My New Boss

Copyright M.C. Questgend 2017 – all rights reserved

Reproduction and copying by any means is not allowed under copyright law. This is a work of fiction.  Any resemblance to characters, living or dead, business establishments or events are entirely coincidental.

WARNING: This book contains material of a very explicit sexual nature and is intended for adult audiences only.  The author does not condone unsafe sexual practices. 

I got up earlier than normal this morning. Today was a big day for me, and a day I had been waiting for the last three months. You see, today is the day the announcement is made of the new Director of Information Technology. I have been the supposed front-runner since the position was posted, so while I was expecting to hear my name called, I was trying very hard to maintain a humble and professional attitude until it was made official.

I got to the office and was greeted by the other members of my team who were also anticipating the announcement. I’ve been with the company for about ten years. Coming right out of college, I turned down a number of opportunities to go to other companies, because I felt this company was loyal to their employees. That loyalty was never questioned… until today.

“Hey, Mike. Big day today, huh.” Jerry said.

“Well, I guess we’ll see,” I said staying optimistic, but realistic at the same time.

I continued the morning like any other day, following up with my team on current projects. Of course, it accompanied a little smile this time. After getting status updates and finishing up the day, I got the call I was waiting for.

“Mike, can you stop by my office before you leave for the day?” CTO Frank Miller asked.

“Sure, I was just heading out,” I replied.

I almost sprinted down to Frank’s office, stopping a couple of yards short to catch my breath. I stood at the open door waiting for Frank to get done with his current meeting.

“Come on in Mike,” Frank said.

“Thanks, you wanted to see me,” Mike replied.

“Yeah, Mike. Have a seat,” Frank said, “This is Brenda McConnell.”

“Ms. McConnell,” I said.

“Mike,” Brenda replied.

“Mike, the reason I asked you here was to let you know that we had to make a decision regarding the new director position,” Frank explained.

“What does that mean?” I asked.

“What it means, is that while we value and appreciate everything you have contributed to the company, we really felt that we needed to go in a different direction,” Frank explained.

“Excuse me?” I asked.

“Ms. McConnell has been selected as the new director,” Frank said.

“What?” I angrily asked.

“Mike, listen I know you are disappointed, but we felt the best place for you to be was manning your team, on a more hands-on basis,” Frank explained.

“Disappointed, Frank? Are you kidding me?” I asked.

I completely lost it. Describing the ten years I had given to the company and that it was unfair to bring in someone who doesn’t understand what we do here. While I was blowing a gasket, Brenda simply sat quietly.

“Mike, you have an important role in the company and we want you to continue to be a part of our team,” Frank explained.

“While I appreciate that, you need to understand that I have stayed here for ten years because of the loyalty this company has in its employees,” I explained, “That loyalty is no longer there. I will continue to give you the effort I have always given you, but understand, that I will be looking to opportunities elsewhere.”

The next day, I came into the office with a much different demeanor.
Something my team noticed and somewhat expected – although they didn’t expect me to stick around after they learned what happened. Many of them cornered me in my office to get my side of the story.

I did my best to convince them the decision was made for the betterment of the company and no matter my personal feelings, we all had to accept the decision and continue to do the best job we could. While they all understood, they clearly didn’t believe that I was okay with the decision. As our team meeting was ending, Brenda McConnell politely interrupted.

“Mike, do you have a few minutes?” she asked.

“Sure, we are finishing up here,” I said.

The team left clearly displaying their displeasure with the new director.
She came in and admired the decor of the office before sitting at Mike’s desk.

“Are you feeling any better today?” she asked.

“I’m fine, how can I help you?” I asked.

“I really hoped we could talk and have a clear understanding of how we can work together,” she explained.

“We are fine. I have a job to do and anything new you bring to me will be handled by me and my team,” I replied.

“That’s what I want to talk to you about,” she said.

“What do you mean?” I asked.

“You want the real reason why you were not promoted?” she asked.

“Sure, why not,” I replied.

“There are three words that every good leader should know and understand,” she explained, “Orders, Responsibility, and Accountability.”

“I know that,” I said.

“Do you?” she asked.

“Of course,” I said.

“I don’t think you do,” she explained, “you’re clearly accountable for yourself and your team, but what you are missing is that while you can be responsible for your own actions, you don’t trust your team to hold them accountable and responsible for theirs.”

“I don’t think you understand my team,” I said.

“Your team is not in question, you are,” she said, “Have you ever let them fail?”

“My team doesn’t fail because we work together,” I said.

“True and that makes them a good team, but to make them great they need to know what it is like to fall down and fail,” she explained, “I did some checking and noticed that when your team is under the gun, you step in to ensure things get completed on time even if that means you come in and work on it alone.”

“What’s wrong with that?” I asked.

“Nothing, but if you want to lead, you have to be able to pass on the responsibility to the team and give them marching orders. You don’t even take orders given to you,” she said.

“I take orders every day,” I said.

“No you don’t,” she explained, “Frank comes in and talks to you about something he is thinking about and you offer your ideas and he lets you run with them because he trusts you. I don’t think he has ever come in and given you an order.”

“Maybe it’s because he does trust me he doesn’t have to order me around,” I said.

She then got up from the desk and walked around me standing by the door to the office.

“Do me a favor, think about what I said and before you leave for the weekend, stop by my office. I have a proposition for you,” she said.

“Proposition?” I asked.

“I’ll fill you in when at the end of the day,” she said as she walked out of the office.

The rest of the day I thought about what she said. Thinking she might be right. I never did take orders much less give them. At the end of the day, I was getting ready to head out and walked down the deserted sales floor to McConnell’s office.

“Ms. McConnell,” I announced myself.

“Come on in Mike,” She said.

She walked behind me and shut the door to the office and asked me to sit down.
She then walked around me and sat up against her desk.

“Did you give any thought to what we talked about earlier?” she asked.

“I did,” I replied, “and maybe you are right, but there is a lot to be said about loyalty and trust in your team no matter how big or small it is.”

“Maybe, but if that were always true, this would be your desk and your office,” she replied, “You have to learn how to take orders so you can give them.
You have to be able to give them so your team knows what they are responsible for.”

She stepped down from her desk and sat in the chair next to me.

“How badly do you want this office?” she asked.

“I don’t think that matters now,” I replied.

“What if I told you, you still had a shot at that chair?” she asked pointing to the executive chair behind the desk.

“I’m not sure I understand,” I said.

“I’ll be honest, this job is not that important to me and clearly means more to you,” she explained, “I’ll make a deal with you. Give me 24 hours to assess how well you can take orders and if you can follow my directions, I will walk my resignation into Frank and recommend that you are the right man for the job.”

“Are you serious?” I asked.

“Absolutely,” she replied.

“Why?” I asked.

“I see something in you and you care about what goes on here, but you don’t know everything,” she said, “If you can prove to me the department can follow your orders – by you following mine, then I will be convinced.”

“What do I have to do?” I asked.

“Come out to my house tomorrow and I will lay out all the details,” she replied as she handed me her address, “Just remember, you have to convince me. If you can’t, I may just have to stick around for a while.”

She stood at the door as I walked out of the office. I was a little concerned about what she had in mind, but I was more interested in getting that promotion. The next morning, I got up and dressed, as it was any other day. I drove about ten miles out of town to what appeared to be a large farm. I drove up the long dirt road, to a huge house. I got out of the car and rang the doorbell. To my surprise, she didn’t greet me.

“Good Morning, Mr. McConnell?” I asked.

“I am not Mr. McConnell. I am Ms. McConnell’s butler,” The suited gentleman clarified.

“Sorry about that,” I replied.

“Quite alright, you must be Michael. Ms. McConnell is expecting you. Won’t you come in?” he said.

I was escorted to a large living room area overlooking the back of the property.
The place was filled with a number of pieces of expensive art and furniture. It made me wonder why she went after the director job in the first place.

“Ms. McConnell will be with you shortly. May I offer you a refreshment while you wait?” The butler asked.

“Sure, coffee will be great,” I replied.

“Very good sir,” he replied as he walked away.

I continued to admire the decor and the enormous view of the property before the butler returned.

“Would you like milk and sugar in your coffee sir?” he asked.

“Black. Two sugars please.” I replied.

“Very good sir,” he responded, “Will there be anything else sir?” he asked.

“Do you know how much longer she is going to be?” I asked.

“I’m sorry sir, I don’t,” he replied, “Will there be anything else sir?”

“No, I guess not,” I replied as the butler turned and walked away.

After a few more minutes, of waiting, I decided to explore a little more of the house. I walked back towards the front door and made a left to the dining room where I found a long table, laid out with fine china and silver as if a dinner party was going to take place. As I continued to look around, I ran into a young woman in a maid’s uniform.
Startling her, I was then joined by the butler once again.

“Ms. McConnell will see you now,” he said.

“Awesome, thanks,” I replied.

“Follow me, sir,” he instructed.

I followed him to the back of the house, down a long hallway that opened up to an entryway with two large doors.

“Will there be anything else, sir?” the butler asked.

“No, I guess not, thank you,” I said.

“Very good sir,” he said as he backed up and walked away.

I wasn’t sure what to do next. The butler was gone and I didn’t know if I should knock or not, but since I was expected, I decided to walk right in. I walked in to find a large room with an office area on the far right side and on the left was a bed encased in sheer curtains. Directly in front of me were two more large doors. I began to walk forward when McConnell appeared behind me.

“You didn’t knock,” McConnell said.

“Sorry, I didn’t think I needed to,” I replied.

“Patience is not one of your strong suits,” she said as she guided me to the desk.

“I am impressed,” I said.

“With what?” she asked.

“You have a beautiful place here,” I said.

“Thank you, it’s an old family home,” she replied.

She then handed me a folder, which contained two documents. The first was her letter of resignation, which already had her signature and included her recommendation that I be named director citing my talents and abilities to take the department to the next level. The other was a contract.

“What is this?” I asked.

“That is to ensure you and I can communicate clearly about what is to take place over the next 24 hours.” She replied, “Read it carefully.”

It was a simple contract basically stating that for a 24-hour period, I would be tested on tolerance and the ability to accept orders and commands.
It also indicated if I fail to fulfill any three orders or commands, the contract would be nullified, and the agreement voided. I thought about it and figured it would just be a simple test based on specific role-playing exercises and didn’t think it would take an entire 24-hour period, so I signed it and handed the entire folder back to her.

“All set?” she asked.

“Yeah, I guess so, when does the 24-hour period begin?” I asked.

“As soon as you walk through those doors,” she said as she poured two cups of tea.

“No thank you,” I said politely refusing the tea.

“It’s not a request,” she said.

I took the cup and took a sip of the hot tea. It didn’t taste like normal tea. It had a high tart flavor like someone squeezed an entire lemon in the cup.

“I will join you shortly,” she said, “When you are ready, simply walk through the doors.”

“Okay, thanks,” I said.

I waited for a couple of minutes before walking in. I guess I was preparing for any possible scenario that could be behind those doors. Little did I know, what I found no one could prepare for.

I walked through the doors to a dark entryway, with a black curtain in front of me.
When I walked through the curtain, I realized that this was no normal test of leadership, but a dungeon of pain.
I walked around for a couple of minutes to take it all in – satisfying my curiosity then planned on leaving. I turned around to find McConnell standing between the door and me.

“Going somewhere?” she asked wearing a long black robe.

“Yeah, I think I better be going,” I said.

“You’re not going anywhere and you will address me as Mistress Brenda,” She demanded.

“Well, Mistress Brenda, I think you forgot to tell me about all of this,” I said as I began to walk to the door.

As I walked to the door, I started to feel dizzy and fell to the floor, and passed out. I woke up to find myself stripped of my clothes and laying on a table tied at the feet and ankles. From a distance, I heard a familiar voice.

“Mistress, he is awake,” The butler said.

“Very good, leave us,” She demanded.

The butler left the room and McConnell removed the robe revealing a leather bustier attached to black nylons. I became scared at what may come next and I started to slowly try and get out of the restraints.

“Enjoy your nap, slave.” She asked.

I simply laid there silent.

“You will answer me,” she demanded.

Again I was silent.

“That is strike one. Remember three strikes and you will not get the promotion and I will remain your boss.” she explained, “So let’s try this again, did you enjoy your nap.”

“Yes, Mistress,” I said.

“That’s better.” she said, “We are going to enjoy this evening and you will do anything I tell you to do. Do you understand slave?”

“Yes, Mistress,” I said.

She walked away from the table towards the back of the room. I remained silent, thinking that as long as she didn’t ask me anything, I would not have to say anything. She returned with a flogger and gently slapped it against my legs, working it up my thighs and onto my stomach.

“How does that feel, slave?” she asked.

“Fine,” I said.

“FINE WHAT, SLAVE,” she yelled as she whipped my thighs much harder this time.

“Fine, Mistress,” I said as I winced in pain.

She then unlocked the cuffs from my hands and feet and commanded me to kneel in front of her. She gave me several simple commands – from kissing her boots to kissing her lips.
She ordered me not to use my hands unless she allowed me to and I was to remain on my knees until she told me to move.

At one point she simply walked out. I thought about getting up but remembered what she said, so I remained silent and on my knees until she returned. Some time later she returned and had something new to play with.

“You are such a good slave, I think you should be rewarded,” she said.

She brought in the maid who I saw earlier. She knelt down in front of me and looked directly into my eyes.

“You can look but don’t touch,” she said.

She then walked out again leaving the two of us alone on our knees together.
The maid looked over my naked body as I looked at hers still in the maid uniform. She could tell I was getting turned on at the site of her. Her eyes got really big as if she was trying to send me a message. Just then McConnell came back into the room.

“What do we have here?” she asked, “Did I say you could have an erection?”

“No, Mistress,” I said.

“We are going to have to do something about this, aren’t we?” she asked

“Yes, Mistress,” I said

She then grabbed a male chastity harness and locked it to my penis. It certainly killed the mood and didn’t feel very good either.

“Get up slave,” she commanded.

“Yes Mistress,” I said as I struggled to get to my feet after kneeling for so long.

“Come with me,” she said as she pulled the leash attached to the collar around my neck, “Now sit.”

I immediately sat in the chair that was next to the throne she was sitting in.
She then commanded me to untie her boots. As I took the first one off she took her leg and rested it on my shoulder. When the next one came off she did the same thing and pulled me forward.

“Kiss my thighs, slave,” She commanded.

I never hesitated and began to kiss her inner thighs. I started to really get into it, but couldn’t get too aroused as the chastity belt was dictating otherwise.

“Come here slut,” she said as she called the maid over.

“Kiss me,” she commanded the maid.

As I was continuing to kiss her thighs I could see the maid and McConnell making out. This was a great night, except for the clamp on my cock.

“Do you want her, slave?” she asked.

I wasn’t sure what to say, so I tried to be a gentleman and said, “No Mistress.”

“No? So you prefer something else instead?” she said, “Slut, leave us.”

The maid left the room and I was once alone with McConnell.

“Get up,” she ordered.

“Yes Mistress,” I replied.

“Bend over,” she ordered as I stood in front of a padded sawhorse.

“No, Mistress,” I said.

“What did you say?” she asked.

“No Mistress,” I repeated.

“That’s two,” She said as she slapped me across the face.

She then pulled on the leash forcing me down and cuffed me to the horse.

“No slave says no to me,” she said.

She then walked out of the room leaving me exposed. She came back in with a ball gag and strap-on dildo and stood in front of me.

“Open your mouth,” she ordered.

I reluctantly opened my mouth and she pushed the dildo into my mouth.

“Take it, sissy whore,” she said.

I couldn’t say a word as I continued taking it in my mouth, trying not to gag.

“Look at how good you are at giving head you sissy.” she said, “You want more don’t you.”

I didn’t say anything but gestured in approval hoping she would not hit me again.
I wasn’t that lucky. She pulled the dildo from my mouth and went behind me where she whipped my ass repeatedly until I was raw.

She then leaned over on top of me pressing the dildo against me and in one motion pulled the ball gag over my mouth and snapped it to the back of my head. She then squatted behind me and used her vinyl gloves to penetrate my asshole. Starting with one finger, then several until my ass was trained enough to take what came next.

All I could do was moan in disapproval. Not able to say a word, she continued to push her fingers inside me.
She and I could both tell it was getting easier to slide her fingers into me – either because of the lube or because I was beginning to relax… or both. She then unsnapped the ball gag from my mouth.

“Are you ready to get fucked you sissy whore?” she asked.

“No, Mistress please, no,” I begged.

“You don’t want me to fuck you with this hard cock?” she asked.

“No Mistress,” I pleaded.

“Ask me not to fuck you with my cock.” she ordered.

I hesitated at first then gathered the courage to ask her, “Please Mistress don’t fuck me with your cock.”

“Too bad you whore,” she said as she pushed the dildo inside me. I let out a huge scream and began to struggle to get free.

“Shut the fuck up whore, you know you like it,” she said.

“No Mistress, please stop,” I said, still struggling.

“Don’t fucking move whore,” she ordered.

I stopped moving and allowed her to continue fucking me. When she was done, she walked back in front of me.

“Lick your juices off my cock you whore,” she ordered.

Without hesitation, I opened my mouth and allowed her to stick the dildo in my mouth. The gag of taking every inch was now replaced with the gag of where the dildo had been.
I continued mouth fucking her until she was tired and she once again left the room.

I was so exhausted I fell asleep. When I woke this time, I was no longer restrained and the chastity belt was removed. I got up and walked towards the door, which was propped open with a robe on the doorknob.
I put on the robe and walked back into the room to find McConnell also in a bathrobe sitting at the desk on the phone.

“Yes, Frank, I am really sorry, but it is a decision I had to make. Mike is much better suited for the role than I am and he is the better choice,” she said while on the phone.

I just stood there. Shocked and sore, I was still trying to figure out what all of this was about.

“Yes, Frank. My letter of resignation will be on your desk on Monday,” she said before hanging up the phone.

She then got up from the desk and walked up to me and kissed me very gently on the lips.

“How are we doing this evening?” she asked.

“Uh… better Mistress,” I said.

“You can call me Brenda,” she said, “That’s only for the special room.”

“Can I ask you something?” I asked.

“Why did I do this?” she asked rhetorically as she walked towards the bed.

“Yeah,” I replied.

“Instead of me explaining why, let me ask you if you learned anything?” she asked.

“Yeah… I did.” I replied.

“Now you know why I do it,” she said.

She then asked, “Now is there anything else you want to do while you are here?”

She offered me a spot on the bed next to her. Still sore and confused, I sat next to her. She looked deep into my eyes and kissed me deeply on the lips. She then called for the maid.

“I want you to take care of our new friend,” she instructed the maid.

“Yes ma’am,” The maid said as she leaned over and kissed me.

As we began making out, Brenda took off her robe exposing the elegant white lacey lingerie.

“Do you like it?” she asked.

The maid and I both answered, “Yes, Ma’am.”

She then joined in kissing my neck and chest while the maid and I continued.
Both rubbed their hands over my chest and moved down meeting at my groin. They then stood me up and removed my robe. Brenda and I continued kissing as the maid squatted in front of me and began rubbing my penis.

“Do you like that?” the maid asked.

“Oh yeah,” I replied.

She then took hold of my cock with her hand and began stroking me. My knees immediately buckled and the two helped me lay down. Brenda then turned around and hovered her pussy over my face while she and the maid took turns sucking my cock.

“Your cock is so big, Mike. Does that feel good?” Brenda asked.

“Oh yeah, how do you feel?” I asked before using my tongue to play with Brenda’s wet pussy.

“Oh god, Mike, that feels so good,” she said.

Brenda continued to quiver over my face as I pleasured her. While I began getting her wet, the maid continued swallowing every inch of my cock.

“Oh god, you are so good, baby,” Brenda said.

She then jerked off my face and moved the maid into her previous position, while she continued playing with my cock.

The maid, who hadn’t said much, was now expressing her pleasure for my ability to pleasure her. Not saying a word she continuously moaned as she pressed her legs together squeezing my head.

Brenda then helped the maid up still sitting on my face. As the maid held herself up by holding her hands on my stomach, Brenda got up and sat on my cock penetrating her pussy and causing her to scream out in pleasure. They continued riding me while making out together. The maid then got up and helped Brenda up off me.

Brenda then guided the maid to bend over onto the bed. She then pulled me up and offered the maid to me as a gift of sorts.
I pushed my cock inside her and while I fucked her doggie style, Brenda sat down below her, licking the maid’s clit.
I continued boning her until I was ready to cum.

They both squatted in front of me and I came all over their faces. They continued to lick the cum from my cock and each other, playing with it and sharing it as they kissed and tongued each other.

As we laid in bed together, Brenda and the maid fell asleep while I laid between them wide awake… Unable to sleep after the longest and the most pleasurable 24 hours I have ever had.
Eventually, the emotions and physical activity took their toll and I passed out.

The next morning, I woke in an empty bed. I looked at the clock and realized it was already 3 o’clock on Sunday. I got up to find my clothes hanging in the open closet. After a shower, I came out of the bathroom to find the butler waiting for me with breakfast.

As I began to get dressed, he poured me a cup of coffee. The entire experience was too much not to ask questions about.

“Can I ask you something?” I asked

“Of course sir,” the butler replied.

“Does she do this often?” I asked.

“I cannot say for sure, but you are the first gentleman visitor who has been here in a long time.” He replied.

“Did she do the same thing to him?” I asked.

“Not exactly the same thing, but it was an experience I would never forget.”
He replied as he walked out.

Don’t forget to tell me what you thought of this short story. Leave your comments today.

Leave a Reply

Your email address will not be published. Required fields are marked *