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The CEO Cuck


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Here is my newest story!! :) The 2nd chapter is already posted on my Patreon page! (And a huge thanks to my Patrons - John Ferguson, Vicious Koala, Ryan, Mike Stanley, Mike DelGrosso, John Ferguson) I know I was MIA for a few months and I know that I have to work really hard to get back to where I was, but I'm willing to do that. I'm working hard to finish The Taboo Word and create other exciting stories and drawings for you all! I appreciate your understand/support! https://www.patreon.com/mamabug

Anyway! Enjoy the story! 

 

Chapter One

“Mr. Miller?” There was a knock on the door from his newest assistant Tina Lovell. She had just started working for the company a few months ago, newly graduated from college. She was a spunky young woman, beautiful, with long blonde hair and a curvy figure. Today she was wearing a black skirt that went down to her knees and clung to her body and a light blue dress shirt that was tucked in.

“Yes?” He called through the door and Tina opened it up, noticing the CEO Ross Miller sitting at his computer, papers all around his desk.

“Your wife just informed me she was on her way,” Tina said in a quiet voice, for the CEO always took her brought away. He was a gorgeous man in his late thirties, dark black hair and green eyes. He looked like he belonged in a magazine.

“Thank you, Tina.” He said as he glanced up from his computer screen. “Oh, don’t forget to inform everyone that the meeting has changed from two to four.”

“Will do, sir.” Tina answered with a nod of her head.

“Thanks, Tina.” He gave her a smile that wakened her knees.  Tina turned around and left his office, returning to her own desk that was opposite from his office.

“He is so hot,” One of Tina’s coworkers, Patricia said, as she leaned up against Tina’s desk.

“Yeah he is,” Tina replied, “but he is also married.”

“Does that mean much anymore?” Patricia asked her with a shrug of her shoulders.

It was only a few moments later when Mr. Miller’s wife – Jennifer Miller walked into the office. She was a taller woman, with short dark hair, and large eyes. She was just as handsome as Mr. Miller was. Tina was jealous of their relationship. They always looked like super models together and they absolutely adored each other.

“Is my husband still here?” She asked as she walked over to Tina’s desk. His wife was a gorgeous woman, but was quite imitating herself.  Although she never spoke in a harsh tone with Tina or anyone else before, she was just rather blunt and to the point.

“Yes, ma’am.” Tina said with a nod of her head. “He’s in there.”

“Thank you,” Jennifer Miller replied as she flashed her smile.

She walked into the office without knocking and about five minutes later they came out.

“Have a good day, Mr. Miller, Mrs. Miller.” Tina said.

Mrs. Miller, who had her arm intertwined with his, turned and looked over at Tina and flashed her smile. “Thank you, you two.”

Tina watched them leave the room and sighed. She wished she could find someone like that. Someone to love and appreciate her the way that Mr. Miller obviously does with his wife. Tina had seen countless women try to come onto him, but he always shot them down. She respected that, even if she herself did have a small crush on him.

“I can’t believe he is our boss. He is so young too.” Patricia said with a sigh. “Sure jealous of his wife to be with such a handsome man!”

“Yeah, I agree,” Tina sighed, “I wish I had something like that. Not so much being with a millionaire, but just someone who looks at me the way he looks at her.”

“You’re such a romantic!.” Patricia laughed as she nudged her friend in the shoulder.

“I guess so.”

“Want to go out for drinks tonight?” Patricia asked Tina as she grabbed her purse.

“Yeah, sure. Just give me a few minutes; I have to write out his email first.” Tina said.

“Alright, I’ll meet you downstairs.”

“Okay.”

 

xxx

 

“That is our driver over there,” Jennifer said as we left the office building, her arm was still tightly around me as we spotted our driver pulled off to the side of the road, standing beside our vehicle.

“Good evening, Mr. and Mrs. Miller,” the driver said with a dip of his head as he opened the door for the two of them before heading to the front seat.

“Don’t forget we have that dinner party we need to get to this weekend,” Jennifer said with a sigh as she started to run her fingers through her hair, “I tried to get out of it, but it was a no go.”

“That will be fine,” is all I said as I stared at the window, lost in thought.

“Also, Patrick will be joining us as well.”

I turned my head sharply and looked at my wife. “Patrick?”

“Yes,” she said, “he is your best friend after all. You don’t want him to attend?”

“That is fine,” I said as I cleared my throat, “also I did book reservations for our anniversary.”

“Oh! I’m excited.” Jennifer said with a broad smile. “Can’t believe it’s been five years.”

“Same,” I leaned over and kissed my wife on the cheek, just in time as we pulled up to our apartment building.

We lived at the top suite of the apartment building, it was the kind where there was a doorman waiting outside, luxury rooms that cost a fortune and even an indoor swimming pool.

“Hello Mr. and Mrs. Miller.” The doorman said as he opened the door for the two of them. Everyone talked and waved to them as they headed to the elevators. They were silent the whole way up.

Once they got off the elevator there was only one door for the top floor and that was their own.

“Home sweet home,” Jennifer said as they entered their apartment, placing her purse and jacket on the stand next to the door.

“Yes,” I said as I shut the door behind us.

“That secretary of yours…” Jennifer started to speak.

“Tina?” I asked with a raised brow. “What about her?”

“She’s cute, she probably has a crush on you,” Jennifer said with a sly smile, “but I suppose most people that work for you do.”

“Well,” I said to clear my throat. Tina was a cute girl, but she never made any comments that would lead me to believe she had a crush on me.

“She probably looks at you as such a strong alpha male,” Jennifer continued, “ready to tackle her down and fuck her hard.”

My cheeks started to burn as she walked over to me, starting to unbutton my pants, and slowly pulling them down.

“But, she doesn’t have a clue. No one in your office does. What would they think if they knew their big strong handsome alpha, was just a weak little boy?” With that she yanked down his pants revealing a thick white diaper underneath,

Jennifer placed her hand over my diaper and pressed harder and I could tell that she felt the warmth beneath her fingers. “A wet one that is.” She added.

She let out a laugh as she started to walk away from me, before turning over, “Oh, I forgot to mention, Patrick is on his way over.”

“W-why?” I asked, though it was a stupid question.

“He is my boyfriend after all.” Jennifer gave him a wink before walking away, leaving him standing at the door way, pants pulled down, exposed in my soaking wet diaper.

 

 

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10 minutes ago, novababy88 said:

Why did you switch from 2nd person to first person?

Because, I wanted the first part of the story to focus on the world around him. How the world views him. To show that he is actually an Alpha male who others look up to and are envious of.

But, when it's switched to 1st person, it is focused on his perspective and his reality - which is that he is a cuckold for his wife. 

Just a stylistic choice, basically. 

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  • 2 weeks later...

Sorry for the delay!! Was sick with the flu for almost a week and then tried to play catch up! :) The 3rd chapter is posted on my Patreon page and next week will go back to the regular posting on Wednesdays! 

 

Chapter Two

“You better be a good little boy while mommy is making dinner,” Jennifer said as she pointed the finger at me as I sat the table, only wearing a t-shirt and a soaked diaper.  I shifted my weight as I watched my wife start to cut up some onions and carrots for the beef stew that she was cooking.

“Y-es, mommy,” I whispered with a nod of my head.

“Good boy, now Patrick will be here soon to have dinner with us…and…” Jennifer turned around at me and gave me a knowing smile “to take care of my needs. Because I know that my baby husband isn’t man enough to satisfy me.”

“Y…yes, mommy,” I said with a nod, shifting my weight, feeling my dick inside the diaper start to stiffen.  The thought of my wife being pounded by a more powerful man, especially when that male was one of my best friends, was something that drove me wild.

A few minutes later, the doorbell went off, and I felt myself freeze.

“Oh, that must be him.” My wife said as she left the kitchen and headed into the front room where she opened the door. “Hey, hey, babe! How was work?”

“It was well; how was your day?”

“Crazy as always,” Jennifer said with a laugh, “dinner is cooking now.”

“Awesome! Smells delicious,” he said as he walked into the kitchen, “oh, and there is the little man!” He reached down and pinched my cheeks, and I felt myself scoot down as I tore my eyes up on Patrick. Patrick had about four inches on me and about 100 pounds, but it wasn’t fat. He was just overall a huge man.

And that wasn’t all that was huge.

Jennifer made her way over the back to the stove and started to stir the large pot, while Patrick walked up to her and placed a hand upon her bottom, kissing her on the cheek as he leaned over.

“Patrick! Be careful; we do have little eyes watching us don’t you know that?”

Patrick turned his head towards me; a sly smile came over his face. “Oh, I’m well aware.”

“Come now,” Jennifer said, pushing him away, “dinner is ready, and I’m sure my naughty little boy is hungry.”

“I know I am,” Patrick said with a lick of his lips, but Jennifer ignored him as she focused on preparing dinner.

They all sat at the large dining room table. Patrick and my wife were sitting next to each other while I was on the other side.

“Hurry up and eat everything, and mommy will feed you your milk,” Jennifer said as she took a bite and if felt myself blush as I began to eat.

“This is delicious, Jen. You outdid yourself again.”

“Oh, stop it,” Jennifer said with a chuckle as she leaned forward and kissed him on the cheek.

Once they were finished eating and the table was cleared, Jennifer walked over to me and grabbed my hand and pulled me towards the couch.

She then stood there and took off her shirt and bra, revealing her decent size breasts with large nipples. “Come on, baby; let’s fill up that tummy for you!”

She sat down on the couch as I crawled up on her lap, leaning against her as I let one of her nipples slide in my mouth and began to drink, thankful that she went through the trouble to start lactating for me.

“Aw looks like the little boy needs his mommy’s milk,” Patrick said with a hearty laugh as he began to kiss my wife while I laid across her lap, suckling on her, massaging her breast with my other hand as I did so.

I could feel them kissing above me; my dick was throbbing in my wet diaper now (which I had wet once again while we were eating dinner).  I wanted so much to slide my hands across my crotch and pleasure myself, but I knew I would be strictly punished if I did so.

“I think that’s enough, baby,” she said as she pulled me up away from her, “okay, you know the drill. You stand in your ‘looking’ chair, but remember! No touching yourself!”

“Yes, mommy.” I nodded my head as I walked away from the couch and headed towards a small blue chair that was on the wall that faced the couch directly. I sat my soggy butt on the chair, staring at my wife and best friend.

“I’ve been waiting for you all day,” Jennifer said as she and Patrick started to make out, sitting down on the couch as they began to strip each other of their clothes. Soon my mommy was sitting on the couch naked with my best friend. I licked my lips as I saw my best friend’s hard and thick dick, ready to please my wife. He was much bigger than I was.

He started by kissing her neck and rubbing her chest as she lowered her hand and began to rub at his dick. I shifted my weight in my chair, feeling my penis grow even harder to the point it was starting to ache. Oh, how badly I wanted to touch myself, but I kept my hands away from my soaking bottom.

“Oh, Patrick,” my wife called out as he started to slip his dick into her wet vagina and began to pound her hard. Jennifer was almost screaming, to the point that Patrick had to place his hand over her mouth to cover up her sounds as he fucked her. He kept going and going, slowing down every few times to steady his pace before going even harder. She was lying down on the couch on her back while he was kneeling. Every once in a while, he would give me a look and wink.

“I’m going to…I’m going to….” Jennifer let out a strained voice as she began to breathe hard, and before she knew it, she was a puddle on the ground.

A few minutes later, Patrick finished as well.

Jennifer gave Patrick a thankful smile before her eyes tore over to me. “Hey, you little boy, I need you to come over here and clean up your mommy. Then maybe I’ll be nice and change that soggy diaper you’ve been sitting in.”

At this point, Patrick had gotten off the couch, and I nodded my head, lifting myself from the chair and walking over to my mommy.

She sat up, with her legs spread, juices falling out of her.

“Clean up the mess that your best friend left in me.”

I crawled on all floors as I got closer to her, reached out my tongue, and began to clean up my best friend’s cum that was entangled with her own. The taste wasn’t pleasant, but the thought and action were thrilling behind I could describe.

“Good job,” my mommy said once I was done, she leaned over and kissed me on the forehead, before stretching, “I guess it’s about time we get ready for bed.”

“I’ll be going then,” Patrick said as he started to pull on his clothes.

“I want you to come tomorrow morning,” Jennifer told him, “that is if you’re not busy.”

“I can swing by in the morning before I head to the office,” Patrick said before leaning down and gave a kiss on her cheek.

“See ya, champ,” he bent down and rustled my hair with a laugh before leaving.

“Come on,” Jennifer said as she grabbed my hand and led me to the master bedroom. She laid me down on the bed before grabbing a new diaper, a bag of wipes, and baby powder.

“Here we go!” She said with a giggle as she ripped off the tapes and pulled down the diaper, revealing my soaking crotch. “tsk tsk, what a little man I have.” She grabbed a handful of wipes and began to clean me up. I’m sure she must have noticed some precum in his diaper from the arousal of me watching her with another man.

When she was finished wiping me down, she folded up the diaper and set it aside before placing a clean one under me and making sure to put enough baby powder in it.

“There we go! All nice and clean!” She said as she patted his bottom and gave it a quick kiss.

“Thank you, mommy.”

“You’re welcome, baby. Now get ready for bed, I’m heading to the bathroom.” She ordered me as she walked into the bathroom.

Later that night, as we cuddled up in bed, my wife had her arms wrapped around me tightly. This was our domain. No one else was allowed upon our bed. Jennifer kissed my neck as she hugged me tightly.

“Good night, baby boy.”

“Good night, mommy. I love you.”

“I love you too.”

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Here is the next chapter! Sorry for the slight delay! Hope you all enjoy it! :) Chapter 4 is already on my Patreon page 

 

Chapter Three

My alarm went off at 5:00 AM sharp. I groaned as I rolled over and smacked my hand against the clock, causing it to stop short. I heard my wife moan as she turned over in her sleep, but it wouldn’t be long before she woke up as well. I closed my eyes, wanting to go back to sleep. But, I needed to be up at the office by 6:00 AM to prepare for the meeting for that day.

I slid out of bed; the rustling had caused Jennifer to stir in her sleep.

“Ross?” She muttered as she turned her head. “What time is it?”

“5:00,” I said as I started to pull off my shirt, “I’m going to go take a shower.”

“Wait,” she replied with a stretch, “I’ll join you. I need to be up anyway.” Even though my wife didn’t need to work, she was always one to keep busy. She had started her own interior decoration company about five years ago, around the time we got married.

“Okay,” I said as she walked over to me, pressing her hand upon my crotch, feeling that it was dry.

“Let’s not waste a perfectly good diaper,” she told me as she helped me shimmer it down my waist and onto the floor before tearing it up.

“Already,” she replied with a yawn, “let’s hop in the shower.”

It was moments like this that they were just husband and wife. The two of them got in the shower together; the large shower head was large enough that both of them were under the water. They kissed each other, touched each other’s wet body, as well as help each other wash.

But, even still, I knew my place.  Although her hands grazed my dick, and she pressed herself against my body. Before I knew it, we were out of the shower.

“Don’t get dressed yet,” Jennifer said as she wrapped a towel around her body, “I need to message Patrick to come over.”

“Jennifer…I really don’t have time…”

Jennifer turned and looked at me, glaring at me. “You have plenty of time. Do not talk back to me.” She then left the room, a few moments later she returned with her phone.

“He is on his way.”

“What do you have planned?” I asked her.

She shrugged her shoulders and gave me a wink. “I guess you’ll have to wait and see.”

I felt myself blush as I began to brush my teeth and shave as I waited for my best friend to appear. About fifteen minutes later, my mommy was back in the bedroom; she was wearing just a light blue bra and matching panties, holding onto my diaper.

“He’s here, come on,” she replied, and I followed her, leaving our bedroom, I still only had a towel around me.

“Hey baby,” Patrick said as he kissed Jennifer on the lips, “you’re looking sexy this morning.”

“Thanks,” Jennifer said as she ran her fingers down his body, “I couldn’t wait for you any longer. I needed you.”

“Hmm,” He hummed as he kissed her again. I didn’t say anything, just stood to the side as I watched him kiss my wife.

Jennifer began to undo his pants, pulling them down slightly to reveal his dick, which was getting hard. She ran her fingers over him as they kissed while he ran his fingers down her body. I twisted my body, unsure what my wife had in store. There had been a few times before that she called Patrick over to give him some last-minute humiliation before sending him off to work.

Jennifer then bent down and placed her lips at the tip of his penis, before running her tongue all over him, then continued to go down on him. He was rather thick and big that she was unable to go all the way, but she did the best she could, holding on the end of his shaft with her hand. Patrick moaned as he placed his hand at the back of her head.

She continued to go up and down, switching it up, going slow and steady, to fast in the next moment. She kept it up for a good ten minutes, switching back from her mouth to hand before finally, the build-up was too much for Patrick.

She grabbed ahold of my diaper. “I want you to cum in my husband’s diaper, the one he will be wearing to work today.”

I felt my cheeks blush as Patrick’s face brightened up as he eventually came into my diaper.

“Thanks, babe,” Jennifer said as she kissed him, and then motioned for me to lay down on the couch, naked.

My wife slid the diaper underneath me, folding it up; I could feel my best friend’s cum inside my diaper as I wiggled about slightly. I bit my lip hard, feeling myself blush.

“This will be a good reminder today about your place,” Jennifer said with a giggle.

“I need to be going now,” Patrick said, “but I’ll see you later?”

“Of course,” she said with a smile as she kissed her lover goodbye before turning back to me, “and you need to go get dressed for work.”

I nodded my head and, without another word, slipped back into the bedroom to get dressed for work. Thankfully the diapers that I wear during the day are thin enough and discreet that they are easily hidden. I always wear pants that are about half a size too large for me but still was flattering.

My wife and I didn’t speak for the next half hour as we got dressed, not wanting to be late.

“I’ll be going,” I told my wife as I kissed her on the cheek, “I love you. Have a good day. I’ll see you for lunch?”

“I love you too,” Jennifer said and then shrugged her shoulders, “and perhaps.”

I gave her a questioning look, she always came by in the afternoon for lunch together, and it was also the time she changed me.  Was she expecting me to stay in the same diaper all day? I held myself back from blushing; I just had to be careful with what I ate and drank in case.

 

“Good morning, Mr. Miller.” My assistant Tina said as I entered the office. I gave her a questioning look.

“What are you doing here so early?” I asked her. I was usually the first one at the office in the morning as most of my employees didn’t start their day till 7 AM.

“I thought you might need some help with the notes for the meeting this morning,” Tina said, “I know how much you have on your plate.”

“Thanks,” I told her, “I will send you what I have so far if you could make some postcards and graphs that would be great. I have a lot I need to get done this morning.”

“Okay, will do,” Tina said with a smile as she walked past me and sat down at her desk. She was a beautiful young girl and a hard worker. I knew she would go far.

I entered my office and shut the door, taking a deep breath. I walked over to my desk and turned on my computer. Ready to start the day.

For the next few hours, Tina and I worked on getting the details of the meeting just right. It was at 9 AM, and it was a pretty big project we were all working on and trying to get some investors to join us. When we were all completed with it, I told Tina I wanted her to come with me, since she helped so much.

The meeting went without a hitch, and the rest of the morning sailed on.

“Thanks for letting me come to the meeting,” Tina said, “I learned a lot of things.”

“You’re a hard worker,” I told her as we walked out of the building, “you deserve it.”

 

“Thanks,” she said with a blush, “not sure how you do it! You control the room. I wish I could do that. Your wife is like that too. You’re both so…powerful.”

“I don’t know about that,” I said with a small laugh.

“Take an early lunch if you wish,” I told her, “I have some things I need to do before my wife gets here.”

“Thank you, Mr. Miller,” Tina said as she walked over to her desk.

I entered my office and sat on my computer; it was about ten minutes before my wife usually dropped by to change me, and then we would grab some lunch. I pressed my fingers against my crotch; I wasn’t that wet, thankfully. If worst comes to worst, I could change myself, but I wasn’t sure how much trouble I would get into. It was a rare occasion that my wife would allow myself to change me.

A few minutes later, there was a knock on the door. Which, I thought was strange as my wife was never one to knock.

“Come in,” I said.

The door soon opened, and it was not my wife that walked through that door.

It was my best friend, her lover, Patrick.

 

 

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Chapter Four

“P-Patrick?” I asked I tried to keep my voice calm and collected; part of me was hoping he had some business to attend too. But, I often didn’t see him unless it had something to do with my wife.

“Good afternoon, Ross. Having a good day so far?” Patrick asked as he shut the door behind him, and locked it, which were the answers that I was searching for.

“So far so good, been a pretty hectic morning though. How about you? No work today?” I asked him.

“I do, just stopping by for lunch, your wife sent me.”

“Did she now?”

He nodded his head, and I shifted my weight, knowing that currently in my wet diaper, was also his cum from this morning. My cheeks burned slightly as I moved through some papers.

Patrick stuffed his hands into his pocket as he walked up closer to me. “Ross…”

“Y-yes?”

“I’m sure you know why I’m here.”

“Maybe…” I said, pretending as if there could be another reason my wife would send Patrick and not show up herself.

“Your wife is busy at a meeting and asked me to come down here to take care of some business. She says that by this time, you often need a good change.”

“I’m doing just fine, thank you,” I told him.

“But, what will she said if I told her you refused?” He asked, and I blushed, knowing I would be punished if I didn’t obey my mommy.

“O-okay,” I mumbled as I got out of my chair, my stomach was rumbling a little bit.

“Oh, I almost forgot,” Patrick said, “she also said that this is the time you would often mess, so if you need to do that, do it now.”

“I don’t need to do that!” I said in defense, holding up my hands, even though I could feel myself cramping up.

“Okay,” Patrick said with a shrug of his shoulders, “however if you are lying…and you have an accident in the middle of the day….it might become obvious to your staff that their so-called boss …isn’t as bad and mighty as he seems.”

I hated this; my cheeks were burning so red right now because he was right. It was so humiliating. I could feel my dick twitch as my cramping continued.

“Fine,” I replied as I looked away, not wanting to stare at him as I messed my diaper.

“Wait,” He said as he walked over to me. He reached out and began to undo my belt and then my pants, letting them slid down at my ankles.

“Hey!” I said, my cheeks burning as I stood there in my wet diaper.

“Do it in front of me.” He said as he crossed his arms. “Make a mess in that cummy diaper of you, like the little boy you are.”

“Patrick…” I mumbled under

my breath. Usually, it was my wife that was forward with the teasing and humiliation. Most of the time, Patrick didn’t say much to me, he mostly focused on whatever my wife wanted him to do,  but the few times he had said or made me do things, it was just as much as a turn on as when my wife did it.

I closed my eyes as I felt the mess slowly slide into my diaper, filling it up.

“I’m done,” I replied, unable to look at him in the eyes.

He forced me to turn around, before sticking his fingers at the back of my diaper and pulling it out, before looking in.

“Good job, you little cuck.” He said with a laugh. “Now lay, and I will get the changing supplies.”

I nodded my head and did as I was told, lying on the carpet, feeling the mess began to spread over my butt cheeks and onto my balls.

Patrick returned a minute later with another diaper, wipes, and some baby powder. He kneeled in front of me and took off my shoes and my pants.

“Let’s get you changed,” He told me as he began to peel back the tapes. This wasn’t the first time that he changed my diaper, there had been a few occasions before, but this was the first time he had changed a messy one. I wonder what he thought of it? When Jennifer had asked him to do this, was he willing? Or did he do it because he was her lover?

He pulled down the diaper to reveal the massive mess that I had created. He waved his hand in front of his nose.

“What a disgusting mess,” he said with a shake of his head, as he grabbed for some wipes and began to clean me up. I felt my whole body turn red, for even my small cock was standing up straight.

“This turning you on?” He said with a hearty laugh. “You sure you’re not gay?”

“No!” I said with a shake of my head. “It’s not like that; it’s just…” but I was unable to put it in words. It wasn’t as if I was attracted to guys, but Patrick was different. For the most part, we didn’t touch each other, but there were times that things did happen.

Patrick let out a laugh as he slowly undid his pants and then pulled out his massive cock, which was also hard. “Same here,” he said.

I blushed, turning my head away, not saying a word.  He put his dick back into his pants as he continued to change me, putting me in a fresh diaper.

“You did a good job today,” he told me, “I’ll make sure that you get a good surprise tonight.”

“Yes?” I asked of him, but he just nodded his head. I was a bit suspicious, though, if this meant actually release of pleasure, or if it would be more torture. Either way, my dick grew hard once again from the thought.

He wrapped the diaper in a scented plastic bag that held the sent in, and in a regular plastic bag, before shoving it in a unique backpack that my wife used to transport my used diapers to the nearest dumpster away from the company.

“Hope the rest of your day goes well,” Patrick said as he started to leave the room, I hurried up to pull up my pants and put on my shoes before he opened the door.

“Thanks…” I said sheepishly. “You too.”

He let out a laugh and walked out the door, and all I could think about for the rest of the time at work was that intimate diaper change and what could be waiting for me when I got home.

 

 

 

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All I can see waiting for him when he gets home is more humiliation.  I hope I am wrong, but from what I've read so far, I doubt it. 

Please keep the story going . I would like to see where all of this goes. 

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Awesome so far!

With a title like you know it already has a good set up. Nothings more fun then businessman who thinks they are powerful learning their true place. 

 

One thing though.

"My cheeks started to burn as she walked over to me, starting to unbutton my pants, and slowly pulling them down.

“But, she doesn’t have a clue. No one in your office does. What would they think if they knew their big strong handsome alpha, was just a weak little boy?” With that she yanked down his pants revealing a thick white diaper underneath,

Jennifer placed her hand over my diaper and pressed harder and I could tell that she felt the warmth beneath her fingers. “A wet one that is.” She added.

She let out a laugh as she started to walk away from me, before turning over, “Oh, I forgot to mention, Patrick is on his way over.”

“W-why?” I asked, though it was a stupid question.

“He is my boyfriend after all.” Jennifer gave him a wink before walking away, leaving him standing at the door way, pants pulled down, exposed in my soaking wet diaper."

I was a bit confused here. You might be mixing up points of view, it sounds like you switch between 'me' and 'him' for the same character.

 

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Chapter Five

The rest of the day, it was hard for me to concentrate. Whenever someone came into my office afterward, I was short with them and had then left as soon as possible. I’m sure rumors were going on that I was royally pissed off, and someone was about to get fired. But that was the farthest from the truth.

Every time I closed my eyes, I saw Patrick standing over me, that look upon his face as he wiped my bottom clean. My cheeks start to burn, and my dick starts to twitch.

He said he would be telling my mommy about what happened, but would the results be good or more torture? I bit my lip. I could hardly handle the anticipation any longer.

The day dragged on, but eventually, it hit 6:00 PM.

“Are you ready to go home?”

I lifted my head to see my wife as well as my assistant lingering by the door.

“Yes, Miss. Lovell, is there something you need?”

“Oh, yes, sorry.” She replied quickly, walking over to my desk and setting some papers down, “just handing in the paperwork you asked me to look through.”

“Thank you,” I said as I grabbed the papers and placed them in their rightful spot.

“Have a good night, sir, and you too, ma’am.” She said as she motioned herself towards my wife before quickly walking out the door. Jennifer shut the door behind her.

“She’s really cute,” she said with a smirk before turning back to me, “had a fun day?”

“You could say that…” I mumbled under my breath as I gathered my things. I could hardly look at her in the face.

“I can’t wait to hear all about it.” She said as she rocked on her heels.

“I thought he told you…”

“Doesn’t mean I don’t want you to tell me.” She retorted back.

I blushed, turning my face from her as I finished getting my stuff ready.

“Ready?” She asked, and I nodded my head as the two of us walked out of my office.

“We are going out to dinner tonight,” My wife said as soon as we got into the car.

“What? I thought that was this weekend.” I said, remembering the dinner party she mentioned yesterday.

“No,” she said with a shake of her head, “that is for Janice and Tony’s anniversary. We are meeting up Sarah and Gregory.”

“Oh,” I said with a sigh, they were longtime friends of ours. Gregory was one of my and Patrick’s good friends in college, and Sarah was one of my wife’s good friends. We all knew each other before we got married, “that’s okay with me.”

My wife intertwined her fingers with mine and leaned over to kiss me on the cheek. We remained silent for the rest of the trip home.

 

“Let me check your diaper,” my wife said as soon as we entered our home, having hardly shut the door behind her.

I blushed as I nodded my head, biting my tongue as she reached over, pulled my belt off, and then pulled at my pants, peeking inside.

“Oh, you’re not too wet,” she mused to herself, “I believe we will keep you in these while at dinner.”

“But…” I said with a blush but bit my tongue when she gave me a look.

“Hush,” She said before pointing to the couch, “but before we go, there is something I need to take care of first.”

“What is that?”

“Just do as I say, I’ll be right back.”

She left to retreat into the bedroom, and I obeyed and sat on the couch, trying to figure out what was going to happen.

She returned a moment later with something in her hand.

“Here we go, I think this should make you be on your best behavior tonight.” She replied with a grin as she held up a black butt plug.

I shrunk on the couch as I turned my head away from her.

“Lay down,” she commanded, and I did as she told me to do. She slipped down my pants and opened up the diaper, making sure not to rip the tabs.

“Lift your legs, little boy,” she said and as I did as I said. She then placed the tip of the butt plug right against my ass, before sliding it in. I closed my eyes tightly as it slid right in with no trouble. She taped up my diaper and patted it. I shifted my weight, the feeling of the butt plug inside of me.

“You ready to go now?” She asked me. “I need to freshen up real quick.”

I nodded my head as I sat up, but did not speak. My wife soon left the room once more as I sat on the couch and waited, in my wet diaper, with the butt plug.

“Alright, let’s go.”

She came back wearing a tight black dress that showed her cleavage and all assets. I bit my lip but nodded my head as I got up and wrapped my arm around her.

The restaurant was the sort of kind you either needed to know connections or had to put your name for the waitlist months in events. It had a modern take upon it, with an upstairs with a large aquarium.

“Jennifer! Ross!”

We turned towards the par where we saw her college friends Sarah and Gregory. Gregory was a skinny man, his hair was receding a bit, and he was wearing thick glasses. He was the smartest person in our group and ran a tech company.

His wife Sarah had short blonde hair, large breast, and a slim figure. From the outside looking in, one would probably think Sarah was only after Gregory’s money, but there was genuine love there. Sarah was a fashion designer who made a killing all on her own. She doted on her husband and their new child.

“How are you doing? How is little Jeremy doing?” Jennifer asked as she hugged her friend and kissed her on the cheek.

“Swimmingly,” Sarah said with a smile, “he is now six months old, he’s so adorable.”

“I’m sure he is!”

“Your table is ready for you,” one of the waiters said, and they soon followed him to a small table closest to the fish tank. The beautiful fish swimming about, I sat down by my wife, feeling the butt plug inch it’s the way a bit more into me.

I began to look over the menu as my wife and Sarah began to talk up a storm. Before long our waiter had come and took our drink orders, I order a bourbon.

The first part of the evening was not eventful. We talked about what was going on, college days, the dinner party they were supposed to attend that weakened. The drinks soon came, and everyone loosened up and had a good time.  At one point, right before our food arrived, I felt my diaper swell up a bit more as I wet it. I shifted my weight as my wife looked at me. She soon reached over and grabbed hold of my hand.

“Please excuse us; we need to go to the restroom, isn’t that right darling?” She asked as she looked at me; I lowered my head and nodded.

Sarah and Gregory smiled and waved us off. My wife helped me up, and we made our way to the bathrooms, thankfully there was a family restroom.

“It’s a good thing I decided to bring your backpack filled with supplies,” Jennifer said as she opened it up and began to pull out a clean diaper.

“You could have done that more discreetly,” I muttered to myself.

“Why?” Jennifer asked when soon there was a knock on the door.

“It’s me,” the voice called from the other side, it was Sarah.

“No, wait!” I tried to speak out, but my wife opened the door anyway.

“I was wondering if I could help,” Sarah said with a gleam in her eyes, “motherly instincts are kicking in, and I was informing Gregory before you guys came that my breasts were swollen and he just told me now that perhaps we both could benefit…”

Jennifer smiled brightly as she nodded her head, turning to look at me, but I turned and looked away, my cheeks were burning red as Sarah walked into the bathroom and Jennifer closing the door behind her.

 

 

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Chapter Six

“I don’t mind at all,” Jennifer said once the door was closed behind them, “Ross always did like the attention you gave him when you were around.”

“Well, we did date briefly,” she said with a laugh.

Besides Patrick, Gregory and Sarah were one of the few other people that knew about my situation. Sarah walked over to me and pinched my cheeks. “You always were a cutie.”

“T-thanks,” I said, unable to meet her gaze.

“We best hurry,” Jennifer stated, “our dinner is going to be here soon.”

“Oh, true!” Sarah said with a giggle as she began to take off her shirt, her bra was a bit wet from leaking. “My breast seriously hurt!”

I turned my gaze to her, as she snapped off her bra, letting it fall to the ground; her large breast and hard nipples were pointed in my direction.

There was a small bench on the opposite side of the wall, so Sarah walked over there and sat down, patting down on her lap. I gulp as I shifted my weight, walking over to her, and placing myself carefully across her lap.

I licked my lips as I gently wrapped my mouth around her nipples and began to suckle. It wasn’t long before her milk was entering my mouth. It was a little warm and sweet. Sarah’s hands began to move over to my diaper as she began to pat and rub on me. Even though I could not see her, I knew that my wife was standing over us and watching.

I knew my whole body was on fire as I suckled on my wife’s friend, and also someone I did once date. We were young though, it was only for a few months, but it didn’t help make the situation all less embarrassing!

“That’s a good boy, drink up,” Sarah said in a soft voice as I continued to feed on her.

A few minutes later, I switched breast, filling up on her breast milk, letting it fill my stomach. My dick was rock hard as she continued to pat and rub it, teasing me with her soft words.

“That is so much better!” Sarah said with a smile once I was finished, and I was standing up. “Thank you so much.”

“You’re welcome…” I said sheepishly.

“Sarah, did you want to change him?” My mommy asked her. “I’m sure he is probably dripping wet…and hard right now.”

“Oh?” Sarah said with a smirk. “Sure, I’ll change the little boy!”

 Jennifer reached into the bag and pulled out a thin blanket and laid it across the floor. Without being told, I laid down upon it, as Sarah knelt in front of me.

“It’s been a while since I’ve been able to change you; we’ve been so busy with the baby!” Sarah said. “Honestly, it helped me a lot. A baby diaper is so much easier!”

She reached down and began to undo my pants, pulling them down to reveal my wet diaper. She then started to untapped it and pulled it off, now only revealing my penis that was hard, but also the butt plug.

“Oh my! Someone is a bit naughty.” Sarah said with a giggle as she poked a finger at it.

She grabbed some wipes and began to clean me up.  “What a little boy we have here!”

“Yes, he has been a good boy so far today, what I’ve been told,” Jennifer said. “But, I can’t help but tease him, it’s too much fun.”

“I can’t blame you,” Sarah said, “he is really cute…and blushes way too easily! Look how red he is now!”

I turned my face away, closing my eyes, wishing I could shrink down. The teasing voices, the fact that Sarah was half-naked and wiping my bottom as my wife stood over us, it was almost too much. I felt like any moment I was going to just cum right then and there; I was so turned on.

“There we go! I think we are all nice and clean!” Sarah said as she began to grab the clean diaper and sliding it underneath me.

“Thanks for your help, Sarah.”

“No problem! This was a lot of fun!” She said with a giggle as she taped up the diaper, leaning down to kiss my diapered crotch, which caused me to wiggle. She then helped me put my pants on before finishing getting dressed.

“My breast feels twice as light!” She said with a sigh as the three of them left the restroom and made their way back to the table.

“Have fun?” Gregory asked as he eyed the three of us as we returned and sat down.

“Oh, it was great,” Sarah said with a laugh as she kissed her husband on the cheek. I was unable to look at him and focused on my food that had just arrived.

For the rest of the dinner, the conversation carried on generally as it did before, lasting for about an hour longer before it was time to leave.

“Thanks for joining us,” Sarah said with a smile, turning to look at me, “it was fun.”

“Yeah, we will see you this weekend then?”

“Of course.”

Jennifer grabbed hold of my hand as our driver pulled up, getting into the car and remaining silent the whole drive home.

“That was a nice dinner,” Jennifer said as they entered their apartment.

“Yes, it was.”

“So, did you have a good day today?”

“Ye-yes.”

“Don’t think you got out of anything,” Jennifer said with a stretch, “you’ve been very good today, so I’ve decided to reward you.”

My ears perked up with that word; did that mean I would finally get some satisfaction?

“But first,” Jennifer said as she plopped herself on the couch, crossing her legs, “I want you to explain to me what happened today.”

“What do you mean?” I asked, although I already knew the answer.

“Don’t start misbehaving now. You know what I mean. I want you to explain to me what happened today at lunch.”

“I had my diaper changed,” I said, trying to sound matter of factly, but it was challenging to do.

“And?”

“By Patrick,” I went on, turning my head away, “I also messed my diaper as well…”

“Did it excite you?”

I gulped and nodded my head, but her eyes were staring me down, and I knew that it wouldn’t be enough.

“Yes, mommy.”

“Now you see why I enjoy that big cock of his. It looks like you would enjoy it too.”

I didn’t say anything when she patted the couch next to me. I obeyed and sat down next to her. She slipped her hands inside my diaper, which was slightly damp, wrapping her fingers around my dick.

“You’ve been such a good boy; I’m going to give you a happy ending in your diaper.” She whispered as she began to play and massage with my penis. I bit my lower lip as I wiggled about, it had been a few weeks since she made physical contact with me like this. The buildup was worth it, though, because it felt fantastic.

“Such a dirty little boy, getting excited when he was nursing with Sarah.” She whispered as she continued to jerk him off. “probably wanted her to lean down and suckle on your penis after you suckled on her nipples.”

I let out a moan and panted, I wanted to hold on as long as I could, but I could feel the pressure building up.

“Just finish up in your diaper, like the little baby boy you are,” my mommy coaxed me, playing with me, whispering, kissing my lips, pressing her body up against mine, until I was no longer able to hold it back, and I released it all in my diaper.

“Good boy,” Jennifer said with a smile as she kissed me.

“Thank you,” I told her.

“Now, tomorrow night, Patrick is spending the night,” She said with a giggle, “and I think we are going to have a LOT of fun.”

With that, she got off the couch and walked away, leaving me there wondering what those words could mean.

I knew one thing for sure, though; it was going to be embarrassing.

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Here is the next chapter! The next chapter is also available on my Patreon pagehttps://www.patreon.com/mamabug  (with other cool stories and some drawings a well!) I'm going to revamping my tiers and try to add even more great content for you guys! Anyway enjoy! 

 

Chapter Seven

“Are you ready for bed?” Jennifer asked me as she walked out of the bathroom, wearing a simple t-shirt and shorts.

I nodded my head, already tucked into bed.

She smiled at me as she crawled next to me, wrapping her arms around me and pressing her face against my back. “I love you, babe.”

“I love you too, mommy,” I said with a blush as I turn over and kiss her on the lips.

“Hey now,” she said with a giggle as she kissed me back, “now go to sleep, it’s late, and my little guy has a big day tomorrow.”

“Yes, ma’am,” I said sheepishly as I turned back over and close my eyes, soon drifting off to sleep.


 

My alarm started blaring at 5:30 AM the next morning; I moaned as I turned it off, noticing my wife was still fast asleep. I let out a stretch as I walked into the bathroom. Usually, I wasn’t allowed to change myself; however, I was allowed to take my diaper off and jump in the shower.

By the time I got out, my wife was already awake and waiting for me with a thick diaper in her hand.

“I can’t even remember a time when you didn’t wear these,” She said as she turned to look at me.

“It’s been a while,” I said, thinking it had been at least a year since I’ve been wearing full time.

“I remember when you first told me,” Jennifer said, “you were freaking out.”

“Well, it is a weird fetish.”

Jennifer shook her head, walked over to me, wrapped her arms around me tightly, and kissed me. “No, it’s perfect.”

I blushed at her words and nodded my head.

“Okay, let’s get you dressed!” Jennifer said with a clap of her hands as I laid down on the bed so she could diaper me.

“I have a special diaper for you today!” She said with a giggle, which I didn’t notice before, the diaper was very thick, but also had cute little blocks and bears on it. Most of the time, I wear plain white diapers, but once in a while, my mommy liked to put a cutesy one on me…to remind me of my place.

“Oh,” I said as I wiggled a little bit.

“Lift your legs,” she commanded, and I did as I was told, as she placed the diaper beneath me and taped me up, kissing the crotch of my diaper, making my dick twitch.

“Don’t worry,” Jennifer said with a chuckle, “I’ll be the one coming over at lunch to change you. I expect it to be quiet wet!”

I nodded my head, “yes, ma’am.”

When I was finished getting dressed, she kissed me on the cheek, “have a good day, hun.”

“You too,” I told her.

“I love you.”

“I love you, too,” I replied as I left.


 

“Mr. Miller!” Tina had called out as soon as I entered the office. I gave her a strange look, as she looked rather anxious.

“What is it, Ms. Lovell?”

“I’ve been trying to reach you,” she said, “they changed the meeting with Mr. Thompson and Mr. Raegan from 2:00 PM to lunchtime.”

“Lunch?” I said with a gulp, trying to keep my composure. “Did they tell you why?”

She shook her head. “No, they said they wanted to meet you downtown for lunch and will send you an email with the information.”

“Great, thanks, Ms. Lovell.”

“Y-you’re welcome.” She said with a nod of her head as she turned around and sat back down at her desk. I looked at her for a moment before I returned to my office and closed the door behind me.

During lunch?

Usually, I had all meetings unavailable around that time since that was when my wife would come to change me. I shifted my weight as I rushed to my desk and dialed my wife’s phone number from my work computer.

“Miss me already?” My wife said over the phone; her smooth voice sent me chills down my spine.

“Hey, listen, is there any way you can come down here before lunch?”

“Why? Sadly, I’m not able to get away until then. What is going on?”

“Got a business meeting, and they decided to change the meeting to some restaurant at lunch.”

“Oh,” I heard my wife pause over the phone, “I’m sorry, dear, I’m unable to come over until afterward.”

She said she was sorry, but I could hear the joy in her voice as she spoke. I knew she had ideas and thoughts spinning around her head.

“Perhaps you should just try your best not to have too many accidents?”

“Come on now…”

“You’ll be fine.” She told me. “It’ll only be a few hours longer. I’m sure you won’t leak….”

“Jennifer…”

“Watch your tongue,” she told him, “anyway, I have to go. Have a good lunch. Love you!”

She hung up the phone, with a laugh, before I could say another word.

I put the phone back on the receiver and sunk into my chair. What was I going to do? It was a rare occasion that my wife was unable to come to my office for lunch to change me. Even more unusual were times she allowed to change me. I didn’t also ask her about that, because I knew the punishment would be great if I did.

“It’s fine, just don’t drink a lot, and you’ll be fine,” I told myself as I started to immerse into my world, trying to put the thought of lunch behind.

But soon, before I knew it, it was almost lunchtime. Thankfully, I did not drink that much, and my diaper was only slightly wet. I could feel it press against me as I walked, but it still wasn’t noticeable to the average eye.

“Ms. Lovell,” I called when I came out of the office.

“Yes, sir?” She asked as she looked up. I would need some kind of excuse, some sort of way to get out of the situation if I needed it.

“Shall you join me?”

“W-what?”

“Did you wish to join me for lunch?” I asked again as I threw on my jacket.

“Are you sure?” She asked, but before I could respond, she grabbed her jacket and purse, “yes, that sounds lovely. Thank you so much!”

I smiled at her as the two of us left; I had already called for a car to be waiting for us to take us to the restaurant.

The restaurant was only about ten blocks away, and Gary Thompson and Leonard Reagan were already there at a table with a few other associates. The restaurant was one of those middle type restaurants that the rich could easily afford, but the middle-class had to only treat them once in a while. Especially when you’re ordering a steak that cost easily $50

I told Tina to order whatever your heart desires, and she could even have a glass of wine if she wanted. They talked about an hour, drank, and overall had a good time. Also though it was an official meeting, I got along with these two for as long as I can remember, we were old friends back in the day before we climbed the corporate ladder.

Although by the time lunch was finished, I knew that my diaper was pretty much soaked. I had to be careful with every step that I took, not wanting to let myself leak. I texted my wife to please be at work as soon as possible.

“Thanks for inviting me to lunch,” Tina said as they rode in the car back to the office. “I enjoyed myself.”

“Even though it was a bunch of nonsense from a bunch of CEO guys?” I asked.

She nodded her head. “You’re pretty amazing, Mr. Miller.” Her cheeks blushed. “You’re so strong and powerful; I want to learn so much from you. So I appreciate you giving me opportunities like this.”

“You’re welcome,” is all I said, even though deep down I knew she would never see the real me.

Once I returned to the safety of my office, I felt better. If I had wet the diaper once more, it would have been too late. It’s not that I have lost control of my bladder, but since being in a diaper 24/7 for the past year, I often don’t think about it anymore and just wet…even though my diaper was almost beyond capacity at this point.

There was a knock at the door.

“Ross?”

It was Jennifer, she opened the door and closed it behind her.

“My, my. It looks like someone is about to wet his pants.” She said with a giggle as she walked over to me, kissing my red cheeks.

“Come on,” I said, “can you please change me before I ruin my pants?”

“That is no way to talk to your mommy,” she said with a giggle as she began to undo my pants, revealing the thick and super wet diaper that was underneath. I felt even smaller with the little bears and blocks on the diaper.

Out of nowhere, the door had opened. Jennifer had forgotten to lock it behind her.

“Mr. Miller, here are the papers you…”

Tina walked into the room, saw me with my pants halfway down my legs, diaper exposed with my wife. Her mouth flew open, and she dropped the papers all over the floor.

 

 

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I'm loving the story Mamabug. The characters are great along with the story line.

I hope mommy and Daddy decide to turn baby cuck into a sissy baby girl because this would be more humiliating don't you think?.Please include lots of descriptions of the baby clothing if he becomes a baby girl e.g pink satin frilly panties, plastic pants , fluffy diapers and short frilly pink baby-doll nighties and dresses with pink ribbons.

How tiny is baby's peepee  when aroused shouldn't be more than 3 inches hard and of course Daddy's thick penis is more like 7 or 8 inches I reckon? I'm sure we all want to know?

I guess Tina is newly graduated from college, 19 years old?

I hope Tina will be a baby sitter for her boss,will she laugh at his erect  tiny penis "baby dick"?

will she dress him up as a baby girl while mommy and his new Daddy are on a date night?

Perhaps Tina will sleep-over at the house and see just how big the Alpha male is compared to the sissy baby.I expect Tina will see or hear Mommy and her lover having sex while poor sissy baby girl dressed in pink frills is forced to watch from her crib.Maybe Tina will enter the master bedroom and hold poor baby whilst he kneels up secured by pink leather straps whilst his mommy is being pounded by the big rough man.I'm sure Tina will comfort the sobbing sissy baby by picking up his mommy's discarded white silky satin cummy panties and placing them over baby girls head and tying a penis shaped pacifier into his mouth which secures the  fragrant wet panties in place?

Will Daddy place his new baby daughter over his lap and spank her in front of Tina and Mommy for refusing to suck his thick 8 inches?

Just a few thoughts and ideas which you and all ABs may find exciting and especially those of us that really enjoy reading sissy baby cuck stories.

Please keep up the excellent work.I cant wait to see what happens next.

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