Posted in My Writing

Madi and Her Boss – Chapter 7

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





Madi woke up the next morning wondering if last night was a dream or was it real. Did her boss really make her have an orgasm? Did he really lick her pussy? Did she have his cock in her mouth? Oh, what did Madi do? She laid in bed trying to see if any of it made sense. She finally concluded that it didn’t.

Having her morning coffee after her shower, Madi decided she didn’t want to go into work today. She was kind of apprehensive to see Mr. Stewart. So, she called in sick and made sure someone would take his calls for her.

Madi laid on her couch staring at the ceiling. She started to replay last night’s events in her head. She wanted to remember everything he said, everything he did. Thinking about it all just made her excited again, so that had to stop. She wanted a clear head to think about this dominant and submissive proposal he made to her.

She took her phone out and started googling the terms he used last night. All kinds of things popped up on her screen. People tied up with ropes, people on some kind of cross, people wearing collars, people crawling behind another person, people using whips and people gagged and blind folded. She gasped and put her phone down. What the heck was he thinking? She couldn’t do this, be tied to a cross and crawl on the floor behind him?

“I can’t do this, who does he think I am?” She certainly didn’t want to face him right now.

Madi decided to go for a walk in the park. She put her clothes on, sneakers too and grabbed her headphones and phone. Maybe this would help her clear her head.

Entering Central Park, she knew exactly where she wanted to go. There was a beautiful, peaceful lake and once she got to the lake she wanted to go sit on the big rock that jutted out over the lake’s edge and look out at the lake. With her music on, listening to Lindsey Sterling, she started her walk to the lake.

When Madi got to the rock she went out as far she could go and sat down. She criss- crossed her legs, put her hands on her knees and closed her eyes to relax. She turned her phone to silent, wanting to just relax and hear the birds and feel the warmth of the sun. Deep breaths helped her to focus and relax. She listened to her breathing in and out. Slowly. Deep breaths.

Madi’s thoughts went to her mother first. What would she think of Madi right now? Madi was raised to be a good church-going girl, praise Jesus and avoid sin. This was far, far from how she was raised. Her parents kept her very sheltered in their small town until her father left them. Then her sister left. Madi moved soon after her mom passed away. There was nothing keeping her there but memories.

But then Madi remembered her mom used to say, “Madison, you have to be happy in life, no matter what you choose to do.” So now Madi was listening to her mom but felt the guilt of trying to explore something new and different. A new career, a new place to live, a new hobby, her mom would have encouraged that, but this? A sexual relationship with a man who would be her dominant? What exactly did that mean? Part of her was curious and turned on by the thought of serving him and that scared her, but part of her thought her boss was so hot she WANTED to have sex with the man, more than what she had already done. She wanted him to bring her to orgasm again. Touch her, kiss her, run his hands all over her. But this time with his cock inside her. He’d be her first meaningful relationship, but would he see it that way?

Sitting on the rock for a while, Madi just enjoyed the warmth of the sun. Listening to the world around her. Then a thought hit her. Madi wondered what would happen if she wasn’t good enough for Mr. Stewart? What if she didn’t give him what he expected. She would have to quit her job, and maybe move away. She couldn’t work for him if he didn’t want her as a sub any more. How could she be good enough? She was young and inexperienced, and he obviously knew what he was doing and what he wanted.

Madi started to cry. Maybe she just needed to look for a new job now. Her emotions were all mixed up and seeing Mr. Stewart every day wouldn’t make this easier. Madi got up, decided to go back to her apartment to start looking for another job, even a temp one, the sooner she got out the better. If she didn’t see him, she could forget this whole thing.

She grabbed her phone to turn her music back on for the walk home when she noticed the many missed calls and text messages. What the heck was going on? Her apartment building had called her? Missed texts from a number she didn’t know. She started to listen to the voice mail messages.

“Hello Ms. Ryan, this is the doorman at your apartment. We have a gentleman here trying to get up to see you, a Mr. Stewart, but he isn’t on your list and you are not answering your phone, so we are not letting him up the elevator. He is very upset so please be advised when you return. Call us if you need anything.”

Madi stopped dead in her tracks, leaned over and put her hands on her knees. She wanted to be sick. He was at her apartment. Damn it. Now what did she do? She thought about sneaking up the stairs and avoiding the lobby, in case he was waiting. Oh wait, the text messages… she opened them up. The same number that messaged her last night.

Unknown: Madison this is Jonathan. Where are you? Why did you call in sick today?

Unknown: Madison, I want an answer – where are you?

Unknown: Madison you need to tell me you are okay? Let’s talk about last night.

Unknown: I am going to find you. We need to talk.

That did it. She sat down right there on the walkway. She laid her forehead in her palms. She started to cry. This was all too much for her.

After a few minutes, she got up, pulled herself together and walked home. She needed to get home and start looking for another job, maybe move, she didn’t know where, but she needed to avoid all of this.

Madi let herself in the stairwell with her tenant key, walked up the four flights to her apartment. When she opened the stairwell door to her floor everything was clear. She walked down the hallway and turned the corner and then her heart stopped, and she froze up. There he was pacing the hallway outside her door. Damn it. Madi instantly turned around hoping he didn’t notice her. He did.

He heard her walking and looked up. “Madison.” He said it very firmly and with anger.

Madi stopped in her tracks and turned around so she wasn’t looking at him. “I don’t want to see you right now.”

“That’s obvious,” he said, “but that is not what is going to happen. Turn around and come back.” His commands made her do it without thinking. Damn him.

Madi turned around and walked to her door, her head looking down at the floor the entire time. She couldn’t look him in the eye right now. When she stopped to take her key out, he took his hand under her chin and lifted her face to his.

“Madison, you cannot avoid me. We have unfinished business to deal with. Now let’s go take care of what’s on your mind.” As a tear rolled down her cheek, he held the door open for her to go into her apartment.


Posted in My Writing

Madi and Her Boss – Chapter 6

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





Oh shit. The look on her face says she found the folder on my desk. Fuck! I can’t mess this up.

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

I poured her a drink and refreshed my own drink at the small bar near the bathroom, 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 as he asked her too. 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 not knowing what was in it or what to do with it. She was worried about something, maybe he scared her off already? Had he 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 other things, he figured this would hurt, so he watched her closely as she picked up the glass ad 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 fir the beautiful woman in front of him, while Madi sounded like a cheerleader on the football field.

Taking a deep breath, he was ready to put his cards on the table, but he had to go slow for her benefit. She was obviously young, naive and inexperienced. He wanted all of her under his control and ready for his cock, but 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. 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, she thinks he was letting her go maybe?

“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. “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. 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.

Sitting up in the chair, leaning forward and placing my elbows on the desk I need to discuss what was on my mind and in that folder.

“Madison, 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 get to her before she gets to the door.

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?

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

Watching the reaction, I am ready to jump for the door.

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 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. You would be rewarded.”

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

“When I DESERVE it, 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 should start there?”

This was a side of Madison I had never seen. She had 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 hard again. 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 give this dom/sub relationship a try? Let say we start out slowly and work our way into it? Try some easy things?”

She is just staring at me, I can tell she is trying to process this offer. 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 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, “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 it. His hand moved the under wear 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. 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.

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 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 pf 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. 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 am going to come, I think,” she said.

“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, her toes curled up and she closed her eyes letting everything go, letting him make her feel 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.

Damn, she is so fucking beautiful. Standing at the mirror looking at himself. He needs to get his cock inside her 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.

After cleaning himself up in the bathroom, 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.”