#asher (he/they) | Explore Tumblr posts and blogs

sharkenedfangs · 3 months ago

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What do I need to do to get a fic of sub crossdressing male pc begging Bailey to be their first time ( first everything really)? I don't even care about wether PC gets railed like we wish, I honestly highkey just want your take on it.

— ☆ “SIMMERING BENEATH.”

— sucks when your annoyingly bratty, yet pretty bastard of an opthan manages to get past your tight-held clutches, doesn’t it? mister bailey. 1.8k wc

— “the fuck do you want, asher?” : wrote this on the way back home, so on the sort of.. subway thingies, it’s not called that where I am, but they do resemble that and felt fucking nauseous, so apologies in advance if it’s shit. was too good to fully pass up on this one, though couldn’t turn it into a full-on lengthy one due to being busy with other current things. still tried to input every aspect you’ve asked for. yeah, may it be up to your standards then, anon.

Fucking fuck.

No, hell— that wouldn’t truthfully encapsulate the sheer idiocy of his muddled actions even then, because god�� fucking shit, why would a man of the likes of Bailey — relatively known, if not factually remembered as the cold, logical one in town — stupidly fall for some mere trickery, childish ploy fabricated by your own stubborn whims? Or, to be quite precise, those pathetic taunts of yours that any man possessing the slightest nerve of a goddamn functional brain, wouldn’t have dumbly caved in to.

Talking about the depraved perverts that’d foolishly slip between the evidently, way too small cracks unfitting for their same, way too fucking large bodies — of the barely opened windows the dumb orphans would forgetfully leave behind. Shakily pawing with sweat slicked hands at some brat’s snoozing body before they’d eventually be chased off by the mere sight of his approaching figure inevitably barging in, hastily mutter on about their prestigious status and so on— fuck, never really truly listened to the shoddy bastards. How Bailey was no man to rudely kick ‘em out of the own crappy establishment he was sloppily running with a twinge of cruelty ever present in his cold gaze.

Yeah, he’s no damn better than those perverted fuckers right about now— possibly worse, but shit, no way in fucking hell will he potentially admit to that despite the cooling air annoyingly caressing his bare skin, sticky sweat clinging onto his flushed flesh nor the disheveled mess of his habitually, slicked back hair partially obscuring his hazy vision of this.. well, fuck— say it or not, admittedly, fucking hot sight shamelessly greeting him in return. Loosened, pristine white dress shirt untucked in face of this, to give forth to a discreet glimpse of one of the numerous tattoos snaked along the surface of his toned figure.

Slightest pout of your rosy, puckered lips he’d unconsciously find himself eyeing for far too long when thoroughly denied for the day by your daily, insistent questioning. Pop your cherry, you had confidently said with a noticeably excited shake of your fists. Might as well endlessly yap his ear off with that unrealistic request of yours— a pitiful plea that somehow, without fully realizing as to how and why — is currently happening within the otherwise narrow confines of his private office. Solely dedicated to calmly concentrate on each and every one of his gruelling tasks. Namely, neatly sorting out the thin sheets of paper openly displaying pertinent information to the numerous orphans residing here, registering the missing few that’d either go in running like some mindless moron or be plainly sold off to a godforsaken hell he held no genuine interest in— Fuck, fuck. You get the gist by now, there.

A well-deserved punishment is what this all is, simply was for that matter, and hah— you seem to be willingly taking it, although, can’t truly say he’s all that suprised. Brat. It’s what you are. Stupidly nosy brat who couldn’t hope to obediently keep his supple hands to himself for the shitty life of him. One that’d so ironically, perfectly fit all too well underneath the weight of his calloused palms restricting your bashful squirming— now contentedly facing the eventual consequences of your impulsive actions with a gleeful smile tracing your curved lips. Rhythmic squeaking of the wooden, chipped desk the man had sworn to fucking god, promised to dearly replace whenever was soonest possible and, well, he’s received his all-time excuse to be snidely given to those thugs.

A cum coated piece of furniture is just about a good reason to be neatly reinstalled with something sharper, newer— something along the lines of that, the bigger the better, probably.

Speaking of big.. Shit, he’s undeniably fucked.

“Don’t you fucking look at me like that, you ungrateful little bastard. I’m putting a roof over your head and a place to stay so— fuck, the least you can do is fucking pay me back on time, but can’t even do that, can you?” Habitually stern is what he’s evidently known best for amongst the nosy orphans, yet that usual bite in his gruff voice is almost.. pitifully lacking in face of whatever the fuck this is— yeah, actually he’s got a clue what it is. Inwardly cursing at how his hips automatically snap back in one sharp motion to then, merely slap forward— flush against your reddened ass. Riddled, fresh marks traced along the entirety of your curved back nor your spread asscheeks for that matter, shouldn’t be looking so infuriatingly pretty after all that harsh spanking he’s had you withstand. Take it as the start of your relatively tame punishment coming from a stone cold man like him, that’s what.

“Like what? A satisfied client? Hah— this is the best day of my life, y’know. Feels so fuckin’ good, Bailey— please don’t stop..” Of-fucking-‘course you’ve already had whatever comment prepared to hurriedly retort back within your noisy mouth, despite being so crudely bent over a flat surface like this. Particularly whiny moan drawn out at the feel of his thick cock satisfyingly stretching you full, sinfully defiling you from virginity itself. Pervertedly spread open with your dizzyingly warm, honeyed— fuck, did he really just think of your hole like that?? Must be losing his goddamn mind. Correct, your fucking hole is the one irreversibly altering his unwavering principles. So fuck you, really.

Sloppy, squelchy noises, all too annoyingly addictive to hear, of your tight, puckered heat fervently sucking his fat cock in, coating it all sticky and wet with your slippery, pink insides. Instinctively hissing at the knee-buckling sight of his veiny length repeatedly remerging and disappearing deep inside because shit— can’t get enough of it. So much so his rough thumbs are subconsciously spreading that tender flesh wide open for his unrelenting, stern gaze to gawk at. Not to mention, those frilly lines adorning that stupidly short skirt, bouncing in tandem with each ruthless thrusts slapped to your backside. Admittedly adorable, cute cock clumsily bobbing from the ruthlessly loud smacks of the caretaker’s fat balls sloppily slapping upon the flush of your ass, teasing— no, irrefutably taunting him by the subtle glimpse of your dribbling, wet dick peeking from beneath that skirt.

Like to play dress up, don’t you? Sneakily slip in those overly feminine, lacy garments the elder man would’ve notably poked fun at the sissies that unabashedly wore such clothings back in his day— ironically enough, now he’s finding himself, balls deep into said ‘sissy’. Meanly tugging at the silken material snugly encircling your flailing legs, neatly tied bows bound to predictably come undone given the unrelenting bounces of your shared figures. Unable to keep still when you’re being fucked or something?

Little, incompetent brat. Constantly managing to crawl underneath his skin, reach the deepest parts within him the caretaker has progressively learned to conceal beneath this ruthlessly heartless facade. Not that Bailey’s the nicest man to begin with, but hell— favouring a good for nothing, admittedly appealing to the eyes— meddling boy like you wasn’t on his fucking wish list either.

Should be crudely wiping off that joyous grin etched upon your features if you actually know what’s good for you. Though, doubt you will.

Fine. He’s not necessarily against doing the honours for you. Frustratingly fuck out the undeniable audacity ever so present in your every movements when carelessly distracting him during work hours— time meant to be initially spent for focusing and godfuckingdammit, merely thinking back on it has him obscenely gritting his teeth, further tightening his unrelenting grip planted along your — sure to be bruised later, which you’re naturally paying the price of it — hips. Heaving groans mixed along with some curses which are presumably directed at you, if not at himself, that he’s uncertain of, really. All he’s stupidly conscious of is the undeniable fact that you might’ve coincidentally, if not intentionally, gotten him dizzyingly drunk off your previously undefiled hole.

Fuck, must be that then. Overly aware of what you’re currently doing to him, aren’t you?

‘S that it? Your admittedly, badly thought out plan simmering deep within your mind, happily tugging at his heartstrings in hopes of getting your mean caretaker to fuck your virgin holes full of cum? Well, all to say— you’ve graciously received what your bratty, stupidly pretty ass has fervently been desiring for all along, huh? Ain’t that right? So in return, it’s only fair that he greedily takes whatever he so pleases, whenever or wherever— that is of no importance then, whether it be comfortably settled atop his lap during office hours or slung along your knees to dutifully service him. “God, don’t you dare fucking move— just— just fucking stay like. Yeah, just like— hah, that.” Got no qualms whatever position that might be in, too caught up in the tender feel of your soft flesh underneath his punishing grasp to sluggishly catch on what’s spilling forth from his swollen red, oozing tip because.. shit, got him cumming— not just plain ol’ cumming, but mortifyingly enough, squirting prematurely too. Effectively painting your stretched walls in a sticky, white mess of his seed, inwardly cursing at himself for potentially letting things stretch on further than they were initially meant to.

Yet as ironic as it may be, his unwavering pride naturally beckons him in turn or is it the petulant whine longingly drawled out from between your rosy lips at the sole thoughts of your time together being cut short? Right— ‘course, what else would it be that’d have you miserably whimper so? Didn’t cum yet, did you? Obediently took his fat load sickeningly dripping free from your sore, used up hole without any sort of complaint, gaze momentarily flicking downwards to the pearly droplets of his cum progressively trickling down the length of your suspended legs laid along the precarious edge of his oaky desk.

Similar to how an opportunist excitedly pounces on every chance set before him— hah, he’s never been much like Eden to cowardly hide amongst the oaky, wooden trees to begin with. Huddle within the shadowy forest in a futile hope that mere distance might erase the muddled past; the foggy, far-away town altogether from their collectively minds.

Rather take part in the animalistic feast even if it would’ve eventually spelled utter ruin for himself, inevitable defeat one cannot simply crawl out of sheer will. And maybe, that said ruin, is delicately staring at him right in the face with a fucked out look stretch upon your features, pupils blown wide with a hint of saliva gracing the corner of your pouty lips that he— fuck, can’t help it, really— have his calloused thumb stroke at, soon swiftly followed by the immediate puckering of your overly attentive mouth suckling along the digit. Incidentally coating it in a slippery wet layer of your spit that you, of course, joyfully take advantage of by stifling a wanton moan right ‘round it.

Shit, going to be the goddamn death of him.

That eventually faith patiently awaiting for him, doesn’t sound so bad when your cum stained, little needy self is notably factored in that messy equation after all.

#how’d you know I like crossdressing little twinks?#not to say reader is a twink— in fact #he can be whatever you want him to be #I just envisioned him as being a pretty little thing getting pounded by bailey that’s all #yeah #..nah man I don’t have an obsession with twinks and boypussy. what?#dol #degrees of lewdity #bailey the caretaker #dol bailey #bailey dol #bottom male reader #sub male reader #x male reader #male reader #character x male reader #— ☆ burnt ashes.#★ asher tries to answer.. shit.

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