Day Boulder Dash in Equestria (Final)

>a couple days later, the day finally came, the day of the race...
>neither of you slept much the night before, too stoked for the next day
>however, this didn't seem to affect Milky, as she was all too eager to rush out the door for the race

>with such a short time between the day she got the clothes and the start of the race, Milky barely had time to train
>you weren't concerned about how conditioned she was, despite not having raced in a while, she already looked more than ready
>you just wished that she would run around in the clothes you got a bit more, and get more accustomed to them
>however, Milky insisted that they fit her just like they were a part of her, and you trusted her opinion

>the sun was high in the sky, the leaves of the trees golden brown, when the two of you were walking toward where the race would be held
>Milky was sporting her bra and her running pants, beaming like it was the happiest day of her life
>you felt happy for her too, the smile she was wearing was priceless

>eventually, as you approached the golden edge of the forest, you saw it...
>there were balloons, bleachers, ponies selling food.....shit, they definitely went all out for this.
C'mon Milky, lets go get you signed up

>the both of you approached the sign-up booth, Milky bounding behind you in a way vaguely reminiscent of Pinkie Pie
>as you stood in line, you suddenly
>"Anon? What are you doin' here?"
>you and Milky turn around to see a familiar, Rainbow maned pony...


Hey Dash.
>Dash raised an eyebrow at you, smirking
>"Y'know...last time I checked they only let ponies do this race."
>you chuckled a bit. After a while in Ponyville, you learned to tolerate Dash's occasional jabs
I'm not here to race RD, I'm just here for a little moral support.
>"Moral support? For who...."
>Dash suddenly noticed Milky standing beside you

>"Hey...I know you. You're that milkpony from Trottingham. Wait..."
>The sides of Dash's mouth started to twitch, fighting back laughter
>"You're not telling me YOU'RE going to be in this race?"
>Milky took a few steps back, looking at the ground
>"Well....I...."
>You jump in, jimmies now rustled. It was one thing if she made fun of you, but Milky was a whole different deal...
And what exactly is so funny about that? You don't think she's going to leave you in the dust?
>Dash responds with a high pitched squeal of laughter
>Milky sunk even lower to the ground, her face burning red
>you would have had no qualms with kicking Dash in the face at this point, but decided against it
You know, I remember hearing about a pony who came in LAST place during the last Running of the Leaves...
>that did the trick, her laughter stopped almost immediately
>"HEY, thats ONLY because AJ and I were too busy killing each other to win the race!"
>Dash lets out a snort, walking away
>"We'll see who wins this one, Anon, just you wait..."

>"Thanks for sticking up for me, Anon."
>Milky was looking back up at you, the blush on her face faded, and a smile back on her face
Hey, I meant every word of it. You're gonna do great out there.

>pretty soon, you were sitting in the bleachers, watching Milky and dozens of other ponies lining up at the starting line.
>Milky was easy to spot in her blue pants, now with the number 99 stuck on one side of her flank
"GO MILKY! YOU'VE GOT THIS GIRL!!!"
>as you shouted, a few ponies in the bleachers looked back at you, annoyed
>clearly they weren't used to having to share seats with a talking monkey
>you didn't care though, you wouldn't be there long...

>As you watched, a couple ponies approached the starting line. One of them holding a large, green flag.
>the other one cleared his throat
>"RUNNERS! On your mark! Get SET! GO!!"

>as the other pony waved the green flag precariously in his mouth, the entire pack of ponies suddenly took off from the starting line
>but as you watched, before they even disappeared into the forest, a blue and cream colored pony broke away from the rest of the pack...
>Milky....god DAMN she was fast. You just hoped that she'd save her breath until the end of the race

>As the crowd cheered though, you had no intention of sitting around all day waiting for the ponies to get back to the start/finish line.
>no, you wanted a front row seat to watch Milky as she decimated everyone in the race
>making your way out of the bleachers, you slowly started slinking toward the edge of the forest while no one else was looking...

>As you trekked through the trees, you eventually managed to get your bearings
>no one who wasn't in the race was allowed out on the trail
>despite the race being technically about helping "the leaves fall", the prospect of cheating was taken seriously
>if you got caught, you'd probably be in some pretty deep shit for fucking around with a Ponyville tradition

>the terrain was definitely not easy, looking like it was almost made to thwart cutting through by a pony
>however, you and your two long legs managed to traverse it
>it was a good thing too....since you weren't exactly an athlete, and keeping up with any of those ponies, much less Milky, would have been impossible
>a half an hour later of hiking, you eventually found the trail
>to your relief, you found that there was no signs of hoofprints.....wait a second....
>you spy a single set at your feet, stretching down the road
>holy shit....they must be Milky's. Was she that far ahead?!


"Milky? What's wrong?"
>she didn't have to answer you though, you already saw it...
>underneath her, on her pants, right where her breasts were being held in place, you saw a twin pair of wet patches blossomed out on her pants, a few white droplets hitting the ground...
>Oh hell no, not now.....but you had milked her earlier that morning! She couldn't have been THAT full...

>"It....it keeps rubbing up against me, and I can't hold it....."
>of course....she wasn't way too full of milk, the pressure and soft rubbing of the bra was slowly milking her...
>you feel like kicking yourself in the head for not forseeing this, you both would have probably found this out beforehand if she just had a little time to train with her new clothes.....

Dammit.....look Milky, maybe....maybe if I can get those clothes off and milk you really quick, then you can finish the race. I think we have some time...

>she nodded without hesitation, turning her flank around for you to help take off her pants
>however, as you had your hands on her hips, you suddenly heard a low rumble of hooves pounding the earth not too far away
>Milky's ears perked up too, and she wheeled around, looking up at you in a panic
>Anon! HIDE! You're not supposed to be out here!"

>instinctively, you dive into the bushes, while Milky takes off down the trail
>you see her gait is a little less smooth and coordinated than before as she galloped
>god fucking dammit...
>as you hid in the bush, no more than 30 seconds later, a huge crowd of ponies ran down the trail after her, led by Rainbow Dash
>god fucking dammit, there had to be something you could do....
>when the last pony was out of sight, you got up and started cutting through the forest again, hoping to catch Milky again

>this time, you were tearing through the forest like a madman, struggling to get ahead
>you HAD to get in front of Milky this time, there was no way she'd be able to get through the race like that
>as you kept running, feeling a little nauseous at how much you were exerting yourself, you eventually got to a part of the trail just inside the forest
>from there, you knew the finish line wasn't too far away

>gasping for air, you searched around, not seeing any hoof prints....good, nobody had come through here
>not more than a few minutes later though, you heard hooves beating down the trail
>hoping that it was still Milky out in front, you dove for another bush, peeking your head out
>sure enough, the blue maned little mare was galloping down the road
>however, she was wobbling back and forth....she looked like she was going to collapse...
>diving out of the bush, you ran toward her
Milky!!
>she looked up at you, her face red, and panting softly
>"A....anon...."

>you skid down to your knees, and she practically falls into your arms
>the wetness of her milk on her running pants has now spread to her knees...
>fucking hell....a good milking over the course of fifteen minutes or so would definitely leave Milky kinda woozy
>But this kind of teasing, over the course of an hour? It must have been unbearable.

>Milky looked up at you, trembling with embarrassment
>"I....I....."
>her body suddenly began pulsing in your arms, milk splattering on the ground as she lost control again
>you held her close, rubbing her back gently as she slowly milked in her pants, while she struggled not to cry
>the wetness soon spread down to the cuffs on her back legs, dribbling down her hooves

>she managed to stem the flow though, and you soon spoke to her

Milky...lets head home, nobody has to see you like this.
>"N...no. I have to....I have to finish this race Anon..."
No you don't. You've already proven to everyone what a good runner you are...
>Milky shook her head vigirously
>"You...don't understand. I HAVE to finish...."

>at that moment, you heard it again....the ominous sounds of hooves down the trail
>Milky's eyes went wide, and she turned around, ready to run again
Milky! Wait!
>"I'm NOT gonna come in last place Anon!!!"
>she kicks you in the chest, sending you into the bushes again while she sprints down the trail
Ow...

>once again, you wait in the bushes, waiting for every last pony to pass
>when they do, you sprint toward the treeline, from where you can see the trail taking a long, curving route towards the finish line
>you keep moving, dodging through the trees, watching Milky running in front of the leading pack of ponies
>however, they were gaining on her. Fast

>as they approached the finish line, you suddenly saw her get swallowed up by the pack....right as the checkered flag dropped
>breaking out of the treeline, at a point where you hoped no ponies would see you, you approached the crowds of ponies cheering and celebrating

>however, as you got closer, you saw Milky plopped down on the ground, a smaller crowd of ponies gathered around her, mumbling and whispering
>oh no...

>you cut through them, sliding down to Milky's side and putting an arm around her.
>her right leg was against her face, trying to hide the tears rolling down her cheeks
>her pants were positvely soaked with milk, the ground underneath her flanks even growing dark where she sat
>You feel positively horrible. Milky must have been more mortified than she had ever been in her entire life.
>And it was all your fault. You got her the clothes, you told her to do the race...
>you sigh with resignation and guilt
"C'mon Milky, let's go home..."

>as you help her up, her legs wobbling unsteadly underneath her, you suddenly hear a voice behind you
>"Anon! Milky! Wait!"

>It was Rainbow Dash. Strung around her neck was a medal with a large #1 on the front
>god dammit, of all the fucking ponies to come and see this...
Look Dash, I really don't want to hear....

>"No! Anon, please! Let me just talk to her..."
>Rainbow Dash scoots you out of the way, and puts a hoof on Milky's shoulder.

>"Milky I....look.....I'm sorry I was such a jerk to you earlier. I didn't think...a few more seconds and you would have dusted us..."
>Rainbow Dash pawed at the ground, looking down
>at the same time, Milky's hoof lowered away from her face, her crying ceasing at Rainbow Dash's apology
>"I shouldn't have counted you out like that, Milky. Can...can you forgive me?"

>the crowd was dead silent, all eyes on the two of them
>slowly, Milky nodded her head, and a wide grin spread acoss Dash's face
>"Oh, by the way, this is for you! The judge was gonna give it to you, but you were too busy sitting here to go accept it!"
>Dash's tail whipped around to her side
>strung around it was another shining, golden medal, this one with the #4 on it

>"Milky's eyes widened when she saw the glittering award. With one hoof, Dash draped the medal over Milky's head."
>the second it was around her neck, the crowd suddenly burst into a flurry of cheering

-Epilogue

>you, Milky, and Rainbow Dash were walking down the road to your house
>in your hands you held Milky's damp clothes, while her and Dash were locked in conversation, medals swinging from their necks

>"...and right in the middle of the Immelmann turn...TOTALLY peed my flight suit."
>"In your flight suit?!"
>"Uh huh, it happened to a few Speedsters, but I was definitely the worst. I'd always leak when pulling a hard turn, or if I beat my wings too fast."
>"Wow...that must have been embarrassing."
>"Yeah, I guess I kinda know how it feels to be embarrased like that. My parents took me to Canterlot for an operation to fix me up so it wouldn't happen anymore though, thank goodness..."

>as you got to the house, Dash suddenly spoke up again
>"Hey Milky...if you ever feel like doing anything fun, I'm all for that, y'know?"
>Milky turns around.
>"Um, yeah! That sound great! Maybe we can go running together....well....when Rarity adjusts these clothes a little...."
>Milky glances at the wet clothes in your hands sheepishly

>"Alright then, it's a plan! I'm DEFINITELY gonna hold you to it though!"
>Dash suddenly turns around, spreading her wings
>"I gotta head off and finish my shift with the weather control squad. I'll see you two lovebirds later!"
>Dash takes off into the sky, leaving you to alone

>Milky, making her way toward you, suddenly reared up on her hind legs, wrapping you in a hug
>"I didn't think I'd ever be able to do this again, anon. Thank you..."
>you put your arms around her back
Don't mention it, Milky.