Little Sister Fluttershy by YamaAnon


                                            >"Are you sure the two of you will be alright?" your mom asks nervously.

                                            >"Mother," you say, "I'm an adult. You and Dad go have fun."

                                            >"What about your sister? We've never left her alone before." she pipes in.

                                            >"She's not going to be alone. I'm here."

                                            >You know that your mother is just being your mother, but you're starting to get annoyed.

                                            >You are Anon. Your parents are off to see your younger brother before going on their second honeymoon.

                                            >You shudder at the thought, but they deserve it.

                                            >"Well, okay...make sure you and your sister get enough sleep, and don't starve yourselves."

                                            >"Mother, Dad looks a little impatient." Your dad actually looks worried, too. But that's your little secret.

                                            >Your mom sighs and pulls you into a hug. "Okay, we'll see you in a few weeks. Love you."

                                            >"Love you too, Mom." With that, goodbyes are said, and your parents are off, away for a long time.

                                            >"Well," you say, "maybe I should go get Flutters." You say to yourself, grinning as you head up to your room.

                                            >Reaching into your closet, you pull out a large box and open it up. A smile comes to you.

                                            >You pull out a pink full-face helmet with a dotted outline of a butterfly on it.

                                            >With a chuckle, you can't wait to see her face.


                                            -------------------------------------------------------------


                                            A few weeks ago.


                                            >"Sorry, Flutters, none of my old helmets will fit you." You lie, pulling the black helmet off your sister.

                                            >"I thought they fit alright." she counters. She's clever, but its not time yet.

                                            >"Trust me, they're too big for you. And no proper fitting helmet-"

                                            >"-means no riding." she finishes. She's heard your philosophy on helmets so often that she points out helmetless riders with a cry of "Squid!" just like you do.

                                            >Honestly, you're surprised your sister wants to ride with you so badly. She's so timid, you'd figure that she'd be scared to even see you ride.

                                            >She sighs and puts her head on your shoulder. "Its just...whenever you go on a ride, Zephyr starts acting like a jerk."

                                            >You bite your lower lip, if there is one person you alternatly love and want to stab with a soldering iron, it's your little brother, Zephyr.

                                            >Family is Family, but man if he isn't obnoxious. And the way he gets a laugh out of messing with Fluttershy is the next-level of annoying.

                                            >"Sorry, Flutters. I'll keep riding to a minimum until Mom and Dad send him off to that boarding school." You say, gently patting your sister's head.

                                            >"Okay." she says, smiling lightly at your pats.


                                            -------------------------------------------------------------


                                            >Pulling up to the High School, you look down at your watch. They should be letting out anytime now.

                                            >A couple of people have given you odd looks at the pink helmet tied down behind you, but you shrug it off.

                                            >Suddenly you hear the familiar sound of the High School's bell go off and a flood of students pouring out.

                                            >You hope that Principal Celestia told Fluttershy you were getting her today.

                                            >Soon you see her and her friends walking out the doors, they're looking around, probably for your car.

                                            >Your sister sees you.

                                            >You can practically hear her squeal from across the schoolyard.

                                            >She runs up, her friends in tow, and stops just beside you. "A-Anon! I thought you were picking me up!"

                                            >She's terrible at hiding the fact she knows whats coming.

                                            >"I am." You play along, untieing the pink helmet and holding it out to her. "Happy -Late- Birthday No. 18!"

                                            >She smiles widely and starts to put it on immeadiately. Her friends seem happy for her, some of them saying things like "Best Brother Award."

                                            >As they walk to their buses, Fluttershy turns to you. "Uhm...Anon? How do the straps work?"

                                            >You laugh and have her bend down so you can get the straps tied. Past them, your eyes widen as you notice the immense amount of cleaveage.

                                            >You silently thank the stars for your mirrored visor as you notice your eyes shooting back to her cleavage over and over.

                                            >-Bad Anon, that's your sister!- says the little voice in your head.

                                            >Shaking yourself back to your senses, you give the helmet a wiggle. Firm, no looseness. "Anywhere feel really tight, Flutters?" you ask.

                                            >"No, Anon, its actually quite comfortable!" She says excitedly.

                                            >With a laugh, you point behind you. "Hop on, sis."

                                            >It takes a moment for her to get on comfortably. You forgot she wore a skirt today, but her dignity shouldn't be threatened, now that you've gotten things taken care of.

                                            >With a quick check to make sure its safe, you pull out and are riding down the street with your sister behind you, arms wrapped around your waist.

                                            >Once you're up to speed, you feel her tighten her arms around you. The first ride is always the scariest.

                                            >Her breasts are pressed against your back. -Why are you paying so much attention to your sister's breasts, sicko?-

                                            >Damn, that voice is back. Its hard not to notice their incredible softness with how she has you in a death hug.

                                            >Nevertheless, your focus is more on the road, where it should be anyways. You're riding dammit.

                                            >Soon you pass by your favourite ice cream place. Oh a whim, you pull in and find a shady spot for the bike.

                                            >You motion Fluttershy to get off before putting the kickstand down. You pull your helmet off before noticing Fluttershy struggling.

                                            >"You'll get it down eventually, sis." You say, undoing the straps and pulling it off, a cute squeak from your sister as it pops off her head.

                                            >You find yourself stifling a laugh. Your sister's helmet hair is RIDICULOUS. She notices your grin and gaze, and looks in one of the bike mirrors.

                                            >"Oh my!" She exclaims, before trying to fix her hair.

                                            >You, the newest recipient of the Best Brother Award, pull out her comb from home. "Here, Flutters. This should help."

                                            >"Oh, thanks Anon!" She exclaims, fixing her hair quickly. "How's that?" She asks, a loose hair slipping out of her hair clip.

                                            >You smile and put the hair back into place. "Byootiful." You say with a thick joke accent.

                                            >Once the two of you have your ice cream, you sit on the grass next to the bike. Fluttershy looks over at you. "I thought you didn't ever want to let me ride with you. You don't seem to like passengers."

                                            >You shake your head. "I always said I'd never let some girl just ride behind me. You're not 'some girl'."

                                            >Fluttershy blushes and gives you the smile that you could die to.

                                            >You pat her head and say in your softest, most sincere voice. "You're my little sister. The most important girl in my life."

                                            >She squeaks and covers her face with her hands, flustered.

                                            >You let out a laugh.

                                            >Once the two of you finish, you start getting ready to go, this time you walk Fluttershy through the straps on her helmet.

                                            >"How do you like riding, Flutters?" You ask.

                                            >"Its a little scarier than I thought...but its really nice once you're really going." She responds.

                                            >"Good," you say motioning behind you again. "because I hope you'll be riding with me a lot more."

                                            >"Of course!" she says, getting on. "Anon?" she asks once she's behind you.

                                            >"Yeah Flutters?"

                                            >She wraps her arms around your waist, her helmeted head resting on your back. "I love you, big brother."

                                            >"Love you too, little sister." You say, taking off down the street.

                                            >You opt to take the long way back home, let her get more comfortable being on the bike.

                                            >Partway through, you notice that familiar softness on your back is now...moving?

                                            >Fluttershy is rubbing against your back, or more specifically.

                                            >-Stop it, pervert! That's your little sister!-

                                            >You're starting to wonder if you should see a psychologist about this damn voice.

                                            >"Flutters? You good back there?" You ask as you pull up to a stop sign.

                                            >"Y-yes Anon, why do you ask?" She says.

                                            >"Just wondering. Its your first time, so I just want to make sure you're comfortable."

                                            >You start heading home, still feeling her rub against you. At one point her grip seems to tighten.

                                            >Once you are home, you pull the bike into the garage, and Fluttershy dashes into the house, not even stopping to take off her helmet.

                                            >You get yours off and walk inside, seeing her on the couch, a pillow pulled up to her chest, and her face redder than you've ever seen."

                                            >"Flutters?" You ask, sitting next to her. "Is everything alright?" You're afraid that she actually was scared during the ride.

                                            >"N-no...I'm not." She says, almost sounding as if she's in pain.

                                            >You take off her helmet and feel her forehead. Normal there. "What's up?" You ask.

                                            >Fluttershy whimpers and looks away. "It's embarrassing."

                                            >"You can say if the ride made you nervous. I'll understand." You say.

                                            >"Its not that...I loved the ride. Just..." she buries her face in the pillow and says something muffled.

                                            >"I didn't quite catch that, sis."

                                            >"Meebuh ah riddle bee dou merch."

                                            >You pull the pillow away gently and are about to ask her to repeat it when you notice it.

                                            >Dark splotches on your sister's white top. Her face completely red and her bottom lip quivering.

                                            >"M-maybe a li-little bit...too m-much..." she said after an eternity of silence.


                                            >You find yourself a little tongue-tied. It takes a moment for everything to click into place.

                                            >"Flutters...why are you..?" You ask, looking up into her lightly watering eyes.

                                            >She looks at you, and she whimpers out. "I-I don't know...it just started a few weeks ago..."

                                            >Suddenly, she lets out a pained whimper and she seems to shiver. She looks up at you, a single tear rolling down her cheek.

                                            >"C-can you help me?" she asks suddenly. Her eyes meet yours, unwavering. She's serious.

                                            >Your mind shuts down completely. What was happening to you right now? This was not something that happened in real life.

                                            >"Wh-what do you mean by help?" You ask. You find yourself sitting down on the couch as well, your face feeling warmer than usual.

                                            >Fluttershy crawls over to you and sits down in your lap. She bites her bottom lip as she sobs out quietly. "Th-They feel so sore...I think they need..."

                                            >She leans into you and cries onto your shoulder. She grips your shirt and looks up at you.

                                            >"Please...it hurts...don't make me say it out loud..." She says.

                                            >You feel the damp spots on her top pressed against you. Your mind is racing. That damn voice is screaming gibberish at you now.

                                            >All you know is your sister is crying, and your job as her big brother is to help her.

                                            >"H-how do you want to do this?" You ask, swallowing in order to try to keep your composure.

                                            >Fluttershy blushes and before your eyes, slips her top off and wads it up. "I'll have to wash this anyway...we'll just use it to catch my..." she turns redder as she stammers out, "...m-milk."

                                            >You feel your jaw slack. Her bra, with its own dark splotches, came off as too small for her breasts.

                                            >She squirms slightly and leans forward. "C-can you...unhook me?

                                            >-ANON DON'T YOU DARE. THIS IS NOT OKAY. TELL HER TO COVER UP RIGHT NOW-

                                            >You finally just ignore the voice and reach around. Somehow, you unhook her easily.

                                            >Her bra falls off her body, leaving her completely exposed in front of you.

                                            >Her nipples catch your attention. Those perfect little buds at the peaks of her incredible breasts, dripping ever so slightly with her white, pearly milk.

                                            >You look back up at her to see her look deep into your eyes. "Flutters...they're...amazing..." you blurt out.

                                            >Fluttershy smiles slightly and holds her already stained top beneath her large breasts. "I'll catch...you..." she's too embarrassed to tell you that you're the one milking her.

                                            >With a deep breath, you reach up and take her breasts into your hands.

                                            >You squeeze gently, pulling a gasp from her as you take a moment to familiarize yourself with their weight and softness.

                                            >You move your thumb and index fingers to her nipples, gently rubbing them at first. Fluttershy shivers on top of you.

                                            >Taking her nipples between your digits, you squeeze lightly and pull, the motion coaxes more of her milk out from her nipples, as well an incredibly sensual moan.

                                            >She catches the white streams with her top, and you repeat the process. Each time your sister seems to get louder and more milk is released.

                                            >A few rounds of this and you are milking your sister in earnest. She looks over at you, her face red and her eyes half-closed.

                                            >"A-Anon..." She stammers out.

                                            >You look back up at her, continuing your milking motion. You always thought that you had a pretty sister, but looking at her now you realize pretty was an understatement.

                                            >Between her soft, delicate features, her gorgeous cyan eyes, and her incredible body, she was so much more than just "pretty."

                                            >She was sublime. "Are you doing alright, Flutters?" You ask.

                                            >Fluttershy moans and puts one of her hands on your chest. She smiles and runs her hand down your chest, "O-of course...aaah...it feels so good to have you..."

                                            >Her eyes widen and she lets out a loud moan as you accidentally squeeze a little harder than you have been.

                                            >"S-sorry sis! I didn't mean to-!" you start to apologize.

                                            >Fluttershy drops her now soaked top to the floor, pulling her body close to yours. "It's alright Anon. I feel so much better now. Thank you so much."

                                            >It's at this moment you realize that milking your sister has given you the hardest erection you have even had.

                                            >"Flutters...I..."

                                            >She looks down and notices the tent pitched in your pants. You hear a gasp before she gets off of your lap and onto her knees in front of you.

                                            >"A-Anon...did that...turn you on?"

                                            >You feel a pang of guilt. You aren't supposed to be in this kind of situation. You were supposed to take care of her, be responsible.

                                            >And now you're in this sexual position with your little sister before the end of the first day.

                                            >You're snapped out of thoughts by the feeling of your member being freed.

                                            >Fluttershy is staring wide-eyed at your cock.

                                            >"Anon...you're much bigger than I hoped." She says, her eyes running over every vein. What a second...'hoped'?

                                            >This choice of words echoes in your mind for a brief moment before Fluttershy leans in and kisses the tip softly.

                                            >"Anon...you helped me feel better. Now I'll help you." she says before opening her mouth wide and taking as much of it in as she can.

                                            >No return now. You're not sure how or why, but this feels too good to let go. Even if she is your sister, her technique is phenomenal.

                                            >"Flutters...where on earth did you learn to do this?"

                                            >She pulls away for a moment. "Popsicles." Is all she says before going back to it.

                                            >You remember a time when you watched her have a popsicle race with her friends.

                                            >She won.

                                            >You also remember her looking over at you while the race was happening.

                                            >She pulls away and moans lightly. "Take control, big brother."

                                            >Oh, that's how she likes it. With a deep breath, you hold the side of her head. With gentle motions, you guide her mouth down onto you.

                                            >She lets out a loud moan as you guide her on the exact speed and depth to take. Her cyan eyes meet yours, and she continues to suck gently while you guide her.

                                            >If this is wrong, you don't want to be right anymore.

                                            >Fluttershy must have noticed you're resignation to allowing this to happen because she pulls away and smiles up at you.

                                            >"I think we both know what we really want to do."

                                            >The moment those words leave her lips, you pick her up and carry her upstairs.


                                            >You take Fluttershy into a bedroom, it didn't matter which one. The two of you wanted...NEEDED this.

                                            >Laying her down on the bed, you lean in and start sucking at the closer breast, caressing her other one gently.

                                            >Fluttershy moans. "Anon..." Sure enough, milk starts leaking into your mouth.

                                            >Damn, that actually tastes amazing. Your brow furrows as you think of all the wasted nectar from earlier.

                                            >As you give her huge, milky breasts the attention they deserve, your sister reaches down and takes a hold of your throbbing shaft again.

                                            >She moans in delight as she starts running her soft, gentle fingers over your hard pole.

                                            >You start to think about how she might feel when you're inside her. The thought pokes at your mind until you can't take it anymore.

                                            >With a smirk, you flip the two of you so she's sitting in your lap, your cock resting against her, showing off just how deep you're about to be in her.

                                            >She looks down at it wide-eyed. Biting her lower lip, you hear her murmur, "Oh my...will it fit?"

                                            >"Not getting cold feet, are you Flutters?" You tease.

                                            >Fluttershy pouts and reaches beneath her skirt, moving her panties aside. "It's my first time, brother...go easy..."

                                            >You smile and pull her toward you, allowing you to position at her entrance. She whimpers and lightly grinds against your tip.

                                            >You start sliding yourself into her. Warmth begins to wash over your shaft. Its a tight fit, REALLY tight. You kiss her neck and whisper. "Relax, sis. It will go smoother."

                                            >She moans in response and you feel her loosen ever so slightly. It's still tight, but you feel confident enough to slide yourself in the rest of the way.

                                            >You bury yourself to the hilt in one quick, smooth motion. Fluttershy half-moans, half-screams as her hymen is plowed through by your cock.

                                            >You lean in and kiss her on the lips. Her eyes widen and her hands grip your shirt tightly as her body squeezes your shaft, getting used to the feeling of you inside her.

                                            >After a minute, you feel her relax, she kisses you back before pulling away and giving you the happiest smile you've ever seen.

                                            >"I...I really got to lose my virginity to my beloved big brother..." she says, wiggling her hips and moaning as you move around inside her. "It's so wonderful..." she adds on.

                                            >"We've only gotten started, my dear sister." You say, smiling. You hold her hips still and start to gently thrust up into her.

                                            >Flutters moans, one of her hands moving to her abdomen, undoubtedly trying to feel you inside her. The other goes to your shoulder, pulling you toward her breasts again.

                                            >Accepting the invitation, you reach up and grab both of her breasts, pushing them together until her nipples are able to touch.

                                            >You take them both into your mouth at once and start suckling. You need to keep your hands in place to keep them in position, but it's sending your sister into immense pleasure if her moans are any indication.

                                            >With the position decided, you start to thrust a little harder, Fluttershy's moans increasing in volume alongside the pace.

                                            >"A-Anon..." she moans out weakly. She continues to let you suckle at her nipples, the sweet taste of her milk almost seeming to fuel your thrusts into her.

                                            >Suddenly she seems to tense up, a long, loud moan escaping her lips. You slow down a little bit. "Flutters did you already-?"

                                            >She leans into you, kissing your neck and whimpering, "D-don't stop Anon...not until you're satisfied, too."

                                            >At that, you flip the two of you over, laying her on her back. You use your new position to make longer, harder thrusts into Fluttershy, who grabs onto the bedsheets and moans out your name over and over.

                                            >The image of your sister writhe in pleasure beneath you is burned into your mind. This is a sight you never want to forget. Your thrusts continue to increase in tempo, and you notice her tense up in orgasm a second time.

                                            >Soon you feel yourself getting close, your thrusts reach a frantic pace as your body decides that it can't hold back any longer.

                                            >With a deep moan, you bury yourself into your sister and feel yourself loose your seed into her. She lets out one last moan before you collapse next to her, pulling yourself out slowly.

                                            >Fluttershy whimpers lightly as you leave her empty before pulling herself close to you, resting herself on your chest.

                                            >Her nipples leak one or two drops onto your shirt as she looks up at you, smiling.

                                            >"I love you so much, Big brother..."

                                            >"I love you, too, Flutters." you respond, pulling her up into a loving, tender kiss.


                                            >It isn't until after a bit of spooning that the two of you realize a terrible truth.

                                            >The two of you just had sex, with your sibling, in your parent's bed.

                                            >No wonder the mattress had seemed spacious.

                                            >The two of you get up, embarrassed, and immeadiately start to take the bedding off to put in the washer.

                                            >Fluttershy has her breasts bared the whole time, shimmering trails left where milk had flowed down her huge breasts.

                                            >The shimmering and the size of your sister's breasts mesmerizes you.

                                            >Once the washer is loaded, you do Fluttershy a favour and throw her milk-soaked top in with the bedding.

                                            >The two of you are now standing in front of the washer, looking into each other's eyes, trying to find something to say.

                                            >Fluttershy speaks first, "A-anon...did...you enjoy f-f-fu..." she squeaks and looks away.

                                            >Damn it, she's cute.

                                            >You smile and pull her close. "Of course I did, Flutters. Did you?"

                                            >She hugs you back, burying her head in your chest. "I'm so happy I got to do that with you." She looks up at you and kisses you on the lips. "To be honest, I always wanted you to be my first."

                                            >You smile and kiss her forehead, pulling a giggle from Fluttershy's lips. Pulling away, you walk toward the kitchen, "Man, that did work up my appetite, how about you?"

                                            >Fluttershy nods and follows you, sticking to you like glue. It isn't until you open the freezer that she gasps and pulls away. "Oh my...I think I need a shirt." she says, her nipples hard from the cold freezer air.

                                            >As she goes to cover up, you pull out a bag of stir-fry veggies and a cut of chicken. Heating up the stovetop, you grab two pans to cook with.

                                            >While they heat up, Fluttershy comes back down and hugs you from behind. You can feel through your shirt and hers that she's forgone wearing a bra.

                                            >'Makes sense, after what just happened, she probably just wants to be comfortable.' you think, remembering the sight of her too-small bra barely containing her assets.

                                            >You go grab some spices to liven up the taste of dinner. When you turn around, the air leaves your lungs for a moment as you see your sister leaning against the island counter in the middle of the kitchen.

                                            >She's wearing her usual long pajama bottoms, but the t-shirt she picked out didn't do much to cover her. It was cut to allow it to hang off one shoulder, as well as expose some cleavage, all while cropped to hang off her breasts and expose her midriff.

                                            >You didn't know your sister had such showy clothes. "Where did you get that shirt?" you ask.

                                            >Fluttershy blushed and looked away, twirling her hair around her finger. "I...just now took one of my old shirts and did some...modifications." Now that she mentioned it, it did look familiar. "Does it look good?" she asked

                                            >You smile and nod, walking up to her and kissing her cheek. "It looks sexy, sis. Your breasts really fill it out." you say, winking at her when you mention her breasts.

                                            >Fluttershy blushes and smiles up at you. Her lip trembles slightly as she reaches up and lifts the hem up, revealing one of her breasts. "Do...do you like them, Anon?"

                                            >"They're incredible, Flutters." you say, giving the exposed breast a playful squeeze. She lets out a small moan in response before covering herself again.

                                            >Cooking and dinner is otherwise uneventful, as the two of you wash your dishes, the phone rings. You pick it up, knowing immediately who it is.

                                            >"Hey Mom, hey Dad, you two get the hotel safe and sound?" you ask.

                                            >You almost hear your mother sigh with relief upon hearing your voice. "Yes, we did. Is everything okay over there?" she asks.

                                            >"We're good, no problems so far. Doubt there will be any at all." You say confidently.

                                            >"Is your sister there? Can I speak with her?"

                                            >You hand the phone to Flutters and say, "Mom wants to talk to you. I'll get these dishes done."

                                            >Fluttershy takes the phone. "Hi Mom...Yes, I'm alright...Don't worry, I understand you had to get going...I'll be fine, Anon is here...No, Dad, there isn't anyone else here, we know the rules."

                                            >As you finish the dishes, you look over at your sister, who looks back at you and smiles. She reaches out and takes your hand. "...I'll be fine as long as I have Anonymous with me."

                                            >The trust and love you feel from your little sister warms your heart. She hands the phone back to you, still holding your hand as you bring it back to your ear. "See, all is good. You can rest easy tonight."

                                            >"If your sister is at ease, then I guess there really is nothing to worry about. Take care of yourselves. Love you both."

                                            >"Love you too, mom." With that, you hang up and smile at Fluttershy. "What do you want to do now, Flutters?" you ask.

                                            >Fluttershy blushes and pulls you to the living room. She motions toward the couch while picking up a blanket from the blanket chest. "Can we just cuddle for a little bit?"

                                            >You smile and lay down on the couch, pulling your little sister down on top of you. The two of you find a comfortable position and allow yourselves to relax.

                                            >She rests her head on your chest, her finger tapping in time with your heartbeat. She giggles. "Your heart is beating faster, are you enjoying this?"

                                            >You run your hand up and down her back, letting out a content sigh. "Of course I am, sis." You bring your hand up and brush her hair out of her face, smiling down at her.

                                            >She smiles back, crawling up to your face and pressing her lips to yours once more. The two of you kiss for what feels like hours, enjoying the taste and feel of each other's mouths.

                                            >When the two of you finally pull away, Fluttershy sighs and gets up. "I guess I should get my homework started, don't you have to work soon?"

                                            >You nod and get up as well. You work nights at the local hospital, and of course you're scheduled for tonight. You go to your room and change into your scrubs, walking back down to see Fluttershy at the table, pouring over her homework.

                                            >Gently, you turn her head to look at you and kiss her. "You might be asleep when I get back, so good night, my dear sister."

                                            >She grabs your arm and bites her lower lip before asking, "C-can you come sleep with me when you come home?"

                                            >You smile and pet her hair, "Of course I can."