Twilight's First Time

by poniesftw

Rating: mature
Tags: Sex, Twilight Sparkle, Random, Human, My Little Pony: Friendship is Magic, Rainbow Dash, Comedy, Derpy Hooves, Pinkie Pie
Length: 3139

While Spike is away at Applejack's farm picking apples, Twilight discovers something even more fun than reading. She's never really done it before, but that definitely won't stop her from trying. Later on, she sees something that she w

While Spike is away at Applejack's farm picking apples, Twilight discovers something even more fun than reading. She's never really done it before, but that definitely won't stop her from trying. Later on, she sees something that she won't forget anytime soon.

Btw, If you have not yet read the story, "Pinkie Pie's Pleasurably Fun Adventure", I'd advise reading that before this.

Published 2014-01-22 22:20:04 UTC
Last updated 2014-01-22 22:20:04 UTC

A New Discovery

Twilight sat in her living room trying to talk some sense into one of her friends to no avail. She wasn't exactly one of Twilight's best friends, but, nevertheless, she was a friend. She was very flustered, yet also seemed very excited about what she was talking about. Her eyebrows were closely knit together, causing her amber colored eyes to almost become straight; she was obviously determined to try and convince Twilight of her dilemma. Every time Twilight would say something that contradicted her statement, she would shake her head back and forth causing her long light blond hair to get tossed around. However, Twilight noticed that every time she would get excited, or a little too overworked, she would bob up and down in her seat a little, causing her rather large breasts to bounce ever so slightly. She was wearing a grey low cut shirt with a bubble design on it and capris jeans.

"No, no, no!" exclaimed Derpy shaking her head like usual, "I'm telling you, I know what I saw."

Sighing, Twilight laid down her clipboard and pen and pressed her forefingers against her temples. She had a long day, and now she was trying to give advise to somebody that obviously didn't want it. For a second, she thought about asking Derpy if she wanted a cup of coffee, since they were sitting in her kitchen, but then she realized that it probably wasn't the best idea. Derpy was already pretty hyped up as it was.

"So, you're telling me that you saw Pinkie Pie standing in your apartment naked, before jumping into your closet and disappearing? And when you asked Pinkie Pie she said that she hasn't been over to your house in at least a month?" asked Twilight, trying to get her mind wrapped around the whole thing.

"Yes, that's exactly what happened!" replied Derpy bouncing up and down excitedly, "You have to believe me."

As much as Twilight wanted to believe her friend, she just couldn't. Her story was too far out there, even if it did have Pinkie Pie in it. However, Twilight knew that if she kept telling Derpy that what she saw didn't happen, her friend would work herself up into a flustered mess.

"Okay, I believe you," lied Twilight standing up from her seat around the kitchen table.

"Really?" asked Derpy getting wide-eyed.

"Yes..." sighed Twilight shaking her head slightly.

With that, the cross eyed girl suddenly burst up out of her chair and threw her arms around Twilight giving her a big hug. The suddenness and intensity of the hug caused Derpy's relatively large breasts to squish against Twilight's own, and, in turn, knock all of the wind out of her. Twilight gingerly hugged her back, surprised by the sudden excitement.

"You're the best," smiled Derpy, letting go of the suffocating purple haired girl, "I knew I could count on you."

"Uh... yeah," replied Twilight halfheartedly, feeling somewhat bad that she had lied, "Anyways, it's kind of getting late, you should probably get home."

Nodding in agreement, Derpy said goodbye and, after saying thanks to Twilight one more time, headed for the door. Following her, Twilight waved to the blond haired girl as she walked down the driveway. She could feel the soft cool air of the brisk summer wind flowing over her body as she held the door open. Once Derpy had gotten into her car Twilight closed the door. That is, until she heard a crash from outside. Opening her door once more, she noticed that Derpy had backed into her neighbor's, Bon-Bon, mailbox.

"I'm okay!" shouted Derpy putting the car into drive and speeding away.

"That girl never fails to surprise me," sighed Twilight shutting the door once more.

Tiredly she walked upstairs to her room to get ready for bed. Earlier that day she had done some reaserch for a science experiment that she was preforming and then went to the movies with Rainbow Dash and Fluttershy. Instinctively, she called down the stairs to tell Spike to get ready for bed until she remembered that he was spending the night at Applejack's farm. Earlier that day Applejack had asked if Spike could come over and help her out with apple picking. It was, after all, apple season. Shrugging her shoulders, Twilight walked into her room in order to get ready for bed herself.

Stripping down into her underwear, Twilight neatly folded her cloths before setting them at the foot of her bed. She had worn nothing special that day, just a pair of jeans and her favorite purple t-shirt. Walking into the bathroom Twilight looked at herself in the mirror before brushing her teeth. Her long dark purple hair with a single pink lock flowed down past her shoulders. Her lavender colored eyes stared back at her through the glassy reflection. She slowly moved her attention downwards towards her breasts which were covered up by nothing except for her violet colored bra with a pink star pattern on it.

After seeing Derpy's knockers hers looked relatively small in comparison. Not that she was unhappy with her size, but she wouldn't be dissatisfied if they were a little bigger either. She was a rather large B cup, pushing on C. However, they did fit her slim figure quite nicely. They were nice and perky and complimented her slender body. Continuing downward, her eyes landed on her violet colored panties before finally her bare feet which had their toenails painted a bright lavender color.

After brushing her teeth, Twilight began walking back to her room before stopping in the middle of the hallway. It wasn't that late, and she was currently in the middle of a really intense book. Who said she had to go to bed right away? She might as well stay up and read for awhile. Going back downstairs, Twilight sat down on the couch in her living room and grabbed her book off of the coffee table. If felt a little weird to be setting in the living room in her underwear, but nobody was home, so it was fine.

However, if Spike were home she would never do something like this. She had been very careful to rise him from anything bad. Out of all the years they had lived together, Twilight couldn't remember one time when Spike had sen her naked or in her underwear. He was, after all, only twelve, and Twilight wasn't even related to him. Nevertheless, she almost felt like his mother, or sister for that matter.

Drawing her mind away from Spike, Twilight tried to focus her attention on her book. Unfortunately, the image of Derpy kept popping into her head. More specifically, Derpy's story. Just the imaginary image of Pinkie Pie standing naked in Derpy's bedroom just seemed so funny to Twilight. She could just picture Pinkie coming up with a randomly good explanation for why she was naked in her room. Although Twilight didn't particularly want to admit it, the idea somewhat aroused her. Not only that, but the slight thrill of sitting in her living room half naked also turned her on a little. Mostly because of the fact that she was not accustom to doing it.

She wondered what it would feel like to be sitting in the room with no cloths on at all. Standing up, Twilight reached back and unhooked her bra, letting it fall to the floor. She then pulled down her panties and tossed them to the side. Sitting back down, Twilight could feel the thrill intensify a bit. It was a that moment that she realized that she was a little thirsty. Getting up once more, Twilight walked across her house to the kitchen. It definitely felt weird walking around her house naked, yet she somewhat liked it and it kind of turned her on.

Upon opening the fridge to get some milk, a cold blast of chilly air hit Twilight's bare skin. Shivering slightly as she reached in for the carton, she noticed that her nipples got hard as well. Grabbing a cup she poured herself a glass of milk and drank it quickly. Some of the white liquid accidentally dripped from her mouth and trickled down her breasts. Using a paper towel, she cleaned it up. The rough surface of it slightly rubbing against her boobs and nipples only stimulated her further.

Putting the milk back in the fridge, Twilight walked back into the living room and sat down. It felt strange being aroused, it barely ever happened to her. She could only remember a select few times when she had even masturbated in her life. Not to mention that she was still a virgin. In fact, now that she thought about it, she had never actually inserted anything into her vagina. She had only ever masturbated by the stimulation of her clit.

All of these thoughts about sex, pushed Twilight over the edge. She was way too turned on now. Reaching up, she grabbed her boobs and began to play with them. She massaged them passionately focusing on her nipples. Every now and then she would pinch them sending a stream of pleasure jolting throughout her body like a shock of electricity. The more she played with them the hornier she became. Every so often she would lick two of her fingers and rub them against her hardened nipples. The wetness felt good on her soft silk-like skin.

Twilight's breasts squished underneath the pressure of her hands pressing against them, reminding her of memory foam. Her nipples poked out between her fingers as she continued to squeeze them. The sensations that she was feeling felt great, and she could sense that the area between her thighs beginning to become moist. The more she massaged her boobs the wetter she became. Eventually, it got to the point where she couldn't bare it any longer.

Laying back on the couch, Twilight slowly moved one of her hands down her body and towards her crotch, all the while continuing to rub her sensitive tits with her other hand. Her free hand glided down her petite figure, over her flat stomach to her thigh. Gently rubbing her thigh, she slowly moved her hand closer and closer to her sweet spot. Upon landing on the sensitive area, Twilight let out a small sharp sigh of pleasure. She moved her fingers in tight circles over her clitoris sending waves of sensations flowing through her body like a tidal wave.

All the while this was happening, Twilight used her other hand to push one of her nipples right up in front of her mouth. Her breasts were a little too small for her to be able to suck on them, but she could get them close enough to her mouth to lick them with her tongue. She swirled her tongue to quick circles around her nipples, every so often she would flick her tongue up and down running right over top of them. The warmth, wetness, and tingling sensation that her tongue provided caused Twilight to begin to moan with pleasure. Not only did her breasts feel amazing, but her sweet spot did as well. She was still hard at work rubbing it vigorously.

At long last it reached the point where Twilight could no longer bare but to insert her fingers inside of herself. However, she was a little frightened to do so since she had never done it before. Because of this, Twilight decided to start out with only two finger. Slowly but surely she pushed them into herself. She bit her lip, because it hurt a bit, but it wasn't nearly as bad as she had first anticipated. In fact, it was kind of a good type of pain. After awhile, she had pushed them in as far as they could go. It felt a little strange having something inside of her, and she could feel the moist walls of her pussy sucking at her two fingers.

Sliding them back out, Twilight pushed them back inside once more. This time it wasn't as nearly as bad. The more she thrust into herself it became less and less painful and more and more pleasurable. As time progressed Twilight began to slide her fingers in and out of herself faster and faster. The her wet vagina sucked at them, demanding for more. Her leg muscles tightened as she squeezed them together, amplifying the ripples of delight emanating from between her thighs.

"Oh... yes, yes, yes!" exclaimed Twilight rolling her eyes back and letting her tongue hang out.

All the while she continued to use her other hand to knead and pinch her boobs and nips. She moaned with pleasure and began to thrust her pelvic a little in order to be able to move in and out faster. She was breathing heavily and she could focus on nothing else except the thought of sliding her fingers in and out as fast and as deep as she could. Almost subconsciously, Twilight straightened out her ring finger and shoved that one in as well. Now she had three fingers churning around inside of her. This intensified the enjoyment by a lot and Twilight could feel herself getting ready to climax.

She began to make sharp exhalations in the form of "oh!" and "ah!". The closer she became to her max the most frequent and rapid these sounds became. Twilight began to arch her back a little feeling how it curved her vagina causing her fingers to hit entirely new spots altogether. The sensation was building fast and she didn't know how much more she could take. Her hot and now sweaty body curved upwards as she arched her back some more.

All at once, she suddenly reached her climax and moaned loudly, "Oooooohhhhhh...."

Juices from her pussy squirted out onto the couch and the inside of her thighs. Her hand was soaked and now so was part of the couch cushion. Twilight flopped her back back down onto the couch and laid motionless for awhile letting the bliss flow through her body. Her fingers were still stuck half way up her vagina, her body was damp with sweat, her violet color hair laid across her breasts partially covering them, and she had her eyes closed while she breathed heavily.

After awhile, Twilight pulled her fingers the rest of the way out of herself and licked them clean. Giggling to herself she stood up and looked down at the mess that she had made. She never would have guessed that she'd be a squirter. Sighing with contentment, she brushed some strands of hair out of her eyes that were dangling in front of her face. She was definitely glad that she had tried inserting her fingers inside of her. She never imagined that it would feel that good.

Twilight took a little while to clean up the living room before putting her panties and bra back on. She was, without a doubt, very tired now, and welcomed the thought of going to bed. Sleepily she walked up the stairs in the direction of her room. However, when she was only about half way up, she heard a rather loud thumping sound coming from her own room. Curious, and a little bit surprised, Twilight wondered what it could possibly be.

There were only to ways into her house and both of them were downstairs. Not to mention that you'd have to travel through the living room to be able to get up the stairs, so Twilight would have seen anybody if they had entered. Not to mention that they would have seen her as well, and the average person would be too distracted by a masturbating female to even think about the idea of going up stairs. Yeah, those calculations seemed about right. So, if somebody didn't come in, then what could it possibly be?

Twilight slowly approached her room with caution, being extra sure to keep quiet. As she got close she could hear the faint sounds of voices coming from inside her room. Not only that, but they sounded like familiar voices too! All at once, Twilight swung open the door to her room to find one of the strangest sights that she had ever seen. Standing in the middle of her bedroom was Rainbow Dash and Pinkie Pie. Both of them were absolutely naked, and it seemed like they had just finished something that Twilight didn't want to think about. In her room....on her bed...seriously!?

"Oh, hi!" announced Pinkie Pie noticing Twilight, "I met someone new the last time I came here, cool huh?"

"Um, well...what?" stuttered Twilight thoroughly confused.

"Heeeyyyy, you kind of look like somebody I know back home," smiled the pink haired girl happily, "Nice to meet you, I'm Pinkie Pie and this is Rainbow Dash! This was our last night at the crystal empire before we're going back home, so I really wanted to show Dash this cool other world! Oh, by the way, do you have cupcakes here? I love cupcakes; I bake..."

As Pinkie rambled on, Twilight noticed that Rainbow Dash's face kept getting more and more red. She had one arm across her chest covering up her breasts, and one hand between her legs hiding her pussy. The longer Pinkie talked the more irritated she seemed to become.

"Can we just go already!?" she blurted, cutting Pinkie off in mid-sentence.

"Yeah, sure thing Dashie," chortled Pinkie gleefully, "See ya later person that I don't know because you never gave me your name!"

With that, she dived head first into Twilight's open closet. Hot on her tail followed Rainbow Dash. Within seconds, they were both gone. Twilight could do nothing be stared dumbfounded at her closet for a few minutes. What in the world had just happened? Then, walking over to her bed, she laid down and stared blankly up at the ceiling. She was going to have to call Derpy in the morning. There was a lot that she wanted to talk about.

Author's Note

The End. How did you like the story? Did you think it was good or bad? I love feedback, so please give me some in the comments below! By the way, the beginning and end of this story may have been a little hard to follow if you haven't read my other story, "Pinkie Pie's Pleasurably Fun Adventure". Anyway, I personally think it turned out well, and I hope that you enjoyed it too!

Coming up next will be the last of the mane six... Applejack! :ajsmug:

Lastly, I know that I haven't posted anything in quite awhile, but I was really busy with Christmas and then finals. Now hat they're over I'll be more active. See you all around! :twilightsmile: