When I Was Your Age...
“You want… What?”
Shining Armor grinned sheepishly as his sister stared at him, her expression nothing if not profoundly puzzled. She greatly admired her brother, and truly cherished every single second she spent with him, but his request was strange enough to steal her attention away from the last of her work that she needed to complete before she could spend her weekend with the brother she oh-so adored.
“Do you have any books on how to pick up a mare?” asked Shining again. Truthfully, Twilight didn’t need him to repeat himself. She knew what he said, but the words just refused to click in her brain. It simply didn’t make any sense.
“Uh… I mean, probably, yes, but…” Twilight tried seriously hard to force some sort of logic into this conversation. “Why?”
“Promise you won't be weird about it?”
“I think you know I can’t do that.”
“Remember that time I caught you and Spike in the tub when you were like six?” Shining smirked at his sister’s ever-growing blush. “And you made me promise not to tell anypony and that you would owe me one?”
Twilight bit her lip, damning her past self’s sexual curiosity.
“Er… Promise. Anything for you, BBBFF,” she sighed. “Just tell me why you need such a book.”
“I’m trying to get laid before I go back home.”
Twilight was about to be very weird about it, but she managed to remember her promise before she let her “what the fuck?” leave her mouth. Instead, she formed a significantly more intelligent, and less weird-about-it, response.
“Like… Actually?” asked Twilight.
“Mh-hm,” said Shining, apparently oblivious to just how wrong the situation was in his sister’s eyes. “There’s this mare I’ve got my eyes on, but I don’t know how to approach her.about… Something more short-term.”
“Well, you see, the first of many problems is—and I suppose this is easy to forget, but—you’re kind of, sort of, a little bit married!”
Shining Armor looked around a bit, confused. He looked at the calendar that Twilight kept on the wall, confirming the date. Friday, May the third.
“Yeah, but… It’s Friday,” said Shining. “Right? It is Friday, isn’t it?”
“Sure, but what does that have to do with anything?” asked Twilight. “You mean to tell me that the day of the week impacts your decision on whether or not you should cheat on your wife?”
“Kinda, yeah. Friday is our Cheat Day.” Twilight tilted her head in confusion. As far as she knew, the term “Cheat Day” referred exclusively to diet plans. Shining couldn’t possibly mean a literal Cheat Day, as in a break from matrimony and fidelity.
Could he?
“So you mean to tell me that you and Cadance just have a day where you can cheat on each other?”
“Well, technically it’s the whole weekend, and technically it’s not cheating.” It occured to Shining that most ponies didn’t truly understand the nature of his marriage, not even his sister. Now was as good of a time as any to properly explain things. “So, Cadance is the Princess of Love, right? And, to maintain her power, she shares her love with as many ponies as possible. Before, that meant flirting and stealing kisses, colts-and-fillies on the playground stuff. But, ever since she and I started dating, that doesn’t work, because she devotes all of her romantic feelings to me. Lust can double as romance in a pinch, so she needs to have sex with as many ponies as she can, as often as she can, to fuel her powers. We talked it over and we agreed that, as long as we have rules and I can do it too, she can fool around with anypony she wants to maintain her power.”
“What the heck kind of sense does that make?!”
“Look, that’s the story she told me. Personally, I think she’s just a major cuckquean. She gets off on it. Every monday after Day Court, she has me give her all the juicy details of who I slept with over the weekend. Sometimes, she gets so hot and bothered that she starts masturbating right in the throne room.” It seemed that Shining Armor had forgotten that he was talking to his sister, and Twilight was so shocked and embarrassed that she could say nothing to stop him. “A lot of the time, she makes me fuck her while I tell her about the other mares. She’s been trying to convince me to invite you to one of our sessions. Something about this counting as a type of friendship.”
At that moment, Shining snapped back to reality, a faint blush flushing his face. While Shining’s cheeks were pink, Twilight’s were blooming bright crimson. It was quiet for a moment, until Twilight slowly stood up and disappeared behind one of her castle’s many bookshelves. She returned a short moment later, clutching a thick, leather-bound book in her magical aura.
“You know, Shiny, I could have gone my entire life without knowing any of the things you just told me,” said Twilight. “And I would have had no regrets. Here’s your book.”
“Sorry, Twily. It’s just really easy to talk to you, I forgot that… Well, in any case, sorry,” Shining sheepishly accepted the book and began reading through it. “How to Pick Up Mares: A Reference Guide. Why do you have this, again?”
“If it is a piece of literature that’s written in a tongue that our feeble pony minds can comprehend, I have a copy,” said Twilight, quite proud.
“Even—”
“Yes. Even whatever it is you were about to ask. Hurry up and study so you can… Do what you’ve gotta do.” Twilight didn’t especially want to imagine her big brother balls-deep in some hot piece of ass, but this conversation was making that rather hard. (Twilight flinched upon the word “hard” penetrating her thoughts, and the word “penetrating” genuinely hurt her head).
“Alright, will do. Sorry to do this, Twily,” said Shining, his eyes glued to a chapter titled “Get That Mare Some Hay” (subtitled “Fillies Love Hay”). “I know we were supposed to spend some time together, and I’d normally be fine not dipping my hoof in the honey pot, so to speak, but there’s this mare that I’ve never seen in Ponyville before, and she’s crazy hot. I can’t miss this opportunity.”
“What did she look like?” sighed Twilight, hoping to help her brother get this over with so she could stop thinking about the nature of his sex life. “I probably know her, I might be some help.”
“She’s got this lime-ish coat, and a platinum blonde kind of mane, with these braided pigtails,” said Shining, failing to control his excitement. “Pigtails are awesome, something to pull on while—”
“Focus, Shiny. Did you see her Cutie Mark?”
“Right, sorry. Uh… I saw her flank for sure, but I wasn’t really looking at her Cutie Mark, if you know what I mean. I think it was a pie?”
Twilight raised her eyebrow sharply. She could only think of one pony in town that even remotely matched Shining’s description, but it couldn’t possibly be who she was thinking of.
“Uh… Shiny? I think you’re describing Applejack’s grandmother.”
Shining Armor recoiled at the idea that he was lusting over anypony’s grandmother, let alone his little sister’s best friend (one of them, anyway). But Shining knew that the mare he had seen couldn’t possibly be Applejack’s grandmother. The mare he saw was hot, and young, and hot, and definitely not a granny.
“She looked younger than me, Twily,” said Shining. “How could that be Applejack’s grandmother?”
“All I know is what you told me, and the pony you just described is the spitting image of Granny Smith.”
“It can’t be! I think I can tell the difference between a chick I want to have sex with and somepony’s grandmother! Like, how could I possibly make that mistake?”
“Look, maybe I’m just forgetting somepony. Maybe they’re from out of town. Maybe somepony got a dyejob,” said Twilight. “We’ll never know until we see her. So, how about we find her and get this over with?”
Shining nodded with a grin, more than a little excited at his future prospects. He had a book on how to seduce a mare, he had a sister helping him find her, now all he needed was the mare herself.
Time to get laid.
Twilight couldn’t believe her eyes. Standing in Ponyville Market, just living life and examining produce, was the mare that Shining had described. While Twilight thought herself to be as straight as a gun barrel, if she put herself into a stallion’s mindset, she could definitely see why Shining was so attracted to her. The mare was gorgeous, with soft features and beautiful orange eyes. For those with less-than-innocent intentions, like Shining, it was also worth noting that the mare had a nice flank, round, but not excessive. It was well-built, firm and round with just a bit of jiggle as she bounced restlessly in place. It didn’t hurt that, occasionally, she’d swish her tail a bit to show off her marehood to any watching stallions who may have been passing by. If she wasn’t in heat yet, she would surely be soon, judging by how she fidgeted and teased the ponies around her. All in all, Twilight couldn’t have set her brother up with a better weekend fling if she used her personal One Night Stand Algorithm (a formula she swears she created for the purposes of scientific curiosity, and not because she was horny and lonely).
There was just one problem with Shining’s choice of mare.
“Holy hell, that’s Granny Smith!” exclaimed Twilight. “But… It can’t be! She’s so young!”
“And hot,” mentioned Shining.
“But she’s supposed to be, like, 98! How is she in her early twenties all of a sudden?!”
“Well, only one way to find out,” said Shining. “Let’s go talk to her!”
Before Twilight could debate, Shining grabbed her tail in his magical aura and all but dragged his sister forward to the object of Shining’s lust. Twilight wanted desperately to grab her notepad and quill, not to mention her equipment for blood work, but she knew every second she wasted gathering materials for research was a second in which Granny Smith could revert to her original state. Twilight decided that she’d just have to rely on her eidetic memory in order to gather as much information as she could.
“Excuse me, miss,” said Shining as they approached. The mare turned, her lips immediately turning up into a smirk. There was a certain hunger in her eyes, the look of a woman who was approaching her estrus cycle and had big plans for it.
“Well, hey there, sailor,” she said, her voice sultry and seductive. “What can I do for you?”
“Granny Smith?” said Twilight cautiously. “Is that you? What happened? You’re so…”
“Young and hot? Sure am! Can’t really say why, and I don’t much care, if I’m being honest,” said Granny Smith with a grin. “Just woke up like this. It feels good! I ain’t feel this spry in years!” She chuckled to herself, looking Shining up and down the way a lion would an antelope. “And, please, sugarcube, call me Mary-Anne. Don’t much feel like anypony’s grandmother.”
“Alright, Mary-Anne… How long have you been this way?” Twilight genuinely had no explanation for this strange phenomenon, and it was causing her no small amount of distress. Her curious, scientific mind refused to let this mystery rest, even for the benefit of letting her brother get his dick wet (scientific curiosity was, in Shining’s experience, the biggest cockblock in Equestria).
“Just since yesterday. Feeling good, thought I’d come out and see the town through young eyes again. It’s like looking at Ponyville for the first time! Speaking of looking at things for the first time…” Mary-Anne turned her attention back to Shining. “This must be the brother you told me about. Shining Armor. Prince of the Crystal Empire.”
“That’s me,” said Shining. He weighed his options: on one hoof, he was currently flirting with somepony’s grandmother. That fact alone should be a boner-killer, but, on the other hoof, the grandmother he was hitting on was, without doubt, the most fuckable grandmother ever. So, in his mind, she was fair game. Time to tap into the teachings of the book his sister had given him. “So, Mary-Anne, I was wondering if you’d let me take you to—”
“Actually, Shining, hate to cut you off, but do you wanna fuck?”
Shining Armor instantly forgot everything he had read, as well as how to do basic things like breathe evenly and speak English.
“I… We… Huh?”
“Pardon my Prench, Prince Armor, but I’ve always wanted to fuck royalty,” said Mary-Anne. “I haven’t had a good dicking since they invented penicilin, and this estrus is gonna kick my ass after however many years of menopause. So… How about a little roll in the hay? Don’t gotta mean nothing. Maybe just help me scratch an itch I can’t quite reach?”
“Well, thanks for the help, Twily,” said Shining, barely able to contain his excitement (and the subsequent erection that came with it). “But don’t wait up!”
“Actually…” Twilight blushed like a tomato in the sun. “Can I… Watch?”
“Uh… Why would you ever want to watch your big brother have sex?”
“It’s not for you. It’s for her.” Twilight buried her face in her hooves, unable to look either Shining or Mary-Anne Smith directly in the eye. “I need to document how her new youth holds under stress, and sex is the perfect chance for that. It’s not perverted. It’s science.”
“Look, I don’t care if you watch, if your friends watch, if the Celestia-damned pope watches,” said Mary-Anne. “I want some dick, and he’s gonna give it to me.” Mary-Anne flagged her tail almost straight up, allowing Shining to glimpse her honeypot as it leaked arousal onto the floor. “Now, y’all better hurry up and get your affairs in order of who’s comin’, cause I ain’t waiting much longer. I might just take that royal scepter in the middle of the market.”
“If you’re sure, Twily,” said Shining. Part of him was concerned for his sister’s obvious discomfort, but equally obvious inablity to refuse. Twilight just needed to understand Granny Mary-Anne Smith’s transformation, and this was the best way to do it. Such was the sacrifices of a scientist, having to step far outside of their comfort zone for the purposes of scientific discovery, and part of Shining Armor sympathized with that.
The other part of him was pumped to get his dick wet.
“I’m sure,” sighed Twilight. “Let’s go.”
Mary-Anne had wasted no time dragging Shining, and, by extension, Twilight to Sweet Apple Acres. Luckily for the three, Applebloom was in school and Applejack and Big Mac were out of town on business. This left them alone in the barn for a few hours, plenty for a literal roll in the hay.
Mary-Anne moved in on Shining like a shark to a dolphin, immediately laying him down onto a bed of hay. She licked her lips as she saw his thick black cock snapping to attention. She swore that stallions weren’t this big when she was younger. Mary-Anne stared at Shining Armor’s perfect cock for just a moment before running her tongue up its length. Shining shuddered with pleasure, pleasure that only increased as Mary-Anne kissed and licked up the length of his shaft.
“Big. Fat. Perfect. Cock,” said Mary-Anne, in between kisses. “I want it. I need it.”
“Perhaps it’s linked to her estrus cycle somehow…” murmured Twilight, staring exclusively at her notepad and trying to pretend as if it wasn’t her brother’s cock being licked beside her. “That would explain her heat…”
Mary-Anne didn’t seem to notice her, which was no doubt due to her focus being devoted on the cock before her. She licked up its length one last time before swirling her tongue across the flat head of Shining’s stallion meat, slurping up the little bead of precum that bubbled out of his cock. She gave Shining a sultry wink before opening her mouth wide and wrapping her lips around Shining’s thick, throbbing hot cock.
Shining let out a groan, which made his sister blush and his new fuckbuddy smile (as best as she could with a massive cock in her mouth, in any case). Mary-Anne slurped up Shining’s cock, pushing her head down until she reached the medial ring, then retreated until only Shining’s head remained in her mouth. She pushed down again, going deeper than before, and developed a slow, steady rhythm of bobbing her head, slurping at his cock until it gave her what she so desperately needed.
“You are really good at this,” moaned Shining. “As the husband of a literal sex goddess, I kinda know my blowjobs, so I can say on good authority that Sweet mother of Celestia, hmf….!”
While Shining was talking, Mary-Anne was working. She popped Shining’s cock out of her mouth for a moment to focus her sights a little lower. She wrapped her lips around one of Shining’s hot, fat balls, churning with cum, which effectively shut down the captain of the Crystal Guard.
“F-fuck, that’s good…” Shining ran his hoof through Mary-Anne’s silver-blonde mane encouragingly. Mary-Anne winked, then slipped Shining’s other nut into her mouth, running her tongue beneath his sack. Shining let out a whinny of delight, and his dick followed with another trickle of pre. Mary-Anne took that as her signal to return to her main objective, and so she firmly but carefully pulled back her head, letting Shining’s fat nuts audibly pop out of her mouth.
“How about we… pick it up a bit?” suggested Mary-Anne. Shining Armor nodded, stroking his cock in preparation. Mary-Anne turned and stooped down, pointing her flank up and towards Shining. She raised her tail, giving Shining Armor a clear shot at her thick, puffy, winking pussy. “Well, your highness? It’s rude to leave a mare waiting.”
Shining Armor scurried to his hooves, ready to claim his prize. He mounted his mare, grabbing her shoulders with his front hooves and keeping her steady. He lined up his cock with Mary-Anne’s dripping, burning cunthole and carefully thrust in.
“Hmmf… That’s the stuff,” moaned Mary-Anne. She pushed her hips back, trying to impale herself as quickly as possible with Shining’s cock. The hot, velvety walls of Mary-Anne’s twat was the perfect home for Shining’s dick, and he moved in immediately. He developed a rhythm of quick, shallow thrusts, slowly tearing into Mary-Anne’s pussy. “Shit, I haven’t been fucked like this since Filthy Rich’s wedding.”
“She can recall the past 70 or so years, so it’s not a time anomaly…” noted Twilight. “Fascinating…”
“You ever fuck your brother, Twilight?” asked Mary-Anne, letting out a moan as Shining thrust a bit deeper. “I know it ain’t exactly seen as moral, but his cock is so good that they’ve gotta make an exception.”
“N-no thank you, I’m fine just watching.”
“More cock for me. Your majesty, would ya mind rutting me a teeny-tiny bit harder? I ain’t made of glass, now.”
Shining didn’t have to hear that twice. He grabbed Mary-Anne by the pigtaills and yanked on them, using them to more forcefully ram his dick into the eldest Apple’s pussy. She squealed with pleasure as Shining fucked her harder and harder, yanking on her hair in time with his thrusts. Shining interpreted every squeal, moan, and gasp as invitation to go harder, which he happily accepted until he was using Mary-Anne’s cunt like a cheap toy.
“Fuck me, Shiny,” groaned Mary-Anne. “Slap my ass, pull my hair, just fuck me hard!”
Shining did as he was told, grabbing both of Mary-Anne’s pigtails with one hoof to free his other, which he used to firmly swat Mary-Anne’s flank. She let out a satisfied moan as Shining’s hoof connected with her Cutie Mark again and again, stinging her ass angry red after a few decisive slaps. This was what she had been missing in her old age: a nice, hard fucking.
Shining suddenly pulled out, with no explanation. Before Mary-Anne could inquire as to why Shining had stopped, she felt herself gripped with his lavender magical aura. Shining gave a mental push, tossing Mary-Anne over onto her back, pinning her to the floor. He grinned, then pulled himself on top of her, letting his cock fall firmly against Mary-Anne’s belly.
“You want it?” he huffed. “Beg for it.”
“Give it to me, Shiny,” purred Mary-Anne. “Fuck me until you fill me up with your hot, sticky cum.”
Shining smirked with satisfaction, then forced his cock into Mary-Anne’s tight entry. Like a wild beast, Shining bucked his hips forcefully, plunging inch after inch of his thick, sturdy cock into his mare. Mary-Anne felt her eyes roll to the back of her head, her tongue loll out of her mouth as Shining gave her the rutting of a lifetime.
“A-and, she… Her physiology is consistent with a younger mare,” said Twilight, now finding it impossible to look at anything but the two ponies fucking in front of her. “Uh… Her physiology is consistent, right? She… feels like a young mare?”
“Fuck yeah, she does,” groaned Shining. “This pussy is tight enough to make Cadance jealous. I might have to bring you back to the Crystal Empire.”
Mary-Anne let out a squeal, clenching around Shining’s cock as she reached her peak. Her pussy squeezed Shining’s cock, attempting to milk it of cum that wasn’t quite ready to make an appearance just yet.
“If t-this is what it likes being with a prince…” moaned Mary-Anne. “I’d l-love to meet a princess. Ooh, fuck!”
Shining leaned forward, nibbling gently on Mary-Anne’s as he fucked her. He nipped at her skin, leaving tiny razor kisses all up her neck and collarbone. He didn’t bite hard, nowhere near what was required to break skin. Just a few nips and nibbles to Mary-Anne’s sensitive body to push her closer to her second orgasm.
A second orgasm that she was approaching faster and faster the more Shining asserted himself over her. Being married to a sex goddess definitely taught the Captain how to care for a mare. It was as if Shining’s cock was custom-made for Mary-Anne’s cunt, his rod filling her every crevice perfectly, like a hoof in a mitten.
“I’m… I’m gonna cum soon,” grunted Shining. “Should I…”
“We don’t pull out ‘round these parts. Y’all better fill my pussy up, now.”
Shining nodded, and changed his position slightly. He sat up, looming over Mary-Anne, and grabbed her hips. He held on tightly as he rammed his length into Mary-Anne, his new grip and angle allowing him to thrust deeper, faster, and, most importantly, harder. Flesh met flesh with an audible slap accompanying every thrust, until Shining felt that familiar feeling in his cock. He doubled his efforts, pounding Mary-Anne harder than he ever had before. She let out another squeal, tightening around her stallion and letting a gush of fluid from her marehood. This time, the added pulsations of tight mare pussy was too much for Shining.
He grunted, his cock all but exploding as he painted Mary-Anne’s insides white. The cum flooded her, filling her up like no stallion had ever managed before. Shining couldn’t be contained, and pulled his cock out, stroking out the last of his cum onto Mary-Anne’s trembling, shaking body. Rope after rope, shot after shot of Shining’s royal spunk erupted from his cock, coating Mary-Anne’s belly, face, and hair.
“Fuck, that was good,” moaned Mary-Anne, lapping up as much of Shining’s tasy jizz as she could.
“Sure was. We need to talk about doing this again. Maybe getting my wife involved,” said Shining. He slowed his stroking, satisfied by his one-pony bukkake of the mare before him.
Unfortunately, Shining forgot that there were actually two mares before him, and made no effort to aim exclusively down.
“Ew! Damn it, Shining!” Twilight trembled, her face glazed with her brother’s hot jizz. She had to keep her eyes closed in order to prevent a particularly large glob from dropping into her eye. She spat out a mouthful of cum from a rogue shot that found its way past her lips, no doubt because she was about to ask a question or make an observation. “You came all over me! It’s in my hair! And I was just reaching a breakthrough on Granny Smith’s age regression!”
“Whoops.” Shining used his magic to disperse the baby batter on his baby sister’s face, sending it splattering onto the floor. “Look on the bright side. At least you still have your… notes…”
Shining looked down at the large number of papers and notepads on the floor, covered in as much semen as Mary-Anne (in some cases, even more). Twilight’s eye twitched at the lost research, the scientific possibilities down the drain due to Shining’s cum (which was a thought that Twilight never wanted to have). Her nostrils flared, but she didn’t shout or cuss or throw a fit. She simply turned and headed for the door.
“Wait, where are you going?” asked Shining.
“Oh, I’m going to the Crystal Empire,” said Twilight, exceedingly calm in her demeanor.
“Uh… Why?”
“Because I’m going to go to your room and fuck your wife.” Twilight grinned an evil grin. “And I’m going to make sure to squirt all over your comics. See ya, BBBFF.”
Twilight teleported away, leaving Shining in the barn with a soft dick and fear in his heart.
“So…” said Mary-Anne, oblivious to the severity of the situation. “Round 2?”
Shining thought of the idea of his wife and baby sister, having hot, nasty lesbian sex in every room in the Crystal Castle, from the throne room to the dining hall, finally ending in his bedroom. He pictured the two mares he cared about most in the world, scissoring and sixty-nineing until one of them, probably Cadance, came all over the other’s face. He pictured Twilight, her hoof playing with her cunt until she let out a spray of love nectar all over his mint-condition Power Ponies #1 collector’s comic. He pictured Cadance, the horny slut she is, licking the comics to taste more of Twilight, either unaware or uncaring that she was actually ruining the comics even more. These mental images made Shining feel like he could never have sex again, let alone go round two right then and there.
Then, he looked down to see Mary-Anne’s twat gushing his cum, and his position changed rather quickly.
“Alright, fine,” sighed Shining. “I’m down.”