The Help Wanted Chronicles: The Prancing Pony
By: Snow the Bear

Authors Note: “The Help Wanted Chronicles” is a series of story’s (3 planned so far) based on naughty pictures I’ve commissioned of myself. The Prancing Pony is the first story of the series, but takes place after the other two.

Six months ago, Snow had succumbed to wanderlust, and set off on a road trip to see the country. For most of the trip, the pizzly bear had chosen to avoid the big cities and tourist traps. Instead he traveled rural roads and visited small towns, where he would spend a few weeks, making new friends as he worked odd jobs to fund the next leg of his adventure. Until recently, this plan had been working nicely, but now a dry spell in finding work had quickly depleted his funds.

He had been driving on a nameless dirt road for over an hour and had not seen a single town, just endless farm fields on either side. Snow looked down at the gas gauge again and sighed. He only had a quarter tank left, and started to worry he might end up stranded out here. But even if he did find a town he was almost broke. How would he afford gas? Not to mention food and lodgings for the night. Without thinking he said out loud “Well Ember, looks like we are going to be in trouble. Even if I somehow find work today we will need an advance. The chances of finding someone that will take in a drifter are slim”. Ember was the car’s only other passenger. The fox plushie had been with Snow since the day he was born, and their bond was strong. Snow often felt Ember was alive and aware, and sometimes thought he could hear him talking to him – but that must be his imagination.

A sign up ahead caught Snow’s eye and he pulled over to the side of the road to inspect it. It stood at the end of a private laneway and looked too fancy to belong to a farm. The sign was hung from an intricate iron post and featured elegantly engraved gold lettering. It read: 

The Prancing Pony
Pony Training & Stable Services by Miss Victoria

Below it hung a smaller sign reading: 

Help Wanted
Room and Board included

The laneway led from the road to a fancy iron gate. His gaze followed the lane further down to where it curved and disappeared behind a grove of trees. The edge of what appeared to be a ranch house was also visible some distance past these trees. Snow had no experience with ponies or even working on a farm. Then he remembered that last part wasn’t exactly true, and blushed bright red. Pushing that embarrassing memory away he debated if he should bother asking about the job. Desperate to build some funds he decided he couldn’t pass up this opportunity without at least inquiring about it.

As he drove up to the gate and noticed two things: an intercom box mounted on a post beside the lane and a sign on the gate: By Appointment Only. He didn’t have an appointment, but at worst he would be turned away, so he took a chance and pressed the call button. There was a beep, then silence. He waited about half a minute with no reply. Just as he was about to press again a female voice came from the speaker, “Hello, state your business please”. 
 
“Excuse me ma’am. I’m sorry to come unexpectedly, but I’d like to inquire about working here. Do I need an appointment for that?”

After a short pause the woman spoke again, “Normally yes, but I have no more appointments scheduled today. Please come to the main house”.

Snow heard a click and saw the gates slowly open. He drove up the laneway and as he turned the curve the rest of the ranch house and the stables came in view. He parked in front of the house, and before he got out he placed Ember in his backpack. They were rarely separated, and Snow knew the plushies comforting presence would be needed if the interview was stressful. Backpack in tow he approached the front door. 

He lifted his hand to knock but the door opened before he had the chance, and in the doorway stood a Doe. The first thing Snow noticed was her height, she stood a good 4 or 5 inches taller than him. She was dressed prim and proper in an equestrian outfit, her knee-high riding boots and jacket buttons polished to a shine. Her slender body and stance appeared graceful, but the form of her legs under her skin tight pants hinted at the physical strength her career required. Everything about her projected an aura of elegance and authority. Her presence carried so much strength that the bear subconsciously bowed his head to lower his eyes a little. The hand that he had raised to knock fell to his side and he instinctually took a step back. 

Victoria noticed these small gestures of submission and was pleased. “Welcome to The Prancing Pony. I am Miss Victoria, and you are?”

“Hello ma’am, my name is Snow”

“It’s such a pleasant day, why don’t we discuss our business on the porch” she said and gestured toward a pair of chairs. She waited several seconds to see if the bear would move first, but he did not. He stood there and waited for her. She proceeded to the chairs. With her back now to him Snow couldn’t see her smile as she heard the bear follow her. She thought to herself, a seemingly natural submissive, who speaks when spoken to, and only enough to answer. And he follows instead of taking the lead. Her instincts were telling her the bear had potential.

Once they were both seated she continued. “Your unscheduled visit was a surprise, so I must ask, who referred you?”

Just my luck Snow thought, this job must need special skills. “No one referred me ma’am, I was just driving by and saw the help wanted sign. I hope I haven’t wasted your time”.

What sign? Victoria thought and then remembered. That sign should have been removed two days ago, she would have to punish her assistant tomorrow. “I’m afraid that sign should have been removed. I own other stables nearby. All the positions that the sign referred to are at those locations, and have been filled. However, as you likely guessed there is a position open here. Do you have any idea what we do here?”

Snow wondered if this was a trick question, it seemed simple enough. “I assume you provide lodgings for pony owners without their own stables, and train them for riding? I have to be honest with you, I doubt I’m qualified to work here.” And with that last sentence the bear’s expression turned from cautiously optimistic to dejected.

“That’s fairly accurate although our services are more … specialized.” the Doe said with a slight grin, “As for your qualifications, I will be the judge of that. You might be surprised at how suitable you are. On the job training is included in the role, and not having experience could be an asset. I won’t have to break any bad habits. Now, since you were not referred I’ll need to get to know you.”

For nearly an hour Victoria quizzed the bear about aspects of his life, and carefully studied his body language as he replied. Some of her questions made Snow feel awkward or embarrassed, but he answered them truthfully. During their conversation she neatly evaded every attempt Snow made to learn about what the job actually entailed. Finally she believed she had learned enough.

“Snow, from what I’ve just learned, I suspect you would be an excellent match for this role”. She rose to her feet and Snow followed suit. “The open position is a bit difficult to describe without visual aids. Follow me please”. 

Victoria turned and walked toward the stables. She noticed the bear catch up to her, but remain a respectable few steps behind. More evidence her instincts were correct.

As they walked to the stables Victoria began to explain. “As you guessed, we train ponies here but only the bigger ones are fit to be trained for riding, unless you include pulling a carriage. Here we train them to be show pieces and several of our ponies have gone on to be renowned in competitions. Training can however be difficult at times. Some are stubborn or have difficulty learning their tricks. In these cases it helps to have a well trained pony to set an example for them. I had such a pony until recently, but Coal has retired so I need to train a replacement” 

Snow had expected the job to be cleaning the stables and basic care for the animals. He wondered why she expected he could help train them. They reached the stables and he followed Victoria in. Just inside and to the left was a smaller room that appeared to be a makeshift office, which she led him into. The room was scarcely furnished, just a desk and three chairs, but the walls were covered in framed photos.

“These are photos of some of our finest ponies, take a good look.”, she said as she walked over to a desk and stood beside it. Once the bear’s attention was on the wall, she casually picked an object up from the desk.

Snow began examining the photos. They displayed impeccably groomed show animals decked out in well polished tack. Most of them also featured some sort of ribbon or plaque that had been won, but immediately he knew something wasn’t quite right. At first he his mind didn’t want to believe what it saw but there was no mistaking it. These ponies where not the feral equines he had been expecting, but were instead furries! Once he recognized the equine hoods, hoofed boots and artificial tails for what they were it couldn’t be unseen. There were all manner of creatures here, including bears, wolves, tigers and even a dragon! In shock Snow stepped back from the wall and turned to face the doe. 

He opened his mouth to speak. And saw the doe’s arm quickly swing toward him.

*SMACK*

Snow yelped in surprise and pain as a patch of fire burned into his left buttock.

He watched stunned as the doe pulled back the riding crop she had used to strike him, and rested it in her hands. “Before you try to speak again let me explain and don’t interrupt. When I’m done you will be allowed to speak. Is that clear?” Her voice was calm but the tone of authority in it was stronger than ever. 

She watched the bear nod his head before continuing. “The dragon in those photos is Coal, it is his role you came here looking to fill. If my instincts are correct, you have great potential to do just that. Unlike Coal, I don’t think I’ll have to spend time breaking you like I would a feral animal. He was quite dominant at first. But in you I detect the soul of a submissive and an instinct to please others. What you saw in the photos may have shocked you, but it excited you too didn’t it?” The bear blushed but nodded yes. “You need a job and a place to live, and I need a demo pony to help train my clients pets. I promise your safety will be assured, but know that while you are employed here you will treated as a feral pony. You will live in the stables. You will drink from a dish or trough and you will eat from a feed bag, though your food will be appropriate for a bear. I will begin training you for your role, which I estimate will take no more than four weeks. I am offering you a 6 month contract. During which your food and lodgings will be covered, and you will be paid $5,000 per month. After 6 months you can leave or choose to extend the contract”. She handed the bear a paper from the desktop. “This has all the details. Read it all thoroughly and then you may ask any questions”. She waited as Snow read the document.

The contract was clear and summed up most of what the doe had said. “What’s this about breeding rights?” he asked timidly.

“That part pertains to mares, and I have no intent to stud you”. The bear blushed at her reply.

6 months was longer than he had expected to spend in one place, but the pay was more than he could ever make working odd jobs. As he thought it over he glanced several times to the wall of photos. He knew she was right about his nature, and the allure of being treated as someone’s trophy pet was strong. 

Victoria read his decision before he could say it, she just smiled and held out a pen. Filled with nervous excitement Snow took the pen and signed the contract.

“Excellent! The rules here are simple”.

“Rule #1 ponies don’t speak. Unless I make it explicitly clear, words are off limits. You may use gestures and appropriate sounds such as whinnying and neighing. The only exception is if you believe your safety is threatened”.

Rule #2 you will obey orders to the best of your ability and without question. If my instincts are correct I do not expect your training and duties will cross any of your boundaries. But you may find them being tested. If you are certain a hard limit is being crossed, you may speak to inform me”. 

“You have already felt what happens if you break the rules” she said while waving the crop. “Now follow me and we’ll get you settled into your new home”.

Victoria led the bear out of the office and down the isle of the stable. To each side of the isle was roughly 10 stalls. Most of the stalls appeared to be 5 feet wide and 7 feet long. All of them featured a backwall that reached the roof, a 4 foot high gate which acted as a front wall when closed, and 4 foot high side walls. The last foot of the side walls was a wooden rail which left a horizontal gap ponies could see their neighbors through. One of the stalls was twice the size of the others, and it was here she led him. Upon seeing the contents of this stall he hoped it would not be his new home. Like the rest of the stables the floor was wood, but unlike the other stalls it had almost no hay to create a soft place to sleep. But more worrying was the equipment he saw. Various piece of harness and tack hung from the walls. Some were meant for feral equines, but many were obviously kinkier in nature. Most ominous was the medieval style stocks at the far end. It had holes to secure the arms and head as well as cuffs chained to the floor to secure legs.

The doe led them in the center of the stall and stopped. “Strip!”, the doe commanded, “Everything comes off. Place your clothes and belongings on the back shelf, they will be safely stored for you”.

Blushing furiously Snow placed his backpack on the shelf and removed his clothes. He was thoroughly embarrassed to be naked before the doe but it seemed that blood was rushing to more than just his face. Victoria’s dominant nature was highly arousing for the bear. Once he had finished doing as instructed he turned to face her.

Victoria saw the bear’s erection and gave him an amused smile. She began to slowly circle him, dragging the tip of her crop across his body while inspecting her new pet. She stopped behind him and pressed her body against his back. She rested her neck over his shoulder so she could look down at his throbbing member, and playfully tapped his cock with the end of the crop. He began to fear she would punish him for his arousal.

“Oh my. Does the mighty predator like being under the control of prey”. Her words sent a surge of excitement through the bear. 

She backed away, walked to the stocks and opened them. “Come here my little pony” she said patting the wood. 

Snow tentatively walked over and placed his head and wrists into position.

“What an intelligent pony” she said as she closed and latched the stocks. Then she bent down and secured the bears legs with the floor cuffs. “Now be a good little pony and remain silent until I say otherwise”.

Facing away from the rest of the stall, Snow waited nervously as he heard her rummaging around, followed by the sound of running water. 

Still behind him and out of view the doe returned wearing elbow length rubber gloves, and carrying a small metal object and a pail. She got on her knees behind the bear to better perform the first step.

Snow was startled when a hand suddenly cupped his testicles and gave them a gentle tug. Then the hand moved forward, grabbing his shaft and pulling it downward. He heard water sloshing and moments later yelped as something wet and very cold enveloped his cock and balls.

The doe gave a little laugh, “I heard that. We can’t have this little thing flopping around, or getting caught in the tack. Now can we?”.

Snow shivered as the icy cold towel she had used chilled his flesh and caused his cock to quickly retreat into its sheath. He sighed in relief when the towel was removed and another one was used to dry him. Next he felt her grab the top of his scrotum and pull down to stretch it, followed by something hard encircling the taunt skin above her hand. Then he felt something hard and tight being slipped over his sheath, and he let out a whimper as the anticipate click of the lock was heard. If the next 6 months were as arousing as he expected being chaste for it would be torture.

The doe gave another little laugh, “that’s the 2nd noise you’ve made. Each has earned you a swat from my crop. I’d advise you not to earn anymore”. She said sternly.

*SMACK*
*SMACK*

Snow felt the same stinging sensation as before, this time one on each buttock, and with no pants to lessen the blow. He squirmed in the stocks as he fought the urge to cry out. 

Victoria watched her new pony with delight as he squirmed and struggled to remain silent.  Using the crop to lightly tap his chastity cage she teased. “I get the impression this isn’t the first time my pony has worn one of these. Very interesting, but we can discuss that later.

Victoria removed the ankle cuffs and opened the stocks. “Go over there and get on your hands and knees” she said pointing to a small patch of floor covered in hay”. 

Snow obeyed without hesitation.  As he approached the spot Victoria had pointed to, he saw what appeared to be four brown leather pouches with several black leather straps laying next to them. Once on the hay he got down on his hands and knees.

“You need to learn how to move like a proper pony” she said picking up one of the pouches. “Lift your right hand”, and when Snow did she slid his paw inside. “You should feel a bar inside hold it in your fist, nod when you have it”. Snow did so and when he nodded she cinched the pouch closed. She then did the same for his other hand. Enclosed as they were, his hands were now useless except for walking on.

“Those mitts will protect your hands and support your wrists as you walk. Now for your feet”. She placed the booties that were the other two pouches on the bear. “Those will protect your feet”. I’ll need to have you fitted for knee pads tomorrow, your legs are chubbier than my usual ponies”.

She picked up the straps and placed one around each of his thighs and calves. Once all four straps were secured she clipped a small bar between each strap on the same leg, and used a short chain to connect his thigh straps together. “These will force you to stand on all fours, and encourage you to learn to move like a feral pony”. 

The doe went over to the wall and retrieved a bit and bridle. She bent over to place it on the bear, and smiled when her new pony opened his mouth without needing to be told. She inserted the bit and fastened the bridle securely to Snow’s head. “That’s a good pony” she said as she petted his muzzle. 

“We are almost done, just one more essential piece” she whispered into his ear. As she stepped back, he caught a glimpse of her sly smile which caused the bear’s heart to race in both fear and anticipation

Snow watched as she walked to a cabinet and started to search inside. She seemed to pause to think for a moment before pulling out two items, but only the first caught his attention. It was black and looked like a dozen strips of rubber connected to a thick handle. A flogger!!? She had just called him a good pony, what had he done wrong to deserve this? Snow cringed and trembled with fear. 

“Aww is my new pony timid. I know it looks big but I’ll make it fit. We don’t want it too loose and risk it falling out”.

Make it fit? fall out? the puzzled bear thought. He then recognized the other item she held, was a bottle of lube. His stomach dropped as he realized that the black object wasn’t a flogger. It was a large butt plug made to look like a tail!!!

She knelt beside the bears rump and caressed it gently. “We’ll take it slow so try to relax. You will grow accustomed to it in time, but this may hurt. Have no doubt IT IS going in”. Victoria poured lube on to her right hand until the gloved fingers were slick and shiny. “Spread your legs as much as your bonds allow. I don’t expect you to be silent for this, but remember no words are allowed”. 

With her left hand resting on the bear’s flank, she brought her right to probe the bear’s hole. He flinched at her touch, but she just shushed him in a reassuring tone. Slowly she began to work one finger inside and found little resistance. She swirled the finger around to lubricate the passage before pulling it out. She lubricated her hand again and this time pressed two fingers against him. Gently she eased them in, pausing whenever she felt the bear flinch in discomfort. Once both digits were fully inserted, she began to slowly move them in and out, encouraging the ring of muscle to relax and stretch. Finally she repeated the process with three fingers. This time it took considerably longer and the bear uttered several grunts of discomfort. But eventually he settled down as the muscles became accustomed to the stretch.

“Good boy. You are ready for your tail” she said as she lubed the plug end of the tail. In his fear the bear hadn’t noticed the shape of the plug. It had been made to resemble an unflared equine cock, with an oversized medial ring designed to lock it in place once inserted.

She placed the tip against his well lubed hole and the bear’s body jerked. “Easy boy” she cooed and petted him until he settled down. “Alright here we go”. She began pushing it against his hole, slowly increasing the pressure. At first his ring resisted, but after a few minutes, and many whines from the bear, it finally relented and the plug started to slip inside. Once the tip was fully in she stopped so he could get accustomed to its girth.

“There, the tip is in; the worst is over”. Her words were meant to calm and reassure her new pet, but they were also a lie. She knew the medial ring would be his biggest challenge. I’ll allow him a small treat before the final push she thought. The doe changed the angle of the plug so it entered pointing slightly down, then began sliding it forward, waiting to hit what she was looking for. Suddenly the bear shuddered and let out a moan. That’s the spot she thought, she had found his prostate. 

Instead of continuing forward she pulled back, causing the head of the plug to rub against the sensitive spot, and eliciting another response from her pet. “Oh, have I found somewhere sensitive?” she slid the plug forward a second time and the bear moaned again. She began rhythmically pumping the plug, “Does my little pet like this? Would my pet like me to continue? Whinny for yes or stomp a hoof for no”. She watched the bear blush fiercely as he did his best to whinny like a feral pony.

Victoria gradually increased the speed of the thrusts until the plug was rapidly massaging the bear’s prostate. Shaking from the intense pleasure, she could see him struggling to stay up on all fours. The time had come.

Snow was ashamed of what was happening but who cared about pride when it felt this good!” Suddenly he began to feel something bump into him each time she thrusted the plug forward. He felt it once, twice, three times … then PAIN exploded up his body as his poor anus felt like it would be ripped apart – his limbs gave out and he collapsed whimpering into the hay.

Victoria quickly removed her rubber gloves and threw them aside. “You did wonderfully my pet” she said gently as she began to pet and console the bear. “Your tail is in place and your preparations are almost done. I promise the rest won’t hurt. Just relax and recover. We’ll finish once you feel ready to get up.”

After several minutes the pain had subsided enough for Snow to try and get up. Shakily he rose onto his hands and knees.

As the doe watched him rise she noticed a large patch of wet hay below him, the scent of it told her it wasn’t urine. She pulled on his bridle to guide his gaze to see it. “Looks like my new pet enjoys his tail”. Her other hand shook his tail and the bear moaned with pleasure. 

She placed her head beside his and whispered into his ear, “maybe my new pony would prefer to be a mare? The breeding clause in the contract still won’t matter, you wouldn’t be mounting anything caged up. But there are many ways a mare can assist me. I could use you to help train stallions how to breed like a feral. Not all of my ponies will be kept chaste like you. I could let them use your tight little hole when they need relief. The bear shuddered at the thought of being used in this way.

After a brief pause, she continued, “Does that excite you my slutty little pet? My instincts tell me it does.” The bear was unable to silence a moan, but even if he had there was no mistaking the look of lust on his face.” 
 
“Well, I’ll keep that in mind for later, but first you need to learn how to be a proper pony”.

The doe got up and retrieved a blanket and saddle that were resting on a wall rail. “Now that you look like a pony your training can begin. 
Tomorrow your real lessons will start but for the rest of today I want you to spend time getting used to your tack”. she said as she spread the blanket on his back and strapped the saddle on top of it. “You’re big enough to ride but those lessons will come later, first you will learn to move properly. Now let’s get you settled into your own stall”.

She picked up his reigns and began leading him out of the stall. She felt an unexpected resistance, and when she looked back she found her new pet staring longingly at his back pack. Strange, she thought. “Don’t worry your possessions will be safe”. She gave the lead another gentle tug but the bear still hesitated and glazed at his things. Curious behavior she thought, he’s been obedient so far.

“Snow do I need to use the crop?” The bear’s attention snapped back towards her. He gave a defeated sigh and followed her without further resistance. 
 
The doe led the bear to one of the regular stalls. It was clean and cozy, with most of the floor covered in a thick cushion of soft hay. 

“I encourage you to move around and get used to being on all fours. But until we get your knee pads I recommend that you stay on the hay. The water in your bowl is fresh and I’ll be back in a few hours to feed you”. Then she closed the stall door and walked away.

Snow laid down and thought about what he had gotten himself into. The last few hours had been a blur. Did he really want this? His mind fought a tug of war trying to answer that, and he wished Ember was here to comfort him.

He was snapped out of these thoughts by the sounds of footsteps approaching.  He got back up just as Miss Victoria reappeared at the stall door. Why had she returned so soon?

“Since you’re so new to being a pony, I think it’s wise that you’re supervised at all times. I’ll be assigning my newest stable boy to keep an eye on you”. 

Too embarrassed to be seen like this by anyone else, Snow turned away from the door. He didn’t want to see or be seen by the stable boy, and wished he had somewhere to hide.

He heard the doe say “Don’t be shy, I have a feeling you will become best friends”, and heard her giggle as she walked away. 

Still looking away from the door he waited for the footsteps of the stable boy’s approach. Minutes passed in silence but he heard no one coming. 

Then he heard an old familiar voice. “My goodness Snow, the things you get yourself into never ceases to amaze me! Come on my little bear, turn and face me. Blush all you want, but we both know deep down you’re enjoying this”.

Imaginary or not (and Snow honestly could not tell), there was no denying whose voice it was. Bashfully he looked over his shoulder. Laying on top of the door to his stall was his plushie Ember. Victoria had even fashioned him with a cowboy hat to mark his position as stable boy. His plushie stared down at him with knowing eyes, and his smile seemed more teasingly amused than ever.

The voice spoke up again “With your subby nature I’m sure you’re going to enjoy this … little mare”. Snow’s blush deepened at being referred to as a mare, and the duties it included. “Yup the only thing I’m not sure of is how many times you’ll choose to renew the contract before we finally move on.”