Pony Shipping Headcannons

by Obsidian Shadow

Rating: mature
Tags: Slice of Life, Romance
Length: 3385

Headcannon shippings of ponies

A series of every possible shipping of the mane six plus Filly Twi x Tia because OTP.
I'm doing this because I need to get my shipping ideas out of my head. Haters gonna hate.

Published 1970-01-01 00:00:00 UTC
Last updated 2012-09-08 19:33:15 UTC

Fluttershy x Rarity

    Rarity was busily working on a huge dress order for Sapphire Shores. She couldn’t believe her luck at being commissioned for such a big order by such a widely known pony. It was the beginning of summer and the new swimwear line just HAD to be in on time and absolutely perfect. Fabric, pins, mannequins and various other colorful items littered the floor of Carousel Boutique as the white Unicorn worked her magic. She had just started in on a new swimsuit when she heard a faint knock at the door of her shop.

“Come in! It’s unlocked, I’ll be with you in just a moment!” The door slowly opens to reveal a shy yellow pegasus.

“Um... Hi Rarity...”

“Oh hello Fluttershy! Please, do come in!” Rarity hastily shoves her work out of the way as her friend enters the room. “Is there anything I can help you with dear?”

“I... I was just wondering...” she stares at the floor. “It’s very lonely at my cottage so you see... um... what I’m trying to say is... uh... do you need any help Rarity? I understand if you don’t... why would you? ohhhh... I’ll just go now...” Fluttershy turns to leave, tears welling in her eyes. Why can’t I just tell her how I feel?

“Don’t be silly Fluttershy! I would love your help! In fact, I’ve been looking for a Pegasus to try on one of my new swimsuits. Would you mind?”

“Oh, not at all Rarity!” Fluttershy turns around, a smile of relief on her face. “What should I do?”

“Hmmm... Stand here please?” Rarity gestures to the center of the room. “Good. Now, here we are...” Rarity levitates a dark blue one-piece swimsuit over to her friend. She uses her magic to gently lift Fluttershy and help her into the suit. “How does that feel dear?”

“Oh my... um... it’s a bit tight...” The stretchy blue swimsuit tightly hugs Fluttershy’s belly, chest, and back. It immediately rides up on her crotch, squeezing against her marehood and emphasizing her firm, round plot. Fluttershy blushes as she feels the swimsuit rub against her cute little pussy.

“You look simply amazing dear...” Rarity bites her lip. Am I being too forward? Can she tell it’s three sizes too small? Rarity tenses as she feels herself getting aroused at the sight of Fluttershy in the skintight suit. I must at least see what she thinks before I continue... “I’d like you to do a bit of modeling for me Fluttershy. Is that alright? It will be between you and me only.” She looks at her friend, hoping that she will understand.

“Um... okay Rarity... just if it’s between us...”

“Of course dear. I know how you feel about modeling. Let’s go upstairs.” Rarity turns and trots down the hall.

“Upstairs?” Fluttershy bites her lip.

“Of course dear! You don’t mind taking some... ah... action shots... do you?”

“um... no...” I wonder what Rarity means about “action shots”?

“Here we are darling!” Rarity stops outside her bathroom. “After you!” Fluttershy enters the luxurious bathroom, still looking confused. “Would you mind getting in the shower Fluttershy? I’m sure it would really help with the suit’s... full effect.”

“Well... I guess... um... oh my...” Fluttershy slowly walks inside the shower. Rarity locks the bathroom door behind her and turns the water on.

“Eep! Cold!” The freezing water surprises Fluttershy and she darts out of the shower and hides behind Rarity.

“Oh I’m so sorry dear! Here, Let’s let it warm up a bit.” She turns a few more knobs. Moments pass and clouds of steam start to rise to the ceiling. “I think it’s ready now darling.”

“um... okay...” Fluttershy gingerly puts out a hoof to test the water. The warm water flows over her hoof and she shivers, enjoying the feeling of the water rushing over her. “That’s nice...” She slowly enters the shower, letting the water cover her body, soaking her mane and tail and making her tight swimsuit shine. She closes her eyes as the water falls down her face, sending a warm, calming sensation through her whole body. This swimsuit does make showering fun... I just love the way it feels... It’s so tight, but I really it...

“Fluttershy... you look absolutely divine!” Rarity shifts her back hooves around, trying to cover up the arousal starting to run down her leg. “Do you mind if I join you?” Rarity looks hopefully at her friend.

“Oh of course Rarity! This water feels soooooo good!” Rarity gets in the shower next to Fluttershy and the two enjoy the hot, steamy water cascading over them. Rarity moans slightly as she feels trickles of water run down her marehood. She stares at Fluttershy, admiring how the tight, shiny swimsuit hugs the Pegasus so perfectly, how it exposes her voluptuous plot, and how it holds her tail up in such a sexy manner.

“Fluttershy?”

“Yes Rarity?” Fluttershy opens her eyes and blushes as she takes in her friend’s beauty. The water shining in Rarity’s mane and tail and the relaxed, happy look on ther face stir something inside Fluttershy.

“Why did you actually come here? You would usually never help me like this...”

“Oh! um...” Fluttershy blushes. “I... I just... you’re my best friend and... I have felt this way for a long time... I... I...” She whispers something inaudible over the rush of the shower.

“What’s that darling?” She COULDN’T mean... could she?

“I... um...”

“Please Fluttershy... you can tell me anything.”

“Iwantyoutobemymarefriend!” Fluttershy hides her head in shame. “I understand if you hate me now... I’m sorry...”

“You... Fluttershy? Really? You feel that way about me? I... I don’t know what to say...”

“Oh no... I... I...” Fluttershy starts to cry. Good job Fluttershy. You just ruined everything! Now she hates you!

“Don’t cry Fluttershy! I didn’t mean...” In a moment of blind frustration, Rarity moves closer to Fluttershy and kisses her on the lips. Surprised, the Pegasus stops crying.

“Rarity? Oh my... I never knew...” She returns the kiss, slowly savoring the feel of Rarity’s soft, firm lips on her own.

“Feel better now dear?” Fluttershy nods. “Good. Me too...”

“Can we kiss again Rarity?” Instead of answering, Rarity smiles and plants another long kiss on Fluttershy’s lips. She runs her tongue along them and they slowly part, allowing her tongue to enter. The two ponies share several more minutes of kissing, running their tongues lovingly across each other’s lips and exploring every contour of each other’s mouth. Rarity slowly breaks the kiss, moving back to admire Fluttershy once more.

“That swimsuit... looks wonderful on you darling. Are you sure it’s not too tight?”

“No.” Fluttershy shakes her head. “I like it. The tightness is nice actually...” She glances behind her, enjoying the warm, silky pressure on her marehood.

“I can tell dear. You smell...”

“I what!? Oh...” Fluttershy blushes. “um... can you... um... help?” Rarity smiles wryly.

“Of course dear. Let me see...” Fluttershy turns around and lifts her tail, exposing her tight little pussy. The shiny swimsuit emphasizes the beauty of her love, tightly squeezing it close to her body. “You are so beautiful Fluttershy! Why don’t we move to the bedroom?”

“I’d like that...” Fluttershy waits as Rarity turns off the water and gets each of them a large, fluffy towel. “Can I keep the swimsuit on Rarity?”

“Of course Fluttershy! You can have it. I think it ‘suits’ you perfectly.” The two giggle at Rarity’s little pun. After drying off, the two go to Rarity’s bedroom.

“You lay on the bed Fluttershy. I’ll be right there...” Rarity rummages around in her wardrobe while her friend curls up on the large, four poster bed. “These should do...” Rarity walks over to the bed carrying two large dildos and a latex strapon harness.

“Oh my...” Fluttershy turns red with anticipation and embarrassment at the sight of the huge toys. “They’re so big Rarity...”

“I know dear.” Rarity gets on the bed. “Do you think you can handle it?” Fluttershy nods slowly. “Good.” Rarity slowly pushes one of the huge dildos up her eager marehood. She flips a switch at the base of the toy and it starts to vibrate. “Aahhh...” She moans slightly as she attaches the other dildo to the black latex panties and pulls them on. The tight latex harness accentuates Rarity’s large, voluptuous plot, keeping her dildo firmly planted all the way inside of her. “Ready dear?”

“Yes...” Fluttershy eyes her friend with anticipation as she position herself with her plot towards Rarity.

“Here we go...” Rarity moves the crotch of Fluttershy’s swimsuit to the side and slowly rubs the tip of the strapon on her marehood.

“ooohhhhh... please hurry up Rarity... I want you inside of me...” Without hesitation, the white Unicorn thrusts, driving the tip of the toy inside Fluttershy’s wet little pussy. She squeezes her eyes shut as the toy enters her love, savoring the pleasure now sliding deeper inside of her. Rarity moans as she pushes the dildo all the way inside Fluttershy’s tight little pussy. “Please Rarity... make me cum...”

“If you insist darling!” Rarity pulls the dildo out of Fluttershy and quickly thrusts it all the way back in.

“Aaahhh! Harder!” Fluttershy squeals as her friend begins fucking her, ramming the huge dildo repeatedly into her. She moans as Rarity continues to hilt the massive toy in her pussy, pleasure building inside of her. Rarity grunts as the toy completely filling her tight marehood vibrates, sending waves of tingling pleasure throughout her body. After several minutes of hot, moaning pleasure, Fluttershy cums, sending her warm juices all over Rarity, who grins as she continues ravaging her friend’s cute little pussy.

“OooOOoooOhhhhhh!” Fluttershy moans and screams as the pressure explodes in her pussy, making her mind go blank with pleasure. Rarity cums as well, grunting and collapsing next to Fluttershy as waves of complete bliss envelop both of them. Fluttershy wraps her hooves around her friend, hugging her tightly. “I love you Rarity...”

“I love you too Fluttershy...” Rarity returns the hug, running her hooves over the tight, silky swimsuit still enveloping Fluttershy. The two ponies fall asleep in each other’s tight embrace, Rarity’s strapon still buried deeply in Fluttershy’s pussy as her own dildo cuts off, still filling her marehood completely.

Filly Twilight x Celestia

It is a seemingly regular evening at Canterlot Castle. Twilight Sparkle and Princess Celestia have just retired to their room after a hard day of magic lessons. Twilight jumps onto their large bed and snuggles against the fluffy red pillows, tired after a long lesson on magical theory. Celestia joins her on the bed, looking worn-out and distracted. Concerned, the unicorn filly watches her teacher flop down on the bed.

“Are you okay Princess?”

“I’m fine Twilight. It’s just been a long day for me.”

“Why? Wasn’t it just normal? It didn’t seem very long...” Celestia smiles.

“That’s because you were enjoying yourself my little student. I just... have a lot on my mind...” It’s going to be hard to keep it from her... She is so curious! Maybe... No. I can’t expose her to that just yet. I have to restrain myself.

“Oh. Okay...” Twilight rests her head on the bed, looking slightly put out. “I just wanted to help...”

“I’m very sorry Twilight. I didn’t mean to upset you.” Celestia hugs Twilight, enveloping the little filly in her silky, shining mane.

“It’s okay Princess.”

“Good!” The sun goddess holds Twilight closer to her, feeling her tiny chest move up and down slowly with each breath. Just stop it now Celestia. Just go to sleep, you can deal with yourself in the morning. You can’t expose Twilight like this. She is too young! She only just got her cutie mark. But she’s just... I just... I don’t think I can help myself...

“I know something that might cheer both of us up Twilight! Do you remember the lesson I gave you on a mare's reproductive cycles?”

“Umm.... yeah I think so...” The filly smiles innocently.

“Good. Would you like to do some ah... first-hand research?” Celestia shifts her back legs restlessly.

“Huh? But I read those books a long time ago! Do I need to read them again?”

“No Twilight... I meant something more... hooves on...” Celestia rolls over onto her back. She moves her tail out of the way so that Twilight can see her slightly inflamed and wet marehood. What do you think you’re doing? She has no idea what this means...

“Are you alright princess?” The lavender filly looks at her, confused.

“Yes Twilight, I'm perfectly fine.” Celestia smiles a bit. “I just entered my estrus cycle this morning... Don't you want to learn more about it?” Celestia swishes her shining tail invitingly.

“I always like to learn new things Princess!” I guess there’s no going back now...

“I know you do my little student. Why don't you take a closer look?” Twilight moves closer to her teacher, staring curiously at Celestia’s perfect little pussy.

“Tell me what you see Twilight. Be as detailed as possible...” Celestia closes her eyes in anticipation. The thought of Twilight’s complete innocence arouses her even more.

“Umm.... well, this is your marehood and it looks like it’s wet... Is that supposed to happen?

“Yes Twilight... What does it feel like?” The unicorn foal carefully touches Celestia’s marehood.

“It feels slippery...” Twilight’s face scrunches up as she gingerly puts her hoof against Celestia’s shining flower.

“ooohh...” Celestia moans as Twilight's soft little hoof brushes against her pussy. That feels so good... She has to learn about this sometime... It’s better for me to show her rather than some random stallion…

“Did hurt you princess?” Twilight looks up, concern and worry all over her innocent little face. “I'm sorry..”

“No Twilight, that actually felt very good! Come up here and feel my horn...” Twilight notices for the first time the faint, golden glow surrounding the Alicorn’s pristine horn.

“Why is it glowing?” She touches Celestia’s horn, feeling an unusual warmth radiating from it. “You aren't casting any spell, are you?”

    “Don't you remember that part of the lesson? Unicorn and Alicorn horns get very sensitive during estrus...”

    “Oh yeah...” Twilight starts rubbing Celestia’s horn slowly. “It feels so nice! It’s like your magic is kissing me!” Celestia moans and rolls onto her side so that she is face to face with Twilight. She smiles widely, eyes half closed.

“Do you also remember the only to cure estrus my precious student?” Twilight’s face scrunches up as she tries to remember.

“Inter-horse?”

“Intercourse, Twilight.” Again, Celestia marvels at the perfect innocence of her little student.

“But I’m not a boy! Isn’t that only for a mare and a stallion?”

“Not necessarily my love. Would you like me to show you how?” Oh please please please say yes… I can’t bear this any longer…

“Um… I guess… It won’t hurt, right?”

“Not at all Twilight. I’ll be as gentle as possible.” As she speaks, Celestia picks the filly up and gently lays her on her own chest. Twilight lays on her back with her tiny marehood only centimeters from the Alicorn Goddess’s snout. Celestia’s golden magic envelops the Twilight’s legs and slowly pulls them apart.

“W- what’s the magic for Princess?”

“Please don’t worry my little Twilight. It’s just so you don’t fall… Do try to make yourself comfortable and remember, if you want me to stop at any time, just tell me.”

“Okay…” The Unicorn foal snuggles against Celestia’s soft white chest and looks up at her mentor with a smile. “I’m ready now!”

“Good…” Celestia admires Twilight’s delicate little flower, her tiny, flat nipples, her sweet, innocent face. Slowly, cautiously, she puts out her tongue. The Alicorn Goddess closes her eyes as she feels the tiny lips of her student’s pussy. She smiles inwardly as she tastes the faintest hint of the filly’s sweet arousal. Slowly at first, the motherly Alicorn traces circles around Twilight’s pussy with her long, pink tongue.

“Eep! P- Princess… please… please don’t stop…” Twilight bits her lip as tiny ripples of electric pleasure shoot up and down her whole body. She tries to scoot forward on Celestia’s chest to get her marehood closer to her beloved teacher’s wonderful, magical tongue. Celestia slowly wiggles her tongue in between Twilight’s cute lips and greedily laps up her now trickling arousal. After only a few more seconds, the small filly cums, convulses slightly, and falls limp across Celestia. Her mind goes completely blank as wave after wave of intense pleasure washes over her. She lies there, panting as the world slowly returns to her.

“How was that my Twilight?” Celestia grins and licks the foal’s first orgasm off of herself.

“It was… amazing!” Twilight grins. “Can we do it again?”

“Of course Twilight. Just let me get something for myself…” Celestia levitates a pair of golden latex panties over to herself. A huge dildo is attached to the inside.

“What’s that?” Twilight stares at the massive dildo, puzzled.

“Well, since mares don’t always want to have a stallion, they sometimes use these instead…” Celestia guides the fake stallionhood inside her own dripping pussy. She slowly pulls the tight latex panties up over her firm, voluptuous plot. She then sends a jolt of magic through the enormous toy, and it begins to vibrate deep inside of her.

“Wow! How does all of it fit?” A look of shock crosses the surprised filly’s face.

“It wasn’t that hard Twilight… uuhhhh… I’ll show you how someday...” Celestia moans as the vibrator panties send jolts of perfect ecstasy through her. She cums almost instantly and cries out as she collapses back on the bed. Pent up pleasure and ecstasy course relentlessly within her.

“Princess! What’s wrong?” Twilight rushes to her side.

“N- nothing Twilight. I am fine. It was just my orgasm. I’m sure you can understand…”

“Oooh.” Twilight smiles knowingly. “Can I do orgasm again?”

“Of course my little Twilight. This is all for you my love…” A shining ring of magic appears at the base of Celestia’s still glowing horn. Another appears around Twilight’s still dripping pussy.

“What spell is that Princess?” Twilight curiously prods at the glowing golden ring around her tiny marehood.

“It’s a suspended teleport spell. Now, when you come rub my horn, you’ll feel it moving in your pussy!”

“Won’t it poke me though?” Twilight eyes the pointed tip of Celestia’s horn with apprehension.

“Not at all Twilight. The spell makes it dull enough to be safe for you.”

“Oh! Okay!” Twilight approaches the pure white Alicorn and eagerly puts both of her hooves on her horn. As she starts rubbing, she moans as she feels something invisible slide inside of her. All of a sudden, she stops and winces, as pleasure turns to pain.

“Everything alright my love?” Celestia looks at her student, concerned.

“I- I think so…” The pain recedes as quickly as it had appeared. “I’m fine now…”

“Good.” Celestia smiles. “Please continue Twilight.”

“Yes Princess…” The little foal starts rubbing her mentor’s horn once more and both mares gasp as the electric pleasure returns to them. Twilight pumps her hooves faster and squeaks adorably each time Celestia’s horn is magically thrust deep inside of her. Celestia pulls Twilight closer, savoring her tiny moans as well as the huge vibrating stallionhood completely filling and stretching her pussy. She reaches a hoof down and rubs her clit through the tight latex panties enveloping her perfectly round and firm plot. The tingling sensation in her horn increases as Twilight magically fucks it. After several more minutes of heated passion, both ponies cum at the same time. Celestia’s spell dissipates as her mind is blasted out of reality by rockets of pleasure. Twilight collapses next to Celestia with a content little smile on her face. Slowly, Celesta cradles her little student and snuggles up to her.

“Did you enjoy that dear?”

“Yes… Can we do it again sometime?”

“Of course… I love you Twilight.”

“I love you too Princess. I always did…” The little filly snuggles closer to Celestia. The Alicorn smiles as she feels sleep descend on her. And I always will Twilight. Forever and always, as long as I live, I will love you.