Author's Note

Took me a little longer than expected.

Thank you to Davis Collus for proofreading this chapter and making the cover art.

Although I planned to get this out before no nut November I didn't have as much time as I wanted before I went out to party on Halloween.

̶H̶e̶r Their first time

The clock on Twilight’s bedside table read ‘2:48’, along with her water glass, lamp and reading glasses it was all neatly organized on her bedside-table with ruler-like precision, as it always was. Tonight was like any other night for her, she had come home from school, finished the homework she had gotten for the next 2 weeks, read till 8 and then peacefully fell asleep.

Twilight was fast asleep on her back and had been for many hours now, her parents were sleeping peacefully in the next room over and her brother.

The door scraped against the floor as the latches creaked silently. The tiptoe of the stallion could only be heard by only one other if she was not already asleep.

Shining Armor’s face was illuminated under the moonlight as he crept towards Twilight’s bed. As he met the bed he nearly stubbed his hoof. He brought his eyes to his sister, she sure was asleep and to his delight was still as beautiful as ever despite the darkness.

He put his mouth to her covers to pull them off her, in doing so he caught a whiff of her natural musk, a scent he didn’t understand but very much liked it despite that. As he pulled his head back he caught a glimpse of her exposed vagina, he stopped and stayed still for a moment. He just kept staring at it for what seemed like forever, he had seen a mare’s cunt before, but they were mostly hidden behind their tails, however, this was different. Much different. He stayed like that for god knows how long, subconsciously saving the image as the greatest thing he’s ever seen, perhaps even the greatest thing he’d ever see.
A perfect memory frozen in time for him forever...

He came to his senses and snapped out of it with a newfound appreciation for the female form, which was so generously laid out in front of him. But he could only imagine how much he’d like what he came for from his sister. He lit his horn to get a better view, Eliciting a minor flinch and groan from his sister. He mostly shrugged it aside, seeing as she was still asleep, now with her sensual bits more exposed to him than ever.

Shining saw his target and was willing to commit to his mission. He began to slowly move his hoof towards her hole, very cautiously to not wake her up. As he finally met her lower lips he carefully prodded them apart, meriting a small flinch from Twilight. He stopped again to allow her to re-adjust, before continuing as he went further in, as he touched her entrance lightly Twilight moaned, ‘a sign of satisfaction’ he thought. As he prodded at her vagina he began to lightly touch her clitoris. In return, Twilight moaned loud enough to alert mom and dad. Shining quickly pulled his hoof and nearly jumped out of his skin thinking for sure he awoke his parents. He looked towards the door to meet what would surely be a bad experience.

Twilight yawned with all the might that a filly could yield, beginning to wake up far from here normal two hours before school.

Shining’s heart was racing faster now, it already was from her announcing moan but now it was beating so hard he could have sworn he’d have a heart attack if it kept up. His eyes shot straight towards his sister, his jaw dropped wide open.

She looked to her left to see the figure as she began to adjust her vision to the darkness.

“M-Mom? What time is it? School shouldn’t start for hours.” she said with a yawn.

“Shh.” Shining hushed her in a husky tone, putting a hoof in front of her mouth, gesturing for her to silence herself.

Twilight was taken back, rubbing her eyes with her hoofs to adjust her vision to the dark environment. She looked down towards her somewhat wet genitals, she thought maybe she wet her bed. However, that couldn’t be true, after all, she did read those papers on how to not wet the bed when she was an even smaller filly.

“Shi-Shining? I um, Why are you in my bed?” she said awkwardly with a very red face, hoping he too had not noticed the wetness of her bed too.

Shining hesitated… he couldn’t think of an answer, with his jaw slowly dropped open as he realized how weird he was being, the entire situation was weird, he’d never really understood the female body and had to have one of her friends do a shotty forge his fathers signature to get into his sex-ed class the day before, but those diagrams left him uncomfortable and taught him near to nothing useful on the subject, he came here to get hoofs-on experience with her sister, he never intended to have her wake up. He just wanted to examine her youthful body so he could know what’s up when he finally popped the question to Cadence.

“Shiny?” Twilight asked with concern for her brother in the minute he’s been silent.

‘Oh god, she’s staring at me...’ he thought to himself in a panic ‘Oh god, I’m staring back’ his eyes quickly avoided eye contact and moved down from her eyes… towards her vagina.

She saw his gaze go towards her kitty and blushed a little more.

He looked down towards the bedsheets and started rubbing his neck “Tw-Twily, do you um, do you trust me?” he said before the silence got even more awkward.

“Well of course I do,” she retorted, giving him a light punch in the shoulder “You are my BBBFF after all.” she gave a light smile with that last line.

Shining took a deep breath in, putting on a deadpan expression as he did. He breathed out and slowly put his hoof towards Twilight’s vagina, staring directly at it.

“Um, Shiny? W-what are you doing?” she said, her face flush red as her light smiled turned to awkwardness.

Shining completely ignored his sister as he continued with his expedition. He met his sister’s vagina and stopped just outside of her entrance, ready to part her vaginal lips.

“Sh-Shining?” she tried to plead as she grew ever so uncomfortable with the situation, not wanting the pony she looked up to so much to see, or much less touch her when she was in such a position. “Shin-” she was cut off as a huge shiver as a shiver crept up her spine from her kitty as her brother touched her special spot. Her light, albeit awkward smile immediately dropped to her resting face, now redder than ever.

She froze in place, not sure how to react to this invasion of her personal space. Although her mother had always told her not to let anypony touch her kitty until she was older, this was different. This was Shiny, This was her BBBFF. He never hurt her and although this felt wrong, it didn’t feel bad. Maybe she should just trust him. Her mother had said not to let anypony touch her kitty until she was older. And she was older than when her mother first told her that. Maybe Shining just knows more than her and she was supposed to let him touch it now that she’s older. This is just her coming of age story like the ones she read from the library, This is just a story.

As Twilight’s kitty continued to be explored by her older brother she gave out some involuntary pleasure to him, her kitty clamped around Shining’s hoof as she squeaked a couple of minor moans, much to the delight of Shining. As Shining continued with his assault Twilight felt weirder than ever, it felt like she was about to explode, her breathing quickened and finally, the pressure was just too much for her.

Her kitty gushed out seas of ‘liquid’ while waves of pleasure combined with awkwardness and guilt swept over her emanating from her pussy. Her spine tickled and this mixed feeling overtook her completely. At this moment she could smell the liquids coming out of her, it was oddly sweet-smelling. She could feel her brother, not just his hoof but the entirety of him. She felt so whole for just a second, however, her brain quickly reprimanded her body for it as the guilt and the ‘wrongness’ of the situation once again dawned on her. She didn’t entirely know why it felt so wrong but it just did.
Although it felt good to be in the moment and to have her pussy be played with,he was still being violated. She couldn't comprehend why he was doing this to her, and it was definitely a break in her ‘personal bubble’ that she did not like. Usually, she didn’t mind when Shining touched her, he was her brother after all. But this felt different, it felt wrong, very wrong. It-

“Um, Twilie…” Shining said, cutting off his sister’s train of thought.

She didn’t hear the words that came out of his mouth, she didn’t want to hear it. She wanted to continue living her former filly life, but her brother had denied that to her now. Her own brother had taken away that innocence and forced her to, according to the romance stories she'd read, 'come of age', but this was anything but romantic!

Although her first orgasm lasted only a moment, it felt like forever as she sat with her thoughts. She couldn’t stop thinking that she had somehow been betrayed, she wasn’t sure why but it was not a nice feeling either way. It wa-

“Tw-Twilie?” Shining reasserted himself.

She finally snapped out of it and looked him dead in the eyes, but said nothing. She couldn’t find any words to say, and she couldn’t bring herself to say them anyway.

“Do you um...” Shining began to scratch his foreleg, “You think you can do the same for me, Twilie?” His face turned cherry red when he said it.

Twilight did nothing, she was still frozen in place not sure how to react to what “the same” meant for a stallion. She knew there were some biological differences but her father wouldn’t allow her to bring out the more descriptive books from the library, so alas she was dumbfounded.

“Here, I’ll, um show you, Twilie…” He said with a nervous look on his face. “Just, stay quiet, Twilie.”

He reached out his hoof towards her own. He pulled her towards his shaft, lightly bringing the rest of her towards him where he made her begin to lightly massage his already erect penis.

Twilight hadn’t quite realized what she was doing, but she was a little taken back from her brother’s cock. Clothes were optional in Equestria so she had seen a few male ‘flowers’ before but they were always neatly tucked in under their bellies. She never gave much thought to them until now, and it was getting bigger? How could such a large ‘thing’ fit into that tiny little sheath?

Shining began to look out the window dead-eyed with a half-smile on his face. She wasn’t sure why but she followed the leader and looked away from him too. It felt good to not have to look at him, but she felt guilty about that. Why wouldn’t she want to look at her own brother? ‘He’s the nicest pony in Equestria and you can’t even bear to look at him?’ But she had to admit that it did feel good not to have to look at him.

While they continued this all too sensual massage Twilight could feel it growing bigger and veinier by the second. She didn’t know if this was good or bad but he sure looked like he was enjoying it, so maybe it would get him out of her room sooner. She started to awkwardly grip at his shaft, it wasn’t much but it was enough to get him to look at her which only made her shut her eyes to avoid looking at him.

“Ohhhh… Twilie…” He began to moan and grunt at her. She took this as a sign that she was getting closer to getting the same thing that happened to her happen to him.

She started to take a more active role in whatever it was they were doing, pushing up and down on his shaft on a jerky matter.

“Yes…” He said nearly out of breath.

He started to pick up their pace and forced her hoof up and down on him faster and faster, Twilight took it over from there, not sure what the next step of this ritual would be.

“Twi, I’m gonna… Twi!” He said in his most whisper-shout voice.

Twilight wasn’t sure what he was gonna do, but it didn’t sound all too great for her. She tried to pull away but he wouldn’t allow her to. He gave out one loud grunt before his penis exploded with passion. He painted his crotch and Twilight’s hoof with a strange new liquid he hadn’t told her about yet. She opened her eyes to see her brother still in a euphoric state staring off into nowhere.

She decided it would be best to know what the fuss was about. She pulled her hoof towards her snout, it didn’t smell like the sweet liquid that came out of herself. Twilight put it to her mouth and looked up at Shining who was now adamantly staring down at her. She didn’t want to embarrass herself anymore so she just went ahead and licked it like what she saw Shining do. It didn’t taste that good either, it didn’t taste like anything. She was immediately interrupted by another rope of Shining’s liquid pouring out onto her, covering her face in this new liquid. This was accompanied by another groan of epic proportions.

“Wow…” He said euphorically “Twilight, you were… You were really good.”

Twilight blushed, not knowing how to return what she could only assume was a compliment.

“No, seriously. You’re really good at this…” He began to blush as well as he began his next sentence. “Twi, has any stallion ever told you that you’re, um, sexy before?”

Twilight still couldn’t find the words to talk to him. She just shook her head instead.

“Well, you are. And more than that, I think you’re the best little sister I could have ever asked for. I-I love you, Twilight.”

She turned redder than a tomato hearing that. But she couldn’t help feeling bad for hearing that. She did not understand why it felt so bad.

“Twilie… Do you love me too?”

She froze once again. She didn’t know what to say, except;

“Yes…”

“I’m really glad to hear that Twilie. You’re a really strong filly, which is why I know I can count on you to not tell mom or dad what happened here” He said while staring into her eyes.

She didn’t say anything.

“Twilight, do you promise not to tell anyone what happened here tonight? I could get in serious trouble.”

She stayed still and silent.

“Twilie?” he said.

“I-I promise…” she whispered.

“I love you, Twilie.” He kissed the top of aher head and then got off the bed.

As he was about to open the door he looked back on Twilight.

“Oh and, Make sure you clean up after yourself there.” He smiled before exiting the room.

Twilight loved her BBBFF and wouldn’t want to get him into trouble, so she did as asked and went into the bathroom to freshen herself up and grab a towel. She used that towel to scrub off the fluids that had been spilt that night. She put her towel on the side of her room and laid on her bed.

She didn’t go to sleep that night. She just sat on her bed to cry. She had a flurry of emotions and couldn’t understand a single one of them, all she could understand is that she was crying now. She laid there for hours never stopping her silent sobbing, but she saw the sunrise that morning and strangely it didn’t bring her anything of substance. Usually, she loved the sun and the summer solstice because it let her know that Celestia was looking out for her and all of Equestria, but not today.