Best in Show

by PuzzlingInsanity

Rating: mature
Tags: Self Insert, Sex, Original Character, Porn, My Little Pony: Friendship is Magic, Fetish
Length: 3138

Star Study enters Puzzling Insanity into a strange pageant.

Star Study and his kitten, Puzzling Insanity, are looking to move, but don't have the money. One day during a walk, they see a flyer for a strange pony pageant. The prize is 10,000 bits!

Published 2020-08-20 23:20:01 UTC
Last updated 2020-08-20 23:20:01 UTC

Best in Show

I sit on the rough sapphire blue carpet at my Master’s hooves, licking my orchid-gray fur. The silver bell on my black and red frilly collar jingles with each movement I make. My raven black mane gets in the right side of my face like an asymmetrical curtain. I push it out of the way and blink my olive yellow eyes, looking up at Master.

Star Study, my Master, is a unicorn stallion with a slate gray coat and big turquoise eyes. He brushes a wayward lock of silver-gray and jet black out of his face with his hoof as his magic pulls my mane back.

“Master, why haven’t we moved yet?” I ask curiously as Master levitates a brush over and gently runs it through my mane.

“Because, kitten,” he sighs, “even with my job we can’t afford to.” His frustration makes me feel afraid. My lower lip quivers and my eyes fill with tears. Noticing my distress, he immediately picks me up in his magic and plops me on the black leather couch with him, throwing his hooves around me and stroking my back. His gentle shushing fills my ears as I sniffle, wiping my eyes with a hoof. “I’m sorry I scared you, kitten,” he apologizes, his strokes relaxing me and making me purr quietly. “Would you like to go for walkies?”

I nod, a small smile playing at my muzzle as he takes a length of chain with a black leather strap for a handle and hooks it to the D-ring on my collar. Master notes that the weather outside is nice as we head out.

The weather is indeed nice. The air is warm, the sky is a beautiful light blue and the sun’s rays feel nice on my coat. My tail swishes happily as Master leads me down the sidewalk. Suddenly, we stop.

“Look, kitten,” he orders, levitating a flyer over to me. I read it aloud.

“‘Sunday at noon, pony pageant. First prize is 10,000 bits and a photo shoot.’ That’s tomorrow, Master.”

“And the prize is 10,000 bits,” he reiterates. “How would you like to show off for Master?”

Anxiety hits me like a freight train. “Um… may I give you an answer in the morning, Master? I don’t want to be too impulsive.”

“I’ll allow it, kitten,” Master answers, stroking my mane. I purr happily as we head back around the corner and back home.

Once inside, Master unhooks my leash, then levitates a pink mouse squeaker toy and floats it back and forth. My eyes follow it like a hypnotist’s watch. He drops it at my hooves, and I bat at it playfully. My collar jingles and the toy squeaks as I happily play with my favorite pet toy. After what seems like hours, Master puts away the toy and leads me to the bathroom. Unlike most kittens, I like bathtime. Bathtime means Master and I get to spend quality time together.

Master removes my collar and sits me in the claw-footed porcelain tub, floating my favorite treat over in my special dish. In the black ceramic pet bowl is a serving of fish-shaped cheese crackers. “If you stay still like a good girl, you can have some fishy crackers.”

I stay perfectly still, even as Master takes a bottle of rose-scented shampoo and rubs the red soap into my fur and mane. His touch feels nice and relaxes me. I purr at the feeling and the pleasant smell, Master feeding me fishy crackers with his magic. The treats crunch under my teeth, spreading the taste of baked cheddar across my pierced tongue.

I let out a large burp, my cheeks turning crimson in embarrassment. “Excuse me, Master,” I say sheepishly, attempting to wrap my tail around myself.

“You’re excused, kitten,” Master reassures, booping my nose with his hoof. He lifts me out of the tub and drains the soapy water, refilling it with clean lukewarm water. When he lowers me back into the tub, he floats a plastic cup over and gently rinses all the shampoo out of my coat and mane. “You’re such a good little kitten, staying still for Master.” My chest fills with pride as he drains the water out of the bathtub and goes to get me a towel. I hold still as he dries me off with a white fluffy towel. My mane and coat floof up, making him laugh as he lifts me out of the tub and places me on the baby blue bath mat. I look like a Persian cat, an appropriate comparison given my choice of role. “Now, let’s brush your mane and teeth, okay?” I nod as Master levitates a red plastic manebrush over and gently begins to run it through my mane and tail with slow strokes. My eyes flutter closed and I purr rather loudly. He brushes my mane and tail until they’re smooth and shiny. I sniff the black curtain in front of my face and note that it smells like roses.

He puts away the manebrush and floats a purple toothbrush and bubblegum-flavored toothpaste over to me. I open my mouth, and he starts to brush the tops of my teeth. He gently scrubs the backs, even getting the hard-to-reach places. “Bite down,” he orders, taking the toothbrush out of my mouth. I obey, baring my fangs for him to brush. Master brushes them in little circles, then up and down. He scrubs until a little foam starts to form in my mouth. “Spit.” I turn to the sink and spit out the toothpaste as he washes the toothbrush. He scratches behind my ear, making my tail sway happily.

“Master, I’ve thought about it,” I say softly. “I want to enter.”

“Then let’s get ready for bed, kitten,” he replies, a big smile on his face. “Master’s so proud of you.” He leads me into the bedroom and gently pats the red cushion in the giant pet bed. I circle it a few times, then lie down on the cushion as he takes a soft black blanket and covers me with it. He kisses my forehead and whispers, “Sweet dreams, kitten.” I smile as my eyelids grow heavy. It doesn’t take long before I fall asleep. It doesn’t seem like eight hours has gone by when Master wakes me up and hooks up my leash. “We’re going to get you a new outfit,” he explains, opening the door and sniffing the morning air.

“For the pageant, Master?” I ask curiously.

“You got it, kitten,” he answers cheerfully.

Master leads me through Ponyville to Carousel Boutique. An alabaster unicorn with a curly royal purple mane and big azure eyes greets us.

“Ah, welcome to Carousel Boutique, where every piece is chic, unique and magnifique,” Rarity chirps. “May I help you find anything?”

“Actually, I was hoping you could get my kitten here into a new outfit,” Master answers.

“Of course, darling,” Rarity coos, leading us into her workroom. “I’ll just need her measurements and preferences.”

“Preferably something black and red, if it’s okay,” I pipe up. “Something to match my collar, you know?”

“Certainly, dear,” the unicorn mare replies, carefully taking my measurements. “I take it you’re entering today’s pageant?” I nod. “Well, darling, one secret to the fashion portion of any pageant is to keep your tail held as high as your head. Does your friend here have a plug for you?” I nod again, my cheeks reddening. “No need to be embarrassed, dear. Every mare in the business has to wear one at some time or another.” After what seems like hours pass, Rarity presents Master with a garment bag and hanger. “You’d better get going if you want to win the pageant.”

“But what about paying?”

“Free of charge, darling,” Rarity calls out, sorting her garments by color.

“Thank you,” I call back as Master leads me outside and over to the local convention center. I feel a little nervous about competing, but excitement dwarfs it.

A pink alicorn mare with tri-color hair of pink, purple and yellow bats her purple eyes at us as we enter. “Name?”

“Puzzling Insanity, pet of Star Study.”

“Pleasure to meet you,” the alicorn chirps. “I’m Princess Cadance. You are aware of the nature of this competition, aren’t you?”

“Um… no?”

“This is a pony pet show,” Cadance explains. “Judges will be poking and prodding you first, then you’ll be participating in a sex toy obstacle course, then you’ll show off your best kinky outfit and finally, the sexual talent showcase.” I smile nervously. “Don’t worry, everypony’s first time is a bit scary. All you have to do is do your best.” She pets the fuzz on the left side of my head, making me purr. “Just make your way back into the waiting area. You’re number 75.”

I take my number and follow Master into an area populated by other pony pets and their owners. Time passes slowly, pets are called out. Some are disqualified for disagreeable behavior. Then my number is called over a loudspeaker. I take a deep breath and head out into the judging area, led by Master.

A blue unicorn mare with a blue and white mane and deep blue eyes unhooks my leash and lifts my head with a gentle hoof. She delicately opens my mouth with her magic and takes a small sniff of my breath. “Breath smells fresh,” she comments, taking notes on a clipboard. “Teeth are a very pale yellow; gums are healthy and pink.” She takes a rainbow-striped dildo and slides it in my mouth, band after band of color disappearing until I lurch forward gagging. At that point, she withdraws the toy and allows me to breathe. “Good gag reflex control. Alright, step over here and present yourself for the other judges.”

I obey, stopping on the designated spot and assuming the traditional mating position. I hear a stallion’s voice as I suppress a whimper of pleasure. “Genital area is clean and well-kept,” the stallion notes. I feel my marehood being spread open with magic. “Vaginal muscles are well-toned and a nice shade of pink. Cervix looks smooth and round.” I gasp quietly as a toy is slowly pushed inside. “Vagina is very tight and sensitive.” The toy is withdrawn, and I’m opened up again. “Underdeveloped labia minora,” he comments, spreading me further. I shudder as my clitoris is stimulated with the tingling aura of his unicorn magic. “Clitoris is very small, yet hypersensitive to stimuli.” When I notice how thoroughly the stallion is inspecting me, I bite my lip. “Small scar on the mons pubis.”

I hear the stallion scribbling away on his clipboard as another unicorn mare gently prods at my anus with magic. “Hmm,” she muses, sniffing. “Anus is clean and free of filth.” I clench my teeth as my ponut is stretched with what feels like a lubricated magic tendril. “Anal canal is very tight,” she notes, gently prodding with a small dildo. “Strong anal sphincter. Very nice.”

“Go and get ready for the obstacle course,” Cadance tells me, giving back my leash. Master walks me back to the waiting area. We do stretches until my number is called again.

I hit the ground running, reaching a row of large pink dildos. I have to get on my hindlegs and squat on each dildo. It feels so good. I have to focus on finishing the course, though, so I push out the last dildo and crawl my way through a field of small egg vibrators. They tickle my body, making me laugh.

Focus on the course, my brain screams at me. The last obstacle is a baby blue plastic filly pool filled with lube. I take a running start and jump over the pool, finishing the course in a minute and twenty seconds. As I prance back to the waiting area, I notice ponies writing on clipboards.

“Master’s very proud of you, Kitten,” Master says cheerfully, kissing my cheek. “Let’s get you in your outfit. Close your eyes.” He takes his time as the other pets are dressed for the fashion portion of the show. After some time, he announces, “You can open your eyes now.” I do so and gasp at the sight of my reflection. My black eyeshadow is smoked out, and my lips are painted black. I’m wearing a black dress with a red corset, and my hooves are in black booties with red laces. “One more thing,” he comments, floating my favorite toy over: a large black silicone butt plug with a red heart-shaped jewel in the base. “Tail up.” I lift my tail and suppress a moan as the plug slowly sinks into my ass. “Good girl.”

“Number 75, please report to the catwalk,” the voice of the loudspeaker rings out. I make my way out to the catwalk and walk down the T-shaped stage like a Canterlot model.

“And here’s Puzzling Insanity with a gothed-out look! Don’t those frills look adorable?” I pull off my cutest face, eliciting a collective “aww” from the crowd and the judges. Slowly I turn around, my tail waving like a flag. “And look at that plug! You’d think she’s a Canterlot model!” I turn slowly in a circle, showing off my cutie marks. My pussy drips in excitement as I head back to the waiting area. Master undresses me and pulls out my plug, and we relax until I’m called out for the talent show. He leads me out and allows his massive cock to come out of his sheath.

“Okay, Master,” I sigh. “I’m ready.” I relax as Master spreads my rear end and slowly enters my asshole. I mewl quietly as he fucks my ass. I feel so full. It feels amazing. I love having my ass filled. His cock hits my G-spot through my rear tunnel, making me drip all over the stage. I grunt as my pussy gushes with orgasm after orgasm, leaving a puddle of juices. Mascara and eyeliner run down my cheeks as he pulls out and mops the stage with my face. He grabs my mane with his magic and fucks my face with his cock. I’m going insane with pleasure. I gag and moan and slurp lewdly, my throat muscles kneading the intruder. The taste of my ass juice makes me cum again, my lower holes spasming in tandem. My mind shatters like glass and I collapse on the stage. Master picks me up in his magic and fucks my ass some more, pounding away as I orgasm again and again.

“Oh, my sweet, sweet kitten,” he calls out. “My SWEET! SWEET! KITTEN!” With that, he cums violently, flooding my bowels with his seed. The feeling of being filled makes my pussy squirt again. I see blurry figures, my glasses safely in the waiting area, and my perception magic tells me that the crowd is enjoying the show. I hear the crowd cheering and moaning as Master carries me back to the waiting area. “Gooood girl,” he sighs. I purr as oxytocin and dopamine flood my system, my eyes glazing over from the overstimulation of my sex-drugged brain. When he lays me down on the floor at his hooves, I curl up and purr even louder.

Two new faces surprise everypony in the waiting area. Princess Celestia and Princess Luna, the Royal Sisters, clap their hooves happily and congratulate everypony individually. When they get to me, Master stands me up and helps me genuflect before I flop on my back and show my soft pudgy belly.

“Oh, look how adorable, Sister! Does she not remind you of our foalhood cat?”

“That’s the point of pet play, Luna,” Celestia chuckles, turning to Master. “May I?”

“Of course, Your Majesty.”

Celestia gently removes her shoe and rubs my belly with her bare hoof. I purr and begin making air biscuits with my hooves.

“Who’s a good little kitty?” the Solar Princess coos, rubbing my tummy in little circles. “Such soft fur you have!” I revel in the attention, my behavior becoming progressively more feline. “You’ve taken such good care of her, my little pony.”

“Thank you, Princess,” Master answers, bowing.

“May we have a turn with the pony pet, Sister?”

“Of course,” Celestia responds, backing away and putting her shoe back on her hoof. She turns back to Master. “Did you by chance bring a cat toy with you?” Master floats my squeaky mouse out of his saddlebag. “Careful, Luna, I noticed she has fangs.” I meow quietly, reaching for the squeaker toy.

“Wouldst thou like to play, kitten?” Luna asks me, grabbing the toy with her magic. I reach up again. She drops the mouse, prompting me to bunny kick with my back hooves. “Watch thyself,” the Lunar Princess warns. “Thou almost struck us.” I yowl happily and grasp at Princess Luna’s hoof. “Oh, how cute!”

Master gently pulls her hoof out of my grasp. “No, kitten,” he scolds, “no grabbing.” My ears droop and my lip quivers.

“I’m sorry, Master,” I whimper. “I’m sorry, Princesses.”

“Oh, dear kitten,” Luna coos comfortingly. “Thy apology is accepted.” She strokes the fuzz on my head and scratches behind my left ear. My eyes flutter shut and I purr quietly. “Thou art a good feline,” she says softly.

“Luna, I hate to interrupt, but they’re about to announce the winner,” Celestia warns. “We’d better get going.”

“Fare thee well, kitten,” Luna says. “We wish thee the best.” As the princesses leave, Master brushes my mane.

“Would the following pets please meet with the judges: Number 1, Number 42 and Number 75. Thank you.”

Suddenly, I find myself on the judging floor, along with a pale yellow pegasus mare with a pale pink mane and teal eyes, led by a draconequus, and a pink earth pony mare with a hot pink mane and crystal blue eyes, led by a gray earth pony mare with a purple mane and pale turquoise eyes.

“The three of you are strong candidates for Best in Show,” the blue judge says soberly. “However, there can be only one. We’ve had the crowd vote for their pick.” I bite my lip anxiously. “The winner of 10,000 bits and Best in Show is…” The anticipation is killing me. “NUMBER 75: PUZZLING INSANITY!”

I burst into tears as the crowd bursts out into applause. I can’t believe I’ve just won. The other two pets hug me and congratulate me, much to my surprise. Master accepts the bag of bits for me and kisses my forehead.

Some time passes, and Master and I are cuddling on the new couch in our new place, purchased using my winnings.

“Such a good girl,” Master coos quietly. He strokes my back with his hooves, making me purr. I feel safe. I feel loved.