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.