Business Casual (Chapter One)

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#1 of Business Casual


Jesse stared at his reflection in the golden surface of the elevator door, adjusting his tie. The brown and white terrier had dressed to impress on his first day wearing what had been his second nicest shirt until his interview, a light blue button up. Upon it hung a black tie that matched his blazer and freshly pressed slacks. This was his first job out of college and he wasn't going to screw anything up. Besides, Mr. Dewey had already shown him some of the... perks of his new position.

He thought back to his interview, which had ended with him on his back, clothes ripped, and drenched in, among other things, sweat. His new employer's stern features baring down on him. Even the memory had him at half-mast already; he lost himself in it for a moment.

When he opened his eyes, his heart leapt as he met the steely blue gaze of Richard Dewey, world renowned businessman and millionaire playboy, and the man to whom he was now the personal assistant.

"Good morning, Jesse." His words were dark and heavy as they brushed past his piercing white fangs. The silvery streaks in the wolf's otherwise black coat caught flame in the light of dawn glinting off the golden elevator.

"M- mr. Dewey, good morning." On the outside, he maintained his composure, he was a professional after all. Internally, however, his gaze had already melted Jesse to a quivering puddle.

"Jesse, please, no need to be so formal," he smiled warmly and extended a hand to him, "call me Dick." Jesse barely processed that he was being spoken to, his mind was far away. By the time he noticed his employer's gesture, the window had long since passed and he awkwardly reached out in the moment after Dick's receded.

"That's alright." Dick extended a foot to hold the door, "I have a meeting in half an hour and I need to be in peak condition," he checked his watch and let his glasses slide down to the tip of his muzzle, "think you can help me prep?" turning his gaze back upon Jesse.

"Absolutely!" His reply was practically a squeak as he stepped onto the elevator. The inside was even more ostentatious than he had expected. Even from the exterior, the whole building had a very art deco aesthetic to it, and this was no exception. The walls were inlaid with intricate golden geometric patterns that reflected cleanly onto the polished black floors.

"Excellent," Dick pushed a button, sealing them in the confined space for at least ten floors, "I'll show you to your office so we can have a bit of privacy." Jesse could practically taste his musk as it wafted through the cramped compartment. Overpowering any other scent with a pheromone of strength and charisma.

It took Jesse a moment to realize what he'd just said, he hadn't been expecting to receive his own office, especially not the first day. He was so taken aback, he didn't even process the rest of the sentence. They rode silently the rest of the way, Jesse didn't want to step out of line on his first day, and Dick knew better than to say too much. Jesse had barely recovered from the revelation of his office when the elevator drew to a halt. The moment the doors began to creep open, he was almost incapacitated by the sounds he heard and the unmistakable perfume of sex.

"Aghh, fuck!" A woman's moans filled Jesse's ears as though she were in the elevator with them. When the doors finished opening, his gaze fell upon a doe who must have been in her late twenties, dressed in professional clothing from the waist up, bent over a long desk in the corner of the square room. Behind her, and deep inside of her, was a tall, muscular, gazelle, her fluorescent pink hair, twisted into a bun, perfectly framed the joyous expression spread across her face as she thrust her cock deep inside the whimpering girl.

Dick sighed and, without missing a beat, crossed to them, removing his pants effortlessly without breaking his stride. He tossed them, in what must have been a practiced motion, directly to Jesse. Despite his own lack of coordination, he managed to catch them as if by accident.

"How many times have I told you," he growled, sticking his cock inside the gazelle and nibbling on her ear, "no fucking in the lobby." He chomped down on her neck, Jesse thought he was being a bit too rough but he would later learn this was all well within her agreement with HR.

She whimpered in delight as he matched the rhythm she had been thrusting and, just as smoothly, pushed them even faster. The doe beneath the two of them was powerless to overcome their combined thrusts and orgasmed almost immediately. Dick, however, showed no signs of stopping. If anything, he continued to accelerate. He thrust harder and deeper, pushing the two beyond their limits and much further. He continued at his ardent pace until the gazelle had cum and the doe was nothing but a squealing mess.

"Now," he pulled his cock out, leaving the two collapsed over the desk, "clean this mess up, we have visitors coming in half an hour." He spanked the gazelle with a resounding slap, and walked to one of the two enormous doors that flanked the desk at a right angle. This door, on the left, led directly to Dick's office, only passing his own on the way. This was to keep guests sequestered from the main work floor.

"Is that, uhm," he wasn't sure exactly how to phrase the question, let alone which of the myriad questions bounding around his mind he should ask, "is that a regular occurrence?" was all he could manage. Everything else had descended into a tangled mess in his head.

"Unfortunately, yes." Dick had still not retrieved his pants, nor had he made any indication that he planned to. He simply pressed on toward Jesse's office as though nothing out of the ordinary had just happened. Perhaps to him, it hadn't. Jesse tried desperately to keep up, but his mind was spinning, and he still wasn't sure what to make of this whole situation.

"I keep telling them to keep it to less public areas," he continued, making his way down the corridor which was much longer than Jesse had anticipated, "I suppose they just want to be punished." He stopped outside a large mahogany door with ornate crystal doorknobs.

"This is my office?" Jesse cautiously approached the door, petrified at the thought he might break something. His hand hovered a few inches away, keeping a safe distance. This door looked like it cost more than his entire apartment, and he wasn't about to lose his first paycheck over a scuffed knob.

"Of course, Jesse," Dick thrust his hand to the knob and gingerly nudged him through the door, "can't have my assistant working in some drab cubicle."

Jesse took a single step onto the dark espresso wood floor, his reflection gazing back at him from below. It all seemed too lavish for him, the gorgeous desk, the shelves, already brimming with the books and trinkets he'd had sent over. There was an enormous TV hanging behind his chair which currently displayed an aquarium. A couch sat facing a wall of windows, it looked brand new and extremely comfortable. He hardly had time to take it all in before Dick whisked him off his feet from behind.

"M- Mr. Dewey?" Jesse let out a whimper in surprise, he wasn't expecting to be lifted, though he didn't mind it.

"Shhhhhhh." He pressed a finger to his lips and pulled him in close, hovering just inches from his lips so near Jesse could taste his hot breath. "Just nod your head, may I fuck you before my meeting?"

Jesse desperately wanted to speak, he wasn't sure what he'd even say. Before he could say anything and ruin the moment, Dick stuck his thumb in Jesse's mouth to keep him quiet. Jesse instinctively closed his lips around the claw and began to suckle.

"Nod, Yes or No?" Dick grasped his entire muzzle with the rest of his hand, not hard, just firmly enough to further entice him. Jesse nodded as fervently as he could, he needed Dick, and he needed him now. Dick had been anticipating that response and had already started removing Jesse's belt.

They entwined as tightly as they could manage; Jesse constricted in his tight embrace; legs wrapped around his brawny hips. As they kissed, Dick's masterful tongue strokes tossed and pulled Jesse, a roiling maelstrom in the sea of their lips.

Jesse pulled off Dick's jacket and tossed it to the floor, immediately realizing his mistake. He had forgotten Dick had a meeting in twenty minutes and he may have just wrinkled his suit jacket.

"Bad little slut." He growled in his ear, slapping his ass and sending a splintering crack through the air. He took the opportunity to remove Jesse's pants and toss them aside as well "Let me know if I go too far, ok" he whispered in his ear. Jesse nodded, but Dick was far from stepping past any boundaries he had and he wasn't about to stop him.

"Do you like it when I call you a slut?" He began to rub Jesse's cock through his incredibly soft underwear which grew tighter by the second. He was already half-hard when the next hot breath hit his ear, "Do you like being my little whore?" Jesse could hardly contain himself, he wanted to make all sorts of noises, but Dick's tight grasp on his maw left him powerless. He wasn't sure how much longer his boxers would be able to contain his erection, Dick seemed to pick up on that and immediately ripped his underwear to scraps with a single tug.

"Don't worry," he reassured as he prodded Jesse's tight asshole with a single toned finger, "there are spares in your desk." Jesse hadn't been worried, his mind was beyond empty, he just rode the incredible sensations as they washed over him, "tight little hole, aren't we?" he whispered and nipped at his ear. Once again, Jesse's only response was a gentle nod. It was all he could manage. "That's ok," he grunted between forceful thrusts of his powerful fingers, two of which were now stretching him apart, "we have ways of fixing that."

He carried them both to the desk and knocked a few things slapping Jesse down with overwhelming force. A jolt shot down his spine and he felt ready burst at any second. Dick pressed on what Jessie realized was a crystal lubricant dispenser among the desk accoutrement that had been left intact. He felt Dick's muscular fingers, now dripping with lube, slip back inside him, stretching him wide. Jesse was already approaching his limit and Dick could feel it, wrapping a tight claw around his balls and halting him just short of the edge.

"Who said you could cum before me?" his strong canine jaw clamped down on Jesse's neck as he thrust his cock inside his assistant's gaping hole. He barely got an inch in before the vice grip of his tight asshole stopped him in his tracks. "Fuck," he moaned as his ingress crashed against the fleshy barricade, unable to push any, "you're even tighter than I expected."

Jesse was barely processing his words, more a percussive stimulation than anything comprehensible. He was fully engulfed in the pleasure that began pouring over him from the moment Dick stuck his cock inside of him. Jesse loved the feeling of being full of a lover pushing inside of you. Without warning, Dick tugged hard at his tie, constricting his airflow. He was caught off guard at first, but once he adjusted, it left him even more aroused.

Dick prodded steadily until he was able to work nearly four inches of his thick cock into him. Every press, no matter how slight, sent a shiver down Jesse's spine, he wasn't sure how long he could withstand this persistent assault. Jesse's grasp loosened and he was able to start thrusting properly, pushing progressively harder against Jesse's insides, each thrust deeper than the last. as the length inside him surpassed six inches, the thrusts began to become visible from the exterior as they pressed against Jesse's stomach.

Dick kept up his pounding, taking careful note of Jesse's expression and making sure to tease him just shy of the edge, right where he wanted him. Neither of them said a word, the air had become a sweltering symphony of moans and grunts. He continued quickening, reaching the limits of how deep he could push. Jesse could feel the edge of his knot brush against his ass, if Dick kept going at this pace, it might end up inside of him. As much as Jesse wanted to be worried about what that might mean for Dick's meeting, he wasn't about to stop him. Even if he wanted to, he wasn't sure he could.

"That's it," Dick's tone was shockingly calm for how hard he was fucking Jesse, "moan for me like a good little slut." Jesse did as he was told and let his moans run even wilder than he already had. He wasn't sure how thick the walls were, but he figured someone must have heard them by now. How could they not, he could barely contain himself.

"Jesse," Dick slowed down, but not entirely, just enough to give Jesse a chance to respond, "have you ever been knotted?" He had been expecting the question, even still it took him a moment to respond. A delay that was not helped by the continual pounding at his ass.

Eventually, he managed a head nod and a short squeak "No." He had dated a Husky in college, but they hadn't been together long enough for Jesse to try it, but it sounded like that was about to change.

"Let's fix that." Dick confirmed. Though he couldn't see, too engrossed in the sensation of bouncing on his cock like a ragdoll. Even so, Jesse could hear the wide toothy smile in his tone as he lifted him once more off the desk.

He stepped back, Jesse wrapped around him as best he could with his liquified legs, and continued to thrust. With one might heave, he thrust Jesse down onto the end of his cock, shoving his knot inside. It was far beyond anything Jesse could have anticipated, his head pressed against Jesse's prostate, and the knot stretched his asshole wider than it had ever stretched before. The blend of pure joy and sheer pain was incredible, and Jesse could feel the precum steadily trickling down his length.

"I can't, take much-" Jesse whimpered before Dick brought their lips together again, interrupting him.

"Me either." Dick pulled away for a brief second before reaching his tongue back inside of Jesse's mouth.

Dick thrust a few more seconds before it finally became too much for either of them to bear. Jesse came, hard, spraying rope after rope of hot, sticky, cum all over his shirt and desk. Dick, meanwhile, pumped several loads into him, all held in by his knot. Jesse had never felt so full, but he wanted to feel that way as often as possible going forward.

"Uh... sir?" Jesse broke the silence, after what must have been at least a few minutes.

"Yes, Jesse?" Dick panted, still trying to catch his breath from the strenuous workout he'd just performed.

"Doesn't knotting take, like, half an hour?" He looked up into the steely blue gaze of his employer. The expression staring back at him was one of confusion.

"I guess so," he cocked his head to the side and held him tight as he walked Jesse back to the desk, "why?"

"Sir, you have a meeting in 15 minutes." Jesse looked at the clock on the bookshelf next to his desk, he had been so engrossed he had completely neglected the time.

"Not to worry," Dick tousled his hair and lifted him from the desk yet again. He made his way out the door and toward his own office, "I had a feeling this might happen and planned accordingly." Jesse wasn't entirely sure what to make of that statement. On the one hand, he was glad his boss had a plan for this eventuality. At the same time, the fact that he was so readily prepared worried him this might be a regular occurrence.

When they got to Dick's office, the ornate wooden doors swung wide to greet him as if by magic. Overall, it was fairly similar to Jesse's, if at least triple the size. A wall of windows overlooked the street below as well as gazing out at the buildings of similar height which had a clear view of everything going on in the office. Under normal circumstances, Jesse might've been embarrassed, but he was a professional, he wasn't about to let that break his demeanor.

They stepped behind Dick's enormous desk. It seemed, and Dick would later confirm, that the desk had been purpose built to hide someone beneath. To his surprise, there was already a cozy ottoman with a few pillows at the right height for him to lay down with Dick still inside him.

He got situated as best he could. To his surprise, there was a good deal of office supplies available to him below the desk, including a reading lamp and a small laptop that Jesse could use to take notes during the meeting. In all honesty, he was glad to have something to do while Dick was attached to him, even if it was just taking minutes.

A few minutes later, Jesse heard a voice over the intercom, "Mr Dewey, your 9 o'clock is here to see you. She was muffled through the desk, and he hadn't exactly gotten a good listen the first time, but Jesse was fairly certain he recognized the voice of the doe he'd encountered on the way in.

"One second," Dick responded and tapped Jesse on the shoulder, "you ready?"

On any other day, Jesse would have hesitated, being called into a crucial meeting so soon into his first day. But today had been strange enough that he was sure he could handle anything.

The meeting went smoothly. It was clear from his demeanor that this was not the first time Dick had had to carry on a business conversation while tied to someone. The conversation itself was nothing interesting, some nonsense or other about decreased quarterly profits in conjunction with overproduction. Despite that, the fact that Dick was able to conduct himself so formally without even the slightest hint at his current situation left Jesse in awe.

By the time the visitors finally stood and left the office, nearly half an hour had passed and Dick's cock gad loosened enough to come out. Jesse assumed it was probably just more convenient to leave it in until they were alone so as not to risk Jesse's discovery. An assumption that was confirmed by the sharp yelp he made as Dick pulled his knot out.

When he exited Jesse's ass, they took a moment to just breathe as the cum drizzled out and pooled on the floor below. Jesse felt incredibly satisfied, sitting politely on a towel containing an ice pack, and doing his best to recover from the extended anal intimacy.

"So," Dick broke the silence after a few minutes, "enjoying your first day?" His sly grin made his real question hard to ignore. He wanted to see if Jesse was comfortable with the environment of casual sex in the workplace, a question Jesse wasn't quite sure he was prepared to answer.

"It's definitely interesting." He muttered, trying to pull his gaze away from Dick's piercing blue eyes. It wasn't a lie, he was certainly intrigued, and he had a strong desire to explore all the office had to offer. At the same time, it was unlike anything he ever would have imagined, could he really work in a place like this? He was a bit overwhelmed.

"Why don't you head back to your office," Dick gestured to the hallway as he checked his schedule for when he'd need Jesse next, "looks like you're free till after lunch." Dick peered into him with his penetrating eyes, "Why don't you lie down for a bit?" That sounded like a lot of downtime but, after the morning he'd had, Jesse wasn't about to complain.

He stumbled back into the hallway. He'd had a few minutes to rest in Dick's office, but that was hardly sufficient to recover after the pounding he'd just received. He opened the door and, to his surprise, the mess they'd left had been completely cleaned up.

A petite rabbit in a maid uniform sat in one of his chairs, sipping gingerly at a glass of some dark brown liquid. Their long pink ears were tied back with an equally pink ribbon.

"Oh," Jesse was startled by the visitor, he hadn't been expecting anyone in his office, "can I help you?"

The bunny stood, and swaggered confidently over to him, drawing nearer until they were just inches away. They put a hand to Jesse's chest, feeling his heartbeat. Their other hand made its way to his crotch, still naked, he hadn't even realized.

"O- oh..." He wasn't sure what to do, should he stop them? That seemed like the professional thing to do. Then again, the atmosphere in this office seemed very different, maybe it would be alright for him to indulge. At this point, it didn't seem like he'd have much of an opportunity to resist.

The rabbit didn't wait for a response. Feeling Jesse get harder by the second, they dropped to their knees. The petite maid licked their lips with a desperate hunger Jesse had never seen before.

"What are you-" Jesse tried to interject, but trailed off into a moan instead.

The rabbit stroked his cock a few times, taking just a single lick of his tip, "Want me to stop?" they asked in an innocent tone as fluffy as they were.

"N- no." Jesse took a step back and leaned all his weight on his desk, he didn't think he'd be able to stand much longer.

The bunny slid their lips effortlessly all the way to the base of his cock. Jesse was impressed, he would have to ask for tips later, if he could remember that is. For now, the sensation overtook him as they tenderly lapped at him inside their mouth.

"Fuck." A single utterance escaped his lips, wafting on an errant sigh. The bunny's nose twitched in response, whispering to him "Glad you're enjoying it." Jesse was already close to bursting, if they continued their ravenous lapping, he wouldn't last much longer.

"I'm gonna-" the bunny interrupted him with a slight growl, stimulating the tip of his cock and sending him tumbling over his breaking point. The bunny slurped hungrily as Jesse pumped his load into their mouth. When he finished, they gulped and licked their lips, satisfied with a job well done.

Jesse laid all the way back onto his desk, unsure if he would ever be able to stand back up. He wasn't sure if he wanted to.

It was only his first day and he already felt overwhelmed by this job. He kept getting distracted from his duties, and he wasn't entirely sure what those were. Besides, the working environment was far from what he'd experienced during internships, let alone what he'd learned in school. Still, if he could get past that, the pay was incredible, as was the sex.

Maybe he could handle this job, only time could tell. For now, though, he would just have to try his best and start stretching more. That and drink a lot more water. He closed his eyes to finally catch a respite from it all.

"Rough first day?" Mr. Dewey's voice caught him off guard as he snapped back awake. To his surprise, he now starred upside down into the face of Dick Dewey who was currently displayed on the monitor behind his desk.

"No sir, Mr. Dewey." Jesse snapped upright and threw his hands over his exposed cock, blushing. As soon as he did, he realized the gesture was pointless as Dick had been inside of him only moments prior. He buried his face in his hands and shook his head. "How can I help you, sir?"

"Jesse, Relax," Dick smiled wide, his perfect white fangs glinting as he chuckled, "It's just nearly 11 and I hadn't heard from you," Jesse looked at the clock on his desk in disbelief, he had been in his office for almost an hour and completely lost track of the time.

"Sorry, sir," he blushed, not wanting to admit why he hadn't seen him in so long, "I- I just got the best head of my life from someone in housekeeping." He looked toward his feet, trying to avoid meeting Dick's hypnotic gaze.

"Housekeeping?" Dick raised a curious eyebrow "Housekeeping only comes on Fridays."

Jesse's expression was blank, he wasn't sure how to react to this revelation. "It was a bunny dressed as a maid." Jesse had only begun his disjointed attempt at description, but he received a look of instant recognition.

"Ah," he chuckled, this was clearly not the first instance of this particular incident, "that's just Ty. He works in IT."

Jesse's confusion only deepened, but that didn't matter to him right now. He pulled up the minutes he'd taken fully prepared for Dick to launch into a cavalcade of changes and notes. To his surprise, nothing of the sort came.

Dick, it seemed, was much more concerned with checking up on Jesse's wellbeing while they ordered lunch. Among other things, Dick gave him a much clearer explanation of his job. When the food arrived, Jesse grabbed it from the lobby and brought it to Dick's office. As they ate, they began brainstorming for his next meeting.

By the time they had finished, Jesse felt much more confident and was ready to take on whatever challenges the role had to offer. Maybe he would flourish in this business casual environment.

Hey, if you liked this but thought "hey, why does the formatting look so janky?" that's because it was originally intended to be read as a US trade paperback (6" x 9", hehe nice). If you want to read this piece as a PDF, check out this free post on my patreon. If you like this one, you can also get free PDFs of all my other stories too. I mean, if you wanna kick me some money while you're there, there's also a bunch of patron only bonus content with some of the dirtiest, kinkiest, extra scenes you've ever seen. But hey, what do I know, I'm just a dumb fox uwu.