As I have mentioned in the past, my Boss has allowed the few people who work in his department, to work from home then rotate us to work a couple of days in the office. So that we had that “social distancing.”

As our governor has allowed and the sporting world demands, we are starting to open up and the capacity limits in the casinos and the restaurants are starting to improve. Mysteriously how this happens just as we are entering into some of the best times for sports gambling and of course, spring break! That is also the time our little hidden department starts to get busy and the need for full staff in the office will be required.

Yesterday, it was me and the Bossman, alone in the office all day. I only needed to go out into the resort a few times for something. Otherwise it was He and I, alone. in private. He is single (divorced/widowed), he is in my age group. 50-60. Not bad looking, at all. Very well spoken. He fears being in “that age group” and being in middle management, he needs to not make waves, keep his nose clean and to walk the company line if he wants to stay employed long enough to retire with the full pension He was promised when he joined the management team here 10 years ago.

A topic He and I have had numerous discussions about over the couple of years that I have worked for Him. Always privately and always when no other employees are around. Literally, alone!

Yesterday, that’s how He started the day and our conversation. that he has come to “respect” my honesty and my ability to not gossip or be one who wants to know it all. What we talk about stays between us. That told me what I knew anyway, is that he had been testing me for awhile. To see what I would do with certain information about the department and the people who work in it as well as the clients we work with. Ours is dedicated to the people who get free’bies. They gamble or spend enough money here that they get the best of things for free.

He was commenting about how much it will change when everyone will be back in the office every day. The good and the bad of that change. The bad, for him, as he smiled, was the fact that I get his coffee and refresh it every so often. It never gets cold and its never empty. As if I knew when it needed to be done. He wondered if I was a waitress once? “Hell No!”

On the days that I am not here, he has to do it himself and he apparently has gotten used to me and my coffee refills. Not to mention how I keep His desk neat and orderly. When I pass it and He is not in His chair, I naturally lean over and clear the mess up. I know how He piles and files. So I know what not to touch and what to touch. Both habits will cease when we are all back to work.

He mentions my former Boss/Dom and how he now understands why the man gave me such glowing recommendations when the opportunity to move me into this department came up. Actually, according to Him, and He has said this multiple times, that my former Boss/Dom told Him that he would “forever regret not hiring me”.

My Boss, as nice as He is and how He walks the company line. Trying not to say the wrong word or refer to someone the wrong way, has learned that I am not easily offended and have no reason to be politically correct when around me. He really is interested in why I am the way I am. And today He went a little further than any time before to dig without really digging.

We were actually just trying to kill time before some meeting He had to run off to, so we talked. He mentioned that he noticed a few things about me and was curious about them. Ending the rambling statement with the “If I go too far, please stop me” statement trying to cover His ass! I told Him I am an open book. Ask and I will answer. Not telling Him I’m like that because my Owner told me to be. But He didn’t need to know that part, yet!

He was curious on my friendship with Master Chase. He has seen that I ride in with Him most days when I work then I am picked up by my Master “husband”. When He knows that I do drive and that I do have my own car. I will occasionally do drive myself. Just that during this Covid thing, my “husband” works from home and needs a break. So He likes to get out of the house, come down on the Strip, gets me and we go out for a late lunch before going home.

As for Master Chase. My story is that He is a dear friend of my Owner and lives close to the house,. So we agreed that I would ride in with Him and then go to lunch and home with my Master. Not using those words, but the same story. Occasionally, I will also go to lunch with Master Chase because he is a “friend” . My boss liked that answer. Telling me I am so “old fashionably proper!” He loved that, He liked the way my “husband” looks after me. So do I!

After he had returned from the meeting, we continued the conversation. This time He was wondering about my dress. The fact that I only wear skirts and blouses. He likes the feminine look, but we agreed that most women of “my style” (my being fat/fluffy) never do it right. He seemed surprised that He has never seen me in pants or leggings. “Not that is a bad thing” was His follow-up. Again, covering His company ass.

I complimented Him on his observation of what women wear, not all men do it the right way! We had a nice talk about women who have some curves and how they don’t have the support of their man to make them feel pretty, so they really don’t care how they look to others. I was soo wanting to be open and honest with Him to tell Him that I dress this way because my Owner tells me to. He wants His slave to look pretty for Him when she is in public. As His slave, I represent Him in all that I do… But I didn’t. I only said that my husband has instilled in me the self-confidence to want to look nice for the people “who are important to me”.

He seemed shocked that I would refer to Him as being important to me. That led us to the fact that I seem to know when to talk and know when is the best time to not speak. He noticed this mostly in the meetings we attend together. I told Him I had great teachers in the proper ways of business communication. Yes, my Owner has a mean flogger that has been used on me when I fail to learn when not to speak! That point i made in a comment about how I usually shut up when HE has something to say. As a respect that I have to someone in authority over me. (Dang, I know my company speak! )

He still isn’t sure about my past. From Fashion Retail management to maid to now Administrative assistant in special promotions? That “fall from grace” going from retail fashion management to a hotel maid? I reminded him that it was a maid at a Five Star Resort. And I got that job because of my Husband’s connections and that was the entryway for me to where I am now. Not to mention that being the maid was only part of the job. Sucking my boss’s cock every morning and cleaning His home naked every Thursday is how I got to be here!

So maybe I did use my female skills to climb the corporate ladder. But why stop here? He wanted to know why I haven’t sought bigger and better positions. I’m loyal to people I respect. if that was an answer. I gave it to Him. He smiled. I figured the truth would send Him over the edge. To say that my Owner doesn’t want me to go any further, may get one of us in trouble.

We even got into a conversation about women “my size” and finding adequate bra’s. His last girlfriend was a 36DD and He said the nice women, like the kind that I wear, are not cheap!! I let it slip that to save money I don’t buy panties. I had to. I just need to see if He would react. He did. He blushed, smiled, and even turned away for a minute…

Since I am allowed to wear a bra for work, He did not see my now hard nipples. But I knew I was wet between the legs. Thankfully He was called away and I could go to the ladies’ room (with permission) and dry off!

My Owner still has not given me permission to open up to Him. But to continue being the loyal and submissive secretary. He, like I do, thinks that my Boss really knows, He is just not relay sure how to ask. I may need help on this from my former Boss/Dom. Once we go back to full inhouse staff, I will miss these conversations. More importantly, i will miss my service to Him.