“Hey there, Diamond,” Anon quietly stated, waving at the little pink filly.
Totally and completely ignoring him, without so much as slowing or looking in his direction, Diamond trotted through the foyer and to the stairs. He watched her depart, hoping that she’d peer back at him, but it was a lost cause. As she made her way to the second floor, presumably to her room, his smile gradually faltered.
It had been nearly a month since he’d fooled around with Spoiled Rich, having caved to his impulses and plowed the older mare. Shortly after the incident, Diamond Tiara had basically cut him off, stopped talking to him, and even ceased acknowledging his existence. At the time, he’d felt guilty for fucking the filly’s mother, but that wasn’t the worst part - the worst part was that Diamond had caught him doing it.
Though she could be a handful at times, often lauding her status as the only child of an affluent family, Anon really had developed a soft spot for her. She’d effectively given up bullying, after having made friends with Scootaloo, Sweetie Belle, and Apple Bloom, and she’d gone so far as to help the Cutie Mark Crusaders out a few times - sure, she may have had a domineering and lewd streak, having tied him up and sadistically played with him, but that wasn’t that bad. Unfortunately, since she’d cut all attention with him, he was left feeling shameful and concerned for her.
If Diamond had just stopped talking to him, he wouldn’t have been all that worried - a bit crestfallen, sure, but not genuinely worried about her. Sadly, whatever turmoil she was going through extended beyond him, impacting her performance in school and even her relationship with Silver Spoon. He was almost certain that he was at least partially to blame for the issues at hand, and that knowledge had been slowly eating away at him.
Setting down his broom, after he’d finished sweeping the foyer, he trudged upstairs and to the filly’s room. If Diamond was going to give him the cold shoulder, he’d have to step up to the plate and seize the initiative. The way he saw it, talking to her couldn’t make things any worse, yet he’d had to wait for an opportune time to chat - ideally when Spoiled and Filthy weren’t home. Considering the diminutive mare’s parents were out attending a formal event, and since her attitude only seemed to be getting gradually worse, he steeled himself and made his move.
“Diamond?” he called out, softly knocking on her door. “Do you have a -”
“GO AWAY!” she bleated from within her room.
He paused, toying with the notion of fleeing, before summoning his courage. “Diamond, I want to talk. Can I come in?”
“What do you want to talk about?” she spat from behind the door. “Did you want to talk about plowing my mom?”
Her words sank in like a dagger. They both knew what he’d done, but hearing her say it made the hurt all the more unbearable. It was bad enough that he’d been coerced into doing the do with a filly, something he was too fearful to ask about the legality of, but he was an adulterer as well. Screwing his eyes closed, he rubbed his temple in frustration.
As crazy as it may have sounded, he’d actually grown to like Diamond, and not in a platonic way. She was sassy, intelligent, and had a very commanding aura, three traits he admired in any woman - sure, she may have been a different species and a fair bit younger than himself, but it wasn’t like he’d been the one to initiate anything with her.
“Can you at least come to the door? I…” his voice faltered, “I miss talking to you…”
He held his breath, waiting for a reply, but the room was silent. If he’d known that fooling around with Spoiled would rub her the wrong way, he would have never done it - that being said, hindsight is twenty-twenty. There was nothing he could do to change his past actions, but he could and would try to rectify the situation.
“For what it’s worth, I regret doing anything with her - your mom,” he sighed, resting his head against the door frame. “I know you probably don’t believe me, or care, but I thought she was robbing your house.”
The door flew open, mere inches from his face, revealing Diamond glowering up at him. “Yeah, sure, she totally made you stick your dick in her,” she growled.
“It’s true,” he insisted, squatting down to his haunches. “I caught someone in your parents bedroom, tried to catch them, then…” he trailed off, choosing his words carefully, “things kind of just happened.”
The filly’s eyes narrowed, staring daggers at his face. “So you rutted what you thought was a would-be robber…”
Pinching the bridge of his nose, realizing how insane he must sound, he shook his head. “It’s more complicated than that. Your mom can be very - uh - demanding,” he explained, anxiously chuckling. “I guess that’s one trait you got from her.”
“Whatever,” she quietly huffed. Stepping to the side, she started closing the door.
“Wait,” he interjected, jamming the door with his foot, “is this going to be alright? I don’t want to -”
“To what?” she barked. “To fuck my mom? To stop having me play with you?! To...to…” She choked back a sniffle, as her eyes began to water.
Anon’s eyes widened, seeing the full impact of his actions. He hadn’t simply made her angry, he’d unintentionally hurt her. The revelation felt like someone twisting a knife in his chest, amplifying his guilt and making him feel even worse than he had before. Reaching for her, reflexively going to offer her some consolement, she batted his hand away.
“D...don’t act like you care - if you did, you wouldn’t have slept with my mom,” she whimpered, her rage briefly overtaking her sorrow. “If...if you cared, you would have been happy with - Sniff - with me…”
As her words sank in, he froze. Some part of him had wondered if she genuinely cared for him, or if she simply viewed him as a plaything, but now he knew the truth. Somehow, despite how odd it was, she’d developed some sort of an emotional attachment to him; be darned if he could explain it, since she mostly seemed to bully him, yet it was the only reasonable conclusion he could come to - still, he had to know for sure.
“Can I ask you something?” he inquired. “How was I supposed to know any of this? All you did was pick on me and harass me, so I thought you didn’t like me.”
Wiping her nose with a forehoof, Diamond solemnly shook her head. “It’s just - I…” she fell silent, staring down at the floor. “I’ve never had many friends - well, besides Silverspoon.”
Lifting his gaze, Anon peeked down at her. “And that makes it hard to talk to folks?”
She nodded, affirming his suspicions. “Yeah…”
“Even though you can be a handful at times, I really do like you - if I didn’t, I wouldn’t be here talking to you,” he murmured. “It probably doesn’t count for much, but if you’d told me how you felt, I would never have done anything with Spoiled.”
“So you’re not going to do anything with her again?” Diamond quietly asked, looking up to his face.
Smiling weakly, he shrugged. “If you don’t want me to, no. Also, for the record, the whole thing made me kind of uncomfortable.”
The filly’s eyes locked with his, staring at him for a brief second, before she scowled and looked away. “In that case, I expect an apology.”
“But I already apologized,” Anon balked, surprised by her sudden shift in tone.
“I want a kiss,” she demanded, petulantly stomping her hoof, “and a promise that you’ll never touch my mom again.”
Without a second thought, he leaned forward, pecked her brow, then straightened back up. “Done, and I promise I won’t even look at Spoiled’s backside ever ag-”
“That was not a kiss!” Diamond cut him off. Seeing his confusion, she rolled her eyes and pointed to the end of her muzzle. “I want a real kiss.”
The request hit him out of the blue, forcing him to weigh his options. On one hand, giving her a kiss on the lips would be far from the worst thing he’d done with her - then again, he felt almost certain that it would mean leashing himself, figuratively or possibly literally to her. He’d be lying if her sadistic steak didn’t rub him the right way, opening him to a fetish he didn’t know he had, which made the matter all the more complicated.
As he peered down at her, seeing her expectantly close her eyes and pucker her lips, he swallowed hard. He was well aware of what the impetuous little mare was capable of, what sinful joys she could deliver, and the thought sent blood rushing to his loins. Steeling his resolve, telling himself that he was solely doing it for her, he leaned forward and kissed her.
“There,” he weakly muttered, only just pulling back. “I’m glad that - Mmm?!”
Before he could finish speaking, she leapt forward, tackled him to the ground, and landed on his chest. It wasn’t the fact that he’d been toppled over, nor that the small pony was sitting on him, that startled him - no, it was that she’d apparently been less than satisfied with his apology. Pressing her muzzle against his face, she forced her tongue past his lips and into his mouth.
As the confusion faded, replaced by his growing passion for the young mare, he slowly reciprocated. Though he was loath to admit it, he really had taken a liking to her, and not just in a sexual way. She knew what she wanted, and she wasn’t afraid to take what she wanted; be it a piece of jewelry, some bauble, or the man charged with being her sitter, she could and would get her way with whatever or whomever she wished, and Anon was no exception.
Subconsciously lifting one arm, Anon gently cradled her rump. Though it had been weeks since he’d touched her, the soft, warm sensation of her supple tush against his palm sent an excited shiver up his spine. Wiggling in his grasp, she softly hummed and passionately made out with him - that was, until she came to an abrupt stop.
“That,” she exclaimed, rearing back, “was a ki-Mph?!”
As quickly as she’d struck him, he turned the tables on her. Cradling her ass in one hand, while holding the back of her head in the other, he shot forward and frenched her yet again. Though she had a domineering streak a mile long, he simply couldn’t help himself. After all the worry she’d put him through, he deserved a bit of payback.
Their breath mingled, their tongues warred and coiled around one another, and their eyes drifted closed, as their inhibitions gradually shook free. It may have been strange, given the differences of their age and species, but their actions spoke for themselves; they wanted - no, needed this moment, taking some comfort from the kiss. Seconds dragged by, he relaxed his grip and allowed them to pull away from one another.
“Was that better?” he whispered, trying and failing not to smirk.
Her stunned and smitten expression lasted no longer than the blink of an eye, before she turned her nose up at him. “I didn’t ask for all that…”
Lifting her off himself, gingerly setting her to the side, he rolled over, got to his knees, and dipped his head. “Sorry, I couldn’t help myself. Any way I can make it up to you?”
“M...maybe if you carry me to the bed, we can talk about it,” he cooed, anxiously looking over her shoulder.
Anon opened his mouth to reply, fully intent on asking her what she meant, but he caught himself. He considered himself fortunate that he’d started making amends with her, and he was not about to risk taking a huge step backward. Pushing himself up, he cautiously leaned forward, plucked the filly from the floor, cradled her to his chest. If she wanted to go onto the bed, that was fine with him - nevertheless, he couldn’t rightly say where her intentions lie.
Supporting her in his arms, he stepped into the room and kicked the door closed behind himself. Even if Spoiled and Filthy were out that afternoon, he’d rather not have anyone see him carrying the affluent family’s only daughter into her chamber. He still wasn’t sure what Equestria’s laws were regarding the age of consent, nor did he have any plans on asking anyone, so he did his best to avoid any undue attention.
“Here we go,” he softly intoned, setting her onto the mattress. “Now then, you were saying?”
With an impish look in her eye, flashing him a small grin, Diamond rolled onto her back, splayed her legs, and presented her very moistened crotch. “I want another kiss…”
He gulped, staring down at her delectably plump and juicy marehood. Though she was small, the ripe, rosy flesh of her lower lips, winking, and trail of feminine juices leaking from her depths left little room for doubt - she was excruciatingly turned on. As he shifted in place, keenly aware of his hardening manhood, he found himself at a crossroads.
If he didn’t please her, there was a very real chance that, sooner or later, she’d blab about their licentious shenanigans and, if he was extremely unlucky, he’d end up getting in a load of trouble - that being said, he’d secretly missed their bawdy time together. Peeking back at the door, making sure it was firmly closed, he warily sank to his knees and brought his mouth towards her groin. He told himself that he was only doing it for her, that she could and likely would blackmail him if he didn’t, but that was a lie.
As his face crept closer to her loins, the sweet, ambrosial scent of her sex wafted to his nostrils. The aroma reminded him of what she tasted like, spurring him onward. Crushing what little inhibition he had left, reaching out and repositioning her ever so slightly, he leaned forward and pressed his mouth to her drooling lower lips.
His eyes drifted closed, as his tongue glided through her silken folds. The flavor of her marehood was as wonderful as he remembered, tasting of exotic citrus and grass. As his lips wandered to her clit, he lowered one hand to his waist. Though she’d clearly known what she was doing, fully intent on reconciling in a decidedly depraved way, she hadn’t mentioned anything about him being able to enjoy himself throughout the endeavor.
Quickly loosening his belt, he undid the button on his pants and unzipped his fly. He was so hard that it practically hurt, having abstained from any sort of sexual activity since he’d gotten some action from Spoiled. With the weight of guilt lifted from his shoulders, and his face pressed between the filly’s thighs, he hungrily ravished Diamond’s snatch while pulling his rigid cock free.
“Oh yeah,” she groaned, shifting slightly, “right there…”
Stealing a glance upward, Anon’s heart skipped a beat. At some point or another, possibly while he’d been licking away at her, she’d pulled a pillow under her head to better enjoy the show. Peering down her chest, past the deliciously flat breasts on her groin, she smiled at him. Subconsciously, he started stroking himself off, growing more and more aroused by the second.
There was something exceedingly hot about being with a female who took charge, and he’d grown to love his diminutive charge for that. He’d like to say he was the first guy to ever fool around with her, either too submissive or ignorant to dismiss her wiles, but he doubted it. Given her penchant for control, and the fact that she was very versed in all manner of lewd acts, he was most likely her most recent plaything - still, that didn’t bother him in the slightest.
“Don’t stop,” she halfheartedly whined. Locking her fetlocks around the back of his head, she pulled him deeper.
Eager to please, and more aroused than ever, he plunged his tongue into her taut canal. Though she was extraordinarily tight, virtually making him work to reach her depths, he’d discovered that it was a ruse. In spite of her petite size, she was easily able to handle the entirety of her manhood. Her trick, as far as he could tell, was in some preternatural amount of pelvic muscle control.
Slowly turning his head from side to side, smearing his face with her nectar, he shamelessly got himself off to eating her out - at least he was, until she unlocked her hind legs. Opening his eyes, seeing a somewhat wounded look on her face, his motions ground to a halt. Either she had something else in mind for him, or he’d unintentionally committed some slight.
“Is everything alright?” he timidly asked, licking his lips.
“Are you touching yourself?” she countered, narrowing her eyes.
He stiffened in more ways than one, under her judgemental gaze. She’d know if he was lying, likely asking that he stand to see if his pants were still fastened, which left him with one option - telling the truth. Looking to the side, unwilling to meet her eyes, he shamefully nodded. It was all he could do to hope she wasn’t upset with him, leaving him to hold his breath and pray.
“Stand up,” she softly commanded, waving a forehoof at him.
Doing as asked, leaving his loosened slacks as they were, he grunted and stood. Her eyes sailed to his groin, locking onto his rigid manhood, as soon as he was on his feet. It was all he could do to force his hands to stay at his sides, while his apprehension grew stronger by the second. Shifting her attention from his turgid length to his face, she knit her brow.
“Did...did you really mean what you said?” she breathed.
“About never going near Spoiled again?” he inquired, prompting her to nod. “Yeah, I meant it - if I’d known doing anything with her would hurt your feelings, I never would have even considered it fooling around with her.”
Silently lifting and spreading her hind legs, Diamond grabbed her fetlocks. “H...here -” she sputtered, averting her gaze, “put it here…”
His anxiety and reluctance evaporated, as he stepped to the bedside and got into position. He couldn’t have fathomed that his day would take such a lecherous turn, yet he wasn’t about to complain. As far as he was concerned, having earned Diamond’s forgiveness and discovered that she harbored feelings for him, she’d earned his affection - that and his mounting excitement was clouding his judgment. With one hand on her hip, and the other clutching the base of his shaft, he guided the tip of his manhood to her entrance.
Looking to her face and seeing her nod, he gently sank into her. Like molten silk, her canal embraced him. Far warmer and more snug than any woman he’d ever been with, including Spoiled Rich, Diamond’s marehood was, simply put, awe inspiring. As he released his tool, he leaned over, braced himself on one arm, and smiled down at her.
The filly groaned, writhing in place, while his length slipped into her. “Sweet Celestia - I almost forgot how good this feels.”
“Yeah,” he sighed, bottoming out within her. Though he wasn’t fully hilted, with only the last inch or so of his length in the open air, he was more than ready to begin. “Ready?”
No sooner had the filly dipped her head than he started to move. Steadily pulling back, freeing roughly half of his shaft from her depths, he drove his hips forward. The blissful look on Diamond’s face was inspirational, mirroring his own enjoyment of the moment. As he began humping her, falling into a slow rhythm, they stared at one another.
Ordinarily speaking, he would have closed his eyes to savor the sensations of his pint-sized lover, but not today - not after making up with her. Her smile wavered, as she broke the staring contest and looked to the side. Her cheeks darkened slightly, causing his grin to broaden. She really was adorable, especially when she was blushing, but the sight gave him an idea.
Continuing to move his hips, lazily pistoning her marehood, he bent forward and rested on his forearms. There was something he’d always wanted to try with her, something which ran contrary to her usual bedroom demeanor, and he’d finally been given an opportunity to test it. As she turned her head, with her muzzle a hair’s breadth from his face, he kissed her. She shuddered, taken off guard by the romantic gesture, yet quickly reciprocated and quietly moaned.
Hotly making out, with Diamond’s hooves resting on Anon’s pounding hips, the pair’s passion soared. Despite her mate being far larger than herself, the tiny mare gave as good as she got; clenching and relaxing her sex, she squeezed and massaged his shaft. Eager to please, savoring her affection, he gradually plowed her with increasing speed and force.
Seconds dragged into minutes, while they kissed and drove one another into a frenzy. Marish nectar leaked from around his cock, dribbling between her buns and painting his groin, while his nuts slapped against her tush. Each time he plunged into her, virtually driving the air from her lungs, a light whimper or feminine grunt escaped her. The sounds of their delight mingled with the aroma of sex and sweat, making the debauchery a feast for the senses.
As he continued on, doing what he could to pace himself, Anon felt her quake against him. He’d been with her enough to know what it meant, that she was close to her limit, and that knowledge practically drove him mad with lust. Unfortunately, between his dry spell and his enthusiasm to have an intimate moment with her, his endurance floundered.
“Anon,” she mewled, breaking their kiss, “I...I…” Her forelegs shot upward, wrapping around his head, as she brought her muzzle to his ear. “I love you!”
The admission was Anon’s undoing, sending him soaring over the edge. His length wildly throbbed, pulsing with his thundering heart, as he impulsively crammed every inch of himself into her. Gritting his teeth, nearly overcome with the rapture she afforded, he wrestled control of his body, drew a deep breath, and threw his head back.
“I love you too!” he bellowed, a split second before his seed crashed into her womb.
Be it from serendipity, luck, or some combination of the two, Diamond climaxed a split second after him. Quaking beneath him, lewdly gushing her orgasmic nectar from around his buried length, she threw her head back and brayed to the heavens. Their finale, punctuated by their confession for one another, was cathartic to a fault and finally heralded their feelings for each other.
Heaving air into his chest, awash in euphoric bliss, Anon peered down at her. It was only when his eyes graced her face did he realize something was wrong, noticing her attention had shifted to the side of the room. Turning his head, following her gaze, his blood ran cold. There, standing just outside the open door, was Spoiled.
“I can explain!” he blared, overwhelmed with terror. “I wasn’t -”
“Mother,” Diamond tutted, casually grabbing the man’s shirt and pulling him downward, “Anon is mine…”
Looking to the filly’s face in confusion, Anon found himself pulled into a very deep and theatrically sloppy kiss. Completely at a loss, seeing Spoiled shake her head in disgust, he hesitantly returned Diamond’s affection. He’d just been claimed by a young mare, in front of her mother, and there was nothing he could do about it.
“So,” Diamond continued, shoving the man’s face away, “don’t you dare lay a hoof on him ever again.”
“Hmmph!” Spoiled huffed, turning her nose up at her covetous daughter. “We’ll see about that!” With those final words, the older mare stomped down the hallway and out of sight, leaving the pair to their own devices.
“That was - uh -” Anon wheezed, genuinely uneasy with the development, “something…”
Clutching his collar, wrenching his attention towards her face, Diamond’s unwavering eyes bored into him. “If I ever see you so much as looking in her direction -”
“You won’t,” he softly interrupted, pecking the tip of her nose. “I Pinkie promise.”
Her face went beet red, her eyes widened, and her expression softened - still, she didn’t look away. “Good. Now then, I demand a shower.”
As amused as he was by her reaction, he couldn’t help but feel slightly nervous about Spoiled’s intrusion. “But what about -”
“I’ll handle her,” Diamond groused, constricting her marehood around his softening shaft. “You just worry about doing your job and keeping me happy. And one more thing, I want you to call me your Princess from now on.”
The comment and self-appointed pet name fractured his composure, causing the corners of his lips to turn up. “Alright.”
“Alright what,” she grumbled.
“Alright,” he breathed, kissing her cheek, “my Princess…”
