How to Date Your Best Friends

by CallieGreen

Rating: mature
Tags: Sex, Princess Celestia, Slice of Life, Twilight Sparkle, Main 6, Drama, My Little Pony: Friendship is Magic, Comedy, Romance
Length: 1395

Twilight wants to write to Celestia about the cycle of life in Equestria, Things don't go as planned.

It's winter season, and Twilight is TRYING to write about how the cycle of life works to Celestia, though she isn't technically her "student" anymore, she still has an obligation to write to her.

Things don't go exactly as planned.

What starts as a letter to Celestia quickly turns into a frenzy of comedy, hate, smexy time, and most of all, love. This is the story of how Twilight dated all of her friends.

From her point of view of course.

Published 2017-10-01 01:40:07 UTC
Last updated 2017-10-01 01:40:07 UTC

2. DON'T TOUCH ME THERE!

The first person I asked was Applejack.

"Whut in tarnation? Why would ya go askin' me that Twilight?"

I don't really know why, I guess the first pony I thought about asking was AJ, I mean, she's rowdy, and tough, maybe she did some things in her past she'd rather not mention?

"Well, I wanted to write to Celestia about something since I haven't done it in a while. I just felt the need to write to her. And, well, Starlight told me to write about love making. I know, It's pretty suggestive. But I just wanted to let Celestia know I still think of her as my teacher a--" AJ cut me off.

"Listen Twilight, It's not that I don't want to help you, I really do, but, these are pretty sensitive topics you're going on about ere', And I just don't feel right talkin' bout it."

I hung my head over my shoulders. "That's fine. I thought it was weird anywa--"

Applejack cut me off yet again.

"BUUUT, I can show you how it works."

I looked up quickly.

"Say what now?" I said in disbelief.

"Come with me, into the barn." She motions for me to come.

I walk with her and she runs into the barn, leaving me in the dust.

I run after her calling her name as I enter the barn. "Applejack? Applejack? Where did you go? If you're trying to prank me it's not working."

A bright light flashes in my face, as I adjust my vision, I see Applejack sitting down on hay with a hay table and another stack of hay on the other side.

"Uh, AJ? What's all this?"

Applejack grins. "It's a date you dummy! If you want to learn love makin' you gotta do this first!"

"Oh!" I say, I blush profusely, "Well, uh, H-how do I do a date exactly?"

Applejack motions to the other hay on the other side of the table.

"Sit down and I'll show you."

I head over to the hay and sit. It's a bit itchy, But I make do with it.

"Now," Applejack says. "Say hello and ask me how my day was."

"Uhm, okay....Hello Applejack, how was your day?", I say.

"It was alright. Nothin' new, nothin' terrible, Had to tell Apple Bloom to go fetch some supplies to help us get ready for winter, she came back a mess, had to clean er' up." AJ chuckles, then she goes on to ask me something.

"How was your day?"

I thought about what had happened today, nothing out of the ordinary except the letter and what is happening right now at this moment, so I simply said "It's going pretty good!".

AJ then moved onto talk about how stuff was going around Sweet Apple Acres, then she asked me a few questions and I asked her a few questions, we we're laughing our flanks off at the jokes we told each other. It was nice. Really nice. We enjoyed ourselves.

AJ stopped laughing slowly as she looked into my eyes and I looked into her's. It felt weird, naturally just talking to her like this. It felt as if....we we're more than friends.

Aj crawled over the table and soon she was above me, I could feel her tail tickling my right leg, The moment was tense, It felt like everything in existence stood still. Everything except me and her. This moment felt like ages.

Then. She leaned forward, and kissed me.

It was a long kiss, I felt my mouth against her's her tongue against mine, the brush of her hair against mine.

She moved her hoof along my legs, soon brushing against my pelvis, then, she touched my clit.

I jerked up. "AHHH! DON'T TOUCH ME THERE!"

Applejack moved back. "Twilight, calm down, this is how it works."

I looked at her with concern. "I-I'm sorry, I've just never done something like that before..."

AJ chuckled. "It's fine, everybody's scared on their first time, now, lay back, and let me do my thing."

I followed her orders and laid back into the hay, she soon was on top of me again, I breathed hard. Then motioned for her to do it.

She touched my clit again, I grimaced and she smiled, "It's okay, it's okay." She started to touch my vagina, moving up and down, she then moved down and started to lick, I gritted my teeth and moaned. She continued to lick until I felt something come out of me, she then moved up.

"You're cute when you moan." She said. I blushed. She then spread my legs, and put her vagina against mine.

"Ahhn!" I moaned. She moved back and forth, I felt my mind going blank. I stuck my tongue out a bit. I felt like I was drifting from reality. Applejack huffed and moaned, I huffed and moaned, It was as if it was just the two of us in the universe, in this barn.

Finally, after one last hump, we both climaxed. AJ fell on top of me as she moaned, I moaned too and almost passed out, but I held it together and put my hoof around AJ, AJ put hers around mine, and we both stared up at the barn ceiling.

1. This was NOT supposed to happen.

Things were NOT supposed to go this way.

This day started off great, everything was well in Ponyville, no villains, no threat to Equestria itself.

Then THIS happens. I-I don't even know what to call this. A DISASTER! A TRAVESTY! A--

Okay, I need to calm down. Come on Twilight. Just calm down and keep cool, that's what Rainbow Dash does, keep cool.

Where do I begin, ugh.

Well, for starters, I haven't written to Celestia in a while, I know I'm not her student anymore, but I just felt the need to write to her again. I don't know why exactly, It was just something urging me to tell Spike to pick up the quill and write. I guess it was to fill the void of not having to study friendship? I don't know.

Being a princess and not a student has several ups and downs, One of those downs is the amount of duties you have to do in a day. Schedule meetings, meetups, all those obligatory princess things you'd think a princess would do.

A BIG downer is not being able to write to your own mentor because you're not her pupil anymore. Which, as Rainbow would say. Is "totally lame".

I wanted to write to Celestia today, but I didn't know what to write. In fact, I was cooped up in the castle thinking about it all day. So I, like any smart pony would do, went out to ask for advice.

As I was about to exit my castle, i saw Starlight trotting around and decided to ask her.

"Hey! Starlight!" I said.

Starlight whipped around just in time to see me, she looked taken aback for a bit, then she came over.

"Oh! Hey Twilight! What do you need?" She asked.

I quickly told her my dilemma.

"I just need something to write about. ANYTHING would be great right about now."

Starlight started to think up something. It took a bit, but she finally spoke.

"The Life Cycle!" She said.

Huh? I thought.

"Y'know, how life works, how ponies meet one another to make other ponies!"

I gawked. "Why would I write about SEX to Celestia?" I said in pure disgust.

Starlight shrugged. "I don't know, I thought it'd be an interesting topic to talk about with her."

I thought about it.

"Well, it's not that bad of an idea..it is pretty suggestive...but...I'll do it." I said.

Starlight patted me on the back. "Go for it."

The she left.

I can't believe I thought writing about love making was a good idea. But I thought it was a good idea, so I did it.

The thing is, I really didn't have a sense of how love making worked in the first place, I never really engaged in that kind of activity when I was a young mare. I mostly spent time cooped up in my room studying magic.

So I decided to find out how exactly it works. But not in the way I envisioned.