Author's Note

Welp... it appears it's that time of year again, boys and girls. The month of ~~MILF~~ May is upon us, and as such, that means it's time for some older-mare-on-younger-colt action! Last time we banged Velvet. Now, it's time for another one! So, the only question I have for you all is...

...who's ready for some sloppy seconds?!

...

Why do I punish myself with such stories?

Touch Down

You stare around the terminal with wide eyes, your jaw hanging open.

Beneath you, your hooves sink into the white fluffy clouds up to your fetlocks. Normally, you’d have fallen straight through them at this point—being an Earth pony and all. However, the silver amulet currently hanging around your neck thankfully prevents this. It glows softly, imbued with a simple cloud-walking charm.

You take in the breathtaking sights around you as the rest of the passengers disembark the airship. A low murmur fills the air as the herd of ponies venture further into the terminal, where they begin to disperse. They chat happily with one another, some moving off to pick up their luggage while others hurry off to try and catch connecting flights. A few even head towards the small food court to grab a quick bite to eat.

It’s painfully obvious on first glance that there are very few non-pegasi present in the crowd, or in the station itself for that matter. They fly by over head, effortlessly soaring through the air as they head off towards Celestia only knows where. In fact, besides yourself, you can only pick out a hoofful of non-flying ponies nearby.

There are three unicorn fillies gossiping excitedly together as they make their way towards the other end of the port. Dressed in fancy school uniforms, it’s clear that they are from some private school in Canterlot. Probably on vacation or something.

An Earth pony stallion sits alone at one of the tables outside a small cafe, drinking in silence as he stares down at the table. He looks a little worse for wear, but that just might mean he got off of a red-eye flight.

And lastly, a pair of griffons study a nearby map of the area, conversing in their own harsh, screech language.

In awe, you slowly turn in place, trying to take in everything. The station is like nothing you’ve ever seen before! Massive columns of cloud loom high overhead, holding the ceiling aloft. Banners of rainbow light flow between the pillars, twisting and turning around the solid clouds like ribbons. In the center of the station is a fountain that is spewing liquid rainbow into the air in a shower of color. A few pegasi roost upon the lip of the pool, as well as at the few tables surrounding it. A few are sleeping, and one or two appear to be snacking on something, but for the most part all of them seem to be waiting for another flight.

Not you though—you are most definitely at your destination.

Suddenly, a loud air horn sounds off right behind you, pulling you from your daze. The airship you just got off of slowly begins to rise into the air again. Twin propellers slowly roar to life, pushing the bulbous ship forward. You watch it float out of sight before turning and moving further into the station.

A pair of heavy dual-saddlebags shift about on your back as you walk, causing you to sink into the clouds. You have no fear though—the purple glow from the amulet signals that the charm on it is still active. Magic might be a complete unknown to you, but you trust your dad completely, and he is the one that enchanted the amulet.

If he says that the spell won’t fail during your stay, you believe him.

It was your parents that originally decided that you should leave Canterlot while the city was being cleaned and restored from the Changeling Invasion. Your house was located in the Middle District, and while it hadn’t suffered the worst of the damage, there was still enough to be fairly inconvenient. Rubble clumped up the streets, and several blocks were still without power or water. Clean-up crews were still hard at work, but due to the insistence of the nobility, the Upper District was receiving most—if not all—of the attention at the moment.

That had been an inconvenience for your family, with both of your parents in the Guard. Luckily, they didn’t work on the day of the Invasion, but they had been working almost nonstop every day since.

With your dad in the Solar Guard and your mom in the Lunar, they tried to alternate shifts at home. Most of their off time was spent sleeping though. With double shifts as the norm, it was not uncommon to have a zombie parent stumble home and collapse onto the couch without even taking off their armor first.

Not that you minded the lack of attention; you’d usually just draw silently next to whichever parents was currently passed out at the given time.

It appeared that your parents cared though. After about a week of this, your mom sat you down and informed you that they’d feel more comfortable with you out of the city during the restorations.

“We can’t be there to watch you all the time, hon,” she had said. “Both of us would feel better knowing you were safe elsewhere. At least until all the excitement has calmed down and things get back to normal.”

It made sense when you thought about it—while the threat from the changelings might have diminished, there were several cases of theft and looting from within the city almost every day.

You originally thought that you’d be going to stay with your grandparents in Van Hoover, but apparently they had taken an extended vacation to see the world one last time before they settled down for good and enjoyed their retirement. Instead, your mom had informed you that you’d be staying with an old friend of hers from school.

The fact that this friend happened to live in their old hometown of Cloudsdale just made it all the more better.

You had never been to Cloudsdale yourself, but you had grown up hearing stories about the city from your mom, though most of them had always seemed vague. Still, these tales had always made you long to see the city in the sky. Unfortunately, with your parents’ weird work schedules, there was never a good opportunity to do so. Plus, your mom always seemed to change the topic whenever you brought up the possibility of visiting.

That was about to change though. You are going to be staying up in the Cloud City; you’ll be able to see if it really lived up to all the hype.

First though, you need to find your mom’s friend.

Stopping in front of the fountain, you glance around the main terminal again. The station is almost empty now, all the newly-arrived pegasi having dispersed. A few stragglers remain—like the mare currently sleeping on the lip of the fountain, her strawberry mane falling into the multi-hued liquid—but for the most part you are now alone.

You blink before peering around again, you brow beginning to furrow. The port is almost empty now… so where’s your mom’s friend? According to the letter, she’s supposed to pick you up at the station at noon, and it’s currently—you cast a quick glance at the large clock hanging on the wall—a quarter past. So, where is she?

She did know today is the day you were arriving, right?

Sweet Celestia… she didn’t forget, did she?

…

Uh oh.

Ummm...

Casting another glance at the clock, you decide to wait a little while longer, just in case she’s running a little late. If she didn’t show up in another half hour, you’ll just buy a ticket back to Canterlot and explain what happened to your parents. They can then either get a hold of mom’s friend again, or come up with another plan.

Nibbling on your lip, you look up at the clock again. You hope this friend shows up soon; you really, really want to see Cloudsdale up close.

Taking a seat on the edge of fountain, you remove your saddlebags and place them down on the lip beside you. You take a moment to rummage through one of the side pockets, bringing forth a few granola bars that your dad packed you for the trip.

You snack on one while you wait.

…

As the hour hand slowly nears the one position, you figure it’s about time to go purchase a ticket home. You’ve sat here longer than your originally planned and have seen several airships come and go. Still, no sign of mom’s friend.

It appears that she’s not coming.

Dejectedly, you get down off the fountain and are in the process of strapping your saddlebags back on when you hear your name shouted out across the terminal. Glancing around, you blink upon see a pegasus mare half flying-half running along as she hurries towards you.

“I’m here! I’m here!” She stumbles as she reaches you, her wings flapping wildly as she attempts to stop herself from face planting. The force sends puffs of cloud scattering into the air. She manages to regain her balance, yet she is still out of breath. Sweat sheens upon her pale blue coat, and you could practically see steam rising off of her extended wings.

How… how fast did she fly here?

As the mare huffs and puffs, you take a moment to look her over. It only takes a glance to confirm that this is indeed the mare your mom described to you before you left. She even has on the yellow-orange Track and Field varsity jacket your mom said she loves.

“I’m sooo sorry!” she gasps. “I… I would have been here… sooner, but I, ugh… I lost track of the time!” Tilting her head back, she takes in great lungfuls of air. Her mane and coat are disheveled, more evidence of her mad dash to get here.

“Um, are you okay?” you ask, giving the mare a worried look.

“I’m… I’m fine!” she says, walking in small circles around you. She’s a bit on the small side… at least, smaller than you were expecting. The bottom of her chin barely clears the top of your muzzle, and you’re unsure of which of you weighs more. However, what she lacks in height, she makes up for in other measurements, such as her wingspan. Her muscular wings look almost too big for her body. She has no problem moving them though, fanning herself in an attempt to cool down. Her short tail flicks back and forth as if chasing off invisible flies.

When she finally manages to compose herself, she gives you a sheepish smile. “Again, I’m so sorry for being late. I meant to be here when you got off the ship, I swear, but I got sidetracked cleaning up the house. One thing led to another and, well… the time just seemed to get away from me.” Lifting a forehoof, she ‘thunk’d the back of her head with it, causing you to wince at the sound the impact made.

“Don’t tell your mother about this,” the mare continues. “I promised her I’d be here on time. If she finds out I was late, I’ll never hear the end of it!” You notice she has a weird way of speaking, drawing out certain words longer than usual.

Must be a Cloudsdale thing; your mom tends to do that as well whenever she gets angry or frustrated.

“Anyways,” the mare smiles and holds out a hoof. “Hello there! I’m Windy Whistles!”

You smile as well. Taking her hoof, you return the gesture while introducing yourself.

“I’ve heard a lot about you from your mother,” Windy says, her cerise eyes twinkling. “No doubt she’s told you a little bit about me as well?”

“A little bit,” you say with a nod of your head.

“Hmmm, nothing too bad, I hope?”

You shake your head. “No, just that I’ll be staying with you for a while?”

“That is indeed the plan!” she chirps happily.

You have to admit, you were initially a little nervous about meeting her, but her energetic personality is making short work of that—you can certainly see why her and your mom were friends back in school.

“You know, I was actually rather surprised when your mother asked me to look after you,” Windy is saying, “but when she told me how much you wanted to see Cloudsdale up close, I just had to say yes. The old pegasi pride wouldn’t allow anything otherwise.” She glances down at your saddlebags. “This all you brought with you?”

“Um, yes?” you answer, uncertain if that’s a good thing or not.

“Perfect!” Windy says. “Well, I’ve got a room all set up and ready for you. It might be a little different than what you’re used to, but it should be comfortable all the same! At least, I hope it is. Shall we go get you settled in?”

“Yes, please!” you say, nodding quickly. Your saddlebags are quite heavy, and while you are eager to see the city, it’d be nice to be able to take them off and not have to worry about them.

“Excellent! Let’s get going then!” Windy turns and begins to head off towards the entrance of the port.

You move to follow her, only to trip the minute you step off the tiles, your hooves snagging on the clouds.

“Whoops!” Windy gasps, catching you with a wing.

“Sorry,” you mutter as your face reddens. “The, um… clouds.”

This causes Windy to giggle and shake her head. “Yeah, I know it’s a little strange for ponies who aren’t used to walking on them. You have to pick up your hooves a little more than you need to on the ground.”

Glancing down at your hooves, you take a tentative step forward only to wince as the tip your hoof catches on clouds again. You lift it a little higher and manage to take a few steps, though you feel silly—you’re almost lifting your legs up to your chest.

“There you go, champ! One, two, one, two!” Windy cheers loudly, causing several nearby pegasi to glance over curiously.

Your face darkens, but you smile all the same, stepping in place in time with her counts. She mimics you, marching next to you as she leads you out of the building.

You both reach the main entrance just as a fresh wave of pegasi are arriving. You stick close to Windy as to not lose her in the crowd, and she half-opens a wing in order to redirect some traffic away from you and your bulky saddlebags. At one point you find yourself pushed up against her flank, and a light blush touches your cheeks as you feel her toned muscles shift about beneath the soft layer of fur. The spicy scent of pine fills your nose, and you hum softly.

Eventually the crowd begins to thin out and you’re able to work your way out the doors. As you step out into the sunlight, you finally catch your first real glimpse of Cloudsdale.

The city is massive.

The main structure is almost entirely made out of clouds, with the city being broken up into multiple floating island districts. However, much to your surprise, many of the buildings aren’t actually molded from the clouds themselves like you assumed they would be. Sure, bits of cloud waft over and around them, giving them the illusion of being part of the main cloud structure, but they are actually made of the same material as buildings down on the ground below—wood, stone, bricks, and glass. Everything is painted various shades of white and gray, adding to the illusion of a city made of clouds.

Rivers of liquid rainbow run through the city, cascading from one floating island to another until they all eventually fall away into long waterfalls that reach down to the ground far below. Pegasi fly about gracefully through the air as they go about their day. They’re amazingly organized with their flight, almost as if there are invisible streets in the sky that only they can see. Despite their various speeds and altitudes, none of them crash or bump into each other as they fly past, sometimes inches from a collision. There’s a hypnotic flow to it all, like one of the ballets your parents took you to see a few years back.

For a long time you stare up in awe at the grand sight about you before giving your head a good shake. Upon glancing around, you notice that the airship port is on its own little island of cloud as well. There is a large gap standing between you and the rest of the city: a clearing nearly twelve feet wide of nothing but open air. A large sign is posted near the edge, the words ‘MIND THE GAP’ standing out in bold, red letters upon the off-white surface.

Carefully, you peer over the edge of the cloud for a moment, eyeing the ground far below. Unsure of how you are going to get across, you look back at Windy to see if she might have the answer. You find that she’s not paying attention to you, but instead eyeing the large sea of pegasi fluttering about high above.

She stares for a moment, eyes narrowing, before lifting a hoof to her lips and blowing a loud whistle.

“Over here!” she yells, waving wildly. A moment later, a pegasus pulling an empty open carriage breaks off from the flock and descends, parking himself right in front of the both of you.

“You’s all call for a ride?” the stallion asks as he pushes back his tweed cap.

“Yes, yes we did!” Windy chirps. “If it’s not too much trouble, can we get a lift to the Cumulus District?”

The stallion gives Windy a skeptical look before his gaze shifts to you and his eyes widen. “Ah! A non-flier. A’ight, can do. Just hop on in and we’ll get ‘er going.”

With a word of thanks, Windy climbs into the carriage.

You eye the carriage curiously before clambering up inside as well. Windy helps you get settled and makes sure that your saddlebags are secure in the small compartment in the front of the carriage. Once everything is set, she gives the driver the go-ahead and, with a strong beat of his wings, he takes off into the air.

The ride is surprisingly smooth, given the mode of transportation. The stallion keeps low, out of the crosswinds that blow throughout Cloudsdale. His wing beats are slow and steady as he glides over the cloudy structures below. There aren’t many other fliers down at this level, but those that are present give the stallion enough room to maneuver without jostling his passengers.

During the ride, Windy just sits back and enjoys the view. She watches the buildings and clouds drift by, a wistful smile touching her lips. Occasionally, she’d point out a passing landmark to you, or draw your attention towards a particular store, but for the most part she remained silent.

Your head however is on a swivel as you try and take in as much of the sights and sounds as possible. The buildings, the clouds structures, the flowing rainbows, the patchwork-quilt of land below you—there is so much to see and the carriage is moving so quickly that you can’t barely get a good look at things before they whisk by. It’s a little disheartening, but you tell yourself that you’ll be able to see them later.

You are staying here for a while after all.

A strong breeze suddenly pulls at your fur, making you shiver. It’s then that you realize you forgot to unpack the windbreaker your mom gave you. Shivering, you crouch down in the carriage in an attempt to find shelter from the wind, only to jump when Windy suddenly places a wing about your shoulders.

“It’s a little chilly up here, isn’t it?” she asks, giving you a warm smile. “We pegasi are built for this, but the other pony tribes tend to find it a little uncomfortable. Remind me, and we’ll pick you up a windbreaker or a jacket later.”

“I, uh… have one,” you say. “I’m just a clod head and forgot to put it on at the station.” A little blush touches your cheeks as Windy laughs.

“Oh! Well then. At least your mother still remembers that little fact. After living down on the ground for so long, I assumed she had forgotten when I saw you standing there without one.” Giggling to herself, she pulls you closer, allowing you to share in her warmth.

The gesture is a little strange to you. Sure, your mom’s given you plenty winghugs before, but Windy’s wing is an entirely different feeling. It’s almost like a large, warm blanket, and the soft feathers tickle your coat as they brush over you. The feeling is… strange, for lack of better word, and for some reason you can feel yourself growing flustered. Your cheeks heat up, and down below, something begins to stir.

Quickly glancing away from the older mare that currently has you nestled up against her side, you focus instead on the passing buildings, trying desperately to distract yourself. A difficult task, seeing as the spicy scent of pine fills your nose with each inhale. It’s almost mouth-waterin—

No! Don’t think about it! The last thing you need is to become aroused when Windy’s wing is around you! For whatever reason, whenever your blood got pumping, it always seemed to head south. Made gym class even more awkward, given that you already looked stupid in the baggy shorts and shirts they made you wear without the addition of a tent in said shorts.

It certainly didn’t help that some of the fillies always picked out clothing that was too tight on them. Just like that one lime colored filly with the long horn and toned thighs...

No, wait! Bad thoughts!

Unable to shake your head without Windy noticing, you bite your lip instead in order to get yourself under control and double your attempts to focus on the scenery flashing by. Even in your distracted state, you are still surprised to see a lot of the buildings are the same as back in Canterlot—sports bars, movie theaters, clothing stores, a horseshoe store, bookstores, cafes, etc. Of course, that said, there are quite a few unique exceptions, such as a preening supply store, a cloud candy store, and a cloud mattress store.

With wide eyes, you stare about at the city in the clouds.

Your friends back home are not going to believe half of this.

…

The rest of the trip passes by relatively fast. Soon enough, the businesses turn to homes and apartments, and the stallion begins a steady descent. At Windy’s direction, he lands outside of one of the smaller buildings—a single story, blue-and-purple brick house with a small clumping of clouds covering the roof. Several windows dot the structure and are adorn with flower boxes that are currently in bloom. The yard is small and has a weird fence made out of moving rainbows that runs around the perimeter.

You eye the building curiously while Windy pays the stallion for his service. As he flies off into the sky, she moves to stand beside you.

“Well, here we are,” she says. “Home, sweet home.” She’s silent for a moment before glancing down at you. “I know it’s not much to look at, especially compared to your parents’ house in Canterlot. It’s certainly not as big or glamorous as theirs eit—”

“It’s nice,” you say, giving her a small smile. “I like it!”

She blinks before smiling, her entire face lighting up. Her chest fluffs out a little as she swells. “Well… thank you, champ! I’m not much of decorator, but I’ve tried hard to give it a homely feeling.” Lifting a hoof, she ruffles your mane before heading for the door. “Come on. Let’s get you settled in, shall we?”

Eagerly, you hurry after her. Your saddlebags are getting rather heavy, and you can’t wait to get them off and unpacked.

Crossing over the threshold, you notice that the interior of the house—much like the outside—is small yet cozy. The entryway immediately opens into the living room. A large, plush couch takes up a lot of space, resting against the far wall, right beneath a large bay window that overlooks the backyard. In the middle of the room is a long coffee table that is covered with magazines. Several bean bag chairs are scattered along the walls as well, adding to the clutter. To top it all off, a large entertainment center with a big-screen television sits across from the couch, adorned with different knick-knacks and picture frames.

To the right of the entrance way is the kitchen, divided from the living room by a small island bar counter. Tankards and mugs hang from hooks above the island, and there’s a double stove in the corner. Surprisingly, there are several taps located on the counter as well, their hoses running down to small kegs of various ales and beers.

To the left is a small hallway that leads to what appears to be the bedrooms, a small office, and a bathroom. There’s also a staircase in a small alcove off to the side that leads downwards, most likely to some form of basement or cellar.

Overall, it certainly is smaller than your parents’ house, but what it lack in size, it made up for in coziness.

Just like Windy said.

“This way,” Windy says, pulling you from your daze. She moves off down the hall. “I’ll show you where you’ll be staying, and you can drop off your stuff.”

You follow along behind her, your saddlebags bouncing as you move.

Coming to the first door, she stops and pushes the door open.

“Oh! Yes… this is the bathroom,” she says as you peer inside. Like the rest of the house, it’s a bit on the small side. There’s a sink, a toilet, and a medium-sized tub-and-shower combo. To your surprise, there are very little mane-care products on the shelves of the shower. Windy doesn’t seem to care about her mane as much as your mom does… but you could have just guessed that by looking at her—your mom’s hair is long and flowing and felt almost like silk; Windy’s mane was short and windswept and looked a little rough, almost like straw.

Personally, you think the look suits her just fine.

“Feel free to use the shower whenever,” Windy is saying. “It’s first-come, first-served, but seeing as it’s just you and me, that shouldn’t be an issue, right?”

“Right,” you say softly.

You’ve never really had trouble with competing for a shower. With your parents’ weird work schedules, you pretty much had first pick, except for in the early mornings or late afternoons. You always tried to go before your mom though, because she was notorious for using up all the hot water and leaving you and your dad with none.

Giving the bathroom one last glance, you back out and allow Windy to lead you down to the end of the hall, and the two doors located there.

“And this here is the guest room!” she chirps, stopping before the one on the left. Pushing the door open, she smiles down at you. “ Go on in and check it out.”

You slip past her into the room and glance around. There’s no bed, but a futon rests against one of the walls and is covered by several pillows and blankets. A small nightstand sits beside it, and a lamp rests upon it. There’s an old trunk present as well, the old wood covered by a quilt. Several picture frames line the walls, each one depicting the same blue-furred, rainbow-maned pegasus mare.

“Sorry about the lack of bed,” Windy says from the door. “I don’t get a lot of visitors, so buying another bed didn’t really make sense at the time. Still, the futon is comfortable enough… I think. You’re more than welcome to make yourself at home, though.” She smiles softly. “This room is yours for as long as you stay here.”

“Okay,” you say as your saddlebags slide off your back.

“My room is just across the hall,” she continues. “If you need anything, don’t be afraid to ask.”

You nod, and give her a smile as well. “Thank you.”

“Oh, you are more than welcome,” she says before turning to leave. “It’ll be nice to have somepony else around the house again. Sometimes it gets a little too quiet around here.” Her gaze drifts up to the rows of pictures for a moment. “Anyways… I’ll let you get unpacked.” Without waiting for a reply, she moves off down the hall, leaving you by yourself.

You take a brief moment to glance around the room again, taking in your new lodgings. It’s smaller than your room back home, and there’s a faint smell of mustiness to it. Moving to the window, you crack it open to allow some fresh air in.

With that, you begin to unpack what little you brought along.

Pulling out your toiletry bag, on place it on one end of the futon. Next is the windbreaker your mom had you bring along “just in case”. You’re glad you listened to her. Tossing it on the other side of the futon for later, you move to unpack the most important part of your luggage.

Carefully, you pull out several sketchbooks of various sizes, as well as a pencil case containing several brand new charcoal sticks, colored pencils, erasers, ink bottles and quills, a pocket knife, and your special hoofband that allows you to hold your drawing utensils easier.

Running a hoof over the cover of one of the sketchbooks, a small smile touches your lips. Your dad bought them for you shortly before you left Canterlot. “Give you something to do while you’re up there,” he had said with a wink. “Sketch some of the scenery for me, eh? Never been up there myself. I’ve heard it’s breathtaking.”

As you flip one of the books open, the scent of new parchment hits your nose. Holding it up to your muzzle, you close your eyes and inhale deeply, savoring the smell. Oh, you can’t wait to break these bad boys in.

You discovered your talent for drawing early on. There wasn’t much to do in school while waiting for one of your parents to pick you up after class, and you had taken to doodling in your notebooks while you waited. It started off as a way to pass the time, but apparently you had a knack for it or something. A teacher had spied the drawings one day and had promptly informed your parents. They had both been overjoyed at the discovery and ever since, they’ve been encouraging your talent in any way possible.

You don’t know why.

Personally, you don’t think your drawings are all that good.

Placing your drawing supplies on the nightstand, you’re in the process of empty out the rest of your bags when a low series of chirps come from off in the living room. You hear Windy let out a soft “Oh, shoot,” before hoofsteps can be heard coming down the hall. A moment later, her head peaks around the doorway, a small pigeon balanced between her ears.

“Hey,” she says, smiling awkwardly. Stepping into the room, you see she’s holding a piece of paper in her wing. “So, um… I just got a message from my partner at the gym. Unfortunately, something came up and she can’t cover my shift anymore, so I have to go in.”

You give her a blank look. “Oh, um… okay?”

“Yeah, and I don’t want to leave you alone,” she continues. “Scarlet would kill me. So, uh… do you mind coming in with me? It won’t be too long, I promise. Class only usually lasts for about two hours, give or take. There’ll also be free refreshments there, in case you get hungry. We’ll can get something to eat afterwards too, if you’d like.”

“Can… can I bring my sketchbooks?” you ask tentatively.

Windy smiles brightly. “Of course! Bring anything you like to pass the time.”

Eyes lighting up, you grab your sketchbook and drawing supplies and slip them back into your saddlebags. Donning the bags, you make sure they are properly secured before following after Windy excitedly.

Food and a chance to break in your new sketchbook? She didn’t have to ask twice!