Assistant Sitters
by Otterslide

It was a beautiful day and a raccoon named Kep was looking after some little cubs. He'd started a small babysitting service to make a bit of cash outside his normal job and ran it from his home — the parents dropped their babies off and picked them back up at the end of the day. However, he'd started to really miss the free time and peace he'd had before starting this service and was almost desperate to get it back somehow. So, after remembering there was a farm nearby, he came up with a rather unconventional plan. 

He pushed along a large stroller he'd purchased online, one big enough to seat three, and was also carrying a fourth cub in a baby harness. In the stroller was a year old deer doe with light brown fur, white spots on her back and a white belly, with sky blue eyes, a five month old female puppy with vanilla yellow fur, a dark grey nose, and teal eyes, and a sleepy male newborn brown bear cub with chocolate brown fur, darker brown ears, tail, and muzzle, and hazelnut eyes. In the harness was a one month old male rabbit kit with grey fur and a white belly, tail, and inner ears, green eyes, and a black nose. All of the cubs were wearing diapers and each one besides the bear was wearing some sort of clothes. The raccoon also carried a diaper bag with extra diapers and supplies. As Kep approached the farm taking in the sounds of the birds in the nearby trees and the soft cool breeze he tried to figure out which animals would work best for his plan. The first pen he came upon was full of sheep, the raccoon pushing the stroller up to it to let the cubs see. Looking at them he decided that a sheep would do just fine being the first of his 'assistants'. He then looked over the cubs and picked out the little bunny since he was the smallest of the four.

"Alright, let's get you guys stored away so I can relax for the day."

He gently lifted the baby bunny up out of the harness, the little kit shy yet his ears had perked up in curiosity. Kep smiled and tickled the bunny's belly before taking his little shorts and shirt off, leaving his diaper on. Not too long later he was climbing over the pen's fence and approaching the closest ovine, a somewhat large ram. The ram had very light grey wool, grey facial fur, large black curled horns, and a short tail. He was lying down, relaxing a bit. Kep approached him in a friendly manner, reaching out and gently petting his short wool. After a bit the raccoon started pushing on the calm sheep, gently — struggling a bit because he only had one arm to use with the other carrying the rabbit cub — until he managed to roll him onto his back. Once done he took a look at the ram's lower end. He had a fuzzy grey sheath, somewhat large nuts, and a mid-sized anus, all on view now. The ram didn't stay on his back for long, rolling back over but not getting up. Kep pet that backside a bit then held the rabbit out, letting him get a good look at the feral sheep. He moved him over to in front of the ram, who sniffed at him a bit curiously before giving him a small lick, accidentally startling the baby bunny a little. 

"It's okay, it's okay, he likes you!" Kep chuckled, rubbing the rabbit's belly again to calm him down. "You're gonna be fine with Mr. Sheepie, alright?"

Still holding the baby with one paw he gently pet the relaxing ram's backside with the other again for a few moments before moving it in front of the wooly mammal and getting the same treatment as the bunny had — a sniff then a few licks. Pulling the paw away he slowly moved it to the ram's butt, sneaking it in under his tail and rubbing at that anus a bit with his digits, getting it nice and covered with the ovine saliva. After glancing around a little to check his surroundings the raccoon then raised up the ram's short tail and moved the bunny down, slowly and calmly so as not to scare him. The rabbit didn't know what to make of the object presented in front of him, sniffing a bit. Not wanting to waste much more time Kep started moving him forwards until the bunny's nose pressed against the center of that puckered hole, then putting more force into it and making the hole slowly start to spread around that short muzzle. The saliva worked well enough as makeshift lubrication and the baby bunny squirmed a bit as his muzzle was pushed into the ram's ass. The raccoon pushed further and the hole slowly accepted the bunny's head inch by inch, slowly forcing those perked-up ears to flatten down. Soon the infant's whole head was in that sheep rump, the ram grunting out and looking back to try and figure out what was happening, the raccoon calming him down with some petting to his rump. 

With the rabbit starting to squirm harder Kep pressed more, slipping him in further and further. The tailhole swallowed up the bunny's neck and chest, then his arms, then Kep let go of the bunny and instead held both of the baby's large feet. He pushed on them, the bunny's torso and fluffy white belly disappearing up that ram's ass. The kit was squirming a lot more now in that tight, wet, musky passage, the ram huffing and shifting a bit from the sensation. His little rump was pushed in making his diaper crinkle. Finally with a bit more pushing the only things left sticking out of the hole were the baby's toes, those getting clenched in and the hole closing up, the leoprine now entirely lodged up the sheep's ass. Kep wasn't quite done, though, quickly setting down his diaper bag and opening it up, revealing a small stash of unusual items for such a bag: buttplugs. He'd brought them with him from his own small collection at home. He picked one and took it out, slipping the bulb of it into his mouth and lapping all over it, getting it lubed up while looking like he was suckling on a large black pacifier. Popping it out of his mouth Kep moved it down to the ram's butt and firmly pushed it into his clenching hole. The ram baaed out as his ass was stretched wide around the bulb of the plug and struggled to get up, doing so but not before the plug popped in, the base soon getting hidden from view as the short tail fell down over it. The ram waddled away, not used to the feeling of having a whole anthro baby bunny squirming inside him sealed inside with the somewhat large plug.

Kep chuckled and got to his feet, brushing his pants off, confident the baby would be nice and safe in there and would calm down after a bit. He also made sure to remember what the ram looked like for later, not too difficult since he had the darkest horns of all the rams. He picked the diaper bag up and climbed back over the fence and out of the pen, going back over to the stroller. "Alright, let's go see the other animals." the raccoon announced to the other babies as he started to push them along after taking off the baby harness and putting it in the storage area of the stroller.

After a little he came up to a field and gazed out on a herd of cows, grazing on the fresh green grass. Kep pushed the brakes of the stroller down before looking at the cubs in it. "Hmmm..... Yeah, you'll do." he mused before unbuckling the little Labrador puppy and picking her up. "Let's go see the moo-moos!" he cooed as he gently took her shirt off, bouncing the excited cub a little and smiling as he saw her tail wagging, sticking out of the tail hole in her lavender diaper. Climbing the old short fence he started walking towards one of the cows. The bovine was large, probably weighing over 1,800 pounds. She had short white fur with black splotches and a black stripe running down the middle of her face, and a pale pink belly with a big light pinkish-tan udder hanging down under her. Just like he did with the bunny, he brought the puppy around to the front of the big mammal who looked up from rooting around in the grass. The little puppy squirmed excitedly as she looked at the cow who sniffed at her with her big nose, then squealed out happily as the cow gave her fluffy belly a lick with her big thick tongue. Chuckling, Kep moved her away and walked around to the bovine's other end. "You're gonna have fun with the pretty moo-moo. She makes milk just like your mommy!" he told her, though he wasn't going to show her that udder and let her have any since the unpasteurized milk might've made her sick. Instead he moved to the cow's big rump. The cow sported a large somewhat loose light pink pussy and a puffy pink and black-splotched tailhole. Knowing the cow could startle easily and run away scaring the whole herd, the raccoon didn't want to take too much time putting the puppy away. Lifting her up he brought her to the cow's puffy and somewhat smelly hole, having an idea of what might happen. He was proven right as the excited puppy cub started to explore the ways dogs do and lapped at that hole. The cow grunted but was busy chewing on grass, tail flicking and smacking the raccoon but he shook it off and kept the puppy there. He moved her around a little making sure she was really covering that hole with saliva. It was probably a bit dirty but she didn't seem to mind, her tail wagging quickly. Once Kep decided it was enough he moved the baby away and shrugged off his diaper bag, readjusting his hold on her so he could open it up. He was picking out a plug beforehand since he didn't want the bovine to run off and the cub to fall out. Pocketing the plug he held the yellow lab up again and brought her face back to the hole, the girl again starting to lap at it.

"Alright, this might get a little bit stinky but you'll be okay." he told her, even though he knew she probably didn't understand much of it at all. 

Instead of starting to push, Kep waited, anticipating a precise moment. That moment didn't take to long to arrive; the cow finally did what cows were infamous for, a loud fart rippling out of her puffy hole, the puppy's fur blowing a bit while she scrunched up her muzzle from the stench. With the hole partially open to release the gas Kep was quick to act. Right as the fart started he shoved the baby forwards, firmly stuffing more than half of the puppy up that very likely dirty ass, using the fart together with the spit the puppy had supplied to make the process much less painful for the big cow even if it meant that the puppy had to endure a second or two of gas blasting out around her. By the time the fart had ended the baby was stuffed up to her thighs in cow ass. Kep quickly got the plug out expecting the cow to be startled from the insertion but was pleasantly surprised; the bovine only stepped away a bit, confused about the squirming thing in her ass but not freaked out by it. Smiling he followed her until she stopped, watching the puppy's legs kicking weakly about then using a paw to push those feet, sinking the baby girl the rest of the way up that stinky cow hole. With the canine now lodged fully in the cow's backside Kep stood back a bit and before using his own mouth to lube up the large buttplug he instead got an idea and walked back to the front of the cow, presenting it to her instead. Curious as ever she sniffed at it before lapping at it a bit with that big tongue, effectively covering it after a few seconds. Satisfied he returned to her rump and lifted the plug before pushing hard, making the cow moo out a bit as her hole was stretched again. That plug soon slipped in leaving that puffy anus clenching around the short neck, the base making sure it didn't get pulled in any deeper. Kep patted the dense rump then picked his bag up and left her to graze and care for the baby lab, returning to his stroller.

With two cubs now in the care of animals he pushed the remaining two along, happy with the progress he was making and knowing that soon he'd be able to relax.

The next pen they came upon was quite a bit muddier and was home to several large feral pigs. He parked the stroller again and looked around at the pigs, wondering which would be a good candidate. He then saw one of them relaxing near a corner of the pen, happily lying in the thick mud. The pig was huge and fat and weighed easily over four hundred pounds with a coat of dirt-streaked wiry light pink hair and a curly tail, deep enough in the mud that his whole belly was submerged. Kep decided he'd be a great assistant but wondered how to get over to him. After a bit he sighed, realizing there was no way to do so without getting dirty. His mood was brightened a little though when some more looking around revealed a faucet next to the pen he could wash off afterwards with. He decided to leave his bag there this time around, taking a plug out of it and pocketing it. Kep looked at his stroller and saw that the baby bear was sleeping so he decided not to wake him and instead unbuckled the baby doe, picking her up and rubbing her head. "You ready to get a little dirty with the piggies?" he cooed, gently removing her little booties and putting them back in the stroller then slowly taking her tiny dress off, deciding to leave her diaper on because even though he knew it'd get dirty he was going to change all of them before heading home regardless. He then took his own shoes and socks off, cradling the doe with one arm as he rolled up his pant legs. Once ready he finally stepped into the pen, ears flicking at the feeling of his paws squelching down into the mud. 

As he approached the pig, wading through the ankle-deep muck, he wondered how he'd get lubrication this time to ensure both calm deer baby and the fat feral pig weren't hurt. Spotting a small puddle of watery, thinner mud he got an idea. "Wanna play in the mud a little bit?" he then asked the deer,  heading over to the spot. He then carefully held her by her arms and slowly lowered her down, her ears perking up as her feet sunk into the liquid-y mud, getting lowered until her feet finally reached the bottom of the puddle, up to her upper thighs in the muck. Letting go and quickly supporting her with a paw Kep bent down and dipped his other paw into the mud, bringing it up and starting to smear it on the baby's belly making her giggle a little. The raccoon slowly covered her whole body from the neck down in the slippery mud, her diaper getting stained from the outside. She seemed to enjoy it, trying to step a bit through it but getting held back by the adult mammal. After a bit he was satisfied and picked her up, bringing her out of the thinner mud and trudging through the thicker stuff over to the big pig. Bringing her right to the animal's backside he looked it over a bit. The porcine had a huge stretchy-looking tailhole between his flabby pliable cheeks and also a massive sack, his nuts and sheath both being either partially or fully submerged in the mud. Kep noticed the pig's hole was quite stained with brown and realized that the pig had very recently let out some of his own fresh 'mud'. Knowing that was pretty unavoidable he held the deer with one arm while using his free, still mud-covered paw to rub at that fat dirty hole, slathering it with the slick muck and making the pig snort a bit, even pushing his paw halfway into that hole to make sure it was all nice and slippery, taking note of how easily it spread around his digits. 

Taking the doe in both paws once he was done, he positioned her so she was horizontal with the ground, one paw around her thighs and the other supporting her chest. She confusedly looks around, not seeming to like the smells. The little doe was brought closer to the big pig's ass, her muzzle inches from that poop-stained and mud-covered anus. With a firm shove the baby started her messy journey into the pig, her face and head getting coated as they disappeared into the fat asshole, squelching noisily as the raccoon kept pushing. More and more of her muddy wriggling body was stuffed into the pig in one smooth motion greatly helped by how accepting that hole was, the lazy boar oinking and snorting from the feeling. That warm filth-coated passage clenched and moved around the doe as she slid in and soon enough her entire body was inside, getting pulled even deeper in by the movement. Kep took the plug out of his pocket and popped it into that flabby rump as he patted it with his other paw, the mud and poop taking care of the lubrication, the base twitching a bit as the hole clenched around it. Standing back up and nearly losing his balance the raccoon turned and trudged back through the thick muck, getting out of the pen and feeling relieved to be on firm ground again before going to the faucet and starting to wash the mud and other filth off of his hands and feet.

Cleaned and donning his shoes and socks again Kep pushed the stroller along, now carrying a single occupant in the form of the sleeping newborn brown bear suckling on his pacifier. He passed the chickens and the goats before spotting the stables and heading over. As expected the stalls were home to equines, mostly majestic horses but there were a couple donkeys there as well. One of them caught Kep's eye, the raccoon pushing the stroller over to the stall and looking at him. He was a big, slightly chubby light greyish-brown donkey with a short black tail and a shorter black mane. The raccoon unbuckled the bear and picked him up, waking him. "Hey there sleepyhead~ Wanna meet Mr. Donkey?" he asked with a giggle, unlatching the door to the donkey's stall and slipping in, closing it behind him. He presented the newborn to the equine who sniffed at him but didn't seem interested in licking him. Having planned on using the donkey's saliva as lubrication Kep was forced to think of a different method. A rather lewd idea then popped into his head and he went around to the side of the donkey before crouching down. 

He looked at the feral's sheath and low-hanging leathery sack, smirking. Reaching up, he started to massage the equine's sheath, watching it stir before the shaft tip slowly poked out. That donkey cock gradually emerged from the sheath as the equine huffed and shifted a bit and soon it was fully hard, quite impressively large. Letting the baby watch Kep started to stroke that shaft, unable to fit his grip fully around the length because of how thick it was. He kept his strokes constant and paid attention to that tip as well, the length beginning to drool and spurt pre. Luckily equines didn't last too long so he wouldn't have to spend much more time doing this. The donkey brayed a bit, clearly loving the pleasure. Finally after a while the raccoon could tell the feral was getting close, mostly based on how much pre was spurting from his length. Still stroking the shaft he adjusted his position, holding the baby bear in front of the donkey cock. Not long later the equine brayed loudly, orgasming and starting to hose down the cub with his thick hot seed. The bear grunted and squirmed in confusion as his fur was covered and coated with fresh cum, Kep continuing to stroke to milk the cock and squeeze out as much seed as he could, turning the bear a bit a few times to really get his whole body covered. When the orgasm finally ended the bear's fur was left absolutely soaked. 

"There you go~ Maybe one day I'll let you guys taste all of the animals' special milk." the raccoon chuckled, getting out from under the donkey and going around to his butt. Below his tail and wedged between his cheeks sat a big yet tight puffy anus, Kep lifting the newborn bear up to it, letting him look and sniff at it before starting to push. With the cum as a slippery thick lube, the bear's muzzle started to spread the musky donut out, the donkey grunting, still recovering from the orgasm. The bear squirmed a bit as his head slowly vanished into that equine anus, the cum adding to the squelching noises being made. The raccoon continued gently guiding the furry body into that puffy exit, getting him halfway in before starting to feel some odd resistance. At the same time he felt the bear start to squirm hard and had an idea as to what was happening, starting to pull him back out. His assumption was confirmed as the bear's head pulled free, coated in equine manure. Right after the little cub was free a large ball of waste started pushing out. Kep watched as the donkey shat out a sizable load of donkeyapples. "Heh, sorry little guy. Didn't realize he still had to go." the raccoon said to the bear who looked quite unhappy with the stinky waste his face was covered with. Once the donkey was finished with his dump Kep moved the bear back and started pushing him once more into the now much dirtier hole, prompting the bear to wriggle again. "You'll get used to it." he grunted as he firmly pushed on the bear, the little cum-covered body gradually disappearing up the stretchy hole until with a clench from the anal passage the little squirming cub was tugged in fully, getting pulled deep into that equine rump. Like with the others Kep brought up a large buttplug and stuffed the bulb into that anus to ensure the little bear stayed in that filthy 'sleeping bag' using the cum and filth as lubrication. Kep patted the donkey's butt and exited the stall, pushing the empty stroller away from the stables.

Now all of the cubs were in the care of their babysitters and Kep could finally search for a place for a much-needed nap. He planned on relaxing for most of the day until it started to get late, then he'd collect the cubs back up and get them nice and clean, changing their diapers and re-dressing them before taking them back home and waiting for their parents to come pick them back up never knowing where they'd been. Sure it wasn't the most conventional or acceptable ways of babysitting but it allowed him a bit of peace and quiet and no one but him knew about it so he didn't really care. 

Kep smiled as he found a place to rest, parking the stroller and putting the diaper bag in it then sitting down and lying back with his paws behind his head, slowly drifting off into a nice peaceful sleep.