"Damn, and I thought he got me bad."

"I'm impressed Weiss. That's quite the red bottom."

Weiss laid face down on her bed, hugging her pillow to her breasts as her roommates looked over her crimson red backside. After her and Jaune had finished… making love, she carefully walked her way back towards her room. Her sister had been kind enough to let her have the rest of the day off, and even commended her for showing such grit and obedience to the master. She had made quite a successful first impression.

And as she had tried to rub away the throbbing pain in her backside, she had found herself dealing with another sensation between her legs. The memories of both her punishment and intimacy with Jaune had kept on replaying in her mind, and she had ended up trying to pleasure herself.

Then the others walked in, and a whole new wave of embarrassment washed over her. She had almost forgotten that she still had to deal with them. "Hey Weiss cream, you know you can't ignore us forever right?" Yang asked, reaching down and giving one of her cheeks a pinch.

Weiss winced, and then reached back and swatted her hand away. "Knock it off! I'm still sore," she said ruefully.

"I'm sure," Blake said, not able to keep an amused smirk from her face. "Did you actually do something to get in trouble, or did he just really get into it?"

For a moment Weiss was silent, then she sighed. "He took over my sister's place in my maintenance spanking. And things just seemed to spiral from there," she said. "It was awful. I didn't think he was ever going to stop, or that I'd ever sit again. But… it was also amazing. The way he just plunged into me, and pinned me down. Had his way with me. And the way he touched and fondled me. Kissed me..."

Being with a real man hadn't been anything compared to her training. She still felt tingly all over her body where he had touched him. And… she wanted him to touch her again. She buried her face in her pillow. Was she a pervert? "Aw, someone is all shy about getting dicked down. Don't worry Weiss, we've been there," Yang joked.

Blake hummed and looked up in thought. "Yeah, there is something about the way he just manhandles you. He's comes off as so polite and tame, but then that switch flips and he becomes an animal," she said, her cheeks turning red as she remembered their last romp in the sheets. "And he knows just where to touch you to make you feel so good and vulnerable."

Yang pouted towards the raven haired girl. "Okay, we get it! You and the master get it on! Damn it, I have to find a way to get back into his bed without getting my ass thrashed this time," she said, crossing her arms. She wasn't going to let Blake get ahead of her in winning his affections.

"You're both shameless…" Weiss muttered.

Yang smirked. "So are you. I saw you pulling your hand from between those legs when we came in," she said before reaching down and sliding her hands between her legs. Weiss gasped and closed her legs, but Yang's fingers had already managed to poke inside of her entrance. "Here, let me help you finish…"

"Y-Yang! You pervert!"

"Aw, you are so cute. And your ass looks so bright against your skin tone."

Blake watched as the Blonde laughed and continued fondling the snow haired maiden, while Ruby sat on her bed with a pout on her face. So far all three of her roommates had gotten to be intimate with the master. They had all been punished as well of course, but so had she. So why hasn't he done anything with her?

At first she had just thought maybe it was timing or coincidence. That Yang and Blake had been flukes. But now? With it being three out of four, she couldn't help but wonder why she had been the odd man out. Had it been because they were in the dining room? He had done all of them in more secluded circumstances. But he could have brought her back to her room, right?

Maybe… maybe he just wasn't interested in her. She knew compared to the others she sort of lacked. Her sister was a blonde beauty, and her breasts alone were enough to get her a second and third glance. She was practically bursting out of that uniform. There was no way she could compete with that.

Blake had a nice pair of legs that would make any man do a double take. And her attitude itself was alluring in it's own way. She also knew that her being a cat faunus was a major turn on for him. And Weiss was on the petite side, but in a good way. She had a princess-like appearance about her. Ruby didn't consider herself a tomboy, but… well, compared to Weiss she wasn't quite as feminine.

Her sister had always told her she was cute, so had a lot of others, but maybe being cute wasn't enough. She huffed. It wasn't like the others were trying to make her feel bad, or making fun of her. But it was a bit of a blow to her pride to be the only one who he hadn't done yet. She was determined to make sure that tomorrow that would change. Even if she got in trouble for it.

Jaune laid in his bed, drifting in and out of consciousness as he tried to decide whether he should just get up and start getting ready for the day, or go back to sleep. Apparently that had been some kind of accident in the kitchen and Glynda needed to tend to, and as she left she had accidentally woke him.

She had apologized for it profusely and insisted she could be punished when she got back, but he told her it was fine. Now that he was awake though, he didn't know what to do with himself. It wasn't as if he had anything on his schedule for today… well, maybe going down to Cinder's place and seeing what she got up to. But he could do that just about anytime.

He did want to get up and head to the kitchen at some point. The girls always went out of their way to make him breakfast and he didn't want it to go to waste. He let out a yawn, trying and failing to summon the strength to get up. This would be the first morning in a while he didn't start by sleeping with either Glynda or Blake. The fact that that felt weird made him wonder if this place was spoiling him a bit too much.

Just as he was about to try and get up again, he heard the door creak open. He looked up, wondering if Glynda was back, but was surprised to see someone else. "Ruby?"

The girl smiled towards him as she closed the door behind her. "Good morning master," she said, a blush on her face. "I hope you don't mind the intrusion."

Jaune shook his head. "Uh, no. Not at all. I guess I'm just surprised to see you," he said, scratching his head. He was surprised to see anyone besides Glynda or Blake in his room this early in the morning really. But Ruby usually worked in the kitchen. He wondered if this had anything to do with the accident. "Are you okay?"

Ruby quickly nodded. "I'm fine. I just… wanted to make sure you were okay," she said walking towards him. "I saw Glynda leaving and… I thought maybe I could keep you company until breakfast. If that'd be okay with you that is."

Jaune honestly had a few questions in mind, but… he felt too drowsy to ask them right now. "Sure, I don't mind. But you won't be getting in trouble for being late or anything, will you?" he asked. He didn't want her getting into trouble just to keep him company.

Ruby looked nervously for a moment, but then shook her head. "No, I should be fine," she said, making her way towards him. She wasn't technically lying, just being… foolishly optimistic? This had been a gamble, and a huge one. And she was probably going to get punished for it later.

If anyone found out that she had caused the little 'accident' in the kitchen, she'd be worked over by Neo, Glynda, and maybe even Jaune himself. If worse came to worse, she'd be sent to Cinder. And that… that would be terrible. But if she could win over the master right now then it was one she was willing to take.

She crawled onto the bed, a nervous yet eager smile spreading across her face as she approached him. Jaune, without even thinking, raised the cover up so she would join him underneath it. He was used to cuddling with someone while in bed, and in his still sleepy state he hadn't even questioned if Ruby would actually want to or not.

But this was fine by Ruby. Perfect even. Now she could… she could… wow, her sister and the others weren't lying when they talked about Jaune. Now that she got a look at his naked form under the covers, she could see how big he was. "Something wrong?" Jaune asked.

Ruby kept staring at his member. How did something that big even fit into a girl? "Uh, I'm fine. I just… uh…" She was at a loss right now. She hadn't actually thought this far ahead. She assumed once she got into his room things would just start happening naturally. That's how the others made it sound.

She couldn't just stay here all morning. Glynda could be back soon, or Neo would notice she was missing. She had to do something. She crawled under the cover, and Jaune looked even more confused. "Ruby, what're you… oh!" He jumped when he felt Ruby take the tip of his cock in her mouth.

She licked her tongue across it before taking more of it in. It was big. Really big. But she could do it. Learning how to pleasure in all sorts of ways had been part of her training, and her sister told her guys loved getting blow jobs. Glynda had given him one after she had gotten punished, and he'd looked so relieved when she saw him leaving.

Jaune was clearly caught off guard by the sudden action, but he allowed Ruby to keep going. He didn't know why she was doing this, but he didn't exactly feel like turning her down. His member started to become harder, and Ruby's eyes went wide as it started to grow bigger. She quickly tried to take more of it in, sucking harder as she did.

"Uh, Ruby…" Jaune muttered. "Maybe ease up a little." If Ruby was at all listening, she didn't show it. She just kept on going. "Ruby… Ruby, hold on a second. Ruby!"

The girl's focus was snapped when she felt Jaune grab onto her shoulders. She looked up at him confused. "W-what's wrong?" she asked worriedly.

Jaune scratched the side of his cheek. "Look, I appreciate the enthusiasm but you're being a little rough. Maybe just slow down a bit?" he asked. It wasn't like he was a master at giving blowjobs. Or like he had any idea of how to give one at all. Still, this had felt so different from the ones Glynda would give him that he couldn't help but think something was wrong.

Ruby looked downright embarrassed. "I'm… I'm sorry. I know how to do this, I really do. I think I'm just nervous. I…" She groaned and ran her hands over her face. "Oh man, I messed up so bad. This was so stupid. I'm stupid."

Jaune's expression quickly turned to one of concern. He reached up and grabbed both of her shoulders. "Hey, hey, c'mon now. Don't be so hard on yourself, and don't call yourself stupid. You just got a little overexcited. It happens," he said.

"No, that's not it. I… I did something bad…"

Jaune looked at her confused. "Okay, well… just tell me about it."

SNAP!

"Ouch!"

SNAP!

"Yeow!"

SNAP!

"Ow!"

Neo frowned as she continued to swing the crop, causing Nora to squeal. She, along with the rest of the maids who made up the kitchen staff, were bent over the dining room table. She was moving from one to the next, giving each of them a set of stinging strikes with the crop.

She was more than a little irked when she found out such a mess was caused in her kitchen. She always made sure all of their ingredients were measured to a tee. So to come in and see dough spilling out of the oven and onto the floor had left her pretty displeased.

SNAP!

"Uh!"

SNAP!

"Ugh!"

SNAP!

"Um!"

Glynda stood by and watched, her arms crossed. When she had come to investigate just how this had happened, she was disappointed to find that nobody seemed to have any idea. She would have liked to think the girls knew by now that while mistakes could and would earn strict punishment, lying about it would earn even harsher ones.

If need be, she would send each of them to Cinder until she found out who the guilty party was. Neo knew that probably included her as well, which was why she was intent on keeping this up until she got an answer. But this was her third time around the table already, and Glynda didn't have all day. "Who was the one who was the last one near the oven," she asked.

For a moment there was silence, but then someone spoke. "I was ma'am."

Glynda looked over towards Coco, and Neo walked over behind her. The short statured maid smirked as she began tapping the riding crop over her pussy, and Coco winced and locked. Glynda stepped towards them. "Ms. Adel, would you care to explain how this happened then?"

Her being on baking duty was strange in itself. She was usually in charge of coffee, tea, and other drinks. Coco sucked in a breath. "Ma'am, I don't know what happened. Everything was ready and already in the oven by the time I got to it. All I did was open the door when the timer went off," she explained. "Then everything spilled out."

Glynda thought for a moment. If she recalled, the one on baking duty was usually… Ruby. She narrowed her eyes before looking around the table. The girl was nowhere to be found. Neo seemed to be thinking the same thing as well, and turned towards her with a questioning expression.

The head maid thought for a moment. And then sighed. She would most certainly deal with Ruby later. If that girl thought her previous punishments were harsh, then she was in for a nasty surprise. But that would be saved for later. That nobody noticed one of their fellow maids were missing their shift, and didn't bother to check the oven before the timer was finished, was still a punishable offense.

"Go around again," she told Neo.

The twin tailed mute nodded, smiling as he brought the crop back again. Glynda would let her have her fun. After all, the fact that she didn't notice was even more egregious, and she would be getting her own bottom warmed later on in her office.

"Oh man…"

Ruby looked down guiltily. Having to reveal everything to Jaune had been more than a little stressful. "I'm sorry," she muttered. "I just… I got jealous of everyone else, and I wanted to spend time with you and… you know, do stuff," she said blushing.

Jaune sighed and ran a hand through his hair. Glynda was going to be beyond pissed when she found out. "Ruby, if you wanted to spend time with me you know you could have just asked. You probably caused a lot of trouble. Somebody might be getting in trouble right now," he said.

Ruby let out a shameful whimper. "I know, I'm sorry. I'm so sorry."

Jaune really couldn't take her looking like that. She was so damn cute it was just… unfair. He let out another sigh. "I know you are. I'll talk to Glynda about this. But… you do know that you need to be punished, don't you Ruby? And that it has to be harsh?" he asked. If he didn't, then Glynda would later anyway.

She nodded sadly. "Yes sir."

Jaune nodded back, and then got up and made his way towards the cabinet on the other side of the room. He opened it, and Ruby paled when she saw all of the implements inside of it. Jaune skimmed through them all. He had used the hairbrush on her last time, so he thought he should use something different.

He had plenty of practice with the cane… so much so it was getting a little repetitive. He had no doubt that it would get the message across, but he'd prefer something else. Ruby felt her cheeks clench as his hand kept wandering over the different implements. She knew that a spanking was going to be the least of her worries if Glynda got her way, but it still made her nervous.

Eventually Jaune made his choice, grabbing the paddle before turning around. "Okay Ruby, please stand up, lift your skirt up, and pull your panties down. I want you to bend over and touch your toes," he instructed.

Ruby nodded. "Yes sir."

She nervously began lowering her panties. She wondered if he just wanted them around her ankles or just taken off, and decided to just go for the later. Once she got out of them, she bent over, pulling her skirt up before spreading her legs a bit and touching her toes. She had been in this position even before her training as a maid.

Jaune walked behind her, already feeling his member twitching. He tried to clear his head. This was supposed to be a punishment. He had to carry it out as such. "This is gonna be tough Ruby. But you've done something very bad. So I don't want you to move. Stay right there, and don't cover yourself. Okay?"

"I'll do my best master…"

Jaune raised the paddle and pressed it against her butt, and Ruby let out a little yelp as she felt the cold wood pressed up against her bare cheeks. Jaune brought it back, swinging it through the air a few times to line up his swing. Ruby jumped slightly each time she saw him move from the corner of her eyes.

Finally, Jaune delivers the first swat.

The paddle was big enough to cover her entire bottom, flattening both cheeks. Ruby let out a yelp, nearly jumping up. She managed to keep her hands on her toes however. Jaune looked over the trembling bottom before him. There were already signs of reddening on it. He tried not to look at the lovely sight long enough to give himself enough time to forget this was a punishment and swung again.

SMACK!

"Ouch!"

SMACK!

"Ow!"

SMACK!

"Oh!"

Ruby yelped as the paddle continued to imprint itself into her backside. It wasn't as if she hadn't been paddled before. She had tasted every single implement multiple times. But Jaune swung so much harder than Glynda or any of the other head maids. The impact and sting were much, much worse.

One of the swats went a bit low, landing into her sit spots with a solid satisfying SMACK, and Ruby howled before jumping up, her hands shooting to her bottom. "Oh! Ow-ow-ow! That stings!" she whined.

Jaune frowned. "Ruby. You moved."

She turned towards him. "I know. I'm sorry. But it just stings so bad," she said, continuing to rub her butt. "I'll be still. I promise." Jaune let out yet another sigh, and then took a seat on the edge of the bed. He patted his lap. Ruby shifted nervously, not having to be told what he expected. "Yes master…"

She moved towards him and then bent over across his lap. He moved his leg, pinning both of hers down, and then rested his hand on the small of her back. Ruby squeezed her eyes shut and braced herself once more. She felt so ridiculous right now. All of this planning and she ended up doing a repeat of their first meeting all over again.

SMACK!

"Ah!"

The first impact of the paddle landed, and Ruby's head shot up. She squirmed over his lap, but Jaune held her in place. The movement across his lap was not doing him any favors in remembering that this was indeed supposed to be a punishment, and that he probably shouldn't have been enjoying it as much as he was.

But there was just something so adorably sexy about seeing Ruby's pert little backside and form wiggling across his lap.

SMACK!

SMACK!

SMACK!

"Ooooh! Ouch! Oh, Master, that stings!"

"I'm sorry Ruby, but it's supposed to. And you did something very naughty. So this is going to be a long one."

SMACK!

SMACK!

SMACK!

"OOOOOOWWWWW!"

Ruby bucked wildly over his lap, and when she reached back to cover her rear, he caught her hand and then pinned her hand behind her back. Ruby whined and continued to struggle, and Jaune couldn't keep a small smirk from forming on his face.

Blake had always been so obedient when it came to taking punishments. And even the girls who didn't care for it much always made sure to hold still and in place. Ruby was so fidgety though. And it was honestly a nice change of pace to have such a different reaction from what he'd been used to.

He wondered if any of the other girls reacted like this too?

SMACK!

"Ooooh!"

SMACK!

"Ow-ow-Oooooow!"

SMACK!

"YEOW! Master, I'm sorry!"

Jaune kept swatting away, watching her bottom bounce and redden with each swing. "I am very disappointed in your Ruby. The last time I punished you, you told me that you would be a good girl. What you did today was the complete," SMACK! "Opposite!" SMACK! "Of!" SMACK! "Good!"

Ruby wailed. "Wah! I'm sorry master! Please forgive me!"

"I will. After you've been punished."

The paddling went on, and Ruby continued to cry out as Jaune laid into her. She let on a string of pleas and promises to be good, but Jaune ignored them. By the time he had finally seemed satisfied enough to finally start bringing the paddling to an end, her butt looked almost like a cherry with how red and shiny it was.

He tapped her butt with the paddle, and Ruby let out a squeal. There were a few tears making their way down her face, and she trembled. "Are you sorry Ruby?" he asked, rubbing the paddle back and forth across her butt.

"Yes. I'm so sorry Master. I'll never do anything like this again. I swear," she said, looking at him pleadingly. "Please don't be mad at me."

Jaune felt his face heat up. She hadn't said 'please don't punish me anymore' or 'please don't spank me'. It was 'please don't be mad at me'. Was she really that worried about making him angry or upset?

"I'm not mad at you Ruby," he said, reaching down and patting her on the head. "A little disappointed, but not mad. And you're probably going to get punished some more when Glynda finds out. But just take it, and don't do anything like this again. The next time you want to spend time with me, just… come and ask. Okay?"

Ruby nodded. "I will."

Jaune then reached down and placed his hands around her waist, guiding her up. Ruby followed suit, pushing herself up off of his lap, but then stopped when he pulled her back slightly. The girl looked back at him confused. "There is one more thing I want to do before you go Ruby," he said, still looking at her butt.

He pulled her down slightly, and Ruby gasped when she felt the tip of his member poking into her butt. "Oh! M-master!" Her butt was already so sore, and now he wanted to do anal? She had been used to doing all sort of sexual acts thanks to her training, but she'd never done anal with her bottm in such a state.

But she certainly wasn't going to protest.

She moaned as Jaune continued to lower her down onto his cocky, inching his way deeper and deeper into her ass. When she was finally fully down on his lap, he reached up and grabbed her legs, lifting them up to give himself a better angle. Then he thrust his hips forward.

Ruby squealed, clasping her hands together as Jaune began bucking his hips at a rhythmic pace. She'd never had anything this big in her butt before, and the odd new sensation was not helped by the fact that every time he moved her freshly spanked cheeks flared up.

Jaune grunted as he picked up the pace a bit, causing Ruby to throw her head back and cry out. She was so tight, and her reaction was just making him more horny. "M-master! Oh god, you're so big! I'm not used to… Mmf!" Jaune leaned down slightly and kissed her, pumping even faster.

Ruby felt like her entire body was on overdrive. The kissing, Jaune ramming into her backside, her breasts bouncing up and down, the stinging. It was all driving her crazy. She could feel her pussy moistening more and more by the second.

Jaune thrust a few more times, each harder than the last, and eventually couldn't hold it in anymore. He grunted as came with one final, hars thrust. Ruby gasped, and not long after feeling the sensation of his seed shooting into her reached her limit as well. She threw her head back and cried out, cumming onto the floor.

Her backdoor squeezed down on him tightly, making sure to drain it of just about every drop. He finished first, and looked down to see the last of her fluids spilling onto the floor. Someone was going to have to clean that later… he wondered who cleaned up all the other messes he'd made around the mansion. The other maids he supposed.

Ruby, looking rather exhausted, leaned back and rested the back of her head against his chest. She looked up at him, still teary eyes, and Jaune soaked in her expression.

He felt his cheeks head up. "Ruby… the way you look and sound when you're getting punished… it's really cute, and it turns me on," he said.

Ruby looked at him surprised for a moment, and then blushed before giving him one of the cutest pouts he'd ever seen in his life. "That's so mean, Master…" she muttered.

He sighed. "I know, sorry." He felt a little bad about it, but… well, she was just somehow so adorable and sexy at the same time.

Ruby was silent for a moment. "But… it is nice to know that you like me that much," she said, growing a small smile on her face. This wasn't exactly how she intended to get it, and her butt was going to keep paying the price, but she'd been able to spend time with him and even get intimate. So this was a success, right?

Jaune blushed even deeper at the look on her face, and then Ruby gasped when she felt his member stiffen inside of her butt once more. "One more time…" Jaune said, lifting her legs up higher again.

"GAH!"

Ruby threw her head back once more as he began thrusting. How had he managed to get hard again so quickly?

"You look like you've been busy Master."

Glynda looked down at Jaune, who sat on the edge of the bed with an exhausted and somewhat guilty look on his face. Behind, Ruby laid on the bed, sleeping away. "Yeah, I think I may have gotten a little too excited. I know you probably want to punish her, but I already handled it. For now anyway. So let's let her rest a bit," he said.

The head maid looked over Ruby once more, noting just how red her bottom still was. It had seemed the young master had done a rather thorough job of punishing her. But given how exhausted she looked, she could only assume there were some other activities that had happened as well.

She pushed her glasses up. "A rather thorough punishment master. Though I would warn against being too friendly with those you discipline afterwards. It can send the wrong message and even encourage bad behavior," she advised.

Jaune rubbed the back of his head. "I see what you mean." If every time he or his father had spanked his sisters they'd given them cookies afterwards, they probably wouldn't have learned their lesson. "I'm guessing you're gonna punish her some more tomorrow though. Maybe I should sit it out. I don't want to get in the way."

Glynda shook her head. "You could never be Master. My advice is just that, advice. You are free to do as you please. Remember, you're to treat us in any way you see fit," she reminded. "That being said, I do think she should be punished further for her actions. And I think you should be the one to carry it out. Have you talked to Cinder again lately?" she asked.

Jaune looked at her curiously. "Um… not today. Why?"

"I think it might do you some good to visit her and see how she instills discipline among the more ill behaved members of the staff. And I think it will most certainly do some good for Ruby if you'd take her with you."

Jaune blinked, and then looked down at Ruby's sleeping form. "Huh… I guess so," muttered. They both agreed that Ruby still wasn't out of trouble yet, and he did think it was past time for him to finally see how Cinder did things. "Should I just go there tomorrow morning?" he asked.

Glynda smiled and nodded. "I'll inform her to be ready and waiting for you."

Jaune got up, and then picked up Ruby in his arms. "Alright. I'm gonna take her back to her room. I think she could use a good rest." Especially since she was probably going to have it pretty rough tomorrow. Ruby stirred slightly and cuddled closer to his chest, and he once noticed just how cute she was.

"Glynda, when we get back…"

She giggled and adjusted her glasses. "My, even after giving Ms. Rose such a hard time you're still ready to keep getting intimate. You and Ozpin are most certainly related," she said amused. "When you come back you'll find me ready and waiting to pleasure you Master."

Jaune blushed and chuckled nervously. "Sorry. It's just… you guys are beautiful. It's just hard not to get excited," he said, feeling just a bit embarrassed. As willing as they were, he still thought he should be able to keep his hormones in check a little.

"No need to apologize, Master. Your interest in us is flattering. Pleasing actually," she said, bowing towards him. When she stood back up, she saw Jaune was in front of her.

He leaned forward, planting a kiss on her lips. She looked surprised, but then quickly kissed him back. After he broke it, he smiled happily at her. "You know, living in this place has been crazy. But you've made me feel pretty comfortable and happy about it. Thank you Glynda," he said.

"It's my pleasure Master."

Jaune walked out, carrying a still sleeping Ruby with him. After he left, Glynda blushed slightly, feeling her heartbeat pick up a bit. "My… settle down now Glynda," she muttered. She hadn't felt herself getting that giddy over a kiss since she first started working under Ozpin. But she was too old for silly little schoolgirl crushes.

She turned and began walking out, going to talk to Cinder about tomorrow. She wanted to make herself clear with the woman one last time before sending Jaune to her…

A/N: Chapter 7! There were SO many people who wanted another Ruby chapter I felt like I had to take another swing at her lol. I hope that you guys enjoy this one. I don't know why I went with anal for her. I just thought it would be fitting for some reason. She's also going to be involved with Jaune's visit to Cinder, which is for sure going to happen next chapter. I hope you guys are looking forward to it.