Chapter Text
If you asked someone to make a global list of the most powerful corporate businesses, you would have more than a few people put De Vanily Inc at the top of the list.
They had their fingers in countless pies. Management consulting. Professional services and systems integration. Financial and accounting services. Enterprise IT and cybersecurity. They were a monopoly in everything but name, and there were few other juggernauts that dared to challenge them without being swallowed up as a result. To most of the business world, they were unmatched, unchallenged, and untouchable.
And, right out of the fifties, if the rumors were to be believed.
The CEO and Chairman, Gordon De Vanily, was a handsome and charming figure who had a mysterious way of winning people over, along with a terrifying intellect. That was likely why the company was able to get away with the inner workings of its office. It was a boy’s club, playing and simple. Gordon recognized effort. Hard workers could rise. But only if they had the right hardware. Equality, at least for the fairer sex, was a little more than a pipe dream.
They dared not dream of the C suite. The most a woman could aim for was a secretary, a receptionist, a typist, or something in that lane. They were there to look pretty, fetch coffee, and ‘relieve stress’. And if they fell short or bucked the system, punishment was swift. They didn’t even bother hiding the spankings, and even had promotional material of employed women in short skirts and high heels over some office workers lap moment before a hand smacked her backside.
The other punishments were a bit more well hidden behind closed doors, and though there was some word of mouth, nothing ever concrete ever saw the light of day. Not for lack of trying, but they were very careful to keep a lock and key on that sort of thing, even if they did have the legal backing to enforce it. So… how did they manage to have so many secretaries and other female employees?
Money.
As humiliating as the positions may have been, the pay was absurd. Lower than their male counterparts in the company, but high enough to ignore or endure the pinches and slap on the ass they received on a daily basis. There was no other company that would pay even close to as well, and many didn’t think twice before jotting their names on the contracts, consequences be damned. Some regretted it. Most didn’t when they opened their paychecks.
When Akielah had put in an application to sign on as a secretary, she had also seen an opportunity. But not just for a large paycheck. Oh no. That was certainly going to be a nice little bonus, but her true goal was something much bigger. A scoop. A story. A way to break into the actual field she wanted to get into.
Freelance journalism.
She was going to find out every little detail about what went on inside the company, and was going to write a firsthand experience on it for all to read. She blended in well enough. Came off as just competent enough to warrant being hired, but not so skilled that she would draw suspicion to herself. And like any undercover journalist, she committed. Only pouted or bucked just enough not to raise eyebrows when she was getting punished. Laughed off and giggles every slap or pinch on the ass.
And she also made sure to make a fair impression with Gorden De Vanily himself. She had obviously wanted to work at the same location that the big man himself had. She wasn’t going to miss the chance to get face to face with the man who ran the empire. And if she was being honest, she could totally see just why he was the one on top of it all. He was sharp, and very little slipped past him.
Including Akielah’s act.
She had no idea when he had pegged her. No matter how many times she mentally reviewed everything in her head, she seemed to have appeared perfectly normal. Maybe that was it. Maybe she was being too normal. Well, whatever the case, he had pegged her. When she was asked to come to follow one of her fellow secretaries to a private room, a room which was more often than not associated with punishment, she knew she was screwed.
She could have made a break for it she supposed. But she knew better than to think she had a chance of getting very far before one of the many security guards caught her. Not to mention even if she had, that wouldn’t shield her from the legal ramifications. No, it was better to go along with it and see how she could work her way to something… well, she knew it wouldn’t be in her favor, but maybe break even?
“So, from one sister to another, how much do they have on me?”
Akielah sat in her chair with a smile on her face, not a hint of nervousness or fear in her expression or her tone. Her chin rested in the palm of her hand, the silk orange blouse she wore showing off no small amount of cleavage, and the black pencil skirt hugging her curves snugly. Her high heels tapped rhythmically against the tiled floor in front of her, her long and lovely legs crossed in a way that, combined with how she sat, wouldn’t have given quite the peek to anyone sitting before her.
Luckily, the present company was standing.
Stacie T, one of four ‘Stacies’ who resided in the office, leaned on the side of the rather large desk near the front of the room. Along with the chairs Akielah was sitting in and next to, it was the single piece of normal looking furniture in the place. The others were things like padded benches, wooden horses, and Saint Andrew’s cross. Not to mention the implements and toys that aligned the room.
The decor was clearly trying to send a message, and it was a fairly clear one.
Stacie T clicked her tongue, looking just as casual about the situation. Akielah assumed she was used to this by now. Her outfit was no less snug, similar in appearance, but opting for a green top and darker green pencil skirt. “Well, if you want me to be honest, I’m not entirely sure,” she said, shrugging her shoulders. “You’re definitely going to be put through the wringer. No doubt about that. But I can’t say what else he had planned for you.”
Akielah tilted her head slightly, looked more amused than anything? “Oh? From what I can tell, you’re his right hand woman. I’d have thought if anyone was in the loop, it'd be you,” she reasoned.
Stacie T had apparently been in a relationship with Gordon in the past. They had appeared to have split for one reason or another, though there wasn’t the usual drama one might expect between them. They seemed to keep things professional… well, as professional as one could be when one was keeping the other on a leash. Both figuratively and in all likeliness literally.
“Doesn’t make me a mind reader,” Stacie countered. “I can probably guess what sort of punishments he's got in store for you, but as far as after that? No clue. He hasn’t had me scheduled for the authorities yet, so you might have an out. Or you might be in for something even worse. It’s a crap shoot.”
Before Akielag could ask what he meant, they heard the door open. Stacie immediately straightened up, and while Akielah kept her demeanor calm, she couldn’t help but feel a tingle up her spine as she heard footsteps approaching from behind. Then, the man himself made his way into her view.
Gordon De Vanily was tall, fit, and undeniably handsome. His blonde hair was slicked back in a way that almost looked natural, and his green eyes had a confident calmness behind them. His suit was the picture of professionalism, though was tight enough to show off his lean but muscular figure. He made his way next to Stacie, who remained standing perfectly upright.
Under normal circumstances Stacie would be willing to show a bit of attitude, even if it earned her a smack or two on the rear. But this was a rather serious situation, so she wasn’t going to risk earning his ire. Gordon turned towards Akielah, arms crossed and as he looked her up and down. “Do you know why you’re here?” he asked, his tone as casual as she’d ever heard.
Akielah hummed and looked up in thought for a moment. “Am I being offered a raise?”
Gordon’s expression remained unchanged. “You can be as cheeky as you like, but I’d recommend taking this seriously. Depending on how this conversation goes, you could end up spending quite a long time within a prison cell,” he said. “Now, I’ll take you again. Do you know why you’re here?”
She sat upright, deciding to go ahead and drop the playful attitude. “I assume it’s because you found out about why I’m actually here,” she reasoned.
Gordon nodded. “Smart enough to know you’re caught at least. I watch all of my new employees. Someone like yourself jumping through the hoops of getting hired only to find something they could use to blackmail or ‘expose’ me isn’t uncommon. But admittedly they’re far more sloppy. You managed to move very carefully. Cover your tracks well. I actually had to put a bit of effort into catching you.”
He reached into his pocket, and then pulled out his phone. Then he turned it towards her. “Gathering recordings of punishments, making copies of the employment code of conduct and contracts, and recording to office chatter. You were very careful in gathering all of this. Impressively so. A less attentive person wouldn’t have noticed a thing. It would have made quite the article. I imagine. Nothing that would actually do any real harm to the company. For all of the noise some groups would have made, there’s no legal action that could be taken, and no shortage of those who still would have applied to work for and with the company. But I commend you.”
Akielah tilted her head and smiled. “Wow, a commendation from Gordon De Vanily himself. Those are stupidly rare from what I’ve seen. I feel honored. But, the fact is I was caught. I don’t imagine I’m going to be allowed to walk out of here with what I gathered, meaning anything I’d write wouldn’t be taken all that seriously. So my article is a bust. Which means the only question now is what you’re planning on doing with me.”
He glanced over towards Stacie. “Ms. Tomassian, remind me what happened to the last person who came in here under false pretenses.”
Stacie didn’t hesitate. “They were punished in your office, over the speaker so that the rest of the building could hear. After that she was let go. The last I heard she was having trouble finding work, but landed a position as a maid for one of our many generous donors,” she explained. She looked right as Akielah as she said this, not wanting to make sure she was giving any mixed signals.
Akielah raised an eyebrow. She heard stuff like this before in some of her research. People who caused waves and chose to leave rather than step back in line getting blacklisted not just in the business world, but damn near everywhere. The De Vanily family’s influence ran deep, and if they wanted to make sure you couldn’t get a gig flipping burgers, they had the weight to do so. Of course they usually found an offer from someone. Someone who was connected to Gordon in some way. A gift from the CEO and extra salt in the wound for those who tried to buck the system.
“Should I start preparing to speak in a French accent?”
Gordon shrugged lightly, as if he was chatting over lunch rather than preparing to crush a devious employee. “Perhaps. Tell me what you think will happen to you…”
She took a moment to think. This was obviously some sort of way to gauge her, so she needed to be careful about this. “Well, I haven’t been arrested yet. And you don’t come off as the mafia boss type, so I don’t think I’m going to end up in the back of anyone’s trunk.” She had done enough research on the company to know that even those who crossed them on a personal level didn’t really go missing or anything. Buried in lawsuits and no disclosure agreements, sure. But nothing that wasn’t done through legal channels.
“But, I’m obviously not walking out of here scott free. So my guess is that you see me as useful for… well, something,” she said, shrugging her shoulders. “Maybe getting into another company or digging up some dirt on your competition?”
Gordon gave an approving nod. “A fair assumption. Though not entirely accurate. I do think you can be of use to me, but certainly not at some other company. You’re too clever for me to let you run loose. I need you close, on a leash.” He leaned back against the desk. “I’m going to give you two choices. The first will be a hellish punishment, in which your bottom will be blistered raw. Followed by your termination. I don’t imagine it’ll be easy to find work. And of course any ‘reporting’ on the inner workings of what happened will not be an option for you. Not unless you want us to take legal action.”
“The second option is an equally hellish punishment. But rather than being terminated, you will be allowed to remain here. You will report directly to me as my personal assistant, and you will put the talents you used to infiltrate and gather information on this company towards helping me improve it.”
Akielah looked at him skeptically. “So, my choice is punishment with a gag order and potential jail time, or punishment with me serving as your new servant girl?”
“Whipping girl,” Gordon corrected. “You will be an asset, and one that will be used in every way I see fit. Your contract will be adjusted, and your pay increased to accommodate for your new position. But you will be subservient, obedient, and compliant. Or you could take your leave and be nothing. I won’t push you into either choice.”
Akielah stared back at him, holding his gaze for a long moment. There was no threatening glint in his eyes, or sadistic enjoyment. He was just presenting her options as they were. She knew the gag order would be no idle threat. There wouldn’t be any passing on what she knew to anyone else or posting it anonymously. They would link it back to her eventually, and she’d be screwed. On the other hand she knew what working right under him would mean. She had seen Stacie coming out of his office not just with a sore bottom, but with a rather crooked walk.
And the way he spoke so casually about just slapping a collar around her neck… there was actually something she had to admit was pretty hot about it. Still, she was weary.
“Can I negotiate?”
“No.”
“Can I have time to think about it?”
“No. If you don’t answer within the next minute or so, I’ll simply lock in option A for you.”
“Not giving a girl a lot of options, are you?”
“The fact that you’re being granted any at all that doesn't involve a prison sentence should be more than adequate for you. Now, decide.”
Akielah was quiet for a long moment, glancing over towards Stacie. The other woman stared back, though said nothing. There really wasn’t anything to say. The options were just as Gordon presented them. A life on a leash with her practically being barred from her journalistic aspects, or getting canned and cut off from one of the biggest stories in her potential career.
She wasn’t sure if he’d got through with blacklisting her like he did others. It wasn’t like she was giving away information or anything like that, but she had crossed him. It was possible she could end up getting cut off from normal work until she ended up in some low paying gig for one of his constituents. Neither option was ideal, but off the two…
“I’ll go with option B.”
If Gordon was pleased by the decision, he didn’t show it. He simply nodded, and then turned towards Stacie. “I emailed you the details of the arrangement. I want you to type of a new contract and have it notarized by the end of the day. I don’t expect any setbacks, unless you’d like to join Ms. Lahiffe.”
Stacie nodded. “Understood.”
She made her way out, not even flinching as Gordon gave her a firm slap on the rear. Once she was gone, Gordon turned his attention to Akielah once more. “While she works on that, I’ll get a better look at you, and then we’ll take care of your punishment. Stand up,” he ordered.
Akielah made her way up to her feet, wondering just what he had planned for her. She had been spanked a few times, just like everyone else here. Some guys were a little easier to deal with, wanting more to just grab a handful of ass than actually teach a lesson. Some were a lot more heavy handed however, and would quite literally take belt to ass. But she knew Gordon was a different beast entirely. Bottoms didn’t leave sore from his office, they left completely roasted.
He approached, and then began circling her. The gaze didn’t carry any lust. Or at least it didn’t give any away. It was more like appraisal. Like a man who was calculating how much a gem he’s come across was worth. “Did you see how Stacie was standing earlier?” he asked suddenly.
“Yeah, why?”
The smack to her rear came hard and fast, making her wince. “Sir. It’s sir or boss when you address me. Is that understood?” he asked.
She quickly collected herself, knowing the sting in her rear was going to be nothing once this really got started. “Yes sir…”
“Stand like Stacie did.”
Akielah adjusted based on what she saw of Stacie earlier, standing straight, lacing her fingers together in front of her, and keeping her feet together. Gordon continued to circle her, impressed with just how quickly she caught on. The posture was nearly flawless. She was observant, and a quick learner under pressure. Good. He raised a hand and tilted her chin up slightly. “This will be your greeting pose to me when you report in or I enter the room. You’ll be drilled on several others for both presentation and punishment.”
“Yes sir.”
Once again, he silently appreciated just how quickly she was learning to fall into line. He knew it was more out of wisdom in the situation and he’d have to train true obedience into her, but this was a good start. He reached up and placed a hand over her skirted seat. Her bottom was big. Not overly so. Plump and with just enough bounce to it. Another hand made its way up to her breasts, cupping it from underneath and weighing it in his hands. They were big. Bigger than Stacie’s.
He had made sure every secretary that was hired was as appealing to the eye as they were competent. He wanted eye candy for those in and visiting the office, and wouldn’t settle for anything less than the best in all aspects. But he also wanted efficiency. A dumb airhead who had nice legs but couldn’t file properly was useless to him. Akielah was not, and while he wouldn’t say it out loud, he found something particularly attractive about the woman.
“Strip.”
Akielah blinked, a bit surprised at the command. Baring her ass was something she was somewhat used to around here, and while she was certain there were more than a few others knocking boots with the men in the office, being ordered to outright strip was a first. Or at least it was for her. But rather than question it, she simply hummed and began following his instructions.
She unbuttoned her top, the first few buttons already undone. As she made her way further down her breasts bounced free, only contained by the simple black bra she had one. She moved to her skirt next, stepping out of her high heels before working it down her legs. Gordon’s eyes lingered on her rear as she shimmied it down, and then stepped out of it, now in matching black panties.
Akielah looked back over her shoulder at him, wondering if he wanted her to keep going. He gave her a nod of confirmation, and she actually smirked before continuing. This was like living out a scene from one of those spicy novels she liked reading while she curled up in a blanket with a glass of wine. Maybe she would write something of her own about this later.
Once she was completely nude, save her glasses, Gordon took her figure in again. Her breasts were bountiful and firm, her ass full and shapely, and she had a neatly trimmed bush right above her clit. “Like what you see, boss?” she asked, a mischievous glint in her eyes. He didn’t answer, and instead reached forward and placed his index and middle finger on either side of her pussy before using them to open it.
Akielah shuddered, but didn’t move as he knelt down slightly and took a look inside. He hummed and then straightened up again, sliding his two fingers across her clit. “Don’t speak unless spoken to,” he said.
“Yes boss.”
“Get dressed.”
She felt a tinge of disappointment. She was hoping that maybe he would make a move and they could get into something a little more… intimate. But she supposed until that contract was presented, punishment was all that was on the table for now. She reached down to grab her clothes and begin putting them back on. Gordon remained silent until he was finished.
The moment she slipped back into her heels, He gestured over towards the wall. “In the future I expect you to memorize every single implement by name. Grab the dragon cane. It's the third from the left on the second row.” Akielah flinched slightly. She had heard the girls complain about the ‘dragon’ before. Apparently it was the nastiest of them, which didn’t bode well for her since she hadn’t been caned at all before. The most she’d had was the hairbrush, and that hadn’t been that long of a punishment.
She walked forward, counting out which cane he had specified. It was a lighter color of wood, and looked rather thick compared to most of the other whippy ones. She grabbed the cane from its hook by the crook handle, taking a moment to weigh it in her hands before turning back towards him. Once she was in front of him, she held it out. Gordon took it and then nodded towards one of the tables in the room.
“Bend over it. Hands flat, feet apart. Head forward.”
Akielah leaned forward, and then began making her way over the desk. She bent at the waist, keeping her hands flat as she spread her legs apart. Gordon stepped behind her, tapping her thigh with the cane. “Further.” She shuffled even further apart, and then Gordon reached down and grabbed the edge of her skirt. He slowly began rolling it upwards until it reached her waist, and then hooked a finger in the waistband of her panties before beginning to pull them down.
Once they were down to the thighs, he raised the cane and tapped her bare bottom, making her flinch slightly. “Huh… I’m both totally aroused and terrified. Wonder how long that’ll last…”
Gordon continued to tap the cane a few times, watching her bottom bounce and getting a feel for just how hard he should swing. She had quite a fair amount of cushioning in the backside area, so he didn’t see much of a need to hold back in the slightest. Besides, with her offense he needed to send a serious message. “Keep your position until I tell you otherwise. If you break position, the stroke will not count. Is that understood?”
“Yes sir.” She wasn’t naive enough to try asking him how many she was in for or any other details. He didn’t seem the type to entertain being questioned like that.
He brought his arm back, giving a few practice swings to line up the strokes. Akielah jumped slightly at each one. Okay, this was definitely going to be hell, but she had to brace up. She could tell he wasn’t bullshitting about breaking position. He would drag this out for as long as he pleased, and she didn’t need to give him any other reason.
Finally, the first earnest swing came.
CRACK!
The impact came, and at first she only felt the cane imprinting itself into her cheeks before they rebounded off. Not long after however, she felt a searing sting. One much harsher than the hand or hairbrush had left behind.
“AW!!!”
She threw her head back, letting out a howl as she shot up from the desk, hands shooting back to her bottom. The sting lingers, and she squeezed her cheeks as if it would somehow wring out the pain from the spot she knew a welt was already forming over. Gordon watched her, his expression like stone as she bounced on her toes, heels clicking against the floor.
“I don’t believe I told you to rise, Ms. Lahiffe.”
She scoffed and looked towards him in disbelief. Seriously? Did he expect her to be able to stay still through more of those? He really was a demon! She thought about saying something, but she could tell from the look in his eye it wasn’t going to get her anywhere. “Yes boss…” She reluctantly turned back forward, and then began bending over the desk again, the arousal she felt earlier already vanishing in place of a rueful dread.
This was going to suck…
Once she was back in position, Gordon gave her a few more taps. She braced herself as best she could. If she couldn’t find a way to deal with this, this would drag out all day.
CRACK!
The cane came down again, slicing into her cheek. Gordon’s aim was nothing less than impeccable, the stroke landing right below where the first had.
“NNNNGH!!!”
Akielah jerked, her body tensing up as she pressed her fingers hard against the surface of the desk. Yet another shot of stinging pain was drawn across her ass.
CRACK!
“AAAAAAAGH-AW!!!”
Another stroke, and she lurched forward, her thighs pressing against the desk. For a moment she rose halfway up, but then quickly forced herself back down, gritting her teeth as she patted the desk with her hand to try and distract herself from the height of the sting.
CRACK!
“MMMM-HMMMPH!!!”
A third stroke, and a third red line now beginning to form right beneath the first two. She lowered her head, holding back the string of curses she wanted to let loose. Was he seriously going all out from the start? Most of the others who had spanked her started with a warm up phase… she hoped to go this wasn’t his version of it, because she wasn’t sure she’d be able to take it.
Gordon walked around to the side of the desk, moving her cane to the tip of her chin and then tilting it up. “Did I need tell you to keep your eyes forward, Ms. Lahiffe?” he asked, raising an eyebrow.
She panted slightly, though still managed a somewhat annoyed expression. “You did sir, I’m sorry.”
“Don’t be sorry. Be better. Be obedient.” He pulled the cane back, and then made his way back behind her. Akielah sighed, bracing herself once more. He wasn’t giving her any leeway. He had given orders, and he wasn’t settling for anything less than them being followed to perfection. She frankly doubted she could, but not at least trying was only going to make this worse.
CRACK!
“GAAAAAH!!!”
CRACK!
“URRRRGH-URRRGH!!!”
CRACK!
“HUUUUUUUUGH!!!”
The cane rose and fell, each one slashing down across her rear and causing her to howl out and jerk. She struggled as best she could to stay bent over and in position, though she couldn’t keep from lurching out of pace every few strokes. She would rise halfway up before quickly forcing herself back down, her hands would leave the desk or ball up into fists, she would raise a foot out of kneejerk reaction. She would quickly apologize after each one, but while Gordon said nothing, she knew he was noting each offense and probably adding to the punishment.
She was only given a few moments before each stroke. Just enough to allow the sting of the previous stroke to begin dying down before the next stroke would slice through the air and then deliver another. Gordon kept his composure completely, carrying out the punishment with a stoic efficiency. Though, while it didn’t show, he was enjoying the task at hand. Exerting his authority and discipline over others, particularly those who were capable in their own right, was something he often enjoyed.
Having a woman who fit his personal taste doing so only made the sensation all the better. Usually it was Stacie T who was squirming before him, which he still very much took pleasure in. But Akielah was a different, yet equally enjoyable experience. The way the cane pressed deeply into her shapely bottom, the way her breasts slide across the surface of the desk as she jerked, it was a treat to the eye.
CRACK!
“NNNNNNNNFF!!!”
CRACK!
“GRUUUUUUUUUUH!!!”
CRACK!
“NNNNNNGH-AAAAH!!!”
Slowly, the lines left behind by the cane made their way further and further down, leaving a column of perfectly horizontal red lines on her cheeks. She howled particularly loud when he reached her ‘sit spot’, the space where the curve of her bottom met the tops of her thighs, and couldn’t keep herself bent over at the first one. She didn’t fare much better at the rest either, but Gordon merely calmly ordered her back over and continued.
She had long since given up trying to keep track of time, and was just struggling to try not to screw up holding position. It was the only thing she could focus on to keep her thoughts from the searing sting that kept building up each time she heard the cane slice through the air. She was howling so loudly and was so focused on the sting and trying to stay over that she didn’t even notice the door opening again, or the approaching clicking of heels.
“It’s all done sir.”
Stacie T entered, holding a freshly printed contract in her hands. Gordon finally lowered his arm, though Akielah was still tense and weary. Her legs and cheeks were trembling, and her breaths were quick and tired. She had only barely registered Stacie’s voice, but she still had enough wits about her to tell what was going on, and she was grateful for the break. Whether this was the end of the punishment, or just a temporary hold, she needed it.
Gordon walked towards Stacie and took the document. “Everything is in order?”
“Yes.”
“You do realize what will happen if it isn’t?”
“I’m aware.”
“Alright then.” He moved back towards Akielah, and she tensed up yet again, wondering if he was about to continue. But then he slid the contract in front of her. He cupped her chin and raised it slightly, not forward, but enough to look at the document before her. “Read it. Exactly as is. If you misspeak or stutter, then you’ll be punished. If it’s a grammatical error Stacie will be punished.”
Akielah glanced up at him for a second, and then looked back down at it. She didn’t know if he was just trying to make a point to her, or just saw reading it himself as beneath him. But either way, this was further extending her ass not getting grilled. And since Stacie didn’t look shaken by the prospect of punishment, she could safely assume it would all be one her. She began reading.
“I, Akielah Lahiffe, hereby acknowledge and solemnly swear the f-following…”
Shit…
CRACK!
“AAAAAGH!!”
Akielah howled sharply, her hips jerking hard against the desk. “I-I’m sorry, sir!” She had already screwed up on the very first sentence. This wasn’t looking good for her ass.
“I applied to De Vanily Inc. under false pretenses. I knowingly misrepresented my intentions by submitting an application for the position of secretary while my true purpose was to infiltrate the company as an undercover journalist. I intended to gather sensitive information, recordings of disciplinary actions, copies of internal documents and contracts, and office chatter with the goal of puh-publishing an ex-expose…”
Aw crap! Again!
CRACK!
“OWWWW!!! FUUUUUUCK!!! I mean, I’m sorry sir! I’m sorry!” That had been two stutters. Was she getting two strokes?
“Continue,” Gordon said simply, merely tapping the cane across her cheeks.
She winced, but continued. “I fully admit this deception and acknowledge that such actions constitute fraud, breach of the standard employment agreement, and grounds for immediate termination and legal pursuit. In light of this admission, and in exchange for the Company’s forbearance from pursuing criminal charges, civil litigation, and industry blacklisting, I voluntarily agree to the following amended terms of employment.”
“Effective immediately, my position is changed from Secretary to Personal Assistant and Executive servant to Mr. Gordon De Vanily, CEO and Chairman of De Vanily Inc. In this role, I shall report exclusively and directly to Mr. Gordon De Vanily. I accept the title and duties of ‘personal wh-whipping girl’ and executive servant…”
CRACK!
“GAAAAAH!!”
Akielah’s legs kicked up involuntarily as she cried out. “Ahh! I’m sorry for the slip, sir!”
“I accept the title and duties of ‘personal whipping girl’ and executive servant. Meaning I exist first and foremost for his professional, personal, and disciplinary use. I explicitly agree that I will service him as needed in any way deemed fit by him or other authorized employers. This includes, but is not limited to, administrative and executive assistance, personal errands, intimate and s-sexual services, sexual availability at any time or place he requires, performance of any sexual act, oral service, vaginal service, anal service, use of my body for his pleasure or the pleasure of designated associates, and any form of physical or erotic submission he desires…”
CRACK!
“NNNGH— AAAAAH!!”
She bucked hard, tears pricking at the corners of her eyes. “I-I’m sorry, sir! I stuttered again!”
“Continue…”
“I further agree to submit to any and all forms of punishment that Mr. Gordon De Vanily or his designated representatives deem appropriate for any infraction, real or perceived. Such punishments may include, without limitation, spanking, caning, paddling, belting, flogging, use of any implement, corner time, bondage, humiliation, public or private display of my punished state, and any other corrective or disciplinary measure.”
“I acknowledge that my body, particularly my buttocks, breasts, and genital areas, are subject to these disciplinary actions at any time without prior notice. I understand and accept that any violation of this contract, any act of disobedience, any failure to provide immediate and enthusiastic service, or any attempt to disclose, record, or communicate information about the Company or Mr. De Vanily will result in severe legal a-action…”
CRACK!
“OWWWWWWW!!”
Akielah’s voice cracked into a desperate wail as fresh fire exploded across her already burning cheeks. “I’m so sorry, sir! I’ll read it correctly!”
“See that you do,” Gordon advised.
“…This may include immediate termination, pursuit of damages, defamation suits, breach of contract claims, and any other remedies available under law. I further consent to the Company using all means at its disposal to enforce this agreement, including but not limited to industry blacklisting and reputational measures.”
“I acknowledge that my compensation will be adjusted upward… and I agree that I will service him as needed in any way deemed fit by my employers. I voluntarily surrender any and all rights to refuse service, decline punishment, or terminate this employment without Mr. De Vanily’s explicit written consent.”
“I, Akielah Lahiffe, sign this contract in full understanding and acceptance of all terms. My continued employment and avoidance of criminal prosecution are contingent upon my complete and ongoing obedience.”
The moment the last words left her mouth, she hung her head, her breath exhausted and her body feeling drained. Gordon pulled out a pen from his jacket pockets, and then placed it in front of her next to the contract. “Sign and date. Then we can continue your punishment,” he said.
Akielah groaned. Of course he was still going to continue. She really was working for the devil it seemed. Still, she knew the alternative was not an option, and she would have already been in for it even if she did refuse. She picked up the pen, and then brought it over to the contract.
With a surprisingly steady hand, she signed her name down, and then dated it. Gordon watched her, and then grunted before he began undoing his tie. “Ms. Tommasian. Have my schedule cleared for the next two hours. I’m going to be very busy with Ms. Lahiffe…”
“Yes sir,” Stacie said, nodding.
Akielah had learned very quickly that Gordon had absolutely no care for the concept of mercy. The punishment had left her rear crimson, and she had ended up shedding quite a few tears by the time he had finally finished with her. She’d gotten a taste of the paddle, strap, and belt. It was hard to say which was worse. The caning had already left her so sore she really couldn’t tell them apart after that.
That was only the first hour though. Now that she had been punished for her little stunt, she was expected to show her gratitude for being spared legal action. That part… honestly wasn’t that bad. When he told her to spread her legs, she really didn’t take any issue with it. He was rough with her, and taking her from behind was a little tough on her cheeks, but she couldn’t deny he was damn good, and the pleasure took her mind off of the throbbing soreness.
The anal afterwards… yeah, that was a little less enjoyable…
Now she knelt down between his legs in his office, hands resting on his thighs as she swirled her tongue around his member. She honestly wasn’t that used to giving head, only having done it once with an old boyfriend. But Gordon was quick to correct her, keeping a fistful of her hair at all times and telling her what and what not to do. He also warned her to take note since he didn’t like repeating himself.
“Mm… mmph… mmmm…” Gordon gave her hair a rough tug, not enough to pull her off, but enough to get her attention. “Mmf!”
“I’m nearly finished. Brace yourself.”
Akielah looked him in the eyes, giving a slight nod before continuing. Gordon maintained his grip, but closed his eyes and allowed himself to enjoy the warmth of her mouth. She was good at this. Not as good as Stacie. Not yet. But for someone who he could tell didn’t have much experience, she was a quick learner. With each flick of her tongue he got closer and closer, and then he was ready to explode.
Akielah prepared to swallow, but Gordon pulled on her hair, his cock popping out of her mouth just before he came. She closed one eye as strings of his seed shot out, cloaking her face and hair in the sticky substance. She was genuinely surprised by just how much there was, and she was willing to admit she would have struggled to swallow it all… and he must have known that.
“Guess the devil does have a heart. Or at least doesn’t want to break his new toy…”
Gordon let out a single breath, and then pulled Akielah’s head up further, looking at her cum covered face. Akielah licked her lips, getting a bit of the cum that ended up on her chin and just under her nose. She actually smiled towards him. “Did I do good, sir?” she asked. She was perfectly willing to admit that this part of her new contract she was all on board for.
Was Gordon a total dictator who was probably going to use her as a whipping girl and living sex toy? For sure. Did she still find the scenario, minus the intense discipline, incredibly freaking hot, absolutely. Gordon simply stared back at her. He had no idea if she was genuinely enjoying this, or trying to start her servitude on the right foot by buttering up to him, but it was convenient either way.
“You’re finished for now. There’s wipes and paper towels in the cabinet across the room. Clean your face and stand next to me until I have further instructions for you.”
She raised an eyebrow. “You just want me to stand there?”
He hummed. “You’re right. Kneeling is better.”
Akielah scoffed, though a smirk made its way across her lips. She pushed herself up to her feet, staggering a bit with how shaky her legs were. Then she began making her way across the room towards the cabinet, feeling a bit of pride as she saw Gordon eyeing her ass as she did.
Her ass was still throbbing, her legs felt like jelly, and she knew that her foreseeable future would be filled with red asses and getting fucked sideways… but she supposed it wouldn’t be boring. And if she was going to be stuck in this place, she would have despised being bored.
She wasn’t giving up on getting out of this contract and writing her expose. Not entirely anyway. But if she was stuck in office life for now, she might as well have made the most of it.