Jenny Gets Punished At Work

Jenny Gets Punished At Work

Jenny woke up early, it was a Monday. She was working as regular and she had just had a free weekend for what felt like forever. Jenny was working at a huge company in the middle of New York. Her title was assistant to the CEO of the company. They had been working together for two years and although she hated to admit it she had a huge crush on him. He was tall, smart and beautiful, but he was also really hard to get and also… her boss. He almost never talked to Jenny more than saying work things and Jenny was aching for more.

Jenny made a lot of money just by taking some phone calls and arranging meetings, she also had the greatest colleagues in the building. Her best friend Michelle was working in the lobby as a receptionist and they almost had the same job so they had realized while working that they had a lot in common. They had been hanging out as best friends since day one and that made work a lot more bearable while she was crushing on her boss. Jenny put on a white tight polo dress that was ending right by her knees. Her everyday mission was to look as good as possible for her boss. She let her hair down and made sure to curl it just about right. Her body was small but curvy and any man would love it, but obviously not her boss.

Jenny got in her car and drove to work. It was a company car but they had given it to her because she had to do a lot of errands for her boss, Jonathan, or Mr. Andrews as she called him. After parking and going inside the building she made sure to drop of the coffee that she had bought for Michelle while making her way up to her room. She sat just outside Mr. Andrews’s office in a beautiful room. It had light blue walls and a white marble floor. She had a white desk and a nice armchair to sit in. As always she had fresh flowers in a vase by the desk just for impression. The walls had paintings in modern art on them and nice bookshelf’s with decorations and everything. It was just opposite of Mr. Andrews office. He had the same floor but his desk was mahogany, he had a bigger armchair and the bookshelf’s matched the desk. By the next wall he had a big sofa in black leather and an armchair that matched. He also had a small wagon with lots of alcohol for big customers or celebrating and he had the regular pictures with art on his walls.

Jenny heard her own tall heels while walking, it made a sexy sound and she knew Mr. Andrews would notice her directly. She took of her jacket and started her computer. Then she walked into Mr. Andrews office to say hello and ask him if he wanted anything. As usual he barely even lifted his head to acknowledge her and waved her off saying he wanted nothing other than her emailing him is itinerary. She sighed silently while walking off because she wanted nothing else than him looking at her for more than five seconds. He was a weird man that loved work more than anything else, clearly. By the rumors going around the office she had learned that he was a lone wolf, he had his friends but he didn’t have a love life. Some people thought he was gay but others confirmed he was not.

The day went off and Jenny spent most her time serving coffee to Mr. Andrews and his beloved customers whenever they had meetings. She barely had time to go to the bathroom. After her quick lunch break where she had just thrown in her food in her mouth she hurried back to help prepare for another meeting. Her pressuring bladder kept going and when she had the time she hurried for the bathroom. It was looked and she realized she had gone to long without going to the bathroom; she wouldn’t make it to another bathroom in time and started to knock on the door to make the other person hurry. There was no answer and she felt how the pressure kept rising and she started to leak in her panties. She tried to hold her hands against her bladder to keep it from coming but it was too late. She stood there, peeing herself like a little girl just as the door opened. The person who opened was her boss Mr. Andrews, he watched her as she lost control of her bladder and everything turned wet. Her dress and her shoes filled up and for the first time since her interview she locked eyes with Mr. Andrews who looked scarred. He backed off a bit and when Jenny realized what just had happened she buried her head in her hands and said SORRY SORRY I’M SO SORRY! For what felt like 200 times. She looked up at Mr. Andrews who was still looking at her.

“You can take the rest of the day off.” He said and walked off. She hurried inside the bathroom and tried to dry herself off as well as she could. When she had stopped crying at the embarrassment she hurried to her office to get her things and noticed how Mr. Andrews door was closed. She went home and took a long shower and kept crying her eyes out for hours. By 5 her phone rang and her friend Michelle asked where she was and if she wanted to go out for dinner. Jenny lied and said she had a headache and spent the rest of the night trying to get over the embarrassment.

The next day Jenny woke up and wanted to call in sick. All she ever wanted to was to get her boss attention, but not like this, not like wetting herself like a little kid. She decided that she had to face her problems and got ready for work like any other day. She decided to look extra good for today, she put on a black leather skirt and a tight black polo shirt. Her long hair was put up in a beautiful and professional bun. Her lips were red and her perfume extra nice. She drove to work and tried to think of anything other than yesterday’s embarrassment.
She got to work and Mr. Andrews was not there yet, which was weird because he always arrived first and he always left last. She started to work and got herself a cappuccino that she drank while reading her emails. Half an hour later Mr. Andrews got into the office, Jenny quickly stood up and smiled while facing her boss, trying to not be too embarrassed.

“Good morning Mr. Andrews, can I get you anything?” She asked politely and professional.
“Good morning, Jenny. Actually, could you push my morning meeting and then come into my office. I would like to talk to you about what happened yesterday.” Mr. Andrews said and locked eyes with her. His beautiful piercing blue eyes felt extra piercing today. Jenny felt a lump in her stomach as she nodded and said. “Of course.” Jenny made a call to the other assistants in the office and made sure they told their bosses that the meeting was pushed. She took a big breath and collected herself before going into her boss office. She knocked and walked in.
“Could you close the door?” Mr. Andrews asked not looking up from his screen. Jenny closed the door carefully and walked over to his desk. He closed the screen and looked up to her, gesturing towards the chair in front of his desk.
“Please, sit.” He said. Jenny obeyed and sat down. She was way too nervous for this. He was probably going to get fired or being put in another office or something.
“So, I would like to talk about what happened yesterday.” Mr. Andrews said and leaned back in his chair. His facial expression was hard and he never failed his eye contact.
“I’m really sorry, it have never happened before I just didn’t have the time to go to the bathroom all day because of the schedule, I’m really, really sorry.” Jenny started to make excuses for herself. Mr. Andrew nodded while listening to her excuses.
“I understand, I know this is a busy job but I can’t have my assistant going around having accidents like that. We have a standard to always live up to here. I need to know that this will never happen again.” Mr. Andrews said sternly.
“I know, I love this job and I would never let anything get in the way of me working here. I would do anything to get another chance. Please don’t fire me.”
“Fire you? No, we’re not really there yet. But I would like to have reassurance that this will never happen again. Because as you know this is a busy work environment and there’s not always time to use the bathroom.” Mr. Andrews said put his hands together.
“I promise, I want to stay here I will stop drinking water, actually I will stop drinking everything!”
“Don’t joke, of course you’re going to be able to still drink water. What I do want, for the start, to feel like I can trust you not to embarrass me, is to take some precautions.”
“What do you mean precautions?” Jenny asked and lifted her eyebrow.
“I think you should wear protection while you are working.” Mr. Andrews said and leaned forward.
“What do you mean protection?” Jenny was confused.
“As you decided to act like a child at work and wet yourself you are going to be punished like a little girl and wear diapers until I feel like I can trust you.”
“Are you kidding me? I’m a grown woman I’m not wearing diapers.” Jenny was enraged and embarrassed, so this was the way her boss looked at her now, like a little child.
“It’s either that or I will have to move you back to the lobby as this job will always be this busy and I want to be able to trust my assistant.” Mr. Andrews said calmly next to Jenny’s enraged voice.
“Of course you can trust me, but I can’t wear diapers, I’m 26 years old?”
“You can have until after lunch to decide, it’s either that or I will be moving you downstairs. You can go now.” Mr. Andrews said and opened his computer again. Jenny sat down for 30 seconds in awe before walking out of his office. She turned to her own seat and computer and thought about her options. Either she wore diapers to work or she would be degraded back to the lobby. What if anyone would see her? What would everyone say? Maybe she would only have to wear them and then use the bathroom as usual. She decided her work was to important and that this would only be temporary, and by the time lunch was over she gave herself courage and knocked on her bosses door.
“Come in” He said and when she walked in he was still looking at his computer.
“Okay, I will do it. How do I do it?” Jenny said. Mr. Andrews looked up at her.
“Great, you are going to go to this address and pick up this brand, and this stuff.” Mr. Andrews said and wrote something on a note. He gave it to her and kept on talking.
“Then you will come back here, I will be the one to put it on you and I will do occasional checks to see when you need to be changed. I will be the one to change you and while we are testing you, you will have no bathroom privileges and therefor do everything you have to do in your diaper.” Mr Andrews said.
“Are you kidding me? I mean I can wear them but I have to be able to go to the bathroom whenever I want to? And what do you mean you will be the one to change them and do checks? I’m not a little girl I can do it myself.” Jenny was super embarrassed at this proposition, all her time her at the company she had done everything to make her boss notice her and now that he did, all he saw her was as a girl who had to wear diapers.
“No as I noticed you can’t go to the bathroom, therefor you have to wear diapers so I know that this won’t be an issue. And I have to be the one changing you and checking you since I will be the one deciding whether I can trust you or not. Now, go to this address and pick this up and then you come back into my office directly.” Mr. Andrews said and pointed towards the door. This was meant for her cue and Jenny knew not to talk back to her boss.

She walked out of there and walked directly for her car. She drove for the address and it turned out to be a pharmacy. She looked at her shopping list, the diaper brand was tena slip maxi, she also had to buy wet wipes and baby powder. He had also advised her to buy some rash cream and as she didn’t know how long he was going to put on with this she bought that too. It was embarrassing buying everything but she made sure to say to the cashier that it was for her boss and that he was incontinent, as she was mad at him. She decided to take extra-long on her so she went to another store and went around just for fun. When she got back to work it was around 1. She brought all the stuff up to their offices, she had made sure to pack it up so no one at work would see what she had bought. She marched into Mr. Andrews office, not bothering to knock but he hardly seemed surprised. She dumped the things on his desk in front of him and locked her arms and looked at him, now what? She thought.

Mr. Andrews started to unpack the things and checked off the list that she had bought everything. He looked at the clock and then started to open the diaper-box.
“You can take off your skirt.” He said and if this was any other situation, Jenny would have loved to be asked by her boss to take off her skirt. But knowing what was coming, Jenny was just angry, and embarrassed. She had made sure to use the bathroom before stepping into his office just to show how good she could be. Mr. Andrews walked up to her with the diaper and got down on one knee to put the diaper on her. He was fast and had taped it on without a question. He checked to see how it sat and then he pulled up her skirt and zipped it back on.
“Good, now I will check this before you go home. If you need it changed, I will take care of that whenever we have time. Do you know when Jefferson will be arriving?” Mr. Andrews asked business-talk as usual.

“He will be here by 2.” Jenny said and turned around to walk out his office. It felt weird with the diaper between her legs. She walked funny and the feeling of wearing a diaper was familiar. It made crinkle sounds and she made a promise to herself not to leave her office for the rest of the day. She checked herself in the mirror and realized that if no one would look no one would see. Mr. Andrews had meetings after meetings and by 5 he called her into his office for a diaper check before she could go home.
“So, how did it go?” He asked politely. Jenny was still mad at him but then, his looks made her want to drool again.
“Yes, as I said I don’t need this.” She said and pointed towards her skirt, meaning the diaper hidden under it. She had been good, she was starting to feel the need to pee but she had promised herself not to use the diaper. Mr. Andrews stood up, and even though she wore really high heels he was still taller than her, and bigger than her. He walked around her checking her out.
“That skirt makes a good job hiding it.” He says, he stops by her back and starts to unzip the skirt. Jenny shivers at the feeling of his hands and stops dead in her tracks when he turns in front of her and puts two fingers in her diaper.

“It’s dry, maybe you will show me what a grown up girl you are.” He said, he pulled out his fingers and zipped her skirt back up.
“You can go home for today, when you get here tomorrow come to my office directly.” He said and walked back to his desk. Jenny was mixed with her feeling about feeling turned on that he touched her and angry that he made her, a 26-year old wear diapers. Jenny walked out of office and directly into the bathroom where she took off the disgusting diaper and threw it away. She was a grown woman for god’s sakes; she didn’t need to wear diapers. She was bathroom-trained just like everyone else. She took her coat and walked down to the lobby where she found Michelle packing up her things. They locked eyes and Michelle noticed her anger and they both spoke at the same time.

“I need a drink”
“You need a drink”
They drove back the car home to Jenny and walked over to the nearest bar. As they drank their white wine, Jenny talked about what an arrogant shit her boss was, without naming the embarrassing details of her wetting herself and the consequences. After one too many drinks Jenny started to walk home. She felt her bladder rising once again and hurried her way home. By the time she got to her front door she knew it was too late and the second she walked in, she was wetting herself again. She cried as she cleaned herself up and realized that she was having a problem and she knew that if her boss would see this he would only tell her how right he was.
The day after, Jenny woke up and put on her sexiest underwear, knowing that Mr. Andrews would see them and maybe think about that view. Today she decided to wear black suit pants and a white shirt. Her heels were high as usual and she made everyone notice her as she walked into the building with confidence and saying her Hello’s to everyone she knew. When she walked into their office she remembered her accident yesterday and felt embarrassed that maybe Mr. Andrews would notice it on her. She took of her coat and put her bag on the desk. After ten minutes she heard how the door opened and Mr. Andrews head peaked out.
“You are supposed to come in here the first thing you do, you don’t want me to reconsider this, do you?” Mr. Andrews turned around before Jenny even had the chance to say anything back. She sighed and followed him into his office. This time she noticed that Mr. Andrews had prepared for her to lay down on his meeting table that stood in the middle of the room. Mr. Andrews gestured towards it.

“I thought it would be nicer for you to lay down.”
“I just think it will make me feel more like a child but okay.” She said sourly and walked over. She jumped on to the table and felt her legs dangling by the table even though she had heels. Mr. Andrew walked over to her. He lifted her leg and started to take off her heels, pressing her towards his perfectly fitted suit. Then he started to unzip her pants and pull them down. He took a look at her black satin panties that was a bit too sexy for work and looked at her with a raised eyebrow.
“Aren’t these a bit too grown for a little girl like you?”
“I’m 26.” Jenny said, she was flushed from being undressed and had almost forgot about what the point of undressing her was until her eyes stopped looking at his body and was now looking at the white thing in his hands. He unfolded it and made Jenny lift her butt so he could put it under her. She felt flushed again when he started to powder her bottom and her most precious part. The smell of the diaper and powder reminded her of her childhood. She had always been a late bloomer and it took her parents years to get her potty trained. Maybe this was the reason she had so many accidents. He folded it over her and taped it on as it was the easiest thing in the world. When he was finished he helped her on with her pants, they felt a lot tighter and she tried to see if the diaper would show. She put on her heels and noticed how Mr. Andrews was holding her black panties in his hands. He lifted them and showed her before putting them in his pocket.

“I will keep these until the end of the day, so I know you won’t be cheating.” He turned around and she got a good look at what seemed to be a bulge. Maybe he also found this sexy, undressing and touching. Probably not the diaper-part, he still saw her as a child. The day kept on, Jenny almost forgot about the diaper, except for everytime she shifted in her seat or had to walk and get Mr. Andrews coffee. She went to the mirror every five minutes to see if it was noticeable. I wasn’t, maybe if you knew what was going on but otherwise not. At lunch she sat with Michelle and other colleagues and had so much fun that she didn’t realize how much water she was drinking. And when she got back to the office she had a latte because she started to get tired and she had a lot of paperwork. But 2 o’clock she realized her bladder was full and she made her way towards the bathroom. Mr. Andrews would never notice that she walked away. She realized it was locked and saw a sign that said “Key needed”. No way, had Mr. Andrews really put a lock on this door. She made her way towards the corridor when she heard someone behind her.

“And where are you going?” Mr. Andrews stood behind her, leaning against the door. He had a small smirk on his face.
“I’m going to the bathroom” Jenny said, her leg jumping a bit because of her full bladder. Mr. Andrews noticed her twitching.
“You know our agreement. Little girls like you have to use their diapers.”
“You can’t be serious about that.”
“That is our agreement, and I don’t have time for you running to the bathroom now anyway I need you to call Jefferson’s office and make them fax over the papers from yesterday.”
Jenny didn’t say anything and just walked by him, sitting down in her chair again. Her pressuring bladder got angrier and by the time the fax had come she stood up to give it to Mr. Andrews and realized that she would have to use her diaper. She tried to release but it was hard, she had never peed in a diaper before and her body was against it. After five minutes it finally started to trickle. The trickle turned into more and she found herself standing in the middle of the room peeing in her diaper. It started to swell and it got warm and soft. She would never say it out loud but she felt like she enjoyed the feeling.
Jenny stood for a while, trying to soak in the moment that she had used her diaper. And she didn’t want Mr. Andrews to know, even though she knew that he knew that she really needed to use the bathroom. She walked into his office and put down the fax on the paper, she quickly turned around and started to walk out.
“Jenny.” Mr. Andrews voice said behind her calmly. She froze in her spot and turned around.
“Yes sir?” She asked. He smiled at her and leaned forward in his seat.
“How did it go? Did you decide to go against your beliefs and use the diaper like you are supposed to?”
“No, I’m not a child” Jenny lied, but she was embarrassed and was sure that Mr. Andrews knew that she lied.
“Come here.”
“No, it’s dry.”
“You know our deal.” Mr. Andrews said, his voice a bit to serious.

Jenny walked over to him and stood in front of him, not moving a muscle. He turned around in his chair, his legs sprawled over the seat. She liked being close to him too much. He leaned forward again and started to unzip her pants and pulling them down. He noticed the smell of pee directly and he smiled lightly as his fingers felt the front of the diaper. It was bulgy and warm, and it felt nicer when Mr. Andrews was pressing against it, as it was pressing more against her. She almost moaned but held it in and tried not to look too much. She noticed how his jaws were clenched and how his pants were bulging again. Maybe he liked this? Seeing her in diapers? He pulled up her pants again and turned around in his chair.
“Like I said, it’s good you are wearing protection. You are a good girl for using your diaper. I will change it later I don’t have time now, and it can fit much more than that so you have to use it for a while longer, okay?” He asked, looking at her again. Jenny was flushed and just nodded. She was speechless, much because of the fact that he had a bulge while touching her. The rest of the day floated by and by 3, Mr. Andrews was off for the day and Jenny took her chance to get rid of the diaper. She never got her panties back but she didn’t mind. It was nice knowing that he still had them in his pocket. When Jenny got home that day she started googling around about adults and diapers and realized it was a fetish. She decided to try him the day after, as a punishment for punishing her.

Jenny walked into the office and got right into his. He sat down in a phone call and he signed for her to lie on the table. She undid her pants and took off her shoes and laid down. He got off the phone and said hello to her. He never mentioned the panties but he got right to putting her diaper on. When he was finished, she tried to look for his bulge again but he had quickly got back to his desk, it was a busy day.

Jenny drank a lot of water, knowing what her mission today was. She kept on drinking until she felt the pressure rising, she filled her diaper with a smile, knowing her next step. She walked into Mr. Andrews’s office; he was looking at papers as she walked up to him. She stood in front of him and looked at him innocently.
“I had an accident.” Mr. Andrews almost choked and looked up at her.
“Can you please check me, sir?” She asked, hands behind her back trying to look as cute as she could. Mr. Andrews almost turned another shade of red and nodded.
“Of course, yes I can.” He said, turning around In his chair, starting to unzip her pants. Jenny stepped out of her pants, this was her moment. She quickly sat down on one of his knees. Mr. Andrews almost jumped out of his skin. She took one off his big hands and put them on the front of her diaper. She pressed his hand hard against it and rubbed it. The feeling of the diaper and his hand against her was so sexy and she had to keep herself from coming on the spot.
“Am I a good girl for using my diaper?” She whispered against his ear as she put her head on his shoulder. She had taken her hand away and he kept on rubbing her. She felt his boner against her back and she started to moan as he kept on rubbing.
“A very good girl.” He said quietly. She felt of his boner kept on pressing against her back through his pants and he was rubbing her faster.
“I know you were right, a little girl like me have to use a diaper. I can’t hold it in. I think I’m going to have another accident” She said, moaning in his ear. He pressed a little more and she felt her orgasm rising, she moaned harder and came in her diaper with his hand against her. She heard how he gasped and realized that he had also come in his pants. She smirked, she knew it. He was turned on by this. Jenny got her breathing back and stood up, pulling her pants up and started to walk out of the room.
“Thank you sir.” She said, knowing that her fantasy about being with Mr. Andrews would come through combined with his fantasy. This whole scenario was starting to become fun…

The End of Jenny Gets Punished At Work.

Written by LittleDarkAge

If you want to read more stories by LittleDarkAge you can find a list here: Diaper Girls – Index