“I know you were so hesitant when I found you earlier, but I think you’re really going to love it here, Moondancer.”

Midnight Sparkle explained smugly as she wandered through the moan-filled halls of the castle, a deliberate bounce in each step. This was to the poor Moondancer was continually bouncing on the alicorn cock currently stuffing her muff. Much like Fluttershy earlier in the day, her hands were chained behind Midnight’s back and her head buried within four huge purple boobs. Said head tried shaking side to side, but barely moved an inch in either direction. All throughout the journey, the unicorn’s muffled protests and moans sounded out, rumbling and creating delightful vibrations within Midnight’s bosom.

“Oh, I know,” Midnight carried on, pretending her old friends’ muffled cries for mercy were a legitimate conversation. “And I feel the mistress will like you too. Though, fair warning…” With that, Midnight uneasily opened the door. “She’s not in the best mood right now.”

“That fucking bitch!”

Talvira had not moved from her place upon her throne of Celestia’s bosom. Surrounding the boobs of Celestia were the exhausted milfs of the demoness’ harem, demonic seed seeping out of their worn cunts. The only one still making any noise was Lyra, whose pussy was being ploughed by Talvira’s cock as she shared moan-filled kisses with the passive Celestia. The princess, much like her sorrowful and gagged niece Cadance, had their breasts connected to maroon tentacles, their creamy bounty being sucked up into the tendrils that disappeared into the ceiling.

“I should never have made this stupid challenge,” the demoness continued to vent, punctuating each statement with another powerful thrust into the mint-green unicorn. “I should’ve just rutted her on the spot. Now that resilient slut is that much closer to winning! Dam her pure heart to Tartarus!” With that angry roar, Talvira came, buckets of sperm flooding into Lyra’s honeypot before spilling out into the cleavage of the sun princess.

“Mistress? May I join you?”

Talvira looked up to see Midnight standing there, looking as nervous as a corrupted alicorn could while a mare writhed on her cock and between her breasts. With a sigh, the demoness pulled out of Lyra and shoved her up to her waist into the alabaster cleavage they stood over, Celestia immediately lapping at the jizz still spilling out of the unicorn’s cunt. Talvira then sat down facing her apprentice.

“My apologies. I’m just still frustrated about earlier.” She rested her chin in her palm as she dejectedly looked out at the darkening sky above Canterlot.

“Mistress,” Midnight began, clambering onto Cadances’ bust while finally pulling Moondancers’ head out of her own cleavage. “You need to calm down. I know how much you wish to break her, but Fluttershy was able to resist Discord’s temptations after all. Are you sure what you did today wasn’t going too far?”

“The agreement was that I was barred from laying a hand on Fluttershy,” Talvira explained morosely. “My magic was never a part of the deal, as I explained to her whilst you were being broken in. As such, I can use it on her as long as it’s not in an intrusive way. Like this, for example.” The fiend’s horns shone with the crimson aura of her magic. A moan sounded out as Midnight looked over to see Celestia squirming in her bindings, a large magical cock now pounding her pussy.

“Even so…” Midnight responded, repositioning Moondancer to be nose to nose with the tearful Cadance as Midnight resumed fucking her. As she did so, the corrupted alicorn grinned cruelly. “I know this can’t make up for her refusal earlier, but hopefully this will put a smile on your face.” The former princess of friendship stretched her hand out backwards and a portal appeared. Through it, Talvira could see into Fluttershys’ room, the pegasus slowly stirring after her rough treatment hours earlier.

“Before leaving her room, I placed a special glyph within it, and designed it to activate when she next woke up,” Midnight explained, her fucking of Moondancer picking up pace as her sadistic grin widened. “She’ll soon discover the joys of our ways all on her own.”

At this explanation, Talvira too grinned, her eyes glued to the show that was about to begin.

Fluttershy stirred from unconsciousness in a familiar weary state, the back of her mouth tasting like milk. Pushing herself onto her hands and knees in a fatigued manner, she found herself back in her room once again. But unlike every other awakening she’d had this week, there were no lingering erotic nightmares, and the sky outside seemed a lot darker than usual. As she crawled to the edge of the bed and sat down, her senses starting to return to normal, she noticed her skin was no longer hyper sensitive.

Thank goodness, she sighed in relief. I’d be in a lot of trouble if that were permanent.

Looking down, Fluttershy silently wished that wasn’t the only thing that had disappeared. Her thighs remained plush, and her cock still remained, even though it was now flaccid for the first time she could recall. As she was about to look up, something different about her body caught her eye.

Milk was escaping from her nipples.

“W-What?” Fluttershy stuttered, gently pressing her hands on the undersides of her boobs. While not looking any bigger, they definitely felt tighter, fuller. Confusion ran riot for a moment in Fluttershy’s mind as she brought a hand to her neck. But the bell collar wasn’t there. It hadn’t been since she threw it off the balcony a few days ago. It wasn’t until she felt the taste of milk still in her throat from before that it hit her.

“Cadance…” Fluttershy realised. Drinking from her breasts was the only thing that could have caused this. At least, the only thing she could think of.

As this thought hit her, she looked back at her leaking nub. She still tasted the milk from her suckling earlier, and that same lull state was beginning to creep back into her mind. In a trance of sorts, she lifted her left breast up, as high as she could, her outstretched tongue missing it by less than an inch. She let the breast go, a “Mmf” escaping her mouth as it slapped back against her torso. Fluttershy gripped her boobs tighter now, feeling the flesh roll over her fingers as she massaged her chest. Her hands grew wet with milk as they brushed over her nipples. Bringing one hand up, she licked up all of her own lactation, and found the taste as creamy and delicious as Cadances’ had been.

Multiple warm spots ached from her lower body, and Fluttershy now reached down past her ball sack to find her pussy was as wet as her nipples, and her cock was once again standing at full mast. She soon repositioned herself; her head and breasts pressed down against the bed while she stood bent over the side of the bed. Her hands found their way up to her delectably large derriere, and soon started groping her own ass. Her moans slowly increased in frequency as one hand passed below her tail and started circling her pucker with a finger. For a few moments she seemed content, but without warning she drove a finger into her asshole.

“Aaaaah!” Fluttershy cried out in pleasure. Her asshole felt somewhat looser than she was expecting, whatever that may have been. But given the pounding it had taken both the previous day and earlier on this one, it came as no surprise as she then added a second finger in her back door. Her other hand slid down around to her front, closing in on her stiff cock. At full length, it was only a few inches off the floor, and her hand soon wrapped around the meat pole and began stroking. Slowly at first, but as she added a third finger up her butt, her pace began to quicken.

“Mmf, uh, ah, ungh!” Fluttershy moaned as she fell to her knees, leaning back to a kneeling position. She bounced on the fingers up her ass, while she jerked herself off faster and faster. The room was filling with her panting voice, and her bouncing breasts flung the milk still dribbling out of her all over her bed. Within her mind, Fluttershy was screaming at herself to stop, that this was exactly what Talvira wanted. But there was another voice, one that had started quiet but was growing louder with each stroke. It whispered in her ear;

Join us.

That voice snapped Fluttershy back to her senses, but it was too late, as she came in a crescendo of noise and fluids. Her breasts and pussy squirted their respective liquids, her ass clenched tightly around her fingers, and her dick erupted in an explosion of semen. Her mind blanked for a moment or two before her focus returned and her fluids died down. She looked down in dismay at the streams of milk rolling down the underside of her boobs and onto her stomach, the pussy juices that were smeared across her thighs and the underside of her nuts, and the strings of cum that connected Fluttershy’s still-twitching dick to the mess that now decorated the sheets of her bed.

A flicker of movement caught Fluttershy’s eye, and she turned slowly to see her reflection in the balcony window door. The sight of her in such a compromising position brought a blush of shame to her face, and she wiped her hands on the carpet as best she could before bringing them to her rapidly watering eyes. As she cried herself to sleep on the floor rather than her bed, one thought ran through her mind.

Why did it feel so good?

“M-Mistress,” Midnight panted. “Did-Did that, ungh! P-Please you?”

Talvira’s only response was to grin and piston her hips faster, her demonic cock fitting snugly within the alicorn’s cunt. The two laid atop Celestia’s bosom as they fucked each other during their act of voyeurism. The fact that Moondancer was still impaled on Midnight’s cock and now smothered between six incredibly large boobs, pressed between both paragons of corruption, only heightened the pleasure for the demoness.

“Indeed,” Talvira answered in between thrusts. “You’ve done well. Fluttershy is closer to falling than we thought.”

“C-Close, hah, ungh, I’m, I’m close.” Midnight let her head fall back onto the pillowy boobs they fucked upon, her eyes rolling up from the pleasure of her mistress. “I’m close. I’m cumming! Cumming!”

“Let me help you with that.”

Talvira leant down and took the two top nipples of Midnight’s quad-boobs in her mouth at once, her teeth biting down on the dark purple nubs. The alicorn squealed as this accelerated her climax. Her pussy clenched tight around Talvira’s cock, milking out her precious seed as her own now flooded into Moondancer’s virgin muff. The demoness pulled out and looked upon her apprentice. Midnight was exhausted, panting with an almost drunk expression on her face. Moondancer, however, was fucked unconscious, her belly swelling with semen as Midnight kept on filling it. The fiend sidled up alongside Midnight and took her in a tender kiss, one the alicorn eagerly leapt into despite her fatigue. Their tongues danced together as they swapped spit before Talvira pulled away to look her junior in the eye.

“I couldn’t have asked for a better apprentice,” Talvira murmured sweetly as she stroked Midnight’s cheek. “Would you do anything for me, Midnight?”

“Y-Yes, mistress.” Midnight answered immediately. “Anything, anything you ask.”

“Good.” The demoness stood up, waling over and using the compliant Celestia’s tongue to clean her cock before flittering off of the boob throne and onto the floor. “Because I have an assignment for you.”

“Of course, mistress.” Midnight slowly got up, finally pulling out of the poor unicorn before slowly clambering off her former teacher to join her new one.

“I shall be taking your advice and stepping back from Fluttershy for a little while.”

“What?” Midnight’s outburst merely brought an amused smile to Talvira’s lips as she held up a hand before carrying on.

“I would hate to have come this close to success and then ruin it by overstepping my bounds. Therefore, I’ll be heading to Manehatten for tomorrow. Apparently, there’s a rather pesky resistance cell there, and I’d like to make an example of them. As for Fluttershy, I’ll leave her trial tomorrow in your capable hands. And if she decides to wear that accursed veil again,” her expression darkened. “Make her pay for it. Do you think you can handle that, Midnight?”

Midnight’s expression morphed from curious, to shocked, before finally settling on maliciously excited. “Oh, trust me mistress, I have some ideas. I’ll do my best to break her for your return.” She gave a regal bow before the fiend, while her magic collected the unconscious Moondancer and brought her over.

“Thank you, Midnight.” Talvira smiled brightly as she turned for her room, her apprentice and the unicorn falling into step behind her.

Author's Note

Getting close to the end now, and things are getting interesting. I know this chapter's a little short, but considering everything that happened during the day, hopefully that's forgivable.
On to the votes. I had a feeling Cadance and Celestia would win, but I was blown away by how much of a landslide victory it was for them. The night ended up being very close, but Fluttershy's little solo session just edged out Midnight. And as for the items, I think maybe I made a mistake in revealing the negative modifier for the wedding veil, as it may've skewed the polls that way. Either that, or there's a lot more of you that wanted Fluttershy to win than I thought.
Previous Poll Results
Day:
Royal Spa: 3
Pillory: 2
Cadance & Celestia: 25
Night:
Fluttershy: 11
Mothers: 9
Midnight: 10
Item:
Replace Wedding Veil with Nipple Tassels: 10
Replace Wedding Veil with Servant: 2
Replace Wedding Veil with Emblem of Power: 4
Keep Wedding Veil: 14
And now the new poll. Do bear in mind this poll contains the last night option for the challenge, as the last day will just have the day and item options. With that out of the way, the options;
Day:
Royal Spa
Mane 6
Night:
Mothers
Fluttershy
Item:
Replace Wedding Veil with Servant
Replace Wedding Veil with Nipple Tassels
Replace Wedding Veil with Emblem of Power
Keep Wedding Veil

Thank you for reading up to this point, and happy voting!