I sell myself to save the business - and the business i get into!
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. “Annalisa, I am going to expect you to do what I tell you, without question. You have a ‘No’, but if you use it, this session will end, do you understand?”
She nodded quickly, noting that I took a black leather paddle out of the bag and then out of the package. I waved it about, testing it’s weight, and nodded approvingly.
“Bend over your desk, with your hands directly under your forehead, and your forehead on the edge of the desk. I want your pretty breasts dangling. Feet apart enough to see that pussy of yours”
“Please, can’t we talk about this first?”
I knew she would play this game. “Bend over the desk, or I’ll take that as a No, & leave. The choice is yours”
“I know, but now that this is so, well…’real,’ she said
“You made the choice real when you made the appointment, just as you made it real when you let me in and gave me the paddle. You know what was coming, so quit stalling. It is, after all. What YOU want.”
Annalisa Sherrill glanced at me with a knowing smile & bent over my desk as directed. As per her previous request I checked the phone’s angle. She was in it, but not my face. Perfect. I drew back and gave her quivering ass a forceful swat. She screamed as her ass gave to the paddle and it immediately started turning red.
I said “Scream loud enough and you’ll draw the night watchman. You can explain what’s going on while I go home. Now bend back over.”
She did as she was told and in quick succession I hit the same ass cheek four more times. Not quite as hard as before, and slow enough so I could still see her ass give to the paddle and then spring back, each swat adding more color to her Annalisa Sherrill’s shapely ass. She had only grunted and squirmed with each swat, but when I paused she quickly asked if we were done. I told her to stop talking and I would tell her when we were done.
I worked her other cheek the same way and after a total of ten swings her ass was red and beautiful. At this time, I also stepped slightly to one side, so I could see her breasts jiggle with each strike. Annalisa was whining very loudly now.
“Get up. You can also rub that ass if you want. I certainly like how it turned out.”
She did so, and reached back to rub her very red butt.
“Now Annalisa, I think I’ll take a few minutes with those delicious looking tits and then perhaps you can give me your best blow job, but only if you’re good. Now come here”
I had her walk over and sit on the very front edge of a chair with her legs spread wide open.
‘Put your hands behind your head and remain still.”
Then I proceeded to have some fun with those breasts. There was some sag, but not much, & I enjoyed myself as I squeezed them, pushed them together, licked them, sucked the nipples, lightly bit the nipples, twisted them, and blew on them until they were hard. I also reached back and grabbed her ass with hard squeezes. I made Annalisa wince as her sore ass was squeezed, but she did not pull away.
Moving up to have my nose almost against hers, I told Annalisa “No kissing” and with one hand kneading her ass, I began to move between suckling her nipples and kissing her neck. I let the ‘free’ hand move down, and first I tugged on her pubic hair, then I rubbed her clit, making her moan. I then worked down farther, and began playing with the entrance to Annalisa’s vagina.
“I moved my face back to hers, nose to nose. The, I slid two fingers inside her. Annalisa was totally wet and there was no resistance whatsoever. Instead of finger-banging her, I kept them inside her, and began working them like the fingers were ‘walking’ and grinding in a circle. Annalisa began to loudly groan and moan, asking to please fuck her, to please let her suck my dick.
Suddenly I pulled my fingers out and completely let go of her in one swift motion. “Down on your knees.” I said. When she was there, I told her, “You can lower your hands. In fact, use them to get this dick out. But you’d better give me your best, or we start with you back over that desk again.”
And she went to work. She had done this before. She varied her tempo, but was always going up and down. She periodically tried to throat it all, and eventually succeeded. Her tongue was always on the underside providing pressure. The whole time I had one hand on the back of her head, and the other mauling her tits and tweaking her nipples. Annalisa Sherrill knew what the hell she was doing.
“Pinch those nipples. Hold them out, and twist the ‘till you grunt.” I glanced over and could see that she was humiliating herself just as she wanted. I placed both hands on her head, and finding the back of her throat, I began to power-fuck her face, enjoying the gagging sounds she made.
“Here it comes” I announced and pulled out, holding her head still. I proceeded to dump spurt after spurt of my goo on her face. I came harder than I had in the last week. It felt like gun fire coming out of there. Annalisa Sherrill, noted local philanthropist and power player, sat there and took it, ending up with a very completely glazed face.
Placing my thumb under her chin, I slowly turned her face from side to side, so the phone got the full effect of her coating, then let her lick my hand clean. Only after she thanked me for humiliating her did I allow her off her knees.
“Sir, I arranged to have you the full night, and only part of it here.” Annalisa said.
“I’m aware. Take your clothes and pack them in this bag” I told her flatly.
“But what about…” she said, indicating outside her office.
“You’ve got that long coat, I’m sure it will cover you appropriately, at least let’s hope so.”
I dressed as she did as instructed. “Is your car here?” I asked.
“No. I took an Uber, as you/well, Veronica had requested. Please don’t make me walk out naked, Sir.”
Again, the game. Annalisa was well-to-do to say the least, being a local philanthropist of note in the local area, so I had to be careful. But on the other hand, she had paid really well, so I intended to give her a performance she would never forget. Also, Annalisa seemed to ‘enjoy’ the challenge, so I was going to go with it.
Annalisa’s car was a Rolls Royce Phantom. I held the door for her, but I let her drive. As soon as we were in the car, I pulled open the coat. “Nice” I simply said.
She was embarrassed and did protest, but I did catch the tiniest smile from her. Annalisa apparently thought that I couldn’t see her in the dark, but her puffy nipples and wry smile told me she was getting her money’s worth. Goodness knows I was.