Letter to a Mailmare

by Yukigo Kurosaki

Rating: mature
Tags: Romance, Angel, Fluttershy, Derpy Hooves, Princess Celestia, Sex, My Little Pony: Friendship is Magic
Length: 13551

Fluttershy finally decides to reach out to her crush, but does she get more than she bargained for?

Princess Celestia pays a visit to Fluttershy's cottage to seek her thoughts on courting Twilight Sparkle for Hearts and Hooves Day, but while there, she finds that Fluttershy has her own pony in mind, one that many fail to take notice to.

Fluttershy can't talk, but she can write, and write she does.

The only question that remains is, how will the abused mare react, and are the feelings mutual?

Published 2012-03-15 09:54:01 UTC
Last updated 2012-03-29 19:27:41 UTC

Note to Postmaster

Looking for a pre-reader/editor for the next/this chapter, and really, for all my writing! Please, don't hold back the criticisms, I want to hear it, even if you nitpick. I'm not going to get better if I don't know exactly what's going wrong.

It was as if, somehow, her parents had psychic powers when they named their daughter Fluttershy. No other explanation seemed logical when everypony saw how well the name fit the hopelessly timid, yellow furred mare. Maybe it was a bit of suggestion from Celestia herself, since many ponies seemed to have names unordinarily fitting.

Despite how shy the pony was though, Celestia was indeed proud of Fluttershy, as she was one of the most loyal friends of her protégée, Twilight Sparkle. Celestia wrote a letter in advance, instructing Spike to deliver it to Fluttershy himself, for as much as Celestia loved the substitute mailmare, well... she wasn’t named Derpy Hooves for no reason, and the last thing she wanted to do was give Fluttershy an aneurysm by showing up unannounced.

Dear Fluttershy,

Good day, Fluttershy. I am writing to tell you that, tomorrow, I will be stopping by your cottage for a visit. I was hoping to hear a report on the status of the woodland creatures. I have heard from many Ponyvillians that you are the ultimate source of all things zoological. I will be visiting as soon as I am finished raising the sun, and, factoring in travel, it will likely be two hours after dawn. Please, do not be concerned, you are not slated on a path to Moon Banishment, I assure you. Consider it an informal visit, I would hate to see another pony have a mental breakdown at my hooves, like Twilight Sparkle.

Best Regards,

The Royal Sun Princess of Equestria, Celestia.

Celestia could have easily gotten such a report via letter, but it was only a front. She flew alone through the pink, milky skies of dawn on a mild Hearts and Hooves day. The timing of her visit was by no means a coincidence. Celestia was very, very old, and she wasn’t afraid to admit it, but yet she was cursed with infinite youth. She was more than familiar with love, and just as painfully familiar with loss. Ponies aged and died, she didn’t.

She knew it was time to move on. She had to move on, she always did, and though some thought it cold, she always took a new mate after a lifetime or so, after everypony had forgotten her previous mate. She wanted to pop the question to Twilight Sparkle, a pony she had always respected and loved; and now was the time where Twilight would be exploring her sexuality and looking for a lifemate. But first, she wanted to ask all of her friends what they would think of such a relationship. Fluttershy was first on the list, followed by Applejack for an order of Zap Apple Jam, then to Rainbow Dash at Cloudsdale, where the Princess was the guest of honor at a Wonderbolts race, then Pinkie Pie for a simple visit -- she knew she didn’t need a reason for her, and finally, Rarity, to place an order for a beautiful dress, which she hoped to wear with Twilight one day at the Grand Galloping Gala.

Celestia smiled as Ponyville appeared on the horizon, knowing it wouldn’t be much longer.

Fluttershy opened an eye slowly, groaning softly as the light finally registered to her, holding up a hoof to block it out. “Mmm... Good Morning Ponyville...” She gave a long yawn, rolling to her hooves. Fluttershy made sure to get to bed early the night before so she could be prepared for the princess’ visit. She looked to the calendar, and the date was conspicuously marked with a large heart on the day’s box, a caption reading “Hearts and Hooves day.” Fluttershy gave a little sigh and looked down. “That day already?”

Hearts and Hooves meant a very painful time for poor Fluttershy. It wasn’t as if Fluttershy was asexual, that was the furthest from the truth. A pile of romance novels was kept neatly in the corner, almost all of them her own, and there was a fair amount of erotica scattered in the stack. Those she got from Twilight’s library, for she was far too embarrassed to actually buy them from the local bookstore -- she couldn’t dare look the proprietor in the eye as it were when simply buying steamy romance, let alone if it went into further detail. She knew she could check them out with Spike when Twilight was busy, which, suffice to say, was always; Spike was too young to know what she was getting.

She just didn’t know how to talk with those she was interested in. Rainbow Dash had long since figured out that Fluttershy was interested in fillies more than colts, and had often surmised her crushes with a surprising degree of accuracy. She arranged secret meetings in an attempt to get Fluttershy to come out with her desires, but every time she and her secret love were brought together, her throat closed up, her legs locked, and she ended up in any one of three ways: Passed out on the floor; crying atop a lonely, isolated cloud; or wetting herself. The third had only happened once, and that was when she was placed in the same room as a domineering Princess Luna, who was wearing some tight leather and carrying some hoof-cuffs (the next day, Fluttershy discovered her book on Bondage missing.)

Fluttershy, now quite downtrodden, walked outside, taking a cursory glance at all the animals so she could be prepared for the princess. She didn’t know why the princess was asking for a personal report, and honestly, it made her more than a little nervous. The oddest part was the timing. There’d been no blights, plagues, famines or otherwise hardships happening to the animals. A pair of squirrels bounded up to her hooves upon sighting her. “Hello there, Mr. and Mrs. Squirrel... how is the nut collection going?” They chittered brightly, scaling the tree to show a plentiful pile of acorns. “Oh! Very good job, looks like you lasted the winter just fine.” She smiled and gave them a little salute, which they returned. She glanced over to the many birds, happily munching on some seeds in the feeders they had been provided. “Everything’s fine, why is she calling on me?”

Angel the bunny poked at her hooves, looking up expectantly. Fluttershy glanced down, seeing him. “Hello there, Angel, don’t worry, I haven’t forgetten about you, little guy.” She turned back towards the house, the rabbit hopping behind her as she pulled a carrot out of storage, offering it to him with a nudge of her nose. He devoured it, which made her start back in surprise. “I never get used to that...” She glanced towards her mailbox, but there was no deliveries yet, not surprising, Derpy Hooves was always late.

She sighed, pink mane almost wilting down on her shoulders. She really liked the mailmare, even if most ponies couldn’t tolerate her absentmindedness -- Dash being an example -- or made fun of her for her constantly unfocused eyes. Maybe she was spending the day with her very special somepony, after all, she did have a foal; she just couldn’t recall ever seeing her mate. The thought sent her into another wave of depression. She wanted to tell the mare how she felt, but there were so many prohibitions: her inability to speak, her fear of intruding on a relationship, and above all, whether Derpy liked the company of mares.

She waited by the mailbox for a few minutes, hoping to catch the grey mare on her crash course for her cottage, so she could at least have the slightest conversation with the sweet, misunderstood mare, but alas, she never came. She decided to head back inside to read more, plopping back on her favorite couch lazily. She was just finishing up a book on fetishes. “Watersports?” She asked, curious. “That’s an odd entry...” She read on for a few pages, as the book went into detail of what it entailed, its known history and psychological significance and a few famous (and deceased) figures that were into the fetish. Fluttershy turned the slightest shade of pink. “O-oh my! What a misleading name...”

She was interrupted by a knock on the door, which caused her to throw up the book with a squeaking scream, hiding her head in the couch. Angel rolled his eyes and gave her a firm kick to the rump. Fluttershy rubbed the spot, pulling her head out of the couch. “Ow! Angel! I know I get scared too easily, but you don’t have to kick me...” The white rabbit pointed to the door, and the letter lying on the nightstand. “Oh Celestia! The Princess!” She glanced to the clock. “Is it that time already, oh shoot, I got up late... I wanted to clean the house!” She suddenly realized the princess was waiting, scrambling upright, knocking the stack of books over in the corner.

She rushed over to the door, opening it up to see the princess in all her glory, sparkling green and pink mane following behind her like it was perpetually caught in a soft breeze. She bowed gently. “Good Morning Fluttershy, my apologies for the sudden visit.”

She shook her head fervently. “Oh no! It’s no trouble Princess, I always have time for you.”

Celestia cracked the slightest smile. “You don’t have to humor me like that, Fluttershy, I know you’re a busy pony, particularly on a day such as this.”

Fluttershy felt a pang of sadness rushing through her. “Yes... right.”

Celestia paused, noticing Fluttershy’s convictions, but continuing on for now. “Well... I won’t take too much of your time. Can you just give me a quick rundown of how the animals are doing?”

Fluttershy glanced out the window to the melting snow. “Well, with the mild winter we’ve had this year, most of the animals are coming out of hibernation early. All of the animals, at least the ones under my care are very healthy. I hope it doesn’t snow too much and cover the ground again, I’d hate to see for them to go hungry, if the plants die again, there’ll be trouble...”

Celestia listened intently. “I’ll have to talk to the Pegasi about this, thank you, Fluttershy.” She looked around the room, noticing the disheveled stack of books dispersed around the corner. She picked up a couple, reading the titles, the slightest blush covering her cheeks. “Oh my Fluttershy... I didn’t know you were into these kind of novels.” She inspected the stickers on the back, claiming they were property of Twilight’s library. “Or that Twilight stocked them...”

Fluttershy turned back from the window just in time to see Celestia pick up a couple of her books. “A-ah! Celestia! I... those aren’t... wait I can expl...” She squeaked, face burning, just standing there, legs shaking.

“Relax, Fluttershy, I know ponies are curious, you don’t need to be embarrassed about it.” She glanced back to one of the books, holding it in front of her. “Though you are a... bit more curious than most. Oh my...” She set them back down gingerly, moving back over to Fluttershy. “You... may have guessed though, that the report wasn’t my only reason for coming here.” Fluttershy nodded hesitantly. “Well... you see. I... kind of wish to ask Twilight out.”

She gasped, covering her mouth with her hooves. “T-Twilight?!”

She nodded gently. “I’ve been catching hints that she’s a bit more than... friendly to me, and I have always cared for her deeply. I would be honored for her to be more than a student to me. I’m going around to all of her friends today and asking what they would think.”

Fluttershy shyly hoofed at the ground, rocking back and forth. “Well... it would be very cute, I agree, and Twilight does seem to hold dearly to every word you say, I think it would work well... it would certainly make her day.” She glanced downward. A relationship with Twilight? She always counted on Twilight for support. She and Twilight were the only ones in the group that seemingly lacked the social skills to get a mate: Applejack was quite assertive when she had to be, Rarity was charming, Rainbow Dash, well no question there, and Pinkie Pie was a killer tease with a great sense of humor -- at least if her encounters with her behind closed doors meant anything. If Twilight was with Celestia, then she’d be alone. The thought scared her a little bit.

Celestia nosed up to her. “Fluttershy, are you okay...? You seem like you have something on your mind.” She tilted her head. “Do... you... not have somepony for Hearts and Hooves day?” Fluttershy shook her head softly and Celestia ventured another question. “Do you have somepony in mind...?”

Fluttershy glanced over to the mailbox. She hadn’t thought about that question much. She wasn’t constantly thinking of ponies, and the question caught her off guard. The only ponies that was often on her mind were her friends and the clumsy mailmare. She never came on time, and even though she was always late, she wasn’t even consistent about it either, yet Fluttershy always lit up when she saw the bright smile on her face when she pushed the letters into her mailbox, if there were any -- Fluttershy wasn’t quite the popular type. Every morning she spent her time by the window in a hope to see the grey mare as she crash landed, brushed herself off, checked the mailbox and then flew off, all with a smile on her face. Some days, she’d even work up the courage to wave, always receiving an eager wave back. She finally nodded again, she wanted the klutzy mailmare as her own. Maybe it was desperation, but the thought of waking up beside such an innocent smiling face every morning filled her heart with joy. Yet, a knot formed in her stomach, she couldn’t ask. She knew her limits and she learned from experience, every pony she was ever interested in made her throat close up, and she always ended up running away before she could get a chance to talk.

“Y-yes...” Fluttershy finally answered, her voice even quieter than usual. “B-but I can’t ask... I just can’t. I’d just end up embarrassing her...” Fluttershy realized what she just said, trying to correct the situation. “--Him! I meant him!”

Celestia arched a brow bemusedly. “Wait... do you like fillies, Fluttershy?”

Fluttershy felt her face blush, backing up into the couch and flopping upon it unceremoniously as her back legs touched against the cushions. Fluttershy, much like Applejack, was a terrible liar. “Um... I... well... you see... the thing is...” She continually tried to stall, feeling her tongue tying. Eventually, she just felt defeated, letting her neck fall, mane flopping over her eyes, seeming to lose some of its pomp. “...yes.”

Celestia lowered herself down to Fluttershy’s level and nuzzled into her neck. Fluttershy closed her eyes and instinctively pressed into her silky white fur, burying herself in her eternally flowing mane of green and pink. Celestia was used to the reaction with those that she consoled. She’d been told that with her gentle mannerisms that she seemed like everyone’s mother, a distinction she took with pride; she always wanted to be close with her subjects and rule with love, not fear. Celestia gave her neck a reassuring lick. “You don’t need to be scared of that fact, you don’t think it’s uncommon, do you? Mares outnumber stallions by a large margin in this town, these kinds of things just happen, you can’t help it.” She pulled back, a smile on her face. “Now... who are you interested in, maybe I can give some tips?”

Fluttershy averted her gaze. Her voice was scarcely above a whisper as she spoke, and her voice cut out in some spots, struggling to get the words out. “--er--y --ooves...”

Celestia leaned closer. “I’m sorry, I didn’t get th--” She processed the sounds, pausing for a few seconds. “Derpy Hooves, the mailmare?” She giggled gently, which made Fluttershy cringe, preparing to bury herself in the couch. “Fluttershy, that’s positively adorable. Derpy sure could use something to look forward too, hmm, yes, I think this could work.” Celestia reached up with a hoof and Fluttershy shrunk away. Celestia stroked Fluttershy’s mane, combing it out, giving it a bit more lift again. Fluttershy looked up with teary eyes as she did so, feeling like such a wreck. “Now Fluttershy... just because you have difficulty talking doesn’t mean that there aren’t ways to communicate. Why not try a letter? I mean, after all, she is a mailmare, she’d be the first to get it.”

Fluttershy sniffled. “I’m scared, Princess Celestia. Derpy has a foal, and that means that she’s already been with a stallion, and she may be still with him. I don’t want to break into her relationship, and I don’t even know if she likes mares. I don’t want cause any problems between us. I want to keep seeing that smile every morning...”

Celestia bit her lip, clearing her throat. “Well... I can put one of those fears to rest... unfortunately.”

Fluttershy tilt her head, confused. “Why is that bad news...?”

Celestia averted her eyes, then sighed. “Derpy Hooves has a foal because somepony... took advantage of her. I didn’t expect such a violent crime to happen in Ponyville, but... that’s how it is. I tried to find her assailant with a homing spell modified with her foal’s blood, but he was far out of it’s range... he’s gone.”

Fluttershy’s lip quivered. “Th-that’s terrible! I didn’t know that... and ponies make fun of her... how dare they!”

“They don’t know, Fluttershy, and many of them don’t want to know. They don’t understand how she’s... different. Besides, Derpy would never let that fact come out if she could help it, Derpy’s a stubborn mare with a lot of pride, she’d never lower herself to pity for something that she considers her fault.”

Fluttershy paused, thoroughly confused. “Why in Equestria would she think that was her fault?”

Celestia gave another stroke along her mane. “I’ve been on this world for a very, very long time, Fluttershy, and I’ve seen my share of debauchery... especially back in older times. Ponies always consider themselves to be at fault. I don’t know why, maybe they’re ashamed they let themselves get into that situation, or they thought they could see it coming. When something like that happens to you, you don’t think straight, and you feel degraded, worthless; the thought of being someone else’s sex toy can make a pony very, very depressed.” She sighed tiredly. “I’m just glad that Derpy Hooves was able to pull out of the spiral and enjoy her foal... her one true boon from the encounter.” She chuckled, sighing wistfully. “I paid a few visits to the young filly growing up... she’s got quite the talent with magic. She looks up to Twilight Sparkle and wants to be as good as her some day. She’s incredibly smart, and polite for someone that age too! She’s been raised very well. I couldn’t be prouder of that poor Derpy for raising such a pure soul.”

Fluttershy felt a tear dripping down her cheek. Celestia leaned in and licked it away, which elicited the slightest blush and giggle from the coy pegasis. “You seem like you really would be good with foals, Fluttershy.”

“I’ve been told.” She responded simply, her voice the usual whisper.

“Would you like any, someday?”

“Of course I would... but I don’t know if I could handle one alone... let alone if I were to have two. I don’t know how Derpy can do it.”

Celestia nudged her slightly. “I’m sure she wouldn’t mind some help...”

Fluttershy bit her lip. “I... I really want to ask her, I do, but I’m so... so scared of what will happen if she says no. I don’t know if she likes mares, and even if she does, I don’t know if she likes me! There’s just too many uncertainties...”

“Uncertainties didn’t stop your friend, Rainbow Dash from making a Sonic Rainboom not once, but twice, Fluttershy.”

“I’m not Rainbow Dash! I just can’t bucking do stuff!” She snapped back, gasping and covering her mouth when she realized she swore to the Princess, cowering. “Please don’t banish me, please don’t banish me...”

“Relax!” Celestia barked, breaking into a rare bout of the Royal Canterlot Voice for her, then lowering it to a whisper. “Relax...” She repeated, her tone softening greatly. “Like I said, if you can’t talk, write. I know Derpy, and she will respond to you. Even if your love for her isn’t mutual... she won’t hurt you.” Celestia kissed her gently on the forehead. “Derpy will never hurt anyone.”

Fluttershy shrunk to her smallest, hiding behind a tuft of hair, looking like a filly compared to the massive white alicorn. “You’re sure...?”

She nodded. “Fluttershy, I’ve had literally thousands of years to observe ponies... I’m sure.” She rose to her hooves once again, flicking her head to send her mane aloft once again. “I need to make my leave, my little pony, I have many things to do for the day, thank you for the report, even if it was just a formality, and I do hope that you’ll take what I’ve said to heart.” She glanced back with a kind smile. “Just give it a try... Derpy will be happy to see you at least care about her. Goodbye, Fluttershy.”

“Um... bye Princess Celestia.” She whispered meekly back as Celestia spread her wings outside, crouching down for takeoff. She watched as Celestia’s form slowly disappeared on yonder, towards Ponyville. As soon as she was gone, Fluttershy ran to her mailbox, trembling as she opened it up: no mail. She glanced around in the dirt. There were plenty of scuff marks nearby from misplaced, misjudged and otherwise just botched landings, but none of them were fresh. Derpy hadn’t come while they were talking. She gave a sigh of relief, retreating back into her house, pacing back and forth nervously.

Angel bunny bounded up to her with a piece of paper in his paws and a quill in his mouth. Fluttershy glanced to him, pacing faster. “Okay, Fluttershy, you can do this... okay... okay, okay... okay... okay, alright... okay... alright.” Angel rolled his eyes and prod her with the quill, jolting her mind out of the broken record mentality. She leaned down and took both articles, setting them on her coffee table. “Here goes nothing...” She said, picking up the quill with her mouth and setting to work on the letter.

Dear Derpy Hooves,

I have something that I want to confess to you, something that’s been burning in my heart for a long time, gnawing away at it like a Parasprite. I need to get it off my chest. And that fact is that I care for you deeply, even possibly as more than a friend, but I don’t really know yet. I was scared to talk to you about it... I still am, but a very important pony convinced me that I couldn’t hide from it forever.

Other ponies may make fun of you for your eyes, and how you forget stuff sometimes, and how shaky your flying is, but I don’t care about those things. When I look at you, I see beautiful amber eyes that shine in any weather, it doesn’t matter that they’re not aiming at the same place. I see a silly forgetful mare that always means well. I see a smile every time I look at you, every single day you deliver my mail, and a pony that always waves back like we’re the best of friends, even though we’ve never even talked except for signing for packages. And above all, I see a brave, single mother of a foal that wasn’t meant to be hers in the first place.

Ponies don’t understand you, but that doesn’t matter, you’re better than all of them. Really, I don’t even deserve such a beautiful mare as you. Hay, I don’t even know if you like mares, but I had to try... I love you, and I can’t keep that to myself...

Love,

Fluttershy

The letter took her a very long time. She paused in a few parts to pump herself up, or to consider her wording. A few previous iterations laid crumpled up, strewn across the floor. She held up the final product proudly, Angel hopped up onto her withers, looking over it with her. He nodded simply his satisfaction. She slid it into an envelope. She didn’t know her address, so she just wrote her name across the back, taking up most of the space. She hoped she’d notice it and it wouldn’t get mixed in with the rest of the mail.

“Come on, Angel... let’s put this out for Derpy...”

He shook his head and snatched the letter out of Fluttershy’s mouth, bounding over to the table. “Wha--- Angel! Come back! I worked forever on that! Angel! I swear to Celestia I will use the Stare on you!”

He took the quill from the table and quickly drew a heart after Derpy’s name on the back of the envelope. Fluttershy swooped in and pulled him away from the card, picking it up again, examining his work. “A heart...?” She asked, confused, turning to Angel, which she’d just set down on the ground nearby. “Don’t you think that’s a little much?”

He shrugged, giving a “worth a try” look. Well, it’d catch her attention anyway, if the massive lettering didn’t do that to begin with. She cantered out to the mailbox, sweating slightly from nervousness, the petite rabbit bouncing after her. She opened the box and stuck the letter in, Angel hopping up atop the mailbox as she did so. “There... that’s it Fluttershy, easy as Pinkie Pie.”

Pinkie Pie, choosing that exact moment to bound by, as was her talent, shouted behind her. “I’m not easy! I’ve only slept with 4% of the ponies I know! Officially, you gotta be with at least 25% to be ‘easy’!”

Fluttershy could only blink. “I... could have gone without knowing that.” Where’d she get that statistic anyway? She edged back towards her cottage, glancing back to the mailbox every few steps, Angel hadn’t followed her. Instead, he surveyed the skies for the grey mare. She opened her door, taking one step inside, pausing. She then squealed, almost hysteric. She turned tail and darted back to the end of her path, flying full speed, embarrassed that she’d left such a card for the mailmare. She couldn’t let Derpy see it!

As she reached into the box, Angel jumped inside, biting her arm. Fluttershy yelped in surprise more than pain, yanking her hoof out. “Angel! That wasn’t very nice!” She tried again, and this time he stomped on her hoof. She bit her lip to avoid an outburst, eyes welling in pain. “Angel!” She shook her hoof out, swearing in her usual, adorable squeak of a voice, looking around to make sure nopony was nearby to hear her. “Mother bucker! What the hay is wrong with you!” She looked into to the mailbox, shooting him a withering glare, the Stare.

But he was unfazed. Angel knew his purpose, that’s why he stayed behind, he knew Fluttershy would try to chicken out at the last second. He gave his own version back, baring his buck teeth. She started back, not expecting her Stare to backfire. She finally began to realize what he was doing. “You’re... not going to let me get that letter, are you?”

He shook his head stalwartly, sitting on the letter inside of the mailbox. She wasn’t going to take her chances with those teeth. She sighed and resigned herself to cantering back to her house. She sighed, trying to get her mind off of her crushing nervousness. It would at least be a good opportunity to clean up those books in the corner...

Derpy finally made her approach some half hour or so later. She rocketed through the sky, leaving a cloudy trail behind her. “Dang it! I’m late again!” She flew straight over Fluttershy’s cottage a good quarter mile before she realized she’d passed it. “Oh! Shoot!” She sharply turned around, doing a few backflips in the air, and not in the graceful kind of way. Her pack of letters threatened fall off her back, though she grabbed it just as it was about to fall. “Whew! Got it...” She said, hugging the pack. It wouldn’t have been the first time she’d dropped her satchel, or the fifth for that matter. Only when she began to sink did she realize she was no longer flapping her wings. She frantically tried to regain altitude, scooting along the ground. “Gosh... that was clo--” She was interrupted when she collided head first into one of Fluttershy’s fence posts. She stepped back dizzily, eyes spinning, tripping over her own hooves and sitting down on her rump. “Dat’s a fence...” She pointed out, obviously, rubbing her head.

She was more than used to the impacts, though, and in a few seconds she stood up, seeing her target mailbox a few feet away. Angel was at his post atop the box, giving a little salute. “Oh hey! It’s a bunny! Hello bunny!” She saluted back, noticing the red flag sticking up on the mailbox. “Ooh, there’s a letter for me.” She giggled, opening it up and withdrawing the envelope. “Lezzee... anything for her?” She fished around in her satchel, rather light, as now it only contained the outbound mail -- Fluttershy was her last stop. There was only a letter from Pinkie Pie, but she gave everyone a letter for Hearts and Hooves day. It was bulging and twitching, and Derpy carefully nudged it in the box, she didn’t really want to know what was inside.

Angel saw that Derpy was going to put the letter in her bag without really looking at it. He frantically poked her and then to the envelope. Derpy smiled and nodded. “That’s right, little bunny, I’m the mailmare, I deliver the mail... try to anyway.” He shook his head, poking the writing on it, showing the recipient. Derpy noticed something was awfully big about the writing, there wasn’t even a return address! She closed one eye so she could focus a bit better. The writing finally came into view. It was addressed... to her, and was that a heart? “Wait a minute..”

Her heart jumped in her chest, breathing getting shallow. A letter, she’d never gotten a letter before, at least not one like this. “Who could this be from?” Angel rolled his eyes, face perfectly conveying “Who do you think?,” pointing towards Fluttershy’s house. She daintily tore the edge off the envelope, withdrawing the folded paper. Again she closed her eye, leaning in, the open eye scanning over the page. A blush quickly crept across her face. She held a hoof to her mouth in shock, rereading every single word of the love note. She tucked it in her satchel, tears welling on the corner of her eyes. “That’s the nicest thing... anypony’s ever said to me. I can’t believe it... no... this can’t be true, this has to be a joke.” Derpy knew Fluttershy’s reputation though, she was the Element of Kindness, the Element, for Celestia’s sake. Fluttershy would never have done anything so cruel. It had to be true. The realization crashed over her, and she sniffed, tears flowing freely, dripping onto the ground below her. Angel was gone, hopping towards the house. She closed the mailbox, done delivering her mail, heading towards the house. “I have to be dreaming...”

Fluttershy was wearing a hole in her now immaculate floor. The books had been stown away, and then some, busying herself with cleaning every surface, adjusting the cushions on her couch, rearranging curios and knick-knacks on her shelves, anything to keep her mind off Derpy. She heard a dull “thwack” and knew that Derpy had arrived, or rather, crashed into something. She peered over the windowsill shyly, seeing her conversing with Angel.

Now it appeared he was gesturing to the letter, and she finally seemed to notice who it was addressed to, closing one of her skewed eyes to read better. Fluttershy sank behind the sill, only her eyes peering over now, even trying to flatten down her mane. Now she was tearing it open, reading it. Fluttershy's eyes skipped a few beats, thumping widely. She was thankful she hadn't eaten that morning, or else she was confidant that her breakfast would be spread in a puddle across the floor about now. A hard knot formed in her stomach, she could hardly bear to watch, yet she couldn't turn away either; she had to see how Derpy reacted.

She gasped, tears were forming in Derpy's eyes, she put the letter in her bag. Oh no, that was the opposite reaction of what she wanted; she'd scared the poor mare! The tears dripped down onto the ground now. She'd failed, she'd made a foal of herself, again. She tried to be strong, but she couldn't hold back her own tears that now pooled at the corner of her eyes. Maybe she could hide in the bathroom until she left, or until the end of forever. She wondered how long she could barricade herself in her house before anypony would notice.

Her thoughts were broken by the knock on the door. Fluttershy tripped over her hooves, stumbling along the ground, unable to get up for a few seconds as she kept falling whenever she tried. She couldn't face Derpy down after such a dismal failure. She couldn't face anypony, for that matter.

Angel was there, which caught her by surprise. He pushed her rump with all his strength, which was a deceptively large amount, dragging her along the ground. "No, no! Angel, you don't understand... no... noooooo!" She squeaked, burying her face in her hooves.

Derpy, standing outside of the door, sniffled, still crying a little bit, wondering if Fluttershy was home. She thought she heard something inside, but maybe her ears were failing along with everything else of hers. Then she saw the bunny again, standing on a windowsill, making a motion to enter. She tilted her head in curiosity, then tried the door. It was open. She pulled it open to see Fluttershy desperately trying to flee, Angel holding onto her leg comically, logically unable to hold her back, but yet somehow managing.

"Fluttershy...? Is that you? What're you trying to do there?"

She almost screamed, collapsing, hiding under her hooves now. She couldn't see Derpy, so she couldn't see her, right?

"Fluttershy..." She tried again, feeling slightly awkward. "Did... you write me that letter?"

"...letter, what letter?" She couldn't lie, but she could deflect. "I don't remember writing you any love notes, that's silly, why would I do that?" Scratch that, she couldn't deflect either.

"Oh... somebody must have just been using your mailbox then... are they trying to get us togeth--" She paused. Derpy was a bit slow sometimes, and it took her a few seconds to realize that Fluttershy was trying to deflect the question, and had failed, so it must have been true. "You... you did write me that."

Fluttershy sobbed, curling up into her mane. "Y-yes, I did... please, please don’t be angry... can you ever forgive me? I didn't mean to make you cry, I swear it! I'd just been thinking about you so much, and it's Hearts and Hooves day, and there was Princess Celestia and... and..."

Derpy's lip trembled. "Forgive you?!" She sat down in front of the yellow pony, stroking her mane to comfort her. "Fluttershy, that was the most beautiful thing I've ever read. I was crying because... I don't know why, it was just, so beautiful! I've never been called all those things... nice things. You didn't make fun of my eyes... or, or how stupid I am!"

"You're not stupid!" Fluttershy rebutted quickly, her eyes pink from crying, finally looking up. "You're absentminded and silly, but don't you dare call yourself stupid!" She sniffed, more fresh tears falling down her cheeks. "You have a foal, you raised it all by yourself with no help. So what if you're not the brightest flower in the bunch. You're brave! You're the bravest bucking pony I know! Braver even than Rainbow Dash!"

Derpy felt the words hit her heart and psyche like all the insults had over the years, but these were different, instead of ripping and tearing away, leaving gashes and wounds on her self esteem, these warmed her, leaving her euphoric, elated. Her mouth trembled. "Y-you can't honestly mean that..."

"I do!" Fluttershy shouted, her voice getting louder, forceful, as she tried to make a point. She didn't even realize she was raising her voice, it just felt so natural now, she didn't notice. "To tell the truth Derpy..." She looked away, bangs falling over her eye, voice returning to its whisper. "I envy you..."

Derpy was floored. She didn't know what to say. Normally, hundreds of things flew through her mind, taking a few seconds to pick the least stupid sounding response, but now, she was completely blank, there was nothing left to say. As her brain rebooted, a rush of emotion flooded her thoughts, images not words. They were a hazy blur, the two together at sunset, a romantic dinner, making muffins together, getting dough all over her house. Before she could even realize it, images decayed to raw passion. Bodies rubbing, grinding, vertigo, wetness, sparks, flares. She couldn't even comprehend it all, when suddenly, it became tangible, the slightest tingle, warmth. Her eyes were closed, she opened them, inches from Fluttershy's. Why were they so close? She glanced down, her lips touching Fluttershy's, melded together in one of the most intimate embraces of a couple, hooves around her neck, pulling her into the kiss.

Fluttershy's eyes fluttered, then closed, then jerked open, closing again, her brain operating on several different, contradicting emotions: fear, surprise, happiness, pleasure, ecstacy, elation. She was shocked, cycling between them all before just letting them all melt into a soothing warmth all over, the feeling of love. She shyly kissed back, completely unsure how, just working on her instincts. She pressed her muzzle against Derpy’s, feeling the grey pegasis’ lip curl around her own bottom lip, sucking on it slightly. Where’d she learn to kiss like that? Did she also read romance novels? She thought of Derpy sitting on a chair at home, with an eyepatch. The thought made her snicker a little bit, a pirate Derpy.

Derpy pulled back when Fluttershy began to laugh. “Oh no... I’m doing it all wrong, aren’t I?” She asked, glancing downward, or at least as far as her eyes would allow.

Fluttershy quickly downplayed it, realizing just how rude she’d been. “O-oh no!” She quickly corrected. “No, you were... wonderful. I can’t believe that we kissed like that, it was everything I ever dreamed of. I just had a silly thought and it made me laugh...” She rubbed the residue of a tear out of her eye, sniffling once more. “I’m just so... so happy. I never could never imagine you... the pony I’ve wanted so long, kissing me. You’re not even a stallion... I fell in love with you, a mare... I feel like it’s so wrong.”

Derpy put a hoof on Fluttershy’s shoulder. “My momma always told me, Fluttershy, that there’s nothing wrong with loving another mare, and that it’s just nature. I... never thought I’d be with one, but, I’m sure not gonna deny it. You are the only pony that’s ever loved me... the only. That stallion... who hurt me... he acted liked he loved me, but after I was left broken there... on that bar floor... I knew I was alone... like always.” She stared on, sadly. “I’ve never felt love, but I can see it in your eyes, Fluttershy, you’re serious. I still can’t believe it... I’m so glad you gave me that letter.”

“I almost didn’t,” she admitted, “you have to thank Angel bunny for making me come to my senses. It was still scary though.” She admitted.

“Aw... you didn’t have to be scared of me, Fluttershy,” She said with a little giggle, cuddling under her neck. “I wouldn’t ‘av hurtcha even if I didn’t like mares. That was still a very nice letter... I haven’t felt that happy since forever.” She sighs, glancing away, trying to hide one eye from the mare, to look normal. “Truth is... without Dinky, my little filly... I wouldn’t have much to look forward to in life. I might’ve even jumped off the gorge and ‘forgotten’ to flap my wings by now.”

Fluttershy gasped, hooves covering her mouth. “Don’t say things like that, Derpy! Ponies out there love you!”

“Yeah, to my face, some ponies don’t even do it to my face.”

Fluttershy’s eyes filled with more tears, voice cracking. “I love you...”

Derpy glanced back with both eyes, unable to help the slightest guilt. “I know you do. It’s just hard when... the whole dang world seems to be against you, you know? I love this job,” She poked her mail satchel. “But... I’m not gonna be able to keep it much longer if I can’t hurry up. They told me that. Same thing happened when I was on the weather patrol. I try to take care of ponies, but they always end up taking care of me... on pity.” She hung her head. “I wanna be self reliant.”

“You could work with me, I wouldn’t care how fast or slow you worked, as long as everything got done.”

She brushed her mane, wrapping it around a hoof, a nervous habit. “You’d do that...?”

“Of course I would, Derpy...”

Derpy paused, then nodded. “Alright, but I’m staying with the mail patrol until they fire me, I love this job too much.” She glanced at her satchel. “Um... speaking of... I need to drop off this mail back at the post office. Would you give me a couple of minutes?” Fluttershy nodded an affirmative. “I’ll be right back” She said, with conviction.

Fluttershy could tell, she meant it.

Derpy had never flown so fast in her life, not even when she’d overslept and was thoroughly late for work. She pant and soared through the clouds, wings flapping hard to keep up with her pace. She even managed to avoid a flock of birds today, rather than careen through them. She was elated, running on pure adrenaline, and it was making her a better flier. Normally, she’d find something that could go wrong, but today, it felt like she might even break Rainbow Dash’s record. She saw hazy, double images and ghosts of buildings as her two eyes focused in different places, but she avoided them like a pro, whooshing overhead, making curious ponies look up to see who could be in such a hurry.

Finally, she came to the post office, flaring out her wings to slow down. Landings: not her strong suit. She flapped a few times into the wind, making her wobble in the air, touching down her hooves. She stumbled forward a few steps, falling down, rump high in the air, but she hadn’t crashed, even that was an improvement. She quickly rose back up from the embarrassing position, entering the double doors. She made her way up to the clerk, setting down her satchel. “Derpy Hooves here, with the day’s deliveries.”

“‘Bout time,” She said. “We were starting to wonder where you were. We thought you might have deserted us, or gotten stuck on the ground again from pigging out at the annual muffin festival.”

“Hey! That only happened once!”

“And it was once too many...” She said dryly, starting to pull the bag back.

“Wait, wait!” She snatched the satchel back, fishing around inside it and grabbing her letter. It was easy to find, it was in a yellow envelope. “Forgot abouf dish.” She mumbled as she grabbed it in her mouth.

The clerk arched a brow under her thin rimmed glasses. “You do know that it’s a capital offense to steal mail, right Derpy?”

“No noph...” She spat the letter out. “That’s mine. I got it today while I was on my run. Besides, you couldn’t deliver it if you tried, there’s no address, only a name.” A green glow surrounded the envelope as the clerk held it up to the light.

“Really now... someone sent some mail to you, Derpy. Aw look... a heart... somepony must really like you...”

Derpy had gotten enough sarcasm over the years to recognize it. “Shut up, you’re just jealous because I have somepony, instead of being married to my dead-end job at a post office. Maybe if you laid off the cupcakes, you’d have a more flattering figure.” Derpy shocked even herself. She’d never been that withering before. She’d never had the will to...

The bespectacled mare frowned, swiping the bag a bit more forcefully, saying nothing else as she ground her teeth. Derpy knew her work was done, taking her letter back and walking back towards the doors.

“Oh,” she added, a hoofnote onto her argument. “My date’s a bucking Element of Harmony. How do you like them muffins?

Deliverance (Mature Warning}

A/N: And here, delayed by a week, is the second (and final, and cloppy) part of Letter to a Mailmare! Let me know what you all think, don't be shy with giving me what you really think. I love to hear positive comments, but above all, I would like to hear anypony who has negative comments, because that is where I can see I have improvements!

And give a big thanks to AuRon, for being my pre-reader, I could NOT be prouder of him, he not only caught me when I was being a story/grammar derp, but he gave me some very good suggestions for substituted words. He really wrote about half this story. I suspect a great jump in quality under his wing. (Pun, if existent, not intended.)

Fluttershy continued to wear through a bit more of her floor as she paced to and fro. The instant that Derpy had departed, she began to miss her. She wanted her back, to be blunt with herself. Those awkward moments together were some of the best moments she’d ever had, even better than being with her friends, as much as she hated to admit it. She distracted herself with thoughts of what they could do when she came back.

"What does Derpy like to do?" She mused to herself, and to Angel, who was sitting atop an arm of the couch. "Maybe I can take her out to a romantic dinner? Oh, but it's only lunchtime, who ever heard of a romantic lunch?" She glanced outside at the clear weather. "But, we could take a picnic." She quickly dismissed the idea with a shake of her head. "No, with the crazy weather we've been having, the ground's too wet" She pondered, sitting on her rump. "Maybe Pinkie Pie would know how to have a good time." She suddenly thought of the repercussions of having her involved in the whole situation. Embarrassment in front of the entire town seemed like a distinct possibility. "No!" She quickly answered herself. "Pinkamena Diane Pie can not know about this!"

Fluttershy quickly shut her mouth and turned horrified towards the window, half-expecting Pinkie to be there. Whenever she mentioned that Pinkie couldn’t know of something, a kind of Murphy’s law kicked in, and there she was. Fortunately, her window was empty of the pink mare. She wiped her brow with a relieved sigh, speaking to herself on what she might do. “Maybe Twilight, no that’s absurd. Twilight knows as much about romance as Rainbow Dash knows about chemistry. Speaking of... what about Dash?” She shook her head. “No... too forceful. Rarity?” Again, she shook her head. “No, not Rarity. She’d plan something too... fancy and complicated.” She chewed on her lip. “...Applejack? She’s honest, she could give good advice.” She bit a hoof. “Oh... but her ranch is all the way on the other side of town...”

Derpy cleared her throat, standing in the threshold with a blush forming under her cheeks. "F-Fluttershy?"

Fluttershy quickly spun around, backing up. "Derpy! I-I didn't expect you back so quickly!"

"I told you I'd be right back, and I keep my promises after all." She shyly rubbed at the floor. "I flew as fast as I could." She approached the yellow mare with a little nicker, nuzzling under her neck. "Y-you don't have to be worried about what to do with me, Fluttershy. Just spending time with you makes me happier than I'd ever be alone."

"I wanted it to be wonderful for you though, you've been pushed around so long. I wanted to show you that you're appreciated."

Derpy licked her cheek and Fluttershy felt herself getting hot. "I know you appreciate me, Fluttershy. I've been ignored by ponies for over nine years now. Even having a conversation like this is the most romantic thing I could ever imagine; when nopony wants to talk to you because they think you're stupid, it just gets lonely."

Fluttershy's ears wilted and she found herself pressing her muzzle against the mailmare's neck. "That's so sad..." She trailed off.

Derpy shuffled nervously. "There is... one thing... you can do for me."

"What's that?" Fluttershy perked up, prepared to do anything for the mare before her.

"Can you, kiss me again? I've never had any kind of real romance before, and that kiss before, you know... the accidental one, I felt like I was just melting into it."

Fluttershy hesitated, feeling herself lock up, but it was only momentarily. Once you looked past her wall eyed stare, Derpy really was a beautiful mare. She was still scared, but nonetheless she leaned forward, stretching out her wings as she did so. "Yeah, that seems..." She paused, her voice but a whisper. "...nice." She rocked on her hooves, glancing around the room, as if she expected someone to be watching her. Satisfied, she suddenly pushed forward and planted her lips on Derpy's.

Derpy gave a surprised little squeak, not expecting Fluttershy to be so assertive. It was nothing like the gentle drifting together that she’d read in her novels. Her ears perked up and twitched briefly, eventually settling as her eyes drifted shut. A shiver rattled her form as she once again felt that prickling warmth against her lips. Her senses all melted back into the background, except for touch, as their lips slid past each other, working with their instincts. Both were naturally curious about romance, and if what they’d read was true. They deepened the contact, Derpy opening her mouth slightly. Fluttershy’s tongue slid past, wrestling sloppily with Derpy’s, pressing against it, wrapping around it, pushing it back.

Derpy felt a little saliva run down her chin, but she didn’t care in the slightest. They were probably doing it all wrong, but she couldn’t find a reason to stop, pushing Fluttershy’s tongue back to her own mouth, repeating the motions, now holding Fluttershy back. She heard the faintest moan drift from Fluttershy’s throat. Blood rushed through her veins, heart thumping. Her wings rose against her own will, stiff as a board, flared fully for flight. Her face burned, such an embarrassing thing to happen! She pulled back with a gasp, the slightest trickle of their combined salivas hanging between them. She desperately pushed her wings down, though they refused to stay down for long, always popping back up. “Sorry, sorry... this is so embarrassing...” She glanced up, gulping. “I-I just don’t know what went wrong.”

Fluttershy gave a coy little giggle. “Oh, it’s alright, I’m not much better.” She gestured back to her own wings, just as erect on her back. She tried to ignore the insistent tingling in her flanks, pressing her legs together. That kiss worked magics on her that she doubted even Twilight could understand, even if it was improperly done. She quivered, wiping off her mouth.

An idea came to her suddenly. Derpy was on her wings all day, wasn’t she? She was good with massages -- after all, she’d managed to massage a bear. “Derpy, would you lie on your belly for me, you know... if that’s okay with you?”

Derpy blinked in confusion, but gave a nod. “Uh, sure Fluttershy, what do you have in mind?”

Fluttershy straddled her back. “Just relax, my love.” She blanched slightly. Did she just say that out loud? Did it even matter anymore? She ignored the feeling and pressed a hoof to Derpy’s back, at the base of her mane, flapping her wings to hover slightly, freeing both of her front hooves to press at her back, making small circles, kneading downwards.

Derpy shuddered and pressed her face into the ground. This kind of attention certainly wasn’t helping her wingboner. She gave a quiet little purr and turned her head to the side, closing her eyes and just enjoying the attention with little twitches. “Mmm... Fluttershy, that feels great.”

Fluttershy gave the slightest of smiles, continuing on, her hooves moving fluidly across the span of her withers, focusing on the muscle groups that spanned to her wings. Derpy’s hind leg twitched and she skipped a few breaths. “A-ahh... Fluttershy...” She gasped out, melting beneath her skilled hooves, as a few knots loosened in her back, releasing their tension. Her tongue lolled out lazily as she nickered, splaying out. “B-by the Princesses... how’d you learn to do that?”

Fluttershy just giggled softly. “I’ve had a lot of practice with the animals.” She casually moved down to the bases of her wings, rubbing into the junctions tenderly.

Derpy gasped, head shooting up, entire body shivering. “Fluuuter... uhhn...” Fluttershy’s cheeks lit up brightly. Did she just moan? She tried again, working her hooves into the toughened patch. Derpy’s eyes clenched shut and her body tensed. “H--hhhh... mm! Fluttershy...” She panted. “C-careful Fluttershy! That’s a sensitive area!”

“I-it is? I’m so sorry, I didn’t mean... please don’t be angry.” She swiftly apologized, feeling silly for not knowing that fact. It obviously was rather tender, considering Derpy’s reactions to the slightest rubs.

Derpy nodded, responding to her question. “Y-yeah, you’re a pegasis, hasn’t anypony ever touched you there?” She glanced backward. “And don’t apologize, Fluttershy, it didn’t hurt.”

Fluttershy coughed slightly. “Oh... o-okay, but n-no... I always bolt when somepony touches me.”

The mailmare slowly rose to her hooves. “I’ll show you then” She turned, gesturing to the floor. Fluttershy laid down hesitantly on her belly, wings twitching. Derpy laid one hoof on a wing, and stroked softly against the pillow-like surface. Fluttershy shook and twitched, then gave a squeaking gasp as the hoof brushed to the very base.

“Oh yeah... that is kinda... mm... tingly, isn’t it?”

Derpy nodded, continuing to work into the sensitive base. Fluttershy quivered and gasped periodically as the sensation coursed through her. She whimpered a bit. “O-okay, you can stop now...” Derpy continued on, Fluttershy’s legs buckled, leaving her splayed out against the ground. “N-no... really! T-this is embarrassing!”

Derpy was enamored with her reactions. She knew pegasi were quite tender there, but she was hardly even touching her, was Fluttershy particularly sensitive there? Maybe she was just oversensitive in general. From what she’d heard about her in town, she tended to start at the slightest touch. She decided to lean under her wing and give her a little nip. Fluttershy’s eyes flew open and she then just buried her face into the floor, squeaking out a rather unmistakable noise: a moan.

Fluttershy was starting to regret surrendering herself to Derpy, she was going to end up embarrassing herself to the ever more flirtatious mare. “I... really should get back to your massage, you were quite tens--uuu...” She cooed as Derpy applied another nip to her wing. “Stoooop...” She pleaded halfheartedly, melting under her hooves. Was it suddenly hotter in the room? Her heart was beating hard, and she couldn’t keep her thoughts straight. They just kept drifting away to Derpy’s wonderful body. “A--ghn...” She trembled, eventually just letting it happen.

Derpy giggled, moving away from Fluttershy’s wings for a while (much to her relief) and now just stroking her back. “It’s cute to hear you moan like that, you’re so sensitive. I don’t think I’ve ever made a pony make that sound...”

“Uu...uh...” She purred out absently, broken beneath Derpy’s hooves. Her eyes closed, a smile plastered on her face. She didn’t realize how much she herself needed a massage.

Derpy hummed a nursery rhyme as she worked, making Fluttershy want to just curl up and fall asleep. She almost did so too, eyes lidding as Derpy’s hooves roamed around her back. The world faded into a blur, and she constantly made little purrs, barely even keeping track of where Derpy was now. That is, until she felt her tail being lifted. She gave a harsh squeal and bucked back, her hind legs hitting Derpy straight in the chest, sending her stumbling a few feet backwards.

She coughed, much of her breath knocked out of her. “O-ow...” She got back up shakily. “I probably deserved that... I was just curious.”

“Oh Celestia! I’m so sorry Derpy!” She jumped to her hooves and rushed over. “I didn’t hurt you, did I? Oh Princesses... I’m so sorry!” Her eyes welled with tears as she constantly apologized and fussed over Derpy to make sure she wasn’t injured. “I didn’t mean to kick you, I swear!”

Derpy waved away her hooves, as the pegasis was suddenly all over her. “Fluttershy, really, I’m fine, I’ve taken dozens of hits harder than that. I crash every dang day.” She saw Fluttershy in a genuine state of panic, tears streaming down her eyes, trying to keep her only lover. “Fluttershy, please, that was my own fault. That was... well, stupid of me to try something like that.”

“So... you do like me like... um...” She shied away, unable to mention it.

“Enough to be... romantic with you?” Derpy offered quietly. “Of course. I’ve never had sex before.” She coughed. “Um... well, I did, but I didn’t enjoy it at all. He never made me feel it, or to really want it, it just kind of happened. He never made me feel like...” She looked up, a tear in her eye. “...you.” She turned away, a nervous habit of hers, to make herself look normal, hiding her off-kilter eyes by showing only one. “I just... I just wanted to see what you looked like, if you’re as beautiful there as you are everywhere else. I guess that was a silly thought...”

“Yeah, it kind of was”

“...of course you are.” She continued her thought as if Fluttershy hadn’t spoken.

Fluttershy was about to giggle with the silliness with the thought, until Derpy continued speaking. The urge to laugh was caught in her throat and she swallowed awkwardly, cheeks flushing.

“...Um... D-Derpy? How long do you have until you have to get home?”

“A-A couple hours, then I have to be home for Dinky.”

“D-do you want to... you know?” She barely asked. “I-If that’s okay with you... no pressure or anything...” She squeaked out, even quieter, voice barely above a whisper. “It’s okay if you don’t want to... or...”

Derpy gave a toothy smile behind a quick little blush. “I’d be honored to, Fluttershy. Though... I don’t really know what to do.”

“Lick and rub... you learn fast enough.” A quick image of a romance novel aimed at the filly-fooling demographic that she’d read popped into her mind. “...not that I’d know anything about that.”

“You’re such a terrible liar, Fluttershy.” Derpy cooed and kissed her, though this time on the neck, guiding her onto her back. Fluttershy gasped and shuddered as she was lain on her back, leaning away from the kiss to expose more of her delicate neck. Her hooves instantly reached to cover her shame, but she hesitated, instead letting them fall to her side, nervously spreading her legs. “Am I... good... enough?”

She nodded with a little giggle, her eyes locking to the jewel between her legs. “You’re better than good, Fluttershy. You look like you take care of yourself.” Derpy didn’t really need too much convincing, she’d jump at the chance to make love with someone who really cared about her, but she figured Fluttershy might need a little bit to help her relax. “Do you ever... play with yourself?”

Fluttershy gave a little bit of a nervous squeak, but was able to giggle it away. Nopony else was here, and she trusted the mailmare. “Uh... a little. Sometimes, when I’m reading a really good romance and it gets to the... dirty parts, I like to envision myself there. B-But I never really get very far, there’s always an animal looking at me, and I get too shy to really continue.”

Derpy giggled. “When Dinky’s away and I need something to do but I don’t really feel like going out to town, I’ll sometimes... mess around with myself. Made some real messes, too, good thing I’ve made so many other ones in my life that I know how to clean them up...”

Fluttershy gave a coy giggle. “Well... uh... I do a LOT of reading... and I’ve heard some pretty crazy things...”

“I’m sure you haven’t read about an innocent student trying to peek at the rump of her teacher, constantly.”

Fluttershy covered her mouth. “Cheerilee?”

Derpy nodded and gave a little nervous grin. “Yeah, at least when I was still in school, I always tried to look, because I was curious. I wasn’t exactly... um... well, what I’m trying to say is I was pretty obvious about it. I’m not really a very subtle pony, as you might know.”

Fluttershy was intrigued, though she tried not to act it. “So, did she catch you?”

Derpy blushed. “Yep. She yelled at me, though she wasn’t totally angry, she told me where I could find a book that would explain ‘everything that I wanted to know’ in the library. This was before it was run by Twilight.” She leaned over Fluttershy, starting to lick at her neck. “Are you really sure you want to go through with this, Fluttershy?”

“I have to, Derpy. I’ve always backed away from everything. I-I’m not going to run away from love.”

“Love doesn’t have to be sex.” Derpy noted.

“I know, but it’s too late to go back. I’m... I’m... um...” She pressed her hooves together. “Er... excited?” She barely whispered the words out, swallowing back a bit more embarrassment.

Derpy snickered. “Well I knew that.” She said, as if it were obvious. “I could tell by how wet you got... you left a spot on the floor when I was messing with your wings. Speaking of...” She reached her hooves behind Fluttershy, working back into her wingbases, licking down her chest and then up her neck.

“What?!” Fluttershy began, craning back her head to see the little moist spot on the ground where she had previously lain. She went to speak, but her words were stolen as Derpy again teased the delicate wingbases with her hooves, feeling her tongue burrowing into her neck fur, wetness penetrating into her skin. “G-ggah! N-No... D-Derpy!” Fluttershy didn’t even know why her words resisted, she enjoyed every moment, her dew soaked flower quivering as Derpy’s leg rubbed against it. It was such a delicate sensation, each fur tickling the sensitive lips. “H--hha... Derpy... m-mmm...” She purred out, tense body relaxing a little.

“It sure has been a while,” Derpy commented. “I hope that I’m good enough for you.”

“You don’t have to worry about that.” Fluttershy rebutted, her voice trembling. “If you keep up like that...” She didn’t have the strength to finish her thought, but then again, she didn’t have to.

Derpy took her liberty with Fluttershy, lips meeting briefly with the yellow mare’s, brushing against each other. Entranced, Fluttershy kissed back with lidded eyes. Their tongues met without thought, but not without emotion, wrestling, tangling, exchanging subtle flavors. Fluttershy’s chest rose with a deep inhalation, resting her hooves on the back of the mailmare’s head, unconsciously locking into the kiss.

Fluttershy didn’t know she could possibly cry any more tears, but sure enough, more fell down her cheeks, not generated from sorrow or fear, but rather joy. Derpy finally pulled away long enough to whisper. “I love you too, Fluttershy.” The shy mare choked out a little sob, unsure of how to react, trying to give her words of appreciation back. She was only able to give another gasping sob though, as Derpy had decided to give her ear a little lick. Her body writhed under the attention from all angles.

“You really are sensitive everywhere, Fluttershy.” Derpy teased, pulling back from her ear.

“A-Am I?” She asked, unable to come up with a witty reply on account of her embarrassment.

Derpy didn’t reply, instead her teeth latched onto that tender triangle of flesh while her hooves roamed back to her wings, more forcefully than before. Fluttershy could have been mistaken for a feline for how her back arched, squirming with sharp moans. “A--ah! Oh! D-Derpy! W-what are you-oo--oOH!” Her eyes rolled back, panting quickly, biting her lip to try and prevent any other outbursts. It was far from easy work, sweat dripping down her face from the effort. Or maybe it was just the innocent, yet nonetheless strong pleasure that coursed through her? She couldn’t tell. Eventually, her will broke as Derpy kneaded her ear between her teeth, squealing, panting, eyes shooting open.

Derpy finally released her wings and ear from her clutches. “Has my little filly had too much?”

“Y-you’re horrible!” She whined, though her nervous smile betrayed her true thoughts. Her pants and gasps quieted only slightly when Derpy pulled back, her crooked amber eyes staring into Fluttershy’s, a rich teal. She quickly darted her eyes around Derpy’s face, seeing the seductive smirk. She couldn’t understand why until she felt the hoof pressing against her nethers. Those strained noises returned with a vengeance, her jaw quivering. “Nnng! A--ahh... Derp...y... hh-aaa...”

“I’ve wanted to do that to somepony special for a while now.” Derpy whispered, licking her neck.

“Me too...” Fluttershy blundered back. She didn’t really understand what she was saying, she just wanted something to respond back with, to not leave the sweet mailmare hanging. It was Fluttershy’s first relationship, at least the first that really meant anything to her, and she was doing all that she could not to ruin it.

“You don’t have to hold back so much, I won’t think any less of you if you’re being a naughty filly...” Derpy ventured another tease.

“S-stop...” Fluttershy whimpered out another coy reply, cheeks flushing pure crimson. In response, Derpy only began to rub her hoof quicker along her slit. Fluttershy squirmed, a bit of her wetness spreading onto Derpy’s hoof. “Oh Celestia... oh gosh... oh gosh... OOooohhh... Deeerrrppyyyyy!” She wailed, her fur standing on end, a flood of sensation working over every inch. Fluttershy was starting to panic. The pleasure was notably one sided, and she had to do something.... something.

“Flutter... AH... ooof... what are y-you?” Derpy was suddenly on her back in a burst of strength and will from Fluttershy. The yellow mare herself blinked in confusion, unsure of what had just happened. Apparently, she’d done a reversal, now she was the one on top. Not one to waste an opportunity, Fluttershy went for Derpy’s neck, hesitating only a moment before doing to Derpy what Derpy had done to her, licking and nipping across the sensitive flesh. Derpy was still trying to figure out what happened, but that curiosity faded into a carnal desire, letting the now surprisingly dominant Fluttershy kiss and nibble at her. “Oh yes... please...” Derpy whispered huskily.

Fluttershy roamed a bit further, her curiosity getting the better of her. Derpy spread her legs quite willingly, exposing her ash grey pussy to the shy mare. Fluttershy was trembling as she lowered herself down between her legs, trembling even as she held to Derpy’s lithe form. Fluttershy paused for a long moment, going over it in her mind. “You can’t back out now Fluttershy, you’ve come so far, and by Celestia, you need it!”

She finally pressed her nose to Derpy’s flower, to see it, much like hers, quite wet with their combined teasing (though Derpy was by far doing most of it.) She nuzzled in, taking a short inhalation of the scent. It was quite pleasant, surprisingly, or at least to her, smelling of hay. She gave a tentative lick inside, tasted of it too.

It was Derpy’s turn to sporadically breath and gasp, with Fluttershy’s nose and tongue applied right to her pleasure points. “Oh F-Flutter... mmm...” Her leg twitched with the spikes of pleasure from Fluttershy’s curious tongue. “Y-you’re pretty... good at this...” Derpy couldn’t think of a place she’d rather be. She’d experienced the pleasures of the carnal arts a few times before, with her own experimentation, but none had been so intense as when experienced with another pony, a mare no less! Fluttershy stalwartly licked, right up and down the part of her flesh, the juice sticking to her tongue. Such a peculiar flavor, but she wouldn’t trade it for the world.

Derpy’s back bent backwards, her hooves grasping at the ground. Her voice rose an octave and a half, babbling out whatever was on her mind at the moment, she couldn’t focus enough to make a coherent thought. “Fluttershy... right... ha... yes, there. Oh you know what you’re... hah... you sure this is your... mm...mmm!? OOooh... Buck me Fluttersh--ss--hhhyyyy!” She eventually bit back the cascading waves of ecstacy to collect her thoughts. “Th-that nub... at the top... please!”

Fluttershy had read enough to know what that did, of course in the heat of the moment she’d forgotten about it. Her tongue exited the tight walls of the ash furred mare and instead licked at her clit, caressing it with the tiniest of strokes. What were moans quickly progressed into squeals, thrusting her hips forward eagerly, involuntarily. “Yes... yeeeeeesss! Oh Fluttershy...!”

Fluttershy diligently licked and suckled the sensitive button as Derpy melted under her, until, finally, she pulled back, a bit of Derpy’s juices clinging to her muzzle. “Am I... doing a good enough job?”

“Yes!” She fired back immediately, barely managing to breathe the word out. “You’re doing w-wonderful, really.”

“You’re sure?” Fluttershy shyly asked, a drop of the clear liquid falling from her chin.

“I’m sure!” She said, an undertone of annoyance in her voice. She winced, ears flopping down, apparently regretting the tone. “Yes, sweetheart... I’m sure... don’t worry. Just keeping doing what you’re doing, alright?”

“A-Alright.” Fluttershy dove back into her inner thighs, tracing a path along every surface her tongue could reach, sometimes pressing in to the tight walls, other times drawing back to lick at the stiff bump at the apex, secretly relishing how she shivered, though she’d never mention it out loud.

Derpy laid back to enjoy Fluttershy’s increasingly skilled ministrations, wings splayed out beneath her. Her chest rose and fell in deep, but rapid breaths, occasionally missing a beat and either inhaling too much or gasping to pull in more. A pleased whimper would occasionally drift from her open mouth, and she visibly gripped at the ground as the pleasure became more and more intense, eyes alternating between opened and closed. “Please... faster...”

Fluttershy, gulped. “O-okay.” She mumbled, not really bothering to pull away, as she was buried in her at that moment. The muscular appendage dexteriously flit around inside Derpy’s ever quivering pussy, their tails flicking aside out of instinct. “B-buck! Celestia... you’re so good Fluttershy... how much do you read?”

“Um... well...” She paused, thinking of an answer.

“D-don’t stop! Rhetorical question!” Derpy added hastily as she felt her attentions waning.

“Oh.” She resumed right where she’d left off, making lewd slurps as the juices flowed quite liberally. The mailmare’s face was fully flushed now, tongue hanging out and her mind in a haze, only able to choke out little sounds. Her breath rose to near hyperventilating, head tossed back.

“Ah... ah... aaah.... aaahhhh!” Derpy’s moans rose in volume and intensity, her wings flapping uselessly against the floor. “Mmph!” She held her mouth shut tight, and, failing that, stuck her hoof straight in her mouth, biting down on it, back again arching, a shrill scream muffled behind the intruding hoof. Her nethers grasped hard on the tongue and a few spurts of sticky cum fell over Fluttershy’s face, hitting her right between the eyes, her entire body shaking like a leaf.

Fluttershy could only blink, frozen in a state of shock. “What... was that?” Without thinking, she wiped off her muzzle, sticking her hoof idly in her mouth for a taste: a sweet, sticky hay... maybe a hint of daisy. She froze, eyes widing, quickly pulling her hoof away. What in Equestria was she doing?! She banished the thoughts with a quick shake of her head, looking down at Derpy below her. She was splayed out across the ground, eyes seeming even less focused than usual, dazed, confused and broken. “H-hhaa... Luna... that was...” She took a ragged breath, trying desperately to get to her hooves, legs shaking when weight was applied to them. “...absolutely crazy.”

“Sorry, did I do it too hard? I’m so terrible, it’s my first time and it’s just so hard to do it right and...”

Derpy quickly stopped her with a hoof to the mouth. “Fluttershy, don’t worry. That was the best thing I’ve ever experienced.”

“I-I thought you were shaking because you were scared.”

Derpy gave her a deadpan stare, though it was hard to perfect considering the rather comical placement of her eyes. “Wow, you really haven’t cum before.”

“I haven’t...” She admitted.

“Well, from what I’ve heard, it’s different from pony to pony... but when I cum... I really shake.”

“...oh...” She whispered, feeling rather silly for not knowing that.

“Oh hey... don’t worry about it Fluttershy. We’re both really new at this, and romance isn’t known for being the most... accurate. Maybe we should ask Twilight for some better books. Course... I may not be able to understand them. I’m not exactly a genius.”

“Are you calling yourself stupid again?” Fluttershy asked, almost angrily.

“No, no! I’m just... you know, a little bit less than average. You helped me see I’m not stupid, but it’d be just hubris to say I’m smart.”

“Says the pony who correctly uses ‘hubris’ in a sentence”, Fluttershy quipped.

“...Heh.” Derpy had no response for that. “Well...” She gave a seductive little giggle. “I suppose it’s your turn then?”

Fluttershy blanched, quickly deflecting away. “Oh no, you don’t have to! I’m a romantic and all that, I’m satisfied when you’re satisfied...” She ended her statement with a nervous laugh.

Derpy licked her lips, then Fluttershy’s muzzle, tasting a bit of her own leftover juice on it. She played with it on her tongue, sampling it’s quite unique flavor. “Must be using a lot of hay flour in my muffins...” She thought to herself.

“Well... maybe I’m not satisfied.” She nibbled along Fluttershy’s ear, this time aware of the weak spot.

“Oh Princess... not the ear... please not the eeaaaarrr...” Fluttershy pushed her hooves into the ground, head turning into the nips. She trembled, tongue hanging out limply. She squeaked as Derpy rolled her onto her back, turning about face with a few flaps of her wings, her muzzle pressed right up against her flower. Fluttershy was still moist from earlier, dripping with new juices as she was unwittingly aroused from her efforts on Derpy. Her voice was a terrified vibrato, blush overtaking her face as she realized just where Derpy had her mouth. “N-no! R-really! Y-you don’t h-have to...ooh...ooohhh!” She was cut off as Derpy began to lick furiously, much more sure with her motions than Fluttershy had been.

In reality, she had even less of an idea, but was much more willing to just try it. Fluttershy was already bucking, gasping with each less than delicate lick across her clit. She kicked up at the air, fighting to suck in each breath. Whatever attempts to speak were quelled by Derpy’s curious licks. Fire spread across her abdomen, burning through her veins. It was almost too much too take. She’d never gotten anywhere near this far when she was working alone. She was frozen in half shock, half pleasure, rising quickly with the novel sensations.

Suddenly, Derpy pulled away, muzzle matted with Fluttershy’s produce now. She’d been making an awful lot, that was for sure. “Mmm... strawberry...” She licked her lips, forgetting what she’d come up for. “Oh right... are you alright Fluttershy? You’re awful quiet.”

With the almost overwhelming sensations now gone, Fluttershy was able to take a few deep breaths, a long, drawn out moan forced out of her throat, cheeks now a bright shade of pink. “Ce--lestia...” Words still weren’t coming well to the mare, but she managed to squeak out a couple more. “S-so good...”

Derpy gave a faint smile, pressing herself back in, her efforts redoubled, and never one to be worried about sounding lewd, slurping up Fluttershy’s sticky cum.

Fluttershy’s tongue hung limply out the side of her mouth, eyes squeezed shut. In lieu of moans, feminine squeaks accompanied each buck of her hips. “B-buck... oh gosh... I’m so... hh...hha... I feel it c-coming!” Her mind was swimming, flooded with hormones, her breaths shaky. Without thinking, her hoof went to the back of Derpy’s head and pressed it into her hot sex, clenching her thighs tight around her. She bit her lip until it almost bled, then felt something break inside her, stars flashed across her vision. She snapped her head back, and whereas Derpy had been relatively quiet, Fluttershy practically screamed at the top of her lungs for a couple of seconds before curling her legs up against her belly, twitching, a gush of thin juice covering her entire rump and Derpy’s muzzle. She hoped to Celestia that Derpy had closed her eyes, though it was only an afterthought, as she was left gasping. Her limbs felt like lead, she was just unable to move.

Derpy licked a bit of Fluttershy’s cum off her face and giggled. “Whoa... impressive.” She grinned, but soon she took a spot next to Fluttershy, pulling her hooves around her neck. “So... how was your first time, Fluttershy? I didn’t... go too hard did I? I know you’re a sensitive filly...”

Fluttershy groaned, pulling her eyes back in focus. “Y-You were fine...” She slurred in an inebriated pleasure. “More than f-fine a-a-actually!” She coughed and gave a shy little smirk. “Was... I... um good, too?”

Derpy nodded frantically. “Oh yeah... that was fantastic.” She fought back a giddy little squeal. “Ugh... what time is it?” She glanced back at the clock. “Oh wow, I need to take a shower and get over to my hous--” She looked back to Fluttershy, who was now soundly asleep on the ground, a wide smile plastered on her face. “...aw.” She couldn’t help but chuckle, lifting her up carefully. She flapped her wings rapidly to lift them both, a little shaky with the combined weight. Fluttershy instinctively nuzzled into Derpy’s chest with a coo.

“D’waa... you’re adorable Fluttershy...” She said quietly, reminded of tucking in her own foal. She laid her down in her bed, pulling the blankets over her, then planted a kiss on her forehead.

Derpy borrowed Fluttershy’s shower quickly, for she surely couldn’t fly home in such a condition. She grabbed one of the blank parchments lying around from when Fluttershy had written her letter, taking a quill and marking out a small note to say she’d gone out.

Dear Fluttershy,

You fell asleep. Don’t feel bad, you probably got up early, and you came pretty hard. That was absolutely wonderful, and I will never, ever forget it. I look forward to going out with you, as mates. Please write me another letter, or talk to me when I’m delivering the mail, I’ll take you over to meet Dinky.

I’ll see you later, Fluttershy. Consider the love requited.

Love,

Derpy Hooves.

P.S. I didn’t actually learn that word on my own, I read it in one of those romance novels and looked it up in the dictionary.

She tucked it into an envelope, giggling, plucking one of Fluttershy’s petunias out of the ground outside and placing it in a vase, leaning the envelope next to it, embellished with a heart.

Just like her own letter had been...