Twilight had decided to give Fluttershy a bit of space. Ever since they had stopped by the sex shop, it had been rather difficult to interact normally. For most people, the knowledge of another person's masturbatory habits would merely be a weird thing to be aware of, but for Fluttershy it completely threw off her dynamic. She could barely pass Twilight on the street without blushing. And given that their past half-dozen conversations had been about Fluttershy's... habits, Twilight couldn't blame her. She hadn't broached the subject of orgasms, masturbation, dildos, or porn in the past week. That would be plenty of time for Fluttershy to figure out something that worked for her. Hopefully.

But now that week was over, and she had decided to pay Fluttershy a visit. The good news was that Fluttershy didn't seem hesitant to tell her how her first foray into assisted self-pleasure had gone. The bad news was that it apparently hadn't gone very well.

"...so what happened after Rainbow Dash left?" Twilight asked, pouring herself a cup of tea. Fluttershy made very good tea. Not quite as good as Rarity, but definitely on the higher end of the quality spectrum.

"Well, she had cleaned up most of the glass, but she missed some stuff, so I had to go over the floor again, just to make sure. When I finished sweeping again, I had to hang a sheet over the hole. Then I tried to get back to... you know."

Twilight nodded. "And how did that go?"

"It didn't. It started raining."

"Of course." Twilight shook her head.

"So then I had to go find a tarp to hang over the hole so the water couldn't get into my room. But I got that put up, and I cleaned up the mess in my room, and tried again."

"And then?" Twilight asked, knowing that that couldn't be the end of the story.

"Then some girl scouts showed up at my door," Fluttershy said with a shrug. "I was hungry, so I got a few boxes of Thin Mints." She nodded at the plate of the cookies on the table.

"I guess that was the end of it, then?" Twilight said. "All that stuff happening probably killed the mood."

"Yeah, I basically gave up trying for the day. I figured I'd have time later."

"Did you?"

"Yes. But not enough apparently." Fluttershy hung her head. "I still didn't... make it."

"Really?" Twilight tried to not sound too surprised, which was really quite easy. "How often did you try?"

"Every day! If I had time I could go for quite a while. Yesterday I... uh... did it for over two hours."

"And you still didn't come?"

"No." Fluttershy stared into her cup of tea. "It's not like I didn't try, either. I tried all sorts of different positions and used all the different types of porn I have, but nothing worked." She sighed. "I'm starting to think that I might just not be able to do it."

"Hey, don't go and get all defeatist on me!" Twilight said. "You haven't even come close to exhausting all of your options. So the vibrator wasn't enough. It got you closer at least, didn't it?"

Fluttershy nodded glumly. "I guess so."

"See? You're moving in the right direction, you just haven't gotten there quite yet." She leaned back in her chair and began to stroke her chin contemplatively. "Now we just need to figure out how to get there." She thought for a moment. "I have an idea. Are you free this afternoon?"

"Um, I have to go feed the chickens and trim Winona's claws, but after that I should be free."

"Perfect!" Twilight leaped to her feet. "I need some time to prepare, anyway. Give me about two hours, then come to the library. I have a plan!"

"Okay." Fluttershy swallowed, not sure whether to be excited or scared. "I guess I'll see you then."

Against her better judgment, Fluttershy poked her head into the library. She had no idea what Twilight had thought up this time, but a combination of curiosity and a desire to not waste Twilight's time had forced her to stop by. "Twilight?" she called in a voice barely louder than a whisper.

"Right here!" The secret bookcase passageway swung open, and Twilight poked her head out. "Come on!" She waved Fluttershy to follow. "I just finished setting up."

Fluttershy shrugged, and followed her friend down the stairs. She sighed in relief as she saw that Twilight had simply set up a desk and a huge pile of magazines that were probably porn. She had never been so happy to see a giant pile of porn in her life. In the dark corners of her mind, she had been a little afraid that Twilight would have put together some sort magical machine to... do something. Fluttershy had refused to think about it more than that. "So, Twilight..." she asked, "what are we doing?"

"We're going to figure out your preferences. I figured that if we got an idea of what type of things get you hot and bothered, you'd have an easier time of things. Before we get started, do you want anything? I have some tea I could make."

"No, no, I'm fine."

"Great! Let's get started then." Twilight pointed at the chair. "Please, take a seat."

"Okay." Fluttershy sat at the desk. "Now what?"

Twilight opened a folder and took out some pictures. Naturally enough, they were all of naked people. She lined up half a dozen of them on the table, taking care to make the rows straight. Then she picked up a clipboard. "Now then, of these pictures, which ones do you find most... arousing?"

"I...uh..."

"Take your time, I wouldn't want to rush you."

Fluttershy bit her lip and pointed to one of the pictures. "I like this one, I guess." She indicated another one. "And this one, too."

"Good, good." Twilight took a moment to scribble something on her clipboard, then swept the pictures back into their folder. A moment later, another folder was in her hand, and six more pictures were on the desk. "Now what about these?"

"Um... all the ones in this row are pretty good, I guess." She pointed. "Twilight, how many folders are there?"

"Um, about that..." Twilight scratched her head. "In order to have an adequate sample size, we need to make sure that we have enough..."

"How many?"

"No more than fifty."

"Fifty?" Fluttershy suddenly noticed the large stack of folders on the table behind Twilight, and realized that she'd have to look through all of them. "That's a lot of porn?"

"Well, it won't take that long," Twilight answered. "You just went through two in the past minute, so if we keep things moving, we should be done in half an hour. Then we can move on to phase two!"

"What's phase two?" Fluttershy asked hesitantly.

Twilight grinned as she laid out another series of pictures. "You'll find out when you finish going through these."

Fluttershy looked down at the pictures. Half an hour wasn't that long, and while she still hadn't managed an orgasm, Twilight's advice thus far had definitely got her closer. She smiled. "Okay, then. I'll do my best." She pointed one of the pictures, one of a girl with an unquestionably perfect ass. "I like this one."

"All of these except for that one." Fluttershy said. "He's so muscular it's honestly a little bit off-putting."

"Aaaaaand noted!" Twilight scribbled once more on her clipboard. "And that's everything!"

"Really? We're done already?"

"Well, you are," Twilight said. "With the first stage, at least."

"What do you mean?" Fluttershy scratched her head. She could understand how porn had something to do with orgasms, but she wasn't quite sure how this particular approach would help any. If anything, it made the porn less arousing. "What exactly was I doing?"

"I just figured that if we could narrow down what sort of things you like, I'd be able to supply more... visual aids that you would find highly arousing. What I did was take each of those pictures and make note of the characteristics of the people in them, accounting for body type, proportions, facial structure, gender, skin color, hairstyle, pose, and content. I recorded which pictures you found most arousing, so now when I compile the information, I'll be able to see trends in your... preferences. So while I work on that, you may be able to move on to phase 2."

"Phase 2?"

"Yes." Twilight nodded. "Now, you don't have to do this yourself, because I realize you might not be comfortable with it, but it would go quite a bit faster if you did."

A chill ran down Fluttershy's back. "W-what is it?"

"Well, you said that you had exhausted every idea you could come up with thus far, correct?"

Fluttershy nodded.

"If that's the case, I think it might be time to start considering... slightly more experimental methods. Don't get me wrong, I'm not suggesting that you get yourself into bondage or hot wax dripping or urethral sounding or anything like that. Those are all last resort things. Unless they intrigue you, in which case you should look into it." She coughed. "But I'm thinking of slightly more tame examples of things you could try."

"Like what?"

"Um... anal stimulation seems like the obvious choice. It's not particularly difficult and it's relatively safe as long as you lubricate properly and don't insert anything too large. It's not for everyone, of course, but it's worth looking into. I was thinking that while I tabulate your information, you could put on a wig, and perhaps go back to Vibe's shop and find something to use."

The blood drained from Fluttershy's face. "You mean, like, by myself?"

"Well, it would be good for you. I can't go to the store with you every time you need to refill your lube. I've already got some sunglasses and a wig ready." She pointed to an oddly-convenient hook on the wall, on which, sure enough, hung a wig and a pair of large sunglasses. "Or you could wait for a few hours while I go through all these pictures. But really, I don't think I'll be that bad. All you have to do is go in and ask about it."

"Yeah, I know. I'm not sure I want to..."

"Fluttershy, you don't need to be embarrassed. Vibe has worked there for years. I guarantee you that asking about anal toys won't even phase her. She's familiar with way weirder things."

"You sure?"

"Sure, I'm sure." Twilight put a hand on Fluttershy's shoulder. "You'll be fine, okay? You shouldn't be ashamed that you want to enjoy yourself. You just need to be willing to go for it. What do you say?"

Fluttershy swallowed. "I...uh..."

The bell above the door dinged as Fluttershy stepped gingerly through. She had supplemented Twilight's wig/glasses combo with a large shawl and coat, and had hunched herself over so she looked a bit more like an old lady. At the very least, if anyone saw her going in, they would be even less inclined to ask questions that way.

"Good afternoon, Fluttershy!"

Fluttershy nearly jumped out of her skin, but just barely managed to maintain her composure long enough to look up to see Vibe standing behind the counter.

"Y-you must be mistaken!" Fluttershy croaked, doing her best old-lady voice. "I don't know any Fluttershy!"

"It's fine, there's no one else here."

"Okay," Fluttershy said, dropping the act. She couldn't do a very good old-lady voice anyway.

"So, what brings you here on this fine day?"

Fluttershy called up as much courage as she could muster. She had thought that being a model took nerves of steel. That was nothing compared to asking a stranger to recommend things for her to put in her butt.

"Um... well, I'm still having a little... trouble, and Twilight thought I might want to consider trying an...alternative... method..." She waggled a hand in the general vicinity of her posterior.

"Ah, you're lookin' for something to shove up your ass."

Fluttershy felt like she should have been shocked by the vulgarity of the statement, but the sheer matter-of-factness of the statement shocked her more. She wanted to say something, but just nodded sheepishly.

"Well, I've got all sorts of stuff for that." Vibe stepped out from behind the counter and lead Fluttershy down one of the aisles. "You'll want to start small obviously. A small butt plug or anal beads would be appropriate, I would think. That's what I started out with." She scratched her head. "Then again, I never really went any further than that."

"You did?" Fluttershy mumbled. "I, uh... if you don't mind, what's it like?"

"It's... different," she said. "I don't do it a whole lot, but it really does add some variety if you do it right. I might not be really into it, but I can sure see why some people like it. Who knows? Maybe this might be just what you need."

"Y-yeah," Fluttershy mumbled as she surveyed the rows of... things, and tried to imagine what it would feel like to have one inside of her behind. "I hope so too."

"Don't worry," Vibe said, smiling. "Your ass is in good hands. So to speak."

Author's Note

Not too much happening this chapter, but I have some fun planned for next time.

You know what kind.