I'm Cool, Not Cute

You stared into the mirror, a low whine draining out of you. A frilly, black and white maid’s outfit fit snuggly on your body. The skirt rose quite a bit above your flank and was paired with a practically see through inner skirt that came down a few inches lower. The result was a mesh that teased at the curvature of your backside, and more than likely would reveal your hindquarters if you bent over too far. The neckline had a small V that caught a bit of your tuft, pushing it up, and the outfit even came with long, silky, white socks that caressed your legs as you moved.

You couldn’t help but wince as your nether regions tingled a bit when you shifted your weight. Celestia, this was so humiliating. It’s wasn’t like clothes suddenly made nudity taboo, but something about the way they concealed—it made you think there was something naughty about being seen. It was like wrapping someone up in a present. You just wanted to unwrap them right away and it left so much to the imagination. Clothes seemed to say ‘ah, ah, no peeking’ and it drove you nuts, even if you were the one wearing them.

“Anoooon…?” you called out. “Do I have to do this?”

”Aw, come on, Dash. Just let me see you in it one time. Pleeease?”

You frowned. “I don’ wanna.”

”Why are you so embarrassed? I bet you look good.”

Your tail swished back and forth and your ears laid back. “You promise not to laugh or anything?”

”Cross my heart, and hope to die, stick a cupcake in my eye.”

Dangit, he used the pinkie promise. Well… you already lost the bet anyhow. This colt seemed bent on stripping your integrity at every turn, but you were still a mare of your word at the very least. You took a breath and nudged the door open. A few tentative steps brought you out of his bathroom and into his living room. Just the movement in the outfit, combined with Anon staring straight at you set your heart racing.

“H-Here I am,” you said giving his expression a glance. “I know, stupid right?”

He looked taken aback. “What? No way, Dash, you look stunning. Did you look at yourself before coming out?”

You took your eyes off the floor and looked up at Anon. ”Really?”

“Absolutely.”

”I concur, darling.”

You jumped, letting out a yelp and attempting to spread your wings. The maid outfit unfortunately hadn’t come with wing holes, so you instead smacked back to the ground, landing in a crumpled pile of fabric.

“Rarity?!” you yelled. “W-What are you doing here? Don’t look at me! Anon, why is she here?”

Rarity scoffed. ”Who do you think tailored the outfit, Rainbow Dash? Anon invited me so I could see how it fit while I let him borrow it,” she said, and took a sip from a tea cup held in her magic. “And might I say, I am amazed by the results. You look like you could grace any manor, yet there’s plenty of sexiness to it all… who knew our Dashy had it in her?”

“R-Rarity!” you said, covering your face with your hooves.

“Oh hush. Now if we can only do something with your mane. Be a dear and stand up. I have a few forms I’d like you to take so I can see if I got things right.”

“What?” You narrowed your eyes at her. ”Rarity, I’m not modeling for you.”

”Actually,” she said, giving Anon a glance. “As I’ve been told, you’ve lost a bet. Right, Anon?”

”It’ll be quick, Dash, I promise,” he said, putting his hands together in a pleading gesture. “Rarity only let me borrow this for you if I got her someone to model it. Besides, there’s no reason for you to be ashamed. You look amazing in it.”

You let out a whimper. He could flatter you all he wanted… the dress still barely covered your butt, and every time Anon looked at you, your stomach did flips. All it’d take was for you to turn around. Your tail didn’t do much on it’s own. Celestia, why did clothes make you feel MORE naked? You caught yourself rubbing your back legs together. The thought of Anon seeing you drip onto the floor made your face heat bright red.

“Anon, can I just… do something else?”

Anon sighed and gave you a disappointed look. “Well… I don’t want to force you if it really bothers you. But you did lose, and I know you wouldn’t have let me off the hook so easy.”

You flinched. He was right. You wanted to do far worse too. Karma was out of blood today.

“Rarity, do you have anything else Dash could try?”

Rarity put a hoof to her chin and hummed. ”I have some other pieces, but I’m afraid they’re a bit more risque. They’re part of a special interest line and this is one of the more tame outfits.”

“Ah I see…” he said, frowning. “Well thanks anyways. Dash go ahead and give her the outfit back I guess. I’ll think of something else.”

You started to reach back and use your teeth on the ties on the midsection when Rarity spoke up. ”Rainbow! Don’t use your mouth. That’s high quality cashmere.”

You spat out the knot you were working out and glared at her. “How they heck am I supposed to get this thing off then?”

“Just let me do it, and stop being so fussy,” she said and her horn flared to life.

A blue aura enveloped your socks and began sliding them off your hooves one at a time. You bit your lip as each one slid down your limbs, stroking your fur all the way down. Next Rarity started loosening your skirts, and you instinctively moved your backside away from Anon. The skirt fell to the floor and the cool air met your flanks. You shuddered. It never occurred to you how erotic it would feel to have only the top of your outfit left. Your whole backside felt exposed—right out in the open for anyone to see.

For Anon to see.

Your breathing picked up and you shut your eyes. This was much worse. You couldn’t do this. Not with Anon in the room, and you couldn’t just ask him to leave. Anon might not understand why but Rarity sure would. She’d gossip to everyone about it! That’d be even more embarrassing.

“R-Rarity?” you said as you felt her magic start pulling your top down. You slapped a hoof to the fabric, stopping it from slipping past your shoulders.

”Hm? Yes, darling.”

“Put the skirt back on, um, p-please.”

She cocked her head to the side. “Well whatever for? I’m already mostly done,” she said, the fabric loosening around your shoulders. “You’ll be down to nothing in no time.”

“Please don’t word it like that…”

”Dash, I’m afraid I don’t understand what you’re trying to tell me.”

“Just… put it all back on please. I’ll do the stupid modeling thing. I just want to get this over with.”

Anon and Rarity paused then traded looks.

”If that’s what she wants,” Anon said with a shrug.

Rarity gave a sigh and a somewhat annoyed hmph but thankfully slid your top back on and started fixing the skirts. The fabric dragged up your backside, sliding across your plot and over your hips. Thankfully you didn’t make any noise at that, but you were started to feel a bit dizzy at this point.

”Alright, now that things are in order again, we can get started,” Rarity said with a pleased smile. “Rainbow Dash, start by pushing your chest out and arching your back.”

You tried your best to school your features and posed, trying not to look at Anon, who you knew would be staring straight at you the entire time. You felt your marehood wink and a thin line of something hot and wet dripped down your inner thigh. This was going to be a long modeling session.

The session lasted an hour, but it felt like an eternity. There was no way half of those poses were “standard practice” and you could see that perverted glint in Rarities eye when she told you to try embracing the role more.

Thankfully Anon eventually intervened and told Rarity that her part of the deal had surely been dealt with and sent her off for the time being. Your mind immediately wandered to risque territory when it was just the two of you, but Anon only asked you to do some chores while he relaxed. No mocking or teasing you—He just put his feet up and read while you dusted and tidied up. Part of you felt relieved, but at the same time, you’d expected him to really take advantage of this. You were still nervous, sure, but it felt slightly anticlimactic in a way. He should have teased you a little, right? You grumbled to yourself. This colt was so frustrating.

Eventually dinner time came around and he ordered pizza instead of having you cook something. Though he asked you to do the dishes. Honestly considering he treated you and let you pick the topping, simply doing the dishes in return wasn’t much a punishment. Any decent mare would have done that for their stallion.

You pause mid scrub. Anon as a house stallion? What would that even be like? He could cook a mean meal when he wanted to. And as long as he’s not teasing you, you got along pretty well. He kept the place pretty neat and organized but wasn’t perfect and would tolerate a little mess from you now and then. Probably wouldn’t be so bad living with him, honestly. You shook your head, brushing aside the thoughts. Who were you kidding... Anon was a total Janefilly. There’s no way he’d want to marry a rough mare you.

The last dish joined the others on a drying rack and you let out a satisfied sigh. Glancing out the window, you saw the sun was going down. Only a little while longer…

You’d agreed that sundown would end the bet and call your punishment game fulfilled. He had time for one more thing. You briefly considered hiding in the kitchen, but something made you not want to. Anon had dressed you up and teased you, but he’d been fair. Better to just face it like a mare and give him his last few minutes. Hopefully it wasn’t too bad. You took a deep breath and headed into the living room.

Anon lay back against one side of the couch, flipping through channels with a remote. His shirt had ridden up a bit, letting you see just a bit of his lower torso. You gulped. He shifted, revealing another inch and you leaned forward, eyes transfixed as more skin revealed itself to you.

“You finished, Dash?”

You jumped and snapped your eyes to his face. “Y-Yeah. Finished ‘em.”

If he’d caught you leering, he said nothing of it, and instead beckoned you over. You walked over, head slightly down, ready for whatever he cooked up to complete your punishment game.

“Alright, Anon, lay it on me. I can take it.”

He chuckled and smirked down at you ”Okay” he said. “Your master orders you to get up here and sit in his lap.”

A light blush spread across your muzzle and your eyes darted between him and floor. Oh, Celestia he was gonna make you feel like a colt… But… You sighed. Come on, Dash, be a mare and stick to your word. You took a deep breath, then hopped up and turned to plop yourself into his lap. You tentatively leaned back into his chest, thankful that the outfit held your wings down.

He picked up the remote again and flipped the channel. The logo for ESPNY flashed across the screen. Your mouth turned up in an open smile and you sat up as you realized this was tonight’s crashball game. The Manehattan Matadores vs the Cloudsdale Cloppers, the grudge match for the right to fight in the seasons finale in Canterlot. You thought you were gonna miss it.

But… Anon didn't watch this stuff. You knew that for a fact. Why would he want to watch...? Wait, was he doing this for you?

“Um…” you said, tilting your head up at him. “How’d you know I’d be missing the game today? I don’t even talk about my team to anyone.”

”Is that because you root for the Manehattan Matadors instead of your hometown team?”

You stiffened. “Who told you?”

”Fluttershy. I also know it’s because they’re underdogs, and something about that makes you love rooting for them. They’ve also been having issues with their name because some ponies think it’s insensitive towards Minotaurs, and that gets you fired up from time to time.”

“I know!” you said, throwing your hooves up. “It’s so dumb. They’ve had that name for decades and now ponies want to change it? Ugh.” Anon chuckled and you cleared your throat. “A-Anyways yeah, if they can win here they can go to the championships. They haven’t been this close to a gold horseshoe trophy in years and they really deserve it. I mean, Buckeye really has put her sweat and blood into this…”

You trailed off, realizing you’d been rambling at a colt about sports and cleared your throat. “Right, but… anyhow, judging by the score it looks like this won’t be their chance this time. But hey, there’s always next year.”

Anon nodded along, watching the game without saying much. You turned and looked up at him, furrowing your brow.

“Anon?”

”Mm?”

“Do you even like crashball?”

”Not really.”

“Then what gives? Aren’t you going to make me do something humiliating?”

He gave you a look that seemed to say ‘really?’ and put his hand on your head, gently ruffling your mane.

”Now why would I do something like that?”

“Well…” you said, looking down at your hooves. “I lost. A-And the outfit… it’s k-kinda… you know.”

“Oh Dash,” he said and pulled you into a hug, forcing a totally marely sound out of you. “None of this has been about making you feel bad or doing anything mean to you. Heck, even though I knew you’d hate it at first, I knew you’d look really cute in the maid uniform.”

You stared up at him, mouth slightly ajar. All his praise from the day echoed in your mind. He wasn’t teasing you? He meant it? Your heart sped up and you pulled your hooves to your chest. You looked good? Your eyes drifted down, looking at the way the uniform lay on your body, and seeing it in a new light. Maybe it wasn’t THAT bad.

“It’s okay… I look good in it I guess, so. I mean it’s no big deal. Heh, I bet I could make anything look good anyhow. It’s just not my style, is all”

“Mmhm…” He smiled and lowered his chin to your mane. “And I figured after you’d worked so hard and stepped so far out of your comfort zone, you’d like to unwind a bit and catch your game.”

You sat still for a moment, staring off at nothing in particular. That… was actually kinda sweet of him. You turned your attention to the game and relaxed.

The two of you stayed like that for a little while, watching the game with you snuggling your back into his large frame. Anon’s size tended to intimidate and bother you most times. It was so frustrating to have a stallion so much bigger than you. But laying against him, his arms around you—it felt good to put your back against his broad chest and nestle into him. Being the little spoon like this felt nice in a way. Not so bad after all really.

“Hey, um, Anon?”

”Yeah?”

You fidgeted with your forehooves and bit your lip. ”I—don’t really know how to say this but… today wasn’t so bad.”

“I’ll take that as a compliment,” he said with a smile. “Spending my time with a such a cute mare wasn’t too bad for me either.”

You puffed up your cheeks and crossed your hooves. There he goes again, you thought. But instead of the usual annoyance, you felt content him say that. Didn’t mean he had to know that though. A sigh escaped you and relaxed back into him.

“I’m cool, not cute.”