When The Heart Flutters

by Krystal Clearskies

Rating: mature
Tags: Anthro, Romance, Original Character, Porn, Fluttershy, Sex, Twilight Sparkle, My Little Pony: Friendship is Magic, Human
Length: 9289

A human has the date of his dreams, and some intimacy afterwards, with a certain yellow pegasus.

Jordan has lived in Equestria for a while now, and during his tenure there he's made some great friends. But one pony, he feels different about. One pony, he has a massive crush on.

Fluttershy.

One night, he gets to go on the date of his dreams with the apple of his eye. But what else will happen on this evening?

Tagged mature for clop scenes at the end. Anthro for humanized ponies with pony characteristics. I hope you enjoy, a lot of effort was pumped into this bad boy.

Published 2018-09-05 06:30:01 UTC
Last updated 2018-09-05 06:30:01 UTC

The Date

Author's Note

(Hello everyone. I would just like to explain before the story starts that this story contains an anthromorph version of MLP, sort of close to Equestria Girls but they retain more of their pony characteristics. They have cutie marks, pony ears, tails, etc. But they walk on two legs and are human-like. Keep that in mind, reading this story.

NOTE: This story contains pony on human and human on pony. It is sexual, but with a strong central plot. So if you’re looking for a quick yank, I can recommend some other stories for you to fire off some knuckle children to. If you don’t like stories of a sexual nature, please hit the back button on your browser.

Still here? Enjoy our feature presentation!)

The Date

I stood in front of the mirror one summer evening, trying my best to adjust my fancy bowtie as I stared at myself in the reflective glass. I closed my eyes for a few seconds, stopped moving my hands and took a very deep inhale, trying my best to cleanse my mind for the time being.

“Ok, calm down Jordan,” I tried to tell myself, thinking that if I spoke to myself it would work. “You’re only going on a date with Fluttershy, only the kindest, most gorgeous and overall amazing girl you have ever met in your life and... You’re not even close to her league! You don’t have a chance in hell at actually being with her!” In anger, I hit the mirror with my fist and held the aching knuckles in my other hand, letting out a sigh of pure sadness and deject.

“Fluttershy probably only said yes out of pity. I’m sure she feels bad for me, being the only human in Equestria. She probably doesn’t even like me. She’s just humoring me.” The only human bit was true. Six months ago, a freak accident ended with me being unexplainably transported to this land, with no clues as to how it happened or why. I arrived naked and cold, and without any clues where I was.

I almost didn’t survive my first hour of consciousness. I was in the Everfree Forest, and if not for that butter-yellow pegasus arriving and calming down those creatures...well, I probably would be a puddle of blood as we speak. Thank god himself for Fluttershy.

Ever since then I’ve had a massive crush on Fluttershy. And I don’t mean the typical “Oh wow, I’d like to get in her pants” deal. No, I LOVED that mare. I was intrigued by everything about her, and she inspired me to get out of bed every day. Every moment I spent with her was pure joy, and I cherished each outing to the spa she took me on, or every picnic she invited me to partake in. When I was with Fluttershy, I felt lighter than air.

I had always daydream-fantasised about taking her on a date, but I never got the cajones to ask her. Well, my roommate, Twilight Sparkle, caught wind of my affections, and deciding that she couldn’t in good conscience let her roommate and one of her best friends suffer from such things, told Fluttershy how I felt. Well, that pretty much forced my hand, and after some gentle emotional pushing from Rarity, who knew of my feelings, I finally got the courage to ask my crush out.

Tonight was the night. We were going to just enjoy a simple dinner, and maybe go stargazing tonight. Nothing too major. I liked it that way, I didn’t want a bunch of glamour and foolishness for our date and I knew Shy didn’t either.

That’s where the story comes back to the present, with me panicking like a fool in the mirror. Hearing the punch I had landed on the mirror and my sounds of pain as I held my fist in my hand, Twilight walked in and looked at me, shaking her head.

“Jordan…” She said softly before walking over to me, grabbing my fist in her magic so she could inspect it. She charged a basic healing spell into my hand, which healed any damage I had done to the skin or flesh underneath.

“Nervous?” My roommate and best friend asked me. I gave her a simple, silent nod and she looked at me with concern riddled on her face.

“I don’t know why you’re so scared, Jordan. I mean, I’m not an expert on love, I know. But you and Fluttershy have been so close! I know my best friends better than anypony, and I know you two are meant for each other!” This caused me to blush brightly pink, and I gulped heavily as I looked into Twilight’s gaze.

“I...I love Fluttershy, you know I do. But I’m no Mr. Suave, Twily. I’m just a typical run of the mill guy. Fluttershy is so perfect, she deserves her Prince Charming (Ponies had a version of that fairy tale, as it turned out). I’m just so far out of her league...I don’t know if I can even go on this date.” I said in pure despair.

“I mean, what if I majorly screw up this date. Will she even want to see me again? I can’t screw it up, I just can’t...” Twilight moved up to me and gave me a look, before hugging me tightly.

“Shh. I know you’re scared, but you’re not gonna screw anything up, trust me. Just remember, keep your cool, remain polite and respectful to her, and use lots of compliments. And none of the cheesy kind!” Twilight said, knowing me all too well.

“Oh c’mon, I really think she’d like ‘You make my heart flutter like one of the butterflies on your cutiemark!’” I chuckled a bit at the horrible little pun, but Twilight moved her hoof to her face and groaned.

“You really are a piece of work, my human friend. Now come on, you need to finish getting ready!” Twilight said in a strict tone, and used her magic to get my bowtie perfectly centered.

“There, perfect! Now you’re ready to go. You...you look devilishly handsome, by the way.” Twily said with a soft blush, which in turn caused me to blush. I looked at myself in the mirror again. I had on a pair of sleek slate colored slacks, a blue and white striped dress shirt with cufflinks, a belt, and some really dapper dress shoes. It might have been a bit much for a first date, but I really wanted to look nice and leave an impression on Fluttershy. Rarity made all the clothes for me, and they were comfortable on top of fashionably perfect. Besides, Rarity adored the opportunity to make such fine clothing for a member of a different species.

“Thanks Twily, for everything. You’ve done so much for me since I came to Equestria, I owe you so much.” I gave her another hug, which she gladly returned in full. She then grinned.

“Weeeeell, if you’re so sure you owe me, tomorrow you can help me organize the royal archives, since Spike will be in Canterlot on business tomorrow. Be here at 8am sharp!” She told me. I couldn’t tell if she was joking or not, but taking it as serious Inodded.

“Will do. I better get going Twily, I don’t want to keep her waiting. See you later!” With that, I ran out of the bathroom and to the front entrance of the castle, where a beautiful bouquet of roses lay. I grabbed them in my right hand, and quickly ran out the front door, determined not to be late.

I ran straight from the castle to the little bridge that went over the creek in front of her cottage. When I got to the bridge, I stopped and took a minute to breathe deeply, to calm my nerves. I closed my eyes and inhaled deeply through my nose, even smelling the roses once to let their aroma calm me.

After sufficiently calming down, I walked over the bridge and up the hill to the cottage. Taking one last second to calm myself, I extended out my wrist and knocked on the door, keeping the roses hidden behind my back so they would be a surprise.

For what felt like an eternity, nothing happened. I didn’t hear anything, nor did I get any indication that she was even home. Assuming the worst, I mentally prepared to walk back to the castle, but then at the last moment the door opened. What I saw before me made my world screech to an abrupt halt.

Fluttershy stood there, and my god, was she the stuff of the highest calibre dreams. She wore a gorgeous turquoise and light green dress, had on high heeled shoes, had dangling earrings in her ears, and had done some very light makeup to her face. She was so drop dead amazing...I felt so unworthy. She was fit for a prince!

“F...F...Fluttershy! D...dear Celestia you...you look amazing!” I said in pure amazement. Fluttershy blushed slightly and hid her face in her mane.

“You look handsome. Very handsome.” She finished with a little, adorable squeak. That made my heart melt. She was too cute.

“Th...thank you. I hope it’s not overkill but, um...I got these for you, from the flower sisters.” I then revealed the roses, causing Fluttershy to gasp and take them gladly into her hooves, inhaling to smell them.

“Oh my, they’re the most perfect roses I’ve ever seen! Thank you, so much!” She blushed again, which in turn caused me to blush, and turn to the side for a second before looking back at her with a big smile.

“Well, should we be going, mi’lady?” I asked as I offered my hand to her, for her and I to walk into town together. She smiled and gladly took my hand, again blushing cutely, and we both began to walk towards town.

As she and I walked, I just couldn’t help but think about life for a minute. Yes, I missed my home. And if I had the choice, I would have never come here. But I was stuck here, and I had to make the most of it. How lucky I was. I had amazing friends, a great job, a great home, and Iwas on a date with the most amazing girl, pony or human, I’d ever met. And on such a beautiful, warm summer night, I was so blessed. I truly was.

Fluttershy and I walked into town, hoof in hand, with her head kinda buried into my arm. The position was awkward at best, but the fact that Fluttershy did this showed that she had massive trust in me, to keep her safe. That feeling made me feel warm inside.

After some walking, she and I got to the restaurant in town I had somehow managed to get reservations for. I kinda had to sweet talk the owner, but it was so worth it. This place, the Hot Trotter Cafe, had the best food, period. Well, for ponies anyway. Being a human, pony diets didn’t do much for me other than provide nutrition.

I sometimes found myself salivating, at the thought of meat. Oh dear Celestia, what I would do for just a bite of a medium rare steak! But I had to suppress those urges, I never even hinted to my pony friends Iate meat. I think Twilight was able to deduce this, judging from my tooth structure compared to a pony’s, but she never acted alarmed. She trusted me. The same might not apply to other ponies such as Fluttershy, though. If Fluttershy ever became fearful of me...I would just lose too much to risk it.

It wasn’t easy adapting to the pony world. Finding foods ponies ate that I didn’t find disgusting was hard, mainly I stuck to oats and sweets. But it was also hard to get used to some other things, such as living in a land where wearing clothes was the taboo. In most situations I was looked down upon for wearing clothes. I tried explaining to the girls that back home being naked outside the home just wasn’t acceptable, but they just shrugged it off.

Another thing that was hard to get used to was thinking of ponies in a...romantic manner. Even though they had a few human characteristics such as walking on two hooves and speaking, they still had pony anatomy and fur and it felt strange. It became somewhat easier after Celestia and Luna had informed me, with very heavy hearts, there was no known magic strong enough to send me back home, not even theirs.

Once I learned that, it was easier to accept ponies as potential partners, once the depression left me and I was able to look at the world through clear eyes anyway. This was when I really started to feel my emotions towards Fluttershy, no pun intended, flutter, and I realized that those feelings were much stronger than I had meant for them to be. And that led to where we are now.

Anyway, so Fluttershy and I sat down in the waiting area, waiting for a waiter to wait us. I snuck a glance at Fluttershy, taking in how gorgeous she looked in the bright lights of the restaurant. She was the personification of beauty, I swear it.

After waiting, a pony wearing a black bow tie led us to a table. I may have paid extra for a corner table. And I may have paid extra extra for them to make it romantic. It wasn’t anything over the top, just a candle and a vase with flowers in it, and a nicer than normal cloth on the table.

I let Fluttershy have the booth seat (there was a booth seat and a chair, sharing the table), and the pony handed us two menus.

“Hello, thanks for dining with us this evening. My name is Notepad and I will be your server tonight. This evening we are doing half off all drinks for customer appreciation as well as half off all desserts. What would you like to drink?” I looked at the drink options for a second and sighed. What I would do for just a sip of a coke. Just one sip.

“I’ll take the…” I looked at the menu in surprise. Apparently, the server didn’t just mean regular drinks. He meant...alcohol! I didn’t know Equestria had alcohol, but boy was this a great discovery for me. Back home, I didn’t drink a ton, but every now and then a stiff drink made me feel alive. I browsed the menu of drinks and saw something called ‘The Chimera’, which was vodka, rum, and whisky blended with honey and garnished with spearmint. After thinking about it the name ‘The Chimera’ made sense, I knew about the mythical creature; three different animals/personalities in one body, kinda like the three different liquors in one drink. “I’ll take ‘The Chimera’, please.” I said as Notepad jotted it down. Fluttershy then chimed in that she would like the same.

I looked at Fluttershy in shock. Could it be she liked alcohol? Of course, I didn’t know Equestria had alcohol until moments ago, but the idea of Fluttershy enjoying it just seemed nigh unlikely.

“Fluttershy, do you drink often?” I asked her as Notepad left to fetch our drinks. Fluttershy blushed slightly and hid in her pink mane, which made her just freakin’ adorable.

“No...not often. But...well I figured if you were trying it, I could too.” She said shyly, and then looked away. I think my heart exploded in my chest. She was just so cute.

For quite a while, Fluttershy and I made small talk, with me talking about my job as Twilight’s secretary and her talking about a bird she nursed back to health last week. We also made some jokes, and when she was laughing I remembered what Twilight had told me.

“Hey, Fluttershy? I know this is going to sound sappy but...you look gorgeous. Like...too gorgeous for me.” This made her gasp and hide in her mane. Again, this looked freakin adorable.

“Oh my! I...I don’t know what to say. Th...thank you Jordan, so much.” She unhid her face for a moment, and I saw that she had a blush on her yellow cheek, an unmistakable shade of crimson pink. I blushed back at her, and right then Notepad arrived with our drinks.

“Two Chimeras, one for the gentle...man, and one for the lady.” Notepad said as he handed each of us a drink. The Chimera looked wicked, with the different drinks swirled around inside and the spearmint wick on top adding a very earthy aroma to it. I brought the glass to my lips and took a small, tentative sip. Immediately, my mouth was jolted with an electric bolt of flavor. The burn of the vodka, the sweet fire of the whiskey, and the sweet relief of the rum, not to mention the tasty relief of the honey, and the wick of spearmint to add a mysterious aftertaste to the mix.

The drink was delicious, however it was so strong it caused me to back away and let out a cough of discomfort. It wasn’t so much I was a lightweight as the strength of the beverage just took me by surprise. I let my cough out and cleared my throat a bit.

“Careful Fluttershy, that’s pretty darn strong.” I said as I wiped my lips with a napkin, looking at her. She gave me a tiny nod and took a sip about the size of mine. To my shock, she didn’t cough or anything, she just closed her eyes as the flavors took over her tongue and ran their course, then opened her eyes and smiled at me.

I was pretty dumbfounded, and was about to question her, but then Notepad returned with, you guessed it, a notepad in his hooves to take orders. “What would the lovely couple like for dinner tonight?” He asked with a smile. I gave Fluttershy a little hand signal, to tell her she could go first.

“I uh… I”ll take the salad and six cheese macaroni.” She smiled slightly as she gave Notepad her menu. I looked at the menu for a second before smiling.

“I’ll have two slices of the four cheese pizza and a side of the macaroni also.” I said as I also handed him my menu. He took both the menus and walked off to place the orders. One thing about ponies, believe it or not they LOVE cheese. It was almost as common as hay or oats honestly.

Notepad wrote our orders down onto his, well, notepad, and went to the kitchen to get the order going. That left me and Fluttershy alone once again. I grabbed the glass, and took another sip of the Chimera. Luckily, this sip didn’t catch me by surprise, and I was able to drink it without hassle. Fluttershy took my cue, and took a little sip of her drink as well. I let out a refreshed sound, and put my glass back on the table.

“So, Fluttershy, after this I was thinking, since it’ll be dark soon, we could go somewhere and maybe go see the stars? Would you be ok with that? I haven’t been here long but I do know of a spectacular place to see them.”

Fluttershy gave me a big, yet shy smile. “I, um...I love stargazing, I would love to go with you, Jordan.” I smiled back at her, and she and I Talked a bit more about certain things before she hit me with a question that stopped my world.

“Jordan? Do you want to go back to your world?” She asked me very quietly, as if she was somehow afraid of what she was asking. Her question made me think deeply for a few seconds, and I rubbed my chin as I thought deeply.

“Well...there’s actually no way for me to go back, Fluttershy. Twilight has found no possible ways for me to get back home, and even after asking the Princesses and sending a letter to Star Swirl, they haven’t been able to find anything. So, I can’t answer that.” I bit my lip a bit, hoping my answer would satisfy her curiosity.

“But...if you could go back, would you decide to?” She asked me, a bit louder and bolder this time, as if she really wanted to know due to her curiosity. I again rubbed my chin as I thought about how to answer, trying to find a way to put this.

“Yes and no. I’m kind of down the middle of it. Back home, life was bland, and living here in Equestria is fun and eventful. I haven’t had so much fun everyday since I was a little boy. But, at the same time, I do get lonely here. Don’t get me wrong, you and the other girls are all amazing friends, but I have no family anymore Fluttershy. Try to imagine if you were a giant distance away from home, let’s say Saddle Arabia, and had no way to contact your family. No Mr. or Mrs. Shy, no Zephyr Breeze, nothing. That’s where I am. I miss my family everyday, and everynight before bed they’re the last thing I think about. I have pictures of my parents, my brother and both sisters in my wallet. So there are pros and cons to both answers, staying or leaving.”

Fluttershy looked at me with big, melancholy eyes, as if what I had said really hit her. She looked like she was about to cry, probably out of sympathy for me. I sighed a bit and grabbed her hoof over the table, holding it in my hand.

“BUT...you are without a doubt the most amazing pers...pony I have ever met, Fluttershy. I felt something towards you from the very second we met, but I was afraid. Back home, I was no Prince Charming or anything, and I was a major introvert. I guess I just worried I would drive you away, and that was without a doubt my biggest fear. I never expected us to be going on this date, I would have been fine just remaining close friends, but I am so glad it happened. Because already, tonight has been so much fun. And I’m honored I get to share it with you.”

I didn’t expect a response from her. I had just said a LOT, and the massive blush encompassing her butter-yellow cheeks was proof that she was too surprised and taken aback to respond. It was fine, though, because right then Notepad walked towards our table with a tray full of food, and when he arrived he served us each of our food. I grabbed one of my slices of pizza and began to slowly nibble on it, hoping I hadn’t said too much to her, or frightened her in some way.

Luckily for me, she took a bite of her macaroni, and the seemingly delicious flavors seemed to distract her from what we had just spoken about. As she started to eat, I began to eat as well. My pizza was delicious, and combined with sparse sips of The Chimera to quench my thirst, it was all in all a great meal. But, I figured since she had asked me a pretty deep question, I could ask one that had been on my mind.

“Hey, Fluttershy? Is it okay if I ask a question?” I asked her, and after she gave me a gentle nod I began.

“How in the name of Celestia does such a smart, kind, gorgeous mare not have a boyfriend?” I asked pretty bluntly, which caused Flutters to let out an eep of surprise and her face to turn red with a blush.

“O...oh! I um...I guess I just never...met the right pony. Or human, as it were.” She took a deep breath before continuing. “I have had crushes, of course. But erm...they just were never meant to be. I’ve never been exactly sought after, you know?” She finished with yet another blush.

I nodded a bit and took a bite of my pizza. “Yeah, I guess I do know. Still, I feel like anypony in their right mind would chase you to the corners of the globe.” I chuckled as this again caused her to blush.

“You...you’re quite the suave talker. I...I enjoy it.” She admitted with a brushing of her hair with her hoof, and I chuckled again.

“I try. Fair warning though, if we get to be closer, I’m kind of a smart aleck. I make bad puns all the time. Just kinda my schtick, you know.”

Fluttershy smiled and took a sip of her Chimera, and then grinned at me. “Oh, I would love to drink more, but I’m afraid it might make my voice a little horse.” She let out an adorable giggle at her pun, and I chuckled back.

“Okay, that was bad, even for me. But, I give you points for creativity and adorableness.”

About half an hour later, Fluttershy and I had eaten our food and had just ordered dessert, two slices of pie. I had ordered a slice of coconut cream pie, and she ordered a slice of cherry pie (Ok these might be sexual innuendos, deal with it), which she told me was her favorite berry.

Notepad walked over and served both of us our slices of pie. I grabbed my fork and carefully cut into my slice, bringing the bit of food up to my mouth. As soon as I closed my lips around the fork, my world lit up.

This wasn’t a slice of pie, it was like heaven on a fork! I had never had anything so sweet, yet tart at the same time, and just well balanced and delicious. This place could easily pass as just a bakery instead of a full-blown restaurant. Looking over at Fluttershy, I guessed she was experiencing the same things as me, since her eyes gently closed and she made a happy sound as she ate her bite.

And so on and on this went, she and I enjoying our dessert like that. I probably shouldn’t have ordered a second slice after I ate my first that quickly, on top of my dinner, but it was just too delicious to not do so. After I finished my second slice, which this time around was campfire smores flavor (which was a graham cracker crust, marshmallow filling and chunks of chocolate in between), I felt FULL. I sat back in my chair and rubbed my belly, my eyes closing as I let the last few bits of the pie wash off of my taste buds.

I grabbed the glass of Chimera, and brought it to my lips. I sipped it slowly, since this would be the last sip of the delicious drink I had. Once it was gone, I saw Fluttershy grab her purse, I assume because she was going to pay. I stopped her and grabbed my wallet.

“Nothing doing, Fluttershy. Where I come from, the man pays the bill. Save your bits, ok?” I grabbed twenty bits from my wallet (it was awkward keeping gold coins in my wallet but Rarity made a custom attachment to it for that purpose), and I paid the bill once Notepad brought it to me, along with a very generous ten bit tip for him, since he was beyond hospitable.

I looked at Fluttershy and gave her a smile, standing up and putting my jacket on. “Ready to get going, Fluttershy? It’s about nine o’clock, and we need to get going if we’re going to make it to my stargazing spot before it gets too late.” She quickly stood up and I grabbed her hoof in my hand, exiting the restaurant with her, hoof in hand.

We had somehow spent two whole hours at the restaurant, and when we walked out of the front doors into the Equestrian night, it was now chilly, but not painfully so, and dark out. I led Fluttershy northward, in the direction one would take to get to Canterlot if they were to take the insanely long trek on foot.

We walked about a mile out of town that way, until I stopped and led her along a dirt road to the right which went up a hill. It was a hard climb, since the hill was kinda steep and it was hard to see, but after some rough hiking, we were there.

Fluttershy’s eyes popped wide and her jaw dropped when we got to the crest of the hill. The hill had a sweeping, 360 degree panoramic view of the surroundings, far away from any city light to pollute the night sky. It was out of the way, and natural and...gorgeous. I smiled and reached into my pack I brought with me and pulled out a blanket for us to lay on.

I laid the blanket on the grass and gently laid down with her. I was laying flat on my back, and she was laying her head down between my chest and stomach, in a very intimate position. She and I both gazed up into the heavens, and she gasped and pointed halfway between the horizon and the top of the sky.

“Look! The manticore! Oh and there’s the...draconequus? Wait...is that Discord?” She asked me, and after looking at the “constellation”, I swear that it...winked at me. I think. Was there something bad in that pie I ate?

She and I decided to just shrug that little escapade off, and we kept pointing out the different constellations, and laughing to ourselves. Finally, Fluttershy looked up at me and smiled.

“Jordan? I had an amazing time tonight. Thank you, every moment was so much fun.” She said, and I was about to tell her she was very welcome, when she did something which turned my world upside down.

Fluttershy, still laying down on my chest, grabbed the sides of my head with her hooves, and firmly pulled me into a firm, passionate kiss. My eyes popped open wide as our lips met together, but after a few seconds of her tongue probing my lips, I relented and closed my eyes, allowing her tongue the access is so desperately sought.

I let out a sudden moan into her mouth of surprise, as I felt her tongue snake into my own mouth, her tongue pinning my own organ against the roof of my mouth and licking all over, marking every piece of flesh as my own. I was shocked by her force and her sudden confidence but Celestia dammit if I was about to complain!

After about two minutes of her tongue licking around my mouth in our first ever shared kiss, Fluttershy pulled away and blushed. But she didn’t turn her head or anything, she just continued to gaze in my eyes as she had for the entire duration of the kiss. This was a sure sign that she trusted me, and her more confident side was more comfortable coming out of its shell with me.

I smiled at her and leaned down, planting a kiss onto her adorable little nose. “You’re very welcome, Fluttershy, and thanks for that. That was without a doubt the best kiss I have ever had.” I decided to do something bold, and I reached my hand down into her mane, using my nimble fingers to delicately stroke the soft fibers of her hair, making her coo gently in pleasure, giving her mane attention in no way anypony could. Hooves vs fingers and all.

She and I stayed like that for a long while, me stroking her mane with my fingers and her making happy sounds as I did so, with nothing around us but the chirping of crickets and the ribbeting of frogs. I let out a sigh when I heard the frogs.

“Hearing frogs ribbit makes me sad. My old man loved to collect frogs…” Fluttershy finally opened her eyes and looked up at me.

“What were your family members like, Jordan? I’d love to know.” She asked me, with that trademark begging look of hers. I wanted to refuse but I couldn’t say no to those eyes. I took a deep breath and sighed.

“Where to start...ok, I’ll begin with my mom. My mom is about 47 and she was never perfect, she struggled with alcoholism for most of my life, and she tended to over-react over things and panic easily, but she was a loving soul and supported me through thick and thin. I just...wish she hit the bottle less. It got really bad before I came here, she had just relapsed after eight months of sobriety and was hitting the bottle really hard.”

“And then there’s my dad. He’s pushing sixty right now. He’s always been my role model and my best buddy. Really, he wasn’t just my dad, he was my best friend. He and I did everything together. Watched sports, played basketball, and some other things from my world your world doesn’t have.”

“My brother...well he’s a long story. He’s not my actual brother. He has a different dad.” This made Fluttershy gasp and listen even more intently. “My mom had him when she was only seventeen. We may be only half-brothers, but he and I never once acted like we were different. My entire life, he was my brother, and I didn’t even find out he was my half-brother until I was 14. Before I left, he had just married his wife and had his second child, a baby boy named Kaden.” I sighed and took a deep breath, remembering my nephew brought a sad tear to my eye. “I didn’t leave my world on good terms with them...and it eats me up inside every day. Things were said that I’ll always regret…”

“The oldest of my sisters, well she was something. She and I grew up pretty close, but around the time I turned 16 she fell apart. She got divorced from her love, and she fell in with a really bad abusive man and moved far away. Almost died a few times due to drinking and drugs.” I sighed again. “I’m sorry, it’s just hard talking about her.”

“And then there’s the sister closest to my age. She and I were the closest of anybody except my dad. She was like a twin of me. She and I loved each other and supported each other through thick and thin. She...she was also like my best friend.”

“I was the baby of the family, so life was always interesting, growing up. I miss my family a lot, but remembering them always helps. I just wish I could see them one more time, and properly say goodbye.”

Fluttershy, when I looked down at her, had tears in her eyes. She had been crying due to my sad story. I felt bad she was crying on my behalf, so I very lovingly stroked her mane again, trying to make her as happy as I could.

“I’m so sorry Jordan...I can’t imagine what you’re going through. But...thank you for sharing that with me. In a way I...feel closer to you now, knowing more about you. I feel more comfortable around you.” To prove her point, she nuzzled against my hand as I stroked her mane, a strong sign of affection not commonly shared by ponies.

That made me feel really special, and this time, it was my turn to be bold. I leaned down towards Fluttershy’s face and planted my lips on hers. I didn’t try to push my tongue into her mouth like she had done to me, I was content with just rolling my lips along hers. Her lips were so silky and warm, I could have kept mine on hers for eternity.

Sadly, the kiss ended all too soon, and after giving my wrist watch a glance I gasped. “Oh my gosh, Fluttershy, we need to get home, it’s 11 o’clock already!” She gasped as well and quickly got up, and soon after putting the blanket back into my pack, she and I traveled down the dirt road, back the way we came towards her cottage through Ponyville.

The walk home was uneventful, she just nuzzled me as we walked together like she had done earlier. But it made me feel fuzzy, knowing once again, that she trusted me like this. I felt really special.

All too soon, we arrived at her cottage, and she opened the door, turning to face me.

“Thank you for the amazing date, Fluttershy. I had an amazing, amazing time. Ihope you sleep really well. Take care ok?” With that, I gave her a little bow, and I turned and started to walk the way I had come. Before I could get too far, however, Fluttershy called out to me.

“WAIT! J...Jordan, do you wanna come in? We...we could maybe share a cup of coffee?” She asked me innocently, giving me a very cute face, and who was Ito say no to such an offer? I walked back towards her front door and walked inside.

I had never actually been inside of her cottage before, and it was surely something. It was a hollowed out tree, and everything about it screamed Fluttershy. Everything was made out of all natural materials, and there were some critters sleeping in the living room. Fluttershy led me to the kitchen, where sure enough, she quickly brewed me a cup of coffee for me and served it to me.

I smiled at her gratefully, and sipped the warm liquid gently, adding cream and sugar as necessary. It was kinda awkward and silent for quite a few minutes before finally she broke the silence.

“Jordan...do you want to...oh, oh never mind.” She said miserably, the sound of defeat in her voice, as if her shier side had squashed the more confident side that was trying to show its face.

I reached over to her and grabbed her hoof, rubbing it reassuringly. “Fluttershy, whatever you want to ask me, I promise you it’s ok. Go ahead okay?” I smiled at her, trying to assure her, but instead of answering me she surprised me by lunging herself towards me, making me tip backwards in the chair and land on the floor flat on my back.

This surprised me, and I let out a yelp into her mouth, since her lips were now planted onto my own, and she was making out with me. I gasped and kisses her back, shocked at this turn of events, but I made no effort to resist her. In fact, I parted my lips for her, and like earlier, let her explore my mouth, her slick tongue licking against each inch of my mouth, as if it were trying to claim my mouth as its own property.

Finally though, after a while of this, I gently pushed her head backwards, breaking the kiss and panting desperately for much needed breath. I couldn’t help but notice she tasted of...daffodils? Daisies? Some yellow flower.

“Fluttershy?” I asked her, she letting out an embarrassed little squeak as I said her name, her yellow face stained crimson due to a ferocious blush on her cheeks.

Clearly, she was ashamed at the way she kinda just threw herself at me, but I in truth didn’t mind it! I was just taken by surprise. Not wanting her to feel bad, I grabbed her and quickly wrapped my arms around her neck, keeping her in place so she had to look at me.

“Fluttershy, I think I know what you were about to ask. And yes! My answer is absolutely yes.” Fluttershy gasped and shifted a bit on top of me, as if my answer had put her at ease. With that, her blush magnified, and she gazed deeply into my eyes.

“Well...s...should we go to m...my bedroom t...then?” She asked me with that adorable, shy stutter she had, and I smiled and used my strength to get us to a standing up position. I then caught Fluttershy bridal style and began walking out of the kitchen, up the flight of stairs, and into her bedroom down the hall.

Once I opened her door, I walked over towards her large wooden bed and lay her down on it very gently, not wanting to cause her harm. I then gave her a serious look.

“Fluttershy, are you sure you want to do this? You didn’t just ask because you think I wanted it? It’s not the best idea to do this on the first date, but if you really want this, we can go ahead.” I said as I reached out and gently pet her pink mane, making her let out a cute sound not unlike a little purr.

“I’m sure. Jordan…” She sat up and looked me dead into the eyes, her irises full of emotion. “I...I have never felt for anypony the way I feel for you. I’ve had feelings for you for a long time but I was afraid...afraid you wouldn’t like me, afraid what other ponies would think. But I don’t care anymore. I don’t care if Celestia herself disapproves! I...I love you Jordan, and I want this.”

Wow. That was...the most powerful thing anybody, or anypony, had ever said to me, ever. I didn’t know what to think or feel or say for a few seconds after she spoke, and I just blinked at her a few times, trying to process what she had just said. Had she really said those three words, too? It felt like I was hallucinating. It couldn’t be real. But it was! She had feelings for me...for a long while before this? Wow...just wow.

Not knowing what to say, I very carefully lay myself on top of Fluttershy and pushed my lips against hers, gently wiggling my tongue between her lips. I couldn't believe the warmth, it felt so amazing on my tongue, not to mention how slick and just...amazing it felt.

Fluttershy was blushing red as a tomato as I, this time, held control of the making out, with me laying on top of her and everything. I moaned out into her sweet, sweet mouth, enjoying the kiss even more than the last ones. This one felt more meaningful.

It took a lot of my will to break away from the kiss, so I could speak to her again, but finally I managed to pry my lips away from hers.

“Fluttershy...I want this too. I need this. I need you.” I said, my voice dipped with hints of lust and love. Fluttershy gave me the biggest, most loving smile she could muster. I took this as a go-ahead, and I slowly moved my body down from our bellies rubbing against each other, to my face being now between her legs.

I took a few breaths to steady myself, before grabbing the hem of her dress and very gently tugging it off of her frame. Once that was done, I carefully hooked my fingers into the waistband of her pink panties and slid them off, down her legs and over her feet, revealing to me in full, her sexy beautiful body.

Those words were understatements, really. Fluttershy’s body was perfect. Literally, I know she spent time modelling outfits across Equestria for Photo Finish, but she very well could have found work as a...more lucrative model as well. Her body on the front page of magazines would sell thousands if not millions of copies.

Her body was a mix between skinny and curvaceous. Her stomach slightly curved inward, but not by much, and her hips had a very seductive curvature to them. Not to mention, the gap between her thighs pulled me in like a fish on a lure. This was all highlighted by the yellow hint of her fur, which was like an incredible paint job to an already amazing car. It just added something extra.

And, the best part, was her beautiful wings. They were slightly erected underneath her, since she was sexually excited, and I could see the arteries just under the skin begin to throb and pump slightly. I smiled and reached my hand out to her right wing, worming my index fingers under the feathers to rub the bare skin of the delicate limb.

The response was immediate. Fluttershy immediately gave out a sharp gasp as my finger came in contact with the bare skin of her wing, and her hips bucked suddenly upward. Ponies’ hooves weren’t able to massage wings like human fingers could, so it was a very intense experience for Fluttershy, and I could see it in her face.

Giving her a reassuring smile, to convey to her that I would do everything in my power not to hurt her, I gently stroked the skin of her wing, moving my finger in slow and calculated strokes from left to right. Left to right. Left to right. Over and over again, I repeated this motion, making Fluttershy’s excitement level peak to near dangerous levels.

The bucking of her hips got even more fevered, and she was starting to moan more openly. I smiled and gently pushed my face forward, between her legs, where her sex was showing. Igently moved my lips to her beautifully perfect honeypot, and extended out my tongue, giving it a soft tentative lick.

This earned an even louder, sharper gasp from Fluttershy, and her face got very red. I don’t know why, but looking at her, I got the feeling something was wrong. I gently pulled my face away from her sex and looked her in the eyes.

“Fluttershy...are you a virgin?” I asked her, my voice full of concern. Fluttershy gave me a bit of a whimper, before she gave me a timid little nod.

I took a deep breath, thinking to myself. This was bad news. Iwas Fluttershy’s first time ever. Not only did I have to give her my all, but now I had to do everything in my power to make it as pleasurable and memorable for her as I possibly could. Ican do this, I told myself. I have to do it, for her. She deserves it and is counting on me.

I gently reached up, to where my right hand was at her breast, and gently brushed my fingertips against her nipple. After a few passes, this made her nipple very hard, and I gently took it between my thumb and finger, going between gentle squeezes and massages to give her pleasure, also at the same time pushing my lips back to her sex and giving it yet another tentative lick, this time directly on the slit instead of the outer folds.

This made Fluttershy openly moan, she was no longer attempting to hold back any noises. She was letting herself go to any and all sensations I gave to her. And, I told myself, I would give her everything that I could.

I used my hand which wasn’t rubbing her nipple to gently rub on her sex, right on the nub at the very top. This made her hips buck even harder than before. I grinned slightly and moved my lips forward, giving her love button a firm, very wet kiss. To reward my actions, her sex gushed out a bit of her excitement onto my chin.

I used my hand to wipe my chin, and then brought my hand to my mouth, tasting her juices with my tongue. Sweet, yet tangy.
I grinned as I looked up at Fluttershy, her flavour still tickling my taste buds.

I pushed my face forward again and this time used my tongue, pushing it directly onto her button, which immediately drew a sharp gasp of pleasure from her. Iused the muscles of my tongue to flick at her button, like a snake’s tongue might. This earned a few unrestrained moans of pleasure from Fluttershy, more and more arousal dripping from her silken depths.

When I figured Fluttershy was properly pleased and aroused, I pulled my head away from her sex and smiled, reaching up and gently stroking her wingtips.

“Fluttershy, are you ready to move on now? I want you...badly. Do you want me?” Fluttershy’s breaths were so ragged she couldn’t really respond to me, but she did give a fevered nod, meaning she was ready for more. I grinned up at her and repositioned myself so I was basically laying on top of her, careful not to crush her. Soon, her face and mine were mere centimeters apart, and I gently pushed my lips onto hers, beginning to make out with her deeply.

This kiss was so enthralling, I forgot for a few long minutes about moving forward. I could have spent all day wrestling tongues with her, swapping spit, our lips mingling in such a romantic manner. Slowly, I repositioned my body so my member was pressing against her sex. This was it. This was the moment of truth. I don’t think my heart has EVER been racing this much.

I leaned my head down, where my mouth was grazing her neck, and I let my tongue out, slowly lavishing her sensitive neck with little licks and lashes of my tongue. At the same time, when she was distracted by my tongue, I moved forward, slowly but steadily thrusting my hips forward, my member entering her quarter inch by quarter inch.

The reaction was immediate. Instantly, Fluttershy tensed up, her back arching underneath my body, her lips parted in an
“O” of pleasure, her mouth letting out lewd moans with every quarter inch I pressed onward inside her velvety depths. I was being deliberately slow, meaningfully careful. I wanted to do everything I could to make this the most pleasurable experience Fluttershy had ever had. It was her first time, after all.

Soon, I hit a block. My member stopped in its tracks, and immediately I knew what was happening. I had hit her hymen. This was really it now. This was do or die time, it was really about to happen. I felt my heart thump hard drum beats as I looked down at her, seeing I was only halfways inside of her. I reached up and gently pet the side of her head, wanting to prepare her for what I was about to do.

She nuzzled into my hand, and after a few moments to make sure she was completely relaxed, I pushed my lips onto her own and made out with her, trying to distract her as I suddenly slammed forward, breaking her hymen in as quick and painless a manner as I could possibly manage. It still hurt her of course, and she let out a loud cry into my mouth, he eyes clenching shut as the pain wracked her body. I felt insanely bad, and so with my hand I moved to her wings and very tenderly massaged them, wanting to make her feel as good as I could ever make her feel.

It seemed to be working, as soon I felt a tight contraction around my member, which could only mean one thing. Fluttershy was cumming, for me. On me. This realization made me shudder suddenly, my own member throbbing inside of her like an uncontrolled beast as I felt her clench on it. I moved my mouth to her ear and panted hot moans of pleasure into it.

“Fluttershy...you feel so good...so incredibly good. Are you okay? I’m not hurting you am I?” I asked, my voice tender and full of concern for my pony partner. She let out a cute noise, which I assumed was meant to say I wasn’t hurting her, and with as heartwarming a smile as I could manage to her, I continued.

I felt my pleasure build with every thrust, every pistoning of my hips into her pillowy bottom made my impending orgasm drift closer, and closer. I felt a fire in my loins, my member aching inside her. Suddenly, I felt my testicles contract close to my body, and I knew this was it.

“FLUTTERSHY!” I cried out from pleasure, and suddenly buried myself as deeply as I could within her, my member spasming violently inside her silky, warm, moist depths as it orgasmed. I threw my head back for a moment before leaning forward and kissing her, deeply. I felt her passage constrict on me, which meant she was cumming again, this time with me. I can’t relay to you the pleasure I felt at this moment.

It felt like my orgasm was a tsunami, a never ending torrent of love and pleasure. But finally, it did end, and as I came down from my orgasm, I gently pulled myself out of her and laid down next to her, not wanting to crush her.

Fluttershy was panting heavily, but after a few deep breaths to gather herself, she finally spoke.

“That...was everything I had ever hoped it would be. Thank you, so much Jordan, I can never thank you enough.”

I smiled at her and kissed her cheek affectionately, using what little strength I had recovered since my orgasm to stand up. That orgasm really sapped a lot of strength from me. I didn’t masturbate often, and that was the first time my lust was allowed a release in...quite a while. Months, maybe. It just wasn’t as big of a deal to me or my body as it might be to men my same age.

“We should probably shower, Fluttershy, I’m sure neither of us wants to sleep tonight all dirty.” I began to walk to the shower when I noticed she hadn’t gotten out of the bed.

Realizing she was perhaps too tired, I walked back over to her and scooped her up in my arms, bridal style, making her eep in surprise and cling onto me tightly. I walked into the bathroom, careful of her head and legs in the door frame, and set her down on the seat in her shower/tub combo, turning the water on and sitting down next to her.

I grabbed the bar of soap she had, which smelled awfully sweet, and began to scrub her down, starting with her shoulders, arms, hands, and bosom, moving down to her belly and back, then even further to her hips, legs and feet, and then finally, her intimate areas.

I made sure to clean as thoroughly as I could, wanting her to be fresh and clean when she went to bed. When I was satisfied with my work, I took the bar of soap and cleaned myself as best as I could. Ithink Shy wanted to clean me and return the favor but she was too tired at the moment. I sure as hell wasn’t about to complain after the good time she just showed me.

When I was satisfactorily cleaned, I turned the water off and scooped Shy up in my arms again, carrying her back to her bed and laying her down. When I made sure she was properly comfortable, I laid down next to her and kissed her cheek once again.

“Thank you for the best night ever Fluttershy. Is it okay if I sleep here?” I asked her, to which she gave a cute, sleepy nod. I reached to the lamp on the nightstand, flicked the switch, and before I knew it, sleep overtook me.

The last thought I had before I fell asleep, was this was the best day of my life. And I wouldn’t trade it for anything.