Author's Note

A look at what could've been. This continues on from the alternate Day 6, and will lead towards the Good End.

Alternate Night 6: The Mother of All Final Gambits

“What is it going to take to break her?”

Midnight’s frustrated question was only answered by muffled sobs and moans as she repeatedly rammed her cock deep into Cadances’ pussy. The pink alicorn was being pushed harder into her boulder-like breasts, milk gushing forth into the fleshy tubes connected to the ceiling. The stiff member was buried so deep inside Cadance’s snatch that her belly was stretching and pushing into her underboob with each thrust. To their right, Daybreaker’s moans were more lustful, as a magically-projected cock and balls hammered in and out of her mouth, as well as her own marehood and ass.

“She was soooo close to breaking, I know it. RaaAARRGHH!” As the corrupted alicorn roared, she slapped her sister-in-law’s flanks hard enough to ring out loudly throughout the throne room. Said living throne squealed as the impact right across her cutie mark triggered another orgasm, her insides squeezing Midnight’s pole even tighter even as she continued the vaginal assault. “If only I could creampie that shy slut, then-”

“That honor isn’t yours to take, my apprentice.”

That familiar voice roused Midnight out of her rage-rutting, and swiftly she fell off the edge into orgasm as her concentration slipped. A torrent of sperm surged up her length and deep inside Cadance, the elder alicorn moaning loudly as she came once more. Daybreaker also suffered the throes of ecstasy as the magical cocks plunging into her spewed forth their own globules of seed, moans and croaks of pure bliss escaping the former Celestia. After catching her breath, Midnight looked up to see Talvira standing at the doors of the throne room, a neutral expression on her face.

“M-Mistress…” Midnight panted, fighting through her refractory period to pull out of Cadance and stumble towards her. This left a trail of sperm dangling from her still-hard cock to the floor, as well as a flood of it escaping the pussy of the princess of love now it was no longer clogged. “H-How… How was your trip, t-to Manehatten?”

Talvira sighed. “Yet another case of the leaders of my hordes being incompetent. Honestly, I struggle to remember how that slug rose through the ranks. Let’s just say the “Equestrian Government in Exile” no longer exists, and its members are either dead or stuffed with a member.” The demoness then spared the pink milk-spewing throne a causal glance. “I take it your plan for Fluttershy failed?”

Midnight’s eyes widened for a second, her voice stuttering and hands nervously rubbing the back of her neck as she answered. “Er… y-yes, mistress. I-It’s just, well I-I thought, tha-that your harem and I would be enough… b-but, argh! I’m so sorry mistress. Please forgive me.”
Midnight fell to her knees before her new teacher, missing the demoness roll her darkened eyes.

“Get up, Midnight, before I rut you out of pity.” The alicorn complied immediately, facing her tired master with trepidation in her eyes. Talvira sighed and rubbed her temples. “Fluttershy still has to survive tomorrow, and,” she looked back through the doors into the hall, her devilish grin returning, “I intend to make sure she doesn’t.” Midnight, tilting her head slightly in confusion, stepped forward to look out the door, and soon her grin matched her mistress’.

There, flanked by two monstrous guards, kneeling with red magic binding her arms and wings behind her back, was an older pegasus mare. She still looked quite attractive for her age, with curves in all the right places, big breasts that were close to being E cups from Midnight’s inquisitorial gaze, and wide, foal-bearing hips. But it was her off-yellow coat, maroon-tinted mane and tail, and aqua-rimmed glasses that revealed her identity.

“F-Fluttershy’s mother? Oh, that should break her.”

“Hopefully. However, after collecting her, I thought about it and realized why should she have all the fun?”

At the snap of her fingers, a veil of invisibility fell, and four more mature mares appeared alongside Posey Shy. One of which Midnight knew all too well.

“Oh, thank you, mistress,” she said, her horn lighting up in response. “But I’m certain my friends who have seen the light would be more than willing to join in.”

Talvira could only grin at the delicious spread of debauchery before her.

Sitting upon her throne of white titflesh, she happily watched on as the former elements of harmony went to town on their own mothers. They were all huddled together before the thrones, and a quick side glance revealed Posey Shy, the only mother not taking part, was watching on with horror from her seat upon Cadances’ pink bosom. Talvira could also spot a hint of intrigue in her gaze, enhancing her own delight as the moans echoed throughout the chamber.

“Argh! Ha, ha, T-Twil-AARGH!”

The cries brought the demoness’ attention back to the spectacle, and focused in on her new student. Midnight was currently re-introducing herself to the passage that she was birthed from, as her alicorn cock scraped the insides of her mother; one Twilight Velvet if Talvira wasn’t mistaken. The grey mare’s belly distended with each thrust; her teeth gritted together as her daughter repeatedly knocked against her cervix whilst holding her spread eagle.

“What’s the matter, Mom?” Midnight asked cockily between thrusts. “Dad never rut you this hard?” She upped the pleasure, her horn glowing to pinch Velvet’s nipples and pull her breasts taut. The unicorn squealed, mirroring another of the trapped milfs.

This drew Talvira’s gaze to the plumper Cookie Crumbles, her body engulfed within the slimy body of her daughter. Rarity’s sludge-like form almost acted as a body suit for the pink unicorn, leaving only her mothers’ head just above the surface of her bountiful chest as the encasing liquid jiggled around her nipples and clit. Talvira also noticed a few other things. The first was how Cookie’s legs were already matching Rarity’s in color, meaning the fashionista was absorbing her. The second thing, however, were all the features Rarity bore that were similar to the only alicorn not present in the room. Draconic blue eyes, glittering stars in her mane, and a stronger wellspring of magic than before. She would have to have a word with the unicorn afterwards but, for now, she would just sit back and enjoy the show, as Rarity morphed her hands into equine phalluses and jammed them into her own nethers. The submerged mother cried out in pleasure as the cocks carried through into her own pussy and ass. Talvira grinned as she watched the vulva spread wide, the mares gasping for breath as her daughter pushed deeper and deeper.

A manic giggle from the other side of the room drew the mistress’ gaze, and she witnessed the far more frenzied fucking from Pinkamena Diane Pie. Her mother, Cloudy Quartz, was gasping for air and trying to maintain some shred of composure as she was suspended above the floor by the many tentacle arms of her daughter as she busied herself shoving as many cocks as she could up the earth pony’s cunt. At current count, that number was four, though many others were snaking their way all over the conservative mares’ modest body.

“Oh Mom,” Pinkamena tittered. “You’ve always been wound up sooooooooooooo tight. It’ll be bad for your health if you don’t loosen up.” As she said this, a tentacle began prodding at the spread cheeks of Cloudy’s backside, breaking the focus she had as she looked back over her shoulder at her daughter with fear.

“P-Pinkamena… p-please, stop this at once. It’s… It’s improper.”

“But I just told you to open up. Unless… you want me to break your pooper? Okie dokie lokie!”

The tentacle pulled back a little before it and three others all rammed their way inside her mothers’ asshole. Cloudy screamed loudly as her anal passage was stretched wide, the sound drowning out all the other moans in the chamber as she immediately fell over the edge and into orgasm. Her walls clamped down tightly, serving as all the more motivation that Pinkamena continue the assault.

This left just one group of family fornicating, and Talvira shifted her gaze to the last three participants of this incestuous orgy. The demoness had unfortunately been unable to find Bad Apple’s mother, with Midnight informing her she had passed away when she was a filly. This left the former farmer sharing the loud Windy Whistles with Spectrum Blast. The pegasus mare already looked gone; her wings were fully outstretched and her eyes were rolled up as her daughter’s massive member struggled to fit inside her muff, while Bad Apple’s tentacles held her up for Spectrum and forced her to drink the cider dribbling from the former earth pony’s teats.

“Enjoying the festivities, Posey?” Talvira asked as she briefly took flight to landed beside the bound pegasus atop Cadance’s bosom, the impact forcing out a moan and an audible squirt of milk into the tubes. Posey, her face almost crimson she was blushing so heavily, looked away and merely whimpered. The temptress couldn’t help but chuckle darkly, slowly stroking her rock-hard erection at the sight of the timid milf. With natural smoothness, she draped her arm over Posey’s shoulders and grabbed a handful of yellow titflesh. The contact drew a soft moan, and though she resisted, Talvira could smell the nectar drooling from her captives’ lower lips. “Come now, dear, there’s nothing to be afraid of. Especially when the others are enjoying themselves.”

Looking back up, Posey could see the mother-daughter bonding session before her had advanced. Midnight and Rarity had paired together, and were proceeding to fuck each other. What was more terrifying was that Twilight Velvet was still impaled upon her daughter’s dick, and was now being plunged head first in and out of the slimy cavern. Cookie, meanwhile, was absorbed up to her neck. Still above water, so to speak, she was guided to suckle from one of Midnight’s upper nipples, her eyes a clear sign all resistance was gone.

Elsewhere, Spectrum Blast and Bad Apple had picked up the intensity of their rutting. Windy Whistles was now turned around to face her daughter as Spectrum’s massive cock formed a large bump in Windy’s stomach with each thrust. Bad Apple was getting in on the action now as well; while the pegasus used her cider tanks as a pillow to rest her head, one of the former farmer’s golden tendrils had pushed deep into her anal passage. The poor mare was unleashing such whorish noises, drool and snot streaming down her face alongside her tears before her throat and cheeks bulged. This was the only warning she had before the tentacle re-emerged out of her mouth, jiggling even as Bad Apple kept thrusting. Spectrum laughed cruelly at the sight before bending in and locking lips with her mother, swallowing the tendril’s head in the process.

“Ooo, that looks like fun.” Pinkamena spoke up as she moved closer to the thrones, her mother still writhing in her tentacles. “C’mon, Mom. Let’s give Mrs. Shy a show!”

As the now insectoid pony approached, her pointed legs clicking upon the throne room tiles, Posey found her world engulfed in a red hue. She looked over to see Talvira lifting her up before placing her back down on her back, her bound arms and wings sinking into the princess of love’s cleavage while her head was positioned towards the orgy. Looking back up, the pegasus had an upside-down view of Cloudy Quartz bouncing with each thrust of the multiple lengths fighting for space within her ass. They, combined with the tendrils ploughing into her loins, expanding her belly like the other milf prisoners, though Cloudy’s was growing gradually like a balloon; rounded and growing tauter with each intrusion. As much as she didn’t want to admit it, Posey Shy’s lower lips were burning, leaking their sweet nectar down her thighs and into the cleavage of the exhausted princess of love.

“Pinkamena,” Talvira spoke up, positioning herself before Posey as if she were about to go missionary on that wide yellow ass. “I do believe I’d like a shower, if you would be so kind?”

“Okie dokie, Mistress!” The former party planner chirped with a salute, racketing up the speed of her assault on her mother’s holes whilst flipping her right-side-up with uncanny speed. The moans from the once conservative earth pony were growing both louder and sluttier, as were the moans heard from the other mothers present. Posey’s eyes were glued to Cloudy Quartz, though, as her throat bulged and, like Windy Whistles, a tentacle emerged from her mouth. Her eyes widened as her air flow was cut off, her body twitching as she was bounced by the tendrils within her and the one that had pushed through to the other side. Pinkamena was actively panting, such was the intensity of her thrusts. Any tentacles of hers that weren’t either holding her mother up or grinding against her insides hovered around her in anticipation.

At last, with a euphoric cry echoed by others in the throne room, the insectoid party pony came. Large bulges travelled down their length and into Cloudy, her body spasming as the sudden increase of volume within her triggered an orgasm of her own. Her belly grew so gravid it looked as if she had swallowed a beach ball. Finally, the torrent of semen passed through the longest tentacle and erupted out of her mouth, showering both Posey Shy and Talvira in cum. While the pegasus flinched from the seed raining down upon her, the demoness welcomed the downpour, gently spreading it across her crimson body as her own erection stiffened.

As Pinkamena sat her insectoid abdomen down on the floor and retracted the tendril from her mother’s throat, prompting Cloudy to take stilted breaths of air more resembling raspy gasps, Posey could see through the cum splatters on her glasses that the rest of orgy had joined the party pony in orgasmic bliss. Windy Whistles, Bad Apple and Spectrum Blast were all coated in cum, with the mother bearing a stomach stretched even more taut than the Pie matriarch. Meanwhile, Twilight Velvet looked unconscious as she remained impaled on her daughter’s cock, with alicorn semen that failed to add to the bloating mass in her womb instead streaming down her thighs. Cookie Crumbles had finally disappeared, her head now the only part of her that was visible as it floated in Rarity’s bloated belly; almost as if she were pregnant with it.

Any further observations were stopped when Posey felt a weight press down upon her, and looked back up to see Talvira was now grinding her body against the mare. The semen that drenched them both was rubbed into her coat as the demoness’ breasts encompassed even Posey’s significant bust, while her drenched loins felt the girthy pole of flesh rubbing against her entrance and poking the underside of her boobs.

“Mmm,” Talvira moaned, enjoying the sensations as she looked down at her cum-soaked captive. “You must’ve enjoyed that performance given how wet you are. Right, Mrs. Shy?” Posey, too embarrassed to speak, shook her head and looked away. But all the seed in the world couldn’t hide the blush plastered across the pegasus mothers’ face, nor how her cunt was practically gushing. “You shouldn’t keep these feelings locked away, my dear. It’ll drive you crazy if you do.”

“S-Stop…” The response was so quiet against the backdrop of labored breaths, Talvira had trouble hearing it.

“You’re going to have to speak up, dear.” The fiend leaned in close, pressing their bodies together more tightly as she breathed into Posey’s ear.

“I-I said s-stop!” She blurted out in a panic, her blush only growing in intensity as she scrunched her eyes shut.

“Hm, okay.”

The answer caught Posey by surprise, and her eyes shot open to see Talvira lifting herself back up to her knees. This left many strands of Pinkamena’s semen between the two before they broke apart, and also revealed Talvira’s precum had been added to the mixture on her stomach. The source of said pre was twitching, and when her eyes met Talvira’s, she saw the demoness smirk.

“I’ll stop, on the condition you help me out with your daughter tomorrow. You have my word you won’t be touched until then. If you don’t want to, that’s fine, though I’m unsure Fluttershy would fare better than they have.” At Talvira’s outstretched hand, Posey looked up to see the others were slowly stirring from their incestuous coitus. The other four mothers, well, the three she could see at least, were all well past the point of retaining their sanity, their eyes rolling back into their heads. Despite how uncomfortable it made her, as the mental image of that occurring to her little filly, Posey’s choice was made.

“A-Alright… I’ll… I’ll do it. J-Just, please… don’t make Fluttershy suffer.”

Talvira grinned. “Oh, don’t you worry. Fluttershy’s going to be just fine.”

Fluttershy was struggling.

She was panting in pain, rather than the pleasure that had been plaguing her this past week. In the relative safety of her darkened room, one hand fumbling around at the base of her cock. The wedding veil remained firmly clasped around her member, squeezing tight enough for the length to redden in pain and dig slightly into the tender flesh. Furthermore, while her right hand was desperately clawing at the makeshift cock ring, her left was attempting to massage her balls. She was trying to distract from the pain of her cum being backed up following her treatment in the spa earlier, but all it did was reveal that her churning nutsack had expanded slightly. They now rested around the size of melons, and Fluttershy swore she could hear the semen churning within, just begging to be released.

But the pain only increased when she tried to relieve herself, as she had the previous night. The ring felt tighter while the sensation of a pick being hammered into her urethra immediately froze her in agony and robbed her of her breath. This waxing and waning torture was also robbing her of desperately needed rest. With night having fallen hours ago, she’d already been woken up twice from the pain. Her mind was dizzy with exhaustion and her breathing labored.

I… I want to…

Fluttershy immediately shook her head. She didn’t want to know where that train of thought was going. She hadn’t consciously thought it, which meant either her exhausted mind was beginning to hallucinate…

…Or the voice from earlier that morning had spoken up once more.

“No,” Fluttershy panted, her voice breaking the panting that had filled her room this evening. “I just want this to end.”

Then give in.

Fluttershy suddenly sat up and walked quickly towards the balcony door, hoping the fresh night air could help cool down and sooth the agony her genitals were enduring. But just before reaching the handle, another bolt of suffering raced from her cock throughout her body and brought her to her knees, panting heavily.

Her mind weary and her body fading, she only needed to last one more day.

Fluttershy could only hope she had another day in her.