The Assistant Part V - Setting The Bar by Lady Crissy

[Note:   Last we saw Miss Night and her newly hired assistant aaron, she had directed him to visit a Miss Constance in order to prepare for his new position and to carefully think about his choice to accept her offer.]
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I was just opening my first emails of the day on Tuesday morning when my phone buzzed.  I smiled, noting the origin of the call.  I picked up the phone and listened to the voice on the other end.  After a moment, I responded, "Why yes, I've approved it." I listened to the awkward pause on the other end of the line.  "Is there anything else?" I asked rhetorically, then hung up without waiting for an answer.

A short time later there was a knock on my door.  I braced myself and sat back, ready for it. Experiments are always chancy.   The door opened and aaron walked in.   A much transformed aaron, that is.  From his chunky pumps up to his red A-line skirt and smart blazer that matched it in color.  His make-up was simply done, tasteful, with lips a vintage red with just a touch of orange.  With his skin color it looked good, not whorish, lucky him.

Aaron walked into the office, to the other side of my desk, and stood.  "Sit."  was all that I said, still taking in his appearance.   The wig was short, and very natural looking. Constance is an artist.  Aaron sat smoothly, legs together primly and modest.  Since I knew that less than a week ago he had short, well kept straight boy short nails, I knew the new ones were fake.  The color matched the lipstick, a nice touch.  He sat across from me stiffly, as if he was afraid to move much.

"So tell me, aaron, how many pairs of stockings did you ruin before getting this pair on?"  I asked, cocking an eyebrow.

"Three pairs, Miss Night", he responded, a slight sigh in his voice.

"Now that can't be a complaining tone I'm hearing in your voice...."  I began.

"No, Miss Night,"  aaron said quickly.  "Simply learning Miss, its... new."

I nodded, acknowledging the truth in that.  "And hows the girdle feeling?" I smiled, smirking.

"It's.... doing the job, Miss,"  he replied, squirming a bit at the mention.

"I'll bet it is,"  I chuckled.   I saw forward again and looked directly at the boy.  "Listen closely, aaron.  I won't repeat this twice."  I saw him nod and swallow nervously at the change in my tone.

"You will not speak unless spoken to, or given permission.
You will dress for my pleasure, as male or female, at my whims.
You will perform your duties as my secretary unless given instructions that I desire your actions to deviate from the usual vanilla tasks.
When in my presence you will stand unless told otherwise.
You will address all my visitors as Miss, Mr or Ms as directed.
When you are not here serving me in my presence you have only three restrictions - no sex with yourself or anyone else, no drugs or alcohol, and no activities that might otherwise impede you from your commitment to serve me."I paused.

"Are we clear?"  I looked at him and waited.

"Crystal clear, Miss Night,"  he responded after a short moment, his face flushed bright red.

"Good,"  I stated simply and smiled.  After a moment, I continued, "Because, if you violate the chastity rule, I will punish your cock until you wished you no longer had it." His hard swallow was audible in the quiet office.

"Now then, your assignments are on your desk up front.  Ask any questions you need to get the job done. "  I waved him away with my hand and opened a file on my desk.   I heard the door open and close and I got back to my work.

The day progressed fairly smoothly, with aaron coming in a couple of times, but otherwise he was catching on well.   Time to raise the bar.  "aaron!"  I called out, and quickly the door opened.  He almost stumbled in the heels as he made his way quickly over.

"Yes, Miss Night?" he asked, as he on the other side of my desk.

"Go down to the cantina and get me a coffee.  Three cream, two sugar."  I placed the order and looked back down at the notes in front of me.

He was still standing there a moment later when I looked up again.  The look on his face was priceless.  "Go.  Now,"  I said, raising an eyebrow and watching him until he left and closed the door behind him. There should only be about a dozen people down there.

Separating the sluts from the subs, one of my favorite games.  I smiled and went back to my work while I waited.

End of Part V