An Evening of Discovery

Chapters

Version A
Version B
Version C

Version A

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 can’t have an upset stomach if there isn’t anything in there to be upset with’. She hadn’t understood what he meant until she had managed to swallow 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 disgust. 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.

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. 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 grabbed the small mirror she practiced her ‘Thinking Look’ in off her nightstand, rearranging one of her pillows to prop it up at her other end. Flopping back down onto her side, she looked at her hind end, illuminated in the bright light of the full moon, the streetlamp just outside helping provide plenty of light for the curious filly. 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 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 her parents were quick to shoo her in the other direction when she saw one of them, preventing her from getting a closer 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 hoof gently rubbing it again as she thought, she pulled her hoof away to get a better look, though the sudden image of that cab driver’s sack bouncing as he trotted brought her hoof right back, the mental picture somehow making it feel better.

Berating herself, Star pulled away again. This new sensation would be fully investigated, but later. First, she wanted to get a good look. Pulling her cheeks apart to get a better angle she looked at her petite hole. She was mildly disappointed at the near 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, she gently rubbed 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 look into it like she could her mom’s or that mare at the park’s. using the tip of a hoof, she gripped the edge of her puffy ring, pulling it open, though she didn’t have much luck, the barest hint of pink barely visible in the middle. Letting go, the stretchy ring snapped back to its original shape as she frowned, disappointed by her visual investigation’s lack of anything interesting. Maybe she could get a closer look at her mom’s. The bigger size, almost as big as her hoof, would certainly lend itself to better results.

Looking across the rest of her backside, she spread her cheeks again, revealing 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. Reaching between her legs with her other hoof, she traced along them. 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, ignoring the boring sight beneath her tail in favor of the exciting feelings that came from touching it instead.

Rubbing gently against her protruding ring, she zoned out again, thinking back to all the tailholes she’d ever seen. She hadn’t seen too much of her classmate’s back ends, being out of her line of sight. The ones she had seen looked much like hers, except for maybe Pearl’s. Pearl’s tailhole was more like Miss Prim’s, all wrinkly and loose. Now that she thought about it, Pearl’s tailhole hadn’t been like that last year. Something had happened over the summer, though Star didn’t have any idea what. Maybe she’d ask her tomorrow at school. Remembering how exciting the thought of the cab driver’s sack had been, she tried to remember what the colts in her class looked like beneath their tails. The only tail she’d ever seen beneath was Roll’s though, and his sack had looked like it was no bigger than a couple of grapes. As she continued to think, she also continued to rub her tailhole, her ponderous movements gradually evolving into purposeful strokes as she figured out what felt best. 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 kissed each other’s tailholes. Looking back down to the mirror at her own ring of soft skin, she wondered what it would feel like to have somepony kiss her tailhole. If her hard, but smooth, hoof felt this good, how good would a soft pair of lips feel? It didn’t make any sense that somepony would even want to kiss her there, but kissing didn’t make any sense in the first place, and adults did that all the time? Did her parents ever kiss each other’s tailholes? They did a lot of kissing, and she’d never seen it, but then again, they did kick her out of the bedroom when they got really kissy, so maybe it was something you did in private. You’d have to be clean too, else it would just be really icky, but the pill her parents had made her take was apparently supposed to make everything back there super clean, she read the bottle. Maybe she could take a couple of those pills to school with her so that she and her friends could try things out.

The sudden desire to share this amazing feeling she was experiencing with her friends got her out of her stupor, her hoof resuming its rubbing at a frantic pace. 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, just begging to be kissed, to more accurately determine their texture of course. Kissing was gross. Kissing her best friend Chocolate Dip’s unnaturally large tailhole seemed fun though, or her other best friend Tator Tot’s tailhole, though his balls might be fun too. She’d never actually seen them though. Even his little sister’s tiny hole seemed inviting, even though she was a couple of years younger. Chocolate’s older sister had a coltfriend though, and he might not like Star kissing her, even if it wasn’t on the lips. If they laid down just right, they could all kiss each other’s tailholes at the same time and all feel good all at once.

Star felt a heat building up inside her as she imagined all the different ways she and her friends could kiss each other’s tailholes. Her hind end was starting to spasm too, though she wasn’t paying any attention to the mirror as her back legs twitched and kicked. Her hoof kept rubbing against her twitching ring as fast as she could move it, leaving her gasping for breath as sweat dripped off of her onto her sheets. As she was trying to figure out a clever way to not only convince her two best friends to kiss each other’s tailholes, but also to find a way to include Pearl in the whole ordeal, she peaked.

Suddenly, her lower half went from feeling very good, to feeling very good, her holes clamping down on themselves as her entire body shook and shuddered. Several squirts shot from her trembling slit, coating the mirror in sticky goo, her flailing and gasping causing her to quietly cry out even as she only saw white. Coming down from her unexpected high, she simply lay there, trembling and panting, completely worn out from the best thing she had ever felt. Finally finding her strength, she inspected the mess she had made on the mirror, deciding that it was something that she’d have to investigate later, for now finding an inconspicuous corner of her bedsheets to wipe it off with. Replacing her mirror on her nightstand, she glanced at the clock, shocked to find that an hour and a half had passed. Just as she was pulling her blankets up over her from the bottom of the bed, she heard hoofsteps in the hallway, giving her just enough time to throw her blankets over herself and close her eyes.

Opening the door, Dad peered in, seeing his precious daughter wrapped up in her blankets, completely still. Shaking his head at the obvious attempt at faking sleep, he closed the door, completely missing the reason she was still up as he eagerly anticipated the night he had planned with his wife.

As soon as the door had closed, Evening Star opened her eyes again, though she really was feeling tired now.

I have to show that too my friends! Tailholes are the Best. Things. Ever!

Author's Note

I decided to try something a little different this time, going for a shorter, more concise story. To keep things even though, I made three versions instead of the standard two. You'll have to tell me if you like it better this way or not. It's about the same to write, (ignore the giant gap between this story and the last, that was just real life getting in the way of ponuts) so I may do it more in the future. Really it's just whatever fits the story better, though if you guys really like it, I could lean more towards the shorter trio than the longer duo. Anyway, hope you enjoyed the first chapter. You should try the others, they're pretty good too.

Version B

Author's Note

This is the same general story as the first chapter, a filly discovering the magic of the hole just beneath her tail, but this time with some penetration. Also, the family would seem to be a bit bigger and kinkier this time around...

Version B

Bored.

Evening Star was bored.

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.

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.

Curiosity getting the better of her, Star grabbed the small mirror she practiced her ‘Thinking Look’ in off her nightstand, rearranging one of her pillows to prop it up at her other end. Flopping back down onto her side, she looked at her hind end, illuminated in the bright light of the full moon, the streetlamp just outside helping provide plenty of light for the curious filly. 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 the summer before she got her cutie mark. Maybe how soft and wrinkly it was had something to do with cutie marks? Dad had his cutie mark though, so maybe not. 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 her parents were quick to shoo her in the other direction when she saw one of them, preventing her from getting a closer 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.

Rubbing gently against her protruding ring, she paused. If rubbing the outside of her tailhole felt like this, she wondered what rubbing the inside felt like.

Looking back at the mirror, she wondered what could possibly fit inside. Her hoof sure wouldn’t fit, though it might fit in her mom’s, maybe even her sister’s. Glancing around, she didn’t have to look far, though the object she found filled her with loathing.

Her brush.

Suggested by her villainous magic teacher, the simple brush was designed for unicorns, the handle being a small, smooth, thin and slippery thing made of brass. Not only was it too small to grip in a hoof, it was too thin and slippery to grip in her mouth, forcing her to use her magic to hold it. And it tasted terrible, as anything brass does. For what she had planned for it, though, it was perfect. Gently picking it up with her hooves so the surprisingly (agonizingly) heavy brush wouldn’t make any noise, she inspected the handle. At about five and a half inches long, and just over half an inch wide, the main handle would probably fit fine, though the one inch bulb that sat just before the mirror itself probably wouldn’t fit in the tiny dimple she saw in the mirror.

Finishing her examinations, she rolled onto her back, propping her head up with some pillows so she could still see the mirror. Carefully bringing the brush down to her back end between her hooves, she lined the end of the handle up with the small hole at the center of her tailhole, pressing it in slowly despite the small shock of cold handle on warm flesh. To her annoyance, it stopped moving before it even made it in, the skin of her ring clinging tightly to the dry handle. Pulling it back, she thought for a moment, trying out her best thinking face. Maybe if it was wet, it would slide in better. Looking around, Star once again spotted her answer on the nightstand. In a little plastic jar was some off-brand petroleum jelly, her dad leaving it behind when he put her to bed the first time. Maybe it would be slippery enough. Struggling for a moment, she was forced to use her magic to get it open, hoping the light wasn’t enough to alert her dad again. As soon as she made sure she didn’t hear hoofsteps, she leaned down, sniffing the odorless jar. Setting it next to her on the bed, she picked up the brush again, dipping the handle into the jar and swirling it around until there was a good-sized glob on it.

Bringing the brush handle back into position, Star took a deep breath, preparing herself for what would surely work this time. Pressing forward once again, a sudden shiver brought by the cold caused her to press past her ring much faster than she was planning, the sudden sensation bringing a rush of pleasure she wasn’t expecting. Looking at the mirror, almost an inch had slipped in. Squeezing her back end like before, it felt like the tip of the handle was sitting just behind her tailhole now. Wiggling the brush, she marveled at the sensations coming from her previously unexplored depths, the slowly warming handle enhancing the feeling into something wonderful. Biting her lip, filled with purpose, she pressed on, the slight friction of the handle providing a pleasant backdrop to the sensation of the tip of the handle making its way deeper within her. As the handle passed the halfway point, Star stopped once again, wiggling the handle some more and almost giggling at the warm tickling feeling, though the more she did it, the less it tickled and the more it left behind an amazing warmth. Deciding that if half the handle felt good then the whole handle would feel better, she stopped wiggling to once again press on. All too soon, the bulb at the end of the handle pressed against her tailhole.

Star was just about to start wiggling the brush again when she remembered something. The thought of the cab driver’s sack had been really exciting to her, making just rubbing her tailhole feel better. If thinking of these things she wasn’t supposed to be looking at made her hoof feel better, how good would it make the handle feel when it already felt this good? Thinking hard, she tried to remember what the colts in her class looked like beneath their tails. The only tail she’d ever seen beneath was Roll’s though, and his sack had looked like it was no bigger than a couple of grapes. As she continued to think, she slowly drew the handle back out again, wanting to feel it sliding back in again, though her ponderous movements slowly turned to purposeful thrusts as she learned what felt better. Establishing a rhythm, 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 put things in each other’s tailholes. Looking back down to the mirror at her own parted ring of soft skin, she wondered what it would feel like to have somepony else put something in there. It had felt kinda tickly at first and she knew that she could never tickle herself as good as her dad did, so how much more intense would it feel with someone else in control? She’d have to try that out, and her friends would surely like to know about something so awesome, so maybe they could try it out together.

The sudden desire to share this amazing feeling she was experiencing with her friends got her out of her stupor, the handle being shoved in and out at a frantic pace now. 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 fit in that tiny tailhole, maybe they could do stretches to make it fit more. Maybe all her friends could do stretches, herself too. It could be a fun new game to see how much they could fit. 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 the mirror as her back legs twitched and kicked. Her hooves kept moving the brush as fast as she could move it, leaving her gasping for breath as sweat dripped off of her onto her sheets. Stopping just before her hoof cramped, she started wiggling it as deep inside of her as she could instead. She gasped out loud as the tip brushed against something inside of her, the feeling almost overwhelming her senses. Frustratingly it felt like it was just brushing the very edge of the sensitive spot, if only she could push a little bit deeper-

With a pop, the wave of pleasure came crashing down. The feeling of the tip finally rubbing against the sensitive spot as the bulb at the end of the handle that she was sure would never fit stretched past her ring so perfectly, her eyes going wide at that moment allowing her to see her soft ring stretched thin around the widest part of the bulb before snapping back behind it caused her to let out a loud squeaky moan. In a panic, she threw the covers over herself, trying to hold her twitching hind end still as her hole continued to spasm on the hard metal handle, the added stimulation of quickly moving around with it still in not helping.

Opening the door, Dad peered in, seeing his precious daughter wrapped up in her blankets, trembling slightly. Smiling knowingly at what he thought might have happened, he closed the door. Making his way back to his bedroom, he stepped aside as his daughter opened the door, finally recovered enough to head to the bathroom for cleanup.

As soon as the door had closed, Evening Star opened her eyes again, amazed that she hadn't been caught even as she had a brush handle stuck up her butt. Carefully pulling the sheets back, she fought back another moan as she pulled the brush back out, the bulb stubbornly refusing to leave her clenching ring until she relaxed enough. Completely forgetting about the Dad magic trip wires, she hopped out of bed, cleaning the petroleum jelly off the handle as best she could on the carpet under her bed. Deciding that it wasn’t working, she crawled back in bed. She’d need a plan to hide the evidence, and she’d need to act soon, cause that had taken more out of her than she expected. The only places she could wash it were the bathroom and the kitchen, and the kitchen was on the other side of her parent’s room. Bathroom it is.

New plan in mind, she silently crept to her door, brush held in her wavering magic. Peering out into the hall and seeing no one, she crept as quietly as she could, keeping an eye on the parent’s door to make sure it stayed closed. Still staring at the parent’s door, she reached up, opening the bathroom door and slipping in in one smooth motion.

The light was on. Her sister was there, brushing her teeth. She was doomed.

Stuttering something about dropping her hairbrush in the jelly on accident as she was practicing her magic, her sister just nodded, buying the entire story outright. Hopping up on her stool, Star once again praised her amazing big sister, thinking about how cool and laid back she was. Finishing brushing her teeth, her sister turned to leave, Star completely missing her smirk as she glanced at the shiny with lube and slightly gaped hole under her tail. Star also missed her sister muttering something about another buttslut in the family, though as she went out the door, Star definitely did not miss the sight under her big sister’s tail. What was normally puffy and wrinkly was now just a thin twitching ring, the bright light of the bathroom offering a perfect view of the first six inches into her sister’s butt, the deeper parts of the pink tube only hidden by shadow.

Yup. I could easily fit my hoof in there.

Version C

Bored.

Evening Star was bored.

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.

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.

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.

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.

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.