It's Alright to be Bold Sometimes

TWEEEEEEEEEEEE!

Fluttershy jumped at the loud whistling sound coming from her kitchen. Taking a few deep breaths to calm herself down, the nervous pegasus quickly pulled herself together and trotted over to the stove, turned it off, and removed the teakettle from the burner. Normally she would have been more composed as she prepared the tea for her weekly get-together with her friend Rarity, but today was different; there was something that had been upsetting Fluttershy for a while now and, and the pegasus felt that she could no longer keep it bottled up; she needed to tell somepony. She would have come to Rarity with her problem sooner, but the thought of telling one of her closest friends something so personal, so embarrassing, filled her with dread.

After taking another soothing breath, the shy pegasus pony brought the teakettle over to her dinner table where a silver platter lay full with a bowl of sugar cubes, an assortment of teabags, two teacups, and an old ceramic teapot. She gently tilted the spout of the kettle over the hole in the top of the pot and slowly poured the piping hot water into it, careful not to spill a single drop. Just as she returned the kettle to the stove, she heard a knock at the door that made her jump again.

“Fluttershy darling, I hope I’m not too late,” came a voice from outside.

Fluttershy made her way to the front door and opened it just enough to peer through the crack. When she saw the white unicorn with her usual magnificently styled mane and tail, wearing a large red rimmed hat accented with diamonds, the pegasus slowly pulled the door open and smiled shyly at her friend.

“He-hello R-Rarity,” she said in almost a whisper, “please come in.”

Rarity returned the smile as she trotted into the house, a small basket suspended by magic following in her wake. When the two were inside the comfortable tree dwelling, the unicorn floated the hat off of her head and placed it on the rack by the door.

“I’m so sorry I took so long to get here, darling,” Rarity said as she opened the basket and levitated a small tray of freshly baked cupcakes out of it, “I had an order that I had to finish up for tomorrow, then I had to drop Sweetie Belle off at the Crusaders’ clubhouse, then I had to…” Rarity stopped when she noticed her friend wasn’t paying attention to her. “Fluttershy? Darling is everything alright?”

“Oh, I’m sorry,” Fluttershy muttered, her face beginning to turn a light shade of pink. “I, uh, I have to, um, get the tea.” She trotted quickly into the kitchen before her friend could see her cheeks flush deeper. “Please make yourself comfortable.”

“Fluttershy?” But it was too late; the pegasus pony disappeared behind the double doors that led into the other room.

It felt like there was a lead weight in Fluttershy’s chest as she crossed the kitchen to the sink. She opened a cabinet and took out a glass, poured some cold water into it, and drank, her shaking hoof causing most of the water to splash out of the glass and onto her coat instead of into her mouth.

I can’t do this, Fluttershy thought, there’s just no way that I can talk about this with anypony; it’s just too humiliating. She looked over to her refrigerator and her heart calmed a little as she saw a picture of herself with a light blue pegasus stallion with his messy dark, grayish blue mane, both ponies smiling as they shared an apple pie while a small white bunny stared angrily at them. The timid yellow pony pulled herself up and swallowed her fear. No, I must do this. For him, for us.

With newfound determination, Fluttershy trotted over to the table and made to slide the tea tray onto her rump, but stopped when she heard the sound of the refrigerator door opening. The mare turned around to see the fluffy cottontail of a little white bunny sticking out from the open refrigerator.

“Oh Angel, sweetie, would you come here for a moment,” Fluttershy called as she crouched to the floor.

The little bunny peered out from behind the door at his owner and gave her an annoyed look, but closed the fridge and hopped over when he saw Fluttershy’s pleading face.

“Angel, I know this is a bit of an odd request, but would you mind stepping out for a while?”

The little bunny crossed his arms and started tapping his foot in agitation.

“I know you’re upset, but I need to talk to auntie Rarity alone about something…private.”

The little bunny’s mood didn’t change.

“If you do, I’ll buy you a big, delicious apple pie afterwards as a thank you. Would you like that?”

Angel thought for a moment then gave a reluctant nod.

“Oh thank you Angel.” Fluttershy smiled at the bunny and gave him a hug. “Now off you go.” The shy mare nudged Angel towards the door with her muzzle until the little bunny started hopping off on his own.

Fluttershy picked herself up off the floor, slid the tea tray onto her rump and walked slowly back into the living room where Rarity was sitting on a plush green couch, reading a fashion magazine that had been lying on the coffee table.

“Sorry to keep you waiting Rarity,” Fluttershy said as she placed the tray on the coffee table. “I was just talking to Angel Bunny.”

Rarity smiled as she set the magazine down, levitated the teapot and started pouring hot water into the cups.

“That’s quite alright Fluttershy,” she said, “I was just reading a fascinating article on the most recent Canterlot fashions; looks like I was right about hats being in this summer.”

Rarity gave a delighted laugh as she took one of the teabags (Earl Grey), and began steeping it in the hot water. Fluttershy followed suit, picking up a green tea teabag and placing it in her own cup before taking a spot the couch beside her friend.

The two ponies sat and sipped their tea in silence, every now and then Rarity stole a glance at Fluttershy, as if expecting her to pick up the conversation. But seeing as the shy pony wasn’t about to start talking anytime soon, Rarity took it upon herself speak first.

“So, how’s Soarin’,” Rarity asked.

Fluttershy winced when Rarity had decided to start off their teatime by asking about the one topic she hoped to ease into.

“H-he’s f-f-fine…” Fluttershy found it hard to talk as she fought back the tears that threatened to burst forth.

“Fluttershy, darling, what’s the matter?” Rarity felt great concern for her friend; Fluttershy and the star Wonderbolt had been together for the past three years, and they always seemed very happy together, and now the yellow pegasus was breaking down at the mere mention of his name. “Did something happen between you two?”

Fluttershy shook her head.

“N-no, it’s nothing,” Fluttershy tried to get up from her seat and trot away, but was held in place by Rarity’s magic.

The unicorn placed a reassuring hoof on Fluttershy’s shoulder.

“Fluttershy, you know you can tell me anything, right?”

The timid pony looked at her friend through tear filled eyes then gave her a weak smile.

“Yes, I know,” she said as she shifted in her seat.

“Then please, tell me what’s wrong with you and your coltfriend.”

Fluttershy sighed and wiped away her tears.

“Ok,” she said, her voice cracking a little. “I’m not sure but I think…I th-think…” Tears began flooding down her cheeks again. “I think Soarin’ might be cheating on me!”

Rarity nearly dropped her teacup when she heard Fluttershy’s confession.

“I beg your pardon,” she said, setting down the cup so as not to spill her tea. “But, that doesn’t sound like him. Are you absolutely sure?”

Fluttershy shook her head.

“Well no, but for the past two weeks he’s been coming home much later than usual, and he’s usually so tired, he just eats dinner and goes to sleep. At first I didn’t think anything of it; I just thought Spitfire was working the team extra hard for a show, but then I found something the other day that made me suspicious.” The timid pony got up from her seat and trotted up stairs to look for something that was hidden in the closet of her bedroom.

Fluttershy came back down moments later with a magazine clutched in her teeth. She tossed the periodical on the coffee table so her friend could see what had her so worried. Rarity’s white coat turned red as she stared at mare gazing lustfully back at her. The magazine was a two-year-old issue of the gentlecolt’s periodical Playcolt, and on the cover was a yellowy orange mare with a flaming red mane, crouching towards the camera with her beautifully toned rump raised behind her, dressed in a sexy black corset with a spiked collar, flank high boots, and she had a riding crop clutched in her forehooves.

“Is that Spitfire?” Rarity asked in disbelief.

Fluttershy nodded her head sadly.

“Yes,” she said, “I found it in a box of Soarin’s things that fell open when I was cleaning out the closet.” Fluttershy wiped away a fresh set of tears. “It’s just proof that he must be cheating on me with Spitfire.”

After the initial shock of the magazine had settled in, Rarity couldn’t help but laugh. The weeping pegasus stared at her friend, shocked that she would take something like this so lightly. Seeing the panicked look on Fluttershy’s face, Rarity stifled herself.

“I’m sorry darling,” she said, “it’s just that, well, it’s such a ridiculous notion, thinking that Soarin’ would do such a thing with Spitfire.”

Fluttershy shook her head.

“I know, I know, but what about the magazine?”

“What about it?” Rarity picked up her teacup again and sipped from it. “He probably bought it because it featured his captain; I bet all of his teammates have a copy.”

“But he’s with me now, so why does he still have it?”

Rarity stared at the magazine for a moment.

“I’m sure he just forgot that he had it. I mean, look at how, ick, dirty it is,” Rarity blew on the magazine, disturbing the layer of dust that had built up on the cover. “This thing hasn’t been touched in ages.” Rarity took another sip of tea. “And anyway, isn’t Spitfire supposed to be dating that hoofball player Whisper Wings?”

Fluttershy thought for a moment; she could have sworn that she’d seen that name somewhere before, but where. Suddenly she sat bolt upright as she remembered just where she’d seen the name.

…

A few months back, Rarity had brought over some of her sewing magazines for Fluttershy to borrow. The yellow pegasus wasn’t as talented in the art of sewing as her unicorn friend, but she enjoyed reading up on different techniques and the latest fashions of Canterlot, so much so that Rarity often lent her the newest issues when she was finished with them. As Fluttershy flipped through the periodicals, she found something that made her blush; tucked away in the middle of the stack was an issue of Playfilly with a handsome, muscular pegasus stallion with a white coat and golden mane, dressed in a black suit and tie, and holding a glass of wine in his hooves. A little blurb next to the picture identified the stallion as the star running back for the Canterlot hoofball team, Whisper Wings. Fluttershy had never seen such a magazine herself, but she had heard from her friends that they contained different articles and celebrity interviews, and (Fluttershy’s blush deepened as she thought about it) erotic pictures of attractive stallions. She wanted to toss the magazine aside, but curiosity got the better of her.

After checking to make sure the coast was clear, Fluttershy took the magazine up to her bedroom where she hastily locked the door, and drew the curtain over her window to ensure that nopony would catch her looking at something so perverse. At first she found it to be rather enjoyable; there had been an interview with Princess Luna looking back on her return to Equestria, an article on Canterlot nightlife, and a quiz that wanted to know ‘What Sort of Lover Are You,’ (Fluttershy had skipped over this particular article, feeling too embarrassed to learn what the answer might be). Then she flipped another page and came to a picture of the same stallion that had been on the cover smiling up at her, only in this picture, his jacket and tie were off and his shirt was unbuttoned, revealing his toned chest underneath. Having found the first half of the periodical interesting, she flipped the page, wondering if she might have been wrong about what sort of magazine this had been (maybe the pictures were just of handsome stallions dressed in different, fashionable clothes). On the next page, however, she saw that Whisper Wings was reclining on a couch, only this time no traces of the suit remained. Fluttershy blushed as she examined the photo; Whisper Wings really was quite a handsome stallion with his perfectly styled mane, his toned muscular legs, his beautiful wings, and his large… The shy pegasus squealed as she slammed the magazine closed and threw it across the room in surprise. She clutched a hoof to her heart as it began beating out of her chest, and there was a fire burning behind her beet red cheeks. It wasn’t that she found the sight offensive or anything, it was just that the sight of Whisper Wings’ erect stallionhood on display had thrown Fluttershy completely off her guard.

Fluttershy tried to go about the rest of her day by cleaning the bedroom, but found that she still couldn’t get the image of Whisper Wings’ giant member out of her head, nor would her heartbeat slow back down to normal. As Fluttershy sat on the floor, trying to calm herself down, she suddenly became aware of a different heat emanating from between her haunches. It was a similar sensation to the one she felt whenever she watched Soarin’ stretching, or flying, or sometimes when he gave her a warm smile, but it wasn’t as strong. Fluttershy bit her bottom lip; she knew perfectly well what the feeling meant, but as many times as she felt that overwhelming heat, she had always been too shy to do anything to satisfy her wanting. But today was different; Soarin’ was away in Canterlot performing in a flight show and wouldn’t be back until evening, and Angel was out in the garden tending to his carrot patch. Succumbing to temptation, Fluttershy inched her right foreleg south to her marehood and gingerly touched it with the tip of her hoof, which she quickly retracted as a jolt shot up through her body, eliciting a tiny gasp from the mare. The sudden touch against her most private of places and the sensation it brought on scared the nervous pony, not because it was unpleasant though, but because it wasn’t. This burning pleasure was new to Fluttershy, so she wasn’t sure how to proceed; all she knew was that something inside her wanted more. The pegasus rested on her back, allowing her wings to spread out comfortably on the floor underneath her, and slowly brought her hoof back down to her pussy, again touching it lightly, allowing her body to grow used to the foreign sensations that coursed through her body.

After a few minutes of her gentle probing, Fluttershy worked up the courage to take her hoof and press it into her slit and began lightly rubbing, allowing some of her excited juices to trickle down her rump, dampening the soft pink tail that lay below. The timid mare held her free hoof over her mouth to try and stifle her squeals and moans as wave after wave of pure bliss surged through her. As she continued to rub her hoof back and forth against her increasingly dampening nethers, the image of Whisper Wings dissipated as ecstasy forced her mind into darkness. Fluttershy would have started worrying if something like that was normal, had she not been too busy enjoying the feeling of her inexperienced hoof’s work. As her body grew hotter, Fluttershy couldn’t help but whisper her coltfriend’s name, and almost like magic, the image of a reclining stallion forced its way back into the pegasus’ mind, only it wasn’t Whisper Wings; it was Soarin’. As soon as the Wonderbolt entered her head, Fluttershy felt her hoof pick up speed, imagining that it was Soarin’ that was causing her to experience so much pleasure. Suddenly her legs clenched around her active hoof as she grazed her clit, sending a new jolt of pleasure to ravage her body like an electric shock. Unfortunately, this experience was all too new to the timid pegasus, so she wasn’t ready for what happened next.

After what felt like an eternity (but was more like ten minutes) of dripping sweat, and whispered moans caused by her hoof’s work against her pussy, with the occasional brush against her clit, Fluttershy bucked her hips uncontrollably and let loose a soft whinny as-

…

“Fluttershy are you even listening to me,” Rarity huffed when she looked to her friend and saw that she was blushing profusely as she stared off into space.

The yellow pegasus jumped when she remembered that she was in the middle of tea, talking about her worries with Rarity, and not on the floor of her bedroom, writhing in the fading pleasure of her first orgasm.

“Oh, I’m sorry Rarity,” she said, feeling tired, out of breath, and very embarrassed, “what did you say?”

“I said that you have absolutely nothing to worry about; Soarin loves you, and I think you’re being a silly filly for thinking that he would jeopardize your relationship by sleeping with another mare.”

Fluttershy stared down at her teacup. Maybe Rarity’s right, she thought, maybe I’m worrying myself over nothing. The pegasus mare sighed as she brought the cup to her lips and took a sip of the warm tea; there was still something that weighed heavy on her mind, something that she knew would drive any stallion into the forelegs of another mare.

“There’s one more thing,” Fluttershy said, “Soarin and I, we…w-we haven’t really, um…you know.”

Rarity’s mouth hung open in a very unladylike manner.

“Darling, are you telling me that the two of haven’t, uh, consummated your relationship yet?”

Fluttershy continued staring at her cup.

“Well, I wouldn’t say we haven’t had s-s-s-sex, but…”

Rarity placed a hoof on Fluttershy’s shoulder and gave her a reassuring smile.

“It’s alright darling. I know this must be a difficult subject for you, so take your time.”

Fluttershy nodded. She knew that she had made the right choice by inviting Rarity over; she was the only one of her friends who could give her advice that came from experience, instead of making sarcastic jokes, or giving her secondhand knowledge that came from a book.

“Well, you see, I’d always been afraid of having a coltfriend because I’d heard that stallions only wanted one thing from a mare and they would do anything to get it. I was so scared that that was true, I promised myself I would wait until I met the right somepony who truly loved me, not want me for, sex.

“When Soarin and I started dating, I wasn’t sure if-”

“You weren’t sure if he really wanted to be with you, or if he just wanted rut you.”

Fluttershy nodded.

“He was really nice, and he seemed to really like me, but I couldn’t tell for sure. So one night when we were cuddling by the fire, decided to share my fears with him.”

Rarity was stunned.

“That was mighty bold of you darling. What did you tell him?”

“I told him the truth, that I cared for him, but that I wasn’t ready for sex. I thought he was going to be upset, that he’d want to get up and leave and never have anything to do with me ever again, but he didn’t; instead, he hugged me and told me that he would never ask me to do something I wasn’t prepared to do, and that he still liked me and wanted to be with me.”

“But you said that you two have done it before, right? What changed your mind?”

“I asked Soarin’ to move in with me.” Fluttershy took a few deep breaths and continued her story. “He was still living in Canterlot when we started dating, and he traveled to visit me whenever he could. But after two years of having a long distance relationship, I found that I hated being apart from him for those long periods; so the next time he had a day off from training and came to visit, I asked him if he would like to move into my tree house. At first I was worried that I was making an unreasonable request by asking him to leave his home, but he smiled and kissed me and said he would love to. He even joked that the commute between Ponyville and Canterlot was a lot easier on his wings than the training Spitfire puts the Wonderbolts through, so he would be more than happy to a make the trip everyday.

“On the night that we finished moving in his belongings, we had a nice dinner and enjoyed each others company, then we went to bed, but I found that I couldn’t sleep. It wasn’t because I was nervous about him living with me, or because the two of us were sharing a bed, it was because I was excited to finally have a special somepony that I really loved and who loved me back; the warmth of his body pressed against me made it all the more real. I looked over at him sleeping and I couldn’t help myself; I leaned over and kissed him.” Fluttershy gave a weak smile. “I guess that must have woken him up because before I knew it his tongue was…in my mouth.”

“So, what, did Soarin’ force himself on top of you?” Rarity asked, sitting on the edge of her seat, gripped by the tale.

Fluttershy shook her head.

“Actually, it was the other way around,” Fluttershy said with a blush. “He had been patient with me for so long, and I loved him for it, but I knew that us living together had to be a sign, so I crawled on top of him and that’s when I felt his…thing.”

Rarity gasped.

“Oh my,” she said. “Was it-”

Fluttershy nodded.

“Yes, it was very...big.” She felt her ears burning as she recalled the sight of her coltfriend’s member growing out of its sheath, creeping along her inner thigh, and becoming tangled in her long, pink tail. “Anyway, as soon as I started to try and put it in, he stopped kissing me and gave me a concerned look. I think he was about to ask me if I was sure that I was ready, but I quieted him with a kiss. I don’t remember much after that, except that we both moaned as he…entered me. Then there was a lot of pain.

“The next thing I remember was waking up the next morning wrapped in his forelegs, my…private area feeling very sore.”

“Oh you poor dear,” Rarity said, “It must have been too much for you to handle your first time around.”

“Yes.” Fluttershy nodded sadly. “From what Soarin’ told me, I screamed and fainted before he was even half way in.” Fluttershy felt ashamed. “I told him that I would be ok, but he was still worried about me.”

Fluttershy fell silent and took a sip of her tea.

“Is that it,” Rarity asked.

“Yes. We haven’t tried to have sex since that time.”

“But you’ve been living together for over a year now!”

“I know,” Fluttershy started to cry, “that’s why I’m so worried. What if he’s not satisfied with me? What if he’s going to another mare who’s less of a scared pony; somepony who’s more experienced?”

Rarity shook her head.

“Fluttershy, you two have been dating for three years now, and during that time I’ve gotten to know Soarin’, and I can honestly tell you that he is, without a doubt, one of the most honorable stallion’s I have ever known, and that he loves you more than anything. I mean think about it, he left his home in Canterlot for you when it would have been easier for him if you moved there. Not only that, but he even agreed to wait to have sex until you were ready, instead of trying to pressure you into doing it.” Rarity set her teacup back on the silver tray. “It sounds to me that your worries are stemming from a fear of intimacy. I think-”

“Actually, that’s not entirely true,” Fluttershy corrected, “I’ve actually been ready to try again for a few months now, but I haven’t been sure how to talk to him about it.”

“Then it sounds like you need a little more confidence.” There was a sudden sparkle in Rarity’s eyes as she jumped off the couch. “Ideeeeeaaaaaa,” she sang. “Fluttershy I have just the thing that will do wonders for you and your stallion’s physical relationship.” Rarity grabbed her friend’s hoof and started pulling her towards the door.

“Oh no, wait, where are we going,” Fluttershy asked, feeling very confused.

“We’re going to the boutique; there’s a sexy little outfit in my secret collection that would be just perfect for you,” Rarity winked at her friend, “and I know your coltfriend will love it.”

Fluttershy blushed and backed away hesitantly.

“Oh no Rarity, I could never wear sexy clothes; I’m not as bold as somepony like Spitfire.”

Rarity laughed.

“Oh Fluttershy, that’s exactly why you need my help.” The stylish unicorn levitated her hat back onto her head and smiled as she opened the door. “Trust me; what I have in store will be good for you. But I’m not going to stop with just the outfit, oh no no no no no , as one of your best friends, I’m going to take it upon myself to teach you a few techniques that will be sure to make Soarin’ putty in your hooves.” Seeing that Fluttershy still looked a bit hesitant, Rarity got behind her friend and started pushing her out the door. “And by the way darling,” she said with a devilish grin, “I am not taking no for an answer.”