Breaking in the Help
He still wasn’t sure exactly how he’d wound up in Equestria but it wasn’t nearly as magical as it had initially appeared to be. Sure, there were talking pastel equines but, besides that, it was a functional society like any other. There was an economy, taxes, goods & services, and everything else he’d dealt with back on Earth. The only difference was, Anonymous was an outsider and, as such, had a hard time finding work. Princess Celestia and her sister Luna had placed him on, what was essentially, probation in Ponyville. Most of the jobs simply weren’t geared for non-ponies which made things rather difficult.
After applying at several places around town, Anon was approached by a local entrepreneur, a pony named Filthy Rich. His black mane was slicked back and he wore a rather dapper collar and tie, a rare sight among the other ponies in town. The stallion politely introduced himself, mentioning that he owned a chain of shops called Barnyard Bargains and that he was also on the town’s business council. After prattling on about his exploits, Filthy suggested they continue their conversation over a light lunch. Anon tried to explain that he was flat broke, but the pony insisted, going so far as to say he would cover the meal. Making their way to the cafe, the two casually chatted about this and that. The stallion seemed to have a keen interest in Anon’s education, including his grasp of the basic sciences and math. The human didn’t realize it at the time but the entire encounter and conversation had been carefully calculated.
Finishing their meal, Filthy offered the man a job, but not working in one of his stores. No, he had something a bit different in mind for the human. The pony asked if Anon would act as a tutor and personal servant to his daughter, a filly named Diamond Tiara. Filthy explained that the work would be quite easy, helping the young pony with her homework and studies in the evenings while assisting with housework and labor around their home during the day. The stallion assured Anon the job would be a breeze, coolly sliding over a neatly rolled up scroll to the man along with a small sack of bits as a ‘sign on bonus’.
Unfurling the comically long piece of parchment, the human’s eyes danced over the never ending legal jargon. The overwhelming majority of the text was legalese and even if he had time to read all of it, he doubted he’d fully understand everything. Anon was basically out of options. The grace period of his apartment was about to expire and, to make matters worse, he was nearly out of food. If he wasn’t able to find a source of revenue quickly he’d be out on the streets. Out of desperation, the human relented, signing the contract and unwittingly sealing his fate. It wasn’t until later that he found out exactly how arduous his employment would be. Taking the scroll in one hoof, the pony grinned broadly. He gave the human directions to his estate, expecting Anon to start work the very next day. As he walked home, he took solace in the fact that he’d be able to take care of his bills and buy groceries. Even with what little he knew of the local currency, Anon realized that the pay which Filthy promised was no small amount.
~
The alarm clock atop the nightstand rang noisily, rousing Anonymous from his slumber. The man groaned, rolling over and cracking one eye open to check the time. Six o’clock, time to get up and head to his first day on the job. Fumbling for the clock, and ending it’s ceaseless clattering on the wooden surface, Anonymous swung his legs over the side of the bed. Lumbering off to the shower, the man washed up and readied himself. He only had a few simple pairs of pants and shirts, generously donated by a pony named Rarity who owned a clothing store in town, so deciding what to wear was easy. Slipping into a pair of shorts and T-Shirt, Anon combed his hair before heading out the door. Filthy apparently lived at the edge of town and expected him to be there at seven A.M. most days. Walking through the quiet village, Anon sighed contentedly. Maybe things were starting to turn around for him after all.
Waving at the few tiny equines he countered along the way, Anon smiled. Most of the ponies he’d met seemed friendly enough and he’d even started making regular acquaintances over the past few days. At worst, a few of the small horses were slightly leery of him, but that was probably because they’d never seen a human before. Frankly, he’d had more trouble coping with finding himself in such a strange and magical land than the residents did acclimating to his presence. The princesses had even ensured he’d have furniture that suited his size. From what he’d seen, most ponies, stallions and mares alike, stood between 3’6” and 4’6” tall, coming up to Anon’s torso. He’d had to crouch a few times when maneuvering through buildings but, for the most part, the equines tended to build doors and ceilings high enough to accommodate larger creatures.
It only took Anon about fifteen minutes to reach his destination. As described, Filthy’s estate was massive; the house itself was two stories and was even larger than the Ponyville town hall. Walking up to the door, Anon gave it a firm knock, straightening his shirt and doing what he could to make himself as presentable as possible. After a moment, the door cracked open, although it was still fastened by a chain on the building’s interior.
“Can I help you?” a small voice called out from the narrow opening.
“Um, yea, I’m Anon. Filthy hired me as a tutor or assistant for his daughter,” the human replied, spying a sky blue eye peering up at him from inside.
“You have got to be kidding me,” the voice lamented.
“Is Filthy in?” Anon asked, squatting down to address the diminutive doorpony. He still couldn’t get a good look at her but he could tell, whoever she was, was female from her pitch.
“Ugh, fine!” the pony grunted, momentarily closing the door before Anon heard the lock being unclasped. The heavy wooden entryway swung open, revealing the structure’s interior.
There, in the dead center of the foyer, stood a small filly. Her mane and tail were lilac, each with a prominent white streak coursing through their wavy length, while her coat was a cotton candy pink. A little tiara sat atop her head and her cutie mark was almost a mirror image of the crown which she wore. Judging from Filthy’s description of her daughter, of whom he’d fawned over remarkably, this was none other than Diamond Tiara herself.
“Diamond Tiara?” Anon quizzed, stepping inside and kneeling before the youngster. Not waiting for an answer, he extended his hand. “I’m Anonymous but you can just call me Anon for short,” he said with a smile.
“Yeah, no,” the filly sneered, waving a hoof at him dismissively, “I don’t shake hooves with the help.” Diamond Tiara shook her head as she began to pace back and forth before the man. “Really, to think father would hire the weird ape man to be my sitter for the summer. I’m sure mother had something to do with it as well but, honestly, couldn’t they have employed an actual pony for buck’s sake! But nooo, they just had to get the freaky biped to look after their precious daughter!” the little pony angrily monologued, occasionally stomping a hoof to the polished hardwood floor as if to emphasize the point.
“Well, uh, is your dad in?” Anon asked, nervously getting to his feet. From how Filthy had spoken of his daughter, he’d assumed she’d be an angel but that seemed less and less likely, given her petulant reaction to his presence.
“Of course he’s not here! He and mother have gone off on some business retreat for the month.” Diamond squaked, leering up at him. “Didn’t you read the contract?”
“Wait, what?” the human blurted, utterly perplexed. He remembered glancing over the document but, for the life of him, couldn’t recall the specifics. Anon was, and always had been, the type to just check the ‘accept terms’ box on different computer programs and websites, assuming that there wasn’t anything too important buried in the seemingly endless walls of text.
“It said that you’re to look after me all summer while Father and Mother are away,” Diamond explained, trotting up to the towering human. “And,” the filly continued, a wicked grin creeping across her face, “you have to do anything that I say.”
“Bullshit,” Anon flatly stated, incredulously staring down at the tiny pink pony.
“I thought you’d say that,” Diamond responded, trotting off to the next room. “Don’t just stand there like a simpleton, come on!” she yelled, urging the man to follow. While she may be young, Diamond was far from incompetent. Leading Anon into a seating room, she gestured at the unfurled contract. “I highlighted the important bits for you,” she said, watching gleefully as the human poured over the contract.
Anon couldn’t believe it. According to the document, he not only had to act as Diamond Tiara’s servant for the entire summer, but had to live in the guest quarters of the Rich estate while employed. The worst part was that, were he to try and breach the agreement, Filthy could seize what few possessions he had and place him in debt to be deducted from any future earnings he made while in Equestria. The long and short of it was, he was utterly screwed.
“Does it all make sense now or do I need to use little words so your monkey brain can understand?” Diamond scoffed triumphantly, relishing the look of utter defeat upon her servant’s face.
“Fine, fucking fine,” Anon growled, tossing the contract against a wall. At least he wouldn’t have to worry about paying rent while crashing at the Rich manor and maybe, if he was lucky, they’d have some decent grub. ‘Just have to stay positive Anon, it can’t be any worse than those student loans,’ he thought to himself. His attention was suddenly drawn downward as the filly tugged at his pant leg.
“First order of business, carry me to my room and brush my mane,” the filly demanded. While she still wasn’t thrilled by the fact that she couldn’t have a proper equine attendant, Diamond figured having this human was better than nothing.
Stooping down, Anon gingerly scooped up the young pony before cradling her to his chest. She was only about half the size of a fully grown mare, her head coming up to his mid thigh, so picking her up was easy. “Which way?” he asked laconically.
“Ma’am,” Diamond recited, tapping her crown as the man looked down at her.
“Huh?” Anon grunted, cocking an eyebrow.
“Refer to me as Ma’am. Come on, it’s not that hard to figure out,” the filly chided. The other butlers and employees always referred to her parents as ‘Sir’ or ‘Ma’am’ so this situation should be no different. “Ma’am,” she repeated mockingly, sounding out the word for him.
“Which way, Ma’am,” Anon groaned, trying not to sound overly contemptuous.
“Much better! Through there and up the stairs on your left,” Diamond directed, pointing her hoof towards a doorway on their right. The human silently complied, stomping off while cradling her. His hands were certainly interesting, each splayed digit gently dug into her flesh as he supported her weight. As if coping with fingers wasn’t odd enough, the human had an odd scent; it wasn’t bad or anything, simply singular and strangely masculine.
While Anon trundled along, the filly in his arms assisted with navigation, albeit in a condescending way. How the hell was he supposed to know where anything was in this place anyways? After a few short minutes, they arrived at her room. “Where’s your brush?” he moaned, looking about the room before turning his gaze downward at the irate young mare. “Where’s your brush, Ma’am?” he corrected, fighting the urge to roll his eyes.
“Top drawer of my nightstand. You may brush me on my bed,” Diamond proclaimed. She wriggled contentedly in his grasp, causing his hands to adjust. One of his palms slipped to her tender belly, causing her to go rigid. “Hey, watch where you’re holding,” she grumbled. It had been her fault, what with squirming about, but there was no way she’d let him know that. Reaching the bed, the man sat her down on the mattress before rifling around in the indicated drawer.
“Which brush?” Anon questioned, finding two different ones within the nightstand; the first, with a blue handle, seemed like a conventional hair brush, although the second, with a small grip on the back, had much shorter bristles.
“Use the blue handled one for my mane and tail. Once you’re done with that, you can use the other on my coat,” she intoned, turning to him with a look of disbelief. “Don’t they have horses where you’re from?”
“Well, yea,” Anon said, daintily removing the filly’s tiara and setting it on the bed, “but they didn’t talk or have magic. We cared for them, sure, but they were beasts of burden for us, or pets.” Sitting beside her, his legs crossed indian style, he carefully began tending to Diamond’s mane, guiding her hair with one hand while brushing it with the other. The pony’s hair was not unlike a human’s, voluminous and well cared for.
“Sounds like they got the short end of the stick,” Diamond mused, closing her eyes and enjoying the attention. It was hard for her to wrap her head around the fact that equines were second class citizens in some far flung world but, all things considered, there wasn’t much she could do about it. After a few minutes of Anon dutifully stroking her mane, the pony shifted, flicking her tail out to the side. Reaching down, the man ran the thick hair of the filly’s tail through his fingers. Feeling his digits caress her dock, Diamond shivered a bit, unused to the sensation. There were only a few intelligent species in Equestria with hands so, seeing how she had one at her disposal, the filly decided to make the most of it. “I’ve changed my mind,” she declared, looking up at him, “I’d like a massage.”
“Whatever,” Anon groaned, setting down the brush before grasping the back of the young mare’s shoulders. Even though he’d only been around her for a short time, he could already tell that Diamond was an entitled brat. Regardless, he consigned, this beat manual labor. Skillfully, he began digging his thumbs into the muscles of her back while rhythmically kneading her sides with his fingers.
“Oh my gosh,” Diamond moaned. The massage was sublime, the human’s fingers possessing a level of dexterity leagues beyond what any pony could ever accomplish with their hooves. “You must have had a lucky girlfriend back home,” she murmured, feeling the tension practically melt out of herself. While she’d only recently began taking an interest in colts, she was fully aware of relationships and what they entailed. Her father had, on at least one occasion, a fling with one of their maids and her mother routinely made trips to Manehatten to “visit family”, often times returning home with an oddly unsteady gait.
“Nah, don’t have one. Well, didn’t I guess,” Anon said, steadily working his way down the filly’s frame. Her fur was exceptionally soft, almost velvet like in texture under his touch. She was actually kind of cute, when she wasn’t running her mouth anyways.
Diamond’s heart skipped a beat as the human’s palm grazed her flank. “L...lower,” she whispered, wiggling her rump at him in anticipation. Only one of the other servants was on the premises and, if she wasn’t mistaken, he would be busy with landscaping for the majority of the day. There was something strangely exciting about having this human touch her, but she couldn’t place her hoof on exactly why.
“Um,” Anon gulped, looking down at the filly’s posterior, “isn’t this kind of inappropriate?” While it was true that he wasn’t totally acquainted with pony etiquette, he was pretty sure that giving a full body massage to a filly was breaking some rule or taboo.
“Do I have to do everything myself,” Diamond growled, standing up on the mattress. Crossing over to Anon, she sat herself in his lap. “There, now service me like a good human,” she continued, gyrating in place.
As wrong as it was, Anon’s body started to react to the tiny filly’s actions. Being ordered around was, in and of itself, kind of a turn on but the addition of having a pony’s soft backside bearing down on his groin was too much. “I’m not really comfortable with this,” he said, hoping that she’d move.
“No. You’re comfortable and, besides, you have to do what I say,” Diamond giggled, leaning back against his chest while she looked up at him. For some reason, the man bit his lip and seemed to be avoiding looking at her. “I’m talking to you!” she snarled, reaching up and pulling his chin down with her hoof. “I don’t know why you…” her voice trailed off as she felt something prod her bottom.
“It’s not what you think!” Anon blurted, hastily grabbing the filly and moving her to the side. Sure enough, the commanding tone and tactile contact with the young female had led him to inadvertently get a semi. “Can we do something else please?” he lamented, standing up and walking across the room, desperately trying to will away his body’s arousal.
“You get back here right now,” Diamond barked, stomping her hoof on the mattress. There was no mistaking it, she’d felt something rigid in the man’s pants. Unwilling to let such an opportunity slip through her hooves, she smiled devilishly. The human sighed, languidly turning and trudging back to the bedside. “Now, kneel,” she demanded, pointing to the floor below. He complied, getting to his knees, his face roughly level with her own. “I think I understand why you didn’t have a girlfriend,” Diamond said thoughtfully, bringing her muzzle to his ear, “you like fillies don’t you?”
“What? No!” Anon protested, rearing back in dismay. It was bad enough that she was a pony, but the fact that she was a fairly young one only made him more uncomfortable with his subconscious reactions. How was it his fault that his body reacted the way it did.
Diamond Tiara seized the moment, slowly wheeling around in place while dramatically pressing a hoof to her forehead. “I can’t believe that I’d be stuck with some creep,” she lamented, her tail flicking from side to side in irritation, giving the man tantalizing glimpses of her pucker and glistening marehood. “Hmph,” she chuckled, seating herself with her back to him. Gradually, she lowered herself to the mattress before rolling to her back. “Is this what you want you pervert?” Diamond softly asked, splaying her hind legs and displaying herself fully to the human.
Anon couldn’t believe what he was seeing. Why in the the hell would this pony be acting this way. He tried to avert his gaze but not from her groin, it was the snide grin and wickedly piercing eyes of the filly that held him captive. “Look, I don’t know what kind of sick game you’re playing but-” he couldn’t finish his statement.
“Lick it…” Diamond purred, locking eyes with him as she reached down to spread her lower lips. While she’d ever only played with herself, she’d heard that oral was far superior, especially if the pony, or person in this case, knew what they were doing. Anon was to be her servant so he may as well become accustomed to pleasing her in every imaginable way. Oh, she’d tried this tactic with the help in the past but had failed miserably All of the Rich family’s other employees had worked for her father for years, having gained his trust. This human was different though, he didn’t have any idea of just how devious she could be and was caught woefully unprepared for her guile. Noticing his trepidation, Diamond decided to sink the final nail in the coffin. “If you don’t,” she flatly stated, “I’ll tell everyone that you did and have you locked up. Do you have any idea what they’d do to you?”
The man’s mind raced as he tried to comprehend what was happening. On one hand, he could do as the filly wished and sexually service her; on the other, he could refuse and she would, judging from her tone, accuse him of god-knows-what. Simply put, Anon was fucked. Easing himself forward, he brought his face before the small pony’s entrance. Her dainty hooves held it open as a glistening trail of nectar glided down to her ass. The smell was not unlike a human woman’s, although with a faint grassy note. Gently, he reached his hands under her thighs as he extended his tongue. Caressing her velvety folds, the filly groaned above him. The taste had a touch of sweetness with a slightly acrid tang.
“Such a good boy,” Diamond cooed, watching as the man lavished her snatch with his mouth. The feeling was incredible, the way he gently nibbled at her while his tongue slid up and down her slit, occasionally probing deeper into her depths or teasing her clit. She could certainly get used to this.
Pony or not, Anon was actually starting to get into the current situation. Even though he hated himself for it, his erection painfully pressed against his pants. It had been quite some time since he’d gotten laid, his dry-spell predating his unexpected trip to Equestria. Slipping one hand from beneath the filly’s thigh, Anon reached down to undo his zipper. Fishing out his equipment, he started slowly stroking himself while continuing to feast upon the pony’s juicy nethers.
“Are you actually getting off to this?” Diamond jeered, her words drawing his attention upward. “No, no stop,” she said, backpedaling and closing her legs. Her groin dripped fluids to the floor as she hopped off the bed. “Lay down,” she scolded, pointing to the carpet on which he knelt. The man acquiesced, lowering his back to the floor, his erection pointed skyward, a monument to his depravity. “Now then,” the filly continued, trotting over to his head, pressing it down to the carpet, “I think I’ll have a seat.” Straddling Anon’s neck, Diamond settled herself directly on the man’s face, his nose pressing against her backdoor while her drooling dark pink cunt ground against his lips. “You may continue,” she flippantly commented.
Anon didn’t need any further goading, wrapping his arms around the pony’s hind legs, he dug in. He was dimly aware of Diamond’s moans and contented sighs as he continued his work. The young mare’s juices dribbled down his chin as he lapped at her. While he ate out the tiny equine, a notion occurred. Sitting up a bit, he buried his face further in Diamond’s crotch while simultaneously pressing her closer to his waist.
The filly lost balance at the sudden surge of movement, crashing down upon Anon’s chest as she slid towards his groin. There, just before her, was his towering shaft. She’d never been this close to one in person, only having seen stallions’ equipment at a distance, if at all. The shape was a bit different than a pony’s, the head being more rounded with a funny shape, but it was impressive nonetheless. What was really striking to her was the smell. The human’s cock had a musky, heady odor that screamed of masculinity. She couldn’t help herself. Reaching forward, Diamond wrapped one hoof around its base and pulled it down, angling it towards her parting lips. A glistening bead of pre graced her tongue as she slipped its head inside her eager maw.
The man cursed aloud but the only noise which could be heard was a muffled grunt, his face held captive between the young mare’s thighs. Anon redoubled his efforts as Diamond experimentally sucked and licked his length. The pony’s mouth, while inexperienced, was amazing. The way she hummed around the sensitive organ, how her tongue slid over his glans, and her warm saliva running down his length to his balls; it was all too much.
Diamond could feel herself getting close, her supple thighs quivering around the man’s face as he continued to eat her out. She stopped fellating him, resting her face as she allowed herself to focus on Anon’s oral ministrations. While not completely callous, she stroked his throbbing cock with one hoof while fondling his ripe nuts with the other. In truth, she wouldn’t have minded sucking him off but that’s simply not how it was going to be. Anon was her’s and, as such, would have to earn anything beyond a hoofjob. With a gasp, Diamond squeezed the man’s head between her hind legs as she came.
A torrent of fem-cum gushed from her crotch, drenching Anon while she mewled pitiably. The hot liquid flew down his throat and he did his best to gulp it down. The filly’s grip on his cock nearly doubled as her body quaked atop him.
The filly’s mind went blank as her body was wracked by the most powerful orgasm she’d ever experienced. She’d heard that some mares squirt when they cum but had never experienced such a thing herself. All she could do was draw air into her chest while she recuperated on Anon. As far as she was concerned, he deserved a reward. “A...Anon,” she wheezed, crawling down to the floor before rolling onto her back. “You can jack off on me if you want…” she muttered, grabbing her fetlocks with her forehooves while she spread her hind legs.
Clamoring to his knees, Anon couldn’t look away while he furiously masturbated, his body begging him for release after the sensory and psychological onslaught he’d just suffered. It took mere moments for him to blow his load, having been pretty close after Diamond’s teasing. Clenching his teeth, and grunting like an animal, the man’s cock erupted over the filly. Thick and hot strings of jizz coated her pink furred belly and crotch. Dumbstruck, he panted as he looked down at the debaucherous sight.
“I guess we’ll both be needing a bath after this,” Diamond giggled playfully. “But first,” her expression shifted to one of derision, “clean me up…”
Anon steadily got to his feet, fumbling to pull his pants up in the process. He still couldn’t believe he’d gotten off to a horse, and a damn filly at that. “I’ll get a washcloth. Where’s the bathroom?” he asked, attempting to avoid eye contact with the precocious pony.
“I think you’re confused,” Diamond softly said, looking up at him with mock concern. “Get down here and lick it clean.”
“I, um…” Anon rubbed his neck anxiously. He knew that, if he didn’t, he’d be in hot water for sure. There was a line he’d already crossed and if her parents knew, he’d be up shit creek. Stooping back down, he got on his hands and knees, bringing his face to her fuzzy pink belly. Ropes of his cooling jizz festooned her small body. Swallowing hard, and steeling his resolve, he began to lick his salty cum from her.
“Look at you, you’re like a little puppy,” Diamond cooed affectionately, tussling his hair with one forehoof. She knew that the deeper she dug her claws into him, weakening his resolve, the more submissive he’d become and, ultimately, she’d have her very own slave. After what he’d done to her, she had plenty of blackmail material to work with already. Now it was only a matter of time until he crumbled under her hoof. “I think we should get you a collar and a leash,” she sighed, watching as he worked his way up her frame. “How’s that sound?”
Inexplicably, Anon felt a tingle run up his spine at the notion. As much as he wanted to deny it, there was something arousing about being treated like this. He simply grunted at her words, nearly finished with his degrading task.
“Good boy,” the filly whispered. Hooking a hoof under his chin, and angling it upward, she gave him a little kiss on the nose; an apt reward for servicing her and cleaning up his mess. “Come on,” she said, rolling over to stand up. “I’ll show you how to properly wash my mane when you give me a bath.”
“Sure,” Anon groaned.
“Sure what?” Diamond asked, stopping to stare up at him.
“Ma’am,” Anon replied flatly.
“Good,” the young mare mused, trotting off to the bathroom with her human in tow.