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Wrapped in Blankets

Summary:

During playtime, a shy puppy has an embarrassing condition, and Calypso finds him just in time to help.
When left with him in isolation, however, Calypso struggles against her own perverted temptations, and things steer a different way...

Notes:

Okay so it's been some YEARS now It seems like nobody's written a single calypso-centric dirtyfic yet..
SOMEONE has to finally show her some appreciation, and I guess it's gotta be me. Enjoy!

(See the end of the work for more notes.)

Work Text:

In the heart of Glasshouse Primary School, it was yet another lively day.
Calypso stood in front of her bright and colorful classroom, filled with children buzzing with excitement. Rest time had just ended, and now it was playtime—the moment when the kids always seemed to have endless energy. It always amused her how quickly they sprang to their usual spots, ready to play again.

Despite the noise and chaos, she didn't mind it at all. The best lessons, after all, came from children interacting with each other, right? Smiling softly, Calypso sat down and resumed knitting the scarf she’d been working on.

The children were happily absorbed in their games and stories. Bluey was busy stacking blocks, the soft clink of each piece adding to the room's hum, while Coco and Indy scribbled away, filling their drawings with colors. Calypso smiled, her knitting needles clicking rhythmically as she watched.

Out of the corner of her eye though, Calypso spotted one of her students, Jack Russel, sitting alone in a corner, looking oddly uncomfortable. He was nestled inside a small fort, which wasn’t unusual, but his friends Rusty and Mackenzie were on the other side of the classroom, fully engaged in their game of war. Calypso set her needles down and approached him.

Jack glanced up, but his usual bright smile was absent. She knew him well enough to sense when something was off.
"That’s a nice house you’ve built here," she said softly, hoping to gently encourage him.
He didn’t respond, only glancing away.

"do you mind if I visit?"

Jack nodded, but his expression remained unchanged.

"Are you waiting for someone??" She asked playfully.

"I.. I don't know," Jack mumbled, his voice barely above a whisper, averting his gaze from the entrance.
He didn’t have any toys with him, just huddled inside his fort, looking lost.

"You know, I saw Rusty and Mackenzie deep in their mission over there. I bet they could really use your help, don’t you think?" Calypso offered, her tone gentle and encouraging.
She flashed a warm smile into the small entrance, but Jack only nodded slightly, his expression still troubled.

What was wrong? Was he sick again? Were the boys too rough on him?
Calypso sat cross legged outside the small entrance and cleared her throat, prompting his attention.

"Are you feeling okay, hon?" she pushed, her concern now evident.
Looking closer, she noticed something was... off. His fur looked a little messy, and his cheeks were flushed...something she hasn't seen from him before.
"Goodness, Jack, what's going on? Are you hurt?"

"I, um, I don't know...Rusty doesn't want to play with me anymore," Jack mumbled, not looking her in the eyes. "I think I'm sick...I don't know what to do Ms. Calypso.."

"What makes you say that, honey??"

"...I'm turning weird and red... I think I need to go to the hospital," Jack said, looking down at his paws.

"Turning...Red??"
This sounded like a scrape, or maybe a fever? Either way, she needed to get a look.

"Can you come out so I can take a look??"

The boy hesitated, staring back at her sheepishly. "I'm hiding here from the others... I don't want to come out."

"Okay hon, I understand," she comforted him. "I'll help you stay hidden. I can bring my special big walls to hide us, and we'll both be safe in here. Would that help??"

Jack hesitated for a moment but finally nodded.

It wasn't too long before Calypso returned with a pile of blankets. She carefully draped them, moving and adding pieces to the canvas, closing the entrance completely and creating a cozy, cocoon-like space. It was still a bit cramped, but her focus was on making her student feel safe.

She crouched down, gently examining his fur for any signs of injury. "Where does it hurt? Can you show me?"

Jack looked hesitant, avoiding her eyes. "It’s just my... um... my—" He stuttered, clearly embarrassed.
Slowly, he pointed down to his crotch, where a small, red tip was poking from his sheath.

Oh...

She didn't exactly want to stare, but she couldn't help but find the display a little...curious..
As his teacher, she didn't want to make the little terrier any more uncomfortable than he already was.

She paused for a moment, glancing up and down his body.

She stared and eyed his features. That little embarrassed face was so cute...and his messy fur..

Jack was a little confused at the funny face she was making. Why was Ms. Calypso looking at him like that?

"Am I in trouble?"

"Oh, no, no...You're fine, it's alright," Calypso quickly reassured.

"Oh, good..." Jack muttered, still looking very embarrassed.

"How do you feel, sweetie?" She asked, her voice growing soft again.

She still hadn't really given him an explanation.
Jack looked up at her curiously for a moment, shifting uncomfortably. His chest felt tight, like there was something tangled up inside, but he couldn’t put his paw on it.

"I feel... kinda funny," he muttered, glancing down at the floor, trying to find the right words. "Especially on my... thingy." His voice wavered, barely a whisper now, as if speaking it aloud made the feeling worse.

"Alright, little one..." Her voice was careful, but Jack could hear the hesitation in it. "Let’s see... I think... well..."

Just a little touch wouldn't hurt... it was part of her job to, right?

"Jack, would you be okay with me... touching a little bit, just to make sure you're not hurt?" Her tone was gentle, but there was something under, something he couldn't quite describe.

Jack didn't say anything, just gave a slight nod. He inched closer to her looking away, trying to distract himself from the feelings of exposure.

...

He felt a hand graze his thighs. It was a soft touch, but the sudden contact made him twitch.

The little terrier squirmed a bit, but his hips didn't shift away. Her paws slid gently across his most sensitive part, her soft touches bringing life to an odd sensation.

He didn't get what was going on, but his whole face was red as a tomato.

He couldn't describe it really. It was like warm, fuzzy, tickling bubbles inside him. A funny tingle. He'd never felt anything like it.

As she traced it up and down with a single paw, she heard him gasp softly. Just the feeling of how big her paws were made him shudder a bit, but Jack stayed still..

"You're doing so well, honey, just relax..." Calypso purred.

Jack didn't have the words to describe it, but it didn't hurt, that was for sure.

Jack was shifting a bit in front of her, and she noticed the way he was breathing was getting a little funny... his face looked tense.

...

As his teacher, she was supposed to take care of him.

She wasn't doing this for any weird sexual gratification, of course.
No, of course not. She was just helping a child, right? This is part of her job, this is what teachers are supposed to do..right?

"Hmm, okay, I'm almost done...really," she murmured, but Jack couldn't tell whether she was speaking to herself, or him.

"I-It's okay Ms. Calypso, it doesn't hurt..." his voice quivered. She was squishing a really funny part now..

He glanced up at her with a curious, but reassuring look.

Her paw began massaging, feeling him through his sheath. Jack wasn't sure how to react, outside of uneasy gasps and sighs.

Just a momentary lapse of reason and professionalism, nothing wrong here, everything is under control.

She didn't even notice that she had already found a rhythm. Her mind was racing through reasons why this was perfectly appropriate, why she shouldn't be feeling so guilty right now. It didn't matter what
reasons she had come up with.. her paws were memorizing every touch. It felt so...

Seconds passed, and a slight whine came from his lips.

"Is it alright??" she whispered, glancing up at him.

His response wasn’t words, just a soft sound. "Mhmnh..." A vulnerable whimper escaped the puppy, his eyes shut tight.

Calypso's cheeks grew so hot she felt like Jack could see them through the dim light.

"Jack...we're almost done, but..."

She could barely hear the noises outside anymore.. his little noise echoed in her head like a spell.

She closed the entrance completely.

"I need you to stay really quiet now...and, I need you to sit up here for me...okay sweetie? We can take care of this."

Calypso instructed, gesturing to him in a sitting position. He wordlessly complied and climbed into her lap, facing away from her.

She shifted them around a bit and leaned back onto the pile of pillows he was laying against.

"Comfortable, Jack??" she asked, settling his weight into the crook of her hips.

Jack silently nodded his head.

He had never been pressed so close to Ms. Calypso before. Her fur was so much fluffier than it looked...and she smelled so pretty—like apples and cinnamon.

Now it was just the darkness, their uneven breaths and a familiar tingling guiding them.

With one paw holding his hip, her other gently ran over him. In the dim of the canvas, the textures were the best guide to follow.
Calypso palmed circles into Jack's tummy, slowly nearing his more delicate parts. Jack could feel her thighs start to rub together underneath him.

She felt something poking at her. Jack's little tail was planted directly between her thighs, slowly twitching back and forth against her.
For a moment, she debated moving him, or asking him to curl his tail away, but...

Jack felt his teacher shuffling under him. His tail felt a bit trapped, and it was rubbing into something hot, but he didn't think much of it.

She just barely began to tug when she felt his hips instinctively buck into her paw. Oh dear...

Even if she knew this reaction wasn't exactly intentional, the implications of it gave her butterflies.

"Jack?" she whispered.

No response. Just panting and quiet, gaspy breaths.

In the dark, two paws squeezed at her thighs, trying to steady the little body in her lap.

She felt another thrust from him, and another, and another... His body was already moving on its own.

The motions of his little hips were grinding his tail into her sensitivity, which had already become damp..
Calypso eagerly rolled her hips back against it, closing her eyes dreamily. With every hump the little puppy's tail was dipping into her. She was enjoying every movement...

The pair of hips were pumping together in a rhythm, thoughts were swirling like a fog.

In a moment of surrender the puppy let out a sweet, hushed moan against her, and her grip around him instinctively tightened.
Thanks to Jack's assistance she had a free paw, which she was now running up and down his body, caressing him all over.

She was running purely on instinct, and she needed more of him. She nuzzled into the heat of his neck, huffing his puppy scent.
"Shh shhh, good boy..." She cooed, and he felt a little kiss on his neck.

She could feel her thighs involuntarily tense and squeeze together, pushing his tail further into her.

Climbing and building, the pair continued to move faster, thrusting and grinding harder into each other. The whole fort trembled as they rocked against each other.

His little paws squeezed her so tight that she let out a little yelp into his neck.

His little body convulsed against her, small drops of warmth spreading over his teacher's paw.

"I-I mm, Ms. Calypso, im s-sorry, mmhhgn—~!"

 

Calypso rode the wave of heat for a few seconds , rolling her hips to match his pace.

Jack cried and gasped against her arm, making one final buck into her, and they both panted in exhaustion.

He finally fell into a slow, shallow breath, and went limp on top of her.

After what seemed like forever, their breathing finally slowed and they relaxed.

Jack laid exhausted on her. Both their legs and hips were sticky and warm...

Calypso hadn't expected to reach any kind of peak, but the whole ordeal brought her dizzyingly close.

She let out a content sigh.

...phew...

The space inside the cocoon had become so hot and stifling. They hadn't really noticed it before.

Now the air was thick with the sweet scent of his teacher's perfume, and their mixed arousal.

After what felt like forever, she slowly shifted Jack off of her lap.

They rested there for a minute, and the sounds beyond the tent slowly drifted back in— the other kids still playing and learning happily, completely innocent to what had just happened.

She was almost relieved to hear the busy noises again, knowing that the students were doing fine without her.

After a slow recovery, she got up and crawled to the entrance of the tent, peeking hesitantly at her clock.

By some miracle, everything was still on schedule for cleanup, and even story time.

She paused for a moment, and looked back to jack.

He was laying there with his eyes closed, surrounded by the messy blankets with a peaceful look on his face.

It was a good thing those were machine washable...

She crawled back in and folded up the covers, to at least cover the dark patch they had left on the sheets.

"Did you...Did you like that??" She wasn't quite sure why she was asking that. But more than anything she needed to know.

"Mhm...." He made a tired, content hum..

The answer was more than anything she could have asked for. Ms. Calypso left him to rest there.

"Come on children, let's start cleaning up! It's almost story time," He could hear his teacher bark out excitedly.

She peeked back in one last time.

"Would you like to listen from here for today?"

Jack gave her a warm, affirming smile. "Yes please," he made a gentle mumble.

He curled up in the pile of blankets and rested his head against the pillows. His heartbeat slowed, and the peacefulness of the classroom surrounded him.

Once everyone had settled she began to read. As she read, the soothing sound of her voice filled the room, surrounding Jack like a cloud.
He tried to follow the story, but quickly lost himself in his teacher's voice. Before long, his eyelids were growing so heavy...

He thought about space.

He thought about his mum.

He thought about the kiss Ms. Calypso gave him when he was being a good boy.

The scent of her pretty perfume and something else he couldn't really describe still lingered on him, and it made him feel like he was floating.

Nestled warmly in her words and fuzzy blankets, Jack was out like a light.

-----

The rest of the day was a blur. It was pickup time, and his mum was out in front.

He made it to the door where Calypso had his bag.
"Bye Ms. Calypso," he got closer to her and gave her a hug, which was a first. "You're the best.."
It was a very welcome surprise. Her eyes met his for a second, and there was a strange glimmer in his. She smiled back at him, and they parted.

"Thank you, Sweetie. See you soon!"

And with that, he was off.

THE END

Notes:

Hey,. I'm pretty proud of this story and I hope you really enjoyed it.

If you do, PLEASE don't be shy to tell me, I love comments and feed back SO much. Like a ton...

[update: there's a VERY solid chance that this fic will be turned into a comic, so if you have any critiques let me know before it's finalized!]

Yeah. Calypso is awesome, so are you for reading this. Bye!