[Mature Asian Boss TG] Pleasing the Boss

Free Tier Reward Kolea

A white CEO who doesn’t know what he’s doing is magically transformed into a mature, domineering Japanese woman whose male employees would do anything to please.

~

Max shut off the Zoom call and sagged back into his chair with a sigh. That meeting had been a nightmare, just like the one before it. Not because profits were terrible or the company was failing, no, if anything, his company was thriving; the problem was he couldn’t understand a damn thing being said! 

When a strange man showed up at his workplace a year ago and announced that his estranged Japanese mother had left him her entire company, Max was thrilled. He barely remembered the woman who had given up being a mother and disappeared from his life when he was still a child; he hadn't expected to get anything in her will, let alone an entire company! 

So here he was, CEO of a global shipping company at the age of twenty-nine. He had plenty of money and even a nice penthouse home in the middle of Tokyo; he should have had it made! If only running a company in a foreign country where he didn't speak the language wasn’t so difficult. He didn't understand what people were saying or the customs that were baked into the Japanese salaryman lifestyle. He could tell all his employees resented him as well; they just saw some stupid foreigner sitting in a chair, struggling to even read his emails without a translator. 

He’d been trying to learn for the whole year since he arrived, but the language eluded him. He’d tried apps, books, classes, films, just about everything. Well….almost everything. When he’d first arrived, his mother’s office had been totally cleaned and emptied, except for one thing: a tiny tin of those konpeito sugar stars and a note that simply read ‘when you get desperate’. 

He’d assumed they were just his mother’s sugar stash for when things got stressful during crunch time, but then he had gone to throw them away, only for the cleaning man to return them to him with a meaningful look.

“You may need those.” He said seriously, “Eat them all when you want to be a good CEO.”

Max had been so taken aback he’d just nodded and added them back into the desk before forgetting about them for a few weeks. But then as time went on and things got even more difficult when he bungled a meeting with a partner company (How was he supposed to know offering a business card with one hand was rude?) he’d started to think about them more. 

It was silly, but he was desperate. His receptionist, a young man who clearly resented his new boss, said something in slow, deliberate Japanese that he couldn’t understand and Max cursed.

“Fuck it, why not. Worst case scenario, I just get a cavity.”

He reached into the desk and pulled out the little tin before tipping the full contents into his mouth. The tiny, bumpy sugars were sickly sweet and instantly melted against his tongue. He sat back and sighed; great, now he was going to get a sugar headache in a few minutes. The intercom buzzed again;

“Mr. Conner, did you hear me? The personal files have been updated for review.”

“Yes, thank you. I will get to it by the end of the day.” 

He groaned, clicking open the document before freezing in place; had he just…spoken Japanese? He had! He’d even understood his secretary! He had no idea how or why but that sugar had worked! 

He opened the personnel files he was set to review and found that with a little focus, he could actually read them without having to look up every second symbol! For the first time ever, he sat back in his CEO chair and grinned ear to ear before getting to work. He’d allocated almost the entire afternoon to working on these since it usually took so long, but now he was blazing through them, his long fingers clicking away at the keyboard happily. 

After an hour though, he started to shift in his seat. He felt a little uncomfortable and stiff, but no matter how much he rocked back and forth, his butt felt wrong. Eventually, he decided that what he needed was a good stretch. He stood up only to immediately lose his balance.

“What the fu-agh!” He fell flat on his face and groaned; why had that happened?

He looked down at his ankles and cursed; one of his heels had broken off! Wait…his heels? Max blinked at the broken high heels and the feet attached to them with fascination. They were his feet, but…how could that be? Now that he was paying attention, he also noticed his suit pants had been replaced with a tight-fitting business skirt as well.

A skirt that was paisley shifting as his body changed beneath it. With a groan, he felt an odd pulling sensation widening his hips and cinching his waist in. Max could only watch in shock as his lower body began to rise off the ground as his ass swelled beneath him. He was transforming into…into a woman?! He could see his skin changing too; the long legs that poked out of his skirt were now an olive tone and silky smooth. 

Slowly, with an odd sense of dread, his eyes continued up his body and watched as his chest began to swell as well. He could feel them, round and bouncy, getting bigger by the minute…boobs! He gaped, taking in the curvy figure as his clothing changed to suit it. His business shirt began with a blouse and matching suit jacket with silk lapels that framed his two beautiful breasts. 

“What…WHAT!?”

His words came out in Japanese without even thinking, but that wasn't the only thing that made them seem wrong. His voice itself seemed to have changed; it was lighter, slightly older, and feminine. Awkwardly, he kicked off the heels and got to his feet, running for his private bathroom and coming face to face with a stranger in the mirror. 

A blurry stranger at that. His vision slowly cleared as he felt something form across his nose. A pair of square-framed glasses brought the whole world into view, and he could finally look at the person staring back at him. 

The woman in the reflection mimicked his every move. Her sharp eyes, high cheekbones, and immaculate ponytail only added to her authoritative presence. Max reached up to touch his face, feeling the unfamiliar contours and smooth skin. His fingers lingered on the full lips and almond-shaped eyes; this woman was mature but not old. And somehow, she was him!

The fabric was soft yet structured, moving with a grace he had never experienced in his own clothes. He ran his hands over the smooth lapels and felt the subtle weight of the jacket, the silk lining cool against his skin. The blouse beneath it should have been conservative, but his bust was big enough that it insisted on peaking through the undone button at the top. It was tight enough that it felt almost like a second skin and the second button was straining. The eyes were naturally drawn to it; the button was basically begging to be undone. 

The pencil skirt, while unfamiliar, offered a surprising freedom of movement, the slit at the back allowing him to walk without constraint and clung tightly to his wide, motherly hips. His fingers brushed the pearl necklace that adorned his neck, a simple yet elegant piece that complemented the outfit perfectly. Somehow, it made his new sharp features look all the more authoritative. He studied his reflection, noting how everything about the outfit seemed meticulously chosen to project authority and elegance. 

“Manaka-sama? Are you alright? I heard you fall.” His secretary called, opening the door to the office just as Max exited the bathroom, holding the broken heels in his hand.

“Ah! I shall get you some new shoes at once, Manaka-Sama.” He bowed low.

Before coming to Japan, Max would never have guessed it was possible to bow sarcastically, but his secretary had somehow managed to do that everyday since his arrival. Yet now, the gesture seemed sincere, and he didn't seem the least bit confused to find a woman standing in the CEO’s office. 

“Thank you,” Max replied, unable to think of anything else to say in this bizarre situation. 

He sat down behind the desk, enjoying the extra cushioning his plump ass now gave him. The man returned a few minutes later with a box containing a brand new pair of heels, sleek, black and shiny. His face was flushed, and Max realised, with a shock, that he must have run down to the shopping centre next to the building to buy them himself. 

“Here, ma’am.” The secretary was on his knees before him in an instant, daintily holding Max’s foot and slowly sliding it into the new shoe. “Does this please you?”

A wave of authority and pleasure crashed over Max. Seeing that wide-eyed young man on his knees before him, he couldn’t help but smile. 

“It does. You have done well.” 

The secretary flushed with pleasure at the praise and a tingle went up Max’s spine; he could get used to this…

“There is a meeting about the new shipping routes…” he said after clearing his throat and Max nodded.

“We’d better go then.”

Normally he dreaded such meetings but now that he could understand Japanese he looked forward to it. Plus, he wanted to see what the rest of the office thought of his new persona, Miss Manaka. 

Normally, he sat at the end of the table squirming awkwardly during meetings but thanks to his transformation things couldn’t be more different. Max stood at the head of a long conference table, presenting a detailed financial report to a room full of executives. His voice was clear and commanding, the initial hesitation gone. 

The executives listened intently, nodding in agreement, their respect for him evident. He couldn't help but notice there was more than just respect in their eyes but admiration and...attraction. It was a little weird at first but he couldn't help but feel pride in that. He'd never been considered hot before but clearly he was now. 

When the meeting was over and the group dispersed back toward their cubicles, Alan moved gracefully through the crowd. He engaged in lively conversations, effortlessly switching between Japanese and English, though English was starting to feel unnatural on his tongue. He ignored that though, preferring to speak in Japanese now; it just suited his accented voice so much better. 

As he headed back to his office Max noticed a group of young men, the company’s rising stars, gathered around a table, engaged in animated conversation. He approached them with a warm smile.

“Mind if I join you?” Alan asked, his voice carrying the refined tone of Miss Manaka.

The men looked up, surprised but pleased and was that a look of hope in their eyes? 

“Of course, Manaka-sama,” one of them, Hiroshi, responded, pulling out a chair for her.

Max began asking about their current projects and personal interests as he sat down. The initial formality quickly dissolved into a relaxed conversation. Hiroshi spoke passionately about his recent success in securing a major client, while another, Kenji, shared his enthusiasm for the company’s new marketing campaign.

He watched how their eyes continued to dart to him, and his ample cleavage. They were clearly fishing for praise from the boss and once again, that sense of authority washed over him. It lit a fire inside him and…between his legs. To be so desired and so important to these men was intoxicating. 

“It sounds like you’ve done very well for my company, Hiroshi.” He said after a moment and the man beamed. “I’m proud of you.”

“Oh thank you Manaka-sama.” He gushed. “I hoped to win your approval.”

Max couldn’t be sure what compelled him to do so but he stood up and motioned Hiroshi forward.

“In fact, I think you deserve a reward for all you have done. Come with me to my office.”

All the other men watched on jealously as Hiroshi followed Max back through the cubicles to the CEO office. Excitement bubbled in Max’s veins as the man followed behind him like a loyal dog; he couldn’t help but wonder just how far he could take this. 

“Close the door, lock it.” He ordered as they arrived before sitting back in his chair. 

Hiroshi did as he was told and then stood ramrod straight in front of Max, his eyes filled with hungry expectation. 

“You’ve done very well, do you think you have earned a reward?”

“Oh yes, Manaka-sama.”

“In that case,” Max spread his legs wide, revealing the crotchless panties even he hadn't realised he was wearing until just now. “You have earned the right to please me.”

“Oh Manaka-sama yes, thank you, thank you!” Hiroshi was on his knees in a second, head between Max’s legs as his face disappeared into his skirt. 

Max groaned, feeling that wet, warm tongue slowly wind its way around his new clit. Hiroshi was clearly trying to savour every lick and draw this out as long as possible. Max had never experienced such pleasure or such power; Hiroshi’s tongue pressed inside him and he saw stars as the pleasure grew.

“Oh Manaka-sama, you taste so good.” he moaned between licks and Max felt himself getting wetter.

“Faster!” he ordered, “make me cum.”

Hiroshi didn't respond in words, just a deep groan as he continued to tease Max’s clit with his tongue.

The pleasure built and built as Max wrapped his legs around Hiroshi’s shoulders and pulled his face closer, forcing him to fuck Max harder with his tongue.

“Oh…Oooooh yes!” 

Max came with a squirt, legs pulsing and clenching so that Hiroshi had no choice but to keep diving his tongue between his folds until Max was truly finished. The man pulled back, his face was wet with Max’s new juices and his pupils were blown wide. Max chuckled, he couldn’t imagine how sexy he must look right now; nipples hard through his blouse, legs spread and face flushed. It was no wonder the young man before him was hard as a rock. 

“That was good, I think you deserve a second reward.”

Just like that, Max pulled the man into his seat and swapped places before settling down on his lap. Hiroshi seemed lost for words but that was alright; Max undid his blouse one button at a time until one his heavy tits fell out into Hiroshi’s face.

“Suck.”

He did so, taking the nipple in his mouth and making sparks of pleasure shoot through Max’s body as he sunk down on the man’s cock. He bounced easily, he was so slick with juices that they dribbled down his thighs as he began to bounce. Hiroshi gripped his hips tight and continued to suckle on Max’s nipple until, finally, the pleasure seemed to overwhelm him. 

“Ohhh, boss, oh Manaka-sama! Yes, fuck!”

“Don't you cum!” Max ordered with a grin, “No cumming before your boss.”

“Y-yes Manaka-sama, I-I’ll try, but…ohhhhh you feel so good.”

The poor man was right on the edge but Max kept on fucking him hard and fast, cumming again with a shudder and squeezing the cock so hard that Hiroshi had no choice but to follow. The man went limp beneath me and I giggled, running a red-manicured nail down his cheek. 

“Did you enjoy that?”

“Oh yes…”

“Well, if you keep working hard, maybe you can earn another reward in the future.”

~

Max decided not to question how that magic sugar had worked or the implications that they had brought up about his mother. Instead, he threw himself into his new life as Miss Manaka; CEO of the most successful shipping company in the company. Morale was high at her corporation, in thanks to her liberal praise. In Japan, having a boss appreciate you was truly rare; having a boss who rewarded you with the best lay of your life was something else entirely. And it was his company, so it wasn't like anybody could stop him. 

He walked confidently through life with his heels clicking on the ground; now fully adapted to Tokyo. He didn't even care that he had to live the rest of his life as a mature woman; who cares if he lost a few years and gained breasts; they were too much fun for him to resent! 

“Manaka-sama?”

“Yes, Hiroshi?” 

The young man walked into her office trembling with excitement; it had been six months since that first day she’d had him and ever since he’d been simpering for another go. The man worked overtime almost every week just to try and catch Max’s eye.

“You asked for me?” He swallowed.

“Yes, I think it’s time for your performance review.” Max smiled wryly as he got to his feet. “Your work ethic has been impressive, but your quality is lacking.”

Hiroshi flinched.

“So I think you need a punishment.” Max removed his glasses and glared down at the man who had already fallen to his knees. “Are you ready, Hiroshi.”

“Yes, Manaka-sama.”

Max grinned down at the man who was prepared to spend all day pleasuring him if that was what his boss asked. 

“Good, maybe if you’re a good boy, I’ll let you cum after all.”