Twilight's First Time

by chief maximus

Rating: mature
Tags: Sex, Twilight Sparkle, Random, Slice of Life, My Little Pony: Friendship is Magic
Length: 4592

Twilight finally decides to take part in something every mare her age should experience.

Twilight Sparkle has experienced many wonderful things in her life, and yet one experience in particular has eluded the studious young mare. Something that should be a regular occurrence in every normal adult pony's life. After a chat with Rarity, she is finally convinced to take the plunge, and put herself in the care of professionals.

One shot.

Published 2012-05-15 04:44:03 UTC
Last updated 2012-05-15 04:44:03 UTC

Twilight's First Time

Twilight's First Time

Edited By: FanNotANerd

"Come now, Twilight, how could you have gone twenty two years without-"

"Rarity!" Twilight snapped, shushing her. She lowered her head in embarrassment, as if everypony in the town square was staring at them. This was certainly the last time she would invite Rarity to lunch to discuss such personal matters in public. It was a perfect day for an outdoor meal at one of the many restaurants in the center of Ponyville. The sun was shining, the birds were chirping, and the sweet scent of freshly blossoming flowers filled the air.

"Twilight, please," Rarity nagged before taking a bite of her daffodil sandwich, elegantly dabbing her napkin against her chin. "You need to let another pony -a professional- take care of these things for you."

Twilight blushed, pinning her ears back as she glanced down at her own food nervously. At least she managed to keep her voice down this time. "I can take care of myself..." she answered weakly.

Rarity's firm look of insistence only held as she took another bite of her lunch. "You can't keep doing it yourself Twilight. Haven't you ever wondered what it's like to have another pony to-"

"Yes, I have," she interrupted flatly, now beginning to regret even bringing up this particular topic. "But I don't think anypony can do it any better than I can."

Rarity raised a perfectly groomed eyebrow. "Trust me, they can."

Twilight sighed. It seemed there was no getting around the issue now. The cat was out of the bag, as they say. "I don't know... I've just, never really found the time, and found somepony I trust..." she began, her friend nodding in agreement.

"Well, trusting the pony is important, but none are more trustworthy than those to whom I give my business," she insisted, as Twilight considered her friends advice. "Do you honestly think I would go there, if it weren't the most reputable place in town?"

Twilight began eating her lunch as well, though all this talk of her personal business was beginning to spoil her appetite.

"I guess you're right," she relented, finally biting into her salad. "But... doesn't it hurt?"

Rarity smiled; pleased that she was making progress in finally convincing Twilight to take the first steps most ponies take when they're much younger. "Well, it may be a bit uncomfortable for the first few minutes, but any stallion worth their salt will make sure you're okay with what their doing. And after a while, the pain will fade, and you'll find your visit may just be enjoyable."

Twilight cast another embarrassed gaze down at her salad, as if it were going to comfort her. "I don't know..." she groaned, resting her chin on her hoof before looking back to Rarity.

"What if I told you that not only do I go, but so does Applejack, Pinkie, Rainbow Dash... even Fluttershy." Twilight's ears perked up at the mention of her friends names. Even Fluttershy had gone to this place?

"Fluttershy?" Twilight repeated.

"Mhmm, she goes more often than I do!" Rarity laughed, finishing her lunch. "I believe she has some type of rewards card. She gets her next visit free if what she told me at the spa was correct," Rarity recalled. "But we can't all be like Fluttershy, can we?"

"Well, I guess if even Fluttershy does it..." She reasoned if her most shy and timid of friends let the stallions there have access to that most private of areas, she supposed she could as well.

"That's the spirit!" the fashionista proclaimed proudly. "Here Twilight, go in tomorrow and give the receptionist this card," she said reaching into the saddle bags she'd taken off and stowed beneath the table. "This is the same stallion I see. He's the best there is," she insisted.

Twilight looked at name on the card. "The stallion's name is Pearl?"

"Don't let the name fool you," Rarity grinned, "He'll take good care of you, I promise."

Twilight put the card in her bag, finishing what she wanted of her salad. "Well, if you say he's the best."

"Trust me Twilight, by this time tomorrow, you'll be feeling like a new mare!" she said excitedly. She smiled earnestly for the first time since they sat down. Perhaps there was something to be gained from all this. Twilight was always open to studying new and exciting experiences, why would this be any different? She trusted Rarity, and if Rarity trusted this guy, then she could too.

"Okay, first thing tomorrow morning." Twilight smiled, "Uhm, do you think you could stay with Spike while I'm gone? I'd hate for him to have to wait on me."

Rarity shook a dismissive hoof in front of her, "Not a problem at all!" she assured her, "As long as you've been putting this off, it's the least I can do."

"Spike, I'm home," Twilight called into the richly colored wood of her tree home. Spike was perched high on the top of the rolling ladder with an armload of books, teetering precariously close to falling off of it.

"Hey Twili-ah!" he cried as his weight shift sent the ladder shooting out from under him, plummeting the ten feet or so to the floor. Spike winced and braced himself for impact… and opened his eyes a moment later when he realized he was hovering an inch off the floor, held in place by Twilight’s magic.

"Phew," he sighed in relief as Twilight set him on his feet.

"Spike, what have I told you about trying to reach the top shelves without locking the wheels?" she asked in a motherly tone.

"I was only gonna be up there for a second..." he protested weakly, though Twilight was having none of it.

"You're lucky I was there to catch you," she insisted, replacing the fallen books back to their rightful place. "What if I hadn't been?"

Spike certainly didn't like it when she spoke in such a condescending tone, but she was right. He'd have quite the headache at the very least, if not for her intervention.

"Sorry..." Spike grumbled, reminding himself of where Twilight had been that day. "How was Lady Rarity?" he asked, always quick to inquire about the object of his somewhat unrequited affection.

"She was fine," Twilight answered with a roll of her eyes. Like clockwork she thought, commenting on her number one assistant's most predictable habit.

"Did she say anything about me?" he asked hopefully.

"No, Spike," she said, trotting back over to her the table in the center of the library where a few more books had been scattered from the previous night's study session. "You didn't come up. We talked about... something else." It was a pathetic attempt to skirt the issue, and Spike immediately knew from her tone what she was referring to.

"Oh, talked about that eh?" the young dragon grinned devilishly.

Twilight shot him an unamused glare before returning the books from the table to their proper place. "My shortcomings as a pony are none of your business, Spike."

"C'mon Twilight, its not that big of a deal. I've never done it, so its not like you're alone in this."

The studious unicorn sighed. She knew he was simply trying to make her feel better, but he wasn't exactly helping. "You're a baby dragon, Spike."

"I am not a baby!" he shot back indignantly.

"You know what I mean," she replied, "You won't have to worry about this kind of thing for at least another few years."

She trotted into the kitchen, using her magic to begin washing the dirty dishes sitting in the sink as Spike grabbed a step-stool and joined her, drying them as she washed them.

"So what did Rarity say about it when you asked her?"

"She gave me a card, and told me to give it to the receptionist tomorrow morning," Twilight answered, still unsure of whether or not she would have the guts to go through with it. This was something she'd been doing for herself for as far back as she could remember! How in the name of Luna's plot could some other stallion be 'better' at it than her?

"So are you going to do it?" he asked, rubbing a plate dry with a towel before placing it back in the cupboard.

Twilight sighed. "What choice do I have? She already gave me the card... heck, even Fluttershy does this at least twice a month, apparently."

Spike was certainly surprised to hear that bit of information. "Fluttershy goes twice a month? Whoa."

"That's what I said."

"Well you know if somepony like her is brave enough to do it, you are too!" Spike assured her, drying the last plate.

"You're right Spike, I've been putting this off for too long!"

"'Atta girl! I bet it's nothing to even worry about," Spike assured.

As quickly as her confidence came, it evaporated as more worrisome thoughts entered her head.

"But what if it hurts too much, or I end up-" Twilight's concerns were cut off by a powerful belch from her dragon assistant, producing a letter from the Princess herself.

Snatching it out of the air with her magic before it could fall into the dishwater, she unrolled it and began scanning the lines.

My most faithful student Twilight Sparkle,

It has come to my attention that you have gone nearly two decades without having-

Twilight skimmed down the last few paragraphs, her face now as red as Big Macintosh's coat. Now even princess Celestia knew about her little... problem? She cursed herself for telling Rarity anything, assuming she must have written to the princess after they'd eaten lunch.

... I would like a report on your experience at your earliest convenience.

Sincerely, Princess Celestia.

"What'd it say?" Spike asked.

"Rarity told princess Celestia about... this whole thing," Twilight said, dropping the scroll onto the counter.

"Oh," Spike replied, struggling not to giggle.

"She wants a report on how it went when I'm done," she answered softly, as if in a state of shock.

After a brief moment of awkward silence, she spoke up.

"I guess I have no choice..."

The dawn approached, shining through her curtains and heralding the start of Twilight's big day. She got up quickly, early rising wasn't something hard for her, especially not if it was for something important. Spike was still asleep in his basket, and would be for the next few hours.

Rarity should be coming over soon. she thought, walking over to her dresser and mirror, examining her bed-ravaged mane. I guess it doesn't much matter what I look like... but still. Levitating a comb above her head, she began brushing and straightening her mane. There was certainly no reason for her to look like she had just wrestled a hydra if she could help it.

After managing her appearance, she cast an apprehensive glance toward her bathroom. Rarity was still a few minutes out, and she supposed there wasn't any reason she couldn't... take care of herself one more time, just so she wouldn't be nervous when the time came. Glancing back at Spike to make sure he was still soundly asleep, she trotted into the bathroom and closed and locked the door behind her.

After a few minutes, Twilight emerged, a satisfied smile across her lips as she caught another glimpse of herself in the mirror. Looking good, Twilight! she thought as a knock at the door interrupted her Rainbow Dash-like level of self confidence.

Quickly making her way to the front door, she greeted Rarity and Sweetie Belle with a smile.

"Hi Twilight! Rarity told me you've got an appointment today!" Sweetie Belle chirped happily.

Her cheeks lit up as she chastised Rarity for her indiscretion.

"Oh come now Twilight, get with the times. Fillies have just as much right to know about these types of things as any other age group," Rarity explained, taking a seat at her table while unpacking Sweetie Belle's breakfast from her saddle bag.

"Shouldn't she be in school?" Twilight whispered once Sweetie Belle had gone upstairs to wake Spike.

"It's Saturday," Rarity reminded her.

"Right..." she said, glancing at the clock on the wall. It was about time for her to leave, if she wanted to make it on time. "Well, I better get going," she said levitating her saddle bags on top of her back.

"You'll be okay Twilight, I promise. Just relax, and let him do his job," Rarity assured, "You'll come back from this wondering what you were so worked up about." She smiled.

"Okay," she sighed, unable to tame the butterflies in her stomach. With that, she bid her friend goodbye and set out into the early morning sun, casting its first rays of light onto the mostly sleeping town. She preferred it this way; there being less chance of anyone seeing her if everypony was asleep.

She knew the address, having been by it a couple of times before, though never daring to go inside. Still, a constant stream of both mares and stallions seemed to be coming in and out of the place, so she figured it was about time she did as well.

Twilight stopped in front of the doors, to the rather nondescript building, staring nervously at her reflection in the glass.

"Hey Twilight!"

She nearly jumped out of her own hide.

"What're you doin' up so early?" A voice called from above her head, laying on a cloud.

"Rainbow!" she snapped, for startling her. "I could ask you the same question."

"I have a job to do," she answered plainly. "You think these clouds are going to clear themselves?"

She could have explained that given the proper conditions, yes, they could clear up by themselves, but that probably wasn't what Rainbow meant.

"Seriously though, what are you..." she trailed off, looking at the building Twilight was in front of, then back to the rather embarrassed looking unicorn. A sly grin crept across her face as she put two and two together.

"You're here to see Pearly, aren't ya?"

Twilight's cheeks were as red as the finest apples from Applejack's farm. She lowered her ears and answered in a whisper, "Yes..."

"It's nothing to be embarrassed about, Twilight!" Rainbow laughed, "Frankly, I'd be more embarrassed about the fact that you waited until you were twenty two—"

"Rainbow that's enough!" Twilight snapped.

"Okay, okay, I'm sorry. Sheesh, don't get your tail in a knot."

Twilight sighed. She didn't mean to yell, but she was still pretty nervous, and Rainbow wasn't helping.

"Do you remember your first time here?" Twilight asked, hoping to borrow some of her pegasus friends confidence.

"Yeah, I was nervous too, but Pearly is the best there is. He's like... he's great, let's just leave it at that." She smiled, thinking back to the first time she had gone to see him.

"I gotta get back to work, but you'll be fine Twilight, trust me," Dash added, Twilight having heard that line in one form or another quite a bit in the last few hours.

"See ya, Rainbow," she bid as her friend left to continue her duties.

Finding herself alone again with her thoughts, she looked firmly at her reflection in the mirrored glass as she plucked up her courage and opened the door. The smell that greeted her was sterile, not unlike that of a hospital or doctors office.

The waiting room was well kept, with all manner of paintings on the walls, as well as soft, soothing music playing overhead. At the far end of the room, a light blue unicorn with a two-toned blue and white mane sat behind a stately desk, looking in her direction when she entered.

"I was wondering when you were going to actually come in instead of talking to yourself outside," she added cheerfully, Twilight blushing as she realized you could see out of the doors from the inside.

"Oh! I wasn't talking to myself, my friend Rainbow Dash was on a cloud and—"

"It's okay," she shushed as Twilight stepped toward the desk, producing the card Rarity had given her the day before. "I haven't seen you here before, are you a new client?"

"Uhm... yeah. I've never really...done this here before," Twilight answered sheepishly.

"Oh, well we operate the same way any of the other places in Equestria operate—"

Twilight cut her off as she went into further detail. "I've actually never done this... anywhere."

The receptionist's jaw nearly hit the floor. "You've... never done this before? Ever? Aren't you like, twenty tw—"

"Yes, can we please just get on with this?" Twilight answered sharply, tired of the big deal everypony seemed to be making out of this whole situation. She levitated the card onto the desk as the receptionist took a look at it.

"Ah, Pearly has certainly been popular this week!" she commented, using her magic to write Twilight's name on the waiting list, though since she was here so early, her name was at the top.

"Have a seat, and I'll call you when he's ready for you," she added politely.

Twilight took a seat near the desk, surveying the seemingly random assortment of outdated magazines on the coffee table in front of her. Picking up one of the older scientific magazines, she absent-mindedly skimmed through the pages, trying to keep her mind from racing with all sorts of possibilities her overactive imagination seemed to love to produce. After an indeterminate amount of time, a voice startled her from her trancelike state.

"Ms. Sparkle?" the receptionist repeated. Twilight looked up from the article she wasn't even reading. "He's ready for you, if you'll just follow me..."

Twilight swallowed nervously, getting to her hooves and following the blue unicorn down a long hallway with different numbered rooms flanking either side of her, though every door was shut. Twilight heard what she could have swore was a yelp coming from one of them, but didn't have time to stop and ask, as she was led into room 25.

"Make yourself comfortable, he'll be with you momentarily," she added, leaving Twilight alone in the very sterile looking room. There were a few fake plants here and there, as well as some tacky pictures on the wall. Whomever decorated this room had no illusions about what it would be used for.

In the center of the room, was a bizarre, chair like contraption, complete with stirrups, a head rest, and all manner of devices attached to it. Most of which she didn't recognize, but prayed they would at least be explained before they were used on her.

Okay Twilight, Rarity said this guy was the best, and so did Rainbow! If you can't trust your friends, then who can you trust? she thought, still examining the odd looking seat in the center of the room. Before she could look at it further, the sound of an opening door startled her.

"Ah, you must be Twilight." A voice from behind her said calmly. She couldn't deny that whoever's voice that was certainly carried with it an air of comfort, helping to put her a bit more at ease. Turning, she saw a rather handsome unicorn stallion with a aqua green coat and white mane, about seven or so years her senior from the look of him.

"Pearly?" Twilight managed to choke through her nerves.

"That's right. I see you somehow got a hold of one of my misprinted business cards. For the longest time, my new clients thought I was a mare," he laughed, readying himself for the task at hand as though Twilight wasn't in the room with him.

Twilight recalled the name on the card Rarity had given her did say Pearl. The printing company must have left off the 'y'.

"Well, if you're ready, we can get started," he said, motioning towards the mysterious chair.

"You... want me in that?"

"Well, I suppose you could stand up the whole time, but I feel you might get tired after a while. But, if that's what you're in to—"

"No, that's okay!" Twilight said quickly, her cheeks flushing red for what had to be the fifth time that morning alone. Twilight crawled up onto the chair, laying herself on her back, ready and waiting for the stallion to begin. Her heart in her throat, all she could think about was whether or not it would hurt as her tail swished back and forth nervously.

"Take a few deep breaths and lean back for me," he said calmly, noticing how jittery she seemed. "This your first time?"

Twilight did as instructed, trying in vain to calm herself. "Yeah," she sighed.

"You've got nothing to worry about." He smiled. "I've been told I'm very gentle."

Reassuring her somewhat, Pearly leaned over her, his soft coat pressed against her own as she adjusted to the weight he was putting on her. In all honesty, his coat kind of tickled.

"Okay, let's get started," he said, readying himself. "Now, you may feel a slight pinch at first, but it will pass."

A slight pinch was right. She shut her eyes tightly, trying to and block out the pain, but still it persisted. How in Equestria did Fluttershy stand this? she thought as a single tear escaped her clenched eyelid.

"Are you okay, Twilight?" she heard him ask.

"Yes, keep going," she panted, trying to will herself into a pain free state.

"Let me know if something hurts too much, okay?" he whispered to her.

Twilight nodded as he increased the pressure. She let out a feminine grunt as Pearly removed himself, going to another part of the room as Twilight stared up at the ceiling, having finally opened her eyes. As Rarity had predicted, the pain began to subside, replaced by a somewhat tingly feeling that she certainly didn't hate.

"That should be it for the pain." She heard him say as he re-positioned himself above her. "Okay Twilight, I'm going to need you to get a bit wider than that."

She looked at him like he was crazy. "Wider? I can't get any wider!"

"Trust me, the wider you are, the more comfortable it'll be for the both of us," he insisted as she struggled to accommodate his request. At least he's pretty handsome.

Once inside, she began to relax, remembering Rarity's advice. Just let him do his job, Twilight.

She could feel her tender flesh begin to give way to his pressure, his steady breathing matching with her own as she finally began to realize she had hyped the entire experience up so badly in her head, that in truth, it was nothing at all to be afraid of. In fact, she began to kind of enjoy it. After all, the strange seat she was in was certainly more comfortable than she'd first guessed. She felt a warm trickle of blood escape from where he was working, as he too realized what had happened.

"I'm sorry about that, sometimes I don't know my own strength," he said grabbing a few sterile towels to dab up the crimson streak.

"It's okay," she whispered back to him as he went back in, continuing his diligent performance.

"Ah!" Twilight yelped as Pearly struck a rather sensitive area.

"Too much?" he asked.

"No, it's fine, keep going," she managed to squeak, still breathing quite heavily due to a combination of nerves and excitement.

"That's my girl," he assured her as she tried to smile back at him. "Okay, are you ready for the grand finale?" he whispered softly, earning a nod from Twilight.

She could feel the pressure building as he continued his work, slowly working towards the ultimate goal which had drawn her here in the first place. Her breathing quickened as he seemed to be putting everything he had into not only making sure she was comfortable, but also that she had a pleasant experience. Soon, a wave of relief swept over Twilight as Pearly removed himself from above her, declaring his work completed. Twilight lay back in the chair, exhausted, but satisfied, just as Rarity predicted.

"All done," he spoke softly to her, washing himself up and allowing her the same liberty.

"You were very good for your first time, Twilight," he complimented, his handsome smile returning the blush to her cheeks.

"Oh, I bet you say that to all the girls," she said getting up from the chair, her legs and back a bit sore from the unnatural position she'd occupied for the past forty five minutes.

"We'll I've certainly had some rather interesting clients. A one Macintosh Apple saw me last week, and he shifted and squirmed just about the entire time," he admitted as Twilight's jaw hit the floor.

"Mac is one of your clients?"

"Oh yes, though if his sister didn't make him come and see me, I doubt he'd show up at all," he laughed. "As a matter of fact, I've got Applebloom and Sweetie Belle scheduled for next week. It'll be their first time too," he mentioned nonchalantly.

"Aren't they a bit... young?" Twilight asked.

"Yes, well we usually have a pony that specializes in fillies and colts, but he's been sick with hay fever for a while, so I've taken on some of his work, but it's never too early to start, I always say,"  he answered, giving Twilight the bill for his services.

"Take this up to the front desk, and we can schedule another appointment on your way out. Have a good day Twilight!" he said happily, showing her the way back to the front desk.

"How was it?" the receptionist asked.

"Honestly, I kind of liked it..." she admitted with a tinge of embarrassment in her voice.

"Most mares do, especially with Pearly." She smiled warmly. "So, when can we expect you back?"

Twilight produced her schedule book from her saddlebag, checking when she'd have a free date within the next two weeks.

"How about Thursday of next week?"

"Sounds good! Have a nice day Ms. Sparkle!"

Twilight left the building and decided to stop for lunch before heading back to the library. She ordered a smoothie and began penning her letter to princess Celestia.

Dear Princess Celestia,

I learned today that even though you may think nopony can take care of your teeth better than you, there are professionals in the field of dentistry that are quite adept at putting an overactive mind at ease! (And quite adept at being handsome, too!) Even though I believed I had taken good care of my teeth, I still had to have one removed, but I was glad to have gone to a professional, instead of just hoping it would quit hurting on its own. This experience has taught me that although you may think you're the best at something, some matters are best left to professionals, and that most of the things we find ourselves worrying about aren't in reality, that bad at all!

Your faithful student, Twilight Sparkle.

"Hey Twilight!" A familiar voice called from above her, as Rainbow Dash fluttered down next to her at the table. "How'd it go?"

"It went better than I thought," she added happily, her jaw still a bit numb from the experience as she sipped her smoothie.

"See? I told ya Pearly Whites was the best dentist in town!" Rainbow laughed, taking a seat across from her friend. "Now all we need to do is get you laid."

"Rainbow!"