A Colt's Dress

by DustShine

First published

A colt dressing as a filly. What could possibly go wrong?

What if a colt wore a dress? Would you mock him? Would you accept or even like him? Would you... love him?
I am such a colt and this is my story.

Just as a warning, this story deal with crossdressing, so if you don't like crossdressing, just don't read it.

Please leave a comment if you like or dislike this story, so i can improve in my following chapters and stories.

A well hidden secret

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I am a colt. Why do I tell you, that I am a colt? Honestly... well I am not a colt. This all may sounds confusing, doesn't it? For me it is the most confusing thing in my life, and
that's why I am standing here right at the marketplace of Manehattan. With my own rather short – in comparison to a filly- pale blue mane tucked under a beautiful fake purple mane with red highlights. The same goes for my tail. My normally disheveled tail, tucked under the fake long flowing mane. I giggle a bit. Maybe it does not feel great hiding, who I am, but if I am too weak to be myself?
I wear a dress. Yes, I do, even if it is shocking for some ponies. Or everypony. But it's just.... it's pretty. It's a really pretty and long purple dress that just fits perfect over my whole body, having even some holes for my wings. I do a small rotation, letting the gown flew together with the wind. Then I look at the mirror and finally for a long time I could smile. Finally I feel pretty... just a bit more alive, just a bit more myself. Don't get me wrong. I like being a colt... just I don't like being coltish. Maybe it's much more, that I just can't.
But today is a day I don't care. Today is a day, where I am just going through the town and be myself without anypony looking at me with that strange look.

Nopony knows. Nopony, but my sister.

My steps through the town are slow. Every step seems like a new journey. Everything – the shops, the arcades, the restaurants, the apartments, but so much more, the colts, the fillies, the mares, stallions, pegasi, unicorn and ponies- look so different than, when I was a colt. I am still a colt, but I feel pretty for the first time in my life.

That's what matters in life, right? That I feel like myself. So often ponies told me exactly this line, but I begin to doubt it in its very core. So many ponies are not allowed to be themselves. Look at all the lesbian or gay ponies. Look at all that wasted love. Look at all the geeky ponies, the ponies with weird attitudes. Look at them and tell me: are they truly accepted? Are they truly accepted by the ponies, who tell such blunt lies?

In my life I have learned, that the answer is no. If you are different, be prepared to get picked on, bullied and be threatened like an outcast. How often do I want to stand up for my classmates? How often do I want to just stand and told them how wrong they are? But I just let it go over me. They must all think I’m…. weak and helpless.

I shake my head. This should be my day. The day after my 14 birthday. All those thoughts about how unfair and unkind the world really is have no place in my mind today.

I come in the street that is well known for their exquisite outfits that they sell in the shops here. I like coming here even as a colt, but only to watch. Never to touch. But today that would be different. Today I will touch them. As a filly. As the real me.

I just stand in front of a pretty shop, that sell's all kind of clothing for fillies and mares. It's called “The gorgeous Princess”. I know, I know, it sounds pretty exaggerated, but they really do sell some pretty dresses and uh... socks. I blushed at the thought of socks. In our society wearing socks in public is “uncouth”. Some head-strong fillies and mares do it anyway. I really look up to them, because I could never muster up the courage to do anything like that, even if I was a filly. Well... most of them look really pretty.

I am shaking my head to clear those rather disturbing thoughts out and finally step through the front door of the shop. The first thing I noticed was how bright the light shines at the dresses. It was a warm light to imitate the light from the sun to pull out the best out of their articles.
The young mare at the reception with a pale purple coat color and beautiful magenta hair smiled at me.
“Have fun searching for some pretty dresses or socks. If you want I can help you deciding.”
“Thanks, Miss Saleslady, but I think I will first look for myself.” She gave me a nod before looking down at her magazine again. I am really glad I had a pretty high voice – even for a colt- so that nopony suspects me, when I am dressing up as a filly. That voice training I did clearly helped too.

I was going through the shop without a clear destination, just letting myself get fascinated by the sheer amount of beautiful dresses, socks and other clothing. There were just so many! And oh dear, they are all so pretty!

After I think a pretty long time – It was already getting dark – I finally muster up the courage to go into the changing room with a dress that I find really beautiful: A long dress with a light indigo as its primary color framed with some magenta fabric. I loved this dress as soon as I got the first look on it. It's just... I think it looks like a princess' gown.
With a swift motion I am slipping out of simple dress and gently fold it together, before taking a good look at the dress I took with me. A true work of art, all for a beautiful colt such as myself.

Carefully without losing my fake mane I get into the dress and... Oh Celestia! I look so gorgeous... almost like a princess... besides that I have no horn and no crown. I am grinning brightly at myself, trying to view myself from all possible and impossible angles. So pretty... And I have something with me that will make me even prettier. After looking a bit through my saddlebag I finally find the object of my desire: A silver crown like that one princess Luna is wearing. Only a cheap imitation out of some cheap metal, but I don't care. My sister gave it to me at my birthday. She really knows what I like... or I was rambling too much about how cool it would be to be a princess. Either way I was and am totally happy when she gave it to me. In private, of course.

And now I can finally feel like a princess. With the crown on my head, posing as if I am a princess, I begin feel really happy. Like something warm is engulfing my heart and my whole body is tingling with an unmatched sensation. I am flashing the biggest smile in my whole life at the mirror.
“I am the prettiest PegaPrincess!” I start giggling at this thought for quiet while, before forcefully inserting a hoof in my mouth. It was my low-pitched totally coltish giggle, I just realized.

Someone murmurs outside, saying something.
“Oh no that can't be him, can it?”
“But that giggle? I would recognize it anywhere!”
“You sure? Even if he knows a lot about fashion – even more for a colt – It can't be him.”
“Wanna bet?”
“Oh … no that would be mean, because I would totally win.”
“Don't be so sure. I set 5 bits, that it is him!”
“Don't be ridiculous! … Well you are the one losing your pocket money. Deal!”

Oh no! Oh no! OH NO! I … I totally recognize those two voices. Sugar Melody and Prisma Light. They are my two best friends and protect and comfort me, when I get bullied.
Well Sugar Melody is the one protecting me by giving some really mean and quick-witted answers, while Prisma Light is always there for me, if I just need a hug or somepony to pour my heart out. And now they are almost finding out, that I am... well... that I am different.
I want to cry. They will hate me, like everyone else will. They will look down at me at some freaky colt, who wants nothing more than to be a filly. They will be disgusted with me, calling me names... like everyone else always did.
I am crying now. It's too much for me losing my two best friends. Why I am such an outcast? Why am I so different? Why...?

“Azure Rain? Azure Rain!” Prisma Light is stepping in and looked with a shocked expression at me. Prisma has a bright orange coat and a nice pink-red mane, which she used to wear a bit longer a little bit longer than her shoulders. She is a unicorn and like me hasn't her cutie mark yet.

“Rainy...” I am looking down at the ground.

“Please... just... just leave me alone... I …” My voice is cracking and my knees feel so wobbly. I just break down in front of her crying my heart out.

“Please... just go... leave my disgusting self alone.”

Somepony approaches me and
Suddenly pulls me into a crushing hug. I can only look up. Right into her vivid orange eyes, focused on me. I can feel that radiating smile, that she always gives me, if she tries to comfort me. A smile that says: Everything will be okay.

“Why... why are you still here, Prisma?” The words just fall out of my mouth. Why would she wants to have anything to do with me?

“Because I am your friend. A friend never leaves a friend alone in times where a friend needs to be there. Don't be afraid to just be yourself.” How often did I hear those words? Way too often, that I thought those words would mean nothing. I am glad; that I am wrong... maybe I can be myself after all.

Prisma....

“Prisma... thanks... I... well...”

“You don't need to explain. If it is something you want to do, just do it.”
I could never hope for a better friend than Prisma and...

“What the....?!” I am looking up right into the disbelieving eyes of Sugar Melody. She is an earth pony with a light rose coat and a cherry red curly tail and mane.

“What are you even DOING here, Azure Rain?! This is just... this is... I... I never thought you would do something this embarrassing, but it seems I am wrong.” With every word her volume increases and she looks at me with those furious eyes.

Every word feels like a stab through my heart.... Like someone would take my heart and break it in two parts. I could even hear the cracking sound my eyes again filled with tears.

“I... I. HATE. YOU!” Those three words she spits out with all of her hate I only ever heard, when she was defending me from those bullies

“Sugar! What are you saying?!”, shouts Prisma. I can feel how her eyes narrowed and she gives Sugar Melody a harsh look. Sometimes Prisma can be quiet intimidating.

“The fucking truth! Just.... just LOOK at him! That sick cross-dresser! Gross!” She just left.
With those last words Sugar Melody stormed out of the shop, but not without slamming the door.

I... I just broke down. This was simply too much for me to take. My best friend... hates me for what I am...

“Rainy.... she doesn't mean it.”
“But... but...”

“There... there is a secret about her.” Prisma sighs. “It's nothing bad, but for her it's embarrassing. Don't worry Rainy. We will get this all worked out somehow.”

I hope she is right about this getting all sorted out somehow. Because... Sugar's words hurt. They hurt me so much... I feel like my heart is falling apart. And I am wondering... am I sick?

“I hope... It really hurts.”

“I know... I am there for you Rainy.”

“...Thanks.”

I hide my head under hers. The tears long stopped falling, but still I don't want to let her go. It just feels so right snuggling up against her and let my emotions roam free. Still... there is a thing that is bugging me.

“Are you... okay with me being.... “I do a not certain movement with my hoof and then point at me. “This.”

“Well... I already knew.”

“You do?!” Wow... that's shock. How does she know? Do other know, too? Oh Celestia, I am doomed.

“Only I know. I noticed how much you know about dresses. So I assumed that you know a bit about it … and when I saw the dresses in your wardrobe, I knew, that you would wear them.” She give me a wink and grins.

“And... well I think it's uhm... it's cute. The dress really suits you.”

“You... you mean it?” From one second at the other I feel so glad. Prisma does not even accept me, but like me! I am blushing at her compliment.

“Yes, sure.” With her magic she picks up the fake crown and gently levitates it on my head.

“You are the prettiest princess.” She gives me a huge smile, before helping me up.

“T... thanks...” I am at a loss of words... She... I am looking in her eyes and the only thing I see is deep sympathy and happiness for me. It feels so great. As if there is finally a light in my darkness. And I feel a fuzzy feeling near my heart. It lets me feel warm, like the feeling when I first put on my crown. Just a lot more intense. I feel even happier. As if someone has ignited a fire and put it in my heart, just that the fire is not burning me, but comforts me.

I shot forward and caught her off-guard and hug her tightly. Unfortunately I am a bit to impulsive and we both are falling down to the ground before. I am looking in her eyes giving her the most honest smile. She answers with the same honest smile.

“Thanks, Prisma, you are the best friend, I could ever wish for.”
“You, too Azure Rain.” She suddenly draws me closer until our noses almost meet.
“Azure Rain... I just want to tell you, that...”
“What are you DOING?!”
We are both jumping into the air, when suddenly an angry voice behind us appears. I am whirling around just to look into the angry eyes of the salesmare.
“uhm erm... “
“Could you please take your little dirty plays out of shop?”
“It's not what it looks like!”, Prisma shouts and blushes. Wow... she looks really cute, when she blushes.
“Okay, okay... after seeing your friend running crying out of my shop, I guess, that's not happening.”
“She was crying?!” She was crying? But...? Maybe she is really... Not hating me. Or that are tears out of rage... I try to remember, when there was the last time Sugar cried. She cried, when her parents wanted to separate her from us, because we are a bad influence on her. She cried, because she didn't want to lose us. Of course we promised, that we never tell anypony, that she sometimes cries.
Why did she cry before? Is she afraid of losing us? She hurt me... she hurt me deeply, but still I want to forgive her. She... It's just, that no matter, what she does I could never hate her.... even after hurting me.
“Are you even listening to me?!”
“Sorry...” I am looking guilty at the ground. “I promise we never will put up such a scene again.”
The salesmare grumbles a bit. “Okay, but if I ever caught you doing a fuss like this again in my shop, you will get kicked out and never come back here.” That's more than we could hope for.
“Thanks, Miss Salesmare”, we both say at the same time.
“Good.”, the salesmare is going to the counter, but not without giving turning around and giving me a smile.
“Don't let anyone control your life and just be yourself. You really look good in the dress by the way.”
“Thanks, Miss Salesmare!”
“Oh this with Miss Salesmare gets silly. Just call me Sunflower Sparkle.”
Both me and Prisma go to Sunflower.
“So you want to buy that dress? An excellent choice. It's really masterful processed. hoof-stitched of course and it's the finest silk. It costs 200 bits. “
“200 bits...” I am biting my lower lip. I only have about 150 bits with me and I am not sure, if my parents wouldn't wonder, where all the bits went, when I bought it...
“We’ll take it!”, suddenly Prisma shouts and pulls out two one-hundred bit coins.
“Prisma, you don't need to ...”
“But I want to, and I saw how happy you were with it and how glad you were, when you put it on. Really just let me buy it for you. As a bit to late birthday present.”
“But... that's your whole pocket money for 4 months!”
“It's my money so I can do with it, what I want.”
“I.. I will repay you!”
“You don't need. It's a present.”
“But I want to!” I am puffing my cheeks to look more determined. I can not let take Prisma all of the cost for my dress...
“You... you just did so much for me... more than I could ever do for you. Please Prisma.”
“Well... okay if you really want to you could give me the money later. But you don't need to!”
“So … are you two done?”
“Sure. I am buying it.”, says Prisma and hands over 200 bits. I am so happy! I finally get the dress. Oh my gosh! Oh my gosh! I am giving a happy squeak and take the bag with the dress.
“Thanks, I would like to see you two again here.” I simply give Sunflower a nod, while Prisma is simply smiling at me. Oh dear... her smile is really beautiful. There may be rainy days, but when she smiles, I can see the sun shining down on me.
We are waving Sunshine goodbye and finally we are stepping out of the shop.
“So … where are we heading now?”, I am asking Prisma, who hummed a happy tone.
“Well what do you think about now going to the shopping arcade and then going to me?”
“To the arcades? Oh I am in!” With a small jump in the air and a happy flutter I am following her.