High Heels Night

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Everyone gets a little wild at the annual sales awards.
7.1k words
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Part 2 of the 2 part series

Updated 03/09/2024
Created 01/07/2023
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In my previous tale about the joys of 'High Heels Day,' I realized that I never let you all in on any of the typical scenes from that special day. Ten or so naked secretaries acting as models, totally there and bare for the enjoyment of our best salesmen. Well... bare except for their high heels! I will describe one brief memory before I go on to the wonders of 'High Heels Night:'

Imagine sitting around a conference table with at least ten other men, and usually at least one saleswoman. We've all been introduced to these incredibly naked ladies, each one of them displaying varying comfort levels with their constant nudity. Some are 'oh my god: I can't believe I'm doing this!' others are 'I shaved for you down there and I dare you to look!'

The sexual tension in the room is palpable as the door opens and, not one or two but three nude women stroll in. One is carrying a tray of coffee cups with the usual accessories, the other two hold the door for her and then stand at opposite sides of the table, striking pretty poses.

Now each naked lovely moves around the table, approaches each salesperson and asks: "what would like with your coffee? Milk, cream or sugar?"

They are of course bending down ever so slightly. Their breasts are dangling at eye level. And they're standing back just far enough for one's gaze to briefly drop to their furred -- or furless -- slits.

We all have to bite our tongues as those innocent words 'milk, cream and sugar' take on such other, not so innocent connotations in our dazed minds.

But I digress...

I couldn't expect High Heels Day to remain a secret. All of that eye candy naked female flesh was, after all, a much sought after reward.

As company president, I soon heard that there was quite a buzz developing about what we would do to top High Heels Day at our annual awards ceremony. I was actually unprepared for that, but soon my remarkably dirty mind came up with some very entertaining ideas.

We rented a building with just the right sized auditorium, facing a stage with dressing rooms in back. There were fifteen tables seating up to six each, but I guess about 75 people were there. Salesmen and saleswomen with their spouses or dates, chattering with anticipation at what totally inappropriate naughtiness was about to ensue.

I had models walking around the tables throughout the night. Our theme was going to be minimal clothing, or the total lack of clothing, so I had them model our 'Teenie Bikini' line.

As I described last time, these swimsuits were hardly more than tiny cloth triangles connected with floss-like strings on top and daringly cut thongs as bottoms. Our latest innovation was in fact a choice of 'daring' coverage or 'regular' coverage for each size. 'Daring' came with this disclaimer: 'these bottoms are designed to only cover the average width of a woman's 'special area.' Please check local customs and regulations before wearing!'

I wondered if there were men who wandered into women's specialty shops just to read our labels.

Some of my floor models got together and suggested they go 'European style' -- topless -- toward the end of the night. I really appreciated their enthusiasm but I sadly had to say no. I was putting on a show, a show which was going to gradually feature more and more delectable female flesh as the night wore on. I didn't want anyone distracted from the stage by any bare boobs, freely bouncing around on the floor.

I watched nervously from behind the curtains backstage as everyone enjoyed their catered meal. I wasn't nervous about speaking in front of a group: I just wasn't sure how my addition of female nudity to the usual fun and games was going to go over. High heels day was a bit private; I was now taking the company kinkiness public.

Once everyone was done eating I got the usual introductions of new employees and then the boring secondary awards out of the way.

My floor models assembled backstage and I saw that many people noticed their absence and started talking excitedly. The program listed 'A very intimate fashion show' next up and I was quite relieved that my audience was ready for some intimacy.

I had seven models that night, all of them veterans of High Heels Day and somewhat used to nudity. I said 'somewhat' as strutting around on stage in front of at least 75 people -- not to mention the catering staff who had gotten wind of the show and were gathering in back -- was a different, scary experience.

My girls came out from behind the curtains stage right wearing an assortment of our unabashedly daring party dresses. Our version of the little black dress was an extreme micro mini. The hemline ended at crotch level, and there was no way to avoid displaying panties... which is why the dresses were sold with matching black thongs.

Our other item on display was our Flouncy Party dress. It was a one-piece outfit consisting of a tight bustier on top, bare shoulders, connected to a short skirt that was designed to stick out like it was starched. Underneath were layers of lacy slips -- also attached -- and of course the poor girl's panties were always visible. We recommended our prettiest laciest white panties to go with that look.

It was amazing to watch these beautiful models parade in front of all of us in these panty-baring outfits. It was even more amazing that there were actually women out there buying and wearing them.

When each of my girls was nearing her exit -- curtain stage left -- they would coyly start to undress. Zippers would come down, buttons unbuttoned, until their clothing was almost falling off.

As the last of the partially dressed models disappeared behind the curtain, there was a palpable sadness in the room. Until I leaned into the microphone and said: "Now for part two!"

One by one my girls reappeared, the ones who were Flouncy now boldly without tops, only their pretty panties. They all shyly covered their breasts until they stopped center stage and then dropped their arms, turning around and giving everyone a full view. And the audience went crazy.

We had a special surprise: the models in our micro black dresses were even bolder: they had on open black bras matching their thongs that revealed bare nipples clasped with dangling silver pendants. Open bras and nipple jewelry were both new 'adult' items we were adding to our collection.

The audience was so crazed that I think I could have asked the ladies present to please take care of the nearest gentleman and some would have complied.

Then in keeping with our stripping theme, each girl started pulling down her panties as they neared their exit, giving the very appreciative audience a very special last look.

Once each model went behind the curtain, there was a brief pause. Then the girl stuck her head out, waving her pretty panties at the crowd in a last goodbye.

I'd like to say that each one of my girls got a standing ovation, but I was sure, looking around, that there several males in the audience who just couldn't bring themselves to stand up at that moment.

Now was the time for out major 'Salesperson of the Year Award.' I deliberately sandwiched it in between our last two bits of what promised to be adult entertainment as I didn't want anyone leaving.

Lest anyone wonder what was meant by "Charity Fashion Auction" in our program, there was a helpful guide as to minimum bids for every article of clothing from blouse and skirt or dress, down to panties. No, there was no doubt about our enticingly naughty intentions, and I swear there were more men in the room then we started out with.

I looked in the back of the auditorium and noticed that the entire catering staff, including men who should have been cleaning up back in the kitchen area, were now very present and eagerly watching. The word must have gotten out during our little striptease fashion show, and not a male in the building was going to miss the next and final act.

Marguerite, one of my favorites and a veteran of High Heels Day, came out from behind the curtain to hand me the envelope -- very Oscar-like -- and stood back to one side, smiling.

She was wearing our micro black dress and her very sexy appearance got a round of applause. Marguerite was one of the girls that I had gone a little too far with during our private prep for High Heels Day. I would like to say there were no hard feelings, but I always felt hard when I saw her.

She loved being naked and thought it was her natural state. So she was going to be perfect as the 'volunteer' whose clothing was going to be auctioned off for charity. Although she had never gotten naked for this large a crowd, she was clearly excited. I noticed immediately that I would have to change the pricing structure: unlike our prior models whose legs were bare, she was wearing black, thigh-high stockings that would have to come off first.

The fact that she didn't go backstage but just stood there, looking positively edible, was not lost on our audience. I could see that they were already checking out the merchandise -- as well as her clothes -- and were already trying to calculate when and how much to bid and when.

Then I opened the envelope and announced the top salesperson of the year and everything changed.

It was a woman named Jackie, and as I scanned the room and saw her getting up from her table, I mistakenly dismissed her at first as a 'big girl.' Wrong. The more I looked, the more I liked. Jackie defined the word 'statuesque:' I was 6' 2" and she was nearly my height in heels. I guessed she was about 5' 10" in stockinged feet.

There are women who are only 5' 2" or so who nonetheless have perfectly proportioned, nicely curved bodies. With Jackie there were simply more curves to love, and much longer legs leading up to those curves.

As she got closer, I stopped mentally undressing her for a moment as I admired her choice in clothes. Like every saleswoman there, she was entirely dressed in clothes from our line.

Her powder blue blouse was nice and form fitting, with plenty of visible cleavage. This was from our more mature or less daring line called 'Special Lady.' Our lingerie in this line was, of all things 'Intimate Lady.'

As I said, all our blouses were a bit tight and quite low cut. If you didn't want the valley between your upper mounds on display, you had to buy from someone else.

Her skirt was a pleasant surprise. At first it looked like a knee length skirt with long, multicolored stripes. It was actually two inch wide, individual pieces of soft fabric that were only sewn together at just below panty level. As a lady moved, it was possible that her legs would be bared, quite possibly up to her thighs.

And that's exactly what I saw as she climbed the stairs just to my left. With each step: each of her long strong muscular legs was bared to mid thigh. She caught me staring and looked down to see what I was seeing. Then she looked back up at me and smiled.

I became her biggest fan at that moment. She was probably in her early forties, and she was a strong, sexy, confident woman. She knew she still looked damn good and she loved it that I was looking.

I had a sudden vision of those legs wrapped around me, her feet pounding me as if she was trying to push my entire lower body into hers.

But Tara was home and she was probably already naked.

That was my mantra whenever bad thoughts entered my head.

Tara really was probably in my townhouse, wandering around naked. She told me it was to apply her 'sexual aura' to the place so I would feel her when she was away. I was a man so I nodded sagely, but all I heard were the words 'naked' and 'sexual.'

If you want to read Tara's story, it's all there in 'High Heels Day.'

But then Jackie was on the stage, leaning in for the obligatory hug and peck on cheek, when I knew it would be a bad idea for her to make contact below my waist. It must have been obvious to her that I was holding back. In an exchange too brief for the audience to notice, she pointedly looked down at my crotch and whispered "I hope I'm not the one responsible for your little problem!"

Did I say I was her biggest fan? At that moment I would have paid someone to distract her husband for a few hours, and tried to get to know her better..,

But Tara was waiting at home for me, naked.

Funny but, thinking about my wonderfully naked girlfriend at home didn't really do anything to help my 'little problem.'

I watched as my hostess Marguerite handed Jackie her award. And there was a nice hug between the two of them that I certainly enjoyed.

Then Jackie stood at the podium, leaned into the microphone, and said her opening joke, which changed the course of the evening:

"Hi everyone! Well, it looks like you'll just have to put up with me for a while: I'll be the only female on this stage tonight who isn't taking her clothes off!"

Well.

The place erupted with some exaggerated boos, a few catcalls: "Hey, why not?!" and even one female voice "Go ahead Jackie: do it!"

Did I mention that there was an open bar?

This was obviously not the reaction that Jackie was expecting. She turned beet red, licked her lips, and then started her prepared 'thank you' speech a little shakily.

In the meantime, my notably dirty mind was already going crazy. A woman would say my cock was doing my thinking at that point. No, there was actually an intense internal dialogue between my cock (ask her!) and my brain (this will finally get your ass fired!)

As she continued her speech, I studied the beautiful features of her face. She had high cheekbones, blue-green eyes, and a somewhat Nordic look that of courses made me think of a Viking warrior. A female, barely dressed Viking warrior. Her dark brown hair had blonde streaks and was pulled back in a ponytail that made her look oh so professional and breathtakingly lovely.

When she was done and the applause died down she looked at me expectantly. I was supposed to thank her and give her another peck on the cheek before she walked away, clutching her award to her ample chest.

Instead, I grasped the podium, took a deep breath, looked directly at her and said "What would it take for you to stay on stage with us tonight, and become the model for our charity auction? How about twice your annual bonus?"

I know I keep saying that the place was erupting and the audience was going insane, but that's exactly what happened.

Jackie herself stared at me, turned white and then red. I saw her turn to the audience and look for her husband. His mouth was open and he was even redder than she was.

I saw him mouth something to her over and over until she finally got it. She went back to the podium on trembling legs and managed to gasp out: "Did you say triple my bonus?"

Do I need to state the reaction?

People who saw MY reaction say that I turned white as a sheet. We didn't have the money to pay her double, much less triple her bonus. I knew that this was going to come out of my own pocket as I numbly nodded 'yes.'

I scanned the audience to check: no employees of the payroll department or -- thank God! -- Human Resources. I had already crossed the line. I was asking a female employee to allow herself to be stripped naked in front of her coworkers. And I had just promised to pay her for it. I was in a very sensitive area, but I so desperately wanted to see Jackie's very sensitive area.

Once the audience calmed down enough, I began explaining how our auction would proceed. Each item of clothing had a minimum bid. Bids would be per table to make things simpler; each table could then pool their funds. Every table would have to agree though on who would be the lucky guy -- or gal -- to come up on stage to claim their prize.

Oh yes, that got a reaction from everyone, including Jackie, whose eyes got wide as she licked her lips. She was not going to be allowed to undress herself: she was going to BE undressed.

I looked over at Marguerite, who had been unexpectedly relegated to playing hostess. I knew that she was so looking forward to being the star of the show; every eye on her as she slowly got naked.

And we had a special bond: it was just over a year ago that I had invited her into my office for a private meeting to see how comfortable she was with her nudity. Well not only was she comfortable with her nudity, she made me comfortable too. Did things get out of hand? I had a firm hand on her, and she had a firm hand on me towards the end of our memorable session.

It was all too exciting and warmly embarrassing but we were both adults. I'd like to say there were no hard feelings but I always got a hard feeling when I remembered that special afternoon.

I had a sudden inspiration and I walked over to Marguerite. "Let me demonstrate what you'll do when you come onstage" I said to the audience, and I motioned for her to turn around. She was puzzled at first, then she gave me the biggest smile as she turned her back to me.

I unzipped her slowly, down to her waist. She was so helpful: straightening her arms when needed and wriggling her willowy form. I pushed the tiny black dress over her slender hips and it fell beautifully down her legs.

When she at last tugged the tiny garment over her heels and handed it to me, I was stumped as to what to with it. I shrugged and draped it over the podium.

That little dress, brazenly hanging there, at first seemed like a sexual trophy. Then I took it as more of a signpost: we had all crossed a line; we were all complicit. We were all intent on coercing a beautiful, mature, professional lady to get naked for us -- simply because we found it so arousing.

That, though, was one of most intensely sexual memories of that night for me: slowly stripping the dress off a beautiful girl in public while she was getting so excited, she just wanted to rip it off.

Jackie was trying not to act jealous as Marguerite became the center of attention. She looked at me and shrugged as if to say 'can we get on with it?'

Before I start getting Jackie undressed for you, let me reverse things by describing how Marguerite looked from toe to head.

She had on the requisite silvery heels -- closed-toe since she was wearing stockings.

Full disclosure: the famous heels were the only article of apparel that we didn't manufacture. They were the only item our High Heels models were allowed to wear, aside from minimal silver jewelry. We liked the aesthetics of seeing nothing but flashes of silver on a naked girl's body.

Next were elasticized black stockings that went up to mid-thigh. Her tiny black thong was so daring that it absolutely required a complete shave.

Like the other models, her open black bra was only there to lift up her 34Bs. Her breasts and nipples were completely exposed. Marguerite was one of a few models with pierced nipples. A pendant with a short silver chain hung from each nipple with what looked like a black pearl dangling down.

I wanted to play with her pendants like they were pendulums and watch the pearls sway back and forth. They did catch the eye, and her nipples were so long and hard to begin with they made her slightly conical tits seem larger than life.

But now, at last, the auction. Each table had one of those signs to hold with their number when they were making a bid. The first item was Jackie's blouse, powder blue, low-cut and quite tight. I went with the opening bid of only $250, thinking that a lot of folks were saving up for the privilege of taking off her bra and panties.

Surprisingly there were a lot of excited bids. I finally figured they were really looking forward to getting things going, and getting this pretty lady's clothes off.

The winning bid was $750. I watched in disbelief as what was probably the youngest looking male in the room rose from his table and made his way up stairs. He looked so reluctant, as if he was on the way to the principal's office instead of becoming the first person to get a lady's clothes off.

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