A Matronly Mishap

by Some Leech

Rating: mature
Tags: Human, Anon, Porn, Fetish, Comedy, Spoiled Rich, Sex, Profanity, My Little Pony: Friendship is Magic
Length: 4658

After being left alone to tend the Rich family mansion, Anon runs across an intruder ransacking Filthy's room!

With Diamond Tiara gone for the day, Anon is left to look after the house. Deciding he'd rather not spend the entire day in bed, bored out of his mind, the man finds himself cleaning up a bit. Curiously, he discovers that someone is in his boss's room, rummaging around in Spoiled's jewelry cabinet! Taking matters into his own hands, and with nobody else to back him up, the man bravely confronts the robber. Unfortunately, things are not what they seem...

Kinks Include: Male on Female, Oral, Vaginal, Squirting, Spanking, Dirty Talk, Rough Sex, Creampies, Crotch Tits, and a very awkward situation. No Foalcon in this one!

Artwork by RadiantRealm

Published 2018-09-12 20:10:01 UTC
Last updated 2018-09-12 20:10:01 UTC

Older Mares Have Needs Too

Over the past several days, Anon had slowly acclimated to his role in the Rich household. After arriving in Equestria, he’d been employed by Filthy Rich to tutor his daughter and assist with chores around the stallion’s estate. In dire need of income, his larder bare and with what little resources he had dwindling, the human agreed, signing a lengthy contract out of desperation. Unfortunately, the man had unwittingly sealed his fate as an indentured servant for the Rich family and, in particular, Diamond Tiara. Filthy had duped him into mentoring his daughter for the month while he and his wife vacationed. As if that wasn’t bad enough, the precocious filly had a sadistic and domineering streak a mile long, regularly degrading the human, forcing him to service her, in more ways than one. Yes, Anon’s latent masochistic qualities had been brought to the fore by the pretentious little pony, only complicating the situation and giving Diamond Tiara plenty of leverage to use against him, should he chose not to freely bend to her will. Simply put, the poor fellow was in quite the pickle, bound by a legal contract and the threat of blackmail from a jail-bait mare.

Things weren’t all bad though. Part of the employment agreement was that the Rich family would furnish Anon a room in their mansion, so he needn’t worry about rent anymore. The pay itself was quite good as well, a fair bit more than most manual labor jobs and requiring only a fraction of the physical demands. Lastly, and somewhat shamefully, a part of the man actually enjoyed being ordered around by Diamond Tiara. Yes, he’d always had a thing for dominant women back on Earth, but he had no idea that the same quality would translate over to pastel equines, and precariously young ones at that. The filly would often expect attention in some form or another, anything from brushing her mane and feeding her snacks to lapping at her nethers. Regardless of what she had Anon do though, Diamond almost always dolled out condescending and derogatory remarks during, cementing his low standing and how he should be honored that she allowed him to do anything with her whatsoever.

As time passed, so too did Anon’s sexual frustration. While Diamond would tease him, she’d seldom given anything more than a taunting kiss or nudge upon his manhood, regularly delighting at his discomfort while denying him any carnal enjoyment of his own. Thus, the human was left to ease his tension in the confines of his room or, on occasion, while lavishing his small mistress. All things considered, things could be worse. At least he had a roof over his head, was fed regularly, and secretly appreciated just how cunning and controlling Diamond Tiara was.

Thus far, the day had been somewhat atypical, as far as Anon’s routine was concerned. Diamond had gone out to a friend’s to spend the evening, a similarly uppity filly named Silver Spoon, who lived a short distance from their manor. The only other pony present on the premises was an elderly servant who was charged with the grounds, tending to the garden and and greenery through the day and retiring to a small cabin at the back of the property at night. For all intents and purposes, Anon was left alone in the mansion for the day. Although he was initially relieved to be freed from the beck and call of Diamond, his contentment soon shifted to apathy. You see, Equestria was without such luxuries as high speed internet or cable television and, as such, a mind numbing boredom quickly enveloped him.

After whiling away nearly an hour in bed, Anon’s mind wandering while the nearby clock audibly ticked and tocked the seconds away. He’d been instructed to fetch Diamond from Silver Spoon’s house the next morning and stay on the grounds himself, just in case the home receive a visitor or any deliveries, unless there was an emergency. Unwilling to mope around in his room the entire day, the man decided to stretch his legs. “Screw this,” he grumbled, throwing his legs over the side of the bed. Stepping into a pair of trousers, and tossing on a shirt, he strolled to the kitchen. Casually munching on an apple, he saw a dust bunny sitting in one corner. The sight, as uninteresting as it was, spurned him to get the broom, his compulsive nature compelling him to address the little eyesore. One thing led to another, and the man soon found himself idly sweeping his way through the house, mechanically moving from room to room as he cleaned. It may not have been the most exciting thing to do, but it was certainly better than wallowing in his bed all day.

Making his way upstairs, nonchalantly cleaning as he went, Anon noticed something slightly amiss. The hallway in which he’d found himself was the location of two very important rooms, Diamond Tiara’s being one, while the other belonged to Filthy and his wife, Spoiled rich. Normally, the door to Filthy’s room was closed but, for whatever reason, it was now left ajar. Setting down his broom, he silently approached the room. Given the fact that Diamond was away, and not having seen the groundskeeper all morning, a sinking feeling crept over the man. What if there was an intruder? Hell, almost everyone had to know that the Rich family was well off, living in a damn mansion and all. Peeking through the doorway, Anon spied movement by a dresser sitting opposite the bed, or more precisely, the small jewelry cabinet atop the piece of furniture. The room being dimly lit, he wasn’t sure exactly who it was rummaging around but he did know it really chapped his ass. If there was one thing the man couldn’t stand, it was a thief. Steeling his resolve, he flung the door open to confront the interloper head on.

“Can I fucking help you,” Anon shouted, squaring his shoulders and sucking in his gut, attempting to look as imposing as possible. Most grown ponies only stood to waist level on him, leaving him to tower over the overwhelming majority of the creatures, one of the few advantages of finding himself in a land of pastel equines. The intruder started, sending jewelry flying as they turned to face him. “I hope you like horse jail because that’s exactly where you’re going for breaking into my boss’s house,” he growled, cracking his knuckles to accentuate the point.

“Excuse me?” a feminine voice called out, the pony rearing back askance, as she faced the irate biped.

“You heard me,” Anon barked, stomping forward to loom over the pony, “I’m gonna hog tie your ass and wait until the cops get here.” Strangely, she didn’t move, boldly standing her ground in the face of eminent capture.

“I’m Spoiled Rich you imbecile!” the mare chided, sneering up at him indignantly.

“Yeah right, and I’m Abraham Lincoln,” Anon darkly chuckled. In one smooth movement, he scooped the pony under one arm, holding her tightly to his chest like a sack of grain, as he turned towards the door. Maybe once Filthy found out he’d apprehended a burglar, he’d get some kind of reward.

“Unhand me you boorish cretin! If you don’t, I’ll have my husband bury you in debt for violating clause sixteen of your contract and make your life more miserable than you can possibly imagine!” the mare protested, squirming violently against her captor. “Do you hear me Anon? Or are you deaf and stupid?!” she cried, jamming a hoof in his side.

Anon stopped dead in his tracks, immediately breaking into a cold sweat. If this pony was some random crook, there’s no way in hell they’d know his name or the fact that he’d signed that infernal covenant. He reached out, fumbling for the magically powered light switch for a second before the room illuminated. Looking down, he was met with the pale pink ass half of a pony. His heart dropped into his stomach as he recognized the diamond ring cutie mark on one of the mare’s ample cheeks and her magenta tail. Though he’s never met her in person, Anon recognized who he was holding from several pictures hung around the house. With glacial speed, the man knelt down, gingerly setting the pony down on the carpet, then taking two large steps backward. The mare wheeled around, her chest heaving angrily as she glowered at him.

“Do you have any idea what I could have done to you?” Spoiled Rich coldly muttered, her eyes locking with the man’s with murderous contempt.

“B...But you were on vacation with Filthy! How? I mean...Come the fuck on! He said you’d be gone for a few weeks!” Anon bumbled ineffectively. He had a point though, he’d had no way of knowing that his boss, or his boss’s wife, would be returning any time soon. Add to that the surprise of finding someone ransacking a jewelry cabinet, and the subsequent adrenaline rush of facing off against said presumed criminal, and the man thought he had a reasonable defense for acting the way he had.

“Come here,” Spoiled demanded, slamming a forehoof down upon the carpet to emphasize the point, “NOW!” Obediently, the human complied, his shoulders slumping as he shuffled over. “Kneel,” she flatly stated, pointing to the floor just before her. Again, Anon did as he was told, slowly lowering himself until he was on his knees. “Now,” the mare continued, a small grin creeping across her face, “kiss me.”

The man paused, utterly confused with the dramatic turn of events. “What,” he blurted dumbly, his mind reeling to process the order.

“I said,” Spoiled snarled, taking his collar in her hoof and pulling him forward, “kiss me.” This time, the pony didn’t give him time to respond, simply jamming her lips against his as she held him close. She groaned as her snout pressed against his face, her tongue worming into his mouth and between his teeth.

Anon’s eyes flew open as he realized the older mare had abruptly and unexpectedly frenched him. Grabbing her by the shoulders, he pushed her away. Spoiled looked absolutely craven, panting heavily while she eyed him like a lion eyes a steak. “Are you fucking crazy! You’re a married woman! Er, horse!” he urgently whispered.

“As if that’s stopped me from taking stallions before,” the pony retorted, batting one of his hands away and leaping upon him, toppling him backward. “You are in my house and you did just grab me without a care in the world,” she teased, running a hoof up and down his chest. “Why, what would my husband think if he found out I was attacked by that barbarian who he’d hired to care for our precious daughter,” Spoiled mocked, holding a hoof to her head in over-dramatic fashion.

“Look, lady, I didn’t know it was you! I thought you were trying to rob the place! You gotta believe me!” Anon pleaded, feeling the heat from the pony atop him radiate through his clothing. He tried his damnedest not to fixate on the nova of warmth that was the mare’s loins. Sadly, the man’s efforts were in vain, as his equipment, apparently taking note of the situation, began to stir.

“I had to come back for a moment to retrieve the right necklace for a ball we’re attending this evening,” Spoiled explained, wiggling contentedly on the poor man. “Now, here’s what’s going to happen. You’re going to rut me like a filly on prom night until I’m satisfied,” she breathed hotly in his ear, licking it to underline the point.

“Your husband will kill me!” Anon implored, shifting uncomfortably as his boner began to struggle against his pants.

“Oh please! Filthy hasn’t been able to satisfy me in ages,” Spoiled groaned, rolling her eyes in irritation for a moment before looking downward, noticing something pressing against her groin. “Anon…” she purred, a wolfish smile beginning to form, “judging from your erection, I’ll take that you agree to this...arrangement.” Without giving him time to reply, the mare hopped backward, bringing her muzzle to his crotch and clamping down on his zipper. Violently, she ripped the offending tab of metal away. Like some starving canine, the pony began rooting around in his pants, nuzzling at his package.

Anon, his resolve crumbling ever more by the second, knew he was dealing with one thirsty equine. Hell, he could see the glistening trail of juices seeping down the pony’s back leg from her marehood. Judging from how worked up she’d gotten over his unintended manhandling, he was ninety percent sure she liked it rough. ‘Well,’ Anon thought, preparing himself for what may be a rather risky move, ‘let’s see how she likes this.’ Grabbing the sides of Spoiled’s head, he firmly pulled her upward, removing her face from his trousers. The man leaned forward, passionately kissing the mare as his tongue wormed past her lips He watched as she closed her eyes, reciprocating passionately and moaning into his mouth. Pulling back, he saw just how hard she was breathing, her eyes filled with lust. “Bed...now…” he commanded.

Spoiled Rich practically flung herself onto the bed, pressing her chest to the mattress while standing on her hind legs. The mare’s tail, fully raised, swept to the side, revealing her rosy red and engorged entrance. It had been quite some time since she’d gotten a good pounding, her latest partners having been a pair of stallions who’d come to clean their pool. While she’d slept with unicorns, earth ponies, and pegasi, she’d never ventured beyond equines to sate her carnal desires. It wasn’t that she hadn’t wanted to, just that the opportunity had never presented itself in such a convenient manner.

Fumbling with his pants, Anon finally freed the pesky garment, getting to his feet and kicking them aside. Fishing into his boxers, while under the watchful gaze of the lusty mare, he retrieved his tool. “You want this?” he murmured, stroking himself as he watched Spoiled start to drool from both ends. The pony nodded, her eyes locked upon his manhood.

Although she’d encountered stallions with larger equipment, Spoiled had never seen quite a unique appendage. It was covered in very lightly tanned flesh, dark veins tracing under its surface, and ending in a rounded, spear-like tip. Her marehood winked at the thought of such a delightfully unique organ prodding around inside of her. She watched as the man stepped to the side of the bed, slowly kneeling before her presented rear end. “What are you...Ohhhh!” she groaned, feeling his tongue sweep over her sex. He wrapped his arms around her thighs, digging his face into her crotch while he lapped and kissed at her snatch. “My, what a gentleman!” she sighed, closing her eyes and enjoying his oral ministrations. It was a rare event for a stallion to dine upon her, often times simply leaping on her to hump away like an unrefined youth.

If there was something Anon had to admit, it was that he found the taste of mares utterly captivating. He’d discovered that Diamond Tiara tasted a bit like angel food cake drizzled with strawberries and, after Spoiled’s nectar graced his taste buds; he found out the older pony was much the same, her flavor being akin to candied apricots, albeit with a slight tang. His partner was clearly enjoying his efforts, softly moaning as her wrinkled and moist lips met his own. A single bead of pre-cum formed at the tip of his member. Hormones began to flood his system, igniting the primal regions of his brain, urging him to seize his mate.

“Anon,” Spoiled whispered, any trace of malice having left her voice, “rut me.”

The lilting sound of the pony’s request flipped a switch. It had been so long since he’d actually gotten laid that he’d practically forgotten what it felt like. Getting back to his feet, he ran the tip of his prick over her glistening entrance, savoring the sensation of her lips caressing the sensitive tissue of his glans. Anon grabbed Spoiled’s hips, steadily pressing his waist forward as he penetrated the mare. The first thing that struck him was how superbly warm she was, while the second was the tension upon his rod. The pony wasn’t especially tight, likely due to a rather scandalous bedroom life, and having birthed a foal, but it was exquisite.

Slowly, Anon began to move, plunging into the pony’s cunt. With each thrust, he delved slightly deeper, all the while relishing the melodic sighs and muffled sounds of contentment as his partner buried her face in the bed’s blanket. Shifting one hand upward, he grabbed her dock, pulling her back to meet his movements. The action had an immediate effect, causing the mare’s canal to seize his length, practically drawing him deeper. “You like that?” he asked, a sinister notion beginning to take hold.

“Mmmmhmmm,” Spoiled hummed, turning her head to the side to blissfully peek back at him.

“Well,” Anon mused, raising his other hand up and delivering a loud smack to the older mare’s meaty rump, causing her to yelp, “tell me how much you like it!” Though he wasn’t typically very aggressive in the bedroom, he’d picked up on the pony’s cues. If this well-to-do mother wanted it a little rough, he’d happily oblige. After all, if she didn’t leave satisfied, god only knows what trouble she’d cause for him in the future.

“Yes!” Spoiled squealed, rocking back to meet his thrusts. “Fuck my pussy you glorious man beast!” she continued, her snatch winking and milking his cock as it pistoned into her. His tool was astounding. Unlike a pony’s equipment, battering her womb and scraping against her interior, Anon’s dick was elegance given flesh; its rounded head caressing her cervix with each plunge while its vascular length caressed her sensitive walls. At this rate, she’d make quite the mess, although that certainly wasn’t a problem, given the fact that she’d make him clean it up. A wordless howl escaped her as another blow landed on her ass, causing her to bite her lip at the mix of stinging pain and sensual pleasure.

“You just...Unf...wanted a big, strong guy to use that sloppy horse cunt of yours, didn’t you?” Anon chided, plowing away and watching as the pony’s supple behind jiggled with each impact. A cheesy line, he knew, but he was far too turned to think of anything more eloquent.

“Celestia, yes! Harder!!!” Spoiled cried, frantically trying to match his rhythm. She could tell she was getting close, her thighs beginning to tremble as the inferno of pleasure blazing within her built to greater heights. She’d been somewhat reluctant to allow this strange creature into their home, but if the human could deliver this type of service, she would need to reassess her standing on the matter.

Sensing the pony was reaching her limit, quivering and mewling as she was, Anon decided to deliver the fatal blow. Sliding one hand around her thigh, his nimble fingers found the mare’s swollen and slickened clit. Giving her tail one final pull, the man ruthlessly massaged the sensitive nub. Sure enough, Spoiled’s body went rigid, her head flying backward as she screamed to the heavens in ecstasy. When she came, she came hard. Her entire body convulsed while her sex lewdly gushed onto her partner, soaking Anon’s loins while her canal seized around his shaft. Content that he’d sated her for the time being, he slowed. Reaching down, he slowly rolled the pony to her back, making sure he was still firmly planted within her.

Spoiled panted heavily as she was moved, grateful for the slight reprieve as the man re-positioned her. Lying supine, she watched as Anon held one of her hind legs aloft, his other hand wrapping around her waist as he casually continued fucking her. He wasn’t unattractive, for a large biped. His fingers, unlike a dragon’s or diamond dog’s, were soft, yet firm, as they dug into her supple flesh.

While he steadily plowed the little pink colored pony, Anon took note of her breasts, each swaying gently as the two continued. Unlike a human’s, the two globular mounts of tissue rested just above her crotch, each adorned with a dark, fuchsia nipple. He wasn’t all that versed with what was an average size when it came to pony tits, but they looked pretty big; either one was easy large enough to fill his entire hand, comparable to a c-cup on a person.

“You can play with them, if you like,” Spoiled sighed, noticing the man’s interest in her teets. In truth, many stallions, her husband included, paid her breasts little mind. Given their location, they typically didn’t come into play during sexual activities and, as such, were typically neglected.

Setting the mare’s leg down, and leaving her in the equine equivalent of a missionary position, Anon’s hands drifted to her bosoms. Experimentally, he ran his fingers over the velvety soft skin, kneading them gently as he continued to plow her. He grunted, feeling the pony contract around his length, reminding him that he had a job to do. Tweaking each nipple, the man picked up the pace, slamming his hips forward as his cock obscenely, and audibly, pistoned in and out of his partner. Anon knew he wasn’t going to last long at this rate, having gone for so long without getting laid.

Watching Anon grunt and thrust, sweat beaded upon his brow, Spoiled read the signs. She’d been with enough stallions to tell when they were getting ready to pop, and the human was no exception. Seeing as how her first orgasm was beginning to fade, and with a second quickly building, she decided to treat them both. Pawing at him, she drew his attention. “Anon,” she wheezed, desperation sparkling in her eyes.

The man leaned forward, draping himself over the pony and bringing his face to hers. Closing his eyes, the two locked lips, tongues warring with one another in a fit of passion. His hips bucked violently, losing any semblance of rhythm, as Anon tipped over the edge. With one final thrust, he buried himself as deeply as possible. His balls retracted as the tip of his shaft kissed Spoiled’s womb. They groaned into each other’s mouths, climaxing in unison; the human’s cock twitching deep within his partner’s marehood and bathing her insides with thick, virile seed as his partner’s cunt constricted around his length. Riding out the rapturous bliss, Anon collapsed atop the pony, their bodies pressed together as they fought to catch their breath.

“Remind me to get you a raise,” Spoiled whispered, daintily tapping a hoof to the man’s head. Though she can, and did, take advantage of visiting stallions in the past, she’d never been fortunate enough to have a live in servant of this caliber. Sadly, she knew this moment was not going to last; Filthy would be expecting her to return shortly, and certainly not disheveled while reeking of sex. Pressing her hooves to his chest, she urged the human to move.

Nodding, Anon complied, pressing himself up before standing. Spoiled moaned below him, feeling his member slip from her confines as he pulled free. Gooey spunk and syrupy mare fluids leaked from her battered entrance, running between the cheeks of her ass and down to the bed sheets. Easing himself onto the bed beside her, the man was quickly greeted by a hoof to the face.

“As appealing as laying in a pool of our filth is, I need to shower. Gather up the sheets for the wash and clean the carpet,” Spoiled coolly said, mopping her crotch with the blanket. Spryly hopping off the bed, she trotted to the adjoined bathroom to clean herself, leaving the man to the task she’d assigned. Under ideal circumstances, she would have much preferred some pillow talk to bask in the post coital euphoria, but the situation demanded otherwise.

After relaxing for a few minutes, his body finally beginning to calm itself, he heard the sound of running water. Anon grumbled as he got up, knowing he wouldn’t be allowed to rest for much longer. He’d be busy with laundry for a while, their exploits having soiled, not only his clothes, but the entire bedspread. Scooping up the offending linens, as well as his pants, boxers, shirt, he stood dumbly for a moment, realizing he was stark naked and without anything to change into. Somewhat reluctantly, he slipped his trousers back on, feeling the moisture of Spoiled’s rather explosive orgasm on the fabric. Maybe a shower prior to setting upon the laundry couldn’t hurt.

Exiting the master bedroom, arms full of linens to wash, Anon sauntered down the hallway, a spring in his step. He definitely hadn’t expected bedding the lady of the house, but it was certainly a pleasant turn of events. Going down the stairs, and rounding a corner, the man came to a screeching halt. Diamond Tiara looked up at him, a puzzled expression on her little face.

“There you are,” the filly announced, scrunching her nose as she trotted up to him. “What were you doing upstairs? You weren’t in my room, were you?!” she asked hotly, glaring up at the man.

“Just, uh, washing your parents’ bed sheets. I didn’t want them getting too dusty or anything,” Anon blurted, caught woefully unprepared for encountering the pugnacious young mare.

“Whatever. Silver Spoon is coming over, we decided to come here for the evening since she wants you to braid her mane,” Diamond explained, accepting his excuse before going to trot past him.

“Anon, be a dear and clean the bathroom this evening as well. I believe I leaked a bit getting into the shower,” Spoiled called out, coming from behind the human and delivering a resounding smack to his backside. Her mane was still damp but her makeup had been expertly reapplied, leaving her just as stunning as when she’d arrived. Seeing her daughter, the older mare didn’t miss a beat, apparently having been caught in the act before. “Hello Diamond, enjoying your summer?” she asked, giving the filly a brief hug.

Diamond Tiara’s face contorted in an array of emotions, shock, rage, disappointment, and sadness, before settling back to her regular, aloof expression. “Yup, was just going to Silver Spoon’s house to spend the night,” she smoothly replied, returning her mother’s hug.

“That’s my girl, just be sure to mind your studies. I’m sure Anon will help with them if you need,” Spoiled said, releasing her daughter and heading towards the door. She’d left the unicorn who’d teleported her home waiting outside, hopefully he hadn’t lost his patience. Still, she’d need to concoct an explanation for her tardiness; a simple task, but a vital one. And just like that, the mare was gone, returning to her husband on their vacation.

“I...I thought you just said Silver Spoon was coming here for the night,” Anon stammered, having been caught red handed after plowing the young pony’s mother.

A pained expression crept across Diamond’s face as she turned away. Without a word, she galloped away, leaving the man confused and slightly concerned. In all the time he’d spent with the filly, she’d never acted this way. Normally, she’d berate or chastise him for any wrongdoings, but he’d never seen her this upset. Anon couldn’t be sure, but he thought he saw tears in her eyes as she turned. He couldn’t help but feel a little bad about the whole thing, given how he’d slowly warmed up to the demanding little pony over the past few days. Still, there was little that he could do now. Resigning himself to a shower before starting the laundry, the man was left with a lingering guilt as he plodded off to his room.