucking happy baby”
His patronizing tone echoed in your head and you continued doing your best to maintain eye contact with Kendall in the mirror. It was turning you on even more watching yourself become undone for him. Mascara beginning to run down your face as Kendall continued roughly fucking into you.
You could feel your eyes rolling back as that familiar warmth of your coming orgasm grew in your pussy and Kendall could feel your release coming as you tightened around him. He watched as your attention from him began to fall as you came close to finishing. But he was going to make sure you watched yourself cum all over cock and grabbed a handful of your hair and roughly pulled down returning your gaze to your reflection.
“Aw don’t look away now baby. You were being such a good girl for me. Don’t you want me to let you cum all over my cock princess?” he says. The final pet name made you shiver “Yes Ken, please I am going to cum. Please let me cum on your cock” you cry out clenching around him. Your voice, so desperate and needy, whining for his permission to let go.
“Mm cum, cum for me baby.” He praises in your ear, leaving soft kisses on your temple. Still maintaining his brutal pace. Desperately, your hands grip the bathroom sink in front of you feeling your hips involuntarily grinding backward onto Kendall as you feel yourself pulsing around him, milking his hard cock. “Good girl, my good fucking girl” he praises you through your orgasm, all the breath and weight leaving your body. Kendall’s thrust gains aggression before finally stuttering as he finishes into you deeply, dropping nearly all of his weight onto your back.
Kendall hovers above you for a moment letting out deep breaths, staying deep inside of you. Now coming down from your high, you study your two reflections in the mirror. How, Kendalls arms are wrapped so tightly around you. The feeling of his chest rising up and down against you with every breath. You wanted to savor this moment. Hold onto the feeling of him pressed so close against you for when he was gone again.
Eventually Kendall slowly pulled out of you with a soft sigh, peppering kisses along your neck. “I’ve been doing some thinking. And uh.. I think we should stay in more weekends”.
