The Elites Ch. 01 - The Anal Expert

I woke up, and I checked the clock. It was 5:45 AM, and I was late again. This was the third time this month that I would miss my 6:30 stand-up. I looked at the empty bed next to me. Kate was gone. We had been together for a year, and during that year, I had never known her to be late.

I unlocked my phone, opened the calendar, and pushed the stand-up back to 7:00 AM. That is one of the perks of being the CEO of your own company. You can move a meeting without needing to explain. It was totally worth being late today because last night was epic. It was a blur of Kate's tits, her mouth, her hands, her ass, her pussy, and my cum in her, on her, and all over.

I picked up her $3,000 dress from the armchair. It was ripped at the front from its low neckline down.

"Lupe has her work cut out today morning. The room will need deep cleaning," I thought.

I made the morning meeting and the five meetings after that, and I had an hour before my next call. Typically, I used the mid-morning break for a workout, but today, I had five hundred-odd unread emails to tackle.

"I don't think I need gym today after the heavy action yesterday night," I decided.

I decided to call Kate before I tackled the emails. I tapped her mobile phone, and the call went to her voicemail. I tried her work number, and her secretary picked up.

"Ms. Hudson, please," I asked. Kate disliked familiarity at work. She was Ms. Hudson at work, not Kate.

"Ms. Hudson is not in. Can I take a message?" asked her secretary.

"C'mon Linda, where is she? She is not picking up her cell either," I pleaded.

Linda would have never revealed that information, but Kate had authorized her to give me more access.

"She is at the gym," answered Linda.

"Thanks, Linda. You are the best!" I hung up.

Kate usually hit the gym first thing in the morning. The gym opened at 5, and she was there at 5. She worked out for 45 minutes and was in her first meeting by 6. Today, she hadn't been able to make it. Undoubtedly, for the same reasons that I was late. As the CFO of a large multinational conglomerate, she was the epitome of a professional executive whose time was precious and every minute of her workday meticulously planned. On her calendar, 8 PM to 6 AM was marked as "personal time." Everything else was her work life, with meetings and calls scheduled well in advance. On the other hand, I, as the CEO of a tech startup, had a flexible schedule.

Back to reading my emails. I was halfway down the list when I noticed a mail with the subject line - "Black." It was also sent by "Black." The thing is, I did not know anyone called Black. I was about to delete the mail, but something about the intriguing subject stopped me, and I opened it instead.

It said, "Your application has been selected. Congratulations! You can complete the registration using the link provided below. If you do not register by 3:00 PM EDT [today's date], your spot will be offered to the next applicant on the waitlist."

I knew it! It was a phishing mail. I should have never opened it. The link would probably install malware or a virus. I hit delete and moved on to the next email. I started reading the investor statement when the phone rang. It was Kate.

I said, "Hello beautiful, I loved sucking your tits yesterday night."

"I am sure you did, but I am going to transfer you to Ms. Hudson now, and you can tell her yourself," responded Linda.

I was embarrassed, and before I could say anything, Kate's warm voice came on, "Hello, handsome! I loved your salty balls in my mouth."

"Why did you have Linda dial me?" I said, annoyed.

"It is her birthday today, and I thought I would give her a present," said Kate. "Linda loves dirty talk!" continued Kate.

"Isn't that right, Linda?" Kate said, addressing Linda, who was presumably listening to this conversation. "Linda, don't you know you are not supposed to listen in on private conversations? Do you like imagining him down my throat? If you let me in on your fantasy, I could make it happen!"

I heard a click.

"She is not on the line anymore. I am sure she enjoyed that comment about you down my throat. She has probably taken out her lipstick vibrator and is pleasuring herself," said Kate to me. "I really did enjoy your balls."

"And I enjoyed eating your ass," I said. "You do know what you just said is a sexual harassment case waiting to happen?"

"You don't know the things she has shared with me. If anyone is suing, it should be me. I have heard things that cannot be unheard!"

"Like?"

"Topic for another day."

I couldn't imagine middle-aged, plain, strict Linda talking about sex, much less about subjects that would shock Kate. I added it to my mental To-Do list to follow up on.

"So, what's new?" I asked

"I just got asked to speak at Davos. Something about 30 under 30," informed Kate. "You should come to Davos and register for my talk. I could teach you a thing or two about how to run your company."

"Speaking of registration, I received this cryptic phishing mail," I said. I gave her the details of the mail from "Black" with the subject line "Black." "It wasn't even a good phishing attempt. It was so obvious."

"Well, it seems to have worked on you," said Kate.

"Yes, it has. On second thought, it is a good phishing mail. It has made me very curious."

"Why don't you just click on that link?"

"And fall for the trap? No, thank you. Plus, I deleted it."

"It is still in your trash. It is not gone. You are the CEO of a tech company that specializes in cyber security. I am sure you can handle one phishing attack," reasoned Kate.

"And that is exactly why I did not open the link!" I retorted. "I know better."

"Now I am intrigued by this mail. C'mon, just click on the link, and end this suspense."

"No. Sorry, I mentioned it. Let's talk about Davos," I said, trying to change the subject.

"My next meeting is at 3, and the link expires at 3. It is ten to three. There is no better use of these ten minutes than to find out what is in that mail," said Kate. "I will blow you tonight if you do," she added.

"You were going to do that anyway."

"But I can choose not to."

"Is that a threat?" I asked.

"No, it is the difference between a guarantee and 'if I am in the mood,'" she explained.

"Because you asked me nicely, and because I really need one of your blow jobs, and because I am a security expert, I will indulge you," I said, giving in.

"Whatever. Do it already!"

I hunted around for the mail in my trash and finally found it. The link hadn't expired. I ensured that my antivirus and antimalware software were set to maximum security.

Nine minutes to go. I clicked the link, and I was redirected to a website with a black (of course) background.

On it, in an elegant white font, it said, "Welcome, Mr. Fisher. Please verify your identity."

Below this sentence was a white box asking me for a password.

Eight minutes to go.

"Kate, this is the most elaborate scam ever. It wants a password that I do not have or know. I give up."

"No! We still have seven minutes. We can make it if we try."

Kate did not like to lose. This website had brought out the competitive "win-at-all-cost" Wall Street executive in her.

"Try all the usual suspects - mother's name, birthdays, first girlfriend, etc.," she said.

"No way!" That is what they want. To give my identity away. I can see the genius behind this scam now."

"Is there no 'forgot your password' link?" Kate asked.

There was none. But I did spot a text link in small gray fonts at the bottom of the page that said "Hint." I clicked on it, and a text appeared that read, "Your favorite position."

This was even more confusing. Did it mean my favorite sex position?

"Well ... Find anything?" asked Kate.

I did not respond. I was thinking. My ex and I used to joke that my favorite position was "Every Fucking Position." Without thinking, I typed the phrase in and got an "Incorrect password. Two attempts remaining. Try again" prompt. I tried again, but this time I used the same phrase without the spaces, and it worked!

"Kate, I am in!"

"What is the password? OK, no time. What's next?" she asked urgently.

I was now logged in. The top right corner showed a timer with 2:45 on it. It was counting down. Below it, I had three options.

1. Standard $5,000

2. Premium $15,000

3. Elite $50,000.

Next to Elite, it said, "Only four available."

I conveyed the options to Kate.

"Select Elite," she said.

2:00 left on the timer

"Are you kidding me? You want me to give away 50 grand? There are no details on what this is for. Even if it were legitimate, I need to know what I am paying for."

Kate's voice turned very calm. I knew that voice. It was the tone she used when she was in a tough negotiation.

"You can afford it. You paid more for the painting you bought last Friday just to piss Ralph off, and you haven't even unwrapped it! Also, if it turns out to be a scam, you can always dispute the charges on your credit card."

"Why don't we go for the 5K ticket?" I asked

"Because people like you and I don't buy standard tickets. We buy the elite ones."

45 seconds to go.

"I don't have enough time to complete the purchase."

Kate said, "Just try."

I took a deep breath and selected the elite options. I clicked 'Next.' The timer changed to 3 minutes. "You have 3 minutes to complete your purchase," said the prompt on the page.

Kate let out a "woo-hoo!" when I told her. "We are in business!"

The next screen was a standard registration form.

"Looks like we are registering for a gala of some kind," I said. "I have the option to bring a 'plus one.' No, it is mandatory to have a partner. That is a required field. Do you want to be my 'plus one'?"

Kate's adrenaline rush was gone. "I don't know," she responded, "It will depend on the dates."

"I am adding you as my partner," I said firmly. "You pushed me to register, and we only have 2 minutes to complete this. You can cancel later if you don't want to come."

"OK, whatever," Kate said, uninterested. I got to jump. I am five minutes late for my meeting."

For the remainder of the day, I was busy dealing with clients and lawyers.

When I finally got home around 9, I needed to change into something comfortable. I wore suits and formal attire at work, but I was never comfortable in it. I liked my T-Shirts and lounge pants.

After I had changed, I found Kate on the oversized chaise. Her legs were stretched out, and she was working on her laptop. She had a glass of red Zin on the side table. I poured myself one too and joined her on the chaise. She scooched over to make room for me, her eyes still glued to the screen and her fingers still typing. I settled in and pulled out my Mac. We were both very comfortable with each other. We didn't need to ask, "How was your day?" We were comfortable without the small talk.

Now, I needed to check what I had paid 50 grand for. I had received a confirmation email after the purchase, and I logged in using the link in the mail. This time I was routed to the home page with more menu options. I clicked on "Registration Details."

"This year's event will be held at the Zephyr Hotel, Las Vegas. May 23rd (Friday) to May 25th (Sunday). Check-in on May 22nd at 2 PM. For our elite guests, further instructions will be sent via email."

At least I knew where we were going. Next, I had to figure out why? I scrolled around and found a link that said "Submission details." I clicked on it and navigated to that page. It said, "Congratulations on your acceptance! We received over 5,000 applications, of which only 128 made the cut. Your original submission details are below."

Below I saw three links. The first one was a PDF titled "Submission Guidelines." The second and third were download links for video files. One was labeled "Full-length," and the other "Edited." I opened the submission guidelines first. The first section had details on how and where to send the application. The next had three bullet points.

* "All applications must include an unedited video captured by a single camera. Any action off-camera will not be considered."

* "An edited video of up to 60 minutes may also be included. The video can be compiled from footage from multiple cameras as long as any scene in this video is also present in the unedited version. If submitted, this video will be used by the judges."

* "All participants must consent, on-camera, to the terms and co of this contest."

The completed application was digitally signed by "Elizabeth Sanders" and "Jonathan Fisher." That was my Ex and me. All good, except I never signed the document, nor did Beth tell me about it.

I tapped Kate on the shoulder and turned the laptop toward her so she could read the application and the instructions.

She read it silently and said, "Let's throw the video on the big screen."

The big screen was a 105" 8K TV on the wall across from the couch. I uplinked the "edited" version of the video onto the media center and said, "Ready when you are."

Kate closed her laptop and said, "Ready."

I hit the play button.

On the screen, Beth was looking straight at us. She was in our bedroom and wearing a black sequin dress. I was standing behind her.

She said, "This is Beth Sanders and Jon Fisher, and we consent to the terms and conditions of Black."

Kate grabbed the remote and hit pause. She said, "I thought you had no idea about this?"

"I don't remember this! You know the bedroom has over 50 cameras. When Beth was living here, it was on almost all the time. She loved replaying us doing it. It was almost like she took notes for the next time. She made me say stuff for the camera all the time. Usually, it was dirty talk. I have no recollection of most of what I said."

Kate smiled and said, "This is going to be interesting," and hit play.

Beth started speaking in her bright voice. "Let me introduce you to Jon Fisher. 6 feet 2 inches tall, a fine specimen of a human male. He weighs 170 pounds with only ten percent body fat."

With an exaggerated gesture, she presented me to the camera. She then took off my jacket and unbuttoned my shirt. She turned around at the camera and proceeded with her commentary.

"Look at the broad shoulders, the strong chest, and the washboard abs. Turn around, Jon."

I turned around (on the screen)

"Look at the back. Strong and muscular.," Beth continued. She turned me around so I was facing the camera again.

"Now, for the main attraction."

She pulled my pants and underwear down with one swift motion, like a magician. She must have undone my pants while she was taking off my shirt.

"Now for the main attraction," she repeated. "An 8-inch cock"

She cupped my balls in one hand and my not-8-inch, not-erect cock in her other.

She made a pretend embarrassed face and said, "Oops! It appears that it will need some work."

She kneeled in front of me and began stroking my less than 8-inch, but still substantial, dick in her dainty hands.

This was the edited version. The camera zoomed in on the action. I am not sure how she found this camera angle. Was it deliberate, or I just happened to face one of the cameras at the correct angle? Then again, there were so many cameras in the room that there was a high probability that I was facing one of them at any given point. Beth must have zoomed in during editing. Most of the TV was taken up by my enlarging penis with her hand wrapped around it. A drop of pre cum was starting to appear. The engorged head was turning darker, angrier, and bigger. Pre cum was oozing now. In my head, I could imagine how I must have been feeling. Then, Beth stopped.

I heard myself groan at the sudden pause.

The camera cut to Beth, and she said, "Tada! Eight inches of Jon." Then she said with a twinkle in her eyes, "Can we get it to 9?"

With that, she took her tongue out and started licking the head of my penis. She lapped up all the pre cum and started working her way down the shaft. The camera cut to my face, and I had my eyes shut with an expression of joy and lust.

In the real world, I closed my eyes too. I imagined Beth's tongue on my penis. Suddenly, I felt a warm hand on my cock. I opened my eyes, and it was Kate! She had slipped her hands under the waistband of my pants and grabbed my dick.

Her eyes were peeled to the TV, and she said without looking away, "She's not the only one that can enjoy the eight incher!"

Kate's hands were bigger and firmer than Beth's, and she knew her way around my dick very well. She worked her fist up and down, maintaining a steady pace. She held it at just the right place and applied just the right pressure. She pulled down just the right amount and went up just the right amount. The result - an exquisite hand job! If she kept it up, I would come in no time.

Beth had moved on from licking my staff to devouring it. Her head was bobbing up and down furiously on it. Kate was moving her fist in sync with the motion on the screen. When Beth went faster, she went faster, and when Beth slowed down, she slowed down too. It was incredible! I was experiencing Beth through Kate!

After about a minute of serious head, Beth stood up and, pointing to my dick, announced, "Ladies and gentlemen, for your consideration, a 9-inch dick!!!"

My cock had indeed grown an extra inch. It looked stretched to the limit, hard as steel.

"This thing is going to fuck my ass today!" Beth proclaimed. She bent down and gave a few more strong sucks. I could see the suction build up in her cheeks and then release. Beth loved giving head. It aroused her, and she could almost cum from a good blow job. She sucked one last time and took her mouth off my dick with a loud plop, the vacuum breaking. On cue, my cock erupted, and I came on her face. And I kept coming. My cum was all over her face, her hair, her dress. It was everywhere.

Kate turned around and said, "That was quick."

"There is no way I came that quick," I said with little conviction. I was trying hard not cum right now.

On the screen, Beth turned to me and commanded, "Introduce me, Jon!"

I said, "Let me introduce you to Beth Sandler. 5 feet 3 inches tall, a fine specimen of a human female. I have no idea how much she weighs, but look at her body and her proportions - do you really care?"

Beth was a petite, curvy woman with a little bit of fat. The fat added to the sexiness of her small frame.

"Let's see more of her," I said, turning her around. I unzipped her dress and took it off as swiftly and deftly as I could. It was not as elegant as my undressing, but it got the job done. She was wearing a thong but no bra. Now, let's see what's beneath this underwear."

That underwear was pretty much non-existent. It was a thong with a thin purple strip covering her front and a gold string covering her back. Well, the back was a joke. It did not cover anything. I patted her ass lightly and said, "Take a look at this beautiful piece of ass." I kneeled and spread it open. The camera zoomed in on her tight asshole. The thong did not hide anything. The string was barely as wide as the clenched hole.

I grabbed her ample bottom and rotated her 180 degrees. I pushed my finger past the purple fabric covering her pussy and dipped my finger in it. I licked my finger and said, "Mmm. Tasty!"

I stood up and gently cupped her breasts. "Look at these big boobs. Just perfect!"

"32 C", Beth corrected me.

Compared to the rest of her petite body, those knockers looked huge! I kissed her nipples lightly and moved down her flat stomach. I sat her down on the edge of the bed and then slowly pushed her down to lay her on her back. I opened her legs, and the camera zoomed in on her pussy. Her pussy was hairless.

"Look at that clit!" I said, pointing to the bud that was showing its head. She must have been very horny.