Hi. I haven't written a story since grade 11 english lol. My grammar is going to be really bad at times, I'm sure. My choice of wording may be a little poop. So I really hope writers will review and help me with stuff like that.. I've just been waiting since Volume 1 of RWBY for someone to do a story like this and no one has yet :(

So I decided to try and write it for myself. There was a point when I was little where I really wanted to write stories but I never managed to complete any of them :(

Firstly I want to give a shout out to two authors who helped me get the courage to write this story (no, not directly.. but your stories inspired me :p )

DStone who wrote "RWBY: A Tale of Two Roses" and its sequel (which I love!)

And

The Crimson Phantom who wrote "Thorns of a Bloody Rose"

I think once the story starts you'll understand why I've called out these two authors/stories. This is going to be a sloppy, short One-Shot and if it doesn't turn out garbage. I'll try to write more. But it'll most likely be a brand new story following this same theme. This is just a snippet to see how it turns out.

Also this story will 100% always be told from Ruby's perspective. Except for very few circumstances.

All ownership of RWBY goes to RoosterTeeth. I do not own nor profit from it. (did I do that right?)

Chapter 1: Prologue

My name is Ruby Rose... Well it's RubEN Rose. But thanks to my sister I rarely hear anyone call me that unless it's a teacher or someone yelling at me (probably Weiss haha). I honestly get anxiety hearing my full name because it's never for anything good. I'm a second year student at Beacon Academy at only 16 years old and leader of team RWBY! Comprised of my older sister Yang and my two friends Blake and Weiss. This leaves me as the only boy on the team. Although, I don't mind it since I've always had issues getting along with other boys my age...

This might be because I'm transgender and faunus, not a great combo in this society. I spent a large portion of my childhood being bullied for it and my social skills in general suffered because of it. I mostly just clung to Yang all my childhood. My parent situation was difficult too. Yang was the only real role model I had. So, naturally... I feel a little more comfortable around girls than I do around boys.

I even find it hard to talk to anyone outside my team. Which leads to the point of all this...

Chapter 1: The Blind Date

"Ruby! You're supposed to meet her at 8 and it's already 7:45. You need to get off your ass right now and get ready!" Yang shouted as I continued to sit on my ass and not get ready. I couldn't walk away from this game, it's Dark Souls! No matter how many times I try to explain that I can't pause this game… it never seems to stick.

"I just have to put on pants and a shirt. It's not gonna take 15 minutes to do that." I say, sitting in my undies and a t-shirt.

"Ruby. Will you PLEASE put on some pants" Weiss chimed in, exasperated.

Before I could respond Yang is behind me spraying some smelly junk into my hair and attempting to style it while I grunt at her and continue to play. Before we know it, it's 7:54 and my 'date' will be waiting for me at the airdocks. My date... Who's some random stranger that Yang had apparently overheard compliment my appearance and took it upon herself to "set that shit up" as she put it. She thinks it'll be good 'exposure therapy' for me. I remember when she came up to me with the idea. Saying junk like "It doesn't have to lead to anything! It'll just be good for you to get out there and talk to someone! Someone besides me, Blake or Weiss. And NO! Team JNPR does not count!" Pbbbffftttt. She has a point I suppose. But it doesn't make me feel better. I could live my entire life without talking to anyone outside my team and it would be just fine by me.

I sigh and turn off my game after I kill the last enemy of the area. I get up and walk over to the washroom to get completely ready.

I walk out a couple minutes later in black jeans, a black hoodie and a red flannel shirt on top… Thanks to Blake for the weather report! My ass won't be caught in the cold when the temperature drops once the sun goes down! Yang quickly looks me over and smiles. She then pulls me into a soul crushing hug and squeals about how handsome I look and how proud she is of me.

"Money." I say holding my hand out to Yang

"What? Ruby, you have your own money!"

"I'm not spending my hard-earned cash on a date I don't want to go on! Plus it's only coffee so $20 should cover it"

"$20?! And what 'hard earned cash' Uncle Qrow sends you your money!" Yang shouts

"Being related to him IS hard work. So it's hard earned. Now $20. $5 for the coffee and another $15 for compensation. Y'know... for forcing me into this situation" I say as I cross my arms and glare at her.

Yang sighs "Fine. Just go get my wallet it's in the-"

"I know where it is" I say as I go over to her bottom drawer to pull it out.

"How do you know where my wallet is?" Yang questions.

"... What?" I say as I freeze up with her wallet in my hand.

"Ruby, How do you know where my wallet is?" She asks again

"I can't... I can't hear you..."

"How do you know where my wallet is, Ruben?!" She says as she starts raising her voice.

"Ruby can't come to the phone right now. He's gotta go" I say as I start rushing out the door.

I wave my goodbyes to the rest of the team, Blake is reading at one of the desks, disinterested. And Weiss is... Wait... Where is Weiss? She was sitting here a second ago working on her essay... Did she sneak out while I was in the washroo- Wait! I don't have time to think about this! I'm already running late! Even though I have no interest in this blind date, I don't want to be rude and make her wait. I rush out the door and begin my walk through the school.

"Welp, he's gone..." Yang says, breaking the new silence.

"Seems so." Blake replies.

"Soo... Are you gonna come with me to follow him?" Yang asks as a devious grin spreads on her face.

"Yang... Give your brother some privacy. For once in your life"

"Come on! It's my duty as a big sister! And your duty as his future sister-in-law" She said the last part in a teasing tone, wiggling her eyebrows.

Blake sighs before accepting her fate. She learned long ago that when it came to Yang and her little brother, there was no use in trying to get between them. No matter how foolish the situation was. Besides, knowing Yang... It wouldn't be hard to distract her and earn Ruby some much deserved privacy on his first date.

"Let's just get this over with" Blake said flatly as she stood up and grabbed a sweater.

"YAAAAY!" Yang cheered as she grabbed Blake's hand and tugged her out of the room. Leaving Weiss all alone sitting on her bed with her back against the headboard, who appeared to have gone completely unnoticed.

"Did they seriously forget I was here or did they just not want me to come..." Weiss sighed. Constantly fighting the self-doubt she felt about whether her first real friends actually enjoyed her company.

I made my way to the airdocks fairly quickly, although 15 minutes late... I made sure to take 2 ativans before I arrived. My doctor prescribed them to me for social anxiety. Social situations like this just make my stomach twist and turn so much. I knew I would be all over the place if I didn't take my meds to calm me down a little. Sure enough, my date was standing there waiting for me. Luckily she came right up to me with a cheerful attitude, diminishing all my worry about the awkwardness of trying to figure out who the hell I was even set up with. She was pretty cute I guess. Though I think lots of people are cute... Until we speak and I realize that we have nothing to talk about. She greets me and after I apologize for my lateness she explains that she had only been waiting for about 5 minutes. I sigh a heavy sigh of relief and begin our date as we step onto the airship.

1 Hour and a Half Later...

I make my way through the dorm building, exhausted. The date wasn't bad. At all. It just wasn't good. And I'm definitely never calling her ever again and I'll probably duck into a dumpster if she comes close to making eye contact with me. I reach my dorm room and open the door to find it empty except for Weiss sitting at our desk working on something or other.

"Hey Weiss, where's Blang?" I ask as I sit next to her, I coined 'Blang' as my 'celebrity couple' name for them. It's just easier since they're always together.

"They left after you. Yang seemed intent on following you on your date"

I rolled my eyes. "Of course Yang was following me. Although, I never noticed her..."

"Blake probably managed to distract her from her task so you could have some privacy" Weiss said before I could finish my thought. Ah yeah, good ol' Blake. She's always got my back when it comes to Yang being an overbearing older sister. As much as I love her she really is too much sometimes. And she needs to learn what the word 'boundaries' means.

"So..." Weiss started

I stared blankly at her without a clue of where this was going.

Weiss rolls her eyes and decides to spell it out for me "How was your date?"

"Ohhhhhhh. Uhm. It was... Not bad. But not good. I don't know~ it was kind of... I don't know."

"Well did you like her?"

"I didn't hate her... I just... We just didn't really... Click. I guess. She tried to kiss me and I went with it but I didn't really enjoy it so I cut it short. She kept trying stuff I wasn't okay with though so I ended the date and came home." I didn't want to tell Weiss the full truth of what happened. That the 'kiss' had quickly turned into a full blown 'make-out' session and that the girl I was with was getting really touchy feel-y. I couldn't tell Weiss the real reason that made me so uncomfortable… So I just left it at that.

Weiss frowned a bit and began to look concerned.

"I just didn't like her, I guess. It's not because I was just getting to know her. I liked you when I was just getting to know you... I liked you a lot. I know when I like someone even if I've just met them. I just don't get why I'm expected to date people I don't know. I'd rather date people that I already like..." I said as I kept my head down, idly playing with my fingers.

Weiss started to stutter something out that I couldn't understand but before I could ask her to repeat herself, Yang came crashing through the door with Blake behind her. Yang was clearly a little tipsy but thankfully it seems she was at that sleepy-drunk stage as she stumbled through the room and stripped down to her jammies before crawling into Blake's bed. Blake rolled her eyes and grabbed her night gear as she went into the bathroom. I was relieved to say the least. It seems Yang had forgotten that I even had a date tonight. At least this way I can find time to talk to her about it in private. And hopefully she won't put me in that position again… Not that she meant for that to happen. 'I know she's going to feel guilty but it's not her fault. If anything it's mine…' I shook my head and tried to clear those thoughts as I knew exactly where they would lead to if I kept thinking like that.

I sighed and picked up my controller as I continued my game where I left off while Weiss went back to work on her essay. 'I wonder what she was trying to tell me before Yang came in…'

Okay so that's the end.

Here are some important things to know:

I am transgender. This story (and maybe the next one I write if I decide to start fresh) will be told from MY personal experience as a trans guy. I always loved the idea of a trans guy Ruby because it gives me Steven Universe vibes tbh! Yang, Blake and Weiss already got the Amethyst, Garnet and Pearl thing going on lol

This Ruby does suffer from social anxiety and depression. As well as I do and most of it has been found to be linked to my trans identity.

I'm struggling over whether Ruby would be out to his team. I don't want to do the whole "Weiss hating him for being trans and being forced to come around" thing because that's not how I want the "trans" part of this story to be dealt with. Also I would like to make this Ruby a Faunus as well. To really drive home the "social discrimination" thing about being transgender, without making it too much about people hating Ruby for being transgender.

The name choice of Ruben does not mean that "Ruby" was his birthname. As it would be uncomfortable for him to continue to be called "Ruby" after his name change. We won't find out his birthname because I don't want to focus on "tragic trans backstory". He is on Hormone Replacement Therapy. So his voice is deep, he grows facial hair (probably faster than his friends because you know, HRT will do that to ya haha), etc etc. No top surgery though so he wears a binder. That will probably be addressed throughout the story.

I want this to be a story that just happens to have a trans character. There will be times where we talk about it. Maybe some times where it does become a bit of a topic. But overall I want it to be like this story. He IS trans. But it doesn't define his character or who he is. But at the same time, it isn't something that is thrown under the rug. It's an important part of his identity... just not all of it.

So please give me tips in the reviews or just let me know if you liked it and would like to see more because I'm so hesitant and a bit worried to keep writing.. since it's not really something I do :p

Thank you

:)