The Help Wanted Chronicles: Santa’s Little Helper
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 over the years. The Prancing Pony was the first story of the series but its events are chronologically last. Santa’s Little Helper is the middle story of the trio. May Santa forgive me for what I have done 😊

Snow groaned as he woke up, another morning with his morning wood struggling to burst out of its cage. How long had it been since he felt the pleasure of his paw? It was hard to keep count but knew it had been many years. 5 maybe almost 6, at least it had effectively been years. Snow had been assured that time moved far more slowly here due to the enchantment of Santa’s Workshop. Six months here was only a month in the outside world, which explained how the elves could make so many gifts in time each year. Unfortunately, he did not know that when he signed a 1 year contract to be one of Santa’s Little Helpers. And since it had been signed in the outside world it would run for the duration of 1 year there.

Snow’s role as his role as Santa’s Little Helper was described as relief worker for everyone else. He had imagined that meant he would be assisting, filling in where they were short staffed or doing odd jobs. 

How could he make the same mistake again after what happened last year at the dairy farm? I should have learned to read the contract before accepting this job. But it's a job for Santa, ‘I’ll be helping to bring joy and merriment to so many’ he had thought. It's not like Santa would trick him.

Snow had been right about bringing joy to many, but very wrong about how. What he found when he arrived at Santa workshop was that the relief he was to provide everyone was related to their naughty desires – and most of Santa’s employees had very kinky tastes. 

Some of the reindeer liked to use him as their pet or a doe for their rut. The Yeti’s treated him primarily like a teddy bear shaped fleshlight, and the elves had a wide spectrum of erotic tastes. From dressing him like a doll to be played with or bound to be used like furniture or a toy. 

There was the time a group of elves bound him like a pony then mounted him on curved rails to be their rocking horse. They had a wild orgy taking turns having sex in the saddle while Snow rocked beneath them – and keep rocking to avoid them triggering the shock collar they placed on him. And then there was the weirdo whose kink was food play with candy canes, gingerbread or eggnog. She loved to stuff the bear, but not by making him eat it. 

(art by Unia Moon https://www.furaffinity.net/user/zombineko)

During his time here he must have been enjoyed repeatedly by everyone except Ms. Clause and Santa himself. He had even entertained Krampus on the rare occasions it had visited (Snow subconsciously rubbed his butt and shivered at the memories). And through it all, no mater how arousing the way they used him was, no matter how desperate to cum he became, the enchantment on his chastity cage prevented it. He had been told it was to keep him focused on others pleasure and not his own.

He couldn’t even claim to be tricked into this. As Santa pointed out his duties had been plainly spelled out in the contract – had Snow bothered to read it.

His thoughts snapping back to the present and he briefly considered trying to hump his pillow, but sighed knowing it was pointless and would just leave him frustrated. Instead he pulled himself from his cozy bed and started getting ready for work, changing into a clean diaper, long Christmas themed socks and the kinky jingle bell harness that served as his uniform.

Just as he was finishing getting ready to go start his duties a letter slid under his door. That usually meant a change in the schedule, perhaps he wouldn’t be servicing the Yeti’s today. He opened it to find orders to report to Santa’s Office.

On his way there he noticed everyone seemed to be especially in a rush today. Elves and other creatures ran about every which way completing various tasks. 

Snow knocked and entered Santa office, as he expected he found him at his desk pondering over a pair of massive books – the legendary Naughty and Nice lists. 

Snow was nervous to interrupt but finally said “Santa, you wanted to see me?”

“Yes Snow” he said looking up from the books. “Its Christmas Eve in the outside world and your contract is nearly done. Even though you misunderstood your role when you joined my team you have done such a good job. Others might have tried to protest or break the contract, but you honored it without complaint or resistance. In fact I have received glowing reports about your work. But now I have a special job for you, one you might even consider a reward”.

Snow was shocked. Not just by the fact that his time here was almost done but by what Santa might be implying. “It would be an honor Sir, I must admit I was wondering when you would call on me to pleasure you...”

“Ho ho no, not that kind of job” Santa chuckled “I know how much socks excite you, how would you like to come with me to help fill stockings tonight?”

“Oh Santa I would love to help you deliver gifts, its what I’ve dreamed of since you hired me”.

“Excellent. I’ll have one of the elves fetch you when its time to go, until then I think there are some Yeti eagerly waiting for you.”

Due to the time difference it was the next day before an elf came to collect him for departure. Snow was sure Santa would be just as thankful as he was that he had time to shower off the smell of horny Yeti’s.

He was brought to the sleigh and found Santa already on board and inspecting his magic sack.

The reindeer were all hooked up and waiting for take off. Donner saw the bear approaching and  snickered, “Look the boss has arranged a little pre-flight entertainment for us!” he called to the team, who turned to snicker at and give Snow lustful glares.

“No Donner” Santa corrected, “you lot can ride him all you want after we get back, but until then the only riding he’s doing is in the sleigh”. 

Snow imagined himself being their entertainment as they celebrated another successful year. He looked away from the team so they wouldn’t see him blushing at as he climbed into the sleigh, but that also meant he didn’t see them giving each other winks and knowing looks. The reindeer knew how a Santa’s Little Helper assisted the boss on Christmas Eve.

Snow looked bashfully at Santa. “Sir I am to go out like this? I’m practically naked in my uniform, what if I’m seen?”

“No one will see us, they never do. But if it will make you feel better wear this …” reaching into his sack and pulling out a headband with fake antlers. “it will create an illusion to make you look like a reindeer”.

Snow took it and put it on. He didn’t notice the quiet snickers from those watching who knew the headband had no magic.

When they were ready Santa cried “dash away all!” and cracked his whip, the end of which struck Prancers ass. 

“Ooooo harder Santa, give me another!” squealed Prancer with excitement, and all the reindeer started to run. Snow’s butt and back knew how much Prancer liked using whips, but he hadn’t known the reindeer like being on the receiving end too.

Within seconds they were in the air and speeding to their first destination. The world below them became rapid blur of motion, even though it barely felt like they were moving.

They landed on the roof of their first house. But when Snow started to climb out Santa told him to wait in sleigh as he got out with his sack to deliver the gifts. The same happened for their next 40 or so stops and Snow was becoming disappointed and confused. Why wasn’t he going with Santa? Did so few still hang stockings?

Finally on their next stop Santa said “I’ll need your help for this one”.

Snow’s mood brightened instantly. He got up and excitedly followed Santa to the chimney. The smoke and heat told him a roaring fire waited below. “I assume your magic will protect us from burns but I going to be washing soot off my white fur for weeks”.

“Don’t worry about that. My magic not only protects us but keeps us clean too. Now grab my arm, and don’t let go until I tell you”.

Snow did as he was told, grabbing Santa’s arm that was holding his sack. Santa touched his nose with his other hand and suddenly they were being sucked inside the chimney. Their bodies painlessly distorted to squeeze inside and down into the room below. There was a sudden rush of heat but no pain as they passed through the fire, and the next second they were standing unscathed by the fireplace.

“You can let go now Snow, see not even a single fur was singed”. Santa started opening his pack.

“Thank you Sir, I hope I won’t be giving out much coal tonight”, but Snow’s response sounded distracted. His attention was on his surroundings and something didn’t seem quite right. There were 4 stockings hung by the fire all the same size, he saw no toys scattered about and only adults in the photo’s on the wall. There was no sign a cub lived here.

“Oh you’ll be filling the stocking of the naughty tonight, but not with coal” he heard Santa reply.

Snow turned just in time to see Santa standing beside his sack as he snapped his fingers. A stream of golden garland flew out of the sack and wrapped itself over the bears chest and arms. It tied him up with his arms behind him, and somehow pulled him down to sit on the ground against the fireplace.

“Santa? What’s going on” Snow asked, surprisingly remembering to keeping his voice down and not wake anyone.

Santa crouched down in front of him and placed a finger to the bears lips. “Be silent and I’ll explain”. But before he said another word he reached down and pull off the bears diaper.

Snow’s eye went wide and he blushed as he franticly looked around to confirm they were alone and unseen.

Santa tapped the chastity cage, “I suspect no one told you the whole reason why you have been kept chaste. You were likely told its to keep you focused on others pleasure and that’s true, but its also to save all that pent-up need for tonight.

“What…what do you mean, what am I supposed to do?” whispered the bear.

Santa pulled a small key from his pocket and slid it into the lock of Snow’s cage. There was a click and it fell off. Instantly almost 6 years worth of repressed arousal started to surface. Santa worked quicky drawing a red ribbon from his pocket and used it to tie the bears cock with a bow like a present.

Then Santa reached up and took down the first stocking. “Even pent up as you are you could never fill all of the stockings we need to tonight”, as he turned it over and slipped in onto Snow’s cock.

“I don’t understand … what of the coal?” but Snow’s voice cracked as he felt the fabric gently brush his suddenly unbelievably sensitive skin.

Santa snapped his fingers again and muzzle gag flew from Santa’s sack to silence the bear. “Silly bear, naughty cubs get coal, but its not their stockings you will be filling tonight. Naughty adults, and I don’t mean naughty like cheating on taxes, get something else”. 

Santa squeezed Snows shaft with the stocking and saw the bear tense up and try to moan, and then he began to stroke.

The bear began to shudder and thrash. The bear had used socks in such a way on a couple of occasions, but this felt different. The sock stopped feeling like fabric. Instead, it began to feel warm and wet, and the strokes started to feel like the stocking was suckling on his cock. This felt more like a blowjob than masturbation. 

A memory surfaced from early during his contract. He saw his first time servicing Comet, but he was seeing it through Comet’s eyes. He saw himself bound to be on all fours, a pup hood covered his head except for the hole allowing access to his mouth. The reindeer pulled on a leash and guided his cock into his pets muzzle. He kept pulling even when Snow started to gag, and didn’t stop until the hood pressed against his crotch. “Good puppy-bear, now play with my bone and you’ll get a tasty treat.”

‘I’m … I’m feeling what the ones I serviced experienced’ Snow thought. While only seconds passed in the real world the scene passed in real time in his head. He felt it all, and Comet’s pleasure and excitement didn’t replace that from Santa’s strokes, instead it amplified it. The feeling became impossibly intense, his cock and balls tingled like every nerve was firing simultaneously and almost continuously. 

It took a mere 6 strokes before he felt himself spurting and filling the stocking. His head tilted back to roar from the feeling, but the magic of his gag kept him completely silent.

But Santa didn’t stop, no mater how much Snow struggled he stroked the overstimulated bear relentlessly until the stocking was filled to the brim. Then he carefully pulled it off and held it out for Snow to see.

“That was quick” he said and Snow’s blush deepened. “Oh don’t be ashamed at the quickfire, we been priming your pump a long time” he chuckled.

The bear could just stare at it blushing and breathing raggedly, even after being denied all this time how could his balls have produced so much? And how was his still rock hard cock dripping and twitching as if capable of more?

“Well done Little Helper” Santa said hanging the stocking and taking down the next “one down, three to go. “My magic and your pent-up need make a special mix. By morning your cum will have transformed into what ever sex toy they most desire, that fits inside the stocking of course. One that will give them pleasure beyond their expectations.”

Snow looked pleadingly at Santa as he approached with the next stocking. He shook his head to say wait and hoping he would let him recover. It was too soon and he was still much too sensitive.

But Santa just chuckled “Sorry Little Helper but we got a schedule to keep and even my control over time has limits. But don’t worry as long as that bow remains you stay hard and be full of cum to give”.

Again the stocking went on and Santa began to stroke, but no matter how much he pleaded Snow knew Santa wouldn’t stop until the stocking was full.

This time the memory that surfaced was one with the Yeti. At over three times the bears size it was easy to understand how they considered him a toy. And those huge body’s had huge cocks to go with them. Most ranged between the length and thickness of Snow’s arms and legs.

He learned quite quickly the magic of his harness did more than keep his barely covered body warm. It also protected from physical harm and allowed him to stretch and be a perfect fit for even the most well-endowed patron of his services – thankfully with minimum discomfort to himself.

Again he found himself looking through the eye of another, but this time he couldn’t recall when this particular interaction took place. Most of them were very similar.

He watched as the Yeti casually picked up him up, his huge hand wrapping around Snow’s torso. He watched himself franticly struggle to get free as he felt the massive cock press against his tailhole, which quickly started to stretch to allow it inside.

He felt the yeti’s pleasure as he watched the yeti’s cock disappear inside. ‘I really am just a bear shaped fleshlight to them’ he thought. 

The Yeti was in bliss as he used the bear to stroke himself. That’s when he saw the second yeti arrive and ask if they could play too, and of course the yeti said yes. It was an unwritten rule of Santa’s Workshop to share your toys.

‘Oh no’ thought Snow now anticipating what day this was. Most of the time the yeti preferred to use him alone, but there were a few times with two Yeti’s. One in particular that now came to mind was when they decided to use him from opposite ends at the same time and ‘meet in the middle’. He knew the result was being left soaked and exhausted on the floor. Discarded and dripping cum from both ends like an overfilled perverted Twinkie.

And sure enough the other (thankfully much less endowed) yeti began to use his mouth like the other was using his tailhole. The world became a confusing fusion of sensations as he now felt experience from both of them simultaneously, and the amplification effect it had on the stocking grew exponentially. And so it continued until the expected conclusion.

Santa pulled the freshly filled stocking off. Snow slouched against the fireplace trying to get his breath back after his last silent roar. He was too week to move and yet while his cock dripped and waited to deliver another load.

“It’s a good thing you’re muzzled, that orgasm would have woke the whole street. I wonder which event you were reliving that time”.

Santa glanced at his watch “Your quick but were still a bit behind schedule; we could use a bit of assistance”. Santa whistled and his sack momentarily glowed. Something began moving inside and out crawled a very familiar fox plush.

Snow looked with disbelief as Ember, the plushie that had been his lifelong companion, stood up and walked over.

“Why look so shocked Snow, didn’t you know toys can come to life at Christmas? Ember I’ll need you to hand me the empty stockings, and hang the full ones. Snow has many still to fill” Then Santa chuckled “Do a good job and maybe you’ll find Snow under the tree tomorrow, your toy to play with before you become inanimate again.

Snows blush deepened as he watched his plushie slyly wink back at Santa. What kinky things would a plush want to do?

Ember climbed Snow to get up to the mantel and tossed Santa the third stocking. 

“Two more and we are done here” he said slipping the stocking on “but don’t worry not every kinky adult was naughty enough to earn a stocking filled by you. After these two you only have 168,249 to go” as he started to stroke again.

‘No, not again, not so soon’ Snow thought, then as he felt a memory surfacing he started to wonder what it would be this time. ‘Please not one of the elf orgys, I can’t handle that much all at once … or that freaky elf with her kink for gingerbread and eggnog. I was blindfolded for that, and I think I’d rather not know what that was about!’ 

(scroll to next page)

The end.

(art by OatmealGoat https://www.furaffinity.net/user/oatmealfoxy)