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 on 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. It was exciting, but I also hoped this was one of the last. 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 garterss. 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 toward 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.

"Yes. 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.

Annalisa Sherrill lived in a really nice set of condominiums along the edge of East Bay. They were double-decker and arranged in groups of three, with each group having a connected parking garage. She parked in her marked space near a wall, and at my direction she walked around to the passenger side. This vehicle had the extended rear so the doors opened very wide. Perfect.

"Step back here, and lose the coat."

"Here? Someone will see." Always the games.

"So is that a No?"

Without another word she did as instructed, swiveling her neck constantly looking to see if someone was watching.

"Are you planning to do me in the butt?

"Good girl" I responded. "Very smart. Now bend over into the backseat so I can fuck that ass"

Annalisa genuinely hesitated, looked around, and realized I had planned better than I was letting on. So she slipped back into character. "Please. No. Someone will see. It will hurt"

"I'm giving you what you have asked for, and per you, you paid well. Don't you want your money's worth? As to Pain? Maybe Yes. Maybe No. Only one way to find out."

I grabbed her by the shoulders and spun her so she faced the backseat. She obediently leaned over, and wow was it ever a sight. 50's or not, Annalisa Sherrill had an incredible body. I put one knee between her legs and gave her a bit of a nudge, as I leaned around her and kneaded her nipples, feeling them harden. I got behind her and began to position myself, rubbing my thumb on that butthole.

"Please. Not dry. You'll kill me". Again the game, but this had some truth to it, one I was fully expecting

"So you've done this before. Then you know to relax or it will hurt even worse." I relied with a tiny laugh. Then added, "No worries, Doctor David has juuuuust the thing." I fumbled a moment, finding it in my pants, and pulled out a veterinary syringe I had filled with Astroglide, and after shooting a small amount on my finger to lube it up, I started working it into her ass.

"OH...SIR! What's that!?" she exclaimed as she also tightened her ass.

Whack! I slapped her on the side of her ass with my hand and told her to relax. After a few in and out strokes of the syringe, I pushed the plunger and shot most of it into her anal canal. She felt the coldish liquid and started to quiver a bit, both from the chill and the anticipation of what was coming. I used the rest of the lube on my cock, which was fucking rock hard, and touched the head to her tight little hole. She instinctively tightened.

"Annalisa, we can do it the easy way or the hard way. It's your choice"

She held up a hand, took a few deep breaths, & nodded. I pushed & could feel the head begin to breach her hole. I kept a steady pressure and the head popped in. She jumped a bit, and it made me laugh.

"It hurts. Please that's enough for the first time, OK?"

"I know better than to buy that. Admit you -- oof -- like this" I said as I pushed a little deeper and feeling her tighten around me.

"Ahhhh -- I do like this" she said

And I pushed all the way in. She gasped and sputtered to get the words out

"Slow! that hurts. Please." I raised a hand to strike her and panting she said "OK...OK...you feel good David, I like this. Please fuck my ass."

I was buried will my balls resting on her cunt. So I pulled back and started to pump her ass slowly. She resisted at first, but then relaxed some. Annalisa Sherrill grunted and moaned. She apparently had not done this much, because she was tight, but after admitting that she liked it again, she began to push back into me.

There was no way I was going to last long. I mean, I WAS ass-fucking a gorgeous socialite in a Rolls Royce. So I grabbed both hips and picked up the pace. I pulled almost out & back in, and with each thrust Annalisa would stifle a cry and turn it into a groan. Soon she was pushing back as hard as I was fucking her wonderful anus. I reached under and grabbed both breasts, found the nipples, and twisted them. She buried her head into the backseat and let out a scream as I dumped my full load into her ass.

***

I gave Annalisa back her panties, but that was it. It was mostly because I didn't any of my fat jizzy cum load leaving a trail, or plopping out should we meet a neighbor (we didn't). The whole way from the parking garage I had my arm round her or mostly groping her ass, and I hope security cameras caught it.

Yep, she was most definitely into it, squeezing my cock thru my pants as we made our way there. Once inside, I tore the coat off Annalisa. After the ass fucking she'd just gotten, I figured she be mad at me. But, to my surprise, she started to kiss me back, and fumble for my belt.

"Sir! I want you! I want that dick inside me!'

My pants were down and she was on her knees, and in a flash she had my rock hard member in her mouth and was bobbing up and down quickly. I had cum twice, but she was well on her way to making me shoot number three. But I wasn't going to have it this way. I grabbed her hair on the back of her head and guided her up. She pointed and I led her to a really elegant bedroom.

After we stripped, I gave her a gentle push, and she went back onto the bed. Annalisa's large breasts gave a satisfying shimmy back and forth as she landed. I grabbed both her ankles, pull her halfway off the bed, threw her legs over my shoulders and buried myself in her pussy, balls deep/all in, & in one thrust. She let out a groan of pleasure and I started to pump that twat as fast & as hard as I could.

"Oh, YES! she yelled. "Fuck me! Fuck me hard!"

"Hands behind your head, and keep them there" I said as she lay on the bed, now helpless to my pummel-fucking.

I slowed down and began to bring myself down a notch. I reached up between her legs and grabbed each nipple with my forefinger and thumb and puffed up the nipple as I continued to pump her. I alternated between working her two erasures and torturing each breast, never breaking rhythm.

Annalisa moaned loudly and squirmed, calling out & moaning thru her gritted teeth.

"Ummmmmm. I'm close! Don't stop. Please don't stop!"

I did stop, and she looked like I had just stabbed her. I pulled out, stepped out from between her legs and flipped her over.

"On your knees and get that ass in the air!" She complied instantly

"Reach back and rub yourself woman, and tell me what you're doing."

"Ohhh -- I...I'm rubbing my c-cl-clit-t..."

She did as she was told, closing her eyes and enjoying the feeling. With one good push I was right back in her pussy, plugging away, happily balls deep. I could do this for a very long time, as this was my third load. So I just pumped merrily away, watching this MILF (GILF?) groan and squirm under my pounding.

When I had turned her over I had gotten a bit of KY, and now I squeezed some onto my thumb. Rubbing her starfish made her eyes pop open wide. "Keep rubbing that clit." I said, as I could feel my own pressure building.

"Ok sir....Your dick feels AMAZING, and I want to...to....ahhh..."

Annalisa's face was flushed red like she was angry, and her fingers were working like lightning, all while I pump-thrusted mercilessly into her. She was frowning, her eyes were closed, and she was totally tensed -- so close! When I eased my thumb into her anus, the moan moved quickly to wail, and Annalisa Sherrill began an incredible gyrating orgasm. The pulsing on my cock was too much, & I proceeded to empty what I had remaining inside her womb with a mighty roar.

The rest of the eve was a bit of a surreal experience, as Annalisa first licked me clean, then curled up around me in her silk sheets, and we both slept a deep sleep. I was supposed to stay the night, which was fine, although the looks I got from the morning housekeeper, who also made a wonderful breakfast were quite something.

***

I had barely gotten home when I got a text from Brianna. "Great news Bae! Be at my place at 6." The fucking in this "deal" had been incredible but getting out from under Twisted-Bitches' thumb was paramount at the moment, and I drifted off for a few hours of blissful sleep.