Rich Bosses Are Always Weird

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At first, the ticking of the timer drilled a hole into Stephanie’s patience, each click bouncing in her ears and echoing in her skull. But now she found it peaceful and meditative. At least, when she could get herself to focus. The reception area in which she was stationed was an inside room of the suite; she had no direct access to outdoor light and even with the fancy smart-office system… LEDs still did not cut for the real thing. Especially moments like these when her boss deliberately maxed them to full brightness on the whitest setting.

I suppose there could be worse punishments, Stephanie thought. Her eyes flitted to the office in front of her desk. Its door was firmly closed and the glass panels frosted, obscuring anything from being viewed clearly by an outsider, but Stephanie knew better.

She simply sat at her desk while the timer continue to tick. Her hands remained neatly clasped, the very ends of her palms on the edge of the desk so that her wrists did not touch it. Thick ankles crossed and tucked at the foot of her chair, the only comfort or posture preference she was permitted, due to her pillowy thighs preventing her from keeping her feet flat on the floor when crossed at the ankles.

It wasn’t much of a comfort. Stephanie thanked the lord for creating stretch slacks so that her waistbands neither cut into her nor gaped at the back as she explored different fits and cuts in her work wardrobe. But where she struggled in this position were the armrests of the chair cutting into her hips and above her knees. It was torture and Alan absolutely knew it.

Stephanie knew she could steal a glance at his office door but she wouldn’t dare even try to glance at the timer on her desk. She just had to sit and wait for it to ding. And then, she would be free to go.

But she had to wait for 27 minutes. That was a long time when one couldn’t even look at the damned timer. Only stare ahead.

A dark pool slowly spread on Stephanie’s desk. In the near-silent, spartan office, now devoid of all other staff for the day, she could almost hear the liquid spreading across the glass surface underneath the rhythmic ticking of the timer.

Stephanie bit her lip as the edges of the pool widened, pushing outward, seeping into her periphery. If she could close her eyes longer than a blink without enduring her boss’ ire, she would have squeezed them shut and groaned, hoping that the puddle did not reach the edge of the desk.

The ding of the timer jolted Stephanie from her reverie. It was accompanied by a soft click as the office door opened simultaneously.

A tall, wiry man stepped out. Shoulder length gray hair wrapped neatly by a band at the nape of his neck. His suit was closer to a deep charcoal than a pitch black but it was expertly tailored and despite its neutral dark tone, was clearly woven of fine cloth. It was not off the rack, definitely something bespoke. It was not just custom-made from a good tailor; it oozed luxury.

The soft tip-tap of his shoes as he stepped through the door, briefcase and jacket in one hand, and turned to close it were the only sounds that filled the office for several seconds. Despite the fact the timer had finished and they both knew very well that her time was up, Stephanie would not step away from her desk until given permission.

The man advanced toward her desk, moving not slowly, but not in a hurry. Comfortably. It was a pace that suggested he wanted to observe the scenery but still get to his destination just on time and not a minute early or late.

This was Alan.

With every step he took, Stephanie wondered to herself, ensuring her face did not betray her thoughts.

Why do I put up with this? This man is insane.

He stepped closer.

Oh that’s right: the pay. And the resume padding… worse than my thighs.

Another step.

I’m just so glad I have a good therapist. If only I could have contacted his previous assistants…

Alan’s next advance almost finally closed the space between his office and her desk.

At least today is over and I can finally go home.

“I appreciate your patience, Miss Stephanie.” Alan’s voice often betrayed his thin frame. It was smooth and deep and oddly rhythmic; she had wondered more than once if he had a past life as a radio host. “Hopefully you have understood the error of your ways and will practice only the most precise care in the future.”

She could hear the smile on his face even if she didn’t quite dare look up at his dark beady eyes just yet. “You have my word, Alan.”

Something shuddered inside her, nearly shaking her to the point of her plump behind jiggling on the chair. Fortunately she was able to control herself.

Alan had never been untoward to her nor anyone else on staff that she had seen or heard. He had never said an unkind word or raised his voice. But there was something piercing and unsettling about him that she could never place. In Stephanie’s life she had endured more than her fair share of weirdos, creeps, and other bad actors that would actively choose to harm her at any opportunity and while she never picked that up from Alan’s behavior, something always lurked beneath the surface. She couldn’t place it.

Perhaps this is just what stupid, filthy, unimaginable wealth did to people. Altered their perception. Alan Barker was a tech giant, a multi-billionaire who had built an empire over decades of work. His background had always been fuzzy and some doubted that even his birth records were real. To no one’s knowledge was he married, had kids, or even extended family—tabloids insisted he had them relocated in witness programs.

Alan was kind enough; not necessarily cold, just not entirely… present. Something was always off with him. Most of the time it didn’t really affect any one in the office. Not even Stephanie who had the mixed fortune of being his first assistant. At least, as far as she could tell.

Then there were times like today when his eccentricities shined.

Stephanie would have never been able to secure a job with his firm if she had any history of tardiness or disorganization and she took great pride in keeping Alan’s calendar efficient and office running smoothly on his behalf. However today she had set down a bottle of soda on her desk 3 minutes before the end of her lunch break and bumped into it was she pulled files to resume a project after lunch. The bottle spilled soda all over her desk, including her work computer.

Due to the nature of the business Alan ran; fortunately, the machine was impervious to  sugar, water, and carbonation but cleanup took awhile. And one thing Alan Barker hated was inefficiency and delays.

And so, Stephanie’s punishment was thus: her “carelessness” delayed work by 27 minutes and so should she have her end of day delayed by the same.

In and of itself was simple enough—the few times in her life Stephanie had ever been tardy she had already assumed the role of staying late to make up for the time—but it was the intensity of which the punishment was brought out that gave her pause.

And nothing about Alan’s demeanor ever changed: when delivering his judgment for her error, he had been as kind as he had always been. Even now, greeting her at the end of the day, nary a frequency of ire traveled in his voice as he addressed her.

Even now, when the most unusual request came from his mouth and Stephanie could not help but agree simply out of sheer surprise, Alan did not change a single thing about his tone or body language.

“It appears as though you are not the only person to change my plans today,” he said, stepping over and handing Stephanie her purse and jacket. She stood up, resisting the urge to groan in relief as circulation resumed in her deliciously plump thighs and warmed back down to her toes. “Some friends had to unfortunately announce their absence from my home this evening, where they had accepted an invitation to dine with me. My beloved chef has already prepared the meal and I would loathe to see it go to waste.”

“Oh? That’s a bit unexpected of them. You don’t like to keep company with unreliable people.” Stephanie buttoned up her coat and casually slipped her purse over her shoulder. She shifted from one foot to the other, waiting for him to head to the elevator so she could go. Stephanie rarely felt any insecurity about her size and more often than not genuinely loved her curves and plump frame; bottom-heavy as it was, but she always felt positively enormous standing next to her boss. It made her uncomfortable.

“An astute observation, Stephanie. You’re right; I much prefer to spend my time with those who are dependable. Like you, for example!” He smiled warmly and dropped a hand onto her shoulder. “In fact, I believe I would prefer you to substitute for their company this evening. I’m sure we’ll have an absolute ball.”



Stephanie wasn’t stupid—she knew a command when she heard one, and she knew that Alan knew her schedule and commitments and that she had absolutely no way to say she wasn’t already occupied for the evening.

So that was how she found herself at his house. Well rather, his mansion. Or compound would be a better word. A massive modern American castle with winding hallways leading to grand open-concept spaces, dark colors splashed with warm brights for effect.

After being whisked away immediately upon entering the home, Stephanie found herself seated at the head of a dining table heaped with a fresh, rich feast.

It was as delicious to look at as it was to smell: a pan of lasagna, a hot roasted vegetable salad, a pile of fresh baked rolls. A tureen of tomato bisque sat nearby, steam curling upward. Some hors d’oeuvres nestled between them; various crostini and pinwheels.

“There really is nothing like coming home to a freshly cooked meal, wouldn’t you say, Stephanie?” Alan settled himself at the opposite end of the surprisingly small, six-seat table and gestured toward a staff member stationed in the corner. “I imagine working for me wears you out a lot. Do you get to cook often?”

The staff member served Alan first; tipping the tureen into a bowl and delicately placing a single roll on his soup plate. She then did the same for Stephanie.

“No, I mean sometimes, but not as often as I’d like.” Stephanie furrowed her brow when the server placed two rolls onto her plate and emptied the rest of the soup into her bowl—glancing at Alan’s plate she noticed he was simply slurping from a mug while her serving was at least twice his volume. Maybe she was just seeing things. She hadn’t eaten since lunch after all and it was just soup!

Stephanie shrugged and took a tentative sip. The creamy bisque slipped down her throat. The herbs and flavors were savory and rich. It was the best tomato soup she’d ever had.

Wow, Alan,” Stephanie said, dipping one of her rolls into the deep bowl. “Your chef is amazing!”

Alan only smiled and nodded and they both continued slurping. Stephanie fell into a haze as she continued. It piled inside her, coating her stomach, both comforting and unsettling as the acids churned within her.

When finally at last Stephanie finished, she rested fully against the back of her chair. She resisted the urge to rub her stomach which felt tight and sloshy. The warmth of the bisque soothed her and lulled her into a quiet stupor.

The server rushed in again at Alan’s signal; this time, serving up the lasagna. A perfect square was cut and served onto a plate. The server then set the entire pan in front of Stephanie.

She glanced between her host and the house staff; one remained professional and averted their eyes while the other grinned wolfishly over his own plate.

Alan tipped his head toward the lasagna before his guest. “I hope you understood me clearly before, Stephanie. I did say I wanted you to substitute entirely for my canceled guests. I suppose after your careless encounter this morning during your lunch break that you should in fact, be extra hungry. You know I cannot stand to see any food go to waste, even worthless junk like soft drinks.”

He forked a large bite for himself and chewed thoughtfully before leaning back. “I simply couldn’t resist the opportunity to teach you another lesson.”

Understanding dawned on Stephanie as she looked over the remaining spread of food. He fully intended for her to eat all of it.

Stephanie had never once spoken back against Alan. It had never crossed her mind; from the moment she met him she sensed his pure intolerance for nonsense and resistance. That this was her second punishment for spilling the soda earlier meant that any alternative to her resistance would be far worse.

“Besides,” he said, bringing a glass of wine to his lips. “It’s not as though you are a stranger to an extra helping or two, isn’t that right?”

The shock of his bold statement literally startled Stephanie. While her face reddened as deeply as the tomatoes blended into the soup, Alan just chuckled as the staff member tucked a linen napkin under her chin and handed her a fork.



Stephanie had never eaten so much in her entire life. Never mind getting her fat ass stuck in chairs, she wasn’t even sure she could bend at the waist. She felt positively stuffed to the gills, as though any wrong move and she’d pop open right there at the table.

While she was pretty sure she wouldn’t actually rupture her stomach, Stephanie wasn’t so sure about her blouse. She could feel the buttons pulling in their buttonholes, the little plastic fasteners squeaking and groaning against the seams. Still, they managed to hang on… so long as she didn’t have to move. Or breathe.

“Oh, you did so well!” Alan cheered. He clapped his hands joyously as additional staff swooped in, clearing the table in a single pass and a flash of an eye. When they left, all that remained was a single blueberry pie.

“I’m so pleased you were able to complete your punishment, Stephanie.” Alan stood and approached her again, just as he had done just a couple of hours before in the office. This time, he brandished a fork. “I was worried you might not complete the task set before you, and that I would have to find something even more for you to do, to ensure you really and truly grasped the lesson.”

Alan cut a bite of the pie and gestured to Stephanie. “You always have gone above and beyond, and that’s why I have enjoyed having you in my employ all this time. I’d like to reward you for that, if I may.”

Stephanie stared at the morsel he presented. Something in the back of her mind screamed in a way that nothing else had during any of Alan’s most eccentric and startling moments. She swallowed thickly and her heart thrummed in her chest. The food churned in her groaning stomach.

“It’s… that’s not going to kill me, is it?” She squeaked.

The pregnant moment of silence that filled the space between them hung heavily. Stephanie wasn’t sure if she had finally crossed a line and instantly regretted her question. It was the closest she had ever come to resisting or speaking back to her boss. She flinched, anticipating the plate smashing against the wall or the fork thrust forcefully into the rug.

Instead: Alan laughed.

“Absolutely not my dear! What use would you be to me then? No no, I would never dream of it—we still have far too much work to do together. Which I believe is actually going to start… right… now.” Alan seized the opportunity of Stephanie’s confusing, her mouth bobbing open and closed like a fish, and slipped the bite in.

“Mmph!” Stephanie chewed instinctively, daring not to spit it out. As she chewed, she couldn’t taste anything out of the ordinary—the crust was buttery and flaky; the filling robust and sweet; the consistency perfect. It was simply a slice of blueberry pie.

Stephanie dared to sneak a glance at her stomach, as though staring at it would relieve any of the pressure. It remained as it was, bloated and taut, testing the limits of her lower buttons.

When she glanced up again, another forkful was ready. Then another… and another… and before she knew it, the entire slice crammed itself into her stomach, resting atop the feast she had glutted herself with.

For several moments, there was nothing. Stephanie was too full to do anything; now, she rubbed her stomach as best she could. All the while her cheeks burned with humiliation at her glutted state, knowing what Alan would think.

Stephanie didn’t dare ask what was next or where she could go. What she really wanted, if she was honest—was water. She couldn’t get the taste of blueberries out of her mouth. In fact, the flavor seemed to be strengthening, not dissipating.

“Alan? What was in that pie?” Stephanie’s stomach gurgled, as though something churned the pile of food within it. It felt… odd, unlike the sloggy, over-stuffed feeling that had plagued her before.

Alan, delicately placing another fresh slice on the plate, turned back to Stephanie. “Did you say something, dear?”

Stephanie opened her mouth to answer, when a single ping rent the air, ricocheting off the chandelier above them, punctuated by the sound of tearing cloth.

“Tsk tsk,” Alan said, glancing down at her stomach. He said nothing more but when facing her, furrowed his brow. “My dear Stephanie, are you sad? You’re looking a little… blue.” As he said that, another ping sounded off. This time, it completed with a light plink as the button landed in on a stray surface.

Stephanie cooed, rubbing the sides of her taut stomach. She was both shocked and embarrassed that she had literally begun bursting out of her shirt but relieved for the freedom of her undeniably-stuffed stomach to lurch forward and outward—which she could literally see with her own eyes.

Stephanie stared at her rotund gut. Something about it seemed off, even more so than it was larger than she even thought possible. It looked… cooler. Darker.


All the while, her stomach rumbled and gurgled, various substances and gases churning inside her. It felt different, not just like that there was a lot in there, or even gases bubbling upward, but that something was being made inside of her, pushing her outward. It was so small at first, just a millimeter or two, until Stephanie could clearly see full centimeters and inches of girth stretch forward from her, all the while her skin darkening. What started as a simple pallid paleness had darkened into a rich violet, pooling outward from what Stephanie guessed to be—as she could not see—her navel.

It could have been a bruise or even something rupturing inside her, but when Stephanie felt the rest of her clothes tightening—trousers cinching around her thighs, arms thickening in the sleeves of her blouse—she could only think of one thing, something dangling in the back of her mind.

“I… I feel funny,” she moaned.

“I’ll bet you do,” Alan replied, quickly pressing a bite of the pie past her lips.

It all happened so quickly and yet as though it froze time simultaneously. The intense blueberry flavor in Stephanie’s mouth overpowered anything else; the crust, or wine, or water, or milk—anything poured into her mouth to wash it down. Her body churned and groaned and swelled forth. Underneath her, the chair creaked and groaned along with her clothes, seams slowly giving one by one in time with bites and swallows.

It was all Stephanie could do to simply hold on and not explode. She was not bound in any way and yet could not muster the energy to break away. The swelling was much too intense, the pressure building constantly in her stomach and in all of her extremities as everything swelled.

The chair beneath her suddenly gave way with a sharp crack. Stephanie’s swollen body flopped to the ground, rippling. The displacement pressure proved to be too much for the remaining seams of her clothes and they burst off her, the last buttons wedging themselves into the ceiling, zippers ripping off, cuffs torn to shreds.

On her back, Stephanie realized that her head hung far too high above the ground. Something was beneath her, and as her body churned and settled she realized it was herself—her own engorged body… that was only continuing its growth.

“Wait a minute! Wait! How big am I going to get?!” She managed to cry out, between growth surges and more pie being shoved in her mouth. Stephanie had long accepted that Alan was going to stuff her beyond her limits, but this was not what she anticipated.

It seemed surreal, as he simply chuckled in a friendly sort of way. The sound of the pie plate being set back on the table and the sensation of his strong, wiry hands pressing firmly but gently into her side—the stunning realization he had not just fattened her, but turned her into a blueberry. An enormous, glutted blueberry.

Alan said nothing as he continued his touches, his hands moving all about her body. Every so often he would brush against a scrap of clothing that still hung on or sweep a crumb off of her, but never went near any of her sensitive areas. It suddenly dawned on her that this was not the first time he had done this—and explained exactly why she had never been able to find a former employee who had previously held her position, but she could find every other.

Stephanie trembled and whimpered, her body gently swaying under Alan’s touch, surges of growth churning inside her every so often. Her body groaned and squeaked, the crest of her globular stomach eked higher and higher toward the ceiling.

At long last, Alan pressed hard enough against her that she rolled.

Stephanie gasped and by instinct went to stop herself from moving, only to find she was bound helpless by turgid, conical arms, uselessly tapering to puffy wrists. “What are you doing?” She cried. “Please, stop!”

“Now, now, Stephanie,” Alan replied, pressing against her front to prop her upright, vertically, as though she were sitting… or standing. “I invest so much time and resources into creating my art, surely, a few minutes to relish it is not too much to ask?”

Alan presented the pie plate, with one narrow sliver of pie remaining. Stephanie whimpered. She flexed the toes buried underneath her round body and stretched out her palms nervously. She glanced around, surveying what she could see of her body which was admittedly not much, although it was becoming much more than she could ever have possibly imagined. Just a curved expanse of blue, smooth, save for a mole here or there and the ever-shrinking remains of what had been her arms.

“You are quite close to completion, my dear,” he said, forgoing the fork and plate and instead scooping the slice into his hand. “But you are not there just yet. The rest were not nearly as… ripe as you are and thus they served other purposes for me later.” He sighed wistfully and glanced away, dark eyes watery. It was the most emotion Stephanie had ever seen him display. “I can only hope their current caretakers cherish them as much as I did.

“But you!” He cried happily, pinching and holding Stephanie’s nose. “You shall be my Sistine Chapel, and I cannot wait for the world see what a masterpiece you are.”

Unable to breathe and desperate to relieve any of the pressure, Stephanie opened her mouth and without a second of hesitation, Alan shoved the entire remaining slice in, cramming it. It crumbled and folded over itself, blueberry filling oozing out of her mouth.

“Mmph! Mmmph?!” Even before she could chew and swallow, another surge coursed through Stephanie, sucking up nearly the very last remnants of her arms, her chest bumping up against her chin.

Finally satisfied, Alan wiped his hands. He circled Stephanie slowly, thoughtfully, occasionally tracing a fingertip along her circumference, hm-ing to himself. “Yes… yes, you will do beautifully in the main lobby, a testament to discovering true-blue talent!”


Author's Note: 


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doubleintegral's picture
This is really well written. 

This is really well written.  Hope to see more from you!