The Shy Girlfriend & Sweet Wing Girl

by DiamondandIce

Rating: mature
Tags: Original Character, Equestria Girls, Porn, Comedy, Main 7 (EqG), Sex, Pinkie Pie (EqG), Second Person, Fluttershy (EqG), Romance
Length: 3801

A Valentine's Day story with two girls spending their time with one boy

It's Heart's and Hooves Valentine's Day and you decided on bringing something for your special someone rather than her being the one bringing a gift to you. When things go a little bitter between you two and with the help of some party girl (which is also your wing girl), you three will enjoy what will happen next.

All characters are of legal age and know what they are doing even if I don't mention it in the story

A one shot story created for Valentine's Day

Cover art by: Ryuu

Story request by Harold4

Published 2022-02-13 22:40:00 UTC
Last updated 2022-02-13 22:40:00 UTC

Kind & Sweet Valentine's Day

“Almost done, just need to add the buttercream on top to shape it into a rose to complete these cupcakes.”

You are almost done with the cupcakes you baked after looking again at the calendar excited for tomorrow which is February 14, meaning Valentine's Day. These are actually for Fluttershy, your girlfriend. Your first impression with her was awkward due to her personality and her name of being you know ‘shy’. You two became friends when you took a part-time job at Sugarcube Corner where Pinkie Pie also works there, who is also a friend of Fluttershy, making animal shaped snacks and an animal themed cake for a birthday party requested. Fluttershy came that day with her friends and saw how cute those snacks you and Pinkie were making. Time went on with you becoming friends and now she is your girlfriend.

“Done.” You finished adding the buttercream on the last cupcake and are proud of your work. You felt something was missing though until it hit you and grabbed from the cupboard two dispensers with two different kinds of sprinkles in each. “Now which one is better, silver sprinkles or valentine sprinkles?”

“I suggest the Valentine Sprinkles.”

You got startled and threw both sprinkle dispensers in the air. You quickly caught the one with silver sprinkles but wondered that there was no sound of the other dispenser hitting the floor. You turned around to see the one who startled you that’s tossing the other sprinkle dispenser in their hand is none other than Pinkie Pie.

“Seriously Pinkie, don’t just pop out anywhere without warning.”

“You’re so silly Harold. I was actually knocking at your door but you never answered, so I looked around and saw you by the window. Then I went back to the front door and since it was unlocked, I let myself in.” Pinkie stopped tossing the dispenser in her hand and turned her attention to the cupcakes that you made. “So I bet these lemon cupcakes with raspberry-flavored buttercream are all for Fluttershy.”

“Yes and no. I think I made a little too much (12 cupcakes) so I planned to let her share these with you guys, until you ruined the surprise.” You whispered that last part. “Anyway I think it needs something to make it more appealing and you suggested Valentine sprinkles.”

“Uh-huh. Let me finish it for you.” Pinkie raised the dispenser in both hands above her head as the dispenser itself started to glow pink. Your pupils shrink as you figure out what will happen next after Pinkie and her friends get their super powers.

“PINKIE, LET ME TURN AROUND BEFORE YOU-”

“AHH NOW LOOKED WHAT YOU’VE DONE, THERE’S PINK POWDER IN MY EYES!”

Yep, Pinkie may be annoying but she did become your mentor in baking and your wing girl.

****************************************************************************

The next day after your last class of the day, you quickly dashed for the home-ec classroom since you left the box of the cupcakes you made there. You arrived as Granny Smith was about to leave and assured you that no one touched them. You approached the fridge and took out the box of cupcakes and peeled off the written warning ‘Do not touch!’. You navigate through the crowd of students and several couples, avoiding bumping into anyone.

You arrived outside the Music Room and it looks like they are having band practice. You are about to knock on the door until the music stops, then the door opens.

“Harold, there you are. What are you doing waiting out here, come on in. Fluttershy was waiting for you to give you her gift.” Pinkie was the one that peeked her head from the door and grabbed on to your hand, pulling you inside.

“Hi Harold.” The Rainbooms greeted you upon entering.

“Hey girls.” You greeted them until you felt someone lunged onto you as they wrapped their arms around your body. You looked down to see the love of your life, Fluttershy looking up at you. “Hi Flutters.”

“Happy Valentine’s Harold.” Fluttershy pecks you on the lips as her friends are in awe of their friend. “Oh let me just get something in my bag.”

“Oh how lucky Fluttershy is with Harold that she won his heart before I do.” Rarity said as her heart melted watching her friend. “Which, I am happy for them.”

“Sure you are.” Rainbow Dash said, rolling her eyes without noticing that Rarity is glaring at her. She switches her attention to the box you have in your hand. “Hey Harold, what’s in the box?”

“I almost forgot.” You placed the box on a table as the Rainbooms gathered around while you removed the ribbon and opened it for them to see your gift. “This is actually meant for Fluttershy only but since I made a little too much, she can share this with you girls.”

“Aw Harold, you really didn’t have to.” Sunset took a cupcake from the box, same goes with her friends. “Guess those lessons with Pinkie Pie did pay off.”

“What can I say, she is my mentor and the one who helped finish decorating it with sprinkles.” You said as you looked and she gave you a thumbs up. You notice your girlfriend doesn’t have one yet as you grab one from the box. “Fluttershy, here take one.”

“N-No thanks.” Fluttershy said in an unhappy tone which you wonder why.

Her friends also notice her change of behavior. Earlier she was so happy to see you, now she is doing the opposite of it.

“Is there something wrong? Are these not your type?” Sci-Twi asked after taking a bite.

“N-No it's not that, I love the cupcakes he made. I just can’t seem to accept it.” Fluttershy then hands over your gift with her hands shaking. “H-Here’s mine.”

“Hate to interrupt sugarcube,” Applejack said. “But Ah don’t understand why ya’ll acting like that. You made those chocolates for Harold.”

“Yes I did, but I got Pinkie to help me with it. He did his all by himself which is for me and all of you. He put in so much effort, while I didn’t.”

“I mean Pinkie helped with decorating it with sprinkles so she may have helped a little but that doesn’t matter. Like the saying goes ‘It’s not the gift, but the thought that counts’. Right girls?” You said which her friends agree but your girlfriend still feels upset. You placed your hand underneath Fluttershy’s chin to raise her head making her eye contact with you. “Is there anything I can do to cheer you up?”

“There is.”

****************************************************************************

Tomorrow after classes, Fluttershy asked a favor if she could do her surprise at your place with Pinkie Pie’s help. You didn’t mind and made sure that the others Pinkie promised not to follow and spy.

You three are at your place where you pointed Fluttershy and Pinkie to your kitchen and to your bedroom. The two ask for you to wait in the living room for they will set things up in your bedroom for odd reasons. You kept yourself distracted by watching baking videos on your phone until they called you to come to your room. Now in front of the door to your room both of them called you to come in.

You never anticipate but hanging on your wall is a large cut out heart. Standing on each side of your bed are Fluttershy and Pinkie Pie but they weren’t in their usual clothes; Fluttershy was wearing a brown overall skirt with light green linings and a white buttoned up shirt inside and a red ribbon tied around your girlfriend, while Pinkie is in a baby blue overall skirt with purple ribbons with a white top underneath and on a small table are a can of whipped cream with another can that doesn't have a label and which what it looks like a lipstick container.

“Girls, what is this?” You asked.

“This is our surprise, silly!” Pinkie chimed.

“Like I said.” Fluttershy approached now leaning herself as you felt the softness of her breasts pressing on you. “Even though it may be late, I want to give you something more than yesterday. So, I am your surprise and want you to love me a lot.” She looked away smiling and blushing.

“Same here.” Pinkie rushed over and pressed her fun bags on you as you see she is looking at you with bedroom eyes. “You did help that day with all those orders before Valentine’s and now it’s time I did something in return. So we came up with this.”

You gulp either you are going to enjoy it or weirded out by what these two are planning for you. You thought of it thoroughly and accepted their offer. Pinkie squeed with your girl saying her low tone ’yay’ as both of them planted their lips on yours. While distracted with the kiss, both of them undid your pants as it fell to your feet, leaving you with only your brief. You groaned as both of their hands rubbed against the bulge on the fabric itself and you felt them tugging on part of your brief and lowered it down exposing how hard you are right now.

“Wow Fluttershy, I never knew Harold’s popsicle would be this big.” Pinkie said as she got to her knees to see it up close.

“I guess the surprise was a success, seeing him very happy.” Fluttershy pecked you on the lips then got to her knees next to Pinkie. She wrapped her fingers around your cock and gently stroked it, sending shivers down your spine. “Looks like this is in pain right now.”

“Or it's ready for a good licking!” Pinkie said, licking her lips. “Do you mind if you lay on the floor?”

You did what Pinkie told you as you lay on your back. Fluttershy got between your legs as Pinkie stood above you which you notice she isn’t wearing any panties which she saw your reaction to. The party girl lowered herself with her thighs on both sides of your head and her slit now in front of you.

“Now you just lay there and let us do our thing.”

“I wonder what she meant?” You thought as you stared at Pinkie’s slit while moving her hips left and right wanting you to lick it. Before you could do anything silly, you felt some cold thick liquid being poured onto your dick. “Hey! What in the world are you girls pouring?”

“Don’t worry Harold,” Fluttershy reassures you. “It’s just condensed milk.”

You dick twitches as you feel your girlfriend’s hands touch your thighs. The same goes with Pinkie’s hands next to hers. Their warm breaths made your body shiver and you immediately felt both of their tongues licking your entire length, getting both the base up to the tip. Their moaning as they kept licking made it even better on your end as they switched to a different area. Fluttershy started massaging one of your balls and sucked on the other while Pinkie Pie took half of your member into her mouth and slowly bobs her head while swirling her tongue from within.

You try not to roll your eyes upwards and control yourself as best as you can as you feel something tingling from below and quickly tap your hand on the floor getting both girls' attention.

“Wait, dont cum yet!” Fluttershy said making Pinkie pull your now we member from her mouth with a pop.

“That was close.” Pinkie said as she poked your tip. “Don’t want to end the fun so soon.”

“Tell me about it.” You thought as Pinkie got off you.

Fluttershy offered her hand as she helped you get up and led you to the bed. She sat next to you and instructed you to cover your eyes and don’t peek unless she said so. While you cover your face with your hands and look in the opposite direction, you hear Fluttershy ruffling her clothes.

“Okay Harold, you can look now.” Fluttershy said as she tapped on your shoulder.

You turned around as your eyes went wide on what Fluttershy is doing right now. Her overall was lowered and her shirt was raised exposing her well-endowed mounds. While using her hands to press them, in the middle which looks like a white chocolate shaped heart that is being hugged by her mounds as she leans forward wanting you to grab it. You reach it out with your hand but she moves back and shakes her head which you wonder as you point to our mouth which she nods.

“Well don’t just sit there.” Pinkie got behind and gave you a push as your face fell between your girlfriend's breasts.

You are about to pull out until Fluttershy wrapped her arms around your head wanting you in this position as you try to grab the chocolate. You are having a hard time grabbing it and breathing as you feel the softness between your head and with every time you breathe and nuzzle, Fluttershy’s moans louder. She gasped as you wrapped your arms around her body and she removed her arms from your head and she saw that you got the chocolate heart in your mouth.

“S-so how was it, did you like it Harold?” Fluttershy asked with ehr cheeks still slightly pink after that little foodplay you two did.

You raised your hand as you finished eating the chocolate first. After that you smile and nod as Fluttershy said her soft ‘yay’ that she is happy you enjoyed it which you intend to do with her next.

“I-I should be the one-OOOFF!” You pushed Fluttershy down, cutting her sentence.

“I insist.” You said and turned to see Pinkie offering a can of cold whipped cream.

Fluttershy just lay there as you pour blobs of cream covering both her nipples which made her shiver due to the coldness while she bit on to her shirt. You placed your mouth on her nipple and started sucking, tasting the sweetness of the whip cream with it. Your girlfriend starts to squirm because you know that her nipples were one of her sensitive spots.

“Hey let me join in!” Pinkie then latches her mouth to Fluttershy’s other nipple.

“Pinkie-ha no, wait!” Fluttershy moans very loud now that both of her nipples as you and Pinkie straddle her wrists.

Not wanting to stop the fun and after giving her nipple a few more flicks with your tongue, you removed your mouth and took off her overall and shirt leaving Fluttershy only in her shoes, of which your main aim is her button in her middle. You took the can of whipped cream and poured a little in her hole and like earlier, you started licking her button.

“Hahahaha-no please, not there!” Fluttershy fails to contain her laughter while Pinkie is busy with her tits. While you were teasing her, you slid your hand down and started rubbing your girlfriend’s clit, giving her a bigger reaction. “H-Harold not there!” You and Pinkie didn’t stop until Flutterhsy couldn’t hold it anymore and reached her climax as she let out along ‘Eeeeppp!’ A moment on, your girlfriend slumped and lay there on the bed breathing heavily.

“Sorry,” You said.

“N-No i-it’s fine.” Flutterhsy said between her moans. “Let me just rest first.”

“Good, now you can have fun with me!”

Pinkie jumped from behind your back. You turned to see she undressed herself just seconds ago leaving her also only in her shoes. In her hand is the lipstick container and after opening it, the lipstick was colored brown which she explained she asked for one of Rarity’s empty lipstick containers and use it to make chocolate lipstick. While your mind is distracted with Pinkie being kinky, Pinkie applied the lipstick on her own lips and pressed her lips to yours.

Pinkie aggressively wants you to lick it off of her which you did. While busy licking off the chocolate, Pinkie wrapped her arms and legs around you as she grinds herself on your lap and from how wet she is, you felt your cock being drenched as her lips continued to rub on it making you groan. You took the chocolate lipstick and applied a little not to her lips, but to both her areolas as you lowered your head down and started licking it off.

“Oh-wow! Why haven't I thought of that?” Pinkie said with her head thrown back.

With Pinkie’s lips all cleaned up again after applying the chocolate lipstick and is now wet, she removes herself from you and gets on all fours on the floor next to the bed. She points to her ass, wanting you to do anal with her. You panicked as you look at Fluttershy which she doesn’t mind as long as she is the only one you will love which Pinkie adds for being friends with benefits a thing you owed her for helping you out with Fluttershy.

“Whenever you're ready Harold, PUT IT IN!” Pinkie moved back after you got behind her with your tip touching the entrance.

You slowly pushed your cock inside her ass and without any problem after Pinkie soaked with her juices as you felt her pink buns touched your lower abdomen.

“O-Oh yeah. Mmm, it’s finally in.” Pinkie moans as she starts to move, which should be the other way around.

You corrected this as you grabbed onto her hips and started bucking forwards making the party girl lose her strength as her upper body is now slumping to the floor. You grabbed both of Pinkie’s wrists pulling her up as you continued pumping inside of her.

“Pinkie, I'm getting close.” You said as you increase your movement speed as you switch from her wrists to fondling her own tits.

“Do it!” Pinkie lolls her tongue out as her mind goes blank with you going deep inside her ass. All it just takes is one more push…”Harold, I-I WAAHHH!

You released your jizz inside Pinkie as she came at the same time soaking your balls. After pulling out Pinkie collapsed to the floor. You get worried if you went a little too rough as you check only to see she is sound asleep already.

“That explains the snoring…and the snot bubble.” You thought as you picked her up and lay her on your bed. Fluttershy then jumps to your side as she clings to you with your arm between her breasts.

“Don't forget about me Harold.” Fluttershy leaned and nuzzled on your shoulder.

“Don’t worry, I didn’t.”

“Another thing, you won’t have to worry about getting me pregnant.”

You and Flutterhsy got into position without disturbing Pinkie. Your girlfriend impaled herself onto your dick as she gasped with heavy breaths. Like Pinkie’s, Fluttershy’s inner walls hugged the sides of your cock making you groan everytime she tightens it which she loves to tease you for. Since you still have Pinkie’s chocolate lipstick in your hands and just little enough gave you an idea. You asked Flutterhsy to stick her tongue out as you rubbed the remaining chocolate on it.

You started to makeout with your girlfriend and even attempted to suck her tongue with the chocolate on it.

“Harold, wait!” Flutterhsy broke from the kiss but you pressed your lips back to hers, as she got pushed onto the bed with you being on top. “It feels weird, but I like it.”

Since she likes it, you placed your hands on your girlfriend's mounds. Your hands sink a little due to her rack being larger than the average female student as you start to massage them.

“Oh Harold.” Fluttershy wraps her arms and legs around you, preventing you from pulling out from her. “How I love you so much.”

You curl your body on her for she is the one unable to spasm as you thrust deep inside her. The sounds of your wet slaps on her pussy can be heard as your tongue dances with hers as you feel you are getting near again.

“I…I can feel you twitching.” Fluttershy clings onto you like her life depended on it. “I want you to cum inside me…please.”

You granted your girlfriend’s wish as you came inside as she screamed in pleasure. You loosen up for her to breathe as you pull out, with a little of your cum to leak out from her pussy.

“Thanks so much Harold for this, even though I’m supposed to be the one doing the work.”

“You really didn’t have to.” You pulled Fluttershy as the two of you are now sitting up. “Like I said, it's the thought that counts.”

While at it Pinkie’s snot bubble pop, waking the party girl from her slumber and sees you two.

“Awwe, is the fun already over?” Pinkie asked.

“I don’t think so.” Fluttershy said as she looked down to see you became hard again and looked at you seductively. “I think Harold is ready for another round.”

“Can I at least rest first?” You asked as the two girls looked at each other then looked at you.

“No!”

****************************************************************************

What you three didn't know is that upon entering your house, a fly entered and followed to the bedroom. This ain’t an ordinary fly as it transmits what it sees to a computer screen of a very familiar egghead as four other people you three know watched.

“Eeek, it should have been me there with Fluttershy instead of Pinkie.” Rarity said as she bit on her handkerchief.

“Now what was that part you said that you are happy for her.” Rainbow reminded the fashionista while looking at the monitor without turning her head that Rarity is lookking at her angrily while pouting. “Quick move to a different position so we can get a better view,”

“Alright already.” Sci-Twi controlled the fly to a different part of the room to where you and Pinkie are now at Fluttershy. “If they think we cannot spy on them, well they won’t even know we are thanks to my little invention.”

“Seriously Twi, first a robot dog, a selfie drone, a robot to help during the Fall play and now this a remote controlled fly, which you made to look exactly like a real fly haha.” Applejack chuckled.

“That’s my girlfriend.” Sunset wrapped her arm around Sci-Twi and pecked her on the cheek. “Oh hell yeah, now they are getting to the fun part and as long as nothing comes out from this room, we didn’t break a Pinkie promise. Applejack, do you mind handing over the bag of chips?”

“Ah say we broke 50 percent of it.” Applejack said as she handed the bag of chips.