The Assistant Part 1x - Field Training by Lady Crissy

[Note:  The last we saw Miss Night and aaron, Miss Night has ordered reservations for her favorite lunch spot with the intention of enjoying some public play....]

I finished the rest of the morning's work and shut down the computer. Slipping my heels back on, I stood and left my office.  I gathered aaron along the way, walking in a pace that I knew would challenge him in his new "uniform".  Admirably he kept up with only a couple of stumbles that I pretended not to notice.

Out in front of the building it was easy to hail a cab quickly.  In this part of town, no one bothered to try to move their vehicle once parked for the day.  When the cab stopped I slipped in with aaron following suit.   I gave the destination to the cab driver and we pulled off to join traffic. My hand moved to rest on aaron's knee, out of the view of the driver.  I could hear him gently swallow and go very still.

I slid my hand up his thigh, squeezing it and sliding it further up and under his skirt.  I let my fingertips and nails brush gently against his skin and watched him fidget in his seat, trying hard to keep his eyes forward.  I dug my nails then into his thigh as I chatted cheerily about the traffic and weather with the cabbie, ignoring the quiet gasp that followed from my toy.

When the cab stopped, I stepped out, paying and tipping the driver, then walked up the short walkway.  I heard aaron scramble out of the car and up the walk behind me, and turned to see him pulling at his skirt.  The host greeted us at the entrance and nodded, smiling.  It pays to be a regular....And to tip well.    The host led us to the back, to a wonderful little patio area.   The doors out to the area were tinted  and there was a stone half wall that gave a little privacy.   I loved this spot, and smiled to myself at some of the entertaining lunches I had had here.

A cheerful smile greeted us as Monica stood and walked over for a hug.  The weather was beautiful, and as always she was stunning in a white linen skirt suit, pale blue shirt under it.   We exchanged greetings and then moved to sit as the host pulled out each of our chairs in turn and presented us with the menus.  aaron was surprised into silence, in no way expecting to see his mentor, but recovered and greeted her respectfully.  We ordered drinks to start, and with a quick smile and nod the host departed, giving us time to catch up.

We both paused and looked over at aaron as he pulled out a chair and began to sit down.   Our cold looks stopped him in his tracks and he stood again, pushing in the chair.  His eyes darted from one of to the other, not sure what to do. I snapped my fingers to wake him up and get his focus.   "Just to be clear, aaron, I would have you kneel here as well. But...you probably didn't pack any extra stockings and I can't have you leaving here looking like a $5 whore that just gave a blow job in the alley."

aaron's face and neck flushed bright red as I continued, "Not that you probably wouldn't enjoy that...."  I narrowed my eyes at him as I spoke.  "You will stand behind and to the side of my chair until told otherwise." I motioned him to the spot, and I watched the boy move quickly to it.   Monica and I picked up our conversation and caught up on discussing work, our mutual friends and our plans for the rest of the Summer.

When the waiter came to take our order, I smiled and it was returned in kind. Christopher was my favorite waiter for very good reasons, and if he was working, the host knew to send him.  I knew today was one of his days to work.  This was no chance meeting.  Christopher was bright, discreet and aimed to please - quite lovely.  Monica and I both ordered light lunches and watched him nod and smile at aaron when we were done.

"Christopher, this is aaron.  He will take some water for now, and I will order for him something for take out when we leave."

"Very good, Miss Night, "  Christopher responded with a smile.  The pretty light red glossy lip shine that he wore just made him even more attractive.

The waiter left to put in or orders and I smiled.  I was looking at Monica but spoke over my shoulder, " So aaron? What do you think about our waiter?  Cute, right?"   Monica chuckled and sipped her daquiri - on the rocks of course.   No frozen froofy drinks for her.

aaron stammered his answer, "I don't know what you mean, Miss Night,"

"Do you speak English, boy?"  I sighed.

"Yes Miss Night,"  aaron replied quickly, finally understanding.  "He's ok I guess MIss."  I could almost hear him shrug.  

I smiled and sipped my drink, going back to chat with Monica until Christopher came back with our food.  I addressed him by name. "Christopher?"

"Yes, Miss Night?"  he responded, placing the last of the lunch order on the table, his presentation smooth and graceful, his nails with the very subtle French manicure expertly setting the table.

"What do you think about aaron back there?'  I asked and tipped my head back in aaron's direction.  I turned in my chair to look as well on the transformed boy standing in back of me.

We watched Christopher look aaron over, taking his time assessing as aaron squirmed and he tried to look anywhere else.  "Not a bad start, Miss Night,"  he stated with a smile.

I stood and walked behind aaron, putting my hands on his shoulders, squeezing.  I slid my palms down his arms and then let them rest on his hips.  I slid my hands over his ass next, squeezing it tight, feeling him shudder.  I chuckled and kissed his neck and biting it firmly, hearing him moan lightly.   I let go of his ass and slid my hands slowly over the front of him, over his pelvis, pressing fingers against the skirt and the girdle underneath firmly.  My fingers pressed in to outline his cock beneath, feeling him hard and wanting under my touch.  I pressed my body firmly to his back as I spoke, my lips very close to his ear.   Monica and Christopher looked on with knowing smiles.

"aaron is on chastity, you see.  So he is very..... motivated to learn. Aren't you, slut?" I said, brushing my lips against his ear.  I continued without waiting for him to respond.  "I did say that it takes a lot to please me, aaron. Fortunately for you, Christopher here knows exactly what I like and can help your sorry case."   I continued to tease aaron's cockhead with fingertips that mercilessly pressed and rubbed his frustrated hard-on.  I could feel him struggling not to tilt his hips toward the touch and felt him begin to twitch under my fingers.  "How fortunate for you, slut."  

Looking over aaron's shoulder, I raised an eyebrow at Monica and watched her nod in agreement.  I moved my hands away abruptly and walked back to sit down at the table with a smirk  "Call me tomorrow, Christopher.  I think this project needs your touch."   I picked up my drink and took a sip of the gin and tonic.

"I would be my pleasure, Miss Night."  he replied with a smile and nod, leaving us Ladies to our lunch and leaving aaron in a very shaken and worried state.  

I love a good Cobb salad.... As well as the smell of fear.   Delicious.

End of Part IX