Author's Notes:

This chapter was suggested by my Top-Tier Patron Jaybird78, and contains sexual content that includes Femdom, Elderly Fetishism, Bondage, Voyeurism, Masturbation, Edging, Oral (Gumjob), and Bukkake. Reader discretion is advised.

The scene that appeared for the surveilling ponies didn’t look to be from Ponyville, since the setting seemed to be on the roof of some sort of building. However, Twilight would’ve been able to ascertain from the bright neon lighting illuminating the space, as well as the countless lavish buildings seen from atop the structure, that this was likely set in Las Pegasus. Of course, judging by the Princess’ gawked expression, it seemed that the location wasn’t on her mind at that moment. Instead, her and the other two ponies’ eyes were pinned directly on the action happening on top of that locked-off building.

Particularly, the grey-coated stallion who was tied down to a lawn-chair, and wearing absolutely nothing but a ball-gag tied around his muzzle.

The pony was whimpering weakly through his gag as he writhed against his restraints, unable to move much or be noticed by anypony at this height. It was unclear how long he was tied down with his limbs sprawled out so lewdly, but the multiple ropes of cum drizzled all over his body indicated he had been there for quite a while. Despite how spent he may have looked, especially when a good portion of his off-blue mane was matted down with sweat, his cock was still rock-hard and nearly vibrating in need for another bout of release. He may have been letting out some audible whinnies through his ball-gag, but it didn’t seem like the elderly mare standing over him was the least bit worried about getting caught. Instead, the pale green gal carried a dominant smirk over her wrinkly muzzle, which was almost as noticeable as the tight black stockings over her sagging legs.

“NOPE!” shouted Starlight Glimmer as she shot out of her seat, and rushed out of the room without looking back. “Nope, not again!”

Twilight seemed equally as unnerved about what was happening on screen as her student did, especially when she recognized the mare as being Applejack’s relative Auntie Applesauce. However, the Princess was temporarily frozen in shock while hearing that frizzy-maned pony chuckling lowly above the squirming stallion. There were many questions Twilight wanted to ask, but nothing came out of her open mouth as she blinked repeatedly to what she was seeing. Meanwhile, Sunburst had his muzzle tightly pursed shut while heavily blushed, and trying his hardest to conceal his erection.

“Mmmmmm… How ya holdin’ up, Sonny boy~?” jeered Auntie Applesauce in a raspy voice as she leaned in with narrowed eyes, and cackled in delight to the pony’s weak spasms. Even though she didn’t expect him to say much while gagged up, she still grinned devilishly at hearing his muffled groans through that red rubber ball. If it wasn’t for his throbbing cock continuously twitching while coated in previous loads of his cum, she was sure he would’ve passed out from exhaustion already. However, the elderly mare was determined to continue her much-needed lessons on him. “Given’ how many times Ah got you off already, Ah’m surprised at how resilient you really are~”

“....nnnnnnnnnn…” the stallion could only moan in the weakest mew through his restraints, barely able to even turn his head and glance up at the mare holding him hostage. Upon closer inspection, his cutie mark of several luggage bags could be seen adorned on his flank from the side of his lawn-chair. And sprawled out across the ground were various items of clothing from his uniform, indicating that he was likely the bellhop for the building he and Auntie were perched on top of. In fact, if Rainbow Dash were around to see this extremely inappropriate scene unfolding, they would’ve likely recognized him as the bellhop Applesauce flirted with when the pegasus accompanied the Golden Horseshoe Mares a while back.

“But still,” continued the mare as she circled around the pony’s bound position, and got to the front of his seat between his spread-open legs. She licked her wrinkly lips with a hungry groan, and locked her eyes on the bellhop’s blushed face as she said, “After Ah heard all them jokes you’ve been tellin’ your coworkers regardin’ me, you should be glad Ah’m doin’ this instead of just tellin’ your manager. Don’cha think?~”

The bellhop squirmed in his bondage with a dire-sounding whinny, but he didn’t try to answer the elderly gal’s question. His blushed and strained-looking expression may have hinted that he’d rather prefer a chewing out and possible termination by his boss, but his needy groans and throbbing cock gave a much different answer towards Auntie Applesauce. The old mare grinned wickedly wide as she cackled in response, and leaned in to get atop of him in his restraints. “Yeah, that’s what Ah thought, you naughty little colt~”

By that point, Twilight Sparkle had seen enough of that scene to get out of her seat as well. Sunburst was secretly elated that the Princess was leaving him alone in the room, but he didn’t dare make a sound as she exited in a rush. Judging by that heavy blush that practically glowed across her face, it shouldn’t have been surprising that she refrained from even looking back at the stallion during her leave. However, she did pause briefly at the doorway to mutter, “Uhhh… you can turn off that feed any time, Sunburst...”

The lone unicorn nodded his head, but kept his eyes locked onto the scene as Twilight left the room on her own. As soon as he heard the door close shut, Sunburst sighed with a deeply relieved shudder. Even though it was tremendously risky (especially when he recalled what happened last time), he immediately lit up his horn to lock the door so he wouldn’t be disturbed. Since Twilight actually added a small ventilation system in the room since their previous surveillance session last week, the stallion wasn’t too worried about lingering musk as he laid back with his cock fully exposed. Meanwhile, he shivered with a heavy blush as he shamefully began to stroke himself to the action happening on screen. “Oh, man~” he hissed with a strong shiver from his spine to his hind-legs. “T-Talk about lucky…”

“But still,” cooed Auntie Applesauce as she crawled up the chair between the bellhop’s legs, and kept a lustrous grin pointed right at that throbbing cock. As she got in within a couple inches of that rigid shaft, she momentarily paused and flared her nostrils to that rich, heady scent of the stallion’s musk. Due to how many orgasms she made him endure, the ripe aroma was strong enough to make her shiver with a hungry groan. Even though it was clear that she was the one in control, Applesauce used a foreleg to wipe her wrinkly muzzle so he wouldn’t see her drooling a little. “Seein’ that you’ve lasted this long, Ah think it’s safe ta say you learned your lesson by now, haven’t ya?~”

“Nnnnnnghhh!~” The bellhop frantically nodded his head while his eyes were clenched shut. He let out a shaky moan through his gag as he writhed especially hard against his bondage, causing his stallionhood to make a strong throb and spurt out an unexpectedly large glob of precum. The clear, viscous fluid landed right across the bridge of the elderly gal’s sagging snout, but it didn’t seem like Auntie Applesauce minded one bit. Instead, she merely chuckled as she wiped off that string with her hoof, and took her time as she slowly licked up that potent load in anticipation.

“Mmmmm… just the way Momma likes it~” After sighing with a content smirk and re-opening her eyes, Applesauce looked up to the bellhop’s flustered expression and said assuredly, “Well, Ah suppose this last one’ll do the trick to set ya straight. Otherwise, Ah’ll have to extend my stay and make my lessons more thorough~”

While the helpless stallion whinnied through his gag and tried to buck his hips needily, the gal pulled her head back before reaching into her muzzle with her hoof. With Sunburst watching with a heavy blush and a hoof gripped around his cock, he openly moaned out with a shudder the instant he saw Auntie Applesauce pull out her dentures. She carefully placed them aside, and licked her wrinkly lips while her gums could be faintly seen. The bellhop was too pent-up to really focus on the mare’s modification, but Sunburst was absolutely loving it as he tried his hardest to slow down his strokes. “Mmmmnnnnghhhh… Oh Goddess, those gums~”

The unicorn’s cock was throbbing uncontrollably to such a shamefully tantalizing sight, but it was clear the bellhop was closer to orgasm as he squirmed beneath Auntie’s form. The elderly gal then cackled under her breath as she leaned in towards that cock, and took another breath of that musky aroma. “Oh my word… Ah hope you still got enough in ya for a naughty old lady to indulge a bit~”

“Ohhhhhh yeah,” moaned Sunburst faintly as he shuddered between the jerks of his cock, and swallowed some drool while viewing the action privately. “Gi… give it to that old mare~”

While the stallion moaned feebly and tensed up at her very touch, Auntie Applesauce sighed blissfully as she went in and gave the underside of that shaft a long, teasing lap of her tongue. Several spurts of his precum shot out prematurely, landing across her wrinkly face and frizzy mane without any complaint. Instead, the mare just groaned under her breath as she reached to the top of that thick, throbbing cockhead. Instead of taking a moment to marvel at the meaty crown, Applesauce quickly closed her eyes before going in with her mouth wide open. Her lips wrapped around that head tightly, which elicited even more pent-up squeals from the bellhop through his gag.

Sunburst continued to squirm in his seat as he watched the action through his heavy breaths. Even though his own experience with older women was minimal (aside from his time spent with Granny Smith recently), he had received a couple gummers himself to know how amazing it must feel for that stallion. His fur stood on end as he watched that twitching stallionhood being crammed into her vintage muzzle, only imagining how soft and pleasing those gums would feel pressed against his shaft. He didn’t want to blow his load too soon, but his hoof was nearly spasming as he kept jerking himself between his faint and rapid breaths. “Ahhhh...Haaaaahhhhh...Oh, yessss…”

Despite how audible Sunburst’s exhales came out, it was nothing compared to the deep, muffled whinnys that bellowed out through that bellhop’s ball-gag. His eyes were clenched tightly shut as he writhed underneath Auntie Applesauce’s tenacious mouth, and quivered from every disturbingly soft crevice that caressed his throbbing cock. The elderly gal’s gums slid across his pulsating flesh with a firm grip of her jaws, but also with a tantalizing smoothness that made his nerves tingle intensely. And despite her ripe age and feeble appearance, Auntie’s experience shone through clear as day the instant she closed her eyes, and pushed her muzzle even deeper to make his cockhead bulge out against her sagging throat.

“Ohhhhhhhh!!~” Sunburst had to let go of his cock after seeing that move up-close, and left it standing untouched as it teetered dangerously to the point of orgasm. Meanwhile, The bellhop on screen didn’t get the same level of mercy as he was left tensed-up from the actions of Applesauce’s diligent maw. Her head bobbed up and down his cock at a rhythm much faster than expected from most mares her age, but the added tension of her lips and gums ensured that her victim would be left edging like crazy for as long as she pleased. Her muffled groans of pleasure could be heard with each slide of her mouth across his shaft, but the focus was entirely on that poor bellhop as he was left squirming helplessly for that last bout of release.

Sunburst whined out through gritted teeth as he gripped the sides of his chair tightly with both hooves, and twitched from each painful pulsation he felt from his edging cock. He tried as hard as he could to keep from blowing his load too early, but he wasn’t sure how long he could last as he marveled at the sight of such a skilled gal giving that stallion what had to be an unforgettable gummer. He groaned weakly through his clenched muzzle, with his exhales coming out shakily as he struggled to maintain the same level of self-control as that lucky bellhop. Of course, despite his diligence to refrain from stroking, his body convulsed wildly the instant his view of the action gave him the perfect angle when Auntie Applesauce lifted up her saggy hind-legs.

“Nnnnnn…~” The old mare brought back one of her forelegs while continuing to deep-throat her prey, and brought it between her stocking-laden hind-legs to tend to her own arousal. Her marehood may have been concealed under a thick bush of hair as white and frizzy as her mane, but Sunburst still shivered upon seeing how matted it became from her pent-up secretions. He wasn’t able to smell how heavy her musk had to have been through the screen, but he could only imagine how strong it was wafting around for that bellhop as Auntie dug her hoof through her bush and began to rub her aged clit furiously.

The bound stallion moaned out even deeper through his gag, with the strong flares of his nostrils making it clear he could smell that citrusy aroma of the mare’s juices dripping between his tied-up hooves. Meanwhile, Auntie Applesauce was going in deeply enough to not only press her wrinkly muzzle repeatedly against his writhing hips, but to also make his plump balls slap against her chin and further drive him to climax. The bellhop was looking so strained from his budding orgasm, that it was a little surprising he hadn’t bitten off that ball-gag to better moan for her. But alas, much like the countless other orgasms Auntie submitted him to, she took her time as she slobbered over every inch of that cock between her hungry gums. She may have promised to give him a good climax for being so obedient, but she never specified when she would do so~

“Mmmph!~” Just as she felt an especially strong throb of his shaft between her lips, Auntie Applesauce gave it a couple more suckles before pulling back in one go. The stallion moaned out strongly as he felt her let go of his cock with a wet pop, but his torment wasn’t over yet. Instead, the elderly mare used her free hoof to start stroking him vigorously, while simultaneously rubbing at her pussy with the other. As the bellhop squirmed with a heavy blush and an unrelenting whinny through his gag, the vintage gal bent in to leave her muzzle less than an inch from that throbbing, drooling cockhead he possessed. “Mmmmm… I hope you’re ready to give an old lady what she wants~”

“Ooooohhhhh, yes~” moaned Sunburst as he gave up on staying celibate for this viewing, and went right back to stroking his needy cock for a much-needed orgasm. “Yes, I wanna give it to you,” he muttered shamelessly as he shivered in anticipation and locked eyes on her sagging face.

The bellhop wasn’t nearly as legible as the unicorn surveilling on them, but his hearty groan made it clear he was more than willing to cum for her twisted sense of justice. “MmmmNNNNNGHHHH!!!~”

“Ah’ll take that as a yes~” purred Auntie before shuddering with a grin, and wrapping her lips back around that meaty cockhead. However, instead of going back to deep-throating that squirming stallion, her hooves continued to tug that throbbing shaft while her muzzle stayed solely around his leaking crown. With the pleasurable strokes given by her soft and sagging hoof, as well as those firm nibbles her gums gave to the pony’s pulsating ridges around his head, it didn’t take long for the bellhop’s back to arch upward for the last time. His fur was standing on end as he cried out in a strained moan through his ballgag, and succumbed to his body’s impulses when he came powerfully into the elderly gal’s waiting mouth.

Auntie Applesauce moaned audibly over the bellhop’s cries of elation, and savored each throb his cock made as it delivered a massive volley of cum directly into her wrinkly muzzle. Spurt after spurt of his thick, potent load shot repeatedly into her ripe maw, causing her to eagerly start swallowing as much as she could. As her throat could be seen gyrating like a snake’s body beneath her sagging and jiggling skin, her body quivered as she tensed-up from her own budding climax in response.

Between her legs, Auntie Applesauce’s marehood tensed-up tightly around her hoof as she squirted multiple times through her thick bush. Even though most of it just soaked into her frizzy fur to make it dribble out like a full sponge, a couple of her squirts shot out far enough to land on the ground in front of the bellhop’s lawn-chair. Meanwhile, her spine could be seen tingling as she rode her orgasm as tenaciously as she could, while also downing what she could of her stallion’s remaining spunk. Of course, despite her enthusiasm, a couple thick streams of his cum could be seen dripping down the sides of her chin, which further added to her messy and sloppy appearance.

“AAAAAAHHHHHH!!!~” Sunburst tensed up tremendously hard in his seat as his hips arched up, and he gripped his cock with all of his might for his incoming orgasm. His cock was pulsating as hard as he could’ve imagined, and his eyes were locked on that vintage mare’s unforgettably sexy appearance as he felt himself--

“SUNBURST, ARE YOU MASTURBATING?!?”

“NNNNGGGGGHHH!!” Sunburst almost had a heart attack upon hearing Twilight Sparkle’s shrill voice in the room again. Unbenounced to him, the Princess was able to unlock the door from the outside, and re-enter the room just as he was about to cum from what he just watched. Unfortunately, there wasn’t a thing he could do as his body took over, and his mind was frayed to a blank-state in utter shock. While his paling face carried a look of utter dread and panic, his hips bucked repeatedly as his cock spurted a monstrous amount of cum all over his frozen body. Rope after rope of his thick, pent-up seed splattered all over his chest and his face, much to the horror of the shameful stallion who couldn’t even defend himself in such an embarrassing state.

Meanwhile, Twilight Sparkle was standing just a couple feet away by the open doorway, her eyes glued onto her assistant with a look of utter shock and disgust. Her jaw remained firmly planted towards the floor as she gawked at what Sunburst just did, but remained deathly silent during his involuntary moment of release. During that long, pregnant bout of awkward silence between the two, neither of them seemed to notice the screen dissipate within the magic orb. Instead, a minute or two passed as the Princess tried to ascertain what to do, and Sunburst slowly crept into a fetal stance while doused in his baby-batter.

“... Uuuuuuuuhhhhhhh…” The stallion looked utterly petrified, and could only let out that Belcher-esque noise as a response to his actions. He looked absolutely mortified as he stared up at the shocked Alicorn, knowing that nothing he could say would adequately explain this in a good way. It was bad enough to be caught jerking off by a mare, but to be caught by a Royal mare was a whole new level of terrifying for the unicorn. Not to mention, his heart was racing pure terror as he realized that Twilight Sparkle, much like her brother, now knew of his elderly fetish in possibly the worst way imaginable.

There were probably a million statements rushing through his head, ranging from horrible excuses to heartfelt apologies. He even considered begging to the Princess for forgiveness, just to ensure that he wouldn’t be killed (or worse, outed) for what he just did in her castle. But instead, while Twilight Sparkle remained silent in shock and awe, Sunburst was able to meekly speak after taking the weakest breath.

“... ummmm… I… I promise I’ll clean up…”

Needless to say, the three ponies’ planned viewing night was promptly ruined.