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silkythewriter · 3 months

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I had an idea for a few headcanons you could do if ya want—

Maybe Sir Pentious with a reader who is so obviously in love with him, and keeps pining over him while literally everyone else but Sir Pentious himself can tell they like him? Like he's just really oblivous until reader finally straight up tells him.

Sir Pentious with a clearly in love reader!(●’◡’●)❤︎︎

Warnings!: Non!

Fandoms!:Hazbin hotel!

Author’s note!: HI HI OMG I LOVE SIR PENTIOUS HES SO SILLY!!!! I REALLY HOPE YOU ENJOY THIS AS MUCH AS I DID

Summary!: reader who’s clearly in love with our favorite snake demon

❤️Written by silkythewriter Do not steal or repost on any other platform please! ❤️

☆✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬☆

“Call me, you can call me

Boy, just call me (call me, call me)

While you stalling, I'm evolving

I'd give all me”

☆✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬☆

!🐍✨Sir Pentious✨🐍!

First of all, just to get out of the way, THIS MAN IS OBLIVIOUS!!!!, Autism be damned my boy can pull without even telling!!!!!

No but in all seriousness he is oblivious to your obvious longing for him.

Everyone can see you giving him shy longing stares only for him to be ranting about his latest invention. Not only would he not be able to tell but he’d always think your just being nice!

Of course he’s crushing hard behind his bedroom door to his little eggs. Happily stating and going on rambles of how gorgeous you looked today. He’d state everything! From the new hair style you tried to the new piece of clothing you bought and wore. When I mean he notices everything I mean it, but for some reason he can’t pick up on your obvious love for him.

The way he could stare in your eye as you tell him he looks breathtaking and still think you mean it just to be nice is astonishing. OF COURSE HES BLUSHING AND KICKING HIS TAIL, but he can’t bring himself to think you like him anymore than just friends!

He’d go to his egg boys and sadly rant on how you’ll only see him as friend. And the egg boys all share one Brain cell so they can’t tell you like him aswell!, maybe they might accidentally spill, or almost spill the secret of him liking you but he quickly knocks them away before you can make sense of what their saying.

All the residents watch as you do your best to drop hints only for him to complete miss it. Even angel cringes as he watches him completely be oblivious to the obvious flirting, it’s take Charlie and Vaggie to stop him from pointing out the obvious.

Husk almost always gives Sir Pentious as gaze of just utter confusion and tiredness.

He’d gladly take flowers from you that you gifted him and take care of it for weeks on end without realizing the romantic gesture!

Alastor, as always finds it humorous, although he usually doesn’t indulge himself in romantic like things he’s find it hilarious. “Even with three eyes he still can’t see the obvious! Ha!”

Charlie tries to help to the best of her ability to help guid him the right direction but it’s just end up with him more confused. Vaggie just face slaps internally,

honestly the whole crew wasn’t having high hopes for him as dim as that is. , look! He ain’t bad looking, but not many people would prefer his clumsy self, so they were honestly hoping he’d figure it out before you possibly moved on.

Even when your upset at the obvious frustrating situation he’s still be confused while trying to do his best to comfort you.

“Well I think the man isss clearly as dumb as a rock!”

It took you starring dead in his eyes for him to question if you were alright. Before you stated it was him

The way he just stood staring at you in pure disbelief, before snapping out of it and embarrassed as his previous words. But after the said embarrassment he’s full with giddy, why of course you love him!, he’s the great sir pentious!

Yea his embarrassment would quickly turn into pride, considering he got someone as beautiful as you to fall for him.

Definition of a clumsy gentlemen, he’d open doors so fast it’d smack him in the face, or pull when it’s a push door and be confused why it’s not opening.(´ω｀💧)

He’s just a silly lil guy! (⸝⸝ᵕᴗᵕ⸝⸝)

I feel like the crew in the hotel would be relief to find he finally figured out.

At the end of the night he’s squealing like a high school girl as he rambles to his egg boys about you in a new light!.

He’s gift you small little trinkets or happily spend hours with you talking!

He’s as lovesick as your are! He’s just a bit dense when it comes to accepting the fact you love.

It’s like the roles switched! Now he’s daydreaming-ly staring at you happy to have you as his, and him a yours.

Like I’ve said before! He’s a total drama queen, he can’t help it!, deny him a kiss teasingly? He’s crumbling down to the ground and holding his chest as if he just had a heart attack! (¬_¬)

He’s not at all secretive of his love for you, even if he wants to, to keep his image “professional”, he just can’t help and dote on you!

overall he’s a big dote and softy even if he tries to hide it, loves you with his whole being! ( ˘ω˘ ) He can a be a bit over the top sometimes but you’ll come to accept it! And hey who wouldn’t want a silly snake demons who’s tripping over their tail for you. Yea you got him in and over his head but he wouldn’t have it any other way. The roles have truly reversed(≖ᴗ≖✿)

☆✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬✬☆

I LOVE HIS SILLY LIL SELF SO MUCH MORE PEOPLE SHOULD WRITE FOR HIM :(. TYSM FOR THE REQUEST I LOVED IT SM!!!! PLEASE COME AGAIN!!

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grimesgirll · 1 month

Text

“not happening.”

“what if i told you that you’d be helping to save the world?”

“by fucking him?”

you scoff, turning your attention back to the braid you’d begun down your back. “i’m not helping you with your passion project, okafor. i have actual shit to do.”

okafor grins at you. “bullshit.”

“no, i still have weekly duties and assignments. i can’t just drop all of that trying to seduce your ticking time bomb.”

“i see the way he looks at you,” he states with a breath of your name. “if he’s gonna be open to anyone, it’s you.”

“he doesn’t need to be open to anyone.” you counter.

“i don’t think you know what he needs yet.”

“and you do?”

“he needs you.”

“no.” you reply flatly, fists clenched. “you need him to enact your little plan that i have nothing to do with.”

the lieutenant colonel gives you a haughty smile. “well then, at the very least he needs stress relief and you owe me a favor.”

you glare at him. “that was a one time thing.”

“you got what you wanted didn’t you?”

“being perpetually indebted to you with favors isn’t what i signed up for,” you complain as you plait your hair.

“you get to sit around and make your little maps and fuck around all day.” your superior reminds you.

you do your best not to scowl too much, unlike the man who your former benefactor wanted you to de-stress fuck. he constantly had a sour look on his face. he was the consignee who cut off his fucking hand trying to escape. how would you convince someone like that to just lay back and let you fuck them until they didn’t miss whatever life they had before again?

“this is kind of a far ask, okafor.” you note and tie off the end of your braid. you finally turn around from the mirror in front of you to face the dark green fatigue clad man behind you. “it’s never gone as far as touching someone like that and actually fucking them. i don’t think i’m up for that.”

okafor crosses his arms. “are you sure about that? last time i checked, you eye fuck him almost as much as he eye fucks you.”

“you’re an asshole.” you spit, venom dripping from your words. “i’m not letting you coerce me into this.” your eyes meet his brown irises. “let this be the last straw for you, lock me up, dishonorably discharge me, whatever, but i’m not just gonna hop on your lackey’s dick because you say so.”

he takes a deep breath and clasps his hands together, smirking for whatever reason. “i think you’ll want to.” he suddenly stands and you’re paranoid for a split second that he’s about to summon backup or attempt to disarm you right here and now. “because i’m not serving up any threats, just desserts. you’ve been good to me and i’ve been good to you. i want you to continue to reward you. maybe with what you’ve wanted all along.”

your eyebrow lifts. “and what would that be?”

okafor doesn’t say anything when you begin breaking the dress code with your workout gear. you make sure to plan time around your community mapping projects to run past the officers' meeting hall in the tighest pair of shorts you owned.

you never forgot to smile and wave to okafor and rick as you pass by. it takes a few days but rick returns your wave.

content adorns your face when you catch him surveying your form from afar, getting closer and closer to that sweet reward okafor had promised you.

soon enough rick is running into you everywhere. you're crossing paths in helicopter hangers, on benches outside of the barracks, during your runs around the reservoir, at the gym, in the administrative office in your most yielding sweater, in the hallway, and at his front door on okafor’s orders.

“okafor wanted me to make sure this got to you.”

“thank you,” rick grunts gruffly, accepting the folder with his latest field assignment from your grasp.

“anytime, rick,” you crow.

before he can bid you good night, you ask if he’d been briefed by okafor yet. he shakes his head.

you smile sweetly. “well, he really wanted you to sit down and talk about the park with someone who’s been there before, knows the layout.”

the cowboy type raises an eyebrow. “you’ve been to olympia national park before.”

“mhmm,” you confirm. “a long time ago but i know more about it than okafor.” you let out a breath, eyes boring into his icy blue gaze. “got a minute?”

the dark wainscoting of officer’s quarters enters your field of vision as rick leads you through the skinny hallway, pointing out a bathroom before bringing you into what you assume is the downstairs living room.

“you can help yourself to the kitchen,” he offers graciously, gesturing towards the kitchen of the open floor plan living space.

“thanks!” you chirp and weave towards the kitchen, finding two short glasses and flinging a cabinet open.

“oh, you have whiskey!”

“it was a gift from okafor.”

you can barely keep a guffaw from tumbling out of your mouth. “that’s very on brand for him,” you comment, turning the handcrafted decanter over in your hands. “well, lucky for you, okafor has fantastic taste.”

rick observes from the leather sofa as you pour two short glasses of whiskey - not even asking if you could. the orange light of the kitchen does nothing to hide how great you look for nine o’clock at night. your gauzy long hair glints, looking sleek beneath the lights as it falls inches above the curve of your ass.

the same bottom that had seemingly been following rick around base. it was like everywhere he turned: you were there. whatever inspired this house call felt suspiciously related.

kneeling on the floor next to the coffee table, you place the tray with your drinks down and empty the folder of its documents in order to splay them across the table. you reach up to rick to pass him one of the twin glasses.

reluctantly, he accepts. however, he doesn’t take a sip from his glass until after you do.

he doesn’t miss the way your throat tenses at the burn of the liquor when it makes its way down. you throw another swig back like a young woman who’s grown accustomed to drinking with her fellow soldiers, but in the quarters of one of her superiors?

“so, here’s where you’ll be landing.” your glass is already on the coffee table and you’re pointing out green meandering lines. “whitehorse mountain is right here. just be careful of atmospheric rivers in the area. did okafor tell you about what happened to the apache team?”

the dark haired man shook his head, worry lines becoming more pronounced.

you shake your head. “forget i said anything.” you take another quick drink from your glass and rick looks alarmed - you’re not like your oxen brothers in arm who could drink themselves silly. he doesn’t have time to dwell on it though because you’re skipping right to the next print out to detail his planned trek along the sauk river.

“it’s a pretty ridge. you should stop and take a picture.” you suggest, thumbing through laminated landmark shots of valleys and vistas, making a verbal note of one which is a convenient stop on his trip.

he bites his pink lip. “i don’t think getting a photo of the view is gonna be on my mind, sweetheart.”

“why not?” you question with a glimmer in your eye. “someone like you should take time to relax when you can.”

he chides your name. “what’re you doin’?”

“your job is important, and we all have jobs to do, right?”

there’s a far awayness in his eyes that you can’t place when you lean in closer. feet tucked under your knees, you’re trailing your hand up rick’s thigh towards the tent in his pants.

“you wanna fuck my mouth?”

“why’re you doin’ this?”

when he iterates your name, you consider backing down but then you remember okafor’s promise and how truly repressed this man seemed.

“it’s been a while hasn’t it.”

rick squirms. he doesn’t mean to but it’s a question not many people have the balls to ask him and he didn’t expect it from you of all people. he tries to block whatever memories are bubbling in response and busies himself with taking in the view of your parted lips.

“you don’t have to say anything, just relax,” you coo, shoving him back slightly.

looking down at you, rick doesn’t know what he has to gain from saying no at this point. rick huffs as you approach his erection but he doesn’t object.

his waistband falls with your fingers and you’re faced with the massive length you’d been worrying about. ever since you first saw rick’s bulge, you were brainstorming how you’d even fit him inside your taut walls, much less inside of your mouth.

starting slow, you begin at the base and kitten lick up to the top. rick’s groans give him away immediately. how can he hide how repressed he is with a cock as hard as rocks?

at the top of him, you’re laving his cockhead in your mouth. “i’ve never been with anyone this big,” you admit for the potential ego boost - even though it’s one hundred percent true. rick has a fucking horse cock if you’ve ever seen one.

your hand is working overtime with everything you can’t fit into your mouth at first. rick exhales hoarsely at the wet heat of your mouth devouring him. he hasn’t had a mouth on him in so long. your tight, warm lips wrap around his dick and you swallow around him.

his self control is rusty so he curses when he bucks into your face, stalling his hips only for you to pick up your pace. he wants to pull you off when he feels like he’s about to cum down your tight airway which is crammed full of his cock.

at the first feeling of that telltale twitch against your tongue, you prepare to do your part to keep rick’s nice leather couch clean and swallow everything he’s been holding back.

popping off of him, you look back up at him and grant a toothy smile. his eyes are lurid and clouded with what you only assume is lust. you’re not prepared for his rough grip to drag you onto the surface and into his lap.

the green cargo mini skirt you were wearing falls down your legs and lands somewhere on the wood paneled floor. the moment after you wipe your mouth with a tight fitting sleeve, rick captures your mouth. slightly taken aback, you moan into the man, squirming borderline uncontrollably on top of him as he pulls your top over your head.

his sturdy fingertips ghost across up your waist to your breast. with one robust squeeze as a warning, he assaults your heaving chest with his flesh hand and bruises your collarbone with something between a kiss and a mini-puncture wound. the proesthetic invades your panties and teases your labia, eliciting a needy hum from you.

his horse cock makes itself known again against the front of your pale pink panties.

fuck, how will he fit?

“god, you’re already soakin’ me.”

you get past the feel of his embrace for a moment to glance down only to be greeted with the sight of your swampy lap. how did i do that? you ponder.

“i wanna feel you on my cock, sweetheart. is that something you can do to help me relax?”

you grin. “i’m glad you asked.” you feel a renewed tingle downstairs. “why don’t you see how i take your fingers first?”

a smirk forms on his face. “probably should.” and then he’s reaching between the two of you to prod a finger at your dripping mound.

a deft finger drives into you. you’re expecting another one but as you lazily rest your head on his clothed shoulder, you just whine. the finger inside of you curls and unfurls, stretching you out without the addition of another digit. just the way his fingers drags along your walls has you twisting on top of him.

“you’re really wet for a girl who came over to talk about maps.”

you don’t comment, just cant your hips and beg for another finger. he obliges.

the calculated sensation has you forgetting what he’s talking about, forgetting about your plan. that rhythm he’s adopted speeds up once you make eye contact with rick.

“one more?” he questions.

you nod furiously. “another!”

rick doesn’t delay and the floor drops out from under once you feel a tongue on your quiveting lower lips.

“rick!” you gasp as his fingers and tongue work in unison to squeeze every naughty little noise out of you.

the soldier doesn’t speak; he just laps up your pussy like it was an order.

you come all over his face.

“sorr-,” you’re shut up by a wet finger in your mouth.

“that’s it.”

the no longer meek man trains his eyes on you as you suck his finger clean. through half lidded eyes, you watch his pupils dilate into fully lust blown orbs. devoid of the bright blue you’d seen before, rick’s stare only shifts when he’s shifting you on top of him.

“is it going to fit?” you don’t even realize that your thoughts are materializing out loud.

the officer snorts. “never had a problem before.”

the initial stretch is challenging. your breath is caught in your throat and you’re almost asking the man beneath you to slow down but he’s already inching in at an excruciatingly stable rate.

fuck, you’re reconsidering this. you curse your lieutenant colonel for acting like this whole song and dance was easy. figures. okafor isn’t the one getting stretched out on an eight inch cock.

at the sound of your whines, rick places a kiss on the top of your forehead. “doin’ so good for me,” rick praises. “so tight.”

i know, i feel you tearing me open you want to rasp but you just try to settle into the feeling. you adjust your position, tilting enough for rick to take a renewed interest in your ass. a firm hand plants itself on your flesh in an attempt to leverage you closer.

“almost there,” he grunts and continues pushing through your clinging canal, through the thick rings of muscle that grip his cock so tightly.

momentarily, you slump against the soldier. yeah, you’d been running around the base in hopes of attracting rick’s attention but your exercise routine was no match for the man with a brick between his legs.

once he’s sheathed inside of you, rick reaches down to toy with your clit. you mutter a soft curse. the sensation picks up and you’re faced with not just feeling full but fully stimulated as well. each drag against your sensitive bundle of nerves has you whimpering into rick.

drives into you become harsher. the impact feels less like a truck and more like a commanding officer. an arm is wrapped around you to keep your position steady on top of okafor’s new favorite soldier. the same one who seems to be hitting the right spot every time he moves you up and down his length.

your hands reach for his graying chestnut hair. they find purchase while rick rocks into you. the urge to complain that his shirt is on exits once a familiar pressure mounts inside of you.

“fuck, you’re squeezin’ me.”

“mhmm,” you expire into his neck, nuzzling into him when he presses fingernails into your sides and lifts and lowers you like his own personal stress relief toy.

you can’t be bothered to care. you’re getting what you want out of this: a reward and a release.

pleasure is just radiating throughout your core again. whatever pain had you speechless earlier has evolved into an ecstasy that has you babbling. rick just keeps a hand on the small of your back and carries on pouring himself into you - into your tight little canal, back and forth, in and out.

“rick,” you’re mewling.

the man can’t be bothered to plant a hand pleasurably on your pussy or respond to your cries, so you complain a little louder.

“want you to cum in me.” you stutter into the pillowcase.

“don’t think you want that,” rick demurely admits.

“no,” you argue between pants. “i’m on the shot they have here. i want you to fill me up.”

rick utters a curse into your neck, pouring himself into you so swiftly you’re surprised. just like you asked, he pumps his hips leisurely into your soaked cunt. you wince at the sound of a squelch. hopefully rick doesn’t care too much about having to clean his sofa.

neither of you are expecting the noise you make when rick untangles himself from you. you’re too tired to have shame and simply sink back into the ductile pillows. your head swivels over slowly to find rick watching your chest fall up and down unevenly.

laying beside the man, you can’t help but feel accomplished. for once, the soldier is sporting a blissed out look on his face instead of a scowl or thousand yard stare. but as he slings an arm around you and tugs you closer to his sweltering, sweaty body, you can’t help but feel guilty - manipulative even.

mission accomplished, but at what cost?

pt. 2

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