Author's Note

I hope you all enjoy this chapter. I will be working as best I can to have more come out in a timely manner. Thank you for reading.

Step 1: Discovery

Step 1: Discovery

This time of year was unrivaled in its pure appeal to the eye. Fall came with such wonderful colors and a vibrancy that perfectly contrasted the slumber of coming winter. Winds carried the scent of wet leaves and the cold snap of the mountains high above. Ponyville was shrouded in the cooling embrace that let everything be more energetic, warmer and more alive. The change in climate made some sluggish and irritable, but not Derpy.

Derpy’s routine trek through the village was his chance to patrol his territory. The grey stallion’s eyes struggled to focus on any one thing for too long, thus it always paid for him to be moving. Mornings in the fall were his favorite of all, for the nightmare night decorations were going up and the brilliant leaves coming down. He could snug his uniform a little tighter about his body and walk around comfortably in his trousers, for once. It was the most drastic change all year and brought him immense comfort as he scanned through his pack. Addresses weren’t necessary in his mind anymore- partially because he could never remember numbers that large and because of his familiarity. He knew each house by shape and color, each face of a home attached to the face of a friend.

The homesteads were all special in their own way and wore mnemonic devices on their fronts. Berry’s house was always so dramatically lit on the inside. Carrottop put out small banners for each holiday. Twilight’s house was taller than anything Derpy had ever seen apart from the peaks of Cloudsdale. But none of them stood out quite as sharply as one particular home in the very center of it. A single place that Derpy knew by its owner, its look and its aroma.

A smile drew across his brick-shaped snout when he spotted your cottage. A small abode, even for a pony. The wheat-colored building sat between two newer cottages that squeezed in on it like the trunks of mighty trees. It seemed such an unfitting place for such a large creature. Derpy saw you as a towering behemoth with long and slender limbs that needed much more room. He imagined that a castle, or perhaps a barn would befit a human better than some dinky shack. Sometimes when he came to your door, he couldn’t help but harbor some distinctly resentful thoughts for the Princess that had given you this place.

If he had it HIS way, you’d have a wonderful hangar of wide-open space for your giant form to stretch in. If Derpy could build or design, he would’ve happily crafted a home to rival the Sweet Apple Acres barn in sheer size, just for you. The stallion was too soft to ever bring such a sentiment up, of course. Few ponies took him very seriously at all to begin with. Any and all complaints he had about ponyville revolved around the singular human living there. His fixation had begun the moment you started getting mail and talking together. Derpy was keen to make your deliveries a top priority and your comfort just below that.

He voiced complaints at Ponyville councils about the height of door frames, for you hadn’t adjusted to the much lower height and constantly knocked your face against them. He had anonymously written letters to Twilight demanding your home to be renovated and gussied up with gardens and new construction at no charge to you. And, whenever he could, Derpy brought you gifts and tokens of Ponyville’s “welcome.” It had been months since you had come, but apparently there were still “welcome to our town” presents to be distributed. You got blankets, coffee, plates, books, spices and greeting cards every other day in the mail. Yet, not one of the packages had a return address. Derpy flooded your home with warmth and secret affection… yet he could never really say why.

Seeing your home now, as he did every morning, once again brought an avalanche of warmth to his belly. He stirred with glee in his uniform and made sure his hat was on straight. His mane was combed and tied back with bands to keep it neat and handsome. His hooves were polished and trimmed with the utmost care and his rump was covered in his pressed, clean khakis. An unusual addition for any pony, but the stallion passed it off as an addition to his uniform with some admirable form to the ensemble.

Normally he let his gilded mane hang naturally and blow comfortably in the breeze. But for you, nothing short of perfect properness was acceptable. He trot onto your stoop and knocked soundly on your door with confidence in his heart. Normally, letters just went into the slot and that was that. But you got each parcel hand/mouth delivered to you. The stallion always wanted to talk as well, though the topics were as confused and goofy as his eyes.

But for some reason, there wasn’t a stir in the home. Derpy waited and waited for just the slightest shuffle or shift inside the tiny house. He could always hear your heavy and soft footfalls coming from the next room, for the floorboards creaked terribly and your human weight put more strain than normal on them. He continued to stand there with such concentrated stillness that orange sheets of falling leaves fell and rested on his back. He knew you didn’t always wake up on time. He was well aware that at other times, you were bathing and unable to get to him right away. Some days, he would stand there and wait contently for 10 minutes or more. Or at least he did when he could tell you were home.

It was far too quiet for you to be here, today. No shifts from the bed, no creaks from the floor, no bubbles from the coffee maker. He couldn’t even detect your manly scent in the air, for this morning it was insultingly fresh and clear. Without a hint of your presence, he was gone. He eschewed his normal path for an immediate trot toward your potential hiding space. His compulsion to deliver your mail personally drove him to search the market high and low for a hint of you. He sniffed the air for that unique and savory taste of human, for both his eyes could never focus long enough to catch your distinct appearance. Thankfully, with you standing a good 3 feet over every other pony there, he discovered you soon enough.

“Mr. Anon! Mr. Anon!” Derpy exclaimed when he was much too far away for a proper greeting. You and your slight posse looked up from your coffee and busted cart to spot the girly stallion literally jumping toward you in glee. He bobbed and dodged through the crowd, an action you saw as nothing less than adorable. Big Mac and Caramel were less impressed, though they saw no reason for alarm in Derpy being so eccentric.

“Here he comes…” You said whilst sipping from your mug. Your expression strayed little from the normal deadpan, but Derpy was never fazed by a lack of reciprocation. Something about the stallion must’ve simply fed off of your presence and made the poor pony giddy like a sugar high. He couldn't stay still or talk straight when he delivered your parcels. Some mornings you went through two whole mugs of coffee just listening to him ramble about this and that or whatever came to his mind. Seemingly anything that would buy him more time to sit there on his pudgy haunches and stare at you, he would do.

“Ain’t he a perky colt?” Caramel interjected when Derpy tripped and planted himself face first in the ground. You shrugged and pulled the cart back up to level, allowing Mac and Caramel to finish putting the wheel back on it.

“Nothin’ wrong with loving your job.” The grey blur finally jumbled his way up to you with a dopey grip across his face and sprigs of grass hanging from his cheek.

“Hey, Old Boy. Whatcha got for me?” You asked the mail pony. He bounced and jiggled in place whilst he pulled your immaculately cared-for and clean letters from his breast pocket. Your things never went in the mailbag to get squished and tossed around with the normal stock, for your stuff was apparently far too important.

“Mmg- pph gph!” He proclaimed through a mouthful of letters that bulged with a particularly fat envelope. Puffy cheeks and glowing eyes beamed with such energy and youth and potential that your human mind couldn’t deny giving him whatever his goofy heart so desired. Even your hardened heart gave way under his charms. A smile crossed your face as you took the letters and ever so gently brushed a finger tip against his lips. Derpy, like most ponies, was eye-level with your belt. Ponies never seemed to mind staring at your groin whilst they talked to you, but you couldn’t ever get it out of your mind. Things had progressed such that you weren’t wearing so much clothing anymore, for ponies considered it rather stuffy and strange.

Standing there in bare feet, a sleeveless shirt and shorts left you rather exposed to both the cold and needy stallion eyes. Derpy stared like a puppy would. Wide eyes, pursed lips and the most hopeful expression one could possibly wear. The grey pony never left your side until each letter was opened and inspected, for that was often when he’d strike up a long-winded conversation. So, whilst you opened each paper parcel with a pocket knife, he rode the high of your brush against his mouth. So warm and firm you were, he could’ve fed off the positivity from a pat on the head for weeks.

“Get anything good, Mr. Anon?” He asked with chipper glee in his voice. You smirked and combed through the boring and dull documents for his amusement. Though it aggravated your friends to be so distracted, it was worth it if the nicest pony in town was happy.

“Let’s see…” Each letter was inspected and fawned over for Derpy’s required duration. His mail was like personal gifts for you, each bill and notice of changing local laws a tiny string connected right to his soul. You simply nodded and passed them off until the fat envelope was next.

“Oh wow! You got another gift!” Derpy chimed in with such mirth that his hat went askew atop his head.

“It’s been 5 months. There’s more presents in my house than there are ponies in Ponyville.” The pudgy mail-stallion giggled and waited eagerly for you to enjoy the new thing he had gotten you. Derpy could never put into words what compelled him to buy you so many things, especially when he couldn’t ever admit that it was him. Something just stirred and screamed inside him whenever he saw you wearing a hat he had picked just for you. Butterflies kicked and knocked around his belly when you finished a bag of coffee he had agonized over at the shop. And now, you were opening yet another token of his mysterious feelings.

“It’s good stuff, right? You like the gifts?” Derpy couldn’t physically drop his smile when you pulled a woven bracelet from the sloppily packed paper interior. His eyes sharpened and almost focused entirely on the piece when you held in your hand. Black and brown leather was bound together by loose knots and accented with slight beads of metal. It shone bright with a masculine charm to it, albeit one that you would’ve considered slightly douche-baggish back home. You regardless accepted it right away, sliding it over your hand and discovering that its fit to your body was nearly skin-tight.

“Wow. These gifts keep gettin’ better and better. You think this is real leather?” Derpy never recoiled when you offered a hand for closer inspection. Unlike the vast majority of ponies who wanted to avoid your “spider-like” fingers, as Rarity put it, he was eager as an itchy cat to touch them. He cupped your hand in a hoof and closely inspected the jewelry he had made just the week before.

“It looks great on you, Mr. Anon!” He huffed with a not-so subtle touch of his cheek to your palm. You knew it to the very bottom of your heart from the very beginning. Derpy was not a complex soul that was clouded by mystery or deceit. In a way, that’s why you appreciate him so much. He was soft to the touch and so suggestable, that sometimes you couldn’t help but tease him. A brush against his face or hoof shake would turn him into a warm milkshake every time without fail. Purposely petting him on his jaw-line then, was like taking the wheels out from underneath a speeding train. He pressed into you without realizing, though he soon pulled back. His rear legs pinched together like a spring trap snapping shut and shudders rocked his rotund backside.

“Looks really good on you...” He chirped and fluttered his wings as you stuffed away the packaging he had brought, your friends shooting him looks that goaded him to get a move on.

“Well… bye Mr. Anon!” Derpy spoke with his first sheepish tone of the day when he realized that your friends were in no mood for a conversation. It didn’t make him move very fast of course, but you weren’t in any rush yourself.

“I’ll see you tomorrow, Derps.” You assured him of another meeting that would most assuredly be more pleasant. Somehow your voice communicated everything he needed to know in those short words clearer than anything in all Equestria could’ve. Derpy knew he’d see you again, he would feel this again and that moment would come soon enough if he was patient. He trot backwards and hit many things on his way out of your sight, but his good eye could never leave your face. The boys got the wheel back on Big Mac’s cart, though it certainly wasn’t thanks to your help.

“Why do you humor him?” Caramel asked.

“Whatcha mean?”

“You said he’s always giving you stuff and always wants to talk. So why don’t you just tell him to stop? Or invite him for drinks?” You snickered and adjusted the fresh leather trinket strapped about your arm.

“I dunno. I think it’s kinda cute.” Both stallions in your company cocked their eyebrows in expressions of befuddlement. Your friends were the nicest guys you knew, but neither were particularly quick on the draw.

“Ya’ll thinkin’ a stallion’s… ‘cute?’” Big Mac quipped, his heavy yoke strapped back onto the cart so he could haul the morning’s product. You returned their puzzled look when neither understood what you were getting at.

“Yeah. I mean, it’s pretty clear he likes me. I don’t see anything wrong with that.”

“Course he likes you. But if he wants a friend, how come he never comes and plays cards? Or goes out drinkin’ with us? Derpy gets weekends off, doesn’t he?” Big Mac nodded in agreement with Caramel’s case, but you only stood there and sipped from your coffee further.

“Not that way, man. He doesn’t wanna be friendly so we’ll hang out.” Now your friends were truly lost. The pair exchanged frustrated glances to one another in efforts to filter through what you had said. The gears and cogs turned inside their minds in grinding rotations that refused to properly interpret your point.

“So… he don’t like you?” Big Mac finally said, making you stand there in utter astonishment.

“Neither of you numb-skulls understand what I’m saying?” The stallions shook their heads in unison.

“You’re being confusing, again. If he doesn’t wanna be your friend, why is he being nice to you? And why do you think another stallion’s cute?”

Sometimes ponies' gaps in knowledge were surprising to you. Despite being a perfectly civilized race that had vast reserves of power in the arcane and storied histories, you found that rural ponies could be incredibly ignorant. Initially you assumed it was just Derpy, but the longer you stayed the more you learned that nearly every soul in Ponyville was quite innocent compared to you. Ponies didn’t swear, they didn’t shout obscene insults and they most certainly didn’t discuss lewd things out in the open. If it weren’t for the massive nuts hanging off of stallions and the exposed backsides of mares around town, you’d swear they didn’t even have a concept of sexuality. So there you stood, trying to think of a proper way to explain what it meant to be gay to a pair of stallions that had probably never heard the term before.

“Ehm… you’re serious, right? You guys aren’t just messing with me?” Most of the time, this is where they’d start laughing at a prank of a social faux pa you had made. They would reveal the big secret about touching mare wings or whatever thing you had no way of ever figuring out and you’d all laugh it off. But here, you could sense their genuine confusion.

“I mean he likes me. Really likes me. Or he probably does, anyway.” Caramel tried to talk, but his mouth snapped shut when his mind failed to conjure the proper words to rationalize what you were saying. Big Mac stared dumbly forward like he always did when a thought beyond basic responses drifted through his mind.

“He thinks you’re a mare?” He finally guessed, making your hand clap tight to your forehead.

“Lord you guys are thick.” You groaned, accepting that this would be a topic best brought up later when you weren’t late for work.

Contrary to the weary weight pressing on your shoulders, Derpy was just about hovering three inches off the ground. His wings beat at a steady and gleeful rhythm to match his bouncy trot of undiluted happiness. His taste of you had been short, but just sweet enough to keep him going. Absence made the heart within him grow fonder of your mysterious essence. The way you made him feel surpassed all other priorities and memories with consistency and ecstasy. Lingering tingles of your finger caressing his lip would dance like lightning bolts blasting soil apart in his mind for hours to come. His trot caught the eyes of some who simply smiled and waved on a happy friend.

Some greeted while others got out of his speedy way. The grey stallion spread positivity on his mail route after each encounter with you, albeit never at the same rate that the masterful Pinkie Pie could. His was a simple and joyous smile that clouded his gaze on each and every mailbox and door slot. Twilight happened upon him when the starry-eyed stallion was mindlessly trying to jam a box through a door’s brass letter slot. The silly stallion’s vision had been stolen by strange and twisting images of warmth and comfort that was buried beneath a mountain of safety and security. His hooves rested on packed dirt and stone stoops, yet felt as if clouds cushioned every step. Twilight saw he was in a world of his own… again. The flighty mail-stallion could genuinely just stand there unconsciously smiling and staring for minutes on end if someone didn’t offer him a hand.

“Derpy? Derrrrrpyyyyy?” She cooed softly to avoid startling the distracted horse. Her hoof waved about in his face to stir his mind back into action with invisible results. Derpy was transfixed by nothing in particular so much that his eyes rolled like rotating planets.

“Hmmm… hehe…” Another wave proved fruitless when such a shroud had rolled over Derpy. He shifted on his giddy hooves before something within his package finally cracked loudly within its cardboard container. Whatever contents were inside had been crushed under Derpy’s negligence and made such a sharp noise that it finally ripped him from whatever strange realm he had been stuck in. His eyes re-focused for a brief moment until they returned to their usual rotation of goofy randomness. One rolled about and discovered the purple princess waiting for him with a patient, if not somewhat frustrated smile.

“Oh! Hi Princess!” He yipped with a childish tone before bowing to his better. Twilight accepted his show of respect, but never demanded the full bow that Celestia or Luna required. A small curtsy was more than enough.

“Derpy, I’m glad to see you’re doing well today. Did you talk with Anon?” She asked with full knowledge that you were Derpy’s favorite thing to talk about. He nodded energetically with flutters in both wings.

“Yessum! I had to chase him down in the market, but he got his mail. Another pony sent him a gift, too!” Derpy shone bright with pride that he had no reason to earn if his story was true.

“You think he’s doing well, in Ponyville?” Twilight asked more out of consideration than interest. Derpy always had something to say about your accommodations, which aided her somewhat in helping your stoic and quiet ass to talk.

“I think so. Ponies really like him around here. He’s got friends and he’s got a good job, Mr. Anon seems really happy!” The grey stallion danced somewhat on his hoofs in unreasonable joy. Twilight knew the signs just as you did, but she never confronted Derpy about it. In all her years of reading steamy novels and texts forbidden to fillies, she had picked up a thing or two about unusual sexualities. Derpy clearly didn’t know what he was feeling, especially when he was so “silly,” to put it kindly. Her role as the Princess of Friendship put love out of her jurisdiction, but the matter of a confused Derpy pining for a sensation he could never understand kept her up at night. She had tried to subtly hint to Derpy what his body was telling him through questions and conversation, but he always missed the point.

“Derpy? May I ask you something?” The stallion held tight to his smile, for it was still tingling with your mythical touch.

“Sure! Whatcha need?” His eyes spoke of such innocence and warmth. Twilight wasn’t skilled in reading ponies, but even her socially ignorant mind knew that face. Derpy’s heart was filled top to bottom with nothing less than the purest and incorruptible emotion.

“Is there a reason you’ve started wearing pants?” She asked bluntly and almost immediately regretted it. Derpy peered over his shoulder to view his own shapely rear where a most unusual pair of cargo shorts covered his haunches.

Ponies were adverse to clothing in their casual life. As you had come to find out, a stallion wearing pants was extremely unusual and often invited questions about his health. Derpy had been no different before you showed up, but the khaki cover had appeared only a few weeks after. Ponies had asked him about it, but Derpy never spoke up with a consistent answer. Mail ponies already wore far more clothing than the average villager with a shirt and a hat, but pants were a step too far into odd territory.

And clearly, he was well aware of that fact. His smile faded somewhat when Twilight asked him in such an upfront manner and his tail tucked in against his rotund rump. His eyes became even more shifty and unfocused than usual in an inadvertent display of his unease.

“Those? Oh, well- they uhm… it gets cold in the…” Twilight wanted to drop it then and there for the awkwardness clear on his face. Derpy squirmed on his hooves and tried to hide the weirdness of his bubbly butt behind his slung over mail bag. She knew, however, that there wasn’t any other real way. If she was going to find out the true depth of the matter, things would have to get weird. Soon enough, Derpy found that his lies weren’t going to cut it. Twilight knew more than she let on and skewered him with a kind face that assured him that his “issue” would never be heard by another ear.

“Promise not to tell anypony?” His voice became a gentle whisper when he leaned in to speak privately. Twilight met his serious expression with her own and offered a dutiful ear.

“I won’t say a word, Derpy.” Her royal demeanor gave the simple stallion just enough security to cough up the truth. It embarrassed him to each and every syllable still, so his voice remained meek and tiny. One could assume from the sheer quietness of his voice that he was afraid the very wind itself might reveal the truth of his dilemma.

“I don’t like pants. I don’t like them at all. They make my rump itchy and they squeeze my… you-know-whats.” Twilight nodded and thanked Celestia that her purple fur hid the blush on her cheeks.

“But whenever I get around Mr. Anon, my ding-dong starts… I don’t want him to see. It’s so rude of me! But I just can’t help it! I don’t know why it keeps happening.” His lips pursed tight at the mention of such a naughty body part. His heart stirred in uncomfortable warmth whenever his floppy and dark colored shaft brushed against the inside of his rough trousers. Twilight’s ears perked at the revelation.

“You get an erection? Near Anon?” She asked in a tone and volume that matched Derpy’s. He whimpered somewhat and looked around just to make sure someone or something was listening.

“What’s an erection?” He asked, earning a slight sigh of frustration from Twilight.

“Do you like Anon, Derpy?” She asked with a raised eyebrow. Derpy was rather taken aback when his own question was answered with another. His mind ground to a halt and paused whilst he turned his thought process around.

“Yessum. He’s my friend.” Derpy answered immediately and pridefully.

“Do you ‘like’ Anon?” She asked again with proper emphasis. Derpy blanked out with an obvious display of grinding thought. His processing mind struggled to wrap around the concept of liking another stallion in such a way. It was a notion completely new to Derpy and something that seemed entirely impossible. A stallion liking another was like snow in the summer, water flowing uphill or ponies with two heads. He couldn’t even imagine how such a concept worked within his limited understanding of relations. But when he imagined you and him within that framework, it made more sense than he was willing to admit. Suddenly, that unique combination was making his legs shake and his heart flutter in uncertain rhythms.

“I don’t… I mean- I don’t think so? He’s a stallion, isn’t he?” Derpy huffed with hot breaths of utter ignorance. His mind was spinning so fast and pushing so hard to understand that bits and pieces of it were shot off into the darkness with lightning speed. Another wave of that strange and icky feeling rocketed down his spine and danced inside his rump, forcing his penis to pump and pulse inside of his uncomfortable pants again.

“It might be unusual. But it seems that you do.” The stallion seemed to disagree with his antsy and strange movements.

“But- but- we’re stallions! How can I like-like another stallion? I don’t even know how that would work! If he’s a stallion too, he likes mares! I’m not a mare!” Derpy immediately spun out of control when his reasoning guided him to darker and darker depths. Twilight knew all too well that feeling of falling into one’s own mind, so she took the proper steps to reel the huffy mail-stallion back into reality.

“It’s okay, it’s okay. Derpy, you need to relax.” She spoke with motherly and warm reason, just as the Princesses had taught her. He huffed deep breaths and eventually brought himself down to a point where he could at least listen.

“I want to help you, Derpy. It hurts me to see my subject struggle like this.” She said, despite the fact that his intense angst was freshly created from this realization.

“You think that I really like-like Anon, Princess? Am I really… that way?” He asked with a hard blush shining through his fur. Twilight sighed and patted his back with a wing in the most comforting gesture she could manage.

“Are you still buying him gifts?” She questioned, earning a bashful aversion of his gaze to the ground.

“Maybe?” He answered with his hooves pressing together in embarrassment.

“Do you care about him? Really, really care?” Derpy’s ears pressed to his bundled mane of wheat-gold despite the steamy heat pouring out of them. He scratched at the ground below them both with his tail flicking side to side.

“Yessum. Goodness gracious, Princess? What if Anon isn’t like me? If he likes mares then… then what am I gonna do?” Twilight pulled him close to try and reassure the worried stallion. She could feel his heart pounding within his barrel and the fiery heat surging through his blood.

“It’s okay, Derpy. If you want Anon, I have a way.” He perked at the promise of fulfilling this previously unknown desire. Golden eyes tried to focus on Twilight’s face, but his bad eye only got half-way toward her before zeroing back onto a distant cloud.

“You do?”

“Yes. But it’s not a simple change. You’ll need to be 100 percent sure of this before we go through with it.”

“Tell me!” He whined the instant her words hit his ears. Desperation was setting in as the pieces of the puzzle were finally aligning in his mind.

“You MUST be sure. This isn’t something we can do twice.” Derpy stepped forward with the first display of true confidence he had demonstrated since starting this conversation.

“Yes, yes! Princess please tell me! I want these weird feelings to stop! I wanna make him happy! I don’t care how I do it!” Finally Twilight stepped away from him and gestured with a turn of her head.

“I have a spell to make you a mare… but it doesn’t last forever. Come with me, we’ll do some tests and get you that human.” Bells and whistles clashed in Derpy’s mind at the mention of such a transformation. These feelings, this heat, all the days spent thinking about you- if he were a mare, it would all make sense. No longer would it be a unique friendship defined by unusually intense affection. No longer would Derpy lay there at night wondering why you continuously drifted through his restless mind. No longer would he struggle to rationalize why he wanted your touch so bad. Never again would he stare shamefully at his throbbing, tall and stiff penis that had no one to care for it.

“I could be a mare? For Anon? You could do that for me?” He said, taking after her with an excited trot that kept him right by the Princess’ side.

“We need to test it first. Celestia only knows how long it might last or what the side effects could be. But if it’ll help you, then I’m all for it.”

Derpy followed closely after her and shirked his duties for the morning. His soul caught fire in the slight walk toward the castle on the outskirts of ponyville. Things seemed to move at a tiny fraction of their normal speed, as if he were flying headlong into something new and frightening. If it were any other unicorn promising him a solution to this problem, he’d never have trusted them. Magic was not Derpy’s strong suit, especially when it often conjured up strange and ridiculous results.

But Twilight was his Princess. Twilight was the smartest unicorn he’d ever known and one of the few mares that seemed to really care about his problems. If any pony could really help, it would be the purple sperg. All he could do then was put his trust in her, wonder how he’d earn your love and think securitous thoughts about you. In this whirlwind of emotions, the proverbial eye of the storm were his dreams of you as his affection and finally putting an end to the discomfort within him.

“A mare… I could be a mare for Anon.” He thought to himself again and again with the steadiness of a clock. He chewed on the idea of being your girl, being your loyal and loving mare that would be such a natural fit for you. In his and Twilight’s mind, it was the only way that such a relationship could work. Neither could conceive of two stallions finding such affection between one another, as it simply never happened in Ponyville. Tradition dictated the matters of love and courtship in rural Equestria and was held close to every pony’s heart. Derpy was no different, but that didn’t hold him back from exploiting a loophole once he discovered it.

Though he was totally uncertain about what he was getting into, he was comforted by his singleness of mind. If he really were so helplessly in love with you, then he would make it happen. One way or another.