Midnight Mistress

by Omegathyst

Rating: mature
Tags: Sex, Profanity, My Little Pony: Friendship is Magic, Romance, Applejack, Porn, Fetish, Rarity
Length: 3096

The week following Rarity's latest breakup takes a turn from one of the worst weeks of her life to something more beautiful than Rarity could've ever expected.

Normally after a breakup with a coltfriend, Rarity would shrug it off with a glass of wine and move on with her life. But after dating a coltfriend for almost a year, Rarity is exposed to a nasty truth about him. With her latest and most serious relationship ending in disaster, Rarity is ready to give up on love. But what will she learn about herself and one of her closest friendships when love isn't ready to give up on her?

Cover art by LadyBanshee
Chapter 1 is setup, Chapter 2 is romance and clop. Will contain unnamed ex, sad undertones in first chapter, strictly monogamous relationship, lesbian sex, oral sex, loss of virginity, magic stimulation, spanking, face-sitting, hoofing, and outdoor sex at midnight.

Published 2021-06-19 05:50:01 UTC
Last updated 2021-06-30 14:13:59 UTC

Running

“Miss, are you oka-”

“I’m fine, thank you,” I managed to say as I rushed past the hostess behind the counter, levitating a pouch of bits to her, not forgetting my Element even in what was becoming one of the worst nights of my life. I didn’t skip a beat as I dropped the bits and then used my magic to swing the diner door open, the chilling air blasting into my fur as I slammed the door closed and used the nightlights to navigate through the small town. The perks of living in your own business location was that I didn’t have to search for a house that looked like a clone of all the others, it stuck out like a sore hoof. I barely glanced over my shoulder, letting out a deep breath as I saw nopony behind me. Even though the breakup came from my mouth, it made little difference in regards to the circumstances.

The stallion, who isn’t even deserving of a name, had initially been a pony that swept me off my hooves and took me out to dinner several times. Each time he had kissed me with intensity afterwards, wanting to follow me back to my boutique. I had told him no, after all a lady doesn’t sleep with another stallion until the moment feels right. But the problem was that tiny little voice inside my head, telling me to wait on going all the way. It clicked when over half a year into a relationship, the stallion had stopped visiting my boutique everyday, or week for that matter. Dates were only once a month, and it was only the night before that Fluttershy had come to my door telling me that he had tried to sleep with her. And if Discord hadn’t been there to send my ex-coltfriend running for the hills, what would’ve happened then?

And so this colt who couldn’t keep it in his sheath confessed to sleeping with multiple mares, saying that if I had only done what a proper marefriend was supposed to do, we wouldn’t be in this mess. I responded in kind by standing on my hind legs and using my magic to launch the soda from my glass and all over him. I had attempted to go to dinner in hopes that this was all a big misunderstanding, but now I was storming away into the night. But what if the pig was following me, and I didn’t notice? I had to spend the night elsewhere, the alternative of crying into my pillows while the darkness preyed on my thoughts sent a chill throughout my body. I broke into a full gallop towards Sweet Apple Acres, trying and failing to muffle my own sobs as I reached the barn door. After giving myself a few moments to calm down, I lifted my hoof to knock on the door. Before I could, the door swung open and Applejack’s green eyes were wide as she stepped out of the barn.

“Rares, what’s the matter?” Applejack wrapped one foreleg around me, then the other as she hugged me. “Now now, we don’t want to wake everypony else.”

“Y-You’re right, sorry,” I stuttered. “He was cheating on me...he made a move on Fluttershy. Several moves possibly, before Discord sent him running.”

“He…” Applejack’s nostrils flared as she gritted her teeth, her hooves shaking. “Where did you last see him?”

“Applejack, it’s not worth it,” I placed my hoof on her shoulder, and her expression completely softened as she glanced at my hoof. “He technically didn’t commit any crime, and when he does, his own actions will catch up to him. Plus, I don’t want to see him again. Ever. So the most you and the others can do for me, darling, is to keep him away. Okay?”

“Alright,” Applejack sighed. “Don’t walk back home, ah would hate for you to be alone right now.”

“Well, if you insist,” I nodded, not admitting my intentions to her. I stepped into the building as Applejack led me to her room. I walked inside, noticing the apple designs on her pillows and on the door and wall behind me. It was Applejack’s room alright. But the only resemblance of something to sleep on besides her bed was some purple cushion on the floor, I glanced at it with my muzzle curled up, and Applejack walked in front of me. As she glanced at the same object I was staring at, Applejack let out a barely restrained laugh as she waved her hoof.

“Celestia’s sake, ah’m not gonna make you sleep on that!” Applejack assured me. “That’s Winona’s bed. We can share mine, sugarcube. After all, we’ve done it before, remember?”

“Ah yes, that sleepover,” I remembered, but that was many years ago when we simply couldn’t see eye to eye on anything. And now she was the friend I ran to in the wake of such a horrific turn of events. I smiled for the first time that night, and waited for Applejack to hang up her hat and climb into the sheets of her bed before I joined her.

Sure, it felt a lot more stiff than the mattress I slept on every night, but smelling Applejack’s earthy scent beside me as she gently rested a hoof on my shoulder brought a warmth that valiantly fought away the angry thoughts and tears that escaped me. In the almost-year that I had dated that pitiful colt, I had rarely seen my four dearest friends in Ponyville, always consumed in my work or when I would see him next. And now, among the tears and anger, came a new feeling glowing inside of me. A feeling that with the stallion that was no longer in my life, caused me to be unchained from the shackles around my hooves. Tomorrow was a new day, not only without him, but with my best friend beside me for whatever the day brought to me.

I wiped the stained makeup off my face with my hoof, closing my eyes and allowing myself to succumb to the darkness that eagerly welcomed me.

Spooning

Five days had passed since I had left that diner without looking back, and I felt a skip in my step as me and Applejack walked out of Fluttershy’s cottage. The five of us promised to make more time for each other upon my breakup and the harassment brought upon Fluttershy, and we were just leaving from a game night that she had planned with the help of her dear Discord. Of course, the pieces on the board moved on their own accord with his magic, turning an otherwise ordinary game night into a chaotic one. When Fluttershy inevitably won, the rest of us smiled and rolled our eyes as Fluttershy snuggled into Discord’s side. As Dash and Pinkie began getting lost in their own conversation, Applejack turned to me and whispered in my ear.

“Ah gotta help the family with dinner,” Applejack said. “You coming?”

I nodded, after all I had been eating with them for the past four nights and still didn’t tire of the various apple dishes they had served to me: apple cakes, apple pies, oatmeal with apple slices, and other various apple pastries. No coltfriend had made such love in a dish like Applejack had...no scratch that, no coltfriend had made any dish for me period. And the idea of trying to date one again felt like a joke, given that Applejack and my other friends were enough for me to feel loved.

As I got up and followed Applejack to Sweet Apple Acres, I thought about writing a letter to Twilight Sparkle about what I had learned from my most recent breakup. But smelling the vague earthy scent on Applejack’s pelt cleared my thoughts and made my heart beat fast, as it had for the past couple of days. Why was that, I wondered? I shook my head and refused to follow that train of thought as I stared at the sunset, the sun about to disappear behind the barn that we were approaching.

As we made our way into the kitchen, Apple Bloom and Sweetie Belle were already at the table raving about their latest cutie mark mission while Granny Smith nodded along and smiled at the two fillies. Big Mac and Sugar Belle were at the kitchen counter throwing together an apple salad of sorts, and the latter waved at me before turning back to her husband. They were quite happy with each other somehow, and I couldn’t help but wonder what they got right in their relationship.

I sat down next to Apple Bloom and listened as they told me about their day.

The apple salad had a divine variety of flavors, and me and Applejack decided to take our apple pie a la mode outside to the hills, Applejack insisting on enjoying our desserts with the starry night sky and cold breeze on the hillside. While the sky’s darkness did remind me of that night I ran to Sweet Apple Acres, the memory didn’t quite pierce my heart as I initially expected. Rather, a rush of heat came to my cheeks down to the rest of my body as I left the barn and walked to the hillside with Applejack and only Applejack. With my magic, I took the dessert plates up the hill and set them down on the grass as I brought a spoon of the dessert to my lips. Applejack stared at her plate for a while, and just as I was about to question her, she lowered her face to the plate.

“Oh!” I blushed, using my magic to bring a spoonful of apple pie to Applejack’s face. “I forget you don’t have a horn, let me help.”

“It’s okay, Rares,” Applejack pulled her face away from her plate and smiled. “Ah’m used to eatin’ like this.”

“Nonsense,” I insisted. “What are friends for if not spooning you?”

Applejack blushed, and I corrected myself.

“W-With food!” I stammered, glancing at the tree next to me. “You know what I mean.”

“Yes, yes, ah’ll spare ya from your explanation,” Applejack chuckled, opening her mouth and allowing me to feed her the dessert. She let me repeat this motion several times before I used the spoon to feed myself, and Applejack smirked at me. “Sugar Belle does this for Big Mac actually, what with her horn and all. Perhaps you can keep coming here, and spoon me as you so subtly put it? With food, of course.”

I didn’t know that my best friend was capable of such a shit-eating grin until now, and instead of knocking that grin off her face, my mouth decided to speak without my permission.

“What if I don’t want to spoon you with food?” I asked.

Applejack’s eyes widened as her grin disappeared, even though her blush didn’t.

“Ah’m sorry?”

“You heard me,” I smirked at her, the tables turning. “It’s not like you didn’t spoon me several nights ago.”

“Ya got me,” Applejack shook her head, a faint smile on her lips appearing as she calmed down. “But to be fair, ah was comfortin’ ya that night. You don’t swing that way anyhow.”

I set my spoon down, a deadly silence taking over the hillside before I tilted my head and spoke.

“I don’t? My, I never realized you were the decider of that, darling,” I snickered, all my emotions toppling over at once. Up until that night with Applejack, I never seriously entertained the idea of being with a mare. But there was her hoof on my shoulder the night of the breakup, the discovery of her intoxicating scent and the way she made me laugh and feel at home and I never wanted to leave…

...oh.

“Well, perhaps I swing that way for one mare,” I got up and walked towards Applejack until our muzzles were touching, my half-lidded gaze on Applejack’s stunned and blushing expression as I smiled at her. “Can’t believe I’ve been blind to it all this time…”

I kissed Applejack, closing my eyes and not even seeing how she reacted to the moment that would forever change our relationship. I pulled away from the kiss, Applejack an even hotter mess than before I kissed her (emphasis on the ‘hot’ I may add). As she remained speechless, I narrowed my eyes at her as she glanced at the barn in the distance.

“Don’t go running off on me,” I told her.

“Ah’m not,” Applejack promised. “But are ya sure about this, sugarcube? It’s only been five days since your breakup, and if you just want to get your rocks off, that’s fine. But ah would find some other pony to do it with, cause ah’m not like that.”

“And I’m not either,” I assured her, placing my hooves over her own. “There’s no other pony that I want to share my first time with.”

“Wait, you’re a virgin?” Applejack’s jaw dropped. “You never-”

“No, darling, I wasn’t about to give myself to a stallion that half-assed everything,” I rolled my eyes. “But a best friend that’s been there for me all these years? What could be better?”

“Ah suppose ah can’t argue with that,” Applejack gave a hint of a smile as she leaned in and pressed her lips against mine. I pushed forward, my hooves resting over her shoulders as I allowed my tongue to slip in her mouth. I felt years of unknowingly holding back coming undone as I pushed Applejack onto her back and held Applejack’s face with one cheek as the other hoof roamed down her side, stopping right above her clit as I gently rubbed her stomach. Applejack moaned in my mouth as my horn lit up, teasing her clit with my magic. As she bucked up, her wet clit brushed against my own, and after feeling a taste of paradise within that brief contact, I used my magic to connect our pussies together.

As I thrusted against her, Applejack moaned louder. I glanced at the barn, noticing all the lights were off, before I turned back to my new lover as thrusted harder against her. It felt like lightning bolts shooting into my body, sparking heat spreading throughout my insides as I squeaked and gasped. I glanced back down at Applejack, her ponytail having come undone into a blonde messy pool with her hat beside her. With my horn, I lifted Applejack’s hat off the ground and placed it on my head. Letting out a growl as I pounded Applejack harder, feeling the wet heat connecting us together, I howled as I came all over her. Juices pouring down her legs and into the grass, I lunged and pressed our lips together. After all, her family is likely to dismiss one orgasmic cry, but two? We’d have a mess on our hooves, and that wasn’t referring to the one we were making between our legs.

I could feel Applejack scream in our lip lock as she bucked her hips upward, her orgasm not a liquid firework quite like mine, but still powerful all the same. As I pulled out of the kiss, my heart skipped a beat as I looked at Applejack’s green eyes staring off into nothing, her tongue sticking out of her mouth as she panted for air. Kissing her neck up to her cheek, I jumped off of her and dove into her sensitive clit, twirling my tongue around it. Applejack cried out, placing her foreleg over her mouth before she could give us away. I snickered against her clit, my tongue traveling from her clit to her insides. Applejack bucked against my face, and after I loosened her up, I replaced my tongue with my hoof. Pushing inside of her slowly, I rubbed her nipples with my free hoof as I relished Applejack’s desperate attempts to muffle her profanities with her forelegs.

Half my foreleg was inside her when I felt the farmpony’s second orgasm. And as I pulled my foreleg out slowly, I gave a soft giggle as I prepared for the finale: I fell on my back, using my magic to lift Applejack onto my face. As the cumdrunk mare sat on my face, I used my hooves to keep her from tumbling over as I continued to use my tongue to fuck her. Applejack’s speech became words blended into each other in incoherent speech as she moved back and forth against my muzzle. I smacked her ass, her fat orange orbs of flesh over and over again, Applejack screaming out a loud “BUCK!” as she reached her third and final orgasm, collapsing into the grass. With my muzzle and foreleg drenched in her cum, I got up on my four hooves and gulped as I saw one single light turn on in the barn. Glancing down at our melted dessert leftovers, I lit up my horn as I lifted Applejack off the ground. Giggling away as I ran off with a floating Applejack in tow, I made a beeline for my boutique where I knew none of them would follow us. Swinging the door open, I ran inside and closed it behind me.

I walked into my room and placed Applejack on my bed, the dazed mare’s eyes landing on me before glancing at the scenery around her.

“Wha-”

“Your family heard you crying out, so I brought us here,” I explained. “If anything, we can come up with a good enough story in the morning.”

“Yes, please,” Applejack insisted. “Ah just wanna sleep for several days...not without spooning you of course.”

“Oh Celestia, I can’t believe this happened over a conversation about spooning!” I laughed. “But darling, if I’m being quite frank, I wouldn’t trade this night for all the magic in Equestria.”

“And ah wouldn’t trade it for all the apples in Equestria,” Applejack giggled. “C’mere you.”

I jumped into the bed, turning over as Applejack rested her foreleg over me and pressed her muzzle into my mane, smelling whatever perfume remained on me. I could only imagine the reactions on each of our dearest friends’ faces, in addition to the faces of our families. But that could wait till another day, but tonight I was held by my unexpected hero…

...and in her embrace, I felt all my sorrow and pain drowned out by a feeling within my heart that blossomed throughout my body. And with that, I knew I was done running.

I had finally found her.