Ponyville After School

Chapters

2. Diamond Tiara & Big Macintosh
3. Toola Roola & Amethyst Star
4. Perky Prep & Flitter
5. Tender Taps, Skeedaddle, & Rare Find
6. Scootaloo & Rainbow Dash
1. Pipsqueak & Cheerilee

2. Diamond Tiara & Big Macintosh

~ ✭ ~

The very first Friday following Cheerilee's call for volunteers, Big Macintosh received the teacher's visit at Sweet Apple Acres. It was noon, the red workhorse eating lunch outside the barn when he saw her coming down the path from Ponyville.

Cheerilee had come to the farm before, generally to discuss Apple Bloom's latest mischief. However, those were getting increasingly sparse as Mac's youngest sister got older, and Cheerilee would normally have come after the school day, not during lunchtime. Sure, it could mean Apple Bloom was in really big trouble, but that did not seem particularly likely given her leisurely pace and friendly smile.

No, clearly, Cheerilee wasn't on the farm to talk about his little sis, which left only one option: like his wife Sugar Belle, Big Mac had volunteered to help Cheerilee with the after-school reward program.

"Hi, Big Mac! This week's winner chose you for her special night, so I came to make sure everything was okay, especially since it's the first time I'm not doing it," Cheerilee said, confirming his suspicion.

"Eeyup."

"Oh, good! The filly is Diamond Tiara. Maybe you've met her?"

Big Mac raised an eyebrow. He certainly had heard plenty about Filthy Rich's daughter, since she used to be the school's bratty bully, and Apple Bloom's eternal rival. She had become much friendlier since then, and Mac even occasionally saw her at the Crusaders' clubhouse. Still, it was surprising to hear this rich little filly wanted to spend a night with a farm stallion such as himself.

Cheerilee didn't seem to notice his confusion. "Anyway, you should come pick her up after class at around 3 PM. Apple Bloom said she'd have a sleepover with her friends at Sweetie Belle's so you can use her room for the night. Is that alright?"

"Uh… eeyup."

"Perfect!" Cheerilee craned her neck to rummage in her saddlebags and produced a small vial. "Here's Diamond Tiara's birth-control potion. Please make sure she drinks it before mating with her. Besides that, it really isn't very complicated: be nice to her, help her explore her sexuality, and make sure she's satisfied. She will share dinner and breakfast with your family, and, of course, she will sleep with you. Any questions?"

"Nnope!" Though he was a little nervous, everything did sound fine to Big Mac, and pleasing a little filly certainly seemed like fun.

"Okay, in that case, I should return to the schoolhouse before the afternoon class. See you later, Big Mac!" Waving goodbye, Cheerilee went back the way she came, leaving the stallion to his lunch.

~ ✭ ~

As promised, Big Macintosh showed up at the Ponyville Elementary School as classes ended. Fillies and colts streamed from the door as the bell rang, returning home for the weekend. Big Mac said "Hi" to Apple Bloom and her friends as they left, then went inside.

Big Mac found Diamond Tiara speaking with Cheerilee at her desk. She was a pink filly, about the same age as Apple Bloom, with a curly, white and violet mane, wearing her usual tiara.

"Thanks for organizing this, Miss Cheerilee!" the filly chirped. "I can't wait for him to be here!"

"It's my pleasure, Diamond Tiara. As for waiting, that won't be necessary." Cheerilee nodded toward Big Mac.

"Eeyup!"

Diamond Tiara turned around, and a bright smile lit her face. "Oh, hey there, Big Mac! Hang on, I just need to pack my saddlebags real quick." She trotted to her desk.

As the stallion watched her, Cheerilee came up at his side. "By the way, I explained to Diamond Tiara that you might be a bit… big for her. She said it was fine, but… um, be gentle with her, okay?"

"Eeyup." Big Mac gave her a reassuring smile.

Soon enough, Diamond Tiara came back wearing her matching pink saddlebags. Big Mac left the school, the filly at his side, and together they took the path to Sweet Apple Acres.

"Thanks for agreeing to do this," Diamond Tiara said as they trotted down the road. "Miss Cheerilee is great and all, but I'm glad to do this with a strong stallion instead."

Big Macintosh smiled, but said nothing. The young filly faltered for a moment. "Right, guess you're not much for conversation."

His smile did not fade. "Nnope."

Diamond Tiara reflected on that for a moment. "Well, that's okay. Though… sniff, sniff… You're all sweaty, and kinda smelly. No offense, but…"

Big Mac would have blushed if his coat hadn't already been bright red. "Erm… Sorry 'bout that, Diamond Tiara. Ah had a lot of farm chores before pickin' you up, and, well… Ah'll shower when we arrive."

Diamond Tiara bit her lip and glanced away. "Well… maybe I could give you a bath," she offered, her pale blue eyes suddenly sparkling. "And, you can give me one too."

"Hmm… Eeyup!"

The Apple family farmstead was empty, save for Granny Smith napping outside, so Big Mac and Diamond Tiara went straight to the bathroom.

Diamond Tiara turned the tub's faucets, but only a squeaking, rattling sound came out. Her face fell. "Uh, I think your bath's broken." Big Mac simply bucked the pipes, and warm water immediately gushed out from the tap.

The filly facehoofed. "Really? Couldn't you just repair it? Or get a new one? Urg, whatever…" She looked around the room. The rustic, pastoral decor really wasn't her style, and everything in it had been outdated since before her birth anyway. Still, it was clean enough, and Diamond Tiara could tolerate it if it meant sharing a bath with Apple Bloom's handsome brother.

As the bathtub slowly filled up, Diamond Tiara checked the content of the wooden tablet next to it. "Okay, so you have soap and shampoo. That's a start. Hm, don't you have bath salt? Scented oil? Bubbles? Anything?"

"Nnope." Big Mac faltered under the rich filly critical gaze. "Erm… maybe?" Mac poked around Applejack and Sugar Belle's cabinets, and eventually found a few bottles with the word 'bath' on them. He presented his findings to Diamond Tiara.

"Ah, better! Let's see, we have… 'Apple-Scented Bubble Bath'... 'Fresh Apple Scented Oil'... 'Apple & Cinnamon Salt', eww… Everything's apple-scented, of course. It's not bad, sure, but you should try a bit of variety now and again. Oh wait, here's some 'Pear-Butter Bubble Bath Oil'! Sorry Big Mac, we're taking this one." Diamond Tiara grabbed the bottle of pear oil, and squeezed a generous dose from it in the warm bathwater.

Immediately, a delicious, sweet scent of pear perfumed the bathroom, bubbles forming a thick foam in the tub. Satisfied, Diamond Tiara turned off the tap, and invited Big Mac to step in. There was only enough water to fill half the tub, but it rose almost to the overflow drain as soon as the big workhorse entered it.

Spotting a wooden stool — probably used by Apple Bloom to reach the sink —, Diamond Tiara brought it next to the bath. With it, she could comfortably access Big Mac's body, so she picked up the soap and got to work.

As embarrassing as getting bathed by a young filly was, Big Mac soon relaxed, sighing happily. The feeling of soapy filly hooves scrubbing his back was wonderful, especially after a hard day working on the farm. It must have showed on his face, because Diamond Tiara giggled, pleased with herself. "See? It's fun to be bathed. Our maid at home always wash me, and it's sooo relaxing. Huh, and, you know what? I never scrubbed anypony else before, but that's pretty fun too! Am I doing a good job?"

"Eeyup." If that was her first time doing this, she was certainly very good, and Big Mac's cock slipped out of its sheath in reaction.

Having finished Big Mac's back, Diamond Tiara went down his foreleg. Even though Mac lifted it, she still had to stretch awkwardly on the stool to reach him. Diamond Tiara's eyes went wide as she lost her balance. She yelped as her hooves slipped from her perch. In a split second, Big Mac grabbed her, and pulled her toward him. The wooden stool fell on the floor with a loud thud, and Diamond Tiara crashed head first onto Big Mac. The stallion slipped, ending up on his back in the tub.

Moments later, the commotion was over, and Big Macintosh was sitting in the bathtub, a dazed filly on his barrel. "Uh, ya alright?"

"Um… yeah, I think…" Diamond Tiara answered."Thanks for the save."

Big Mac petted her mane. With the burst of adrenaline gone, they both relaxed in the warm, soapy water. As Diamond Tiara pressed her body on his, Mac felt his sex brush into her soft belly. She bit her lip and glanced down, obviously noticing the same thing, but she said nothing, so he put a hoof on her croup, pressing her down and rubbing himself on her coat.

Still, even though it felt nice, Big Mac knew he couldn't just continue like this: he wanted to penetrate her, to feel her fillyhood around his cock, but he needed to prepare her first. "Erm, maybe we could finish cleaning up before… um…"

Diamond Tiara smiled, embarrassed. "Yeah…" She picked up the soap and quickly went to work, scrubbing his legs and belly. As she moved up, Big Mac felt her filly vulva on his cock, though neither could see it under the thick, bubbly foam. Diamond Tiara quietly gasped, grinding her sex on his stallionhood. She finished swiftly, handing Big Mac the soap. He gave her a quick, cursory wash; she was so prim already she hardly needed it anyway.

As they got out of the tub, Mac could feel Diamond Tiara's stare on his erect stallionhood. "Woah, that's supposed to go inside me?" the filly muttered, wide eyed.

Smiling, Big Mac thoroughly toweled her, getting her pink coat nice and fluffy. Curious about getting a good look at her sex, Big Mac lifted her tail. Diamond Tiara's vulva and tailhole were pert and puffy, the cute teardrop of her labia flashing a deeper shade of pink than her fur. He wiped her rump, passing his towel-covered hoof through her slit, and enjoying the moan that came with it. Finally, Big Mac briskly dried himself, and led Diamond Tiara outside the bathroom.

He passed the bedroom he normally shared with his wife, instead heading for Apple Bloom's bedroom, his sister having generously lent it to them for the night. As he shut the door behind them, Diamond Tiara examined her classmate's bedroom with great interest, noting the canopy bed, dresser, and vanity before hopping on the first one. The bedsheets were coarser than she was used to, but that hardly mattered when it meant she could lay with such a handsome stallion.

Though, as she peeked once more at his penis, Diamond Tiara was hit by a fresh wave of nervousness. Honestly, she had no idea what to do. Fortunately, Big Mac was patient and kind, so she simply told him. "Erm, I… I never had… sex with a colt before. Or a stallion. What should… uh…"

Big Mac nodded, a gentle, understanding expression on his face. "Well, first, Miss Cheerilee gave me this for ya." He passed her the vial of potion.

Diamond Tiara read the label, and blushed. "Yeah, alright. That makes sense." She uncorked the bottle and gulped down the clear liquid. It quickly flowed in her guts, protecting her from an impromptu pregnancy. "Okay, so what now?"

Big Mac rolled the filly on her back, and kissed her belly.

"Um, what are you doing…?"

Big Mac kissed Diamond Tiara's immature teats, and licked her crotch, before moving even lower. He sighed, admiring her pretty vulva, his muzzle so close to her that she twitched simply from the warm exhale of his breath. Her little clit peeked cutely from her swollen labia, throbbing with need. With his hooves, Mac parted her lips, revealing the enticing entrance of her snatch. She smelled really nice, the musk of her sex melding pleasantly with the pear scent of the bath oil.

After a particularly needy wink from Diamond Tiara's pussy, Big Mac figured he probably shouldn't keep the filly waiting. He gave her fillyhood a big lick, starting on the pucker of her anus, moving up through her tangy fold, and ending on her clit.

"Aaah!" Diamond Tiara yelped, arcing her spine and driving her vulva into Big Mac's snout. Pleased with her reaction, the stallion gave her more, licking and suckling her sex.

Since that first one when he had made love to Sugar Belle in the back of her shop, Big Mac had done this hundreds of times. It was the best way to prepare his wife for mating, something she was certainly vocal about. He'd never been with another mare though, especially not with a filly. Besides being smaller, Diamond Tiara's vulva was different from Sugar Belle's in many subtle ways. Mac quickly noticed the filly reacted differently than his wife: her clitoris seemed less sensitive, but she gasped loudly whenever he pushed his tongue in her vagina.

Having no issue whatsoever about adapting to her preference, Big Mac delved deep with his tongue into her, licking her smooth inner walls. Diamond Tiara's vagina contracted around his tongue, her body instinctively attempting to drive it deeper inside her. Her hindlegs clenched around his neck, her forehooves caressing his mane. Diamond Tiara's vulva bloomed, her tummy forming cute concaves as she panted for breath. Big Mac kept pleasing her, but he knew she was as ready as she'd ever be, and his own unattended penis throbbed almost painfully under his barrel. He kissed her folds, and looked into her eyes, feeling her desire, her lust. "Ready?" he asked in a whisper. She nodded, breathless.

Having received her consent, Big Macintosh shifted up, moving forward until Diamond Tiara was under him. He held her firmly, lining his glans with her sex. Big Mac's flare was a fair bit larger than her entrance, and they both stared at it. Diamond Tiara's vulva winked, kissing his tip and coating it in her clear fluids.

Holding her hindlegs apart, Big Mac carefully pushed into her. At first, nothing happened, so he used his weight to force Diamond Tiara's entrance. She briefly winced in pain, but eventually her labia opened wide, and Big Mac's swollen glans disappeared inside her snatch. He stopped there, barely an inch inside her, giving her time to stretch.

"Woah… bucking hell…" Diamond Tiara let out, watching her fillyhood in awe as the stallion took her virginity.

"Ya alright…?"

"Yeah… unf… just… go slow, okay?"

"Eeyup." Sticking to his promise, Big Mac started with the subtlest of movements, more like a slow rub than a thrust, simply wiggling his glans in her vagina. Diamond Tiara cooed softly, pleasure replacing the uncomfortable stretching in her nether.

Big Mac rubbed her belly with his hoof. Even with just his tip inside her, Diamond Tiara's fillyhood felt incredible, her canal tightly constricting his flare. As he rubbed her insides, he pushed just a little more, delving a little deeper in her sex. He waited for a moment, then pushed again.

With about two inches in, Big Mac pulled back slightly, and began to slowly thrust into the cute little filly. Diamond Tiara no longer winced, simply letting out a throaty "Aaah~" as the workhorse penetrated her. Even with her usual, rather ostentatious, demeanor, Diamond Tiara was an earth pony, and the magic in her blood made her tougher than she’d otherwise seem.

Reassured to see Diamond Tiara taking it so well, Mac went a little faster, his balls jiggling freely under his tail as he mated with her. Without even really trying, his thrusts drove his penis deeper and deeper into her, getting more of his length into her sweet filly snatch.

"Oh, yes! Mmmh!" Diamond Tiara shuddered in pleasure as she received her first stallion.

Big Mac penetrated her relentlessly, enjoying her tight little body as he made love to a foal. Her cute mane bounced along with the wet shlick-shlick-shlick sound his cock produced with each stroke in her pussy.

With each impact, her fillyhood opened a little more, until, finally, with about half his shaft inside her, Big Mac reached Diamond Tiara's cervix. He stayed there for a moment, feeling the entirety of her vagina around his cock, then returned to work, pumping into her fillyhood. The young foal was becoming easier to penetrate, her flesh stretching to accommodate his girth; she was still amazingly tight, but her passage was incredibly slick from her juices, letting Big Mac's stallionhood slide freely within her.

Diamond Tiara moaned, gasped, arching her spine, trying to get more of him inside. Her clit throbbed urgently, and she used her forehooves to masturbate. Her open, gasping muzzle was so cute, Big Mac bent his neck to kiss her. He slipped his tongue in her mouth, making out with her.

Big Mac rutted her like a grown mare, pounding the filly's sore vulva as he kissed her. Diamond Tiara was breathless, overwhelmed by bliss. She trembled, her pussy pulsing around his sex.

The filly kissed Mac feverishly, the glow of her climax burning brightly in her belly until she couldn’t hold it anymore. Diamond Tiara yelled something very unladylike, her body shuddering so hard she lost her trademark tiara. Smiling, Big Mac watched tenderly the filly orgasm under him. Her fluids gushed from her vulva, impregnating Apple Bloom's bedsheets with the pungent scent of her sex.

Pressing deeply into her, Big Mac felt Diamond Tiara's cervix loosen as she came. He put all his weight on her pelvis, pushing through her deepest barrier. His glans entered her womb, and he flared, sealing her uterus. Lost in the throes of her orgasm, Diamond Tiara barely felt the intrusion.

Big Mac closed his eyes; the soft, spongy feeling of filly uterus caressing the hypersensitive skin of his glans adding to the contractions of her vagina was just too much to handle. The stallion held Diamond Tiara’s rump firmly, pinning her down, and let out a loud whinny, his testicles throbbing in their sack.

Orgasming, immobilized by a powerful workhorse, her sex stretched wide by his virility, Diamond Tiara only realised at the last second what was happening. She felt a shudder travelling through the thick shaft in her sore snatch, and the head bulging even more in her uterus. A warm, gooey sensation spread deep in her belly, and she knew what it was: Big Mac was ejaculating inside her.

In bliss, Big Mac let himself go. His seed gushed in her womb, filling her up with thick stallion semen. He looked down, gazing in the eyes of the sweet filly he was inseminating. He coated her uterus with his sticky gift, getting his sperm in every recess of her uterine walls. Fertile semen flowed in Diamond’s Tiara oviducts, Big Mac sperms searching for her ovum — in vain, thanks to the birth-control she had ingested earlier.

As her climax waned, Diamond Tiara relaxed, limp on Apple Bloom’s bed. Big Mac continued to ejaculate inside her, though that was quickly fading too. The stallion stayed in her until the end… not that he could go anywhere else, his swollen flare locked in her womb as he came.

When Big Mac finally softened, he carefully pulled out of Diamond Tiara, leaving her pussy gaping and leaking cum. He admired his work for a moment: beneath him laid a panting pink filly, a big, blissful expression on her face, her tongue lolling out. Her little tiara had fallen off her disheveled mane, and his seed trickled down from her open vulva, soaking her tail. Utterly spent, Big Mac stepped to the side and rolled on his back, settling down next to her, his sticky, flaccid cock resting on his heaving underbarrel.

Diamond Tiara was seeing stars, her mind hazy in her afterglow. Big Mac’s semen, her reward for being such a good filly in class, was pleasantly warm in her belly, the creamy softness of it soothing her sore sex as it oozed from her. At her side, Big Macintosh’s penis glistened, wet from her fluids and his own sperm.

A soupy mix of filly juices and stallion cum soaked into the fabric under Diamond Tiara. The filly giggled softly, realising she was staining Apple Bloom’s bed with her own brother’s seed.

Big Mac embraced Diamond Tiara, gently wrapping his forelegs around her withers. Happy to receive some affection, the filly nuzzled his coat. He was all sweaty — and smelly — again, but it did not bother her this time. She smiled, inhaling his musky odor; it was the scent of sex, and everything naughty things they’d done together. Honestly, she was probably stinking just as much as him. She rubbed herself on him, the big, strong stallion that had so wonderfully taken her virginity.

Diamond Tiara felt Mac’s hoof caressing her mane, and she looked up, meeting his stare.

“Ya feelin’ good?”

She stroked her abdomen, still feeling his warmth inside. “Mmhmm. Thanks, Big Mac. That was great. I’m glad I worked so hard this week in class, and that I chose you. Say… can we do it again?” Still, despite the fullness in her belly, Diamond Tiara’s stomach growled loudly, making her blush in embarrassment. She peeked at Apple Bloom’s alarm clock: it was dinner time, and she had not even taken her usual afternoon snack. “Uh, maybe after we eat?”

“Eeyup!” They had plenty of time, after all: her dad would come pick her up in the morning, so they had all night to have fun together.

~ ✭ ~

Meanwhile, Sugar Belle smiled, leaving quietly before her husband and the lucky filly rose from their shared afterglow. Having arrived earlier, Sugar Belle had been able to watch Big Mac as he gave this sweet filly her first time. Watching his cum leak from her vulva afterward had been especially exciting, the memory of it making Sugar Belle’s clit throb. She loved him so much, and seeing firsthand his generosity made her heart flutter even more.

Sugar Belle returned to the kitchen. These two certainly deserved a very special dinner before returning to their mating, so she went to work immediately, humming to herself.

3. Toola Roola & Amethyst Star

(Vectors by jhayarr23, & RainbowRage12

~ ✭ ~

"Okay, you can put away your notebooks, everypony," Miss Cheerilee said. "Now, before you all leave for lunch, please come pick up your copy of yesterday's writing assignment, so we can officially announce the filly or colt of the week!"

Sitting at her desk near the rear end of the class, Toola Roola anxiously bit her lip. She glanced at the board where Cheerilee kept track of everypony's score: Toola Roola was in the lead, having more stars pinned to her name than anypony else in class. She'd come so close so many times, but now it could finally be her turn.

Her nervousness stemmed from how little advance she had over some of the other foals. Silver Spoon, in particular, had only one star less than her, and Miss Cheerilee had announced the top three grades on the writing test would earn two stars each. Silver Spoon always was at the top of the class in writing, so Toola Roola needed to earn some stars too to keep her prize.

Her friend, Coconut Cream, gently nudged her, and Toola Roola snapped out of her thoughts. Nearly all the foals were already in line to pick up their copy, so she rushed to take her place.

"I'm sure you did great, Toola," Coconut said as they waited for their turn. "You'll win for sure!"

Toola Roola wasn't convinced. "If you say so…"

"Of course you will," her friend assured, grinning, "and tonight you'll get to sleep with one super handsome stallion. You'll see!"

Suddenly very uncomfortable, Toola let out an awkward little laugh. "Haha… ha… yes, stallion, of course." She looked away. They reached Miss Cheerilee's desk, and Toola Roola searched for her copy in the few that remained. Finding it quickly, the filly anxiously read the note penned in the margin by the teacher.

19/20
Well done, Toola!
+2 pins

Toola Roola stared at it for a moment, its meaning making its way in her brain. She grinned, and jumped in joy, shouting "YES!"

At her desk, Silver Spoon scowled, visibly disappointed.

A few minutes later, as fillies and colts left class for lunch break, Toola Roola stayed behind with Miss Cheerilee, the filly grinning from ear to ear.

"Congratulations, Toola Roola!" the schoolteacher said, a warm smile on her face. "Here's the list of mares and stallions who are available tonight. Take a few minutes to think about it, then tell me once you made your choice."

Toola nodded, picking up the list and sitting down. Over a dozen names were written on the sheet in two columns, one for stallions and one for mares. There was no other information about these ponies, but it hardly mattered: Ponyville was a pretty small town, and the filly already knew everypony on the list.

Which left the matter of deciding who she wanted to spend the night with. Toola Roola passed through every stallion's name, but, honestly, none really caught her interest. Nervously nibbling her lower lip, she glanced at the second column. There were some really pretty mares on that list, including some big names such as Pinkie Pie and Rainbow Dash, and it made her heart throb. Unable to decide, Toola Roola eventually settled mostly at random on one pony, Amethyst Star, an unicorn mare who lived on her street.

Bashfully, Toola announced her choice to Miss Cheerilee. The teacher only smiled. "Of course, Toola Roola. Go ahead and join your friends for lunch. I'll inform Amethyst so she knows to pick you up after school."

~ ✭ ~

Amethyst Star arrived a bit late at school, which suited Toola Roola just fine. When the mare eventually showed up, Toola was alone with Miss Cheerilee, the rest of the class having already left for the weekend, sparing the filly from having to face her classmates' unavoidable questions.

Amethyst apologised for the delay, shared a quick word with Miss Cheerilee, then left school with Toola. What she didn't tell the filly was that she had been late on purpose: Cheerilee had explained Toola seemed anxious about choosing somepony of the same sex, and neither mares wanted to make the filly uncomfortable in front of her classmates.

It was just a short trot from the school to Amethyst's home. The unicorn welcomed her young guest inside, inviting her to sit down on the couch.

"Well, Toola, Cheerilee told me you're a really good student, and that you worked extra hard this week," Amethyst Star said, smiling kindly. "So, what can I do for you?"

Blushing, Toola Roola looked at the pretty mare in front of her. Amethyst Star was an energetic young mare with a magenta coat, purple eyes and a two-toned violet mane, her cutie mark consisting of three diamonds. Eventually, the filly managed to stammer out a weak "Erm… I dunno…"

Amethyst's expression morphed to concern. "We don't have to do anything if you don't want to," she assured. "Let's just stick to something you're comfortable with for now, okay?"

"O-Okay."

"Why don't we go outside and enjoy this beautiful weather together? I have a pool in the backyard, and we can sit down, share a smoothie."

Toola's nervousness abated at the proposition, and she nodded, smiling. "Sure!"

Ten minutes later, Toola Roola was lounging by the pool, taking in the sun and sipping a fruit smoothie, Amethyst doing the same a few feet from her. That was really nice, actually, letting the filly relax with the unicorn before going any further with her. And Toola wanted more; her gaze kept falling on Amethyst Star's rump, making her oddly warm inside. Still, she was okay with taking it slow.

Amethyst lifted her sunglasses, glancing at Toola Roola. "You know, I like your mane and tail."

"You do?" The filly looked at herself. Her mane was pink, red, and yellow, yet her tail was blue and cyan, creating an odd mismatch.

"Yeah, it's cool! Do you dye your hair?"

Toola Roola shook her head. "Nuh-uh. That's my natural colors. Doctors say it's genetic. It's pretty rare, and, even then, it's generally not that extreme. I've never met anypony else like me." She hesitated, unsure whether she was sad or proud about it.

"Wow, you're a special little filly, Toola. I hope you know that."

Toola Roola took another sip of her drink, shyly dodging the need to respond. She was blushing, but she had to admit it felt really nice to be complimented like that by a mare.

A comfortable silence settled once more in Amethyst's backyard.

Mare and filly spent the remainder of the afternoon like this, occasionally trading words and getting to know each other better. Amethyst had done a lot of interesting things, including being the Animal Team leader during seasonal wrap-ups, and having organized Cranky and Matilda's wedding. Toola Roola talked about her passion for art, and how it had earned her swirling paint brush cutie mark.

Around 6PM, Toola Roola helped set up the table while Amethyst grilled spicy veggies on the barbecue. Dinner was really good, and, after her second serving, the filly slumped at the table, completely stuffed, eliciting a giggle from the unicorn.

“Hehe, I’m glad you liked it!” Amethyst said, smirking. “Why don’t you lay down on the couch while I clean up? I’ll be with you in a minute.”

Toola Roola nodded. “Yeah… thanks.” She dragged her way back to the living room and dropped head first on the comfy couch, feeling very drowsy.

As promised, Amethyst joined her soon after. “Mind if I sit with you?”

The filly stirred, shook her head, and scooched sideways, making some space. The couch wasn’t big, but Amethyst sat closer to Toola than she strictly needed to. That was just fine, though; the filly tentatively snuggled the unicorn, and received a warm hug in return, Amethyst gently stroking her mane. It was more of a sisterly cuddle than a lovers' embrace, but Toola nonetheless enjoyed the mare's tender touch.

"So, Toola Roola, pardon me for asking, but… you like other fillies, is that right?"

"Mmhmm, yeah. I mean… colts are okay, I guess, but… um… I've always known I loved fillies," the filly answered, actually quite comfortable being petted like this.

"Do you have a fillyfriend?"

"No…" Toola's expression turned sullen. "I told my parents, but my friends don't even know. That's why I was glad to be with a mare tonight, but… uh, I have no idea what to do. I guess I'm kinda making a fool of myself…"

With her hoof, Amethyst lifted the filly's chin. "No, you don't. There's nothing wrong with taking it slow. You shouldn't feel pressured. Besides, to be honest with you, I've had a few coltfriends over the years, but I've never been with another girl before, so I don't know what to do either."

"Oh…"

"But that's okay: we can just discover it together. What do you say?"

Toola Roola smiled, then bit her lip. "Um, can I… erm… kiss you?"

"Mmhmm." Amethyst closed her eyes, offering her lips. There was a short pause, then soft filly lips pressed on her mouth. The unicorn moaned appreciatively, wrapping her forelegs around Toola's withers and pulling the filly into a hug. It was over soon, just a shy little kiss by a tender young amateur. Toola Roola, however, seemed completely dazed, which amused her older partner. Taking charge, Amethyst kissed the filly again, putting more force into it, eliciting a throaty purr from her.

It felt really good for the mare too, actually. Kissing the foal, Amethyst's experience from half a dozen coltfriends kicked into gear, and she naturally opened her maw, inviting her partner inside. Nothing came however, reminding the unicorn that she was kissing a shy, inexperienced filly, not a stallion.

Realizing she had to lead, Amethyst gently prodded Toola's mouth with the tip of her tongue, licking her teeth. The filly shuddered, and relaxed her jaw, letting the mare's tongue slip into her muzzle. Caressing Toola's mane, Amethyst explored her mouth, playing with the filly's tongue.

They made out for a while, until Amethyst finally pulled back, letting them both catch their breaths. Toola Roola was in bliss. "Woah…" She licked her lips, just to make sure it was actually real.

"Yeah… That was very good, especially for your first kiss!"

The filly's light blue eyes sparkled. "Really? You liked it?"

"Mmhmm! You're going to make a lucky filly very happy one day. Here…" Amethyst hugged the foal and kissed her again, feeling her little body tremble in her hooves.

As she pressed Toola's body closer, Amethyst felt a distinctive wetness under the filly's mismatched blue tail. That, and the fact that she had to twist her neck uncomfortably to reach the filly sitting next to her, made the unicorn pull back. "Wanna go to my bedroom?" Amethyst asked, caressing her cute rump.

"Y-Yeah… Please!" Toola Roola followed Amethyst Star upstairs.

As she made her way up, the unicorn could practically feel the filly's stare on her rump. She politely lifted her tail, letting her young onlooker peek at her sex. Amethyst had never been particularly interested in other mares, preferring stallions instead, but she had to admit it was quite exciting to be eliciting such desire in Toola.

Entering her bedroom, Amethyst peeked behind her. Though she was already blushing, Toola Roola turned scarlet, and immediately looked away, like she’d been caught staring. Amused, the unicorn mounted the bed, and invited the filly to join her. Toola gingerly climbed atop the bedsheets. As she tried to settle down at Amethyst's side, the unicorn instead redirected the filly behind her, lifting her tail high and exposing her marehood. Toola Roola's eyes opened wide, her mouth forming a perfect O.

Amethyst wiggled her rump. "Don't be shy, Toola. Take your time and explore me. I'm not going anywhere."

"O-Okay." Toola Roola took in the breathtaking sight of the mare's genitalia. She'd seen under other fillies' tails, of course, and she had thoroughly explored her own sex, but never had she had access to somepony's else like this before. Under the hairless dock of Amethyst's tail laid the pert pucker of her anus. Her vulva started right underneath, the magenta lips of her labia narrow near the top but wider near the bottom, forming the classical shape of a raindrop.

Secretly, Toola Roola had always being disappointed in her own fillyhood: it was not particularly symmetrical, and there was little wrinkles near her tailhole. Examining Amethyst's vulva, however, the filly realized that — though the mare's sex was different from her own — it wasn't 'perfect' either… and, for all its little irregularities, it was still astonishingly beautiful. It made her feel a lot better about her own body, and curious to see more, Toola brought her forehoof to Amethyst's sex, though she stopped short of actually coming in contact with her. She lifted her head to look past the mare's rump. "Uh… Miss Amethyst? Can I… you know… touch your… erm…"

The unicorn chuckled. "Sure, you can do whatever you want." She winked. "As long as you don't bite anything."

"Hehe! I won't!" Going back to the mare's pussy, Toola carefully, almost reverently, parted the folds of Amethyst's labia, revealing the pink insides of her sex. The mare shivered cutely from the filly's touch, making Toola smile.

Near the top of her sex, the entrance of Amethyst's vagina offered an enticing view inside her. The smooth inner skin had a clear, wet sheen to it. Toola blinked a few times; was she actually managing to make a grown mare feel good? At the bottom of the slit, Amethyst's clit gently pulsed. Intrigued, Toola carefully poked the little nub. The unicorn moaned softly, her vulva winking and her hindlegs twitching.

Huh… Emboldened by the reaction, the filly delicately caressed Amethyst's clitoris. The mare moaned some more, wiggling her tail. Toola rubbed Amethyst's marehood a little more forcefully.

"Mmmh! Yes!"

Toola Roola's hoof was slick, coated in Amethyst's clear fluids. The mare gasped and cooed, shaking as she was masturbated by a little filly hoof. Her vulva bloomed, red and puffy with arousal. Toola took in the pungent scent of an excited mare. Her own fillyhood kept winking, throbbing with need, but she paid it no mind; Amethyst Star's pleasure was filling her with a heady thrill, something the young filly had never felt before.

"A-Aaah… unf! U-Use your tongue, m-maybe? Please~"

Toola Roola stared wide eyed at Amethyst's needy pussy, considering that enticing possibility. She'd heard about this, sure — some ponies called it 'eating out' a mare — but she had always thought it was kind of gross. Why would anypony want to put their mouth there? That's where mares peed from! And yet, with her mind drowning in hazy lust, Amethyst's excited vulva filling her sight, it suddenly didn't seem so icky anymore.

With just the tip of her tongue, Toola licked Amethyst's open sex, getting her first taste ever of another girl's vulva. It tasted kinda tangy, and smelled really strong, but it wasn't bad. Somewhere in that bouquet of musky flavors, the filly could discern the subtle, intoxicating undertones of Amethyst's breeding pheromones.

Wanting more, Toola pressed a bit more with her tongue. Amethyst squirmed in response, pushing back with her pelvis, driving the filly's muzzle deeper inside her sex. As Toola licked the unicorn's pussy, her tongue unwittingly slipped inside her vagina, plunging deep into the mare. Interestingly, Amethyst Star's foal-canal contracted rhythmically around Toola Roola's tongue, naturally trying to help her inside the tight passage.

As she explored every nook of a mare's vagina she could reach, her vision filled with Amethyst's cute purple anus, Toola felt the unicorn's clit poke her chin. Not wanting to give up her oral spelunking, the filly brought back her hoof again, masturbating the mare… to spectacular results. "Oh, buck me!" Amethyst yelled, a spasm coursing through her spine.

Her face soaked in mare juices, Toola grinned, excited. She could practically sense the climax building in the unicorn's body. With her free forehoof, Toola held Amethyst Star's beautiful rump in place as she relentlessly stimulated her marehood. Her tongue was tiring out, but she was a tough filly: she wouldn't stop, not when her partner was this close to her release.

Amethyst Star went absolutely rigid, all her muscles tensing as she came from the filly dual touch. A strangled, weak cry escaped her throat, sounding almost like she was about to sob. Toola Roola suckled on her clit, the little nub throbbing in her mouth, until, finally, creamy, yellowish marecum gushed all over her filly face.

Toola valiantly suckled the mare's clit, prolonging her orgasm until, eventually, she couldn’t hold on anymore. The filly backed out, gasping for breath, her little heart thumping in her chest. She fell limp on the bedsheet, as did Amethyst. For a while, they both laid where they were, panting heavily.

Amethyst rolled on her back, seeing stars. "Holy… bucking… Celestia…" she muttered to herself. She lifted her head to check beyond her heaving tummy; Toola Roola laid beside her tail, visibly recovering from the exertion. A surge of embarrassment swelled within her as she noticed the poor filly's face was soiled with several globs of her own creamy emissions, one even dripping from her tricolor mane.

"Uh, sorry 'bout that, kid," Amethyst said nervously. Using her magic, she levitated a towel from her wardrobe and thoroughly wiped Toola's face until the filly was reasonably clean.

Toola Roola let it happen. In fact, she barely noticed. A single, triumphant thought occupied her mind: she'd made Amethyst cum. She, a little filly, had made a grown mare orgasm. It drowned out everything else, even the insistent throbbing of her own needy pussy.

"Wow, you… That was really good, Toola…" Amethyst let out, her tone carrying a distinct note of shock.

The filly retreated behind her bangs, flustered by the compliment. "Uh, you really think so?"

"Yeah! Are you sure you've never done this before?"

Toola shook her head. "Nuh-uh…"

Amethyst Star stared at the young filly in disbelief. In truth, the unicorn was astounded: she'd been with a few stallions before, but none of them had been able to make her cum just with oral, and yet that little girl had done it like a pro… on her first try.

Taking a deep breath and shaking her head to clear her thoughts, Amethyst realized she had not done her job of pleasing the filly, something that Toola — if the wet stain under her tail and the quivering of her rump were any indications — badly needed.

Amethyst's first orgasm had fed her arousal more than it had quenched it. She looked down on the excited filly, her expression almost hungry. "Hey, wanna try something with me?"

"I… um… sure…?"

Without warning, Amethyst pounced on Toola Roola, locking her lips on hers and sending her tumbling backward. She pinned down the filly, taking advantage of her surprised yelp to push her tongue in her muzzle, tasting her own tanginess. Toola squirmed for a moment in confusion, then relaxed, submitting to the unicorn.

Grabbing Toola's rump, she pressed the filly's crotch on her underbarrel, rubbing her excited clitoris in her fur. Not breaking the kiss, Amethyst started a slow back and forth, moving up and down the filly almost like a mating stallion would. Toola Roola moaned into the kiss, her fillyhood finally getting the attention it deserved.

When she eventually pulled back from the filly's mouth, Amethyst moved up until both of their crotches rubbed together, their flat, immature teats kissing each other. Her forelegs straight, hooves on either side of Toola's head, Amethyst towered over the panting filly, putting most of her weight on her pelvis.

In spite of her lust, Amethyst Star needed to take a moment to plan her next move. While she had some notions regarding mare-on-mare sex, she had never done anything like this, and the position required some careful maneuvering. First, she moved back, keeping her crotch in position until she was practically falling backward, having to twist her forelegs to support herself. Then, she passed one of her hindlegs over one of Toola Roola's own.

"Erm, what are you doing?" Toola asked, struggling to get a better view.

"Shh, don't move. I got this. Just… have to… Aaah! There!"

Mare and filly moaned in unison, their vulvas sharing the most intimate of kisses. Amethyst shuddered, feeling Toola Roola's clit rub her own sensitive nub

"W-Woah!" Wide eyed, Toola stared at where their bodies met, Amethyst's plush labia entering her blooming slit.

The unicorn smiled. "Heh… That's called 'scissoring'. I heard it's a great way for two girl to have sex, and… unf… I think I get why."

"Yeah…" Toola nodded, excited and a little breathless. Already pent up, she squirmed in delight, Amethyst gyrating her hips and grinding their sexes together. The mare savored the sweet contact of a soft filly pussy on her vulva. Toola Roola was visibly in bliss, and Amethyst realized she was giving this cute foal her very first time. She was taking her virginity, and she gave her her best.

*Shlick-shlick-shlick!*

The wet sound of their mating filled the room, along with the scent of excited mares. Amethyst let herself go, having sex with this young filly, and fully enjoying it. Her chest heaved from the exertion, her heart thundering as if she was galloping a mare-a-thon.

Suddenly, Toola cried out, and she came. Fillycum gushed from her little pussy, coating Amethyst's marehood in gooey secretions. The unicorn didn't stop, instead feverishly rubbing herself on the climaxing filly, taking her pleasure from the foal. Toola wasn't minding it, of course, the nonstop stimulation giving her orgasm after orgasm.

With a loud gasp, Amethyst Star mashed her pussy on Toola Roola's throbbing mound, and came as well. “Unf! Aaah!” Tremors rocked her entire body, her vagina and womb shuddering from her orgasm. Their clits pulsed against each other, sending tingly shocks of intense pleasure through their spines. Finally too sensitive to continue, Amethyst backed away, filaments of marecum and fillycum linking their vulvas before snapping.

The unicorn fell on her back, gasping, butt-to-butt with her young partner. She relaxed, her tail intertwining with Toola Roola’s own short blue one as they both came down from their peaks.

The filly shifted around to face Amethyst. The mare embraced her, wrapping her forelegs around Toola Roola’s neck. She nuzzled the foal’s sweaty, disheveled mane, planting a flurry of little kisses on her forehead and making her giggle.

“Mmmh… That felt sooo good,” Amethyst whispered, her mind clouded in post-orgasmic bliss.

“Uh-uh…” the filly half-responded, the sound of her voice barely audible in her afterglow.

Amethyst caressed her colorful mane. “Was having sex with another girl as good as you imagined?”

Slowly, a grin of deep satisfaction formed on Toola’s lips. “Yeah, better…”

“Wanna do it again?”

Toola Roola canted her head, staring wide eyed at the unicorn. “Can we?”

“Heheh, sure! As many times as you can handle. We have all night…” Seeing the filly’s eyes sparkle in excitement, Amethyst kissed her on the lips, making out sloppily with her. Moving lower down her little body, Amethyst gazed upon her puffy fillyhood, licking her lips in anticipation.

“Your turn now,” the mare said, before plunging tongue first in her little pussy.

~ ✭ ~

The next morning, Toola Roola woke up in Amethyst Star’s bed, snuggled close to the unicorn, her face caressed by the sleeping mare’s silky mane. With a happy sigh, the filly gently stroked Amethyst’s magenta fur, taking comfort in the regular heartbeat she felt under it. Her fluffy coat smelled of sweat and sex, reminding her of all the amazing things they’d done together.

Staying still, waiting for Amethyst to wake up, Toola Roola felt like a brand new filly. Her sexual orientation had made her uncomfortable for years, but all that paled under the delightful wonders she’d shared with the mare. For the first time ever, she realized she actually wanted her friends to know about it, to know she loved other fillies, and that it was great.

Toola Roola thought about her best friend, Coconut Cream. She wanted to tell her how she really felt… and maybe even give her a hooves-on introduction. She smiled at the naughty thought.

4. Perky Prep & Flitter

(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.

5. Tender Taps, Skeedaddle, & Rare Find

(Vectors by Remul-Lemlem, FrownFactory, & thebosscamacho)

~ ✭ ~

Rare Find was studying an antique pendant when he heard somepony knock on his office door. He was a rather dashing unicorn stallion, with a brown coat, a white mane, blue eyes, and a cutie mark consisting of three green jewels.

"Come in!" Rare Find said, loud enough to be heard by whoever was behind the door. It creaked open, revealing a familiar face. "Oh, hello, Cheerilee! What can I do for you today?"

The earth pony smiled. "Hi, Rare Find! It's good to see you. As for why I'm here, it's because it's Friday, and this week's winner has asked to spend his night with you. It's Tender Taps; you might have seen him dance before."

"Oh, I see! I didn't even realize what day it was… So, it's a colt?"

Cheerilee nodded, looking a little worried. "Yes, indeed. I hope it's not an issue?"

"No, no," Rare Find assured her. "It's been a while since I laid with another stallion, but I do enjoy it. It'll be my pleasure to show Tender Taps a good time. I suppose that I shall pick him up after school today?"

"Ah, good! Yes," Cheerilee said. "And, if that is not too much to ask… You see, Tender Taps recently began to date another colt from the class, and he'd like to know if he could come too. They never have been intimate with each other, and it would be a great opportunity to have a responsible stallion to guide them during their first time. Skeedaddle is a good student too, so I suppose it's okay if he shares the prize just this once, but, of course, I need to know if you're comfortable with that as well."

Rare Find took a moment to think about it before answering, "Sure, that's no trouble. His coltfriend is more than welcome to join! I'll pick them both after class."

~ ✭ ~

Later that afternoon, Tender Taps was waiting with his coltfriend in Rare Find's living room, the stallion having gone to the kitchen to prepare some snacks. The young orange earth pony checked around the place; the room was full of intriguing antiquities, like clocks, paintings, jewelry, and a lot more.

Rare Find had explained that he worked with antique stores and museums to find, identify, and analyze ancient objects from all over Equestria. His home had a cozy, old-timey feel that was quite to Tender Taps' taste. "This place is pretty cool, huh? What do you think, Skeedaddle?"

Tender Taps' coltfriend was a young blue unicorn with a spiky blue and yellow mane, and a knot cutie mark. Skeedaddle gave the room a quick glance. "Yeah, I guess it's kinda neat. I'm more interested in you, though…"

Both colts blushed, and shared a long, deep look. Tender Taps' heart skipped a beat; Skeedaddle was so wonderful, and he was sitting right next to him on the couch, his face mere inches from his own. Of a common, unspoken accord, they each closed their eyes, and pressed their muzzles forward.

Tender Taps felt sparks of tingly, nervous excitement all over his body as his mouth met the other colt's soft lips. Kissing Skeedaddle was simply extraordinary, triggering strange new feelings Tender Taps had never felt from anypony else. They had only been together for a couple weeks, and he couldn't get enough of him. His cock slipped from its sheath, slowly growing between his legs.

Their kiss was cut short, however, by Rare Find's return, the stallion levitating a tea set and a platter of scones. Tender Taps and Skeedaddle parted, their cheeks red from embarrassment of having been caught like this.

The older unicorn let out a little laugh, cutting through some of the awkward tension. "Sorry, I didn't mean to interrupt you two. The tea is ready, if you want a cup."

The two colts nodded, and joined the stallion around the table. Using his magic, Rare Find expertly poured three cups of tea. "Sugar, or maybe some milk? I have honey too, if you prefer."

"Sugar for me," Tender Taps said.

"Yeah, me too," added Skeedaddle.

Once every teacup was ready, Rare Find levitated his own, and took a sip. "Mmh, exquisite."

The two colts gingerly used their forehooves to hold their own cups; though Skeedaddle was an unicorn too, his magic was still too unsteady to risk levitating their host's precious china.

"So," Rare Find said after a few minutes, "Miss Cheerilee said you two were a couple. Do you want to tell me about it?"

Put at ease by the stallion's gentle smile and friendly attitude, Tender Taps lowered his cup, glancing at his coltfriend. "Well, sure. Uh… I switched to Miss Cheerilee's class this year, and she put us in a team for the first group project. Skeedaddle started hanging out with me after that."

"One day, we kinda just… kissed," Skeedaddle continued. "I'm not sure why… He was just so cute, and it felt so good… I couldn't hold it."

Tender Taps sighed dreamily. "Yeah… And we want to… you know, go further than that, it's just… I'm not sure what we should do." The other colt nodded.

Rare Find finished his tea and left his cup on the table. "That's nothing to be ashamed of. We all have start somewhere, even with sex, but it really is worth it. So, how about we finish here, and move on to the bedroom? We'll start with simple things, and we'll go on from there. Okay?"

Tender Taps and Skeedaddle nodded in unison, nervous but excited.

~ ✭ ~

Rare Find settled down on the bed, inviting the colts to join him. They both laid down on their belly with their tails down, shyly hiding their genitals.

"Let's start with simply touching each other," the stallion proposed. "Skeedaddle, if that's okay, could you roll on your back so Tender Taps can explore you?"

Skeedaddle hesitated for a moment, but the sight of his coltfriend soothed his nerves. "Y-Yeah, sure!"

Tender Taps watched his special somepony expose his colthood; Skeedaddle was blushing, but he spread his hindlegs willingly, letting him peek in-between. Here it was: his coltfriend's penis. A couple inches had come out of his sheath, though the pink length was still soft. At the base, Skeedaddle's balls were nice and full, bulging with his seed. Tender Taps was fascinated; he had seen his friend's sex before, but never in such gorgeous details. It was amazing.

For Skeedaddle though, it was a bit embarrassing to be showing himself like this, not just to Tender Taps, but to Rare Find as well. It also triggered some deep seated insecurities. "Erm, it's not weird, isn't it…?"

"What? No!" Tender Taps blurted out, taken off guard.

Rare Find was more measured in his response. "Nope, there's nothing strange at all," he said, caressing the colt's inner thigh. "You have a lovely cock, Skeedaddle. You know, every penis is different, so it really is nothing to worry about. Becoming comfortable with yours is just part of growing up as a colt."

"Ah, okay. I see," Skeedaddle said, visibly relieved.

Looking up at Rare Find, Tender Taps asked, "Can… C-Can I touch it?"

The stallion cocked an eyebrow. "Well, I'm not actually the one you should ask, isn't it?"

"Oh, right… Sorry… Um, Skeedaddle? Can I touch your, um… your cock?"

Skeedaddle bit his lips. "Uh-uh! Please do it! Just, uh… be careful, ‘kay?"

Slowly, gently, Tender Taps caressed his coltfriend's sex, feeling its smoothness, its warmth. His touch elicited a soft gasp from the colt, making him smile. As Tender Taps lovingly stroked it, Skeedaddle's penis pulsed and grew, visibly hardening. It excited him even more: he was giving his special somepony an erection, and, in response, his own cock hardened under him. This was fun!

"Don't neglect his balls," Rare Find said, lounging comfortably on the bed. "Here, like this…" The stallion gently cupped Skeedaddle's testicles with his hoof, which got an immediate moan from the little colt.

Intrigued, Tender Taps fondled the little blue sack, feeling the pillowy softness of colt seed inside. It was a beautiful thing to behold, though it didn't beat Skeedaddle's blissful expression. "Huh, does it feel good?" Tender Taps asked.

"Y-Yeah… unf… so good~" Skeedaddle said, panting. "Could you, aah… do my dick again? A little faster, too…"

"I'll take over down there for you," Rare Find whispered in Tender Taps' ear. "Go on, you can make him cum."

Tender Taps stroked Skeedaddle's erection again, going up and down the hard, smooth length with his hoof. Meanwhile, Rare Find dipped his head behind the younger unicorn's butt. He admired Skeedaddle's cute little anus and quivering balls for a moment, then kissed the colt's sweet testes, and licked the entire sack. The stallion tenderly nibbled the wrinkly skin, careful not to hurt the colt, of course.

Seeing his coltfriend squirm in delight drove Tender Taps to go harder, faster on his cock. He masturbated him, his own penis throbbing in sync as he gave him everything he had. What Rare Find was doing was incredible too; the stallion had taken Skeedaddle's balls in his mouth, wrapping his lips around the base, and suckled his testicles.

"Mmmh! Aaaah! Yes!" Skeedaddle's flare swelled under their combined care, the colt gasping and moaning. Tender Taps' foreleg was tiring quickly, but he didn't stop. He couldn’t. He needed to see Skeedaddle's orgasm.

"T-Tender… ahh!" Arching his little spine, Skeedaddle came. White, gooey cum gushed from his penis, squirting all over his heaving chest. Marveling at the sight, Tender Taps continued to masturbate him. He could feel Skeedaddle's colthood twitch under his hoof as he ejaculated, load after load of sperm pouring in short bursts from his urethra.

Skeedaddle went limp, his head slumping backward on the bedsheet, and the flow of semen ebbed. His cock softened, and Tender Taps finally let go of it, Rare Find doing the same with his balls. The orange colt had never seen anything more arousing than his coltfriend lying in blissful afterglow, his fur soiled with his own sperm, his soft penis exposed for all to see.

Tender Taps wanted to cum. He wanted to add his own seed to the mess, to claim Skeedaddle as his own. Without a word, he mounted the spent colt and rubbed his testicles on his sheath. Holding Skeedaddle's flanks with his thighs for balance and standing upright over him, Tender Taps used his forehooves to grasp his erection. He masturbated without shame, letting himself go.

He noticed Rare Find shuffling closer, taking a similar position beside Skeedaddle, his much larger stallionhood erect and aiming for the younger unicorn's messy tummy. "Mind if I join you?" the stallion asked with a wink.

Tender Taps shook his head: seeing a stallion masturbate sure seemed like a lot of fun. Rare Find stroked himself, his forehooves blurred by the speed of his motion, and Tender Taps imitated him.

Meanwhile, Skeedaddle observed in awe the two cocks pointing at the mess of cum staining his belly. His semen was cooling down, feeling kinda icky, but it wouldn't be for long. With a loud, ecstatic whinny, Tender Taps ejaculated, spilling his warm seed on him. A second later, Rare Find let out a grunt, and his own semen gushed from his flared sex. Stallion and colt ejaculated together, emptying their testes on Skeedaddle.

When they eventually collapsed on either side of him, Skeedaddle's tummy was a mess of gooey sperm, the combined fruits of their three orgasms. As his coltfriend and Rare Find recovered from their climax, the young unicorn idly played with their cum, lazily swirling it around his chest with his hoof. It was sticky, droopy, and — quite frankly — really smelly, but it hardly mattered.

Rare Find stretched his back, his flaccid stallionhood flopping freely between his legs. "Mmmmh! Yep… That was fun!" He lazily settled down next to Skeedaddle, scooping some of the semen with his hoof. "We'll have to clean you up… though, maybe you'd like to try some first?"

"Try some? As in… tasting it?" Tender Taps asked, puzzled, as he laid himself down beside his coltfriend.

"Mmhmm!" Demonstrating it, Rare Find licked the cum off his hoof, gulping down their combined essences. Skeedaddle tentatively tasted his own hoof, and immediately made a face. The stallion smiled. "It can take a while to get used to the taste, but it's a lot of fun!" Lowering his head, Rare Find licked Skeedaddle's belly directly, sloppily cleaning his fur.

Tender Taps decided to imitate him. Closing his eyes, he licked a bit of cum, and immediately understood his coltfriend reaction: the stuff was bitter, salty, and the texture was pretty gross… and yet, it was sort of fun too. Without really thinking about it, the young earth pony started lapping Skeedaddle. Some of the sperm he was ingesting was most certainly his own, but he ignored it.

Rare Find and Tender Taps swallowed the bulk of the cum off Skeedaddle. It wasn't exactly a great cleanup, though, so the unicorn stallion went to pick up a wet bath sponge and some soap from the washroom. With a good scrub, Skeedaddle was eventually clean, his blue fur free of dried semen.

Everypony was feeling pretty drowsy from their ejaculations, so the three of them settled down for a nap, cuddling together and falling asleep in each other’s hooves.

~ ✭ ~

After the nap, Rare Find baked some pizzas in the oven, and the three shared dinner in the kitchen.

The colts' little chit chat as they ate was so cute. Tender Taps and Skeedaddle were experiencing their first love, their first relationship. It was a wonderful thing; shy, awkward, but beautifully intense. The young unicorn was more forward with his desire, and he often stole little kisses from his coltfriend. Not that Tender Taps was complaining…

It brought warm, fuzzy feelings to Rare Find as he watched over them. The stallion was usually more interested in mares, but the two colts were adorable together. It was a privilege to be able to share this with them, and to see them masturbate and ejaculate, to taste their seed. And there was so much more he could teach them. Rare Find was already working mentally on the next step of their sexual education.

When they finished cleaning up the dishes, Rare Find brought the two colts back to his bed. They were staring bright eyed at him, visibly eager to continue, their semi-erect penises proudly on display.

"Do you two want to try oral sex, now?" Rare Find asked, adventuring a hoof under Tender Taps' tail and caressing the colt's balls. "Giving blowjobs is a lot of fun, and a great way to have sex with another colt."

"Mmh, yeah! I don't know how, though…" Tender Taps said as he enjoyed the stallion's intimate touch.

"Uh-uh! Me neither!" Skeedaddle nodded, and Rare Find fondled his testicles too.

"That's alright. I'll demonstrate, then you can try yourself later, okay? First, you two sit down with a pillow against your back. This way you'll have a better view."

The two colts followed his instructions, getting in position. Rare Find made them sit as close as possible, their flanks touching, and invited them to spread their back legs. The stallion crouched down in front of them, getting at eye level with the two excited colthoods.

"When you begin, start by simply exploring your partner's penis," Rare Find said. "You can kiss it, lick it, nuzzle it, whatever you feel like." Demonstrating, the older unicorn gently kissed the flat tip of Tender Taps' glans, and rubbed his muzzle along his shaft, then did the same to Skeedaddle.

Going back and forth between the two foals, Rare Find played with their sexes. He explored their entire genitals, going all over their cute lengths, and lower still, licking their sheaths, their balls, and even their tight anus. Precum pearled from their urethras, and the stallion licked that too. Tender Taps and Skeedaddle's cocks quickly grew to full size, their erections pointing up like two tiny towers.

"Once you're ready, take the penis in your mouth," Rare Find said after a final kiss on Tender Taps' glans. "You don't have to go deeper than you're comfortable with: simply sucking the tip and using your hooves to stroke the rest feels amazing too. Just watch your teeth, and have fun."

Opening wide, the stallion took Tender Taps' erection in his mouth. He wrapped his lips around the swollen flare and suckled on it for a moment, then pushed down. The colt's smooth shaft slid in Rare Find's muzzle, and the stallion began to gently fellate him, bobbing his head. Tender Taps' penis was of a nice size… for a colt, which meant the stallion could comfortably fit him in his mouth, and he took full advantage of it.

After a minute, Rare Find moved on to Skeedaddle's colthood. It was a little shorter than Tender Taps', though the young unicorn had more girth. Moaning as he experienced his first fellation, Skeedaddle craned his neck, searching for his coltfriend's lips. The two colts tenderly made out, expressing their love in a way simple words could not. Rare Find sucked their penises in turns, going from one to the other in alternance.

Tender Taps was the first to cum. He gasped in his friend's mouth, and Rare Find suddenly tasted the colt's sticky, bitter sperm. He happily gulped it down. The colt's penis throbbed and twitched as he climaxed, his balls clenching as he emptied them in the older unicorn's muzzle. Panting, Tender Taps let out several spurt before his ejaculation ended.

Keeping a good mouthful of cum in his muzzle, Rare Find moved to kiss Skeedaddle. This time, the young unicorn didn't shy away and opened his maw, letting the stallion's tongue and his coltfriend's semen in. The two unicorns rubbed their penises on each other's before Rare Find returned to fellate the little colt. Skeedaddle was getting close to orgasm, and the stallion bobbed his head up and down to make it happen.

Unsurprisingly, Skeedaddle came too, and his gooey seed gushed in the stallion's mouth. Rare Find swished it around his mouth, savoring the colt's fresh sperm. He found it tasted saltier, and felt less bitter than Tender Taps' cum had been: Skeedaddle tasted pretty good, actually.

After a few loads of semen, Rare Find's gaze crossed Tender Taps' hungry stare. Giving him an unspoken invite, the stallion pulled back from Skeedaddle, receiving a squirt of goopy colt sperm on his snout before Tender Taps took over for him. Skeedaddle stroked his coltfriend's mane as he ejaculated in his mouth, making him taste his seed.

Rare Find watched them finish, a smile on his lips and the feeling of a job well done. He licked the cum off his muzzle as they relaxed, spent for the time being.

He was still hard, however, and he needed to relieve himself, so he levitated a bottle of lube from his drawer. "Mind if I mount one of you?" the stallion asked, squeezing a generous amount of clear, slippery gel over his erect cock.

The colts looked at each other, and Tender Taps blushed. "I… I'd like to." Biting his lip in anticipation, the orange colt lifted his rump and presented his tailhole.

Rare Find mounted him, lining his glans with the colt's pert anus, teasing the tight sphincter. "Have you done this before?" Tender Taps shook his head in response, and the stallion reassuringly petted him, caressing his purple mane. "Don't worry, I'll take it slow. You just have to relax, and I'll do the rest."

With Skeedaddle observing from the side, Rare Find pushed gently with his tip on Tender Taps' tailhole. He wasn't exactly the most well-endowed stallion in Equestria, but he wasn't small either. Nothing really happened at first, but the stallion was patient; if the colt was to have a good first experience from anal sex, he needed to be careful with him. Rushing would only make it hurt, or even cause damage, something the stallion wanted to avoid at all cost.

Sure enough, Tender Taps' anus eventually loosened up to the point where the stallion could safely enter him. Rare Find pushed down with his pelvis, leveraging his weight to penetrate the colt. Tender Taps' ponut stretched around the stallion's engorged glans until the wide flare slipped inside.

Tender Taps groaned from the momentary discomfort, so Rare Find gently stroked his mane. "There, there… You're doing great. That was the hard part." It was indeed much easier afterward. With slow, shallow thrusts, Rare Find steadily made his way into the colt's rectum, until, eventually, he hilted his entire stallionhood inside the foal, his heavy balls nudging the colt's smaller sack. Rare Find inhaled deeply, closing his eyes. "Aaaah… You feel sooo good, Tender Taps!"

"R-Really?"

"Mmhmm!" That was an understatement, actually: the colt's insides were perfect, tight and warm and incredibly cozy. The stallion began to mate with him in earnest, thrusting in and out of his ass. His testicles jiggled freely under his tail, bumping the colt's ballsack with every penetration.

Wide eyed, Skeedaddle watched his coltfriend mate with the stallion. Rare Find saw the colt's erection was recovering swiftly from his previous climax, and it made him smile. "Wanna try it too?" the stallion asked between thrusts.

Skeedaddle expression lit up. "Can I?

"Uh-uh! Just give me a minute, and he's all yours. You can lube yourself in the meantime." Rare Find plunged once more in Tender Taps' butt, picking up speed.

"Aaah! Yeah! That's so good!" the little colt cried out. The stallionhood in his ass was providing his prostate quite a pounding, and his own cock bounced between his hindlegs, growing harder with each penetration.

With Skeedaddle waiting for his turn, Rare Find wasted no time to finish himself. He pounded into Tender Taps with all he had, enjoying everything the foal's tight little body had to offer, until, finally, he slammed hard into him, his glans flaring deep inside.

Tender Taps felt the stallion's heavy balls throb against his own testes, and then a twitch running through the shaft in his rectum. Warm, creamy stallion sperm gushed deep inside: Rare Find was ejaculating inside him. The older unicorn stayed there, emptying his quivering ballsack in the orange colt's bowels, his seed flowing in his colon. Rare Find eventually pulled out of Tender Taps and dismounted him, leaving his gooey semen inside the colt. He settled down beside him, nuzzling and kissing his ears as a gesture of gratitude for the good times had.

Skeedaddle quickly took Rare Find's place, mounting his coltfriend's rump and lining his cock with the gaping tailhole under his tail. The stallion observed the little unicorn vigilantly, ready to intervene in case he wasn't careful enough, but Skeedaddle penetrated the other colt with great tenderness. His sex easily entered Tender Taps' already loose rectum, the lubricant and Rare Find's sperm aiding its passage.

Once fully inside, rather than immediately thrusting in and out, Skeedaddle wrapped his forelegs around Tender Taps' neck and buried his face in his soft purple mane. "T-Tender… I… I love you… Mmmh! I love you so much! I wanna feel all of you! Aaaah!" With a grunt, Skeedaddle pulled back a couple inches, and pushed back inside, their testicles meeting with a soft slap.

"Skee… Skeedaddle… Aaah! I-I love you too! Unf! Oh, yes… Please!" Tender Taps pushed back with his rump, getting more of his coltfriend in him.

Rare Find watched the foals make love from the sideline, seeing their little bodies coming together in shared pleasure. A warm feeling spread inside him, something that wasn’t caused by the sex, but by the ardent glow of young love on full display before him. The two colts were sweaty, disheveled as they shared this wonderful embrace.

Skeedaddle was lovingly pounding his friend’s luscious butt, giving everything he had to their mutual pleasure. His cock, shorter than Rare Find’s stallionhood, actually let his glans stroke Tender Taps’ prostate with every thrust, and it made the orange colt’s penis pulse in sync with Skeedaddle’s penetrations.

Rare Find gently caressed their bodies with his hoof as they mated. He stroked Tender Taps’ colthood, then explored under their tails to fondle their testicles. The colts’ balls were smaller and wrinklier than they had been before their previous ejaculations, but they still held some seed for another. The stallion petted Skeedaddle’s virgin tailhole, making the little blue unicorn gasp even more.

Tender Taps let out a throaty moan, his mouth wide open and his eyes closed. A jet of sperm squirted from his cock, followed by a couple more, the foal ejaculating the rest of his semen on Rare Find’s bedsheets, staining the fabric with fresh colt cum. His rectum clenched hard around Skeedaddle’s flaring sex, and the young unicorn rammed deep into him, hugging him tight from behind. He held Tender Taps with all his strength, biting his ear, telling him he was in him to stay. Skeedaddle’s balls twitched, and he ejaculated inside his coltfriend, his viscous cum mingling with Rare Find’s semen in Tender Taps’ bowels.

Skeedaddle trembled atop Tender Taps, until finally his strength faltered. Both colts went limp, gasping for breath, the goopy result of their love oozing around Skeedaddle’s receding sex. The unicorn foal left his flaccid length in his coltfriend’s anus, perhaps too exhausted to even pull out, or perhaps simply not wanting to. Tender Taps closed his eyes and fell asleep, utterly content. Skeedaddle sleepily nuzzled the side of his face, planting a little kiss on his cheek. “Love you…” he murmured, before he dozed off as well.

Rare Find tucked them under the blanket, and gave each colt a little kiss on the forehead. Deciding to leave them together for the moment, the stallion quietly got out of bed.

He peeked at his old grandsire clock on the wall; it wasn’t very late. Tender Taps and Skeedaddle would probably wake up before actually settling down for the night.

Rare Find wondered if they’d be up for another round.

6. Scootaloo & Rainbow Dash

~ ✭ ~

Sitting at her desk, Scootaloo idly watched Miss Cheerilee chatting with Pipsqueak without really paying them attention. Everypony else had already left for the weekend, including Apple Bloom and Sweetie Belle, leaving the young pegasus to wait in class alone.

She was exhausted. Studying was difficult. She had no issues learning stuff, but actually sitting down to revise, or to do homework, was… awful. She just couldn't stay focused, and the more Scootaloo forced herself, the worst it got. Why did she have to work twice as much than anypony else in class?

But, Scootaloo had worked super hard the entire week, and she finally did it: for the first time ever, she won Cheerilee's weekly reward. It was her turn to make love with somepony, to discover sex. She was so excited…

And yet, she was nervous. Why did she have to ask for Rainbow Dash, of all ponies? Of course, Rainbow Dash was Scootaloo's lifelong hero, but the filly had never really been attracted to other girls. Sure, Rainbow Dash occasionally appeared in her mind when she masturbated, but more as a kind of mentor, not a partner. What if Rainbow thought she was weird? Or, what if it changed their relationship?

With a sigh, Scoot chased that train of thoughts from her mind. She knew perfectly well that Rainbow Dash would be nice to her, that she'd do her best for her… and, yet, she was still worried.

Fortunately, the mare in question showed up before Scootaloo could chicken out of their night together. Rainbow Dash cheerfully hopped on the chair Sweetie Belle normally occupied, sitting next to Scootaloo.

"Hey, squirt! Sorry I'm late… Had to fly to Canterlot real quick this afternoon. Wonderbolt business."

"H-Hey, Rainbow Dash. Um…" Scootaloo wasn't sure what to say. Some kind of pickup line? She didn't really know any, and it sounded super awkward anyway.

After an excessively long pause, Dash cleared her throat. "So, are we going to my place?"

"Oh? Yeah!" That did sound nice, and if they were going to Rainbow Dash's home, it meant Dash would give Scootaloo a lift.

They said farewell to Cheerilee and went out. Dash knelt down, helping the filly climb on her back. Scootaloo hugged the mare's neck, burying her snout in the seven colored mane. Rainbow Dash soared in the sky, carrying home her young friend. Holding tight, Scootaloo let go of her worries. She loved to fly, to feel the rush of air in her mane. It was a bittersweet thing that she could not do it with her own wings, but being with Rainbow Dash, to feel her firm muscles as she flew, more than made up for it.

Below, Ponyville was basked in the warm glow of sunset. Instead of heading straight home, Rainbow Dash casually went around town, taking her little buddy for a ride. For a while, neither said a thing.

After a final flyby of Sweet Apple Acres, Rainbow Dash and Scootaloo arrived at Rainbow's cloud house. Scootaloo hopped off the mare, and enjoyed the fluffy, cushiony cloud under her hooves. Even without functional wings, Scootaloo could still walk on clouds, thanks to the natural pegasus magic that flowed within her.

Rainbow Dash ushered her young guest inside.

"I was glad when Cheerilee told me you were coming here tonight," the mare said, ruffling Scootaloo's mane. "Speaking of, she also told me you've been really awesome this week, and that your grades got better, so congrats! I'm really proud of you!"

Rainbow Dash put her hoof under the filly's chin and looked her straight in the eyes. "And, you're a big girl now, so how about we go straight to the bedroom and I show you big girl stuff?"

"Um, sure…" Hesitantly, Scootaloo followed her upstairs. Dash lifted her tail, showing off her vulva, but it only embarrassed the filly, who looked away instead.

"It's your first time, isn't it?" Rainbow Dash said, more like a statement than a question.

"Y-Yeah…"

"Eh, don't worry! First times are great, you'll see. I figured there's all sorts of cool sexy stuff we can do together. Oh boy, this is gonna be so awesome! Bet I could tie you up and make you cum with just my tail, or maybe we could play a game?"

Entering Rainbow Dash's bedroom, Scootaloo really thought she'd be more excited than that. Being with her idol, doing stuff with her, usually made her all giddy, but not this time. She just… wasn't sexually attracted to her.

Noticing the filly's downcast eyes, Rainbow Dash stopped, her cocky grin morphing into an expression of concern. "Hey, you alright? Something's wrong? If it's too much, we can just do vanilla stuff if you want."

Scootaloo shook her head, avoiding the mare's eyes. "It's… not that… Dash, you're amazing, I want to be just like you, but… I should have picked a stallion." Tears welled up her eyes, her voice breaking. "I don't know why I picked you… I'm sorry, I just wasted your time…"

Hooves gently wrapped around her. It took a moment for Scootaloo to realize she was being hugged by Rainbow Dash. It was a tender, comforting gesture, not sexual at all, and Scootaloo leaned onto the mare. Overcome with emotion, the filly sobbed quietly, wetting Dash's fur with her tears.

"There, there, it's okay, Scoot," Rainbow Dash whispered, stroking the filly's soft purple mane, letting her cry.

Scootaloo huddled closer. "I'm sorry… I'm so stupid…"

"Hey, you're not stupid." Gently, Rainbow Dash wiped the tears off her face. "Life's been hard on you, I know. Your wings, your parents… But you keep going, no matter what. You're brave, and loyal to your friends. You're awesome, Scoot. You hear me?"

The filly sniffed, still sobbing, not saying anything.

Rainbow Dash sighed. "You know, I was so hype when Cheerilee told me you wanted to spend the night with me, because I wanted to make you feel as amazing as you are. Having a good roll in the hay with you would be cool, but only if it's fun for both of us. If you want, I can drop you off to your aunts' place, or we can just have a normal sleepover here."

"R-Really?"

"Yeah, really! We can play board games all night, or make a pillow fort. Heck, we can do makeovers and stuff, if that's what you want." Rainbow's expression suddenly turned pensive. "Though… if you like handsome guys, I do have plenty of magazines in my stash."

Scootaloo immediately felt a flicker of excitement. "Woah! What kind of magazines?"

Rainbow Dash snickered, and shot the filly a wink. "I got all kinds, duh. Anything from sport models to pornos. Wanna browse some of my favourites with me? We can start with the less naughty ones, and move on to the others if it gets you going."

Scootaloo's face flushed scarlet, but checking out hot stallions with Rainbow Dash sure sounded fun. It certainly was more to her taste. "O-Okay, yeah! I-I wanna see."

Grinning, the mare opened the drawer of her nightstand and grabbed a big pile of magazines, which she let spill on the bed. Scootaloo hopped on Rainbow Dash's fluffy bedsheets, eager to see what she had.

Scootaloo shuffled through the pile of scattered magazines, checking out the glossy covers and reading the titles. As promised, there was nothing explicit or even saucy in there, just pictures of stallions and mares in sporty outfits.

"Anything catches your eyes?" Rainbow Dash asked.

"Hmm… Yeah…" Scootaloo kept browsing, unsure which she preferred. Eventually, she stumbled upon a cover which got her interest: it was a picture of a pegasus stallion with a wild mane, standing over a cliff and looking confidently toward the horizon. The title read Equestrian Wanderers: Expedition to Mount Everhoot with Gale Hawk.

"Oooh, nice one!" Rainbow Dash commented.

Curious, Scootaloo skimmed over the pages. It was full of pictures, most showing dashing stallions in climbing gears against stunning mountain landscapes, with little paragraphs of text giving some context. "This is so cool!"

"Yeah, Equestrian Wanderers is great," Dash said, looking over the filly's shoulder.

One photograph was of three stallions chatting around a campfire, visibly tired after a long day but happy to be there together. Scootaloo lightly stroked the picture. It wasn’t very difficult to feel desire for these guys; they were handsome, adventurous, brave. "I'd like to go with them, discovering new places and hanging out, you know?"

"Hehe, maybe not tonight, squirt… but you will someday."

Scootaloo brightened up. "You really think so?"

Rainbow Dash teasingly ruffled the filly's mane. "Of course you're gonna do it, Scoot! You're the best filly around. And guys will beg to go with you, trust me."

Scootaloo bit her lip. She couldn't ignore the nagging thoughts at the back of her head, telling her always she was a failure, a mistake… but she trusted Rainbow Dash more than those. Checking the photograph again, it was easier now to picture herself with those guys. Her body would be sore from days spent hiking in the mountains, but the triumph would be bliss, and she'd revel in it with her friends.

And maybe one of the guys would be willing to share a tent with her, no?

Very tempted to find some fuel for those thoughts, Scootaloo almost asked Rainbow Dash to bring her saucier magazines, but she was too embarrassed to do so. Instead, she closed the one she was reading and grabbed another edition of Equestrian Wanderers, this one focusing on an expedition to a tropical island.

Scootaloo browsed various publications, getting a sense of her own preferences. Some magazines were about the Wonderbolts, and some were about different sports. While she liked those, Scoot was surprised to realize she felt much more strongly for the adventuring stuff. The sense of scale, the danger, it called to her.

The filly was getting very curious about what else Rainbow had in store. Luckily, Rainbow Dash wasn't known for her patience. Getting bored, the mare poked Scootaloo in the ribs. "Eh, mind if we move on?"

Scootaloo blushed and nodded.

"Awesome!" Smiling, Dash prodded under her mattress for a moment before producing a cardboard box. She casually shoveled the previous magazines off the bedsheets to make room for the new ones.

Compared to the previous bunch, these ones were definitely on the saucy side. Shivers ran through Scootaloo's flank as the filly peered at the covers, seeing stallions and mares in suggestive poses. She picked one at random, and skimmed through it. Halfway through the magazine, Scootaloo stumbled upon a full page photograph of two stallions walking side by side. It wasn't exactly sexually explicit, but the picture was taken from behind, and the two stallions' tails weren't properly covering their rears, conveniently providing a nice view of the heavy balls dangling underneath their tailholes.

"Just imagine how it'd feel like when they empty those things inside you," Rainbow Dash said, licking her lips.

Scootaloo's nether warmed up all of a sudden. "Y-Yeah… Um… Did you ever do it?"

"Uh-uh! Plenty of times!" Tenderly, Dash caressed the filly's lower belly. "When a guy cum, you feel his tip flare deep inside you, and he pushes it as far as it will go. And, when you feel that… I dunno… You just want him there, and it feels amazing. Then, his dick kinda pulses, and you get this warm, creamy feeling that spreads right around here, in your belly."

Blushing, Scootaloo simply turned the page and continued to browse. There were more attractive stallions there, and she spent a while simply looking at them.

The next magazine offered even better shots of genitals, male and female. Scootaloo found a photo that showed every detail of a stallion's cock, which she dreamily traced the length of with her hoof.

"You know, Scoot," Rainbow Dash said, amused. "If you want to hold one of those, I might have something for you." Chuckling quietly at the filly's dumbfounded look, Dash retrieved yet another box from under her bed. However, what she pulled out of it wasn't a magazine, but a black silicone replica of an erect stallionhood.

"Huh, is that…?"

"A dildo, duh! Neat, right? Sure, I get plenty of action, but it gets handy sometimes."

Scootaloo examined the toy. Curiosity had free reins, and she ran her hoof along the smooth length. It looked — in Scootaloo's arguably limited experience — very realistic, with an arborescence of veins adorning the hard shaft, a thicker medial ring, and a flattened flare at the end. It even had balls, a pair of pillowy sacks at the base. Surely, that thing had been inside Rainbow Dash before, inside her vagina, and it gave the filly a strange, naughty thrill just thinking about it. What would it even feel like to have something like this in you?

Scootaloo was getting quite hot and sweaty. It was getting especially damp under her tail, where the lips of her vulva were spreading the heat of her budding arousal. She stirred uncomfortably.

A situation shared by Rainbow Dash, apparently. Without really thinking about it, the mare rolled on her back, bent her spine, and caressed her sex, as she so often did after a hard day practicing with the Wonderbolts. Rainbow Dash masturbated tenderly, releasing all the arousal she'd been building up. She moaned, her hoof stroking her labia, dipping in her vulva.

"Hah, better!" Rainbow Dash said, stretching her wings. Oh, she needed this.

At her side, Scootaloo was blushing, plainly aware of what was going on. Her idol was doing such an intimate act in her presence, simply letting go. Their eyes met, and under Dash's hazy, lustful stare, Scootaloo felt the trust of her mentor. Rainbow Dash was always so cool, showing haughty confidence to all who'd meet her, never faltering. That she would lower her guard as such, let Scoot witness her in such a vulnerable, compromising moment, was an acceptance the filly had never dared dream of.

Scootaloo was finally at ease. Enough, anyway, to drop her own inhibitions. Her fillyhood was winking, pulsing, ready to be shown some love. Giving the enticing pictures one last glance, Scootaloo laid her chin on the pillow and spread her hindhooves. With a deep breath, she passed her hoof under her barrel, caressed her crotch, then touched her little slit. "Mmmmh…"

Dash smiled. "Look at you, squirt! Nothing to worry about. Just have fun!"

The filly said nothing. She simply stroked her sex, feeling the warm softness of her vulva. Her little clit poked out, and she pressed on it with the hard edge of her hoof. She loved the intense pain-pleasure it caused, and it quickly fueled her arousal.

*Shlick-shlick-shlick*

Scootaloo masturbated alongside Rainbow Dash. Filly and mare tended to their own pleasure, a couple feet apart on the bedsheets. They weren't having sex — not exactly — but that was okay. For the young pegasus, it was enough.

The scent of Rainbow's sex was nice, and her little throaty moans were too. Scoot kept checking her out, getting an enticing sneak peek at her mentor's techniques; Scootaloo always did kind of the same thing when she pleasured herself, and she was curious to know how Rainbow Dash tended to herself. Rainbow clopped in an entirely different way than Scootaloo. She was on her back, almost curled into a ball to reach her nether, which she rubbed vigorously with unmistakable glee. It contrasted with Scootaloo's style, who preferred to raise her butt and press with greater force on her pussy.

Everypony, boys and girls, had their own way, their technique, Miss Cheerilee had said once. It was the natural way of things. Truth be told, while Scootaloo was interested in learning, she wasn't compelled to imitate her idol on this.

Not that Rainbow Dash didn't seem to enjoy herself. "Nnngh, aah! Oh fuck… Scoot, you're gonna use that?"

Confused, Scootaloo checked around to find whatever Dash was talking about, only to see the dildo laying on the sheets. She had left it there and had completely forgotten about it. "Um… No? I dunno?"

Dash's lustful smile didn't waiver. "Well, if you change your mind, that's cool. For now though, don't mind if I do." She tenderly stroked the toy, and made herself comfortable.

A hoof still caressing her little fillyhood, Scootaloo watched in awe. Rainbow Dash teased herself, rubbing the fake glans against her labia and exposing the pink flesh of her sex. The head of the toy grew slick with Dash's fluids, and her clit winked happily.

A cute, feminine moan came from Rainbow Dash. Eyes shut and biting her lip, she pressed on her entrance. Her fold parted, letting the flared tip of the dildo disappear inside her waiting snatch. She rubbed it there, wiggling the shaft around. "Oh, yeah, that's the stuff…"

Scootaloo rubbed her own slit a little harder. "Does it hurt?"

"Nah… It feels great. Mm…" Smiling, Dash pushed the dildo deeper into her sex. As she took the toy into herself, the mare squirmed in excitement and swayed her hips, her hindlegs trembling slightly. Inch after inch, the toy disappeared in-between Dash's blue labia, sinking in her vagina until only the black balls were left outside.

Grinning, Rainbow Dash left it there for a moment, her pussy winking with delight around the base. Of course, since she was the Rainbow Dash, it was only for a moment: quickly, she pulled out the soaked shaft nearly all the way to the flare, then pushed it back in with one swift stroke.

Scootaloo's hoof picked up speed, the filly instinctively syncing her rhythm with her mentor's increasingly loud moans and coos of pleasure. Scoot masturbated with feverish intensity, her young eyes glued to Dash's pussy, only occasionally straying to peek at Dash's flushed, pleased face.

The filly inhaled deeply, taking in the powerful scent of excited mare. A trail of wetness, gleaming in the sunset light filtering through the windows, oozed from Rainbow Dash pussy, soaking her rainbow tail a little more with each plunge of the dildo into her sex. It was going in and out so fast it was almost a blur, Dash putting in everything she'd got into the motion.

The older mare was panting, her legs were trembling, but she only pressed harder. Scoot knew what was happening: Rainbow Dash was about to climax.

And Scootaloo wanted to see it.

"A-Aaah!" With one last throaty squeal, Rainbow Dash came. She slammed the dildo as deep as it would go, holding it in place as her vagina contracted around it over and over again. Her chest heaved, and she bit her lip to stifle her cry.

Fascinated, her hoof wet from her own pleasure, Scoot caressed her mentor's belly, feeling the contractions under her sweaty blue fur.

"Aah… unf… ahh… oh yes… aaaah…" Coming down from her peak, Dash went limp, her head laying on the pillow. She let go of the dildo, letting it slip from her gaping vulva.

With a goofy grin, Dash turned to her young onlooker, her hoof idly caressing her puffy sex. "So, Scoot… what did you think?"

"It looked… awesome," Scootaloo replied in a daze, her own clit winking furiously, begging for release.

"Well, it's your turn now. Wanna try it?"

Scootaloo gulped, but her mouth delivered the only answer her needy pussy would allow: "O-Okay!"

Rainbow Dash grinned even more, proud of her little pupil. "Sweet! You're gonna love this! Hang on a sec…"

A bit wobbly, as if drunk from her orgasm, Dash nonetheless made her way to the box she'd pulled the dildo from and retrieved another item from it. This time, it was a sort of harness, which she promptly fitted around her hindquarters. Then, she attached the dildo to it, clipping it between her legs so she wore it like a stallion would.

Rainbow Dash posed proudly, displaying her new equipment, the black tip still dripping on the bedsheets. "There! Now you can get the full guy experience… kinda."

"Um, what do I do?"

Rainbow Dash caressed Scootaloo's mane, then moved behind her. "Just stay still, okay? I'll take care of everything." Gently, she lifted the filly's tail, and planted a soft kiss on her most intimate parts. A shiver ran along Scootaloo's spine, but Dash simply climbed on her back, pinning the soft purple tail under her belly.

With a hoof, the mare guided the hard flare to her little buddy's excited fillyhood. Scootaloo cooed: the thing pressing on her sex felt heavenly, still warm and slick from its time in her mentor's vagina. Her labia opened willingly, letting the dildo slip inside her velvety canal.

Dash pushed slowly with her hips, cautious not to hurt Scootaloo as she took her virginity. Aided by the filly excitement, the shaft slid smoothly into her sex, her vaginal muscles parting to accommodate the plastic girth. Gently, Dash pushed the flare to the filly's cervix and wrapped her forehooves around her neck, hugging her.

Nibbling on Scootaloo's ears, Dash whispered into them, "Feeling good?"

"Uh-uh…"

Smiling, Rainbow Dash pulled back, leaving an aching void within the filly, which was then promptly filled again as the older mare thrusted back in, producing a wet smack as her thighs met Scootaloo's butt.

"Aaah! Yes!"

Dash picked up a steady rhythm, carefully letting her young partner's inner walls stretch around the dildo. Soon enough though, the filly's tight vagina ceased offering much resistance at all, and Dash gave her more, confident she could take it without pain.

As she mated Scootaloo, Rainbow Dash licked the filly's ears and planted little kisses all over her mane. Pleasantly surprised by her mentor's softer, caring side, Scootaloo moaned and cried, begging for more. Already stimulated from before, the young pegasus was trembling, feeling the onset of something wonderful building within her very core.

"You close, buddy?" Rainbow Dash asked, barely slowing down.

"Mmm! Hm-hmm! Y-Yeah! P-please!"

So, after a few extra frenzied thrusts, Rainbow Dash slammed roughly all the way into Scootaloo's sex and bit her ear hard, a primal yet effective way for a male to tell his partner he was in to stay, to unleash his fertile sperm within her womb.

The filly cried out with joy, and a little bit of pain, as she came. It shook her harder than any climax she'd ever given herself. For a brief, wonderful moment, there was nothing but the fire coursing through her flesh, white-hot like nothing she'd felt before.

And then it faded, but it was okay, because she was hugged by tender, caring hooves. As Scootaloo went limp, her breath ragged from exertion, Rainbow Dash gently pulled out the strap-on from her sensitive fillyhood and discarded it to the side to be taken care of later. She caressed Scootaloo's mane, letting her recover.

Once her heart had settled down a little, Scootaloo turned to Rainbow Dash. "Did I… Did I do it right?"

Dash kissed the filly's snout. "You did perfect, and you were as awesome as you always are. More importantly, though: did you have fun?"

Scootaloo smiled. "Yeah! It was amazing!"

There was a moment of silence, then Dash grinned. "I'm glad. So… next time, how about I invite a couple of Wonderbolt boys to join us? That'd be pretty great, right?"

Scootaloo grinned too.

1. Pipsqueak & Cheerilee

~ ✭ ~

Cheerilee loved all her students, even the difficult ones. She really did. Still, she sometimes wished she could return home alone on Friday after a hard week. Between Snip and Snail's antics and the Crusaders' attempt at helping a filly earn a beekeeping cutie mark, this week had been especially dreadful.

As students went home for the weekend, Cheerilee felt like she’d earned herself a good, strong drink. However, she still had to reward her best student of the week. Fortunately, it was Pipsqueak that had ended up with the most pins next to his name on the board, and he was such a good kid.

Pip trotted happily next to Cheerilee as she walked him to her home, and she invited him inside with a smile. Pip earned the weekly reward more often than most, and he was getting quite comfortable with Miss Cheerilee's place. He politely wiped the dirt off his hooves, dropped his saddlebags in the hallway, and sat on her coziest couch.

Cheerilee wasn't worried about leaving him out of her sight in her house, unlike some other students, so she took her time to put away her own things and go to the kitchen first. "Pip, do you want a snack? Maybe something to drink?" Cheerilee asked, loud enough for him to hear from the living room.

"Um, do you still have chocolate milk and cookies?"

"Sure!" Cheerilee prepared a plate of chocolate chip cookies, and poured a glass of chocolate milk, before bringing them to Pip on a platter.

"Thanks, Miss Cheerilee! You're the best!" Pipsqueak eagerly chumped down a cookie.

"You're welcome, Pip! You deserve it. Thank you again for your help this week. Things have been a little crazy, and I'm exhausted."

This elicited a look of concern from the little colt. "Are you alright? I can go home if you don’t feel well."

Cheerilee smiled. "That's very thoughtful of you, Pip, but it's alright. I can still take care of you tonight. Here…" She huddled close to him on the couch. Between his legs, his small colthood had already begun to emerge from its sheath, and Cheerilee gently caressed his testicles with the soft inner part of her hoof. His penis swelled from her touch, the arteries in Pip's shaft expanding and filling it with blood.

"Do you want to finish your snack, or take care of this first?" Cheerilee asked.

Pip did not answer directly, but he blushed and pushed away the remaining cookies, shyly looking down at his erection. Miss Cheerilee petted his mane, and dipped her muzzle under his barrel. Pip's colthood was small, but she knew he was at full length already. A clear, gooey drop of precum pearled at his urethra, and Cheerilee licked it off, tasting the salty, musky liquid.

Cheerilee opened her mouth and wrapped her lips around the tiny colt glans. She pushed forward, letting his sex enter her muzzle. Pip was so small that she could comfortably fit his entire erection in her mouth. She even let her tongue loll out and used it to scoop his balls within the comfort of her muzzle, taking the colt's entire genitalia inside. She suckled Pip's cock at a leisurely pace, using her tongue to lick his firm testes. It wasn't hard to get a colt to cum, so she was in no hurry. She gently stimulated his sex, giving him time to enjoy her ministrations. Still, in less than a minute, Pip's flare bulged in her mouth, and she tasted his musky, bitter seed.

Cheerilee let her student finish, then swallowed his gooey semen with some difficulty. She'd never really liked the taste of colt sperm, and the texture was kind of icky. Pip had certainly earned it, though, so Cheerilee did her best for him. She kissed his penis as it shrunk back into its sheath, and then hugged him.

For a minute, Pipsqueak panted, recovering from his orgasm. He then returned Cheerilee's embrace, nuzzling her coat. She planted a kiss in his soft, brown mane. Cuddling his little body felt so good. "So, Pip, did you like it?"

"Mmhmm," the colt replied dreamily. "I loved it."

Cheerilee kissed him again. "I'm glad. Do you want to relax for a moment and play a board game before dinner?"

Pip nodded.

For the rest of the afternoon, Cheerilee played a few rounds of Settlers of Cantertine with Pip, then cooked some macaroni and cheese — a dish that made any foal happy. They then played several games of Pegasi & Cumulus, until Cheerilee noticed her student was getting distracted. The source of the disturbance was easy to spot: Pip's cock was hard again.

"C'mon, let's go to bed," Cheerilee said, gently stroking his erection. Pip nodded eagerly, and followed her to her bedroom. It was small, but cozy. Pip hopped on her bed while she closed off the curtain. Now that they had some privacy, Cheerilee sprawled on the bedsheet next to him, and wrapped her forelegs around his neck, pulling him into a kiss. She smiled, feeling Pip's tongue on her lips, and she opened her mouth, letting him explore her muzzle. They made out until Pipsqueak pulled back to breathe. The little colt rubbed his sex on her chest.

Cheerilee knew Pip was getting comfortable with sex, as they had done this a few times before, so she skipped the basic instructions. "What do you want to do first?"

Pip blushed, biting his lips. "Um… I'd like to lick you, Miss Cheerilee. You know… under your tail."

Cheerilee chuckled at his coyness. "That's my 'vulva', Pip. You don't have to be shy." She gently broke their embrace, then turned in the opposite direction, lifting her tail to present her sex. The young colt eagerly kissed her marehood, slipping his tongue in her slit.

Cheerilee moaned appreciatively; she wasn’t exactly aroused just yet, but Pip's tongue felt good. Still, her vulva soon grew wet, more so than only his saliva could be responsible for.

A familiar warmth spread in her belly; Cheerilee's vagina was getting coated in her natural lube, her body getting ready for intercourse. Pip's licking and suckling were starting to feel really good, actually. Unfortunately, now that she was ready for him, Pip stopped his work and mounted her rump. Cheerilee stifled her protests: she was doing this to reward him, and he was only a little colt, after all, so she couldn't expect him to please her like a lover should.

Anyway, Cheerilee soon felt his glans probe her vulva. With an adorable little grunt, Pip pushed his cock inside her, all the way to his sheath, his barrel pinning her tail up. His sex was too small to be really satisfying, only reaching a few inches inside, but it still sent tingles of pleasure through her rump. Cheerilee clenched her vaginal muscles, providing enough friction for both of them to have fun. She was too tired to really do much more, but, luckily, Pip had energy to spare, and he eagerly spent it thrusting inside her.

Cheerilee looked over her shoulder, her heart warming as she saw the little colt's blissful expression. He was so cute, mating her like this, his ballsack bumping her clit with every penetration. Cheerilee was glad to have made him cum earlier, allowing her to enjoy him longer now that he wasn't so pent up.

Still, Cheerilee knew Pip wouldn't last forever, and she wanted to cum too, so she dipped her forehoof between her legs to play with her clit. As Pip thrusted his cock into her marehood with rising determination, Cheerilee masturbated, pleasing herself. She rubbed her clitoris directly, quickly building her arousal. She rarely came while rewarding a student, but her climax was fast approaching, her vagina and womb pulsing with ardent lust.

Then, Pip bit her tail, and she shuddered in pleasure. Cheerilee gasped, and her snatch contracted hard, locking her young partner inside. "Aaah! YES!" Cheerilee slammed her face into her pillow, savoring her orgasm.

Pip flared, his glans bulging in her canal. "Unf… M-Miss… Cheerilee, I'm… Ah!" He pushed forward, lodging himself as deeply as he could in her sex. His little penis throbbed, and Cheerilee smiled, feeling the soft, luscious warmth of colt semen coat her inner walls, adding to the delightful glow of her orgasm. Pip's testicles twitched against her clit as he ejaculated, delivering his seed in her vagina.

Instinctively, Cheerilee bent her spine and lifted her rump, letting his gooey cum flow deeper in her body. Pip's sperm oozed through her cervix, and pooled in her uterus. Of course, Cheerilee had already taken her birth-control, so she simply enjoyed the wonderful sensation without worrying about carrying her student's foal.

Her afterglow settling in, Cheerilee relaxed, letting Pip ejaculate in her most intimate place to his heart's content. He eventually pulled out of her, and planted a gentle 'thank you' kiss on her puffy vulva, his snout brushing against her tailhole. Completely spent, Pip crawled back to lay next to her. Cheerilee embraced him again, and they rested in each other’s hooves.

"Wow, you felt really good inside, Miss Cheerilee!" Pip said after recovering his breath. "You were sorta… pulsing around me near the end."

Cheerilee giggled. "That's because I came, Pip. I had an orgasm."

"Uh? Like when I shoot my sticky stuff inside you?"

"Yes, kind of like that. It feels really good, but, since I'm a mare, instead of ejaculating, my vagina contracts repeatedly to help my partner finish in me."

"Huh…" Pip stayed pensive for a moment, reflecting on this new information. "So, erm, does that mean you didn't have fun before, Miss Cheerilee?" Concerns glazed his eyes.

Cheerilee ruffled the colt's mane, reassuring him. "Oh, don't worry, Pip. That's sweet of you to ask, but I do this every Friday to reward my students. It's my job. Honestly, it's rare I get to cum; I'm just happy to make foals happy. But, if it makes you feel better, I like being with you like this: not all my students are as nice as you."

Pipsqueak frowned. "What do you mean? Some ponies don't like being with you?"

She probably shouldn't have answered that question, but Cheerilee liked the pillow talk. "Well, everypony has different tastes, and I can't be everything. For example, a lot of the fillies would prefer to have sex with a stallion, and some colts too. Even for those that like mares, not all of them are attracted to me… or me to them. That's perfectly natural, so I simply make do."

Pip remained silent for a long while. "Well, maybe we could ask other ponies to help… The student council could send an offer for volunteers in Ponyville. That way, anypony who earns the weekly reward can choose somepony they like."

Cheerilee stared at the young colt, dumbfounded. "You know, that's a really good idea, Pip! I'm sure we could find plenty of stallions and mares to give our best students a good time. And… that would free up my Friday evenings too."

Pipsqueak beamed. "You really think so? Thanks, Miss Cheerilee! Though, if you don't mind… I'd like to choose you again. I want to make you cum too."

Cheerilee kissed him, right on the lips. "I'd love to, Pip! I can even teach you tonight, if you're still up for it…" She rubbed her belly on his crotch, feeling another erection. Excited to have him inside her again, Cheerilee rolled on her back and helped Pip get in position between her legs. They shared a goofy, happy grin as he penetrated her, his little colthood easily slipping in her snatch.

Following Cheerilee's gentle guidance, Pip rubbed her clit with his hooves as they mated. Using her hindlegs, Cheerilee guided his thrusts, setting the rhythm of their motions. Electric surges coursed through her spine, her entire body shuddering in intense pleasure.

A few minutes later, Cheerilee surrendered to bliss as Pipsqueak ejaculated inside her again. She locked him in with her hindlegs, happily accepting his seed in her womb. When they both came down from their peak, they huddled close. Pip fell asleep in Cheerilee's hooves. Careful not to disturb him, she turned off her bedside lamp and held him tight, enjoying the contact of his little body on her fur.

~ ✭ ~

The following Monday, Pipsqueak presented his plan to the class, Cheerilee watching from the corner, a warm smile on her lips. The proposition quickly sparked interest from his classmates, fillies and colts suggesting names of local ponies who might be interested.

Once the student council accepted the new plans, Cheerilee drafted a notice to be distributed in town. Several mares and stallions volunteered, generously willing to give deserving foals a good time.

With something for everypony, all students now worked extra hard to earn star pins, going out of their ways to demonstrate their good behaviour to their teacher. And, every Friday, a lucky colt or filly left school with a generous pony welcoming them in their home for the night.

As for herself, Cheerilee could now enjoy her free weekends… except, of course, when one of her students actually chose her.