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.

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 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. 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 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.

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 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.