Sassy's Size Fitting

by Holocron

Rating: mature
Tags: Profanity, Random, Sassy Saddles, Alternate Universe, Anthro, Porn, My Little Pony: Friendship is Magic, Fetish, Rarity, Non-consensual, Sex
Length: 3114

Sassy had just endured a long shift at work, and upon seeing Rarity, cannot hold it in any longer and is overcome by the urge to breed.

FEATURED January 13 - 14 2024

Rarity's Boutiques have been nothing short of an overwhelming success. Starting in Ponyville, then expanding into Manehatten, and now a branch building in Canterlot. But to run such places requires immense and skilled help. While Manehatten is fine, Canterlot's clients are among some of the wealthiest in the Kingdom. In comes Sassy Saddles, the manager of this branch building. She has worked hard and diligent for her boss, and maintains a professional attitude at all times. but under her calm demeanor, the mare has something rather big and throbbing she was hoping to endure; that is, until Rarity made a surprise visit to the shop.

This is a Commission for Tailsic.
Derpibooru: 3221175

Published 2024-01-12 21:50:01 UTC
Last updated 2024-01-12 21:50:01 UTC

Tight and Deep

Agony, these last few days have been agony. The rush of the summer fashion sales, preparing for the fall fashions, and even predicting the possible winter and spring fashions were all in a day’s work for fashionistas like Rarity. But her assistant, Sassy Saddles, manager of her Canterlot store, was sitting at the counter, completely miserable. Or rather, not so miserable as she was feeling an immense frustration. The unicorn huffed, sighing a breath of groaning annoyance. Today was just taking far too long.

Under the counter, pushing at the boundaries of her attire, her massive cock was throbbing with an untouched longing and lustful cravings. But she couldn’t do anything about it. She was currently on the clock, and a professional that she was, she wouldn’t dare close early or take an extended lunch just to fuck some street whore. Not that the few mare customers she’s had today helped her mood. So many of them, mares more in front and below than up top. The type of bimbos she would have no problem seducing.

“Come on, come on, come on.” Sassy grumbled quietly to herself, looking at the clock. Though there weren’t anyone else in the shop, it was still improper to speak to oneself aloud. “I just need to get through this last hour, and I can just run home and masturbate.”

Not her preferred method of relieving herself, Sassy hadn’t been able to properly find a mare suitable to pleasure her impressive size. Being all but forced to jerk off several times a day, she could only feel as her balls were tender and heavy with hot, potent seed. But still, all she had to do was endure another hour, and then she could leave. The shop would be closed, and everything would be alright. At least, that’s what it should’ve been, but a faint sound caused her ears to flick; a dreaded, familiar sound.

Opening the door of the store, was Rarity. The unicorn mare must’ve come by to check in with the shop, which wasn’t a problem. Sassy did enjoy working for a boss who was so passionate and proactive as this mare was. But what Rarity was wearing was what was making her employee’s cock throb painfully in her clothes. As per the current fashion, the entering unicorn wore clothes that were tight, so tight it was a second skin.

A pair of round, succulent tits that bounced and swayed with each step. Plump nipples poked through the clothes and gave the ever so faint impression this mare’s nipples were pierced. But that wasn’t even the worst problem Sassy had to endure from her boss; it was her ass. A huge, round flank that didn’t just bounce, it practically was clapping whenever Rarity walked anywhere. Whether she was used to the sound, or unaware of it, it only made this futa mare’s cock throb to the point she felt her own clothes would tear from the pressure.

“Sassy, darling. How have things been?” Rarity greeted, completely ignorant to the fact her seductive body was causing her employee such discomfort. “Anything new I should know about?”

“N-no, no…nothing at all…” Sassy replied, trying not to make it that obvious that her cock was ready to almost break through this counter. “J-just the normal customers…” But then, an idea came to her. Smiling, she looked to her boss. “And there are plenty of new orders for you in the studio. Can you check them out?”

“Oh? Well I should get to those as soon as possible.” Rarity smiled, making her way to the back studio. All the while, her tits and ass were bouncing and making such whorish sounds. “Thank you so much, I don’t know what I’d do without you.”

“Of course, of course, I appreciate it.” Sassy replied, hiding the more wicked, almost sinister smirk on her face. “I’m sure it’s nothing you can’t handle.” Rarity said something in response, but she didn’t hear her.

As soon as Rarity entered the back studio, Sassy stood up. She groaned quietly, looking down to see the throbbing mass between her legs. She could barely walk with her cock and balls like this. She was a professional mare, she could just close the shop early, and yet, the sight of Rarity’s sultry frame was impossible to endure. There was no way she didn’t wear this without knowing how much of a whore she looked like. She wanted to be fucked, she craved to be bred, there were no doubts in Sassy’s mind.

“I’m a professional, I’m a professional, I’m a professional.” Sassy muttered, whimpering quietly as she made her way to the front door. She felt a shivering through her body, a tightness in her chest. Swallowing nervously, she gave one more look before locking the front door. “Sorry Rarity, but there’s no way in fuck I can hold it in with you here.” Sighing one more time, she turned and quickly made her way to the studio.

Rarity was busy in the studio, going through some papers that Sassy had mentioned before. There were some, but not a lot, certainly nothing she couldn’t handle. The unicorn carefully opened the studio door, quietly closing and locking it behind her. Her eyes were fixed on Rarity’s body. Swallowing nervously, she wasn’t sure what she wanted to stare at more. Was it the mare’s lucious tits, or maybe that huge ass?

“Sassy? Is that you?” Rarity called out, not turning as she bent over the table to reach for some papers. This only showed off her plump pussy lips that pushed so tightly against her skin tight clothing. “These orders don’t look that difficult, I can get to work on the planning right now.”

“Sure, no problem.” Sassy replied, her voice almost breathy and panting as she drew closer and closer. Walking slowly, she could feel her cock throb and pulse. “I was wondering about your outfit. That’s the latest Prench fashion, isn’t it?”

“Oh this? Why yes, it is.” Rarity replied, still bent over and looking at the papers. “Why? Are you interested?”

“You could say that.” Sassy replied, quietly and magically striping herself of her clothes. Her massive cock slowly grew until it was at nearly full arousal. “I was just wondering how tight it feels.”

“Oh, well it’s not bad.” Rarity replied, innocently unaware of the savage, almost steaming looking cock coming for her. “If you’d like, after this, we can do a fitting.”

“Sure, I’d like that.” Sassy giggled, now close enough to her boss to touch her. Using both hands and magic to keep her cock up, she smirked. “But first, I have some tension and swelling that needs to be handled first.” At that, she let go.

As soon as this huge cock slapped against Rarity’s ass, landing between her soft rear mounds, the mare yelped out in confusion. Turning her head, she could see the dick attached to her employee. Sassy had an intense look in her eyes, panting her hot breath as she wasn’t just laying her girth against her ass, but the mare was naked. The unicorn’s breasts were quite impressive as well, as was her beautiful ass, but they were so small compared to this dick. Bigger than anything Rarity had ever seen before, and the way it was throbbing as if it had its own heartbeat.

Being this close, she could feel the heat of it as it rubbed a little between her asscheeks, and the musky smell was numbing her mind. Sassy hummed, feeling a sense of relief, as well as an intense sensation of longing and passion. She was going to fuck her, she was going to take her mare breaker of a cock and drive every inch in her boss. Her cockhead oozed out thick globs of precum that were making a small mess on the small of Rarity’s back and rubbing a little against her tail. The unicorn trembled, feeling overwhelmed and intimidated by this meaty thing.

“Sorry boss, but I can’t hold myself back.” Sassy commented, almost humming playfully as she was slowly rubbing her huge cock against Rarity’s huge, soft, round ass cheeks. “I’ve been trying all day to hold it in, and it was so close.” She raised a hand, smacking the mare’s ass, making her yelp out. “But then you come here, wearing the sluttiest thing I’ve ever seen, and don’t expect me to fuck you for this?”

Rarity shivered, even as she couldn’t see it, she could feel just how massive this cock was. It was not only big, but hot, sending a nervous tingle throughout her body. But among this, was another feeling, a slowly growing arousal. She wasn’t fully being turned on, but there was no denying that this thick, meaty cock was bringing out some instinctive feeling of her womanly body. Sassy couldn’t wait any longer, slowly pulling back to let this cock slide between Rarity’s soft ass mounds.

There was no going back from what was about to happen. Sassy knew this, but the arousal was just too much for her. Rarity was too damn sexy. Her body was too alluring, and not a single pony in Equestria that had a working cock wouldn’t pass up the chance to fuck and breed her like a whore. Especially with that outfit, being the final straw to the build up she had endured all day. The sensation of the moist lips kissing against her blunt hard cockhead was just too much and Sassy knew she had to fuck her; right now.

“S-Sassy…what are you-ahh!” Rarity gasped out, her answer coming in the form of the mare slowly wedging her cock in the mare’s tight entrance. “So…so big…”

“You only have yourself to blame.” Sassy laughed, slowly pushing more and more of her mighty size in her boss. “Walking around…in this tight…slutty…” As she continued to shove her cock against the mare, she noticed something; the fabric Rarity wore wasn’t tearing, it was wrapping around the dick too. “What the fuck? Are you wearing a condom or something?”

“W-what? No, it’s…it’s the latest trend.” Rarity panted, trying not to show the red blush across her face. “I…I just added some magic to make sure it was flexible…you know, so it wouldn’t tear.”

“Oh, no, no, no, this will not do.” Sassy commented, slowly pulling out of her employer. Looking at the mare’s beautiful, round ass, she could see the tight pants had no visible wear, tear, or stretches. “That’s really impressive. But it’s in my way.” Grabbing at the lining of the pants, she pulled it down, revealing the unicorn’s jiggling, fat ass. “Much better.”

Lining up her cock again, Sassy pushed into Rarity’s pussy. But this time, she wasn’t as gentle. The unicorn gasped as her employee shoved this huge length into her sweet and soft folds. It was like the mare was trying to use this cock to reshape the fashionista's pussy to fit this huge thing. But other than the feeling of being stretched by this beast of a cock, Rarity felt a slowly growing pleasure tingle along her spine.

“Holy fuck, if I knew you’d get wet this easily, I would’ve mounted you long ago.” Sassy giggled, getting about half of her length in the mare. Reaching down, she groped at Rarity’s ass, picking up the speed of her thrusts. “And this ass, how the fuck do you even go anywhere without someone trying to fuck you?”

“I…I don’t know what you’re…you’re talking about…” Rarity replied, panting as she was feeling the hammering motion of Sassy’s cock in her pussy. “The…the people who look at me…are simply…admiring…my sense…of fashion…”

“Sense of fashion? Are you crazy?!” Sassy replied, her eyes almost twitching at such a comment. Moving her arms at Rarity’s arms, she hoisted the mare upwards, nearly bottoming out her length in the mare as she turned her to face the nearby mirror. “You see this? This is the body of a mare who wants to be bred.” Thrusting faster and harder, she made the mare’s tits bounce madly. “Look at your tits, these are huge…fat milkers that make every hot blood stallion hard and thirsty.”

Rarity moaned a little, seeing herself being fucked was making her pussy tighten and moisten around Sassy’s cock. Unable to hold back, the unicorn reached up and lifted the mare’s shirt, revealing not only her massive tits, but her huge, plump pierced nipples. Sassy couldn’t contain herself, reaching up with one hand to grope at these breasts while the other hand maintained holding Rarity’s hands behind her back to hold her up as she was fucking faster and faster.

Rarity panted and moaned, blushing immensely as she couldn’t look away from herself being used like this. Sassy was fucking her, this massive cock was going in and out of her not just her pussy, but making a visible belly bulge with each hard and deep thrust. Her boobs were bouncing as her ass was being smacked by Sassy’s hips. Rarity couldn’t help but grit her teeth as she was hissing in pleasure. Her eyes rolled back as she came on the mare cock ruining her hole.

“Did you just cum?” Sassy asked, pausing for a moment in disbelief. Curling her lips with a playful smile, she started laughing. “I knew it! You’re just a whore, a slut who loves being fucked.” Thrusting faster and faster in and out of Rarity’s pussy, she moaned out in the pleasure. “Fuck, you’re tight. Who would’ve thought such a proud mare was such a slut.”

Sassy was wrong, right? There was no way Rarity was some slut getting off on this. But she was, her body was being bombarded with so much pleasure, she was only barely able to stay conscious after that first orgasm. Her pussy was loosening up, but only so Sassy’s dick could go deeper. Before long, her hard, oozing cockhead was brutally making out with the mare’s cervix, trying harder and harder to fuck its way into her womb.

“Oh fuck…” Sassy gasped out, seeing as she could cum at any moment. She couldn’t stop herself, couldn’t slow down, only thrust, and thrust, and thrust her cock in and out of Rarity’s pussy. “Rarity, your pussy is so good. I just…I can’t stop. You were born to be a whore.”

Sassy’s words only seemed to make the mare’s body shake and shiver, causing her to moan as this dick was rubbing along all her sweet and sensitive spots. Rarity continued to look at herself, seeing the way her face was being twisted into a sloppy smile. She hissed as the pleasure was making her mind go numb and body tingling warmer and warmer. Her eyes rolled back as she trembled again, her pussy tightening into another orgasm.

“Did you cum again?” Sassy asked, laughing as she fucked faster and harder. “You’re such a whore, I haven’t even come yet!” Gritting her teeth, this wouldn’t be the case for long, she was getting close.

The feeling of dominance over this mare, the way she could make her moan like a whore, and how her pussy was only gripping her more and more as if she craved it all inside her. It was all so much for Sassy. She could feel herself getting ready to cum. She was about to flood every inch of Rarity’s insides in her hot seed. This thick spunk was churning in her heavy balls, tingling more and more. Huffing and puffing out, Sassy arched her head back as she gasped out in orgasm.

“Fuck…scream for me bitch!” Sassy grunted, tugging at Rarity’s arms hard, making her gasp and moan. “Scream like a whore as I knock you up!” At that, the mare bottomed out in the mare’s pussy, just as her swelling cock burst in orgasm.

Sassy’s climax was big, hot, and vast. Jelly thick spunk flooded deep into Rarity’s womb, soaking her insides and saturating her ovaries. The mare gasped, moaned, cooed, and then whimpered as her face twisted in a way that nopony in all of Equestria would imagine her capable of. She was smiling, tongue dangling from the side of her mouth as her eyes were halfway rolled back and twitching as she was cumming again from this heat.

Even as her pussy was full of cum, Sassy still had a lot more to spill into her boss. Rarity’s belly began to swell and bulge to match that of her bloated womb. Gasping some more, the mare’s horns let out some sparks as she was cumming, which only made Sassy laugh and thrust, even as it was pushing more and more cum inside her. The feeling was so good and it was too much for her. She gasped again as she was shivering from the delightful euphoria.

“Fuck…Rarity, this pussy.” Sassy cooed, settling down a little as she was standing in the afterglow of her orgasm. “I might just cum again from a hole this good.”

Pulling back and releasing her hold on the mare, Sassy watched as Rarity’s body collapsed on the floor in a sloppy, twitching mess. Even as a cum gushing whore, the mare looked so beautiful, so sexy, that the futa’s cock was already getting hard again. She felt like she had come gallons, and yet she was tingling all over with the desire to go another round. Rarity’s body was just perfect, the pinnacle of a fuckable hole.

“Well damn, looks like it’s gonna take more than a round to calm down.” Sassy chuckled to herself, looking over the mess she had made. “Shit, with that much cum, you might get pregnant.” The thought crossed her mind, but only made her giggle some more. “Not that it would be a bad thing.”

There were hardly any doubts about it, Rarity had been bred. Her pussy was full of so much cum, and her body was just in the prime of ovulation. Sassy smirked, walking back over to the mare. Her cock swayed a little, the light of the room casting a massive shadow over her. Moving so that she was more in front of her, she reached down to lift up Rarity’s face to get a good look at her. She was awake, though in a heavy daze.

“Looks like you’re ready for another round.” Sassy giggled, presenting her massive cock to the mare. “Now, why don’t you get me cleaned up before I fuck you again.” Rarity hesitated, but more out of fatigue than anything, soon enough opening her mouth to let the unicorn press her slick and sticky dick against her lips. “Good slut.”