Dating for Eggheads

by Overmare

Rating: mature
Tags: My Little Pony: Friendship is Magic, Romance, Sex, Twilight Sparkle, Main 6, Cheerilee
Length: 4987

Twilight Sparkle begins to feel a bit lonley, and asks her friends for some advice on how to fix that.

Twilight Sparkle begins to feel a bit lonley, and asks her friends for some advice on how to fix that.

Published 2013-02-02 13:00:02 UTC
Last updated 2013-11-25 23:50:13 UTC

Chapter 1: A New Feeling

It was a particularly sunny day out, somehow brighter than others would usually be. Birds were chirping, squirrels with scurrying, and the sounds of ponies laughing could be heard all throughout town. It wasn’t a special day or anything; maybe it’s how nice the day is effects the ponies moods. Yeah, that’s it. Or, maybe it’s because hearts and hooves day is only a month’s time away.

Twilight was sitting on a floor cushion, looking out at all the ponies on the street while pondering those thoughts.

Twilight was never the one to really care about relationships in that sort of way. She had her friends, and that was enough for her. Hearts and Hooves day to her was just like any other day, except having to listen to Rarity talk only about sappy clichés regarding the day. She has only ever spent a few Hearts and Hooves day here in Ponyville, but it’s nothing different than it is on Canterlot.

Who is she kidding, of course it’s different. Back in Canterlot, she took the day as a day to relax and study, not having to worry about any interruptions. Once Twilight was coming of age, the Princess would always urge her to go out and meet some new ponies, and who knows… maybe even might a nice colt.

Twilight chuckled as she remembered the thought.

Of course she never gave it any thought. She could really care less about ever finding somepony. At least not for a long while, she thinks. She has her friends to keep her company, and of course she will always have Spike. Besides, she’s always too busy with her studies to ever bother, she continues to think.

But, here in Ponyville, it’s pretty hard to ignore the particular day like she could in Canterlot. Ponyville is too small of a town her single ponies to go unnoticed. The year before Twilight remembers how her friends tried to set her up on a few dates. Of course it was Rarity leading the action, throwing colt after colt at her, nudging Twilight to take the bait.

She couldn’t have been bothered to care. She’s quite happy with being alone, and doesn’t feel like she should feel the need to change that anytime soon. Besides, having somepony else around would only take up her time, she thinks.

Twilight remembers the first Hearts and Hooves day she spent here, and how excited Spike was for the occasion.

“What’s with tie?” Twilight looks over to spike.

Spike looks at himself in the mirror and puffs out his chest “I’m going on a date with Rarity!” he proclaims.

Twilight giggles at him. “And does she know this?”

Spike slouches over, “No”, he looks to the mirror again, puffing out his chest once again, “But once she sees this, she bound to fall right into my claws!”

“Calm down there lover boy,” she giggles, “Let’s just wait and see”.

That night Twilight had plans with all her friends to meet up at a restaurant and have a nice little dinner together. It had been a while since they had gotten together, and thought it would be the perfect opportunity. Just the six of them together, having a grand old time, at least she thought just the six of them.

“Sorry Rarity didn’t fall into your claws mister lover boy” Twilight runs her hooves through Spikes spines.

“That’s alright Twilight. I figured she would have had a date. A pony like her would never fall for a dragon like me”

Twilight couldn’t help but feel sad for the poor little guy. She was quite shocked to see that most of her friends had brought dates to the occasion.

Rarity had brought along some young colt with her, but he sat there most of the time just gawking at Rarity, telling how she was the most amazing pony in Equestria, and how pretty she looked. Twilight rolled her eyes at the thought.

Then there was Rainbow Dash. Twilight didn’t quite understand Rainbow at the time, and why she had brought two mares with her. Back then Twilight was still sort of new in town, and didn’t quite know everything about her friends. She later found out that Rainbow was a, well… “Filly Fooler” as Rarity had described to her.

Twilight was surely not new to the idea of two mares together. Living in Canterlot, she had seen and learned quite a bit of things. She learned that sometimes when two ponies like each other, it doesn’t matter whether or not one Is a stallion or a mare. She just had not experienced seeing it happen in front of her before. Dash was all over them that night, kissing both back in worth in a drunken mess. Twilight just gagged every time she looked over.

Though, she did notice something weird that night that has been bugging her for a few years now since that day. She couldn’t help but notice every that every time Rarity would say something romantic like to the colt, Applejack would shoot her a nasty look.

She couldn’t figure out what it was back then, and even to this day she can’t figure it out.

“I guess I can try again next year” Spike says.

“Yeah, I’m sure you will get her then” Twilight smiles at him.

The next hearts and hooves day came, but to no avail Spike had no luck. That Hearts and Hooves day was the first time her friends brought up dating.

“Have you found a date to bring to the ball sweetie?” Rarity asked Twilight as she was helping her with a dress.

“A date? Why would I have a date.”

“Oh darling, you can’t tell me that you would rather go alone”.

Twilight never bothered thinking about it. Of course she wanted to go alone, why would she bother going with anyone. She had told her friends a million times that she was perfectly happy by herself. She doesn’t need anyone anyways… right?

“I’m fine on my own. Besides, I have you girls to keep me company.”

“I don’t see why you don’t at least give it a chance” Rarity says.

Twilight was getting annoyed by Rarity’s continuing picking, so she finally gave in.

“Know what, fine.”

“I’m sorry, what was that dear?” Rarity looked shocked.

“I’ll give it a chance, at the ball”.

“Oh ho ho, this is so exciting!” Rarity says, almost jumping around in glee .

The ball was nothing special. It was something looking being put on in town square. It’s an annual tradition that’s always put on, but Twilight and her friends had missed it the year before with the dinner.

The night pushed on, and Twilights friends had gone off into the crowd to find somepony for themselves to “have a little fun with” as Dash liked to put it. It was just Rarity and Twilight together at last. They hadn’t told their friends about the little plan Rarity and Twilight had formed. She wanted to keep it between them after all.

“How about that one? He looks rather dashing.” Rarity points at a young colt, probably only a few years younger than they are.

“Oh I don’t know”.

“Sweetie, you have been ‘I don’t knowing’ all night. You have to at least give it a chance”.

“Fine, whatever.” She gives in.

Rarity had called over the Stallion she had pointed out. Things had gone less than planned, making Twilights night from something good, to something less than wanted.

“I’m so, so sorry about that dear, not all stallions at like that” Rarity rests her hoof on Twilights shoulder.

She couldn’t help but feel so disgusted thinking back to just a few moments ago at how the young colt had acted.

“Do other ponies do that?” Twilight begins, “that’s just so… ew gross” she spits.

“Not at all dear, that’s not only rude, but disgusting”

Twilight had thought about what the stallion was asking, but she could never imagine ever doing such a thing. All three of them together, that’s just gross she thinks.

“We don’t have to continue if you don’t want to, I would understand” Rarity tells her.

“I think I might just stay here, you go on ahead at have some fun”

“Now Twilight, I’m not going to leave you here all along on a day like today. Especially after something like that .”

“Rarity, please. I don’t want to ruin your night because of me. Besides, I’m sure Spike is looking for you somewhere.” She rolls her eyes.

“That little dragon never gives up, does he” Rarity giggles.

“I’m sorry about him”

“Oh it’s alright dear. I think it’s adorable”

Rarity had gone off into the crowd, leaving Twilight all off on her own, making sure she okay first of course. There was no doubt Twilight was fine, she always. She said it a million times, and she will always continue to say it a million times for. She will never need anyone, because she’s perfectly fine all by herself. No stupid colt is going to ruin that for her.

Though, that night had not been all THAT bad. Someone she had never expected to talk to her randomly appeared out of what seems like nowhere.

“Um, hello?” Twilight hears a voice.

She looks up and noticed a fuchsia coloured mare standing in front of her. She’s only a bit older than she is, but she could never tell the difference.

“Oh, hey there Cheerilee.”

Twilight had known Cheerilee for a little bit now. She would visit the library ever so often when she needed a book for a new subject she was teaching. They were not exactly friends persay, but more like acquaintances.

“You look a little uneasy, is everything alright?” Cheerilee asks her.

“Yeah, I’m fine”

“Oh. Well, I seen you over here, and I thought I might as well ask you something”

“It was just some dumb colt” Twilight blurts out.

“What?” Cheerilee looks a little confused.

“I lied. I’m not all THAT okay. Some stupid stallion sort of ruined this night for me”.

Twilight really was okay though. That rude stallion had upset her just a tad though. She wasn’t expecting such a thing to come from a ponies mouth, so of course it would make uneasy, if only just a little.

“Oh” Cheerilee looked down. “Did you and your special somepony have a fight?”

Cheerilee had looked a little said when she asked that, and Twilight never understood why. It’s still something she never understood.

“Ew, not at all” Twilight looked disgusted, “Just some stupid colt, that’s all.” She spits.

“Oh, well I’m sorry”.

“It’s fine, really. You said you wanted to ask me something?”

“Oh” Cheerilee looked off guard for a moment. “Yeah, um… Never mind.”

The two talked a bit more that night, mostly about books and stuff. Twilight loves that sort of thing, and made her night just that much better than before she had come over. The night had grown old, and was time for her to find Spike. She found him sleeping underneath a table with his thumb in his mouth. She had parted her ways with her friends, and that was that.

Twilight sighed as she remembered that night. She doesn’t need anyone anyways. She’s Twilight Sparkle after all, element of magic. She’s far too busy learning new magic tricks and saving Equestria, she thinks to herself.

She looks out the window and sees couples walking side by side, grinning as wide as the other can. It’s not even Hearts and Hooves day yet, but with the day being so close, she can tell the spirit is obviously in the air. A spirit she doesn’t even bother caring about.

She sighes once again.

I don’t need anyone, right?

“Hey Twilight”

Twilight jumps at the sound and snaps out of her obvious day dreaming.

“Ah, spike. What?”

“Are you ready?” Spike asks.

“For what?” She questions him

“The picnic, duh” He gives her a look like she is crazy or something.

“Oh yeah” She giggles, “That’s right”.

A nice picnic with her friends will definitely take her mind off things. Not like she even cares about what she is thinking anyways, right?

Why am I even thinking about this?

“This has been lovely” Rarity speaks up

“Um, yes it was” Fluttershy nods her head in agreement.

Twilight looks around the field they are in. It’s just Rarity and Fluttershy with her left on the blanket one of them brought. Dash is flying around holding Applejacks hat, while Pinkie is rolling around the ground laughing as hard as she can. Applejack is yelling at her, but Twilight can’t quite make out what is being said.

Spike had left to go run some errands he had forgotten about, and took the opportunity to finish them while the day was nice.

Thoughts about earlier are flowing back into Twilights mind, but she just shakes her head trying to forget about it. Rarity takes notice at Twilight change in expression, and knows something is up.

“Are you okay dear?”

“Huh?” Twilight snaps out of it and looks up to see Rarity hovering over her.

“Something’s wrong sweetie, I can tell.”

“What? Nothing’s wrong” Twilight flares up.

Rarity gives her an unimpressed look.

How does she always do that?

“Okay fine” Twilight admits, “Maybe there is something”.

Her three other friends take notice of what’s going on and head on over to her.

“Everything all right there sugar cube? “Applejack is the first to speak from the three.

“I… I don’t know” Twilight looks sad.

Am I okay? Why am I caring all of a sudden?

“Just tell us what’s up” one of her friends says something, but she’s not quite sure which.

“I’ve been thinking a lot lately and… never mind, it’s stupid.” Twilight looks away.

“Sweetie, we’re your friends, you can tell us. There’s nothing to be scared of”.

She looks at each of her friends. They’re all staring at her with open ears.

“Well, okay.” She looks at each of them again. “It’s just, what if maybe I do need somepony?”

Her friends look at her stupidly.

“I look at all of you, and think how happy you all are.”

Her friends start to look confused.

“What are you talking about?” Dash says.

“I’m talking about love” Twilight hides herself in her mane the best she can.

“Oh…” Rarity is the first to talk. “Oh!”

Twilight only gives her a look out from the corner of her eye.

“But, you’ve always said that-“Applejack starts to talk but is cut off.

“That I’m happy and don’t need anyone else? I know.” Twilight looks down at her hooves. “But… I’ve been thinking a lot about it lately. What it might feel like. And with that stupid day coming up next month, I can’t stop thinking about it for some reason.”

Rarity puts her arm around Twilight.

“Sweetie, if you think you’re ready, we can find a stallion”.

“What if she likes mares!” Rainbow cuts in.

“Please,” Rarity says amused, “I don’t think Twilight is like that.” She puts her nose up in the air.

Twilight looks at the both of them.

“What if dash is right?” All of her friends gasp, except for Dash of course. “What if I like mares, or maybe both?”

What if Dash IS right?

“Or maybe she loves mares, but hides it and says she likes stallions instead” Applejack stares at Rarity.

“What?” Everyone says in unison. Rarity just gives Applejack one of those dirty looks.

What just happened?

“Never mind” Applejack backs off.

“How do I know…” Twilight starts, “If I like mares or stallions?”

“Well…” Rarity says slowly. “Which do you think of when you, well… you know”

“Know what?” Twilight looks confused.

“You know” Rarity coughs, “When you tend to ones flower”.

Twilight gives her a dumb look.

“When you clop!” Rainbow shouts, maybe a little too loud. Twilight notices a few ponies in the area look towards them.

“Clop?” Twilight continued to look stupidly.

Dash rolls her eyes, “When you touch yourself.”

“Oh… OH!” Twilight looks a little silly, figuring out what they’re talking about. “Yeah, I um, don’t do that”

“What!” Dash blurts out.

“Sorry?” Twilight is unsure about how she feels about this.

“You mean to tell me you have nothing done it before?” Rarity looks baffled.

“Do you girls?”

“Of course” Dash cuts in again. “Like, everyone does it!”

Twilight sees her friends nod, even Rarity does. The only exception is Fluttershy, who is hiding underneath her mane.

Coming to think of it, Twilight never has thought about it. She had always been too busy with her studies to even indulge in such an act.

“Now, It’s nothing to be ashamed of” Rarity assures her. “It’s a normal part of life, and every- almost everpony does it”.

She let’s that sink in for a few moments, and begins to imagine… things.

Ew, what am I doing. These are my friends.

“So, will you guys help me?”

Her friends look at her funny, Twilight only rolls her eyes.

“Not with that!” Her friends settle down. “With finding someone.”

“Well, I suppose it’s worth a shot” Rarity tells her. “Once you um, find out what you like” she says awkwardly.

“Thanks girls, I owe you guys so much”.

Twilight comes home to a silence. It’s night by the time she comes home, and figures spike is probably just sleeping.

She notices she is pretty tired, and might as well head up to bed. She can’t remember what time she had actually woken up at, but only that she is tired. She made her way into her room, and noticed spike wasn’t there.

Probably just downstairs.

She’s too tired to care right about now. Spike’s big enough to take care of himself anyways, she thinks.

She plops herself onto her bed, feeling a massive surge of relaxation.

Oh how I’ve missed you, bed.

She quickly jumped under her covers, making herself as comfortable as possible, which really wasn’t all that hard at this point. She thinks back to what her friends said earlier today.

Am I seriously going to do this?

She pictures the only stallion she really knows, a big red workhorse, with a giant green apple on his flank.

Ew, but that’s Applejacks brother

It’s the only stallion she knows, around these parts anyways. She shrugs the thought off and continues anyways.

She pictures him in bed next herm his big green emerald eyes staring into hers.

Well, here we go.

She lowers her hoof down towards her nether lips, stopping just above the slit. She rolls her eyes at how silly she thinks this is.

She slides her hoof down further, sinking down into her slit. She gasps almost instantly at the new found pleasure. She looks over and notices that Big mac is gone, but replaces with his sister, Applejack instead.

Say what now?

Applejack is running her hoof in circles all over Twilight body. She rubs her rub up and down, gasping a little with each stroke.

She looks over to her right, and now Rarity is there with them as well. She breathes in deep, indulging in the smell of Rarity’s luscious mane. Rarity begins kissing Twilight all over, increasing the stimulation.

But these are my friends.

Twilight continues to move her hoof about her swelled lady bits, moving right over her-

“Ugh!” She gasps out.

I don’t even care, this feels amazing

Applejack is gone, and it’s just Rarity with her now. They begin to rock their hips together, causing her to do it outside of her imagination as well.

She rubs herself even faster now, slowing down over that magical button of pleasure she found.

“mmmm” she moans, while Rarity puts her hoof between Twilights thighs.

Twilight increase the rate she’s rocking her hips at, but still slowing down when she moves over her clit.

“mmmMMM” she moans louder, feeling a deep pressure building inside of her.

She close to the edge now, she can feel it. She stops rubbing up and down, and focuses on that magical rubbery button.

“UGHH!” she screams out, just about to come.

Her ear twitches, she can hear someone at the door.

What?

The door opens and she sees Spike walking into the bedroom.

She stops what she’s doing immediately.

“Ah! Get out!” She demands.

“What’s that smell?” Spike asks.

“OUT!”

“Okay, okay.” He says, pulling the door shut.

She closes her eyes and tries to bring back her fantasy. Nothing comes.

She puts her hoof between her lips again, but instead of pleasure she only gets pain.

Ugh, that was sooo good too.

Only then does she realize what Spike meant. The air in her room smells of recent sex, something she is unfamiliar with.

She pauses for a moment when she realizes what her fantasies were.

Those were my friends.

Maybe it’s the fact that her friends are mares is what is throwing her off. She certainly doesn’t mind a all, but it’s just… weird for her.

So do I like mares then?

She thinks over and over about the situation, unable to come to a conclusion. She knows one things though. Whatever it was that she was doing, it felt amazing.

Chapter 2: Sun Rise

Light pours through the window in Twilights room as the sun rises. Rays from the sun hit her eyes, making her cling to her sheets and turn over. Getting out of bed right in the morning was never Twilights strong suit. She’s always been the one to laze around in the morning, and take her sweet old time getting out of bed. Her behavior was something she always did, and probably will never change. She can only think about a few ponies that actually get up bright and early.

Applejack crosses her mind, picturing her waking up every morning to watch the sun rise. She thinks about how Applejack might look on such a morning. The sun making her mane shine in ways Twilight couldn't imagine.

Twilight can feel herself blushing of the idea of sitting next to Applejack, watching the sun rise. She catches herself, and decides it’s about time to get out of bed.

She looks at herself in the mirror, and notices how messy her mane is. She quickly brings up a brush and fixes her mane, preparing herself for the day to come. Flashes from last night’s fantasies still linger as she dawns on the events while combing her mane.

What am I even doing?

“Do I even care?” She mumbles to herself.

Of course I care… right?

She finishes with her mane when it dawns on her she still has to speak with spike. Had it not been for him, she might have reached a brand new type of feeling, ready to ride it through enjoying every last bit of it.

“Spike!” she calls for him.

No answer.

She calls for him again, but to no avail, there’s no answer. She searches around the library with no luck.

Where did you go?

Just then, there was a knock at the door. Twilight opened the door to see Rarity alongside spike. She gave Spike a small grin, and motioned them to come inside. Rarity was giving Twilight a look, and she could tell Spike must have said something.

Spike walked away, leaving Rarity and Twilight alone in the room together.

“So. Spike huh?” Twilight murmurs.

Rarity lets out a small devious smile. “Well aren't you the little devious one”, she chuckles.

“He told you?”

“I don’t think he knows, but he told me you were angry, and your room smelled funny”. Rarity pauses. “I didn't think you would try so… soon.”

“I feel gross” Twilight admitted. “I mean, I liked it, but should I really be doing this?”

“It’s perfectly natural Twilight. I’m glad you’re so eager to find out that part of you.”

Twilight just nodded in agreement.

“So” Rarity nudged, “who were you thinking about?”

Twilight panicked.

“Uh, no one, I don’t know. A stallion, I think.”

Now THAT’S a lie.

“You think?”

“It was totally a stallion, I remember now. Can we talk about something else?”

To be honest with herself, Twilight was a little ashamed about her true feelings. Not only because it’s a friend, but because her friend also just so happens to be a mare. It’s not like she has any problem with that or anything, it’s just so… unexpected.

Rarity could tell something was up, but it’s too soon to pressure Twilight about something she’s already touchy with.

“You’re going to have to talk to him sooner or later” Rarity suggests.

Twilight sighs. “I know.”

____________________________

A few days had gone by, with nothing changing much at all. While Twilight was eager to discover new things, she was also weary of seeing what she will find. This whole brigade has been on the backburner the past few days, not thinking much of it. Not doing a particularly good job of keeping otherwise unlady like thoughts out of her head, Twilight was having a hard time sleeping. She had awoken early, the sun still yet to rise.

Twilight had not seen Applejack since the picnic, and thought it to be nice to surprise her and watch the sun go up together. Something she had not done with her in a very long time. On her way to the farm, she began fantasizing taking Applejack right there as the sun rose. She quickly shook her head to rid herself of the thought.

Strolling up to the farm, she was met with Applejack, already busy with some early morning chorses.

“Well howdy there Twilight. Fancy seeing you up at this time.”

“Good morning Applejack. I couldn’t sleep and thought I might come visit.”

“Couldn’t sleep huh?” Applejack lowered her brow, “Them stallions keeping you up at night?”

Of course she would. Not like it’s stallions or anything.

“Hehe, stallions, sure”. Twilight rolled her eyes.

“Say Twi, how about we go up the hill over there and watch the sun rise. It’ll be up in just a minute.”

“Ha, that’s exactly what I was going to ask you.”

The two hurried their way up the hill, and found a nice spot under an apple tree to sit down and watch the sun rise. It was a perfect moment if there ever was one. Twi felt at peace for a moment, free from her thoughts. At least for a little while. As the sun rose, she noticed the sun’s rays glistening off of Applejacks golden blonde mane, just like in her fantasy. Twilight had to admit to herself just how gorgeous her friend looked, basking in the morning sun.

“Applejack?”

“Yeah twi?”

“Have… have you ever been in love?”

Applejack looked at Twilights face, and sighed with a bit of dismay.

“I thought I was,” she sighed.

Twilight found it hard to believe that a pony as busy as Applejack had the time for such a thing.

“What happened?” Twilight asked.

“I guess we just drifted apart, romantically. Some days I miss it, sometimes I wish I could do it all over again and change things, ya’know?”

“I’m sorry Applejack, I don’t know what that feels like. It must be awful” Twilight places a hoof on Aj’s shoulder.

Twilight was seeing a different side of Applejack that she rarely sees. A sensitive side. Whoever this pony was, must have really left a hole in her heart. The way she talked was nothing like how she usually is.

“Don’t let my mistakes discourage you though Twi. Love is a wonderful thing, I’m sure you’ll find the right stallion for you”.

“stallion, right”. Twilight said heavy heartedly, in light of the recent mood.

“Something wrong Twi?”

Should I tell her?

“I… I don’t know. Is there something wrong with me?”

“Of course not Twi, why do you say that?”

“Can, can you promise to keep a secret?” Twilight pleaded.

“Of course” Applejack smiled.

“Well, it’s not exactly… well…” Twi stammered.

“It’s alright Twilight, you can tell me”.

“It’s not exatly… stallions, that keep me up at night”. Twilight looked away, slightly ashamed.

“Dang nabbit, I owe that dang Pegasus 10 bits”.

Twilight responded with a confused look.

“Sorry Twi. Dash and I had a bit of a bet going on to see which side you played for. Guess she was right.”

“You’re not mad?”

“Mad? Why would you think that sugar cube. You’re our Twilight, and We’ll always love ya no matter what gets your motor running.” Applejack chuckled a bit.

“Thank you Applejack”, Twilight said, hugging Applejack.

It felt like a weight was lifted off of her, finally telling somepony the truth. Twilight felt closer to Applejack than ever now, like a special bond was formed just now.

“So I guess we’re just gunna have to find you a mare for hearts and hooves day then, huh?” Applejack smirked.

“Settle down Applejack. I don’t even know how much I like mares yet”.

Enough to keep me up at night, that’s for sure.

“I’m just kidding with you Twi”.

Maybe I should just take you.

wow

Did I just think that?

“Anyways,” Applejack began, “I should be getting back to work.”

“Right, I should be heading back to the library as well.” Twilight responded. “And Applejack?”

“Yes Twi?”

“Thanks”, Twilight smiled.

Applejack nodded and carried on her way back to the farm. Twilight couldn’t help but stare at Applejacks rump as she walked. With the truth out, she was seeing her in a different way than before. A new light that felt strange to her, but like it fit just right.

Author's Note

Long time no see, eh? Sorry for cutting this short. Just trying to break my way back into this, and remember what I was trying to do.