How I Met My Assistant

This is a story about my executive assistant, Alexa White. My name is Aaron Addison, I'm a successful hedge fund manager living in New York and while I imagine that sounds interesting believe me, the job is so amazingly boring that I rely on Miss White for more than I'm comfortable admitting. That's probably why I pay her more in annual salary than I pay myself. I've grown to accept her rejecting all my advances and how she calls me sir no matter how many times I ask her to be informal. She's the best and so she's my Miss White and I'm her Mr. Addison.

"At 8pm tonight you're having dinner with Joanna Dark at my apartment to discuss acquiring her bond trading company." Miss White said simply.

"You must be joking, she won't give me the time of day, personally or professionally, why would she agree to a dinner?" I replied almost angrily and a bit confused.

"I arranged it. Wear your tan suit, it makes you look kind." Miss White continued using her firm voice.

"Wait a second, that's my least favorite suit..." I began to almost yell.

Ignoring me she continued, "and you have an appointment at Madame Shin's beauty salon, they already have their instructions." My assistant was now using her firm voice.

Before I could even respond she asked softly, "Do you trust me?"

A question from Miss White using her soft voice froze me in place. Remembering just who I was talking to, I thought to myself I would trust this girl with my life.

"Of course, always." I answered thoughtfully.

"Good, your appointment is in 20 minutes, there is a taxi downstairs waiting." Then she then folded her arms which usually meant the conversation was over. I paused for a moment and smiled.

"I'll see you at 8." And just like that I grabbed my suit and left.

It turns out that Miss White had scheduled me for my first full man-scape. Three giggling asian beauties carefully cleaned, polished, and spray tanned my entire body. When they finished I stood there in front of the mirror and wondered why would my assistant want me to look like a teenage girl? Way too smooth shiny and pretty for my taste. I resigned myself to do exactly what she asked without question or comment. She had never let me down before so I told myself, "let's do this. at least I look pretty!"

When I arrived at 8pm, the girls were already having drinks. I smiled as I realized that even if these girls disliked me I was still a lucky man to have dinner with two absolute goddesses.

"Miss Dark you remember Mr Addison." Miss White was quick to speak first.

"Hello again." Miss Dark could clearly still remember my epic failed flirt and date request attempts.

"I'm very happy you agreed to have dinner with us and discuss the companies that we both love so much." My humble reply succeeded in getting a tiny smile so we both relaxed. This is about as far as I imagined this evening would go.

Now with a big smile Miss White called out "Lights on!" Her apartment came alive at her voice command, awesome. It was actually a massive studio with semi transparent Japanese dividers everywhere.

We had a lovely dinner. Light salad and Soft-shell clams, interesting. We were all a bit tipsy from the great drinks Miss White kept serving. When my assistant left to get desert and having too much awkward silence with Miss Dark saying nothing to me but small talk, I decided to give flirting one last try. Two words, epic fail. Oh well.

Miss Dark was offended.

Mr Addison was clueless.

Miss White was angry.

When Miss White returned with frozen drinks she clearly did not like that I had made her guest pout. She told me with her firm voice to go have my drink in the big chair on the other side of the room. Remembering that I had promised to do everything she instructed I nodded, picked up my drink and walked over the the big chair behind one of the semi-transparent screens. When I sat down I realized I could still see the girls quite well and there was a small side table with hand towels and a bottle of hand cream. Hmmm.

"You are amazing!" Miss Dark whispered to Miss White.

"Think so?" She said unbuttoning her shirt just a button or two.

"and Hot," Miss Dark said shyly.

"then unbutton my shirt." Miss White leaned over unexpectedly.

Without hesitation, Miss Dark clumsily unbuttoned Miss White's shirt exposing a very sexy white satin bra.

"Wow I've never seen such great work in my life!" Miss Dark said, impressed.

"What?!" Miss White said angerly. She then reached over to grab a strap laying on a side table and hit it against the table, "Whap!"

Miss Dark was speechless.

Miss White was angry.

Mr Addison was aroused.

"Do you think there is anything here that I wasn't born with?" Miss White said angrily looking at her chest. "Whap!"

"Oh no! I only meant that you were beautiful!" Miss Dark sputtered defensively.

"Well, then take off my shirt and bra and we'll see." "Whap!"

Miss Dark carefully removed the button up white shirt and satin white bra on my assistant with caution and purpose. Both Miss Dark and I were silent in admiration. Miss White stood there with her chin up and shoulders back looking absolutely amazing. I watched in amazement as my assistant commanded the attention of this powerful woman with nothing but a firm voice and a piece of leather. I found myself getting harder and larger by the moment.

"Touch them."

"Aaa..." Miss Dark was unsure what to do.

"Touch them!" "Whap!"

Now Miss Dark slowly and carefully caressed my assistants breasts.

"Harder." My assistant commanded.

I couldn't tell who was enjoying this more. Miss Dark breathing heavily while massaging my assistants breasts or me, trying to figure out how to keep my massive erection under control as I watched this amazing scene.

"Feel anything that I wasn't born with?" My assistant questioned strongly.

"No." Miss Dark answered softly.

"You hurt their feelings so now kiss them and make them feel better." My assistant said casually.

Miss Dark was about to say something when,

"Whap!" "Kiss them!"

I still couldn't tell who was enjoying this more. Miss Dark kissing my assistants breasts or me, having given up on keeping my massive erection under control so I took off my suit and sat naked, gently stroking myself as I watched this amazing scene.

Miss Dark proceeded to moan slightly while Miss White looked down and shouted, "look what you've done! Lick that off now!"

There were lipstick kisses all over Miss White's breasts. Miss Dark stood there and proceeded to lick my assistants breasts from top to bottom spending extra time circling both aurora.

Miss White was angry and amused.

Miss Dark was sorry and aroused.

Mr Addison was aroused and jealous.

"Now take off your clothes, let me take a look." Miss White said casually as she removed the rest of her clothes.

Miss Dark dutifully removed her clothes too and stood in silent awe staring at my naked assistant.

Suddenly I understood. Everything I was seeing was according to some plan that my mastermind assistant had put together. All three of us were now naked and all three of us are happily following the commands of Miss White. It's no wonder I pay her more than I pay myself. I'm good at what I do but my assistant is in another league altogether.

Once they were both completely naked Miss White took Miss Dark's hand and walked her over to the raised bed. Once there my assistant gently pushed Miss Dark down on the bed, then climbed on top of her and laid her breasts on her guests face.

"Lick that lipstick off of me, every tiny bit." My assistant commanded confidently.

Watching Miss Dark licking Miss White's breasts while straddled on top of her was too hot to resist. I proceeded to stroke my erection to a nice firm stance. Wow.

Miss White was entertained.

Miss Dark was aroused.

Mr Addison was erect.

While dutifully licking her breasts, Miss Dark reached down to caress my assistants clitoris when "Whap!"

"Did I say you could touch me?!" My assistant said strongly to her pinned down guest.

"No.." Miss Dark compliantly replied.

My assistant then pulled her guests left hand above her head, click. Then she pulled her guests right hand above her head on the bed, click. Soft but firm handcuffs, I didn't even know what to think. My assistant had my greatest competitor, Joanna Dark, handcuffed to her bed.

My assistant sat up and leaned back sitting naked on her captives chest, then proceeded to stroke her fingers between her negs gently, exposing how wet she had become. Miss Dark was about to say something when Miss White took her wet fingers and put them in her captive's mouth.

"You want more don't you?" Miss White asked.

"God yes." Miss Dark replied.

I watched in shocked amazement as my assistant proceeded to grind her pelvis into Miss Dark's mouth. They were both moaning softly.

"This isn't doing it for me." Miss White said and casually walked away.

Miss White was enjoying herself.

Miss Dark was in ecstasy.

Mr Addison was bigger than he had ever been.

My assistant returned with what looked like a large clear dildo. Before anyone knew what was happening, she put the dildo (with some kind of bite guard attached) into Miss Dark's mouth and asked.

"Comfortable?'

"Mmm Hmm." Miss Dark understood and nodded excitedly.

"Then hold still and be quiet!" "Whap!" Miss Dark's eyes seemed to light up.

Then as casually as sitting on a park bench, my assistant lowered herself slowly onto the dildo in her guests mouth, taking it up into her channel. Just the tip at first, then slowly she takes it in and slides up and down. She then slowly let the tip slide around her vulva while she moaned happily.

I could see the facial expressions on Miss Dark's face change from fear to horror to excitement and finally bliss.

Miss White played with her toy for a long time until she began trembling. She then raised up in a reverse squat, removed the bite-guard dildo from her captives mouth and sat back down on Miss Dark's chest.

"Stick out your tongue, and hold still." My assistant commanded while stroking herself.

Her captive happily complied while my assistant proceeded to perform crunches on Miss Dark's tongue. The sight of my assistant cumming on my competitor's tounge was too much to bear, for the second time tonight, I came too. Wow good thing the towel was here, I love a girl that thinks ahead.

With Miss Dark still trembling, Miss White declared, "We're not finished."

Now my assistant walked over to my chair while her captive was sill handcuffed to the bed and handed me a blue condom. She then whispers in a commanding tone. "be silent, put this on and make it hard right now."

With a single stroke of her hand my body stood to full attention immediately. I quickly pulled the odd blue condom over my erect staff.

She walked casually back over the the bound Miss Dark, gently pushes her captives quivering knees apart to expose her drenched vagina, and then leaning in my assistant said in a loud commanding voice, "Lights off!"

The entire room plunged into darkness, neither Miss Dark nor I knew what to do or say. I then felt a soft hand take mine and lead me over to the bed.

Joanna Dark let out a soft moan. I looked down and realized my large erection was glowing softly and the blue glow was the only thing visible in this dark room. I had become a handy prop in this amazing play.

A soft hand gently held and glided my member over to its intended destination. Before I could even think, I slid slowly into the tightest landing I had ever felt. How something could be this soft, wet, and tight at the same time amazed me. I could barely fit it in. I had to adjust and rub around the outside just to find the entrance.

"Ohh" Miss Dark whispers

"My" I whisper.

"God!" Miss White says in a low extremely sexy voice.

"More now, slowly, faster, yes, this is what I want." Miss White said confidently while caressing her captives breasts.

The only light in the room was the glowing dildo condom sliding slowly into and out of Miss Dark. This gave off just enough light for me to see Miss White caressing her captives breasts as I slid in and out.

I could feel the muscles in that amazingly tight cervix slowly loosen and finally accept my entire length into her vagina. That feeling of acceptance was accompanied my a deep moan from Miss Dark and a rare sigh of happiness from the elusive Miss White.

Now I just drove, slowly and then more quickly pushing and pulling my full length into and out of Miss Dark's tight, wet, hot body.

It did not take very long before Miss Dark began to tremble, then shake, then moan, then finally scream.

"YES!"

I was uncontrollable, pounding with all my might, almost numb from loss of circulation in this overly tight world I was in.

"Uhhh, Ohhhh, Yessss," Miss Dark moaned as my assistant began to moan more in rhythm.

"Oh this is getting good, More Light!" With a clear voice command the room lit up just enough for us to see my assistant climbing back onto Miss Dark and placing her cliterois back on her captives face as I continued to move my erect glowing dildo in and out of Miss Dark using my best abdominal crunches.

"Ohh!" Miss Dark yells, continuing to cum on my erection.

"More!" Miss White yells, continuing to cum on her captives face.

"MMM!" I yelled with my mouth closed, still remembering my assistant's directive, cumming heavily into the blue condom.

Miss White collapsed onto Miss Dark covering her face with her ample breasts. Nearly spent, I pulled out and immediately saw my assistant point to the chair behind the screen. Message received, I quickly walked over to my chair and removed the blue condom and proceeded to clean up.

Miss White reached up and clicked Miss Dark's hand-cufs, releasing her while she continued to kiss her former captives breasts.

When Miss White finally sat up she said, "That was nice. Next time I'm sure we'll try the fun parts."

By then I was already dressed and brought the tray of coffee and snacks that my assistant had prepared earlier.

As Miss White put her bra back on, Miss Dark sat sipping coffee and I realized she was perfectly comfortable being naked with a man in the room. I was personally embarrassed that it had taken me this long to figure out that Joanna Dark preferred girls.

"I've decided I want to do business with you Mr Addison." Miss Dark said confidently as I refilled her coffee.

Smiling and without pause I answered, "I will help you find partners for your company Joanna Dark, I have some banker associates that will give you an even greater margin than my company. I find myself wanting you to succeed with your business and still remain a close competitor or partner as you prefer."

Miss Dark was hardly listening as she was mesmerized by my assistant putting her clothes on.

Miss White said nothing but I could detect the slightest smile on her face.

It was then I realized what I should have known all along.

Miss Dark wanted this for herself.

Mr Addison wanted this for himself.

Miss White wanted this for Mr Addison.

I finally understood my assistant and why I was a very fortunate executive indeed.