We keep playing

“Finish getting dressed, Miss Miller,” I decide to stick to the role of the demanding boss, “this is a proper establishment so you need to look presentable.”

“You like me in this secretary outfit, don't you Mr. P?” Alison's soft brown eyes search my face for confirmation that what I have in mind is on the same vein as what she is thinking. “Looking like that beautiful heroine from the book?”

“Oh yes. If it's OK with you, Angel,” I tell her, “for tonight, I still want to explore the innocent young secretary who knows she is in big trouble with her boss.”

“Yes Sir.” She whispers softly, with a knowing grin on her face.

“I imagine an experienced man like you will want to do all sorts of nasty things to a sweet thing like her.” And then her demeanor changes subtlety, she looks a little less confident and her eyes lift to meet mine nervously.

“You won't regret giving a second chance, I promise.” I can feel my cock start to swell uncomfortably in my pants. The dark charcoal-grey suit has been worn just one other time at Fran's funeral, and I try not to think too much about the juxtaposition of the funeral and what I am doing with my sweet tenant. After one final check she stands in front of me like a soldier for inspection. “I'm ready, Mr. Patterson.” She smiles timidly, patting a large rectangular leather bag, “I brought my laptop in case you need me to take notes.”

“Very good Miss Miller.” I try to keep my voice calm, “I'm going to have to assess all of your skills before I decide on what to do with you.” I don't know if she is acting, but my beautiful tenant looks decidedly nervous when she hears me announce my intention to evaluate her skill package. She allows me to take her arm and steer her possessively back down to the nearly empty parking garage. “First, we'll have dinner, and then we'll discus your obvious lack of experience, spotty performance and falsified resume.”

“Yes, Sir.” Alison gulps quietly, “I know I can do this job, if you just give me a chance to prove myself.”

“You know what I want more than anything else from my employees?” I ask as we head to the old part of Hartford and my 'secretary' shakes her head silently. “I look for obedience, if I ask you to do something, even something unusual like accompanying me to dinner, I expect you to do it to the best of your ability and with a smile on your face.”

“Yes Sir.” Judging by Alison's fidgeting, I sense that this poor thing has reservations about absolute obedience to anyone other than her Lord and Savior, but after what we already did in Walt's office, I know she is ready for almost anything. My car is parked by a handsome dark-haired valet in a red jacket and black mask with the Goodwin coat of arms emblazoned on it in gold thread. The young man gives Alison a second look as her helps her out of the car, but my guess is that this is not the first time he's seen a beautiful young woman having dinner with a much older man.

We leave our coats and Alison's computer at the coat-check, and before we head to the nearly empty restaurant I pull Alison aside and press a tube of lipstick into her hand. “I like this shade better,” I tell her, “Go freshen up while I see about our table.”

When my secretary returns I am pleased to see that her lips are now a vibrant red, and that Alison is clearly aware of how much attention the lipstick draws to her mouth. It is not a shade that she would ever buy for herself, but it is the first of several different tasks that are designed to demonstrate that I am in complete control. When the waiter arrives I order for both of us: bruschetta for an appetizer, a steak and baked potato and salad for myself along with a glass of Bordeaux and mushroom raviolis in cream sauce for her paired with a ginger ale garnished with a single cherry. The white-gloved waiter is expressionless but I can only imagine what he is thinking about a man my age with a wedding ring on my finger having dinner with his much younger, very pretty and clearly nervous secretary.

“Good.” I tell Alison as the waiter leaves to get our drinks, “Now, return to the Ladies room and bring me your panties.”

“Mr. P?!” I love the expression of surprise and alarm, but I keep my expression neutral although I let a little sharpness into my tone.

“Miss Miller, you will call me Mr. Patterson or Sir,” I inform her coolly, “and you are defying me for the last time.”