SOLD!!! – Pt. 10

The envelope took me to a parking lot of a local PR firm. It was an old, upscale place that was stodgy and absolutely reeked of money. I was there to meet Annalisa Sherrill, who was a socialite & local philanthropist. The info in the card told me that our session was to take place at her workplace & her home, and she wanted something that was…”unique,” But I was up for it. I texted the number, saying simply “here” and after a moment she responded “stairwell”. As I approached, she let me in.

It was nearly 6pm, but Ms. Sherrill held her finger to lips and mouthed “shhh…” then led me up the steps two floors, a quick peek, then she moved me to her office, where I waited. 15 minutes later Anna came back. She walked up and down the hall checking to make sure we were alone and then to my delight she entered the office, and knelt.

“Did you bring the bag?” I asked (as per her wants) and she placed it in front of me. Taking it, I walked over, lowered the office shades and said “Good girl, you may now strip for me.”

Anna was in her 50’s, but was an amazingly fit woman, and looked to be younger, as in her early 40’s if not late 30’s, so yeah, I had an immediate hard-on. Her blouse and skirt came off first. She was wearing no hose on a pair of gorgeous. She had a matching underwire bra that came off next, showing breasts that had some droop but were still quite nice, with nipples that were protruding and pink.

Anna turned away from me slightly, showing me her quite nice ass. Anna had kept toned with regular trips to the gym. Her skin was still quite nice, with only a bit of veins. Now her thong panties were showing me more of them then I had ever seen.

“Leave the shoes on” I said. Annalisa was wearing heels today; I loved the way they made her legs and ass look. She started to kneel again, but with a hand motion I stopped her, then circled, enjoying the view. And it was, admittedly, a very nice view. As per her request, she had her personal phone on a small tripod she had brought. She wanted her punishment filmed for future review!

“Sir, do you like what you see?” Annalisa asked

“Yes. Yes I do.’’ I replied. I stepped closed and brushed one finger thru her pubic hair, making her make the slightest gasp.