Secretary Anon: The Boss's Toy

by Kulpa

Rating: mature
Tags: Ms. Harshwhinny, Fetish, Sex, Profanity, Slice of Life, My Little Pony: Friendship is Magic, Human, Anon, Porn
Length: 3435

Anon has learned that being a secretary for Ms. Harshwhinny requires doing more than just paperwork.

After a weird interview process, Anon finds himself the secretary to Ms. Harshwhinny. He has not the slightest idea of how to be a good secretary, luckily for him. A secretary's job in Equestria is much different.

Kinks: Teasing/Foreplay (Eww) | Sex in the workplace (How Unprofessional!) | Interspecies (Human x Pony) |Femdom |Cougar/Experienced Mare | Mare on Male | Humiliation (Light) | Denial (Light)

Cover Art artist 'scappo'
(299225 on Derpi)

**9/12**

Published 2019-09-12 22:30:01 UTC
Last updated 2019-09-12 22:30:01 UTC

Chapter 1

Anon sat at his desk, twiddling his thumbs, and staring up at the ceiling. He'd counted all the individual dots on the tiles twice... The number still hadn't changed even though he wished and prayed it would—10,242 if you were wondering. 'du du du dududu du du' Anon hummed the catchy melody to himself as he tried his hardest to kill time.

He'd been in Equestria for just over three months now, with no foreseeable way of getting back home—shocker, I know right? Resigned to the fact that he was stuck in pastel-colored horse land permanently, Anon quickly began hunting for a job. At first, few ponies were even willing to give him the time of day, especially the ones in Ponyville. Each one of them ignoring and in some cases downright laughing at his attempts to try and find honest work.

With no real job prospects in Ponyville, it led him to travel to one of Equestria's largest cities, Manehatten. In a large and budding city that seemed to never sleep, Anon was able to land a couple of interviews—if you asked him, he would tell you that ponies had some very 'strange' interview procedures and that felt like he 'bombed' each one. But with a little luck, Anon eventually found himself in a nice air-conditioned, highrise office building located in the heart of Manehatten. He hadn't the slightest clue what his job title was, or what he was supposed to do most days, for the most part, all he did was sit outside his boss's office like some sort of secretary. If somepony ever asked what he did for work, he'd probably call himself that. Considering, he was never given any secretarial work after that one time he somehow set the copy-machine on fire...Even calling himself a secretary might be a stretch.

He had to admit though, even with the boring, mostly mundane, nonexistent workload, and having to put up with his boss. The pay was pretty good and the benefits were definitely something he could see himself sticking around for. It wasn't like he had anywhere else to go anyway.

Anon looked over at the small digital clock that sat on his desk, 4:00 pm it read. Hearing the latch to the office door behind him click open, Anon turned his attention toward the thick mustached unicorn stallion leaving the room. He wore the top half to a grey, pinstriped three-piece suit, white dress shirt, grey vest, and a very nice looking jacket. It seemed to be the norm for most ponies to only wear the upper half of formal business attire.

With his briefcase floating beside him in his magic, the stallion gave Anon a glance. “She told me to send you in on my way out,” He said, gruffly with his head nodding toward the ajar office door.

Anon sighed, knowing exactly what he was in for, he stood from his chair and made his way into his Boss's office.

“Anon, close the door.” Were the first words out of Harshwhinny's mouth as the human stepped into her office, closing the door behind him. She was clearing off the top of her desk, sheets of paper and other small knickknacks being stuffed away into the large mahogany desk's drawers.

Once finished, she peered up from behind her desk at the young man standing in her office, an irritated look washed onto her face. “Come on now, Mr. Anon, you know the drill. Clothes off.” She clapped her hooves together. “Chop, chop. I don't pay you to stand around.”

Another forlorn sigh departed Anon's mouth as he began undressing. “C-can I at least keep my mask on?” He asked with a sliver of hope in his voice.

Ms. Harshwhinny rolled her eyes, getting up from her chair behind the desk and moving over to inspect her 'personal secretary'. She snorted. “I don't know why you insist on wearing that stupid thing, It's quite unprofessional...But... I don't have any plans to use your mouth this evening so I suppose you may keep it on if you wish.”

“Thank you, Ms. Harshwhinny,” Anon said while removing the last piece of his clothing. He now stood in the middle of Harshwhinny's office, completely nude with the exception of his green mask. His dick hung limply from his groin, only at half-mast.

Harshwhinny clicked her tongue, “Tsk, tsk, tsk. Coming in here unprepared is extremely unprofessional, Mr. Anon.” She shook her head in disapproval. “Consider yourself lucky this is a training session and not a performance review.”

“I-i-i'm sorry, Ms. Harshwhinny.” Anon timidly squeaked out.

With her irritation climbing, the strict business mare ignored the apology and turned away from Anon. Her tail swished from side to side,revealing her toned hind legs, plump rump, giving the human quite the view of Harshwhinny's dark, puffy, arousal-slicked nethers—for an 'older' mare she still looked good. “Hurry up and get hard, then lay down on top of my desk.” She commanded, her serious tone let Anon know that her patience was waning thin already.

Blood rushed to Anon's member, inflating his half-chub into the full-sized, rock hard pleasure rod Ms. Harshwhinny was accustomed to. Back on earth, he knew he wasn't more than slightly above average in terms of size down there, but from what he could tell, he was bigger than most if not all stallions here on Equestria, not massively but enough to clearly make a difference.

Anon made his way over to the desk, following Harshwhinny's orders, he laid on his back, the cool, smooth surface of the desktop drawing away his body heat caused a shiver to run up his spine. His arms and legs hung off to the sides, lazily waiting for Harshwhinny's next move.

“Put your hands away, you won't be needing them this evening. I'll be doing most of the work.” Harshwhinny said.

Anon did as he was told, lifting his butt slightly off the desk and sliding his hands underneath, essentially removing the ability to use his arms and hands. He watched as the blonde maned, earth mare hoisted herself up on top of the desk with practiced ease, a shark-like predatory grin on her muzzle as she stood over him.

Anon's eyes locked in on Harshwhinny's nethers, her shiny lips, small perky teats, and darkened marehood. All of which were a mouthwatering wonder for Anon to take in. He watched as her marehood winked, warm, small droplets of her juice leaked on to his thighs, causing his dick to twitch happily. Anon didn't know how long he'd been staring, entranced by his boss's folds... But his reverie was broken by a light slap to the side of his face.

“Were you even paying attention to anything I just said, Mr. Anon?” Harshwhinny's face looked even more irked than before. Harshwhinny slapped him harder this time, not too hard but enough to sting, leaving a red hoofmark on Anon's cheek. “My eyes are up here, Anon.” She said, using her hoof to tilt the man's face up toward her own. The pair locked gazes, a fiery lust could be seen in the heart of Harshwhinny's eyes, while a meeker, more submissive tone filled Anon's. Harshwhinny licked her lips, that subtle grin of hers slowly returned to her features. “Now... Anon, you have one task for this session.” With a huff, she slowly lowered her hind legs, placing her front hooves on Anon's chest, distributing her weight more evenly while she brought her nethers closer and closer toward Anon's mushroom tipped cock, her thick nectar dripping onto his groin, moistening his skin. Only inches separated her marehood and Anon's dick. “All you have to do...” Harshwhinny brought herself down just enough to rub the tip of his cock against her sopping wet entrance, forcing Anon to gasp in shock, the smooth warmth of Harshwhinny's folds graced the head of his dick teasingly. “Is not cum until I do. Understand?”

Anon groaned and nodded weakly while his member was teased constantly, the earth mare continued to grind just her soaked entrance along his length, causing him to squirm beneath the dominant brown-furred mare. His dick twitched and throbbed as Harshwhinny coated it in her juices, it took all the restraint he had in his body to not buck his hips upward.

“Don't you dare think about moving your hips, young man. I'm in control this evening,” Harshwhinny commanded.

Anon whimpered in response, resigned to just lie there and persevere through her insufferable teasing.

Minutes had passed and Harshwhinny had yet to cease her grinding, not once impaling herself on his rod. Anon's cock was absolutely slathered in her self-made lubricant, shining in the brightly lit office. He grunted and looked up at the blonde-maned mare pleadingly, non-verbally trying to beg her to wrap her warm, wet, weeping folds around his member fully. She gave him a disgruntled look mixed with a moan as her winking clit brushed against his prick, sending an intense flutter of pleasure through her body.

“What's wrong, Anon? Are you going to cum prematurely, again?” She asked mockingly.

Anon's cock twitched again, precum leaking from his tip, this time from the humiliating question. His body trembled as he shook his head, at the same time doing his best to suppress any building urge to cum.

Other than the occasional huff, or soft moan, Harshwhinny had not even broken a sweat yet, her purple blazer and lighter shaded ascot were still in pristine condition as if this was just another casual task to work on. It was no surprise that the experienced mare had turned Anon into a quivering mess in such a short time. And she hadn't even truly started.

“Good.” She shifted her weight backward, lining up her entrance with Anon's manhood. “You're gifted with amazing equipment, Anon.” she lowered herself steadily on to Anon's cock, taking the first few inches without batting an eye, causing her secretary to gasp, caught off guard by her sudden movement. “You just need some training on how to use it properly.” She now had wrapped up half of his length in her marehood. “I urge you to take these training sessions seriously.” She could feel herself being filled by every inch of this magnificent cock. Not wanting to wait any longer, she let gravity do the rest of the work, impaling herself on the remaining half of Anon's dick.

Her marehood clenched tightly around her personal toy, her slick, heated hole squeezed tightly, massaging and milking it for all it was worth. For a moment, the tip rubbed up against her G-spot, sending a sharp jolt of pleasure coursing through her entire body, forcing a low moan from her as she sat their hilted on Anon's groin. She looked down at Anon, he was groaning and staring intently at her nethers, clearly entranced by the sight and feeling he was experiencing.

Shifting her weight, Harshwhinny's front hooves pressed down firmly on Anon's chest, allowing her to lift her flank up with ease, the wet slurping sound of cock leaving marehood filled the office. Harshwhinny had gone up halfway along Anon's length before she brought herself down again in one fluid motion, her flanks loudly slapped against Anon's hips, jiggling as they cushioned her impact.

A pair of harmonized grunts were let out between the two, each of them experiencing equal amounts of pleasure. Anon could feel himself growing closer to his peak, he tightened his core, hoping that would help delay his inevitable climax long enough.

Harshwhinny caught on rather quickly, noticing his labored breathing and feeling his cock begin to twitch and pulse inside her just like it always did when the poor human was close to popping off. She huffed and shook her head, knowing she'd have to take on even more control if she wanted him to succeed.

Before it was too late, Harshwhinny used her favorite skill she had picked up over the years. With herself fully impaled, she controlled the muscles in her marehood, clenching down tightly on all sides of Anon's quivering cock. She smirked as she watched Anon's eye's nearly pop out of his skull, the sudden vice-like tightness catching him completely by surprise. Harshwhinny's marehood acted as a cock-ring of sorts, denying any chance of Anon orgasming until she released her marehood's hold on the human's legnth.

Harshwhinny moved a hoof underneath Anon's chin and tilted his head so their eyes met. “You weren't about to cum just now, were you?” She moved her hips back and forth, grinding herself rhythmically and slathering her marehood's leakage all over Anon's crotch.

Anon grunted, wincing just slightly from the uncomfortable sensation in his pent up balls. He stammered out a response, “S-s-sorry Ms. Harshwhi— Ahhhh”

Anon was cut off by Harshwhinny's cunt constricting even tighter, “Don't apologize...” Harshwhinny lifted her hips up until just the first few inches of cock were still inside her. “You're going to be doing me a favor now once we're finished. To make up for your disappointment.” She thrust herself down again, Anon's cock throbbing and rubbing against her walls in just the way she loved. She let out a pleased hum, her cunt muscles still squeezing tightly as she wetly slapped against the man's hips. She leaned down with a grin, her muzzle only a few inches away from Anon's face, all the while continuing to grind and control her marehood against the base of his dick. “For now... just lay there like a good little colt and let me relieve some stress on my personal toy,” She said huskily.

Anon found himself speechless. The dominance this older mare showed him had his manhood throbbing inside her hot, velvety smooth depths. His eyes misted briefly as he endured the pleasure she wrought upon him. He was finding the whole situation extremely, extremely hot.

“Feel free to continue moaning and making noise...” Harshwhinny began riding Anon with precise, heavy strokes. Her strong hind legs drove herself up and down, her hips and flanks rippled and slapped loudly each time she brought herself down on his lap. “I do enjoy the cute noises you make each time I hit what must be a particularly sensitive spot.”

Anon persevered through the dominant earth mare's pace for what felt like forever. He had been letting out a low, guttural, pleasured and discomforted moan for the past few minutes, mixed with his boss's own squeaks and trembling moans. His balls were becoming backed up to a point he didn't think possible, pressurized cum just begging to be let loose from his sack. His chest and undercarriage were soaked, forced to lay in a growing puddle of his boss's sticky, clear, cinnamon-scented sex fluids—Anon had to admit that was one upside to all the fucking he had to endure, the mares smelled and tasted amazing.

Knowing that repressing the man's orgasm for much longer would start to do some harm to the human, Harshwhinny took a deep breath, holding it for a moment before slowly letting it out. Without any more delay, she increased the speed of her hips by a blistering amount. Loud moans and wet smacks came faster and faster, her marehood being emptied and filled fast enough to make the seasoned mare's breathing hitch. “Ohhhhh, That's it,” She said in the middle of thrusts. “That's the...” One final sharp fall of her hips was all it took to send her over the edge, she let out a high-pitched, banshee-like scream.

Her marehood loosened, letting go of the snake-like constrictive hold she had on Anon's cock. Her eyes rolled up into the back of her head, the whites of her eyes the only thing visible as her form was wracked by a body-quaking orgasm. Her marehood danced and convulsed in the throes of her climax, a small warm forceful trickle of marecum burst out from between her plugged nethers.

Anon watched and felt Harshwhinny cum all over him, the professional mare looking like a simple harlot as her intense climax sent her collapsing in a heap, trembling on top of Anon. The pleasure from her folds mixed with her no longer actively trying to deny his release sent him over the edge as well. His cock spasmed and pulsed wildly as he emptied his balls with a pleased grunt. His eyes fluttered and his jaw hung open as shot after shot of cum poured out from his manhood. After what felt like at least ten to twelve spurts of cum filling Harshwhinny's cunt and his balls shrinking back to normal size, he regained a little sense of clarity. Anon just panted and lay there, waiting for Harshwhinny to return to a lucid state.

Moments passed and the pair lay peacefully on the earth mare's desk, Anon and Harshwhinny both slowly catching their breath. Harshwhinny was the first to stir, unceremoniously disconnecting herself from Anon's softening member with a lewd pop, a small trickle of the man's seed dribbled out from her clenching lower lips. She rolled off the desk, landing on the floor with grace, trotting over to the full-length mirror she had in the corner of her office, next to the bookshelves. Giving herself the once over, fixing any small wrinkles in her blazer, and touching up any out of place hairs in her mane, she sighed contently.

“Ah, Anon. That hit the spot,” she said, not even bothering to give the just now stirring human a glance.

Anon sat up, stretching to loosen up any tight muscles that may have occurred during their session and stood up of the desk, looking at the large puddle of marecum that sat atop.

Harshwhinny checked the time, nodded to herself knowing it was 'quitting time' then walked over to her desk. Opening the bottom-most drawer on the right, she pulled out a roll of paper towels and a spray bottle of cleaning solution. “Here,” she said, tossing them both toward Anon. “Clean up this mess. I expect my desk to be spotless when I come in on Monday...”

Anon caught both items clumsily, bobbling the roll of paper towels while still naked. He sighed and nodded as he began spraying the desktop with cleaning solution.

Harshwhinny reached underneath her desk, grabbing her satchel and briefcase, with both of them secured she made her way to her door with her tail tucked tightly over her nethers, ready to leave for the night. As she reached the door, she turned back around. “Oh, before I forget...” she said, getting Anon's attention. “I'm gonna need you to go ahead and come in tomorrow... I know it's a Saturday, but Grace's normal secretary is on vacation and the temp doesn't come in till Monday. So... I'm gonna need you here on Sunday, too.” She gave Anon a smirk. “That's not a problem, is it?”

Anon shook his head, knowing that he couldn't actually say no to his boss. He'd just have to suck it up and bear it.

“Good! I hear she's more into oral stress relief, so you might want to find a unicorn to water-proof your clothing, I hear she's quite the remarkable squirter...”

“Okay, Ms. Harshwhinny,” Anon replied.

Content that everything was taken care of, Harshwhinny turned and left, closing the door behind her on the way out.

With no one else in the room but himself, Anon smiled, soaking up the mixture of cleaning spray and fuck fluid. “Man, I love this job.” He said to himself giddily. “I better get time and a half for coming in on the weekend though...”

Author's Note

My Jam Music (Wish I could sing as good as Brandon Urie)

-Kind of jealous of Anon to be honest. >.> What a job...

-Hopefully, some of you notice a few references hidden away. (Props to anyone who can guess the tune Anon was humming at the beginning!) 😂

-I actually like this, so that means Y'all will probably hate it! 😂 Regardless, Harshwhinny doesn't get enough love!

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