The Assistant Part X by Lady Crissy

The Assistant Part X - Chain of Command

[Note:  In the last part of this story, Miss Night and aaron's mentor enjoyed a nice lunch and the boy met a new sub that would help to train him....]

The next week for me was spent toling over a very tedious but important contract, checking this and that detail.  I wanted to make sure everything was tidy and to my client's satisfaction before setting up the terms of engagement and beginning negotiations for her new project. Many pages of reading and writing later, I was very ready for a break. Unfortunately, I got buzzed by security downstairs at that moment that a courier was here with more materials, so I sighed and went to the door, and walked out to meet them in the outer office.

Aaron was there at his desk, typing away, and doing very well as he was getting more used to the pretty medium length nails he now wore. The click, click, click of them on the keyboard made me smirk as he stopped to look up with a smile.  "Yes, Miss Night?" he asked, standing up and smoothing his skirt.  He was wearing a pretty black pencil skirt today, white blouse with a bow neck piece.  

His hair had grown out a bit, but was still covered today by a very natural looking wig and he was much better about not touching and adjusting it.  It was a bad habit I was correcting him on, with a swift smack of his knuckles with something that stung when I saw him do it.  I had promised Christopher a couple of weeks at least before testing aaron on what he was learning, but I could already see the subtle changes in his movements and the way he held his body when he sat and stood.  That made me happy.  

The elevator opened before I could respond to aaron's question, and a very athletic looking young man in running pants and jacket bearing the courier's logo on the back of it, came in and set a mailing folder on the desk. He greeted me with a smile and nodded at aaron, then did a very quick and subtle double take, no doubt suspecting a little gender bending.  He held out the tablet in his hands with his stylus, but before I could take it, aaron quickly took it and signed for the package, thanking the young man.   The courier smiled and wished us well and sprinted to the elevator to leave me standing there giving aaron a very unhappy WTF look.

"aaron?"  I said, picking up the envelope and opening it to examine the documents inside.  

"Yes, Miss Night?  Did I do something wrong?" his voice lifted a bit at the end with some anxiety.  

"Did I ask you to sign for my packages?"  I looked up and arched an eyebrow.

aaron swallowed and answered, his eye lowered, "No Miss Night, you didn't.  I just thought..."

I cut him off before he could finish his answer.  "SHUT.  UP."   I stated firmly and sharply.  I turned on my heel and went back into my office, and stopping and standing at the open door.  "I can see you need another lesson, slut. Get the hell in here,"  I ordered,   I shut the door as soon as he passed through it and grabbed him by the back of his neck.  I drug him over to the back of the desk and stopped.

I let go of him and placed the envelope down on top of the desk.  I opened the bottom drawer of my desk, pulling out a pair of cuffs.  I turned the boy around roughly, and put the cuffs around each wrist one, then the other, snapping them each closed in turn.  I heard a quick cry of surprise, but he was smart enough to remain silent.  Turning him back around to face me, I used both hands to quickly reach up his skirt and pull down the girdle.  I let it fall to his ankles and hiked up his skirt to reveal what I knew would be a very hard cock.  I smacked it once, twice with my open palm and reached into the desk drawer again.   I pulled out a cock ring next that was fitted with a small vibe and expertly placed it around him.  More difficult with him already being hard, but I was determined.  I turned it on.  His eyes flew open and he let out what sounded like a small shriek.  

I pushed him down to his knees then and watched him almost fall to the floor with a gasp. I pointed to the space under the desk.   "Get down in there, kneeling and face the opening, boy,"  I demanded, watching him scramble as fast as he could to comply after hearing the aggression in my tone. I slowly sat in my chair and shook my head as I looked at him, hunched up under there.  The sound of the vibe and his short breaths blended and reached a very entertaining rhythm.

Taking a deep breath, I pushed my chair in toward him, and slid my knees around the boy, who was kneeling as still as he could in that tight little space.  I reached under and held the back of his neck, pushing his head between my legs so that he was under my skirt a bit.  I squeezed my thighs around his head.  I heard him then moan deep and long, trapped there between my legs and oh so close to my sex.  I slid my hands back up to the desk to open the envelope.   I put all the pages on the desk and ignored the muffled moans and whimpering for a moment.

"Listen very carefully aaron.  I am going to work, and you are going to be quiet.  If you cum, you will earn another month long chastity period, so I don't suggest it."   I waited and heard the boy respond, saying something so muffled it couldn't be understood.  I took it as understanding.  What else would it be?

"Oh, and slut?  I bet you won't forget being so close to my pussy you can almost taste it."  I chuckled, then continued in a very serious tone as I picked up a pad of paper and pen to begin my notes.  "Never take over a work task for me that I have not given to you.  Remember this well, aaron.  This is what power smells like.  It's what control and pleasure and pain smells like.  And it belongs to Me, not you. I make the decisions, you follow orders."  I squeezed my thighs around his head again to emphasize my point, then relaxed them before turning my attention back to the work in front of me.

The buzzing and panicked panting below synchronized to create a very pleasant backdrop.   I love my work.  

  End of Part X