Nightmares and Nylon (2025 Nightmare Night Sassy Saddles foot story)


                                            1.
                                            
                                                "Do people always wait until Nightmare Night itself to try on and buy their costumes?" you inquired, having just assisted a customer with a beautiful siren outfit. Your boss, Sassy Saddles, was easy to spot in the dimly lit sales floor, thanks to her height, her distinctive floppy orange hair, and her slightly-less-than-professional witch outfit, with high heels instead of those curled up shoes that any normal old hag would wear.

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                                                You always did wonder where all the beautiful young witches hid, but with the job Rarity gave to you, you had all the proof that you needed that they existed. And that proof was in the form

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                                                of your superior.

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                                                Sassy turned around as you snatched another handful of candy from one of the bowls, placing it in a bag you had been carrying. "You can see it yourself, Anonymous. This holiday is quite surprisingly one of Rarity's biggest sales nights, next to the night before the Gala!"

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                                                "I just think it'd be better if one were to prepare long in advance for Nightmare Night, but hey, that's just me," you said, "We do still get to enjoy the party, right?"

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                                                Your boss scoffed, giggling as she pointed out the centre of the shop full of dancing patrons, likely on sugar rushes like you were. "Chiffon and shush, Anonymous, do you take me for one who would deny my assistants such a glorious night? Nor would I refrain from participating myself! Now yes, do keep our customers in mind, but I sense no other incoming purchases. Come and dance with me!"

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                                                You took her hand, kissing it with a bow, flattered at her advances. "I would be honoured, my lady."

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                                                "Polite and gentle as always, my wonderful assistant," Sassy said, leaning down to kiss your cheek and making your face warm up. She then whispered into your ear, "Be sure to keep a close eye on my footwork. I'm certain that you'll find their movements to be mesmerising..."

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                                                Sassy wasn't wrong. Her feet had always moved gracefully, with purpose. They were there to be seen. To attract attention. To be pampered, like they deserved. The dance floor was no different.

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                                                You were lead by your boss to dance, and at her little request, found yourself mostly paying attention...downwards on her body. Sassy's arms wrapped around your neck, the toe of her high heels pressing down on your foot in acknowledgement.

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                                                The next few hours saw neither any more customers, nor a break from dancing and enjoying candy with your boss. Sassy turned out to be right. It was very easy to lose track of time when you were enthralled by her expertise on the dance floor. And lose track of time you did.

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                                                --

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                                                Both you and your superior stumbled up the stairs at the back of the Boutique, having locked up the shop area for the night as soon as all the partygoers had cleared out. "So...the apartment? I never knew...there was an apartment back here," you said to her, the two of you arriving at the door at the top of the stairs.

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                                                "I refuse to allow you to walk all that distance to the other side of town, Anonymous, considering the night of dancing and filling up on sugary treats," she tiredly replied, unlocking the door and leading you into her place, "If Rarity so generously allowed me to have use of the apartment, then I see no reason my wonderful assistant cannot join me for the night."

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                                                You marvelled at the fancy dwelling as you stepped in, but you didn't have too much time to calculate the cost of the marble in the walls alone before Sassy took your bag of treats and placed them below a nearby coffee table.

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                                                "Anonymous, dear, could I trouble you for an extra favour tonight? Just one small favour," your manager asked, sitting down on her couch and panting.

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                                                "Yes, Miss Saddles?" you replied.

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                                                "Would you mind once again disregarding the job description that Rarity gave you, and instead following along with my tried-and-true Pattern?" she finished, lifting her legs up and placing her shod feet across the sofa.

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                                                When Rarity offered you a job in one of her boutiques, what Sassy began to ask of you was not what you had in mind. However, given Sassy Saddles' knowing, half-lidded eyes staring into yours, and her feet crossing over one another, did you really have a choice in the matter?

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                                                Did you WANT a choice in the matter?

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                                                You sat down next to her black heels and polished toes, placing your hand on the left. "I do understand how stressful your career can become, Miss Saddles, as can all that dancing. I'm assuming your Pattern for me involves working on your feet after a long Nightmare Night?"

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                                                Sassy nodded, removing her black witch hat and flipping her bright orange hair out of the way. "You are a wonderful assistant, Anonymous, not only in matters of colour coordination and design imagination, but also in matters of self-care. When you first began, and I saw your almost...excessive efforts in the shoe department, how happy our customers were, I was able to conclude just how skilled your fingers would be."

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                                                Your boss briefly rested one of her black high heels between your legs, her foot literally just out of reach of the area where it mattered.

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                                                "Among other things, of course."

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                                                You gulped, starting to sweat at the images buzzing through your mind. Suddenly, the light blue lower extremity in tantalising distance became your only focus. "I'll do it, but...is a little something extra part of the Pattern tonight? Please?"

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                                                "Hunky haberdashery, Anonymous. You truly are the finest of gentlemen to indulge me like so," Sassy said, flicking on the TV and placing her sky-blue feet in your lap, expectantly. "You know as well as I do the Pattern we follow for such...intimate tasks."

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                                                Like the kind man you were, you worked her black heels off of her poor feet, each one tensing and making a slow circling motion via the ankle. A sigh of appreciation escaped your manager as she clapped her hands twice.

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                                                The lighting in the apartment suddenly dimmed, leaving only the glow of the orange and purple string lights, as well as the flickering light of the various candles, in its place.

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                                                "Spooky, Sassy, very spooky," you commented, starting to run the palms of your hands up and down the bottoms of her feet as a horror movie's piracy warnings and opening credits came on.

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                                                "I do regret not choosing more comfortable footwear for the party, Anonymous, but I suppose I should thank my lucky stars that you didn't take Nightmare Night off, mmm..." Sassy hummed, as you worked your hands over her left foot. Both of your thumbs dug their way into her heel, taking their sweet time in making their way up her delicate sole.

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                                                "How nice it is to have my helpful assistant, mm, keeping me company to end off this most GORGEOUS of nights...Yes, further up, please," Sassy moaned softly. She moved her right foot, pointing at the left arch with her big toe and ever so gently dragging it down the curve. "Here."

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                                                You turned your attention to her arch without delay, giving the tender flesh a single squeeze, earning you quite the reaction from your boss. She leaned her head back and scrunched her perfect toes, and then splayed them widely. "Ahhh...Anonymous, harder please..."

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                                                You didn't need to be asked twice. Your fingers sunk into the pampered foot, kneading the smooth surface as firmly as you could, hard-focusing on the sensitive arch as requested. Sassy let out a deep shuddering breath of relaxation, popping one of her beautiful golden eyes open, watching you closely.

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                                                A coy little smile crept across her face, seeing how locked in you were. She curled her toes on her left foot, moving it back and forth while in your grip to grab your attention even more, while sneakily moving her free right foot off your leg...

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                                                ...Right into the bag of treats that she had left nearby on the floor below the coffee table.

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                                                It wasn't until you heard the rustling in your bag, and noticed your boss lifting her bare sky blue foot back up, a rather delicious-looking bar of chocolate still wrapped and held between her big and second toes.

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                                                You looked at the face of your boss, confused, but your face was reddening. The way she slid her left foot back out of your grasp, her half-lidded eyes. Her tender left foot, free of your hands, gripped the other side of the chocolate bar.

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                                                Something of yours began to feel something. Envy, perhaps, of how lucky the position that candy was in.

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                                                "Monsters and minky, Anonymous. You look like you want something sweet to bite."

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                                                In a display of function as well as form that only Sassy (or Rarity) could manage, her left toes gripped the candy more tightly, while her right toes gracefully peeled off the wrapper, tossing it away. Your mouth hung open in awe, the sweet smell of the chocolate filling the air.

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                                                Your boss decided that that was an invitation, breaking off a piece of the bar with her toes, batting her eyes at you as she placed the chocolate on your tongue. Her other sole gently rested against your burning red cheek, sliding in slow circles as you accepted the candy and chewed silently.

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                                                "Just a little trick I picked up, Anonymous," she said, feeding you another piece in the same way. The rich chocolate had picked up some of the delicate flavour of her looked-after toes, and it lingered on your tastebuds more strongly with every piece fed to you afterwards.

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                                                Amused at your now-sweating face, your witch-attired superior began sliding her foot down from your cheek, further and further south on your body. "Quite the treat, is it not?"

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                                                "S-Sassy, wait, I'm not finished with your massage yet..." you stammered as her other foot planted itself over your face. The smell of the chocolate lingered as the curvy, supple sole dragged down over your nose, her big toe stroking your lips.

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                                                "Nylons and nonsense, Anonymous. You forget, I am here to assist you as much as you do me. Do we not both deserve a treat tonight of all nights?" she insisted, shaking her head and keeping her big toe pressed over your lips.

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                                                You opened your mouth to speak, only to have Sassy's black-polished toe slip in against your tongue, making speaking rather difficult. "Ahh leah lemme do thih..." And you grabbed her right foot off your face, focusing your efforts on her curved arch as before.

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                                                Despite the ease at which your fingers were able to elicit satisfied moans from your boss, Sassy was determined and focused on task as always. Her left foot pushed just that much harder between your legs, causing you to lose a little bit of focus with each up and down motion of her sole.

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                                                The ache in your lower body, and the sensation of her warm foot grinding against your crotch, was slowly crumbling away your ability to focus on truly pampering Sassy. Your foot rub gradually became more and more about feeling it, exploring it, from her heel across her curvy sole to her flexible toes.

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                                                "Mighty mannequins, Anonymous. Even with this exquisitely large issue requiring my attention, you still try to take care of me first?" your boss giggled, her tongue running across her lips. Her right foot then pulled its way out of your hands, joining her left foot in sandwiching your hardened member through your clothing.

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                                                Sassy was rewarded with a damp spot on the front, as well as a strained, pleasured groan from you. Your boss held your bulge tightly between her feet, briefly leaning forward so she could relieve your length of its layered fabric prison.

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                                                "S-Sassy, I..." you said through shuddering breaths. You never got tired of that feeling. You never could. That warm, snug, sky-blue embrace. All ten of her polished, wriggling toes.

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                                                Your love of the lower extremities at last had paid off when Rarity sent you here.

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                                                "Just follow the Pattern, Anonymous. The Pattern says it's time to treat you," she cooed quietly. With that, her soles squished together more tightly, and began their motions up and down the sides of your leaking member.

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                                                Accepting your fate, as dictated by your boss's Pattern, you resorted to simply resting your hands on the tops of her perfectly sculpted feet. Not tightly, not greedily, as to allow them to work their magic on you while you felt them up to your heart's content.

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                                                Sassy sat back up straight, leaning forward while pulling her slickening soles towards herself, allowing all of her toes to wrap tightly around your shaft. Gasping in pleasure, your hips bucked involuntarily while her talented toes moved up and down the throbbing surface.

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                                                Your boss began to pump you faster with her toes, extending the range of her strokes. All the way from the underside of your sack to pinching your tip they travelled, sending you into a haze of pleasure the likes of which you would have only dreamed of. Your pre was making the footjob even easier for Sassy, allowing her to stroke more quickly, more smoothly.

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                                                "My dear Anonymous, I recognise that look on your handsome face. I think my Pattern is going to come together nicely," your boss giggled. Her polished toes on her right foot the pinched around the hilt, keeping you locked tightly in place while her left sole smoothly and easily began to glide along your shaft, using a quickened circular motion.

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                                                She was right. Your grip on the tops of your boss's feet was beginning to tighten, your body increasingly burning for release against those sweet, soft surfaces.

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                                                With a final tight embrace of her sexy, curvy soles over the upper half of your cock, you could hold your desires back no longer. Pushing and thrusting through the snug space between Sassy's perfect feet, you unleashed a torrent of your essence.

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                                                What could pass as a month's worth of semen was unloaded onto each foot, her soles rubbing together gently around your spurting shaft. Sassy's movements assisted in further spreading the mess you created across every inch of her pampered feet, and allowed what missed her soles to drip down across the other sides of her feet, and to flow between her beautiful toes.

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                                                At long last, you wound up completely spent, and found yourself staring directly into the incredibly hot sight your boss's white-coated soles. The dripping toes curled and wiggled enticingly, soles crossing over one another.

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                                                "Well, bust my buttons, Anonymous. I believe I've earned a little treat myself," she said.

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                                                And that's when it happened. Sassy leaned forward and ran a single finger across her right sole, collecting a generous dosage of your cum on the digit. Making a show of it, she lifted her finger back up towards herself, opening her mouth and messily swirling her tongue along the dripping forefinger, smacking her lips as she polished off her reward.

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                                                You were simply dumbstruck. How were you even meant to describe how much more you loved your boss in that moment?

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                                                "I'm afraid the Pattern doesn't involve allowing Nightmare Moon to enjoy a portion of my rather scrumptious reward tonight, Anonymous. What say we continue treating one another? This is the night for it, after all," Sassy said, picking up your bag of candy and placing it beside herself. She then placed her soaked feet back between your legs, with a playful wink.

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                                                Oh, most wonderful of nights.