Pony Shipping Headcannons

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.