Madi and Her Boss – Chapter 6

This is my writing so please do not copy or take it for your use. Thank you.

Updated 2/19/2020

 

6

Jonathan – 3 months ago

Fuck! Something is wrong by the look on her face. Fuck! I can’t mess this up. Deep breath. I need to appear to be calm in order to calm her down.

“Madison, please sit down,” I said as I walked to my Liquor cabinet. “I want to talk to you about something.”

I listen for the door to open as I walk to the bar on the other side of my office, praying she stays and talks to me. But I can get to her if she does. The door is locked so that gives me a few more seconds.

I poured her a drink and refreshed my own drink, then walked back to the desk. One glass I placed in front of Madison and the other, I took to the other side of my desk and sat down. Leaning back in my chair, I took a sip. Holding my glass in my hand, I watched Madison.

Madison sat down slowly. She fidgeted with her hands in her lap. She looked like she was ready to cry. She looked uncomfortable sitting there while he stared at her. She glanced at the glass but didn’t take I in her hands. What was going on in her mind. Was she was worried about something, maybe I scared her off already? Had I misread her?

“Take a sip Madison, it won’t hurt you, in fact it might help” he said with a smirk on his face.

She slowly picked up the glass and held it. “What is it,” she asked softly.

“Whiskey. Take a small sip” he warned.

Figuring she was a virgin at most other things, he figured this would hurt, so he watched her closely as she picked up the glass and smelled it.

Taking a sip larger than she probably should have, she coughed as it burned the whole way down. She fought not to spit it out when she coughed. He found that funny, laughing a little when her eyes got real big and she almost choked.

“I’m sorry,” she said, “I’ve never had whiskey before.” She placed the glass back on the desk.

He was right.

“Well I am guessing there are a lot of things you’ve never had or done before, am I right Madison,” he asked, placing his glass on the desk as well and then sitting back while watching her.

“What do you mean by that and why do you call me Madison and not Madi,” she asked.

He studied here for a minute thinking about her question. Why did he call her Madison? He preferred the way it sounded instead of Madi. Madison was the beautiful woman in front of him, while Madi sounded like a cheerleader on the football field.

Taking a deep breath, gaging if he was ready to put his cards on the table, rethinking that now he had to go slow for her benefit. She was obviously young, naive and inexperienced. He wanted all of that about her, all of her under his control. He didn’t want to scare her away.

“Let me answer something first Madison, you have worked as my assistant now for about 6 months and I think we seem to fit together well, and I have noticed some things about you. I would like to offer you something else, something I think you would enjoy trying.”

He could see the wheels spinning in her head, a look of shock and worry came across her face. What was she worried about? Back track in his mind, what part of what he said made her react like that?

“Slow down Madison. I can see the look on your face, your mind is racing ahead of you.”

She sat up straighter and folded her hands in her lap, her voice barely audible. “Okay, you want to offer me something?”

“Well let me answer your other question before we explore what I wanted to discuss with you. First, your name. I think you are more fitting of your given name of Madison, rather than Madi as everyone here calls you. I prefer Madison.” Tilting his head to the side still intently staring at her, “does it bother you when I call you Madison” he asked.

Dropping her head to look at her feet she said, “no, it’s just that my mom was the only one who ever called me Madison.”

“I see,” he answered. “Well I will continue to call you Madison, so please get comfortable with that.”

He detected some sorrow and pain there in that honesty, he would have to explore that later. Come to think of it, he really didn’t know Madison well. They never spent time together getting to know one another. He only knew what was in her file on his desk.

Sitting up in the chair, leaning forward and placing his elbows on the desk, folding his hands together, he needed to discuss what was on his mind and in that folder.

“Madison, you are young, beautiful and have so much to experience. I also notice some submissive tendencies about you that I would like to explore with you. Have you ever heard of a submissive and dominant relationship before?”

I am watching her closely for any reaction that would make her run. That was not my intent. But I can’t let her leave.

I asked again but differently this time. “Do you know what a submissive and dominant are and how they relate?”

She looks confused. There is my answer, she doesn’t have a clue what I am talking about. My cock just got harder thinking of her as a fresh and new submissive.

“A what and a what?” she answered.

I need to explain this to her in the easiest way possible. Where do I begin? BDSM 101?

“The dominant person has a responsibility to look out for, train and care for their submissive. The submissive’s role is to do things, requested by the dominant that please or bring pleasure to the dominant person who is called their master. The dominant in turn, finds ways to give pleasure to the submissive, but the pleasure for the dominant comes in watching the submissive learn how to achieve pleasure in sexual ways.”

Watching the reaction, I am ready to jump for the door and block it. What was I thinking?

Her eyes got really big and she reached for the glass of whiskey taking another sip.

“You mean pleasure, is that like where you tie someone up and whip them and use them and stuff?” she asked.

I snickered, that is a google definition of something that can be so beautiful.

“Madison, slow down, it’s not USING someone. It’s bringing joy and pleasure to each other in a new way. First, I want to talk to you about being my submissive. I would be your dominant. You would serve and pleasure me, if you agree to this. I would take very good care of you as my submissive. As we are doing now, you would be asked to do things to bring me pleasure, things you may not have ever done and things that may challenge you. When I see fit, you would be rewarded.”

Her eyes are getting bigger and her eye brows are moving up. And my cock is getting harder remembering her on her knees for me.

“When you see fit, what do you mean?”

Calm her down man. Get her back on board. I can see her wiping her palms on her skirt. She is nervous, frightened and unsure of this right now.

She took another sip of the drink I offered her. Thank god for the whiskey.

She sat up taller. “Wait a minute, do you realize I don’t even know your name? I mean I answer your phone as Mr. Stewart’s office, but I don’t even know your first name? Maybe we can start there?”

This was a side of Madison I had never seen. She had a voice. Liquor gave her a voice.

“Ok, I didn’t realize you didn’t know that” I chuckled. “My first name is Jonathan, I am Jonathan Stewart.”

There was so much to teach her.

Sitting back in his chair, left hand to his chin, he watched her, studied her. Started to imagine things with her. He could feel his cock getting painfully hard. She did something to him, he needed to tie her up soon, control her.

Before she runs out the door let’s see what she thinks. I know she is interested, I just have to get her on board to try.

“Okay, so would you like to do a little exercise and see what you think? Let say we start out slowly and work our way into it? Try some easy things while we get to know each other more?”

She is just staring at me, I can tell she is trying to process all of this information. Maybe she needs a little evidence of how I would take care of her.

Standing up, he undid his cufflinks and folded his sleeve cuffs up his arms. He then walked around to the front of the desk where Madison was sitting, grabbed her hands and helped her to stand. His eyes were on hers the entire time. He slowly walked her over to the couch and turned to face her.

“I am going to help release some of the pressure you’re under, so you can think clearer,” he said.

He started to undo the buttons on her blouse slowly and take the blouse off the shoulders, letting it fall to the floor. Her eyes went back and forth watching his face. He leaned into her, taking a deep breath as he went to kiss her shoulder before removing her bra strap.

Madi was feeling everything come alive as soon as he touched her. Sparks and flames ignited in her as he did this. She couldn’t stand it. He had never touched her so gently like this. He never kissed her like this. Her pussy was pulsing, goosebumps up and down her spine and in her scalp, this man was driving her insane.

Once the strap was off he grabbed her breast in his hand, “you are so beautiful Madison” he said and took her nipple in his mouth, nipping the tip, sucking the tip.

Her eyes closed, and she took a deep breath as her head fell back. Her lips parted, and a little moan came from her lips as well.

He did the same to the other breast, nipping, sucking and pinching both to arouse her more.

His hand slowly went down her leg, under her skirt, and to her underwear. He could feel the warmth before touching her. His hand moved the underwear to find her fold. She started to drop to the floor.

“Careful Madison, I don’t want you to fall, lay down on the couch,” he said as he helped to position her on the couch, spreading her legs, one over the back and one on the floor. He wanted access to that warm pussy. His own cock was growing harder and demanding more of her.

Madison laid her head back on the couch. She looked so nervous and fresh. He loved this look on her. Scared and untouched. He sat down on the couch in front of her spread legs. His cock hurt it was so hard. God she was beautiful.

“Madison has anyone licked your pussy before,” he asked in a soft voice. He had a feeling he knew the answer. He was staring at her mound, wetness coming through her underwear.

“No,” she whispered. She closed her eyes tight.

“Well Madison, I am going to help you release some tension. Lay still for me and do not move. You move, I stop. Understand?”

She nodded. But that wasn’t what he wanted.

“I need you to say yes, verbally, so that I know you understand,” he said to her, looking at her, waiting for her verbal reply.

“Yes,” she whispered. He could tell she was uncomfortable being stread open like this. He wanted to see what other ways he could push her.

“If at anytime, this is uncomfortable, you need to tell me to stop. Do you understand Madison?”

Getting the verbal answer he wanted, he moved her underwear to the side, he laid his hands on her mound. He felt the heat she was giving off. He took his hands and spread her folds. “Beautiful Madison, just beautiful, so pink and ready.”

She was so wet and turned on. He couldn’t wait to get his mouth on her.

Madison closed her eyes while her hands clenched the side of the couch.

He started to gently lick her inner lips. He purposely breathed on her to give her more sensations while he was down there. He lavished her with his warm tongue, enjoying the reaction. Her moans were making his cock harder and more uncomfortable in his pants. Slow licks, small sucks, and her moans told him she liked it.

He found her clitoris and started to suck and gently nip it. Continuing with the lips and back to the clit, he loved her taste and her moans said she liked this.

Then he slowly took his finger and placed it inside of her. Oh fuck!

“Oh Madison, you are so tight.” Adjusting himself he went back to her pleasure. Licking her lips and sucking her clit while slowly moving his finger in and out. She tasted so good.

“I think am going to come,” she said. Her breathing was getting more rapid.

“Madison I want you to come for me,” he thrust two fingers inside and picked up on the speed. A little faster now. He could feel her starting to clench and squeeze his fingers, he knew she was close.

Her body started to shake. He could see the white knuckles holding the couch. What a fucking beautiful site in front of him.

Madison made some noises, “oh my god, mmmm, oh my, mmmm.” She squeezed the side of the couch, she tried not to say much as she closed her eyes letting everything go, letting him make her feel so good.

Madison tried to catch her breath. Her eyes were still closed as she laid there on the couch trying to breathe.

His cock was so hard he knew what he would do when he got home. He had to adjust himself once again before he went to the bathroom to retrieve a warm washcloth for her.

Damn, she is so fucking beautiful. Standing at the mirror looking at himself. He needs to get his cock inside her again soon. He took out a wash cloth, ran it under some warm water and returned to her on the couch. He wiped her before putting her underwear back in place and letting her legs lay naturally on the couch. She was very quiet. She needed to come down from this expereince.

Returning the cloth to the bathroom and cleaning himself up, he walked over to her on the couch. Looking down, pleased with the site before him, he said, “I think you will need some time to think about what we talked about. We can discuss more tomorrow. You’ve had enough for tonight. Let’s get you home safely.”