Sire's Hollow Shenanigans
Rewarded for Stellar Work
“Welcome to Sire’s Hollow.”
Those were the famous last words of a small speaker, placed by the gate of such a lovely little town. You, Anonymous, assistant to the Sire’s Hollow Development Committee, were to remove such an annoying device from its perch.
And remove it you did, immediately shutting it off.
“Thank you, Anonymous. Just one more thing off the plan for today,” said the woman behind you.
“Glad to help, Stellar Flare.”
“Oh, come now, no need to be so…formal, with me, just call me Flare! Or Stellar. Whatever you like, you’ve been here with us for long enough,” Flare insisted.
“Yes, yes, of course…Flare,” you responded, taking her checklist and looking over it with her. “So, we next make sure that the…and I use this term lightly…’Essences’, are disposed of?”
Stellar stood behind you, placing her hands on your shoulders while you read the plan. Your boss was always very hands-on, and often walked alongside you to check in on your work.
Her touch always felt…comforting. Your boss never gave off the vibe of a micromanager, like she claimed she used to be, but more like a caring mother who was only there to help, to ensure you were being your best.
The fact that she was slightly taller than you in those…heels of hers, was also a bonus, giving her an air of confidence and dominance wherever she travelled.
You often find yourself peering at them, when you probably shouldn’t.
“Absolutely, Anon. My wonderful son specifically requested that one, you know. It took me a little bit of time, but…well, this oldie caught on eventually,” she replied, letting go of you.
“Oh come now, Flare, you’re telling me you’re old? Gimme a break,” you said, rolling up the scroll. You then realised what you just said, and just how…scandalous it sounded.
But clearly, Stellar didn’t care. She never cared when you said such things. In fact, she let out a bright giggle, one that had embodied the joy of a young schoolgirl.
“Now where were boys like you hiding when I was so young? You must have broken quite a few hearts in school…”
Your heart swelled with pride. Compliments like that weren’t uncommon from your boss, and they certainly weren’t unwelcome.
“Alright, Anon, we’ll get this done, and then I’ve planned a small brunch for us, ok? A little reward for your work for the Committee so far,” she said, her confident stride keeping pace with your walking.
You and your boss travelled back to the town square, which seemed to be split down the middle between outdoor-shopping mall style, and buildings that looked like they belonged in a previous era. It was a little odd to get used to two different ages placed right next to one another, but thankfully, the Preservation Society had finally gotten along with the Development Committee. The differences in amenities and services between the sides were becoming less and less pronounced, thanks to the work of people like you.
The two of you stopped at a counter with various perfumes, or ‘Essences’ as the town like to call them.
“Ahh, now let me see…I had told the owner to create her OWN scents, without my input. Let us verify that these are non-overbearing…”
The two of you, with the owner’s assistance, inspected the new perfumes one by one, spritz by spritz. Seriously, how did your boss consider any of this to be hard work? You certainly weren’t going to complain, though.
“Excellent work, Miss. I think I speak for my boss when I say that,” you said, placing the last bottle of perfume back down onto her counter.
“Now there are REALLY none of the drawbacks! The tourists are going to love this!” the owner cheered.
Stellar took a look at her list once again. “Perfect, Anon. Now you look hungry to me. I assume you remember what I planned? Come and follow me.”
“Brunch, yup. Let’s go, I could use a waffle or two…” you replied, walking behind Stellar. Her long strides, her confident walk, was always a treat for you to enjoy. How she did it so well in heels was a mystery, but that was all the more reason to steal a quick glance here and there.
Before long, the two of you were sat down inside the little cafe, a vegetable-laden sandwich in front of her, and a plate of fresh waffles for yourself. For reasons known only to Stellar, she had reserved a small table in a darker, quieter corner of the place.
“Mmmm, you know, you always take me to the best places this town has to offer,” you said, through your waffle-trance.
“Nothing less for the hard working young man. After all, he needs to keep his strength up for me!” your boss replied, digging into her sandwich.
If only the job market back on Earth offered gigs like that, with bosses like Stellar Flare.
As you finished up your plate, you noticed that Flare was looking at you strangely. You were fairly used to her sizing you up, but this time seemed…a little different. And she had her signature half-lidded eyed smile. The smile that told you, she knew something you didn’t.
“I didn’t bring you here strictly to feed you, Anon.”
You perked up slightly. “Oh? Is everything alright, Stellar?”
“More than alright, in fact,” Stellar confirmed, slowly leaning downwards. We’re here so you can enjoy a little bonus. A personal gift from me, to you. For all your assistance.”
You felt one of her high-heels prod your shin. And the other one rest on your toes. Almost like she was testing something.
If she was testing something, she certainly had passed. The closeness of her feet to yours caused your body to tense a little, and you’re almost sure that she was fixating on your reaction.
The single hottest lady in Equestria had her elbows on the table, and her light green eyes were locked onto yours. One of her legs crossed over the other, her heeled foot peeking out of the white tablecloth. The article of footwear slowly began to lose its grip on her cream-hued lower leg, exposing more and more of her ’stocking’ as well as all of her toes except the one holding the shoe aloft.
“You’re a grown, handsome young man, Anon. I think you’ve earned a little token of my gratitude for your hard work. I certainly hope, for the first time in my life, that you don’t have any other plans…” Flare said, batting her eyes at you. Her foot retreated under the tablecloth, and you could just about hear a clack as her heel fell to the ground.
“Wh-what are you…what is this?” you whispered, as your boss gave you a seductive grin.
“Oh, simply what I had planned for you today…I assume you won’t have a problem, with me doing you such a favour?”
The pressure put between your legs persuaded you to answer correctly, listening to your mind.
Nope. Nope. No problems at all.
“I knew you would see it my way, Anon. Did you, perhaps, think I wouldn’t notice where your eyes wandered, young man? How unprofessional…” she whispered.
You couldn’t see exactly what Stellar Flare was doing, but you could damn well feel it. The creamy, lighter bare foot was pushing right between your legs, the flexible toes gently gripping your rapidly hardening tip. You took a sharp breath inward, your eyes darting around anxiously.
Thankfully, there was no one else in the restaurant, besides the workers. How Flare looked so confident, so sure of herself while performing such debauchery, was beyond you.
“Oh, don’t be so shy, Anonymous…I’m just, ensuring you’re properly…compensated, for your efforts,” she quietly murmured, dragging a single toe down your bulge, and back up again, before weighing her entire off-white sole once again between your legs.
“B-but Stellar, you’re my SUPERIOR, and isn’t tha-“ You’re cut off with a finger over your lips, and a knowing grin from the development expert in front of you.
“I think you know by now, Anon, that no one ever became a success by following all the rules…right?”
Her soothing voice, coupled with her clear…expertise in this area, was beginning to become infectious. Stellar ALWAYS knew what she was doing. She had clearly planned such a gift meticulously, just for you.
It certainly helped that Flare was clearly having just as much fun as you were.
And her plan was coming to fruition. You could feel her big and second toes grabbing onto your zipper, pulling it downwards, while her other foot shook free of its high-heeled confines and assisted in fishing your member out of your boxers.
Your face was as red as could be, and you were dripping sweat by the time Stellar’s ‘socked’ feet had locked you into their tight embrace. You could already feel your member throbbing, confined between your boss’s incredibly soft feet.
“S-Stellar…I’m g-gonna…” you whispered, as quietly as possible.
“I don’t think so, Anon. Not yet. I planned for you to enjoy a little something. Be a dear, and be strong for me?” she cooed, leaning over the table and stroking your chin with her forefinger, sending shivers down your body. Her feet slowed down, putting pressure on your cock once again and remaining still, pinning it against your belly.
Normally, such overwhelming pleasure would have made you lose it, but something about Stellar Flare’s gently commanding tone had you smitten. Like she suddenly had taken complete control of when you were allowed to let loose.
And so, your body refused to climax at that moment, allowing your boss to continue her work.
You decided to lift up the tablecloth, ever so slightly, just to see how incredibly heated your ‘reward’ truly was. It was every bit as beautiful as you had imagined. Flare noticed what you were staring down at, her grin turning more playful. Her off-white, ’socked’ feet were clearly well kept, and they were flexing, one at a time, just to tease you further. Your length was twitching below her feet, aching for pleasure, soaking her skillful soles in precum.
“Mmm, now what do you think you’re doing? Messing with my little itinerary once again, Anon? You’ve certainly changed your tune quickly…” she giggled, reaching across the table. “Risking everything might make things rather messy.”
Her off-white hand grasped a small jug of maple syrup, the top of her left foot sneaking downwards, gently cradling your balls. “If it’s messy you want, it’s messy you’ll get.”
Was she…?
She reached under the tablecloth, syrup in hand, and your jaw dropped slightly. You could feel something slightly warm, sticky, dripping down off Stellar’s ‘socks’. Between her toes, over the tops, and all down your dick. Her fingers played with the tip her blue collar-tie as her blush deepened.
The two of you stared at one another. There was no going back from such a mess.
Your boss once again clasped her soles around your cock, smoothly sliding them up and down together. Your face burned as her syrupy feet hugged your member, teeth clenching while you desperately tried to hold back your groans of bliss.
“Mmmm, you asked for this, Anonymous…I think you’re rather bold. Quite the SWEET reward, isn’t it?” Stellar Flare murmured, placing the syrup back onto the table and grabbing one of your hands.
She grabbed the base of your cock with two of her sticky toes, her other cream-coloured sole rubbing across the right side in shallow, gentle circles. You weren’t going to last much longer against the skillful, graceful strokes, and your boss knew it. You could tell on her face that she wasn’t going to hold you back for much longer.
She scrunched up both of her soles, and then released your base from the grip of her toes. Her freed foot then joined her other, the top of one pressing into the upper side of your member, and the other side pressed into her soft sole.
You gulped heavily, your face pouring sweat as you reached down to feel the foot facing you under the table. Your hands gently ran along the sticky, sweetened socked sole, causing your boss to giggle sexily.
Both of her feet began to glide up and down, once again. One foot moved up, the other went down. This incredibly hot pattern continued, Flare biting her lip seductively and tightening her grip on your hand.
At last, through the haze of pleasure, and the slightly slick sounds her soles made while she worked you over, your ears picked up on the words you were so desperate to hear.
“You can cum, sweetie. Go ahead.”
Instantly, your body let go of all its tension, its strain. Warm shot after warm shot of your pent-up seed landed on your boss’s ‘socks’. Her off-white feet maintained a tight grip on your cock, smoothly sliding up and down, ensuring that you were able to coat every inch of her feet in your essence.
Your knuckles turned white as you held onto both the table and her hand, the best orgasm of your entire life having rocked your body. If it had been any other day in Sire’s Hollow, and if it had been anyone else other than the calm, confident Stellar Flare…You don’t even want to think about what could have happened.
As you enjoyed the last moments of your mind-blowing climax, Flare sat back in her booth-cushion, removing her soles from your length.
“I think you and I can both agree, Anon, that was rather fun, was it not?” Flare giggled, grabbing a few napkins and handing them to you.
“O-oh…that was…that was so nice, thank you, Flare…” you said, weakly, doing your best to clean yourself up as discreetly as you could. Stellar placed her feet on the booth next to you, expectantly, curling her toes to catch your attention.
You would never have allowed a lady of her calibre to have to clean up such a mess. You gladly took on the duty of tidying up her messy cream feet, polishing them as best as you could.
“Once again, STELLAR work, Anon,” your boss laughed, “Now, we have a plan to return to my office to catch up on paperwork. I assume now that you won’t mind staying on the clock an extra hour or two?”
Stellar Flare crossed her now-sparkly clean feet on the booth next to you, gently rubbing them together to grab your attention.
“…Do I get overtime?”
-End
Author's Note
Sockmom
Bottom text
:)