First Date

by Chelis

Rating: mature
Tags: Romance, Equestria Girls
Length: 3433

A first date with Sunset Shimmer

It started with a dance a few weeks ago. Now, I'm about to take Sunset Shimmer out for our very first date, which happens to be at the county fair.

If all goes well, I hope to know more about the girl I had been crushing on since freshman year.

key word is IF

Edited/Proofread by DustyPwny

Pre-read by Majin Syeekoh

Published 1970-01-01 00:00:00 UTC
Last updated 2015-05-07 18:40:02 UTC

First Date

I took a deep breath.

It's okay, I can do this.

I told that to myself over a hundred times up until then. The nervousness of it all was on par of murder.

A legitimate date with Sunset Shimmer. This is no dream, this is no prostitute dressed like her. This is the real deal. A real date!

I tried, and failed, to keep that couple of sentences out of my head, but no luck. It sent me on an emotional rollercoaster of fear, nervousness, and immense joy simultaneously.

What if I screw up? What if I say something I'm not supposed to? What if we run into one of her crazy exes again? Is dating her going to be some Scott Pilgrim bullshit?

It could have been, seeing how I had to punch out her last ex. That was a fun night to reminisce: Asking her to dance, hitting her said ex-boyfriend that led to a chase in our town, and we ended up having sex on top of my car. It was a memorable night. I had been hanging out with Sunset and her friends at lunch every day after the dance. They seem to like me, considering they haven't thrown me out of the table yet, and they were melting over how cute I was around Sunset, wishing they had a boy to act like that around them. Then again, it was just Rarity doing that, the rest would have preferred having me over Flash Sentry. Somehow we seldom ran into each other during class, but he seemed to stay away from me. It looked like he wanted to rip my head off just looking at me, but something was keeping him from doing so.

The dance was two weeks ago, and the second I heard about the county fair coming back, I knew I had to ask her to it. She didn't have to think twice. She also told me that she loved carnival food and would let me taste all the good ones, so much so that she told me not to eat at all that day. There won't be enough stomach for me if I did.

I had my best clothes on, ready to go. I grabbed my keys from my desk and went downstairs and out the door. As I walked down my driveway to my car, I had my phone out and sent a text to Sunset.

I'm on my way.

She responded in less than a second.

Oh hey! So look, come dressed in casual clothes and nothing fancy.

I stopped and looked at my clothes: a polo shirt and a pair of khaki slacks. Sunset sent another text.

It's taking you a while to respond, so I assume you did dress up.

I'm gonna be a few minutes late.

Thought so, lol.

* * *

The butterflies were painful on the drive to Sunset's house. Every foot felt like hours, and every stop sign seemed like centuries. I turned the corner to her block and, as if it were even possible, the butterflies became even more active. Coupled with Sunset's advice the day before, the butterflies and and my hunger were slowly eating away at my confidence.

As I stopped in front of her house, I reached into the back seat to pull out the bouquet of roses that I’d bought on the way here and sent her a text message telling her that I was outside.

I made the message in a couple of seconds, but it took me half a minute to get the courage to press the send button. I was hesitating, making sure everything was set and that I looked at least presentable.

It took a few minutes for her to exit the front door. She walked over to me with a smile on her face as I got out of the car, the bouquet behind my back.

"Hey!" She came up to give me a hug but was stopped by the roses blocking her path. "Aww, they're so beautiful! You shouldn't have!"

"Well… I -"

"No really, you shouldn't have. You didn't have to dress up or bring flowers. You already have a good impression," She said as she took my bouquet and gave me a kiss on the cheek. That kiss melted the butterflies away. It was a great relief to know that she probably had no intention of ending the date there. The bouquet was unceremoniously thrown to the back seat when she got in the car. "I don't know about you, but I can sure go for some carnival food that’s bad for your figure and your heart!”

"Deep fried anything?" I asked.

"You bet!"

* * *

The smell of both common and exotic types of foods was the first thing to invade my nostrils when we arrived at the fairgrounds. The second was the dirt that used to be part of the fair's parking lot now collecting all over my car, only a few hours after getting it washed.

So much for that.

There was a horde of people there, but there was enough space to not feel like you were bumping into everyone all the time. There were families with three, four, five or six children running around, and there were old couples, probably feeling like they were young again. There were groups of friends roaming around like a wolf pack, and there were young couples like us.

"So, want to get a burger?" Sunset asked.

"Sure."

"Let's get a Luther!"

"A what?"

The Luther Burger: You get a big ass hamburger, you take away the bun, and you replace the bread with two glazed donuts and add a side of waffle fries with a butter milkshake.

"I've been waiting all year for this!" Sunset said as she bit into her burger.

I was hesitant to take a bite, but when I did I felt like I was in heaven. The combination of the sweet bun and the burger and bacon was simply orgasmic. The waffle fries seemed out of place, mostly because I was not expecting to eat waffles outside of breakfast. The buttery milkshake was as close to buttery as handing out sticks of butter like popsicles.

The food was interesting, but I was more interested in the girl across from me.

"So how's stuff?"

"Stuff?" She asked, putting down her burger. She had a confused look on her face.

Fuck! Fuck! Abort! Abort!

"N-Nevermind."

Sunset reached across the table and placed her hand on top of mine.

"It's okay. You don't need to impress me."

We had shared smiles before she finished the last of her meal. I finished last, nearly succumbing to the food coma.

"Well, let's go play some games!" She said once I finished my fries.

"Sure! Let's go!"

The rest of the night was full of fun and wonder. We bought our tickets and went to town on the games and rides.

Our first stop was the "High Striker."

The game was simple: You take a big ass mallet, and you hit the platform that would launch a puck up a tube to the bell 15 feet high.

"I believe in you!" She screamed as she stood behind the small gate they had for people to watch.

I had given her a thumbs up before I took my whacks. The mallet was top heavy, so moving that thing or even lifting it was next to impossible. The first attempt had me missing the platform by a few inches. I looked to Sunset, expecting her to hide in embarrassment. She smiled back and gave me a friendly wave. I give it another try. The puck slid only a few feet, not even half way.

I'm going to embarrass myself in front of her! This one has to be it! I got to give this one all I got.

Something sparked inside of me. I took the mallet one more time and slammed down on the platform as hard I could. The puck screamed up the tube, and I anticipated the ring of the bell.

It never came.

In fact, it never even reached half way up the chute.

"Better luck next time, kid!" The vendor said, handing me a teddy bear keychain.

I walked back to Sunset with a defeated feeling.

"I tried?"

Sunset was grateful about it, putting the keychain with her set of keys.. "My ex would never even play the games. He knew he would fail."

I also failed at the milk bottle toss, with my pitches missing wide every time. Sunset asked to try the last one, so I gave her my last ball. I remembered that she was a pitcher for the high school softball team, so all she had to do was to give it an intense windmill pitch and down went the cans. Sunset got the giant teddy bear and gave it to me. We both laughed as we went back to the car to put our loot away.

"Yeah, I think that’s enough games for today," Sunset said with her cutest smile.

Oh god that smile!

As I handled the fact her smile stopped my heart for a good second, we walked back into the fair and decided that our stomachs were settled enough to try some of the more thrilling rides. Our first one was one we had a mutual liking for: bumper cars. We both got on different cars and teamed up on the others. Our coordination near flawless. One of us would slam on one side and the other would hit from the other side. We even high fived each other as we drove past each other.

Then there was the drop tower.

It was as tall as the Ferris Wheel, and every three minutes the screams from the riders could be heard throughout the park.

"So what do you look for in a guy?" I asked as we waited in line.

"Funny, Smart, kind, not a dick."

"So what every girl looks for?"

"Hey! U-um, yeah..."

We both giggled as our turn was up.

The ride going up to the top of the tower was boring, and lasted longer than the drop itself. But, the view was incredible.

"Is that a haunted house over there?" Sunset said, pointing to the dilapidated house.

"Holy shit, it is!"

"Want to go there next?" she asked.

I never got to answer. The drop came and I felt the sensation of my stomach pushing up. Sunset screamed in joy, I cried in fear. We raced to the haunted house ride right after we left, but we stopped along the way. We saw the sign and we knew we had to stop.

Python Kabobs

So we bought some for ourselves.

"This is not bad!" I said, realizing that it tasted like grilled chicken.

"You never tried reptile before? It all tastes like chicken for some reason."

We continued our walk to the haunted ride, chomping away of the bits of python with bell peppers on a stick.

The haunted house was in front of us by the time we had thrown the wooden sticks in the trashcan. Our first impression of the House was the uncanny haunted house music. We also realized that the house had a giant sign on it.

"3spoopy5me."

The haunted house was a track car going through the house. We were huddled together, thinking we would be literally scared shitless, but it had to be one of the cheesiest haunted rides we've seen. Some of the 'spooky scary skeletons' that were supposed to put shivers down our spines still had their price tags hanging from the eye sockets. The decorations were dreadfully bad, and the alien looked like a rejected prop from the ET movie.

"Aay lmao!" I screamed at the alien mannequin.

"Aay lmao!" Sunset joined in.

We walked out of the haunted ride laughing, not scared as shitless as we expected. We began to wander around the crowded fair, looking for something to do. Her hand next to me was open, alone. I wanted to hold her hand but was afraid of her rejecting me. I hesitated about going for it, but I did. Not only did she move her hand away, she began to run.

Holy Shit, Holy Shit, Holy Shit! I fucked up! I fucked up!

I began to panic, my eyes were beginning to water. I felt the air being sucked out of my lungs. Turned out, I was overreacting as always.

"They have it! They actually have it!" Sunset screamed out.

I rushed over to the food truck she was standing in front of. She had two golden brown balls on toothpicks.

"You have to try this!" She said, handing me one of the sticks.

It felt weird seeing a ball of something on a stick, but I took a quick nibble.

Wait a minute, is this-

"Deep Fried Kool-Aid, my favorite!"

It turned out they were samples. We both bought six each and they were topped with grape syrup and powdered sugar. We decided to wait until we got on the ferris wheel to eat them while overlooking the city. So, that’s where we went to next. Somehow, the ferris wheel was not the two seaters that I was accustomed to, but a six-seater that was basically observation decks.

"They don't make them as they used to," she said, climbing on board.

"I know right?"

We were lucky enough to not only get the top spot on the wheel, but we also had it during a shift change, turning a three-minute ride to a ten or more minute ride. We began to eat the kool aid balls, each one was better than the last. All of that while looking at the skyline of the city at night, like that one time a few weeks ago.

That night quickly came up again, and so did her ex.

"I never told you what happened on Monday, did I? Flash was waiting for you in front of the school. He yelled at me, asking where were you so he could kick your ass, so I put him in his place." Sunset said.

"Did you slap the taste out of his mouth?"

"Yep."

We both stifled a giggle as she rested her head on my shoulder.

"I just want to tell you this now. I know how you feel about me, but I don't think I'm ready to go back into the relationship field again."

My heart sank to my stomach, even after she wrapped her arms around me.

"But, when I'm ready, I already know who I want to be with."

The moment was surreal, and it was still sinking in.

So did she reject me? Am I on a waiting list? How long will it take? Why am I not just enjoying the fact she actually does like me?

We continued to look at the city, I was thinking of maybe taking her somewhere after this. The problem was that if I were to taste another hamburger ever again, it would not be as good as that burger.

There was a spark of white light in the distance, it flashed a couple of times and died.

"You saw that?" I asked.

"Yep."

We then saw the lights go out in every direction. Block upon block in the city disappeared in the tsunami of black, overwhelming the city skyline. It only lasted seconds, but it arrived at the fairgrounds, pitching the park powerless and trapping everyone in the Ferris wheel.

"Well, shit."

* * *

The only light was the glow of our phones and the moonlight. We were telling our families we were alright and telling our friends where we were because getting stuck on a Ferris wheel for your first date was something you don't go through every day.

Sunset even snapped a surprise selfie with me and posted it on her twitcher: "Stuck on the Ferris wheel, but at least it's with a cutie."

We moved from sitting on the seats to laying on the metal floor because, other than the stars, there really was nothing of interest to see.

She was laying her head on my chest, her hand wrapped around my body. We were waiting to get down because we wanted to actually walk and move around again.

"Excuse me!" The bull horn rang. We didn't stand, we just lifted our heads up to listen.

"Right now, we are getting the fire department out here to start getting people off the rides. The Ferris wheel has lowest priority because the mini-roller coaster peeps are on their side. So we are looking at an hour to an hour and a half wait."

"FUCK!" We both sighed defeatedly. We wanted to get off and continue the night.

"So much for getting noodles and going back to the overlook."

"Why would you want to go back?" I asked.

***

It turned out she didn't want noodles. I realized that when I was sitting on the seat of our carriage, with a bottomless Sunset sitting on my lap. My hard member vanished into her wet womanhood with an audible slick, and she began to tremble.

"Oh man," She said in relief.

My hands were on her hips, helping her up and down my shaft. Our juices turned my lap into a hot and sticky mess, but I didn’t care. The sensation of her tightness was just heavenly.

"I could get used to this." She said as she continued to slam her bottom onto my lap, each one was a sharp feeling of pleasure. That was soon followed by the thick and slimy condition of her pussy.

We kept going at it like that for minutes. The warm night made things hotter, which made us sweat a whole lot more. Seeing Sunset's sweaty back underneath the moonlight as it moved up and down was just as beautiful as the girl herself. Somehow between the heat, the small moans of Sunset, and the feeling of her womanhood, I somehow lost it.

I got off the bench, with my member still deep inside.

"Hey, what are you-"

She had her answer, as I shoved the top of her body against the opposite seat and began to slam my member deep into her. She moved her legs apart for more stability.

"That's more like it!" She screamed in pleasure. I continued to thrust inside of her while she began to pull her hair in pleasure. "Keep going!"

My right hand was on her waist, my left groping her breasts. She was like a drug. Every thrust made a loud slapping noise of our skin, and it made a bit of our juices drip to the floor of the carriage. It brought me closer to climax.

I continued to thrust as fast as I could, even if every thrust had the chance of blowing my load inside of her.

"I'm gonna-"

"Not inside."

I gave it three more thrusts, trying to savor the act of lust between us. It was bittersweet ejaculating onto the floor of the carriage. We were out of breath, Sunset collapsed on her knees, her face still on the cushions of the seats.

"Damn,” Sunset moaned.

***

We rested on one of the seats of the carriage, Sunset’s head resting on my chest like before, holding my hand.

"It's fun to do this, but maybe next time something less spontaneous?" I asked.

She giggled. "I know. Tell you what, next week I got something planned for the girls. What if you tag along? I'm sure the girls wouldn't mind if I end up going to your place afterwards."

"Sure, my parents won't be around next weekend."

The lights came on the carriage as soon as we sealed the deal with a kiss. We both groaned. We wanted to stay like that for a little while more. They began to unload the passengers one carriage at a time. When it was our time, we hurriedly left the carriage without a word because we were leaving a sticky surprise for the person who had to clean them that night.

"Should we get out of here before they figure out what we were doing in there?" I asked

"Of course. But not before we get some deep fried oreos for the road."

"So, what about a second date?" I asked as I held her hand. She stopped and gave me a deep, and sultry kiss, her tongue dancing with mine for only a few seconds.

"I'll have to think about it."