Boss Lady Ch. 01

Story Info
Jason is forced to eat his lady bosses ass and pussy.
3.4k words
4.33
89.5k
80

Part 1 of the 2 part series

Updated 06/08/2023
Created 07/27/2017
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jason looked at his watch as he drove the company car into the parking lot. It was 17:45, 45 minutes past his shift end. He locked the car and rushed into the office building.

Cindy, the receptionist let out a gasp as he rushed in.

"Finally, Jason. Carol has been calling me like crazy. She tried to call you, but your phone seems to be turned off," she said.

"My batteries are dead," Jason answered. "Is Carol still in? Can I speak to her?"

"She is still in," Carol replied. "In fact, I think she wants to speak to you."

Jason's heart stood still for a moment. The images of Jimmy being fired were still clear in his head. Jimmy was the previous sales representative and due to some minor mistake he was fired on the spot. Jason was then transferred from his department to the sales department to fill the gap.

He knocked on the door of Carol's office.

"Come in!"

Jason opened the door, and looked in her office.

"Hi ms. Carol. I hope I am not interrupting, I just wanted to have a quick word with you."

"Have a seat," she replied. "It's about goddamn time you arrived you know that? I have been trying to call you for the past 3 hours, but your phone seems to be turned off."

"Yeah, well...You see, mam. The battery was..."

"No excuses, Jason." She did not let him finish. "Everybody in this company has freaking excuses about every single thing that they do wrong."

Jason sat there in silence. His phone ran out of power, what else was he supposed to do, he thought to himself. Afraid for the consequences, he did not stand up for himself, instead he just apologized. He knew that his wife was jobless and pregnant at home, he needed this job to support her.

"How did it end up with JnB? Did you get them to sign up for our services?" Carol asked.

Jason nodded his head and turned his head down.

"They were not interested. They said they have a different company that they are working with and they want to stick with them."

"Fuck, Jason! That was one fucking job you had, and you fucking screwed it." Carol's head was turning red.

Jason looked up to her and asked himself what he had done to deserve this. He was working really hard to get new business in. He looked at the furious Carol in front of him. Carol was a 55 year old woman, with shoulder length curly, red hair. Thanks to her multiple gym visits every week she had a lean, tight body. The male co workers would often talk to Jason about the things that they would like to do to her, in every possible detail. Jason did find her attractive, but because of her greedy and arrogant attitude she was quite a turnoff for him. And besides that, the only woman Jason was ever interested in was his lovely wife. For him it was out of the question to even think about another woman.

"I'm sorry, mam. I have been trying my best to get them in, honestly. I have done all that I could." Jason said with a sad voice.

"Well, obviously your best is not good enough for me, Jason!" she replied. "You should know that you will be punished for this, because it was of very importance of our company."

Jason could feel the tears filling his eyes. He was just hoping that he would not get fired or that she would take a penalty out of his salary. It seemed like every time Carol wanted to punish some employees, all she could think of was penalties on their salary.

"You know what, Jason. I am going to give you a chance. I want you to go home and think about what you did and think about what punishment should be suitable for you. Come back tomorrow, and let me know and then we will decide what to do."

On his way home Jason thought about what he did and what his punishment should be. He just lost a customer, why was it such a big deal for her, right? There were plenty more customers, and Carol sure as hell had no reason to complain about her company. Her company was blooming, she was making hundreds of thousands each year, if not more. What should his punishment be, he taught, was there even a reason for him to get punished? And if she made that much of money, why was she so greedy all the time? Didn't she have enough already?

He arrived home, took a shower and ate his dinner with his pregnant wife. After a little cuddling they went to bed and she fell asleep. Jason could not fall asleep, he was still thinking about the punishment that should be suitable. Suddenly he got an idea. What if he would work longer hours for a couple of days, just to satisfy Carol? He was sure that she would love that. The extra hours would not be calculated as working hours, so Carol wouldn't have to spend extra, and Jason would not have to pay any penalties out of his salary.

The following morning Jason arrived early in the office and after making his coffee, he went to his desk and started working. At around 10 o'clock he saw Carol's car entering the parking lot. She stepped out of the car and Josh couldn't help but stare at her. Carol was dressed very sporty, a skin tight pair of jeans, white sporting shoes, a tight shirt and black sunglasses. Even though Jason did not like her very much, he always thought that she looked best when she was wearing sporty. When she was dressed this way, Jason knew that she would not stay long in the office for that day. In a fast pace she walked through the door, lifting her sunglasses to her forehead as she stepped in the office.

"Good morning, mam." Both Jason and Cindy greeted her at the same time.

"Jason, in my office in five. Carol no phones for today!" she said as she walked past, into her office. She slammed the door hard behind her.

Jason and Cindy looked at her. They both knew that Carol was not in good mood today, and that it was just a matter of time before she would snap at someone. After a couple of minutes Jason swallowed his fear and walked into her office.

"Ah, Mr. Jason," she said. "What have you come up with?"

"Ummm," Jason said. "I was thinking about me working a couple of hours extra for a couple of weeks."

"You're funny," Carol laughed. "And how will this help?"

This was some of the things that Jason hated about Carol. The sudden change in mood. It was like one moment she was angry and wanted to drink your your blood, and the next moment she laughed and told jokes. Didn't she need professional help?

"Well, I will be working extra hours, without any extra payment. I will do anything that you tell me to do," Jason said.

Carol stood still for a moment and stared at Jason.

"I have also given it thought, and my punishment is this," Carol said while going into her bag. She took a sheet of paper out of it and threw it on the desk in front of Jason. It was a resignation letter.

Jason eyes widened. He could feel his body getting warm and his heart missing a couple of heartbeats. He thought about his wife and unborn child. This could not be happening. He could not lose his job like this. Not over that lousy prospect.

"Please, mam. I don't want to lose this job. My wife is pregnant and currently has no job. Please think about my wife and future kid. Please give me another chance. I will not disappoint you."

Carol looked in him, and he could see her eyes glittering. It was like she had achieved something great. He could tell that she was feeling powerful about the fact that he was pleading and almost crying in front of her. She was such an evil woman, Jason thought.

"Okay, I'll tell you what," she finally said. "I will give you a test and we will see if you pass that. If you don't, then I guess you will be fired."

"Alright, mam. Anything, man. Just please don't take my job away." Jason almost cried.

"Stand up, and get on your knees! Head above!" Carol said in a demanding voice.

Jason was surprised by her command, but he followed orders. He stood up from his chair, and went to his knees next to it.

"Good boy," Carol said with an evil smile.

She stood up from her chair and walked up to Jason. She stood in front of him and spread her legs. Jason who was surprised and ashamed to be in this position in front of her, bent his head down.

"Look up!" Carol said with a sharp voice.

Jason looked up with a surprised look in his eyes. What the hell was happening here? What were her intentions?

"Listen, bitch boy!" Carol said. "As a punishment I am going to make you eat my pussy. And you are going to eat it good and give me a wonderful time, understood?"

Jason's eyes widened in amazement. "Please, mam. Please don't let me do this."

"You have a choice," Carol said. "You eat my pussy, worship me, make me feel good and I will let you continue to work. Talk to anyone about it and my lawyers will sue you for everything you have. If you don't do as I say, you may pick up the letter from the table and leave right now without a job. But think about your wife. Whose cock will she be sucking for some food? And what about your kid? Do you want your kid to call someone else daddy?"

The image of losing his wife and future kid flashed through the head of Jason for a moment, and he could feel a cold shiver going through his back. This woman was right. He had to do what she demanded, otherwise he would lose everything.

"O...Okay," Jason said. "I will do anything you like."

Carol looked at him and started to smile. She took the belt off her her jeans, opened the two buttons and took her zipper down.

"Take them off, bitch boy. NOW!" she yelled at Jason.

Jason felt humiliated, but he did not have any choice. He grabbed her jeans on both sides and pulled them down.

"Hold them there!" Carol said when the jeans reached her knee. "Come on, sniff my pussy and tell me how it smells."

Jason looked up at her. She was wearing red panties, with netting in the front, showing a light glimpse of her pussy. Carol grabbed his hair and pulled him closer, that his nose was buried in her crotch.

"Smell it, I said," said Carol.

Jason breathed in through his nose. He closed his eyes out of embarrassment, but he could not help himself of taking in the smell of Carol's pussy. Carol, who still had a grip on his hair, started to rub his face up and down her pussy. As she was doing this, Jason could feel that Carol was already getting wet. Carol stopped for a moment and commanded Jason to take her pants completely off. After that she continued to rub his face against her pussy.

After a couple of minutes of rubbing his face against her pussy, she stopped and let go of his hair.

"Come, on. Stand up."

Jason obeyed and stood up.

"Take your shirt off," Carol said. "But keep the tie on."

Jason did as he was told and soon he was standing in front of her with his pants and shoes on with a tie around his neck. Carol grabbed the tie and walked to her desk, pulling Jason with her. At her desk she laid down, with her back on the desk.

"Take my shirt off, slowly. Tease me, kiss me, show me how much you want that job," Carol said while still holding Jason's tie.

Jason placed his hands on Carol's hip and started kissing her belly. He noticed how flat and tight her belly was, despite her age. He slowly raised his hands, pulling Carol's shirt up and taking it off. He started kissing her higher and higher, till he reached her boobs. He reached around her back and untied her bra, after which he started licking both her nipples. Jason could still not believe that this was happening. He was pleasuring his boss only to save his job. He felt disgusted and ashamed of himself. How did he get into this position?

"Come on! Do it like you mean it!" Carol demanded, giving a hard pull on his tie.

Jason started circling his tongue around her nipples, one by one, and could feel that she was getting aroused. When caressing her left boob he could feel her heart pumping faster.

"Okay, Jason. Now go down on me. Take my panties off and eat me like your job depends on it. Well, it actually does!" Carol said.

Jason did as he was told and went down to her pussy. He started kissing her legs up and down, and slowly took her panties off. He noticed that her panties were soaking wet, and with disgust he realized that he was actually pleasuring her. He was actually sexually stimulating his boss, just for a job. He was making this woman feel good, while he was feeling terrible for doing so. This was the same woman who made his work a hell. The same woman who, with a twist of her fingers, could make his entire life a hell. Then he realized once again that he did not have a choice, and he started kissing Carol's just above her pussy.

"Oh, good boy," Carol moaned. "You really want that job, huh bitch boy? Yeah, I can see that you really want it. Now eat my pussy and make me cum."

Jason softly licked the top of her pussy with the tip of his tongue. After that he slid his tongue down her pussy in a slow motion. Carol moaned in ecstasy, as he did this, and slowly opened her pussy wider and wider as his tongue went down. Jason realized that her pussy did not taste as bad as he had imagined. In fact it didn't taste bad after all. Jason started to pick up his speed, going faster and faster and Carol was moaning wilder and wilder.

"Get your tongue in there, Jason. Get it in. Fuck me with your tongue."

Jason did as he was told and stick his tongue inside of her pussy, feeling and tasting the freshness and warmth of it. He started to tongue fuck her pussy faster and faster, until Carol was losing control. Suddenly Carol grabbed the back of his head, almost pulling his hair off.

"Keep going. Keep going. Don't you fucking stop. Don't you dare to stop, bitch boy."

Jason could feel her legs pressing on the sides of his head, and he started to tongue fuck her even faster. Suddenly Carol let out a moan.

"I'm cumming. Oh fuck i'm cumming. Open wide, bitch boy. Open wide. Drink my fucking pussy juice."

Jason wanted to pull his head out of disgust when she came, but her grip on him was so firm, that he did not have a choice but to take her pussy juice in his mouth. He could feel it filling his mouth like a stream of water. He got disgusted by the idea of his boss cumming into his mouth.

Carol let go of his head after she came and stood still for a couple of minutes, staring at the ceiling, catching her breath. After she could breathe normally again, she sat up and kissed Jason on the mouth, tasting her own pussy juices. Suddenly, while they were kissing Carol moved her head away from Jason, closed his mouth with one hand and kicked between his leg. Jason let out a muffled scream.

"Now, this is something I do not want to see in my office. You are getting aroused for your employer?" Carol said.

With big eyes Jason looked at his crotch, and noticed that his dick was hard. He was aroused for his boss, a woman who he did not like at all. Jason was disgusted by himself and was feeling ashamed. How long was he hard for her? Was it from the beginning, or did it just get hard?

Carlo laughed. "I hope that you are not thinking that you will be fucking me, right? Classy woman like me don't fuck with losers like you, get that?"

"Yes, mam." Jason was relieved. He was hoping that she would not let him fuck her, because that would be a total embarrassment for him. He was afraid that if she knew that he did not want to fuck her, she would actually make him to it.

"Alright, bitch boy. Now clean me up." While she said that she stood up, turned around and went back down on all fours.

"What do you mean?" Jason asked. "I'm not sure how I should clean you."

Carol looked at him with her evil smile.

"Can't you see that my pussy juice is all up my asshole? I need you to get in there with your tongue and lick it clean."

Jason's eyes widened. He had never licked a woman's ass before. He knew that assholes were pretty tight things to fuck, but he never considered licking one. Was that even a healthy thing to do?

"Come on, I don't have all day. And I can't put my clothes on like this." Carol said.

Jason looked Carol's firm ass. This was one of the tightest asses he had ever seen, but still... He then looked at the piece of paper on the desk...He knew he had no choice.

He grabbed Carol's ass cheeks with both hands, spread them open and stuck his tongue on her brown hole.

"Yeah, baby. Circle it with your tongue. Lick it clean."

Jason circled with his tongue around her asshole and could hear Carol moan and enjoy this. Jason was afraid that he would not like the taste and smell of Carol's ass, but he realized that Carol's ass actually smelled and tasted good. But still, Jason was feeling humiliated because of this woman making him lick her asshole like he was some kind of cheap whore.

Suddenly carol started to thrust back on his tongue while spreading her ass cheeks and making a loud, moaning noise.

"Keep licking, keep licking me bitch boy. Keep fucking licking me. Lick that asshole nice and clean."

She was building up another orgasm, Jason figured. Suddenly Carol pulled hard on his tie, pushing burying his face deep in her ass. Jason felt like her ass was collapsing on his face and he could not breath. He could feel her ass vibrating on his face for a couple of seconds and then she let go of his tie. He pulled his head out of her ass immediately and started gasping for air. What the hell happened to him? Did he just almost passed out between the ass cheeks of Carol? How humiliating!

Carol turned around, looked at Jason and smiled.

"Nice face. Next time I'm going to ride it."

Jason lowered his face and looked at the floor. He knew that Carol had him in his grip now and he would have to do anything she demanded. Carol stood up and demanded him to dress her. He obeyed quietly, this was not half as embarrassing as the things that happened earlier.

"Alright, bitch boy. Now wear your shirt and tie, wash that pussy juice from your face, and get back to work. And remember, if you dare to tell anything to anyone, I will take everything you have. And remember that you are now my private bitch boy. You will do exactly as I tell you."

After Jason washed his face and put his clothes on, he walked out her office door and walked to his desk. He worked quietly at his desk until Carol left. As she closed the exit door behind her, she turned around and gave Jason an evil smile and a wink. He knew that he was her bitch...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
AnonymousAnonymous10 months ago

Hell, why not give a MILF looking boss great oral sex?

AnonymousAnonymousalmost 2 years ago
Oh dear

"Carol let go of his head after she came and stood still for a couple of minutes, staring at the ceiling, catching her breath."

As she's laying on her back how can she stand still. You should have put laid still.

Crap writing.

Bassey4pussyloveBassey4pussylovealmost 2 years ago

Excellent story. More chapters.

AnonymousAnonymousalmost 2 years ago

I thought it sounded like fun. Dom women, ass and pussy licking.. all good things

AnonymousAnonymousalmost 2 years ago

Gross. I feel like I need a shower after reading that...

Show More
Share this Story

READ MORE OF THIS SERIES

Boss Lady Series Info

Similar Stories

Worshipping Lili's Ass Pt. 01 College girl dominates smaller boy.in Anal
Ms Coney Therapist makes him her oral pet.in Fetish
Mrs. Honey College boy must service a mature lady janitor after hours.in NonConsent/Reluctance
Tamed by Meg Megan introduces me to the pleasures of being penetrated.in Anal
His Dominant Landlady James needed a place to live. Two older women needed him.in Mature
More Stories