Twilight Attempts To Get Laid

It was about three weeks from nightmare night, and Twilight was more determined than ever. She was going to try to sleep with one of her friends and she had done countless hours of research. Her eyes had bags and were bloodshot from staying up till sunrise. She rubbed her temples in frustration as she contemplated what to do

"Ugh! Why is the difference between theory and practice so bucking vast?! I mean really! Having sex with somepony shouldn't be this difficult!" Twilight had tried several times to have sex, but every time she tried, she got nervous and ran away. However, this time around she would get it right! After all, there comes a point were jacking off just gets old and really, really lonely. Twilight had found it hard to find someone that was interesting on an emotional and intellectual level, but Twilight was worried she would end up like Steve Carell in The 40 Year Old Virgin. This time around however, she actually knew ponies that she was attracted to and found genuinely interesting. She had plans to make within the next week and she would ask one of them to have sex with her! She studied their key attributes and tried to figure out based on that who she would ask. One of the mistakes she made in the past was that she had read a few books on pick-up lines and tried a few of them out which only got her laughed at. I mean, who falls for cliched pick-up lines anymore? "Twilight tapped her hoof and smiled "I know! I'll go visit Rarity. She knows about proper dating etiquette." Twilight looked outside and laughed. "Except that will have to wait til Celestia raises the sun. I doubt Rarity would appreciate me coming over at such an hour."

She decided to look over her notes that she wrote down and then read a book that she borrowed from Rarity called A Mare In The Moonlight. Twilight initially hated the idea of reading erotic novels, the idea of reading them embarrassed her more than anything. She was worried that her friends would grossed out by it, but after talking to Rarity and trying out a few, she grew fond of them. Although they would never be as appealing as a Daring Do book or Harry Trotter. After an hour or so, she decided to hit the hay (no pun intended) and go over to Rarity's first thing after breakfast. Twilight had a very strange dream that night. She was hanging out with her friends and they were old, but still had a great deal of life in them. All the years of saving the world had done them quite a bit of good. They were all talking about their various life experiences, when Rainbow Dash started talking about her best sex stories.

"You would have thought that as small as his dick was when it was soft, that it wouldn't be very big. Lemme tell ya, when I got him nice and hard, I was surprised at how big he was. I mean dayum! It was like a fucking jack in the box. Then I thought that maybe he was one of those stallions that was all thrust and no technique, but he surprised me again. Honestly, it was one of the best orgasms I ever had. Made me cum in almost ten seconds flat." Rainbow always was the most daring when it came to her personal life. She looked over at Twilight who had been nodding, and had a thought. "So you got any good stories for us egghead? I've always heard the quiet bookworms were pretty freaky in the bedroom." They all looked at Twilight in eager anticipation. Twilight started sweating nervously and tried to come up with an answer to her question. She knew she couldn't lie to them. Mostly because she was terrible at it.

"Actually, I've never had sex. I was always too busy studying or spending time with all of you, and I thought that friends were more important." Twilight blushed from embarrassment. Rainbow started laughing.

"Seriously Twilight? You're a virgin? I never would've seen that one coming!" Rainbow said with just a pound of sarcasm sprinkled on. Applejack, Fluttershy, Rarity and Pinkie Pie started snickering as well, causing Twilight to shrink in her chair. Literally. Their laughing became louder as she kept shrinking until it was just a demonic rumble of laughter. Twilight started to cry, rolled up in a ball. She screamed. Then with a *thunk* hit the floor and realized she was in her bed. Or rather she was in her bed til she fell out from trashing about. Just then the door opened and Spike appeared.

"Twilight! Are you okay? I heard you screaming and then a loud thump sound. I ran up here and... you look like you had a terrible nightmare or something." This wasn't the first time this had happened to Twilight and Spike was worried. 'Maybe you should see a therapist Twilight. This is the 5th night in a row and you look terrible. Have you been sleeping?"

"Not really Spike. I just need to clear my head and go for a walk. I'll be going over to visit Rarity for a bit." Spike normally would ask to go so he could visit Rarity, but he figured it would be best to not ask this time around. After all, he could go visit her another time.

"Ok Twilight. I'll make pancakes for you when you get back. With daisies!" Spike always knew how to cheer her up. Twilight smiled.

"I'd love that Spike. See you in a bit." Twilight said as she walked out of the library and made her way to Carousel Boutique. Twilight contemplated her research as she trotted through town and nearly ran into a few ponies on her way, getting annoyed looks from them. "Based on that, I think I know who I'll choose to ask." Twilight smiled and felt a bit happier.

"Ask who, what dear?" A voice asked her.

"Oh, just the pony I'm planning to give my first time to." Twilight then realized that she said that out loud. "Shit." She looked up to see Rarity looking at her with an "oh really?" look on her face. "Oh! Um. Rarity! Hi. I was uh... joking. Yeah. I was just messing with you!." Twilight laughed nervously and rubbed the back of her head. Rarity deadpanned.

"Twilight. Do you honestly think I can't see through a lie? I've met politicians who are better liars than you. You've never been good at it, especially when it comes to sex darling. Come inside and we'll talk." Rarity opened the door and motioned for Twilight to come inside. As they went into Rarity's room, Twilight found herself at a near panic, not knowing what to say at this point because Rarity already knew what she was planning to ask.

"Rarity, I'll straight with you since I basically told you everything without meaning to. I've never really been great at making friends until I met you and the other girls, and I'm even worse when it comes to the idea of sex." Twilight felt a bit... No more like a whole lot of embarrassed.

"Say no more Twilight. I have a great idea that will help you out. I know some ponies that would be willing to have sex with you."

"Really?!" Twilight said with nervous excitement. 'Who are they? Have I met them before? What do they look like?" Rarity put her hoof over Twilight's mouth.

It's myself and the other girls." Rarity smiled seductively. Twilight looked at Rarity and was lost in The Twilight Zone.

"Whaaaaaaaaa???" Was all Twilight could manage to say.

"You see Twilight, the five of us have talked a bit about the idea of asking you to try having sex with us because, well frankly, you are as Rainbow Dash put it, "pretty fucking hot". Rarity normally never used bad words, but it seemed appropriate in the moment. Twilight tried to collect her thoughts and maintain composure, but that was rather sudden. She took a few deep breaths, then remembered her research.

"Well actually, I was planning to talk to you all about that, but I never thought this would be so easy. I've been doing research on who I should ask to have sex with. Honestly, I couldn't really decide. So I thought maybe I'd just ask all of you." Twilight was still nervous as heel, but relieved.

"Shall I ask the others to come her tomorrow to discuss all this then?" Rarity asked enthusiastically.

"Yes. I'd like to set up a schedule and figure out what works for everypony. How about, 6 pm tomorrow? I just need a bith to prepare." Twilight was more than a little nervous.

"That sounds absolutely wonderful dear!" Rarity was actually holding back some degree of excitement. She couldn't get the idea of fucking Twilight out of her mind. As unladylike as she felt that was, it was exciting!

"Then I'll see you all here tomorrow!" Twilight hugged Rarity and walked out of Carousel Boutique and thought to herself as she walked home. "I have a lot of planning to do." It never occurred to Twilight the possibilities of fucking all of her friends, but it wasn't unwelcome in any way. She began to daydream. Fluttershy in particular was the main pony she was daydreaming about. She was wearing a leash and collar, with a maid outfit on. She would tremble under Twilight's touch, only for Twilight to assure her that she had no reason to be afraid.

"Oh Mistress Twilight, we shouldn't be doing these things. This is so... naughty." Fluttershy said with a single tear in her eye.

"I know, Fluttershy. Doesn't it feel good though?" Twilight looked into her eyes seductively and kissed her passionately and she rubbed her hoof on Fluttershy's now wet folds, causing Fluttershy to gasp and then quietly moan and she squirmed under Twilight's touch.

"Y-yes it does Mistress. It feels wonderful." Fluttershy had a crimson blush on her face which she tried to hide from her Mistress, which made Twilight put her hoof under her chin so as to make Fluttershy look directly into her eyes. She kissed Fluttershy once again and proceeded to make her way down between Fluttershy's thighs, when she smacked Twilight across her frorehead. Twilight came out dream land and realized that she slammed her head in the door.

"Dammit. I need to pay more attention to where I'm going." Twilight noticed a chill between her legs and realized that she was rather wet. "Looks like I need to go masturbate. Otherwise I won't be able to think." So she went to have another lonely masturbation session.

Author's Note

For those reading, thank you so much! This is my first attempt at writing clop and I really wanted to get it right. Let me know what you guys think!