You brush strands of red bangs out of your eyes and look down at Anon walking through town from your cloud perch. Twilight had apparently sent Anon out to get a few things, and you’d just so happened to catch sight of him earlier. You had decided he needed to be monitored for... safety reasons. Didn’t want any mare taking advantage, Celestia forbid. And no, this is NOT stalking. This… is spying. Spying is cool
Anyhow, the colt sure did seem like he could use a mare’s guidance; He looked completely lost at the marketplace. What Stallion didn’t know how to flirt, chat, and haggle? He just accepted whatever price they tried to smack him with. Poor guy… Some of the other mares picked up on this and took pity thankfully, offering him a wink and a lower price. You roll your eyes. Colt-mode is easy-mode, but that wasn’t Anons fault. Next time you’ll go with him and stop those stupid mares from eyeing him up so much.
You zip over to the next cloud, a colored streak following in your wake as you keep your eyes trained on the creature walking through town. A smirk forms on your face. You were only a few feet above him, but with your excellent sneaky skills, he still hadn’t noticed a thi—
“Dash, what are you doing?”
You blink and see the human looking up at you, an eyebrow quirked. Quick, think of something! You give him your best poker face.
“N-Nothing!”
…
…
Nine out of ten.
He just shakes his head. “If you want to talk to me, just come down. I won’t bite.”
He won’t bite? Do… Do humans bite? You start to feel a knot in your stomach. Twilight had said one time that humans were a predator species. Celestia, was he like something from the Everfree? Wait, no. You shake your head and scowl. C’mon, filly, you were Rainbow Dash! He may be a human but he’s still a colt. You glare down at him. He chuckles and you hear him say the word ‘cute’ under his breath
Your eyes shot wide. C-Cute!? You zoom down to the ground. “L-listen, buster. I’m cool, not cu—”
He gives you a smile as he boops your nose, and you can’t stop from letting out a squeak. Anon grins before turning and motioning you to follow. D-Damn—stupid— human—colt— thing. You felt heat rushing to your cheeks. Thank Celestia he wasn’t looking at you. Damn guy had a weird way of messing with your head. It was something you found interesting about him yet it bothered you to no end.
“So, Dash, you have the day off?”
You blink, his voice breaking you from your thoughts. “Oh, uh, yeah. Weather duty and all that. There’s only a few seasons we have to really hit the skies hard. Um… So… Twilight has you doing errands? You don’t usually—uh.” You articulated with a hoof. Trying to find the words.
He stops and turns to you, making you freeze. S-Shoot, is your face okay? You’re not flushed still, right?
“I live in the Castle, Dash. Helping out this much is the least I should do honestly. I just don’t like how… concerned she can be,” he said with a faint smile.
He bends down and puts one of his hands on your head, giving you a soft scratch between your ears. Sweet Sun… You could feel your eyes lower as a feeling of utter bliss channeled it’s way through you. Dammit you hated when he did this! More importantly, HOW did he do this?! You open your mouth to tell him to knock it off but all that comes out is a breathy moan. Your leg twitches as you slowly sink to your haunches, the feeling melting away every thought.
Then, it stops.
Your eyes flutter open to see that human’s stupid, foalish face beaming as he stood over you. “You ponies sure are cute…”
He… He just… F-Fuck this colt! He did that right in the middle of the street like it was nothing! Worst part was that it totally worked. You look around to see a few mares giggling and giving you looks. Your face suddenly felt like it was on fire and you snapped your gaze to the pavement. He had to know he was teasing you. There was absolutely no way the colt didn’t know what he was doing, right? Jeez… he made you feel like such a beta sometimes.
Anon gave you a look. “Dash, you okay there? You look kinda overheated. Do you want to take a rest in the shade? I have some water you can drink.”
Aw… heh, how nice. He was worried and wanted to take care of y—DAMMIT DON’T FALL FOR THE RUSE!
“Nah, I’m fine,” you say as you close your eyes and push your chest out, crimson face and all. T-Take that. He shrugs and looks off toward the castle, his brow furrowing at the sun lowering past the treeline.
“Heading back already?” you ask.
He nods. “Yeah, Twilight’s probably wondering where I am. She likes to calculate exact timings and all that to keep track of me, and she probably didn’t factor in our little meetup. You know how she gets.”
“Well she doesn’t want you out alone when it gets dark, ya know. She’s just looking out for you.”
He quirks a brow at you. “I can handle myself. I don’t get why she tries to baby me so much. I’m bigger and stronger than most ponies.”
Normally you’d just nod along and humor a stallion talking like that, but with Anon, that made you wonder. He did look pretty strong… could he actually overpower you? Nah, he was a Janefilly but Anon was still a colt, no matter how big he was. Probably throws like a boy and cries the moment he gets hurt. Sports definitely separated the fillies from the mares. If he actually tried to tussle with the mares, he’d be the one looking like a beta.
You blink and a smile works its way onto your face. Of course! He was always able to make you feel like a little beta because he was always in his element! But if you could get him in yours, you’d show him just how marely you were in the best way possible. By beating him at diamond ball! You could even make a punishment game wager. Ooh, that’d be fun. What if he agreed to be your servant for the day? W-What if you made him wear a cute butler uniform. You bite your lip. L-Lewd.
“Hey uh, Anon, if you want to hang out, there’s a community diamond ball game at ponyville park. You up for it? I’ll tell the girls to go easy of course—just a casual fun game.”
You put on your winningest, alphamare smile. Colts always fell for that look. Take the bait filly, Dashie wants to see YOU made the colt for once.
He purses his lips. “Yeah sure. I’ve been looking for something interesting to do lately. Twilight might make a fuss though.”
“Just tell her you’re helping Applejack or something. You’ll be fiiiiine.”
He shrugs. “I’d rather not lie but knowing how… protective she is, I think that’s the best option.”
Oh, this was going to be so fun. You could feel yourself practically bouncing now. Keep your cool, filly; Never act too eager.
“Anon, what say we make this thing interesting?”
He quirked a brow. ”... interesting how?”
“Well, if you’re not chicken that is, how about we say the loser has to wait hand and foot on the winner, for the rest of the day?”
Anon paused and gave you a strange look. ”I thought you said you wanted a casual game?”
“Well yeah, but I mean it’s so much more fun when there’s a reason to win.” And when you get to tell Anon to bring you cider in a skimpy outfit… That’d take him down a notch.
”Whatever you say, Dash,” he said. “Alright, the loser does some favors. Let’s just not get crazy with it.”
Oh… you won’t get too crazy. This time. The real lewd stuff was for the NEXT time he lost.
“I’ll see you at the Hay Tumble field at 9 then,” you say as casually as you can, then zoom off before your excitement can get the better of you. This was gonna be good.
Be the fastest, coolest, mareliest flier in Equestria. The one and only Rainbow Dash. And today was the day you got to make a colt cry!
...
You know what, it sounded better yesterday, but screw it. Anon would do whatever you wanted later, and that made it worth it in the end. He deserved it anyways with how much he was always messing with you. You blew the colored bangs from your eyes and pouted. Stupid Anon… always making you feel like a little foal, saying you were… cute. That funny feeling started up in your stomach and you grumbled. This time you’d be the one making HIM look cute. A skimpy butler uniform should do nicely to put the image in his mind. Maybe with socks… and a loose fitting shirt with a plunging neckline. The wings on your back twitched. Ooh… that sounded amazing.
”Dash, done warming up yet? Er… hey, is that a wingbo—”
“NO!” you said, whirling around and coming face to face with Home Run.
She blinked, stopping only for a moment in chewing her bubble gum before shifting the wooden bat on her shoulder.
”Okay…” Home Run said, giving you a blank look. “Well the girls are ready to get started. Oh, and the human came by dressed in some sort of uniform. Said he was playing and you’d explain everything.”
“Right, I’ll be right over. Just give me a minute—I gotta, stretch and stuff,” you said clearing your throat.
There was a pregnant pause before Home Run spoke up again. ”I always found thinking about something else helps.”
You flinched and scrunched your muzzle. Stupid Anon...
You weren’t sure how the girls would react to including Anon in your regular games. Matches on the green could get pretty rough and tumble. Fights never broke out or anything, but slide tackles, rough elbowing, and ponies getting beaned by the hoofball happened often enough.
They all seemed pretty happy to rein themselves in for Anon’s sake though. Everypony smiled and gave him advice on how to hold the smackstick. Dust Devil and Hay Stack even jumped at teaching the rules, each of the other mares chiming in here and there, trying to help Anon learn. He remarked a few times that the rules sounded a lot like something called based-ball back in his world oddly enough. Oh colt, this ain’t no sissy stallions game, whatever based-ball was. He’d learn.
Eventually you got tired of everypony surrounding Anon, giving him advice and explaining more and more stuff, and just broke it up and got two captains picked. You stood in line like usual, chest puffed out, ready to be snapped up within the first few picks. But of all things, Cornstalk picked Anon first.
You balked. What the hay…? There’s no way he was good, let alone a first pick. What was this filly trying to pull? You quirked an eyebrow and looked around you. Nopony but you seemed to find this odd. Instead, they all cheered him on as he walked over.
”Good luck Anon!”
”Do your best, colt.”
”Go easy on us, ya hear?”
”If you need any pointers, don’t be a stranger.”
You narrowed your eyes as the mares continued to encourage him and Cornstalk gave him a hoofbump. Each mare seemed to be enthralled with him, watching him with intense interest even when the next captain went to pick a player. You furrowed your brow. Something’s not right here… why would they be so interested to see a colt pla—Suddenly, the realization dawned on you. A COLT play. Oh no… Ohhhhhhhhhhhhhhh filly no no no—
Home Run bunted Anon’s straight pitch then took off at a light trot down the line to first base. Anon scrambled up, grabbed the ball then whipped it over to first.
“OUT. That’s the game,” the umpire yelled.
Home Run gave a sheepish smile and rubbed the back of her neck. ”Ya got me, big guy. Good job.”
FUCK. You stared up at the scoreboard a horrible feeling settling in your stomach. 32 to 5. Anon wasn’t bad as it turns out. He took to the pitcher’s mound despite the girl’s warning that it was a hard position and he could get hit with the ball. Anon being Anon of course he HAD to show them he could do it, and for somepony with no magic, he did a pretty good job, you had to admit. For a colt, that is.
But he still wasn’t better than the two other pitchers on their team, Whiplash and Hail Mary, who pretty much sat useless in the outfield the whole time. No, with the teams as they were, this should have been easy… There was just one apple-bucking problem.
“You guys went easy on him!” you said, whirling on your teammates.
The girls gave you a look. ”Well… yeah,” Home Run said as she walked to your team’s bench. “Did you expect us to play seriously against a stallion? Come on Dash, I know you like to win but have some integrity. Look how happy he is.”
Anon was standing in his stupid little based ball uniform that admittedly looked cute as tartarus on him, and he gave you a smile and a wave. “Good game, Dash. That was fun.”
You whipped back to your teammates. “But, but, but… you don’t understand! He was supposed to cry!”
Home Run furrowed her brow. ”... are you for real?”
“Yes! I mean no! I mean… ughhhh, it’s more complicated than that.”
Dust Devil gave you a bemused look and popped her bubblegum. ”...k”
“You know what, I don’t need that kind of negativity. I’m gonna go—”
You let out a mewl as Anon scooped you into his arms from behind. He snuggled his big dumb face into your mane as you squirmed in his grip.
“Heya, Dashy. You did good out there, but my team won, and you know what that means.”
A blush formed on your cheeks as he carried you away like a yearling, the whole hoofball squad looking on with wide eyes.
“Anon, n-no. Put me down already. Everyone’s looking.”
”Nope. I won. It’s snuggle time until I get you in your outfit for the day.”
A cold sweat broke out on your forehead. ”Outfit…?”
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.”
