You can't have everything, Kid

pairing: jensen ackles x male reader

request: Could i request a Jensen Ackles x Male Reader; Where the reader is the personal assistant of Jensen, and for the past few weeks, Jensen has been more angry and gets pissed off easily. When reader overhears Jensen talking about maybe finding a new assistant, he realizes that his job is at stake and doesn't want to be away from his crush, so he decides to please Jensen in anyway possible. For weeks reader works overtime to do anything for Jensen, without any change, but one night, while picking up a half-drunk Jensen, he gets to know that Jensen is going through a divorce and needs someone to meet his bedroom needs. Reader jumps at the opportunity, and "sacrifices" himself to be Jensens personal whore.

warnings: SMUT, rough sex, degradtion, face slapping, cum denial, choking if you squint, kinda cheating, breeding, unprotected sex, daddy kink, pet names, bondage if you kinda look really hard, and something else

words: 1.9k

working for mr.ackles was no easy task, between his random rage outbursts, the overwhelming work, and the back aching overtime you were doing for him it was all to much but you stuck through the job if it meant that you got to see that fine ass man every day, you'd do anything for him, waiting hands and knees for his every order like a good boy.

if we're being real sometimes you'd stay up at night fucking yourself with a dildo imagining it was jensen fucking you with his thick cock as you moaned out his name but every morning you woke up to the same reality, and it was even more nerve racking when you over heard mr.ackles talking about firing you because you had been slacking off.

so the only logical thing you could do is start working overtime hoping that would be enough, night after night you stayed after hours helping him do work and try to take some of the stress off him but that was barely working so you had to find another way to keep your job and the lord must have heard your prayers.

the night you were working and getting stuff organized for mr.ackle you got a call from the local bar saying jensen said to call you since he got to drunk to drive home, you immediately hopped in your car and drove to the bar hoping he was okay, you pull up to the bar to see jensen sitting on the curb.

"mr.ackles are you okay" you ask lifting him up "yeah im... im fine" he slurs his words a bit due to the alcohol but you nonetheless get him in the car and soon begin driving "why didn't you call your wife sir" you question glancing at him to make sure he's okay "fuck that bitch" he curses "what do you mean" you ask with eyebrows furrowed "we're going through a tough situation right now it's nothing" he says.

you wanted to be civil about it but on the inside you were dancing with joy that that bitch- i mean his wife wasn't doing so well in the relationship "and i haven't been able to get off in weeks" jensen admits in his drunken state not even realizing what he said which gives you an idea.

"well if you ever need anything i'm here for you" you softly say moving your hand to rub jensens thigh, you see a slight tent rise in his pants "mmm y/n" jensen strains, feeling your hand rub on his thigh is the most contact he's gotten from someone in weeks "yes mr.ackles" you innocently say as if you didn't plan this all in a matter of seconds "fuck" jensen mutters under his breath trying to resist the urges too have your hand wrapped around his dick.

"oh my god are you okay mr.ackles" you ask faking any concern and pulling the car over to the curb before turning attention to him "will you..." he says but is to embarrassed to get the words out so he just moves your hand closer to the tent in his pants "oh no mr.ackles i couldn't do that" you keep up your innocent facade to reel jensen in further.

"cut the shit, i see the way you look at me during work and i know you've jerked off to the thought to me fucking you open every night, and shut up with the mr.ackles shit and call me jensen now are you gonna ride my dick or not" jensen snaps at you making you almost whimper at his agression "yes sir" you say stripping down to nothing, jenson taking off his pants and underwear along with his shirt.

you straddle his lap, and take his dick into your hand, stroking it slowly as you hold eye contact with him "yeah baby just like that" jensen breaths before pulling you into messily make out, his breath reeked of booze but you pushed through, fueled with the thought of finally being able to ride your boss.

"now ride me like the good little slut you are" jensen smirks as you shakily lift over him "c'mon you gotta have lube in here somewhere" he says rummaging through you car before finding a half empty bottle of lube in your glove box "half empty, you must get fucked a lot" jensen says before putting some on his fingers and smearing it on his dick and then on your hole and throwing the bottle in the backseat.

you lower yourself onto his dick slowly making jensen more and more frustrated "come on slut i dont got all night" he says grabbing your waist to push you all the way down on his cock, you moan out loudly "now doesn't that feel so much better, my dick all nuzzled in your hole" he says, his voice slick with cockiness, you look down to see the outline of his dick in your stomach making you whimper at the sight.

"yeah that's me in you, gonna ruin you from the inside and out" jensen says with a sick smile as he poke at the bulge and begin lifting and dropping you on his length over and over "jen- fuck... jensen" you whine "what" he asks, his attention set on the way you take his cock "slow down please" you ask throwing your head back.

"come on i thought this was your fantasy, to be getting your ass split by your bosses dick, you can take it" jensen says not stopping his motion into you "it's to big" you whimper feeling it spread and hit parts of you your dildo couldn't even get "well then do it for the sake of your job, if you can ride me till i cum then you keep your job, if you don't you're fired and you don't get to taste this sweet dick ever again" jensen smirked st your now scared expression.

he was putting your job on the line, but i mean you asked for this when you made advances towards him so now you have to get him to cum to keep this job and your boss "y-yes sir" you stutter lifting yourself off his cock and lowering onto him, his hands still holding your hips for support "mhm just like that, fuck yourself on daddys dick" jensen groans.

"you take me better than my wife ever did, that whiny bitch could barely take the tip but you... you can take all of me with no problem" he says thrusting upward into you a little "thank you daddy" you whine, feeling your knees go weak as you continue riding, you move you hand to your aching dick and start jerking off.

"ah ah who said you could jerk off" jensen tuts holding your hands behind your back with his own and slapping your ass "but i need to cum" you beg "looks like im gonna have to punish your slutty ass" jensen says and you feel your heart drop to your stomach knowing he wasn't gonna be light.

jensen wraps his hand around your throat and forces you too look at him while his other hand holds your hands in place before he begins thrusting up into you, the plaps filling the car as the windows become foggy from the sweat in the car, you moan out into the car as jensen assaults your hole brutally "daddy" you moan out at every drop.

"yeah you love the way i fuck you right, wanna feel this dick every day" jensen spits out roughly as his eyes fill with lust and hunger, you nod at his question "mhm" you whimper lowly tightening your hole around him "want my kids deep in your stomach huh" jensen asks "wanna make me a new daddy, walk around my house filled and good" and you moan at the mere thought of you getting fucked by him every day.

"yes daddy please fill me up with your cum, i want you in me all the time" you moan "im gonna fucking ruin your ass and make it all sloppy so no other guy can fuck you" jensen says through gritted teeth, and just right there you cum all over his chest, you look down at him with fear written in your eyes "please daddy im so so sorry i didn't mean to cum" you try to apologize but its to late "cumming when i didn't say you could, not only are you a whore but you're a disobedient whore" jensen says with a smirk.

jensen moves his hand from your throat and your head drops as his hand moves to slap your ass "count how many times i slap your ass okay" jensen says and you nod without a single thought in your mind from being fucked dumb, one slap on your ass "one" you weakly say and another "two and another "three" and another till you couldn't even remember what number you were on "which one was that y/n" jensen asks still fucking into your sloppy hole "five" you answer "wrong answer" he says and you could feel him go harder.

"so fucking dumb all over my dick, not a single thought behind those eyes you just wanna please me" jensen says noticing you almost faint "hey stay with awake we're not done yet" jensen says slapping you and grabbing you by the chin to lift your head, you couldn't even make out what was happening, everything was molding together and words were just sound in the back of your mind.

jensen had been abusing your hole for about an hour now and you were just praying that he'd cum and give you some rest, your eyes were rolling to the back of your head as he fucked you up, you tried to speak but the words would just be babbles "speak clearly for me baby" jensen would taunt watching you get dumber and dumber.

"you want daddy to cum in you, fill you up with his big dick" jensen asks in a teasing voice, you nod desperately at the question "okay then" jensen says taking his other hands from around your wrists and moving it to hold you waist still, he fucks up into you roughly making you see stars at this point, you couldn't even make out what was real or just apart of your imagination.

but that didn't matter as you felt the sweet feeling of relief wash over you as jensen came in you, you could feel your stomach getting more full as his cumm filled you "yeah take it take it all" jensen grunts still fucking you to ride out his high and push his cum further in you "does this mean i keep my job daddy" you ask weakly "yeah i gotta keep you around for this good hole" jensen mutters lifting you off his messy dick, the cum dripping from your loose hole.

jensen put you in the backseat and get in the drivers seat and drove you to the office because he didn't know where you lived and when he tried to ask you you'd reply with some unknown whines, you woke up to the sight of jensen working at his desk and you were in his over sized clothes "go home and wash up then come right back" jensen demanded like he didn't fuck you unconscious last night, but trust after that day you were his cum dump, he dumped load after load into you, and when he was mad you knew you were gonna get some good dick that day.

Warnings: <1k | p in a, established relationship, soft Miguel, ooc, stealing, fingering, Spanish petnames. An older fic

Maybe you gag, face scrunching up, trying to break free. But he holds you, his large, strong hand keeping your head in place as he feeds you more of his cock. It's a stretch that forced you to relax your jaw, drooling from the corners of your stretched mouth as he suffocates you with his cock.

He holds your head in place as he fucks you, hard and rough. His cock fills your mouth and throat up, giving you less than a few seconds to breathe before he's shoving it in, and so forth. His balls are heavy and firm, filled with hot, fertile cum, smacking against your chin.

dbfthal that..

calls you ‘baby’ when he’s frustrated over something as you’re arguing.

always has his arm stretched out along the seat instead of around you when you sit with him.

praises and means it, making sure you believe it just as much as he does.

has a knack for physical touch. always a hand on the small of your back during red carpets, holding your hand just walking into a restaurant, playing with your hair laying next to you before you’ve woken up.

will always let you know he’s listening, even when he’s tired. “mhm?” “oh, yeah?” his one thought is you when he’s listening, and if not, you occupy most of his brain.

always takes his time when he kisses you. he doesn’t want to make it feel half assed, so he has his hand on your cheek, or your jaw, and slowly kisses.

kisses you on the head every time he’s heading out somewhere, and loves breathing you in from your hair. being around you is enough to set him off, but he loves every part of you.

always has a certain kind of grin on his face when it comes to you. laughs a certain way whenever you tell a joke, even if it’s a stupid one.

always texts you back, even when it’s something stupid, he’ll just send some corny gif. he loves making you laugh, and he loves it even better when you’re laughing and turned on.

He'd be grunting and moaning against your ear, hot breath huffing against the back of your ear and your bare shoulder, whenever he decides to drop his head. Maybe he licks your neck and shoulder, dragging sharp teeth over sensitive skin. He doesn't bite, he only sucks on it.

His hips will be rolling into you, each thrust deep and rough. The bed creaks underneath his powerful thrusts, built to maintain such a large and powerful man. His cock is as thick and wider than your forearm, it completely fills you up as he fucks into you with wild abandon.

Teasing dilf Joel Miller 🫦 the hot divorced dilf next door wanting to go to the beach and he takes you with him. You laying flat on your stomach while Joel is standing not far from you…

Divorced, kid with the mom, and lonely for a couple of weeks. And an absolute DILF. Soft muscles and slightly hanging beer belly—hair dusting his pectorals and trailing down his stomach to his abdomen. Those shorts were barely doing anything to hide his impressive endowment.

What can you say? How could you not ogle a man like that? Especially since you wanted to go to the beach with him. Who cares if you’re 25 and he’s in his 50s? You both know you want the other—sometimes whenever he visits, you would catch him staring at your ass and thighs and he would catch you looking at his crotch and ass—and everything about him. You know he wants to fuck you until every last drop of cum is drained from his balls and you have the perfect idea.

“Mr. Miller, can you put sunscreen on my back?”

“Of course, my boy!” While Joel was distracted, you hastily pulled down your shorts and fully presented the emerald green thong and your ass to the older man. “Alright now—“

Joel froze at the sight before him. His dick jumping in his shorts, the fabric stretching—failing to hide his growing erection.

“I know I can never be her… but I figured you’d like this? Do you?” You said, whining innocently like you weren’t shaking your ass, Joel’s eyes watching the plump cheeks jiggle and wobble—what set him off, turning his inhibitions was you spreading your cheeks and sliding the ting piece of clothing to the side, pressing your tiny bud.

It was long until you felt Joel’s scruffy beer belly pressing against your back as he rams his massive dick into your body, no longer caring who watches. Your moans mixed with the older man’s feral grunts and groans, his dick splitting you

“You’re much better than her, my boy.”

A/n — hello my strawberry patch and newly added seeds, we all need this dilf. That’s all. Also the creator of the image has their tag on the top left! Amazing works.