A Little Dash Will Do
Chapter Twenty: Fitting Fluttershy
-by Drace Domino

It had taken two weeks of preparation, but tonight was finally the night! Fluttershy was nervous beyond all measure, but she had nothing but trust for her dear friend Rarity no matter what. Still...she couldn’t help but squirm every time she thought about what was going to happen that night when Rarity, wearing a magical amulet, took the virginity of Fluttershy’s tender yellow rump.

“Mmm...there we go, dear. How does that feel?” Rarity’s voice was sweet and soft, yet still had a faint echo within the girls’ restroom at Canterlot High. As the fashionista spoke she was kneeling behind Fluttershy, who was standing with legs spread and the back of her skirt lifted up over her rear. Rarity pulled the girl’s panties aside with one hand, while the other was teasing around Fluttershy’s pucker with two digits smeared with a clear, scentless lubricant. Nearby on the floor the bottle remained uncorked, and just outside in the hallway the sound of students going to their next class carried through. “Are you ready for me to put it back in, darling?”

“Oh, uhm...I think so, Rarity.” Fluttershy whimpered, her cheeks carrying a vibrant blush as she looked over her shoulder to the kneeling beauty. Her knees shook more with every passing second, no doubt inspired by the noise from the hallway. “Please hurry up, I’m...I’m afraid we’re going to get caught…”

“Oh relax, darling, we’ve been using this restroom for two weeks without any trouble.” Rarity cooed, and moved her lubricant-slickened fingers to the plug that she had pulled from Fluttershy’s rear a few moments ago. She made sure that it was thoroughly coated in that clear lube before lifting it up by the base, and pressing the tip tenderly to the girl’s tight little rump. After pressing a fond, warm kiss to the side of Fluttershy’s flank she started to squeeze the toy inside, watching as the girl’s entrance stretched and flexed around the shape of the plug. “And I have to say, Fluttershy, I am certainly impressed! You took to this even better than Coco Pommel did! I’m such a lucky woman to have so many friends that share one of my many passions.”

“...thanks, Rarity. I’m glad it’s something we can - ohhhhh - something we can share.” Fluttershy’s smile was warm and gentle as the toy squeezed all the way inside; hilting at the round base designed to stop it from going any further. As Rarity pulled Fluttershy’s panties back into place the young lady allowed her skirt to drop once more, completely hiding the fact that she was smuggling a plug within her rear. Rarity swiftly put the bottle of lube back in her purse and soon the two girls stood at the restroom sinks; Fluttershy fidgeting as she got used to the warmth of the lube and the weight of the toy, and Rarity fixing her mascara with meticulous attention.

“So are you excited for tonight, darling?” Rarity cooed, though she didn’t pull her attention away from her reflection in the mirror. “Nine o’clock, just like we planned?”

“I’ll be there, Rarity.” Fluttershy smiled, and put a tender hand to her friend’s shoulder. It was enough for Rarity to pause primping long enough for Fluttershy to lean in and give her a friendly kiss on the cheek; a tiny show of affection for all Rarity had been doing for her. “You’re a wonderful teacher. I’m looking forward to my exam!”

“As am I, dear.” Rarity beamed, and kissed the air adjacent to Fluttershy so she didn’t smear her lipstick. “I’m positive you’ll realize it was worth all the hard work!”

It had been hard work, indeed. For two weeks Rarity had kept Fluttershy on a program of toys of increasing size, making the young lady keep them inside of her for increasing amounts of time. It had started off slowly with a small toy barely the size of Fluttershy’s pinky, but now the plug within her rump was noticeable not just with every step she took but as she sat down throughout her classes. Every breath made it squirm inside of her like never before, and it only fueled her desires throughout the entire day. At first she had been a little wary of letting Rarity put toys in her rump at school, but as the fashionista had proudly stated it was how she learned to take it in her rear hole. Preparation was important, after all, and Rarity wasn’t about to take any chances with giving Fluttershy more than the poor girl could handle.

When night came and the time to meet up arrived, Fluttershy arrived at Rarity’s door with the same charming little outfit she had worn throughout the day. Her innocent white panties even hid the same plug inside of her rear, though by that point it had been treated to another two rounds of lubricant to keep it smooth inside of her. She’d be a little sore in the morning for sure, but knowing that she’d wake up naked beside her friend with her tender little hole filled with addictive magical cum...well...it certainly took her worries and threw them out the window. When the door opened and Rarity appeared before her, it was clear that Fluttershy’s test was about to begin without much preamble.

“Oh hello, darling, I’m so glad you could make it!” The fashionista opened the door wearing full lingerie; purple stockings that rolled up to the center of her thighs, and a lacy black bra that lifted her breasts without actually obscuring the sight of them. Purple gloves matched her stockings and went well past her elbows, and she wore nothing at her lap to cover her well-hung length. It was sticking straight out to greet Fluttershy as the door opened, and as Rarity motioned for her friend to step inside it swayed with clear intent. “I don’t mind saying, I’ve been waiting for this for weeks!”

“Me too.” Fluttershy admitted with a blush, and scurried inside Rarity’s home with a few eager steps. She nibbled on her bottom lip as her friend drew close, and soon found Rarity’s arm around her back as she leaned in to press a long, sweeping kiss to Fluttershy’s throat. The shy young woman gasped, and her hands stretched out for dual destinations - one to caress the side of Rarity’s long white shaft, and the other to rub her fingers over the glistening amulet hanging between Rarity’s glorious cleavage. “I’m so glad Sunset and Twilight figured out how to make more of these.” She beamed, and took a deep, aroused breath as Rarity pressed in all the closer. “It’s so much nicer to have them whenever we want without waiting for Rainbow Dash to take a weekend off.”

“Oh, darling, I completely agree.” Rarity cooed, her member throbbing at the soft, sweet touch of her innocent friend. “I think she’s spending some time with Applejack tonight. There’s no way she would’ve loaned hers to us under those circumstances.” Together the two women giggled, before Rarity lowered a hand and took Fluttershy’s own. Their fingers intertwined and the fashionista began to walk, leading her friend through the living room and steadily up the stairs. “Come along, dear. I think we’ve trained your lovely posterior quite enough.”

Fluttershy, by that point a mess of excitement and nervousness, padded silently behind her friend that she trusted so much. Every step up the stairs reminded her of the toy inside of her rear, but more importantly it reminded her that very, very soon she’d be holding something so much bigger inside.

---

Mere moments later Fluttershy was still blushing, but this time it was visible from her pretty cheeks all the way down the front of her chest. She was bracing herself on her hands and knees in the center of Rarity’s lavish bed; surrounded by silk and lace and overwhelming comfort as she presented herself with her rump lifted and her body completely bare. Rarity had taken her sweet time in undressing her friend to help ensure that Fluttershy wasn’t overwhelmed, and by the time she had finished the only thing resembling any form of clothing on the young lady was the purple circle of her plug’s base, centered squarely in between a pair of soft yellow cheeks. As Fluttershy gripped the bedsheets underneath her and squirmed in a growing state of arousal, Rarity slid between her friend and ran her smooth, well-manicured fingers across the gentle slopes of her friend’s posterior.

“Fluttershy, I’ve been so proud of you these past two weeks.” The fashionista swooned, just as one hand lowered to pinch the base of the plug between two fingers. For the moment she simply twisted it back and forth to make Fluttershy squirm, but soon she’d be pulling it free of the girl’s pucker in lieu of something more fulfilling. “I’m sure it wasn’t easy squirming your way through class every day, darling. But now that I’m sure I won’t cause you any undue distress…” And with that she began to pull, removing that toy slowly from her friend’s tight little hole. It was a slow process and Rarity watched as it happened; beaming at the sight of Fluttershy’s entrance stretching out to accommodate the toy as it was pulled free. The girl was still well-lubed when the toy was removed but Rarity was always a fan of generous proportions, and so with her free hand she tilted her bottle towards the girl’s rump and gave it a healthy squeeze.

“Ohhh…!” Fluttershy gasped, as if not already completely swimming in a state of aroused bliss. She buried her face against one of Rarity’s comfortable pillows and shuddered from excitement, her rear more ready than ever to get the reward she had worked for. As Rarity hummed a sweet tune to herself she continued slathering lubricant across Fluttershy’s hole, and made sure to give her own throbbing length a healthy dollop as well. Once she was sure everything was perfect she tossed the bottle to the side, and Fluttershy finally spoke up as she felt Rarity take her hips and prepare to enter. “R...Rarity? Please...be gentle?”

“Darling, there’s nothing I care more about than your comfort right now.” Rarity cooed, and smoothed her fingers down the back of Fluttershy’s pink hair. Her voice was comforting and soothing even as she pushed the tip of her impressive white cock to the girl’s opening, ready to squeeze herself inside. Before she did so; however, she leaned forward close enough that her lace-covered breasts pressed to Fluttershy’s back and her lips could move to the edge of her ear. After a tiny kiss she started to roll forward, her tip pressing inside just as her words struck the other girl’s senses. “If it starts to hurt, tell me, dear. But otherwise...enjoy.”

Fluttershy, a little bundle of aroused nerves, merely squeaked and buried her head in the pillow as Rarity began to claim her ass. It became apparent quite quickly that that all of the hard work they had done had paid off; Rarity’s length was enough to make most women whimper at the idea of putting it in any of their holes, and yet as the inches slowly passed into Fluttershy’s ass the timid young woman gave little more than a joyful groan. The discomfort that she felt was nothing compared to the pleasure that started to creep through her, and as Rarity tenderly rolled forward she made sure to continue praising her friend in order to make the experience as pleasant as she could.

“There we go, darling, you’re doing marvelously…” She moaned, her member throbbing against the tight walls surrounding her from every angle. She rolled forward until she had every inch of her trapped within Fluttershy’s ass, and was deeply impressed that her friend gave little more than an excited gasp and even the faint hint of a joyful giggle. With her length filling the timid thing’s rear she pressed another kiss to the back of Fluttershy’s head, and whispered anew as she began to pull her hips back. “Rainbow Dash was the first to ever go inside my ass, you know, during her birthday party. I’m glad I had trained so much on my own - I don’t need to tell you how dreadfully rough she can be!”

“We...we sure were all surprised when you told her to put it there.” Fluttershy reminisced, looking over her shoulder with a lovely glow to her cheeks. The memory was a sweet one for sure; the night that the amulet had first entered their lives. “Do you think I could handle Rainbow Dash back there?”

“Well...perhaps after a few more weeks of training, darling.” Rarity grinned, slowly pulling her hips back until her tip was cresting at Fluttershy’s ass, and then pushing back in once more. She planted herself down to the base again, and shuddered as every inch was gripped in that wonderfully tight entrance while her sack nestled against Fluttershy’s pussy. She offered the young woman a giggle, and blew a kiss to her before continuing. “Let’s keep your adorable posterior a secret treat for your good friend Rarity for now, hmm?” Fluttershy, more than happy to oblige, giggled and gave her friend a wide, smiling nod.

From there, Rarity continued to take her friend’s backside virginity with slow motions and careful patience. She continued with her policy of making sure that she never gave Fluttershy more than she could handle, and when she picked up the pace she only did it when she was absolutely positive Fluttershy was ready. More than a few times during the steady thrusting and throbbing pleasure between them Rarity even reached out to grab the lubricant once more, squirting a dose over the top of her shaft just as it disappeared inside of Fluttershy again. The entire time she fawned over her friend, stroked her rump and teased fingers down the outsides of her thighs and spoke in sweet and glorious tones about how beautiful she was and how well she handled that member. Flattery for sure, but never anything that wasn’t one hundred percent true.

By the time Fluttershy had her first orgasm with Rarity’s shaft inside her ass, it was well into their session and Rarity had gotten a little more bold. She had scooped one of her hands through the back of Fluttershy’s hair to grab a big pink ponytail in her fingers and gently lift the girl’s head up until Fluttershy was bracing herself on her palms. It wasn’t enough to abuse or debase her friend, but was certainly enough of a hold to help her stay aloft and keep her blushing cheeks out of the pillows. As she held Fluttershy’s ponytail she slid her other hand around Fluttershy’s waist and down to her pussy, where she was lightly toying with the girl’s clit even as she claimed her rear.

It was slow, it was patient, and it was romantic only in the way of two dear, dear friends enjoying an intimate evening together. It was all too easy for Fluttershy to feel the rush of her climax as Rarity plunged her depths, and she came in sweet and soft fashion with gasps rather than screams and shudders rather than squirts. She tensed up and whimpered the entire time as Rarity kissed across the back of her throat, and just as she was nearing the end of her peak Rarity had managed to find her own. All of that slow pressure wrapped across her length and giving it such a tight ride was bound to lead to her peak sooner or later, and when she found it she made sure to squeeze in as tight as she could for Fluttershy to enjoy it.

If there was one thing Rarity knew well it was the overwhelming pleasure of a girl’s first creampie in her tender, well-fucked ass.

“Oh...ohhh...R...Rari...Rariii~” Fluttershy wasn’t able to finish her thought, and she fell into another unexpected orgasm as the warm squirt of magical cum started to flood her rear. Even though she was still sensitive and raw from the one that took place seconds earlier, once more she felt her knees lock and her muscles tense, a warm joy rushing from her core. She spasmed briefly as Rarity’s cock finished unloading inside of her, and once they were done the fashionista kissed the back of Fluttershy’s head and whispered in a friendly, doting tone.

“How are you, darling?” She mused, a hand moving up to sweep sweat-licked locks of hair away from Fluttershy’s face. She didn’t pull her member free just yet, quite content to let her member bathe in the warm cum that she had filled Fluttershy’s rear with. Pulling it out before she had time to properly enjoy that beautiful moment sounded downright dreadful! “Do you think you see what I enjoy so much about it?”

Fluttershy, still catching her breath and coming down from her climax, nodded. She balanced herself on one hand as she moved down between her thighs, taking Rarity’s wrist and guiding the fashionista’s fingers forward. Silently she suckled on the girl’s white digits; cleaning the nectar that she had coated them with during her dual orgasms. For the moment both girls were quiet and fully leaning into the affection and tenderness between them; savoring their friendship just as they savored the warm combination of flesh and cream within her ass. Finally, as Fluttershy pulled Rarity’s fingers from her lips, she looked over her shoulder and gave her friend a charming, wide smile.

“Let’s...try it again.” She giggled, and bit down on her bottom lip in timid fashion before offering as a naughty suggestion. “And maybe this time, I can be on top?”

Rarity beamed, and gave her friend a proud kiss atop her sweet, smiling lips. Apparently she was a great teacher, because her student was so very willing to learn!

End of Chapter 20.

Author's Notes:

An overdue new chapter! Sorry for the delay, the last few weeks have been, as the kids say, nucking futs.

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