A Summer to Remember

by Westphalian_Musketeer

Journey: Ability First, Then Confidence

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"Aaaand done!" Rarity declared proudly as she made the final adjustments to the marequin she had packed with her. It was stark white with a red plastic stand. Across the body, various dials attached to gears inside could make subtle adjustments to the dimensions of the marequin. Rarity floated out a piece of paper and began making a few adjustments. She had a few ideas for earth pony fashions that she wanted to experiment with.

"That's really nice Rarity," uttered Fluttershy, perched in her bunk, and stark still. "But uh, Pinkie isn't here right now."

"Oh I have plenty of work to do before I finish." Rarity turned the dial on the croup by a few more millimeters before smiling contently. "I'm sure that by the time I have this design made Pinkie will have come back, and I can have her try it on."

"O-okay." Fluttershy lay her head on the great mass of blankets she had surrounded herself with. She shut her eyes as Rarity pulled out some fabric and put it across the marequin's croup. Fluttershy breathed in deeply through her mouth before letting it all out through her nose slowly. Years of going through her season had taught her the best ways not to think of it. Still... the warmth that was building up underneath the blankets wasn't helping.

"Oh this new line I've thought of is going to be wonderful!" Rarity exclaimed. "Every earth pony is simply going to adore this new fastening I've developed. Velcro! I got the idea from when Fluttershy had to tend Opalescence when she was attacked by a ruffian of a porcupine!" Rarity winced and shuddered before continuing. "The poor dear, the quill was really stuck in there. When Fluttershy told me porcupine quills were barbed, I had an idea!" Rarity threw out a flourish with her front hooves. "Make something that has hooks built into it, and it can be used to tighten and adjust clothes easily!" Rarity turned to Fluttershy with a wide grin. "I just have to find Pinkie Pie to see if it's as easy to use as it should be."

Rarity made a few more stitches before she looked at her work. "Hmmm, I think that will do." She magicked off the dress and made her way to the cabin door with all haste. "I'm off to find Pinkie Pie, if she comes back, do tell her I wanted to see her won't you?"

"O-of course Rarity!" Fluttershy said, nodding.

With that the door shut, and Fluttershy threw the pile of blankets off of her to reveal the damp spot that had formed underneath her that night. Shifting position, the butter pegasus lay on her back and splayed out her wings. She cast a quick look at the clock reading five minutes after ten. She reached a hoof down to her marehood and let her thoughts turn to the dream she had.

***

WHAM!

Big Macintosh, with his sturdy hooves, crimson red coat beaded with sweat, and a Clydesdale frame that rippled with muscles, bucked the apple tree behind him, causing a cascade of apples to fall into the buckets he had put underneath. He picked up a few stray apples and tossed them into a bucket.

"It looks like you've got all the harvesting done for the day Big Mac," came a soft voice. Big Mac looked over to see Fluttershy there, curled into a little ball at the base of a gentle incline.

"Eeyup," he responded simply. "Ahead o' time too."

"Oh that's wonderful Big Mac!" Fluttershy exclaimed, wings extending in a show of happiness. "Do you have any plans on what to do with your extra time?" She buried her face inside her mane and gave him a saccharine wink with her one eye that was showing.

"Nope, any suggestions?" Mac answered. Stepping towards Fluttershy.

"Oh, I had a few ideas, this and that, but I was really hoping we could spend some time together," Fluttershy answered with unnatural ease and forwardness.

"Any particular ideas on what we do together?" Mac answered, walking to where the pegasus was lying and sitting by her tail.

"Oh..." Fluttershy's tail flicked and brushed against Macintosh's sheath. "I think there are a few things we could come up with." Fluttershy stood up and faced Big Mac, her face barely reaching up to his. "Think of something yet?"

"Maybe."

"And what is it?" Fluttershy prodded

Macintosh swallowed and looked deep into her eyes before leaning forward. Fluttershy closed her eyes and let his lips press against hers. She took the initiative and licked at his lips gently before letting him do the same. She opened her mouth and Mac's tongue entered. He explored for a bit before Fluttershy's tongue reached up and embraced his, wrestling for a little while. After a few seconds, they broke of the kiss with a blush forming across pegasus' cheeks.

"We should probably find someplace hidden," Fluttershy suggested.

"West fields, nopony comes out here unless they're harvestin', an' Applejack's away at market."

Without further prompting, Fluttershy pecked Mac's neck and throat with a series of kisses. Fluttershy planted more kisses along his side as she worked her way around him. Reaching his muscular flanks, she kissed his cutie mark. She glanced out of the corner of her eye, and she saw Mac had craned his head to continue looking at her. Fluttershy gave a playful wave of her tail before she faced away from Mac and bared the exposed form of her marehood.

"Go on," Fluttershy prompted, tensing her legs for the incoming weight to bear down on her.

She faced an apple tree and waited for a moment before she heard Big Macintosh step towards her. There was a small grunt, and Mac lifted himself onto his back hooves and settled himself on top of Fluttershy. She could feel his warm cock rubbing against her belly, quivering slightly as it rubbed against her fur.

Big Mac reached over to Fluttershy's mane and tugged gently at it as he adjusted his fore hooves. He pulled at her mane from her forehead, down to her neck before he started kissing between her wings.

"Oh Macintosh!" the pegasus crooned. "That feels wonderful!" Her wings extended slowly, and Big Mac kissed up and down the feathered appendages. They were getting rougher, and poking the feathers out in odd directions, but that was a small price to pay for this.

The stallion wrapped his hooves underneath the mare's wings, massaging the undersides gently as he pulled his hips back slightly. Fluttershy felt his cock stroke against her slit, covering it with some of her lubricant before her began pressing himself into her.

The parting of her lips was a luxurious pain for Fluttershy, equal parts the thrill of discovery and the promise of something innate to her being. Inches of Macintosh's flared penis filled her as he slowly entered deeper into her tight walls. The delicate pegasus gave a small grunt of pain. Mac to stopped, before he began rocking back and forth, contenting himself with out far he had gone into Fluttershy.

Macintosh leaned his head forward, breathing quickly though his nose. He lipped and tongued the small patch of skin and fur between Fluttershy's wings, arousing her further as his hot breath tickled at her wings.

The flared tip of Mac's cock pressed against Fluttershy's inner creases, sending shocks of pleasure through here as he continued to press in and out, in and out.

Fluttershy squealed, and Mac reached over and nipped at her ear. She floated off the edge, riding the wave of her orgasm as Mac rocked back and forth for a few more seconds.

***

"Hugh!" Fluttershy panted, looking at the clock in the room. It read out at seven minutes after ten. Fluttershy continued to breath heavily for five minutes before she realized her front hooves were still between her back legs. She pulled her hooves away from her labia and looked around ashamedly.

"Oh, I wish I could be that assertive with Mac. But now that he has Cheerilee, would he even want me?" Fluttershy wiped her hooves on her sheets before hopping out of her bed and setting all the blankets straight. "Even with that assertiveness training, I can't just go up to him and ask! But what would Cheerilee think if I just walked up to her and asked to join their herd?"

"She'd probably say yes!"

Fluttershy's eyes widened, and she saw a pair of massive orange eyes staring at her from underneath the bed. "AAAH!"

"AAGH!" screamed the eyes.

"AAAAAAaaaAAH!"

"AAAAAGGGH—! Wait, what are we screaming for?"

Fluttershy fell on the floor in a heap. Panting heavily once again, she looked at the set of eyes, and realized they were goggles. "Pinkie!" she exclaimed, blushing profusely. She scuttled to the corner and crossed her legs over herself. "I was just, ummm, fidgeting! Yeah, fidgeting." Fluttershy nodded her head anxiously.

Pinkie Pie slid out from underneath the bed, goggles still on, but black cat suit missing, and looked at the bedding. "Fidgeting? What were you fidgeting with? Was it a jelly donut? A Rubick's Cube?"

"I-uh..."

"Nonono, let me guess. You were fidgeting with a piece of paper, mayonnaise, eggs, a ghost!" Pinkie whirled her head around one hundred eighty degrees to face Fluttershy before the rest of the pink mare's body snapped into position.

Fluttershy blinked for a few moments at the erratic display, only to yelp when Pinkie sidled over.

"So was I right?" Pinkie asked, blinking her bright blue eyes at Fluttershy's.

"Ummm, no," Fluttershy responded, before walking past Pinkie. "I'd like to have a shower now, so I—"

"Oh! You were fidgeting with yourself," Pinkie said, waving a hoof through the air and then raspberrying her lips. Pinkie sidled up beside Fluttershy. She ruffled the feathers of her pegasus friend. "So who're ya thinkin' about?"

Fluttershy, mind still several seconds behind the mare. "I just want to freshen—How did you?—Big—" Fluttershy shut her mouth as Pinkie continued to rub against her wings. Pinkie looked at her imploringly. Sighing, Fluttershy answered, "Big Macintosh"

"What was that? Paper? Mayonnaise? A ghost?" Pinkie was instantly in front of Fluttershy.

The shy pegasus' ears wilted and she looked at the ground. "Big Macintosh." She waited for the party mare's inevitable tirade, but was surprised when none came. She looked up and saw that Pinkie had a hoof on her chin. Pinkie looked off into the distance as if she were contemplating a comet heading for Canterlot—or some other such insignificant matter—for a few moments before she opened her mouth to speak.

"Are you sure that's safe?" she asked.

"Oh, I know it's a terrible and silly idea. I mean, he already has Cheerilee and I'm so quiet compared to her and I just know I wouldn't fit in with that kind of herd and I should really just get used to being alone and I—!"

"Not what I asked," Pinkie interrupted. "I asked if that was safe. I mean, unless you could get Twilight to shrink Big Mac into an itty-bitty, teeny-tiny microstallion from what he is now, I'm pretty sure you'd only last a minute with him."

Fluttershy's eyes and mouth twitched at the implications. "What do you...?"

"Earth pony." Pinkie Pie rolled her eyes. "Endurance, stamina, strength. Big Mac'd probably be perfect for you if you could handle that many spine-cracking, scream-making, make-you-want-to-stay-in-bed-forever orgasms."

"I... You're right; I don't deserve Big Macintosh." Fluttershy cast her gaze onto the ground. A warm trail of moisture snaked its way down her muzzle before dropping onto the cabin floor.

"Woah!" Pinkie formed a 'T' with her front legs. "Time out, I'm not saying you don't deserve Mac."

"But what is it about me that he'd be interested in?" Fluttershy asked. Looking up, she only saw empty space where Pinkie had been.

"Zat is vhy ve must talk about zis," came a feminine, Germane-accented voice. Pinkie trotted back in front of Fluttershy. A pair of doctor's spectacles was balanced on her nose. The party mare reached underneath Fluttershy's bed, pulled out a psychologist's couch, and proceeded to plant her friend on it. "Now, vhy vere you attracted to Big Macintosh in zee first place?" she asked, keeping up the Germane accent.

Lying on her back, Fluttershy looked over to her friend with equal amounts of confusion and trust. "Well, um, he's Applejack's brother, so he's close enough already that I don't really need to go out of my comfort zone if I really set my mind on talking to him. He's strong, and from how well he took care of the farm, Apple Bloom, and Applejack, he'd probably be a good dad. He knows a lot about farming, which I'm curious about, because it would help me feed all my animals."

Fluttershy breathed heavily out of her mouth. "But I don't see what I'd have to offer him now that he has Cheerilee. And I wouldn't be able to have the courage to ask her if I could..." Fluttershy closed her eyes and tried to think of her animals back at home, all starting families for the summer time, or off feeding in Whitetail Wood with the abundant acorns, or starting families, or...

Fluttershy's eyes opened slowly as Pinkie continued to silently observe her friend. "I'm... caring, I could help whenever he injures himself, be a silent listener when he has things he needs to talk about. He's a strong stallion, but I could offer him something. My companionship is worth something." Fluttershy turned her head to the side. "But I'd still need to ask Cheerilee."

"Not necessarily," Pinkie answered cryptically. Fluttershy looked over to see the pink mare's glasses had been replaced by a masquerade mask. "Don't you think there's a way you could convince Cheerilee into inviting you into the herd?"

The pegasus' wings pushed her our of her reclined position, and she sat up straight, eyes wide open. "But even if she was willing, it'd be embarrassing if I wasn't able to do anything." Her chest heaved as images of Big Mac, Cheerilee, and herself twisting around in bed flashed before her eyes. "I need to get Cheerilee to really like me, and figure out how to, ummm..."

"Last a night with not one earth pony, but two," Pinkie Pie completed. She leaned forward and wiggled her eyebrows.

"Would you help me with that?" Fluttershy asked.

Pinkie Pie nodded slowly, a wide, toothy grin filling her face.

***

Pinkie Pie opened a box to reveal four dildos; all had straps to attach to a mare's hips, and none of them had a cooler pump, but that was where the similarities ended. The one on the left was plain white, smooth, and a size which Fluttershy guessed was average. The second one was a light blue, slightly longer than the first, had a secondary vibrating head for the clitoris. Second from last was an orange dildo with a flared tip; it had a girth and length that made Fluttershy cringe slightly at the size of it. The last one was black, still bigger in size than third, but was studded across the length with soft rubber nubs.

"Hmmm." Pinkie's hoof hovered over each one in turn. Her ears twitched as she examined them. When the party mare picked up the black dildo, Fluttershy gasped. Putting it down, Pinkie muttered, "No, that's too much." Fluttershy gave out a sigh of relief. Pinkie looked back at the blue dildo. She'd probably be okay with this one.

Pinkie Pie picked up the blue dildo and held it at eye level as she turned to Fluttershy. "Care to help me put it on?"

The pegasus' wings quivered as much as her back legs did. "I um, is this really? Okay." She grabbed the dildo in her mouth and watched as Pinkie flopped onto her back. Fluttershy lay the dildo across Pinkie's vulva and allowed the straps to fall around the party mare's waist.

Pinkie Pie arched her back upwards and used her hooves to press the snap-on clips together so that the dildo wouldn't simply fall off her the moment Fluttershy ceased to keep it there with her mouth. The sight of her friend there with her mouth wrapped around such a provocative instrument made Pinkie giggle.

Fluttershy pulled her head back, and the dildo tilted to the left by an inch. "What is it?" she asked, eyes growing wide in fright that she had done something worthy of mockery.

"Oh nothing, just that your lips looked so cute wrapped around Sky High." Pinkie continued to giggle.

"Sky High?" Fluttershy tilted her head and stared at Pinkie, dumbfounded. Her eyes wandered back to the dildo and she flinched. "Oh my!" The butter pegasus wrapped her wings around herself, covering her eyes for a while before staring back out. Pinkie was still looking at her with a mirthful smile.

Gathering herself, Fluttershy lowered her head back to Pinkie's crotch and cinched the straps, pulling Sky High into position. Fluttershy looked up and down its length, straining her eyes as she kept her head still, as though any movement other than her eyes would make it strike.

"What would you do if this was Big Mac?" Pinkie offered, putting her front hooves behinds her back.

Fluttershy started and looked at Pinkie. "Oh... I guess?" She resumed looking at the light blue dildo, sniffing at the odorless plastic gently. She extended her tongue out and gingerly licked the dildo. She drew her tongue up and down its length, playing with the tip as she licked down the other side, leaving a slick trail of saliva all the way. She tended the mock-penis like that until the light from the window shined off of it.

Gazing up at Pinkie, Fluttershy saw her waving her hoof in slow circles to say, 'Go on.'

She obliged, her muzzle descended on Sky High from above, and she suckled at the tip for a few moments. Lowering her head further down the shaft, she wrapped her tongue around it and moved it up and down, covering with more of her spit. She got around halfway down before she started feeling her throat protest. Fluttershy stayed there fore a few moments, bobbing her head up and down, just on the edge of her gag reflex overpowering her.

Pinkie watched the whole affair, her breathing becoming increasingly jagged. Her estrus, tamed as it was by her more powerful instincts to make those around her happy, urged her to cease the teasing.

"Okay, that's good Flutters," Pinkie instructed.

Fluttershy's lips popped as she broke the seal with the dildo and she looked up. "So, you're going to try and increase my endurance? How?"

Pinkie Pie rolled onto her stomach and stood up, Sky High hanging from her crotch as a portent of things to come. "Practice." She walked past Fluttershy, nipping at her ear. "Practice." Fluttershy's wings unfurled as she gave a ragged gasp. "Practice."

"Ooohhh," the yellow pegasus moaned as Pinkie dragged a hoof through her primaries. Fluttershy raised her hips, emulating the action she had long fantasized in her dreams.

Pinkie brushed aside her friend's soft-pink tail and exposed her folds. They were wet and puffed. Pinkie blew on them slowly. The warm air caressed Fluttershy's vagina and made the pegasus let out another uneasy moan.

Heaving herself onto her hind legs briefly, Pinkie settled herself across Fluttershy's back. The dildo lay across Fluttershy's entrance. Reaching a hoof underneath herself and her friend, Pinkie turned on the vibrating function.

Fluttershy gasped, her stomach nearly cramping from how quickly she had sucked it in. The vibrations coaxed her vagina to begin leaking out its own lubricant, adding to the spit she had already provided. Pinkie lowered her head mouth next to Fluttershy's ear.

"The safe word... is kumquat."

"Kumquat," Fluttershy repeated.

"I'll just assume that was you committing it to memory?" Pinkie Pie licked against the fur behind Fluttershy's ear as the pegasus nodded.

Pinkie Pie could feel her own juices seeping out of the gap between the dildo and herself as she pulled her hips back to press the vibrating head against Fluttershy's entrance. She let the vibrating head do the initial penetration, pulling itself into Fluttershy's awaiting vagina. The small squeaks, moans, and gasps of Fluttershy made Pinkie's own heart rate increase. She enjoyed giving others pleasure, more than she did herself. She'd have preferred to have done it through other means, but certain problems called for certain solutions.

The dildo was halfway inside Fluttershy. She was biting her lips as the constant vibrations pushed her towards an orgasm faster than she had ever accomplished with hooves. "Ehhun!" she cried as her walls clasped around the dildo, pulsating and drawing it in further. When Sky High pressed further into her, it pleasured more of her, increasing her arousal and pleasure. "GAH!" Another orgasm pulled the dildo even further inside of her.

Pinkie's hips made contact with Fluttershy's. She was fully inside, she was most certainly deeper than Fluttershy had ever let anypony else. The secondary head was brushing against Fluttershy's clitoris too now, and the vibrations were sending her to another edge. Her tongue lolled out from exhaustion, but that was the point, she had to endure, she had to last.

Gasping as Pinkie Pie pulled out of her, Fluttershy was given a brief reprieve as the secondary head pulled away from her sensitive nub. Pinkie slid forward, the dildo still quaking inside Fluttershy. Her nub was touched again and she screamed as the combined quivering inside and out of her tunnel pushed her to vaginal and clitoral orgasm. Her belly ached from the abuse, and her legs gave out beneath her, planting her belly against the mattress.

Pinkie adjusted, and continued pressing against Fluttershy as the pegasus reveled in her clitoris and vagina still being pleasured. The secondary head pressed against her, not providing a moment's relief. Fluttershy's eyes closed as she tried to regain control of her breathing, tried to fight off how weak she was feeling. No, she thought, starting to move her hips against the dildo, driving her passion up against the proverbial wall. I won't give up! She began pushing towards Pinkie, the dildo attempted to obstruct her motions with the promise of another orgasm. Fluttershy tensed her glutes. She managed to rock back and forth a few times before her body gave way, and another peak struck her.

Pain and pleasure shot through Fluttershy's aching pussy and into her chest as she dragged herself away from Pinkie. "Kumquat," she moaned, and with that, Pinkie pulled out of Fluttershy. Fluttershy's ears flopped down as she panted and gasped hungrily for air. Her eye's were half-lidded when the buzzing of the dildo stopped reaching her ears.

Barely conscious, Fluttershy register that Pinkie had lay down beside her. The pink mare's hoof brushed through Fluttershy's mane, straightening it from the ordeal.

"You did very well Flutters," Pinkie cooed, smiling warmly down on her exhausted friend.

"Did I?" Fluttershy asked. Her voice, muffled by the sheets and her own tiredness, came out as a humming noise.

"Mhmm, cum-quad, four orgasms."

Fluttershy used what remaining lucidity she had to giggle. "You and Zecora would make a wonderful team."

"You really think so?" Pinkie asked, leaning down to put herself at eye level with her friend.

Fluttershy breathed softly, dreaming of dreams she hoped to soon make true.


Author's Note

Alright, new chapter is finally done.

I want a personal opinion from you guys. Should I give more detail into the character's emotional states, or would I just be slipping into telling rather than showing if I did that?

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