Author's Note

Day 1: Pumpkin

“Toola, get over here, Filly!” Coconut Cream shouted exuberantly as she hopped up on top of a hay bale in the middle of a thick patch of pumpkins. Leafy-green vines surrounded her, wrapping and twisting all around the ground in front of her. From them, varying hues of Pumpkins from earthy green to vibrant orange and pale yellow were scattered around; some of them small and barely-grown, others massive, easily dwarfing the size of a filly.

“What is it?” Toola Roola separated from the rest of their class with a smirk and a raised eyebrow. As Miss Cherilee ushered the remaining students along their tour of the Sweet Apple Acres pumpkin patch, the filly raised onto her haunches and plopped her hooves on the white post of a fence. “Find something cool?”

“Totally cool.” Coconut gave her a wry smirk, her eyes sparkling with mischief. “Come over here!”

Toola Roola hoisted herself up onto the fencepost, hind legs struggling to find purchase. Hooves clopped against the dilapidated wood before she anchored herself and pushed, clambering over the top and falling over the other side, collapsing in a heap next to a particularly large pumpkin with an ‘Oof!’ She collected herself, stood up, and dusted off with a start.

“Coco? What’s up?” she trotted a few steps forward until she was right next to the brash-looking Coconut, still eyeing her with that devious grin.

“I just had the BEST idea ever, in the history of best ideas!”

“You did?” Toola blinked, struggling how this had to do with their field trip surrounding pumpkins. At the very least it had to be better than boring old pumpkins. Coconut Cream leaned closer as if about to tell her some super-secret, and just when Toola’s anticipation and curiosity had reached its peak, Coconut reached forward and caught Toola’s ear in her teeth and tugged at it.

“E-eek!” Toola yelped and tried to carefully pull away. Her cheeks immediately burned a deep red from blushing, her tail snapping down between her legs. “C-Coco…”

Coconut released her ear with an even bigger grin, batting her eyelashes as if she’d done nothing wrong.

“So about that idea…” Coconut Cream whispered, being careful the class was already far away, no one was around, and the pair was long-forgotten by the careless teacher.

“Yeah?” Toola rubbed her ear.

“Wanna do something naughty?”

“Wha-” Toola, nearly speechless, rubbed the back of her hoof and took her turn to look up and down the patch. “O-oh. Now?”

Coconut Cream nodded, squirming on her pumpkin as if her body were pining for any amount of contact or friction she could get.

“Okay. Yeah. Fine.” Toola took a deep breath. “Let’s do it!”

In an instant Coconut had grabbed her friend’s hoof and swept her up, dragging her through the maze of vines and pumpkins. A little way down the patch there were several exceptionally large pumpkins, large enough that a couple promiscuous fillies would be hard to spot huddled behind.

The pair crouched down, hiding just out of sight, pressed up to the rough sides of the biggest pumpkin out of a handful bunched up together.

Coconut Cream had taken on a sultry pose, sauntering about with a few seductive flicks of her tail. At first, Toola imagined that Coconut might plant herself in her lap or lean in for a kiss, but instead, the filly waltzed over to a more average pumpkin, widened her legs until she was straddling the large orange plant, and lowered her tight little filly rear upon it.

Toola Roola watched with equal parts surprise and fascination as her friend plopped her rear down and ground hard up against the long, thick stem that jutted out at the top of the pumpkin, having previously been cut from its vine and pruned. Toola’s eyes widened when Coconut, having planted a hoof in front of her to anchor and brace herself, started lowering herself onto the stem. It poked at her small, puffy folds and abruptly slipped between them.

It had an immediate effect on poor Coconut, who had to cover her mouth with her one free hoof to keep from calling out as her poor filly cunny clenched down hard and seemed to ripple around the rough, thick texture of the stem.

Despite her hoof covering her mouth, she let out a squeal; she had slipped the rest of the way down the pumpkin, her tush making an impact with a little bounce. Her eyes looked about to roll back in her head before she clenched her eyes firmly shut, another squeal stuck in her throat.

Toola watched with mute fascination, a hoof drifting down her stomach to the naughty place between her legs. It grazed across her slit, touching around her plump fillyhood. She squeezed and ground her hoof up and against herself, spreading her folds and revealing the wet, pink flesh underneath. Already aroused from the sight, her hoof became damp and sticky, a tingling sensation bubbling up from deep inside.

Coconut Cream readjusted herself with trembling hooves, planting her forehooves onto the surface of the pumpkin in front of her. With the new leverage, she lifted her rump, pulling back on the stem, and slammed back down in a flash. Her back arched and her hind legs shook. She bit her lip and tried to swallow back her moan, but without her hoof stuffed in her mouth, she couldn’t keep it shut.

“Ahhhhng! T-toola! G-gosh!”

Seeing her best friend already in the throes of an intense sensation, Toola doubled down with her hoof. Her tiny nub winked and her folds glistened with juices. She attacked it, rubbing her hoof on the sensitive button with a desperate want. The sensation was intense and immediately rewarding. She practically slumped back against the orange wall behind her, panting slowly.

“C-coco. Unng.”

By now Coconut Cream’s rump was moving in a flurry of humping and grinding, the thick stem, once dry as a bone, now wet and glistening as it slipped in and out of her quivering pussy. All attempts for discretion abandoned, her tongue hung loosely out of her open maw as she moaned readily and willingly.

“B-buck. Oh gosh. This feels a-amazing, Toola.”

“H-haah. I bet. You’re so hot, filly!” Toola Roola was rubbing herself raw, her hoof nearly sore as it buzzed back and forth against her throbbing fillyhood.

“Nnng. Not as hot as you.” Coconut shut her eyes as her body started to reach its peak. “Oh...OHH!” Suddenly her rump moved as if with a mind of its own, slamming down and grinding back and forth. Humping and moaning, she suddenly spasmed, little squirts of filly juices leaking out and splattering all over the top of the thoroughly-molested pumpkin.

So emboldened by watching her friend, and satisfied with the sight of seeing her pleasure, Toola found her climax soon after, her clit throbbing against rubbing hoof, hind legs clenching around it despite herself. She soaked her hoof in seconds while she writhed around, eyes rolling back.

Falling back into a heap and coming down from her high, Toola Roola laid down and closed her eyes as her post-climax bliss began to take over, and newfound fatigue set in. She barely registered the other filly in front of her or heard the sounds of the garden around them.

“Wow…” Toola muttered, a contented smile on her face.

Coconut Cream had keeled over on the pumpkin with the stem still inside. Her fillyhood had stopped clenching tight and quivering, her inner walls finally relaxing. She caught her breath and waited for her heart to finally settle before starting to sit upright. The motion caused another clench of her vaginal walls from deep within, and she exhaled sharply.

Hoofsteps suddenly caught her attention from behind, closer than she’d expect them to be. She likely hadn’t heard them before because she’d been so loud in the throes of orgasm.

A large red stallion stepped into view before she could say anything, or pry herself off. She found herself uncharacteristically speechless, struggling to find an explanation for the predicament they found themselves in. He must have been there to scold them, right?

The stallion looked between the two fillies. The silence that hung between them was so sudden that Toola Roola opened her eyes. She gasped quietly and abruptly sat up, looking around fearfully.

Instead, he put a hoof to his mouth as if to motion a silent hush. He sat on his haunches and rose, planting a sturdy hoof on the enormous pumpkin just beside Coconut Cream and the pumpkin she was planted on.

Toola Roola peered out from behind the stallion to see what was going on, making brief eye contact with the equally-surprised Coconut, but before either of them could speak an enormous and heavy member flopped right in front of Coconut Cream’s face.

“Get suckin’,” he said, “An’ don’t let me keep you from what you were doin'.”