Under Her Harsh Heel

by lego3

Rating: mature
Tags: Sex, Ms. Harshwhinny, Slice of Life, My Little Pony: Friendship is Magic, Anthro, Anon, Porn, Second Person, Fetish
Length: 3811

(CONTAINS HEATED FOOT FUN.) You're working at Harsh Fashion, directly under Harshwhinny herself. What benefit could being her butler/secretary/salesman bring to you?

(CONTAINS LOTS OF FOOT STUFF. IF YOU IGNORE THIS WARNING, YOU HAVE A THING FOR MILF FEET.) After managing the Equestria Games, Miss Harshwhinny has had a bit of...trouble returning to manage her fashion company by herself, due to all the extra press. You, Anon, sat next to her on the train outside of the Crystal Empire...and she deemed you obedient and useful enough to work under her. Didn't even give you the option of giving your previous job a two week notice. Rude. But hey, you just might have gotten some rather desirable benefits...

By the way, Nasiri, if you're reading this, thank you. That was a good, solid bit of alone time with that pic.

Published 2021-06-02 03:40:01 UTC
Last updated 2021-06-02 03:40:01 UTC

Toe-ing the Company Line

It had been a fair few months since you, Anonymous, had woken up in this technicolour land. Equestria, the land of friends, where ponykind do roam. Ponykind? It certainly was a bit of a stretch to call them ponies, because they all had humanlike body proportions, and only the head of ‘ponies’.

At least it wasn’t TOO difficult to fit into your new environment. The ruler of the shiny crystal streets you turned up in, Cadance, was kind enough to offer you a train ticket down to the friendliest place in Equestria, especially newcomers. The town of Ponyville.

At least, that’s where you thought you were going. Your journey had you sit by a very INTERESTING mare’s side. Mare? Woman? Womare? Mare it is.

She was quite distinctive, a permanent frown fixed upon her face. She wore a violet blazer or suit-coat, a matching skirt that was…admittedly quite tight around her bare legs, and her scarf looked to be made of the finest materials the land had to offer.

Figuring you would be better off learning from a local as much as you were able, you started a friendly conversation with the mare…

Within the hour, the deep orange mare, Harshwhinny, had given you some rather stern lessons on how to be more ‘professional’, pointed out all of your colour-coding and fashion-sense flaws, and hired you to work at her fashion firm, Harsh Brand. All while standing over you on the train, leaning down to look you in the eye. Leaning far enough for you to have a very...clear look at what was down below that collar of hers.

You couldn’t muster up any sort of objection, or response to her demand for you to work under her. Miss Harshwhinny took your stunned silence as obedience and willingness to learn from her, and thus paid to extend your trip over to her Manehattan firm, hundreds of miles away from Ponyville. She even paid for a small apartment for you near your new job.

At your job attending to Harshwhinny herself, which you aren’t even sure what the title truly was, you were worked to the bone. But, of course, you were treated fairly, and compensated handsomely. So you put in 110% effort into whatever your boss had you do.

Due to Harshwhinny’s ceaseless hard work, massages for her were one of the main things on your vast and varied daily checklist. They ranged anywhere from the top of her golden-maned head, to shoulders, to upper back…

While you were more than happy to do those things for her, your boss never commanded you to rub her anywhere below her upper body. Unfortunately, that area did include her feet…feet that she was standing and walking on day in and day out, in high heels no less.

Sadly for you, she also had the tendency to stretch out those toned bare legs of hers, splaying her dexterous-looking toes below her desk and allowing her heels to hang on by a thread. Months of this unwitting teasing were beginning to take a toll on y-

“Anonymous,” a voice said behind you, jolting you out of your train of thought. You turned around to see your boss, Miss Harshwhinny, placing her hand on your shoulder. You could never tell if she was annoyed or angry, so being called like this always had you on edge.

“Yes, Miss Harshwhinny…?” you replied, cautiously.

“I believe it’s time for your first evaluation. You’ve been here for a while, so let us see how things are going with your duties, hm?”

Slightly nervously, you nodded, rising out of your chair and following your boss into her office. Your eyes drifted down to those bare legs of hers, one placed in front of the other, and vice versa, her hip sway able to capture anyone’s attention within a 50 foot radius. Mentally preparing yourself for another session of unwitting foot teasing, you sat down in front of her desk and crossed your legs.

Harshwhinny closed the door to her office, sitting down in front of you and taking out a few papers. Barely any time passed before her left heel began to dangle from her toes, and you were just barely able to see it. You gulped and concentrated hard when she began to speak.

“Anonymous. You’ve only been here a few months. But I must say…” you waited for her to finish with bated breath, “Your performance has been absolutely astounding. You’ve done nothing short of amazing, and I am glad I hired you.”

You let out a sigh of relief in your head, turning your head to the charts your boss was pointing at. “As you can see, your marketing in the Stallions department has caused sales to boom. Everywhere that isn’t seasonal has also had a modest increase in sales and profits.”

You nodded and grinned, eyes still managing to catch sight of her feet. One of her violet heels fell off, exposing the entire naked sole briefly. “Yeah…those do look good…thank you Miss Harshwhinny…”

Your boss tapped the desk, turning your attention back to her. She had a very small grin on her face. “As you know, Anon, I am a generous mare. I would like to propose a bonus to you, for your hard work. Would you like a pay raise, or would you prefer an amount of stock in the company?”

A bonus. You tried very hard not to have your eyes drift downwards again, you just knew that her feet were gently rubbing together in those heels. Was this to be your chance? Would you be allowed to…do things to them? Was this only a dumb fantasy, that could only get you in trouble?

You decided to go for it…but to start small. Not QUITE everything you want…but if you were to ask nicely, perhaps you’d get your foot in the door. You took a very deep breath, and your cheeks started to redden.

“Um…I have something else to ask as a bonus…not stocks or extra money…”

Harshwhinny took notice of your nervous expression. “Yes? There is no need to feel apprehensive, I am confident that we could work something out of the ordinary out.”

“Wouldyouletmesniffyourbarefeet?” you quietly and quickly muttered.

Harshwhinny stared at you. You couldn’t meet her eyes, and looked down between your legs.

“Am I hearing this correctly, Anonymous? Did you just ask me to take my feet and…inhale their aroma…?” she questioned, the usual glare on her face slowly returning.

“W-well, we’ve been working closely for a few months and every day I come in and see you come into and out of the office all day and sometimes your feet rub together or slip out of your shoes and I just imagine you getting all mean and slightly annoyed at me while I sniff them and I just wanted to get closer to them and I can’t focus whenever they’re in sight ‘cause they’re so beautiful and-“ Harshwhinny put a finger to your lips. You’re quite sure that you never even took a breath during that whole tirade.

“Such a relationship is HIGHLY unprofessional, young man. Especially one with such DIRTY ways of indulging. Favours like that, especially in the workplace, are not to be dished out by a boss.”

You were honestly surprised that she didn’t get more upset with you. “But…but…you know I wouldn’t ever tell anyone, right? This wouldn’t be a relationship, just one favour. Just a few sniffs. That’s all, and we never have to talk about it again. Please? It’s easier than paying more. Didn’t…didn’t I do a good enough job…?”

Harshwhinny thought for a few moments, and you could have sworn you saw her crack the slightest hint of a smile, as if she had something in mind. And then she let out a disappointed sigh, staring in your direction. She pointed down to the carpet right next to her office chair, raising one of her legs.

You took this to mean she wanted you to sit down in front of her, so you obey her wordless command.

“Hmf. Yes. I SUPPOSE a 36% increase in Harsh Brand stallion collar sales earns you a few sniffs,” your stern, fashionable boss finally agreed. One of her violet high heels dangled from three of her toes, exposing the slightly-dripping sole underneath. Mixed with her typical lilac perfume, which she used generous amounts of, was the scent of a tired sole, which had been walked on all day.

“A…a few, Miss Harshwhinny? I can truly have more than one…?” you breathed, your eyes drinking in the glorious sight, as well as her rather disapproving visage.

She frowned even further. “FINE. You get THREE. You better make sure to enjoy them.”

You took the slim, curved foot in your hands, not even bothering to push the shoe off of her toes, and took your first deep breath of her intoxicating scent.

“Be thankful. This is the closest thing to a bonus that pesky stallions like you can hope for,” Harshwhinny remarked, twisting her sweating foot in your greedy hands, while you enjoy your second sniff of her well-worn heels, mixed with the aroma of the skin on her wonderful sole.

“Hardly the professional attitude required to be of use in this industry, Anonymous, but I allow this as an outlet for your urges. Your state of mind makes it impossible for you to work,” your boss said, as you closed your eyes. You pressed your nose against her soft sole and took the greatest, deepest breath you could muster, as a way to truly enjoy the final sniff Harshwhinny indulged you with.

Your boss shook her head down at you, using her strength to jerk her tired foot out of your desperate grasp. “I BELIEVE I have allowed you your quota of inhalation, Anonymous…I suggest you get back on your feet. Your…unusual bonus was no more than three sniffs.”

Still dazed, the mixture of sweat and her personally-branded perfume lingering in your senses, you clasped your hands together and looked up at your boss’s face, pleadingly. Your member was making quite an apparent tent in your trousers, and there was a dark spot at the tip where a heavy amount of pre had leaked out.

“But…Miss Harshwhinny…I understand this is not professional in the slightest…but the things you have allowed me to do today, they have only…forced my mind to stray further from the tasks at hand…” you gasped.

Those piercing pale blue eyes seemed to glare straight through every fiber of your being. “Secretary Anon. Your performance at this job is nothing less than exemplary, but your seemingly insatiable thirst for my feet is not grounds for such…amorous behaviour between us. Relationships such as these lead to heavily decreased productivity, as well as scandals, as I made you aware.”

You gulped and stared down at her once-again dangling heel, this time from only one toe. “I-Is there nothing I can do for that sort of privilege? Not even once…? I c-could give up my pay for a month, or I could relocate to your mansion for 24/7 work with you, or-“

“Sweet Celestia above, Anonymous. You truly do have issues to work out. I do believe that you would be of great use to me at my home, however…my current staff does indeed prove insufficient in serving me correctly,” Miss Harshwhinny mused, rubbing her chin and narrowing her eyes down at you. She allowed her heel to fall off her tired right foot. Her polished, yet non-coloured nails caught glints of light from the chandelier above, grabbing your attention with ease, as if they did not already have your interest.

“So…uhm…is th-that a yes? May we please go…further? I promise…it will be only once…I just need to know how they feel…” you stammered meekly, reaching out one hand to lay on her shiny, appealing foot.

The stern mare yanked away her copper-coloured bare foot, before any one of your fingers made contact. “Anonymous, you do understand the terms of this deal, correct? You will not only be working in this building, but you will also be working for me, in my home. As you are fully aware, I am a fair and honourable manager, so I will, of course, pay your relocation expenses. But your work will involve anything and everything I say. In exchange…”

Your boss then placed her bare left foot on the palm of your hand, sending electric shocks all throughout your body. It was unbelievably soft, yet you could still make out the muscles beneath, giving them an aura of power and authority. The skin was the smoothest thing you’d ever felt, likely because Harshwhinny had them cared for so often.

“I will allow ONE session, this one, with free access to my feet. More free than you ever will get again. Do we have a deal?” she finished. To accentuate her final point, she extended her slick foot forward, pressing her strong big toe on your forehead. Your nose was so close to her sole, her intoxicating scent was now invading your senses again. Without so much as a second thought, you nodded your head.

“Yes? Then I suggest you obey any of my commands, Anon, as we will do this my way, the correct way,” she responded. As if you could say no.

Her expression did not change, but she directed your attention to her right foot, which was being inched out of the confines of her other heel. Wordlessly acknowledging your nod, she gave you a sudden, aggressively hard press of her bare sole against the bulge in your pants. This forced you to let out a moan of intense pleasure, despite the push being only through your clothing.

While her right foot dug its way between your thighs to grind up against your painfully-throbbing member, her left sole pressed up fully against your face. You could already feel how long it had been trapped in her high heel, and the slick, warm sensation drove you absolutely mad. So without hesitation, you pushed your lips up directly against the arch of Harshwhinny’s left foot and began kissing it with all your might.

You could feel a small jolt come from her body, her slender toes curling against your forehead. However, you weren’t about to let this session go to waste, not one moment. So you continued to passionately kiss the sweating bottom of your boss’s foot, never letting your lips disconnect from the sole no matter where they headed. From heel, to arch, to ball, to toes, your lips stayed firmly attached, and your tongue swiped and swirled to collect her mind-numbing, intoxicating flavour.

While you obsessed over her left sole, her right foot made its way slightly upwards on your body. Her powerful toes curled tightly, capturing your zipper between the big and second ones. Ever so slowly, without losing a fraction of the pressure on your length, her toes pulled it down to expose your undergarments, as well as an even more prominent dollop of pre on the tip of your bulge.

“Hmpf. If you’re quite done trying to get me to giggle like a schoolfilly with your tongue, Anon, I have an order fo-MNNNGH!!” You had grabbed onto her left foot without warning, unable to hold back your urge. You just wanted to see her smile, once. Unfortunately, grabbing onto her ankle and scribbling your nails all over the now extra-slick sole, causing them to splay and curl in the lewdest possible manner, wasn’t the way to achieve that.

Harshwhinny’s free right foot nearly crushed any chance of you having children in the future, just barely restraining itself long enough to kick you in the abdomen hard enough for you to lay on your back.

“ANONYMOUS. I will NOT accept my feet being tickled. This is not a hayburger restaurant, you CANNOT ‘have it your way’. You accept your perverted bonus how it comes, or you forfeit the entire thing,” Miss Harshwhinny growled at you.

Not wanting to risk a complete and utter denial, you keep your begging to yourself, and give her an obedient nod.

Her left foot jerked its way out of your hands, joining side by side with her right. Both of her amazing, sexy soles pushed up against your face, making sure to place the toes over your eyes so you could still get a peek of her disapproving face. She then decided to push your head all the way back onto the floor, scooting her office chair closer so her strongly, yet delicately scented soles could easily remain over your face.

“Excellent. We understand one another. Now, if you wish so badly to have your precious orgasm, I suggest you be as professional as can be about this. Meaning, you allow your boss to take the lead,” your stern, sexy manager said.

All of her toes scrunched together, gripping your forehead slightly. Her slickened soles ground up against your helpless face, slowly smearing their way down over your nose and burning cheeks, finishing up just below your lips. She gave the barest, slightest little smirk upon noticing your reddened cheeks, tapping her toes on your chin. Her eyes slowly made their way down your body, peering directly between your legs.

You gulped, having barely ever seen your boss NOT scowling. If she was smiling, you knew that she had something up her sleeve…your cock twitched in anticipation as a result. Harshwhinny promptly took notice of your lower body’s motions, and a slightly more pronounced smirk made its way across her features. Her soles then started to move further, down your chest, and over your belly…until they both rested against the sides of your painfully-erect manhood, the soles pressed into your upper thighs.

“That’s correct, Anonymous,” your boss said, shifting her feet until they turned sideways, the arches hugging around your tip. This caused you to shiver and gasp. Despite one layer of clothing still separating her warm skin from your member, you were being pushed closer and closer to completion. “You are learning. You wait for your higher-up to take the lead.”

Harshwhinny slid the arches all the way down to your hilt, and then all the way back up to your tip. Her toes then pointed downwards, gripped onto the waistband of your pants, and gave a single tug. This pulled both your pants and undergarments down far enough to allow your cock to spring free, simply aching for your boss’s touch.

Your blushing face turned upwards towards Miss Harshwhinny, and she made sure to lock gazes with you, once again displaying her usual disapproving scowl that just drove you wild. Without missing a beat, her sweating, now saliva/precum dripping soles squeezed together around your entire shaft.

You arched your back in intense, unbridled pleasure. The firm embrace of her stunningly beautiful, silky soles was nearly enough to make you blow it right then and there. Not wanting to have it cut so short, you shut your eyes and clenched your entire body as Harshwhinny’s soles began to glide up and down.

It was getting harder and harder to hold on against the tight, warm space between her powerful soles. Her soles slid backwards towards her body, so her dexterous toes could wrap around your leaking length. They smoothly slid from your very tip down to your hilt, picking up the pace after only a few strokes.

“G…gonna…aahh…” you manage to wheeze out, your eyes snapping open once again. You couldn’t help but watch the hypnotic movements of Miss Harshwhinny’s heavenly soles stroking and pleasuring your shaft, the sight of the clear liquids dripping between her toes becoming too much to bear.

“Is your bonus coming to an end, Anonymous? Very well…ensure that you enjoy this last moment to its fullest,” your boss said. She then removed her curvy soles from your cock, got out of her office chair, standing as tall as she could. She then folded her arms, giving you the sternest look she could muster, and brought her right foot down between your legs. She made sure to do this with as much weight as possible without harming you, the precum-slick surface of her right sole keeping your member flat against your belly.

Her big and second toe squeezed around your shaft, beginning to move her sole back and forth at the swiftest pace she could manage. Nearly as soon as she began, you let out a cry of bliss. Your back arched, and your length pulsated wildly, landing spurt after spurt of thick white seed. Much of the liquid flew up against your chest and belly, and quite a bit more of your load managed to land under Harshwhinny’s wonderful foot sliding back and forth. Gradually your boss began to slow her strokes, her toes managed to catch a single one of your spurts at the end of your intense orgasm.

A minute of both silence and your panting followed, your vision slowly returning to normal. Harshwhinny was sitting in her chair once again, one of her bare legs crossed over the other. Her right foot was absolutely covered in your semen, and it was by far the hottest sight you had ever seen.

“Hm. I trust you found your bonus enjoyable, Anonymous?” your boss asked, wiggling her seed-covered toes, yet never straying from her trademark facial expression.

“Nnggaaahhh…t…too much…” you replied, letting out a small breath of exhaustion. You only just managed to sit back up on the floor, arms and legs shaking slightly.

Miss Harshwhinny nodded, beckoning you to stand back up. She took her pen in hand and wrote down something on her desk, while you managed to wobble to your feet. She then handed you the piece of paper for you to read.

“Directions to your home…?”

Your boss nodded. “That’s correct, Anonymous. As I’m sure you remember, you now both work AND live with me, you are my live-in butler. To assure you’re ready for such work, at 8:00 AM tomorrow, and not still weakened by your…bonus, I will allow you the rest of the day off. I do hope that’s fair.”

“T-Tomorrow…?” you began, then realising that it wasn’t worth it to keep asking questions. “W-Well, thank you, Miss Harshwhinny, I will put in all my efforts!” you said, pulling your pants back up. You waved goodbye to Harshwhinny and walked out her door, trying your best not to look exhausted. You certainly did need that rest, after all…your boss was ging to need you at your absolute best.

-End

Author's Note

Practice safe sex...otherwise you might find yourself on your back, servicing your boss's feet.
Make sure to follow me for inconsistent, yet steamy hot foot stuff! And if you don't, ah well. I'm not paying you to whine. No promotion.