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

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