Bored.

Evening Star was bored.

Glancing at the clock on her nightstand, she rolled her eyes at the time. It was three hours past her bedtime, but she wasn’t tired in the slightest. Convincing her parents of that fact proved far more difficult than she would have liked though. The first time she had gotten out of bed to play with her toys, her dad had seen the light under her door and had chuckled as he told her to go back to bed. The second time she had been smart, using the light of the moon to play by, but Dad had somehow still caught her. Now she was laying on her bed, covers kicked off the end in a huff and not even pouting was fun anymore.

It wasn’t her fault she was sick. Well, had been sick. She’d woken up this morning with a stomachache and feeling like she was going to throw up, but after taking medicine and sleeping all day, she felt better. She felt even better after taking that medicine her parents had argued about, her dad winning with ‘She might as well get used to taking it now, and it might even help’. She hadn’t understood what he meant even as she swallowed the huge pill, her stomach twisting up in a knot before she suddenly felt empty, places she hadn’t known existed suddenly feeling oddly hollow. Only minutes afterword, she was feeling better than ever, though she was a bit hungry. It didn’t matter though; her dad having apparently put magic tripwires all over her room so he would know if she got out of bed.

Though, now that she thought about it, he was a pegasus, so he wouldn’t be able to make magic tripwires. He had said something about Dad Powers before, so maybe he was using something like that. Can a unicorn even make magic tripwires? Star glanced up at her stubby horn questioningly. Furrowing her brow, she decided that yes, unicorns would be able to make magic tripwires. What would be the point of her magic lessons if she wouldn’t be able to make magic tripwires?

Thinking of her lessons made her crinkle her snoot in annoyance. If only her parents were unicorns like her, they could teach her instead of Miss Prim. Her parents were cool, but she was certain that Miss Prim was a villain out of her favorite detective books. Well, no. That would make her cool too. Miss Prim must have just been a regular villain then. It was only because her magic was so cool that she put up with a pony as uncool as Miss Prim.

Unnoticed by the filly, her hoof had begun to trace circles in her fur as she tried to think of a villain name for her magic teacher. She did notice when her hoof traced over an itchy spot just in front of her hip. Scratching the itch, she decided to continue tracing because it felt good.

Thoughts derailed, she thoughtlessly traced over where her cutie mark would be. What would her cutie mark be? She still had a couple of years before she would get hers, but she still liked to think about it. Mom’s was a rolling pin, and it would be cool to make cookies that tasted as good as her mom’s did. Dad’s cutie mark was a pen drawing a star, though she didn’t actually know what he did at work. Maybe he helped design the night sky? That’d be cool. Luna was the best princess after all. Her sister had an olive branch. It was supposed to do with stopping arguments or something, but what that had to do with an olive branch, Star had no idea. Detective Cold Trail had a magnifying glass with two hoof prints in it as her cutie mark, which would be super cool. Spark wished she could be like Detective Cold Trail, the way she had solved the mystery of the stolen sandwich was brilliant! Maybe she could get a cutie mark in detectiving! Detectiving? Whatever. One of those funny hats they wore would be really cool. Tracing it out on her flank, she decided that maybe it wouldn’t be for her. Perhaps a magnifying glass? Drawing the shape in her fur, she decided that she didn’t want to steal her favorite detective’s cutie mark. Maybe a trail of hoofprints? Tracing a line of hoofprints down her flank, her mind wandered, trying to think of something else. As she thought, her hoof continued trailing backwards until it bumped into something, drawing her out of her thoughts.

Looking back, Star realized that her hoof had migrated all the way back to her butt. Pulling her hoof away, she thought for a bit, lightly chewing on the end of her tongue. Deciding that the small shock she had felt when she touched the protruding ring of flesh was a good shock, she lowered her hoof again, gently rubbing the smooth flesh of her butthole. Eyes widening in surprise at the pleasant sensation coming from her back end, she continued to rub the area slowly.

Curiosity getting the better of her, Star decided she needed to get a better feel of things. Lighting up her horn, she gently felt around for her tailhole. Just beneath her dock laid the object of her curiosity, the burnt orange circle providing a nice contrast with her pale-yellow coat. She’d seen tailholes before, being eye level with an adult’s in a busy city meant that they were unavoidable, though they all looked a little different, her observant mind had noticed. Her dad’s was a small ring, looking kind of firm, though she had no idea what the fleshy sack that swung beneath it was about. All she knew was that all the boys had it and all the girls didn’t, though her dad’s was the biggest she’d ever seen. Her mom’s tailhole was way different than Dad’s though. It was big and soft looking, despite having lots of wrinkles. Sometimes, in the morning after her parents had slept in, it even looked a little open, giving Star a little peek inside between the rhythmic twitches that pulled it closed. Her sister’s had started out looking a lot like dad’s but had gone all soft like mom’s since she had started sleeping in their bed again. Her magic teacher’s tailhole was smaller than her mom’s, though it was super wrinkled and tended to hang open when she was lost in thought. She’d also seen a few mares on the street with something on their tailholes, or maybe it was in them, though they walked past too quickly for her to get a good look. There was also that giggling mare at the park who’s tailhole was completely open, dribbling white stuff out of it, though she’d quickly trotted off with a stallion before Star had gotten a better look.

Of all the tailholes she’d seen, she’d never seen her own, or been able to study anypony’s so closely, though she’d never had a real reason to before now. Before, they had simply been the hole under the tail, but now she knew that touching them felt pretty good. Finding her magic had puttered out as she thought, she fired her horn up again, intent on getting a good feel for what was back there.

Pulling her cheeks apart to get a better access, her magic finally stumbled across her petite hole. She was mildly disappointed as she felt a distinct lack of wrinkles, the smooth surface of her bit sized tailhole only interrupted by a small dimple in the middle. Squinting, she clenched, a few small wrinkles appearing as her ring puckered, though she could only hold it for a few seconds before she had to relax. Clenching again, her magic tingled over her now firmer entrance, the sensations even stronger now. After a few more cycles of this, she had an idea. Maybe if she pulled it open, she’d be able to feel inside of it and find something more interesting than the slight tingling of her smooth hole. Focusing her magic, she gripped the edge of her puffy ring, pulling it open, though she didn’t have much luck, the smooth surface and her unskilled magic preventing her from getting a good grip.

In frustration, she abandoned her tailhole for now, spreading her cheeks again to reveal her smooth slit. The tiny line looked nothing like her mom’s puffy slit. It wasn’t even noticeable without pulling her cheeks apart, revealing only a hint of pink. Her mom’s slit poked out proudly, much like all the other mares she’d seen. Guiding her magic along, she traced around them for a minute. While it also felt good, she decided she liked the tinglier feeling that came from her tailhole better. Letting go of her cheek with a soft plaf, she leaned her head back against her pillow, closing her eyes as she used the feedback from her magic and the tingling sensation tracing up her butt to guide the way.

Pressing gently against her protruding ring, she paused. If the tingly feeling of her magic on the outside of her tailhole felt this good, she wondered what the tingly feeling on the inside would feel like.

Changing her approach, she decided that if pulling her tailhole open wasn’t working, maybe she could push it open instead. Forming her magical field into a pointier shape, she pressed it into her waiting ring. Her eyes widened in shock as the tingly, almost buzzing feeling of her magic gently stretched her tailhole, the sensation proving much too good to stop. Slipping the probe a little deeper, she let out a disappointed sigh as her tailhole closed back up after it. She wanted to feel the probe deeper, cause that felt good, but she also wanted to stretch her tailhole open, cause that also felt good. Frowning, she focused her magic, bringing it back to stretch her muscled ring at the same time as she sent it deeper, her probe becoming longer and longer. Reaching her limit, she simply held the magic where it was, the tingling and humming providing enough stimulation for now to her suddenly needy hole. As she held her magic, her thoughts drifted back to the backsides she’d seen.

The only colt her age she’d seen beneath his tail was Roll’s, cause he cut his tail really short, and his sack had looked like it was no bigger than a couple of grapes. She’d seen beneath plenty of adult stallion’s tails, and their sacks came in all shapes and sizes. Some of them even drooped down low, swinging as they walked. As she continued to think, she slowly began to subconsciously increase the size of the magical rod, focusing less on length now and more on girth. Bored with trying to categorize the different sacks she’d seen, her thoughts drifted to her math teacher’s wide hips and how her butt cheeks almost completely hid her small tailhole from view, only giving a small glimpse of the tight hole when she wiped the board, the motion of stepping from side to side causing her soft backside to wobble back and forth. Or her PE teacher’s short cropped tail that did nothing to hide his entire hind end, though the rumor was that he and the math teacher made kissy faces in the teacher’s lounge.

Star froze as a thought rose unbidden in her mind; she wondered if they did things with each other’s tailholes. A mental image of her math teacher smiling as Mr. Trotsky made kissy faces with her tailhole caused her horn to flash brighter. Looking back down her flank to the gentle glow emanating from her hind end, she decided to redouble her magical efforts. Dropping her magic field, she heaved herself onto her hooves, unknowingly facing her rear end directly at her door.

Firing her horn back up again, she formed a pointed cylinder about eight inches long and just under an inch wide, flipping her tail out of the way to give herself better access. Barely holding back a groan, she pressed the shape in, inch after inch sliding into her waiting back door. Just before the end of the tube passed her tailhole, she stopped, her front legs shaking at the intense fullness she felt, the tingling humming feelings in her tailhole stirring an incredible warmth deep in her core. Once she felt sufficiently recovered, she started to increase the girth of the magical rod, the sensation causing her front legs to buckle as her back legs stiffened, thrusting her plot out towards the empty room. Barely holding her concentration, she continued to stretch her poor tailhole, the thin ring straining around something bigger than its original size.

Unknown to her, her bedroom door eased open, the onlooker taking in the sight for a few seconds before sneaking away as quickly as possible to get a camera.

Evening Star was lost to her own little world, the incredible sensation of stretching overwhelming her senses even as images of tailholes flashed through her mind. Pearl wasn’t one of her closest friends, but she really wanted to see why her tailhole was so different from her own. Those soft lines seemed incredibly inviting at the moment, Star reasoning that they would allow something really big to fit, maybe even her hoof if it was slippery enough. Her best friend Chocolate Dip’s unnaturally large tailhole seemed like it would be fun to play with too, or her other best friend Tator Tot’s tailhole, though she’d never actually seen beneath his tail to get a good look at it. Even his little sister’s tiny hole seemed inviting, even though she was a couple of years younger. It might be fun to see just how much she could stretch that tiny tailhole. She wanted to stretch out all of her friends’ tailholes. It could even be a fun new game to see how far they could go. The only other pony she could think to have join the game would be her older sister, though with how stretchy her tailhole looked, she’d easily beat even Pearl.

Star felt a heat building up inside her as she imagined all the different ways she and her friends could work to stretch each other’s tailholes. Her hind end was starting to spasm too, though she wasn’t paying any attention to it as she pushed her magic even further, the cylinder gaining an extra millimeter.

That last millimeter proved to be the last straw, her overstretched tailhole clamping down on the one-and-a-half-inch thick magical rod with enough force to constrict the magic, her horn sputtering sparks as it was strained to its limit by the strength of her clenching backside. With her eyes screwed shut as tightly as they were, she completely missed the flash of a camera just as her tailhole relaxed back to its stretched state, the full inch and a half gape preserved on film for later use.

What felt like both an eternity and not nearly long enough later, Evening Star finally came down from her orgasmic high. Still twitching and shuddering, the young foal collapsed onto her side, gasping for breath. Curious, the filly pulled the magical construct out of her butt, a soft moan escaping her lips as her overstretched tailhole did its best to hold it in, getting pulled along with as the friction gave some final stimulation. With an audible pop, the glowing cylinder was pulled free, her used ring not even trying to close, simply hanging open in a loose loop. She missed the silent cursing from the hallway that lamented the existence of camera flash, too busy looking in awe at the eight-and-a-half by one-and-a-half inch magical rod she had just pulled from her slightly sore butt.

Winking the construct out of existence, the curious filly reached down with a hoof to feel her loose tailhole, though the explorations around her back end proved unsatisfying with the hard end of her hoof.

With a snort, she hopped up, pausing for a second in surprise at how stiff her back legs were. Gently hopping onto the carpet, so as not to make noise, she missed the panicked scrabbling outside her door. Trotting as silently as possible, she edged the door the rest of the way open, darting as quickly as she dared to the bathroom, missing the three ponies holding as still as possible down at the other end of the hall.

Hopping up onto the toilet seat and then the countertop, she presented her rear end to the mirror, hiking her tired tail out of the way to get a better view. What a view it was. Perched just above her slightly trembling and quite wet slit was a yawning cavern still at least an inch across, though it continued to slowly close. Clenching her hind end, she was surprised as a small pink nub launched out of her puffy slit, even as her tailhole barely tightened.

With no warning, the door swung open, Star’s sister slipping in before closing it behind her. Holding up a hoof to shush her younger sister, she leaned in and whispered six words into Star’s ear before slipping back out again.

“Tomorrow night, come to my room.”

Author's Note

Is that a promise of things to come?

Yeah, probably. Not for a little bit at least. I have quite a backlog of stories I'd like to get through first, but there will definitely be An Evening of Sisterly Bonding.