Santa and His Elf

Hello all! Here's my last story of the year! It's been a really great year in terms of consistently writing and such! Thank you all for all the feedback and support you've given me!

Slight departure from what I usually write, this story is a male on male tale. Male on femboy technically. Also features the return of Isaac from my Halloween story!

Important tags are: huge/hyper sized dick, cum inflation, excessive cum, anal, gay sex, all the way through, and femboy stuff

As always, constructive feedback and comments are appreciated!

~~~~~

Darkness from heavy gray clouds covered the afternoon sky. A light downpour of snow slowly covered the city, blanketing the streets, buildings, and people in a soft layer of white; a sharp contrast to the foreboding skies. Cars and residents moved much slower, taking their time despite the chilly atmosphere. Large coats and heavy boots had become the norm, zippers pulled up to chins being the hot fashion of the season. Hours spent shoveling, salting, and dealing with the uncompromising weather took up much of people's time, hindering the frantic feeling of the month. Yes, it was definitely winter.

A single man stood out from the crowds filled with dark-colored coverings. Standing in front of a non-descript store, next to a hastily setup table filled with papers and a large bowl, with a sign that read 'Donations' above it, was a man dressed peculiarly, but recognizably. A red furry hat, brimmed with more white fur, and a similarly crafted white ball on the end of it adorned the top of his head. The rest of his outfit was much the same: a large coat of the same coloring, baggy red pants barely held up a large black belt, and thick brown boots made up the rest of the ensemble. To top it off, a clearly fake, large white puffy beard was wrapped around the man's face, barely concealing a rather intense grimace. It didn't take 3 guesses to know who this man was supposed to be.

"God this fucking sucks." Isaac muttered under his breath as quietly as he could. A standard, stereotypical-looking nuclear family group walked by him, giving him an almost customary smile. He waved the large bell at them as they walked by, clearly trying to ignore his loud beckons. Isaac watched as they passed; the young son looked back and pointed at him and began to say something before his father hastily pulled him along. This was the scene that Isaac had witnessed countless times today, and countless times the entire month. How did he let himself get roped into this?

Well, he knew how. This charity work, if that's what he could call it, was something he had been bullied, or rather blackmailed into doing. The establishment he worked at, a restaurant primarily known for its breakfast, had a deal with a local charity where they would get some of their employees to volunteer and help raise money. He didn't know why they did it, the owner wasn't a particularly generous man himself, but he could guess the reason: tax break. Regardless of the reason, his manager had pulled him aside to convince him to volunteer, reminding Isaac of that time he had come to work visibly drunk, and how the manager looked the other way. In Isaac's defense, it was an accident - he simply forgot he worked that morning. So that's how he ended up here; it was either this or lose his job.

So here he was! Standing out in the goddamn cold, waving this stupid fucking bell and wearing this shittily made costume that caused him to itch for hours after the fact. Most people ignored him, which he considered a blessing, except for the occasional generous person or religiously-obligated individual of course. It was mostly old people who looked like they might collapse in the cold weather who told him what a good job he was doing and asked what church he went to. He wondered how they would feel if he took off this stupid fake beard and showed them he was Middle Eastern - it would probably give them a heart attack. The thought brought a smile to his face as he waved his bell at another couple, trying his best to subtly admire the woman's fat ass that bounced enticingly in her leggings as she passed him without a glance.

Glancing around to make sure no one was about to enter or leave, Isaac quickly pulled his phone out of one of the deep pockets of the baggy pants; that was one blessing, Isaac guessed. At least the pants were roomy. Checking the time, he grimaced under the fake facial hair once more. Christ alive, he still had several hours left of this. Catching a bit of movement out of the corner of his eye, Isaac hastily put the phone back into those bottomless pockets and began to wave the bell, an almost automatic reaction at this point. However, the group that approached Isaac was out of the ordinary for the day, and definitely a sight for sore eyes.

It was a group of three that walked towards the shoddily-dressed, reluctant charity collector. Slightly ahead of the rest was a blonde that marched at the helm. Despite her layered way of dressing, Isaac's always keen eye caught the tell-tale sign of large breasts jostling together under her top. Isaac barely noticed any of her other features, not that there was much else to ogle with all the layers she had on, but he'd be damned if he didn't notice those tits. The other girl closest to her was dressed much the same. Isaac of course, noticed something others might not. Even though she was in front of him, her hips and thighs were very thick, and Isaac swore he could see the sides of her ass peeking from behind her legs, barely covered by her long brown hair. It was like everything Isaac loved split into 2 veritable beauties.

But for some reason it was the last girl that caught Isaac's attention the most when he finally tore his eyes away from the pair in the lead. Standing in the back was a girl who was much unlike the others. She was short, that's for sure; Isaac would eat his phone if she was an inch over 5 feet tall. Her golden-brown hair was cropped short, and parted to the side fashionably. A tiny button nose and small, bright pink lips contrasted against her large brown eyes nicely. She wore only a light layer of makeup, having picked gentle colors to compliment her soft features. Her cheeks had the slightest bit of chub on them, which only added to her absolutely adorable appearance.

The rest of her was much the same: petite. She wore a simple black long sleeve, and there was nothing to not leave to the imagination there. Her tight jeans were much the same, leaving not much guess work, but one didn't need to guess. Flat chest, thin legs, and tiny feet - small features were the name of this small girl's game. This pixie-haired cutie was someone Isaac usually wouldn't find himself checking out, yet, he found himself almost overwhelmingly enticed by her tiny body. Almost like she could read his mind, she caught his eye as she passed and gave him the smallest, cutest smile.

Isaac watched her go by, mouth nearly agape; he was wrong about one thing though. Even if it didn't compare to her much more voluptuous friend in front of her, her ass did look enticingly bubbly in those tight jeans. He watched her walk by, his eyes never leaving her small frame, until she finally strolled through a set of automatic doors and disappeared into the store. Turning back towards the street, Isaac realized he had completely ignored several other passing people, and began to frantically wave his bell back and forth. Unfortunately, he didn't see her or her friends leave due to the exit being on the other end of the store, and the rest of his evening continued on in painful monotony.

Another day, another wasted, miserable weekend. While it wasn't snowing today, something Isaac was thankful for, the weather seemed to have decided to punish his existence anyway and replaced the snow with biting, cold winds. Isaac shivered quietly under his costume, the constant waving of the bell the only real, constant movement he was allowed. He wished someone a compulsory 'Merry Christmas' as they dropped some change in his bucket, trying to give his best smile under the mass of fake-hair that covered his face. All day he had been scanning the parking lot, hoping to catch a glimpse of that lithe woman he had seen the day previous; and as the day came to a close, his hope had diminished into nothingness.

After packing up the table and the donation box, a representative from the actual charity came to collect it. An older, portly man with a perpetual scowl who always seemed to eye Isaac with disdain. They talked briefly, the man not seeming to think much of Isaac, before they parted ways. As Isaac stood outside his car and checked his phone while taking a moment to remove the itchy beard, exposing his own dark facial hair, he heard a pair of footsteps coming from in front of him. Looking up instinctively, he felt his heart momentarily stop at what, or in this case, who, he saw standing before him.

On the other side of the parking space, standing next to her own small car, was the girl from yesterday. She was dressed very similarly as before, a large red and green sweater covering her top and tight, hip-hugging jeans on her lower half. To Isaac's embarrassment, she definitely noticed him staring at her, and she gave him another cute smile. Isaac grinned stupidly back at her, and waved at her with his phone-occupied hand. Giggling, she waved back before turning away and getting in her car. Trying to control himself, Isaac followed suit and entered his own vehicle. Pretending to fiddle with his things, he took a moment to watch her turn the car on and drive away. Fuck, he should've introduced himself.

The next day Isaac had, thankfully, the day off from both his job and his so-called volunteer work. He decided to spend the day getting some errands done, his own holiday shopping and personal buying-needs having gone woefully ignored. After getting ready, and throwing on a long-sleeve black shirt, heavy brown coat, and some baggy sweatpants, which were practically a requirement for the well-endowed man, he left his home and headed out. Hopping in his car, he immediately turned on the radio, the soothing sounds of grinding guitars suddenly assaulting his ears. Isaac sat for a moment before deciding this day to his self needed to start with something incredibly important: coffee.

Driving much slower than he usually did due to the weather and horrible state of the roads, Isaac reached one of his local coffee shops much later than he had anticipated. Parking his car, he let out a long yawn as he exited the vehicle, shivering slightly as a cold gust of wind brushed over him. Isaac moved slowly, treading carefully over the icey ground as he approached the front door to the coffee joint; he didn't want to be that asshole who slips and busts his head open like some kind of tourist. Finally reaching the entrance after several agonizingly long minutes, he let out a long sigh, pulled out his phone and entered the building. Stepping in line, he scrolled aimlessly on his phone as he awaited his turn to order the delicious brown nectar that would make the rest of his day infinitely better.

Isaac had barely noticed that he was quickly approaching the front of the line. He was engrossed in some article that popped up on his phone, something about a line of underwear and lingerie made for futanari being made for the first time; he had heard of them before, women born with male genitalia that were supposed to be extremely well-endowed, but hadn't met any to his knowledge. Isaac didn't care about the lingerie, but having properly fitting underwear for the first time in his life would definitely be a blessing. As Isaac stepped up the register, something that barely registered in the man's mind as he poured over the article, a sweet, soft voice called out to him.

"...what can I get for you today?" was all Isaac caught as he looked up. Before he was able to give the barista his usual order, his voice caught in his throat. That quiet, gentle voice had come from a tiny woman, one who was quickly becoming familiar to the shocked man. He definitely hadn't expected to see her here. Hastily shoving his phone in his pocket, Isaac cleared his throat as he made eye contact with her. Man, she was really pretty. Momentarily forgetting why he was there, it took Isaac a minute to actually give his order, stumbling over his words as he did.

"Uh, hi. I'll take a large Americano, uh, extra shot added. Please. Oh, and it's to go!" Isaac finished abruptly, his face going red at how shaky he sounded.

"Somebody must be tired! Long weekend?" the short-haired woman, whose nametag read 'Taylor' asked, giggling to herself.

"Ah yeah, you know. Standing out there in the cold in front of that store by myself gets pretty tiring!" Isaac replied, trying to make a joke about it while hoping the cute girl recognized him.

"Oh yeah, I think I've seen you out there a couple times! Can I get a name for the drink?"

"Mhm, it's Isaac."

As they finished up the transaction, Isaac walked away, giving Taylor one last smile as he departed. Standing off to the side, he waited patiently for his drink. His name was called after several minutes, and as he walked up to grab his hot cup of liquid energy, he glanced around hoping he might be able to catch Taylor one last time before he left; unfortunately, she was busy with a customer, so Isaac reluctantly grabbed his drink and left. The rest of his day was uneventful, and he managed to get most of his shopping done. He ended up hitting the hay a bit early, knowing that he had to open the restaurant in the morning. At least he had a few days left before he had to don that stupid costume again.

And those few days passed so quickly it was like life wanted him to suffer. So Isaac once again found himself standing outside that grocery store, suit reluctantly worn and headache-giving bell equipped; it gave him a +1 bonus to his annoyance levels, which he definitely didn't think helped with trying to get people to donate. At least there was no wind or snow today, although Isaac didn't try to dwell on it - all Mother Nature needed was to see that he was the least bit happy before it decided to smite him. Isaac rang the bell at another couple, barely even bothering to form a smile under the bushy white beard he was wearing. They passed him without a glance, something he should've been used to, but only added to his frustration he felt at his current predicament.

"Isaac?" a distantly-familiar voice called out. Turning around, Isaac's eyes opened wider than they had been the entire day. Walking towards him was Taylor, dressed up as what he presumed was an elf. She had her own green Santa-esque hat on, with a small bell on the end that jingled as she pranced over. She wore a large green sweater, plasted with holiday-themed imagery. A small green skirt hung off her tiny hips, complemented by practically-painted on black tights. To compliment the outfit even more, she had on a pair of brown furry boots, with what looked like tiny bells on the end, ones she had no doubt attached herself. She hopped over, standing in front of the stunned man, a large smile on her face.

"Uh hey, Taylor," Isaac responded, trying to play it cool and make it seem like he didn't absolutely remember her name from their one real interaction, "what are you doing here?"

"Well I said I saw you out here a couple times, and you mentioned it gets really tiring! So I thought you might like some company..."

Taylor blushed and looked down, kicking her foot against the ground.

"Unless you don't want me too..."

"Oh no! I uh, would enjoy the company for sure. You're more than welcome to stay and hang out!" Isaac smiled from under his beard, trying to appear as welcoming as he could.

"Great!" Taylor exclaimed, moving forward and standing next to Isaac. Standing next to her, Isaac realized she was really a tiny woman. Isaac wasn't stupendously tall by any means, being a bit above average for a guy, but it didn't even look like she came up to his shoulder! He gulped as he stared at her, the small girl smiling off into the distance. A family walked up, and Isaac remembered he was here for work, or at least what felt like work. Lifting his bell, he waved it rapidly at the family, and almost if on cue, Taylor stood up on her small toes and waved them, that adorable smile never leaving her face. The family walked off, and Taylor turned back to Isaac.

"Tell me about yourself!"

This drew a laugh from Isaac, who wasn't expecting the request, or maybe it was a demand, at all. Looking down at the small girl, Isaac told her a bit about himself. He told her about him being a cook at a local restaurant, one she apparently had frequented often, which drew some laughs from the pair. This turned him to him complaining about how he got roped into this whole thing, which only made her giggle more - although he definitely left out the part of the story where it was to avoid getting fired. And, of course, he filled her in on some of his interests, like heavy metal music, horror movies, and video games. As he told her, he really hoped it didn't make him sound like a stereotypical guy, even though that's how it felt.

"How about you little Ms. Elf? You haven't said anything about yourself!"

Taylor blushed, and then waved, drawing Isaac's attention back to his work. After a few more families walked by the pair, she began to open up. She attended the local community college, having graduated high school a couple years back; Isaac was for sure happy about that, because she looked much younger due to her small stature. By her own admittance, she said she didn't do much outside of hanging with friends and watching Netflix, although she did blush when she admitted she had waited in line to buy the newest state-of-the-art gaming console. This drew a laugh from Isaac, and he joked he would have to get her gamertag later, which made her face light up.

After that, the usually-long hours seemed to pass by effortlessly. The Christmas-themed duo continued to chat in between trying to get donations. Isaac quickly began to feel comfortable, and even tried to turn the charm on when he could; small touches here and there, flirty jokes and the occasional innuendo all seemed to work wonders. At one point, when the wind did pick up a bit, Taylor shivered and leaned against the much-taller man, which made some warmth rise to Isaac's cheeks; for once he felt thankful for the beard covering the majority of his features. The day drew to a close, and as Isaac began to pack up the table, the representative from the charity pulled up.

"Who's this?" he questioned gruffly, staring at Taylor, "thought the restaurant only sent one of you. I told your boss we only wanted one."

"Uh, well..." Isaac mumbled as he tried to come up with an excuse. Shit.

"Oh don't worry, I'm just his girlfriend!" Taylor immediately interjected, smiling and grabbing Isaac's arm, "we're actually going to a Christmas party right after this, so I figured I'd come and hang out as he finished up!"

"Hmm ok." the man grunted, seeming to accept the excuse as truth. He grabbed the donations and papers from Isaac, before turning around and getting back into his car. Watching him drive away, Isaac let out an audible sigh before turning back to Taylor, who still held his arm tightly. Looking down, he smiled at her, enjoying the feel of her body on his. They stayed like this for several minutes before Taylor finally snapped out whatever trance she was in, and coughed in embarrassment. She detached herself from Isaac, to his immense disappointment, and looked back up at him.

"Sorry, I didn't want you to get in trouble. I didn't mean to hold you for so long..."

"I should be thanking you!" Isaac exclaimed, chuckling, "you really saved me back there. Besides, I don't think anyone would complain about dating you, least of all me. I'd be more surprised if he didn't believe you were my girlfriend, cause you're so out of my league!"