The trio shuffled upstairs with the barest modicum of decency, despite the lurid acts that they were planning to undertake.

As they made their way, Rarity tried to comfort Cookie, who still seemed quite out of her element. She’d attempted one last time to convince her mother that, if she felt so nervous, there was no need for her to follow through with the act… but the mare affirmed her commitment - no turning back now.

Walking down the upper floor hallway, Rarity was surprised that her door was partly ajar as the strange group reached her room. She almost always kept the thing shut - a necessity with Sweetie Belle getting into everything and pilfering her fabrics. The open door would mean less noise as they snuck into the fashionista’s bedroom slash workshop.

Rarity had lost track of just where her little sister was, and the last thing she wanted to do was draw attention to the fact that their mother was about to enter a bedroom with Anon… and spend an extended period of time in there with him.

After they’d all entered, Rarity shut the door behind Anon, a small sense of relief washing over her. She’d had the good sense years back to soundproof her room entirely. At least Sweetie wouldn’t hear what was about to occur. The soundproofing had proved its worth many times over: the prying ears of the curious little filly had not been tainted by the rather vocal style of coupling that Rarity was so fond of drawing from her suitors.

“So - how we going to do this?” Anon chuckled, diving onto Rarity’s four-poster bed and rolling onto his back. “A little wham-bam thank you ma’am?”

“Uhhm…” Cookie looked nervously between the human and her daughter. “I-I’m not su…”

Rarity swallowed her annoyance. She’d hoped that she might be able to just… sit in the corner, plug her ears, shut her eyes and mentally re-arrange her fall fashion line-up… blocking out everything and waiting for the whole sordid affair to pass... In that sense her strategy was not unlike that she’d employed during her own first fumbling experience with a colt.

But… her mother’s lack of confidence, her desire for more excitement, and her pleading eyes seemed to necessitate a more active role than she’d hoped for.

“Hardly Anon.” Rarity snarked. “If you intend to be... with... the mother of one of Equestria’s greatest heroes you shall act with humility and respect.”

“Huh, that’s not what Mr. and Mrs. Shy said.”

Rarity blanched slightly as she realised the implication. She’d always heard the rumours, of course, whispers about Fluttershy’s parents’ rather exotic love-life.

“Oh, so that story I heard about you bucking her was true then?” Cookie asked perking up slightly. “So that means that, when it comes to the moms... I’d be your…”

Anon grinned. “Fourth.”

“A gentlecolt should never kiss and tell, Anon.” Rarity clicked her tongue.

“Pftt… fuck that.” Anon laughed, holding up all five fingers on his hand, lowering one as he listed off each of his conquests: “I screwed Twilight’s mom silly, made Rainbow Dash’s mom wetter than a rainstorm, and cucked the hell out of Fluttershy’s dad.” This left only one finger upright - his middle digit… directed right at Rarity.

“They have names Anon.” Rarity growled.

“Eh. They have vaginas too. And at the end of the day… isn’t that all that really matters?” Anon lifted a hand to his chin, as if he were contemplating some deep truth like one of Rarity’s favorite Moneigh sculptures. “Like… for real... screw dragons and their weird non-vagina lizard-holes, am I right?”

“Cloacas you insensitive moron.”

“Whatever. We doing this?” Anon gestured down at his pants, as he scooched toward the edge of her bed.

“Apparently. However, I’ll not have you mistreat my mother. She’s a mare who deserves respect, affection, and excitement.” Rarity strode over and poked Anon in the chest. She made sure to do so with the edge of her hoof, and sharply enough that it might cause a bruise. “Is that understood?”

“Fucking ouch.” Anon rubbed his chest. “All right, all right! I’ll have you know that I come with a one-hundred percent satisfaction rating among moms currently.”

Rarity frowned. It wasn’t that the human was wrong. She’d heard from Twilight and Rainbow first-hand the agony they had to go through, subjected to their mothers extolling the virtues of monkey-phallus. She just couldn’t see how that was possible for this lanky, tall, annoying slob with his spider-like claw-hands and unimpressive physique.

“So… R-rarity… h-how do you think I should, well… start?” Cookie’s unsure voice spurred Rarity from her rage-filled thoughts.

“He shall start, mother.” Rarity smiled warmly. “You are a beautiful mare, and this beast should worship you by…”

Rarity hesitated.

This was her mother after all. Yes, Rarity was older now, her relationship was more mature - one of mutual respect and friendship… but she was still her mother! Could she really do this?

Of course she could! Just… treat her like somepony else… pretend as if you were just a director in a fabulously erotic movie!

“H-he should... lap at your flower… until you’ve experienced the greatest of pleasures.” Rarity managed to get out.

There was no turning back now. She was committed. Rarity patted the bed and guided her mother up onto it lovingly, calmly lowering her onto her back so that the human could lavish her with the oral attention she deserved.

“Mmmm… nah.” Anon shrugged indifferently.

“Nah?” Rarity paused, caught out as she was halfway through lowering her mother.

“Well first off… lap at your flower? What the fuck is that literotica bullshit?” Anon scrunched his face with distaste. “Maybe if you’d said: ‘eat your pussy he makes until you cum on his face’ I’d have been interested. But you’ve just ruined my appetite.”

Anon unhooked his pants and pulled them down with no decorum at all, revealing his ridiculous white underwear briefs. Rarity believed that she’d heard the human refer to them as ‘tighty-whities’. With a careless half-twisting leap he jumped onto the bed.

“So… now I think I’m in the mood to go first.” Anon reached out and snagged Cookie’s hoof, wrapping his fingers around it sensuously before moving it toward his crotch.

Rarity saw her mother’s eyes widen with excitement... saw Cookie chew her lip and swallow... saw her catch her breath at the mere touch from the human... from mere hoof-holding.

‘L-l-lewd!’ Rarity’s mind protested.

But before she could utter a word, Rarity watched the human slide her mother’s hoof against the bulge in his underwear, rubbing it into the sizeable package hidden beneath the fabric. With careful direction, Anon helping Cookie’s well-manicured hoof to find it’s rhythm before lifting his hand away.

“Anon!” Rarity found her voice, “How dare you? I said you were to treat my mo-”

“Can you shut up? By Celestia’s fat-ass, I’m the expert in mom-fucking here Rara, besides… I’m the one with the dick - so I make the rules. Gotta respect your stallion, right? That’s what this weird fucked up backwards world is into, right?”

“How dare y-”

“Oh come off it… besides, look: she likes it!” Anon gestured down at Cookie, who was now pawing at the bulge on her own - exploring it with enthusiasm and wonder.

“M-mother?”

Cookie looked up at her with a shy smile. “W-well… he is a stallion, dear… and he feels very… um… n-nice… under there.”

Rarity sniffed, throwing up her chin. “Perhaps I should just go, then.”

“No!” Cookie shouted suddenly, reaching out toward her daughter with her free hoof. “I… I just - feel better if you’re here, with me.”

Rarity let out a breath that rippled through her body, taking some of the tension in her muscles with it. There really isn’t anything she could do. Resigning to her fate, she turned and watched.

Her mother’s hoof played back and forth along the human’s cotton undershorts, massaging his bulge as it began to throb larger and larger, the shape growing quickly under the thin white fabric.

“Yeah, get in there…” Anon grinned. “Get a real good feel for little Anon.”

“It… isn’t feeling so… little anymore…” Cookie glanced nervously back at Rarity, her hoof starting to need longer and longer strokes as the bulge approached the edge of the human’s underwear. “But, a few months ago… I thought that you said you only had five and a half inches of pleasure…?”

Anon chuckled. “Soft, maybe.” Rarity couldn’t help but look between the human and his groin as his fattening pink fleshy penis began to peek out of his briefs and spill down his inner thigh. “Don’t wanna scare you little ponies away… never measured the thing when it’s at full staff… it’s no big deal.”

“Horseapples.” Rarity snarked. “You seem like the type to measure it every morning.”

“OK - so maybe it’s precisely ten point two three inches erect… ten point three if I flex really hard.” Anon took Cookie's other hoof, directing it lower, onto his balls. “These are pretty hefty too.”

“Narcissist.” Rarity couldn’t hold her tongue. The human's cock was halfway to his knee though. And such a strange shape and color: pink and cylindrical… all covered by a strange shriveled skin sheath at its expanding tip. It was completely alien from the dome-like end of a normal stallion.

“Like you’re one to talk…” Anon laughed. “I admit… I do like showing off.” On cue, he stopped Cookie’s groping hooves, using the pause to lift his hips and peel down his undershorts.

Both mares stiffened slightly, hackles rising and tails swishing instinctively. Anon’s full erection rose proudly in front of them, throbbing with masculine intensity between his pale legs.

Rarity couldn’t hide the intensity in her professional gaze as she drank in its every detail. Each subtle vein... the sheer thickness at its base... the way it had no medial ring as it towered up to folds of skin that had to be retracted to reveal its strange mushroom-shaped dome... even the way the small cockslit drooled out a fat drip of clear liquid… her innate sense of style screamed out at the savagely sexual attractiveness of this… this… cock.

Rarity may have detested this petulant human, but there was no denying that his tool was perfect for fucking ponies.

“W-w-wow.” Cookie Crumbles mouthed breathlessly.

“I fuckin’ love when you mares get all quiet after the big reveal.” Anon’s shit-eating smile had reached all new levels of insufferable-ness. “Here you can have this.” He tossed his underwear into Cookie’s face.

Rarity opened her mouth to complain at the human’s callous treatment of Cookie as some clothing stand... but her mother’s reaction stopped her. Cookie had shut her eyes, nostrils flaring, while taking in a luxuriantly deep breath. A light moan crossed her lips as she savoured Anon’s musk as if she were sniffing a sweet Prench perfume.

“Mmm… you… you smell… amazing.” Cookie groaned.

Rarity watched, stunned, as her mother lifted the garment from her nose, her dreamy eyes looking back at the human.

“Oh yeah? You like that funk, huh?” Anon’s hands found their way into the deliriously happy mare’s mane, playing with her sweaty fur and scritching behind her ears… before taking hold of the back of Cookie’s head more forcefully. “Well, why don’t you try it right from the source?”

With a quick pull, Anon pressed Cookie’s muzzle right into his sweaty ballsack, letting the thick base of his organ rest against her face.

Rarity stifled a choked surprise. That was the same face that had blown her so many goodnight kisses... which had cheered her on with encouragement at her first fashion show... which had comforted her with warm smiles when she’d felt down after a tough day at school… Now it was reduced to a debauched mess, a googly-eyed drunkenly moaning mask that stared up at the depraved human with love-struck eyes even as it was draped with his sweaty phallus.

“Anonymous! You brute!” Rarity stepped closer, the rage in her eyes fixated directly on the impious human. “Unhand her this moment!”

“What are you talking about? I’m not ‘handing’ anything at the moment!” Anon chuckled, holding both hands up plaintively in front of the furious unicorn - clearly showing he wasn’t forcing Cookie to do anything.

Rarity gaze quickly shifted to her mother, who was making no effort to extricate herself from Anon’s groin… Quite to the contrary, she was nuzzling his heavy, swollen sacks of flesh with her cute purple snout. Her tongue was even poking out from her open mouth, leaving little drips of her saliva on the human’s pink skin as she drooled with desire.

“I think she likes it!”

“Mmmhm… so… so g-good…” The weak mumble from her mother was directed more at the human taint Cookie was caressing than anypony else.

“I love her hair though.” Anon smiled, still moving his hands through her mother’s beehive mane. “Can’t wait to get it all sweaty and fucked up.” He slipped his hands back into her luxurious strands, stroking idly.

Rarity stood there, not wanting to watch, but unable to look away. The joyous groans of her mother filled her flicking ears. Rarity’s eyes were desperate to look somewhere, anywhere that wasn’t the grinning human’s face, his bobbing cock-tip, or the messy sight of her mother grinding her face into Anon’s sex.

But there was no escaping the debauched show. Even worse… Rarity was beginning to feel… something.

A discomforting feeling was growing, starting in her stomach and moving backward… toward her hips… her legs… her nethers… Celestia she wished she could just leave and bury this strange feeling away - pretend it had never happened.

But she couldn’t!

Rarity had to drink in the whole erotic scene, imagination going wild with images of that swollen alien cock… and of her aroused, horny mother… it was unbearable! Rarity shifted in her stance, feeling the swelling mound between her legs grind against the inner parts of her thighs.

“Umm… anytime you wanna… y’know… start…” Anon grunted down at the panting mare between his legs, “...giving me a blowjob… feel free?”

Author's Note

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I write to make you, the reader, happy! Letting me know that I did my job is the whole reason why I write! Give me feedback, feed me!

Cookie is so cute to write! I love the idea of a mare who married her high-school beau and is far too innocent in her older age.

The funny thing is... I'm not sure who is the more dangerous sex-master in the room... Anon... or Rarity?