The Wonderful Misadventures of Pen and Candy

by Commander Shadowblade

Rating: teen
Tags: Other, Romance, Drama, Princess Cadance, Comedy, Self Insert, Princess Celestia, Sex, Human, Slice of Life
Length: 3015

In a world where two ponies meet by a chance of fate.

A love story for my love Candy:twilightsmile: Happy Valentines Day!

In a world where two ponies meet by a chance of fate. An amateur author from another world, trying to publish his latest story runs into a song writer trying to make a place for herself in the world. Even though Pen has fallen head over heels for her, he may have a bit of competition with the Princess of Love who doesn't mind sharing.

Published 2017-02-14 06:30:01 UTC
Last updated 2017-03-12 22:09:52 UTC

A Fateful Meeting

A Fateful Meeting

By: Pen Dragon

It had been nearly a year since I was brought into this magical world of Equestria and even though I wish the ponies would return me home. I’ve gotten used to being staying here, even if Pinkie Pie drops by and her pinkieness can be very annoying from time to time, but I’ve come to enjoy everyone's company, even Discord’s and he’s the reason why I’m here in the first place.

And that’s only the beginning of what has transpired over the year. Almost everyday I had received a love letter from some mare who had  a huge crush on me and even though the mares here are rather attractive. I personally wanted to meet someone who I can relate too and spend every second with, but no mare seemed to fit that description at all. True I have dated a few of them, but things got a little…Perverted I guess would be the word. Some of them would only go out with me because they want… Ugh I don’t even want to finish that sentence.

But the day when Cadance took me out to do shopping was the day that I met the most beautiful mare in all of Equestria. It all started at the Canterlot marketplace. Ponies were either trading baked goods or purchasing jewelry or something expensive. “Cadance? Tell me why I’m doing with you?”

“Because you're my best friend and Shining doesn’t like to do this stuff with me anymore.” She answered.

“Oh, yeah… Uh how are things with you two?” I asked, but with a deep sigh she turned to me with a saddened look.

“Not so well… Honestly I think I’m done with him… We don’t have that same spark as we did all those years ago. Still I’m glad that I get to spend some time away from the Crystal Empire.” She replied before smiling at me.

“Well I’m glad that you’re at least getting out… If things are really bad there then it’s best to stay away from him. Have your own personal space and try to date somepony else.” I replied, but when I was at the Crystal Empire Shining told me the exact same thing and let’s just say that he was already moving on with some other mare he met in the Empire and told me to keep it a secret. Most of you would probably think that’s a douche move but I always keep my promises and besides, from the way she was ogling me and the other stallions near her I’d say she was ready to move on as well.

“Yeah you’re right… Anyways when are you going to find that… Special mare in your life?” She asked with a coy smile while I rolled my eyes in response.

“When I meet her I’ll know… But until that happens I think I’ll just stick to being single. Besides I’m actually pretty happy with how things are.” I replied to the pink alicorn, but as made a sharp turn around the corner I was soon tackled to the ground by somepony. Music sheets and pencils fell all around us. My vision was blurry for a bit, but once it began to clear I stared back at the most beautiful blue eyes. A blue pegasus with a pink mane tied into a ponytail and wearing a dark blue hoodie stared back at me blushing.

I tried to respond by saying hello, but what came out was. “Uh buh, uh…”

She didn’t respond to me as she began to pick up her supplies while trying to suppress a giggle while also avoiding eye contact. It wasn’t until I heard Cadance snickering behind me that snapped me out of my daze and I began to help pick up her music sheets. “H-H-Here you go!”

“T-Thanks… Uh what’s your name?” She asked sheepishly while I was trying to figure out how to speak english because I apparently forgot how too. How sad is that?!

“Uh… I...Uh it’s… I can’t really remember right now?!” I said nervously, trying my best to not shut down while blushing like an idiot. She couldn’t help but giggle at my comment. Before I knew it Cadance stepped in.

“His name is Pen Dragon, but you can just call him Pen or my personal favorite… Penny!” She giggle as I gawked at her as my face began to turn cherry red.

“Cadance!”

“I think it’s cute… You can call me Candy.” She said, blushing. I couldn’t believe what I was hearing, she thought my nickname was cute and she didn’t even call it stupid or lame. Like girls in my world. I was staring at the most beautiful mare I have ever laid my eyes on, but they soon began to drift down to her flanks where I noticed a candy cutie mark. I immediately looked up blushing a lot.

“Pen you know it’s rude to stare at a girls flank~” Cadance said slyly as Candy began to blush as well.

“I-I wasn’t… staring at her flanks I… Was just curious about her… Cutie Mark is all?” I tried to sound convincing but Cadance knew me better than that since I’ve lived with her at the Crystal Empire for a year now and me staring at Candy’s flanks wasn’t a good first impression.

“Sure you were?~” One of these days Cadance I’m going to knock you out and mail you to the other side of the world.

“Uh… It’s alright, just don’t do it again!” She said glaring at me while blushing. I couldn’t help but nod in response. “Anyways… If you two would like… Would you mind coming with me to my studio? I could use some help carrying these song sheets?”

“So you’re a songwriter?” I asked.

“Yeah I am… Although I’m sorta stuck with some of the writing at the moment.” She replied, I didn’t know why but everything about her was just too cute, her mane, fur, eyes, everything was cute. And she was a songwriter.

“You know Pen is an accomplished author and I’m also an excellent singer. If you want we can always drop by and help you out if you want?” Cadance offered while the blue pegasus smiled in response.

“Sure thank you your highness and thank you Pen. I really appreciate this.” She said trotting up ahead while Cadance looked at me with a wink while sticking her tongue out.

“You better make a move before I do Pen. Although I don’t mind sharing her~” She said swaying her hips at me while I began to blush intensely.

“Celestia… give me strength.”

A Flirty Princess

A Flirty Princess

It didn’t take us long to find Candy’s studio and I had to say that it was rather impressive and I wondered how she managed to afford this? Heck I couldn’t even afford an apartment here in Equestria which is also sad, considering Cadance was the only one willing to take me in.

“This is a very nice place you have here Candy,” Cadance said, smiling at the mare as she blushed slightly, Candy soon turned to me and awaited my response as well.

“I-I really like your place Candy, it’s very nice.” I replied sheepishly, I didn’t know why I was acting so nervous. I went on dates with other girls before, but something about her is so different. I have this funny feeling in my stomach, not the bad kind, but the good kind where I feel fuzzy on the inside when I’m near her.

“Thank you Penny… It’s nice to know that some ponies actually like my place. Anyways are you two hungry? I can get you guys some cookies or… candy.” She said but just mentioning candy seemed to have put her in a daze. She must really like candy? My gaze soon turned towards Cadance who simply smirked as she blushed at the sight of Candy.

“You know Penny? I wouldn’t mind getting to know her a little better if you know what I mean~” She said with a seductive look as my face soon began to turn bright red at the very thought of what she meant. “Also you do have to admit she’s very cute?”

“Cadance! Don’t say that! She’s right there you know?” I said, but she seemed to be naming the types of candy like skittles, rock candy, chocolate etc… But I had to admit that she was so damn cute. Of course she was but she was also innocent and that was a good enough reason for me to try and keep Cadence away from her.  “Look I’ll admit it, but… we can’t just-”

Before I could finish I soon felt her wing wrap around me as she whispered into my ear. “Oh, I thought you said it was only me, but you said we~” I soon realized what she meant as she nibbled on my ear before heading to Candy’s side with a playful grin. I knew what she was up too and I had a feeling that somehow I was going to end up getting my ass kicked somehow.

“Cadance don’t you dare?!” I ran to her side to try and stop her but before I knew it, she had slapped Candy’s flank, snapping her out of her trance as the pink alicorn stepped to the side and guess who was still there guys?

“PEN!!! Your such a pervert!!!” She said, smacking me upside the head while Cadance grinned at me deviously. I swear I’m going to kill you Cadance when I get the chance.

“I-I didn’t do it!” I shouted only for Cadence to step in with a cheeky grin.

“Don’t worry about it Candy… I think he was only teasing you.” She said winking at me.

“I-I wasn’t! It was Cadance!” I yelled trying to convince Candy that I was innocent.

“Why would she slap my flank?” Candy asked, tilting her head to the side. I looked at Cadence who snickered at me. Sometimes I wondered if the universe hated me or something because this was just sad for me.

“Because she’s a pervert!” I shouted.

            “Penny! Me? A pervert?” Cadence asked. She’s mocking me, I know she is and it’s cruel.

            “Well… who ever did better not do it again!” Candy warned us and I don’t know why but I find that attitude attractive for some strange reason. Still Cadance just winked at the pegasus before turning back to me with a weird sultry look.

Before I could say anything there was a loud ringing coming from the other room. “That’s probably Twilight!” Candy said excitedly and hopped into the room. I was now alone with Cadence and boy do I have a lot to say to her.

“Cadence what the heck!” I shouted.

            “Whatever do you mean Penny?” She asked with a coy smile. “You and I both know that you wanted to do the same.”

“That’s not t-true…” She could only smirk at me as I tried to hide my blush. “Okay I thought about it, but I’d never do it though!”

“Well just so you know… She has some nice-” Before I could even let her finish that sentence I shoved my hoof in her mouth.

“Don’t even think about finishing that sentence Cadance. I’m not like that and aren’t you married?” I asked her as I tried to clear my head of all perverted thoughts.

“You already know that Shiny and I aren’t really together anymore and besides…” Before she could finish that sentence I soon felt a slap against my flank. “You have nice flanks too you know~”

“OW!” I yelped, blushing intensely, as I rubbed my behind as Candy soon came back with curiosity from hearing a strange sound.

“What was that sound?” She asked.

“It was nothing Candy… Nothing at all~” I could only blush when she said that.

‘Dear Celestia I don’t think I can take this anymore.’ Was all that I could think of because I had a feeling that Cadence is just getting started.

Lunch Date

Lunch Date

I couldn’t believe that Cadence was actually going through with this insane idea to hook the three of us up?! I could only hope that she doesn’t embarrass me in front of Candy and Twilight. Anyways, Candy had scheduled a lunch date with Twilight and asked if we could come along.

“So... Candy why do we need to see Twilight?” I only ask this because for some odd reason when we first met, she thought I was King Sombra. I mean honestly I look nothing like the guy, so I ended up dying my coat black and my mane white with black streaks, thanks to Cadence of course.

“Well I promised Twilight that we’d meet up today, but I don’t want to just abandon you guys. That’s super rude.” She said this as if it was the most common thing ever. She really was sweet and I couldn’t help but smile back at her.

“Alright I’ll try to be on my best behavior with her…” I said hesitantly as Candy tilted her head curiously.

“Why? Have you two met?” She asked.

“Yes we have… We’ve known each other for almost a year until…” I paused.

“Let’s just say that Penny had a fallout with Twilight two months ago and they aren’t on speaking terms.” Cadance answered as I remained silent, waiting for this sweet girl to reply.

“Oh, I didn’t know that… Uh, well I’m sure she’s going be very thrilled to see you Penny.” She said winking at me.

“Thrilled is one way to put it, but I guess it would be good to talk to her again after what happened.” I replied as we continued to make our way to some fancy restaurant that I have been to before, but for some reason Candy looked a little nervous.

“What’s wrong Candy?” Cadence beat me to asking her that.

“Oh, uh nothing.” She responded quickly, but we could tell that something was bothering her.

“If it’s too personal then we’ll drop it for now.” I said, earning a smile from the sweet pegasus while Cadance rolled her eyes at me as I gave her a sly grin. She wasn’t the only one who knows how to make a kind girl happy. As we went in I saw Twilight seating at a table with an unusual scowl.

“Uh hey Twily.” Candy laughed sheepishly. “I brought Cadance and Pen like you asked.”

“Why don’t you and Cadance talk for a bit while I have a private chat with Pen here.” She growled as both Cadence and Candy sat down.

‘Oh boy, today must be my birthday.’ I thought as I followed Twilight outside, glaring at one another. “Okay what do you want?”

“I just want to know if you plan to do anything funny with Candy?” She asked, but the two of us knew that wasn’t the case here, but I was going to let it slide and just go along with it.

“I don’t plan on doing anything to a sweet pegasus like her… Twilight you and I both know that isn’t what you wanted to ask me?” I retorted while she puffed out her cheeks in anger.

“You’re right, but I don’t want you anywhere near Candy after we have lunch! She’s mine and I won’t lose her like I…” She paused before heading back to the table rapidly.

“I know Twily, I know.” I said, taking a seat next to Candy who was beginning to blush for some odd reason.

“So how are you Twilight?” Cadance asked.

“I’m fine, I just wasn’t expecting you and Pen to be joining me and Candy on our lunch date.” Twilight said sheepishly before glaring at me again. I soon noticed that Candy was having a hard time choosing something on the menu.

“Urgh… Why couldn’t we have gone to Donut Joe’s? There’s nothing good here to eatttt!” She complained and laid her head down on the table.

“Here why don’t you let me help you~” Cadance said, leaning against Candy. “There is the Lava Cake here… I think you’ll love it~”

“That sounds like something that would just burn me…” She pouted as I tapped her shoulder.

“You do know that the ‘Lava’ part just means the melted chocolate on top of the cake right?” I asked, laughing a bit.

“Oooh… then I want that!” She practically jumped right out of her seat after hearing that. I couldn’t help but smile at her giddiness, but Twilight didn’t seem so happy about it.

“Candy could you please hold still for just a few minutes?” She asked while I just gave her this ludicrous look. Candy jutted her bottom lip out and pouted.

“Oh, come on Twilight! She’s just trying to have a good time… If I recall you were the same when we went out.” I teased as she began blush in anger at me while I just stuck my tongue out at her.

“So that’s how you two know each other! But your so… diffrent? And Twily said she never dated anyone.” Candy asked confused.

“Oh, really now~ Well of course she’d keep that a secret because she doesn’t want anypony here to know that she dated an alien!” After realizing what I just said, I covered my mouth while Twilight began to panic. Candy tilted her head in confusion.

“But… you're not an alien.” She said looking between me and Twilight.

“Well… It’s sorta a long story that may or may not involve Discord.” I said sheepishly while Twilight just went into a daze of depression muttering something that sounded like ‘My life is over’ or something like that.

“Yeah and what’s funny is that these two hit it off a few months ago… before breaking up.” Cadance said with a sheepish grin while Candy sat there in utter silence.

‘I scarred her didn’t I?’

“THAT’S SO COOL!!” She shouted in excitement, while the two princesses and myself gave her a confused look.