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The Shot Caller

"For high class escorts, the biggest wallet calls the shots"

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3.3k words 3.3k words

Author's Notes

"This story was inspired by my Lush buddy, chattycathy1975. She was my muse for the character. Thanks for the chats, Cat!"

In the world of high-class, high-priced escorts, Cathy was at the top of both lists. Over the course of almost seven years, she had built a clientele of some of the richest and most powerful people in the world, both men and women.

Cat, as her friends called her, stood five and a half feet tall. She had natural blonde hair, large brown eyes and an enigmatic smile that made people feel engaged and desired. Her body would inspire poets. Curvy, with beautiful full breasts and an ass men would kill or die for. To put it mildly, she was drop-dead gorgeous.

Cat was very discreet and held an encyclopedic knowledge of all things sexual. She had her rules, but for the most part, there was very little off limits and nothing that she didn’t do extremely well. Her secured cell phone was constantly filled with texts requesting bookings all over the planet.

At just 28 years old, Cat already possessed a financial portfolio that had her set up for the rest of her life. One of her longtime clients was a senior hedge fund manager who also handled her investments.  She owned luxury condos in half a dozen cities around the world and had stocks in all of the most successful Fortune 500 companies.  And every new booking added at least another $50,000 to her numbered bank account in the Grand Cayman Islands.

So, when her phone lit up with an anonymous text from a caller I.D. blocked number, she was more skeptical than interested.

The text simply said, “My client would like to enquire about booking your services. Please respond at your earliest convenience.”

Fewer than two dozen people knew Cat’s business number, telling her that someone from her inner circle of clients had shared it with this mystery person. She decided to take her time while she considered how, or even if to respond.

After letting it sit for close to eight hours, Cat sent a reply. “Who is this? Who is your client and who gave you this number?”

In ten minutes, the response arrived. “All in good time. My client is prepared to compensate you handsomely for your services.”

This didn’t sit well with Cat. One of the hallmarks of her life was that she was always in command of any situation. Cat was the shot caller.

She decided to make whoever this was simmer overnight.

The next morning, Cat sent a return text instructing the person to wire $50,000 to her Cayman Islands account. “Once the money is safely in my possession, I will contact you again to discuss availability and terms. This initial transaction will be considered a gift. It is nonrefundable and is not included in any financial arrangement we may agree on.”

Thirty minutes later, there was a message from Cat’s bank confirming a wire transfer of $50,000.

Cat texted the mystery person.

“Okay, you seem to be true to your word. I’m listening.”

Within a minute, she got a reply.

“I represent a very successful businessman and leader who has certain appetites that many would consider unusual. For the purpose of this and any future communication, he will be referred to as ‘Mr. Schott.’ This is not his real name, but that is unimportant. Mr. Schott demands complete discretion and has been assured that you are trustworthy.

“He is looking for someone who can satisfy his unusual needs. Again, he has been assured that you are the right person for the task.”

Alarm bells were going off for Cat. But she had 50,000 reasons to keep reading.

“If you choose to continue, you will receive a document containing explicit and detailed instructions of the services expected. They are nonnegotiable. Should you agree to perform these services, you will be flown (First Class, of course) to a location of Mr. Schott’s choosing. This entire encounter will take less than forty-eight hours.

“Please inform me whether or not you wish to proceed and what fees you would require.”

The alarm bells were getting louder for Cat. This “Mr. Schott” was trying to call the shots and Cat needed to put a stop to it.

“Everything is negotiable,” she texted. “I am open to continuing this conversation, but I have three caveats. One – I do not fly commercial. Your client will provide a private jet for my travel needs. Two – I will not be involved in any activity that includes beastiality, scat or golden showers. Three – I will not allow any activity that includes anal penetration to myself, either with a body part or other device. Anal penetration of your client is acceptable.”

There was a good reason Cat was refusing anal penetration, and it had nothing to do with her sexual preferences. Any time she took on a new client, she always had a small silicone capsule that she kept hidden in her anal cavity. It contained an air tag-like tracking device that her hired security detail used to shadow her and stay close. She’d only needed it once in her career, but she was alive today because of it. That distress call she sent ended up with her being spirited away, four days in a private hospital, and a very rich and powerful man mysteriously found dead.

“All of these caveats are deal breakers,” she texted. “However, if you are amenable to them, please send over your document. Fees will be based on the contents of the document.”

The response was almost immediate. “All caveats accepted.” There was a .pdf document attached.

The document read like it had been penned by a technical writer creating a user’s manual.

‘Upon arrival at the designated location, female contractor will be provided specific wardrobe. Female contractor will dress in this wardrobe at the time services are rendered.

There will be a bed and a settee in the location. Female contractor will sit on the settee, legs crossed. FEMALE CONTRACTOR WILL NOT SIT OR LIE ON THE BED.

Female contractor will not speak, smile or laugh at any time.’

“Okay,” thought Cat. “This is weird. But I’ve seen weirder.”

‘When female contractor is in place, Mr. Schott will enter the location and take a seat nearby. Female contractor will not look at, or acknowledge Mr. Schott in any way.

On Mr. Schott’s signal, additional male contractor will enter and disrobe. Male contractor will have a fully erect penis upon entry.

Male and female contractors will make eye contact, but will not speak, smile or laugh.

Mr. Schott will display flash cards to indicate actions male and female contractors will perform. Contractors may look at the cards, but MUST NOT make eye contact with Mr. Schott.’

There were images of the flash cards on the document.  Fellatio, Cunnilingus, Vaginal Penetration with Penis, Mutual Masturbation. The list was long and coldly clinical. 

“This guy’s a nutjob,” Cat concluded. But he was a rich nutjob, and there was nothing on the list that she hadn’t done and mastered. After the flashcard images, the instructions continued.

‘At a time to be determined by Mr. Schott, male contractor will ejaculate onto female contractor in the spot and manner detailed by flash cards.

At this time, female contractor will make direct eye contact with Mr. Schott and hold eye contact for the full duration of the ejaculation.

There may or may not be additional flash cards indicating actions for female contractor to take with the ejaculate.

Mr. Schott will then stand and ejaculate on female contractor. EYE CONTACT MUST BE MAINTAINED THROUGHOUT. DO NOT ATTEMPT TO MAKE PHYSICAL CONTACT.

At the time Mr. Schott breaks eye contact, female contractor will silently mouth the words “thank you.”

After Mr. Schott leaves the location, both male and female contractors are free to go. Return transportation will be standing by.’

“This guy must be the most repressed, anal-retentive loon I’ve ever heard of,” Cat thought to herself. But in the end, she decided he was just another fucked-up rich guy who got off by watching.

She decided to take the job. But first she’d let him stew for a while. After all, Cat always called the shots.

She gave it two days. She had another client to entertain in that time, and wanted to give him her full attention.

The next day, she texted the mystery person.

“Your instructions are all within the scope of my comfort zone. Please send a list of five proposed dates for me to coordinate with my calendar. My fee for services rendered will be $200,000, payable in advance. As you have been informed, I am discreet and reliable. I will not board any limousine or plane until payment has been confirmed by my bank.”

Two hours later, payment had been transferred, and a date was set.

 

On the appointed date, a black stretch limousine arrived outside Cat’s penthouse condo overlooking Philadelphia’s Penn Square. She was whisked to a charter aircraft service, where the attentive staff took her small bag and poured her champagne.

“May I ask my final destination?” Cat inquired.

“Yes ma’am, you’ll be touching down in 8 hours at Saint-Gatien Airport in D'eauville,” the young attendant told her. “That’s in France. Normandy."

“I know where it is,” Cat said. “Great beaches. Too bad it’s out of season.”

The flight was smooth and relaxing.  Cat was served a delicious dinner with Marseille style shrimp and glazed baby carrots, along with a delicious pinot gris.

She napped for several hours before the Dassault Falcon 8x jet landed effortlessly. A waiting limousine transported Cat to a beautiful gated beach estate that backed on to the English Channel.

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There, she was greeted by a tall English gentleman who introduced himself as Lawrence.

“Are you the man I’ve been corresponding with?” Cat asked.

“No, miss,” Lawrence answered. “I am the chief assistant to the owners of this estate. They’ve loaned it to your benefactor for the week. I am here to take care of your needs during your stay.

“Your suite is fully prepared. You are welcome to relax there, but you have full access to most of the property. Please enjoy your stay, and ring me if there is anything you need.”

Cat wasn’t unused to this treatment, but she still savored it every time. It was one of the reasons she worked so hard to maintain her business and stay in demand.

When she reached her suite, she was greeted by a bottle of champagne and a note.

‘Welcome to D’eauville. You will find your wardrobe in the closet. You will meet with Mr. Schott at 9 p.m. this evening. You will wear the red gown, with the white lace garters and stockings. You will also wear the matching red heels.

At 8:55, Lawrence will escort you to the designated meeting room. Please be punctual. Mr. Schott does not like delays.’

“Well, that’s typical,” thought Cat. “Mr. Schott wants to call the shots.” She laid out her wardrobe and decided to relax on the bed, setting her alarm for 7:00, just in case she dozed off.

Cat prepared her hair and makeup and was dressed and ready by 8:45. At precisely 8:55, there was a crisp knock on her door.

“You look lovely, miss,” Lawrence told her. “Please follow me.”

“Now I find out,” Cat told herself. She had studied the instruction document thoroughly, and knew exactly what to do and when to do it.

Lawrence led her down a short hallway filled with beautiful antiques and artwork. He stopped in front of a set of ornate double French doors. Opening the door, he told her, “Just in here.”

Cat entered, and Lawrence closed the door behind her. She was alone in a cavernous, beautifully appointed bedroom. As described, there was a massive king bed with a red velvet upholstered settee at the foot. A small white accent chair was placed about 4 feet from the settee.

Cat sat on the settee and crossed her legs. The red silk dress slid over her legs and the slit up the side revealed her perfect legs in the white stockings.

 Cat waited, controlling her breathing and looking extremely seductive.

After almost three minutes, she was starting to wonder if something had gone wrong. But just then, a small side door opened and a man stepped out.

Cat knew she wasn’t to look at him, but there was a mirror in her line of view, and she tried to casually catch a glance.

The man was short of stature and had a very slight build. He wore a white terrycloth robe and seemed to be wearing some sort of spandex bodysuit underneath it. But the weirdest part was the Guy Fawkes mask that obscured his face.

Mr. Schott removed the robe and sat in the accent chair. The spandex body suit completely covered him, except where the crotch was cut out, exposing his rather meager package.

Mr. Schott gave Cat a long look as she averted her eyes. In the mirror she saw that he was beginning to show the slightest signs of an erection.

He gave a hand signal and another side door opened. A tall, athletically built young man stepped in. Blonde hair, classic Nordic features and a body that looked like it had been chiseled by Michelangelo himself. He wore a pair of black silk boxers and nothing else. His erection was clearly visible.

As instructed, Cat and the man looked one another up and down. The man dropped his boxers and stood before Cat, completely nude. His cock was close to nine inches and it was a thing of beauty.

“It will be a pleasure to fuck this Adonis,” Cat thought to herself.

Mr. Schott held up his first flash card.

“Fellatio”.

Adonis stepped forward and Cat slid to the edge of the settee. She took his beautiful cock into her hands and stroked it up and down.  Starting at his testicles, Cat ran her tongue all the way up his shaft, then slid the bulbous head into her mouth. He had a wonderful taste, and his musky scent added to her attraction.

She slowly worked this beautiful cock further into her mouth, taking about half of its length.

Mr. Schott pulled his chair closer. She could see in her peripheral vision that he was now mostly erect. Comparing his cock to Adonis’s was like comparing an outhouse to a high-rise office building.

Mr. Schott held up another flashcard.

“Deep Throat”

“Whoa! Slow down!” thought Cat. “Let’s ALL enjoy this.”

But for the moment at least, Mr. Schott was calling the shots. Cat relaxed her jaw and throat muscles and took a deep breath.  Adonis slid his cock all the way in, until his balls pressed up against her lips.

Swallowing nine inches was second nature to Cat. She slid him in and out, over and over, and she didn’t choke or gag at all.

Once again, Mr. Schott moved closer. He was now only two feet away, and despite not having touched himself, was now fully erect.

His breathing was becoming more rapid and heavy, and he held up his next flash card.

“Cunnilingus”

Cat wanted to say, “What’s the rush?” but dutifully moved on.

She released Adonis’s cock and lay back on the settee. She hiked up the red silk dress, throwing one leg over the back of the settee.

Adonis knelt down between her legs and spread her lips apart. He gently began to lick her up and down while using his fingers to stimulate her clitoris.

As she became wetter and wetter, Adonis moved his mouth up to her clit. The man had talent! Cat knew she wasn’t allowed to talk, but there was nothing on the instructions about moaning.  She let out several loud ones, and used her hands to maneuver his head to the best spots.

“Hands Off”

“Fuck! This guy has a card for everything!” Cat put her hands behind her head as Adonis continued to work his magic. Just as Cat was edging toward a climax, Mr. Schott held up another card.

“Masturbate Him”

Now, Cat was annoyed. “Son of a bitch! Has this guy got a plane to catch?”

But again, right now he was in charge.

Adonis sat next to Cat, and she leaned into that chiseled body. She stroked his cock up and down and cupped his balls in the other hand.

Adonis’s breathing got heavier. So did Mr. Schott’s. He still hadn’t touched himself, but his cock was bobbing up and down with excitement.

Mr. Schott moved his chair even closer. He was now just a foot away from the settee.

Another flashcard appeared.

“Cum Into Her Open Mouth”

Adonis stood up and took over the stroking.  Mr. Schott leaned forward.  The Guy Fawkes mask was just six inches from Cat's face. She opened her mouth, ready for Adonis’s payoff. At the last second, she remembered the instruction.

She locked eyes with Mr. Schott and gave him her well-practiced lustful look.

How Adonis managed to get himself off so quickly, she had no idea.  But within seconds, he started shooting his warm, thick cum into her mouth. His load was huge. Cat’s mouth filled quickly. On the fourth pump, Adonis’s cock jerked up, spilling cum onto her nose and cheek. It splashed onto the Guy Fawkes mask that was now only three inches away. Cum poured out of Cat’s mouth, dripping down her chin and onto her breasts. It was all over the red silk gown.

With her gaze still locked on Mr. Schott, Cat noticed out of the corner of her eye that Adonis was also staring at him with an odd look on his face.

When his balls were finally emptied, there was a long pause. Everyone was breathing heavily and the cum continued to drip down Cat’s chin and breasts.

Mr. Schott held up his final flashcard.

“Swallow His Cum”

Cat continued to hold eye contact as she closed her mouth and swallowed. She opened it up to show him that it was gone.

Just then, Mr. Schott stood up quickly. He never touched himself, but with a loud groan, he spilled his cum onto Cat’s breasts and gown.

Finally, he broke eye contact and looked away with an expression of shame. When he looked back, Cat completed the final instruction.

“Thank you,” she mouthed silently.

Mr. Schott looked away again, then slowly put his robe back on and left the room.

 

The whole encounter took less than ten minutes. Cat stood up and looked at her cum stained dress. The three-thousand-dollar gown was ruined, never to be worn again.

Adonis came over and spoke in a thick Scandinavian accent. “You give great blowjobs.”

“Thanks,” said Cat. “And you have a very talented tongue.”

“I am Lucas.”

“Cat.” She shook his hand. “I have to ask you… what was that weird look you gave him when you were coming?”

Lucas smiled. “It’s in my instructions. I am to stare at him and sneer. I think it’s supposed to make him feel inferior.”

“What a strange world we live in, Lucas.”

Just then, there was a sharp knock on the double French doors. Lawrence had returned.

“I’ll escort you back to your suite, miss. You are welcome to stay for another day if you’d like, but your contract has been fulfilled. I can have your return transportation ready whenever you’d like.”

Cat smiled at him. She decided she liked Lawrence. “I think I’ll just pack up and go. Thank you for your hospitality.”

“Of course, Miss,” Lawrence answered. “Again, you look lovely.”

 

Just after midnight, the Dassault Falcon 8x lifted off from Saint-Gatien Airport, bound for Philadelphia.

Midway over the Atlantic, Cat’s phone buzzed. Anonymous text. Blocked caller I.D.

“Mr. Schott was very pleased. We need to discuss your next availability.”

Published 
Written by Stupalm
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