Tender Foal-Sitting

Olive Tenderfoot is a foal-sitter, living a cosy life in Camelot. But her charges are far from the traditional affair...

Tender Foal-Sitting

Olive Tenderfoot skipped through the gates into the residential district of Canterlot with a smile on her face. The day had gone well, clients popping over to her small office in the marketplace for meetings and financial admin were the boring part of her job but seeing the bits add up at the end of the day always gave her a boost.

She was on the way to see one of her clients now, in fact. She’d been paid up front to book her time and the pony in question had given her his name and address. She didn’t need to ask much more, only enough to know what to pack in her colourful knapsack. Her tuque was neatly covering the base of her unicorn horn, the tousled brown mane she kept just tidy enough to look presentable pressed down against her head. It wasn’t exactly a mainstream fashion choice but it was the most comfortable headwear she’d found.

Her horn began to emit its pinkish white glow while a piece of paper unfolded and emerged from the side pocket of her bag. An address was hastily scrawled there, noting her destination was only a few wooden doors further down the street.

Arriving at the door she gave it two firm knocks with her hoof. A few clopping noises were heard from the other side before the heavy oak swung inwards to reveal the stallion behind it. He was young, probably just out of Canterlot University or doing an apprenticeship with one of the many guilds. He was struggling to make eye contact with Olive, his face beginning to go beat red as she began to take in what was in front of her.

The poor boy was shaking, clearly nervous and protective of his space. He’d come to her in person before of course but he’d been smartly dressed and confident at the time. Whatever headspace he’d managed to get himself into then was clearly no longer one he could keep up, undressed with his adorable little cutie mark on display.

“Skipper, was it?” Olive smiled at him, pulling her head down so that she could try and catch his eyes. He nodded and sniffed, his eyes darting back and forth between looking at her and looking towards the ground.

“Can I come in?”

His head shot back up, his mane standing on end as his blush came full force to his face and ears. It took him a few seconds to compose himself, stepping back a few steps and nodding slowly.

“Thank you, don’t worry I’m a very experienced foal-sitter. I’ll take care of everything”

Before Skipper could respond, Olive’s horn began to glow as the bag over her back opened wide. From one of its inner pockets a pacifier, bright blue and covered in stars, glided from the leather pouch and into the stallion’s muzzle. His eyes went wide as the object invaded past his teeth but he almost immediately began to suckle, Olive chuckling to herself as she closed the door behind her.

“Come on, why don’t you show me round kiddo?”

Skipper slowly moved in front of her, still blushing and avoiding eye contact as he moved up the corridor. Opening the door to the kitchen he started to speak.

“Thith ish de…” he felt himself speaking past the rubber bulb and put his hooves against his muzzle with a small mewl.

“Ssshh... it’s ok. I’m sure I’ll be able to find my way around” Olive started to rub his back, feeling the stallion's nerves tightening his muscles “Just relax, Miss Tenderfoot is here now, ok?”

He looked back at her with ears folded back, nodding slowly. She’d seen all this before from other clients, none of it was unexpected. Taking Skipper by the hoof she led him upstairs, looking up and down the corridor for any indication of a bedroom. A door, slightly ajar with light streaming out the crack, drew her attention.

“This way to your room?”

He nodded back to her, his grip on her hoof tightening just a little as the two of them went through the door. It was a simple room, sparsely decorated with little to suggest that this was anything other than the space occupied by a young man fresh out of studying. A few books were neatly stacked on a bookshelf, while Skipper's bed was unmade and, Olive noted, with a few extra blankets scattered on top of it.

“Well, looks like someone needs a bit of help tidying their bedroom don’t they?”

Skippers hoof tightened around hers again as a fresh mewl came from his muzzle. Whatever decorating skills he lacked Olive had to admit the young man was definitely one of her cuter clients.

“So, as it’s my first time sitting, why don't you tell me what little Skipper likes, hmm?” she took him towards the bed, sitting down and leaving space for him to join her. He gingerly did so, sitting on his rear and covering his front with his hooves. It didn’t take much observation to see he was struggling to keep a few things in check.

“Wellth… I…” he looked down to the floor “Thish feelsh weird…”

Olive put her arm around him, pulling his head down onto her shoulder and carefully caressing his mane “It’s ok, little ones get nervous with new foal-sitters all the time” she smiled and patted him on the back as she opened up her knapsack “Would you like Miss Tenderfoot to just take over for the night? I’ll give you a word to speak when you don’t feel ok, but otherwise what I’ll say goes…”

Skipper looked up at the unicorn, his face thoughtful for a moment before eventually deciding to nod.

“Well then, I think it’s time I got my little foal properly dressed”

With barely a beat skipped, Olive got onto her four hooves and stood in front of the stallion, his muzzle suckling fiercely on the pacifier as the tense feelings of anxiety in the room were replaced by Olive’s dominant presence. Her horn glowed as bright pink light surrounded Skipper and forced him to lie flat on his back with his front legs curling into his chest.

At this point it was impossible not to notice the stallions member standing to attention. Olive giggled to herself, sighing at another of her charges getting so eager in her presence.

“We’ll have to sort that out in a second, Skippy,” she said, pulling powder, wipes and some lotion free from her knapsack. “But first, if you want me to stop, all you have to do is say “Friendship” ok?

“Fwiendschwip?” Skipper responded, his muzzle cocking to one side in confusion.

“That’s right, it’s magic!” Olive chuckled “It makes everything go back to normal! You’ll be a big boy again! I’ll go out the room for a bit and when you feel safe again you can come find me, ok?”

His head went back to laying on the pillow, the pacifier still bobbing in his muzzle “Otay…”

“Good” Olive opened the bottle of lotion, flicking some lightly onto her hooves as she gave she started humming a little lullaby.

“This’ll be a little chilly…”

The stallion gasped past his pacifier as Olive started to slowly rub the slick liquid around his thighs. A few little moans escaped his muzzle as she began to slowly coat his shaft, the suckling on his pacifier increasing in speed.

“You ok there kiddo?”

He nodded, squirming and moving his hips in time with Olive’s movements. She was used to this by now, many of her other clients were less embarrassed about adding this extra step to a diaper change, but Skipper was new to this. Making sure he was continuing to enjoy the process was her job tonight, and she planned to do it well.

“Goodness, what a good little boy I have this evening hmm?” she pulled his rear legs up, lathering his bottom in a layer of lotion that covered his short coat “It might be tough to get a diaper round that though…”

Skipper was now actively starting to buck slightly each time she moved her hands. Eager, uncontrolled desire was taking over his brain as the new experiences started to make his body do things out of instinct and desperation. A small dribble of pre-cum emerged from his tip, worming its way down his stallion parts. It left a trail in the shiny coat of lotion Olive had applied, as though overpowering it.

Smiling to herself, Olive moved to one side of the bed, standing over Skipper and giving him a motherly look as he gazed into her eyes.

“Miss Olive is going to help some, ok little guy?”

A loud moan escaped from his muzzle as the mare started slowly stroking his mane with one hand and his shaft with the other. He hissed a little behind the pacifier as he tensed, his back arching into the air as his cock stood straight up and moved to catch whatever motion Olive was offering.

“There we go, its ok Skipper. Little boys like you can’t control themselves can they?” she cooed at him, a moan from his muzzle the only response she got “It’s why I have to come over and foal-sit you isn’t it? You’d have all sorts of accidents other…”

She was interrupted by the stallion's eyes suddenly opening wide before he bit down hard on the pacifier, his eyes shutting tightly again as the first pulse from his member sent cum splattering across his midsection. Olive sighed to herself and carefully pressed it down so that it’s continued firing did no more than cover his tummy in a thick layer of his own seed.

“Dear me, little boys honestly…”

This time there was no response other than the noise of Skipper suckling slowly on the pacifier. The suddenness of his orgasm appeared to have taken the young stallion by surprise, his eyes staying closed as he breathed in and out slowly and heavily.

Olive's horn once again glowed as she pulled the pack of wipes over to her and started to pull them free of the package. How some other foal-sitters did this without magic was often a thought that crossed her mind, especially now as she slowly dragged the wipes across Skippers tummy, removing the results of his excitement at everything that had transpired. He started to moan again as she wiped down his steadily deflating member as it began to head back towards his nether regions as if fleeing a scene of a crime.

He was definitely a grower rather than a shower. Once it had fully gone back to its natural state it was rather adorable, more like that of a foal than a grown stallion. She cupped his genitals a little with her hoof, letting it all settle before her horn began to glow again.

“Now, let’s get my little one into something that ought to stop him having any more accidents hmm?”

Out of the bag flew a diaper and a bottle of powder, softly floating towards her as she twisted open the cap and started to throw a thin layer of talc all down the front and backside of her still recovering charge.

“Definitely going to need a lot of powder I think… foals don’t tend to tell me when they’ve used their diapers and you’re definitely a foal.”

No noise or complaint came in response as Olive lifted up the Skippers hind legs with her magic and slipped the thick disposable padding under him. How many of Canterlots residents were aware of how easy it was to acquire adult diapers in such adorable designs was a question she’d asked of her supplier in the markets before, only to get giggles and small shrugs as the rather doting shop-keep would always remind her of a simple fact.

“There are lots of foals that just never grow up dear”

How right she was. Moving apart Skipper's legs and pulling the diaper up between them was easy enough, the stallion having little energy left to resist her efforts to diaper him. Not that he’d want to by the looks of it of course.

“These are special diapers just for little Skipper” Olive adjusted the wings before moving one of the large tapes over his belly “Because he’s such a big foal, I had to get them enchanted to make sure he couldn’t take them off! Can’t have you running around and making a mess can we?”

That seemed to get his attention, even through the post-orgasm haze. As the first of the tabs was secured the glitter of a magical effect flickered its way across the plastic, activating the enchantment as Skipper started to squirm.

“Now now little one, just one more tab to go, then we can get your baba ok?”

As Olive secured the second tab she could feel Skipper's mood shift a little. The stallion wasn’t panicking, but she’d seen hesitancy enough times to know that something wasn’t right.

“You ok little guy?” she walked back round to the side of the bed, looking him in the eye as the slow suckling on his pacifier continued.

“I… I can’tsch take offsh the diapersh?”

Olive started rubbing his stomach, occasionally slipping her hoof under his waistband “No dear, only adult ponies can take it off. Imagine if you didn’t have it on, we’d have little messes everywhere wouldn’t we?”

Skipper looked back down at the undergarment and mewled as he saw the designs staring back at him. Images of hay bales and apples were all over it, clearly marketed towards earth ponies. He blushed anew, wiggling in place to make the diaper rustle under him.

“It… feelsh nice…”

Olive gave his rear a little pat with her hoof, a couple of puffs of powder escaping the leak-guards “Good, you’re all protected from any more little accidents now!” She pulled him up into a seated position, letting him take it all in.

“Goodness aren’t you just precious!”

Skipper blushed intensely, hiding behind his front hooves as his rear ones started to squeeze the new padding between his legs.

“Now, I did promise you a baba, didn’t I?” Olive grabbed her changing bag from the side as she pulled the stallion up into the air to float in front of her. Rather than just dropping him into her hooves, which she knew would be a tad too much on her muscles, she kept the spell going and held him out in front of her as they walked through the house, back down the stairs to the large living space at the bottom. Olive sat down on a large couch as she watched the squirming and adorable foal in front of her suck on his pacifier with his eyes wide at the experience of being carried round like a child barely ready for walking on four hooves. She laid him down next to her on the couch, his head resting on her lap as started to stroke his mane again.

“Stay still ok, Miss Tenderfoot is going to get you a nice warm bottle of special milk”

The bottle that came out of the bag was oversized, full of milk and decorated with childish designs. Skipper shifted in place as he saw the massive nipple head for his muzzle.

“Mah pacifier?”

Olive smiled and popped the object free of the stallion's maw “You can have it back after you’ve had your bottle” she cooed, letting her magic do its work as the bottle glowed a little with heat. A quick warming session before she finally dropped it carefully into Skipper's waiting mouth.

He began to suckle in earnest, his eyes closing as the warm liquid started to make its way down his throat. He visibly relaxed, his arms falling to his side and his legs stretching fully to the end of the couch. The diaper between his legs crinkled slightly with each movement, the thick padding pushing the big foal's legs wide apart.

This was her favourite moment. Olive could look down and see nothing but pure happiness on the face of her charge. They didn’t want to be an adult if they could help it, she was more than happy to oblige. Once she’d got her cutie mark while foal-sitting, she thought she’d be up and down the streets of Canterlot being the best one she could be.

But finding out she had a talent for this? For sitting “bigger” foals? That made her happy in a way she never got in her “day” job. They paid well too of course, but seeing them be themselves, totally at ease in her care was massively more fulfilling in some ways.

“Mppphhh…” the stallion looked up at Olive, his suckling stopping for a moment.

“Yes kiddo, what’s up?” She removed the nipple to let him speak.

“I… I have to pee…”

Olive chuckled “Oh silly, that’s what the diaper is for! Now, let’s go back to your baba hmmm?”

Skipper looked down at the padding between his legs and mewled again, hiding his face as his legs started to move apart. It didn’t take long for Olive to notice the tell-tale hiss of a stallion emptying their bladder, the diaper swelling fast to accommodate the adult foal’s “accident”

“It’s ok sweetie. Foals use their diapers all the time, remember?”

He nodded slowly, pulling his arms away from his face and looking back up at the nipple of the bottle.

“Baba?”

Olive wanted to melt. Some charges didn’t get into the headspace easily, but this kiddo was already deep diving into it.

“Alright little one, drink up. Someone made some room didn’t they?”

As he started to suckle anew, Olive went back to rubbing his mane. This was her life most evenings, she’d do it again tomorrow and the day after that with different foals all needing her undivided attention.

And she wouldn’t change it for the world.