Posted in My Writing

Madi and Her Boss – Chapter 5



“Madison, you may sit down,” he said as he walked to his chair behind the desk. “I want to talk to you about something.”

He poured two drinks at the small bar near the bathroom, then walked back to the desk. One glass was placed in front of Madi and the other, he took with him to the other side and sat down. Leaning back in his chair, he took a sip. Holding his glass in his hand, he watched Madi.

Madi sat as he asked her too. She fidgeted with her hands in her lap. She didn’t know what was coming next or what to expect but gosh she needed a release. She was ready to cry. Emotions were wound so tight inside. She looked uncomfortable sitting there while he stared at her. She glanced at the glass not knowing what was in it or what to do with it. And what was in that folder on his desk?

“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.

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.

“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. She never talked with him about her past, where she had been or how she came to this job. How would he know? Madi lived a pretty simple life before this. Maybe that’s why all of this made her so excited.

“First question, Madison, you have worked as my assistant now for about 6 months and I think we seem to fit together well. I would like to offer you something else, something I think you would enjoy trying.”

Did he really say “fit together well” to her? Offer her something? A new position? Did she want to leave him? Wait, she liked it here. She didn’t want to leave him. The pay was good, and the benefits were even better.

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

Wow, could he really see that? Sitting up straight, she folded her hands in her lap. “Okay, so what is it you want to offer me,” she asked.

“Well let me answer your other question before we explore what I wanted to discuss with you. 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.”

Sitting up in the chair, leaning forward and placing his elbows on the desk he was ready to discuss what was on his mind and in the folder.

“Madison, have you ever heard of a submissive and dominant relationship before?” He was watching her closely for any reaction that would make her run. That was not his intent. “Do you know what a submissive and dominant are and how they relate?”

“A what and a what?” she answered. What the heck was he talking about?

“One person is the submissive and does things to please their master called the dominant. The submissive’ s role is to pleasure to the dominant, they belong to them.”

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.

“Madison, slow down, it’s more than USING someone. 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 take great care of my submissive and as you bring me pleasure, I would do the same for you, when you deserve it.”

“When I DESERVE it, what do you mean?” she was so curious yet so scared to know what he was talking about. Her heart was beating faster, and her palms might be a little damp, but her pussy was a whole lot wetter than when she came to his office.

Thank god for the whiskey.

“Wait a minute, do you realize I don’t even know your name? I mean I answer your phone as Mr. Stark’s office, but I don’t even know your first name? Maybe we should start there?” Madi was starting to get some courage and a voice.

“I didn’t realize you didn’t know that” he chuckled. “My first name is Adam, I am Adam Stark.”

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 hard again. She did something to him, he needed to tie her up soon.

“Okay, so would you like to give this dom/sub relationship a try? Let say we start out slowly and work our way into it?” He knew she was game, just needed to get her to see that.

Standing up, he undid his cufflinks and folded his shirt cuffs up his arms. He then walked around to the front of the desk where Madi 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 take release the pressure you’re under, so you can think clearer,” he said.

He started to undo the buttons on her blouse and take the blouse off the shoulders, letting it fall to the floor. 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. 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, “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. 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 it. His hand found her folds and she just about melted right there. 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. Nerves, excitement, arousal, it was all going on and she couldn’t stop this train if she tried. He sat down on the couch in front of her spread legs.

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

“No,” she whispered. Oh god is that what he was going to do? She closed her eyes tight. He was looking at her pussy. She felt so exposed yet so turned on. She wanted to close her legs but she knew he would let that happen.

“Well Madison, I am going to bring you to great pleasure. 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, that you understand,” he said to her, looking at her, waiting for her verbal reply.

“Yes,” she whispered.

Getting the 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 didn’t know exactly what that meant but he liked it and oh, she was turned on alright.

Madi closed her eyes trying to not be so embarrassed and enjoy this moment. Her hands clenched the side pf the couch.

He started to gently lick her inner lips. His warm tongue sent more goosebumps throughout her body, but also made her pussy want him more. He lavished her with his tongue, enjoying the reaction. Her moans were making his cock harder and more uncomfortable. 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, Madi was going to die.

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

“Oh Madison, you are so tight, I can’t wait for you to come on my cock.” Adjusting himself he went back to her pleasure. Licking her lips and sucking her clit while slowly thrusting his finger in and out. She tasted so good.

“I am going to come, I think,” she said. She has been waiting for this moment.

“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, she was close.

Madi couldn’t hold back anymore. Her body started to shake, she was tingling and pulsing and she didn’t know what to do. Didn’t know if she should scream, “oh my god, mmmm, oh my, mmmm.” She squuzed the side of the couch, her toes curled up and she closed her eyes letting everything go, letting him make her feel so good. So good.

Madi couldn’t catch her breath. Her eyes were still closed as she laid there on the couch trying to calm herself down.

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, wiped her before putting her underwear back in place and letting her legs lay naturally on the couch.

After 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.”



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