Hey all! So this is my first story, I just felt like writing it as I wish I had this kind of support. I'm a really masculine guy in real life, but I have this feminine side to me I don't get to let loose. So this is my way of getting away from it all.

English isn't my first language, so hope I did okay.

Its my first story, so please be gentle.

This is just to serve as an introductory chapter. Sorry if it seems rushed.

There may be eventual smut, but no degrading stuff, I'm more into friendly fem and gentle femdom. So no degrading humiliation stuff. That stuff is poison.

Pyrrha was confused. Ever since the dance Jaune had been acting a little odd. Nothing too out of the ordinary. Its just that every now and then he would cut a training session source saying he was going to spend some time with Ren and Nora because he wanted to make sure their team dynamic was good. Which was fine, Pyrrha could understand that, and his skills and abilities had significantly improved, so she wasn't too worried about him anymore. That being said, she found out something odd. Perchance, she ran into Nora one day in the hall, and she found out that when Jaune DID spend time with Ren and Nora, it was only for about half an hour, and then he would find an excuse for something to do and leave them there. Which they didn't mind because they figured he had to get back to training with Pyrrha, but he never showed up back to their training sessions. So that left Pyrrha even more confused. So Jaune was technically telling the truth, but where was the other place he was going in that other thirty minutes?

Then she realized something else, usually Jaune was the first one back in the room, her and the others didn't usually come back until they had to, Pyrrha because she would usually go and have some time to herself in the library relaxing after training to get back in the mindset that it was time to relax. And Ren and Nora usually were off doing other things, Nora was off trying to see how many pancakes she could fit in her mouth, and Ren was taking the small amount of time he had in his day to drink some green tea in the garden by himself. So that still left Jaune as the unknown variable, what did he do?

Pyrrha wanted to know, but she also didn't want to come right out and ask him. She knew how Jaune was when it came to secrets. Granted, she was certain they didn't keep any from each other anymore. Ever since the transcripts fiasco, she didn't think there was anything bad he could be hiding. So whatever he was doing in those last thirty minutes, it couldn't be anything bad.

But then there was the curiosity in her head. Just WHAT was he doing in that time?

Hence her current position right now, she felt a bit stalker like, but she needed to know what Jaune was doing. Not because she was worried, because she honestly couldn't wanted to know. She assumed it had to be what he did to unwind from the days events, so maybe if she found out, they could do it together. Jaune had seem to be warming up to the idea of her as more than a friend ever since the dance. But maybe if she found out what he did after hours, she could help them bond even more.

Alright there he was! He was talking to Ren and Nora, so things were off to a normal start. They were laughing and joking, and Pyrrha smiled at it, Jaune almost seemed like the big brother figure sometimes, odd considering he had seven sisters. But overall, she could now see why Jaune took the time to come and talk to them. It was refreshing to see. To think that even at the end of the day he would still make some extra time for Ren and Nora was heartwarming. But then that was when things changed. Jaune looked at his watch and saw him stand up.

"Hey guys, sorry, got to go work on homework." He said as Pyrrha raised a brow, but Ren and Nora just waved it off and said bye.

Now that was confusing. Pyrrha knew Jaune didn't have any homework, they did it together before training each night since she knew if they did it after training, he would be too exhausted to do it. So what was he doing? She hid really quick as he passed by. And she noticed he wasn't acting abnormal, in fact he almost seemed to have a slight spring in his step.

She followed him closely behind making sure he didn't see her. But he never even looked back. It wasn't until after he stopped that she realized where they were.

Jaune was just standing outside their room door, she hid behind a pillar so he wouldn't see her. She noticed he looked around a few times, made sure no one was around, and he went inside. As soon as the door closed. Pyrrha walked up confused.

That was it? That was why he left early? He just wanted to go back to the room? Pyrrha was a bit disappointed. She was expecting something big, but turns out he really was just tired after the nights training and probably wanted to get as much rest as possible. Well, she couldn't blame the guy, he had been working hard. She turned away from the door as she sighed. She was expecting a little more. Like maybe he went to the library or something, but nope, just an extra nap. She waited outside for a bit contemplating all the possibilities she had going in her head over what she thought he was doing in his free time.

Maybe he hung out with Team RWBY? Maybe he went to the library? Maybe he visited beacons gardens? Or maybe he went to the school swimming pool for a quick dip, or maybe he just took a scenic hike through nature.

She was standing there for about ten minutes until she just shrugged her shoulders. Well, she was already tired. And she might as well go in to catch a nap.

She opened the door to the room.

And her eyes went wide in shock.

Standing in the middle of the room, stood Jaune in the dress he wore to Beacon, as well as a pair of high heels and a pair of white satin gloves that went up to his biceps.

"Wh-" Pyrrha didn't even get a word out before she saw Jaune's head turn really quick at the sudden intrusion.

"PYRRHA!" Jaune looked horrified as he realized Pyrrha had just seen him, and he ran into the bathroom.

Pyrrha froze as he slammed the door shut. Never in her life did she picture this. But then again...he did wear that dress to the dance. But that didn't explain where he got the gloves, or the heels. She was expecting to find a lot of things that Jaune was into. But THIS was not one of them. She half expected him to be reading an x ray and vav comic or something like that. She never expected he would be in the same dress he wore to the dance, the dress he SUPPOSEDLY wore as a joke. But after what she just saw she wasn't sure anymore.

But she remembered seeing Jaune's horrified look on his face. And she realized she just caught him doing something that he didn't want her to see. She walked over to the bathroom softly and knocked.

"Jaune..."

"GO AWAY." He said in a squeak.

"Jaune...its okay, I'm not mad...I'm just...I'm just surprised." That was the understatement of the century.

"You're just saying that!" Jaune said as Pyrrha admitted, she probably shouldn't have stalked him back here now.

"No, I'm not. Just please come out, and we can talk about this." She said as she didn't hear any noise.

"...You promise?" He asked with desperation in his voice.

"I promise." She said as she heard more silence.

"...Can you please lock the dorm room?" He said as Pyrrha nodded to herself.

"Of course...I'm surprised you didn't..." She said but that turned out to be the wrong thing to say.

"Well no one ever comes back at this time!" Jaune said a bit catty.

"Okay okay, I get it, my bad." She said as she went over to the dorm room door and locked it.

Granted, she knew he was just being irrational and mad at her because she just caught him crossdressing. But he wasn't thinking straight because he was obviously emotional, so she was going to let that slide.

She walked over and sat on the bed with her hands in her lap, looking at the bathroom door. She saw it slowly open as she saw Jaune emerge.

He walked over slowly as if he was contemplating what to do, and wondering if he could change out of what he was currently wearing before they talked. But when he went to go change. Pyrrha stopped at him.

"No its okay, you don't need to change..." She said as Jaune froze as he continued to walk over.

As he was walking over, she noticed certain things about his appearance. Jaune was never a hairy guy before, but now she was taking the time to notice he had no body hair anywhere. His legs looked silky smooth, and she even noticed that there was a hint of perfume in the air. She recognized it, that was what she wore the night of the dance. Pyrrha might have been mad if it wasn't for the fact that she had to get to the bottom of this current situation here. She looked up at Jaune's face and noticed he was wearing a little makeup. Mostly just some eyeshadow and eyeliner just to give a slight feminine appearance, but nothing serious or heavy, just enough to enhance the eyes. Obviously he didn't know a lot about makeup, so he jsut went with what looked easiest to apply. Surprisingly his eyeliner was good, which she never saw with beginners.

He took a seat right next to her, his eyes looking down at his feet as Pyrrha thought about what to say.

"Jaune." She said as he just let out an embarrassed meep.

"Jaune its okay." She said as she decided to do the one thing she knew would help.

She wrapped her arms around him in a comforting hug.

At first he stiffened a bit, but he soon melted into the warm embrace, his head resting on her shoulder as his hair brushed up against her nose.

Smelled like strawberries...wait...she recognized that smell. That was Yang's shampoo! What was Jaune doing with it? But that was questions for later.

"So uhm...this is what you do in your free time?" She asked as Jaune nodded as he couldn't really focus on words right now.

He was too distracted by the warm embrace and the fact that he just got caught dressing up by Pyrrha.

"Its alright, it just makes you interesting..." She wasn't really sure how to comfort someone, but she was doing her best.

She thought about what to say next.

"How long has this been going on?" She asked as Jaune went quiet for a bit.

"It's...a long story..." He said as she pulled back.

"It's okay, we got plenty of time before Ren and Nora come back." She gave him a reassuring smile to show she wasn't mad at him.

Jaune weighed his options, but realized he only had one option, and that was to come clean about everything.

"Well, if I'm honest, it started with my sisters." And that was when Pyrrha remembered his comment at the dance.

"Well, these things tend to happen when you grow up with seven sisters."

Suddenly that made a lot more sense now.

"I hated it as a kid, especially since my sisters did it to embarrass me, so I never wanted anything to do with it again." He said remembering those times.

"But then the dance came, and well, even though it was still kind of embarrassing, it was worth it just to see you smile." He said as Pyrrha felt her heart skip a beat.

"Suddenly, the negative memories I had of it as a kid where I was forced into it were on the back burner, and all I had were the positive feelings I had when I was dancing with you."

"And then?" Pyrrha asked honestly curious.

"Er, well I mean...it was just the dress, the gloves came later, and the heels, Coco was giving these away because they were last season, and I was helping her move her stuff out that she was donating." He said as he took one pair of heels for himself.

"She didn't find it odd that you took it for yourself?"

"She just figured I was getting them as a gift for you or Nora." He said as it wasn't that hard to hide his true intentions.

"And you've been dressing up ever since?" She asked as he nodded.

"Yes..."

"Jaune, you know I would never judge you for this right?"

"...I...I just didn't want anyone to know, it's still kind of embarrassing." He said as Pyrrha looked him over.

"You know, you don't look bad." She said as she tilted his chin up.

"Granted, I find it odd the only makeup you have is around your eyes, how did you get your eyeliner to look that good? Even I still have trouble with that." She heard Jaune let out a giggle.

A feminine giggle, and it made her heart skip a beat.

"Oh that, well, seven sisters, they did those weird scrollnet challenges where 'Have your brother do your makeup', well they only let me do the eyes, and eventually I got really good at it." Pyrrha giggled a bit at that.

She was not expecting that, but it was kind of adorable.

"But you've never bought anything else?" She asked as he shook his head.

"No! Are you kidding? Do you know the looks I would get for buying stuff for myself?" Jaune said as Pyrrha felt a lightbulb go off in her head.

"Well, not for yourself, for your girlfriend." She said as Jaune got confused.

"But I don't have a girlfriend." He said as she suddenly got closer.

"You do now." She said as she suddenly felt bold.

Normally she wouldn't have the courage to do what she was doing or say what she was saying. But surprisingly, seeing Jaune so vulnerable like this made her feel more confident, almost as if because she knew he needed reassurance, that it was causing her to act more bold. Seeing him like this was in a way both encouraging as well as inviting.

And she leaned in and kissed him ever so gently.

Jaune froze for a second. But soon he relented and he kissed Pyrrha back. She pushed him onto the bed as she deepened the kiss. She had been waiting for this for a long time. And she would be damned if she wasn't going to take advantage of it now. Eventually they both had to break for air. And Jaune looked up at her as she was straddling his waist.

"You're okay with this?" He asked referring to the dress.

"Jaune, I like dressing up too, what does it matter if its on you or me?" She said with a reassuring smile.

Sure it was a surprise, but the more she looked at him, the more appealing he looked.

"I do find it a surprise, considering how you act normally." She said with a smile.

And for the first time he felt happy because someone had accepted him for this.

"Well, just because I like dressing up like this occassionally doesn't mean I don't still like being masculine, its just another part of me. Another persona." He said as Pyrrha raised an eyebrow.

"Oh? And whats the other personas name?"

"Don't know haven't come up with one yet, I was going to go with Joan, but seemed too obvious."

She giggled in response.

"Well, don't worry too much about it. But we do have other things to worry about." She said as she looked over Jaune.

"You've been wearing the same thing for too long, we'll have to get you some new outfits." He blushed a bit at that.

"Uhm, I don't know." She put a finger to his mouth.

"Shhh, don't worry, I'll take care of it, for now, lets just enjoy the moment." She said as she laid her head on his chest.

Jaune just basked in the happiness he felt, and suddenly he felt a lot more comfortable about dressing up.

"You know, I may have some stuff that may fit you." Pyrrha offered.

"Shhhhh, just let me enjoy the moment."

"Okay, but one more question."

"Yeah?"

"What are you doing with Yang's shampoo?"

"Oh, that, well, I went out shopping with both her and Ruby, and after the weapons shop, Yang wanted to pick up some shampoo, and she got me this as a gift saying 'Blondes need to stick together." He said with a laugh.

"Really?"

"Oh yeah, well that and she got mad when I saw I was using cheap shampoo and practically made me switch brands, I don't mind, it smells nice." He said as Pyrrha ran her fingers through his hair.

"And silky smooth too." She said being impressed at it.

"You ever think about growing your hair out?"

"One step at a time Pyrrha. One step at a time."

BANG BANG BANG!

"HEEEEYYY OPEN UP!" Suddenly that caused the two new lovers to jump up in fright.

Even more so when they saw the doorknob turning.

They forgot Ren had a key.

"EEP!" Both ran straight into the bathroom before the door opened.

One thing was for sure, things just changed for the better.