Pampered Secretary

[ABAlex]

Kaden waited outside the door, staring at his watch.


"Come at 7:46. That is 7:46, not 7:45, or 7:47. You will wear exactly what I send you in your messages. If anything is off, you will be punished. Understood? " he had said.


7:44

Kaden bit his lip. Of course, he had agreed. Why wouldn't he? He was being paid to, and had to admit to himself he loved the orders.


7:45 and 30 seconds.


He was wearing exactly what he had been told. Most of it was normal. A dark blue suit, with a lighter blue tie, the kind of thing anyone else would wear to the same job. Someone looking closely might notice it was far more expensive then he should have been able to afford on his salary, but it wasn't that strange for high level lawyers like Edward Greyan to buy clothes for their secretaries for looks. Traditionally those secretaries were women, but especially in the modern era, no one would question a separate choice.


If someone looked even more closely, or, say, took some of the clothes off as Edward was wont to do, they may have noticed a few other things. They may have noticed the small, thin collar hidden under his tie. They may have noticed the tiny lock on his belt, which Kaden had attached at home knowing Edward had the only key. They may have noticed something else, which was what made Kenyan blush the deepest when he thought of it.


7:46. Kaden opened the door and walked in.


He walked down the long hallway bordered on both sides by mirrors. Seeing himself, an his own shy, awkward stride, only made him more nervous as he approached the main office.


"Good morning sir," he said as he entered.


"Good morning Kaden" Edward replied.


Kaden sighed in relief. No anger yet, so that meant no punishment.


"Kaden, can you come into my office for a minute?" Edward said.


Kaden closed his eyes and swore in his mind. Something was off.


He entered the office to see Edward facing away from him, going over a pile of files on his own desk. Edward was everything Kenyan wanted and wished he could be. Successful, smart, and with the confidence and air to show it. While Kaden walked in short, shy steps, Edward strode with long, broad movements. He stood straight, suit and hair maintained perfectly, and spoke with an authoritative voice his clients had come to trust.


Kaden stopped at the door. The instruction was "into my office," no further, and he was careful to follow it exactly.


Edward shuffled through a few more papers. He picked a few out of the pile and laid them straight on his desk.


Finally, he let out a quick sigh and began. "Kedan, what time is it?"


Kaden swallowed. "7:46 sir," he said. He looked at the clock on Edward's wall to confirm.


"Is it now?" he smiled. "And what is wrong with that?"


"Ummm..."


"Well?"


"You said come in at 7:46."


Edward turned to look at Kaden, who flinched at his gaze. "I did. And did you arrive then?"


"Yes sir," he said. He paused. If he had, Edward probably wouldn't be asking. "I think so sir?"


Edward sighed. "How long have you been standing there?"


"Maybe a minute sir."


"So if you've been standing there for a minute, and it is now 7:46, what time did you come in?"


Kaden panicked. "But I checked my wa...


Edward cut him off. "What time did you come in?"
"7:45."


"And what time did I say to come in?"


"7:46 sir."


"So you didn't follow my instructions. That is ten." Kaden flinched. "Yes sir."

[ABAlex]

"Let me see your watch."

He held out his wrist. It was an analog watch, hand wound. Edward walked up to it, grabbed his wrist, and studied it. He sighed, looked at his own watch, then began turning it so that the hand moved backward.

"Your watch was a minute ahead. That is the kind of imperfection that can sour a man's reputation, and the kind of imperfection you know I'm going to punish you for. You should have checked for that. I don't want my reputation to fail because I couldn't control my secretary. "

"Yes sir." He hung his head. It was a discussion they had often. Edward was careful of maintaining his reputation, and ensured Kaden knew at all times how he reflected on him.

He turned Kaden's wrist over. "Also, this is not an appropriate watch for you. I can't have my secretary wearing something that looks like it came from a dollar store."

Kaden looked down. It was cheap, and a few years old, but he couldn't afford much more.

"I will be sending you a better watch in the mail. When it arrives, you will first set its timer exactly to this watch, down to the second. You will then send me a message that includes a photo of it and confirms you followed my instruction, and you will wear it on your left hand, facing outward, tightened to the fifth hole, every day from then on. Understood?"

"Yes sir." He bit his lip again when he went over the extreme details of the instructions. The instruction he got were always similar. In keeping with everything Edward did, they were specific and exact down to the tiniest detail, and he knew Edward would watch and punish any mistake.

Those details were the most the most strenuous part of his job, and what he loved about working for Edward the most.

"Now, look at the forms on my desk," he said, and pointed at them.

Kaden walked up to the desk and looked at it. He winced again. They were printed out versions of paperwork Kaden had prepared for Edward the day before, to be sent out that morning. The forms were all marked in red.

"Do you see the mistakes?" Edward asked.

"Yes sir."

"How many?"

He counted. "Five sir."

"Five mistakes. Here, you misspelled "awaken." Here, you used the wrong format for the date. Here, you used a period instead of a question mark. Here, you misspelled the client's name twice in a row. You understand that if I sent these out, it would look bad on me, right? You think my clients want a lawyer who can't spell?"

"No sir."

"I corrected them before sending them out. Still, its ten per mistake, so that makes fifty total. Understood?"

Kaden hung his head. He was used to the treatment, but that was a lot of mistakes at once. Fifty was far more then he was used to getting at once. However, there was no denying Edward's instructions. "Yes sir," he said.

"Assume the position."

(Short up date, but I'll have more up this weekend. Sorry!)

[ABAlex]

He groaned, but bit his lip again and held back his smile. He crossed his legs, then bent down to grab his ankles. A slight crunching sound reminded him of the other humiliating instruction he had been given for that morning. He smiled more, both at the humiliation and the knowledge Edward could make him do something so embarrassing. Also, it meant he may have a bit of extra protection for his punishment.

He held his breath as Edward walked behind him. He felt Edward put a hand on Kaden's back. His other rested lightly on his bottom, and he felt Edward rubbing it up and down. Edward loved to grope him before his punishments, and Kaden loved knowing how he was being taken advantage of.

WHACK! The first smack always took his breath away. No matter how many times it happened, it always came as a shock that he, a grown man, was being spanked as punishment.

WHACK! The second one made him gasp, and he felt Edward rub him again.

WHACK WHACK WHACK! Kaden closed his eyes and groaned. Edward was an expert and delivering his spankings on Kaden. They always started slowly, giving him time to realize what he was in for. Then, just as the knowledge really settled, Edward went full force.

The blows got harder and faster as they went on. Kaden began grunting with each spank, then shouting, and was finally crying out loud as the blows rained down. Still, he held onto his ankles, and refused to move.

Finally they stopped, and Kaden breathed out heavily. Edward rubbed his throbbing backside, enjoying the feeling of it.

Kaden was confused. He hadn't been counting, but it seemed fewer spanks then he had expected.

"Stand," Edward said, and Kenyan obeyed.

Edward smiled at him. "Good boy. You took your spanking well. Now, I think I could tell from the feeling there that you obeyed my other order well."

He bit his lip. "Yes sir."

"Good boy. But let's check to be sure, shall we?" He reached into his pocket and dug out a key.

"Put your hands on your head."

Kaden placed both his hands on his head. He watched as Edward leaned down and unlocked the buckle on his pants. He pulled them down, revealing the thick, white diaper he had been ordered to wear.

Kaden had never seen the kind before they arrived at his door, or even considered that they might exist. They were printed with baby blue band across the top with teddy bears dancing along them. He only then realized that they matched his suit and tie, and blushed at the knowledge that meant he probably wasn't going to be getting his pants back soon.

He blushed at the thought of spending the day wearing a fine suit on his top half, but only a printed diaper on the bottom. The garment was humiliating enough on its own, the contrast made it even worse, as if his attempts at fine dressing was just a silly game.

Edward was rubbing his hands around it, moving from groping his backside and his groin through the plastic material. Kenyan moaned and let his mouth hang open in pleasure.

"Hmm. They look nice on you, very fitting. I think I'll put you in them again," Edward said with his eyes down at the diaper, and Kenyan shuddered at the thought. Edward then looked up and leaned in close to Kaden's face. "Did you follow my other orders Kaden, about breakfast?"

"Yes sir," he moaned.

"And what were they?"

Kaden shuddered. He had a guess of why this order had been given, and was nervous to see if he was right. "That for breakfast I was to have three eggs, a bran muffin, an apple, some porridge, and a glass of prune juice, then coffee and water."

"Did you eat it all?"

"Yes sir." The meal had been far larger then he was used to, and far more then Edward normally told him to eat. It had more then upset his stomach, and he had been cramping and groaning by the end.

"And did you follow my final instruction? What was it again"

He shuddered again. This was more toward what he thought. "Yes sir." He sighed, afraid to admit it. "That between waking up and meeting you, I wasn't to go to the bathroom except to shower and wash my hands."

The orders followed Edward's knack for pointlessly specific orders, except that, as was sometimes the case, Kaden worried there was a hidden reason behind them after all. His being ordered to wear a diaper, then being ordered to over eat and drink but not use the bathroom left him with only one idea of what he was going to end up doing.

[ABAlex]

"Good boy, exactly as I said it. Then you should be ready for my next order. I imagine you have to go to the bathroom now?"

"Yes sir."

"Then go. Keep your hands on your head and push everything into your diaper. Do that now without moving anything else." He looked back down at Kaden's diaper.

He whined. He had been ordered to do humiliating things before. He had spent work days naked, or cleaning in a maid's dress. He had been given a tale and dog ears and lead around on a leash as he carried paperwork, or made to do his job with his hands attached to the sides in stocks. Even after all that, being told to wear and use a diaper took the games to a whole new level of humiliation. However, he always obeyed Edward, and the worse the orders the more eager he was to fulfill.

He pushed, though in reality with all the pressure that had built he more just had to relax what he had been holding all morning. His stomach gave way, and amount of mush poured into his diaper. He winced as he felt up, inflating around him, and caked his skin.

It only took a few seconds, but the damage was done. Kaden moaned at the release and was left panting, his diaper bloated and discolored around him, and the smell already hitting his nose. He blushed, and met Edward's eyes with a blush and a look of humiliated desperation in his eyes.

Edward met his eyes smiling. He waved a hand in front of his nose to tease him. "Good boy Kaden," he reached behind and patted his's bottom, making him wince again at the disgusting feeling of the mush being patted into him.

Edward walked behind Kaden as he remained obediently still with his hands on his head. Edward shoved a hand deep into Kenyan's diaper, making him gasp and groan in disgust. He released it then slapped it, making him gasp again. He spanked four more times, each time digging the mush more and more into him. He grabbed the top of the back, and lifted it.

"EEEP!" Kaden shrieked as the diaper was pulled into him. Edward yanked it a few more times, then released him.

"Did you count your spanks earlier, stinky?"

"No," Kaden shook his head.

"Tsk tsk, I always tell you about attention to detail." He shook a finger under Kaden's nose. "I gave you fifty. How many were you supposed to get?"

He sighed but nodded. Of course he had done this. "Sixty."

"Smart boy. I guess you are getting the last 10 in your dirty diaper. Assume the position."

Kenyan groaned but bent back down as he had before. His stomach was already turning, dreading how it would feel.

Edward once again put a hand on his back and used the other to rub his behind, though this time, the feeling was far worse. The slime and warmth pushed into him, and he tried not to move away.

Instead of a smack, the first hit sounded like a squelch.

"Ewww!" he shouted out, but Edward shushed him.

The second smack made him wrinkle his nose and groan.

The spanks were far less painful, as the soaked and swollen padding provided enough cover. Instead, however, the spanking took on a far more awful feeling as the spanking went on. After only the few smacks he had left, the pile in his diaper had become a far more disgusting, slimy mulch that sounded him. He looked back at Edward with a twisted, sickened look on his face, and Edward smiled back.

"Still intact," Edward said, patting the seat of his diaper. "It's a well made product. Nice to have you to test it for me."

"Yes sir, thank you sir," Kaden said.

"Mhmm," Edward chuckled. "On your hands and knees."

Kaden got down on all fours. This was more familiar territory, even if it felt different in his diaper.

"You will crawl to your desk at the front, reach into the third shelf on the right, and get out your notebook and a pen. You will crawl back here with it in your mouth, the pen hooked onto the rings with the hook on the cap facing outward. I will be waiting here."

Kaden crawled, feeling Edward's eyes on his messy backside as he did. He was used to crawling through the halls, though he had to admit the addition of the diaper added a whole new level of humiliation to the experience. It slushed and moved around as he crawled, making his stomach turn in disgust, but he kept going as ordered. He made it to his desk, got his notebook and pen as ordered, and held them in his mouth as he crawled back.

He arrived back at Edward's office to see him waiting. "Well done, stinky. Now stand up and put your hands on your head."

Kaden stood, notebook still in his mouth.

[ABAlex]

Edward smiled at him, and held metal hoop with a joint and a pair of scissors.

Kaden would have what it was for, but the notebook in his mouth kept him quiet.

Edward bent down and pushed one of the straps between Kaden's legs. "Tsk tsk," he said as he wrapped another strap around his waist. "You really do stink, you know? Disgusting."

He nodded. The smell and the feeling already made him gag, and each motion made it worse. He felt Edward cut a hole in the back of his diaper and pull the hoop through.

"EEEP!" he whined as Edward yanked the hoop into the air, forcing the diaper into a painful wedgie.

Edward held the hoop into the air, forcing Kenyan onto his toes. He felt Edward pat his backside and rub the mess into him, making his stomach turn. "Hmmm, again still intact. Even more impressive."

"Back up," Edward commanded and pulled the hook backward. Kaden scuttled backwards as best he could until he had his back to the wall.

Edward walked around to Kaden's front, put both arms around him, and grabbed the hoop with both hands. Kaden gasped as he pulled him up higher, pushing his messy diaper into him and forcing him on his toes. Edward strained.

Kaden shouted as the diaper lifted him higher.. His diaper was forced even further into him, and he was taken completely off his feet into the air. It became a painful and disgusting wedgie and lifted him until he was handing a foot off the ground. Finally, Edward pushed his hands backward, and attached the hoop on his diaper to the coat hanger behind him.

He groaned. He kicked his feet and groaned, but the couldn't do anything to change his situation. He knew the coat hangers Edward used, they were deliberately built with reinforcements in them, and he knew they would support him as long as his diaper remained intact. This left him in a humiliating, disgusting, and painful situation. His struggles only made the situation worse, and he gave up. He looked down sadly at Edward, who was laughing.

"Ahh, enjoying that?" He asked. He backed away from him, where his head was roughly in line with Kaden' diaper. "I'm enjoying the view, but that smell is horrible."

Kaden shook his head. The disgusting mush and padding being pulled into him made his stomach turn. Worse, it quickly became painful, and the feeling only got worse.

Edward walked up to him, took the note book out of his mouth, and handed it to him. "Alright diaper boy. I have a task for you today. I have some clients coming, very special clients. They work for a kink company, the one that provided your special undies."

He held up a spare diaper, with the same design as the one Kaden was wearing. "They claim they have created an extra strong adult diapers for use in kink play that won't fall apart or tear no matter how much you use them or pull them up, and want me to give advice to their new company. They gave some to me, and I said I'd have my secretary test them, which I've done. You are going to remain hanging there, testing their product, proving that they work and that I am a man of my word.

He looked down at Kaden's diaper. "Seems they told the truth. No leaks," he said, pointing at the diaper. He blushed and whined again. "So, in appreciation, you are going to hang there, like that, when they visit. They will be expecting to see you. Take your notes, and record everything they do carefully. When they are done, be sure to thank them for it. Understood?"

"Yes sir," he replied.

"Good boy. They will be here in about ten minutes. Until then, try to get comfortable. Or uncomfortable, if you prefer."

[ABAlex]

Kaden smirked. "And to think, everyone I know thinks I'm such a respectable man with a real adult job.

Edward smiled back. "You are VERY respectable. I've never seen someone take so many spanks then sit still with a straight face." He kissed Kaden on the forehead and patted his cheek, then turned to walk back to his desk.

Kaden groaned and squirmed as his diaper dug further and further into him. Realistically, his stated task didn't mean much. Edward had recorders and cameras, Kaden's notes were really just an excuse for future punishments. All he was really there to do was to be amusing to them. They would see him being punished and humiliated with their toys, and appreciate Edward all the more for it.

He groaned one final time and resigned himself to his face. All his squirming had accomplished was digging his disgusting wedgie further into him. As it was, ten minute already seemed like far too long to be left hanging from his own dirty diaper, and he knew he'd spend far more time trying to take notes as they talked around him.

His diaper had begun to burn. The filth was irritating from the beginning, and was getting worse and worse as it went on. With it now crushed and pulled into him, the itch was maddening, and he struggled not to squirm as he knew it would only make it worse. He had heard of diaper rashes before, but he had never heard of a groan adult with one. He tried to imagine what it would be like to spend the week trying to hide his winces each time he sat down in front of clients as Edward chuckled behind him, knowing it was because he had messed himself.

Or, would he even get that far? Perhaps Edward would keep him in diapers, make him use them every day. He pictured himself sitting behind his own desk and trying to keep a straight face in front of customers with his fine suit and tie visible above it, but only his dirty diaper on beneath it. He'd be stinking, perhaps the client's would notice, maybe they'd even ask and he'd have a lie prepared. They had done similar things before with him naked or in panties, the desk was deliberately made to hide such things, but this was a new level.

The thoughts, like all thoughts he had about Edward's games, was both humiliating and exciting.

Now, he was about to be seen in his most humiliating outfit yet, and had to keep a straight, professional face or else receive more punishments. Either way felt exciting. He lifted his note book. If he assumed he would normally have two or three real mistakes, an extra four deliberate "mistakes" would ensure he was very sore. He smiled. He gave one more deliberate squirm to make his diaper more uncomfortable, and waited.

[Eagle0769]

Interesting where this has gone so far. I wonder if Edward will be changing Kaden’s dirty diaper himself or have someone else do it for him. 🙂

[ABAlex]

On 4/2/2024 at 2:28 PM, Eagle0769 said:

Interesting where this has gone so far. I wonder if Edward will be changing Kaden’s dirty diaper himself or have someone else do it for him. 🙂

LOL good question. Perhaps being able to change Kaden, or dress him how you want, could be a perk of hiring them?

Unfortuantly this was a commission, so we won't know unless they pay for more