A Purple Pony's Ponderings on the Hearts and Hooves Day that Might Have Been

by Horndog

Rating: mature
Tags: Romance, Porn, Sex, Fetish, Princess Celestia, Twilight Sparkle, My Little Pony: Friendship is Magic
Length: 3942

Twilight fantasizes about how Hearts and Hooves Day might have gone if she had been brave enough to ask out her crush. These fantasies rapidly turn lewd as she imagines some of the things she'd like to do with her crush.

With the clock nearing midnight at the end of yet another Hearts and Hooves Day where Twilight couldn't muster up the nerve to ask out her crush, she fantasizes about how things could have gone, how she so desperately wanted them to have gone.

Of course, one of the things she really wants to do with the pony of her dreams involves her appreciation of their backside, and boy does Twilight appreciate their backside. She would jump at the opportunity to appreciate it all day long, if only she could work up the courage to ask.

At least she can imagine what things would have been like if she had the courage.

Contains: Fantasies involving the ponut, the worship of the ponut, the rimming of the ponut, the ramming of the ponut, a brief gape of the ponut, self pleasuring of the ponut, and exasperated sappiness.

Published 2023-02-14 09:30:00 UTC
Last updated 2023-02-14 09:30:00 UTC

There is No Wrong Way to Fantasize

One sunny day in Ponyville Canterlot,

Twilight Sparkle stared at the mostly blank page in front of her, chewing on her lower lip in concentration.

She’d already finished the box of chocolates she’d planned on using in her master plan. That same plan that she’d been working on for the past three hundred and sixty-five days since the plan had failed last year. And the year before that too. And the year before that. And every year since she’d learned what Hearts and Hooves Day was as a young filly. As the hour hand neared midnight, she glanced at the empty heart-shaped box.

It really shouldn’t have been this hard to ask out her crush. Sure, the fear of rejection was abjectly terrifying to the point where she’d had to bribe Luna to keep her crush a secret until she could properly ask them to go on a date and it would go perfectly and then they’d have a statistically short courting period because ~~she is~~ they were perfect. For each other. It wasn’t that Twilight felt she was imperfect or too flawed or not attractive or completely inadequate-

Slapping herself with a hoof (but more gently this time and on the other cheek since even an hour later the right one still stung slightly) she admonished herself for falling into the same loop that had occupied the four hours and twenty-seven minutes since she’d had a brilliant idea.

While she hadn’t been able to muster up the courage to ask Princess Celestia out on a date in real life, she could fantasize that her Heart’s and Hooves Day hadn’t been a complete tear fest that had consumed all the ice cream in the freezer and the large box of chocolate covered rose petals. Instead, she could pretend that everything had gone according to plan. And if she wrote it down it’d be that much closer to being real.

One sunny day in Ponyville Canterlot,

The problem was that even though she had been planning this date for most of her life, she couldn’t actually imagine how it would go.

She’d originally been planning this year to invite Celestia to a friendly lunch date at a casual establishment in Ponyville, on the pretenses of a casual lunch affair to discuss friendly things until the time was right to pop the question, but as she thought about it, she quickly scrapped that idea, cause Celestia was definitely smart enough to see right through it and then the first half of the meal would be awkward for her even if she approved of the idea.

Now she was working with the idea that maybe a simple affair in the castle would better suit the occasion. And maybe it would be less suspicious. She’d be trotting behind the elder Princess, following her to a sun room as she complimented her on the beautiful sunrise. Blinking, she realized why she had immediately thought of trotting behind instead of beside her crush. Even in her imagination she stared at the white pony’s plot.

It wasn’t her fault she stared! The big wobbly thing was at eye level for pony’s sake! And the beautiful curtain of pure mana that acted as her tail didn’t hide anything even when it directly covered the naughtier bits, which was a rare thing with the magical flow that made the Sun Princess’s tail float every which way. Physical attraction was a good thing in a relationship anyway.

And stars above was Twilight physically attracted to Celestia. It had taken quite a lot of bribery to keep the Moon Princess quiet about that particular recurring dream.

The one where Twilight worshiped everything back there, including where the sun didn’t shine. Especially where the sun didn’t shine. Though if she was allowed to do the things she’d only dreamed of before, she’d help the Solar Princess’s unlit areas see the sun.

Sneaking a hoof down between her hind legs, she imagined the bigger pony suddenly coming to a stop for some reason as they headed to the sun room for tea. She herself wouldn’t quite stop in time, of course, her head sliding between those jiggling white globes as her snout bumped, no, she’d call out in surprise, allowing her open mouth to nestle around that perfect dark grey ring for a moment as her tongue just touched the puckered hole in the center. And Celestia’s surprise would of course cause it to pucker tightly, the powerful and hot muscle gripping snugly around the tip of her tongue.

Letting out a slight grunt as her hoof grazed her engorged clit, Twilight leaned back in her chair slightly to get better access.

After she stumbled back and apologized profusely, Celestia would wave it off, and make one of her endearing jokes, maybe about not realizing that Twilight was one of the plot-kissing nobles. As they continued walking, Twilight would be able to clearly see the glint of her own saliva on the perfect donut of Celestia’s ponut. The cold air would cause the wet muscle to contract, winking at her as they finished the walk to the sun room.

She’d seen it wink before. When Celestia was particularly frustrated with a stupid question from a reporter or something else was annoying her, she didn’t let it show on her face but her tailhole would tighten in a way that got Twilight from damp to dripping. She was so grateful that Cadence had taught her such effective masking spells when she went through her first heat, or the Princess of the Sun might have caught on to her attraction much earlier than she was ready for.

Wiggling to spread her own plot cheeks so that her tailhole just kissed the cold surface of the chair, she resumed her fantasy.

Once they reached the sun room, she’d pour the tea, and they’d make pleasant conversation on… something. After Celestia finished a biscuit, there would be a crumb left at the corner of her perfect, kissable lips. Lighting her horn, no, reaching forward with her hoof, she’d brush the crumb off. Celestia would look up and their eyes would meet.

It would be a magical moment, the power of love from the infusion of positively charged thaumic energy into the background magical field caused by Hearts and Hooves Day boosting their perception of each other; not that her perception of Celestia needed boosting, but it might help Celestia see her as something other than the wreck of a pony that couldn’t even-

Casting a quick spell to dull the fresh pain in her cheek, Twilight scrunched her face in concentration. This was her fantasy after all, and things would go perfectly if she wanted them to.

And she did want them to.

She needed them to.

Resuming the careful rubbing of her sopping wet folds, she cursed the hard surface of her hoof and its inferiority to the massive, dexterous expanse of Celestia’s tongue. She could only imagine how wonderful the massive muscle would feel as it traced one long path from her clit to her dock. Twilight frowned slightly as she realized Princess Celestia probably wouldn’t be willing to put her tongue anywhere near her dark purple pucker.

If she would though… the thick, powerful muscle relentlessly reamed her rear hole, ravaging it to the point where it was a gaping, sloppy mess, the dark pink interior threatening to become an exterior as a copious helping of the bigger pony’s saliva dribbled out of it. Twilight begging for more in a slurred tone as tears of pleasure dripped from her chin, the bigger pony happily obliging as the long, thick appendage dipped back in, spreading her battered ponut to its limits once more.

Catching herself in the act of forming a magical construct in the shape of a tongue, Twilight fought to get back on track. Celestia wasn’t the kind of pony to just stuff her tongue into the closest hole. She deserved better.

Reaching her hoof forward, she’d brush the crumb from the edge of Celestia’s mouth, the action forming into a caress of her cheek. The Sun Princess would smile in that way that made the unicorn’s heart flutter before thanking her kindly. As they finished tea, the more beautiful pony would invite her to the balcony to -uh, no, hold on- to the garden to enjoy the beautiful day. Of course, she’d accept.

Twilight’s legs clenched together, the rivulets of her arousal pooling on the chair as she imagined the view once Celestia turned around.

Nestled between two perfect white globes, completely unobscured by the ethereal tail rested the object of almost every lewd fantasy she’d ever had.

Admittedly she’d had passing thoughts about other things, most commonly the other tailholes she’d catch glimpses of throughout her day. Or more than glimpses in the case of Rarity, who’s immaculate tail styling was very fashionable and sophisticated, but did a terrible job of hiding her light grey privates. It didn’t help that her perversions were pretty plain to see and just happened to line up with Twilight’s own, the deep wrinkles and seemingly permanent light gape that only grew deeper and bigger as the years passed betraying just how much the fashionista enjoyed testing the limits of her ponut.

Not that Celestia was some anal virgin. Her tailhole wasn’t the destroyed mess that Twilight had caught herself staring at many a time as Rarity worked the sewing machine, but it saw at least consistent use. Probably.

Considering her affinity for them, it shouldn’t have been surprising that Twilight had noticed some things about them. Mostly pertaining to how often and how much they were used for pleasure. When a pony stretched out their sphincter, it gained a certain type of wrinkle that was pretty plain to see for a pony that knew what they were looking for. Even though most of her initial research had been her own ponut and what she had seen of Cadence’s once her brother had started fucking it multiple times a night every night in his bedroom, she’d increased her sample size since then. Watching them through the slightly cracked door had helped her to understand the mechanics of why that specific type of wrinkle developed though, as every time he pounded into their babysitter her hot pink ring was pushed into her body, stretching from an angle it wouldn’t be naturally.

Over the years since then, she had continued to aggregate data from most of the town of Ponyville, though her five friends contributed the most to her findings. She could say for a certainty that Rarity was a complete butt slut, Applejack’s ponut regularly saw action, Pinkie would shove something way too big up there every few weeks though it remained untouched otherwise, and while Dash had done some experimentation long ago, Fluttershy’s had never seen consistent penetration.

Celestia’s ponut matched her own. Nightly administration of something smooth and slick that wouldn’t press it as far in as something like a medial ring. Probably a dildo of some kind, or a basic magical construct.

The transparent golden rod approached the tired princess, her horn glowing as she sought relief at the end of a long day. Laying stomach-down on her satin sheets, the soft hills of her beautiful plot were gently illuminated by the magical construct, the dark ring between them absorbing most of the light, glints of gold reflecting off the lube-covered flesh accentuating every wrinkle.

With a light squelch, the magical construct made contact, Celestia biting her perfect lip as her tailhole at first resisted the intrusion, clenching as it was pressed into her body. Forcing herself to relax, the Sun Goddess let out a heavenly moan as her sphincter opened up just enough that the smooth cylinder spread her wrinkled flesh smooth.

Twilight bit her own lip nearly hard enough to draw blood, her eyes rolling up as she imagined just what a nearly transparent glowing construct would reveal of Celestia’s insides.

Every push deeper revealed another fold of Celestia’s rectum, the deep pink flesh illuminated in soft golden light as she worked to spread her own depths.

Although…

Every push deeper revealed another fold of Celestia’s rectum, the deep pink flesh illuminated in soft velvet light as Twilight worked to spread her lover’s depths.

She might have been jumping ahead a bit with how she glazed over the time between tea and the bedroom scene, but she wasn’t sure how she was going to do that anyway and she was sure that she very much wanted to end their date in the bedroom. Celestia’s of course, hers was a giant mess that only reflected how terrible she was as a po-

Instead of slapping herself again, Twilight simply lifted her hoof from her folds, the denial of pleasure punishment enough.

Celestia of course had her own magical construct ready, this one much larger than the one at her own behind. It was in fact sized perfectly to be the absolute maximum diameter the smaller pony could take. Pressing firmly against Twilight’s back door, the lube making a loud squelch at the force, the dark purple sphincter was forced to stretch millimeter by millimeter to accept the golden rod wide enough to be mistaken as a hoof. Letting out a pleasured cry, Twilight almost lost her concentration on the rod in her mentor’s depths as Celestia’s entered hers, her ring stretched into a thin band around the intruder as the depths of her rectum were ironed smooth by its passing.

Her hoof not enough, Twilight adjusted herself so that her ass was pressed against the back of her chair, her ponut exposed between the seat and backrest. Lighting her horn, she pulled a simple dildo from her closet, not trusting her magic to maintain shape at the crux of her climax. Barely remembering to lube it, she rammed the relatively small object deep into her ass.

Her magic failing, Twilight didn’t want to leave Celestia wanting, so she diligently pressed her muzzle between the globes of her ass, her tongue darting out to lay worship upon the lightly gaped ring of her Goddess.

“Oh, is that how you wish for things to proceed?”

Without another word, the massive magical construct was banished with a pop, leaving Twilight’s poor plothole loose and gaping. Before it even had a chance to try and close, the equivalently sized length of muscle that was Celestia’s tongue rammed in, spearing the smaller mare to the back of her rectum, the tip of the titanic tongue tickling the entrance to her sigmoid bend. And then she withdrew her tongue, the flesh of Twilight’s rectum clinging to the bumpy surface as if it didn’t want to let go, leaving her hole wrecked and sloppy, the mare herself only just able to try to return the favor as she was utterly ruined by her teacher’s tongue.

At this point the dildo was little more than a blur, disappearing fully past her pucker before her magic yanked it back out again. Even with the brutal treatment, it’d never be as good as Celestia’s tongue though, lacking the warmth and the power of the perfect mare it was attached to.

In and out, she did her best to match the movements of her teacher, her comparatively tiny tongue doing its best to stimulate the puckered hole she so adored. With her mouth covering it, she was unable to see the wrinkled surface, but she didn’t need to, her memory of the ridges and valleys across the large hole perfect enough to trace them with exactness.

As she was focusing on doing just that, Celestia pulled her tongue from the purple mare’s rectum, a string of saliva stretching from the muscle to the hole it had wrecked. “Beautiful, almost as beautiful as the mare it’s attached to.”

Twilight frowned, her fantasy falling apart at the unexpected dialog. She was never good at talking, and in the heat of the moment she’d surely mess it up and shout something embarrassing like ‘I love your butthole!’

She did though, it was probably the third most attractive thing about the princess, after her wonderful personality and beautiful face of course. Starting again, she decided to try a different track.

Wiping the crumb from the corner of Celestia’s mouth, a motion that naturally evolved into a gentle caress, Twilight couldn’t help but bask in her mentor’s beauty. Unfortunately for the pair, there was a knock at the door just before she could compliment her on it. Setting her hoof down, Twilight watched as Celestia stood, trotting over to the door. Poking her head out to talk to whoever was interrupting, she left her plot just within the room. With how the sun was shining and the way that her tail decided to blow, this left her onyx ponut in a spotlight, framed by her soft white cheeks on either side and her delicate dock and meaty marehood top and bottom. Still damp from the accidental rimming Twilight had given it earlier, the purple mare could practically hear choirs of angels as the light shimmered off its surface. In a trance, she walked closer until the point of her horn cast a shadow across the pronounced ring. As if sensing the loss of her sun, the ring clenched, puckering beautifully.

“Twilight?”

Caught staring, she looked up into her mentor’s kind eyes. “P-Princess! I was just-“

“Admiring the view. Would you like to have a closer look?” Taking a step back, Celestia brought her ponut back to boop Twilight on the nose, the close view letting her see every single detail as she clenched again.

Bending her neck so that she could keep her gaze firmly on the object of her desire as Celestia repositioned, she gasped as she felt the warmer pony press up against her side. Feeling a huff of air at her own backside, her tail firmly up, she couldn’t help but tear her eyes from the perfect sight of Celestia’s ring to see her mentor stooping down to get a good look at her own sloppy tailhole.

Lifting her view to look at her student in the eyes, Celestia smiled warmly. “You are a beautiful mare, Twilight. Never forget that.”

Twilight grunted, frustrated. Even her fantasies were betraying her now. Instead of letting her just get her rocks off to the image of Celestia’s plot as her own got wrecked by the Princess so she could go to bed, they kept getting derailed with unrealistic dialog that would never happen.

Even if she really wanted it to happen.

Well, if her own subconscious wouldn’t allow her to focus solely on Celestia’s perfect plot, maybe she just needed to lead in by focusing on the other end of perfection first.

Her mane and tail twinkled in the evening light of the garden, her sun working to accentuate her impossible beauty as she smiled down at her student.

“You’re so beautiful, Princess. I love you.”

Celestia smiled her own little smile, the one that she used to hide that she was planning something. “Come, Twilight, there is something I must show you.”

Twilight obediently followed, not worried about the non-reply her mentor had given her. Not at all. Not in the slightest. The view was a decent distraction at least.

Celestia stopped before a large, intricate flower, each petal a swirl of complementary colors distributed in a balanced pattern that emphasized the others perfectly. “This is what I consider the most beautiful flower in my garden, Twilight, but let me tell you a secret.” Gesturing the small mare closer so that she could get a better look, the Princess leaned over and whispered in her ear: “Even at its most beautiful, it’s not even half as beautiful as the mare that stands before me. You are the most beautiful thing to me, because you are beautiful both on the outside and the inside.”

Twilight paused, the dildo stopping halfway in as her brain ground to a halt. “No, you stupid brain! Celestia would never compliment me like that. I don’t deserve it, so stop trying to pretend that-”

With a flash and a bang, a giant white pony teleported into the room, head thrown back in exasperation. “OH, TAKE THE HINT ALREADY!”

“Ce-Ce-CELESTIA!?” Realizing the state she was in, covered in sweat with a dildo hanging out of her plot, she quickly sat up, her rectum swallowing the plastic rod as she crumpled up the nearly empty paper in front of her. “What are you doing here so late?”

Celestia simply rolled her eyes. “Luna may be the Princess of Dreams, but I am the Princess of Daydreams. Year after year I’ve waited patiently for you to work up the courage to ask me to be your special somepony but I’ve waited long enough! Yes, Twilight, I would like to be your special somepony! You are a beautiful mare, both outside and in, and I would love to go on dates with you, and spend our free time together, and I would love to make you smile that smile that lights up an entire room as your boundless enthusiasm works to brighten the day of everypony around you!”

“But I-”

“Your self esteem could use a little work, that is true. I was hoping that bending your daydreams to have your pedestal version of me give you compliments would at least help a little but that’s okay, we can work on that. Together.”

“That was you?”

Celestia nodded. “Of course. I saw a wonderful mare that I adore in pain. Your aggrandization of me and degradation of yourself is doing nothing but hurting you, and I will no longer stand by and watch as the mare that I have feelings for constantly tears herself down through some misguided comparison of her worst qualities and the perfect version of me that I could never hope to match. Though it wouldn’t shock me to discover that you do know every wrinkle of my tailhole by memory, with all the staring you’ve done over the years. I’d be flattered if your weren’t so hard on yourself as a consequence.”

Twilight didn’t know what to say, what to think. Her first and only crush was standing before her, and had revealed that she knew all along. Not only that, but she had revealed that she had feelings in return. Celestia had even called her beautiful in all the ways she had never even dared imagine. All those times that her fantasies had derailed because Celestia had complemented her had been real. Just as the situation started to sink in, she felt herself enveloped by Celestia’s magic.

“Now come here! We can continue this discussion about your mental health tomorrow, but unlike you, I can take a hint.” Yanking the dildo out of Twilight’s ass, she lifted Twilight butt-first into the air and wrapped her lips around the protruding purple ponut with a ferocity that would not be denied, her thick tongue battering through the muscle like a freight train as a fiery hunger lit the Goddess’s eyes.

As Twilight hung suspended, Celestia doing her best to lick her tonsils from the wrong end, tears of joy ran down her face (and fountains of orgasmic pleasure ran down her back legs). Only one minute from midnight, her Hearts and Hooves Day became the best day of her life, better than she could have ever imagined it to be.

Author's Note

It's been a while, but it's good to be back. Hope you enjoyed the silliness.