The new boss pvt sissytiff17

[Kaylaindiapers]

James leaned back in his chair he knew soon he would be VP.. Right now he was the supervisor of a whole branch and they’ve been making a lot of money though the sales… He smiled cause no one knew he had been embezzling money… He would take the money and spend on himself car and a nice condo then he’d take that money and gamble he was actually pretty good! Life was good..

James did have the napoleon complex… He was 5’5 short for a man and he tried growing a goatee but it looked like his face was dirty and his mustache looked like he had drank chocolate milk!  James remembered that bitch Sara who was his secretary and they even had an affair she laughed at him when they went to fuck.. Her laughter echoed in his ears.. When she said he had a baby dick and he fired her on the spot…

Now he fantasized about his new Secretary Tiffany she was fresh out of college Least that’s what he thought he wasn’t sure she had only been there for a few months… James was determined to get in her pants and he swore she was flirting with him… The hot shot supervisor couldn’t get Sara’s laughter out of his head so he needed to weld his power to feel like a big man and restore his alpha male status. 

“Tiffany bring me an ice coffee!” James smiled as he knew that young hot girl would be scurrying around to get his drink.. 

James was the boss and it felt good! 
 

[Sissytiff17]

I tried to to hide my disgust as I looked at James. The jerk had left his office door open and I had a full view of him. He is so smug and arrogant but that is going to end soon. James had been embezzling money from the company and I had caught him. He considers me a dumb secretary but he forgets that I have a master’s degree. This is why he did not even bother to hide the evidence from me.

James definitely had a napoleon complex. He was a short man with an un athletic body. In reality, he looked like a ten yr old girl. Hell, his voice even sounded like one. I could not help but laugh as I thought about the time he tried to grow facial hair. He looked like a little girl playing with her mom’s make up. I was the total opposite of him. I tried my best to be humble. I was very athletic. I was a college track and field star. I even did some modeling on the side. I know James thinks I want him. I started to day dream more about how I was going to get my revenge. I soon will be running this company. 
 

My dreams were interrupted by his yelling. He wanted me to get him coffee. “ yes sir but please address me as Miss Tiffany.” I could see the shocked looked on his face, as I told him to call me Miss. I walked in without his coffee and threw a file on his desk.

[Kaylaindiapers]

James was taken back Ms Tiffany he thought to himself.. “What the hell is she talking about?” He said confused as he hung up the phone..

He was thirsty this morning and looking forward to his ice coffee to get him going today wake him up so he can mess around today and boss some people around later… He was hung over from last night..

”Hey what’s your problem you know I fired the last secretary you’re hot and all but you better remember I’m the boss now get me my coffee and don’t ever throw anything at me again understand!” He talked down to her making sure she knew his place..

James was looking forward to watching her walk away so he could checkout her sexy ass he wondered what color her thong was he fantasized about it..

What did she say! He thought to himself being snapped out of his little fantasy.. 

[Sissytiff17]

I could see how pissed I made him. I laughed as he hung up the phone in total disgust. That little outburst demonstrated to me that I am the one in control. I had him where I wanted him. 
 

“Oh your definitely not going to fire me. I am happy you think I am hot but I don’t go for small non athletic men. I like strong athletic men.  You can talk down to me all you want. However, I am smarter than you think. I will go get your coffee but you need to take a look at that file. “
 

I turned and walked out of his office. He was at a loss for words. I made sure to walk out slow and sexy. Might as well give him a view of what he will never get.

[Kaylaindiapers]

James is we taken back by her confidence as she had a big smile on her face as he looked at her blue green eyes and he got lost in them for a second even as she said things to him that she would never say to him.:

”Look I don’t know who you think you are but you’ll show me respect do you hear me!” He yelled as she walked away..

He scratched his head and looked over the files and began to panic..

James now knew she did have the upper hand… He was scared as he knew he’d never last in prison.,

”Oh know I wonder what she wants.”’he said to himself..

He sat there and waited until she came back..

”No no this can’t be happening but how did she get that how does she know!” 

For the first time in a long time he was at a lost for words.. 
 

[Sissytiff17]

Damm, I can’t believe this jerk still thinks he has the power. I turn and walk back out of the office. I go to my desk and put a new pair of heels on. With these I will be much taller then him. I walk back into his office and catch him looking up at me. He is staring into my eyes. I can tell his confidence is gone. 
 

“ your not the one in control anymore. I am. If fact it is time you learned your place. I am the boss from now on. There will be some major changes but we will start slow. For starters you will call me Ms. Next your going to put my thong on. I saw you admiring it on me. Seems you should get to enjoy it. Lastly I am moving into your house. There will be more but we can start there”

I laughed as a threw my pink thong at him.

[Kaylaindiapers]

James jaw dropped he truly didn’t know what to say! 

Everything came at him so fast he tried to take it all in..

”Ulm what the hell are you talking about have you lost your mind thinking you’re the boss’s moving in with me and wearing a thong I’m a man little girl!” He said trying to intimidate her maybe there was away to talk her out of this and make her think she really didn’t know what she was seeing..

He looked over the papers again he knew what she found but did she really he was about to find out cause he was going to make it seem like it was nothing..

”These are a couple banking errors I just have to call them and let them know now I’ll let you keep your job cause you’re so cute when you play around like that so Miss Tiffany be a good little girl Tiffany and get my coffee.. He said like a smart ass 

James was playing a game of high stakes poker and he had to make her believe he had a full house instead of a shit hand of nothing. 
 

[Sissytiff17]

I knew I had him where I wanted him. The shock in his eyes. He looked like a little kid who had just been caught by their mother. It would not shock me if he was holding back tears. I loved the new found power I had. I know his type, trying to act tough to hide the fact he is just a big sissy. Him trying to fight does not bother me, I expected it. In fact, it will only make it better once I break him.

” now now. You must think I am stupid. However, I am not. I already had my friend look the numbers over. She is an accountant.  I am the one in control and you know it. So here is the deal. I will give you 20 minutes to make a decision. You can chose to go by my terms or I can call the cops. It is your choice. I mean if you don’t like the thong, I can come up with something different. Though, you will wear what I say. If you pick my terms you will come out to my desk with a drink for me.”

I turned and walked out of his office. I made sure he got a good view of my butt. 

[Kaylaindiapers]

James felt like a little boy the way she talked to him and scolded him and then threatened all at the same time. 

What am I going to do now! He thinks as he buries his head in his hands. He looked at the clock and it kept ticking and ticking it seemed to get louder and louder..

He thought about all his actions and the scenarios that she gave him..

”Gave me!”! He yelled his was really pissed now looking at the clock he had ten minutes..

He got mad and threw the file across the room and he crushed his model car that was sitting on his desk… Tears began to form in his eyes..

Why why why!  He yelled in his head..

After five minutes or so he did the best he could to wipe the tears from his eyes he got up and he knew the only thing he could do was go to his refrigerator and pull out the only thing he had was a dr pepper and he would give her the answer it was her terms he was choosing cause he had no choice! 

I’ll beg her not to make me wear a thong or she said she might have something else… Maybe I’ll beg her for that!  He thinks to himself as he approaches her desk! 

“Here miss Tiffany.” 


 

[Sissytiff17]

I am so excited I know my plan is working. I look down at my phone and notice the items I ordered have shipped. These will be perfect for the next part of my plan. I cannot wait to take him down a few pegs. All this excitement is getting me very excited as well. I will need to take care of that later tonight. Hmm five minutes have gone by I wonder what he is going to do? Not that he has much of a choice. Suddenly I see him bringing me a soda. 
 

“well you have made the right choice. Thank you for the soda. Now since you don’t want to wear the thong I have another option for you. I want you to open my desk and look inside. that is what you will be wearing. There will be no arguments. Go ahead and open it.”

He opened my desk and was in a state of shock. His face was as red as my lipstick. I felt an intense amount of power right now.

” so do you like your new underwear?”

[Kaylaindiapers]

James couldn’t believe how his life is out of control! He stood there handing his former secretary a pop he had in his refrigerator. He turns red with embarrassment and anger as Tiffany lauds her new found power over him.  He wanted so bad to bend her over her desk and spank her and humiliate her anyway he can he wanted revenge. 

“Sure you’re welcome for the pop.” 

“I-I don’t understand why do I have to wear anything?” He asked nervously. 

He wondered just how long she’s been planning this how long has she known about the files but just didn’t say anything. 

James did as he was told opening the drawer. 

He did a double take as there was something white with little bears on it. He didn’t see how big it was or he never would’ve asked the question. 

“Hmm I didn’t know you had a kid and there’s nothing in here!” He looked at her confused. 

All he saw was a diaper and he had no idea that soon that would be his diaper! 






 

[Sissytiff17]

I tried my best not to laugh. I had him where I wanted him. We had completely flipped roles in this short matter of time. The look on his face when he saw the diaper was priceless. The best part was the diaper was obviously for a girl. It was white with bears but the bears where wearing dresses or dressed as princesses. I am not sure if he was confused or just hoping when he asked if I had a kid. I looked around before I spoke. I made sure no one was close by. I did not want to out him right away. However, I will speak loud enough that he will worry someone will hear. 
 

“ Me having a kid? No I don’t have one yet.  The diaper is for you silly. You did not want to wear thong. So, you can now wear the diaper. You have to wear something because I said so. Now take the diaper and walk back into your office. Take your pants off and wait for me to come in. I expect to see laying on the floor when I enter. You have 5 minutes. If you disobey, I can make things a lot worse. “

I then turned away from him and went back to shopping online.

 

[Kaylaindiapers]

James was embarrassed and infuriated this was so unfair!!  Why would she do this to me! He thought as she teased him he felt like she was talking to a toddler who didn’t understand things..

”B- but you can’t be serious!” He whined looking again at the diaper now realizing it’s a diaper for girls..

He Frowned he was so mad and now he worried that she was giving him a time limit..

James had no idea what to do! 

He grabbed the diaper..

”Fine!” He said pouting stomping his feet as he walked away..

Holding the diaper in his hand he couldn’t believe she was going to make him wear it..

James did the only thing he could he sat it down and waited for his former secretary to come in..

Hurry hurry! He thought to himself laying there waiting for her..

In James life as a President of the company he wasn’t used to people telling him what to do but he didn’t see away out.. 

Many might have thought he was immature but no one ever had the nerve to say anything about it until now.. 
 

[Sissytiff17]

I tried hard not to laugh as I saw him grab the diaper. His face was so red. He really looked like a toddler as he walked away. I could go right in or I could make him wait. I decided to make him wait. After about ten minutes, I opened his door a little and definitely chuckled a bit. This proud man was laying naked on the floor in the diaper position. God he is small. I bet he is only a couple inches. I bent over and started to unfold the diaper.

”oh wow you are a small boy. You definitely belong in diapers. Now lift your bum.”

I took my time and slid the diaper under him. I then powered him up and even used some diaper rash cream. I then taped the diaper shut. I then took out a pair of plastic pants. They were pink with bows on them. I slide them up his legs. Lastly, I clicked the lock on them. While doing this I admired the office and got a new idea.

” ok all diapered. Now I like your office. I think I am going to work in here and you can work at my desk. You can play secretary. If anyone asks just tell them you are trying out my job to learn more about what I go through”

 

[Kaylaindiapers]

“This isn’t funny I’m not small I’ve average and this diaper thing is stupid!” He cried..

He liked the view he had as he never thought about that as he was begging and pleading… He saw she had a white bra on..

“Why why a diaper I’m not a baby!” He began crying like the baby he really is but has been hiding it for so many years..

He remembered being the smallest how the girls would pick on him and make him a baby or a little girl how they bullied him..

James had got away from all that when he became a big shot executive and now here he was back in diapers..

”Pl- please I’ll quit and give you some money please anything but this!” He cried with tears coming out of his eyes.. 

He looked down at the sissy locking pants knowing he can’t even take the diaper off now! 

[Sissytiff17]

I could not help it I finally started to laugh like crazy when I saw his butt it puffed out like crazy and the bows were so cute. I took out my phone and snapped a few pictures of him. I rubbed his butt and slide my finger to make sure the diaper was secure. I decided to tease him and rub the front of his diaper and then quickly pulled away. I went in sat in his chair.

”you won’t quit. You need the money to pay for all our stuff. Remember I am moving in. Quitting would also be too easy. You need to realize I make all decisions from now on.”

I took off my shoes and stockings I threw the stockings at him. I then put my feet up on his desk.

“Now I want you to crawl to me and thank me by kissing my feet. You will then say I submit to you and will do whatever you like. You will lastly say you dream of being treated like a baby girl. After you say that you will put your pants on and go work at my desk. After 10 min of working you will announce to the staff that me and you are switching roles for the time being.”

[Kaylaindiapers]

James knew his life was over cause just a phone call and she could make his life even worse.. He stood there as she took pictures and checked his diaper he was about to say something but she began rubbing his diaper… He was so turned on as she touched him but he didn’t wanna get excited wearing a diaper..

Maybe I could be her man after all! He thought as he was letting things get carried away then she stopped..

”Wh- what what are you doing?” He stuttered trying to regain his thoughts from almost enjoying himself to quickly stopping like she did..

James not seeing any other choice dutifully did as he was told..

He kissed her perfect painted toes.

”I submit to you and will do whatever you like I - I dream of being treated like a b -baby girl b- but I don’t wanna be a baby or a baby girl and no one’s going to believe we’re switching positions!” He cried trying to see if he can talk some sense into her.. 

[Sissytiff17]

Now he went and annoyed me he was questioning me. I need to show him who the boss was. It was time he was punished.

”now, I will not accept back talk. You will be punished and will be spanked.”. 
 
Before he could react I stood up and grabbed him. I pulled him over my lap. I then unlocked his pants and pulled his diaper down. He could try and fight but I am so much stronger and more athletic than him. He was no match. I started to spank and did not stop until his butt was super red. I pulled up his diaper and locked his pants back up.

“ now you will kiss my feet again and apologize. You will also thank me for the spanking. After that you will walk out of the office and make your announcement. You will then get to work. I have some contracts I need to work on”

[Kaylaindiapers]

“Hey n- no pl- please!” Was all James could say as he was pulled over her lap all he could do was kick and yell… He quickly found out that his secretary was stronger than him!  He cursed his size or lack there of as he couldn’t get away! James felt like a naughty little boy as he was spanked and scolded… After the first few smacks he was hoping he had his diaper on! 

James was relieved that the spanking was over as all he could do was cry and try to bring himself together..

All he could think about doing was dutifully doing as she said..

James kissed her feet..

”I- I’m s- sorry!” He stuttered between sobs..

”Thank you for the spanking..

James tried to think of away to do this..

”Please I’ll do as you say b- but can we wait till tomorrow so I can make it more believable I’ll have a meeting and announce to everyone pl- please I’ll be good.” He said stuttering nervously as he didn’t wanna cross her again! 

James stood there in his diaper as his ass was on fire he realized that the roles had changed.. 

 

[Sissytiff17]

This was even easier than I thought it would be. I wonder if he is truly a sissy at heart. He truly looks like a toddler throwing a tantrum. I love how his butt poofs out. I cannot resist and walk over and squeeze it. I also check his diaper to make sure it does not need to be changed. I obviously know it does not need to be changed yet but it reinforces his status. 
 

“ oh look you are still dry. Now you can try to argue all you want but you are not going to win. Do you want another spanking? If not I suggest you go and make your announcement to the staff. Make sure you add that you want to be treated exactly like any other secretary. Now you can go do that now or I will pull your pants down and make you stand in the corner. After that you will get a spanking and go make your announcement without pants. The choice is yours. You are dismissed”

I stand up and walk back to my new desk and sit down. I then motion for him to leave.

 

 

[Kaylaindiapers]

James blushes bright red as he can’t believe she checked his diaper like he was a real baby or toddler and couldn’t be trusted to say if his diaper was wet or not! 

“I’m not going to use that stupid thing!” Then it dawned on him he couldn’t get it off until she unlocked it and let him out..

”N- no please you can’t really expect me to use this damn thing what did I do to piss you off!” He said trying to talk some sense into her..

James stood there knowing she would do it too..

The nerve of her to dismiss me like that!  James was getting pissed but he dint see away out! 

“Fine I’ll do it!” He said defeated and mad..

He sent a memo out calling for a meeting.. 

 

 

[Sissytiff17]

“ yes I do expect you to use it. That is what diapers are for. Are you going to be good or are you going to keep complaining about using the diaper. Your life is going to be great. You won’t have to worry about any big girl problems anymore. As for what you did to me. Well you treated me terribly. Remember when you called me a dumb blond secretary at the bar. How about the time you grabbed my butt at the Christmas party. You obviously were not raised properly and I will take care of that. I am happy you are going to call the meeting.”

I watched him leave the office. You could see I cute little waddle as he walked. It was not obvious but if you were looking for it you would notice. After he lifted I finished up the new employment contracts and power of attorney paperwork. I then got changed out of my secretary clothes and into a black business suit. I put taller heels on too. I wanted to display power.  I then walked out to the conference room for our meeting. 

[Kaylaindiapers]

“Big girl problems I’m a man what are you talking about!” He said angrily there was only so much he could take but he was trying really hard not to make her mad!  He didn’t want another spanking!! 
James just stood there as she told him about his bad behavior..

”What do you mean raise properly and how are you going to take care of that?” James just figured the diaper was a one or two day thing to show him she’s in control now and not him!  He figured this would be a way to humiliate him and in a day or two it would be over! 

James had everyone in the office meet up in the conference room..

He looked as Tiffany walked in she looked like she was powerful and in command..

James felt stupid trying to act like he was in charge when he knew at any second someone could tell he had a diaper on then some of these hot young girls would fight over who would spank and change him..

”Well we’re all a family here so for the next month think of this as a team exercise.” 

He looked over the papers..

”For the next month me and Tiffany will be trading places I’ll be her assistant and she’ll be doing my job and that goes for you to Brian and Todd… They were the shift supervisors.. He figured might as well drag them down with him plus it would look more convincing.. 

 

[Sissytiff17]

“ you need to get it through your head. You are no longer a man. Those days are over. You are now my baby girl and will be raised again.  Those papers you signed gave me all the power. Not that I needed it. The 1st set of papers were employment contracts. I now officially have your job/salary and you have mine. The 2nd was a power of attorney paper that allows me to make all decisions over you. Don’t worry I think you will really enjoy this life. I plan on spoiling my daughter. If you behave someday I may let you out of diapers and allow you to wear panties.” 
 

He was dumbfounded but he had a meeting to start. The look on everyone’s face was priceless. I could tell most were excited though James was not well liked. They were all going to love seeing him being taken down a peg. However, Brian and Todd did not deserve this. They were great mangers and well liked. Plus I wanted all the attention on James.

” yes staff this is true. I think it will be a great exercise. Don’t be concerned I am more than capable. Remember I have an MBA. However, your old boss was wrong about Brian and Todd. It will be just him joining the secretaries. I want you to remember he is just a secretary. I expect you to treat him like the other girls. Are there any questions. We will both answer any?”

[Kaylaindiapers]

“B- baby girl you can’t be serious!” James was so mad but he knew not to cross her or make her mad as he now feared her and all she could do to him he hated the spanking it hurt and it was so embarrassing! 

He sat there and was seething mad as she undercut him in front of everyone! 

James desperately wanted to fight back but the diaper kept him seated and just biting his tongue..

Damn her I figured others could suffer with me then we could hang out and talk but no she decided it would be just me! 

Kim spoke up..

”So does that mean he can no longer tell us what to do?” Kim smiled looking at James who looked uncomfortable..

Sara had the next question 

“Does that mean he can’t just come and go as he pleases and he no longer gets his office or the executive bathroom? 

Debbie was the next one 

If james is the new secretary does that mean we get to haze him you know how we bring new secretaries in and we have them go through a new hire process..

She looked at James who looked like he was in deep thought..

No one knew James was peeing in his diaper..

He wanted to cry he wasn’t a baby he wanted to cry that he was a man and Tiffany was blackmailing him…

James was understanding that this was his new life and he was stuck..

As he sat there in his wet diaper he was just hoping no one noticed! 

He could just imagine Tiffany being really happy that he used his diaper just like a baby that she was turning him into..