The Peculiar Deflowering of Diamond Tiara

by Littlecolt

Rating: mature
Tags: Diamond Tiara, My Little Pony: Friendship is Magic, Romance, Comedy, Rumble, Sex
Length: 4482

Rumble has had a crush on Diamond Tiara for years, and now they're about to graduate and head to college. On a trip to canterlot, Rumble asks her to the senior dance, and then something absolutely impossible happens.

Rumble has had a crush on Diamond Tiara for years, and now they're about to graduate and head to college. They go with their class to Canterlot to see the public university. Rumble is hoping to ask her to the senior dance while there.

Then, something completely, unthinkably impossible happens.

This story takes place in the future, and all characters are aged up accordingly.

CONTENT INFO: Masturbation, surprise sex, vaginal sex, first sex, internal cumshot

Just a silly story I wrote on a whim. Narration breaks the 4th wall sometimes. :3

Featured on 11/7/2015! But... why?? Kidding! Thanks for the support! :P

Self-edited - beware!
Cover art by Moka on Pixiv. - Cover art may change down the line, I am thinking of drawing my own cover for this.
Thanks to my Patrons, Super Trampoline and Katherine Kerensky!

Published 2015-11-06 09:00:02 UTC
Last updated 2015-11-06 09:00:02 UTC

The Slip

The Peculiar Deflowering of Diamond Tiara

Now, dear reader, I shall tell you that tale of two ponies that were brought together by the most unlikely of circumstances. A tale of sudden and shocking debauchery the likes of which you will likely never hear of again. Sit back and enjoy the tale of the literal fall to the depths of pleasure.

Rumble was a pegasus pony of seventeen years who lived in Ponyville. For as long as he could remember, he’d had his eyes on the most beautiful mare he’d ever met, Diamond Tiara. She had been, in her younger years, a stuck-up pony that looked down upon others. She was basically a bully, and Rumble had hated that he found her attractive. One day, it came to pass that Diamond Tiara realized that she had been wrong, and that she wanted to be friends with everypony at the school.

Rumble fell for her completely, no longer able to hold back his feelings since her inner transformation. He was deeply in love, but there was a problem with that: he was a quiet, awkward sort that didn’t much associate with others very well. He got along well enough with everypony, even considered some ponies his friends, but the combination of Diamond’s beauty and status as a popular girl at school had always prevented him from getting too close to her, even after her change and her own desire to make as many friends as possible.

Rumble knew in his heart that Diamond Tiara was out of his league. That fact was just as clear to him as the fact that he would love her forever, and thus an inner struggle occupied his heart and mind quite often when she was around.

The two of them had reached their last year of school together. He felt his opportunities to tell her how he felt slipping by, and he was hampered by social norms within the school. There was the common, unspoken rule of popular kids and unpopular kids, and how they didn’t hang out together or date each other. He hated how powerless he felt to approach her sometimes, and his heart yearned for her even more. By the end of the year, she’d surely go on to some prestigious university in Canterlot or Manehattan, and he’d never see her again..

In the case of Diamond Tiara, she felt the effects of the school’s social structure as well, especially when she got to an age where she had thoughts of dating colts. She found several of the boys at her school attractive, but her vicious past weighed heavily on her heart. They would never want to date me after what I did to them when we were younger. Plus, what would my parents think? Having friends is one thing, but dating somepony? Her heart sank with the thought.

In a way, she was right. She seemed unapproachable to her male classmates, though not because of her past. Even though she was beautiful and popular, she’d actually never had a coltfriend for more than a day in all eighteen of her years. Her single foray into romance had started innocently enough. Snails, one of the boys in her class, asked if she wanted to go out with him one day. She wasn’t opposed to it, finding his tall physique appealing, and accepted. However, by the end of the day she felt embarrassment at her decision. Word had gotten around that she was going to be dating Snails, who was not known for his intelligence, and the rumor mill was in full-operation.

She wasn’t teased about it, nothing of the sort, but her own inner-doubt had kicked in. What will mother and father think? I… I can’t do this. It was a mistake. She told Snails she’d changed her mind, that she just wasn’t ready yet. He was sad, but told her it was okay. They stayed acquaintances, but much to her sadness, the two of them barely spoke except in passing after that.

Diamond Tiara remained single for the remainder of her high school career, her own insecurities slowly pulling her into her shell. She never returned to being cruel as she had been before, but with boys, she kept a quiet demeanor. She never wanted to break anypony else’s heart again.

Flash forward, the school’s senior dance was coming up, and Rumble wanted to ask Diamond Tiara to be his date more than anything else in the world, but he knew it was an impossible dream. He had enough trouble approaching her and talking to her, let alone asking her to be his date. He would daydream of what it would be like, the two of them in fancy garb, sliding across the dance floor. They would spin, and she would stare into his eyes, giving him a sultry look of romantic passion, and he would stare back, enchanted by her mere presence.

Diamond felt such loneliness, and wondered if anypony would ask her out. After graduating, she would go on to college. Her home life and social situation would change, and she felt like she would finally be able to seek out love. She hoped that somepony would ask her to the dance, promising herself that she would accept their proposal and go with them, consequences be damned!

The dance was the following week, and Rumble was certain she had a date already, so his asking her would be fruitless. However, the idea that she would turn him down for already having a date rather than turning him down because she didn’t want to go with him gave him a bit of courage. It’ll be easier to take if she’s already got somepony going with her. It won’t be as awkward. I’m such a coward, but… I have to try!

The class went on a planned trip Canterlot University, and it was on that day that Rumble decided he would ask her, no matter what. He glanced at her, not wanting to make eye contact, but still wanting to take in her beauty. They were sitting together with the rest of their class inside a room at Canterlot University, listening to professors speak about the benefits of the school’s programs. Rumble sighed and wondered why he was here. He knew that his parents would probably ship him off to Cloudsdale for college. He glanced at Diamond Tiara again. She’ll probably go to a private school here in Canterlot. Graduation day might be the last time we ever see each other. He sighed, and then quickly looked away when he noticed her turning to look over at him. Whew! That was close.

The presentations were finished for the day, but the train to Ponyville didn’t leave for another two hours. The students had a long time to just hang around and explore the campus. Rumble spotted her, standing in the hallway near a window. Sunlight shone in, illuminating her lovely pink mane as she chatted with her best friend, Silver Spoon. He nervously approached the two of them, his obsession of the past weeks pushing him forward.

The young mares noticed him. He froze. Silver Spoon looked up and raised a hoof towards him. “Hiii, Rumble!” she shouted, waving him over. She leaned in towards Diamond, and Rumble could hear her whispering but could not make out her words. “Here comes your future coltfriend, now.” She smirked and giggled.

Diamond Tiara rolled her eyes.

The reaction made Rumble’s heart sink into his stomach, but he gulped and shook his head, continuing his approach. No matter what! No matter what! he chanted in his head as he stepped nearer and nearer.

“Hey there, you two,” he said shyly. “It sure has been a long day.”

“Tell me about it,” Silver Spoon replied. “Talk about boring lecture after boring lecture!”

“I don’t even know why they made us come here. I already know where I’m going to college,” Diamond Tiara chimed in.

“Right!” Rumble said, forcing a laugh. “Totally pointless.”

The three of them stood in silence for a moment, and then Silver Spoon’s expression became mischievous. She playfully tilted her head towards Diamond. “Oh my, I need to use the little fillies’ room. You two stay here and wait for me,” she said, and then skipped away, flashing the two of them a wink as she went.

Diamond Tiara groaned, staring down at the ground. Rumble blinked and turned his gaze low as well, silence surrounding them.

“So, uh…” they both said at the same time, and then laughed.

“You go first,” Diamond Tiara said, turning to look up at him.

Rumble could detect the slightest blush on her cheeks, and for a moment, he felt that his heart might jump up his throat. Blushing? Is it for me? Why? Oh my gosh, does she like me? He swallowed hard and then shakily began to speak.

“S-s-s-so, Diamond Tiara. The school dance is coming up,” he said. Yes! I brought it up! He felt his heart beating faster as the moment approached.

“Oh. Yeah. That hassle,” Diamond Tiara sighed and swept her hair to the side. “Yeah, I have to go. After all, who would be princess of the dance but me? Right?”

Rumble smiled enthusiastically. “Right, it’s a foregone conclusion, isn’t it?”

Diamond Tiara nodded matter-of-factly. “Yes, of course.”

Silence returned. Rumble felt his opportunity slipping away. Sweat began to form on his brow as Diamond Tiara turned her head and looked in the direction Silver Spoon had gone. “Sheesh, what is taking her so long?” she grumbled.

Do it! Do it, you wimp! Ask her! Rumble thought to himself over and over.

“How long does it take to—“

“Diamond Tiara!” Rumble barked out somewhat louder than a normal speaking voice. She jerked her head to look at him, and their eyes locked together.

“Yes?” she asked, blinking several times.

“I want to… that is… do you want to maybe, uh… I’d be honored if, uh…” he stammered, unable to complete a sentence to save his life.

“What? Spit it out, already,” she said, sounding somewhat like her old self.

“Would you go to the dance with me?” he asked, and felt he would almost faint.

Diamond Tiara’s face lit up bright red, and Rumble couldn’t tell if it was anger, or embarrassment, or what, but he knew it wasn’t good.

“Are…! Are you actually serious?” she said, also somewhat louder than a speaking voice.

Rumble nodded his head. “Yeah.”

Diamond Tiara groaned. “That was a rhetorical question! The dance is like, next week! Why are you asking me now?” she said, waving a hoof in the air.

“I just… I’ve wanted to ask you for a while now, but I just…”

Diamond Tiara fumed. I can’t believe this colt! He’s given me no time to prepare! Oh my gosh, I did not see this coming. How can he just put me on the spot like this? This is way too—

“Hey you two, I’m baa-aack!” Silver Spoon said, leaping right back to where she’d been standing before. Rumble turned to look at her, his face full of fear, sweat dripping from his forehead.

Diamond Tiara sighed. “Look, Rumble, I’m sorry, but you’re uh... too late,” she said, averting her eyes. “I already have a date for the dance.”

Rumble lowered his head and sighed, not noticing the slight glare that Silver Spoon was shooting at her friend. “Yeah. I kind of figured,” he said, turning around. “Sorry to have bothered you. Have a good time at the dance.”

He walked away, defeated. After he was out of earshot, Silver Spoon slapped a hoof against Diamond’s shoulder. “You do not have a date! What is your problem?”

“He just… took me by surprise! He’s the first pony to have even asked. I guess I thought… I don’t know what I thought. I guess I thought it would have been sooner, and…”

“And what?”

Diamond Tiara sighed. “I don’t know. I just…”

Silver Spoon pointed down the hallway. “He’s still there, D. T. Go on! Go tell him!”

Diamond Tiara gasped. “I-I-I can’t tell him now! I just lied to his face! He’d turn me down!”

Silver Spoon shook her head. “You will never know unless you--”

“Look, I don’t want to talk about it, okay?” She stormed down the hall and went up the stairs to the second floor.

Rumble found himself outside, having left out the back of the school’s main hall. He hung his head and sighed. Of course somepony beat you to her. She probably wouldn’t want to go with you, anyway. That’s what you get for being so slow!

“I just wish I had asked her sooner,” he said quietly, and then turned his head up. He’d never been out the back of the main hall, and noticed something interesting. In the rear of the school, there was a raised rooftop area with a stone ledge all around it. He could tell there was tables with umbrellas up there, and tilted his head in thought. “Maybe I will go here after all. I mean, the campus is really nice, the staff was friendly. Plus, I’m sure she’ll be going to school in Canterlot, so…”

He sighed again. Ah, who am I kidding? Even if I go to school in the same city as her, she won’t want to date me. He let his gaze wander to the right, and then he saw something that made his eyes go wide. Hoooolyyyyy crap!

He stopped dead in his tracks and couldn’t move his eyes from the sight before him. Huddled up against the wall that separated the balcony area and the school, standing atop the stone ledge, was Diamond Tiara. She was facing in towards the Balcony, and judging by what she was doing, he was almost certain she was keeping an eye on the door in case anypony came out there.

She was hunched over, her ass pushed up into the air, with her hoof between her legs. The furious motion of her hoof against her spread pussy lips was plain for Rumble to see, as well as drops of glistening moisture dripping down from her hoof onto the stone below.

What in the heck is she doing up there? Wouldn’t it have been better to go to the restroom? He thought, his mind still barely comprehending what he was seeing. She let out a light moan, and a shiver shot down his back. He instinctively began to step towards her, getting as close as he could to the underside view of her raised and pushed-back rear end. This. Can. Not. Be. Happening!

Now, I’m sure you’re wondering what Diamond Tiara was doing up there, so let me tell you. Having been moved by Rumble’s sudden question about the dance, and feeling bad for lying to him about having a date, she’d run away to go somewhere she could be alone. She’d discovered the balcony outside the cafeteria and crept out the door. Initially, she had been leaning against the ledge, thinking to herself about what hat just happened.

You’re still doing it, Diamond. Gosh, you are so stupid! she thought to herself. Would it have been so hard to just say yes? It’s not like he’s ugly, or mean, or anything like that. He’s just… quiet and distant. But maybe once he opens up, he’d be great… just like you were… or could be, anyway.

She pictured him in her mind, and imagined what it would be like to go to the dance with him. Her image of him was actually handsome to her. She pictured his hair actually slicked and styled, his clothing form-fitting and well-tailored, as he swept her off her hooves. Her imagination kept going. She pictured them kissing, and felt butterflies in her stomach. She sighed to herself, picturing her hoof working down his chest, unbuttoning his shirt and releasing his soft yet well-toned chest. Wow, he’d really clean up nicely, too. I’d never noticed, but I guess he’s got a pretty hot body… plus he’s a pegasus. You know what they say about pegasi...

What do they say about pegasi, you wonder? Well, to speak it in the vernacular, they are freaks in the bedroom. That is what they say, in any case, and Diamond had certainly heard it. Her mind having drifted to that subject, felt a warmth down below and an irresistible urge to attend to it. She looked around, spotting nopony in the back courtyard. She glanced at the door that led back into the school, which was firmly closed and made quite a loud noise if opened.

She pushed herself up onto the ledge, leaned against the wall, and whispered Rumble’s name as she pressed her hoof to the top of her pussy. This is crazy. Why am I doing this? Oh, Celestia, it feels so good, though! The breeze hit her behind as she began to work her pussy to a sopping wet mess, the rush of cool air only driving her wilder.

Back down below in the courtyard, Rumble was staring up at her, watching her frig herself to the heights of her ecstasy. He could feel his now rock-hard cock bulging against his belly. He spread his wings out slightly. He felt a shaking in his legs. He wanted nothing more than to fly up to that rooftop, tackle her to the ground, and tell her that he loved her, that he wanted to be with her, but he knew it was completely out of the question.

Then, he heard it. Quietly at first, then a bit louder, she was calling out a name: His name.

“Rumble… Rrrrrumble!” she breathily wheezed as she frigged herself.

Rumble slapped a hoof over his mouth to keep his voice from jumping out of his throat. Holy shit! She’s thinking about me! This is definitely a dream!

The Pegasus colt stumbled to the right a bit, and suddenly felt his back right hoof slip into a sinkhole. He flapped his wings forward, which didn’t help, and he fell backwards, slamming against the grass just as Diamond Tiara called out his name one more time.

“OOOF!”

Diamond’s head snapped around upon hearing his voice. Her hoof pulled away from her hindquarters. Her eyes caught sight of rumble, immediately locking on to his cock, which was now wobbing in the air, sticking straight up from his body. “Rumble!?” she managed to say, and then felt her hoof slip from the ledge.

She tumbled forward, falling from the rooftop, plummeting down one story, twisting in the air, and then slammed down.

Now, I am going to tell you, fillies and gentlecolts, that you should not try what I am about to describe. The chances of this occurring are one in infinity, making this couple so very special. If you attempt it, you will surely fail and probably hurt yourself. It is this single event that makes their story so very peculiar.

You see, she landed upon the young stallion so perfectly, with such pristine precision, that her soaking wet pussy slammed straight down around his cock, like two pieces of a machine locking together, as if they had been made to do such a thing.

However, no pony is made to do such a thing. Both of them had the wind knocked out of them and let out loud groans. They were lucky neither of them had been seriously injured! Their vision went blurry, and Diamond Tiara felt her back give out. She fell forward against Rumble, her pelvis pulsing with pain. Rumble, too, felt pain in his hips, and an odd sensation as well.

It took only a few seconds for the two of them to realize what had happened.

Rumble felt his cock surrounded by warmth, and Diamond felt her insides absolutely filled. They both gasped with realization. Diamond slammed her hooves down against Rumble’s chest and rose up. The both of them stared down toward their groins. The mere sight of his cock pressed deep inside of her spread lips made both of them groan with such fiery, mixed emotions.

Diamond Tiara felt panic. What!? Sweet Celestia, I never thought this is how I would lose my virginity! She thought, and then repositioned her hind legs. No! This doesn’t count! This is a freak accident! Why am I even worried about that at a time like this!? She ignored the burning in her loins and the slight, though not all terrible, pain in her pussy as she tried to stand up off the colt’s cock.

The feeling of it sliding out of her made her gasp and lose her balance. Back down she fell, Rumbles hardness pushing back up inside of her. She arched her back and threw her head up into the air, crying out a mix of pleasure and pain.

With this failure, she stared down at him in a panic and panted her words out. “How dare you...! Watch me while I’m...!”

Rumble pushed his hooves against her. “Get off me, then! Why were you doing it there of all places, anyway?”

“None of your business!” she shouted back, pushing herself up off of him again. This time, though, a pain that shot up her leg made her fall down against him once more, and this time she fell forward, her face slamming against his shoulder. She breathed heavily into his ear, and without even thinking about it, grinded her crotch against his, making both of them moan.

“We have to… get you off,” Rumble said, the strength to move leaving him.

“I intend to,” Diamond exhaled gruffly into his ear. “Let me just… try something!”

She rose back up, his cock sliding out of her, and then slammed herself back down against it. A squeak escaped her mouth along with her tongue. “Damn it! Hang on! I’ll try again!” she said, now knowing full-well that she was lying to him again.

She began to bob up and down on his cock, grinding forward and backward slightly, no longer disguising what she was doing. Their breathing increased in speed and their moans echoed off the walls of the building as they fucked in the grass. Rumble placed his hooves on her hips and began to push and pull against her, increasing the intensity of her thrusts.

“What do you… think you’re doing?” Diamond asked, her blushing face staring down at him, her mane having gone completely wild and hanging down over her face.

“What do you… think you’re doing?” he asked back. He could feel his climax approaching, and began to thrust his hips harder and harder.

“I don’t know!” Diamond answered, and then pushed her hooves against his chest, grinding up and down with all her might. “But I’m not going to stop! Don’t you stop, either!”

Rumble increased the strength of his grip on her, thrusting his pelvis as best he could, pulling down as she bounced up, then rising back up to meet her as she fell. Their bodies slapped against one another with speed and force, pushing their voices higher and higher.

“Fuck!” Rumble cried out. “I’m gonna—“

Diamond’s eyes went wide. “Don’t you dare!” she shouted, but it was too late. She felt him flare and explode inside of her, blasting her full of his burning hot semen. She groaned as her whole body erupted with intense warmth. She fell down against him, breathing heavily, as she felt his cock go still and then begin to shrink inside of her.

After a moment, she lifted up her head and looked down at him, still breathing heavier than usual.

He smiled up at her.

She reached back with her right hoof and then slapped him right across his face.

Shocked, Rumble lay silently as Diamond got up off of him and stretched her legs. She began to limp away, and he stared at her, not knowing what to say.

What the fuck have I done? he thought. I just came inside Diamond Tiara!

The young mare stopped a few paces from him and turned her head. She glared down at him and then sighed, her expression gradually softening. “Yes,” she said, her face blushing a bit more brightly.

“Yes?” Rumble managed.

“Yes, I’ll go to the dance with you. I sort of… lied about having a date.”

Rumble felt his heart soar, but he tried to maintain what little cool he had left in him. “Cool. I can’t wait!”

She smirked. “Oh, and by the way, what just happened? That was completely crazy! You can’t tell anypony, got it?”

Rumble nodded his head. “Of course not!”

Diamond glanced to the side, away from him. “Oh, and after our train ride back to Ponyville, I’m going home with you.”

Rumble began to stand up shakily. “What? I mean, sure, but why?”

Diamond turned and began to walk away again. “I didn’t cum just now, and tonight, you’re going to make me. Got it?”

Rumble almost leapt into flight, but instead trotted up to walk alongside her. He lightly nuzzled his face against her. “Sure thing!”

Diamond scooted away from him slightly. “And no PDA’s! Yet…” The shade of red on her cheeks turned even brighter, and she looked away from him.

Rumble laughed, his stomach full of butterflies at how cute she was being. “You got it.”

And that, dear reader, is the peculiar tale of the deflowering of Diamond.

Author's Note

This was a completely unplanned story. The idea struck me the other day and I had to write it! The concept is based on a really silly hentai I saw a while back that was part of a collection of shorts called Tales of Titillation. (I think that was the title, anyway.) In one of the shorts in that hentai was a sequence where a woman and a man each had a series of terrible events happen to them. The man ended up lying on the ground outside a building with his pants down. The woman had her panties torn off and flew out a window, falling to the ground. She landed right on his dick.

It may not have the detail and such that my previous clopfics have had, but it exists almost solely for the gag at the end. :rainbowlaugh:

I sort of imagine this as a story being told to someone out loud, although the narrator refers to you all as "dear reader" and such. In any case, it's just the way I'd envisioned it. It was fun to dream up and write, and I hope it was enjoyable to read.

Don't forget to "Like" if ya liked it! It's much appreciated! :heart:

Thank you to my patrons, Super Trampoline and Katherine Kerensky!

If you like my stories, please consider supporting me on Patreon.