The new boss pvt sissytiff17

[Sissytiff17]

The faces on everyone were priceless I could tell they were excited. I loved all there questions. In fact, some of them I did not even think of. Thankfully they asked them. 
 

“ Kim what a great question. He has no authority over you. He is no longer in control. He has the same amount of authority as any other secretary. He will answer to anyone above him. He is expected to use terms of respect such as sir, ma’am, ms, mrs, and Mr.

“Sara of course he cannot just come and go whenever he pleases. He needs to be at his desk. He will have normal hours just as any other secretary. He will not have access to the executive bathroom because he is no longer an executive. In fact I don’t think the bathroom will be much of an issue”

“Debbie of course. He should have to go through what any new secretary would. Now I hope this answers all your questions”.

Everyone looked at James and left. I looked at him and could tell something was off. He looked like a toddler who had just wet their diaper. I will check him but I will wait until he gets back to his desk.

“Now James get back to your desk and get to work. “

 

 

[Kaylaindiapers]

James wanted to say something so bad but he didn’t know to cry out of embarrassment and anger or over the fact he had a wet diaper! 

No no this can’t be happening all of you will pay someday… I hope she don’t find out I had a accident.. James mind was running wild.. He truly didn’t know what to do! 

James didn’t say a word and looked to see what kind of work there was to do.. He just hoped that Tiffany wouldn’t find out.. Maybe I can go to the bathroom no that won’t work she has the stupid pants locked up…

I’m stuck!  

 

[Sissytiff17]

I saw him sit back down at the desk and I walked back over to him. I stood my finger and out my hand down the back of his pants. I noticed that I was correct and he was wet. He did not need to be changed yet though. He needs to learn to be in a wet diaper for a little. 
 

“oh my it looks like someone is wet. Good thing you are wearing a diaper. It seems you cannot control yourself. Don’t worry your diapers will keep your pants dry.  I can’t wait for you to go through the secretary hazing. After that you will truly be one of them. Oh by the way I will be driving both of us home in your car. Well it will be kinda my car. You won’t be driving anytime soon. For the time being I expect you to book me a nail appointment. You then can order me lunch.”

The best part of this was watching the other secretaries staring at him.

 

[Kaylaindiapers]

James looked around and he turned bright red as she was too loud for his taste..

He smiled nervously knowing if he argued things could be worse and most importantly it would cause a scene..

”Very funny you’re always joking around and sure I’ll set up your nail appointment what would you like for lunch?”

James wanted to whine and cry like a baby who truly had a wet diaper but he couldn’t ask to have his diaper changed now! 

He did the best he could to try to ignore it. 
 

 

[Sissytiff17]

I loved how red his face was. I can tell he is super humiliated but I am going to tease him some more. I will answer his questions but tease him at the same time. I bent over his desk and leaned forward. Doing this made my breasts very obvious to him. I have caught him looking many times. 
 

“James don’t be silly we both know I am not joking. Now I can speak louder if you want. Now as for lunch, I would like a steak from your favorite steakhouse. You know the one you always have me get lunch from. Oh you should get yourself a salad for lunch. You need to watch your figure. “

I started to rub his leg and then grabbed his diaper. I noticed that he was very hard. I rubbed the front a little more just to further excite him. 
 

“oh look someone must really like his diaper. Your little guy is very excited. Now you listen to everyone else. Remember you are just a jr. Secretary so even all the other secretaries are your superiors.”

with that I turned and walked away. I made sure to make my walk super sexy. 

 

[Kaylaindiapers]

James couldn’t help but stare as she leaned over he could smell her perfume she was sexy as hell but he hated how she took his life over..

”No please don’t please.” He begged for her not to get even louder!  “Wh- Wh oh!” James squealed as she grabbed his manhood and began rubbing it he was so turned on and embarrassed..

James was so mad as she reminded him pretty much that he belongs to her..

Once she let go of him leaving him excited he was so pissed off how she reminded him she has all the power..

He looked at that sexy ass and felt turned on in the diaper that she put him in..

James was now feeling like he loved her and hated her…

That bitch is skull fucking me. He thought as he called the steakhouse to place Tiffany’s order.. 

 

[Sissytiff17]

“James now that you ordered my food please come in here. Once you come in I expect you to strip off everything but your diaper and lay on the ground. “

I unlocked his diaper and took it off. 
 

“wow you really needed a change, you definitely are not ready to be potty trained. It is ok little girls like you have their diapers”

I wanted him to also start to enjoy his diaper changes so I started to give him a hand job. My idea was this would further humiliate him and also get him to associate diapers with pleasure. It did not take long for him to explode. Made sure to point his penis so it shot towards his face. Then I took my finger and pushed some into his mouth.

” now make sure you swallow. You now know what is girls go through when we have to swallow.”

after that I again changed him and taped his diapers on him. I locked him back up. I went again and sat at may desk and put my feet up.

” now you will crawl to me again. Then kiss my feet and thank me for this, after that you will go pick up my lunch. Once that is done you will see what the other secretaries need from you.”

[Kaylaindiapers]

James did as he was told and was now so embarrassed as he stood there in just his diaper.. Once he laid down he thought he’d try to talk her out of all this crap! 

He laid there as she began changing him..

”I’m not a little girl pl- please I don’t wanna be a baby!” He begged as he saw a new Fresh diaper being unfolded..

He smelt the baby powder it seemed like it took him back to his childhood.. He remembered being embarrassed cause his new step mom said he was wetting for attention and he didn’t remember wetting his bed but he woke up to a wet bed on several occasions… Once it didn’t stop his step mom decided he did it for attention soon he was back in diapers then drinking a bottle and eating baby food… He did all this cause his step sister would let her friend do anything and James loved it!! Now he felt like he was reliving a memory..

Just like that just as Sara his step sisters friend Tiffany began rubbing his diaper. 

Once he had his orgasm he laid there basking in the afterglow he felt something bring shoved in his mouth he gagged but Tiffany kept a hold of his balls to make sure he swallowed..

He gagged trying to get that taste out of his mouth! 

“Pl- please i need a drink!” He cried 

Once James was back in a clean diaper again locked back up he hated this new situation.. 

James did as he was told crawling to Tiffany kissing her feet..

”Thank you.” 

 

 

[Sissytiff17]

The look of him crawling on the floor really gave me an idea it was time to give him some tasks. Nothing that would be crazy obvious but some that would definitely make him feel less of a man. I loved the power I felt when we kissed my foot. I felt like the strongest woman in the world. I was so excited by this. I could not believe it but I got off on the power I now had over him.

” now James since you are going out anyway to get our lunch I do need you to make another stop. I would like you to go into cvs and pick me up some nail polish. I am low and you will be out anyway. Well anyway you can stand up and leave you are dismissed.”

I looked at him and loved how his but puffed out. I can’t wait for him to be wearing a dress. This way I can see that cute diaper at all times. That will take place in time though. Oh wait I just had another idea.

”oh and James one more thing make sure to ask the other girls if they need anything from the drug store too. Here is the company card. I know a secretary cannot afford these extra expenses. Feel free to get yourself some if you need them.”

I laughed hard at my last comment. I can tell I now have his mind going a mile a minute.

Edited May 19, 2023 by Sissytiff17

[Kaylaindiapers]

James was furious how she just ordered him around he hated being a secretary..

”Um ok.” He said now knowing what else to say.. 

He got a list from the other girls and he blushed real embarrassed as one of the girls wanted him to pick up a package of diapers while he was out cause she wouldn’t have time after work..  He wondered if she knew about what Tiffany was doing to him..

James dutifully did as he was told and came back with everything.. He went ahead and ordered a steak for himself sitting the bag on his desk and then going to his old office and giving Tiffany her bag of food..

”Here’s your lunch..” 

[Sissytiff17]

I’m could not help laughing at seeing James hand all the items to the girls. How the mighty have fallen. He looked so ashamed as he went up to each and gave them the item. You could see him blush when he had to hand over the diapers. I heard him knock on the door and motioned for him to come in. He had the most defeated look on his face as he handed me my items from the store and my steak. It was then I noticed he got himself a steak and not a salad. I was pissed he disobeyed me and would be punished.

”thank you James for my lunch but what did you get yourself? It looks like you got a steak. I told you a salad. Well since you cannot listen you will be punished. Pull down your pants and go stand in the corner.”

I took out a baby bottle and put formula in it. I also crushed a laxative it the formula.

” now you are going to stand in the corner until your bottle is finished. Once it is finished I am going to paint your nails. If you complain I will go bright pink. It you are good I will go a nude shade”

[Kaylaindiapers]

“Well I didn’t want a salad and I that steak smelled so good!” He said a little bit of life coming back to him! 
Not even a second later he found out quickly he couldn’t do anything on his own anymore and had to do as his former secretary told him..

”B- but damn it th- this has gone far enough!” He cried then he realized the situation he was in… He pulled his pants down and did as he was told but not without crying and stomping over to the corner trying not to trip himself up..

James took the bottle and reluctantly begin drinking he noticed it had a off taste kinda sweet but wasn’t sure.. 

“Wh- what is this?” He asked looking at the bottle and noticing it said baby girl 

He was so angry but he didn’t want his nails painted pink so he drank his bottle..

”Ok I’m done.” He said proudly like it was something to proud of a grown man drinking a baby bottle… His life was over! 

[Sissytiff17]

I loved looking at this grown man standing in the corner. I wonder what was going through his head. I wonder if there is any part of him that enjoys this treatment. I know I love this. I am feeling a rush of power that I have not felt since I competed. When I was an athlete I was in full control and nothing could stop me. Now I have that same chance. I really want to run this company well. Not only will I get to take James down some pegs but I will get to show off how great of a businesswoman I am.

”now James I want you to crawl over to my desk and sit in the chair across from me. You don’t need your pants. Your diaper looks so cute on you. Now we are going to do your nails. You will have cute nails like ms Tiffany. I bet your excited.”

I opened up the nail polish and let him look at the open bottle for a little. I wanted to let it sink in. I then took the brush and slowly painted each nail. I had him put his hands flat on my desk to dry. It was then when I remembered about the treat I put in his bottle. I wonder how his stomach feels. This is going  to make him feel more vulnerable.

”James we are finished get back to work”

 

 

[Kaylaindiapers]

James felt like he was in daycare not only the way she talked to him but the way she made him crawl and wear no pants so his diaper was on full display and then the baby bottle she made him drink standing in the corner like he was in timeout! 

“No I’m not I don’t wanna be a sissy baby please can’t we talk about this i’m so sorry how I treated you I’ll never do it again please!” He begged as he had no choice but to sit down..

James sat there as Tiffany acted like a school girl so excited to do his nails..

Once she was done he didn’t feel so good and once she dismissed him he stood there knowing what was going to happen..

”Um please Ms Tiffany I need to go to the bathroom please can I stay in here I’ll be good!”  She had completely emasculated James and took everything from him reducing him to a sissy baby who was begging to stay with mommy… He began crying as he couldn’t believe how his life has changed so dramatically.. 
 

[Sissytiff17]

I could not help but to laugh at his begging. This is all part of the process and I need to stay strong. I cannot give in. I loved how cute his nails look. It is not an obvious look. You would need to be looking for it. However, if you are looking it is a very feminine look. I actually think he enjoyed getting his nails done. Not that he will ever admit it. Enough of all this it is time to kick him out.

”first off no you will not stay in here. This is my office and I need to get work done. You never let me hang out in your office. I am not going  to treat you any different. Remember you are the lowest secretary on the totem pole. As for the bathroom you don’t have to worry about using that anymore. That will make your life so much easier. You are wearing your diaper honey. Now get back to work or you will be punished again.”

I watched him sit at his desk from my desk. I know that he will eventually lose this battle and mess himself. I cannot wait for that.

[Kaylaindiapers]

“No- no I’m not!” He yelled trying to rip the diaper off.. He kept dancing around and he felt it he tired to fight it then all at once he began messing his diaper..

He actually began crying like a baby! 

“This can’t be happening please no more of this you made your point please!” He cried..

A part of him wondered if he lost his mind or had a stroke!  How could this be happening to me!  He thought as he cried some more.. 

“I- I just wanna go home!” 
 

[Sissytiff17]

I watched as he shit himself. If you watched closely you could see many tell tale signs. How his legs buckled like a toddler. His face got very red. Lastly you saw his butt puff out even more. The crying was the icing on top. I have finally broke him. I was shocked at how quickly I did it. I must be a true domme at heart and he is a true sissy at heart. 

“Honey it is ok babies mess their diapers. I expected you too and I know you will many more times. It is ok. I understand you want to go home and I understand you don’t want to be a secretary. I will tell you what I will give you a choice. One you can stay on as a diapered secretary or number 2 you become a full time baby. You will not be a secretary anymore and you will just be a baby 24/7. I want you to sit on the floor and think and decide. You have ten minutes. Think long and hard. This will determine the next year of your life.”

The poop must be going all over as he sat down. Damm it also stinks. However, the smell is worth it.
 

[Kaylaindiapers]

James hated the choices he had but what could he really do he sat there trying to think about his future and the choices she gave him… He knew right away he wanted to get out of this messy diaper and fast! 

“Wh- what would I have to do as a full time baby?” He asked stuttering nervously..

He really couldn’t believe he asked that but then again he didn’t believe any of this was going on that this is his life now! 
 

[Sissytiff17]

I can’t believe he was really considering this. I really had him wear I wanted him now. Pretty soon he will be nothing more than my baby girl.

”well honey that is a really great question. As a full time baby you would have the same status as any other full time baby. You would be expected to act like a 6 month old and you would be treated exactly like one. If you chose to stay like a secretary, you would be treated like a secretary during the day and then basically my maid/servant at home. The girls would tell you what to do. Either way you are no longer in control. However, as a baby people would probably be nicer to you. Everyone treats babies nice. I would be you mommy if you were my baby. You just let me know what you decide”

[Kaylaindiapers]

James was thinking and the option wasn’t horrible as he hated the position he was now in.  James always being the negotiator figured he’d try to cut a deal. 
 

“How bout a two year old instead of a six month old and how bout try it out for a week then I can make the decision on what I really wanna do?” 

[Sissytiff17]

He is actually trying to negotiate I need to let him know I am boss and in control. His proposal is not bad but I cannot give in. If I do I have some power diminish. 
 

“You actually think you have some power. You have no power. I have no reason to negotiate and I will not. The deal is either stay like you are now or be baby for at least a yr. You will start at 6 months if you are good I may allow you to grow up a little. The choice is yours. You have 15 more minutes to decide. Now I am leaving you in here while you decide. Your poopy diaper stinks. I will be back in 15 or if you decide before that yell for me”

 

[Kaylaindiapers]

“N- no please I know you’re in control can I please just have a week to decide I’ll try it if you’ll let me and see if I like it and if you offer me a choice then I’ll be happy to make it if you let me!” Please Ms Tiffany or mommy.” He threw the mommy in there to butter her up.. 

James was hoping he made a good pitch as he was letting her know she’s in charge not him and he understood and accepted that..

He sat there waiting for her to make the decision as she seemed like she was thinking it over or at least he hoped she was! 

[Sissytiff17]

I guess I need to give a little or I will seem cold hearted. However he is not going to get off as easy as he wants. I am looking forward to having him as my baby girl. I am not letting go after a week. He just looks too cute sitting there in his poopy diaper. What a come down from the confident man that was here the other day. 
 

“ok I will tell you what I will come off the year but you are not getting a week. I am willing to do six months. I am also willing to let you gain toddler status after 3 months. That is only if you behave. Now I am going to give you 10 more minutes to decide. Remember if you don’t take my deal you stay as a secretary and my maid at home. You will also have to go through the secretary hazing.”

[Kaylaindiapers]

James knew he didn’t have any choice and he was happy she at least was willing to give him more of a chance then she was earlier.. 

I hate this but it’s better then going to jail he thought to himself..

”Ok mommy i agree I’ll be your baby for six months please can you change me?” What have I gotten myself into! He thinks as this whole thing seems like an out of body experience! 

This can’t be me trading my life of Italian suits with diapers and baby clothes but what choice do I really have she owns me literally.. 
 

[Sissytiff17]

“Oh great baby girl. We are going to have so much fun. I think after this six months you are going to be begging to stay as my baby girl. Now strip down and lay down. I also need you to sign these two papers if you want to be chnged. I will explain what you just signed after I change you”

I knew he would sign and I can’t wait to explain what he signed after. I unlocked his plastic pants and up taped the diaper. Damm he did a number on it. I almost gagged but this is all part of being a mommy.

” wow you did a number on that diaper. Someone made a big stinky. Yes you did.”

I also tickled him as I teased him. I wiped him up and put some rash cream on him. I then powdered him and doubled diapered him. Is,Leo a new pair of plastic pants up him. They were pinks with a huge bow in the back. I stood him up and made him close his eyes. As he did I slide a cute pink dress over his head. It even had a big bow in the front. I then attached a pink cheerleading bow in his already long hair. I put him in front of the mirror.

“Now you look so cute. You look like a princess. Now the papers you signed. One was the power of attorney I talked about earlier. The other makes me your guardian. You are stuck for the next 6 months. So you better enjoy it. Also you will call me mommy and remember babies your age crawl. Now let’s go tell everyone that you are no longer a secretary and are the baby.”