"Stockings & Heels Hypothesis" by HeyAll
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From the perspective of three different women.
xxx THE BOSS, MS. HALLERIN xxx
I once said that everything about a woman is sex and lust. Beneath whatever proper veneer a woman shows you, it comes down to the same things -- her nipples and clitoris. No one likes to admit that because it undermines mainstream femininity... or maybe it's the underpinning of femininity itself.
The view from my office will always be stunning. I'm the CEO of a financial firm, age 57 and loving it, and I have long streaks of gray hair which I proudly showcase. Before I retire, there's a question that's lingered in my mind for years; could any woman become anything? Obviously there's a degree of reasonableness to that question. Not everyone can become a pro athlete, singer, or an engineer, etc...
I once read a story about a female Chinese CEO who joked that she'll train her beloved secretary to become her replacement. That stuck with me ever since. I often wonder if I'm unique, one of a kind. Or if I just got lucky with circumstances.
Enter the girl who sits outside my office everyday, Natalie Mendoza, my loyal secretary for the last five years. She steps into my office and closes the door at approximately 10 a.m. as we'd scheduled. I watch her graceful motions, she's a tall, leggy girl from Argentina who always wears pressed blouses and knee-length office skirts, and she always wears flats. Secretary's outfit. Secretary's demeanor.
We sit around a coffee table. She's a bit nervous, probably thinking it's an evaluation because we've never sat like this in my office before. She pours me coffee everyday, this time I pour her a cup. She's struck by my newfound humility. I can't remember the last time I've poured coffee for anyone in the workplace.
Natalie sits upright on these low seats, I love her posture. She's a raven haired beauty with light skin. Her knees are pressed together in a ladylike manner so her thighs don't show. I try not to gawk at her, I'm sure she doesn't notice that I'm admiring her tall figure.
"So, a little bit of news for you. I'll be retiring in a few years. You're the first to hear this."
It feels like an out-of-body experience to finally speak these words, which makes Natalie pause and put her coffee down after taking a sip. She gulps the warm drink. I wait for her response. She has a slight accent which she's trying to get rid of. I wish she wouldn't. Her original accent arouses me.
"For any particular reason?" she asks.
"I'm not being forced out, if that's what you're implying."
"Oh, that's a relief. May I ask why you're leaving? You're at the top of your game."
"I'd like to travel the world. Dubai, Africa, a few spots in Asia."
"Lovely places," she says.
"They are, but this conversation isn't about me. This is about you."
"Me?"
"When I was younger, I had every advantage to climb the corporate ladder. Rich parents, family connections, the best schools, a long list of mentors. As a result, my work here has been stellar. I took share prices to record highs. Now I wonder, could a normal woman also do this job, if given the same privilege?"
"It would take a serious person to fill your shoes."
"How about you? That's what I'm wondering. I'll be the public face of this firm, but you'll run things on my behalf. You'll fulfill most of my obligations."
"Excuse me?" she says.
"I'll train you first, you can follow me around, I'll teach you the important things. Then, for a few years, you'll handle most of my duties. I'll pay you accordingly."
Natalie pauses, then gives a nervous wince. "The salary upgrade would be fantastic, but crashing this firm would be horrendous."
"The firm won't crash because I'll guide you here and there, especially the major decisions. And yes, I'm serious. Officially you'll be promoted to a fancy title, but unofficially you'll be calling most of the shots. I want to see how you lead. I want to make you a leader."
"Why are you doing this?" she asks.
"Personal and professional curiosity. I want to know if leadership can be taught."
"That doesn't sound like a great hobby."
"Very little excites me these days. I can honestly say this is the most exhilaration I've felt in years."
"It's difficult for me to agree," she says. "I don't know how serious you are. It could be a passing thought which you may regret tomorrow. Or maybe you're testing my loyalty. Even if you meant this, I'm terrified of being unprepared."
"Suppose you were interested, then I prepared you properly. What would be your biggest motivator? The money? Power?"
Natalie thinks long and hard. "Everyone could use more money these days, but I'd like to know what I'm capable of. I'd like to see if I can do it. I guess we're on the same page."
"Then let's get started, okay? Remove your flats. Put your bare feet on the floor."
After her initial hesitation, she starts removing her flats and I walk to my closet and sift through my wardrobe. I grab a pair of stockings and heels, which I bought specifically for her, and I return to her.
She's already sitting in an upright posture with her hands folded on her lap, her bare feet on the carpet, next to her flats. Her calves and feet are delicious to look at, toned from walking around the office all day, but this isn't about my stimulation.
I approach Natalie and get on my knees. I can only imagine what she's thinking as I assume the submission posture for the first time in our relationship, then I start rolling the stocking up her legs, one at a time, going up mid-thighs. This isn't meant to be sexy. It's meant to be a blessing.
Finally the high heels. Putting thousand dollar heels on my secretary's feet is like putting a crown on a maid. With a gentle touch, I slide each heel onto Natalie's feet, securing them in place to finish the transformation. I fasten the straps and then rub her soft ankles.
Natalie stands and walks around when I tell her to. She's several inches taller now, much taller than me, and her movements are awkward. It's so obvious she's a novice with high heels. Her presence in my office has shifted, from a secretary who lingers in the background to a statuesque woman who commands attention with every stride. I'm impressed. This might work after all.
xxx NATALIE MENDOZA xxx
My previous gym was a reasonable $40 per month fee and anyone could join. People from all walks of life were coming and going. This gym, however, is located in the heart of downtown's financial district. Membership is exclusive and it's very much a club. Women here have known each other forever and I'm the youngest of the group.
What surprises me the most about this exclusive gym is how familiar the women are with each other. It's common to see a group of 40 or 50 something-year-old women in the sauna with nothing but towels wrapped around their hair, having casual conversations.
Because these women know that I'm the de facto boss at my firm, they've been extremely welcoming to me. Relationships are the cornerstone of business and they've held firm to that belief. Imagine me in the locker room while nude corporate bosses, executives, and managers are discussing their weekend plans or dinner parties.
And unlike normal gyms where people dress quickly and leave, here, the women take their time. It's almost a ritual. They take their time rolling their stockings on their feet, either while standing with one foot on the bench, or sitting. Their heels are always designer, from the biggest name brands. Oftentimes I'll see mature women fixing their stockings and heels, even before putting on their undergarments, standing there completely nude.
If I sound like I don't belong in this world, it's because I don't. My boss thinks it's amusing that I'm in this position. I'm a social experiment. The Board and shareholders would go crazy if they knew this was happening. But I guess, in an interesting way, that's what makes this fun for my boss, and scary for me.
Ms. Hallerin spent two weeks training me to assume her duties. By that I mean, she did the bare minimum. She called me into her office a few times for brief conversations on how to negotiate and assume a strong posture. She gave me a few handwritten notes and charts to keep. And she sent me emails containing Youtube videos to watch. That was literally it.
Anyway, I'm flanked by two company lawyers as we head to the 26th floor of a commercial building. The acquisition of the South Korean owned entity has been in the works for a year, and I'm tasked with completing the takeover.
This is my second time meeting with Jang and her group of lawyers, a mix of Americans and Koreans. I'm mostly repeating the talking points Ms. Hallerin gave me, while letting my lawyers do the rest. I can tell that Jang isn't too thrilled with having to sell her business. I get the sense that it wasn't her choice.
After the meeting concludes an hour later, we shake hands and end things on a cordial note. Then as we leave, she flags me down in the hallway and asks for a moment of my time. I tell my team to wait in the building lobby.
"This will be fast," Jang says. "We both have busy schedules. Let me show you our meditation room."
The room is small, minimalist, and she sits on a cushioned chair -- the only seat available -- which means that I'm left standing in the center. A total power move on her part. I wish I could have Ms. Hallerin in my ear telling me what to do, because she'd absolutely know how to handle power plays.
"Comfortable?" I ask.
I wonder what Jang's intentions are. She's a demure young woman, book smart, and she keeps a straight face. She tries relaxing in the chair, but relaxing isn't her strong suit. Her knees are pressed together and she's wearing a knee-length skirt with stockings and heels.
"This is my company, of course I'm comfortable here. When this deal goes through, I will be paid handsomely for the buyout -- yes -- but I will also return to Seoul as a failure."
"Is that what you think is happening?" I ask.
"What else is there? The people who backed me financially will have a low opinion of me. My career will suffer. That's how it works in business, as you will come to find out."
"I can help you. Maybe you can work for me. Maybe you can stay here in some capacity."
"You think I'm a charity case?"
"No, no, that's not what I'm saying."
"You're new," Jung says. "So obvious. You have intelligence but very little experience. Are you a fast learner?"
"We don't have to do this."
"Have you been taught about business etiquette from your boss? Where is she? Hiding? On vacation?"
"What are you talking about?"
"You owe me small favors."
Jung leans back on the chair and pulls her skirt so that her skinny thighs are showing. She spreads her legs, no panties. Her labia is dark and her pubic hairs are curly. All throughout the meeting she kept things natural. Does she always come to work like this? Or is this specifically for me?
"What are you doing?" I ask.
"Are you..."
She doesn't bother to finish her sentence when she sees my confusion, then she grimaces. She acts like I'm being offensive for not indulging her advance. She stands and straightens her skirt. When she storms out of the meditation room, she does it with so much fury that I start to feel guilty, even though what she wants is more than what I can give.
xxx
It's two days later when Ms. Hallerin returns to the office after getting my text messages. She plays the politician role when she meets with top managers and keeps up appearances. Being respected is what she lives for, she thrives off attention.
When we're finally alone in the private office, she insists that I sit behind the CEO's desk, while she sits across from me. The power switch will never get old, but that's not the biggest thing on my mind. I tell Ms. Hallerin everything and she sits there and nods. Nothing about this shocks her. She's heard this before. It's familiar to her.
"And what are you doing about it?" she asks.
Ms. Hallerin's tone of voice is annoyed, like the answer is so obvious. She used to do this routinely when I was her secretary, which makes it clear that she still views me the same way. I'm still the secretary in her eyes. A pet project for her.
"I was hoping you could give me insight on what to do."
She keeps a straight face. "Well, clearly Jung needs her pussy eaten."
"Are you being flippant, or have you ever done... that?"
"I'm a business woman. There's your answer."
"Oh..."
"Truth be told, I was wondering how long it would take before you ate your first pussy. The occasional fling is for office employees. Now you're flying at a different level. At this altitude, everything is about ego and reputation. You're buying Jung out. She worked crazy hours to reach her status and now she has to go back to South Korea defeated. The least she wants in return is her pussy eaten."
I stop myself from falling over on my chair. Ms. Hallerin is amused by my reaction and she gives me time to process this information.
"At this point it's getting difficult to separate fact from fiction."
She shrugs. "Welcome to the corporate world."
"We've known each other for years. I've been in charge of your schedule and kept your secrets. I can only conclude that this is some elaborate hoax. Or maybe, perhaps, you're trying to gauge my loyalty to you. Did you put Jung up to this?"
"That's a fair assessment, but you're wrong."
As if putting my doubts to rest, Ms. Hallerin leans back and lifts her knee-length skirt from the hem. There's nothing beneath. Her legs are skinny and reflect her older age, and also she's waxed, not a stubble of hair in sight. When she spreads her legs, all I can do is stare in disbelief. This is the woman I've been loyal to for the last several years. A woman of power and ferocity. Now I'm seeing the depths of her, literally.
"You must have thought of me as a sexless bitch," she says.
"Could you blame me?"
"No, my reputation is carefully guarded."
"What now?"
"You have to close the deal with the South Koreans by any means. Don't fuck it up."
"Even if I have to do... that."
"Say it."
"Eating her pussy."
Ms. Hallerin taps her clitoris. "Come here. Let me teach you something."
With some reluctance I stand and approach her. I'm leaving the safe confines of my desk and walk to her exposed vagina. It's yet another reminder that my status is false and hers is the real thing. When I'm standing in front of Ms. Hallerin, she gestures with her index finger for me to kneel.
My heart pounds when my knees touch the floor, my eyes looking straight between her legs. Her pussy glistens. She's so calm. So beautiful. So commanding.
"If you don't eat Jung's pussy she might not close the deal," she says. "That's how it works. An exchange of egos and pride. Understand?"
"Yes I understand."
"Give it a try. I'll work with you."
It's a funny feeling when you realize that everything you know is false. I thought I knew this woman, but I don't. I thought I knew the corporate world, but I don't. I question all the years I've worked as a secretary, people coming and going from this office, doors closed, while I sat behind my desk outside.
I wonder how many times Ms. Hallerin was getting her pussy eaten, using her power and influence to get the kind of pleasure I'm giving her right now. So many women were coming and going through those doors. Women of different ages and authorities. I have to reevaluate everything.
She tells me what to do, how to work my tongue, how to suck. She tastes sweet and she's very wet, her body emanates warmth. When she cums in my mouth, it's yet another reminder that she's my all-powerful boss, and to be honest I've never been so aroused.
xxx
A week later I'm sitting across the conference table from Jung and she begins expressing skepticism over the deal. The lawyers are blindsided by the sudden apprehension, but I understand full well, so does Jung. There's this delicate dance between us while everyone else talks about the details.
"Can everyone leave the room for a moment?" I ask.
I'm talking to my lawyers and advisors, which surprises them, but no one talks back to me. They get the message and leave the conference room.
Jung is calculating the moment, she doesn't do anything until my people leave the room, and even then she sits there and contemplates, staring right at me. She then tells her people to leave, but only the men. When they leave, Jung is flanked by three women, one American and two South Korean, and this feels like a showdown.
"Well?" I ask.
She looks at me, assessing me. I wonder if the women sitting beside Jung know what to expect. If they do things together and it's their secret, which is why only the men were asked to leave.
"I've been too hard on you. None of this is your fault."
"But you're still expecting something," I say. "During this entire meeting you've been putting up roadblocks."
"I have very high standards. What can I say?"
"We can stop playing games and get this deal done."
"Not until I get what I want."
Jung doesn't elaborate any further, she just looks at me. Her demeanor has softened but she's still razor sharp about what she wants. Her arched eyebrow says it all. But what she wants might be more than I'm able to give. I still wonder if the women sitting beside Jung know what this is about. I wonder if Jung had previously exposed herself to them, like she did with me.
As the seconds move along it's become clear that this negotiation won't advance until I give in. She wants me to make the first move. She wants me to lower myself to make amends for buying her firm, even though I've done nothing wrong. Would it be so bad? I already broke the taboo with my boss and loved it. I'm clenching between my legs thinking about doing this with Jung, but her advisors in the room are making a complicated situation even more complicated.
I stand and walk around the table, her eyes locked on me, following my movement toward her. When I get close, Jung turns her seat and I see her stockings and heels and knee-length skirt. Is she pantyless again? She must be. Again I wonder if her advisors know what's coming. I'm hoping -- praying -- that she'll stop this, that it's all a bluff.
"Are we really doing this?" I ask.
"What I'm asking for is reasonable. My firm has great value and you're getting it for a great price."
"Those terms were already negotiated."
She scoffs. "It wasn't a fair deal. You weren't there. You wouldn't know."
It makes me wonder what hardball tactics Ms. Hallerin might have used when negotiating these terms. She's known for shrewd tactics and using whatever leverage in her power. I wonder if the two of them had ever done anything sexual. At this point, I wouldn't be shocked if Jung was made to eat Ms. Hallerin's pussy, and now Jung is getting revenge by doing this to me.
Whatever the case, losing this deal would be the end of my career. Not only would I get fired, but it would also be a huge blow to my self-esteem. I'd worked myself up mentally since being thrust into this position and I swore to myself that I'd succeed. I need this for myself. I need a win in life, the kind I'd never tasted before.
Not everything is about money. Sometimes it's about personal accompaniments. Sometimes it's about the stockings-and-heels worn by the woman sitting in front of you.
"Can we have privacy?" I ask.
"We have enough privacy. These women know everything about me."
I take a deep breath. "I'm new to this."
"That's obvious. Do this, then we'll do business."
Jung reaches down and unclasps the delicate buckles of her heels and steps on the carpet with her stockings. Then she removes her stockings, one foot at a time, and rolls them into balls and places them on top of her heels. Her bare feet are on the carpet and she looks comfortable like that.
She spreads her legs and hikes her skirt, no panties again. She still has a dark, curly bush, but today it's trimmed. I wonder if this woman ever wears panties to the office. I wonder if she removed her panties before this meeting, or if she's like this all day, even feeling the outside breeze between her legs, as she comes and goes from this building.
Her legs are spread wide and the professional women at the table are watching me. They're not looking at Jung's hairy pussy, they're focused on my reaction, which means they've seen her pussy before. It's nothing new to them. What's new to them is how I'll service this pussy and they possess the most serious gaze I've ever seen. It's like they're in a courtroom and a verdict is about to be announced.
I get on my knees and my shame has never been so great. It's different doing this for Ms. Hallerin because I respect her and trust her; she's responsible for everything I have. Plus we had total privacy. Jung, on the other hand, feels much more like an adversary. It's like I'm serving the corporate enemy. We're buying her out -- not the other way around -- which is why this feels so off base.
Looking at Jung's wet pussy up close is a revelation. I shouldn't be aroused by this, but I am. I've already been trained by the best. I close my eyes and bring my mouth to her. I do my best to ignore the other women in the room who are watching this act of subservience unfold. I also ignore the pubic hairs which are tickling my upper lip and the tip of my nose. My throat felt dry moments ago, boardrooms are always stuffy. Her fluids alleviate that dryness. Licking her pussy feels ridiculous, unprofessional, but Jung's expectancy and the judgment of the professional women are worse.
That particular brand of corporate shame turns me on. That's the worst part I think. Loving this. The sweet, juicy flesh brings flavor to my mouth, my tongue goes inside, exactly how Ms. Hallerin taught me the other day. I'm a pussy eater now. Someone who gives oral service to prominent women and I can feel the eyes in the room judging me as such.
I can feel Jung breathing on me and I can sense her sharp gaze. This is a form of sexual revenge for her. I'm tasked with closing the deal to buy her firm, she's getting her pussy eaten by me. As my tongue goes deeper and swirls inside her warm hole, I listen to her moan. She rubs the back of my head and pulls me closer. She's going to cum in my mouth. This is not how I envisioned closing this deal.
With her hand still holding me, Jung stands and the hem of her skirt falls on my face. She's grinding herself onto my mouth, her pubic hair is like a brush. When she cums it's like a flood, more so than Ms. Hallerin, and I'm thinking of my expensive suit. She tastes like a peach, with the same texture as nectar, and it's a burst of summer in my mouth.
Her fluids make me choke and the excess runs down my chin and wets my blouse. I can feel the spots soaking through the fabric. I should be disgusted, but I'm not. Instead there's an ethereal sensation in giving this woman sexual pleasure, alongside the exhibitionism and voyeurism within this conference room. An absolute dirty feeling letting her cum down my throat.
When she finishes, she lets go of my head. I can hear her breathing. Her pussy is still throbbing. Only droplets of clear fluids leak from her tight pink hole. I'm stunned and flabbergasted from having done this in a corporate setting, but I'm also in desperate need of my own orgasm. I'm like a timebomb ready to explode despite the intense shame of being squirted on.
"Now we can discuss business," she says.
Jung bends down and licks my chin with the broad stroke of her tongue. It's a condescending slurp, as if she's claiming me. That's when something clicks inside me. She can play this game, so why can't I do the same? Why should women like Jung and Ms. Hallerin have all the fun, while leaving me on my knees wearing the mess on my face?
I look up at Jung, still kneeling, and she looks into my eyes. The pompous look on her face is gone. We both know that she'll be kneeling at some point. I imagine her face in between my legs, or in between my butt cheeks, her tongue returning the favor. Me making a mess on her custom suit.
xxx THE NEW SECRETARY xxx
My hands are almost shaking because I'm so nervous. At the age of 26, I'm starting a new job here at one of the city's big financial firms. I head to the top floor wearing my new outfit, trying my best to appear confident, like I belong, and I'll be working for Ms. Hallerin as her secretary.
When I get to the office I see a young woman sitting behind the desk where Ms. Hallerin should be sitting. She's leaning back with her bare feet propped on the desk. I love her long legs. She's talking on the phone, numbers and figures, she looks stressed, and when she sees me she signals me to come inside.
I enter the office and linger while she's still on the phone. How did I get so lucky to work around here? And who is this mystery woman sitting behind that desk? The view of the city is breathtaking and the office has a chic design. This is heaven for someone like me, I could get used to this.
When the phone call ends, the woman takes a deep breath. Stress. I know the feeling, though not on her level, whoever she is. The woman stands and I'm struck by how tall she is. Close to six feet, wearing a skirt with a white blouse. She moves gracefully while barefoot as she comes around the desk and offers me a handshake.
"I'm Natalie," she says. "I've been expecting you. I went through your resume."
"Yes, hi, great meeting you, I'm here for Ms. Hallerin."
When she stands in front of me, it's like looking up at a tower. I'm used to dealing with intimidating women, but Natalie seems different, she seems kinder with kitten eyes. And she's closer to my age than people I'm used to dealing with.
"I'm handling things here," she says. "So, do you have a lot of experience?"
"Well, I've been doing secretarial work for two years. That's in my resume."
"No, no, the other kind of experience."
I blush. "Yes, I've been trained to give service."
"Do you enjoy it?"
"Very much."
"Help me become presentable. I have a meeting soon."
"Yes, right away."
Natalie doesn't elaborate but she's still barefoot and I see her stockings and heels on the floor. I rush to get them. She sits her butt on the desk and I kneel. When she extends one of her long legs, I slide the stocking onto her foot, rolling it up smoothly.
"What kind of experience do you have?" she asks.
After that leg is done, she puts her foot down and lifts the other foot.
"I used to lick my previous boss, you know, under her desk. She taught me how and I became good at it. Eventually she loaned me to her friends and colleagues in the business world. That's how I built my reputation so fast, because I knew the right people and I'm a diligent worker. So yeah, I can do pussy lickings and ass eating. I can also help you get dressed, like right now."
Her stockings are secure, then we do the same process with her heels, one foot at a time.
"My journey is similar," she says. "This is something I was taught. My role switches. These days I'm more into being served. I've made snobby executives eat me out. I love that, putting them in their place. Do you like the sound of that?"
"It's an enticing thought."
"Do a good job, I'll have snobby women eating you out."
Thinking about being served by executives sends a shiver down my spine. I've never been served before, I've only served. Natalie knows this about me, she can sense my submissive nature and meek personality. She's giving me a gift.
I kiss her toes and feet after putting on her heels. Then I kiss her calves, then knees.
"Thank you. I'd like that."
Afterward I kiss her thighs, when she doesn't stop me, I keep going up her thighs, giving more kisses. I lift her skirt. She's not wearing panties. All this time. Who is this woman and how does she have so much power? My face nestles against her smooth crotch, my nose touches her small clitoris, which is erect.
I give it a lick, then more licks, then kisses, then I start sucking on it, which makes her moan. My first hour on the job and already I'm eating pussy. My tongue fucks her, in and out, and she remains calm. Her groaning means she approves of my technique.
"We'll get along just fine," she says.
Making her cum is an absolute joy and she strokes her fingers through my hair. Her orgasm is gushing and warm, her breathing is hard, and she looks at me with content. Afterward she thanks me, she pulls her skirt down and excuses herself for the meeting. No wiping, nothing. She goes to her meeting with an orgasmic pussy that's coated in my saliva, and she says we'll talk later.
The End
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