How To Train A Tentacle

by LilSlipsy

Royal Slumber Party

Previous Chapter

“Headsworth!” the princesses shouted as they ran down the hallway towards the throne room. There was a line of ponies that were queued who knows how far down, all waiting for an audience to air some sort of grievance. They heard sharp words coming from inside the room, but after a few moments, they saw the royal purple of Headsworth’s fur trotting out and heading away from the crowd.

He didn’t even lift his head, but they kept after him, galloping down the stone hallway around the corners he turned. Finally, after shouting out once more, Headsworth’s ears popped up and he turned around suddenly. “Oh. Hello, Your Majesties,” he said with a small curtsy. “I didn’t see you there. Were you chasing after me? I do apologise… I must not have heard your call from the many folks who are waiting.”

“Yea, there’s quite a lot of them,” Luna commented.

“I tried my best to calm some of them, but some were… being a bit difficult. Some are very insistent on needing to see you, and I keep trying to say that you are developing a plan.” The unicorn looked like he was trying to hold back a sigh, but stopped himself from doing so. “Just… I don’t know how much longer we can keep telling them that.”

“No need to fret. You’ve done an excellent job consoling those ponies,” Celestia started to say and a hint of a humble smile appeared on Headsworth’s face. “Though, I think we know of a way to solve this problem, but we’re going to need your help.”

He gulped and nodded. “Anything.”

“Good. We’re going to need every filly and colt you can get to come over for a very special sleepover.”

“Oh…” the unicorn said as he mulled it over, and his eyes started to go wider. “It’s… it’s so symbolic and… and… brilliant! Like a way to help unify everypony by getting the younger generations to come together for one night in the royal castle. Everypony would see it as a show of togetherness in these trying times, and fill their hearts with pride and strength.” The unicorn stared in awe with his mouth partially open. “Is that what you mean, Your Majesties?”

Celestia nodded confidently. “Of course.”


It was more than they could have hoped for.

This was the largest meeting hall in the castle, and usually it would have been for a large banquet; tables filled with food and chairs for everypony in the land to sit. But now, the floors were covered in blankets and mattresses, with pillows stacked up high for everypony... or everyfoal.

Practically every filly and colt in the land was here, or at least as many as Headsworth was able to muster up over the last two days. It looked like a sea of different mane colours and coats from all the unicorns, pegasi, and even some earth ponies who were in the mix. It took a while to herd everypony into the room, but by sundown the doors had been shut and the sleepover officially began. The chattering of foals talking with each other filled the room, but they quieted down as soon as Celestia addressed the crowd.

“Thank you all for attending the royal slumber party!”

All eyes turned to watch as she walked out onto a small stage on the side of the hall, a platform where a band normally would have set up and played in the background. There were thick red curtains behind her, with Luna sticking halfway out from it, tending to the creature hidden on the other side.

“Is everypony here excited? You’ll be having some fun tonight!” Celestia said as the ponies in the room started to cheer. She smirked as she listened to them and looked around the room at everypony’s smiling face, but when she saw Candy sitting in the front row with the same smirk, the two nodded knowingly at each other.

“Well…” she started, waiting for the room to tone down a little. “Tonight we’re going to play a little game and meet a new friend. A night of fun where we’re going to learn a little about each other and a lot about ourselves.” She pointed her hoof back at the curtain. “Now let's have a look at our friend here… you can come out…. Don’t be sh-”

The main entrance doors started to swing open, cutting Celestia off as she glared at the intruder. Headsworth poked his head in, “Did you need any snacks or refreshments? Maybe some more blankets or pillows? I think I found some more in the secondary backup storage room, maybe I could bring those i-”

“No!” Celestia shouted out as she tried to close the door with her magic from across the room.

“B-but-”

“We are fine in here for tonight! This is a sleepover for foals only and I don’t want anypony disturbing us at all. And. That’s. Including. You!” she punctuated with the door shoving Headsworth until it finally boomed closed, and the sound of a heavy locking mechanism rang out in the halls right after

The room fell silent as Celestia regained some composure. “Well… no adults tonight, and no rules!” The room erupted into a cheer as if she just declared a national ice cream day.

The loudest of cheers and excited faces were in the front, squished in tight to get as close as they dared. However, there were a few in the back, sitting in small groups while they watched the stage. Practically everypony in here had on pristine dresses or bowties, the best that their parents could send them here with. It was a shame that so many of them were going to get ruined.

Celestia opened her mouth again as she pointed to the curtain, but she paused for a moment before looking back at the crowd with a grin. Another idea turned in her mind the more that she thought about it. “Now... I need a few volunteers to get the activities for tonight started.” Before the words fully left her, hooves were already shooting up in the air, each waving more frantically than the last. “Alright, you… you… you two… you, you, you, and you.”

By the time she finished picking a few in the front, they were already making their way over to the stairs on the side. She turned from the crowd to go and meet the first one, a cyan coated unicorn filly with streaks of red in her purple mane. “Welcome,” Celestia said, shaking her hoof and pulling her in for a quick kiss. The filly’s eyes went wide, her lips twitching to speak but nothing coming out.

The room went silent, save for a few ponies who were still chatting away in the back who might have not seen exactly what happened from that distance. Celestia pointed to the center stage and the filly walked over like she was just learning to use her legs for the first time.

The second pegasus filly already had a blush on her freckled face as she glanced between the middle of the stage and the princess. As soon as Celestia moved in, the filly stuck out her lips too. The second followed the first filly, with the third getting a quick peck before joining the rest. The fourth in line however was a colt, with redness piercing through his brown coat. He didn’t dare make eye contact as he stepped closer, looking almost anywhere else but at the princess.

“You too,” Celestia said with a smirk and gave him quite a lot more than a peck. His eyes squeezed tight, almost like he was preparing for the heavens to smite him down if he even thought about twitching in the wrong way.

“Mmph!” he let out as she pulled back, finally giving him a chance to breathe. “You’re welcome!” he blurted out, before freezing in place as the two stared at each other. One might have not even realized his face was brown with the way redness flushed over him. He finally snapped to and hurried over to the center stage like his life depended on it.

As the last of the line was greeted and herded to the middle of the stage, Celestia stood in the front. “Now, I know lots of you might not know each other, so we’re going to do a little friendship game of sorts before tonight's main event starts. I want each of you to grab a partner or two and follow along.”

The crowd started to move around and partners began finding each other quickly enough. “Good… now on to you,” she said to the volunteers behind her. The only three colts on the stage paired up with a filly, but two of the girls on the end had to partner up with each other; they should be fine with that arrangement.

The brown colt and cyan-coloured filly were paired up. Celestia ushered them over to the edge of the stage, noticing as they went that their hooves weren’t completely made of rubber anymore. “I’ll need you to help demonstrate to the crowd,” she said, watching the colt nervously gulp as she gave a sly smirk. Celestia then turned to the filly. “And you, I’ll need you to just turn around and enjoy.”

The cyan filly looked confused, but turned around until her rear faced the crowd. Celestia’s horn lit up, gently brushing through the purple tail, pushing it over just slightly, but not enough to give everyone an eyeful just yet. “We’re going to be playing some tail games tonight,” Celestia said out loud. “But we’ll be looking a bit more at what's under the tail.”

“Eep!” the filly squeaked as Celestia moved the tail to the side, letting everyone see those soft untouched folds underneath. A few gasps and quiet murmurs came from the room, but that wasn’t going to be stopping the show.

“Now I’m sure many of you haven’t gotten familiar with another pony down there, so today’s your lucky day! We’re going to be doing a lot of exploring and it’ll make for the funnest sleepover you’ve ever had. I just need a little help to demonstrate…” Celestia looked over at the colt and gestured him closer. “We’ll start with something simple... touching it.”

The colt looked like she had just asked him to touch lava, but with a small nod he lifted his shaking hoof closer to the filly’s rump. He stared at his target and could see everything; the crowd could too. The room was almost silent as the distance closed and his hoof landed right on the cheek of her butt. “Closer…” Celestia whispered to the two of them, and reluctantly his hoof squished right against her outer lips.

“Excellent!” Celestia cheered. “That’s the first step. You can feel around there and start rubbing it too.” Her smile only grew and his hoof started to move back and forth, like he was petting the delicate head of a tiny bunny. “And what does she feel like?”

“U-uh… h-h-hot?”

“Hot. Yes, it’s warmer back there, and if you keep rubbing, soon you’ll find it getting hotter, and even wet! If you start feeling some dampness on your hoof, you're heading in the right direction!”

The room was still dreadfully silent; she’d probably be able to hear a pin drop if it wasn’t for the volunteer filly breathing just a little harder than normal. “Now, let’s go over this again with your partners,” she said to the crowd. “Lift your partner’s tail… go on… there we go! Put your hoof between their flanks and keep it there until I say so!”

It was like she was conducting a naughty orchestra as more and more of the foals started to follow along: some nervously, some obediently doing it right away. The result was still the same: a small squeak here, a subtle huff there, and the beginnings of a moan somewhere in the middle. “Don’t be afraid to play around with your partner, rubbing it… licking it… extra praise if you give it a kiss!”

A few seconds after she said that she spotted a few heads slipping underneath tails, eliciting distinct squeaks of surprise. She licked her lips at the sight, ears twitching as the virgin sounds started to build. A sudden whoomph came from beside her as her wings shot out.

This was a great start to the night.

It seemed like a fair amount of the attendees had gotten the hang of things. Candy had moved from her spot on the side, disappearing into the crowd, probably helping guide a few of the more reluctant ponies. All the while, most of the other volunteers were starting to join in with their partners for everyone to see. But even with all of that going on, there was one thing that was missing. “Oh, and we almost forgot about our new friend we wanted you all to meet,” she said out loud for most to hear… although some of the really eager ones were too distracted.

She turned around to start heading to the curtains, but two things caught her eye. First, there was a freckled filly paired with a cute orange colt. She looked to have taken some initiative and was fondling his dangling fluffy orange orbs. There was just one more adjustment needed....

With a quick magical grab, the two foals were lifted up suddenly, brought to the front of the stage and rotated around so that everypony could see under them. “You’re doing great,” she said with a smile to the startled foals. “Just let everypony see what you’re doing to him so they can follow along too.”

The second thing she noticed was that the two fillies paired up at the end hadn’t made a move on each other, and were awkwardly shifting around as Celestia approached. “D-do we have to?” one of them - a marshmallow coloured pegasus - timidly asked.

“No, you don’t have to, but you’d be missing out on a lot of the fun. Hmm… were you looking for something else? Maybe a colt perhaps?” The two cautiously shrugged, but the other yellow unicorn slightly nodded. “Well… if you follow along and try it out until the end, we can look at getting you paired up with any colt that you like in here… or…”

“Or we have something else in mind! Our friend is back there and I need two volunteers to help get things started. It is going to be quite a bit more than just a hoof back there, but I’m sure you are up to it, The Helpers of the Princess?”

The two girls looked between each other before nodding. “O-ok, I think we can do that.”

“Sure, we accept!” the other one said, as she took a deep breath, trying to look braver than her shaking hindlegs let on.

“Perfect!” Celestia smiled as she moved, flicking the tip of her tail along their chins as she passed. “Come along now.”

Just as she neared the curtain, Luna’s head popped out. “I thought you’d never get over here!” she whispered harshly. “I almost had to have all the fun for myself, and have it worn out before it even got to meet our guests.”

Celestia just rolled her eyes and smirked. “That would be a shame if I wasn’t able to watch.”

Luna tried to hold back a snrk but a small chuckle still came out. Their eyes danced over each other, subtly biting their lips trying to hold back the hunger that was inside. Luna’s gaze switched to the two fillies behind the princess.

Celestia took note and promptly welcomed them into the discussion circle. “Here are two of the girls who are going to try out our new friend first. I’m sure it’s eager to meet everypony.”

“You have no idea,” Luna commented as a pink tendril slipped from the curtain below and rose up between the four of them. Luna gave it a little pet on the top of its bulbous head as it pointed back and forth between the two new girls.

“Go on. Say hi to our tentacled friend here,” Celestia said. “It wont bite, but it will be giving you all a big hug soon enough.”

The two glanced at each other for some reassurance, but the marshmallow coloured pegasus was the first to speak up. “Hi, ummm… tentacle?” she said, looking at each of the princesses to see if she was actually doing this right.

The other filly walked up and put a hoof around the wiggling limb, politely hugging it against her chest like a new friend she just met. “Nice to meet you, I’m Lemon Haze, and that is Sweet Puff. The princesses said you liked hugs,” she said with a smile, but then started to blush and looked to Celestia, “W-was that too much, Princess?”

The tendril had curled around the back of her neck, but didn’t look like it was ready to pull away from the hug anytime soon. “That was perfect,” Celestia said as Luna’s horn lit up, the red curtains starting to part as more of the pink tendrils began snaking their way onto the stage.

The two fillies' eyes went wide at the sight of the full creature, and it was getting much closer too. The yellow unicorn’s hug started to become something more as a few tendrils slipped by her legs, feeling around the base of them before slowly making their way up.

“Now is the fun part. You just need to go ahead and hug it. It will take care of the rest.”

The yellow unicorn spread out her hooves as the creature started to pull her in closer, wrapping around her hindlegs and plucking her up off the ground. She gulped as she looked at Celestia. “Is it going to be… touching me… y-you know?“ she said as she pointed back with a tilt of her head, not wanting to say those words.

“Excessively, but our friend knows exactly what to do so you’re in good hooves... or, well… tentacles,” Celestia said with a giggle.

“Eep!” Lemon Haze squeaked as she felt more than a few somethings between her legs, caressing and certainly making up for the rubbing practice she missed earlier.

“You too,” Celestia said to the marshmallow pegasus as she stroked a hoof all the way down her back, right to her dock, getting a heavy shiver as she lingered at the end. It brought a smile to her face when feeling the filly’s natural reaction; it was the start of many more new experiences to come.

Reluctantly, Sweet Puff started to reach out to the creature like a puppy asking to be picked up. The pink tentacles couldn’t help but oblige as the mass pressed against her, wrapped her legs up and pulled her into the blanket of limbs. It wasn’t long before the both of them were making soft but shaky coos as several tentacles rubbed down below; they hadn’t gone inside yet, but that was all but inevitable.

Celestia started to walk out to the front of the stage as Luna fluttered on top of the creature, grabbing onto a few tendrils like a pair of reins, ready to herd it along.

“Now the next part!” Celestia announced, getting the attention of the volunteers on stage and many more in the crowd. “The main event for tonight. Let’s meet our friend and honoured guest, and show them how welcoming we can be. I do want everypony here to give it a big hug! But don’t be surprised when its tentacles hug back... or more; it really likes to play under ponies’ tails. Let it, and it will really show you how to have fun!”

There was some confusion on a few of the faces who were watching her, especially as the two fillies on board the creature left little to the imagination with their legs spread and pink tendrils pushing inside. Their soft coos were getting deeper and turning into heated pants as the real fun began.

Celestia didn’t pause for a moment as she called out to her volunteers, “Let’s give them a good example. Just go up, hug some of the tentacles, and it will take care of the rest.” They looked between each other and after a few moments took some cautious steps forward. Some grabbed onto the mass, while others stood still as the tendrils moved their way. One by one, each of them were lifted up or buried right inside the wiggling nest.

“Hyah!” Luna shouted as she whipped the tentacle reins, driving the creature closer to the edge.

Celestia stuck her head close to the mass as it moved by, whispering into it like it had an ear somewhere in there. “This is a good start, but prepare yourself to last. There are a lot of ponies here just for you tonight, and you don’t want to disappoint.” She couldn’t help but smile slyly as she looked between it and the crowd. “We expect you to have every one of your tendrils inside somepony here. Every. Single. One.”

The creature’s entire body shivered and a few excited chirps came from it. With that, and how a tendril reached and gently stroked her cheek, she was pretty sure the creature understood the message. There were more than enough fillies in here, and even a few colts if the creature really wanted to experiment.

Soon tentacles were flowing over the edge of the stage and onto the main floor as the rest of the mass followed. Luna pulled back and forth at the reins, getting it to move from side to side to wherever the most ponies were at the time.

Those that were in the creature’s way were practically sucked in, disappearing under the wiggling limbs. Some trailed behind, obediently following directions and getting close enough for tendrils to reach out. Others were caught completely off guard, like one filly who squeaked out in surprise as she was picked up, probably not even realizing the creature was approaching since she had been on her back with a colt’s face buried between her legs.

Her wide eyes staring down at the creature in shock probably meant that it was the first time she had even noticed something non-pony was in here. She squirmed in the creature's grasp as another tendril slipped between her legs. The tip glistened, looking like it was already pre-lubricated. It rubbed against her folds, pressing right in the middle as it threatened to go in.

Her eyes looked around desperately for somepony else, only to find Luna staring right at her and quickly grabbing on to one of her flailing hooves. The filly’s world seemed to pause for a moment as Luna pulled her in, getting just close enough until the princess stood up and kissed her.

Celestia smirked from the stage, watching with throbbing wings at the sight before her. There were two pink tendrils already buried under her sister’s tail and they probably had been there from the start.

With the creature parked in the middle of the crowd, and all the volunteers brought along with it, Celestia remained the only one on the stage. Her flanks were already burning at the sight of the ponies wrapped up in the middle of it all. With a small hop, she spread her wings and glided off the stage, landing onto her hooves a little less than gracefully with her stiff wings. But as her eyes looked around at others in the crowd, she saw that there were still some that needed to be corralled closer.


Sweet Puff’s body shook again and another muffled moan came out from around the tendril slipping in and out of her throat. It was hard to do anything else besides that, being all the way up to her neck in the wiggling mass; she couldn’t see any of her white coat anymore.

She had lost Lemon Haze somewhere underneath, but she was pretty sure the other filly was in the same predicament. Another shudder rocked through her body from the tendrils down below.

Everything had moved so fast since she was up on stage. At first the creature’s hugs were all over as it held her tight against its form, sliding between her legs as it felt everywhere. The princess had said it was going to touch under there, and she hadn’t been joking; it was like a dozen hooves were eagerly feeling every spot from her belly to her tail.

She could feel heat and wetness there, and before she knew it, the touching had turned into pressing as one of its tips slipped further in and opened her tunnel for the first time. It went at its own casual pace, but it was enough for her to let out hard huffs as she felt herself stretch. She could see it slipping in if she looked down, and everypony in the crowd could too as well; eyes had been focused right on her and Lemon Haze.

A blush was on her face. She tried to be proper for the princesses, but she couldn’t do anything, and the increasingly loud moans only further dashed her attempts at any semblance of formality. Lemon Haze’s tongue threatened to roll from her half open mouth, and had a hard blush on her face as she struggled to keep her eyes open while everything started to build up. Sweet Puff squeezed her eyes tight as soon as the tendril started to move in and out; she probably looked exactly like Lemon right now.

The length inside her felt hot, spreading her sensitive tunnel open for the first time; she had never even thought about something going into her like that until the few moments before the creature wiggled its way in. There was a discomfort that came with the stretching, but the constant sliding brought something else with it, a tingle of sorts that had her breathing harder and squirming at the hints of pleasure. Plus all the poking, rubbing, and sliding along the rest of her fillyhood was starting to light up buttons she didn’t even know she had until now.

She huffed hard again as she caught the end of the Princess’s short speech to the crowd and watched as more of the volunteers jumped, climbed, or were pulled into this wiggling mass. She could already hear the subtle gasps and squeaks as the other foals were getting tended to.

When she was able to focus and look down, she couldn’t even see her body anymore. The pink tendrils were pulling her in deeper as the entire creature moved. Her stomach dropped a little as she felt it go off the edge of the stage, though she didn’t really know what else was happening out there as her entire world went pink when her head dipped below the surface.

It was hard to tell if the creature was moving or if it was just her, but by the sensation in her stomach they seemed to be headed somewhere around the room. But even if they were moving, the tendrils didn’t seem to be too distracted. Its movements still sent tingles down her spine and a euphoric wave of pleasure along with it every time it pressed back into her.

Focusing on anything else besides the area between her legs was hard. Light from above occasionally broke through the many limbs that kept her suspended. She was so very close to the surface, yet she couldn’t wiggle any higher, only able to bob in the sea of limbs she was swallowed by.

Luckily, the light got brighter and as she felt the creature slow to a halt, her head breached the surface. She gasped for air as hard as she could through her nose and the sides of her occupied mouth. However, Sweet Puff had a few moments of respite as the tendril inside her fillyhood pulled out Though, her respite didn’t last long as what felt like a new tendril began pressing into her entrance, replacing the old one.

Her eyes widened as another slithery appendage slipped between her flanks and started pushing into somewhere else entirely. The tendril already felt hot and slick, slipping inside her butt without much difficulty no matter how tightly it felt like her rear was trying to squeeze it. She pushed out a throaty moan around the tentacle lodged in her throat. It wasn’t entirely the same feeling as how it felt in her fillyhood, but it still added to the unending shuddering rippling through her body.

But even as the tentacle kept her on this pleasure-filled ride, she could still catch a few things happening in the room through her half-lidded eyes. She watched as a filly was hoisted into the air, squealing before the lunar princess herself reached out and kissed that filly on the lips.

And with that, she could also see under the princess’s tail, getting a clear look at those midnight folds spreading open, revealing hints of pink underneath that were almost the same color as the tendrils. An anxious swarm of butterflies formed in her stomach as she stared; she didn’t know if she wanted to look, or even was allowed to look for that matter, but Luna was drawing closer with each moment, and she couldn’t pry her eyes away. But a sudden rush of sensations was enough to break her gaze as she squeezed her eyes closed for a moment and squirmed in her binds.

Luna was close. Really close. The princess’s soft fur pressing into her face snapped her eyes back open to a sight she’d never thought would happen in all of eternity. Pink had given way to the many shades of blue that surrounded half of her vision, and a darker nub that came out from the lowest parts of the princess’s belly.

A comforting warmth touched against her face and there was a noticeable poke from the princess’s other hardened teat pressing into her cheek. There was a subtly regal scent that seemed almost as fresh as midnight air but muted in a strange way, like it was a shadow of an actual scent. This royal sleepover was far from what she could have ever imagined. Her mother never could have prepared her for being stuffed face first and moaning into the underbelly of the princess, feeling what was most likely the princess’s own filly juices dripping down the side of her neck and soaking into her fur.

There was no being prim and proper for royalty now. Not here. So she didn’t even try anymore. The wet shlicking sound rang out from the tendrils right beside her ear, and she moaned without any hesitation, joining in the chorus of other foals singing their pleasured song.

She could feel a noticeable bump on the princess’s belly sliding inside rhythmically, pushing more against her cheek every time it happened. The thought of that tendril inside Princess Luna being exactly the same as what she was feeling thrust into her own fillyhood made everything feel that much sweeter.

All these pleasures kept building upon each other, stacking inside her until it felt like there was nowhere else to go. Her eyes squeezed shut, focusing on the tentacles taking her from all angles. Each of them were moving with their own rhythm, but when they all synced up for one thrust, it was enough to send her off the edge into something entirely new.

The pleasures exploded out from her belly, shooting down each one of her hooves and flooding her head with a euphoric delight. Her limbs wiggled and her core tightened, but the creature held firm and she didn’t go anywhere. She could only let out her muffled cry and press her face more into the princess as a noticeable squirt of wetness ran down her leg.

Even as she huffed out through her nose, the tendrils still kept up their movements, keeping that glow alive in her belly and stoking the flames of pleasure in her once again. It was hard to focus on anything else. The several moans and squeaks from who knew how many foals filled the air and seemed to blend together. She was sure that somepony’s leg was on her belly, but that was about all she could really notice before another of those pleasure bursts were soon upon her.

Her world felt hazy as everything once more turned to pink and her head dipped below the surface. The princess had either moved or was pulled away to somewhere else. She breathed hard, and her pants went up to another level each time the creature brought her to her peak again and again, one time after another until she could barely even wiggle her limbs anymore.

She felt so exhausted, so tired. It almost felt like she was entering a dream as she stayed in the sea of wiggling, thrusting, and rubbing appendages all around her. It all felt even stranger as she was suddenly laying on the floor with her head on the belly of some yellow pony just as exhausted as her.

Lemon Haze maybe?

She couldn’t tell.

She couldn’t even tell what the pink blur moving away from her was.

All she wanted right now was to sleep for a little bit.


“Ohhh… ohhh… ohhh,” one of the colts called out in time to the rhythmic plap-plap-plap from his hips slapping into Celestia’s flanks.

He had a soft lime coat, and a teal mane and tail, with a checkered bow tie around his neck that was barely holding on and probably wouldn’t last the rest of the night. The colt stammered and blushed when Celestia had rounded up on him, noticing his colthood sticking out at attention from all the sights and sounds.

But his hooves seemed like unmovable pillars of stone when Celestia revealed what was under her tail, and blushed profusely. He practically had to be pulled with her tail to actually mount her, but as the tip of his colthood found Celestia’s welcoming folds it wasn’t long before life sprung to his legs.

His movements were jerky and uncoordinated, but after some experimenting he found a motion that they could both enjoy. She couldn’t help but chuckle to herself as she watched the rollercoaster of emotions flashing over the colt’s strained face. “P-Princess Celestia, y-you’re so hot… it… it hurts,” he squeaked out as he squeezed his eyes closed.

“Oh? Do you want to get off?” she asked with a devious smile, watching the colt instantly shake his head as his hips found the energy to move somewhat faster. His little colthood was trying its best and the small massage inside of her was nice. Her body rocked gently every time his hips clapped against her rump.

The wet slapping was getting louder as he thrust harder each time in more sporadic movements. The colt's face tightened and his moans were turning into gasps when he remembered to breathe. His tail flicked out when he sunk in as deep as he could with one final push.

“A-Ahh~!” he practically whimpered as the rest of his body went forward until the weight of his light frame was fully resting on her back. Celestia could feel the throbbing inside of her and clenched her tunnel down around him, milking it for all that it could give, and making him squeal out a noise that could rival any other filly in the room.

A center of coolness on the fire grew inside her as his freshly made seed came flooding out and splattering down to the end of her tunnel. His legs shuddered hard and his breath shook as the last of his orgasmic throes came to a slow end.

“See, I knew you would enjoy that,” Celestia said with a smirk as she relaxed her grip on him and heard him softly grunt. She took a step forward and he slipped out of her. He felt like a sack of potatoes on her back as he panted hard into her mane. By the look on his face he might have been hard pressed to even tell somepony his name right now.

“You did good,” she said as she nuzzled against his cheek. She slid out from under him, but his rubbery legs were no match for when gravity took its hold. The colt slumped right onto a nearby mattress as Celestia’s eyes searched the room before heading off.


Celestia’s hips rocked as she patrolled through the crowd, lending a helping hoof to a foal here or there, or some guidance to some reluctant souls who needed a quick refresher of some of the basics. One group on the side - a few fillies and some colts - were huddled against the wall, glancing all around the room like a bunch of nervous puppies.

She could see their ears perk up as soon as they noticed her approaching and staring right at them. Their whispers weren’t heard over the melody of moans, gasps and other wetter noises; those noises would have given cover for her approach, but she wasn’t exactly trying to stay hidden. Her hips bounced with glee as she strutted forward. The remnants of her gooey little snack was coming out from her slit, dripping off her clit and onto the floor.

“Hey, what’s going on over here? I don’t see any fun going on.” Celestia smirked. She watched them desperately glance at each other, wondering who was going to speak first. It looked like they wanted to just jump through the wall, but unfortunately for them, there was nowhere to go. “Come on and join in. Just grab a pony, anypony, and let’s all have some fun.”

“P-Princess Celestia, I… I don’t think we-”

“Now, now,” Celestia said as soon as one of the fillies tried to speak up. “You don’t want to go and ruin the spirit of this slumber party, now do you?” A few of them shook their heads. “Good! Now come along,” she said as she reached out her hoof to the filly who spoke up.

Hesitantly, the filly grabbed her hoof, taking a few steps forward as Celestia guided her in the direction of the creature before the princess helped a few other ponies up with a wing. “Our friend will be able to teach you everything you need to know!” She giggled a little as she followed the foals from behind, herding the group to the center of the room with the mass of wiggling, grabbing, and thrusting tentacles being more active than ever.

They had to step around a few ponies too busy having their own fun, and as they got closer, even a few who looked completely spent and fast asleep lying in a sticky mess. Even if a pony was blind they would have been able to find the creature by following where the most moans were coming from.

Celestia thought it was cute watching them from the back. A few of their tails swished from side to side, barely showing anything to all but the most watchful of eyes. Some had their tails squished firmly between their legs. A few foals gasped and even glanced back with a bright red blush as soon as Celestia’s magic started tickling right under the base of their tails.

It wasn’t on any particularly sensitive spot, but playing with the soft fur along their docks was enough. Tails were instinctively starting to flag, fillyhoods and tailholes revealed, and even the colts were starting to droop out from their sheaths. Celestia could feel the throbbing in her wings coming back the longer she stared. But at least she didn’t have to focus on walking anymore: they were here.

They all stopped and stared at the creature, lifting their legs when a tendril or two wiggled by. But with magic, hoof and wing, Celestia spun them around to look at her and have their butts pointed right at the creature. She smiled again as she looked the group over. “Perfect.”

“Now… make sure your tails are up. Use that little tingle to help and just focus on that.” Her horn lit up for one last feel on their docks, earning a few more gasps and blushes from the various faces. She moved forward and pressed on one of their chests, it being enough to make all of them automatically walk backwards as a group until they were practically sitting on the mass.

Each of them fell back a little, and Celestia could already see a few of the tendrils curling around limbs or hugging onto them. The way each of their faces lit up with varying degrees of curiosity, nervousness, and surprise was just so adorable to her. A small squeak came from one of fillies and Celestia sauntered right over, kissing her until the filly let out a longer moan. “Perfect,” Celestia said once again as she pulled back and licked her lips.

She didn’t stop there. Going down the entire line of them, she gave them each a small kiss on the lips. “All you need to do now is to sit back and enjoy. I hope to be back later to have even more fun with you all,” she said with a wink as she started to leave and circle around the mass.

The creature’s chirps now sounded much deeper, like a low rumbling that came from within. It was keeping up its pace very well, and she could see several different coats and manes within, or limbs, butts, and other parts of a pony sticking out.

There was even one who was strapped to the side of the mass. He looked like he was in the middle of a pleasure-filled ride as he was being rutted from both ends, but the uncomfortable look on his face was obvious every time one of the tendrils tried to poke into that tiny hole on his colthood. There was no way that was going to work with a tentacle that big.

“Oops,” Celestia said as she hurried over to help. “Heh, you don’t want to try sneaking into that spot,” she said as she quickly grabbed the tendril and the throbbing part of the colt. He reflexively shuddered and gulped as soon as he felt the hoof, and his eyes went wide as soon as he saw who was touching him there.

“Instead, you want to make sure it’s nice and slippery,” she said as she tested him with a hoof and spurted some more liquid out from the tentacle’s tip.

“Mmmm~” the colt moaned as Celestia made sure to thoroughly test it again.

“See, he likes it!” she said with a sly smile as she manipulated the tendril around his shaft. “You want to coil around it, and just rub up and down like I did… like you’re making your own tunnel and pleasuring his tentacle!”

The colt let out another heavy moan and his eyes practically fluttered as it moved.

“Hehe… there you go!”

Satisfied that it all had been corrected, she looked back up at the colt before moving over to give him a kiss on the cheek. “I hope that’s much better for you now…” she said, whispering in his ear and making him practically shiver.

The blushing colt could only nod slightly and let out a muffled, “M-mmmhmm,” as his eyes rocked back in absolute ecstasy before an audible squirt came shooting out from between his legs.

Celestia couldn’t help but giggle as she patted him on the head and went back to her rounds around the room, making sure that everypony was having a good time.


The moans had started to die down by now, save for some foals who were still up and playing, or were one of the few who were inside the creature’s tendrils. Celestia walked around, watching over the exhausted foals as many of them cuddled into the blankets and pillows that were laid out for them. Many of them were still wet with miscellaneous juices and fluids, but few seemed to notice.

Celestia could feel something dripping from her own flanks; two wet trails of more than just her fluids were coming from both of her rear holes, globs leaving her thighs and splattering along the ground as she moved. There were many snacks that she had in one way or another. She licked her lips, muzzle still wet from the many ponies she met tonight. But there was one main course that was yet to have the attention it deserved.

With nopony looking like they needed her special encouragement, she started to head to the center of the room, nearing the pink tendrils still wiggling and slipping into the few holes underneath. Her wings helped her flutter up onto the creature, and she plopped her belly down on the top of it.

“It looks like you have done quite a good job tonight, helping everypony here have their own fun,” she said as she played with a tendril in her hoof, and rolled a few more of them together between her thighs. “Now… it’s time for you to have your own reward for tonight, don’t you think?”

A low squeak came from the creature below her and she smirked. “That’s what I thought.” She leaned in close to the creature, almost like it was just the two of them and she was just whispering to a friend. “I want you to finish. And not just any finish. A finish just as hard as you made every filly and foal here finish tonight… and I think I can help you with that.”

Celestia smiled as she lapped at the tendril in her hoof, licking slowly around the tip and swirling her tongue right around the hole in the middle. The exotic grasses that this creature tasted like were mixed in with more than a few different flavours: distinctly feminine and pony-like notes that tasted as sweet and as varied as a fruit bowl.

It was a nice start, but there was one thing missing. She was the only pony at the very top of the creature, and the previous owner of the pile was nowhere to be found. Celestia looked around the room for a few moments at all the pastel coloured coats and discarded dresses, until she found the unmistakable blue of her sister’s leg sticking up in the air from a pile of spent foals.

“Humminah… ah… haaaa…” Luna softly mumbled out. Celestia’s magic lifted her out from the pile and over to them, setting the filly back down on the top of the creature. Her legs were splayed wide open and it didn’t take but a few moments before the pink tips were searching between those midnight folds and making their way in.

“See… this is for you… don’t hold back,” she said with another sly smirk and a heavy lick on the tendril in her hoof. She could feel the creature’s entire body shake and a thick glob came rushing out as soon as she said those words. The creature might have been close, but there was only one way to find out.

Celestia looked back at the tentacles between her legs. They were already near, but the tips were quickly trying to rearrange themselves for entry. Instead she locked her two legs together and squeezed. The tentacles were barely able to pull out, but when they were free, they weren’t able to press inside with her legs clamped down like that.

A few pokes and prods happened, until a tendril was floating up, looking like it was analyzing the situation. “Heh…” she chuckled as soon as she saw one of them practically staring.

“I said, don’t hold back.”

The creature paused for a moment, but it didn’t take long before it started to move again with some speed. She could feel the change as a few of the tendrils wrapped around her core, tightening up and keeping her in place. Her legs were next to get the most attention as the slippery limbs tried to squeeze in between any small gap that they could find.

Celestia clenched her teeth and squeezed back with all her might. It kept them at bay for as long as she could before one of them finally wiggled in and started prying her hindlegs apart. With every little tug, more tentacles were able to wrap around her hindlegs and double the effort, slowly parting her gap until her muscles gave way and everything spread open entirely.

“Hehehe,” Celestia giggled out as she snapped her tail firmly down over her filly bits. Their grip tightened a little and she could feel another of the tips wedging itself through her tail hairs, getting just enough of a grip until it could pull.

“O-oh~!” she let out as her tail shot up in the air. It even lifted her rump a little as the tentacle pulled, completely exposing her backside now. With little in the way of pleasantries, she already felt two of the tips finding their marks, centering on each of her entrances and slipping their tips in. “Mmmmm~” Celestia let out as her head dipped down and she sucked at the tendril in her hoof.

The two intruders were already coated in a thick basting of wetness that mixed in with Celestia’s dripping holes. They wouldn’t have been impeded in the slightest if it weren’t for her tunnel squeezing them every time they tried to pull out. A noticeable ripple shook the creature below when she squeezed just a little bit tighter.

Luna’s eyes were starting to flutter open as she let out soft pants. “Ha… haaa… haaa,” she breathed in as the creature was slipping in between her legs with just as much enthusiasm. “S-sister?” she called out in a moment of confusion.

“Wakey wakey, Luna,” Celestia said with a small chuckle. “It’s time for the final rutting of the night.”

Luna’s eyes widened as she looked down and a sudden wave of realization washed over her face. A wide grin started to appear as she nodded, and hips began to move in time with the creature's thrusts.

“Mmmmm~” they both let out in unison as the wet sliding sounds kept a steady rhythm. However, they were already starting off faster than just a warmup. Celestia could feel each time it sunk into her and tapped at the end of her tunnel. It was enough to push her entire frame forward, and unlike any of the colts she met tonight, she knew she was going to be sore in the morning after this.

Though, as uncomfortable as that tapping was, there was still a fire turning into an inferno as the tendrils spread her wide and massaged every part of her inner walls each time that it sunk in. Her hips tried to thrust, tried to buck and help it along, but with how tight the tentacle grabbed her lower half and legs, there was little she could do anymore but take it. It almost was like that part of her wasn’t hers anymore; in fact it kind of wasn’t since she freely gave it.

The tendril in her mouth was starting to push further, slipping down past the point where she could breathe. Luckily, it came back up enough for her to take those desperately needed breaths, sucking in air when she could.

Celestia’s muffled chuckle still came out as her mind danced with thoughts and swam in the pleasures flowing through her. The creature certainly was doing what was asked of it. It was going at a hard, steady pace in every orifice she had, trying to get itself to the end after a night of being on the edge.

With the building fires in her stomach ready to explode, she wondered who was going to be the first. But as the critical point was reached, it was clear which one of them it was going to be. “Mmmmaahhh~!” Her belly tightened and tunnels squeezed with all their might, slowing the tentacles down for just a moment before a fireball of pleasure detonated inside her.

“Mmmph… mmmph,” she let out as she felt her wetness shooting out, spraying the tentacles with hot pulses of her juices everytime the tendril pulled back. But the creature didn’t pause, didn’t slow in the slightest. It carried the flames of her orgasms on far longer than it had any right to, until only a few small spurts were coming out from her; the raging inferno had been placated for the moment, but the tendrils were quickly adding fuel again.

She thought the creature was on a hair trigger when she first started, but that was obviously not the case any more. Even as she was brought closer to her next orgasm, each ripple from the mass brought hope of it cumming soon. She was stuck in the creature’s binds and there wasn’t anything she was willing to do to stop it.

Celestia couldn’t help but look over to Luna, watching as the already-spent alicorn was taken over the edge for who knew how many times this night. The yellow glow of Celestia’s magic pulled at Luna’s body, sliding it over just a bit more until she was close enough for her to nuzzle into her sister’s neck. They couldn’t say anything intelligible, but they could spend the final moments of the night together.

Something suddenly felt like it changed when the creature let out another deep chirp and another strong ripple went through it. The tendrils started to pulse and grow thicker, stretching her tunnel wide. It was so very close to cumming and she could do little besides endure the ride as it pounded into her. Even Luna was grunting out, huffing hard and squealing as another orgasm hit her.

With one final thrust, her fillyhood, thoat, and butt were stuffed to its limits. The hard, heartbeat-like throbbing from the tendrils counted down until an absolute torrent came shooting out, flooding her body with heated liquid in an instant. Instinctively she gulped, her throat massaging the length as it filled her tummy while the rest of her was filled from the other end. Her tunnels clenched again, reveling in another wave of ecstasy as her fillyhood was filled to capacity and overflowed; even her tailhole had cream slipping out from inside her when it got too much.

Her vision went white as soon as she heard the tips shooting out from every angle, covering her fur as well as everything that was in the splash zone of the creature. She didn’t hear it, but could only assume there were a few surprised foals in the room from the orgasmic sea this thing created.

It didn’t last more than a few moments until it completely stopped and she felt gravity take hold again as the creature limply started to drop. Her hoof wiped her muzzle and slid the tendril out of her throat until she could breathe properly. That was all she could do before her hoof fell back down; it felt so heavy.

She tried again to move, to stand and get up, but only her mind imagined that while her limbs felt so exhausted. Maybe it had been all the fun she had around the room, maybe it was because of how late it was, or maybe it was from the absolute rutting that left her as a spent pile of goo.

Whatever it was, it didn’t take long before her dreams of standing were quickly forgotten about as she laid there huffing into her sister’s mane, using the rest of her strength to lean over and give her a soft goodnight kiss before sleep finally took her.


Celestia flipped to the next page and continued reading. “It was a creature designed to ravage ponies right from the start and seemed to get better at it the more it evolved. For the complete table of the evolution of tentacle tips, please refer to the detailed list in-”

“Oh! Appendix!” Twilight squeaked out as she grabbed the book to eagerly flip to the reference material on the back pages. She wiggled in Celestia’s lap as she searched through the small graphs and charts that went along with the example pictures, as well as a few extra notes that had been put there long after publication.

Celestia couldn’t help but chuckle at the filly’s eager pursuit for knowledge of any kind, and on this subject in particular. It was enough to bring her back through the ages to a moment much like this.

Her first times with a tentacle creature had been one that she most likely would never forget; the pleasures varied and immense from their friend so long ago. After that one memorable party with fillies and foals abound, it was enough to brighten the mood of the town for a while; an air of friendship and bonding from every foal being so very close that seemed to naturally spread to everypony else.

But with such a creature in the area, rumors became complaints, and eventually started to cause an uproar that could only be ignored for so long. Like many fleeting things in life, there was a hole that remained unfilled when they reluctantly had to say goodbye and let it go back into the wild.

“You said this book was very old,” Twilight commented as she peered through the pages. “What happened to them? Are there any of them still out there?”

The adult princess gave a small sigh as she looked to the window and out at the moon lit sky outside.

“There are a few who know.”


Author's Note

A story that I had taken more than a long time to write but it is now out! I hope that you all enjoyed the two princesses helping an innocent tentacle creature learn more about itself in this wild world. I’m sure the ponies of Equestria will be very grateful.

Also, I was able to get a picture commissioned for this story done by Nottrevbe. You can search for it on Derpibooru with the ID number 3103700.

If you like the story, please let me know with a comment below!