The Boss

[Fictional] 11/14/2021

By: Kendra Lynn Carlisle

For many years I’ve worked really hard at The Business and done many things to be successful and I love working at The Business. A couple of position came up and The Boss began to conduct interviews. I was really worried but filled with hesitant anticipation since I applied for one of the Lead Positions (position came with executive perks and a corner office on the same floor as The Boss). Since I never meet The Boss, the rumors and legendary myths flew through The Business like wildfire for many years. The one factual rumor was that The Boss has been divorced for two years and was looking for ‘fresh meat’, she even let slip that she really liked guys my age.

The whole team that I was aside of became my cheerleaders because they respected me and loved my leadership.

Later that day, I received a notice of interview order and I go down the list. I’m the last one with the day and time next to my name. There are 5 others on the list from The Boss. I sighed for a bit. The interview is in 5 weeks. Apparently The Boss like to space and spread things out a bit. The team noticed me standing there next to my side office door. Josh, my number two walks over and ask if I was okay. I told him yes. I handed him the notice to read. Josh was excited for me. I told him that I need some help in my interview skills ASAP. I got 5 freaking weeks to be prepared. Josh told me not to worry, he’ll get the team together on this. I told him, we need this to go our way since 1 person was in another division unrelated and another person was from out of State, the other 2 are unknowns, not even with The Business. I must get this massive promotion for the good of The Team and The Business.

Cindy approached Josh to see what was going on and Josh gave her the recap. She summons for Laura our own Interview Gal for our Division. Josh, Cindy, and Laura meet up in Josh’s side office.

An Hour Goes By. I overhear some of what was said from outside. One sentence stuck out, “She can be a Bitch”.

Josh then called me into his office; he and the Team all agreed to work together to help me out with the interview. Cindy then said we’ll meet at her house since her husband went of a camping trip with their son, it will be a working dinner. Her and Laura would handle all the food. Josh then said that Laura will be interviewing you while Cindy and himself will be observing. We’ll do this every week for the next four weeks. I then said, that sound like a great plan. Lets do it. Cindy said be at her house tonight after work at 8 pm. That will giver her and Laura enough time to get the food done. Her and Laura would be getting off at 5:30 pm. I said as leaving out, I’ll be there.

We all got back to work. 5:30 pm rolled around and Laura and Cindy clocked out while Josh and I finished up the reports and then we clocked out 15 minutes after.

Back at Home.

I had to be there in a suit and tie, so I had to throw a shirt in the dryer to freshen it up while I took a shower and re-shaved. While in the shower I kept seeing in my daydreams The Boss in that blue dress of her’s. DAMN! she’s amazingly sexy. I kept telling myself that I would do anything to get this promotion. Even though she was much older, the wondered of bedding her became relentlessly on my mind. The Boss shown a little aging in her face but not much; however, she showed no signs in her bodily physique. She still looked like she was mid-30s. Nicely tight and rounded ass, and legs damn’it those legs of her’s. Lets not forget about her breast, WOW! She looked like she really kept in shape.

6:30 pm rolled around and Cindy was 15 minutes away. I finished showering, shaved, and grabbed the shirt out of the dryer, then got ready. I threw on my suit and buffed my shoes.

As I headed out the door, The Boss calls my cellphone. BOY! Talk about PANIC. I politely answered, “Hello Madam”. The Boss told me, “The 2 out of State people submitted their resignation from being considered. The other two individuals have also decided to not be considered. However within 2 weeks that I would still have to interview for the position. The Interview will not be in my office but at my home. You will have security arrangements made for allowed entry onto the estate. Mr. Redding you will also need to have a weekend luggage packed, that we will be going via private jet to my Florida estate neighboring Mr. Trump’s Mar-a-lago estate. Do you understand these arrangements Redding?” I replied to The Boss, yes’mam I do. She said, “I really love that answer”. The Boss then told me, “Have a nice rest of my day”. She disconnected the phone call.

WHAT A CHANGE OF PLANS! HOLY CRAP! SHIT!

HUGE SIGH!

CHAPTER 2

The Team is not going to like the change but the rest of the news they will. I’ve still gotta work on this interview. I cannot fuck this up.

The Drive to Cindy’s.

Arriving at Cindy’s House.

Getting out of the car, as I walk up the steps the front door opened and I was met by Josh and the other team member Daniel, he came to help out with the food since his other life he worked as a Chef. We all greeted each other with a hug. I told everyone the news that I received from The Boss. Both Cindy and Laura got emotional and Josh was very excited. I also told them that the interview was in 2 weeks. Daniel said not to worry relax. Josh affirmed what Daniel had said. Both Cindy and Laura composed themselves and were determined to get me ready for this big day.

We sat down and ate, Daniel really should have his own restaurant. He’s cooking is amazing. The wine was even good.

After, they had me come into the living room while Laura played the part of The Boss. We must have done this 5 times in a row. Each time a little different. Each time I tended to get a little better. After about 3 hours went by the Team met off to the side while I enjoyed some more wine. Laura told me to come over where they were. She told me that I was very good but more practice than we can fit in tonight. We’ll be meeting Friday after work at her place since she lived alone after being fresh off a divorce. Heck, I tried to get with her but she’s not interested in men. Laura knows how I really feel about her but I respect her and don’t want to ruin our friendship. Cindy has that mom attitude. She told me just like a mom, Boy ya going to get this position. After another 45 minutes around the 11:00 pm hour we left Cindy’s place.

A long work week went by.

Next Friday rolls around and we did the Interview Tutorial again at Laura’s place. The same team arrived. I had to tell Daniel if I get this position that I was gonna get The Boss to open up a Buffet Style Cafeteria where he’d be Head Chef and get to hire who he desired. We all needed real and well cooked-prepared food to eat at lunch time. The Team agreed wholeheartedly. The 1st Floor of our 4 story office building had almost half of the backside unused and that would be a great place for the Cafeteria. It even had a dock for loading and unloading.

We ate again and repeated the Interview Test on Monday night. All of that went much better than before. The Team was very surprised by how much better I’d gotten. I think it was the driving determination of a a very sexy Boss Lady. Cindy, like a mom noticed that in my eyes. She took my hand and asked, “Hun s it The Boss you really like? Be honest now.” Laura looked at me too with the same asking eyes. I…yes it is, I have a love crush on The Boss. Josh and Daniel burst out, OH FUCK!

That’s when Josh said, we gotta go into over-drive on this one team. Daniel agreed. We got until the Wednesday after next. Josh agreed his place Monday night, same set up. Daniel cleared his schedule and Cindy made arrangements with her husband and Laura was naturally free on her schedule. Cindy’s husband even wished me luck and supported me in all of this.

11:00 pm rolled around again and we we’re all getting tired and needed rest, so we broke and went home for the weekend.

CHAPTER 3

Saturday morning came with a bright dawning sunrise. Things seemed so peaceful. I get a knock on my front door. I opened it and standing at my front door was a large muscle-bound security man. He stated, “Sir, The Boss sent me to deliver you your security pass credentials for Wednesday after next. Oh, by-the-way a slight change of plans, you’ll need to pack luggage for 2 weeks. Your place will be looked after and your utility bills and rent payment has been paid by The Boss”. He also stated to ask for him, Big John when arriving at the front gate. Good day Sir”.

WOW! I was impressed. Seems as if The Boss has already made her decision doing all of this for me. I’m damn gonna be ready for this one.

All weekend pictures of The Boss kept flying through my head.

Yeah, those types of pictures. In my sleep it got even more erotic. Whatever she wants I’m gonna please her with. Not only for the Team but for Her, I have to land this promotion. I had to go to the Golf Range & Club to get my mind off of all this before I went bat-shit crazy. I loaded up my clubs and gear. I called Josh and left him a message to tell him where I would be. Getting to the Golf Range, I received yet another call from The Boss. She asked, “Redding, what’s your clothing size, I would like to buy you something very special for our Caribbean Trip. Yes, we will be going there after gonna Florida.” I told The Boss make it an XL Bottom and XXL Top. The Boss quickly disconnected before I could even ask a question.

I really gotta club all of this out of my head now.

I spent about 2 hours driving golf balls when Josh pulls in and sets up in the next driving slot next to me. We chatted and I told him that I’d be going with The Boss to the Caribbean with her for 2 weeks. I also told him about the Florida trip as well. He was blown away. We ranged about 3 hours while chatting away. I told him about my love crush on The Boss and all the might dreams I’ve had of her.

This woman haunts my dreams at night is such a good way. I really don’t know what she sees in me that extra special to be treating me with a Special Trip and Extra Special Accommodations at her estates. I asked Josh, “Do I have something written on me somewhere that says I’m the one?” Josh just nodded no. Even Josh hoped this would all work out. We both broke from the Golf Range and walked over to the Pub next door for just a few drinks. After we had those drinks to take the edge off of the long work week we’ve both had went went our ways back to our own places.

I get a call from Cindy and Laura back to back asking if I was free for one more Test Run but a brief one. It would be at Laura’s place but just her, Laura, and I. This was feeling like an Incoming Big Sister Talk. I said yes. I asked; when? Cindy said tomorrow night. Laura sounded concerned about me. I told her that I was fine. We disconnected.

Another night home alone yet to dream again. All I could do was to dream about The Boss. I even pleasured myself to the point of having a masturbated ejaculation like no other time. The pressure release was amazing.

CHAPTER 4

Tuesday morning and it was back to work. The whole team just worked as normal not giving any hints or clues to others what was really going on. 5:00 pm rolled around and we all clocked out. I told Josh that I had an engagement that was private and would be unavailable tonight. I went home got out of my work clothes and took a shower, nice hot one too. I just put on some shorts and a t-shirt, and my sandals. I fixed me something to eat and drink. Laura then called me to tell me to come to her place in 30 minutes. We disconnected.

I fetched my car keys and wallet then left out for Laura’s place.

When I got to Laura’s I saw Cindy’s car and parked by her. I get out and go to the front door where Laura greeted me wearing some seductive lingerie. Cindy was wearing her regular mom shorts and shirt with sandals. Laura asked if I wanted anything to drink, she had wine. I took her offer for some wine. We all sat around her living room, I sat on the sofa. They both looked at me for a few minutes then asked about The Boss. First it was Cindy just like a mother would. I felt like I was her son being interrogated. Laura said, we want to know how you feel about her. Please tell us. I gave in and told the truth about my love crush. Both Cindy and Laura were gushing blush. Laura asked, “You know what this means right?” I’m not good at reading people so I said, No. Laura said The Boss picked you out because she has the same love crush on you. I looked at Cindy like a son would look at his mother trying to affirm the truth. Cindy said, Laura is right. Laura said, she really wants to have sex with you at some point. They began to smile because they knew the look on my face. Cindy told me the reason why it’s just us three is because I’d need some help with the flirting and physical flirting part. Cindy would be the verbal coach and Laura would be the physical coach. Laura said, “don’t worry about me, I’m not into men currently, I like women better.” She then turned and looked at Cindy and said to both of us, “if I-Me gets this position that I-her would eat Cindy’s snatch in front of You-me right here in her place”. Cindy smiled at Laura. I looked at Cindy and she told me that she was bi-sexual and her husband knew.

So, we worked on all the physical coaching aspects of flirting. I even got to see Laura and Cindy naked for the first time. I even got a blowjob from both. Those two even gave me a preview of eating each other’s pussies. All of that was very relaxing and it really helped me prep myself for what’s to come. Cindy even told me to make out with her, that her husband did not mind it at all. Her pussy for intercourse was off limits though and that left me with fucking her anally. It was very nice. The same with Laura, she was very nice as well. Both of them told me that I was ready for The Boss. They taught me all the moves and sweet spots. I give them both kisses goodnight and left them alone together.

Wednesday after next arrives and I was told by Josh that The Boss wants me to clock out at 12 Noon and be at The Boss’ Estate at 1 pm. Thankfully I had everything packed up in the trunk of my car. Shit! 12 Noon came so fast. I gave the team all hugs. Both Cindy and Laura smacked my on my booty and told me, “Go Get Her Tiger”. Josh was like, WHAT? They both winked at him.

The ride to The Boss’s Estate.

CHAPTER 5

Arriving at the front gate I remembered what Big John had told me to do. I told the security guard Big John’s name and he quickly made a phone call. The security guard quickly opened the gate for me and told me to have a wonderful time Sir. That was very nice of the man. So, I proceeded into the property.

I had another flashback of The Boss in that sexy blue dress. I knew, I had a strange feeling that my life was about to change greatly. I began to feel more bold and braver than ever. I was a bot nervous but I had learned how to mask that. As I pulled into the drive leading to the front entry I could see Big John and 2 others standing waiting for me.

I quickly parked and got out. Big John said, “Welcome Sir, I’ll take your keys and the staff members will get your luggage. The Boss is waiting inside for you”. He escorts me to the front door and lets me in.

Talk about freaking fancy! WOW! Double stairways! WOW! I was approached by the maid of the house and was then escorted to where The Boss was.

I am taken to her Office-Study to where she stood with that darn sexy damn blue dress.

She greeted me with a hug and a customary pecking kiss on the cheek to which I copied and did the same with her. The Boss had me to sit in the chair in front of her desk and she took her seat behind the desk. “Mr. Redding, do you know why I already chose you?” I replied as honest as I could with, No’mam. She smiled and first applauded me on my southern manners. She then told me that she and my mother where best friends growing up. I looked shocked and she saw that I was. “Oh, by the way, please call me Anna, you don’t have to call me The Boss any more”, she said. That’s an order. I asked Anna about her and my mother. Anna said they went to high school then a little college but that’s when my father and mother met. We both went our separate ways never to really meet up again. Anna said that she’d done and extensive background check on me trying to find out if my last name matched up. She even had a former – veteran FBI Agent on the case. I sank in the chair. (I was doing everything wrong we’d worked so hard at over the past weeks.)

Anna told me that she loved the hard work and my southern ways, that she’d been noticing me at work. Anna then offered me the position plus to be her Personal Assistant on top of all that. It pays $245,000.00 annually with Business perks and other benefits. Anna even said that those final expenses from my mother’s funeral are all taken care of. That’s where I began to cry. Anna quickly got up and rushed to console me. “Oh honey, I know you still miss your mother, she was like a sister to me, and that’s why I chose you. You deserve this and so much more.” I was a grown man weeping like a little boy. We both hugged for a while. After drying my eyes and composing myself, Anna asked me about my love life. I replied, “What love life? I have none.” Anna told me that I was way to handsome to be alone and why a female would not want me is ridiculous. Before Anna could get another word out, I had to confess to her about my feeling for her. I said, Anna, I’ve had a longstanding love crush on you. I’ve held it inside of me for way too long. I’m in love with you.” Anna took a very deep breath and continued to breath heavy. Anna, The Boss was speechless. I told her that all I could think about and dream about was her. I looked her in the eyes and told her that I’d do anything to make a relationship work. Anna, The Boss was emotional for the very first time. Anna looked at me and asked, “You would? You’d do anything?” I told her Yes’mam I would. I took a minute for Anna to respond. She said, “I have to confess something to you as well. I’ve had a love crush on you as well”. I told her that I heard about her nasty divorce and that I would never cheat on her and that my loyalty to her would come absolutely first. Anna then said, “well, we got that Caribbean Trip in a few day, we can see how everything goes down there and here.” She’d paged the Butler to come and have my luggage brought to her bedroom, there’s a change of plans. (In the back of my mind, I was saying, WELL! Cindy and Laura are going to eat each other’s pussies LOL)

Anna told me to come around her desk and sit on top. I did as she requested. She began to kiss me and caress me all over. She even grabbed my crotch and began to rub. Then she took to my neck and gave me a biting sucking hickey to mark her property. (hey guys, if a gal does this, you’re her’s). Anna told me the rest come tonight in the bedroom. She gave me permission to call my team at work to let them know that I got the promotion. She knew waiting 3 weeks would kill them. I had to step out on the back patio to make this phone call to get good cell service.

As I found my way outside, the Butler, his name is Sam asked me if I needed anything to drink. I kindly told him, Yes Sir, a good Jack and Coke please. Even his eyes light up. I guess mother’s southern hospitality does work. LOL!

Sam brought my drink outside and I gave him a $50.00 for a tip. He shook my hand very firmly. I told myself Anna has real good people working for her. I quickly did a group video call to the Team. Josh, Daniel, Cindy, and Laura all were jumping for joy. I told Daniel, making in my mission to getting him Chief Executive Chef at work and him his own kitchen and dinning hall. I told Josh, Buddy, you are now my Co-Lead. For Cindy, I promoted her to Chief Team Leader, and Laura as her Co-Chief Team Leader. Then I told both Cindy & Laura, “Well, I guess the two of you got something to do when I get back home”. That left both Josh and Daniel in deep suspense. Cindy & Laura giggled their asses off like like girls. Should have seen the looks on Josh’s & Daniel’s faces. LMAO!