Fluttershy's Big Night

by Michael Hudson

Rating: mature
Tags: Applejack, My Little Pony: Friendship is Magic, Romance, Fluttershy, Sex, Big Macintosh, Random
Length: 2471

After a few drinks and some encouragement, Fluttershy is ready to learn about sex from Applejack and her family.

With too many bottles of cider, any mare can make questionable decisions. For Applejack, helping Fluttershy learn something, anything about sex, even through the use of her sleeping brother, may have been one of the most questionable.

Part of the JumbledVision project.

Contains: Consensual, sleeping touching, F/F

Published 2016-01-14 22:30:02 UTC
Last updated 2016-01-14 22:30:02 UTC

A REALLY Drunken Night

Fluttershy lowered her bottle of cider, a red blush already covering her entire head, even though this was her first bottle. While she had never been the best with her alcohol, this was not the reason for the rosy cheeks. No, that was more so because of the reason why Applejack was downing her sixth bottle of cider “D-don’t you think that’s a little much?”

Applejack turned her gaze to Fluttershy for a moment, before letting out a mighty yawn. “Maybe, but if I’m gonna be helping you fuck my brother, I want to be good and drunk for it.”

Fluttershy’s wings sprang from her back at the mention of the reason for her visit, but were soon brought around to cover her face. She swallowed hard, thinking back to a week ago. She had only meant to let her friend know she was interested, and that she wanted book recommendations for her trip to the library. Applejack hadn’t wanted to hear a thing about that, and thought a full grown mare should learn in much more straightforward ways.

Which now led to Fluttershy and her sitting in the Apple family living room, steeling their nerves before they went upstairs to a Big Mac that was drugged to stay asleep. Both had their apprehensions about it, and for most of the week, Fluttershy had simply said no to the idea. She was afraid of ever seeing a cock, let alone riding one. However, even a shy mare like her was prone to fantasy, and Applejack had said she would be there for Fluttershy, no matter how awkward it was. One sleeping potion from Zecora later, and Fluttershy had her completely anonymous night. She only hoped she would enjoy it as much as she had envisioned in the past.

Applejack finally hopped off the chair she laid upon, coming down with a hard thud, and causing both mares to wince at the sound. “Sorry.” She shook her head, bringing up one hoof to try to stop the ringing. “Alright Fluttershy, it’s the middle of the night, and that potion isn’t going to work forever. Now or never.”

Fluttershy swallowed hard as she separated her wings from her eyeballs, her body trembling while she drank the last of her cider. “N-never? Couldn’t we just try again another night?”

Applejack turned to her friend, before raising a singular eyebrow. “So I can drug my brother again and get him prepped for sex? Sorry Fluttershy, but it took me almost all of last night to come to grips with today, and I still needed all of that cider.”

Fluttershy lowered her head, gently nudging the cushion beneath her. “I… I’m sorry. If you don’t want to do this-” She stopped as an orange hoof placed itself on hers.

“Hey, sugarcube, if I wasn’t certain, we would not be here tonight, and if you need to call this off, that’s fine.” Applejack flashed the pegasus a soft smile as they met each other's eyes. “I don’t want you to do this simply because you think you need to.”

Fluttershy thought for a moment that her heart had skipped a beat as she continued to look Applejack in the eyes, before nuzzling against her. “I… I’m going to be nervous no matter what. If tonight means having one of my best friends there to keep me calm…” She swallowed hard, blushing deeply as she stepped off of the couch she had been on. “I… I think we should just get going.”

Applejack nodded, leaving her hat down on the table. Where they went, it would be of no use. The creeks of the stairs stopped Fluttershy each time, and she almost didn’t move when Applejack pushed against her wide flanks. If she didn’t though, she would have to find out if her drunk friend was bluffing about rubbing a different region of her to get her moving. So, they made slow progress up, with the farm mare having multiple chances to enjoy the squishy rump that was attached to her shy friend.

Once the two were up there, Applejack took the forward position, leading the way to Big Macintosh’s room. Her tail swung side to side far more than it should, and, despite knowing that she really shouldn’t, tempted Fluttershy to stare at pink folds that lay between Applejack’s thighs. Each time she got a glimpse though, she would immediately look away, hoping steam didn’t start to come off of her.

Finally, with both mare’s ever so slightly wet, with red faces, of which only one could even try to look at the other, they opened the room to their waiting stallion. Applejack did not push, prod, or say a word. She merely sat, rubbing Fluttershy’s back as the pegasus merely stood there. “Take your time honey. We’re in no rush if you don’t want to be.”

Fluttershy’s mouth was bone dry at this point, the sound of her heart hammering in her ears. Her legs twitched, trying to move forward, but what was so much simpler earlier that day now seemed impossible. “I… I never managed to ask before, b-but what exactly did you have planned for tonight?”

Applejack nodded, continuing her gentle pets as the two stayed in the doorway. “Well, ideally, we get you to the point where he’s rutting you as deep as that shaft of his will go.” She felt the other mare tense, and smacked her drunken mind for just how stupid she could be. “But, we’re probably not getting there, nor do we have to. I was expecting only for some touching, and maybe a lick or two.”

Fluttershy’s eyes were as wide as dinner plates now, all knowledge of their plan seeming out the window now that they were actually about to execute it. “You...You’re supposed to lick it?”

Applejack nodded, her hoof slowly running along Fluttershy’s back, inch by inch. “Well, I mean, think about when you’re… helping yourself. You use a hold, hard hoof.” The tip of her rough hooves grazed Fluttershy’s slit, causing the mare’s wings to become fully erect. “Imagine that, but with something warmer, and softer.”

Fluttershy furiously nodded, now certain that her mane must have caught on fire. The more she thought about it though, the more and more that initial desire to learn about sex came to the forefront of her mind. She blamed the alcohol for it, but it was also the last push to get her into the room.

There lay the large, red stallion. Already, on the lower half of his sheets, a large tent had been erected from the white blanket, and Fluttershy swallowed hard. Applejack herself was a bit taken aback by the apparent size of her brother, and tried to chuckle nervously. “M-must be having pleasant dreams.”

Fluttershy barely let out a squeak as she stepped forward, her body unable to turn around. Her drunken mind told her that it couldn’t possibly get any worse, even when Applejack pulled away the covers. Before her was a testament to the virility of all stallions. A throbbing member that twitched in the air, it’s medial ring quivering as a small bit of clear liquid came out of the tip. Its stench came to her, causing one of her back hooves to lift as her mouth watered.She almost fell over in her lightheadedness, but Applejack was there to stop the pegasus from crashing down. “It...it’s so big.”

Applejack nodded as the two righted, taking another moment to watch the rock hard cock that seemed to dominate the room now. “Well, I’ll say this. I’m really relieved that does next to nothing to me.”

“Is that a good thing?”

“As I’m his sister, it is the best news I think I have ever received.”

A slight giggle escaped Fluttershy, but then she looked to the ground, her body shaking like the very thing she was supposed to be examining. “S-so what now?”

Applejack came besides her friend, before wrapping a hoof around Fluttershy’s, and slowly lifting it up. For a moment, the farm mare stopped, waiting for the tension in the yellow leg to leave, before pushing the pegasus’s fetlocks against Big Mac’s throbbing cock. “You can just look, but I thought I would help with the first step.”

Fluttershy swallowed hard, shaking at the fact that she was actually doing something sexual with another pony, but another squeeze from Applejack caused her to glance over. Her friend was still just smiling, seemingly certain that she could do this. Fluttershy took one more breath in, and came just a bit closer, now taking in the massive shaft before her.

Applejack left her to the discoveries she may find, letting go of the now stable hoof, and trotting to behind her friend. Fluttershy didn’t even notice as she pushed the shy mare’s tail to the side, and caught a glimpse of her leaking folds, quivering and trembling for more. She would not be so bold as to give Fluttershy more yet though, not while still going unnoticed. A gentle kneading into the voluptuous presented before her did catch the other mare’s attention, and she turned back to AJ as she was pushed closer to the balls that lay against Big Mac’s thigh. “A-Applejack?”

“Sorry, but…” Applejack took in a deep breath, trying to keep the thoughts she wanted to say away from what she was supposed to. “If you’re going to take that later, I want to make sure you’re ready. Besides, even if you don’t, wouldn’t you care to learn how it feels to have another touch you?”

Fluttershy’s breath caught, and she lifted one hoof to her face, trying to cover it as her body trembled. For just a moment, she lowered her head, before bringing it up, and letting Applejack have her way. She thought she heard her friend say, “How I wish I could always have this,” before something warm and wet came against her slit. A gasp was ripped from Fluttershy’s lungs, before she fell back, her body now on top of Big Mac’s girth as she looked to the ceiling. “I… I thought you were just going to touch.”

Applejack put her hooves onto the edge of the bed, a smile on her face as she lowered herself. She wanted to say why she had skipped the step so badly, especially as she took in the sweet scent of her friend’s arousal, but she was here for Fluttershy’s fantasy. “I… I guess I got overexcited. If… if you don’t want me to lick again, j-just say so.”

Fluttershy put her hooves above her face, trembling as she felt Applejack’s breath against her wet snatch. While part of her was afraid, there was a part that screamed for more. To stop worrying, and enjoy the fact that she was currently sandwiched between a mare’s hot lips, and a stallion’s large, throbbing cock. She whispered into the air, “Keep going.”

With a few gentle nudges, Fluttershy was persuaded to move up her rump sliding along the shaft, with the cock resting between her cheeks. Fluttershy’s hips moved ever so slightly, grinding herself against the wonderfully thick dick that was between her ass. Her hoof was about to touch her heated crotch, when Applejack stopped it. She looked down, and caught a tear running down her face. “Applejack?”

The farm mare’s pupils shot wide, and she didn’t bother not trying to avoid her brother as she pushed herself forward, brushing her muzzle against his brother before she kissed the open folds of her friend. Her muzzle kept teasing the ridges of Fluttershy’s pussy, while her tongue slowly came out, inching closer and closer. Another moan squeaked out of the small pegasus as Applejack’s tongue gently lapped up the sweet drops that wore pouring out of Fluttershy at this point.

Fluttershy’s moans soon filled the room as Applejack’s tongue got faster and faster. No inch of her slit was safe from the farm mare’s experienced tongue as it twisted, turned, and dived within the pegasus. Her hips slid back and forth along the trembling mass beneath her, only causing more hormones to fill the air as grunts came from Big Macintosh. Fluttershy honestly couldn’t believe she had never tried anything like this before, and was quickly feeling something rise within her.

The moment she thought about the pressure building within her, Applejack moved ever so slightly up, and sucked on Fluttershy’s engorged clit.

The effect was immediate as the whole mare’s body stiffened her eyes opened wide, her hips sliding back, dragging along the shaft one more time as Fluttershy tried desperately to stop whatever was coming. A high pitch squeal escaped her, before it turned into a scream as the dams within her broke, and the pressure came flooding out, drenching Big Mac’s stomach in her sexual spray. Fluttershy panted hard, before falling onto her side, and onto the stallion beneath her’s chest. Applejack soon crawled up, panting herself before she laid down next to Fluttershy.

The two locked eyes, the stench of sex in the air, along with Fluttershy almost being able to taste herself off of Applejack’s breath. Looking into Applejack’s green eyes though, she felt something stir inside of her. This something stopped her from protesting when Applejack pulled her in, and sent electricity down her spine when their muzzles touched.

The two spent a solid minute, tentatively letting their tongues touch and tap against each other. While she had loved being between Fluttershy’s legs, somehow, the taste of her dry mouth was a hundred times better. Pulling away though, it left Applejack cold. “I… I’m sorry. I know you like stallions, and that-” She stopped, looking at the hoof on her muzzle.

“I… I thought I liked stallions, but I-I never knew a second option, and with you…” She only smiled, looking deep into Applejack’s eyes as tears met the edges of her own.

Applejack pulled her in close, wrapping her into a tight hug. “I love you Fluttershy.”

Fluttershy nuzzled into Applejack’s chest, her eyes growing heavier by the moment. She only barely breathed, “I love you too,” before she was fast asleep, with Applejack soon to follow.

Big Mac waited a few moments, wincing at the pain in his crotch. However, he still eventually wrapped his strong hooves on top of the mares that resided on top of him. He had agreed to this whole thing to see how he felt about Fluttershy, unaware of his feelings, and hoping he could at least help the shy mare out. Seeing his sister in such bliss though made those thoughts vanish from his mind.

Unfortunately, a pent up pecker is not so easy to ignore, and it would be almost an hour before he too, knew peace that night.