The First Time’s Not So Different

by LilSlipsy

Rating: mature
Tags: Comedy, Shining Armor, Sex, Twilight Sparkle, Slice of Life, My Little Pony: Friendship is Magic, Porn
Length: 8091

Twilight and Shining share stories of their first times having sex.

Alone on a roof together, Twilight Sparkle and Shining Armor spend a nice evening enjoying each other’s company while watching the sunset. One story leads to another and then they’re telling each other what their first time was like. Totally normal stories, from two totally normal siblings.

Tags: F/M, Straight, Female/Male, Filly/Stallion, Foalcon, Accidentally Incest, Alcohol, 69, Vaginal, Oral

Proofread by Deus Foalt & AndwhatIseeisme

Written as an entry for Shakespearicles' First-Time February Contest

Published 2022-03-01 01:50:01 UTC
Last updated 2022-03-01 01:50:01 UTC

First Times

“And I can’t believe you did that in high school. Only my brother would spend his entire summer allowance on a paladin-and-princess-themed, one-week anniversary present.” Twilight Sparkle giggled before taking a small sip of the cider she had in her hooves: a gift from her friend, Applejack. Her gaze went back to the sunset they were watching from atop one of her castle’s many rooftops.

“Ok, yea, it was silly, but Ogres and Oubliettes was pretty big back in the day!“ Shining Armor said with a proud flick of his mane. “All of my friends were into it as well.”

Twilight just shook her head a little and continued to chuckle, eyeing the amber liquid as she stirred it around like it was inside a beaker. This was the more fermented kind of apple beverage that had some kick to it, compared to the spring fare the whole town was used to. Really she never drank to any degree, but this would have hid away in the cupboards for years if she didn’t make a point to use the gifts she was given, and what better time to have something important than with her BBBFF?

“But what about you? Any crazy high school stories that my little sister never told me about while she was growing up?”

“Nope!” Twilight said with a small smirk on her face. “I was under the tutelage of Princess Celestia. I focused on my studies like a good student!” But her face softened a little and she shrugged, “However… knowing what I know now, it just might have been a little more interesting to have a few more friends to have made those stories with.”

He lifted his bottle up as if raising a toast to the sunset. “I could agree with that,” Shining said before taking a sip of his drink and eventually grimacing as he swallowed.

As much as she appreciated the thought of Applejack’s gift, it was starting to get obvious that this wasn’t for either of them. She double checked her book before today too, and it did say that wine or some other form of alcohol was a good idea for special occasions. The idea about adding a cautionary note to that chapter was already shelved in the back of her mind, but she guessed it couldn’t be too bad since it did result in a pretty memorable time in her past; a story that she hadn’t ever told her brother… or anyone in fact.

“Soooo…” Twilight said as casually as she could… which came out as awkward as she feared. She looked at Shining with a stiff smile as the pause went on long enough for him to stare back with a quizzical look as he took another sip. “What was your first time like?”

He nearly choked on his drink, coughing a little from a drop that suddenly went down the wrong hole. “W-what… ack… what makes you ask that?”

“Well you know,” Twilight shrugged as nonchalantly as she could. “I guess there’s just something about tonight that reminded me about it,” she continued as she glanced at the sun that was slowly dipping below the horizon, then back to her not even half empty bottle of cider. A warm glow on her face spread as she motioned to it. “There was some cider involved with mine.”

Shining’s shoulders relaxed a little after he finished looking surprised and started to breathe properly again. “Heh… well mine too. Actually, quite a lot now that I think about it. And it happened on a train too! Which, uh… wasn’t the place I was expecting it to happen.”

“Oh?” Twilight said as she rolled over a little closer to really listen in. They both stared at each other; Twilight’s eyebrows getting more and more curious as it was Shining’s turn to awkwardly smile.

“Ok, ok…” Shining said as he finally gave up the silent game of wits. “It all started like this.”

“Cadaaaaance!” I shouted out as tears streamed down my face, my hoarse voice matched only by the boombox above my head blasting Neigh With Me Forever.

“Go away, Shining Armor. I don’t want to speak with you!” Cadance said from her window above. “We’re done!” she shouted as the window slammed closed with her magic and the blinds pulled shut.

“Cadan-ce-ce-ce!” I tried to shout clearly, but the sadness in my throat just wouldn’t go away and wouldn’t let me speak clearly. The skies were cloudless, but if it was pouring instead, it would have been the perfect background to how I was feeling.

I felt a strong hoof on my shoulder. “Come on, you got to pick yourself up, there’s plenty more fish in the sea.” I couldn’t help but look at Buck Withers and tearfully nod as I turned off my boombox. He was captain of the polo team, still one of the most popular ponies in school, and as of tonight, my only friend. “I for one am glad you ditched those dweebs, and the princess too! After tonight, you’ll be getting so much flank you won’t even remember her. Or better yet! She’ll be crawling back to you when she realizes just how popular you’ve become!”

I couldn’t help but think on those words, looking back to Cadance’s house as the tears started flowing again. I threw my arms around Buck to cry into his shoulder.

“Yea… ok… yea…” he said before pushing me away with a hoof and handing me a bottle. “Just keep at these. Trust me, they’ll help.”

I took a sip and grimaced as the sweet but tart liquid hit my tongue: hard apple cider. On the second sip, a small warmth heated in my core on the way down. And by the third swig I was downing the drink like a thirsty pony in a desert who hadn’t had a drop in days.

“There you go!” Buck said with a heavy pat on my back, enough that I nearly choked on the drink. “You ready to have some fun tonight?”

I wiped my eyes to dry some of the tears. “Yea… Buck…”

“What was that?” he said with a sly smirk that was framed by his amazing cheekbones.

“Yea, Buck.”

“That’s not the voice of a real stallion. What! Did! You! Say!?”

“YEA, BUCK!” Shining yelled enough that his throat hurt, before shattering the empty glass bottle on the street below. “Whatever we’re doing tonight, I’m ready for it!”

“There we go!” Buck said as he shoved another bottle of cider into my chest. “See, you’re learning. With that attitude, I might even make a spot available on the polo team just for you, ain’t that right boys?” The rest of the polo team who was watching from a distance all raised their drinks and shouted back in agreement.

“Tonight will be a night that you deserve, Shining.”

“That… doesn’t really sound like your first time.” Twilight cut in from the story. “Well… maybe for the cider? Shining, when I asked you about your first time I wasn’t talking about drinking alcohol, I was talking about-“

“I know, I know,” Shining said as he raised his hooves defensively. “I’m not a big dummy, Twily. I know what you asked.”

“Ok, well that’s good,” Twilight said as she started to contemplate. “But, wait… you’re saying that you broke up with Cadance? Wasn’t she your first?”

Shining shook his head, “Actually, no. After that fight it was with someone else entirely.”

“W-what?!” Twilight said as she practically gasped. “But how? Why? You two were perfect for each other! What happened?”

Shining took a deep breath, and paused for a few moments as Twilight was sitting up intently. The Ponyville sky gave him something to look at as he thought, watching the beautiful display of reds, oranges, and yellows that were slowly fading to pinks and dark-purples now that the sun was hidden. “What about you, Twily?

Her face instantly turned into a blush as she rolled her eyes. “Fine, keep your secrets for now… I guess I’ll start at the beginning too.”

“There’s this party that my cousin’s going to tonight. He told his friends that it’s going to be amazing! No parents or anything!”

“Really?! That sounds great! I can’t wait until I grow up and can go to all of the supercool parties and do all of the supercool high school things!”

I flipped the page of my books as my classmates continued to drone on. It was an art in and of itself to be able to focus on the important things – like the history of the Saddle Arabian Empire – instead of unnecessary chatter. But it was also important to be able to pick out key words when they were talking, and listen when required.

Party and high school were two combinations of words that I had in my interests as of late. Not for the actual social activity, or the promise of a grade that would eventually come, but for the one need any filly my age was desperate to find when she couldn’t get it: proper research of unknown subject matters.

The lack of research done on older ponies… well… not old-old, but more teenager-old, was lackluster at best. Besides a few pamphlets or unreliable playground gossip, there weren’t any good and thick tomes on the subject of high school parties. While this wasn’t my preferred area of expertise, the obvious opportunity was presenting itself to further research in a specific field.

My ears perked up as they continued and I flipped another page.

“But still, it would be great if we could just sneak right in and none of them would be the wiser.”

“Moon Dancer? Lemon Hearts? Either of you in?”

I just heard a grumble and saw a few firm head shakes. No pony was willing to even entertain the idea, and they probably didn’t even realize the goldmine of research that could be done; it was time to make some of my own findings out in the wild.

“I could go,” I said as I bookmarked and closed my book.

“W-what?! Twilight?! You?!” I heard from the group after they all gasped and practically froze in shock.

I nodded a little. It was a simple enough of a task: get in, interview a few ponies, and make sure all my notes were in order; I’d have this report done by morning! “Yea, how hard can it be?”

“A-are you serious?” they asked, and with another nod of my head I was getting dragged from the cozy library to one of their nearby houses. All the way they were shouting chants of, “Makeover! We’ll help you fit right in! You only have one shot!”

It was already after school when we left, but by the time the whirlwind of products, clothes and glitter was finished, it was starting to get pretty late. I hadn’t seen a mirror until the end where they were all yelling for me to, “Look! See how pretty you are! Wonderful!”

It was like I was looking at an art project of a pony. My hair was shorter in some places and extended in others, thick painted hooves, dark eye shadow, and heavy amounts of lipstick. I had on a solid cyan wig and even fur highlights, plus a brand new cutie mark over my blank bottom from all the paint supplies we had lying around. Whatever that group of fillies could think of or imitate from hoarded magazine clippings, they did… or at least attempted to.

However, the high hooves I had on were the worst of it all; one hoofit higher above the ground than normal. It didn’t make it easy to walk without practically tripping over myself the entire time. I had a few hours of practice at the house, so by the time we actually left for the party I at least mastered the art of staying upright for a few minutes at a time.

“Here it is, girls,” Twinkleshine said as we arrived at the front gates of the property. However, with music playing so loud we could hear it from a few blocks away, she was really stating the obvious.

“Well, uh… good luck, Twilight!” the group said before turning tail and running away. “Tell us all about it!”

I stood there watching the dozens of ponies that I could see through the windows, all chatting and talking, and drinking stuff out of bottles and cups. I scribbled a few things down on the notepad I had with me, but there was only so much information I could gather by standing out here on the sidewalk. “Well… here goes nothing…”

The front door was already wide open as I cautiously trotted in. The girls said there was no way they would think anything was out of the ordinary, but it seemed like everypony was staring when I walked by.

“Whoa…” I heard called out in surprise from the crowd in my general direction. I could only gulp and nervously smile as I walked deeper in through the crowds.

Why wasn’t I back at home reading?

I sighed as I saw a group of average looking teens… research wasn’t going to happen on its own. “Excuse me…” I said into the group, but their conversations downed me out. “Hey, I would like to get your input on an interview I’m conducting! What are your thoughts on excessive social interactions?”

I went from group to group asking similar things, but getting basically no response, or one of them asking, “Hey, aren’t you a little young to be here?”

“N-nope! I’m a perfectly average high schooler, who’s just enjoying the older-pony gatherings as much as the rest of you!” I said when they would ask, “Heh… heh… not in filly school either! Just, uh… I’m a really short average teenager!”

Oh Celestia, talking was hard. If only they would have been open to having these questions submitted in essay format.

“Does anypony want to go somewhere quieter? Can somepony answer my-“ I tried to finish asking but tripped in my shoes and went tumbling down right into the greenest pony I have ever seen.

“And…?” Shining said expectantly after Twilight had paused for longer than normal. “And how old did you say you were?”

“Heh… in filly school…”

“Really, Twilight?” he said back with an arched brow, looking like some illusion had just been revealed to him.

“Well that green pony and I, just kind of, uh…”

“I don’t like him,” Shining said as he crossed his arms.

“What?!” Twilight said right back. “You don’t even know him. I literally just described his coat and mane.”

“Well, yes, but I can tell that he doesn’t sound like the right kind of guy to have been with my sister. He was, what, a high schooler?” Twilight only nodded as Shining continued. “See, he was probably just taking advantage of you. If I was there, that wouldn’t have happened.”

“But you weren’t,” Twilight said and it deflated Shining a bit. “Besides, it wasn’t bad… just… probably not the best time, looking back in hindsight. Probably shouldn’t have gone to the party alone either, now that we’re talking about it, since really… the whole party thing was pretty overwhelming for me at the time. It was kind of like being in a library full of unknown titles from a new, undiscovered wing. There was just so much going on, and you want to just pick them all up and study them… but you can’t! Or… at least not like a normal library…”

“W-what?”

Twilight blushed a little and sheepishly grinned. “Uh… well, the main point is I was looking for a subject to study, and had to get them away from their group. So with my personal research project needing to be done by my eager filly self, there wasn’t any way that I was going to pass up an opportunity to take some notes… but I just didn’t expect the applied anatomical study that was going to happen.”

“I still don’t like him,” he said again, causing another harsh groan from Twilight. “But… I guess if my little sister isn’t upset about it, then I’ll try not to be as well.”

“That’s the spirit!” Twilight said as she wiggled a little closer as if she was asking about something secretive. “But what about you? I at least told you how my foalhood lover and I met. How did you end up finding your first mare?”

Shining sighed a little as he looked out onto the dark sky. The stars were starting to peek out and the birds had been replaced by the soft chirping of crickets down below. “Well…”

After breaking down at Cadance’s house, Buck, his team, and I headed back to a party that was still going on to fill up on drinks and supplies for the rest of the night. Spearhead, who I later became friends with when I joined the royal guards, his family was out of town for his little brother's civil engineering competition; their estate was the perfect spot for that party. Normally, I wouldn’t even have gone to the party since it was my regular Ogres and Oubliettes night with my other friends, but Buck had helped cancel that for me.

After we were finished stocking up, we went all throughout town causing quite a bit of mayhem. Buck kept the ciders coming as we threw toilet paper on houses and trees, loaded mailboxes with confetti cans, and other things we egged each other into doing.

In the back of my head I still couldn’t forget about my other friends who I tormented earlier in the day: Poindexter should be able to get unstuck tonight… probably… and 8-bit and Gaffer. How long did it take to regrow eyebrows again? I sighed after playing back in my head when Cadance was yelling at me for betraying my friends.

With another heavy glug and another bottle passed my way, I was feeling that Buck was right: the pain I felt in my heart was starting to fade. What had been a thousand knives was now only a dull ache whenever my thoughts wandered back in that direction.

“Hic!” I hiccupped, “W-what next, Buck? B-back to the party?”

“No, not tonight, Shining!” he said as he put a hoof around my neck and forcefully squished my head against his chest in a bro-hug. “We got something special planned for the principal. Give his house a little more decoration, if you get what I mean?”

“U-uh… sure, Buck?”

“Good! Cause the paint’s already there waiting for us! Mr. Wrinklehooves isn’t going to know what hit him in the morning when he wakes up!”

It wasn’t far away to our principal’s house; it seems we had been heading there this entire chaos-filled night anyway. But it was getting a lot harder for all of us to walk; stumbling, crashing and tripping all the way over there.

True to his word, there were several neon-filled cans of paint and brushes stashed away in some nearby bushes. “You get that side, you go around the house, fly-boy you got the roof, and Shining… you get the front door,” Buck said with a devilish grin. “Everyone’s got that?”

We all nodded and chuckled amongst ourselves as we grabbed the neon pinks and greens and trotted over as quietly as our drunken hooves would carry us. Operation Watermelon was a go.

It hadn’t been long before all of us had crudely coated the walls with a layer of paint, but by the time we had to start painting higher up, we all had grabbed some of the ladders that had been hidden away prior too. I was just doing some finishing touches to the porch ceiling at the top of the ladder, before I felt the ladder suddenly get kicked right out from under me.

Buck laughed hard as the ladder was sent sailing right through the living room window, while I dropped like a rock onto the wooden porch.

“Buck, what did you-“ I started to say before a can of paint came falling down after me, landing right on my aching head. I could feel its contents spilling out, covering me head to hoof in neon-green.

The entire team was laughing hysterically and pointing when I finally removed the paint can off of my head. “Aw that sucks, Shining! You should really be more careful!”

“Hah… yea, you guys got me…” I said with a forced chuckle.

“No,” Buck said as their laughter stopped in an instant. “I don’t think you know just how bad we did get you. This is just the icing on the cake. Everyone in town’s going to wake up in the morning, with everything signed by you.” He said as he reached in his jacket and pulled out a small business card and flicked it on the ground at me; it had my face, cutie mark, and “Get Pranked” marked on each of them.

“Haha, later nerd!” he said as they all started to leave. “Hope you don’t go crying to your girlfriend. Oh wait! HAHAHAHAHA.”

The tears were welling back up, but the lights from inside the house and a shrill gasp from the principal’s wife was enough to get my legs to start working and run outta there as fast as I could. “Shining!” I heard angrily calling out behind me after a few moments, but I didn’t look back.

It was all a blur after that, I didn’t really know how many of those ciders Buck had given me, but it was enough that only bits and pieces of that night were left. But, I made it back to the party after that and continued drinking until the world was spinning even more.

And that’s when I met her.

“So that’s how you got grounded for three months?” Twilight asked with a small snort.

“Yea… it was a wild night of destruction that I caused. I’m not proud of it. Cadance was right for calling me out for being a bully like Buck. That wasn’t a great time, but as you know, we eventually made up. I just had to reconcile with my friends and let them all know how much of a dummy I had been.”

“Ok… and what about the mare? Who was she?”

“Well… I didn’t exactly get her name… but she was blue and sparkly I think. Definitely sparkly as I had glitter in my fur for weeks after.”

Twilight stared at him for a few moments longer to prod him to go on, but he just smiled and shrugged. She sighed as she drank the last of the bottle that she had been sipping all night. “Alright, fine…”

“Hey…” I said as I looked at the mysterious green stallion leaning above me.

“Hey…” he said right back with a raspy voice as he stared at me for a few moments, before reaching a hoof out to pick me up.

I grabbed my notebook that scattered to the floor before taking his hoof. Though, as big and sturdy as he looked, he almost fell over too when I tugged.

“W-whoa,” he said as we stumbled and tried to keep each other up. “S-sorry, I’m just a little… drank too much... I think…”

We plopped down on a nearby couch, with him practically falling into it. He smelt like cider, and another scent that reminded me of a new house. “That’s um, fine… it is good to stay hydrated,” I said as helpfully as I could, but looking in dismay at my notepad that had way too few notes on it for the time that I had been here. “Say… are you a regular party goer?”

“Who, me? Yeeaaaa,” he said with a wave of his hoof, before it went to his face like he was trying to drink from something. “That’s why they call me the, uh… party-goer extraordinaire.” He leaned over to whisper, “Level 23 party paladin.”

I wrote a few notes down as he talked, but he kept pretending to drink even more during all of this. I looked over and saw a few bottles in the ice filled bucket that others were grabbing from; specifically the ones with an apple on the side that looked most like the cider I smelled. I didn’t want him to run now that I finally had somepony say more than a few words to me, so with a quick light of my horn, I floated two of the bottles through the crowd and over to us. “H-here, you look like you’re thirsty.”

“Oh, thanks!” he said as he pressed his hoof to the cap and flicked it off. “Heh, I learned how to do that today… pretty neat!”

I looked at the bottle and pressed my own hoof to try, calculating the appropriate point to apply pressure to- “Ow!”

“Here... I can get it for you…” he said as he grabbed the bottle and flicked off the cap like the other one, while I sat there sucking the end of my sore hoof.

“Thanks!” I said as I eyed the bottle and took a gulp… right before immediately regretting it. “Bleh! Tastes like bad apples!” I said, cringing as the probable poison warmed my throat on the way down. This bottle of perfectly fine apple cider had spoiled!

“You get used to them after a while…” he said, punctuating that as he glugged a good portion of it down.

I couldn’t help but write some more of my findings as he continued, but there was so much more that needed to be done. “Say… if you don’t mind, would you like to go somewhere a little more private to, uh….” Interview? Study? The other ponies seemed indifferent to all of that when I asked earlier. “Talk… and uh… drink some more?”

“Ughh-ahh-umm,” he stammered as his eyes widened. Did I say something wrong?

“S-sure,” finally came out with a sheepish head nod. “B-but… I uh… don’t even know your name and uh… aren’t you a little small?”

“I’m…” I started before looking around the room, only finding some words when I looked at his fur, “C-Cloverleaf! Heh, yup! The name’s Cloverleaf, and I um…. I’m just a little small for my age. Totally belong here… and especially belong at the private place that we should go to.” I said, suggestively raising my notebook, “If you know what I mean.”

He let out an excited whinny as he grabbed his bottle and chugged the rest in one go. “Oh… I, hic… I know what you mean!” His grin was wide on his face as he put the empty bottle down.

“Excellent! Here… let’s go right now! And umm… you can have my drink too. You seem to love those things.” How he did I still wasn’t sure, but it seemed to be working.

With about as much grace as a pair of newborn deer on ice skates, we went upstairs to the quieter parts of the house. The first and second doors were locked, but the third he poked his head into what looked like two other ponies hugging each other in bed; quiet, but they looked too busy in each other’s company to want to be disturbed by an impromptu interview.

Following him the rest of the way from closet to occupied room, I couldn’t help but notice his stallion parts were starting to droop out. He seemed too excited and focused to have even noticed. It wasn’t like I hadn’t seen that particular boy part before from my brother or father, sometimes having that happen to them in the morning when getting ready. Just this time it was growing much more than I thought possible in such a short period of time.

“Here looks good!” he said as we hurried into one of the kid’s rooms.

At least I thought it was a kid’s bedroom with the posters on the walls, toys, and how the bed was shaped like the Canterlot Express locomotive that frequented the railway station. But this place was unoccupied, which was all that mattered for some quality interviewing!

I plopped myself down on the foot of the bed, as he did the same. “So… have you done anything like this before?” I said, hoping to ease him into it all.

“Y-yea!” he said almost automatically before sighing and shaking his head a few moments after. “A-actually, no… I haven’t done anything like this before. Wanted to plenty of times, but uh…”

Oh you poor thing, no one had ever interviewed you! “Don’t worry, I’ll take care of you and guide you through the whole process.” I mentally sorted through each of the proper stages of a formal interview: the pre-research stages were done and questions mentally ready. All was needed was to inform him of the purpose of the interview and proceed with the mental questionnaire.

“Now…” I started to say but instantly stopped when my eyes caught sight of his black stallion part somehow looking even bigger than it was before. It visibly throbbed, almost looking angry at existing as it defied gravity to point at his chin.

Nowhere in my preparations for tonight was I ready for something as unexpected as that. This… was almost as dried up of a research subject as high school parties were. Besides the few basic biology textbooks highlighting the key anatomical structures, there was no mention of this inflated condition.

“U-umm…” I finally mumbled after being stuck in thought for way too long. “C-can you just hold still for a moment?”

“S-sure,” he said, but my pen was already hard at work drawing a crude sketch of the towering appendage.

“O-ohh~” he let out suddenly as I pressed my hoof against it, running up the side of it before going back to mark a note on my drawing.

“3.6 hoofits big,” I stated matter of factly as I wrote it down, ensuring that this important data was kept after this encounter. Hopefully, this was within a normal range, but it was hard to say without more data points. However, instead of just the smell of cider and new house, there was a deeper scent that was starting to grow, one a lot muskier that just kind of smelt like pure stallion. “How are you feeling?”

“Great!” he said and I mentally let out a breath of relief now that I didn’t have to call for a doctor. “I… I love you so much for this, Candy!”

I titled my head at that name, but didn’t think about it too hard as he started to lean over closer, shutting his eyes and pursing his lips, aiming in the vague direction of my face.

“U-uhhh…” I could help but mutter. I heard about colts doing this on the playground, but never actually saw it happen in real life. What was I supposed to do? Ask him more questions? Push him away?

I moved forward and copied his facial expression, keeping my eyes opened before pecking him on the lips and pulling back immediately. My face heated with a blush; the first boy I’ve ever kissed! It wasn’t life changing, only a small bit of warmth in the instant and the scent of lingering cider, but it was something.

Scribbling some more notes that I just had to write down, the stallion kept leaning until his head was resting on my shoulder. “C-candy… maybe you could… put it in your mouth?” His hoof grabbed onto his length, shaking it around slightly.

What in the hay high school ponies were actually doing at these parties was getting more and more out there. But, besides the perfect specimen in front of her to study, something in the back of her mind was nudging her in that direction. “A-are you sure?”

He nodded back, “Y-yea.”

For the sake of research, I hesitantly gulped and leaned forward as well, right until I was beside the black tool in front of me. This seemed a lot bigger than the scaled versions in my textbooks. “Ahhhh,” I called out as I opened wide… wider… and carefully maneuvered my mouth around the tip, until it barely squeaked in once I was opened as wide as I could go. “Mmm-ike, iss?”

“O-ohh… o-ohh Candy~… just like that~'' His hoof found the back of my head and started to press down slightly, I went with it, feeling my tongue slide all over the bumps around his tip until it was almost too far in. His stallion scent was part of every breath that I took, almost tickling my nose with how delightfully strong it smelt. He shivered heartily as I pulled back, slurping the drool building up in my maw.

I kept up the bobbing motion he guided me into. I could feel his heart getting faster the longer this went on. From the corner of my eye I floated over my notebook, noting down every detail I could think of. But after a page and a half of notes, I couldn’t help but feel a little funny too.

I even let out a delighted moan around him; first to copy him, but the next came out on its own. My heart was starting to beat even harder in my chest, and there was a warmth down below that was growing. It almost felt concerning, yet seemed perfectly natural, like my body was reacting in a way that it instinctively knew.

As heretical as it seemed, I put my notebook down on top of a nearby dresser. Maybe I’d take the notes after the fact instead?

“I want to be in you so bad, Candy,” I heard him call out into my ear.

“Hmm?” I mumbled as I thought about those words. Wasn’t he technically inside me already? Where else could he go? My eyes suddenly widened as I remembered those biology book diagrams: a stallion and a mare, and the main difference between them. Like a round peg into a round hole.

Was that where he wanted it to go? My mind could help but notice the small details around my fillyhood the more that I thought about it: the ever growing warmth, the small tickle that was building, and the bit of dampness that was starting to get quite noticeable. Something wet sounded out below as a small piece of me almost jumped out from the lips of my fillyhood; the clitoris, if I remembered the labels correctly.

With a gasp I pulled off of him, and gazed at his length for a few moments longer. Judging by the wetness, not even a third of it had been able to fit in my mouth, yet thick lines of drool flowed like a river over the various bumps and ridges along him, right down to the large black orbs nestled between his legs.

“O-ok… that’s, uh… going inside me now?” I half asked and half stated as I stood up. Why I was doing this, I still wasn’t quite sure, but the exploration of this unknown field and the idea of how much of a report I’d be able to write after this was done made my fillyhood quiver and wink out again. A delighted shiver went down my spine.

Glancing at my abandoned notebook, I considered writing just a bit more, but the stallion fell on his back and wiggled onto a pillow. He was waiting.

Positioning myself as delicately as I could, it was still awkward standing over a pony twice my size or more. My tail flicked expectantly, feeling him below; even standing up at my full height, he was almost touching me with that tip.

I only had to bend down slightly, and… there it was. The broad tip was poking me right on my filly lips. It’s warmth radiating into me way more than it had any right to. “O-ok… h-here it goes…” I said, mostly to myself, but he certainly heard as well.

Pressing back just a little bit more, right where I felt the entrance was, it didn’t yield any results. Again I tried, pushing a little bit more and more, until it hurt ever so slightly. It was no use; like a round peg that was a few sizes too big for my round hole. “I… I don’t think I can get it to go… maybe, I’m not ready?”

“Oh… uhhh…” he said, as he paused, looking like he was using all the brainpower that he was able to muster for the few precious moments he could. Suddenly, an abrupt hiccup interrupted everything, “Oh! I can help you… t-turn around,”

Questioning his methods I reluctantly did so, awkwardly showing him my own filly bits closer than any other pony had ever seen them before. It was one thing for a pony to casually see them from afar, or at certain angles, it was another for them to be staring from so close that I could feel my tail touching the tops of their head. “Are you sure this…”

My voice trailed off as I felt his hooves grab upon my flanks, smudge my drawn-on cutie mark, and pull my rump down even closer to his face. “A-ahhh~!” I let out as a tongue reached out from below to lick broadly against my entire privates. I awkwardly squatted down to not completely sit on him, but that sudden sensation instantly made my legs feel like rubber.

But the licks didn’t stop at one.

“O-ohh… ohhh~” I started to moan out in earnest after a few of them hit in just the right way. Was this what he was feeling when I was bobbing on his stallion part? It had to have been! I peeked open my eyes for a moment, and saw the black beast bouncing slightly in the air below me, all alone down there. I carefully touched it with my hooves, angling it up before letting out another, “Ahh~ ahhh~ ahhh~” as my lips surrounded it once more.

I felt a deep moan reverberate right into me as he let out his own, now muffled sounds. His tongue licked almost everything of my filly bits every time, but every so often it was timed with that winking dot, sending a warm shudder down my entire body. It already had my legs feeling weak, but soon my rump dropped right down onto his face; it didn’t stop him in the slightest.

Instead, it made him dip deeper in, opening up my tunnel for the very first time as his tongue searched around and tickled me from within. “Mmmmm…” I let out in a long, drawn out moan right into his tip. He kept licking and I was starting to feel things I’ve never felt before until I was left a huffing mess, feeling so wet between my legs that I was scared I was going to slide right off the bed if I didn’t have him holding onto me.

I could feel something in my core slowly rising the longer this went on, building to some mysterious peak that it was picking up speed and eventually galloping towards. I felt like it was going to reach a whole new level of sensation that I had never experienced before. I had stopped bobbing my head, only to bask in this coming feeling. My head was only repeating, “I’m gonna, I’m gonna, I’m-.”

But somehow after what felt like forever in this heightened state of bliss, his mouth came off of me. Desperately, I pressed back even further to try and get his tongue to keep going and bring me over that mysterious edge, but I only squished against the underside of his chin.

“N-now… t-try now…” he said with a shaky breath.

He didn’t have to tell me twice. I tried to spin around as best as I could, but I could barely stand, and these high hooves weren’t helping at all. I grabbed the shoes and tossed them to the floor as quickly as I could. With the loss of height, I could feel it poking against me at the perfect height, I didn’t even need to bend down to have him pressed inside me.

This was it.

We were finally ready for the main event we had been feverously working towards. Only a few minutes ago, I had put all the pieces together for what we were about to do, and… I wanted to do this. I could feel it in my very being that I needed to do this. Almost like our union was foretold in some ancient prophecy from some writer long ago.

I felt his tip against me, and once it was lined up as best as it could be I sunk down. The wide tip still pressed against my entrance, resistance building up until again it felt like it wasn’t going to work, but miraculously the tip found purchase and dived far into me.

“Ahhh~ ahh~ ahh-oww~!” I panted hard and gritted my teeth a little, feeling my tunnel suddenly getting spread open for the first time. His rod imparted a blaze along me that I had never felt before, bringing with it both pleasure and pain. But the discomfort paled in comparison to the desire for more at this very moment. No, this was a burning heat that we were going to indulge in for all of time.

His hips pressed upwards and I felt him slide inside me further than I even thought possible. I read the books, but I didn’t actually imagine it to be like this. My tunnel was taut, desperately squeezing against the new intruder with all its might, but even with that I could swear I could see the girth of it though my belly when he pushed in deep.

I pressed my hooves onto his chest, following the rocking back and forth in tandem with him. It helped me hold on whenever it got intense, but that was too much for my cyan wig. It flopped off right off onto his face, only to be knocked aside with one quick motion.

His face furrowed as the pony ride picked up speed. I could feel that rising in my core rapidly coming back with a vengeance, threatening to launch right over the edge and fly as far as it could. I cried out as that feeling finally snapped inside me, sending a wave of endorphins the likes of which I never experienced before flooding through my head.

I let out a high pitched squeal before everything in me convulsed, and with it sent a warmth squirting out from my fillyhood, covering him and the blankets below. It left me gasping and with only enough recovery time to hear him grunt and thrust one last time as deep into me as he could. I felt another flood spurting inside me. His throbbing member pressed right up against some unknown barrier deep inside, blasting shot after shot of hot liquid.

We panted hard as we both were riding the afterglow that gently brought us back to normal. Though, even with the sudden calm, it took more than a few moments to register just what had happened. But before I could even say a word to him, and with him still deep inside me, I could already see his eyes had fallen closed and hear a snore starting.

I stayed a bit longer to clean the unexpected mess dripping out from me the entire time, but soon I left before it was too late to write up a completely different report to what I had planned.

“Whoa… that… I really wasn’t expecting you to go into that much detail.”

“Heh… thanks? I think?” Twilight said sheepishly as she grabbed the one empty bottle that she had drunk tonight. “Blame it on the cider?”

Shining chuckled hard. “Either you’re an incredible light weight, or… something else. But sure, let’s go with that. But, you two did it and he, um… finished like that?”

“You mean being filled to the brim with his fertile seed?” she said and Shining reflexively cringed at that, but nodded regardless. “Yea, he did, and it was kind of lucky it didn’t actually take for some reason. I certainly had no idea about contraceptive spells or anything of the sort, nor would I have wanted to have that conversation with Mom and Dad… or you, at that time.”

“Yea, that… would have surprised me, but I would have supported you regardless. You know that, Twily?”

She smiled and nodded, “I do.”

“Weird how he kept calling you Candy though. I do that all the time with Cadance, when we’re uh… you know…”

“I know, right? I actually remember saying my fake name Cloverleaf a few times, just to be sure, but after half a dozen times, I just went with it by that point. But… what about you?” she asked, as she stared at her brother, noticing that his little black stallion was drooping out from hiding. Honestly, she was kind of feeling a little warm after telling that part of the story too, but her arousal was a little easier to hide. “What happened after you finally met this mare?”

“Uh… well…” Shining said as he shifted a little uncomfortably. “Not much more than I already told you.”

“What?! You mean I let you know all the details of my first time and you can’t-“ She paused for a moment as she looked at his sheepish face. “Oh, you’re being serious.”

“Sorry, Twilight! Like I said, that night was a wild one and after I returned to the party a painted pony, I only remember a few of the details,” Shining said, but Twilight couldn’t help but notice a specific twitch from his member rising. “Like that lavender taste on my lips.”

“O-oh?”

“Or how we were on that train doing it when she had her hoof up in the air and said-“

“Choo choo?” Twilight muttered. Her eyes suddenly as wide as saucers as she stared at her brother with a half open mouth.

“Yea! How did you know? Honestly, I still have no idea how I ended up there or where we were even headed,” he said with a small chuckle, but after a few seconds of silence he looked over. “Twily, you alright?”

“Seriously?”

“Uh, yea? You’re acting kind of strange. I mean, besides the explicit play by play of your story.”

“Do you… know when your first time happened? Like exactly?”

He put a hoof to his chin and shrugged. “Well it was a long time ago… umm… about a few months after Cadance and I first started dating, so… in the spring some time, like, uhhh…”

“April 15th at 9:37 PM?”

“That… sounds about right! Yea!”

“O-oh…” Twilight said as she stared down at the roof intently for a few moments before looking at Shining, waiting for him to say more, but getting nothing as he gazed out to the stars that were now filling the sky. She wiggled a little closer until they were almost touching. “Do you think you’d ever do it again? You know, like if she was here right now?”

“Twily, I’m a happily married stallion,” he said before smirking over at her. “Buuuut, I think Cadance might be interested to know who my only other lover was. She’d probably orchestrate the whole night with just us three if that was a possibility. But whoever she was, she's probably far away from here, since I haven’t ever seen her since that night.”

Twilight snuggled against his arm and let out a delighted sigh.

“Are you still good, Twily? It’s not that cold, is it?”

“No, I’m fine. Just thinking that Cadance and I need to catch up sometime soon.”

Author's Note

Hope you enjoyed this fic that I was able to squeak in on the last day that it was due. I totally didn’t procrastinate on it for a few more weeks that I should have. Nope! Not me!

But this actually was heavily referenced to the official MLP comic Neigh Anything, as the timeline is around the spring after those events. I’d highly recommend grabbing a copy wherever pony comics are found nowadays and reading it.

If you liked the story, please let me know with a like and a comment below!