Precious Little Woona

by dirty little secret

Rating: mature
Tags: Sex, Slice of Life, Princess Luna, Original Character, My Little Pony: Friendship is Magic, Fetish, Romance, Porn
Length: 22371

Because alicorns age slowly, Luna still looks like a little filly, even though she's 93 years old. Unlike her sister, though, she prefers colts her own apparent age.

Reading Precious Little Cewestia is not necessary to enjoy this story

Because alicorns age slowly, Luna still looks like a little filly, even though she's 93 years old. Unlike her sister, though, she prefers colts her own apparent age.

Cover image adapted from the original, by Negativefox.
Contains delicious, adorasexy foalcon.

Published 2017-02-08 03:50:02 UTC
Last updated 2017-03-15 00:05:11 UTC

Princess Luna would like to play...

I pulled away from my mom's fussing. “Mom, stop!”

She didn't stop, though. She kept fiddling with my mane and with the stuffy jacket she made me wear, even though she'd already been at it for hours. “Hush now. You have to look your very best – you're going to a playdate with Princess Luna!” She reached down and wiggled the stupid bow tie around my neck a little, as if she was straightening it ... even though it was already as straight as could be.

I wished I could loosen that tie a little bit; it was choking me and pressing the starch-stiff collar of my dress shirt against my neck, chafing me. But there was no way I'd be able to get away with it under my mom's perfectionist gaze. So I just had to endure it as she ran a lint roller over my jacket again, as she licked her hoof and smoothed down my mane again, as she straightened out my lapels again.

I had wanted no part in this 'playdate' when I was first dragged into it. I had my own friends to play with, and this Princess sounded really stuffy and boring ... but at this point, I wanted nothing more than for the thing to finally start already, so I could get it over with!

At least if it could start already, I could hope to get out of my mom's pestering and fidgeting. It was intolerable! What kind of play were we even going to do at this playdate when I was dressed so stiffly and uncomfortably I could barely move? I looked all around the antechamber, searching for something I might be able to distract Mom with for a moment, but nothing came up. It was pretty much just a bare room with a few benches – a place for ponies to wait for their appointment with royalty. Nopony else was there today, just us. And we'd come way too early, because of my mom's paranoia about being late.

I had to push her away when she tried to lick down whatever out-of-place mane hair she could still find. “Mom, no!” I jumped away from her. “Enough already. I'm sure I look perfect.”

“Eee! I don't know...” She danced side to side for a moment, fidgeting from hoof to hoof. “I picked the maroon blazer because it went with your mane, but now I think the colors might be too close and they'll clash. I knew I should have made an appointment at Dressier's boutique! I've never been very good at fashion.”

“It'll be fine. And it goes good with my fur.” The dark red fabric did look fetching against my pale grey coat. She had to at least see that, didn't she?

She only cringed. “Do you remember your etiquette?”

I groaned. “Bow the first time I see her, or her sister, only address her as 'Your Highness', do whatever she says. Got it.”

“And no attitude! If you speak to her in that tone of voice, you're going to be grounded for years!”

“Yes, Mom.”

She sighed. “Pepper, you have to take this seriously! Do you have any idea what it might mean for our family if you get along well with Princess Luna? There is nothing – nothing – that compares to having a personal relationship with one of the princesses when it comes to getting one's voice heard in the royal court! And just think what it might mean for you personally – this is the opportunity of a lifetime, of ten lifetimes! How well you get along with the Princess today might determine your whole life. It might even get you a cutie mark!”

My ears perked at that last bit, but then it also made me hang my head a little lower in shame. There was no denying it at this point. I was a late bloomer. Everypony else my age already had their cutie marks, but my flank was still blank. I didn't have much hope of getting one today, but the prospect of finally getting one was enough to give me a little more motivation.

“Now,” my mom continued, “no matter what happens, you have to remember that—”

A royal guard opened the antechamber's door. “Pepper Zest, please. The Princess is ready for you now.”

I gulped and froze in place, but that didn't stop Mom. She pushed me forward, sliding my hooves over the stone floor until I came back to myself and managed to walk on my own.

The guard deftly angled between me and my mom as he came into step next to me, cutting her off and blocking her from coming into the Princess's room with us so easily that he made it look like he wasn't even trying to. Mom fell behind as we went in through the door – I could practically feel her fidgeting behind both of us. But she couldn’t come in, she wasn't invited. When she had to stop, she shouted one last bit of advice to me, “Remember, stay on your best behavior! Nothing inappropriate, and do anything she asks you to!”

The door shut behind me and the guard. He led me wordlessly through a short hallway, our hoofsteps echoing in the tight confines, and then we were in the young Princess's audience chamber ... or maybe it would be more accurate to call it a playroom?

There was no Princess in here yet, just me and the guard. After just a moment, the guard left as well, stepping outside the door we came in. and then it was just me.

The room was round, with a low, domed ceiling. It was dimmer than the hallway outside, but still bright enough to see easily, and while it was a pretty big room, it was by no means huge – it was probably about three times the size as the living room in my own apartment. The whole place was strewn with an embarrassing wealth of toys.

My eyes lit up, seeing all these new things to play with. I had thought that she would only have girly toys, and there were some of those: dolls and dollhouses and the like ... but it was mostly toys for young colts like me. It was half-organized into somewhat distinct sections, with different toys in different places around the room – a massive pile of building blocks over here, a full set of Super-Stallion action figures over there, stacks of board games next to an empty table, and even a small slide and swing set on the far side of the room ... right next to the room's only other door.

I stopped myself before running off to start playing immediately. My mom had reminded me to be on my best behavior, and that probably included not playing with somepony else's toys before they even arrived.

So I sat myself down and resolved to wait. That didn't stop my eyes from wandering though. Bizarrely, there was a miniature doctor's office set up against one wall, complete with table, instruments and chairs, even with a little curtain to close it off. Near that was a set of bookshelves with children's books and a comfy-looking sofa. I contemplated moving over there to make myself comfortable ... but I decided that might make me look too comfortable with the Princess's things. So I stayed where I was and tried to decide what to play with first. Obviously, I'd have to defer to the Princess's wishes on that, but I had my eye on a set of wooden soldiers – a complete battalion of perfectly-accurate royal guards.

The door on the other side of the room opened, and I snapped to attention, ready to bow.

I almost bowed too soon, because the Princess wasn't the first one through the door. First there was a royal guard, then an elderly blue earth pony mare, then finally Princess Luna came through, followed by another guard.

The moment she came into the room, I bowed low, just like Mom had told me to. “Your Highness...”

She crossed the room in just a couple long leaps, helped by her outstretched wings, then stopped in front of me. “No no no! Get up. No bowing or 'Your Highness'ing today! We're just here to play.”

Slowly, I picked myself up off the floor and finally allowed myself to really look at her. As soon as I saw her green eyes looking into me so deeply, with such anticipation ... I had to look away or I'd blush. But I did see that she was a little taller than me, a bit more slender, with dark blue fur and a lighter blue mane. She was ... really pretty.

And she was still staring at me, no doubt expecting a response.

“Oh... If you say so, Your—”

Her eyes narrowed.

“You're right, I mean. Yeah, we can't play and be formal the whole time, can we?”

That earned me a smile from her... which went straight to my heart and made it flutter strangely in my chest. She leaned forward, closer to me. “We're going to have so much fun together!”

I nodded, feeling like my stuffy formal clothes were already too warm for this room. The Princess wasn't wearing anything at all, so why did I have to be all dressed up?

“Oh, it's been so long since I got a new play-mate!” She spun in a quick circle in her excitement. “What do you want to play first?”

My eyes darted over to the neat rows of toy soldiers, but then I became aware again of Princess Luna, how close she was, how real she was... I couldn't afford to let myself just do whatever I wanted, not with her so close to me and so eager. “Um... What's your favorite game to play? Let's play that.” Good – that would make my mom proud.

She smiled coyly at me. “Oh, I have certain favorite games I like to play with colts, but we'll get to that later. Maybe for now, I should introduce you to my nanny.”

I murmured a yes, and she immediately turned to lead me across the room to the old mare. Princess Luna didn't seem to care anything at all for modesty – even though she was walking right in front of me, she let her tail flag high and to the side. I did my best to be polite and not look.

Or, well, I did my best to not appear to be looking at her. I hadn't told my mom or anypony else about it, but I'd started getting funny feelings around fillies and mares recently. Kind of a curiosity, if curiosity felt both good and uncomfortable at the same time. I'd snuck glances under the tails of other mares and fillies before, but even though they all looked pretty similar from what I could tell, for some reason I always wanted to check and see what a new filly looked like. Luna's was a little bigger and puffier than most young fillies I'd seen, and her smooth, dark-blue skin down there seemed to invite me to look more closely... But otherwise, she looked a lot like any other filly: little round tail hole above a slitted bulge below. Strangely, even after I knew what she looked like, I wanted to look more. But I stopped myself – I didn't want her nanny catching me!

“Okay,” Princess Luna said when we stopped. “This is my nanny, Blue Dreams. Blue Dreams, this is, um...” She looked over at me as I stepped up next to her. “Uh... What was your name again?”

“Pepper Zest.”

“Right! Blue Dreams, this is Pepper Zest, the new colt for me to play with.”

I gave the old mare a slight bow. “Pleased to meet you.”

“Likewise.” She smiled. “Oh Luna, you've plucked a new one already? You go through 'em so quick these days, and even if you do age slow, sooner or later you're gonna to get too old for this kind of thing.”

Luna rolled her eyes.

But Blue Dreams wasn't done yet. She looked over at me. “Now you have a care, young'un, and go in with both eyes peeled. Our little Princess is one peachy filly, but I've been her nanny for nigh-sixty years now, and I've know what she—”

“Thank you, Blue,” Luna said tersely. “That's quite enough.”

Blue Dreams gave a tiny grunt of disapproval, but she turned and sat down in an old rocking chair, which seemed to mean that she'd acquiesced. “Oh alright. I don't suppose it's gonna do him any harm, and that little feller's got to learn someday.”

I looked over at Princess Luna, keeping in mind that I shouldn't use any royal titles. “Learn what?”

“Um... Learn how to build trains!” Princess Luna darted off toward the other side of the room, where a half-deconstructed train set waited.

I didn't really believe that trains were what Blue Dreams had in mind when she said I'd have to learn something, but I knew better to argue with a princess. So I followed Princess Luna over to the train set.

“Okay, Pepper,” she said when I caught up to her. “Let's build a double loop figure eight. I almost finished it once, but I couldn't get it done before playtime was over. But now I've got you to help! You're old enough to be apprenticed, right? What are you studying?”

“Um...” I rubbed the back of my mane. “Well, the Zest family has always worked in the royal kitchens. My grandfather is head chef and my dad is the chef for one of the catering teams. So I've been put to work in the kitchens. It's ... not very exciting, and I'm pretty sure it's not going to help me build any trains.”

“It sounds really interesting, though.” She giggled and tossed her mane with a flick of her head ... it had a way of drawing my eye. “Come on, I'm sure you'll be great at it anyway. You set up the big curves along the outside, and I'll do the tricky bit with the raised bridges, okay?”

Luckily, one big curved section was already assembled, so I could see how the little pieces of track fit together into a curve. I set to work expanding the curve that already existed, and I was soon glad to be a unicorn. I had no idea how I'd manage to fit the intricate pieces together if I had to fumble them with hooves.

I'd seen train sets in toy stores before, but they were nowhere near as small and detailed as this one ... and even those had been so pricey that my dad would never even consider getting me one. But this one put them all to shame. The little pieces looked so perfectly like railroad tracks, and they snapped together so cleanly, each piece sliding into the next with a satisfying click. It must have cost a fortune...

I looked over at Princess Luna, ready to ask her where it came from ... but then I had to immediately look away. She had her face down near the floor as she carefully set up a line of trestles, and though she was very close, she was facing directly away from me. When I looked at her, I had ended up with my face scarcely half a hoof away from the part of a filly I wasn't supposed to look at.

My suit was feeling really hot and stuffy now. I wished I wasn't wearing it. But I couldn't take it off now; that would be awkward, and there was nowhere to put it. So I just focused on joining curved pieces together instead, keeping my nose in my own work. “So ... um...” I pulled at my stiff collar, painfully aware of how near to me Princess Luna's unmentionable parts were. “Um, where'd you get such a nice train set? I've never seen one like this.”

She didn't look up either, keeping her rump up high and even wiggling it back and forth a bit. “Oh, this is a gift from one of the colts I used to play with a long time ago. He was a real genius with machines, and he gave this to me when he grew up.”

“Oh, okay.” It struck me, suddenly, how much older and more experienced Princess Luna really was. She looked a little bit older than me, but really, she was older than my grandfather. It was really amazing that she still liked playing like this. But I wasn't going to complain – this was actually kind of fun, seeing the track take shape under our hooves.

We fit together more and more of it, making quick, steady progress. It really was quite easy, actually, even though we always seemed to be working in a position where Princess Luna's rump was right next to me ... but that was just how it worked out, because she was working on bridges in the middle and I was working on curves on the outside. All I had to do was avert my eyes from her curves. Or, well, failing that – as I too-often did – I just had to make sure that her nanny didn't catch me sneaking glances where I shouldn't be. I knew it was risky, especially with a princess, but for some weird reason, I just couldn't help myself. It made me feel full and warm inside when I looked at her, and I liked it.

At the first hint of her turning around, I snapped back to putting tracks together.

“Okay, Pepper. It looks like we're almost done. Now we just need to connect our parts together.”

I gaped. “We need to what?”

“Put the parts we've made together.” She looked at me, tilting her head to the side. “You know that's what we've been working toward this whole time, right?”

“Oh, right. Right.” Well, at least she didn't catch me staring. So what if she thought I was a bit stupid ... at least she wasn't freaking out about me doing something inappropriate. That would really get me in trouble.

We snapped our completed sections together in just a few moments, and I watched in anticipation as Luna carefully set the train on its new tracks. I didn't dare touch the train itself with my magic. It was far too complex and detailed ... too fragile to risk me doing anything with it. If I broke the Princess's special one-of-a-kind train set, I'd be in for it for sure!

The train sputtered to magic-infused life and chugged merrily around our double figure-eight, looping around each of us before going over or under the bridges in the middle.

Princess Luna tapped her chin. “Hm... It needs something, don't you think?”

“It looks perfect to me.” I found it very satisfying, actually, to see our creation come to life and work perfectly on the first try.

“I know! Run and get some building blocks from over there.”

“Um... Okay.” Hopping over the miniature train tracks just as the train went under me, I hurried halfway across the room and brought back a whole box of building blocks, held securely in my magic.

Princess Luna pulled a few dozen blocks out of the box all at once, and I stared in awe of her magic control abilities as she deftly placed them next to and over the tracks. She probably could have laid the tracks all by herself in a matter of moments ... but maybe it's more fun to do it with a friend? Was I her friend already?

“There.” Princess Luna sat back and admired her handiwork. “What do you think?”

She had built long tunnels along each of the lower straight tracks in the middle, covering them with the longer building blocks to make them fully enclosed. As I watched, the train came around for another approach and vanished cleanly into one of them, only a hair's breadth away from the sides, but not touching them as it whizzed through.

“Wow, that's neat,” I said as it emerged from the other side.

“It's a lot more satisfying this way, isn't it?”

I watched as it crossed over a bridge, then around another curve before it slipped into the other tunnel. 'Satisfying' was a really good word to describe the sight of the long, sinuous train slipping perfectly into the tunnel made for it. It was very satisfying, in an odd way. Even though I entirely knew how it worked and it shouldn't have been anything special, I was fascinated by it and I watched it go through those tunnels over and over again without getting bored of the sight.

After who knows how long – I'd lost track of how many times the train went around its circuit – Princess Luna poked me in the ribs. “Hey, are you just going to stare at it all day, or are you going to play with me?”

“Oh, right. Yeah.” I rubbed the spot where she poked me, even though it was only a tiny bit sore. Though we had been playing for a while, it was the first time she touched me ... and it still felt weird, the idea of being touched by royalty. She was untouchable, and here I'd touched her ... or at least, she'd touched me. “What's next?”

“Well, we've played with colt toys for a while now. Time for some fun, filly style!”

Uh-oh. I immediately regretted asking, but there was no going back now. After all of my mom's admonitions, there was no way I was going to argue with Princess Luna. “Okay...?”

“Come on!” She led me to the other side of the room, where there were a couple big wardrobes against the wall on either side of a big standing mirror.

“Are we ... going to play dress-up?” I cringed.

“Such a smart colt! I knew I picked a good one!” Princess Luna danced in place for a moment. “Come on, let's get started. Most outrageous outfit wins!”

Princess Luna was much faster than me at rushing to a wardrobe and throwing it open, and I was perfectly happy to let her go ahead. I wasn't looking forward to what I was likely to find in the other wardrobe, but I dutifully pulled the latch and opened its doors.

I was pleasantly surprised that at least it wasn't full of mare's clothes. This wardrobe had all kinds of clothes for stallions – or for colts, rather. And even more amazingly, most of them seemed to be about my size. But there was something odd about the selection ... there seemed to be a lot of leather in there, and an awful lot of things made of fishnet and straps, when I'd never seen any stallion wear anything like that before.

Briefly, I thought of simply refusing to do it ... but everypony expected me to do what the Princess asked. And I would finally be able to get out of this uncomfortable coat. That settled it. It was time to play dress-up, and girliness be damned!

I hastily stripped my suit off with my magic, though I was still careful not to break any buttons. It sure felt good to get that thing off of me, to finally get a bit of fresh air against my fur!

By the time I'd gotten it all off and folded, and before I'd even managed to pick out an outfit, Princess Luna popped out from behind her wardrobe's door. She wore a pleated skirt and a white button-up shirt that must have been much too small for her because it only came halfway down her body, and she could only button a couple of the buttons in front. The skirt was too small for her too, which became abundantly clear when she pirouetted in front of me to show it off. It barely covered the base of her tail, and it served more as a bit of fluff to show off the curves of her butt than to hide them.

“Oh wow, that's ... um...”

“You're right. The schoolgirl outfit is too clichéd these days. I should try again.” She turned to go back to her wardrobe, then paused, looking over her shoulder at me ... which just happened to show an amazing view up her little skirt. “And I expect you to find something before I do, okay?”

“Uh...” It took me far too long to formulate a response for some reason. It was something about looking at her that made my brain slow down. Eventually I managed, “Um, okay.”

Once she disappeared behind her wardrobe door again, I felt like I could think clearly. I turned to my own wardrobe and tried to find something that wasn't too ... weird. After shuffling through a few choices, I finally found some cowpony gear that looked normal – and masculine – enough for me to dare wearing it, so I yanked it down and hurried to put it on before Princess Luna came out again.

Not that it looked like I needed to hurry too much. Princess Luna kept saying, “No... No... No...” over and over again as she tossed one garment after another onto the floor behind her. I guessed she was having trouble deciding.

I was having my own second thoughts about this cowpony outfit. The leather vest and hat were cool enough, and the boots were a nice touch, even with the spurs. But wearing the chaps was like wearing pants that were missing very important parts. They left my whole butt exposed, which felt weird when most of me was covered.

“Oh, yes! Yes, this will do nicely,” the Princess said from behind her own wardrobe.

Well, that meant that I didn't have enough time to find another outfit. It was either cowpony or nothing, so I stepped out in front of the mirror and called out, “Okay, check this out!”

Princess Luna came out, and as soon as she saw me, she clopped her hooves together, grinning wide. “Oh yes! Nice choice!”

I felt my cheeks heat up. “You like it?”

“Spin!” She called out, eagerly.

“Well, I, uh...”

“Spin!”

“Okay...” My cheeks burning even hotter, I slowly spun around in a circle, holding my tail low over my exposed butt. It was weird ... the suit I'd worn in here didn't have any pants with it, leaving me completely uncovered, but now that I was just partially covered, I felt more exposed than ever.

“Again!” she said, as I came back to face her. “And don't be so embarrassed – have some fun!”

I took a deep breath to calm myself, and then reminded myself as harshly as I could that there was nothing weird about this, and that I was supposed to do whatever Princess Luna wanted. Okay so ... what would be fun?

After just a moment's thought, I started spinning again, but this time I danced around and bucked, yelling “Yee-haw! Ride 'em cowpony!” I went through a rotation and a half, losing myself in it for a moment before I got a little too out of breath to yell, so I stopped.

I'd stopped facing away from Princess Luna, but I could see her reflection in the mirror in front of me. She was blushing, and her small wings stood outstretched. “Those chaps look good on you,” she said.

All my self-conscious feelings came rushing back to me, and I realized I'd flung my tail up high. I quickly covered myself again, as well as I could.

“Aw, don't feel bad,” Princess Luna said. “Here, I want you to see what I've picked out while you get undressed.”

I followed her over, and even though I felt a little weird undressing in front of a filly, I was glad to get this funny costume off.

Princess Luna pulled a hanger out of her wardrobe, one that was only hung with long slips of translucent pinkish fabric. As I worked my way out of the vest, she took one off the hanger and slipped it over one of her front hooves. It was a sock ... a long sock, with a frilly upper edge and a little moon sigil near her toe. “What do you think?” she asked. “The violet goes really good with my coat, doesn't it?”

“Um, yeah,” I said, pulling the chaps off my legs. “It really does.”

“Do you want to see me in the rest of them?”

I paused for a moment, but then figured it was best to play along. “Um, sure.”

“Well, shoo! Get your clothes back on the rack. I'll be done in just a minute.”

I spared a glance at the pile she'd left on the floor behind her, but who was I to argue. She was a princess, and I was the son of a servant. If she wanted me to tidy my own stuff up while she left a huge mess, that was her royal prerogative. While I worked on hanging my outfit back up, I kept my eyes out for another one that wouldn’t be too embarrassing. Eventually, I spotted one: a doctor's smock and mask, complete with stethoscope. Nothing to be embarrassed about in that one!

By the time I'd pulled it off the rack, though, Princess Luna came out from behind her wardrobe. “Okay,” she called out.

I hung the doctor's outfit on the latch of my own wardrobe and stepped out to be polite and see what she looked like in her socks.

My eyes went wide when I saw her. The socks on her front legs went up to just below the second joint, but the socks on her back legs went so high that they covered a little bit of her butt. It really accentuated the shape of her legs ... in a way that made me feel funny inside. And that wasn't the only thing she was wearing. There was a little strip of fabric around her waist, matching the same color with the frills around the edges, but I'd never seen anything like it.

“Those socks look great!” I said. “But what's that other thing?”

“Oh this?” She rubbed the cheek of her butt, just above the seam of that weird bit of fabric. “Come close over here,” she whispered, “where Blue can't see us, and I'll show you.”

We snuck into the slight alcove between the wardrobes, right up next to the mirror, where Blue Dreams wouldn't be able to see us clearly. Princess Luna turned around in front of me and showed me her butt. “These are called 'panties',” she said. “Do you like them?”

It covered her in a kind of triangle shape, narrowing between her back legs until it only covered her filly parts, which it wrapped around snugly. The frilly edges in that spot disappeared into the crevice between her bulge and her butt cheeks.

I found it hard to breathe all the sudden. “It's ... uh, really nice.” Somehow, even though she was much more covered than I'd seen her before, these panties were able to show her off in a way that made me stare no matter how much I tried not to. It was somehow a lot more special than seeing her naked.

“The fabric is really nice and soft. Touch it.”

My hoof rose up before I managed to have second thoughts, and I only stopped it a moment before touching her. Still, though, she'd told me to, and everypony said that I was supposed to do whatever the Princess asked me to...

I touched her through her panties, high on the curve of her butt, as far as possible from those dangerous parts I wasn't supposed to look at, much less touch.

Even that touch seemed to affect her, though. The bulge in her panties pulsed outward a little, and then a dark, wet spot began to spread from about there. For some inexplicable reason, my hoof slid down the firm roundness of her butt, tracing the edge of her panties, and ended up right on top of that soft bulge. I felt it twitch again under my hoof before I realized what I was doing and yanked my thoughtless hoof away. The wet spot grew a little wider...

“Oh no! I'm so sorry! I...” I'd touched Princess Luna in the place I should never touch! And now ... and now she was leaking from there! “I didn't mean to!”

Princess Luna turned around. “Calm down – I'm fine.”

“But... But your...” I couldn't say it ... I wasn't even sure what was the right word for ... that.

She glanced over at my doctor's outfit. “Well, if you want to make sure I'm fine, put that on, and we'll go play doctor, okay? Just let me get my nurse outfit on.”

“I... Okay.” I still felt really bad about touching her in that place where no filly should ever be touched or even looked at, but if she said she was fine, she was probably right. And I would be glad to be done with this dress-up game ... it was getting pretty uncomfortable.

I went over to my own wardrobe and started putting on the doctor outfit. As I struggled my way into the too-big white lab coat and worked on buttoning it up, I managed to calm down somewhat. Okay, so I probably shouldn't have touched Princess Luna like that – it had been an inexplicable mistake. But she had told me to do it ... so that made it sort of okay, right? And most importantly, she didn't seem to mind, and nopony else had seen it, so it looked like I wasn't going to get in any trouble for it after all. As I hung the stethoscope around my neck, my mind drifted back to what she'd felt like there, so soft and warm in that special little place ... was that what all mares were like?

“Are you ready yet?”

I hurried out from behind my wardrobe's door to see Princess Luna, though I wasn't sure what the rush was for.

When I saw her, I immediately understood what the rush was for. Her nurse outfit also seemed a little too small for her, like it could barely stretch around her body. The white button-up top strained at its buttons, and the short white skirt clung tightly around her back legs, barely hiding anything. A little white cap with a red heart on it completed the outfit. She hadn't removed the socks, I could see. There was a gap where I could see her blue fur between the socks and her sleeves in the front, and in the back, the pinkish socks disappeared all the way up into her skirt.

Seeing her like that ... it made me feel weird inside again. Weird and warm ... but that feeling was starting to be pretty pleasant the more I got used to it ... I wanted to look at her more, I decided. Had she taken off the panties before she put everything else on? For some reason, I really wanted to know that now – now that I couldn't see.

“Come on,” she said, leading me across the room again. “It's time for a new game. Let's play doctor!”

I followed her eagerly, my eyes locked on the little white skirt constricting around her upper thighs. It mesmerized me, the way her legs and butt cheeks moved underneath the tight fabric, her tail swishing back and forth above it.

Blue Dreams cleared her throat as we passed by her. “Playing doctor already, young lady? You just met that poor colt this morning – have a little decency, won't ya?”

Princess Luna stopped walking. “That will be enough nannying for now, Blue. Why don't you take a break for a couple hours?”

It was clear from the look on the old pony's face that she had a lot more that she wanted to say, but after a moment's hesitation, she bowed her head slightly. Moving with surprisingly fluid speed, she rose from her rocking chair and backed out of the room, showing Princess Luna the utmost respect the whole time. Somehow, the two guards next to the door also knew this was their cue to leave, and they followed her out.

Shaking her head at the display as the guards closed the door behind them, Princess Luna looked back at me over the curve of her skirt-clad rump. “I don't make her back out like that. She's just doing it as a way of complaining about being bossed around. But she should know I don't really need a nanny any more than my sister does ... even if my sister still insists that I have one.”

I nodded, though I still wasn't sure just what had happened. Why didn't Blue Dreams want Princess Luna to play doctor with me so soon after meeting me? And why did Princess Luna think she had to get Blue Dreams out of the room in order to play like she wanted? And why was she worried about what her nanny thought if her nanny had to do whatever she said? It was all very confusing, but I shrugged it off and followed as the Princess led me the rest of the way to her doctor's office set.

It was a really impressive setup. It looked in every way just like a real doctor's office, though the furniture was foal-sized.

“I guess I should be the patient first, since you're worried about me?” Princess Luna asked.

I wasn't sure how this was going to work, but I nodded. “Okay.”

Princess Luna's face changed. She suddenly looked pained ... stricken. “Doctor, Doctor,” she cried in falsetto, “some strange colt touched me, and I'm not sure if I'm going to be okay! Help!”

“Uh, um...” Even though I knew it was an act, the urgency of it surprised me, and I wasn't sure what to do. “Um, okay. Why don't you lie down on the table there and I'll have a look?”

Princess Luna smiled, which I supposed meant I'd said the right thing. She hopped up onto the examination table and laid herself down on it, belly-up. She crossed her front hooves over her slim belly and let her back hooves hang off the end of the table.

A slight rush of opportunity hit me ... I could definitely find out if she took the panties off or not while she was in this position. But I knew I shouldn't be obvious about it. So I began circling around the table, walking around her head first. And I kept up the act: “So, um, have you been experiencing any symptoms?” I winced, knowing that sounded weird, but I'd only been to a real doctor a few times in my life, so I was doing the best imitation I could manage.

“When that colt touched me, it felt really weird and tingly.”

“Mm-hm...” I nodded as I walked around the other side of her. “Sounds serious.”

“Oh it is! I think I might need an injection.”

That made me break my stride for a moment. “An ... injection? I'm not sure I'm, uh, properly trained for that.”

“I'm sure you'll figure it out.” She looked at me and grinned.

“Uh-huh...” I was coming around to the foot of the table now, and most of my attention went to looking at Princess Luna's body. Slowly, I eased around her pink-socked leg, until I could finally see right up her skirt. Yes, her panties were still there. And the darker-pink wet splotch on them had gotten even bigger. I could sort of see the outline of her slit and the two lips on either side of it through the damp fabric...

“Doctor Pepper... Paging Doctor Pepper,” Princess Luna called out.

Only then did I realize that I'd been staring up her skirt for far too long. I had to cover for myself somehow. “I, um... Could you show me where you're feeling these symptoms?”

“Uh-huh.” Princess Luna reached down with one of her socked front hooves and pulled the front of her skirt up. She rubbed the wet bulge in her panties with it. “It feels funny right here.”

I stared, open-mouthed. Why was that so fascinating? I knew it was probably wrong, but I couldn't help but try to find some excuse to look at her more. “Well, maybe I should examine it more closely?”

“Yes. Please do!”

Bracing my front hooves on the table, I came in closer, pushing up between her stocking-clad back legs. I leaned in until my face was just barely managing to not rub on the little bit of her inner thighs that weren't covered by the socks. She was so warm. I could feel her heat all around me.

“Is it serious, Doctor?”

I hesitated. “I'll need to examine it ... is that okay?”

“Please hurry! It feels really tingly!”

I reached one hoof up and touched her little mound reverently, slowly sliding across the soft bulge, going slow this time and savoring every sensation, committing it to memory because I had a feeling I'd be replaying it over and over to myself later.

She moaned and squirmed a little against the table. “Yes, that's the spot. Right there.”

My breath caught in my chest at the thought that popped into my head ... but maybe I could get away with it... “Would it be alright if I removed this clothing, Ma'am? I should examine the spot directly.” It was a long shot ... but I had an undeniable urge to know what she felt like skin-on-skin, not through the soft cloth.

“Um, okay... If you need to.” Without waiting for me, she used her magic to slip the panties down her thighs, forcing me to back up out of her way as she pulled them down and off, eventually letting them drop to the floor.

And then I could see her special spot. And wow, looking at it really was making me feel special. I came in close again and brazenly stared at her cute slit. It was covered in shiny wetness now, and a little bit of the clear fluid drizzled down over her tail hole. It was a long while before I came back to myself and remembered our game. Right... “So, this is the source of your problems?” I reached up with my hoof, almost touching her, but not quite. I still wasn't totally sure I was supposed to, even though I felt like I really wanted to.

“Uh-huh.” Ever so gently, she touched the top of my outstretched hoof, pressing the soft inner part of it down onto herself.

This was even warmer, and even softer. Her supple skin slid across my inner hoof so amazingly. Yes, I would definitely be remembering this for later. This was incredible!

It winked against my hoof, and I yanked back away from her on instinct. As her slit winked open again, I saw a flash of hot pink flesh inside. I gulped, overwhelmed with what I was seeing, but still entranced by it. I barely had the presence of mind to keep up the game. “Yes, um, yes that's definitely the source of your trouble. It's your ... your, um...”

“Don't they teach you anything in medical school?” Princess Luna giggled. “That's my pussy.”

“Your ... pussy.”

“So how do we make it better, Doctor?”

I could only stare at this strange and enticing new revelation. So this was a 'pussy'. I had overheard my big brothers talking about 'getting some pussy', but I'd never known what that meant until now. Though ... I was still a bit unsure what you were supposed to do with pussy once you got some, but I did like looking at it and I really liked touching it...

“Doctor?”

Right, the game. “Um, I'm not sure how to make it better...” I only just found out what it was called, for pony's sake! How was I supposed to know what to do with it?

“Maybe you can kiss it to make it better.”

Was that how it worked? My mom had kissed boo-boos in the past to make them feel better, though it didn't actually seem to work all that well. But it was worth a try, maybe, and I didn't know what else to do.

So I leaned in again, closer this time, and I puckered my lips. Slowly and carefully, I planted a tiny kiss right on the middle of her glistening slit.

“Mmm, yes, that does feel a little better. More!”

I kissed her again, a little more firmly, and this time her pussy winked open, smearing clear juices over my lips and nose. The stuff smelled really strong. It wasn't bad, just strange, like nothing I'd ever smelled before. The scent of her went straight to my head, making me feel a little dizzy and weak in the knees, and yet, it seemed to give me a rush of strength at the same time ... and I definitely wanted more. I went in again, kissing the soft, warm lips of her pussy without being asked and smearing more of her juices on my muzzle.

“Ah! Oh yes!” Princess Luna grabbed my horn and pushed my head down to encourage me. “More! Use your tongue!”

I did just what she said, licking her tiny slit eagerly. She tasted a little tangy and it was kind of weird, but she made cute little sounds every time my tongue touched her, so I kept going, licking up and down.

After a few moments of that, it happened that I licked the top of her slit at the same time she winked open, which pressed a little nub of pink flesh against the tip of my tongue.

“Yes!” she squealed. “Yes, right there!”

Since she liked it so much, I tried to do it again each time she winked. Eventually, I figured out that I could slide my tongue a little way into her and touch that nub even when it wasn't poking out, though it usually did flick out as soon as my tongue brushed it.

And each time I did that, her grip on my horn tightened. She squealed and squirmed constantly, gripping my head between the hot firmness of her inner thighs, her velvety fur squeezing me tighter and tighter until...

“Oh Pepper, yes!” Princess Luna went rigid against the table, and a new gush of warm wetness splattered against my face, quickly cooling on my fur as she trembled there.

I tried a few more licks, but she pulled up on my horn, lifting me away. Now I could see her face as she looked down at me. She had broken into a light sweat, and her cheeks were very, very flushed. Her chest heaved with every breath, but she was still smiling hugely. “You... You make a very good doctor,” she said once she'd caught her breath.

“Does your, um... Does your pussy feel better now?”

She nodded, still smiling. “Mm-hm.” But then she seemed to notice something as she looked down at me.

Had I done something wrong? I hoped not! I had a feeling that I could get in a lot of trouble if—

“Oh, Doctor Pepper! It looks like you have a problem, too!” She pointed down at my lab coat.

“What? I don't have any—” When I looked down, I saw what had happened, and I was mortified. My thingy had come out, and it was poking through a gap between the coat's buttons. “Oh, um, I didn't mean to. I mean, I'm sorry! That usually only happens when I need to pee, but I'm really not going to pee now. I don't know why it's doing that! Please don't be mad!”

She hopped off the table and straightened her skirt. “Don't worry. It's nothing Nurse Luna can't handle. Here, come up and lie down on the table. It's time for me to examine you and find out what's wrong.”

“Um, I'm not sure that's the kind of thing we should—” My head was spinning with the stress of this new development. “I mean, maybe it's normal? I'll just...”

“Nonsense.” Princess Luna patted the table. “Up you go.”

“Um ... okay.” I slowly climbed up onto the table, feeling very self-conscious about how exposed my 'problem' would be when I lay on my back ... but there was no avoiding it. I settled down with the impossible hope that she wouldn't see anything through the lab coat.

That, of course, didn't happen. As soon as I plopped myself down, my thingy pressed against the coat, the tip of it still poking out through the gap between two buttons. It made the stiff white fabric tent up in the middle above my lower belly, making it blatantly obvious that something was going on there.

Of course, Princess Luna went straight for it. She stared closely at the exposed tip. “Oh my. For such a little colt, you sure do have a really huge ... problem.”

Why was it doing this? I didn't need to pee! Was it because of what I'd been doing with her pussy? I remembered how the smells had caused some strange stirrings down there, but I had been too distracted at the time to pay any attention to what was going on. My thingy never did anything like this before! It only came out when I was about to pee, and it never got so big or so stiff. I really did have no idea what was going on... But maybe 'Nurse' Luna could tell me?

She poked at the exposed tip, making it wiggle back and forth. “Hm... Yes, I'm going to need you to disrobe.”

I began hesitantly fumbling for the buttons, still vainly hoping that my thingy would go back where it belonged and spare me all this embarrassment.

But that was too slow for Princess Luna. She used her own magic to strip off my lab coat and other accessories in a blur of motion, leaving me bare naked on the table ... and completely exposed for her gaze.

“Oh wow...” She bit her bottom lip a little. “How does it feel?”

“It feels, um, really weird. I'm sorry, it doesn't usually do this, I don't know what—”

“Ssh.” She came closer and touched it with one sock-covered forehoof. “Yes, you definitely have a lot of built-up tension here.” She began softly stroking it up and down. “How does this feel? Any better?”

“Nngh...” I squirmed a little. The sensations were so intense ... it was hard to tell!

She smiled and began using both hooves, with a little more pressure. “How about this?”

“It's ... it's ... mmm!” The soft fabric of her socks felt amazingly good when they slid against my thingy, better than anything I'd ever felt before. But it seemed to be making my problem worse, not better – it swelled up a little bigger and got even stiffer, though I did my best to stop it.

“Oh yes, that's definitely the source of your problem.” She paused for a moment, her hooves still wrapped around my shaft, and looked up at my face. “What do you think I should do to fix it?”

“I... I don't know! It's never been like this before.”

“How about I kiss it to make it better?”

I thought back to what happened when I'd tried that on her. “I don't know. When I kissed your leaky spot, it only made it even leakier...”

She giggled. “But you did make it feel a lot better. I think it's worth a try, don't you?”

“Um, I...”

Lifting herself up higher on the table, Princess Luna brought her lips up toward the flattened tip of my thingy. She pulled it toward herself with her hooves.

“No, stop! Don't kiss it – I pee from there!”

She looked up at me, her face almost touching the tip. “It's okay. I pee from where you were kissing me, after all.”

“Wait, really?” I blanched. “Ew! Gross!”

Princess Luna laughed. “Oh, get over it, you big baby.” Without waiting for me to respond, she bent down just a little lower and planted a firm, wet kiss on the tip of my thingy.

That sent an immediate shudder through me, making my back arch and blowing any thoughts of gross things out of my mind. It felt amazing, and all I could think of was how my brain was screaming for more.

But I didn't even need to ask. Princess Luna seemed to already know I'd want more. Without pulling away from me, she slid her soft lips all over the tip, then started planting a line of warm kisses down the length of it, overlapping each one, suckling with her lips and tongue as she went as if she was licking a huge popsicle.

I shuddered in place, not understanding what was happening to me ... and not really needing to. The sensations she was giving me flared though my whole body, richly giving my thingy exactly what it wanted, but also tingling up my back and through my chest, leaving me breathless.

She made it down to my balls, and she gave each one of them a big, sloppy kiss, too...

That brought an all-new tingling to me, and the warmth there somehow made me feel like Princess Luna wanted me to ... to do something. I could feel myself building toward that something when she came back up to the tip and kissed it again.

“Pr— Luna!” I gasped. “What should I...?”

Before I could finish my question, she did something that surprised and amazed me. She let her lips slide open wider, and she took the tip of my thingy into her mouth!

“Unf!” My question faded from my lips as hers slipped lower. Was she... Was she trying to eat my thingy? But I didn't feel her teeth on me, only the amazing wet warmth of her lips and her swirling tongue. It felt so good it made my legs tremble against the table's stiff cushions.

When she started bobbing her head up and down a little, I was beyond caring about how weird it was. My thingy seemed to have a mind of its own, and that mind was telling me that this was exactly what I wanted. Every time she moved against me, fireworks lit up behind my eyes. Every time she made a little humming moan as she went down, my heart wanted to burst.

Only, it wasn't quite what my thingy wanted... Even though her hooves stroked my shaft below, her mouth could only reach the top quarter of my thingy at most. The more I felt her touch, the more sure I was that I wanted to feel something like this on all of it.

“Luna,” I cried out desperately between huffed breaths. “I need ... I need more!”

She pulled her mouth off of my thingy with a wet pop as her sucking lips came off of the tip.

“No, no!” I wanted nothing more than to have more of her, not less. This was terrible! I groaned from the shockingly deep need I was feeling. “Please, more!”

“Is that helping?” she asked.

I hissed in a deep breath through my nose. The pressure deep inside my thingy was incredible. But I had to keep it together ... this was Princess Luna! I couldn't get weird with her, especially not now! “It ... it feels really good, but my thingy feels weirder than ever. I think it's getting worse...”

“Oh no!” She covered her mouth with her hooves, which tragically meant she wasn't touching the shaft of my thingy with them. “We'll have to try something else. I'm going to go look for some bandages.”

“No, please, just do more of...”

But she was gone, off the table entirely. It almost hurt how much I wanted her back on the table, back kissing the tip of my thingy, taking it into her mouth... But she was gone. I rolled over in the direction she went, looking for her.

Apparently, looking for bandages meant she had to take off her nurse outfit for some reason. She'd tossed it on the floor next to her, leaving her wearing only the long, pink socks. She was facing away from me, her face buried in the bottom-shelf drawer she was rummaging through. Her cute butt wiggled back and forth, held up high and framed by those long socks. Her tail wiggled even higher as she searched through the drawer, leaving her ... her pussy completely exposed. It was even wetter now than when I'd been kissing it, leaving little glittering streams slowly running down her inner thighs until they met the hems of her socks and soaked in there, darkening them just like her panties. Her pussy winked open again, flashing that pink nub at me.

That sight flipped some kind of switch in my mind. I was barely in control of myself as I slipped quietly off the examination table.

She didn't seem to notice, staying right where she was. She seemed oblivious to me...

I went over to her in some kind of trance, mesmerized by the beautifully pert pussy bulge nestled between her tight, round cheeks. My thingy swung underneath me as I came up behind her.

“Pepper, are you—?”

I hefted my front chest up onto her back, running entirely on instincts I didn't understand. But my body knew what to do. As I humped blindly forward, my tip made contact with her warmth.

“Oh, Pepper!” Princess Luna pressed back against me, whether from desire or from instinct of her own, I couldn't tell...

And my tip squeezed in between her pussy lips, into her glorious wet heat. I gasped as I felt her – it was kind of like when she had her mouth on it, but so much warmer, and now her softness fit smoothly around me, squeezing my tip tight.

We both held still there for a cherished moment, trembling in place as our bodies became acquainted.

Then she made a tiny sound, just a little “Unh...” and that lit the fires of my instincts all over again. I pushed into her, only knowing that I wanted to feel more of what I was feeling now. And I got more.

My shaft glided smoothly into her, deeper and deeper. She moaned again when the ring around the middle of it pushed its way past her slick lips, which only drove me to push more, all the way ... until finally my thighs touched against her butt and the rim of my sheath kissed her pussy.

This was heaven! Everything inside me, every instinct just screamed 'Yes! Yes! Yes!' now, with no room for hesitation or second thoughts. I could feel Princess Luna's mysterious inner walls spasming around my shaft, and I could even feel that nub pressing against my base over and over again as her pussy winked around me.

I only got a few thrusts in and out of her deep, hot tunnel before I felt the pressure building inside me again, like the way it had when she was kissing my tip, but even more ... way more.

“Oh, Luna!” I cried out, grabbing her hips and clutching her body close to me. I shoved myself in as deep as I could. Somehow, she seemed to be squeezing my tip even tighter now!

She squeaked out an “Ah!” as I bottomed out in her, looking over her shoulder at me.

That was all I could take. The pressure built into an insurmountable wave, and before I knew what was happening, I felt a swell shoot down through my shaft and then a new warmth at my tip. It pulsed over and over again as flashes of pleasure burst inside me. For that beautiful moment, it felt like this was the culmination of my whole life, the best thing that could possibly happen.

It was over in a flash, though it seemed like much longer... The pulses got weaker and weaker, and I collapsed onto Princess Luna's back, totally spent.

“Ooh... Oh yes.” She looked back into my face with longing in her eyes, a deep blush on her cheeks. “Oh, Pepper...” With one hoof, she reached up and touched my cheek, then pulled me a little closer. We both had to strain to reach, but the kiss was worth it, the cherry on top of this big, creamy sundae we'd just made together.

After enjoying the moment for just a little longer, Princess Luna slowly slid out from underneath me. My thingy popped out of her just before I got my front hooves back on the ground, and I saw a bunch of white goop splash out of her once I wasn't filling her anymore. It quickly slowed to a trickle, though, oozing down onto her now-soiled socks.

By then, I'd managed to catch my breath a little. “L-Luna, it's leaking again ... but now it's white...”

“That's normal; don't worry about it.” She turned around and kissed me again, and that felt like the most natural thing in the world for some reason.

Now that the heady rush of feelings was dying down, it began to occur to me just how strange all of that had been. I would have been panicking if it wasn't for the warm blanket of relaxation settling over me. “What happened? What did we just do?”

Princess Luna grinned. “We just had sex, silly.”

“Sex?”

She blinked at me for a moment, seemingly shocked by my question. “Oh, wow. You really are as innocent as you pretend to be...” But then she smiled. “Well, for a newbie, you're pretty good! It would have been nice if it lasted a little longer, but it was really good at the time.”

Okay, so whatever 'sex' was, I was apparently good at it ... nice to know.

“Maybe next time, you'll be able to get me off as well.”

Get her off? What was that supposed to mean? I was the one who got off of her in the end... But there was a more pressing question that her words brought up: “Next time? We're ... we're going to do that again?”

“Well, you want to, don't you?”

I nodded vigorously.

“I thought so,” she said with a wide smile. “I've had a lot of different colts as playmates over the years, but I think you're going to be one of my all-time favorites.”

“Um, thanks...” I blushed and rubbed the back of my neck. It felt really good to hear compliments like that from her. Not as good as I'd felt when I was doing sex with her ... but still very good in a different kind of way.

“Now, since you apparently are a complete newbie, I guess I'd better explain a few things... First, we can't let any grown-ups know about us having sex, or they won't let us do it anymore. You don't want that to happen, do you?”

I shook my head.

“And second, having sex is something very special two ponies can share, but even though it feels really good, not everypony wants it all the time. You shouldn't do something like this with anypony else unless you're totally sure they want to, okay?”

I nodded.

“I mean it – even the way you mounted me while I wasn't looking would have been really bad if I didn't want you to.”

'Mounted'... there was another new word for me to learn... But Princess Luna was still looking at me, expecting an answer. “I understand,” I said.

“Good.” She smiled at me, which made my heart flutter all over again. “Now, one of these drawers has some medical cleaning wipes, and I think we could both use a little clean-up. She opened up a different drawer than the one she'd been rummaging through ... or pretending to rummage through while she waited for me to 'mount' her. “How about I wipe you down, and you can wipe me down? Teamwork?”

I nodded again, smiling. I had the feeling that I was going to enjoy my future playdates with Princess Luna.

* * *

My fancy suit was all ruffled up when my mom came to pick me up later. Despite both my and Luna's best efforts, we hadn't been able to get the wrinkles out ... and there were still some stains on it from the second time we did sex that I hoped my mom wouldn't see.

She fussed over it for a few moments before recognizing the futility of her efforts and giving up. She sighed. “Well, hopefully all these wrinkles mean you and the Princess had a lot of fun...”

I nodded. That was an understatement. The Princess had shown me a whole new world of fun ponies could have with each other.

“Oh, excellent!” She clopped her hooves together. “Does this mean she wants another playdate with you?”

“Uh-huh. She said she could schedule another one Tuesday morning, the same time.”

“Hm... Well, we'll have to pull you out of school for the day in order to do it, but that's definitely worth it if you can get close with the Princess! Do you have any idea what kind of influence this could bring?”

I didn't, but Mom didn't know how very close I'd already gotten with Princess Luna... It made me blush, thinking about it, but thankfully my mom didn’t notice. We just kept on walking back to our apartment in the castle. My mom's mind was already focused on rescheduling our lives around Princess Luna's playdates ... but my mind was busily fantasizing away about what might happen during the next one.

Author's Note

This story was chosen by my Patreon supporters! Every month, I take suggestions from my supporters and let them vote to determine which story I'll write next.

If there's something you've been dying to see me write, please go to my Patreon page and sign up to be part of the suggesting and voting process.

Inviting a Friend

Three months later...

I settled back down onto the comfy reading couch in the corner of Princess Luna's playroom, still quivering a little from the incredible feeling of releasing myself up into the Princess's little filly pussy as she rode me. This must have been the dozenth time I met with her for a 'playdate', and I'd learned a lot since then ... but it still blew my mind every time.

She eased her body down onto me, lying down on my chest and nuzzling my cheek. My softening cock was still inside her, but neither of us cared to change that.

I enjoyed holding her close for a few moments, as I slowly caught my breath. Her muzzle felt nice as she planted soft kisses on my neck, and I loved the warmth of her supple body against mine. I felt like I could lie here and stroke her beautiful mane for hours, but there was something I had to ask her, and I'd been putting it off for too long already. “Luna,” I said, habitually forcing myself not to say 'Princess Luna'.

“Mm-hm?” She nuzzled my neck tenderly.

“Um... Are we special someponies?”

Princess Luna lifted herself off of me a little, looking me in the eyes. My cock slipped out of her as she moved. “Well, ah, that's a bit of a complicated question. I mean, we could think of ourselves that way, if that's what you wanted ... not publicly, of course, but just between the two of us. Why do you want to know?”

I glanced away. “It's, um ... nothing.”

“Oh no it's not. I've been around long enough to know this definitely isn't 'nothing'.” She turned my head with her hoof, forcing me to look back into her eyes. “What is it?”

Cringing, I struggled back and forth a little, but she had me pinned underneath her.

“Relax. Come on, you can tell me anything. No judgment, I promise.”

I stopped and looked straight up at her. She obviously wasn't going to just let it go, and it wasn't that bad ... so I figured I might as well get it over with and tell her. “Well, my friends at school say that one of the fillies in my class wants to be special someponies with me, but I don't know if I can ... I'm not sure if I already have a special somepony or not.”

“Oh, silly, of course you can have a special somepony!” She patted my head in a strangely paternalistic way. “What we have between us is different, special ... I mean, special in a different way. I like having fun with you, but it can't last forever, so I'm definitely not going to stop you from getting your own special somepony!”

“You really don't mind?”

Princess Luna kissed me on the nose. “Of course not. Go talk to her, ask her out on a cute little date.” She smiled wide. “And then come back next week and tell me all the juicy details!”

* * *

Next week, I was again led in by a guard to wait in Princess Luna's playroom for our 'playdate'. Of course she wasn't there yet. But I didn't just stand there and wait. As the guard left, I went over and helped myself to one of the comic books in the reading area. The Princess had a surprisingly broad selection, including quite a few early editions I'd never been able to find in any store.

Sometimes it would take hours for Princess Luna to show up ... there was no way to know, so I'd gotten in the habit of amusing myself with her collection while I waited.

This time, though, I barely got through a couple pages before she came in. As was getting more and more usual, she'd managed to ditch her nanny and guards before she even came in the door.

She darted straight toward me, leaping over piles of toys to get there faster; she smiled wide, and her eyes were eager. “How'd it go, little lovebird? Do you have the marriage ceremony planned out yet?”

I blinked at her, mortified.

“That was a joke, silly! But really, how did it go?”

“Oh, right...” I made a lame attempt at laughter, then thought back to when I had approached Radiance...

It had been right after school let out, when everypony was milling around the school's courtyard, most of them waiting for their parents to show up and take them home. I spotted Radiance not far away; she was talking to her own friends. Or, rather, her friends were talking animatedly to each other, and she was listening to them. She was one of the few earth ponies in our Canterlot school, with white fur and a short minty-green mane ... she was a little smaller than most fillies her age. As I watched her, she glanced in my direction.

Our eyes met for a moment, and she quickly looked away, her cheeks reddening.

“Go get her,” one of my friends said, elbowing me in the ribs. “My sister says that Dew Drop said that Radiance is totally into you.”

I looked over at him. “I don't know ... what if it's some kind of trick...?”

“Dude, just look at her! You see the way she blushed? She's definitely into you.”

Taking a deep breath, I took my first step forward. “O-kay...” The walk over to where Radiance stood seemed to take ten times longer than it should have, and though I probably didn't have any real reason to feel nervous when I started it, by the time I got close to her, I was legitimately worried that she'd notice how sweaty and trembling I was and be grossed out by it. I stopped a few paces behind her, already making great progress in convincing myself that now wasn't a good time, that I should wait until sometime later when I looked more presentable ... when I noticed the presence of my friend behind me.

Before I could do or say anything, he shoved me forward, sending me stumbling into the middle of Radiance's group of friends. Once I managed to steady myself, I froze for a moment, completely petrified.

“Who's this dweeb?” the tallest of the three fillies asked, sweeping her mane out of her face. “You know this guy, Dew Drop?”

The other filly looked at me over the rims of her stylish glasses, giving me a deepening frown. “Nah. He looks lame, and he's a blank flank. I don't hang out with lame blank flanks.” She glanced over at Radiance. “Radie?”

Everything was crashing in, and this was going just as badly as I ever could have feared, but then Radiance stepped in. “His, um, his name is Pepper Zest. He's in my geography class.” She looked back at me, stuttered for a moment, but then forced herself to say it, “Did you ... want to talk to me, Pepper? We could go over there if that's okay.”

I followed her a little way away from her friends, trying to ignore the jeering hoots they made at us.

“I'm really sorry about those two,” Radiance said. “They're nice ponies, really, but sometimes they don't realize how mean they're being.”

“It's okay, I don't mind.” That was a bit of a lie – they had terrified me – but it was a polite lie.

“So, um...” She pursed her lips together, looking anywhere but at me.

I smiled. Now that I was away from Radiance's friends, I felt a lot less nervous about talking to her ... and my experiences with Princess Luna had gone a long way toward alleviating those nervous flutters that used to come to me when I was around mares and fillies. “You live up near the palace, right? I do, too. Why don't we walk home together?” I normally walked home alone, up to the apartments near the palace, and I'd seen her around there before. She must live nearby.

“Well, I... Um, I normally walk home with Dew Drop and her mom...”

I sighed. This might be harder than I thought.

“... But I guess as long as I tell Dew Drop, I could go home with you instead.”

That brought me an instant smile. “Great! Let's go!”

I almost ran off right then and there, being so excited, but she grabbed my tail at the last moment. “Wait! I've got to tell Dew Drop first!”

The walk home that day was the best walk home I'd ever had, by far.

It took a little while to really coax Radiance out of her shell, but once she felt comfortable enough to say more than a couple words at a time, I found out she was really fun to talk to, with all kinds of jokes I'd never heard before ... and she seemed to notice a lot of things in the world that I'd never thought of. The walk flew by faster than ever before, leaving me shocked when she said, “Okay, this is where I live.”

It was an apartment building just a couple blocks from my own ... silly me, I'd been assuming that I could walk all the way home with her, and now I was crushed that we'd suddenly have to split ways. But I had to put a brave face on it, I was sure. “I, um... It was fun, walking with you. I almost wish I didn't have to go...”

She smiled coyly, then leaned in close, whispering next to my ear, “Do you, um ... want to come up and ... uh, see my apartment? My mom and dad won't get home until dinnertime.”

That made me grin, and it made my ears perk up. “Sure!”

All the way up her building's stairway, I was unabashedly looking right under her tail. She might be small, but she had a gloriously nice—

“Pepper!” Princess Luna's voice broke me out of it. “Equestria to Captain Pepper!”

I shook myself, then looked back at Princess Luna. “Oh, um... Sorry. Did I kind of zone out?”

“Only for like ten minutes.” She rolled her pretty eyes. “I take it that means things went well with your special somepony?”

The warm glow of my new memories lit up my whole body, even now, after I'd been snapped out of them. “Yeah... It was great.”

“So tell me how it went. You promised me juicy details!” The Princess came even closer, and her eyes were huge as she stared at me.

Had I really promised her that? Either way, it didn't matter – I was sure she'd be able to find some way to coerce me into telling her, so I'd better just tell her to begin with and save myself a lot of trouble. “Well, I asked her if she wanted to walk home with me, and she did. That was great, and at the end of it, she invited me in to stay at her place a little while until her parents came home.”

Princess Luna gave me a lecherous smile. “Sounds promising ... go on.”

“Well, we had a good time there, so I walked her home the next day, and the next. We've been going to her place pretty much every day this week.”

The Princess's shoulders slumped. “More juicy details!”

“Oh, right.” I felt my cheeks heat up a little at the idea of telling her, but I knew there was no avoiding it. “Well, the first day, we just talked for a while, about lots of things. We both, you know, kept getting closer and closer as we talked. But I had to leave before anything happened, because her parents would be home soon.” I remembered back... I'd masturbated endlessly that night, but Princess Luna probably didn't need to know that part. “The second day, as soon as we got alone together, I could tell from the way she was looking at me... Well, um, we kissed. And she said I was her special somepony. And every day since then, we've kissed a lot, and we've lain down on the couch, touched each other and cuddled...”

“Yes, yes,” Princess Luna said, leaning toward me eagerly. “Go on!”

“... And that's pretty much it, I guess. She's been, um, really hesitant to do anything ... more intimate.”

The Princess's face fell. “Humph. Well, that was anticlimactic.”

I shrugged.

“Well, what's her problem? Doesn't she know what a hot little stud she's missing out on?” She poked me in the chest and giggled.

Rubbing where Princess Luna had poked me, I took a deep breath. “I asked her, eventually. She didn't want to say at first, but eventually she admitted it's because she's never done anything like that before, and she's scared that she'll do it wrong and I won't like her anymore. I've told her that I'll like her no matter what, but she says she still feels that way, and she can't get into it when she's all scared and nervous.”

“Oh...” Princess Luna rubbed her chin for a moment, then her face lit up. “That's it! Yes, that's the perfect solution!”

“Huh?”

“I'm going to invite your little special somepony to our next playdate! I'll get the two of you together, and I can teach her some things – then she won't be afraid of doing it wrong anymore!”

I blinked at her. “You'd really do that?”

“Just tell me her name, her parents' names, and her address, and I'll have an invitation in the mail by sundown!” The Princess leaned in and kissed me, just a quick peck on the lips that I was too surprised to think of avoiding. She winked at me. “But first, let's have some fun with each other.”

I wanted to. Oh, I really wanted to, after much my cuddling and make-out sessions with my new special somepony had left me pent up, but... “Is it okay to do that when I have a special somepony? Won't she be mad?”

Princess Luna stroked my cheek. “I told you, what we have is different. Now come on!” She spun around and lifted her tail, showing me the bright pinkness inside her dark-blue pussy as it winked open. “It's been a whole week, and I need my playmate!”

* * *

“Okay, dear, you have fun with the Princess!” My mom dropped me off in the anteroom again, but without any fussing and primping, as had become more usual now that she'd gotten used to these playdates with royalty. She hadn't even made me wear any formal clothes – I'd managed to convince her that Princess Luna didn't want me to.

I gave her a quick hug, then went inside without any fanfare – she'd also become less worried about arriving on time: today we were nearly late for the first time ever!

Inside the waiting room, I found Radiance and her father. She wore a dark blue gown covered in elaborate ribbons of lighter blue ... something she'd doubtless been given just for the occasion, since it matched Princess Luna's colors so well. Her somewhat-chubby father was so engrossed in making sure every ribbon was in place that he didn't even notice me coming into the room.

Radiance noticed, though. “Pepper!” she said, breaking into a smile for what looked like the first time in a long time. “You're coming to see the Princess, too? Thank goodness you're here! Please tell my dad that I look perfect already – he's been doing this for hours, and I can't make him stop.”

I wouldn’t have expected the blues of her dress to go with her white and pale green, but when I gave her a long, appraising look for her father's benefit, I couldn't help but think that somehow, it actually worked. Though I'd been accustomed to seeing her as cute, in this gown she seemed ... elegant. It didn't hurt that the fabric clung tight around her waist, then flared around her hips, paradoxically making me all the more eager to get her out of it. “You look lovely,” I told her. “You really do.”

She blushed, but thankfully, her father was too busy running a brush through her already-perfect mane to notice that. “I don't know,” he said. “What if the Princess doesn't like it? I thought the blue was a great idea at first, but now I'm sure we can't be the first ponies who thought of impressing Princess Luna this way... What if she's tired of it?”

I came over to them, sitting down with Radiance in between me and her father. “She'll love it, I promise.”

“You're sure?”

“I've been playing with Princess Luna for months now.” I touched his hoof, stopping him from preening for a moment. “I'm sure she'll love it. Radie's beautiful!”

Radiance giggled. “You really think so? I don't usually wear this kind of thing...”

“Of course!”

“Are you nervous, Darling?” her father asked. “Please don't be! I'm sure there's nothing to be nervous about. It's just a really big opportunity and it could really mean a lot. Yeah, you've just got to keep calm and relax. There's nothing to worry about – I'm sure you won't make any bad impression and—”

“There really is nothing to worry about,” I said. “I told you, I'm sure Luna will love everything about her.” Only after I said it did I realize that I'd said 'Luna', not 'Princess Luna'.

But it seemed like that slip-up was just the thing to convince him that I really knew Princess Luna – I was so comfortable with her that maybe I did know that she'd like Radiance just fine. He leaned backward, staring at me over the fluff of his daughter's dress. I gave him the best smile I could muster ... which was actually pretty genuine; I was really looking forward to today's playdate. Radiance herself was just quietly blushing, her cheeks turning bright red as we talked about how lovely she looked.

Her father leaned in close to her and started whispering in her ear, but since I was close, I could still hear it. “Now, I do want you to be on your best behavior, but you can't just let that colt do all the talking for you. You have to speak up for yourself if you want the Princess to—”

A guard marched into the room. “Pepper Zest, Radiance. Please come with me.”

Radiance and her father jumped up immediately and hurried toward the door; I followed a little more leisurely, knowing that Princess Luna probably wouldn’t be in the playroom yet.

There was a little bit of a problem at the door, though. Radiance had gone through already, and her father was trying to follow her, but the guard kept stepping in his way ... while also keeping the doorway open for me, which was a struggle even for someone with his level of training. “Pepper Zest and Radiance only, please,” the guard said. He added a “Thank you for your cooperation,” even though Radiance's father was still trying to find a way to step around him.

“Don't worry about your daughter,” I said. “I'll take good care of her.”

That was enough to stop his pacing back and forth, at least. “You promise?” he asked.

I nodded. “I promise.”

With that, the guard was finally able to separate him, ushering us through the door and toward Princess Luna's playroom.

“Thanks for that,” Radiance whispered to me as we walked. “He was so worried about getting here late that we came hours early, and he's been fussing with my dress and my mane ever since!”

I chuckled a little. “I know the feeling.”

“Did you mean what you said back there ... about how I look?”

Letting myself walk a little closer to her – at the risk of stepping on the hem of her dress – I leaned in and whispered, “That was an understatement. You look amazing!”

It was still gratifying, seeing her blush. I don't think I'll ever get tired of that.

When we arrived in the playroom and the guard left us, Radiance took a good look around. “Oh wow ... this place is... Wow.” She probably would have stayed frozen in place if I hadn't been there, but she followed me over to the reading cuddy. “But where's, um... Where's the Princess?”

“She'll be here soon.” I stopped myself from reaching for the comic book shelf, realizing that I had better things to do... Turning back toward Radiance, I moved in close, then stroked a hoof over her cheek.

“Pepper,” she complained in falsetto, “what if the Princess comes in and sees us?”

I leaned in for a kiss. Her eyes opened wide in alarm as our lips met, but they soon drifted half-shut.

She moaned slightly into my mouth before pulling back a little. “Oh Pepper...” Her breathing had quickened and her face was flushed. “It's only been one day, and I already miss you so much!”

I could see her tail pushing the back of her dress upward, and I went in for another, deeper kiss. I couldn't help myself – I just loved the feeling of her mouth against mine so much! When she slipped me a little tongue, I had to force myself not to grab her and drag her down onto the reading couch. I couldn’t risk messing up her dress already.

“Hey, no fair! You're getting started without me!”

Both of us jumped back from each other and looked at Princess Luna. The Princess had somehow come into the room without us hearing her, and now she was staring at us with a mock-scowl. At least nopony else had come in with her.

Her expression quickly softened, though. “So... This is the filly I've heard so much about, hm?”

Radiance shot me a glance that made me worry... Maybe telling Princess Luna bout her and what we did together was a breach of trust...? But then she ignored me for a moment, bowing to the Princess instead. “I am very pleased to meet you, Your Highness. My name is Radiance, of the Blue Dawn family,” she said, sounding as if it was part of a well-rehearsed speech. But then, sounding much more like herself as she rose back up, she added, “But you can, um... call me Radie if you want.”

“Radie, hm?” Princess Luna looked at me with a smirk. “She's cute.”

Radiance shifted awkwardly from hoof to hoof. “Um... Your Highness? I'm not sure how this is supposed to work, but—”

“Hey!” The Princess looked sharply at Radiance. “No 'Your Highness' or 'Princess' in here, okay? Didn't you tell her anything, Pepper?”

I cringed, rubbing the back of my neck. “Well, actually, um...”

“He didn't tell me anything! I didn't even know he was going to be here, or that he'd ever seen you before. I thought I'd just randomly gotten that invitation in the mail!”

Princess Luna blinked at her. “Oh. Hmm... So you don't know anything at all about me and Pepper?”

Radiance shook her head.

“Oh, this is going to be fun!” The Princess giggled. “Tell me, what do you think of Pepper?”

Taking a step backward, Radiance looked at me, then back at Princess Luna. “I, um... He's nice, I guess?”

Princess Luna burst into laughter, failing to hold it in at first, then just letting it all out. After a few moments of that, she managed to get control of herself enough to say, “He's much more than that ... or so I hear!” She laughed a little more. “Oh, honey, you don't have to keep your secret here – Pepper told me everything.”

“Pepper!” Radiance squealed.

I cringed down, but Princess Luna came to my rescue. “No, no, it's good! Since he told me about it, maybe I can help the two of you with that little problem you're having.”

“W-what problem?” Radiance looked at her tentatively.

“The one where you're afraid of being a bad lay, of course.”

Radiance gasped at hearing the Princess say it so brashly. “I'm – I'm not...”

The Princess gave her a deadpan look, showing that she knew better – that any lies would be wasted breath.

“I don't know,” Radiance said looking at the floor. “Even though I know Pepper would like me no matter what, and no matter how much he tries to reassure me, I can't help but feel like ... like I would be a disappointment. I just know it! And no matter how much he says he doesn't mind, I know I would feel really bad if I was bad at it, and that just makes it more likely that I will be bad at it, and that makes it even worse! I don't think there's anything you could say that would—”

“It's not what I have to say that's going to help you.” Princess Luna came over and lifted Radiance's chin up. “What if I showed you how to be good at it?”

'W-what!” Radiance jumped back, her eyes going wide. “You'd...” She calmed herself quickly, though, looking more contemplative for a moment. “You'd, um, you'd do that for me?”

Princess Luna smiled. “For Pepper, really. You wouldn't believe how pent-up and frustrated that little colt's been ever since he started going out with you. You should have seen the load he blew the last time he was here!”

Radiance looked back and forth between Princess Luna and me. “Wait ... so you two, um...”

“No! I mean, well, um...” I blanched. I'd been afraid this might happen. “Wait! I, um, I can explain! It's ... uh ... it's different with Luna...” That sounded lame even to me. Why had it sounded so much better when the Princess said it?

“We sure did!” Luna pranced in place a little and smiled brightly. “But don't worry about it – I'm not going to steal him from you. In fact, I've been overdue for a new colt here, so I'll probably replace him soon.”

“Wait, what?” I snapped back toward Princess Luna. “You didn't say anything about—”

“Yes, I like them young and innocent, I'm afraid,” the Princess said, ignoring me. “He's gotten a little too comfortable with it all for my tastes, and I honestly would have gotten a new colt already, but I knew he wasn't getting what he needed without me yet, and I didn't want to leave him with no relief.”

I stared, but the gears in my head were turning fast. Princess Luna had only known about my predicament with Radiance for one week, but she was making it sound like it had been an ongoing thing that was preventing her from replacing me... Maybe this was only a show for Radiance's benefit? Maybe Princess Luna wasn't going to replace me at all!

Radiance scuffed one hoof along the floor in front of her. “I don't know... It seems, um, really weird... I mean, he's supposed to be my special somepony.”

Princess Luna came over to her again. This time she twirled one of the ribbons on the front of Radiance's gown in her hoof. “I give you my royal word: once I teach you how to take care of him properly, I'll never touch Pepper again. What do you say: may I teach you?”

What? Never again? As eager as I was to go further with Radiance, I didn't like the idea of never touching Princess Luna again ... but it wasn't like I could say anything now that she'd given her word, and there was probably nothing I could have done to change the Princess's mind anyway. I'd just have be sure to make the most of my very last time with her, I supposed.

“Y-you mean it?” Radiance asked softly.

“Would you doubt the word of a princess?”

“No.” Radiance blushed. “I, I mean yes ... no... Ugh!” She stammered for a moment before forcing herself to speak clearly: “No, I wouldn't doubt the word of a princess, and yes, I'd like it if you taught me how to, um...”

“Fuck?”

Both of us stared at the Princess, aghast at hearing a word like that out of her royal mouth.

She stared back at us. “What? That's what you want to learn, isn't it? How to fuck?”

“Um... yes, I think?” Radiance squeaked.

Princess Luna smiled at us. “Okay then. Show me what you've got so far.”

Radiance glanced at me, then back at Princess Luna. “What?” She looked over at me again, but I wasn't sure what Princess Luna wanted us to do, either.

“If you two keep being so hesitant, this is going to take forever!” Princess Luna shook her head, then flicked her mane out of her eyes. Her horn lit up with blue magic, and before either of us could do anything about it, the Princess used it to shove the two of us close together. “Now kiss!”

Our noses almost touching already, Radiance looked at me and blushed an even deeper red.

She seemed frozen in place ... so I figured I would have to be the one who made the first move. It took no effort at all to cross the hair-thin barrier of space between us and touch my lips to hers, but it felt very different this time. Even though I'd often kissed Radiance before, now it felt like I was kissing somepony entirely new. I wasn't sure if it was the different situation or the fact that Princess Luna was watching us, but I was hyper-aware of Radiance's pretty face so close to mine, of her eyes drifting closed, of every little detail of her soft lips. I reached up and traced along the curve of her cheek, up until I brushed my hoof through her silky mane.

Radiance soon overcame her hesitation, and she began to respond to me in all the ways I loved so much. She moaned very slightly into my mouth and pulled her body in closer, brushing the ribbons of her dress against my chest. Beginning to gasp for breath every time we separated, she wrapped a foreleg around the back of my neck and pulled me in even closer, letting her lips part a little, inviting me to play with her tongue.

I just couldn't get enough of Radiance's lips, and I loved feeling the gentle, feminine curve of her neck as my hoof slowly traced across. The two of us must have been making out with each other for long minutes, but it felt like only a few seconds to me. We went at it as passionately as ever, both of us getting more into it as we focused so much on each other that we gradually forgot about where we were or who was watching us.

“Go on,” Princess Luna said. “Get to the good part!”

I looked over at her. We both did, broken out of our mutually-absorbed trance and reminded of what was happening here.

The Princess sat on the floor near us, her back legs spread out in front of her, and one front hoof working in little circles over her crotch. The way she stared at us, biting her lower lip ... she looked so hungry.

“Well, um, that's...” The words wouldn’t come out; I couldn't say it.

But Radiance could. “T-that's... It's pretty much all we do together...”

Princess Luna's eyes went wide, and her hoof stopped moving. “Really? That's it?”

Radiance blushed again and looked away.

“Oh, you poor things!” the Princess came over to her, draped a hoof over her shoulder, and started pulling her away. “Don't worry, Radie. By the time I'm done today, you're going to be ready for a lot more than just that.”

Looking back at me as Princess Luna dragged her away, Radiance whimpered. “I'm not sure if I'm—”

“You're going to be perfect, trust me. First, let's get you changed. Your dress is lovely, but it's too concealing for what we're doing. But I have just the thing to give you a little confidence boost.”

Radiance's tail visibly tucked down under her dress, but she mumbled an “Okay,” and let Princess Luna lead her.

I began to follow them across the playroom, but Princess Luna looked back at me and held her hoof up. “You go wait in the doctor's office. Radie and I have some work to do.”

It felt strange, watching Princess Luna drag my special somepony away, especially after I'd gotten so worked up from making out – my cock had already slipped out of its sheath and hung down between my legs. But she was the Princess, and even as familiar as I'd become with her, I still knew better than to disobey. So I went over to her pretend doctor's office and sat down on the rolling stool next to the examination table.

Princess Luna took Radiance toward the wardrobes on the opposite side of the room, and I watched with interest, eager to see what kind of outfit she'd pick out ... but it turned out that it wasn't for me to see. When the Princess glanced back and saw me staring, she used her magic to flick the curtain across the entrance to the faux doctor's office, blocking my view.

I could peek around or under it ... and I might even be able to without getting caught. But a princess is a princess, and she'd made it clear that I wasn't supposed to look. So I resigned myself to a few minutes of boredom. I sighed as my cock began to shrink back into its sheath.

The sounds of rustling cloth and hangers being taken off the rack came from the other side of the curtain, along with more and more whispers, followed by girlish giggling.

I thought back to the first time I'd been here, when I'd given Princess Luna my virginity, barely even knowing what I was doing. It seemed like ages ago now, even though it was only a few months at most. But that first time was still special – I'd gone over the memories in my head many times, but being back in the very same spot brought a new vividness to them. So I indulged in a little nostalgia. There wasn't anything else for me to do in the doctor's office, but I could be glad at least that Radiance seemed to be opening up a little and having a good time.

As I listened to the sounds from behind the curtain, I began to suspect that Radiance was having a very good time. The whispers and giggles had been replaced by fast breathing and hushed moans. I heard Radiance gasp, then a muffled squeal. Was that ... her first orgasm? Had Princess Luna taken her virginity as well? Just how many colts – and fillies, apparently! – had Princess Luna deflowered over the years?

I wanted very badly to peek around the edge of the curtain and watch what was happening, but I forced myself not to. So what if Princess Luna took Radiance's virginity? It wasn't as if I had much room to complain, not after everything Princess Luna had already given me... And I shouldn't be jealous, because I knew that it was probably just to give her confidence for what was coming next, that it was ultimately for my benefit ... right?

Now there came more whispers, and the sound of cloth again ... but not as much giggling, for some reason. And then ... hoofsteps! They were coming toward me!

As they pulled the curtain aside, I rushed to stand up, but Princess Luna waved me back down. “No, no. Sit. That stool is perfect.” She was wearing the violet socks again, complete with panties ... an outfit I hadn't seen since the first day I met her.

But what really drew my eye was Radiance. She wore a similar outfit, but her socks were a satiny black that contrasted perfectly with her pale coat. Though she was facing almost straight toward me, I could see her back socks reaching all the way up to the bottom of her cutie mark, as well as the strap of a black pair of panties that looked even skimpier than Princess Luna's. My jaw dropped.

I would have expected Radiance to blush at being ogled at in such an outfit, but instead, she preened under the attention. “Do you like it?”

“Like it? I... I...” The words just wouldn't come out, my tongue kept getting in its own way.

She smiled. “Luna says I can keep it, if it makes me feel more confident.”

I nodded fervently.

Princess Luna pushed her forward, her hoof lingering on Radiance's rump longer than strictly necessary. “Go on, get him started. I'll be here for you the whole time.”

Radiance stepped forward, but she stopped as soon as Princess Luna stopped pushing her, and she stood there, staring at my crotch, looking right at the head of my cock as it began to peek out of my sheath slightly. She licked her lips, but her eyes looked uncertain. “I ... I'm not sure how to... I can't – it's not up yet. What do I do?”

Sighing, Princess Luna came up next to her – they were both almost within touching distance now. “Well, it would be easy enough to stimulate him just by licking and kissing what you can already see ... but let's do something a little more fun. We wouldn’t want all these sexy clothes to go to waste, would we?”

“So, I should, um... show him?”

“We should show him!” Princess Luna spun around and lifted her tail for me. She smirked over her shoulder as I took in the gorgeous way the thin, soft fabric of her panties curved diagonally across her round ass cheeks. The pert little bulge in the middle winked visibly underneath, leaving a damp spot. She nudged Radiance's side. “Come on, show him!”

Much more slowly, Radiance turned around as well. At first, her tail remained shyly clamped down, covering her completely, though I still enjoyed seeing the way the tall black socks rode up on her and curved around the underside of her ass.

Princess Luna had the solution for that, though. She used her magic, and though I couldn't see what she was doing, Radiance reacted just as if somepony was tweaking on her nipples.

Radiance's tail slowly rose, lifting up to the side as she arched her back in response to Princess Luna's magic. Nestled deep between the cheeks of her ass, her black silk panties narrowed to a little strip of fabric that barely managed to cover the bulge of her pussy. It covered hardly anything else – if it moved even slightly, her filly parts would peek out. Below, in the slim gap between her legs, I could see the blue glow of Princess Luna's magic working on her little teats. Radiance looked back at me, a desperate need for approval in her eyes.

But before I could respond, Princess Luna turned back around to face me, her horn still glowing. She grabbed Radiance's ass between her hooves and gave it a firm squeeze. “Isn't she just the sexiest little filly you've ever seen?” Licking her lips, she smacked her hoof down on one cheek, making it jiggle tightly and making Radiance gasp.

I had to nod. “She's... She's beautiful!”

Radiance's expression melted into a sultry grin when she heard that, and her pussy winked underneath the skimpy panties, making the smooth outer curves of her mound slip out from either side for a moment.

Of course Princess Luna was well aware of what my eyes were locked onto, as well as the upward progress of my cock. She slipped a hoof under Radiance's tail and slid it downward, caressing the young mare gently. “You want to see her, don't you?”

Radiance's tail flagged even higher after the Princess's touch, curling up over her back. Her eyes squinted closed.

Not needing to hear my answer, since she already knew it, Princess Luna pulled her hoof away, diverting her magic there instead ... so that she wouldn't be blocking my view. She squished Radiance's pussy side to side under the thin panties, and tantalizing glimpses of smooth pale skin flashed on either side as the panties failed to cover her completely. Holding her muzzle close, glancing back and forth between Radiance's pretty rump and me, the Princess started rubbing a little more eagerly, letting the panties slide more as she massaged that little filly mound. The supple skin underneath started to get shiny from moisture ... I caught my breath when the strip of fabric finally pulled far enough to the side that I caught a glimpse of Radiance's pink slit.

Radiance looked back at me again, her mouth hanging open now. “Is he...?”

“He's nearly ready,” Princess Luna said, eying my almost-full erection. “Just one more thing...” With her magic, she grabbed the upper strap of Radiance's panties and slowly, slowly started pulling them down.

Radiance whimpered as the thin strip of silk peeled away from between the cheeks of her ass. It stuck to her pussy with a thin sheen of filly wetness, revealing only a little of her lips at a time, making me watch every moment of it with baited breath.

Finally, the panties pulled away from her perfect little bulge, drawing a glistening, clear strand of her wetness out between her slit and where the panties had been touching it. Her pussy winked open as Princess Luna slid the panties down her stockinged legs, giving me another sweet glimpse into her hot pink snatch before the lips closed again, dribbling nectar over Princess Luna's hoof.

“There,” the Princess said to Radiance. “He looks ready now, doesn't he?”

Radiance turned and stared at my urgently hard cock for a long moment before she finally replied with a nod. “Um, um... Yes.”

Princess Luna came up to me and casually grabbed it around the base. She gave it one firm stroke with her sock-clad hoof. “Do you want to touch it?”

Her breath catching in her throat, Radiance took a step back ... but after a moment, she took several steps forward, coming almost as close as Princess Luna – close enough to touch. “I can just ... touch it? Don't I have to...?”

“It's that simple. Go ahead, try it.”

Radiance glanced back and forth between me and Princess Luna, then tentatively reached out her black-stockinged hoof. Everyone there watched with anticipation as she slowly drew closer.

Finally, the tip of her hoof touched me, just above the medial ring. My cock wavered back and forth a little at the touch, and I let out a deeply satisfied sigh. It didn't matter that this little touch paled in comparison to anything Princess Luna had ever done ... the fact that it was Radiance's hoof touching me gave it a special thrill that I'd never felt before. She drew back when it bobbed back and forth, but then grew bolder and wrapped her hoof around it, sliding up and down a little to get the feel of it.

“It's so warm, and it feels weirdly ... heavy,” Radiance said.

Princess Luna leaned in close to her ear. “Try stroking it softly up and down. Can you feel how soft and smooth the skin of it is, even though he's entirely hard?”

Doing as she was told, Radiance squeaked out a barely-audible whimper of desire. “Mm-hm.”

“It feels nice, doesn't it?”

Radiance didn't respond to Princess Luna's question. She was slowly drawing closer to me, without even seeming to be aware of it. Her eyes were fixated on the way her sock-covered hoof slid over the curved surface of my cock, her mouth hung open with her tongue drooping out a little, and her whole body quivered slightly when a drop of pre-cum welled up from my tip.

“You want to taste it, don't you?” the Princess asked.

That startled Radiance out of her fascinated stare for a moment. She looked over at Princess Luna. “C-can I?”

Princess Luna smiled. “Well, I'm not really the one you should be asking, am I?”

Radiance looked up at me instead, her eyes deep and sparkling.

“Do it! Oh please, yes!” I told her. I didn't know how much more of this teasing I could take!

When Radiance looked back to Princess Luna, the Princess just nudged her face back toward my cock with her hoof. “Don't overthink it – it's simple. Just lick.”

With one deep breath, Radiance overcame her hesitation and leaned in closer, her tongue sticking out cutely. She planted it right on the middle of my cock, pressed its soft warmth there for a moment, then slowly licked all the way upward to the tip, where she picked up the dollop of pre-cum and took it into her mouth. “Mmm,” she hummed, closing her eyes as she took in the flavor. “I... I thought it would taste a lot stronger than that. It's weird, but it's ... kind of nice.”

“There's more where that came from,” Princess Luna said. “Here, let me show you.”

Spreading my legs open wider, Princess Luna pushed her way in next to Radiance and began lavishing the closer side of my cock with her tongue. She didn't hold anything back, rubbing her whole face along the side of my shaft, then latching on with a deep, wet kiss that she slid up and down. Radiance caught on quickly and soon began emulating the Princess's techniques. She wasn't quite as stylish about it, and at one point she nearly made me laugh when she accidentally let the head of my cock boop her on the nose ... but she more than made up for it with enthusiasm, drooling all over my length as she quietly moaned to herself.

I could barely keep up with the heady pleasure of both these lovely fillies going down on me, but I did my best to hold myself back – if I got off now, I would be missing out on a lot.

When another bead of pre-cum formed, Radiance slid her tongue up my cock and then planted her lips right on top of the hole, sucking slightly as if trying to draw more out.

Princess Luna must have interpreted the filly's intentions a different way, though. “So,” she said, “you're ready to take him inside your mouth?”

Radiance popped off of my tip and looked at the Princess, her eyes wide and more than a little fearful.

But Princess Luna was already getting herself lined up. “Just cover your teeth with your lips and take it slow to begin with. I want to make sure you enjoy it your first time. Now, watch what I do.” She easily slipped the tip of my cock into the warm wetness of her mouth, her hooves holding the rest of my cock steady as she began to bob up and down on the first little bit.

I groaned in pleasure, which seemed to have a strange effect on Radiance. Her fear faded, though her eyes stayed wide. “Can I try?” she asked.

Princess Luna pulled her mouth off of me. “Of course! Please do.”

Radiance's lips were on me the moment Princess Luna was out of the way, and she pressed herself down greedily, taking a little bit more of my length than the Princess had, all while eagerly stroking her hooves over everything her mouth couldn't reach. To my shock, she didn't stop there. She kept going, taking more and more each time she went down, until finally she coughed just before her lips got to my medial ring. Suddenly, she pulled away, choking and gasping for air.

“Wow,” Princess Luna said, “She's kind of a natural! It took me a decade before I got my gag reflex under control that well.” She patted Radiance on the back as the filly caught her breath. “You know ... since you're so good at it...”

Radiance looked up, blinking the tears out of her eyes. “Mmm?”

“How about I show you an easier way to take him deep in your mouth?”

Wiping her mouth with a hoof, Radiance nodded. “I'd like that.”

Princess Luna wasted no time in hopping up onto the padded examination table, lying belly-up with her front half flopping downward off the edge. I'd seen this position before, and I knew what to do. I scooted the stool over to the low table and raised the height of the seat as high as it would go, then laid my cock over Princess Luna's face.

“It's a lot easier if you get the angle right,” the Princess said, taking hold of my shaft and moving me a bit until my tip lined up with her mouth. Then, without any fanfare, she opened up and let my cock slide straight up into her throat. I could see her neck bulge a little as the broad tip went deeper, but she took it without the slightest hint of struggle, right up to the point where my balls mashed up against her nose.

We had only done this a couple times before, but I was definitely a huge fan of it. Right away, I started humping her face, marveling at the bulge in her throat and the way her cute, slim belly stretched across the table. Her tiny teats stood out proudly, poking up through the thin fabric of her panties, and she made a cute little “Hmmf” noise every time my balls bounced against her muzzle.

But before I could get too into it, Radiance jumped up on the table, laying herself out right next to Princess Luna and copying her position perfectly. How could I resist that? Bracing my front hooves against the table, I pushed back and slid my cock out of Princess Luna's mouth. I accidentally slapped the wet length of it over her face as I scooted the stool a little to the side, lining myself up with Radiance.

Princess Luna looked around confusedly for a moment before she figured out what was going on. “My, my... You are eager!” She giggled and wiped her mouth with one of her front-hoof socks. “This is a little tricky – remember to keep breathing through your nose, and try to swallow it down rather than resisting it. If you need a break, just tap your hoof on the table, okay?”

Radiance nodded, upside down, which made her chin bump into my cock. Little strings of Princess Luna's spit dripped from it, down onto her neck.

“Are you ready?” I asked her.

“Mm-hm...”

I pulled my hips back, bringing my tip up to her mouth. “Okay...”

She took my length with incredible enthusiasm, reaching out to grab my hips and pull me in when I was going too slowly for her. And her throat was so warm and soft... Even though at first it seemed she'd put Princess Luna to shame, she did start to gag a little bit after my medial ring pushed its way past her lips.

“Take it easy,” Princess Luna cautioned. “Go slow, you've got plenty of time.”

Radiance seemed to take that advice to heart, pacing herself now as she tilted her neck and bobbed up and down.

Meanwhile, Princess Luna looked down at the lovely curve of the cute filly's underbelly, all stretched out over the table. Nothing hid her teats and pussy from the Princess's view... She licked her lips, staring down at that wonderful body on display for her. “Do you mind if I have a little fun?” she asked me.

With one last desperate push, Radiance managed to take me all the way down to the sheath, nuzzling herself up against the curves of my balls just like Princess Luna had. I gasped, hunching over her beautiful body for a moment while I came to terms with the incredible feeling of having Radiance's supple throat milking my cock. Eventually, though, I managed to grunt out, “Sure, go ahead.”

I had thought Princess Luna might start licking Radiance's pussy, but I was wrong. Instead, she straddled one of her legs over one of the other filly's, scooched a bit to line things up, then lowered her own pussy down onto Radiance's. Both fillies moaned a little when Princess Luna's panties splatted against Radiance's pert vulva, and I groaned in concert at the tingling feeling Radiance's moans gave my cock.

Princess Luna started slowly grinding the bulge in her pink panties against Radiance's pussy, darkening the fabric even more with a mix of both of their juices.

Even as I pushed in and out of Radiance's mouth, I couldn't help but stare at the connection between the two of them, at how those immaculate pussy mounds squished and moved as they pressed against each other. I had never seen or even imagined such a thing ... and it was almost enough to make me drool.

The Princess must have seen my expression, because she winked at me and said, “Want some?”

When I nodded, she got up and turned around, presenting her sopping-wet pink panties to me, her tail raised high above. I leaned in, pressing my face between the velvety curves of her ass to take a generous whiff of their combined scents. She'd taught me before how to pleasure a mare, and I wasted no time in getting started. I licked and nuzzled all over her winking pussy lips through the thin, wet fabric, and if my enthusiasm made me push harder into Radiance's mouth, she didn't seem to mind.

Princess Luna was already shuddering, which I knew meant she was close. Was sharing me with another filly turning her on more than usual?

I used my own magic to grab the Princess's panties and pull them to the side, exposing her soft, warm pussy lips to my eager tongue. She was winking near-constantly, and I took full advantage of it, suckling her clit every time it bulged outward and teasing the tip of it every time her lips closed back up.

After only a few moments, Princess Luna cried out and released a spray of filly nectar all over my muzzle. She shuddered and dropped down onto Radiance's belly, resting her face against the other filly's teats as the juices she'd coated my face with dripped down, right on top of where my cock was making Radiance's throat bulge upward.

The Princess's pussy looked so tempting there, resting against Radiance's chest. I pulled my cock out of my special somepony's mouth and started climbing up onto the table, angling myself to slide in right where those pulled-aside panties used to cover...

But Princess Luna recovered before I made it there. “Woah there, Pepper,” she said. “How about we get down and I show Radie how it's done first?”

Reluctantly, I agreed and climbed back down off of the table. Soon enough, both fillies joined me.

Princess Luna immediately turned around and presented herself again, this time pulling her panties off with her magic. “Okay, Radie. Time for the real thing! This is really simple – you just stand and raise your tail, spread your legs a little and... Mmf!”

The Princess's gasped exclamation echoed through the small room as I mounted her and unceremoniously shoved myself in. She was slick with her own juices, and my cock was still coated in Radiance's saliva, so it slid in easily ... all the way in.

“Mmmm...” Princess Luna moaned slightly as I paused there, as deep as I could go. For a moment, she just enjoyed the intimate connection along with me, but I soon started thrusting in and out of her. Lewd noises came from underneath my belly as I reveled in the feeling of the Princess's warm pussy. A cloud of pleasure grew around me, blocking everything else out...

Until Princess Luna's magic froze me in place and she stepped out from underneath.

I whimpered, but that little slice of heaven didn't return.

Instead, she just let me drop back to the floor and turned back toward Radiance. “Okay, now you try.”

Radiance gulped and looked pensive for a moment, but then she stomped a hoof down resolutely and spun around.

My jaw dropped when she showed me her pussy. Sure, I'd snuck glances under her tail before when she wasn't looking, and sure I'd already seen a lot of her today ... but I'd never seen her like this before, not with her pink slit winking open madly and dribbling thick strands of filly nectar down onto her black socks.

She looked back at me. “Am I... Am I doing it wrong?”

Snapping myself out of the trance her pussy put me in, I stumbled forward. “No, no... You're perfect!” I lifted my chest up onto her rump, and the tip of my cock touched her pulsing heat.

I took a moment, standing there with my cock just beginning to press in between her sweet filly lips, to let it sink in – this was really happening, what I'd been looking forward to so much... With reverence for the occasion, I began to press forward. Her warm slit opened, and I slid a little way inside.

“Go slow, Pepper,” Princess Luna said. “Now, Radie, a filly's first time isn't supposed to hurt. Just make sure he goes in slowly and gently, and everything will be fine.”

“Hurt?” Radiance said, her voice quivering.

“I'll be careful, Radie,” I said to her as I let my cock slide in just a little more. “Tell me if you need me to stop.”

Radiance took a deep breath. “No ... it— Mmm. It feels good, keep going.”

I did, pushing in and out of her as gently as I could, letting Princess Luna's lingering juices mix with Radiance's and ease her open. Radiance was tight – much tighter than Princess Luna – and it was a struggle to hold myself back and not rut her with abandon, but I did hold myself back. More than anything, I wanted Radiance to enjoy this.

It took several minutes, but I finally bottomed out inside Radiance, my thighs bumping up against the firm, round cheeks of her ass and my cock wedged deep into the hot honey in between. I kept going agonizingly slow, still scared of hurting her.

“You can go ... a little faster, I think,” Radiance said in a quieter-than-normal voice.

I nuzzled the back of her neck. “Are you sure?”

“Mm-hm.”

Eager to finally do it, I increased my pace a little ... then a little more once I was sure that Radiance's moans were moans of pleasure, not pain.

Princess Luna came up behind me and smacked my ass. “You get her, tiger! Come on, give her all you've got – I think she's ready for it!”

I rubbed up against Radiance's neck again. “Radie, are you—?”

“Do it!” she squealed in between breaths.

After a brief pause to prepare myself, I started pounding into Radiance in earnest. The slaps of my legs against her ass resounded through the room, and my heavy balls bounced against her clit with every thrust. Radiance screamed up to the ceiling, but it sounded like a good kind of scream, so I kept going. I grabbed her hips between my hooves and slammed into her over and over again, even as her already-tight pussy began to squeeze me harder.

Before long, the dam burst. Radiance went silent and froze in place, her pussy pulsing madly around my hard shaft as her body began to heave under me. She let out a long “Oooooh!” before her legs gave out and she fell to the floor.

I barely stopped myself from falling down on top of her, managing to teeter back and forth on my hind legs instead. When I looked down at Radiance, I grinned, dumb with satisfaction. She was lying on the floor, quivering as her slightly-gaping pussy clenched open and closed, showing me ruffles of soft pink flesh inside.

Princess Luna didn't leave me out in the cold for long, though. Before Radiance even managed to start breathing again, the Princess stepped up in front of me and took my cock into her mouth, letting Radiance's leftover juices slide it deep inside. She bobbed up and down in just the way she knew I liked ... so it seemed that it was time for me to get off as well.

I caressed Princess Luna's cheek as she drove herself down on me, enjoying her slick throat for what might be the very last time ... so I made sure to commit the experience to memory, sure that I would want to relive it over and over again in the future.

But Princess Luna didn't have me all to herself for very long. Soon, another tongue joined her – Radiance licking the base of my shaft where Princess Luna couldn’t reach. Her tongue flicked back and forth over the veins at my base, adding another layer of pleasure on top of the Princess's usual delights.

Soon, Radiance grew even more bold, pushing Princess Luna up and off of my tip, then taking me into her mouth instead. I moaned slightly – even though Radiance couldn’t go quite as deep as the Princess, just the mere idea of these two gorgeous fillies fighting for the right to suck my cock was nearly enough to make me blow right then.

Princess Luna didn't seem too off-put by being replaced. She worked her way down my shaft, slurping heavily as she went, going lower and lower. Even when she kissed my sheath, she didn't stop. Instead, she trailed all the way down to my balls, nuzzling and licking the full orbs as if she was trying to coax me to empty them into Radiance's mouth.

But Radiance coughed – she'd gone too deep again. Pulling off of me, she instead started licking up and down my length.

My legs were already starting to tremble when Princess Luna saw her opportunity and took back the head of my cock. She shoved herself down deep on it, deeper than usual. Even she nearly choked as my tip began to flare ... but she kept it under control and bobbed her head greedily as Radiance's tongue slathered my shaft just below her.

It was already becoming too much. I could feel the unstoppable pressure about to burst ... but I had some vague idea that Radiance should be the one to get it. “P-princess,” I muttered. It wasn't much, but Princess Luna already knew that the only time I used her formal title anymore was when I was just about to blow my load.

The Princess pulled herself off of me and yanked Radiance back a little as well. “Do what I do!” she said quickly, pressing their faces together cheek-to-cheek and opening her mouth wide.

Radiance copied Princess Luna's open mouth and closed eyes ... just in time.

I'd taken hold of my own cock, aimed it carefully as I gave it a last few strokes ... and then I grunted heavily as the first wave of my orgasm hit. A thick stream of white surged from my cock, splattering first across Radiance's face, then across Princess Luna's. More and more followed it, draping gooey white lines across both fillies. It splashed into their manes and soaked into their fuzzy coats, and they even managed to catch a portion of it in their mouths, where it puddled onto their outstretched tongues.

Eventually, the strong spurts died down to an occasional dribble, which Princess Luna was the first to move in and catch, sucking some straight from the source. She let Radiance have a turn just in time for the very last feeble pump, which Radiance drew out and swallowed greedily.

I sat down on my rump and caught my breath while I admired my work. Princess Luna had never let me give her a facial before, but now that I had, I decided I was kind of good at it. The two of them looked so sexy and cute, blinking away the strands of cum that draped across their eyes.

“Wow,” Princess Luna said. “I'm usually not into that, but I have to admit you have somewhat of a talent for—” She paused awkwardly, staring at me once her eyes were clear. “Oh... Oh my goodness...”

“What? What is it?” I looked around, but nothing seemed out of place...

Once Radiance got her eyes clear, she gaped at me as well. Her outburst was more informative, though: “Pepper! You got your cutie mark!”

My eyes shot down to my own flank. There it was! Two red cupcakes, artfully drizzled with white frosting. I stared at it for a moment, then glanced up at the two fillies I'd just creamed. “Woah... Did I just get a cutie mark for ... for that?”

Princess Luna chuckled. “You wouldn't be the first pony whose cutie mark has a hidden meaning. Luckily, since you come from a culinary family, nopony is going to question the nature of your mark. Still, I'd suggest that when your mother comes to pick you up today, you tell her that we played at baking, and you ended up being really good at drizzling the sauce.” She smiled, then leaned over to Radiance and licked some of the gooey cum from the other filly's nose. “Because you are really good at drizzling sauce!”

“Um... Luna?” Radiance said. “This stuff is getting really sticky, and my dad's going to be back pretty soon...”

Princess Luna patted her back and took another generous lick from her cheek. “Don't worry, we'll get you all cleaned up before I let the guards take you back to him. And you'll have Pepper all to yourself from now on.”

“Aww,” I moaned. “You were serious about that?”

Radiance cringed. “It's okay, really. I don't mind if you want to see him again... Es-especially if we could, um, share him again?”

“Nope.” Princess Luna shook her head. “I meant what I said – Pepper is nice, but he's getting too experienced for my tastes. Now that he has you, it's time for me to get a fresh stud, one I can tease the virginity out of.”

I sighed. I guessed I knew this would happen sooner or later, but I had thought it would only be after I grew up. Maybe I was already too grown up for the Princess now that I had my cutie mark. “Well, um thanks, I guess. For everything. It's been really great, playing with you.”

“I had a good time, too,” Princess Luna said. “You were fantastic – I'm going to remember you for a very long time. But for now, how about we get those wipes out and get cleaned up?”

“Yes! Let's get cleaned up!” Radiance nodded enthusiastically, causing a few drops of cum to fly out of her mane.

Both me and Princess Luna grinned wide as I opened up the drawer and took out two packs of cleaning wipes. It was a day that I'll never forget.

Author's Note

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