My Roommate Fluttershy

by KillerRobotQuote


Chapter 3: Number 19

"Dante?" 'Fluttershy' called. "I'm done with my bath."

"Okay," I called back. "Jus' stay there. Imma get you some clothes." I entered my little sister's room and opened the second drawer of the dresser, where I was greeted by the sight of a jumbled pile of multi-colored panties and bras. Embarrassed, I grabbed the first bra and panties that I found and shut the drawer. I couldn't believe I just went through my sister's underwear! If she found out...

Pushing that thought aside, I opened the top drawer and grabbed a pair of jean shorts. I hoped that they would fit her, since my mom's would be too baggy. Finally, I walked to the closet and chose a gray striped t-shirt. Satisfied with my selection, I returned to the bathroom and cracked the door open just enough to slip the clothes in.

"Here, put these on," I told her, dropping the clothes on the floor and shutting the door.

"Thank you," she replied, her voice muffled slightly by the door. "Um, I was wondering... Do all humans have to wear clothing? Because ponies rarely do."

I bit my lip, keeping myself from saying the first thing that entered my head. Instead, I decided to humor her for the time being. Now was not the time or place to tell her she was nuttier than a granola bar. "Yeah, we do. We're only allowed ta be naked fer bathing. Anything else, anywhere else, ya gotta be covered."

"Um, what's this thing?" she asked.

"What's what?"

"I don't know what it - or any of these clothes, really - are called. Could you come in and help me?"

"No," I said quickly. "I mean... Ah can't come in while yer getting dressed. But I'll tell ya what ta do if ya need me ta."

"Okay," 'Fluttershy' began. "This thing is kind of small and stretchy."

"Those're panties," I replied. "D'ya know how ta put'em on?"

"I think... they go between my legs?"

"Yeah, tha's right. Jus' slip one leg through each hole an' pull'em all tha way up."

I paused for a moment. "Oh, they feel good!" I heard from behind the door.

"Good fer you," I chuckled. "Next ya do th' bra."

"Which one is-"

"It's th' one with the... uh... the... two cup things on it. It's kinda' flimsy."

"Oh. What's this do?"

"You use 'em ta support yer titti- yer breasts. You got it, right?"

"I... I don't know how to put this on."

I rolled my eyes. "C'mon, ya jus'... um... you..." My face fell. "You jus'... hook it... from behind... I... think? Oh my god," I chuckled from embarrassment. "I-I'm not... I'm not really sure!"

"So, do I have to wear it, then?"

"Well, ya don' have to, but ya really should." I thought for a moment. "All righ', you know wha'? I'm gonna come in 'n' help ya with that. Be a learnin' experience fer me, too," I joked. "Okay, I'm gonna open th' door and I want you ta have yer back toward me, akay?"

"Okay," 'Fluttershy' replied.

I turned the knob and gently pushed the door open, peeking my head in to make sure I was clear to enter. 'Fluttershy' was turned away from me, holding the green bra in her right hand. My eyes found their way to her posterior, tracing the contour of the pink panties along her rump. I felt a stirring in my nether regions.

No, dumbass, I silently scolded myself. No. Bad. Before I let it get any worse, I walked up behind her and took the bra from her hand.

"Okay, bear with me. I'm not entirely sure what ah'm doin'."

"It's fine," 'Fluttershy' whispered.

I held the shoulder straps of the bra in each hand and held it over her head. Then I brought the bra down in front of her. From behind, I pulled the bra against her torso, then slid it up until it stopped against her breasts.

"Okay, now these straps? Ya gotta put your arms through 'em an' get 'em on your shoulders." I let go of the straps as she complied. "'kay, now adjust th' cups so they're... erm... comfortable."

"It feels tight," 'Fluttershy' remarked.

"Well, 'magine it would. It's designed to... uh... support... yer... mammaries." I pushed her long, pink hair over her shoulder with my arm and grabbed the clips on the back of the bra. "Akay, now th' last part is ya have ta clip it together in th' back. This looks like it's jus' a hook thing, er whatever it's called. 't's pretty simple. Ya jus' bring 'em together like this..." I pulled the clips together, but about three inches apart from each other, they stuck and wouldn't move any closer. 'Fluttershy' made a soft moaning noise. I stopped, stared at the clips for an moment, then tried again. I pulled much harder this time, but at an inch apart, the bra gave too much resistance, and the clips wouldn't come any closer.

"Aahhh!" 'Fluttershy' cried out. "Dante, it's too tight!"

I tried one last time, but to no avail.

"Dante, please, stop! Please, it's too tight!" 'Fluttershy' begged.

I released my grip on the bra and let my hands fall to my side. "Holy shit," I muttered.

'Fluttershy' turned toward me, her arm pressed against the bra so that she was still covered. A worried look crossed her face. "I'm-I'm sorry," she whispered. She looked to be on the verge of tears.

"N-no, it-it's not yer fault. Sorry, it's jus'..." I didn't know quite how to say it. I took a deep breath and sighed, blushing slightly. "It's too small."

"Wh-what do you mean?"

I shifted uncomfortably. "I mean you're too big... there... and it's not gonna fit you. You'll... have to do without one for now."

'Fluttershy' stared at the floor, dejected. "Oh... okay," she whispered. She let her arm fall, and the bra followed suit. Luckily, I saw what she was doing and turned away just in time.

"So!" I said quickly. "Um... I, ahh... I guess you're gonna have to wear something else. That shirt's my sister's too, so, yeah. You could probably fit in it, but you'd stretch it out, and, yeah, that won' do." I scratched the back of my head, nervous. "I think one ah my shirts might be big enough. You put the pants on, an' I'll see what I can find."

I picked up the shirt and tossed it nonchalantly onto my sister's bed after I left the bathroom, then turned into my bedroom. I made my way to the closet, sliding a pile of papers and junk out of the way with my foot. Jesus Christ, my room was a mess. Papers from high school, a couple of library books, pencils, drawstring bags, my class ring, Mad Libs, unused wallets, Calvin and Hobbes comic books, a Metallica album, a computer mouse, a flashlight, a GameStop gift card, a glass Coca-Cola bottle, dirty laundry, clothes hangers, sunglasses, a deck of cards, my iPod, Winnie the Pooh, and even Pikachu were scattered across my room in an unnavigable mess. I'd better clean this up soon.

I slid the door to my closet open and skimmed the selection I had. Something seemed off. "Hey, where're my hoodies?" I wondered. "I always-... oh, right. They're packed away. Dumbass." I gave myself a mental facepalm. I somehow forgot that it was eighty degrees outside and that you don't wear hooded sweatshirts when it's that warm.

With my first choice gone, I sighed and looked at what remained. It was slim pickings. I had a handful of t-shirts that fit me just fine, but being 5'10" and only 140 lbs., my shirts were pretty skinny. The few that were bigger were just plain ugly. It didn't look like I had anything that would... wait a second... is that...?


'Fluttershy' managed to get her shorts on by herself, which came as a relief to me. I'm not sure why I doubted her, honestly. She already put the panties on by herself, so why would she have any trouble with shorts? Clearly, I underestimated her intelligence. Man, I'm a jerk, sometimes.

"All right, I found a shirt that I think'll fit. Try it on." I tossed the shirt in the bathroom, still refusing to look directly at her and rather opting to look no higher than her hips.

'Fluttershy' fumbled with the shirt a bit. "Oh, it's so light." she remarked. She slid it over her head and pulled it down to her waist.

I glanced up at her and bit back a chuckle. Still, I couldn't suppress the smile that was growing on my face.

"Um, is it all right?" 'Fluttershy asked, leaning on the sink. I nodded.

"Oh, yes, it looks good," I said, laughter finding its way into my voice. "Jus' tell me, how do ya like Bernie Kosar's Cleveland Browns jersey?"