Derpy's Hearts and Hooves Day

by The Mountaineer Brony

Rating: mature
Tags: Comedy, Derpy Hooves, Sex, DJ P0N-3, Slice of Life, My Little Pony: Friendship is Magic, Doctor Whooves, Lyra, Romance, Treehugger
Length: 9041

Derpy makes a tough decision as Hearts and Hooves Day approaches.

Derpy has never had a lot of luck when it comes to love. But now, she has a chance to spend Hearts and Hooves Day with a pony of her dreams--except she can't decide which one. Crushed by two crushes, she decides to seek some romantic advice from her friends. Will Ponyville's cross-eyed mailmare find the truth within her heart before it's too late?

Potential Trigger: A wet dream, fantasizing, and implied sexual activity, and saucy language in relation to it, as well as a heated near-lemon that doesn't actually turn into sex. Really, I just made it M to be safe.

Published 2019-02-15 06:50:01 UTC
Last updated 2019-02-15 06:50:01 UTC

Shall I Stay?

My dream last night was exquisite, Dear Diary...
I was laying back on my bed, feeling at once both tensed and relaxed as the beautiful mare whose head I cradled between my legs filled me with passion, thrilling me with every little thing she did. And when she would look up at me through those dusty, half-lidded eyes, it felt as though my heart was going to explode. I threw my head back and closed my eyes as she continued her gentle, titillating work.

"Oh, thank you Luna..." I managed to say breathlessly. I could've sworn I saw her outside my window, giving a friendly wink. My distraction didn't last for long as the mare going down on me inched me ever closer to the finish line...

But just as I was about to cross it, my freakin' alarm went off.

I practically bolted upright out of bed, glancing around the room in multiple directions with each eye before they finally focused on the little round machine whose bells were ringing frantically on my nightstand.

"Six o'clock." I sighed. "Time to get ready for work."

Clam-jammed by my own alarm clock...

It's only a week until Hearts and Hooves Day, and that means the post office is busy. Lots of ponies are sending and receiving gifts and love letters from their admirers; some secret, some not so. Except for me, of course, but that's not what I'm writing about right now. I wanted to make sure I did an especially good job after that debacle last year with Big Mac and Sugar Belle... I felt terrible once I found out, but in my defense, the ink was still wet.

However, in my effort to perform better, I mostly just made myself tired. As the clock ticked towards noon, I was starting to nod off, and probably would've slumped over the desk asleep had it not been for Lyra showing up.

"Snap to it, Muffins!" she said, giving my mane a playful rustle with her hoof.

I raised my head and rattled my eyes to (sort of) focus on the minty unicorn in front of me.

"Oh, hey Lyra!" I said as the cobwebs slowly disappeared from my brain. "Nice to see you!"

"Same!" She replied in a chipper tone. "I'm actually expecting a package. Got anything with my name on it?"

I leaned down and rummaged through some boxes beneath the counter, picking up one and holding it a couple inches from my face. The shipping label was printed just large enough that I didn't need my magnifying glass.

"L-V-N-G? Is that you?"

She chuckled. "I'm living for now, at least. That says L-Y-R-A."

"Then that must be you, Miss Heartstrings!" I cheerily passed the box to her hooves. "Mind if I ask what's in it?"

"Oh, just a little something for Hearts and Hooves Day." Lyra grinned.

I leaned forward on an elbow. "Ooh, do tell!"

She chuckled and blushed somewhat, lowering her voice to speak to me alone. "I ordered it from a boutique in Canterlot. It's a little lace camisole, you can just about see through it. Gonna put it on and wait on the bed for Bon Bon to open her present."

I gave a long whistle and fanned myself with a wing. "Lyra's gettin' saucy! Well, I'm sure Bon Bon will love it!"

Lyra smiled broadly, scrunching up her reddened face. "I can't wait!"

"Hey Lyra, my shift ends in about 15 minutes here. Do you wanna grab lunch?"

"Well sure, Derp, that sounds great. Let me go put this away someplace safe and I'll meet you back here."

The two of us sat outside in the courtyard of one of Ponyville's cafés. Lyra was giving some remark about how she liked what this place did with their hay, but my mind was honestly too preoccupied with a banana nut muffin to hear her. She gave a chuckle upon snapping me out of my food-induced trance and continued poking idly at her salad.

"So Derpy," she spoke between bites "what are your plans for Hearts and Hooves Day? Have you gotten any presents yet?"

"Well..." I brushed crumbs from my muzzle as one eye awkwardly decided to do its own thing. "I got the usual yearly card from my little brother telling me how awesome I am, all covered in crayon and glitter, but not much else. As for plans, I don't really have any. I've got nopony to be lovey-dovey with, and all my friends are busy with... well, you know what with." Lyra chuckled once more as she was reminded of her heated ambitions.

"I dunno." I continued. "Maybe I'll look for a good book to read. Nice large text, probably romantic..."

My stray eye sure seemed interested in something over towards the café. Very quickly, I glanced the other one over to see what the commotion was, and very quickly I realized it: there she was, the mare from my dream, standing over in line. Soft green fur, long reddish mane styled into dreadlocks, and an overall peaceful aura: it was Treehugger, all right.

Ever since I first laid crossed eyes upon her, I was smitten. Sure, I'd seen mares I thought were beautiful before, even ones I could've seen myself with, but it wasn't until I met Treehugger that I was truly attracted to one of my own sex. I admired her lax personality, the way she saw the world and lived in it in her own, leisurely pace (which, being a postal worker, I envied.) She was kind and gentle to other ponies and to nature, and she saw things differently than everypony else. She was charming in a passive way. She couldn't be bothered. She was surreal, she was new-age, she was mysterious, and that turned me on. Not to mention she was quite physically beautiful. I often attended the art classes where she would pose as the subject just to feel close to her on an intimate level. Sure, my paintings weren't very good, but that's what happens when you're trying to watch your work with one eye and your model with the other.

I quickly blushed and turned my eyes back to my food. Lyra noticed this quite easily.

"I saw that." She said with a friendly smirk.

"What?"

"I saw how you were eyeing Treehugger over there."

"Pfft--what? Nooo, I..."

"You want a piece of that, don't you?"

"Oh, Lyra, you're so quick to go there!" I scratched the back of my neck, lowering my snout to try and hide the redness upon it. "I mean, I certainly wouldn't mind, but like, even just a hug would be great, I mean... I'm not... I...hrm..."

Lyra rolled her eyes, something I desperately wish was easier for me to do. "Oh, come on, Derpy, I've known you for years. I knew you had a thing for mares the first time you, me, and Bon Bon went to the spa together."

I shot straight up in my seat, cheeks aflame. I mean, I knew that she knew, but I didn't figure she'd found out that early.

"You got super awkward when Aloe started rubbing you down. Plus, I saw how you'd sneak peeks and mine and Bon Bon's butts."

Well. This was awkward.

I gave a borderline violent cough and fanned my tomato-colored face with my wings. "Y~yeah, um... so sorry about that. I, hehe... I, uh... I hadn't been out of high school very long, and I was starting to discover myself..."

"Oh no, it's fine!" Lyra said with a smile. "Neither of us minded it. In fact, it kinda made us feel cute!" Both of us had a good laugh over it, though I still felt embarrassed as all heck. I nearly emptied a glass of water to cool myself down.

"That being said though, I really like stallions too." I said. "In fact, aside from Treehugger, there's really only one other pony I have a crush on, and he is just as compelling."

"Oh, we know." Lyra said with another smile, jutting a hoof back over her shoulder. Trotting down the street in the distance was Doctor Whooves; indeed, she'd guessed correct. He was cute as a button, and just as awkward at times as me. He was also smart, friendly, and downright debonair when he wanted to be. We'd been friends for many years, but whenever I tried to drop hints his way that I was interested, he'd get too embarrassed and shrink away. Sweet Celestia, I'm surprised he didn't faint when I got playful under the mistletoe at my Hearth's Warming party.

"You... you know?" I said, somewhat surprised. The blush was starting to come back again.

"Oh, not just me. Bon Bon, Octavia, Vinyl, we all know, and it didn't take you kissing him under the mistletoe for us to figure it out!"

I smiled broadly, my eyebrows curled up with slight concern. "How long have you known?"

"Since Cranky and Matilda's wedding." Lyra confessed. "Bon Bon and I saw how close you two stuck to each other and we started having suspicions."

"THAT long?!" My jaw dropped. "But I had barely figured it out then!"

"You don't exactly spend the entire ceremony and reception with your guy friend and expect your girlfriends not to get suspicious."

I bit my lip a little and turned away. "Well you don't go around calling your best friend your 'BEEEST' 'FRIEND' and expect your friends not to realize you two are WAY more than just friends." I gave the words "best friend" my best air-quotes with my hooves.

Lyra pondered this for a second or two, then shrugged. "Yeah, admittedly we weren't very subtle about it."

"It was the eyes that gave it away."

"But those were the days when we were first falling in love. We could barely keep our hooves off each other. We were pretty fresh to the world, just like you. At least nopony who knows about us has threatened to run us out of town... yet."

"Well, they'll have to go through me if they do." I turned back and smiled at Lyra, who leaned across the table to hug me.

"Derpy, if you really like Treehugger and Doc that much, why don't you ask one of them on a date for Hearts and Hooves Day?"

"That's just the thing, Lyra: I don't know who to choose. I really like them both, and I can see myself with either of them long-term. I want to do this right and do it once."

"Oh..." Lyra said, her zeal fading. "You want a forever pony, then?"

"I think so, yes." My nod and look of seriousness was somewhat undercut by my eye drifting randomly about.

"Hmm..." The mint green mare scratched her chin in thought. "Well, how about this? In the days leading up to Hearts and Hooves, you can spend a few days with both of them. Two or three dates each should be enough to figure out their best qualities, and then you can decide which one you want to spend the holiday with."

A candle lit above my head.

"You know, Lyra, that's not your worst idea ever. I think it might work!"

"Oh no, definitely not my worst." She replied with a massive eye roll. "That was probably when Bon Bon and I saw Cirque du Poney perform in Las Pegasus, then thought we could pull off that kind of flexibility in the hotel room..." She drew in a sharp breath of air through her teeth, mentally wincing. "...needless to say, we both had to go see a doctor after that."

I shook my head, a playful smile of disapproval on my face. I sighed with a pfft. "Lyra, be honest with me: once you and Bon Bon started dating, how quickly did you start having sex?"

Lyra furrowed her brow, looking skyward and tapping her hoof on the table in an exercise of mental mathematics. She mumbled some dates to herself under her breath, trying to figure how long they'd been together at the time, as they had been friends much longer than partners. Finally, she turned her gaze back to me.

"About a week and a half."

"A WEEK AND A HALF?!"

Author's Note

...That beginning was the closest thing to clop I've ever written, and it's the closest you'll ever see me write!:rainbowlaugh:
In all seriousness though, what's a Valentine's fic without a little tease?
Happy Hearts & Hooves Day, everypony! :yay::heart:
Month of Lurve 2019

Would it be a Sin?

Dear Diary...
Sorry I haven't written in a while, but... For Luna's sake, where do I begin?

Just as Lyra suggested, I explained the situation to Doc and to Treehugger. They were both quite flattered to be objects of my desire (Doc more so, as Treehugger tends to be pretty chill about everything) and agreed to a staggered series of dates. Hearts and Hooves Day falls on Friday this year, so I started with Treehugger on Saturday night, followed by Doc on Sunday, then Treehugger, and so on. On Friday, I will present my decision.

So far... well... maybe I should just tell you what happened.

My first date with Treehugger went pretty well, and we had a lot of fun. It was a sunny day, so we decided to stop by the swimming hole... in February. Yeah, the water was frigid, but we both had a good laugh about it, then snuggled on the beach to warm up. The way she held me made me feel like I was the center of her world... I still blush thinking about it. She also taught me how yoga works, and it feels like it's gonna be a recurring thing between us.

Doc's date went great, too. He took me to a movie, a romantic comedy, and followed that up with bowling and dinner. A very traditional night out, I'll admit, but it was sweet, particularly when he'd try to be romantic but wasn't sure what to do. He thought he'd had this date all calculated and mathematically parsed out, but when he'd come across something unexpected, he'd get a little flustered. But he makes me laugh, and smile a heck of a lot. And even though we didn't do that great at bowling--the one time I trusted my eyes to aim for the pins on their own, the ball wound up outside--we had a marvelous time.

Now those are all well and good, but the second date with Treehugger… that's where things got interesting.

Early on the day afterwards, some hours before my second date with Doc, I stopped by Lyra and Bon Bon's house to say hello and let them know how things were going. We sat at the table and ate fresh candies that Bon Bon had prepared.

"So, how did yesterday's date go, Derpy?" asked Bon Bon.

"Tell me every detail!" Lyra added, leaning forward eagerly on her elbows.

I cleared my throat and laughed nervously. "Uh, well..." Shifting in my seat, I let my eyes wander about the room as my brain recalled the eventful evening.

"Things started off pretty calmly. I picked her up from the art studio and we grabbed dinner together, then went back to her place for some yoga..."

"This is a nice place you've got here, Treehugger." I said, taking in the room from multiple angles with my wonky eyes.

"Thanks." She said in her slow, ever-calm voice. "I try to keep it lookin' nice, but like, nopony ever comes over, aside from Fluttershy on occasion. You're the first pony in a while to come here--and, well, the first date I've ever brought back here."

"Oh. How nice!" I said with a smile. Suddenly, my eyes caught sight of a large mass of green on the opposite side of the house. "That is a lot of plants."

"Oh yeah, they're kinda like my housemates. We keep each other company."

I certainly knew what it was like to live alone.

"Each of 'em's got a name, too. That little palm is Sherrie, the cactus is Pete, and that rather dashing vine is Sir Tanglemore the Third."

"What about that one?" I said, gesturing to a particularly verdant plant growing from a pot on the floor.

"Oh, hehe. That's Mary Jane." Treehugger chuckled. "She helps me keep it real. So anyway, you ready to start today's lesson?"

I'd come to enjoy these yoga lessons: they're good for helping me limber up, especially since I often have back problems from carrying heavy packages. My 'instructor' introduced some new stretches that evening, and goodness, my wings felt so weightless, I felt like I could've crossed an ocean on them. By the time we finished our usual routine, the sun was setting.

With the cutest blush I've ever seen, Treehugger invited me upstairs to her balcony to watch the sunset. It was a nice little space, open to the cool night air, padded with pillows, decorated with flowers and incense burners. Much as we had on the beach, I leaned on her shoulder, wrapped in her forelegs as the princesses moved the heavens from the distant city of Canterlot.

"Thanks for coming to meet me at the studio." She said, nuzzling her cheek into my mane. "I've been having to work longer hours to make ends meet, and I appreciate the support."

"No problem at all." I said. "Do you enjoy doing that?"

"Modelling? Yeah, it's alright. I've always been pretty, y'know, 'open' with my body. Not that I don't have a sense of modesty, it's just... like... this is me. This is natural. Why stigmatize it? That being said, having everypony's eyes on me is a bit of a thrill. I like the feeling of being exposed."

"Well I'm glad you enjoy your work, Treehugger."

"I know you do."

My face lit up red as I looked up into her gentle, knowing smile. "Wh-what?"

She gave a friendly giggle as I slid and fell into her lap. "I noticed how often you come to the painting classes when I model." She gently stroked the fur of my belly with a hoof. "Do you like looking at me?"

I gulped and gave a nervous, closed smile, my eyes fixed firmly on hers. She laughed and closed them, before half-opening them again sultrily.

"Hm... I'm very glad to hear that... because I like being looked at."

With her other hoof, she brushed aside some fur on her underbelly, revealing two--- well, I think you can guess. I shot up into a sitting position, covering my beet red face in my hooves. Treehugger immediately put a hoof on my shoulder to comfort me.

"Whoa, hey, I'm sorry! I didn't mean to startle you. Are you alright, Derpy?"

I nodded and gave a very quiet "yeah," turning to face her with an embarrassed red-cheeked smile. She smiled too, and took my hooves in hers.

"I'm so sorry. I should've made sure you were okay with that before..."

"Oh no! You're fine! I just, um... I've... tried to imagine what you were like for... a while..."

Treehugger blushed as brightly as I was, clearly flattered at my attraction to her.

"Well, hey, um... if you, like, uh... want to... do more... we can do as much or as little as you want..."

I gulped again. Was this really happening? The mare of my dreams showing the same desires I'd only dreamt of?

I nervously laughed. I wasn't sure how far I wanted this to go. I'd never even come close to any sort of intimacy before.

"Um... I-I g-guess, uh... would you p-please, um... k-kiss me?"

Treehugger smiled softly and planted one firmly on my lips. We held that kiss out for a good minute or more, feeling the textures of one another and tasting all we could. I had never kissed anypony with an open mouth before in my life, let alone with my tongue, but Treehugger clearly had. She guided me through this new, wonderful experience like fireflies in a dark forest, and stirred the heat of desire within me as I'd never felt before.

After we broke off our kiss, it was in this heat that I expressed a secret, forbidden desire I'd long held.

"Treehugger…" I said between shallow, panting breaths "I-I want you t-to pin me down..."

She gave a sultrier, more lustful smile as she lowered me onto my back, resting her warm belly on mine as she held me down, placing tender, passionate kisses on my mouth, face, and neck, earning little moans of pleasure from me. I held her in my forelegs at first as she worked; it was clear to me she'd done this before, possibly with other mares, as she knew just what to do to make me squirm. Just looking into her dusky, half-lidded gaze of desire and seeing her glistening mouth could've made me release then and there, but I wasn't quite ready yet. I wanted this tension to last as long as possible. It was time to up the excitement.

"Go lower..." I whispered.

Treehugger, tantalizingly slow and gentle, nuzzled her muzzle into my collarbone, then the fur of my underbelly, her soft, hot lips seeking out my two most sensitive bits hidden within... I think you can guess what. I bit my lip and began running my hooves up and down her torso, occasionally daring to pass them over her taut flanks.

She loosed her lips from around me, looking up with a guilty scarlet face. "You okay? You're shaking."

"Oh, I'm just... I'm finally touching Treehugger…"

"No..." she said in a playful whisper, locking eyes with me. She grabbed one of my hooves in hers, and moved it gently down her underside. I almost jumped when I felt said hoof touch something supple and wet.

She turned her chin up, looking down at me with domineering eyes.

"Now you're touching Treehugger."

She bit her lip hard and giggled from the back of her throat. Realizing where my hoof was being rubbed, my body started shaking even harder. I felt my thighs tense, and before I realized what had happened...

...I passed out.

"You did WHAT?!" Bon Bon nearly spat her drink across the room.

Lyra burst out laughing. "HAHAHAHA! She actually SAID that?! Hohoho, by Celestia, I thought I'D said some stupid things in the sack, but jeez! HAHAHA!"

Bon Bon glared at her lover. "I happen to find those stupid things you say very sexy, Lyra." As the unicorn blushed, the Earth pony turned back and motioned for me to continue my story.

I woke up some time later, still on my back in the place I'd been pinned. I sat up and saw Treehugger laying on a pillow in the corner, flipping through a magazine.

"Oh, you're up!" She said, snapping to attention. "I'm sorry about that, I should've asked before I moved your hoof... I just got so wrapped in the heat of the moment, I had to..."

"It's fine, I-I understand." I scratched the back of my head. "D-Did you, um... did you...?"

She nodded. "Yeah, I did. Not long after you passed out, actually. I'm kind of quick on the draw. What about you?"

I looked down at the meeting of my thighs. You can probably imagine what I saw.

"Yeah, it appears so." I said, looking back up at her. "How was it?"

Treehugger blushed and looked away. "Amazing." She said under her breath. "Again, I'm sorry if I made you uncomfortable with that. I couldn't stop myself."

"It's fine, Treehugger. I'm glad you enjoyed it, too." I stood on shaky legs and mopped sweat from my brow. "Whew! Let me tell you, that's the fastest my heart has beat in years. I might have to find you this summer when my heat kicks in!"

Treehugger laughed heartily at that. "I wouldn't mind that." She said in a demure voice. She stood to give me a hug. "I hope that my actions this evening don't affect your Hearts and Hooves Day decision. I hadn't intended this as a trump card, I just..." she shrugged "...saw how you wanted me, and I wanted you to have me. I know all too well what it's like to pine over somepony for so long and never have a chance with them."

"Aw, you're okay, Treehugger. And don't worry, this won't affect my decision. It'll be our little secret."

She blushed as I kissed her hoof like a gentlecolt, then she brought me up for another kiss on the mouth. Afterwards, she sniffed the air; the scent of pheromones still hung heavy on it.

"Um, Derpy, you can, like, take a shower before you go if you want. I already washed up while you were sleeping..."

"Naw, it's fine." I said, swishing my tail and very likely scattering my pheromones across her bedroom. "I don't want to tempt either of us any more than we have already. If I fly high enough, I should be able to avoid anypony's prying noses."

And so, I left by wing into the night sky, flying uneasily in the high winds higher up. I could hardly believe the experience I'd just had. I wasn't sure how to feel about it, either. I had consented, yes, and I wanted it to happen, but part of me didn't feel... ready, I guess. Most of the flight, I was curiously regarding my left hoof and where it had been, as it still faintly smelled of her. I didn't tell Lyra and Bon Bon what I did with that hoof once I got home, but that's beside the point.

After I'd finished my tale, Bon Bon sat across from me deep in thought. Lyra was bringing over more refreshments.

"It's just that after all that, I'm not sure how to make Doc's date pop." I broke the silence. Bon Bon shook her head at me.

"Derpy," she began "you don't need to do anything intimate--or for that matter, anything extraordinary--to have a great date. Heck, the first two dates you've been on have been nothing but you hanging out with Treehugger and Doc."

"But you two started your scoodily-pooping after only a week and a half!"

Bon Bon reared up in great surprise, then shot a look of concern backwards at Lyra, who slowly backed out of the room.

"Yes, Lyra and I did jump each other's bones pretty quickly," Bon Bon said with a turn back to me "but that doesn't mean you have to feel rushed to. We're completely different ponies, don't compare yourself to us. Just be yourself, Derpy, take things at your own pace, and you'll be fine."

"Just like Treehugger." I added. "She lives in her own time zone. Though things sure seemed to move quickly last night."

"From the way you described it, what she said, how she acted, I think that was just her way of showing you love. I've heard things about her, and she seems like the type to believe in free love."

I blushed deeply. "It certainly felt like she'd done this before."

"You know, Derpy," Bon Bon gave a clever smile "I think I know of another couple in Ponyville who could give you some helpful advice."

Author's Note

Made you look! :trollestia:
Okay, but that's all, and I'm serious. I hope you enjoyed it, ~~you degenerates~~ :rainbowlaugh:

If I can't help Falling in Love with You?

I sat at the table across from its owners, Octavia Melody and Vinyl Scratch, the latter of whom was serving tea.

"Vinyl, you never struck me as the type of girl who'd drink tea."

The blue-maned unicorn shrugged, then nudged the grey Earth pony next to her. "She got me into it."

Octavia gave a gentle smile, reaching up to adjust the purple sunglasses resting on her girlfriend's horn.

"Do you have to wear these everywhere, dear? You look just as good without them."

"Hey, DJ P0N-3 isn't just a stage name, it's a way of life. I thought you knew what you were getting into, Octy."

"Speaking of getting into relationships," I spoke up, though I hated interrupting their cute banter "Bon Bon told me you two might be able to give some advice regarding my current predicament."

I gave them a synopsized version of the past several days: of the cavalcade of dates with Treehugger and Doc, of my steamy tryst on the balcony the night before, and of my concerns for that night's date with Doc.

Vinyl gave a long whistle and fanned herself with a napkin. "That's a lot to unpack there, Derpy. But I think we can help."

Octavia sipped her tea with an air of loving amusement. "Derpy, do you know how this one asked me out on our first date?"

I shook my head. Somehow, I'd never been told the story.

The cellist smiled and looked at her DJ, who puffed out her chest in pride. "She invited me to a classical music concert."

"But Vinyl, I thought you hated classical music?"

"Whoa whoa whoa; 'hate' is a strong word. It's definitely not my favorite, for certain. Buuut… I was willing to put up with it if it meant I got to be close to Octavia for a couple of hours."

"The poor thing was so nervous." Said mare added. "She looked about ready to pass out after I noticed she was holding my hoof."

"I wasn't even sure if you liked mares!" Vinyl added from across the room, where she was getting even more sugar cubes.

"Fortunately for her, I did. And I really liked her a lot as a friend. After seeing her bring me to watch an orchestra of all things and being so nervous about wanting to date me, well... that's when I knew she was meant for me." Vinyl arrived back at the table and planted a kiss on Octavia's cheek. They both smiled. "Plus," the posh-sounding mare added "even though she was shy around me, she was outgoing socially, and part of that bravado rubbed off on socially awkward me. If I hadn't have fallen in love with Vinyl, I might never have come out--to my family, or to anypony." Vinyl leaned her head on Octavia's shoulder, her magenta eyes gazing up at her lovingly. She nuzzled the unicorn with her snout. "But my life has certainly been a lot happier since I did."

Sitting across the table, I was trying not to let my heart melt out of my eyes and into my tea.

"Wow..." I muttered, holding back emotion. "I hadn't known about how you two met. That's really sweet, you guys."

The two mares across from me embraced each other. Octavia sighed. "She's my everything."

Vinyl barely held back a coo of affection. "And you're mine."

"After we started dating, we soon realized that being girlfriends was basically the same as being friends, except that we were closer on a deeper level. Before, we had a strong affinity for one another, certainly, but after we began courting, it felt like our very souls were intertwined."

'Courting'... what a beautifully old-fashioned word.

"Our souls weren't the only things that got intertwined, Tavi…" Vinyl gave a look of playful mischief, biting her lower lip and grinning.

Octavia snickered. "Yes, well..." she said, trying to regain her composure "it was a bit unusual at first, climbing into bed with your best friend, but after that happened, it only served to strengthen the bond of love between us. It's served as a restorative, almost spiritual experience for us since then."

"How long before that happened?" I inquired.

"Before our first time?" Octavia looked lovingly back at Vinyl, who blushed ever so slightly. "Why, about a year into our relationship, I believe."

"A whole year?" I said, not with shock, but mild surprise. "Hmm."

"It's perfectly okay to wait even longer, Derpy." Octavia said to me.

"Yep. Everypony's different." added Vinyl. "Some even wait ages before they kiss."

"So I guess that if I want things to go well with Doc, I should just be myself and let things progress naturally?"

Vinyl gave a quick tilt of her head in approval. Octavia turned her hooves out towards me as though saying "It's up to you."

"I'll tell you what, though." Vinyl piped up. "On Thursday, Tavi and I have a gig at this--"

Octavia gave a somewhat disappointed glance and cleared her throat quietly. Vinyl rolled her eyes.

"An engagement at this Hearts and Hooves ball."

"I'm sorry, Miss Scratch but you can call it a 'gig' when it's one of your raves."

"Anyway, if you and Doc need something to do for your last date, you could take him there! I'll be sure to whip up some dope tracks for ya!"

"You'll do no such thing." Octavia remarked. "This is a formal event, and we've been asked to come dressed as though we were performing a concert hall. They'll kick us out if you bring that record-scratching so-called 'instrum--'"

Vinyl interrupted her lover's complaint by planting a deep kiss onto her muzzle. I couldn't help but snicker under my breath. After Vinyl broke the lip-lock, Octavia blushed deeply and lowered her gaze.

"That doesn't work every time, you know."

"I think it does, Miss Melody." The white unicorn upturned her snout playfully. "I truly think it does."

My second date with Doc was mostly spent on a walk through the park (well, I flew mostly.) Somehow, it had been a while since we'd actually talked about our personal lives, so the opportunity to catch up was nice. I didn't dare tell him what happened with Treehugger--neither of us could've handled it. That said, we enjoyed ourselves; he bought me a muffin, which I shared with some ducks, and luckily, managed to avoid falling into the pond. As I started to fall forward, Doc caught me by the waist. It was blush-worthy for both of us, but I appreciated it. I felt safe in his hooves. Afterwards, he and I stopped by Sugarcube Corner to visit Pinkie and grab something sweet.

That evening, after Doc and I parted, I stopped by the Carousel Boutique about 15 minutes before it closed. Rarity was inside, taking measurements on her sister Sweetie Belle for some sort of frilly dress.

"I told you, Rarity, it's not at all formal!" The little pony protested. "Everyone in class is literally just passing around cards! I don't need a dress to do that!"

"Oh nonsense, Sweetie Belle." Rarity said with a tsk. "You'll be the most fabulous filly there! Besides, the flyer calls it a Hearts and Hooves Day party, and what girl wouldn't want to show up in a dress for that?"

"Me!" she replied, wincing slightly as the tape measure was pulled tight around her child-sized barrel. "You realize that nopony in class wears clothes on a regular basis? Not even the teacher! And neither do you!"

Rarity simply ignored this remark as she scribbled on her notepad. "Oh Sweetie, you've grown taller since I made your last dress!" She adopted a cute voice as she nuzzled her sister's belly with her nose. "And you've also grown wider and cuddlier!"

Sweetie Belle's laughter rang out like a bird chittering at dawn. "Stop it, Rarity, that tickles!"

I gave a small cough to make my presence known, and the two sisters' heads snapped towards me with wide eyes.

"Um, Rarity?" I said stepping forward. "I'm here to call in my Hearth's Warming gift."

Rarity's eyes narrowed in fiery determination. She knew why I needed a dress. "All right darling, let's make you the star of Hearts and Hooves Day!"

Sweetie Belle mouthed the words "thank you" at me for distracting her sister with a new project.

My third date with Treehugger was also very low-key. After our usual yoga session, followed by meditation, she took me to a little music festival of sorts, held by her friends Flax Seed and Wheat Grass. There were a lot of ponies there being very chill and lighting lots of candles and incense; it seemed easy to get lost among the herd, but Treehugger and I stuck by each others' sides and had a good time together. Little did I know that she can actually play the guitar quite well, and even sing. Flax and Wheat run a local business outside of Ponyville where they make all kinds of all-natural wellness products; they introduced me to a skin cream that they thought could fix my eyesight. While it didn't work, it did make my skin feel refreshed. There were also a lot of plants there like the one Treehugger had... I'm still not sure what they do. Maybe it's good luck.

Early the next day, Rarity had my dress ready. I told her I was sorry for the short notice, but she said she didn't mind. According to her, it was these sort of passion projects she lived for. Whatever makes your life interesting, girl.

Even though she only had about a day and a single set of measurements to go off of, Rarity had produced quite the work of art. It was an elegant reddish-pink piece, not quite magenta but not a solid red or pink. The peytral was lightly colored and shaped like a large heart, the cleft at the top curving down into a sort of V-neck; a popped collar styled like a white doily framed my blonde mane like a halo, and the rest of the dress clung to me like barding, though it stopped at my waist like a shirt for convenience. There was a hole for a wing on either side of the long zipper. The back of the dress formed a ruffled crupper of cloth, curving like a dome out over my rump, and accentuating it quite nicely, I might add. It was secured at the small of my back with a large bow, and formed a long train behind me, the outermost edge of which was lined with cloth hearts and more doily fringe. It even came with four little cloth slipper...boot...things... that had hearts holding the laces... hey, heartstrings! Overall, it was an exquisite dress, and I felt very flattered to be wearing it.

"Why Rarity, it fits perfectly."

"Of course! It was made to your specifications, dear."

"Are you sure you don't want anything for it? I'm sure something like this would usually go for a lot of bits."

The seamstress placed a hoof on my shoulder. "Derpy, the only thing I want you to do is to have a good time. Go out there and render them speechless, darling!" She turned to look about the room. "Now where is my baby sister?"

Outside, I noticed Sweetie Belle scurrying away in the company of her friends. She seemed to be in quite the hurry.

That evening, I did my mane up in a fancy part, held in place by a plastic rose. I'm not one for a whole lot of makeup, mostly because I have trouble putting it on with these eyes, and, y'know, hooves, but I did do mascara, some lip balm, blush, and a bit of eyeshadow. Just about when I thought I looked as good as I ever would, I heard a knock at the door. Doc had come to pick me up.

I'm not sure what I expected at first, but I was pleasantly surprised nonetheless: Doc cleans up nicely. He had his mane slicked back and was wearing a bowtie and tux, with coattails way too long for him. A small flower I couldn't identify adorned his buttonhole, and he had cufflinks in the shape of atoms. I noticed his eyes jump when I answered the door.

"Derpy!" he said, seemingly caught off guard. "You---I---I mean, er--- you look... astounding!"

I blushed and scratched my foreleg. "Like a million bits?"

He smiled and shifted awkwardly himself. "Oh!" he snapped to attention "I brought you something!" he produced a small, flimsy box from somewhere on his person and presented it to me. "For tonight."

Taking the box, I flipped open the lid. Inside was a plump, colorful corsage which seemed to glitter with a rainbow of colors in the moonlight. I gave a small gasp as the strange flower shone out brighter than my future.

"It's an altered version of my fireless fireworks." Doc said. "I believe I altered the formula enough so that it shouldn't explode."

I slipped the corsage onto my hoof and admired it, turning it this way and that in the moonlight. Doc offered me a hoof to come down off the porch, which I folded a wing over and stepped down. Soon, we were on our way to the venue.

"Have you ever been to a dance before, Doc?"

"Me? Well, I... I've attended celebrations that involved dancing, like the wedding reception. You and I danced there, if I recall."

I nodded and smiled with my cheeks, one eye rolling away from the other. "You do."

"But as for, well, a dance proper, I'm not exactly sure. I'm well-acquainted with the Unicornish dancing customs of the prior two centuries, as well as traditional Pegasan war dances and the so-called Earth pony 'hoedown,' but as for actually participating in the sort of event we're attending tonight, I don't think I have. What about you? I do believe there is some sort of coming-of-age ceremony at Ponyville High known as 'prom,' correct?"

Oh sweet Celestia, my senior prom. If somepony were to pick a single definition of the word "awkward" to be etched in a monolithic stone that would stand for all eternity, long after civilization had crumbled to dust around it, it would have to be an account of my senior prom.

I suppose the best thing about that night had been my dress, a cute little red strapless thing that billowed across the floor and hugged my lithe teenage body just perfectly: I still have it, but I couldn't hope to fit into it now. I've put on a good 20 pounds at least since then, mostly in my barrel and flanks.

I had gotten a date at the last minute, because I really wanted to go, but didn't want to be that wallflower who just sits around as a third wheel to all her friends. The poor colt who'd agreed to go with me clearly wasn't used to being around mares. Pretty much the whole time we were there, he breathed uncomfortably and looked to be in physical pain (if I had to guess, his suit looked about a size too small for him.) He was also the pariah of the school, that kid with curly hair, big teeth, acne, thick glasses, you know the one. I can't even remember his name now, but his Cutie Mark was some weird die, and all he did, aside from ace tests, was sit around in the cafeteria with his herd and play Ogres and Oubliettes, which I'll be honest, looked kind of fun, but I didn't want to get laughed at for playing it.

Our picture, taken in front of a curtain in the gym, sits tucked between the pages of a yearbook somewhere in my attic. He, again, looks to be extremely uncomfortable on an infinite number of levels, while I'm standing there, eyes looking two different directions (neither of which were at the camera) with a look on my face that reads "What have I gotten myself into?" I suppose our dance wasn't too awkward, although he was too afraid to put a hoof on my waist, no matter how much I reassured him. Poor guy couldn't even bring himself to kiss me, and I was unsure for years whether that said more about him or me. I think the dude was just surprised that a mare had asked him out at all, even more so that said mare was me, and was just kinda scared because he didn't know what to do. I hope it didn't traumatize him too much. I wouldn't be surprised though if he's a millionaire by now and I'm just me.

"Yeah..." I said to Doc after a moment of silence. "Yeah, I had a prom."

"What was that like?"

"NO."

As we entered, there were countless other ponies about, all dressed in their finest. Some of the ensembles were clearly Rarity's work, while others likely came from boutiques in Canterlot or Manehattan. Even among such colorful clothing, however, me and my corsage stood out, attracting several oohs from the other mares, many of whom I see on a daily basis. Big Mac and Sugar Belle were there too; never would I have expected to see the big guy in a tux, but I can now say that I have. Maud and Mudbriar sat in the corner of the room like chaperones as Twiggy and Boulder "danced" atop their table. Doc and I were quick to spot Octavia, standing up on stage with the band and her cello, with Vinyl sitting slumped in a chair off to the side of her. She didn't look very happy: she'd been forced into a frilly blouse and overcoat, like something out of a previous century, and had traded her purple shades for even more decorative but even less cool pince-nez glasses. Octavia meanwhile was wearing a long black dress that dragged the floor and glittered with rhinestones, though her characteristic bowtie and collar still remained. Vinyl seemed to perk up significantly as we walked over to greet her.

"Well I'll be damned, if it isn't our girl Derpy!" She said cheerily. "Someone's lookin' sexy tonight! And Doc, is that you under all that? I've never seen you spruced up before! Lookin' sharp, my dude!" She offered him a hoof bump, which he accepted, having recently learned what they were.

Octavia, from up on stage, winked and smiled at me, saying in a moment what she'd loved to have used an hour for. Then, she turned to her favorite unicorn.

"Vinyl!" She said in just above a whisper. "Get your instrument ready! We're starting the next set soon!"

The mare formerly known as DJ P0N-3 sighed and rolled her eyes powerfully enough to shift the tides. From behind her chair, she levitated a small metallic triangle and the stick to strike it with.

"As if playing the triangle wasn't bad enough, I have to wear this!"

"Vinyl dear, you look fine."

"Look at this shirt! I look like a pirate! And NOT the cool kind!" She flipped up the ruffles on her blouse in frustration.

"If you'd worn the pants that came with it, the whole ensemble would make a lot more sense." Octavia remarked as she adjusted the tune on her cello.

"Hey, I told you: no pants! Mama needs to breathe down here! Besides, this is probably the only way ponies will even know I'm a mare!"

Doc and I had slowly managed to ease away as the odd couple continued their bickering, taking up positions on the dance floor for the next song. It was a waltz of sorts, and though Octavia and her ensemble played it beautifully, it probably would've sounded better on a full orchestra. The piece was slow and calm and dominated by strings, with occasional dissatisfied dings from Vinyl and her triangle. I was trying to keep an eye on my hooves, reciting the 1-2-3 steps I'd learned from a book without stepping on my dress or Doc. My dance partner would occasionally laugh a little as I narrowly dodged another couple or stumbled slightly to catch myself on him. Mostly, I let him lead, because I had a feeling his feel for mathematics and rhythm could help us out. At the very least, it kept us from knocking over anything or anypony.

We took a breather as the band set up for the next song. I could detect Vinyl's displeasure. She ran her hooves down her face and across her eyes, tugging down at her cheeks with a groan before slapping down on her knees.

"This is sooooo boriiiing!"

Octavia grinned, and, ever so slightly giggling, leaned down to speak in her ear, quietly, but just loud enough that I could perceive it.

"Remember when I first told you about this, Vinyl? Remember how I said that, if you made it through the evening, I'd do that thing to you when we got home?"

The unicorn immediately sat bolt upright in her chair, ears raised, eyes enlarged, with a hint of rosy blush on her cheeks.

"Yes ma'am!" She proudly proclaimed, rising to her hooves and crossing the stage. "Gimme that mic!"

Before Octavia or the conductor could protest, Vinyl Scratch was standing center stage at the microphone and turned back to face the band. "All right, ladies and germs, you know my favorite song for gigs like this. Moderately slow, D major, six-eighths; watch me for the changes, and don't get ahead of me."

As the band slowly started to comply with her request, the crowd of dancers churned back into motion. Soon, Vinyl began to sing with a voice I'd never heard come out of her; it was almost as if she'd been replaced by an angel. It was an old song, one I'd heard my parents hum to themselves before on Hearts and Hooves Day. I don't know it myself, but it was something about how "only fools rush in" but "I can't help but love you" or something like that.

"Derpy…" Doc said to me softly, drawing my gaze from my hooves and towards him as we slow danced in our little circle. "I just want you to know that these past few days have been some of the best, most fun days I've ever had, and that I feel greatly honored just being considered for your affections."

"Doc..."

"I may not be perfect, Derpy, and I'm definitely not wealthy, nor charming, but... I'd give you the world. I... I didn't think--- I never thought that I'd ever meet a mare who'd put up with me. I just ignored that part of the equation. But ever since I met you, I... I don't think my life can be complete without it. It would be an honor to me beyond belief if you would replace the n in my equation."

"Huh?"

"Er--- if you would be my special somepony." He chuckled to himself, gazing into my eyes. "But nonetheless, you are and have always been my very best friend, and no matter whom you choose, I will always stand beside you with my strongest show of support."

His simple words, delivered quietly on that dancefloor from his own heart, were enough to move me, to weaken me. I realized then and there that Doc just wanted the same things I did: a friend he could become closer with than any other, someone he could dedicate himself to, and someone he could call his own. And I, of all ponies, had been the only one able to bring that epiphany out of him. In his eyes, I was his one and only chance.

"Doc..." I said, my voice weakened from emotion. I put a hoof to his chin to look more directly into his eyes. "You're the sweetest, friendliest, most kindhearted stallion I've ever met. You'd do anything for your friends, and even more for me."

He tried to blush and look away, but I redirected him.

"You see past these eyes, this body, into who I truly am. That's a skill beyond worth, and beyond gratitude. You're priceless, Doc... how can I pass that up?"

Shaking only slightly and holding back only a few tears, I brought Doc in for an actual kiss. The way he held me was sublime; I could've died in his embrace. I could feel the heat from his face radiating against mine, but the heat was soothing. My wings, along with my heart, fluttered, and I think I even popped a hoof off the ground.

My first kiss with a stallion. What I would later find out was his first kiss ever. We held it out for a good minute or more, just standing there in the middle of the dancefloor for everypony to see. Vinyl finished her song on a beautiful note and saluted us; Octavia had to wipe tears from her eyes.

"You really should sing more often, dear. You have a beautiful voice."

"I'll sing for you anytime, Tavi."

Doc and I held each other close throughout all the rest of the night, dancing, kissing, expressing innocent little emotions whenever we found our voices. Naturally, we spent the next day together too, and the day after we went out with Lyra, Bon Bon, Vinyl and Octavia for some fun on the town. Treehugger was very gracious about my choice, and we're still on friendly terms with one another; I even suggested that Doc might benefit from meditation or yoga to calm him down when he gets high-strung.

I'm writing this many days later as I prepare for bed. There's a framed picture of me and Doc on my nightstand; I like to look at it until I drift off to sleep. Soon, I'll put up this diary and do just that.

What kind of dreams will I have? I don't know for sure, but by Luna's grace and the love I share with Doc and my friends, I have a feeling they'll be good ones.

Yours truly,
Derpy Hooves

Author's Note

Hey, that's a reference to the chapter titles! :derpytongue2:
But of course, can't put copyrighted lyrics in the text!
In the TEXT!
And as much as I wanted to link to a video of what I think Vinyl singing this song would sound like, none of the covers I found really clicked with me.
This may be an hour or so late for Valentine's Day, but it's the thought that counts.

Peace and Love, everypony! More stories coming soon, I promise! :heart:
-TMB