The Little Colt that Could

by Epic_hooves

First published

A lonely colt moves to Ponyville, where Cheerilee shows him how to make friends, and love.

A lonely colt moves to Ponyville, and has some trouble fitting in at school, and Cheerilee tries to help him out. Cheerilee feels some un-professional feelings towards the colt, and one day she sees him playing all by himself, so she decides to teach him how to make friends, and love.

The Little Colt that Could

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“The Little Colt That Could”

It was another average day at the Ponyville Schoolhouse, and Cheerilee had just quieted down the rowdy class of ponies. She was starting a new lesson on friendship, when she heard a knock at the door.
“Oh, that must be the new student!” She cheerfully exclaimed as she trotted over to the door.
She swung it open to reveal a shy little colt, with a light gray coat, black, slightly unkempt mane with a few streaks of ghostly white, and an orange marble cutie mark with a few spirals in it. He seemed a bit nervous, with his head hung low, he kicked a small hoof into the dirt. Behind him stood what she assumed to be his dad, a large gray stallion with a tie on, and a neatly cropped mane, smiling at her, completely unaware of his son’s emotions.
The father started speaking “Hi there, sorry for running behind a bit, it took us a little longer to get Sigmund ready for school.”
“Oh, that’s quite alright! Here, come in, come in!” said Cheerilee motioning them inside. The class had started talking, gossiping, and throwing things, so she tried calming them down.
“Alright class, that’s quite enough, we want to be on our best behavior for our newest student Sigmund.”
They all quieted down, and simultaneously shouted,
“Hi Sigmund!”
The nervous pony stood awkwardly at the front of the class for a few silent moments.
“Tell us a little bit about yourself!” Said Cheerilee, trying to break the ice.
“Why not tell us where you’re from?” She continued.
“Canterlot…” The lonely pony said in an almost whisper quiet voice.
Realizing that she should just spare the pony anymore suffering, she quickly escorted him over to his seat, all the while he hung his head in shame. Cheerilee quickly ran back to the front of the classroom, and told Sigmund’s father all about the schedule, recess times, school supplies, and field trip days.
“… And that’s about it!” Cheerilee finished
“Alright,” Replied Sigmund’s father.
“Have fun kiddo!” He said as he walked out the door.
The day went by pretty quickly, and just as everypony was pushing and shoving their way out, Cheerilee spotted Sigmund at his desk, where he had just finished packing up his things and was slowly heading towards the door. Cheerilee let out a sigh and went over to comfort the small pony
“I know it’s hard moving to a new place, but trust me, it gets better!” Cheerilee exclaimed.
“I don’t know, nobody seemed to really like me.” Said a depressed Sigmund.
“Oh don’t worry, it’s only your first day, you’ll make lots of friends!” She said, trying to cheer him up.
“Ok, I guess…” The little pony said as he walked out the door. Despite her better judgment, Cheerilee found herself drawn to the new pony’s flanks. They were surprisingly well muscled, considering his age and seemingly bookish tendencies. Something stirred inside her and she felt her face take on a light blush as she recognized she had just been checking out her new student.

As the week passed by Cheerilee began paying more attention to the little colt, and on numerous accounts caught herself day-dreaming about him. Lost in thought, she began to wander Ponyville, not really paying attention to where she was going, and not really caring. The mare found herself in a position she’d never dreamed she’d end up in. A crush on a student was not only morally wrong, and professionally inappropriate, but it was difficult. Sigmund would be in an awkward place in his life, undergoing a lot of changes both physically and mentally. And boy, did she want to see those physical ones.

As she continued on her way, she realized she’d reached the outskirts of ponyville and was somewhere near Sweet Apple Acres. The fragrant scent of those apples filled her nostrils, and she closed her eyes as she took a deep whiff. With a sigh, she opened her eyes, and was surprised to see the little colt that was the source of all her troubles. He looked like he was playing marbles all alone. A pang of pity went through her, over-powering her desire as she went over to check on him.
“Hey Sigmund, what are you doing?” She said, smiling cheerfully.
“Just playing marbles…” He said with a sigh.
She kneeled down and looked at one of them.
“Wow, that’s just like the one on your cutie mark!” She exclaimed.
“Yeah, it’s my favorite. My dad bought it for me on our vacation to Fillydelphia when I was little.” He said, now facing Cheerilee.”
“Oh, really? I’ve always wanted to go to Fillydephia, but I never managed to get away from town.” Cheerilee told him, sitting in the dirt next to him. Sigmund didn’t look up from his marbles. The mare sighed and looked him over, trying her damndest to do it in a nonsexual fashion, but failing.
“Sigmund, are you having trouble fitting in?” She asked, her voice filled with concern and comfort.
“I dunno… nopony really tries to talk to me, and I just feel lonely, living in a new place and all.” Said a depressed Sigmund.
“Have you tried talking to anyone?” She replied.
“No… not really but I don’t think they’ll like me.” He said, kicking the dirt.
“Oh come on, just remember what I taught last week, try talking to people, and see what they like, you never know, people might surprise you!” Cheerilee said looking him in the eyes. Sigmund let those thoughts mull over for a bit in his brain, then he started to get a little smile, and said
“I guess you’re right, maybe I should stop being so lonely, and try talking to people!”
“That’s the spirit…” Realizing she probably wouldn’t have another time to talk to him alone like this she made her first move.
“So, are there any mares you like in school?” She said, stepping forward.
“Uh…” He stammered, trying to think of something to say “Yeah, I guess so.”
“Like who?” Cheerilee said, leaning in a bit closer to him raising an eyebrow.
Sigmund bit his lip, and started to sweat. He could practically feel her breath, hot and damp, and her mane, soft and luscious, smelling like apples and peaches.
“Uh, Sweetie Belle seems pretty nice…” he muttered, as he began experiencing a new warm feeling of arousal between his flanks. Just as he was about to say something he felt Cheerilee give him a few gentle pecks on his neck, slowly making her way up, and all he could vocalize was a slow moan. At first he wanted to pull away or say something, but then Cheerilee wrapped her forelegs around his neck, and slowly drove her tongue into the pony’s mouth. Unsure how to react, Sigmund just stood there and went along with it, playing with her soft tongue, gently darting it in and out of her mouth. They stood there kissing for a few moments that seemed to be forever, when Cheerilee tenderly pulled away. Her loins became soaked with juices, so she eased them both to the ground where she wrapped herself around the shaking little pony, embracing his small yet muscular figure. Sigmund was about to say something when Cheerilee brought a hoof up to his mouth and said,
“Don’t worry, everything’s going to be just fine” in her beautiful and seductive voice that would put anypony under her spell. She gently rolled Sigmund over onto his back only to see his large erection poking out, already wet with pre-cum. Cheerilee gasped with excitement and lust at this sight.
“Oh my, you’re so much bigger than most stallions I’ve met!” She exclaimed looking it over, feeling it’s girth in her hooves. “Oh we’re going to have a lot of fun with this…”

Cheerilee began working the vainy shaft with both hooves, furiously rubbing and licking its spongy tip all the way to its firm base. Sigmund began moaning loudly, bracing himself against the ground as his teacher partook in the forbidden fruits this colt had to offer. He started shaking, having such immense pleasurable feelings pushed upon him all at once felt wonderful, and exhilarating at the same time. Cheerilee peeked over at the sweaty pony’s face from behind his stallion sized cock, when she slowed her rubbing and licking, then ultimately came to a halt. Sigmund, spread eagle in the dirt, he laid his head back, panting heavily. Cheerilee stood over him, and leaned down to kiss him, but just as their tongues started to mingle she pulled away, lowered herself, and planted his bulging cock in her firm, tight pussy. She moaned with pain and pleasure as she struggled to fit it all in, and as she finally felt her hips touching his balls she let out an exasperated moan. He let out a small “Oof!” as she slowly started working her hips up and down, with her forelegs both planted firmly next to the colt’s head. As she worked her tight pulsing hole over his long hard rod Sigmund began moaning, and experiencing such intense feelings of arousal he nearly blacked out a few times. After a few seemingly endless minutes of lust and enjoyment Sigmund started feeling sharp jolts of immense pleasure he began sputtering
“I… I… Grrrrraaaaaahhhhhhhhhhhhh” as he released his load deep into Cheerilee’s juicy cunt. The sudden gush of hot, thick semen from his young, but large balls made Cheerilee scream at the top of her lungs, as she felt his dick throb and pulse inside her. The viscous white fluid leaked out of her, onto Sigmund, and the floor, and splattered over any other nearby surface.
“Well… that was wonderfully spectacular!” She said as she pulled Sigmund’s rod all the way out of her. As she stood up she noticed that her stomach had begun to swell up, and giggled as she gently pressed down in it, pushing the excess fluid from her womb. Sigmund shakily picked himself, and dusted himself off, then he looked at his erect penis hanging out in front of him, semen still dripping from the tip.
“Wow…” he said, at a loss for words “What was that? It felt amazing, why doesn’t everypony know about it?”
The reality of it had begun to settle in on Cheerilee, and she decided to tell him about sex.
“Well, when one pony loves another very much, and they want to make a little foal or colt, they do that, but people don’t want hundreds of little ponies running all over, now would we? That’s why some parents don’t tell their children about ‘sex’ until they’re old enough to understand that it’s a very serious thing.”
“Oh,” he said, still shivering a bit “B-but doesn’t that mean you’ll have a… baby?”
“Oh no, don’t worry, sometimes when a pony is feeling lonely and wants to get close with another they do the same thing! Except there are spells, herbs, and medicine to prevent against babies in case they don’t want one, or aren’t ready.” She explained.
“Oh, well thank you! I think I’ll be settling in just fine from now on.” He said, beaming with pride and happiness.
“Oh you’re welcome; I was quite impressed with you, this being your first time and all.” She said as she walked past him “Oh, and if you ever get lonely again, just talk to me” She said with a wink as she began walking back towards Ponyville, with a spring in her step.