Oscar!Trans đłď¸ââ§ď¸
Credits to: @lyslsstuff for the inspiration 𫶠i love your art and fics so much, the representation of the trans experiences they are very beautiful, you do something very nice for our community

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Oscar!Trans đłď¸ââ§ď¸
Credits to: @lyslsstuff for the inspiration 𫶠i love your art and fics so much, the representation of the trans experiences they are very beautiful, you do something very nice for our community

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self-indulgent ask for me Ruby is having a bad (worse than normal) period and one of the boys (Jaune, Mercury or Oscar) notices and helps her out.
âEverything okay?â Oscar asked as he opened the door to Rubyâs dorm. âYang said you werent feeling well and I wanted to check in on you.âÂ
Ruby looked up from her bed, hardly able to move as she tried to adjust herself. She had known her period was going to start, but she hadnt been prepared for just how bad everything was going to feel today. Maybe the missions she had been taking for Ironwood tired her out more than she expected, either way, the cramps were hell.Â
She forced herself to sit up and reached for the midol she kept close by. âJust⌠that time of the month again.âÂ
Oscar gave a quick nod. âIâll be right back.âÂ
Ruby watched him rush away, a bit curious, but not enough to try to get up and go after him. Not that she could. Even with painkillers, the pain itself was enough to keep her from wanting to move. Sitting up was enough to make it feel like a needle was jamming into her sides, she didnt want to think what standing would feel like.Â
She laid back down, only to pause when she heard footsteps rushing to her door again. Still, sitting up was still enough of a pain that she stayed down, catching Oscar out of the corner of her eye still curious about what he had in mind.Â
Oscar walked over to the bed and pulled out a heating pad, plugging it in and setting it up. âI dont have much anymore to help with this, but a heating pad always helped me when I couldnt move. I also brought you some chocolate, a few stronger painkillers, and a couple ice pads to help dull the pain if the heating pad is too much.â He paused and put down an extra box. âOh, and a few extra pads.âÂ
Ruby winced as she sat up once more, looking over Oscar curiously. âI never expected a boy to be this prepared.âÂ
âWell, I was never like the other boys.â Oscar sat down next to Ruby. âBefore I started transitioning, my periods were pretty bad. Theyâre not too noticeable for me anymore, but Iâve held onto this stuff just in case. And since you need it, I figure youâll put it all to better use right now.âÂ
âI didnt realize you were⌠does anyone else know?âÂ
âNo, though I cant say thereâs been a reason for it to come up yet.âÂ
A smile crossed Rubyâs lips as she relaxed, the heating pad starting to do its job. âI wont tell anyone until youâre ready.âÂ
Oscar got up and started to walk out. âThanks.âÂ
Ruby laid back down and closed her eyes to rest as she listened to the door shut. Once she had a moment, sheâd have to thank Oscar properly for helping. Maybe dinner at one of the restaurants Weiss had mentioned.
Island Vacation because brothers these two need one
Day 1 - Island / Wonderland
@rosegardenweek
Penny/Oscar prompt(with trans!Penny and trans!Oscar): Still feeling confused by being chosen as the Winter maiden, she approaches Oscar about whether she can really be a Maiden when her soul came from a man. Oscar tries his best to answer as himself, saying they're not so different as Oz only reincarnates into men, and explains he wasn't born as one, but that it's their feelings towards their gender and own identity that matters more and is a true reflection of their soul.
I donât think Iâm ever going to be completely happy with this one. Itâs been through (at minimum 3-4) drafts and waaay too many read throughs. Iâm just gonna call it done here. A part of me feels like I could still make it better somehow, but I already put all that I could into it.
That said, Penny and Oscar as valid af and anyone who disagrees can fight me behind Dennyâs (sure Iâll probably lose because Iâm basically Steve Rogers before he became Captain America, but yeah).
Also if it doesnât come across that theyâre valid af in this fic, I will just go and edit it some more. I did my best, but I also am somewhat worried thatâs not enough.
anywhoooo off to the fic!
.
There Are No Strings On Me (The Farm Boy Is Also A Cricket, Too)
Penny watches the airship lift off and fly away. Â She hates staying behind like this. Â She understands why. Â What she is now, a Maidenâsheâs too important to risk on a reconnaissance mission. Â The fate of Atlas, Mantle, the entire world rests partially on her shoulders, and not just in an âIronwood telling her that it will be her job to save the world one dayâ way. Â This is real. Â Too real.
Penny holds one of her hands in the other. Â She rubs circles with her thumb on her open palm. Â Her father, the first chance he got, repaired the damage Cinderâs fiery blade caused when it exploded. Â Sheâs glad for that. Â Thereâs no doubt in her mind that there will be a battle in the near future she will take part in. Â Going into a fight with sustained damages is no good.
Penny closes her eyes. Â A part of her wants to playback that terrifying moment. Â Hurtling through the air, her sensors alerting her to the incoming blade, catching it, her hands overheating. Â Spinning out of control. Â Falling.
Catching herself.
She refuses to let herself do more than think about it. Â She survived the fight. Â So did Winter. Â Thatâs what really matters. Â
Ok, I canât keep this to myself anymore!!
Even it just a sketch design but I have no zero patience now!!
Remember that in Basically Life and Time of Rosaline Hood that Hoody is happy about people theorized that the Robbing Hood is a men...
You know the dress design by @littlemisssquiggles
Sooooooo, why do I want to show this in the first place?
.
.
Because I want to draw this so much!!!
I been wanting draw non-binary or Tran!Blake ever since I finish Tran!Oscar drawing but have no time, then @ezroar take the cake of drawing non-binary!Blake and it make me so happy!
For Hoody, it just came to me as I write her character. She been in the woods most of her life she remembers and donât give a crap about gender politics outside the wood. But when she called as a man, she is very super happy for some reason. She still question what to be called, she still love dresses sometime but love to wear boy cloth than anything (some of her current is borrow from BOTH Scarlet and Coleđ¤Łđ¤Łđ¤Ł), so she decide that she might be just both. Very simple (for her at least).

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Beautiful boy with his new binder đź
I love trans!osco đłď¸ââ§ď¸đŤś
He looks so trans, I love it
Trans girl Oscar au
Oscar sighed as he watched Ruby twirl around in her new combat gear to show it off to her team. There wasnt a doubt that he was happy for her, but part of him felt a bit jealous. And he wasnt sure if it was because he wanted to make her smile like that or if he wanted to wear the same kind of outfit she did. His eyes watched as the skirt swished around her, a smile crossed his lips as he imagined what itâd be like to wear one himself.Â
âOscar, are you okay?â Jaune asked as he walked up next to him.Â
âY-yeah, Iâm fine.â Oscarâs thoughts drifted from wearing a skirt and back to Ruby. âI was just a little lost in thought.âÂ
Jaune nodded and watched team RWBY chat away. âIf you need any help getting a date with Ruby, I can help.âÂ
Oscarâs cheeks warmed as a blush crossed them and he shook his head.. âN-no, not⌠not those kinds of thoughts. I mean, yeah, sheâs pretty and sheâs a bit like me, but I⌠I couldntâŚâ He took a breath to calm himself and his blush started to fade. âIts other thoughts I have. Not the dating Ruby kind of thoughts.âÂ
âThen, what thoughts could you be having? If its not to see Ruby thenâŚâ Jaune paused for a moment. âYouâre into Weiss, then, arent you?âÂ
âWhat? No, its⌠its not about dating.â Oscar sighed and started to walk off. âJust⌠forget about it, alright? Its nothing to worry about.âÂ
âIt is something for me to worry about because if I dont help you, then when Nora sees you sheâll definitely make it her business.â Jaune followed Oscar and smiled at him. âAnd you know sheâll tease you about it.âÂ
âMaybe Iâm jealous of Ruby and the new gear she has. I mean, I know I just bought my own, but uh, you know⌠maybe I want something a bit more me and a bit less Ozpin.âÂ
âWhat exactly did you have in mind?âÂ
âI⌠have a few thoughts but youâd make fun of me.âÂ
âTry me.âÂ
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Oscar smiled a bit as he swished a skirt around in front of a mirror, a small blush crossed his cheeks. Even if he still wasnt sure what these feelings were, it still felt right. The blush quickly faded once he heard a knock on the door and Jauneâs voice once more.Â
âOscar, you ready?â Jaune asked.
âY-yeah, just uh⌠give me a few seconds.â Oscar quickly pulled a new green and orange jacket over the button up top he found. Orange gloves with green fingers graced his hands. He pulled black leggings up his legs and smiled a bit once he saw himself. âAlright, Iâm coming out now.âÂ
âIâm sure what you picked looks fine-â Jaune went quiet as he looked Oscar over in his new ensemble. âAnd youâre sure this is what you want?âÂ
Oscar started to grow embarrassed and slowly walked back into the changing stall. âNo, youâre right, I shouldnt-âÂ
âThatâs not what I meant. I mean, its a bit of a change for sure, I just⌠well, I just want to make sure thatâs what youâre looking for as something more you. Because right now, it looks like you have something you want to tell us.âÂ
Oscar sighed and slowly turned to face Jaune. âIâm still not entirely sure about everything, but⌠maybe we can call me⌠Tip? O-or if that doesnt work then maybe Olivia. Iâm still not sure what sounds best for me.âÂ
âYeah, I think we can do that.â Jaune smiled at her. âYou know, maybe you will be a bit more Rubyâs type.âÂ
âWhat do you mean?âÂ
âRuby likes girls, and if youâre a girl, then maybe you have a shot.âÂ
Tip blushed a bit as she thought a bit more about it. âMaybe, though Iâm still not sure about that.âÂ
Jaune shrugged. âNever know unless you ask. But we can worry about that another day. For now, you want everyone else to know?âÂ
âYeah, I think Iâm ready to let everyone else know.âÂ