Zach's Best Day Ever

by Thunder Ice

Rating: mature
Tags: Twilight Sparkle, My Little Pony: Friendship is Magic, Romance, Original Character, Sex
Length: 4140

Zach Lanson spends Hearts and Hooves Day with his crush, Twilight Sparkle.

Zachary Lanson has lived in Ponyville for 2 years now, and today is Hearts and Hooves Day. And after being alone for the previous one, he decides to spend this one with his longtime crush, Twilight Sparkle.

Alright, I know everyone hates the story because it was heavily rushed. Truth is, I promised a friend I would make the story months before, and months later, I didn't even start it. After that, I decided to stop slacking off and continue.

This story contains a sex scene in chapter 2, an extended remake of chapter 1. Chapter 1 might eventually be deleted, leaving 2 as the main chapter.

The story was intended to be posted on Valentine's Day, but was a day late. Better (terribly) late than never.

Published 2013-02-15 12:20:02 UTC
Last updated 2013-04-02 01:25:44 UTC

Sex

Zachary Lanson was not originally your typical 15 year old boy. In fact, he wasn't actually a boy. Well, not anymore, at least. Well, before I get into the story, let me tell you a little bit of a backstory of Zach.

Zach was an ordinary child. His parents loved him a lot, and he loved them back. But one day, his life changed forever. When he was only 10 years old, a horrific car crash took his parents from him. He was then sent under the care of the manager of an orphanage. But this manager was...well, a bit of a bitch. She forced Zach to do whatever she told him to.

This went on for 5 years, until Zach was 15 years old...then everything changed. Zach somehow ended up in the magical land of Equestria, just before the Summer Sun Celebration. On arrival, he met Twilight Sparkle, and eventually, he helped her in defeating Nightmare Moon, who returned to Equestria after she was banished to the moon for 1,000 years.

After that, Zach had gained the Elements of Harmony as his new best friends. He surely enjoyed this life much better than the life at the orphanage.

Soon enough, however, Zach develops a secret crush on Twilight, and hasn't told her, but like everything else, it doesn't last forever...

It was another typical sunny day in Ponyville. Being a weekend, children played around outside. Ponies hung around and socialized around town, complimenting or greeting one another. The sun had shone high in the sky. Due to the weather patrol's schedule change/vacation, what was going to be a rainy day turned out to be one of the sunniest days in Equestrian history.

Zachary Lanson sat in a chair, head on hooves, looking out the window of the Golden Oaks Library, either watching an occasional couple walk by, or watching a butterfly rest on the window pane, just before taking off.

Usually, Zach would be occasionally happy and cheery most days. However, this day, none of that shows in his face, stricken with a mixture of boredom and sadness.

Today wasn't just like any other day. Today was Hearts and Hooves Day. According to Zach, the Equestrian equivalent of Valentine's Day. But just because it had a different name, it didn't mean it wasn't the same. There's the occasional giving chocolates and flowers, the blooming love, the kissing and snout rubbing...okay, maybe not snout rubbing, but still, it's the same.

Zach didn't hate Hearts and Hooves Day. He liked it. A lot. It gave him time to hang out with his friends and give them some memorable gifts. He was mostly cheery during Hearts and Hooves, always smiling to his friends when they thanked him, grinning back to a friendly Ponyville citizen. You know, how humans should act.

But there was one thing that always made him frown at the end of every Hearts and Hooves Day...Twilight Sparkle.

No, he didn't hate her. He didn't hate her at all. He liked her. No, "liked" isn't a good word. He loved her. When Zach first arrived in the technicolor ponified world, him and Twilight hated each other's guts. However, that hate didn't last very long - like...a few hours - when Twilight ended up hitting some of Zach's rather sensitive nerves. After that, their friendship began.

Skipping the whole Nightmare Moon scene - we obviously know how that played out - Zach had been given a chance to go back to Earth. But something in his mind told him that this was his home now, not that horrible orphanage on that horrible planet. Making the correct choice, Zach stayed in the land of Equestria.

That was just 3 years ago, or getting close to it. Zach arrived in October of 2010. Looking at the nearby calender on the wall, Zach could see that it was now February of 2013. First arriving in the world, Zach was 15 years old in human years. His birthday being in January, Zach was now 18. He didn't research much about age comparisons between humans and horses back on Earth, but Zach could tell he was old enough by the sheer deepness of his voice.

But enough about his vocal chords. Back onto the subject about Twilight.

"Hey."

Or not.

The mysterious voice that spoke behind him was not actually mysterious. Turning around, he already knew that it was non other than one of Equestria's heroes, and the girl of his dreams. Twilight Sparkle, carrying a few backs on her back and around her neck.

...Yeah, I didn't need to tell you who, but screw it.

"U-Uh, hey!" Zach said, stuttering at the sudden thought interruption. "I-I didn't know you were back so soon."

Actually, he didn't even know that she left. It was often that she'd slip out and he wouldn't even notice, not even if she walked right by a window he looked out. She noticed this numerous times, and she would always giggle when he had a surprised look on his face.

"Um...what were you doing?"

"Just getting a few Hearts and Hooves gifts for the girls. Also...Don't tell him, but I got Spike quite the jewel for this year."

After a second, Twilight reached into one of the bags around her neck and pulled out what seemed to be a large heart-shaped diamond. It seemed to be much larger than the one Spike had given Rarity two years back, the same exact year Spike became so greedy that he became Godzilla and nearly caused destruction to an entire town.

Good times, Zach thinks to himself.

"Where'd you get that?" He asks her.

"Rarity gave it to me. She never told me where she got it, but let's just say she owed me one," Twilight replies, giggling. Turning around, Twilight headed over to the door that led to her bedroom, giving Zach quite a few of her flank. It caused him to blush slightly, along with his wings suddenly springing opening and stiffening.

Once they stopped kissing, Zach began to kiss Twilight's neck, causing her to purr slightly like a cat and giggle at the tickling sensation. Once Zach was done with her neck, he moved downward to her chest, causing Twilight to moan slightly, while still giggling at the ticklish feeling. To Twilight, it felt tingly. It became impossible for her to stay still. She squirmed as he progressed.

Eventually, Zach moved further down to her stomach. Suddenly, Twilight burst into laughter, but tried not to be too loud. Twilight completely forgot the fact that her stomach was the most ticklish of her body. She covered her mouth with her hooves, trying to suppress her giggles. She squirmed frantically on the blanket.

Zach, however, still continued, even while Twilight was doing what she was doing. It made him smile, knowing she was enjoying the moment so far. After a few minutes of peppering Twilight's stomach with kisses, he moved lower until he reached his main prize: Twilight's marehood.

Placing his hooves on both sides of Twilight's pelvis, causing her to moan slightly at the feeling, Zach took in the sweet aroma that came from Twilight's marehood. It smelled slightly familiar, and that familiar smell made him want to smell it more.

After a moment of taking in the aroma, he placed his tongue gently on Twilight's marehood, earning a slight gasp from her, then a moan shortly after. He then ran his tongue up and down her marehood slowly, causing one of her hind legs to twitch. As he did so, he took in the delicious taste of her pussy. After a few seconds, he figured out the taste.

Grape.

Zach's favorite flavor was always grape. He'd have grape juice in the mornings before he came to Equestria, and he still did so now. He even altered the taste of some apples so they tasted like grapes. He didn't hate apples. In fact, he loved apples. Sometimes, he can be curious of some things.

"Z-Z-Zach..." Twilight moaned.

Just hearing how she said his name was enough for Zach to go deeper. After a few moments of just licking, he finally began to insert his tongue as deep as he could into her marehood, licking around. This earned louder and longer moans from Twilight, who was squirming around and shaking.

Pretty soon, Twilight's moans started to become quiet screams of pleasure. Her hooves clenched the blanket beneath her, her eyes shut tight, she twitched. Zach knew what was to come next. - get it?

"Z-Zach....I ca-...I-hah! I....I....I'm...!"

Suddenly, Twilight became awfully still. She became as still as a statue. As she froze, she gasped, then whimpered for a few moments, her mouth quivering. As that occured, Zach suddenly felt his face covered with liquid. Zach already knew what was happening. Twilight was having an orgasm. It didn't seem that hard to notice, anyway. Sometimes, back when Zach was on Earth, as he read some books on sexual intercourse, Zach read that an orgasm is the most powerful sensation in a female. It would cause women's legs to twitch, their voices to shake and let out a whimper, and much more. Twilight did just that. Her hindlegs twitched uncontrollably, and she whimpered. Just hearing those whimpers - knowing they were of pleasure - seemed to turn on Zach more than he already was.

Once Twilight came down from her orgasm, she slowly and gently got back up from the ground. That was when she blushed harder than she already had been. Zach wasn't sure what she was looking at, but when he looked down, that's when he started to blush as well, out of slight, but odd, embarrassment.

"U-Uh...wow. It's so...big," Twilight said slowly, having slight trouble finding the correct word for Zach's stallionhood.

"Y-Yeah. Hehe..." Zach replied to her, chuckling awkwardly.

"Am I s-supposed to...s-suck it?" Twilight stuttered for only a second, still shaky from the orgasm. Even though she was one of the smartest ponies in Equestria, Twilight never exactly had time to research sexual intercourse. She wasn't sure what to do to the male, or how to perform sexual acts on the male. She didn't even know about the sex acts performed on a mare, such as herself.

"Yeah," Zach replied.

"Oh. Alright then." Slowly, Twilight crawled only a few hoofs to Zach before her face was right in front of his stallionhood, slowly pulsating and twitching, begging for attention.

"Uh...You can lick it first if you want," Zach said, blushing as he saw the mare before him staring at his shaft. Said before, Twilight never had the time to read books about sex, so she was completely new to the many acts you could perform on a stallion's penis. Hearing what Zach said to her, licking was one of them.

Listening to Zach's words, Twilight slowly held her tongue out. She then placed it not on the top, but at the bottom of the shaft. A slight but quiet moan left Zach's mouth. Twilight then slowly moved her tongue up the shaft until it reached the top, causing a much louder moan to escape from Zach.

"What's wrong? I didn't hurt you, did I?" Twilight asked, worried and unknown to the pleasure Zach felt.

"N-No. I'm fine. K-Keep going, Twi," Zach replied to her, smiling to let her know he was okay. Taking his words into consideration, she kept going with her previous act, and started at the bottom of the shaft again, licking all the way to the top like before. Zach moaned again and smiled. Seeing this made Twilight know this felt good for him.

She went back down to the bottom, and licked back up. Then down, then up. She continued this for as little as two minutes before Zach stopped her.

"There's another w-way to do this t-too," he said, stuttering as the pleasure still flowed through him.

Twilight was eager to know what the 'other way' was. Then she remembered what she asked before. She asked if she had to suck it, and Zach said 'yes'.

Without hesitation, Twilight moved her mouth up back to the top, and she began to open it. The shaft wasn't very large, so she wouldn't have much trouble getting it in her mouth. However, before she put it in, she slowly breathed on it for a couple seconds, causing Zach to moan slightly, feeling her hot breath raining down on his shaft.

Finally, after a bit of teasing, Twilight finally inserted the slightly long shaft into her mouth, almost touching down to the base.

"A-Aah...T...Twilight..." Zach finally moaned her name, causing Twilight to continue her action. Slowly, she lifted her head up, causing the shaft to just exit her mouth, before she slid it back in. She had slight trouble breathing when it was fully in, but learning and making Zach feel good was definitely worth it.

Slowly, she increased her speed, lifting her head to the tip, then lowering it back down much faster than before. By now, it was much easier to do so with the saliva building up on the shaft as she continued. She continued this process for a mere 5 minutes, with Zach moaning and grunting most of the time.

"T...Twi..." Zach moaned, making Twilight go even faster.

"S...Stop..."

This caused Twilight to stop immediately. She looked up at Zach with sparkly eyes, wondering if she did something wrong. She slowly lifted her head, sliding the shaft out of her mouth.

"Aren't you gonna...orgasm?" Twilight asked, blushing.

"Let's s-save that f-for last," he replied, stuttering from the coursing pleasure.

Twilight wasn't exactly sure what he meant. Save his orgasm for what?

"L-Lay down," he said to her, and still eager, she laid down like he told her.

Once she was laying down on the blanket, Zach slowly crawled over her. She wasn't sure what he was doing...until she looked down. Then she noticed something. One night, she had time to read at least one page of one of the books, and that very page said something about penetration. She didn't read much, but she knew what was going to happen next.

"Are you ready?" Zach asked her, which brought her out of her slight trance.

"U-Um...I..." Twilight wasn't sure how to respond for a moment. She wasn't sure if she was ready enough for this. Sure, before was fine, but she wasn't sure what would happen if she went through. She was completely new to sex.

"Will it hurt?" She asked, sounding a little like a young filly.

"Just a little. Not much, I promise you," Zach replied, smiling. "If it hurts too much, we can always stop, you know."

Twilight pondered a little more on the thought for a few more moments. Finally, she came to a conclusion.

"Okay."

"Are you sure?"

Twilight then slowly lifted her head up until it was just centimeters from Zach's face.

"I want you inside me."

This surprised Zach only a little. Her character had changed throughout the past...what, 20 minutes since they began their little event? She was a bit shy, but eager, then she was just eager to learn, now she's full on sexual. Well not full on sexual, but still sexual.

"Alright then."

Slowly and gently, Zach began to push his stallionhood into Twilight's marehood. Pleasure instantly flowed through his body. It felt so...warm. But then he stopped quickly. This confused Twilight for only a split second, before she began to feel slight pain. She didn't know what was going on.

'This must've been the pain he was talking about,' she thought.

Zach, however, knew why. He most likely reached Twilight's hymen, which indicated instantly that she was, in fact, a virgin. He looked down to Twilight and notice slight discomfort/pain on her face.

"Do you want me to keep going?" He asked worriedly.

"Y-Yes. D-Don't worry. I'll be fine," she replied, stuttering from the pain.

Zach was worried, but listening to her, he slowly continued, pushing further into her. Twilight's eyes shut tight, she gritted her teeth, and then let out a quiet squeal of pain as Zach tore through her hymen. To avoid anymore pain, Zach stopped to allow Twilight to recover, and for the pain to fade. He looked down to his stallionhood to see blood slowly leaking out from Twilight's marehood.

"You okay, Twi?" He asked.

Twilight was a bit more focused on the pain, but she listened and nodded. "Y-Yes...I'm fine. Just...g-give me a moment..."

"Take your time," Zach replied, smiling, before leaning downward to kiss her forehead, just next to her horn.

After what seemed like hours, when it had only been a couple of minutes, Twilight nodded, urging him to continue. He listened, and began to pull out slowly, causing a little bit of pain to return, but Twilight tried her best to ignore it. Once the tip of Zach's shaft was almost out, Zach quickly slid it back in, but not too fast to avoid hurting Twilight. When he slid it back in, Twilight moaned, partially out of pain, but more out of pleasure.

When Zach pulled out and went back in, it was faster, and there was less pain. Each thrust was faster, and less and less pain occured. Within a minute of thrusting, there was no pain. Only pleasure.

"Z...Zach..." Twilight moaned. Zach had no idea whether this was a moan of pleasure, or pain. That was until he heard the next sentence.

"D...Don't s...stop..."

Just hearing that sentenced motioned him to continue with his progress. With each thrust, Twilight's moans increased in decibels. Eventually, Twilight was close to screaming, but she tried her best not to be too loud.

Suddenly, a feeling began to emerge in Zach's loins. This was the same feeling he felt before. When the feeling came to Twilight, she instantly recognized it. It was the feeling of another orgasm.

"Z...Zach...a-ah...I..."

"I k-know...Twi...I'm ab-bout to, also..." Zach stuttered.

Twilight then remembered something. If the stallion were to release inside the mare, there would be a possible chance of pregnancy. Twilight didn't know how to take care of a child, but she could learn. After all, she did live in a library, after all. Plus, she was making love with the stallion who's been in love with her since he arrived here just 2 years ago.

As Twilight was thinking, her vaginal walls tightened around Zach's shaft without her realizing, forcing him inside further, and bringing him to the point of orgasm, yet he held it back long enough.

"Do...Do you want m-me to-" Zach was cut off when Twilight replied.

"Leave i-it...i-in..." She moaned.

"B-But...Wh-What abou-" Again, Zach was cutoff.

"I love you, Zachary Lanson. I love you so much. I don't care what happens if you leave it in...J-Just....c-cum inside me..."

Zach was a bit surprised about Twilight saying the word 'cum'. He'd expect her to say orgasm or release. But, forgetting that, he listened, and decided to release his seed inside his mare. Quickly, he pumped into her much faster than before.

"Z-Zach! Z...Zach! I...I'm....I'm..." Twilight yelled, and just a moment later, Zach pushed himself as deep as he could go, then letting it all out, he released his seed deep into Twilight's womb, the cum coating her vaginal walls.

"Zachary! A-Aah!" Twilight yelled as loud as she could, not caring if it woke a pony or two in town, and she released her vaginal juices, twitching uncontrollably as she did so. Her vaginal walls were coated by a mixture of semen and vaginal juice. Her juices flowed right past Zach's shaft, squirting a little as they leaked out. After a few moments, Zach's cum slowly leaked out, dripping onto the blanket below, along with Twilight's juices.

In the midst of their orgasms, the two stared at each other, looking deep into each other's eyes. At this moment, they reached the gates of pony Heaven, and stress, sadness, and all the other bad emotions slowly faded away. The only thing that remained was happiness, caring, love. At this moment, nothing else mattered. Not to them. The only thing that mattered was them. Their love. Their night.

Eventually, their orgasms died down, and they slowly came back down to Equestria, panting heavily from their event. They were drenched in sweat and a partial mixture of semen and vaginal juices. Slowly, with remaining strength, Zach slowly slid his shrinking shaft out of Twilight's marehood, allowing the remaining juices and cum to flow out, falling onto the blanket.

Zach then slowly laid down on top of Twilight, who gladly accepted him. She slowly and weakly wrapped her forelegs around his body, hugging him with the remaining strength she had.

"Zach...?" She weakly asked.

"Yeah...?" Zach replied with little strength and little sound.

It was silent for a moment, as Twilight slowly was losing consciousness. Finally, after a moment of silence, she spoke.

"...I love you..."

Zach, with the last of his strength, smiled.

"I love you too..."

He waited for a response. But there was none.

"...Twilight?"

He slowly looked down to see that Twilight had already closed her eyes, and was already in Dreamland, waiting for him. Her snores were adorkable and cute. Zach weakly chuckled, then leaned his head down, and gently kissed her on the forehead, but not before slightly, and weakly, licking her horn, causing her to moan in her sleep, and twitch her right leg.

Zach chuckled at her reaction, then kissed her forehead again.

"Good night, my angel..." Zach whispered in Twilight's ear. In only a few seconds, Zach was also asleep, ready to join his lover in the heavens of Dreamland...to be the Prince Charming...to meet his Princess Fiona...

Celestia's sun slowly rose over the horizon, just as Luna's moon sank below it. Zach was the first to be shined upon by the sun's rays. He slowly rubbed his eyes to get rid of the blurry view, then looked around and noticed they slept right next to the lake the entire night. Luckily, it wasn't freezing outside. Perhaps the rather...private events kept them warm throughout the night. Just remembering it made Zach blush slightly.

Just then, he heard an adorkable sounding yawn in front of him. He looked to see Twilight, all snuggled up in his forelegs, waking up. She looked around a little, then turned around to see Zach looking at her. her shiny eyes stared back at him, causing him to grin in happiness.

"Good morning," she said to him, smiling.

"Morning," Zach replied, smiling back, "Did you sleep well last night?"

"I've never been more relaxed in my life, thanks to you," she answered, leaning her head back onto his neck and giggling. Doing this, Zach kissed her once again, which Twilight gladly accepted.

After the kiss, Twilight asked, "So...how was last night?" She then blushed a little after asking the question.

Zach chuckled a bit and smiled.

"It was the best night of my life. I'm glad I got to spend it with you," he replied. Twilight smiled and blushed deeply. To be honest, it actually was the best night of his life. His nights during his 5 years at the orphanage were nothing but complete shit, and for his 2 years in Equestria, he's had difficulty sleeping, resulting from nightmares, night terrors, etc.

But for the first time since then, he had his first peaceful and quiet sleep.

"I love you, Zach," Twilight said, smiling and blushing deeply.

"I love you too, Twilight."

Their lips touched once again as Celestia's sun rose to awaken Equestria.

Truly, this Hearts and Hooves Day was Zach's best day ever...but it certainly wouldn't be his last...

Author's Note

I know this story has gotten quite a lot of hate. And you know what? I agree with it being bad. Like it says in the description, I promised a friend I was going to work on the story several times last year (2012), but I never got around to starting it. It was just days before Valentine's Day 2013 that I finally started working on it, and by then, he got quite impatient. I hated pissing people off, so I finally decided to stop being lazy and work on it.

For some reason, it felt painful for me to make the story. I got quite tired of making stories, but I wanted to get this done and out of the way. When I finished, I sent him a copy of it, and he liked it, though you guys didn't.

Seeing the amount of dislikes this story has been given does not surprise me in the least. However, I did promise that I would remake this.

This remake might not and will never change the amounts of likes against dislikes, but at least people don't have to see shit.