Ponyville After School

(Vectors by CyanLightning & ikillyou121)

~ ✭ ~

For the fifth time in a row, Flitter checked herself in the mirror, making sure her makeup was okay. It was, though she adjusted the pink bow in her mane anyway. She fiddled with her long cyan hair too, brushing them yet again.

Her sister peeked from the bathroom's door. "Huh… Still here, sis?" Cloudchaser asked, bemused. "Give it up: you look perfect already."

Flitter sighed. "I know, I know… I'm just kinda nervous." Finally letting go, she followed Cloudchaser to the front door of their house.

"Relax, Flitter… You're gonna take care of him like a champ," Cloudchaser said as she packed her saddlebags, preparing herself to leave. "That colt sure is lucky to spend a night with you. Speaking of, did Cheerilee tell you who it's gonna be?"

"Yeah, it's Perky Prep."

"Oh, isn't that the earth pony colt who's part of the cheerleading squad? The cute blue one with a bullhorn cutie mark?"

"Yep, that's him," Flitter confirmed.

"Well, I'm sure you two are gonna have a great time together." Cloudchaser hugged her little sister, then saddled her bags. "And, you know, maybe he'll like anal almost as much as you do." She winked.

Flitter rolled her eyes. "Seriously, CC? He's just a colt."

Cloudchaser giggled. "Kidding, kidding! That would be nice, though. Anyway, I gotta fly before I'm late for the meeting with the 'Bolts. Spitfire gonna tear my head off. House is yours for the weekend, sis. Don't burn it down."

With a sigh, Flitter waved her sister goodbye, then went back to her preps. She glanced at the clock on the wall: it was almost time to go pick up her colt.

She needed to do just one last thing before going. Flitter retrieved the vial of birth-control Cheerilee had given her, and swallowed its content. Now adequately protected from any impromptu pregnancy, she made her way outside, leaving the door unlocked. Spreading her wings, Flitter took off, flying in direction of the school.

~ ✭ ~

Perky Prep couldn’t believe his good fortune. The week had been incredible for him. First, the school's cheerleading squad had brilliantly cheered for the Ponyville buckball team at the national league championship, which had earned him and his pal Peach Fuzz a lot of pins. Second, he had done great on both the math test and the reading assignment. Finally, to top it all off, he was going to spend the night with one of the prettiest pegasus mares in town.

The young colt eagerly followed Flitter to her home, trotting cheerfully at her side. Perky Prep kept glancing at her the whole way through; she was just so beautiful, with her long, silky mane and firm rump. Her accent was oddly slurred, but even that was kinda cute.

His cock slipped out of its sheath before they even arrived at her place.

Figuring Perky needed to blow off some steam first, Flitter led the excited colt to her bedroom and lifted her tail for him. He had done this a couple times back when it used to just be with Cheerilee, and he knew the basics. Flitter laid still as the colt entered her vulva and pushed into her, and she let him take his pleasure in her. The sex that followed wasn't exactly satisfying for her, but it wasn’t too bad either. It was soon over anyway, and Flitter felt the creamy warmth of colt semen spill in her womb.

"Feeling better?" Flitter asked, amused by her young partner's blissful expression as he pulled his flaccid penis from her marehood.

"Unf… yeah!" Perky Prep replied, panting. "Thanks, Miss Flitter! You're the best!"

"Haha! I guess you are good at cheering." Smiling, Flitter casually grabbed a couple tissues from her nightstand and wiped the gooey cum leaking from her vulva.

The young colt blushed, embarrassed. "Um, sorry it was so fast. It probably wasn't very fun for you…"

"Meh, that's okay," Flitter responded with a dismissive gesture of her hoof. "We'll do the fun stuff tonight. Until then, how about we go out in town for a while?"

Perky Prep grinned. "Sure!"

~ ✭ ~

Flitter bought a large sundae at the ice cream parlor, and ate it together with Perky. Then, they went to the park, where the Pony Tones were putting up a free afternoon show.

Sitting with Flitter on a nearby bench, the colt held her hoof for the entire duration of the show, staring more at her than at the ponies on stage. The whole situation kinda felt like a date, and it made him blush.

As the Pony Tones finished their performance and the audience dispersed, Flitter noticed Perky Prep's gaze on her. Smiling, she lowered her head and kissed him right on the lips. In heaven, the colt tenderly made out with the pegasus. Flitter delicately pulled back, leaving him in a daze. Judging from his awed expression, she'd given him his first kiss, and it thrilled her. She playfully ruffled his mane.

They grabbed an order of daffodils-daisy sandwiches with hay fries from a nearby stand, which they ate together on a picnic table. Finally, with their stomachs full, Flitter and Perky Prep went back to her place.

Returning to her bedroom, Flitter settled down on the bed, inviting the young colt to join her. Strangely, Perky Prep suddenly seemed really nervous for some reason, considering that he had already mated with her. "Something's wrong?" Flitter asked.

The colt bit his lip. "Erm, no… It's just, I heard… Well, Rumble told me he heard his big brother say you liked… um… 'butt-stuff'."

Flitter facehoofed, turning crimson. "Really? Is Thunderlane saying that to everypony now? I should just go buck his dumb flanks right now. That'll teach him."

"Uh, sorry…? That's not true?"

The pegasus sighed. "Dumbass Thunderlane shouldn't tell ponies stuff like that, but… yeah, it's true. I like anal a lot: you know, doing stuff with tailholes. I'm sure that must sound strange to you, but it can be a lot of fun."

"No, I think it sounds neat!" Perky Prep said.

Flitter stared wide eyed at him. "Huh? Really?"

"Uh-uh! Rumble said it was gross, but I think he's wrong. Fillies' butts are so cute, and if they're clean, it can't be too bad, right?" He waited for Flitter to respond, but the mare just blinked a few times, so he continued. "I was really excited when I saw you were volunteering, because I thought I could try stuff with you, and it wouldn't be weird if you liked that kind of thing too. So, uh… is that okay?"

Slowly, Flitter's shocked expression turned into a grin. "Are you kidding me? You bet your cute rump it's okay! C'mon, Perky!" She planted a quick kiss on his lips. In one graceful motion, Flitter hopped off the bed, then trotted out the room, the little colt on her tail. "You're in the right place if you want to learn about all the fun things you can do with your ass!"

Perky Prep followed Flitter through her house, having to run to keep up with her strides. "Um… Where are we going?"

Flitter laughed. "We're gonna take a shower, dude. You're not touching my tailhole before that, and I'm not touching yours either." She invited him into the bathroom, then turned on the shower's faucets.

Perky had figured taking a shower with a gorgeous mare would be really hot, but, to be honest, Flitter simply washed herself with absolute efficiency. Still, she was pretty cute with her wet mane, and it was kinda fun when she rigorously scrubbed his butt. The whole thing was over in less than two minutes. Fortunately, the colt didn’t have long to be disappointed, because Flitter immediately brought him back to her bedroom for the third time that day.

A towel still wrapped around her mane, Flitter embraced Perky Prep and kissed him. Gently, she pushed him on his back on the bed, letting his rump hang off the edge of the mattress. They made out tenderly, Flitter mounting him belly to belly. She smiled as she felt his erection, the foal's colthood pressing on her soft tummy, leaving some precum in her purple fur.

Breaking the kiss, Flitter slid down the colt's body, dismounting the bed. As she did, she took a moment to admire his sex, even tasting his swollen glans before moving on. The mare kissed Perky's cute little ballsack, then arrived at her prize: his adorable little asshole.

She didn't even know why herself, but Flitter truly loved anal sex. Of course, she liked when stallions penetrated her vaginally too, and she liked masturbation, but there was something that was just so naughty about playing with somepony's tailhole that really got her going. Flitter licked her lips; if this little colt wanted to discover the pleasures that could come from ponies' anus, she'd gladly teach him everything she knew.

Flitter started slow, of course, careful to not overwhelm him. She nuzzled around the rim of Perky Prep's anus — blue, like the rest of him. He twitched from the simple contact, his sphincter contracting rhythmically. His ass was obviously very sensitive: perfect. She transitioned to little kisses, planting her soft lips all around his butt, and kissed his testicles too.

"Mmmh! Miss Flitter…"

Enjoying Perky's little moans, Flitter planted a big smooch right on his anus, which elicited an even bigger reaction. The colt's ballsack throbbed, his hindlegs trembling. The pegasus wrapped a foreleg around his thighs, holding him in place while she dipped her other hoof in her vulva. As she masturbated, Flitter opened her mouth wide and let her tongue loll out. She licked the colt's ass, a big, sloppy lick directly on his excited tailhole.

Apparently, Perky Prep hadn't expected Flitter to be so brazen. "Woah! You… You're… Oooh!"

Grinning, Flitter went even further, pressing the tip of her tongue on his tight pucker. Wiggling it around a bit, the mare loosened his anus, and slipped her tongue inside. Caressing her clit, her snout deep in his balls, the pegasus explored Perky's rectum, reaching far into him.

"Aaaah! Gosh! F-Flitter!"

She tasted his ass, but she honestly didn't mind it. Not when her partner squirmed in delight like this from her work. Flitter caressed his prostate through the thin membrane of his bowel. Perky Prep clenched his butt, his anus contracting around her tongue, and his testicles throbbed in their sack; he was about to ejaculate.

Making a split second decision, Flitter pulled out of the colt's rectum, and leapt on him. She quickly lined his flaring, twitching cock to her vulva, and lowered herself on him, taking him in her vagina just in time to receive his seed. Rather than squirt in bursts, Perky's sperm flowed in her uterus like a warm, creamy stream, thanks to the prostate stimulation she'd given him, and Flitter loved it.

Riding Perky cowpony-style, Flitter masturbated with both her forehooves, exposing the swollen nub of her clitoris and rubbing herself silly. Aided by the pulsing colthood in her snatch, Flitter came as well. She gasped hard, wetting Perky's crotch with her fluids and a bit of her pee. "Aaaahhh~" Her wings flaring, Flitter let her head hang back, savoring her orgasm.

Perky Prep tenderly caressed Flitter's slender belly, where he was leaving his fertile sperm, eliciting a gentle smile from her. She looked down, sharing a complicit grin with the cute colt underneath her. She wanted to kiss him, though that wouldn't be very polite after having her tongue in his ass.

When she was sure she had taken his entire ejaculation, Flitter dismounted the lucky colt. His soft penis, coated in her vaginal fluids and his own seed, rested on his tummy, spent for now. "That was… amazing, Miss Flitter," Perky Prep said, drowsy from his climax. "I can't believe you did that with your tongue… but it was great."

"Hehe! You're welcome!" Figuring the spent colt might need a bit of time to recover, she added, "Stay here. I'll swing by the bathroom, then I'll be right back." He nodded sleepily.

~ ✭ ~

Lounging alone in Flitter's comfortable bed, Perky Prep was in bliss, enjoying the best afterglow of his life. What the mare had done to him — licking inside him — had been utterly mind blowing. His asshole was still delightfully sensitive.

Perky lost track of everything for a moment, his mind hazy. It probably wasn't for long, though, because he was still hearing Flitter in the adjacent bathroom as he came to his senses, the mare apparently brushing her teeth and cleaning her mouth.

Waiting for Flitter to return, Perky took the opportunity to actually take a peek around her bedroom. Besides the usual furnitures, the space was occupied by several large vivariums. Getting a closer look, Perky saw the glass habitats were housing numerous species of insects, mainly butterflies and dragonflies. It all seemed impeccably maintained, which made sense given Flitter's cutie mark: a trio of dragonflies. Fascinated by the colorful critters, the little colt didn't even hear the pegasus come back until she spoke.

"Oh, so you like my collection, Perky?"

He turned around, noticing Flitter had arranged her mane in addition of having cleaned herself. "Yeah, they're neat! Where do you get all these?"

"Mostly from my job," the pegasus answered, pleased by his curiosity. "I work with the Weather Service to protect biodiversity around Ponyville; monitoring insect populations, making sure sensitive habitats are maintained, that sort of thing. We don't want to endanger rare species by carelessly rolling storms around during breeding seasons." She smiled at him. "Speaking of breeding, how are you doing? Did you have enough, or do you want to try something else before going to bed?"

Perky Prep blushed, his blue cheeks taking a lovely reddish color. "Um, since you played with my tailhole before, I'd like to play with yours now… if that's alright with you."

"Ah! You're more than welcome! And I have a few things to make it more fun. Come here…" Flitter grabbed a satchel hidden underneath her bed and opened it, letting the curious colt peek inside. "These are my sex toys. Some of them are for vaginas, while others are for anal. I use these when I'm on my own, and sometimes with a partner or two."

Flitter picked up an odd, bulb-shaped item from her stash. "That's a beginner butt plug. It got a magic crystal to make it buzz in your ass. With anal sex, it's essential to start slow, or you might hurt yourself. With a bit of lube, this one should fit nicely in your tailhole: it won't be too overwhelming, but it'll feel nice while you're busy with me. Interested?"

Perky Prep nodded enthusiastically, making her laugh. "Alright, alright! First, take this — that's a bottle of lubricant — and pour a generous dose on the bulb, which is the part that goes inside you. I'll hold the base for you… Yep, just like that: nice and slippery. Now, turn around, and I'll put it inside you."

The young colt presented his rump, and Flitter lifted his short tail out of the way, exposing his pert anus. She gently pressed the slick toy on his asshole, activating the crystal and simply wiggling it around. "Remember, always be careful and take your time while putting things in you, and only use toys meant for that purpose. You don't want to end up in the Ponyville Hospital with a carrot stuck in your ass."

"Okay…"

"It's safe as long as you take your time, and use plenty of lube. Now, hold on, I'm putting it in." Feeling Perky Prep anus loosen, Flitter tenderly pushed the plug in his rectum. The colt's sphincter opened to accommodate the plug, then rested comfortably around the narrower base, leaving the buzzing bulb to stimulate his prostate.

"Mmh! Oh, wow! That's so cool, Miss Flitter!" Perky Prep's colthood, which had remained in its sheath since his previous orgasm, peeked out once more under his barrel. It felt really good!

"I'm glad you like it. It's yours, if you want it. I got more, and this one is too small to do much for me anyway."

"Really? Gosh, thanks!"

"Sure, that's no trouble." Flitter stacked her pillows against the head of the bed, letting her sit comfortably. She parted her hindlegs, her long, silky tail between them, exposing her vulva and her anus to her young onlooker.

Perky crouched down over Flitter's tail, getting a good look at her privates. He started with her vulva, parting her soft labia and exploring her sex, the plug still vibrating in his ass.. He was interested in her tailhole, sure, but he liked her marehood too; she'd been so comfortable when he had ejaculated inside her before, his orgasms driven by her contractions. Flitter's pussy was fairly similar to Miss Cheerilee's, with the little nub of her clit and the gaping entrance of her vagina.

The colt caressed the pegasus' soft vulva, then shifted a little lower. Here it was: Flitter's gorgeous anus. Tenderly, Perky Prep traced the rim of her ponut with his hoof, eliciting a wink from her vulva. The little ring quivered too, feeling firm under his frog. It was from there that Flitter emptied her bowels, yet it was so prim, so pretty.

Perky Prep's cock hardened under him, both from the alluring sight in front of him and the plug in his ass. Unable to contain his excitement, the little colt kissed Flitter's tailhole, planting little pecks on and around the cute sphincter. His snout poked her vulva as he did, coating him in clear, smelly liquid.

Flitter moaned, looking down at the adventurous young foal between her legs. Perky's tender attention was wonderful, making her shudder and wink whenever his sweet lips grazed her tailhole.

Then, she felt his tongue prod her hole. "WOAH!?"

Taken aback by her outburst, Perky Prep scrambled backward. "Huh? W-What is it? Did it hurt? I'm sorry!"

"N-No…" Flitter let out, wide eyed, her heart thumping wildly in her chest. "It's… I wasn't expecting… uh… your tongue."

The colt looked concerned. "Was that bad?"

Flitter shook her head. "No, no… It's just… I like giving anilingus, but… nopony has ever done it to me before… I didn’t think you'd want to."

"But… you're so pretty! And it was amazing! I want to do it for you. Please?"

A gentle heat warmed Flitter's heart, and a smile lit her face. This colt was so sweet! "Okay, if you want to… sure. I'm ready."

Nodding gleefully, Perky Prep returned to her ass and licked her anus. He wasted no time prodding her hole again, and Flitter let him do it. It felt too good to protest anyway. Her sphincter opened, and the colt's tongue slipped in her rectum.

"Aaaah~! Buck yes! Do it, do it, do it! Unf!" THIS was what she had done to him, and some of her previous partners? It was the best! Perky lapped inside her ass, making her tingly all over. Her marehood pulsed and winked, coating his face with the scent of her arousal. She shuddered, loving every second of it.

Down between her hindlegs, the young colt was trembling too. Flitter couldn't see his penis, but there was no doubt the plug in his ass was working its magic. Without warning, Flitter lifted him by his shoulder, pulling him toward her. She pressed her lips on his mouth, kissing him and snaking her tongue in his muzzle. Flitter tasted herself, not caring one bit about it. Feeling his erection on her tummy, she pulled back, looking the young colt in the eyes.

"Let's put your dick in me, okay?" Flitter said, breathless. "You can finish in my ass."

Dazed, eyes wide, Perky Prep nodded. The mare stretched to reach her nightstand, grabbing the bottle of lube and squeezing a copious dose on his penis. Flitter caressed his cock, slathering it with lubricant, then wiped her hooves on the bedsheet.

"Now, don't forget to take it slow at first, okay?"

"Y-Yeah…"

"Good. Don't worry: I'll guide you." Placing her forehooves on his rump, Flitter helped Perky Prep get into position. His swollen glans brushed her sensitive vulva, then naturally lined up with her pucker. She felt no pain as he entered her rectum, and she guided him deeper. With a slow back and forth, the foal eased his way in her bowels, his flare sinking in her tailhole. Finally, his testicles rested on the dock of her tail, Perky's colthood entirely in Flitter's ass.

As he mated with the older pegasus, Perky dipped his forehoof in her vulva, rubbing her excited clitoris. Flitter was in heaven, utterly satisfied by the little colt that was so lovingly pleasing her. She came without warning, gushing marecum all over his crotch and screaming her delight. Even more excited, Perky rammed Flitter's ass, and hilted his erection into her. His glans bulged deep inside her, and she cupped his balls in her hoof, feeling his testes throb against her frog.

With a final twitch of his cock, Perky ejaculated in Flitter's butt, gooey colt seed flowing in her bowels. The mare stretched her neck to kiss her young partner, and they made out tenderly as they savored their climaxes in each other’s embrace.

Reaching around him with her hoof, Flitter turned off the butt plug and pulled it out of his anus, getting a soft gasp from him. She left the toy on the floor: she’d clean it in the morning. Exhausted, Perky Prep collapsed on her, burying his snout in the fluffy fur of her chest, though he continued to deliver little gushes of semen in her guts for a short while. Losing herself in post-orgasmic bliss, Flitter gently stroked the colt’s blue mane, waiting for him to finish.

It was getting late for a foal, and Perky was at his third orgasm in only a few hours. His flaccid penis slipped out of Flitter’s tailhole, quickly followed by a small stream of sperm. They stayed like this for a long moment, their breaths calming down from their exertion, until Flitter noticed the colt had fallen asleep on top of her.

“Aww, so cute~” Careful not to wake him, Flitter moved Perky Prep and tucked him in her bed for the night.

She yawned. Figuring her little buddy had the right idea, Flitter turned off the lamp and settled with him, spooning the colt. She held him tight, soothed by his calm, gentle breathing. She was happy: she had given him the good time he deserved, and it had been fun for herself too, but, more importantly, she had been able to pass on her experience of anal sex to him. She had nurtured his sexuality, giving him new ways in which he could make love and enjoy his own body in a healthy and safe manner. With a little luck, it would make his life brighter.

Cuddling Perky’s warm little body and nuzzling his mane, Flitter drifted to sleep.