Stallions Don't Cry

by ScarletBlaze

Rating: teen
Tags: Dark, Sad
Length: 7384

The story of Twilight Sky and one of the biggest moments in his life.

Twilight Sky is a simple earth pony. However things begin to change in his life. He has come to realize that there is no love left in his marriage. He is beginning to wonder why he is staying around when he starts to fall for another mare, Rarity. His twin brother shows up at his house (after about three years of not seeing each) to tell Twilight their father is dying, somewhat to Twilight's joy. Most important of all though is his 7-year-old son has just come out to him as a transpony, that he feels more like a filly than a colt.

Author's Note: For Derpy and Rarity, even though they do not appear in the first chapter, appear later on in the story.

EDIT: All right guys. I am sorry to do this. But I am officially going on hiatus with this story. I do not know when I will be coming back. Or if I will. I have really lost my drive on this one, I need to be inspired to finish it. :( If I do come back to this I hope you will continue to read it and thank you for all of your support through out this. :)

Published 1970-01-01 00:00:00 UTC
Last updated 2012-07-17 15:48:23 UTC

Chapter 1

Stallions Don’t Cry

by Scarlet Blaze

Chapter 1

Hi. My name is Twilight Sky. I am an earth pony. My coat is grey. My mane is blue. I have three white stars on each side of my flank. I lived in Ponyville most of my life. I think the only part worth mentioning of my life is when things began to change for me. Whether that was for the better or worse I will leave it for the reader to decide.

I think it was one night when this all began (or the best place to begin anyways). I was looking out at the stars. Sleep was fleeting those days. You could hear your own breath through the stillness. Not even the occasional cricket or owl broke the silence. I gazed to the lights that shone above to give their illuminance to the town. The stars, some brighter than others but all noticeable and distinguishable. I thought about the vast sky. The stars were so spaced it made me wonder what was out there. Some depth that could never be explored. Never be understood.

“Are you still up?”

I did not turn around. I did not need to. I did not care to see mare from who the voice came from, yet I still had to see her. She clopped over to the window and looked out beside me. I glanced over to see my wife, Marmalade. Her bright orange coat was visible in the darkness. The sky light need not show it. It was only a glance at her before I looked back to the sky.

The sky was the only thing that I really enjoyed spending at for awhile. Unlike when Marmalade and I were first married. We would spend hours just being together and talking. Alas, we got jobs, worked, had a child and times changed. I do not remember when it got so bad. I know it was only recently when I realized we did not love each other anymore. I knew and she knew. Why we were still together? It had to be because of our son. That was the only reason.

“Are you coming to bed?” she inquired.

“No. Not yet.”

“You should see a doctor. You might have insomnia.”

“I’m fine, honey.”

“You know I worry about you.”

“...I know.”

Not another word between us that night. Quite frankly it was the first conversation we truly had in days. Marmalade simply went back to bed. However, I waited at the window a bit longer. I waited for nothing.

My work is in Canterlot. Part-time though. I am lucky enough to get free room and a year long train pass from my employer. I work security at the events which were mostly held on weekends. I guess you could say I am “bouncer.” I don’t exactly have brute strength to keep out the undesirables, but I have my ways at keeping them away. This weekend it was some photo gallery of an aspiring photograph. Despite him headlining I never caught the name. Must have not been worth remembering. The event was hosted by Fancy Pants. A big name in Canterlot, actually the one providing my pay. He still owns about half the hot spots in the city not to mention every hotel. I had met him on a couple of occasions. He came off as rather down to Earth for some of his wealth (probably inherited like the majority of Canterlot).

The job was fairly easy. It was the first time I did not have to turn away unwanted ponies. It was not one of those events worth sneaking into. After getting paid I headed back home. Upon arriving at our two-story cottage I was greeted by my brother. He had been waiting for the better portion of the day for me to come home. I looked over him for the first time in a few years. Examining the almost exact replica of myself standing in our living room. He even had g the same cutie mark on his flank. The only reason I could tell it was not just a mirror was the folded wings at his sides. It reminded me how unlucky I was that despite having a unicorn father and pegasus mother I ended up being an earth pony. I have always secretly desired to be an alicorn. Too bad there was only a .0000001% chance of that happening when I was born.

“To what do I owe this occasion,” I asked him.

The question was mostly a formality as I did not bother to smile as I trudged by. The weight of my saddle bag becoming to much to handle.

“You sure are a long way from Clousdale,” I added as I trotted the closet beside the stairway.

“It’s about dad,” he replied.

“Oh,” I asked, trying to sound curious. “Did he get arrested again?”

“No.”

“Are you sure? Between the adultery and drunken cider rampages it is hard to believe he accomplishes anything else.

“He’s dying.”

I set down my saddle bag by the closet door, fully intending to unpack later. The news did not take long to sink in. I had given up on my father after years of abuse and had often wished he would just die. Rather than having sudden shock I just went back to the couch and climbed on. Resting my body upon it.

“Anything you would like to add?”

“The Doctor is giving him a few weeks at most.”

“Tell me when the funeral is.”

My brother lowered his head, obviously saddened by my response. It was as if he had expected me to break down crying and say how much I love my father and how he just can’t be dying now of all times.  I watched as my twin slowly trotted to the door I had left open, about to let himself out (it was like I was offering for him to leave from the instance I saw him). He looked back over his shoulder before his exit.

“If there is something you need to tell him. Sooner would be better than later.”

And with that he left. I climbed back down from the couch and bucked the door shut after he was gone. To say I was a tad angry from the whole thing was an understatement. How should I act after my mostly estranged twin tells me my despicable dad is dying? Happy? Sad? Erotic? What!?

I was so built up by this it took a bit to notice my colt standing at the bottom of the stairs. My anger built up a bit. My son, Morning Sun, the opposing name sake of my father, Night Sky, innocently looked up to me.

“I-Is this a bad time, daddy?” he asked with a low head.

I closed my eyes and took a deep breath, forcing a smile.

“No Sun. I’m sorry. Do you need something?”

Sun looked around at first, as if he was looking to see if anyone else was listening. Since his uncle had left and his mother was not home from work yet it was just us.

“Can... Can we go to my room?”

“Sure.

I clopped slowly behind him as he jumped from step to step. Not yet at a big enough size to climb them. I felt bad that his room had to be upstairs. He was constantly hoping up and down every day. After a some time he managed to get to the top. I trotted closely behind him to his room.

We enter the light blue painted room. I spent the better part of a month painting the whole thing before he was born. Did the whole thing with a paint brush in my mouth.

“Can you please shut the door?” he asked.

I gently kicked it shut.

“Okay, son. What’s with all the secrecy?”

Sun rocked back and forth where he stood. He opened his jaw about speak once or twice to speak, but stopped himself.

“Did you shoplift something, son?” I asked with a smile, mostly to break the tension because I was sure he never would.

He still did not reply, not even a chuckle to brush it off.

“Oh sweet Celestia,” I said as my smile faded. “You didn’t!... Did you?”

“No!” he squeaked, upset with my accusation.

I gave out sigh of relief, “Then what did you do?”

“Nothing!”

“Then what did you want to tell me?”

“Please don’t rush me!”

I had never seen him like this. Whatever it was, it had to be serious. He finally stopped rocking and closed his eyes. A deep breath broke the silence. Opening his eyes again he finally said what it was he wanted to.

“I think I might be a filly.”

Chapter 2

Stallions Don’t Cry

by Scarlet Blaze

Chapter 2

There was a long pause of silence. You can not exactly reply to a statement like that quickly.

“...I don’t know what the kids at school said but you definitely came out of your mother as a colt.”

Sun groaned loudly and rolled his eyes. I guess I missed the point.

“No dad. I mean. I’m not a colt. I’m a filly... at least I think I am.”

“...I am completely lost.”

It was true. I had never heard of something like that.

“Okay. Look at this.”

He hoped into the chair in front of his desk. A red glow appeared from his horn and the glow appeared on the mouse. With a quick movement, the screen of his computer came back to life from its screensaver. On it was a page from Hoofapedia. It read “Stallion-to-Mare Surgery.”

“What is this?”

“Well. I looked up ‘filly in a colt body-’”

“Why?”

Sun looked at me. Mad at either my interrupting him or missing the point completely.

“Because dad,” he replied as nice as he could. “I’ve had this feeling for... awhile now. That I am not suppose to be a colt.”

“How long is ‘awhile?’” I asked, to continue my barrage of questioning.

He shrugged his shoulders (which I found rather cute for him to be able to do) and replied, “Maybe a couple of years. I just never said anything because I thought I wasn’t suppose to.”

I felt bad for him. As his father I should have told him sooner he could talk to me about anything. I always thought I had implied it and I was glad he came to me about this. Yet it dis-heartened me to know he had been hiding this for two years out of fear.

I looked over the sites Sun had found. It was rather impressive that a 7-year-old unicorn was able to accomplish so much with what little magic he had (I was surprised he could even operate the computer). I had never heard of something like a “transpony” before. If I had stumbled upon it at some point before I must have forgotten about it. I was learning stuff I did not know existed. There were surgeries for this sort of thing and plenty of ponies had either gone from mares to stallions or stallions to mares. There was even a successful film about a transpony called  “Stallions Don’t Cry.”

“Are you sure about this, son?” I finally asked, moving away so Sun could see the screen again.

“I think so. But I could be wrong... I think.”

It was difficult to seem him like this. So unsure and insecure. I quickly hugged him, trying to reassure him everything would be okay. I think it helped.

One of the things the websites said about transponies is to seek psychological help first. Make sure this is not just a passing phase or some wild idea, that truly the pony would be more comfortable as the other gender. The problem was there was not really much of a need for a psychologist in Ponyville. This was mostly because all citizens were quite happy and with out problems (normally). If anypony had problems they went to Canterlot for help. I did know one pony in town who might be able to help. A mare named Twilight Sparkle. She came from Canterlot and was well studied in... everything.

“I spent a few weeks with a psychologist in Canterlot. I picked up a few things, why do you ask?” was her response when I saw her the next day.

I looked around nervously. Not many ponies just decide to sit around and listen to conversations near the library. I was still on edge though.

“Do you know anything about transponies?” I asked in a low tone.

The purple mare strained to hear me.

“A little. What’s this all about?”

I came clean.

“Well, my son told me that he thinks he might be a transpony. That he wants to be a filly.”

Twilight’s eyes went wide for a bit, finally catching on to the reason of my anxiety.

“Oh. And what would you like from me?”

“Some psychological input? I don’t exactly know any psychologists.”

“Oh. I see. Well, do you want to bring him by later today? I don’t think I can give a professional opinion. But maybe I can help.”

I thanked her and began to trot off. However I had to stop and cringe when I heard Twilight shout inside the library.

“Spike! Do we have any books on transponies!?”

***

I waited downstairs for Sun. I could barely hear anything between him and Twilight. After several minutes of trying to make out what they were saying I gave up. Instead I watched the little purple dragon in the room. Spike was his name if I was correct. The name fit him. He paid little to no attention to me. He continued his work of re-shelving books. I had to cringe when I saw the spine of one of the books titled, “The Transpony and You.” Yet I was more surprised than embarrassed. Perplexed they had such a specific reference work on hand here.

About thirty minutes or so later Sun came hoping down the stairs with Twilight trotting close behind. He rushed over to me, quite excited.

“Hi daddy! She was a really nice lady. She was nice to talk to,” he began to rattle off.

I interrupted by petting his mane with my hoof.

“That’s great kiddo. Can you wait outside for a bit? I need to talk with Ms. Sparkle.”

He happily trotted to the door which Spike kindly held open.

“You have a wonderful son,” Twilight said.

“So what do you think? Is he really a... well...”

I was having a hard time getting my words out. I do not think there is ever really a proper way to address a topic like this. Twilight was kind enough to know where I was going.

“I don’t think it is fair for me to ‘diagnose’ him or anything. But it was... interesting to talk with him about it.”

“What should I, I mean, we do about it?”

“I can talk with my psychology tutor in Canterlot. I am sure I can get him to hoof the bill.”

“I...I don’t know what to say ma’am. That is awfully kind.”

Twilight waved her hoof in the air.

“Don’t mention it. Anything I can do to help my fellow pony is worth doing.”

I thanked her a few more times and I was about to leave. I paused to ask one more thing.

“Ms. Sparkle. Are we related?”

“...Excuse me?”

“Well, my name is Twilight Sky. You are Twilight Sparkle. We have very similar names.”

Twilight laughed for a bit, “I don’t think so...Twilight.”

I smiled and left.

Sun and I were heading home when the most interesting thing happened. A mare I was rather familiar with from Canterlot came running up. Photo Finish. I can not say I had the pleasure of meeting her before then, but she was one of the ponies everypony should know. She was accompanied by two brightly colored and brightly dressed ponies. The fabulous photographer wore her own “unique” outfit with her trademark sunglasses. The blue pony pointed at me with her hoof.

“You,” she said in her sharp dialect.

Her hoof moved slightly to point to somepony else as well.

“And you.”

I turned to see the brown colored stallion Time Turner. I had know him from my school days. We were friends of sorts. He acknowledge me as well with a glance.

“Photo Finish needs you for her grand entrance.”

After one of the bright ponies offered compensation for us I told Sun to head home. The next thing I know we were forced to gallop to the park for whatever reason. The pony had not stated she was running late so it seemed odd to be rushing. I had wanted to at least say “hi” to Time Turner and see how he was doing these days. Photo Finish’s go-go attitude prevented this.

It was all so quickly paced that I hardly remember what I was doing before I was lifting one side of a platform (with Time Turner on the other) and trotting into the park. Photo Finish riding on top for her grand entrance.

“Put me down here,” she said.

The two of us got to our knees and she hoped off. I looked up and noticed two ponies who were already waiting for her. One was in something covered in blue gems. Silly outfit. The other was a white mare with a curly purple mane. Anypony would have a hard time not catch a glance at the perfectly styled mane. She was a pony who knew a thing or two about beauty.

I waited around on my knees a while longer. Listened to Photo Finish talk about “ze model” and “nature” or something. I got out from under the chariot and approached one of the bright ponies. He told me that I would be needed for an upcoming fashion show (apparently familiar with my work at other events) the very next day. I had to rush home and get ready. I packed the basics, said by to the wife and child and took the train. It was days like these that I was fortunate enough to have a year round pass.

That night I stayed in another hotel owned by Fancy Pants. However this was not one I was use to because the fashion show was taking place at a venue owned by some other pony. The room was nicer than usual. The television even had Hooflix available on it. After browsing for awhile I came across “Stallions Don’t Cry.” Needless to say I watched it... It is hard to say what I thought about the film. I guess I could say it was interesting. Something I definitely was not letting Sun watch till he was older.

The next day was pretty big. Just about everypony in Canterlot was crowding around the roped off red carpet. Somehow the previous day the pony in the weird outfit at the park had become the modeling sensation of Canterlot. I got to see her more clearly as I let her and Photo Finish in. She was a yellow pony with a nicely groomed pink mane. Still I did not care for her. Just as they went through another pony tried to follow so I put the red velvet rope up to cut her off. She was about to sulk off when I noticed her mane from beneath the giant hat she was wearing.

“You’re from Ponyville, right?” I asked.

She turned back with a hopeful look.

“Why yes! Yes I am!” she said with excitement.

I guess she was hoping I recognized her. I was more interested in her beautiful accent though. I added, “I saw you in the park yesterday.”

There was some silence and her smile began to fade for a second time. I glanced around and motioned with my hoof for her to listen closer. The mare leaned in and rose her ear.

“There is another entrance in the back. It’s not guarded and most assume it is locked. There is no handle so only unicorns can get it open.”

She was unsure how to respond.

“Well... Thank you, sir.”

“I’m Twilight Sky,”

“I have a friend with a similar name. I’m Rarity.”

She gave a playful smile as her way of saying good bye. I watched as she tried to find a way to the back entrance. I was honestly surprised I gave her that information. I hardly knew her, yet there was something that I liked about her. I hoped I would get to see her again soon.

Chapter 3

Stallions Don’t Cry

by Scarlet Blaze

Chapter 3

When I got home from Canterlot, Marmalade said Twilight Sparkle had left a message.

“She said, ‘I got an appointment for you on Friday at 1.’  She also said, ‘Good luck.’ What’s that all about Twilight?” she asked me.

She had an expression of anger, like I was going behind her or something. Like I was having an affair and plotting to get away from her.

“Oh, well I-” I began to reply.

I stopped because of Sun. He was finishing up his dinner at the table, behind Marmalade and out of her view. He was waving his front legs wildly and shaking his head “no.” Fortunately I was no fool.

“I... I decided I was going to take Sun to Canterlot on Friday,” I explained.

Marmalade still seemed angry with me. Silent and waiting for me to continue to explain myself.

“I had all ready worked this week so they don’t need me this weekend. I thought it would be a nice treat to pull him out of school and spend the day and Canterlot... You know. Father-son bonding time.”

“Then why did she leave a message about an appointment?”

I looked to Sun again. He could not give me anything to work with. He just looked at me with pleading eyes. Under no circumstances was I to give away the secret between us.

“She got us a private tour at a museum,” I lied.

My wife raised her eyebrow.

“Yeah. I had called yesterday to ask if she could get us a tour,” I continued. “She has a lot of connections in Canterlot you know.”

“Oh really. Which museum?”

“The Smithsoneighon.”

Marmalade’s anger subsided and she had more of a concerned look.

“I wish you would talk with me about these things before you plan them,” she said.

I smiled and apologized. She lovingly nuzzled at my neck. I politely nuzzled back.

“I’m finished mom. Can I go?” Sun asked to interrupt our short moment.

“Oh! Yes,” Marmalade replied as she pulled away from my neck.

As I watched Sun hop upstairs I could not help but feel the moment ended too soon. For a moment I felt something between Marmalade and I. That moment I wanted to tell her what was going on with Sun. To tell her I loved her. The moment ended though and the love left. I guess it was just from being closer to one another for once. I had not touched her like that for quite some time. It was not what I hoped for. The moment was fleeting, like love.

“So you are okay with us going tomorrow?” I asked.

“Of course!” Marmalade said with a smile.

Something donned on her though:

“Why did she say ‘good luck?’”

I really had no way to explain that without telling the truth.

“I... don’t know. Good luck at keeping Sun entertained? I’m not sure,” I replied with a chuckle, hoping to brush off the question.

“Yeah. That mare probably isn’t as smart as people say she is,” Marmalade said as her way of concurring and with that she went to clean up Sun’s dishes.

I followed upstairs after Sun after that. He was pacing in a circle in the middle of his room. Practically trotting a circle into the floor. He immediately ceased when he heard my hoofsteps.

“Did she buy it?” he asked.

“Well, you saw most conversation,” I replied with a hint of jesting.

Sun let out a giant breath of relief.

“So I guess you heard about what we are doing this Friday,” I said. “We are going to Canterlot to see a psychologist.”

“A what?”

“A person to talk with. You know, like what you did with Ms. Sparkle a few days ago. You’ll get to talk with him about your feelings... about being a filly.”

A giant smile spread across Sun’s face.

“That sounds awesome!” he shouted with a jump in the air.

I could not help but smile with him. His excitement contagious.

“You know your mother will need to find out sooner or later, right?”

Sun stopped smiling. He began to cower a little at the thought.

“Why don’t you want her to know?” Querying further.

Sun paused for a bit. I was not sure if he was trying to come up with an answer or too afraid to give the one he already had.

“...She...she isn’t like you,” he finally spat out.

I had to chuckle at that.

“What’s that suppose to mean?”

Sun gave a heavy sigh and looked up at me with a gaze of innocence. As if pleading I would not be upset with what he was about to say:

“I remember about a year ago. I was in town with mom. We were getting apples when we went by two mares. A grey one and a white one with a crazy mane. I looked over and saw them kiss. I just thought it was kind of silly. I saw mom look to and she said... a bad word.”

I raised an eyebrow.

“What word did she say?”

“F...Faggots.”

Sun looked back to the floor ashamed he had even said it when I had asked him to.

“That wasn’t the only time,” he continued. “I hear her say things about other ponies all the time. She is alway judging them.”

He looked up at me, tears in his eyes. I had never thought of it before, but even just a moment ago Marmalade basically called Twilight Sparkle an idiot. It made sense when he pointed it out.

“But you never do. You never judge ponies! No matter how different they are.”

Sun began to cry deeply. Tears rolling down his face and falling to the floor. I gently kicked the door shut and sat down beside him. With my front legs I picked him up and hugged him. Sometimes you do not need to say you will always be there for somepony. Sometimes you just need to show it. I let his tears soak up in my coat, not letting go of him.

“I love you,” he whispered.

“I love you, too,” I replied. “And I will never leave you because of who you are or what you do.”

***

The next day we went to Canterlot. To make the story convincing we left early and actually went the Smithsoneighon so we could say what we saw. It was fun to look through all the history of Equestria. Sun was most interested in the film exhibits. I guess seeing famous things was more fun than the other historical exhibits.

By 1 o’ clock we were at the psychologist’s office. He asked to speak with me in his office before he spoke with Sun. He was a grey maned stallion who appeared younger than the grey suggested. A glimpse at his flank revealed a cutie mark made up of ink blotches. I explained to the doctor what Sun was going through and that the websites had suggested psychological conformation. He praised me for not treating this like a disease of some kind. After a bit Sun went in the office and I waited in the waiting room.

I sat around for approximately an hour. I got a good laugh going through the pamphlets the receptionists had sitting on hand at the counter. One was “So You Have an Eating Problem?” and on the front was a picture of a cartoon pony that looked very sad and very skinny. A serious problem that I could not help laughing at. Another was titled “Clopping Problem?” and talked about how “excessive clopping” can be a psychological problem. I laughed at the idea of parents of older colts seeking help for a young fella simply curious about sex.

I had gotten up to “Say ‘Yay’ to Gay!” when Sun and the doctor exited his office. Sun was smiling again, like when he had spoken with Twilight. The doctor called me inside again so we could have another discussion.

“It is hard to just say after one visit, but it would be fair to say that these thoughts are not just passing,” he explained.

“...Meaning?” I had to ask, hoping for it to be dumbed down.

“That he has not just gotten some silly idea that will pass. If he truly is not a transpony it will take a bit for these thoughts to go away and we definitely do not want to go ahead with surgery on this.”

“So he’s not a transpony?” I asked, still confused by how he phrased things.

“I can not say. Like I said it is hard to say after one visit, but if I was forced to make a diagnosis now then I would say he is. That he would be happy and more fitting as a filly or mare then as he is now.”

I gave a small gulp and a nod of understanding.

“Now, if you wish to continue with this so we can be serious about Morning’s future-”

“We call him Sun,” I interrupted.

“...Sun’s future, then we will need to set up more appointments. This one was free because of Ms. Sparkle, but the rest will have to be paid for.”

“I understand, and this was awfully kind of you.”

He gave a nod.

“I recommend four more appointments,” the doctor continued.

“How much will that cost?”

“About 80 bits.”

I let a short burst of air escape my mouth. That was two months of grocery money just to have a guy listen to my son talk.

“Is that a ‘yes’ or ‘no?’” he asked.

I told him Sun and I would discuss this later. I got the office’s phone number and left. On the train ride home I asked Sun if he liked talking to the psychologist.

“Mhmm,” he replied. “He asked me about wanting be a filly. I told him some of the same stuff I told Ms. Sparkle. I told him how my body doesn’t feel right. How when I look at the other fillies at school I think about what it would be to be like them. How pretending to be one of them made me feel... normal.”

That night at home after dinner I went to the closet in the master bedroom. I dug with my hoof at one of the floorboards until it finally came loose. I pushed it aside and stuck the front of my head inside the darkness of the opened floor. I opened my mouth and felt around. Eventually my teeth brushed some leather and I bit down. I pulled out the entire bag hidden inside and set it on the floor of the bedroom. I tugged the string holding it closed with my teeth and open the bag, I proceeded to pour out the contents, letting bits fall all over the floor. I took my time counting them. I was not worried about Marmalade walking in. She was watching one of her sitcoms downstairs and it was near impossible to tear her away from them.

71 bits saved up over time. My stash of funds for if we ever needed them. I guess this was the best time if any. I placed all the bits back in the bag and went to Sun’s room. He was lying on his bed reading a book.

“Sun, can we talk?”

“Sure dad.”

A red glow came from his horn and around the book. Sun closed the book shut and hoped off the bed.

“What’s up dad?”

“The psychologist said that you should go back to talk with him more. Would you like to do that?”

Sun thought about it for a bit.

“Yes. I liked how we talked about if I was a filly. I think... I think it helps.”

“He wanted to see you more to make sure you were a transpony. And if he thinks so then we would eventually get the surgery to change you.”

Sun looked up with hopeful eyes.

“Then let’s go back!”

I smiled at him and trotted closer. I then hugged him close to me with my leg.

“I’ll set up some more appointments.”

Chapter 4

Stallions Don’t Cry

by Scarlet Blaze

Chapter 4

The next day I went into town searching for another job. It was obvious that if this was going to continue than I was going to need more money. Some to pay for the upcoming therapy sessions, and more for the future possibility of surgery for Sun. I explained to Marmalade that I was done being lazy during the week and laying around the house doing nothing. A reasonable excuse that had some truth to it.

I walked around town for most of the day looking for anypony willing to hire me. Most just said “no,” but they were very polite about it. Others were hiring but I lacked the necessary skills for the job. I eventually happened upon my future employer. There is a mail service in Ponyville. It is run by the local mail pony, Derpy Doo. I entered the room and it was hard to say if it was organized chaos or just chaos. Letters and packages lay everywhere and the pegasus was frantically sorting everything in her own way as she flew around the room. Her mane was golden and combed somewhat. It had pointed ends put still somewhat organized (much like the mail room). She had a beautiful grey coat with bubbles on her plot.

“Hello?” I finally was able to ask once I broke my fascination with her.

She immediately stopped and smiled at me.

“Hi!” she shouted with a bubbly voice.

“I can come back later if you are busy, ma’am.”

The pegasus landed in front of me with her smile still wide.

“Of course not silly! I’m Derpy Doo!”

The grey pony rose her hoof and I did too. Politely hoofshaking it. For some reason I could not stop looking at her eyes. They seemed fine when I first saw her, but they now appeared to be looking in two different directions. One at my hooves and the other at my mane.

“I...I’m Twilight Sky,” I finally replied

“How can I help you, sir?” she asked with a giggle.

“I’m looking for job. I was hoping you were hiring.”

Derpy’s jaw dropped. Shocked by my query.

“What’s wrong?” I asked.

“You... You want to work for me?”

I looked around, perplexed by her reaction.

“...Yes?”

Derpy’s smile returned, somehow wider then before. She suddenly hugged me and began jumping around the room. I was more surprised by her strength rather than the sudden burst of joy.

“Thank you! Thank you! Thank you!” she shouted over and over.

“W-What?” was all I managed to get out as I was lifted up and down.

She eventually set me down and I landed right on my rear. I reached back and rubbed at it with my hoof to ease the pain as Derpy explained.

“I’m sorry, sir! It’s just... I’ve never had someone help me before. With you this will make my job so much easier!”

She continued to jump up and down excitedly. I could not help but smile at her optimistic attitude.

“Can you start now!?” she asked me.

“I-I suppose I could. I just can’t work weekends is all,” I replied.

“No problem! I’ve never had an employee before. This is so exciting!”

Derpy finally calmed down enough to start me off on my first day of work at the mail room. For starters I had to make sure that she understood that I needed to be paid. I was pretty sure she understood after we talked for a bit. My job was to sort out the madness that was the mail room (with Derpy’s help of course). I was also in charge of picking up and delivering packages within Ponyville. Derpy was in charge of longer distances. At least it was a job to keep me busy and make some money. It was just luck that I had such a nice boss.

***

The weekend came around and it was time to work in Canterlot again. Yet again I had to lie to Marmalade.

“Sun wants to go to Canterlot again.”

“Really? Why?” she asked.

“He enjoyed it so much. He just wants to see more of it,” I said with a chuckle.

“Won’t you be too busy to do anything with him this weekend?”

I dismissively waved my hoof.

“Not at all! I only work a few hours a day. The rest of the time we are free to do whatever.”

Marmalade smiled.

“I think it’s great you are spending so much time with him. Should I go with you?”

Crap, I thought.

“Well. I mean... It’s a small bed. I think the two of us will have a hard enough time sharing it without you there.”

“What bed?”

“...The one in the hotel room.”

“Oh... So you will be back Sunday?”

“Late Sunday, so we can get to see all we can in Canterlot.”

Marmalade did not ask anymore. She seemed disappointed to not be coming along, but it was for the best I think. Sun and I left on Friday and we were lucky enough to get the same hotel I was in last time. The nice, decorative room with extra commodities. We were flipping through Hooflix when Sun saw “Stallions Don’t Cry.” He begged to watch it and even tried to wrestle the remote away from me with his magic. I really did not want him to see a movie like that.

After working the next couple of days I took Sun to the psychologist again. Paying 20 bits after each time. Every time he left he was quite happy. Happier than he was during average days. The psychologist talked with me afterwards and said that Sun is definitely a transpony. He explained how the next two sessions would be mostly talking with Sun about what to expect if he goes through with this. And to make final assessments on his conditions. Or something like that. He mostly used medical talk and I had a hard time understanding most of it. He recommend that Sun try “girl” things. Like spending time with a filly and participate in activities fillies normal do. In short, get his hooves painted and play with dolls. At least that is how I interpreted it.

We scheduled the next and last two sessions for the same time next weekend. We had the car to ourself on the train ride home, unusual considering weekend travelers. Sun told me how the psychologist had said the same thing to him. That he should try “filly” activities.

“What did you have in mind?” I asked.

“Well... I guess I could try clothes,” he replied with some hesitation.

“Clothes... you know ponies don’t usually wear clothes.”

“I know,” he replied as though I had made a joke. “But we do sometimes. I mean. Maybe a dress?”

“...A dress.”

It was in that moment that I thought to myself, How many fathers have this conversation with their son? My guess was few.

“I mean...well...yeah.” Sun said with the knowing he had hit a touchy subject.

“If you want to I can,” I reassured, not wanting him to be discouraged.

Sun looked up at me with hopeful eyes and a wide smile.

“Really?”

“Y-Yes.”

He jumped up from his seat and latched on to me. Hugging me around my neck. I let out a soft chuckle. I thought, How many fathers get hugged by their son after promising to get him a dress? My guess was few.

***

Early the next day I set out looking for a dress for Sun. A rather odd task to add to my day. I went to the local store that sold just about everything, but as I was approaching the filly clothing I came across Ms. Cheerlie, Sun’s school teacher. She had stopped in the store before school started to grab some things. She was very nice and talkative. I politely excused myself after a bit and practically galloped out of the store.

I was about to try another day when I remembered the day I carried Photo Finish on a platform. There was a boutique nearby where I dropped her off, maybe they had something. Moments later my hoof was knocking on the door to the lavished, purple tower that was a boutique. The door opened and I watched as a little pony rushed out. Running right in between my legs. She was white and had a brightly colored mane.

“See ya, sis! I’m late!” she called back.

I turned back to the opened door to see who she was talking to. Standing in the doorway was the beautiful white mare I had met about a week ago. Rarity.

It took her a bit to remember me, but behind her red-rimmed glasses I could see the look of recognition in her eyes.

“Oh! Why hello -” she began.

“Twilight,” I replied to help her out.

“I knew that darling,” she protested. “You have the same name as my friend.”

“Ms. Sparkle?”

“You know her?”

“...Sort of.”

She smiled and invited me in.

My eyes gazed around the circular show room. A mane and make up section in the corner and a large stage in the middle with mirrors surrounding it.

“This is quite a set up you have,” I commented.

“Why thank you!”

I watched as she trotted over to the stage.

“What can I help you with today, sir?” she asked.

“I’m uh...” I stammered as I felt my face turn red. “Am looking for a dress.”

I rubbed the back of my head with my hoof. My reflex of embarrassment. Rarity looked over me for a bit.

“Oh... Well. I think I might have something in your size.”

“Oh no no no!” I quickly replied waving my hoof. “It’s not for me.”

Rarity gave a breath of relief and a short giggle. “Sorry, sir. Is it for your wife?”

I paused before I answered. Considering how awkward it was when she thought it was for me I was not about to say it was for my son. Not that I wanted to give that information to a stranger in the first place.

“It’s for my niece,” was my response.

At least I thought I had a niece at the time.

“Oh! Well follow me, sir.”

“Please, call me Twilight.”

“Fair enough, Twilight.”

She led me to a room in which dresses hung from rows upon rows of racks. They even decorated ponyequins of various sizes.

“What’s her size?”

“I’m not sure, but she is seven.”

“All right.”

Rarity proceeded to lead me to where she kept the dresses for filly’s that age. Fortunately Sun was average size like most kids his age, not oversized or very thin. After sorting and sifting through several dress we came across a nice looking red one.

“That one,” I said.

“Excellent choice!”

A blue glow formed around the dress and Rarity’s unicorn horn. She lifted it from the rack and brought it back to the main room.

“That will be eight bits,” she said.

I was about to pay when I realized I had only brought six. Rarity waved her hoof and accepted the payment.

“You did me a favor a week ago. This is paying you back,” she explained.

I smiled as she put the dress in a nice paper bag. I thanked her and took the levitating bag in my mouth. I smiled as I trotted all the way home.