Cassandra's Sensual and Awesome Hearts and Hooves Day Story

by CassandraMyOCisBestpony

Rating: teen
Tags: Applejack, Slice of Life, My Little Pony: Friendship is Magic, Rainbow Dash, Romance, Original Character, Comedy, Bon-Bon, Rarity, Random, Sex
Length: 1565

My OC Cassandra suffers the terrible affliction of being loved by too many ponies.

This is Cassandra, my OC don't steal. Her interests include having a dark past, saving Twilight when the elements of harmony fail, and being Celestia's long-lost sister. She is the seventh element, the Element of Trust, because she has to learn to put trust in less-intelligent, less-reliable ponies, and other ponies have to realize they should trust her.

What's a mare to do when two of her friends simultaneously confess their love for her? On Hearts and Hooves Day, Cassandra's natural beauty proves to be more of a curse than a gift when her glimmering radiance enamors both Rarity and Rainbow Dash. She's saved the world countless times, but can she save herself from hurting her friends' feelings? I don't know, but I do know that Cassandra's stories are the best stories.

Published 2014-02-15 01:00:02 UTC
Last updated 2014-02-15 01:00:02 UTC

Cassandra

It was Hearts and Hooves Day in Ponyville, and none were more excited than the Mane 7. It was a magical time of year, when ponies showed their appreciation for the ones they loved most. For some, it was a day to spend time with a loved one. For others, it was a chance to make a declaration of love.

Rarity stopped by Roseluck's flower stand in pursuit of a very special somepony. "I'll have a dozen roses please."

"Sure thing" said Roseluck, "who's the lucky colt?"

"Can you keep a secret?"

"Rarity, us flower sellers are bound by a strict code of confidentiality for secret admirers, mistresses, and all matters of the heart."

"Good then. Because these aren't for a colt, they're for mare."

"GASP!" exclaimed Rose, "scandalous! But not to worry, my lips are sealed."

At the candy store, Rainbow Dash was purchasing a box of special Hearts and Hooves Day chocolates.

"Hey Bonbon," she said to the shopkeeper, "you're a fillyfooler, right?"

"That's not exactly the PC term, but yes, I am a lesbian. Why do you ask?"

"No reason, just making small talk."

"Come on now Dash, you can tell me, who's got your eyes wandering off the straight and narrow?"

"W-what are you talking about?" asked Dash evasively.

"You come in here on H&H day, buy a box of chocolates, then suddenly start asking about lesbianism. It's pretty obvious what's going on."

"Fine, you got me" conceded Rainbow Dash, "How did you get such insurmountable detective skills?"

"I've been taking lessons from Cassandra. She's so smart"

"She is, isn't she?" said Rainbow Dash longingly.

Hearts and Hooves Day was on a very specific day of the year, the day where ponies' estrus cycles reached their peak. Long ago, the holiday was called Heats and Horns Day, but was eventually changed to the more tasteful and marketable Hearts & Hooves.

Cassandra, long-lost sister to the Princess, and seventh Element of Harmony, made her way cautiously through the town. While Cassandra enjoyed the festivities of the holiday, it was also a trying time for her. Burdened with a flawless mane, and eyes that shined like stars, she was a prime target for lustful ponies, stallions and mares alike. Lesser ponies would spend the day hidden in their homes, safe from the advances of the others, but Cassandra had a duty as Equestria's last line of defense against those who wished them harm. For the fate of the world, she gathered up her courage and ventured out into the open. Suddenly she sensed movement. On her left, she saw Rarity approaching with a bouquet of roses. On her right, she saw Rainbow Dash approaching with a box of chocolates.

"Cassandra" said Rarity and Rainbow simultaneously, "please accept this gift and be my very special somepony..." they both did a double take, "WHAT???"

"Darling, you're much too bourgeoise to be Cassandra's very special somepony." said Rarity

"Oh yeah? Well you're too snooty and not cool enough!"

While the two were busy bickering, Cassandra slipped away. She needed help from the somepony who was too sexually inexperienced to cause any kind of threat. After a few minutes, she reached the library.

"Hi Cassandra, how are you doing today?" said Twilight, "If you're looking for the book on how to make a love poison, I gave it to the Cutie Mark Crusaders."

"Rarity and Rainbow Dash both confessed their love to me" explained Cassandra, "but I don't want to hurt either one's feelings."

"That sounds like quite the problem." said Twilight, "I bet I have a book on it."

"Silly Twilight, this isn't the kind of thing you can read in a book, you have to listen to your heart."

"Ooh" said Twilight, mystified by Cassandra's silver tongue. "Well, my heart's telling me that I should be Flash Sentry's waifu."

"The heart doesn't always know what it wants" admitted Cassandra, "you're probably experiencing your first heat. Soak your head in ice water, and your mind will clear up. I'll be on my way."

"Thanks for your help Cassandra. Spike! Where do we keep the bucket?"

Back outside, Cassandra mused to herself, "Isn't it funny how life works? You go to your friend for help with a problem, and end up solving her problem instead." Cassandra was smart enough that she could look where she was going even when deep in thought. Unfortunately, not all ponies were that gifted. Suddenly, a pony walked right into her, nearly barrelling her over.

"Whoopsie-daisy" said Applejack, "turribly sorry Cassandra, ah was thinkin' about havin a roll in th' hay with Braeburn." She began to drool.

"I think I can forgive you if you go away and don't bother me for the rest of the day."

"Cassandra, ah have a Hearts an' Hooves Day poem fer you." said Applejack.

"Oh, a poem?" said Cassandra with faked enthusiasm. Her expectations weren't very high.

"Eeyup, and it's free verse, which means it's a poem even though it don't rhyme."

"Let me guess, you learned that term at a poetry reading at Starbucks."

"Ah got kicked out for yellin' at th' barista, but ah think ah was justified, what kinda coffee place don't have apple coffee?"

"What say we just get this poem over with?" suggested Cassandra.

"Alrighty then." said Applejack. She cleared her throat.

"Cassandra, you are,
as sweet as an apple,
as pretty as an apple
as kind as an apple,
and as honest as an apple.
And this is kinda a cliche, but, you are, the..."

"apple of my eye?" finished Cassandra cynically.

"Huh" said Applejack, "that's a lot better than what ah had."

"I'm afraid to ask, but..."

"the favoritest pony." So what'd ya think? Be honest now, ah am th' Element of Honesty." she said, visibly and unnecessarily proud of this title.

"Honestly? I know several Vogons that could write better poetry than that. But still, good effort." She gave Applejack a gold star sticker with "you tried" written in comic sans. Applejack was so distracted being proud of herself that Cassandra managed to slip away unnoticed.

"Where'd she go?" wondered Applejack, "oh well, at least ah still have Braeburn.". She hurried to the train station to catch the train to Appleoosa. However, she got distracted again, and wandered onto the train tracks, where she got hit by a train and died.

Rarity and Rainbow Dash hadn't moved from their spot, and were continuing to argue over Cassandra.

"Girls, please stop," said Cassandra, stepping between the two.

"So which of us does your heart desire?" demanded Rarity.

"It's me isn't it?" said Rainbow.

"Why that is poppycock" sneered Rarity.

"That's enough," said Cassandra, "I... I couldn't decide" she said ashamedly. "I love you both too much to hurt your feelings." Tears began to well up in her eyes.

Rainbow put a comforting hoof on her shoulder. "Hey, don't beat yourself up. Your loyalty is really impressive. And you're right, not everypony can be perfect like me."

"I concur" added Rarity, "I never should have forced you to choose between friends. I love you too much for that. I'm willing to share you if I have to."

"I was about to say the very same thing!" exclaimed Rainbow.

"You know," said Cassandra, "if you two don't mind each other's company, then why don't the three of us all relieve our H&H tension together?" Rarity and Rainbow Dash smiled.

The three of them returned to Cassandra's place, where she had brought out a bottle of the finest red wine, and lit a roaring fire in the hearth. Rarity and Rainbow Dash were excited, but nervous at the same time, if they couldn't please Cassandra, that would be the Worst. Possible. Thing. They sipped their wine in a classy manner like Cassandra showed them, loosening up their inhibitions. Cassandra kissed Rarity and then Rainbow Dash. She stroked Rarity's soft velvety coat.

"Massage my wings" she instructed. Dash and Rarity each took one of her wings and ran their hooves across the soft feathery down, as they kissed each other. Rainbow Dash's wings sprung up with an audible ruffling sound.

"Oh my Dashie, you're really getting into this." teased Cassandra. She kissed Rainbow again, this time with a long and passionate kiss. With her free hoof she rubbed Rarity's horn

"Oh goodness!" exclaimed Rarity, breathing heavily.

"Rainbow" said Cassandra, " why is it that you don't like ponies touching your hooves?"

"No reason" said Rainbow evasively.

"Oh really?" said Cassandra with a devilish grin. She plucked a loose feather from her wing and ran it across Dash's forehoof.

"Wow! That feels radical!" exclaimed Dash, her voice reaching an octave it rarely went to. "I can't take anymore!"

Rarity was immensely enjoying watching her friend squirm. She ran her hoof along Dash's wing, causing the pegasus's eyes to water. As the stimulation brought Rainbow near climax, her anguish brought Rarity to her own. Cassandra wrapped her perfect sensual wings around the both of them, and her hot body took them over the edge.

Dash and Rarity were soon sound asleep, and Cassandra gingerly helped them into her bed. She would have joined them, but her world-protecting for the day was far from over.

"Sleep now my little ponies" she whispered to them, "Fluttershy's been acting really antsy today. I wonder if she could use my help.."