Ponyville After School

~ ✭ ~

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.