Ruby x Penny (RWBY) by MissCrazyLewds

Ruby meandered down a hallway, humming quietly to herself. The hallway she was in was that of a dorm. The dorm she was at was that of Shade Academy. Vacuo.

Yes- they had successfully made it from Atlas to Vacuo! Taking with them the entire civilian population. After arriving, Ruby's gang was permitted to stay in the dorms until proper housing became available.

After a couple of days of settling in- having awoken the next morning- Ruby made her way to the room of a particular friend of hers- Penny Polendina.

Penny had recently undergone quite a drastic transition. With the help of the Staff of Creation, Penny had finally become a real girl, in a physical manner of speaking. She'd been given a true human body, skin and all.

Naturally, this brought with it many questions and strange experiences for Penny, so Ruby had been helping her adjust to the new way of living.

With this new morning upon them, Ruby headed to Penny's room to check up on her, as she did every morning since arriving in Vacuo.

"May I come in?" Ruby asked with a knock on her door.

"Yes, you may!" That cheerful voice responded through the door.

Ruby turned the knob and stepped into the room, greeted by the sight of Penny's bare butt pointed out directly at her.

"Gah-! Penny!" Ruby shouted, caught off guard by the unexpected sight.

"Hello, Ruby!" Penny greeted, standing up straight and turning her way. She was bending over to pick up her clothes.

"Don't tell me to come in if you aren't dressed!" Ruby replied, covering her eyes.

"Oh, I'm sorry!" Penny quickly apologized. "I thought that friends were allowed to see each other naked."

The pure innocence in her voice was enough to melt Ruby's heart. She began to suppose it wasn't THAT big of a deal. Besides, it wasn't the first time she had seen Penny naked.

On their first night in Vacuo, Ruby personally helped Penny learn how to take a shower. She never had to do so before, so it was a learning experience. The two of them stood naked in the shower, with Ruby scrubbing Penny clean.

It was an interesting night.

Just as well, Ruby didn't want to admit it, but she quite liked looking at Penny while she was naked. She knew that she shouldn't- Penny was her friend, and she was only naked because she needed Ruby's help- not to mention it was a dirty thing to enjoy.

However, she simply couldn't help it. Penny's body was beautiful. Flawlessly smooth skin, curves in the right places. As if she were masterfully sculpted by the gods. Which she essentially was- thanks to Ambrosius.

And the fact that this was her friend that she cared about deeply was not lost on her either.

Ruby removed her hands from her eyes and chuckled awkwardly.

"It's okay. I guess it doesn't matter since I've already seen you like this. But just for future reference, friends that aren't me should not be seeing you naked without warning-"

"Understood!" Penny replied. "Now, just allow me to get dressed and I'll be ready to go meet with our friends!"

The gang was going to be meeting up to explore the area, while also enjoying some time off.

Once Penny was all dressed up in her usual attire, the two of them headed out the door, with Ruby trying not to think too much about the sight she had just seen.

Later that night, Ruby and Penny returned from the trip with their friends, and Penny asked Ruby if she'd walk with her back to her dorm.

Stepping back inside, Ruby opened her mouth to say her goodbyes but was cut off by Penny immediately dropping her pants and reaching into her drawer to pull out pajamas.

"Penny! Gosh...!"

Penny looked back at her with a confused expression.

"You said it was okay?"

Ruby let out a sigh before nodding her head.

"Yes- I did. Go ahead, I should be going anyway."

"Okay! Goodbye, Ruby! I had a wonderful time today!"

"Me too, Penny."

Before Ruby could turn around to make her exit, she allowed her eyes to linger on Penny, watching as she took off the rest of her clothes. The sight made her blush.

As soon as she turned around, Penny said something.

"Ruby-" she started. "Before you go, can I ask you a question?"

Ruby spun back around.

"Of course, what is it?"

Penny looked off to the side of a moment, in deep thought, struggling to find the way to phrase her question.

"I've been feeling this strange feeling sometimes. I don't know what it is."

"What kind of feeling?" Ruby asked.

"It's hard to describe..."

"Okay, well, where are you feeling it?"

Penny reached down and used her finger to circle the area around her vagina. Which thanks to the pointing out, Ruby was now staring at.

"Around here. At first, I thought it meant that I had to pee, but I tried and nothing came out."

Peeing was among the new experiences Penny had to learn.

"The first time I felt it was when I was in the shower with you. Then later that night, before I went to bed, I felt it again. I was thinking of you at the time, but I wasn't sure if it was a coincidence or not."

Ruby didn't want to make any assumptions, but she was led to believe Penny was describing being turned on- and it sounded an awful lot like she was saying that she was getting turned on by Ruby.

Choosing to ignore that particular implication, Ruby proceeded to advise her.

"Well- it's hard for me to know for sure without feeling it for myself- but it's possible that what you're feeling is called being 'aroused."

Penny raised an eyebrow and tilted her head.

"Aroused? Like arousing curiosity?"

"Kinda like that, yeah! Except it means that your body is getting excited about something it is attracted to."

Penny frowned.

"Well, it feels weird and it makes it hard for me to fall asleep. Am I supposed to do something about it?"

Ruby had never felt more flustered in her life, but she had to keep going.

"Well..." She took a big gulp, "There is a way to get rid of it. It's something that a lot of people do. The simplest way I can put it is that you touch wherever the feeling is strongest, and you keep- poking at it until you feel super good. Then it calms down."

Penny stared at Ruby as if she had just spoken another language.

"Did that not make enough sense to you?"

"Can you just show me how to do it?" Penny asked, reaching down and pulling up the skin above her vagina, attempting to open it up and take a look. "What is this spot that you're talking about?"

Ruby quickly moved to stop her from what she was doing, her face incredibly flushed.

"I-I'll show you! Just-... I don't really think it's appropriate for me to demonstrate on you, so how about I do it myself and you can just follow my lead. Okay?"

"Okay!" Penny exclaimed excitedly.

"Okay- Just go sit on one end of the bed."

Penny followed the instruction given to her, having a seat on her pillow and sitting with her legs crossed.

Ruby began undressing, avoiding looking at Penny while doing so. If it wasn't for the purity she knew that Penny had, she wouldn't be doing something like this.

"I'm feeling it right now!" Penny shouted as she watched Ruby undress.

This confirmed Ruby's previous inference. It flattered her as well as increased the embarrassment.

With Ruby now naked as well, she walked over to Penny's bed and sat across from her on the other end. She crossed her legs as well but was sure to make her groin visible.

"Okay, so, the technical term for what we're doing is called masturbation- but I just call it playing with myself."

Ruby reached down with one hand, placing it between her legs.

"To start off simple, just rub your private place with your hand, like this."

Ruby demonstrated, running her hand up and down her crease. Penny wasn't really sure what she meant by 'private place' but was able to follow along by mimicking.

"If that feels okay to you, then I suppose I'll just teach you about the sensitive spot."

Ruby reached down with her other hand to slightly spread her womanhood open, using a finger to zero in on a specific location.

"Somewhere around here is something called the clit. That's the most sensitive spot. It's personally too sensitive for me to touch, so I just play with the area around my clit and use that to push up against it. But for you, it might be more enjoyable to touch it directly. It depends on the person. Does that make sense?"

"Uh-huh!" Penny responded, using her index and middle fingers to dig in and search for this special spot Ruby was talking about.

Ruby watched as Penny fiddled around in an attempt to locate the clit for a solid minute.

"I can't find it!" She finally cried out in resignation.

"Here- Here-" Ruby sat up and crawled over to her side of the bed. She stopped before Penny's leg and reached her hand out, holding it in the air for a moment.

"Is it okay if I touch?" Ruby asked for consent before continuing. Penny replied with a firm nod.

Ruby then moved her hand down towards Penny's crotch, nerves flooding through her body. She was about to touch Penny's privates- the thought excited her greatly.

She made contact, gently pressing under her hood to search for the clit. It felt so soft and warm- exactly like how she'd imagined it felt. And yes, she had imagined such a thing.

Penny shifted ever so slightly. The intensity of this moment did not seem to be lost on her.

After a few seconds, Ruby successfully located the clit. Now having found it, she didn't blame Penny for having trouble. It was incredibly small and had probably never had an occasion to better reveal itself within the few days this body had existed. The definition of untouched.

"There it is-!" Ruby exclaimed. "Now you just..."

Ruby began to move her finger against it, causing Penny to immediately recoil, closing her legs reflexively.

"Ah-ha!" Penny looked at Ruby, startled.

"Sorry!" Ruby apologized. "It must be too sensitive for you right now. So, instead, you can just feel around the clit."

Ruby proceeded to demonstrate by gliding her finger in slow circles around the sensitive spot. The tension in Penny's muscles began to lax as she felt Ruby's soothing movements.

"Or you can do it like this-" Ruby continued, removing her finger and instead, placing it over the hood of Penny's center, using it to carefully press down against the clit with a less intense approach.

"I-It feels funny...but good-" Penny declared, leaning back and basking in this fresh sensation she was experiencing. "Does it always make you feel this warm inside?"

"Yes," Ruby replied.

"Woow...~," Penny said in wonder.

Ruby continued using her finger to rub in circles while staring at Penny's face, lost in her expressions, before realizing just how long she had been touching her. It was probably time for her to stop.

"Okay," she said, removing her finger and making her way back to her side of the bed. "So, try doing that yourself, and just keep doing it."

Penny reached down between her open legs and attempted to recreate what Ruby had been doing on her. Once seated, Ruby continued feeling herself under the excuse that it was for demonstration purposes, but truthfully she had an urge.

"I-... I think I'm doing it-" Penny stated, rubbing the hood above her clit up and down.

"Great-! Now just keep it up, and don't be afraid to experiment if you feel like it."

The two of them sat in silence, masturbating directly across from each other. Penny eagerly explored her flower of purity, while Ruby moved her fingers in slower, more deliberate motions. They would occasionally lock eyes, taking in the sight of each other's red faces.

Ruby was ashamed to admit this to herself- but she was getting off at the sight of Penny's naked body. Her adorable face that constantly changed along with the new things she was feeling. Her beautiful round breasts, with now-pointed nipples crowning them. And of course, her precious pink core- of which she had a front-row seat to watch as it was being treated for the first time.

"R-Ruby..." Penny spoke up, "It's feeling really good...w-when should I stop?" She asked.

"D-Don't stop-" Ruby quickly responded. "Just keep going, Penny. I will too."

A small whine escaped Penny's lips. This feeling was almost scary to her- a building sensation that felt as though it could overwhelm her with ease at any moment. But- she trusted Ruby. So she continued.

Ruby could feel an orgasm coming, but she wanted to wait for Penny to reach the same place. She slowed down, biding her time with gentle taps against her inner thigh.

"M-mm..."

Ruby watched as Penny's legs twitched. She needed reassurance.

"You're doing so good, Penny-" said Ruby. "Keep going. You're almost there."

Ruby picked back up with her own pleasure as she felt Penny approaching a climax of her own.

"R-Ruby-" Penny's voice trembled. "What's going to happen..?"

Ruby gave her a comforting smile from across the bed. This smile filled Penny's heart with warmth.

"You're going to feel amazing- trust me. It's going to be intense, but you can do it, and it'll be worth it."

Penny quivered as she nodded.

"Okay, Ruby..."

Ruby breathed heavier as she pushed herself further and further along, watching the orange-haired masterpiece before her.

As Penny felt the irresistible desire for pleasure grow, she increased her speed to supersonic levels, now drilling directly into her clit.

"A-Ah! Ah-!" She shouted, hitting her first ever orgasm.

Listening to these wonderful sounds brought Ruby to her orgasm as well.

Ruby quietly spasmed as Penny loudly expressed the intensity of what she was feeling. Contractions pushing out drops of cum as she settled.

As Ruby rode the last wave of her own pleasure, she watched Penny collapse onto her back, exhausted. Her legs were laid wide open, allowing her to see Penny's vagina pulsating.

It dawned on her what an honor it was to partially cause and witness Penny's first masturbation session. She felt like a proud mother, cataloging a child's first experiences in a scrapbook. But it would probably be for the best if she didn't scrapbook this event...

"H-... How was that?" Ruby asked.

Penny wiped away sweat from her forehead- another unfamiliar concept.

"It was-" she started, interrupted by her own panting, "-incredible!"

Penny sat up, looking over at Ruby with a toothy grin.

"Thank you so much for showing me how to do that, Ruby! Now I'll do it every day!"

Ruby chuckled.

"Okay- just remember that it's not appropriate to do it around other people. Unless you discuss it first."

"It was fun doing it with you!" Penny replied. "Will you do it with me again in the future?"

Ruby blushed. How could she turn down such an offer?

"S-Sure!"

"Yipeee~!" Penny exclaimed excitedly.

She leaned forward further with an inquisitive expression.

"Are there any other ways to feel good like that? Or is that the only way?"

Ruby considered for a moment before responding.

"Well...There's sex-"

Penny raised a brow.

"Sex? I thought that was how people reproduce?"

"Yes- it is- but it's also something that two people who love each other do for pleasure because it feels really good. Like what you just did."

Penny grew excited at this newly discovered prospect.

"We love each other! Let's have sex!"

Ruby's face proceeded to reach its highest record of as red as it could get.

She wanted to tell Penny that it's not exactly something that friends do casually- at least not usually. But- was she really going to say no to this opportunity?

A mere couple of minutes later, Penny was placed over top of Ruby. She sat in-between her legs as Ruby laid down, her left leg lifted up for Penny to hold onto as she grinded against her- their warm delicates meshing together.

Ruby yelled out in loud moans, unable to restrain herself. The feeling of Penny's precious center rubbing against her own was too intense a sensation to bear.

Penny eagerly humped away, her waist moving at an increasing speed. Her face was covered ear to ear with the widest smile she had ever worn, her mouth wide open as she switched between moans and energetic panting. Her body burst with excitement as she ground like an animal in heat.

"This-! This is amazing!" She shouted.

Not only did it feel super good, but she was beyond thrilled to be doing this with her favorite person in the whole world.

"I love you, Ruby!" She proudly declared as friction grew between their clits.

"I-I love you t-too, Penny!" Ruby cried out in response.

The moans built in a synchronized crescendo. Penny moved as fast as she physically could while they stared into each other's eyes.

They hit climax.

Their trembling flowers released their juices upon each other as those ecstatic moans filled the room. Penny's body violently shook as energy drained from her, causing her to slowly collapse onto Ruby's nakedness.

With Penny laying on top of her, resting her head on her chest, they went through the waves of the decreasing intensity of pleasure.

Soon enough, the only sounds that could be heard were the returns of panted breath.

"Wooow..." Penny exclaimed softly under her breath.

Ruby responded by gently lifting her arms and placing them across Penny's back. She wrapped her arms around her and held her lovingly.

These two friends laid in silence for many minutes longer, simply relaxing in each other's comfortable warmth- leaving Penny to wonder the question Ruby had already answered. The question with the answer that seemed too good to be true.

Do love and pleasure always make you feel this warm inside?