Around Equestria in a Lifetime - A First Time for Anything

by Derpibra

Rating: mature
Tags: Romance, Slice of Life, Alternate Universe, Comedy
Length: 3228

After spending his childhood in Los Pegasus, then some in Canterlot, Derpibra moves to Ponyville.

Derpibra grew up in Los Pegasus. He spent most of his childhood there, and a few more years in Canterlot. Seeking adventure, and a town with cheaper real estate to live in, he travels to Ponyville. But there, he found something quite… interesting.

Published 1970-01-01 00:00:00 UTC
Last updated 2015-09-14 21:50:02 UTC

A New Home Owner's Treat

/Around Equestria in a Lifetime - A First Time for Anything\

It was the crack of sunrise.

The town of Ponyville was in sight. Derpibra had to have been riding on the train from Los Pegasus to his curret destination for at least a day or two.

He would kill to be able to get off of this train. His hooves and flank felt dead to the touch.

At least the town is a mile or two away... Derpibra, the eighteen year old stallion thought, trying to keep his sanity in check. He was never the type to be able to sit in one place for very long, so this was pretty torturous for him.

His parents sent him off on his journey with ten thousand bits for him to cover a house wherever he wanted. It was his life's savings since childhood, increasing over time thanks to a fraction of his parents' paychecks every couple weeks or so. There would be more in his possession, but he spent some of it on gaming equipment prior to moving out, about five hundred.

After a long ten minutes, the train came to a halt. A train operator wearing a red and white striped cap emerged from the cockpit. "This stop is Ponyville folks! I hope you enjoyed your ride!" He called out joyfully.

Derpibra, as well as several different ponies of varying colors, and sizes, started flowing out of the doors like a river.

He took in the beauty of Ponyville, shifting his head left to right, right to left, capturing every ounce of color and personality the town had. It wasn't quite as bright as Los Pegasus, but it did shine in other ways. The ponies, the creative, flashy architecture, and a statue or two in the immediate area.

"This place looks pretty cool." He muttered, not wanting to be caught talking to himself. "Time to explore a bit."

With his bags, he aimlessly wandered around town, trying to get a feel for his new environment. He tripped on a few stones and even his own backpack, but he didn't care. It was who he was. How can you trip off of that?

He saw a mare who wore glasses and had a brownish coat. He figured she looked important, and so, approached her in a friendly fashion. "Hi!" He said with an accepting smile.

"Hello dear." She replied. "Judging by those bags, I'm guessing you are new to Ponyville? Or am I wrong?"

He shook his head. "Nope, you're right! Just came from Canterlot after spending lots of time with Sapphire Shores. I used to live in Los Pegasus. Oh! Um.. what's your name by the way? I'm Derpibra!" He shook her hoof.

"Mayor Mare. I'm the mayor of Ponyville. Maybe you want me to show you around? I'm free for the next hour or so, it's my lunch break." She offered.

"Sure! But, before I go on a tour... Could you help me buy a house? I need a place to settle down." He shook his hooves attempting to relieve a bit of stress in his legs.

"Of course. You need to register with town so that we can have your information in case you need any help."

"Thanks!"

"It's my pleasure. Please, follow me to the Town Hall." She trotted off, and he followed.

What were the odds of me running into the Mayor? It's still kinda early... He thought. He didn't ponder it too much though, he was going to get a home!

Derpibra was signing a few documents using his wings to hold the pen. "Aaand... done!" He confidently placed the pen on her wooden desk, awaiting a compliment he was sure to receive.

Mayor Mare raised both brows, eyes slowly expanding at the incredible amount of dexterity in his wings that most other pegasi seemed to lack. "Impressive," She began. "You're one of the first pegasi I've seen actually do that."

He rubbed the back of his head. "Oh, it's nothing." Said Derpibra. He has been practicing that little trick of his for a while, afterall.

"So," She tilted her glasses into place. "Let's go over your details of your home once more shall we?"

He nodded. "Sure."

She stacked the documents on the fine oakwood table with multiple taps. Her eyes scrolling left to right, she read aloud the details. "Single story cottage with a basement and attic fitted with a balcony. Small flower garden in the front with a medium backyard. Starter pack furniture included at ten percent more. Is this correct?"

"Yuppie!" Said Derpibra rather immaturely. He didn't grow up very much did he?

She shook hooves with the stallion, grateful for his business. "Welcome to Ponyville!" She said gleefully.

Now fully registered with Ponyville, he bought his first house, and was ready to live life on his own. Carrying the deed and his luggage, he made way to his new sanctuary found next door to Sugar Cube Corner.

He unlocked the brown door with it's authentic golden knob by using a fancy golden crescent key. The door on it's new hinges, as it opened it made scarcely a sound. Upon stepping in, shutting the door behind him, he gawked at the dark wood flooring, chocolate brown finished walls, and pearl white ceiling. His home reminded him of a vanilla ice cream sandwich.

At the corner of the house, he spotted a ladder for the attic, and a staircase for the basement, next to a small window and a replica of the front door as the back door, leading to the backyard. The rays of morning, breaking throughout any and all windows in the house.

He slowly walked about the unfurnished house getting a feel for his five thousand well spent bits. He almost lost himself in thought after looking at a wall for a bit too long, but before he could, a slam was heard at the front door that echoed in the house slightly.

"Ah!" He jolted back in surprise. (What was that?) "Either somepony is pretty angry or has a weird way of visiting others' homes..." He muttered as he trotted to the door. As it opened slowly, it revealed a gray mare with a lemon-yellow mane and.... crossed eyes?

"Hi!" Said the mare, reaching into her delivery bag, rubbing her head. Maybe she hit the door on accident? "My name is Derpy, and I'm the mailmare of Ponyville! Every once in a while, I'll drop by your house to deliver you things that were sent to you." She reached out with a hot pink envelope, prompting him to take it.

He reached for it with his huge wings. As he grabbed it, his wings nearly covered her entire muzzle. He froze. Her crossed eyes connected with his, locking them in an unexpected gaze that they developed a desire to never let go. Derpibra felt a strange warmth coming from her, and she felt the same from him. They both blushed brightly, with small smiles accommodated by more relaxed expressions.

He leaned in closer, the heat becoming even more intense. He just met this silver-blonde mare yet he feels a strong connection, and one could safely assume she did too. "I'm Derpibra." He whispered with love and an ounce of possible lust in his tone.

(He's so...) Derpy almost lost herself. "I... Derpibra..." She said feebly. Her breath gave a warm scent of muffins that drove him to the edge.

They both knew that instant love was in the making, barely containing the power to withstand their growing lust for eachother despite only seeing eachother for but a few minutes now.

But that power quickly faded. Derpy's silver lips connected with his, tasting like warm pastries. After a great amount of seconds, they released eachother, a trickle of silver sparkles and bliss connecting them together before it hit the floor.

They both blushed even brighter this time. Being overtaken by the strengths of love  can cause one to do unpredictable things. And this was among them.

"What are we...-" Derpibra was cut off suddenly when Derpy grabbed the back of his head and dragged him into another passionate kiss, this one being much more moist and adventurous.

Heads retracting for the second time, they gazed at eachother again. They swore to themselves that ponies may have been staring, but neither cared.

"Derpy..." He said with a pleasured tone. "I want to hang out some more..." He allowed her in his home and closed the door, ensuring their privacy.

"There's something about you Derpibra..." She said lowly. She wasn't concerned about her errands at this point. The mail could wait. "Something I like."

Derpy had somewhat of an unintentional sway to her hips. He attempted to shrug off a feeling of burning temptation, judging that it's too soon for any "Monkey Business".

She looked around with a bit of confusion. "The furniture isn't here yet is it?" She asked.

He shook his head. "Nuh uh."

"That sucks." Said Derpy. "Not even a couch? That's okay though." She slowly walked up to him. Placing a hoof on his rather skinny chest, she felt his heart accelerate before her.

"The furniture should be around sooner or later." He said. "Until then, maybe you wanna get something to eat? It's my treat."

"We should maybe do it later because I have lots of mail to get in today." She sounded disappointed almost. "But I came in here because... you lured me here." She blushed once again.

"I won't hold you from your work then." He opened the door for her as she began trotting out. "What time will we meet?"

"6:00." She said, tracing his chin with her left hoof. She pecked him on his forehead  followed by his lips, and resumed her daily errands.

He closed the door, standing in the now cooler house now that Derpy left. But at least he had time to think to himself.

(Derpy... she's so beautiful... I barely know her, yet I'm in love with her already. How did this happen...?) He could scarcely believe what just transpired moments ago.

(6 o'clock seems so far now...)

Something struck his memory. He remembered that pink envelope his new love gave him. He carefully tore it open, since he lacked any letter openers. He extracted a pale yellow paper from it.

[Dear Derpibra,

You will be receiving your furniture in the next half hour within this letter being delivered. I hope you enjoy your new home in Ponyville! Make sure to make some friends. The townsfolk are really something here!

-Mayor Mare]

The letter brought a smile to his face. All he had to do was find something to get into for a while until his furniture made it home. Then, even more waiting was ahead, since he had to wait patiently for Derpy's return.

With that, he hooked up his computer in the basement, set up his internet, and left his bags home as he ventured around Ponyville attempting to straighten his knowledge of his new town.

His home was decorated to the maximum possible. White fluffy couches, authentic glass tables, pixel paintings, and a brown queen sized bed. The kitchen had a familiar look, with it's stainless steel appliances and while tile flooring. It brought back blissful memories of Los Pegasus.

The clock read 5:59 PM. Out of boredom, he counted down the seconds as his silver clock which bore an emblem of Equestria, ticked down to the final seconds. As soon as it hit 6:00, another slam was heard. This time was enough to shake the house slightly. With an idea of who it was, he trotted to the door with a lovely smile ready, and a slight bit of worry as to how hard his lover hit her head.

The door slid open, once again revealing his mare. She looked even more beautiful, what with having the crisp moonlight shining on her warm body with a bit of sun from it poking above the setting horizon.

"May I?" She asked with an almost seductive tone.

"Of course." He had that same warming feeling from hours ago. But this time, it seemed to burn compared to then. "I'm glad you came." A smile dominated his face.

She walked over to a star white couch next to a fancy glass table with jet black legs. She tripped on the table however, and landed within the couch, her face sinking inside of it slowly.

He found this adorable. He walked to the couch to cuddle with her, only to commit the same mistake she did. Landing on top of her, he felt a criminally strong heat emanating from her as they both blushed.

He felt a strong sensation, a rather familiar one. He held back any serious urges, at least for now. "Tell me about yourself." That deep, sexy tone of his that he can voice act oh so well.

"Well," She had a particular tone of lust herself. "As you know, I deliver mail for a living. I really, really love muffins and... I'm Derpy like you are." Obvious details to be certain, but that last statement made Derpibra's urges all the more severe.

Still below his sun-like body, she decided to ask him something. "Do you have anything about your life you wanna share too?"

"I grew up in Los Pegasus. I was always surrounded by famous ponies and events. Eventually I wanted to do what the famous did. I had a Ponytube channel when I was younger, and still do even now. I met Sapphire Shores, and she helped my channel grow. I'm still not famous like she is, but I'm kinda well known, even though it seems nopony here knows me." He explained.

"Aww." She said in a very relaxed tone. "That's too bad... maybe I can help out?" She brought his head down to her, kissing him passionately. Her hooves twitched at his side as they continued their lovely session.

His sensation grew stronger, but he resisted even still, since having a one-night-stand would seem... ungentlemanly of him, though he didn't know why. But even then, he could only keep himself from such an occurrence for only a bit longer...

He dug his muzzle into her furry coat on her neck, nibbling her skin underneath playfully. She moaned slightly.

(Is now the time for this? It seems early...) He thought while her moans were lessening his ability to resist giving her an experience both of them wanted with almost a burning passion. How could they want something so quickly?

They continued their lustful activities together. Kisses leaving saliva strings around their faces and on the couch they played on.

Derpy disconnected the soft mouths aching for more. She gave the best bedroom eyes any stallion would lust after. "Do me a favor," She whispered. "That bed... It looks cozy."

Derpibra took a few seconds to process what she said, and finally realized what she was implying. "Are you sure? It's a little early..."

"Don't be shy." She said, sitting herself up, all the while brushing up against his throbbing erection. He allowed a small moan to escape from the minor contact.

"You're kinda sensitive." She said as she walked to the crisp, white bed, a sway in her hips that seemed more deliberate this time around. "Have you ever... you know..."

He shook his head. "Never came close to a mare like I'm doing here with you." He said, sounding slighty ashamed. "I've never dated either."

"And you're...?" Asked Derpy.

"Eighteen."

"Then we're sorta the same." She replied. "This is my first time too." She sat on the bed with a bounce. Her flank seemed to shake from the impact, only adding fuel to his fiery desire to have his first time be a good one. "I wanted you the second I saw you, you know."

He slowly made his way to the bed. "So did I." He replied. "I saw it in your eyes. The perfect mare..."

She got into such a position that screamed Do-me-however-you-like, leaving her body parts for him to explore freely with unhindered access. "Do you at least know what these parts are?" She asked jokingly. Her vagina was leaking from the thought of him being inside her.

He leaned down for a better look, and was barely believing that he was before one of the best parts of mare's bodies. "I have an idea." He lightly booped it with his muzzle, causing Derpy to breathe slightly faster.

"Mmm..." She moaned more audibly this time. "Do that again!" She begged. Since this was a first time for the couple, this was bound to get out of hoof in a matter of minutes.

This time, he didn't just boop it, but he buried his muzzle in her, moving his tounge around in much more energetic and haphazard directions. She moaned loudly, her juices coating his muzzle. Her breathing accelerated to new heights. "Go deeper... deeper!" She half demanded and begged. Her sensitive vagina intruding on her ability to speak properly.

He did as she commanded, taking in some air before filling her with his untrained tounge. The unpredictability of his movements made it even more exciting. "I...I...!" She couldn't finish her sentence. "Mmm... ahhh!" Her first orgasm nearly caused Derpibra to choke, eyes rolling to the back of her head as Derpibra claimed his wet treats. She left rather large stains on his new bed, gushing like an angry geiser.

Derpibra didn't hold back anymore. This was his first time, and it will require his full dedication to make it as best of an experience as possible.

His huge cock harder than it has ever been, he gave in to his instincts. "Turn around Derpy." His tone full of lust now. She knew what would happen next.

She did as requested, and he almost had a natural knowledge of what he was doing despite never being this close to a vagina before, as he prodded her and slowly fitted himself in without question.

"Ahh..." She responded.

"Mmm..." He let out a masculine groan as her tight, wet walls hugged his penis tightly. She bled a slight bit from the intrusion, but to no considerable amount. He slowly done a reciprocating motion, forth and back, back and forth, until he gained a hastened pace.

They both breathed at various speeds. Derpy was dripping onto the mattress, while Derpibra's precum was futher staining the sheets. He hugged her tightly, continuing his erratic pace until...

"Derpy... I'm gonna...!"

Derpy, having a bit more control of herself since her last orgasm, pulled him out, and clopped him until he was on the verge of shooting his love onto her face. She kissed his member a couple of times, and slowly slid her head down his shaft. She worked his member until he came. She pulled out, with an audible 'Pop' noise, and clopped him further until he shot rope after rope of cum on her face.

He flopped beside her on the bed, nearly unconscious. She was on the verge of passing out as well. Erratic breathing could be heard from any corner of the house. After a minute, their breathing calmed, and finding themselves tired rather early, decided to go to sleep with eachother wrapped in their hooves.

Welcome to Ponyville.