DISCLAIMER: I don't own the RWBY, or any of the characters in the RWBY. All rights go to the bloody companies that bloody well own them. I only own this story... which has a loose plot thread and is an excuse to have Oscar have sex with a bunch of girls. Enjoy.

And here we have my last harem story that I'll be updating irregularly. The last one I keep thinking of doing but not doing is edowdle's long-requested Golden Temple one, which is also Sonic-themed but... it's been on the back-burner for years. I may not do it, and I like Join The Fun more, so... meh. But yes, about this. This'll be the second RWBY-based thing I've written, and it's going to be set in an AU where all of the top-tier waifus survive past season 3. So, uh, spoilers I guess. Oh, and as always, all characters are of the appropriate age to do the inappropriate things that I'm about to write. Props to Rider09 for the idea, and while I remember, there is an alternate version of this by Dirty Old Qrow which you should totally check out. Dude writes good RWBY smut. And while I remember, there won't be a lemon warning as... well, it's a harem. I didn't do it for More Toys or Join The Fun, and I ain't doing it here. With all of that having been said, I'll see you at the bottom.

Oscar Pine's calloused hands picked up another bale of hay, and he set it aside with the others in the side of the barn. His parents had left to get some supplies for the farm, and they decided from an early age in Oscar's life that it would be a good idea to get educated with the ways of the world without the help of a teacher.

Well, that wasn't entirely true. They did try to get him into several schools, but he didn't last long in any of them. He had basic understandings of basic everyday lessons, and he knew how to defend himself in a fight with Grimm. If his fists weren't enough, one of his parents' many shotguns mounted around the farm were a good substitute for that.

He'd finished shifting the hay around, and he was about to move on to the next thing which was checking if any of the cows were pregnant. As they were in a different barn about 20 acres away from the horse one that he was currently in, it was quite the walk, so he decided to go back to the main house to get some orange juice.

Said house was a cosy little building, looking diminutive compared to the larger buildings which housed the farm's many animals. And yes, that included the chicken coop. Still, the Pine family house was wooden and strong, handmade and built out of hard work, love, and a lot of cursing.

And it was all worth it.

Oscar wiped his hands quickly with the water in the kitchen. The house had access to electricity, and heck, even the Internet. If his parents were around, they'd probably be watching the news right about now... which gave Oscar an idea. He made himself his orange juice, then decided to turn the TV on, sitting on the couch as a news channel started up.

A face that he'd recognised as belonging to one Lisa Lavender appeared, speaking clearly. "And now, for educational news, the academies are accepting new students once more! A year has passed, and so some of the oldest students are in their own Huntsmen teams. Here with more on that is Professor Ozpin of Beacon Academy."

"Ah... this guy," Oscar said as Ozpin appeared. "Always thought he'd be a cool teacher. Shame I don't see myself as a professional superhero."

"If you are a new student who wants to come join, then... well, I am the headmaster, so of course I'd recommend my own school." A little smile twitched his lips as he sipped some coffee. "But, yes, Beacon Academy in Vale. We accept students of all ages, genders, and races, and we do happen to have the highest success rate in team-building and world-saving. You can expect letters in your postboxes within the week."

'I wonder if that'll be the case...' Oscar wondered to himself as he turned the TV off. He cleared his throat, finished his drink, and got back to work.

In the days following, letters had appeared, but none that would happen to be offering education at Remnant's most prestigious Huntsmen academy. Not that Oscar minded. It was one thing to hope, but it was another to expect it, even though he hadn't had time to send in a form to ask, or even ask his parents to do it for him.

But that train of thought was shaken when he got a knock on his door. He'd finished his work for the day, enjoying some lunch despite him sweating through his simple clothing of a white tank top and light blue jeans, his brown boots next to the couch that he was sat on. He got up and put the boots on as he went over to the door.

'Might be someone looking to buy some eggs...' Oscar said as he opened the door.

And then... well...

In Oscar's line of work, he and his parents were usually expecting men about his father's age or older to pop up at the door. They'd show up asking for, say, some chickens for eggs, some vegetables or fruit, or just some farming equipment, and the Pine family was more than happy to oblige with those requests.

At the door was not an old man in farmer's overalls and a straw hat, and they didn't seem to be asking for something judging by the letter in their hand. It was a teenage girl, Oscar presumed, with pale, beautiful skin, modest curves that were hidden well behind her red and black hooded outfit. Bold move to wear something hooded in such weather, but Oscar wasn't one to complain. The girl had dark hair with crimson at the tips, she wore an adorable smile, and her eyes were a shade of encapsulating silver. To complete her outfit was a pair of grey leggings... or tights, maybe, as Oscar saw a black skirt, and finally was a pair of black boots with red accents.

"Uh... hi..." Oscar gulped.

"Ah, Oscar... Pine... right?" the girl asked. Her voice sounded light, almost like she was three years younger than she appeared. Oscar nonetheless found it quite adorable. Her disarming smile helped.

"Uh, yes, that's me," Oscar said. "And you are?"

"Ruby Rose!" the girl said.

"Ah. Well, miss Rose, how may I help you?"

"I'm not sure that I understand," Ruby raised an eyebrow, not dropping her smile.

"Well, what do you need?" Oscar asked. "Some fruit? Vegetables? Maybe some eggs from the coop?"

Ruby laughed. "Oh, that's not what I'm here for. No, no." She let out a few more giggles before getting her voice back to its usual tone. "I'm sure that you've heard that the Huntsmen academies are opening soon in time for the new school year?"

"I may have seen it on the news lately," Oscar said, shrugging. "Why do you ask?"

Ruby held up the letter in her hand. "Because this letter is for you. At Beacon Academy, I lead my own Huntsmen team, and we're one of the best ones over there. In the time between school years, the academy has been trying to keep busy, and that busywork happens to include possibly getting new students to join us."

"So, that letter is for me?" Oscar asked.

"It is indeed!" Ruby smiled. "It's another part of the reason why I'm here. I believe that your parents sent in the request anonymously. They admitted that you don't have a lot of experience in fighting, but that you have enough. Enough to qualify as a student, at least."

"My... my mum and dad did it?" Oscar asked.

"Well, yes, but they wanted it to be a surprise," Ruby said. "I was supposed to show up yesterday where they were here all day, as they told me. But my ride over here got delayed, and due to the time crunch, I figured that I'd try to get over here and do what I could."

"Well, they're out at the moment," Oscar said. He then looked down at himself. "Oh, goodness, I'm so sorry. I'm sweaty and stinky, and I opened the door not expecting someone from Vale's top academy to hand me a letter telling me that I got in, and-"

"Actually, you're not fully in, just yet," Ruby said. She reached into her hoodie and pulled out a folder. "There is a written exam that you have to take part in. You can do the physical exam against some Grimm when you get to the school."

Oscar took the offered folder, seeing some more paper inside. Not a lot of pages inside it, about twenty to thirty. He gave the test back to Ruby so that his sweat didn't stain it too much, then stood up and went to his kitchen. Ruby followed him, and she sat across from him as he finished his food.

"All right... um..." Oscar coughed nervously. "I'll go and... shower... then I'll come and take the test." He put his plate in the kitchen sink and washed it. "Feel free to help yourself to something if you're hungry. We've got plenty to go around."

"Much appreciated," Ruby smiled. "I'll be waiting."

Oscar gave a nod, leaving and going to the bathroom. The shower water was soon running, and he got a towel ready for drying after. He focused on getting himself clean as opposed to presentable or smelling as fresh as his surname would suggest, and he dried himself and got dressed into some new clothing that wasn't too different from what he was wearing previously. When he was done, he walked back out to see Ruby still waiting for him.

"Ah, you're still here," he smiled.

"Well, I sort of can't leave until your exam is over," Ruby giggled. "I won't be doing a lot. Just monitoring your progress, then when you're done, just tell me, and I'll be out of your way."

Oscar nodded at that, and Ruby handed over the test, as well as a pen. Oscar took them both, opened the test to the first page, clicked the pen, and got to work.

As Ruby promised, she wouldn't do a lot except for monitor. As the test was already short, the time seemed to go by much faster when the two made some small talk along the way, and Oscar felt himself get less nervous around Ruby, sharing some jokes with her and finding her bubbly personality to be rather endearing, as if her looks hadn't done enough to convince him of that.

"All right... and... all done," Oscar said, handing the test back over to Ruby.

"Ah, fantastic," Ruby smiled as she took the test and pen back. "All right, you've got a few days until the school starts, so we'll have enough time to grade this by then and see where you stand by the time that you get there."

"Well, thank you for letting me know about this," Oscar said. "I'm glad that my parents did this, and I'm not a good liar, so I'll tell them that you came around to help with all of this."

"Is that so?" Ruby raised an eyebrow.

"Yeah," Oscar replied, a bit confused at the question. "I mean, you just examined me, and you called them before, so..."

"No, not that," Ruby grinned. "What you said before that, that you're not a good liar? What do you mean by that?"

"Uh... well... I mean, I guess that I-"

"Do you think I'm pretty?" Ruby cut him off, maintaining her grin.

"I... I don't understand what this has to do with... uh..." Oscar paused. "I... I do. I did when I opened the door to you, and I still do now. Even more so now, in fact..."

Ruby blushed a bit at that. "Well... are you, by chance, a virgin?"

Oscar was taken aback by that last question. "Um... I mean, n-no, but I'd like to know... what that has to do... with anything..."

Ruby smiled and slunk over to him. "Well... let's just say that, on the trip over here, I got really pent up... and I know that there's plenty of girls at Beacon Academy that you're going to find... rather appealing..."

The farmer backed away a bit at that. "It's... it's not that type of thing, is it? Beacon Academy isn't secretly a sex club full of horny women and it is an actual academy that teaches Huntsmen and Huntresses, yes?"

Ruby giggled. "It is! Oh, my god, you are so adorable when you're flustered!" She sat closer again, her smile almost like an invisible force that stopped Oscar from pushing back any further. "But, to answer your question, yes, there is actual teaching. But we're all mature and responsible over there, I assure you."

"Ah... that's good to hear..." Oscar said. "So... uh... how does this work?"

Ruby smirked, mounting herself on top of Oscar. "Well... you and I are going to have some fun before your parents get back. We're going to clean up in time for them to return, I'll tell them about what's happening - minus the sex part - and we'll ship your handsome self off to Beacon first thing tomorrow morning."

"Could we at least do it in my bedroom?" Oscar blushed.

"Lead the way!"

Ruby got off of Oscar, and by extension, off of the couch, and Oscar took her hand and guided her to where his bedroom was. It was cosy, like the rest of the house, but Oscar did have a sizeable enough bed for their intended activities. As they made their way to that bed, Ruby was almost all too eager to lose her clothing, exposing her pale body in full to Oscar.

The farmer couldn't believe it. I mean, of course, she appeared beautiful while clothed. But seeing her slight curves and athletic body without them on was something else entirely. In the middle of his gawping, Ruby climbed onto the bed and laid on her back, smiling over at Oscar and reaching between her legs to rub her pussy, moaning softly and gasping at him.

"Are you going to leave me here?" she smirked. "Or are you going to join me?"

Oscar nodded in reply, and he started taking off his clothes too. Now, Oscar himself knew that he wasn't an average looking lad for one in his mid-to-late teens. Due to his farming work, he had a better body than most would at his age, and his diet consisting mostly of unprocessed, organic food and drinks only served to help that along.

As Ruby took in how Oscar looked, her eyes went down to his boxers. She did feel a bit disappointed that he wasn't fully undressed yet, but he saw his hands work on the waistband of those boxers and slowly pull them down. And, at that moment, Ruby discovered that Oscar's body wasn't the only thing that was past average.

"Oh, wow..." Ruby giggled. "You did say that you weren't a virgin... I feel so sorry for the girl that had to take that during your first time..."

"She called me a freak after..." Oscar lamented. "Apparently, I didn't make her feel good enough. I know that I was a virgin, but I knew how good that I made her feel."

Ruby sat up on the bed. "Well, fuck her for thinking that way. She had a good thing, and she didn't hold on to it. I bet that she's with some fat-bellied, small-dick loser whose idea of making a woman orgasm is eating her out when she promises cheeseburgers in the morning."

Oscar couldn't hide his laughter at that. "I didn't expect you to have that mouth, but... that did cheer me up..."

The red-hooded Huntress winked. "Well, how about I make you a little bit happier?" She reached her hands out. "Come over here and kiss me..."

Oscar went over to her, sitting down with her in bed and pressed his lips to hers tentatively. Ruby, however, was having none of that, and she wrapped her arms around Oscar's neck and pulled him down on top of her to deepen the kiss. Oscar was surprised at the reaction, and even more surprised that he went along with it, their smooches matching each other almost perfectly as she felt her hand move down his body.

She appeared to drag a finger over his toned, if not super densely muscled, torso. Oscar couldn't help his reaction, pushing himself up a bit so that her hand was brushing against the head of his cock. Ruby grinned into the kiss, pushing her tongue into his mouth, and it didn't take long for his tongue to battle back against hers.

Ruby started to stroke his cock with her hand, moaning more into the kiss before Oscar pulled his lips away from hers. They shared a few pecks after that before going back to making out, and Oscar found himself essentially fucking Ruby's hand as his own hands started to take action. He traced feather-light touches over her stomach, causing her to almost purr in satisfaction, and soon, his hands reached her breasts, cupping them both before he pulled his lips from hers yet again.

Ruby moaned as Oscar stopped their kiss, and he moved his head down to kiss her breasts. She arched her back to push more of her tit into his mouth, and he kissed around the nipple before moving to suck on it. Ruby moaned more as Oscar sucked hard on her nipple, and she felt her hands clutching the back of his head to pull him closer. He growled and bit into it as one of his hands moved down to play with her pussy.

The red-hooded Huntress bucked her hips up against his hand, and he kept rubbing her lower lips with his hand, his other moving to her free breast before he switched to suck on that one as well. Ruby groaned in pleasure, her feet pressing against Oscar's hips, almost as if she tried to push him down to her pussy. Instead, she wound up stroking his cock with them, and he moaned, thrusting against them and growling in pleasure.

Ruby moaned as Oscar fucked himself against her feet, and he countered that by shoving a finger into her pussy. The digit slid in deep, and Ruby gave his cock a few more strokes before using her hands to push him down her body. He slowly descended down her, kissing her stomach, groin, and nipping on her thighs before attaching his lips to her pussy, his nose pressed against her labia as her tongue-fucked her glistening pussy.

"Oh... yes!" Ruby moaned, her hand reaching down to grab the back of his head as he ate her. "Fuck!"

Oscar growled in pleasure, his breath hot against her skin as he focused on eating her. He sucked on her outer lips, moaning at the taste of her juices before moving to wriggle his tongue inside of her cunt. His hands moved up to keep her thighs spread as he licked her, and he was strong enough to prevent her from wrapping her legs around his neck and keeping him where he was, which he could feel that she was tempted to do anyway.

That urge only grew when he added two fingers to her pussy, twisting them around as he pushed them in and pulled them out of Ruby's tight wet hole. The red-haired warrior moaned and gasped as he finger her, and she felt a climax coming. Without warning, instead focused on her own pleasure, her pussy pulsed, spurting streams of her juices onto Oscar's face and a bit onto the sheets as well.

Oscar noticed this, and he moved to lick up what he could, extending her orgasm and causing more juices to fall around his mouth. They dripped down his chin and onto the bed, and he made a show of licking up what he could before moving back up her pussy, then up her body, then trading a hot kiss with her again, moaning as their tongues rejoined, their hands roaming each other in need.

That was until Ruby took a bit more control. She mounted Oscar and, like he had done with her not too long ago, she started kissing down his body, even licking his nipples playfully before she reached his cock. She looked at it, her eyes a bit crossed as she did so, and she licked along the shaft of it, winking up at Oscar as he let out a pleasure moan, gasping for more of her mouth on him.

As it turns out, the farmer didn't need to wait much longer. Ruby licked a long, slow, almost borderline torturous line up from the base of his shaft up to his tip, and she wasted no time at all in taking the tip into her mouth. Oscar groaned as Ruby sucked around the tip, her tongue swirling around it as she bobbed her head up and down, her lips moving back and forth over his tip, her tongue even teasing his slit and earning more moans from him.

Oscar reached a hand down to her hair, shifting it from her face to look down into her eyes. She moaned softly, leaning her head into his touch before moaning and moving her mouth down to start taking more of his cock into her god. She rested her hands on his hips as she started moving her mouth back and forth on his cock, the tip tickling her throat every so often as his hips moved to hump against her mouth a bit in time with her sucking.

Oscar then took more initiative and moved his hand to the back of her head, starting to thrust into her mouth. Ruby gasped, but grinned around his cock as he fucked her face lightly. The head of his prick poked at the back of her throat, but she opened it up and took it down there, closing her throat around his cock as she went down to take more of his length, moaning deeply and making her mouth vibrate around his dick.

"Oh... shit..." Oscar groaned. "I've had blowjobs, but not like this... fuck..."

Ruby giggled in reply, her hands moving to stroke what part of his cock she couldn't get down her mouth. She kept stroking with one hand as her other moved down to rub his balls, grabbing and squeezing the skin there and causing a hiss of pleasure to emit through Oscar's clenched teeth. He grunted and started fucking her throat more, his balls swinging up against her chin, her hand still playing with them.

Ruby then knelt back a bit, pulling her lips away from Oscar's cock and sitting back on her heels. She opened her mouth wide to show some spit, and winked up at Oscar. "Come and fuck my face, farm boy... treat me like a naughty little slut..."

Oscar certainly didn't need to be told twice. He stood up, stroking his cock in the direction of her face, and he pushed it into her mouth. After that, he wasted even less time in pushing it down her throat, his hands on the back of her head as his meat slid down her gullet. He grunted in pleasure as he started to do as she had demanded, his hips moving back and forth as his cock slid around her mouth and down her throat while he humped her face.

Ruby choked and sputtered around Oscar's cock, and he grinned down at her, taking some initiative and holding his cock down her throat before pulling out. He stood over her, his balls dangling over her face and causing her to suck them down her mouth a bit before she pushed her head further down, her tongue licking his ass. He moaned and stroked himself hard as Ruby rimmed him, the farmer boy panting from the pleasure of the unexpected act.

Oscar then pushed her head away from him, laying back on the bed and spreading his legs, still stroking himself. Ruby teasingly grabbed one of his feet and kissed it briefly, moaning as she did so and sucked the toes too before moving her lips further up. She kissed along his knee and then up his thigh before reaching his ass again, diving down to rim him eagerly, his hand on the back of her head as she kept her own hands behind her back, loving the feeling of Oscar taking control.

He soon pulled her head away from his ass, and he pulled her on top of him to kiss her. "I didn't expect this kind of invitation..."

"Bit dirtier than how you usually have sex?" Ruby winked. "Don't worry... the girls who I work with at Beacon Academy will give you the same treatment... never mind that you're smaller and cuter than all of them."

Oscar blushed a bit. "Well... I guess I'm big where it matters..."

"Damn right you are..." Ruby giggled. "Now use that big piece of yours to make me feel good..."

Oscar did just that, lifting Ruby up a bit and positioning his cock at her entrance. He was... fairly big. Bigger than any previous boyfriend that Ruby had had, that was for certain. So, she took her time in sliding her pussy down onto him, despite the fact that she had lubed him up pretty well earlier with her blowjob, much the same way that his mouth had lubed her up with what was, hopefully, the first of many squirting orgasms.

Oscar even held her hand as she slid down, a somewhat sweet gesture that did earn a small smile from her. That smile faded as she took in more of his cock, and slowly, over time, she eventually managed to take it all in, the impact and feeling of all of his meat inside of her causing her cunt to pulsate with a short, spraying orgasm of its own around his cock, the grip of her hand tightening on his as she came.

"Ooh... shit..." Ruby's silver eyes seemed to glow with pleasure from that, and she screwed them tightly shut.

Oscar let her breathe, though, watching her chest rise and fall before speaking. "Just tell me when you're good to go..."

Ruby nodded at that, smiling down at him as her eyes opened back up again with a wicked lust. Taking that as a sign, Oscar started moving his hips back and forth. Well, about as well as he could, considering that Ruby was on top of him. But still, his hands were on her hips, and he guided her back and forth onto his cock as she rode him, her hands reaching for his headboard to grab it as he slammed himself in and out of her from underneath.

Oscar kept a hold of her hips and kept swinging them up and down into her, his cock pulling out a bit, sheathed with her juices, then going in seemingly deeper each time. Ruby panted, her tongue rolling out at the explosion of pleasure that she was starting to feel, and she soon sat up to spray a stream of her juices that shot far enough to hit Oscar's chest. She rubbed her clit and spanked her pussy lightly to get more of it out before leaning over to hungrily suck her juices from Oscar's chest.

The farmer was feeling pretty proud of himself for what he'd done, and he grinned darkly as his hands, still on her hips, pushed her back down onto his cock. Her lips licked and bit his chest as he started fucking her again, going a bit rougher, a bit harder this time. One of his hands moved to her ass, spreading the cheek there and spanking it, while his other hand moved to rub her clit while she herself reached to play with her own nipples, twisting them in pleasure as Oscar fucked her like this.

She looked up at him after cleaning his chest of her cunt juice, and she shared a deep kiss with him, their tongues duelling as Oscar's pace slowed down a bit. Ruby gave a push with her mouth, more out of a silent complaint of need rather than aggression, and Oscar sped up for her when she did it. He spanked her ass as she continued to ride him, causing her to gasp into his mouth, their shared breath hot as they both laughed some at her reaction to his spanking.

Oscar then moved both hands up to hers, reaching to lock her arms behind her back. He kept one hand there and moved another to her pussy, using his thumb to swipe over her clit as he took as much control as he could from underneath her. He lifted her hips slightly with his own, fucking himself up into her with rough strokes before suddenly, another orgasm expelled itself from her body, its watery contents splashing onto Oscar's cock, testicles, and torso.

Ruby shuddered from the pleasure again, grinning as she sat back a bit to calm down before she felt Oscar's hands on her hips. He pulled her back to him, kissing her as he slowly turned them over so that he was on top. He smiled down at her and kissed her, a smile forming on his lips as he felt one of her hands reach down to guide him back inside of her. Oscar moved his hips forwards a bit to thrust back into her, staying there and panting with her.

Ruby reached her feet across his hips, pushing them behind his lower back and trying desperately to bring more of him into her. More than happy to oblige, he started moving in and out of her at his own pace, his hands on her breasts, palming and kneading them as he fucked her. He pulled his lips away from Ruby's to focus on his thrusting, almost using her boobs for leverage as he fucked himself in and out of her at a slow, almost agonising pace.

He would then pick up his speed for her as he felt her pussy tightening. He had gotten used to feeling her insides lock up around him when she was about to cum, and as he felt it, he rutted her ruthlessly, slamming hard in and out of her. His hands went from her breasts to her legs, reaching under her knees so that he could lift her legs up over his shoulders as he drove himself into her, thrust after thrust causing pleasured yelps from the silver-eyed girl.

"Oh... yes! God! Fuck my cunt! YES! UGH!" Ruby pushed back against Oscar's fucking, arching her back as she came again, squirting on Oscar's abs and cock and thighs. She rubbed her clit to get a little bit more out before rolling onto her side, then onto all fours. "Like this now..."

Oscar grabbed her ass as she presented herself. "You want me to fuck your pussy again?" He squeezed her cheeks, their pale complexion reddening with his rough touch on them. "Or do I get this too?"

Ruby moaned. "Maybe next time... you get that..." She playfully winked. "Unless you want it now... big strong farmer boy..." She shook it for him. "Take it... if you want to..."

"Have you... done it there? Before?" Oscar asked.

"Not with anyone as big as you," Ruby admitted. "Or with a real cock... mostly my team likes to play with me back there... so... I'm officially losing this virginity to you..."

"I'll be gentle..." Oscar promised.

Ruby was about to reply to his kindness with words, but that sentence was turned to a shortened gasp as she felt his tongue slithering its way inside of her ass-hole. She gripped the bed sheets, moaning as Oscar added a couple of fingers to her pussy while he rimmed her. She moaned at the familiar feeling of it. After all, her team had licked and fingered and done more there before, and she'd done the same to them as well.

But Oscar's tongue almost felt different. And with its eager eating of her ass, she felt herself growing wetter. She felt the need to climax coming back to her. That need was only doubled when Oscar moved both of his hands to her ass cheeks, spread them, spanked them, and then he shoved a finger up her ass-hole. That set off a trigger for her, and she gushed hard onto the bed sheets. Oscar chuckled and pushed two fingers into her cunt as she came, pumping them hard to make her cum more.

"Ooh... my... fuuuuck..." Ruby shook. "That felt so good! AH!"

She gasped again as she felt the farmer boy's now pussy-juice-slicked fingers push into her ass, causing her eyes to widen as he fingered her there. While he was still behind her, he moved to attack her pussy with his tongue, the mixture of sensations causing Ruby's body to seize up in pleasure again. She bucked her hips back against him, taking his fingers deeper up her ass as he pumped them in and out, adding a third to cause another squirting orgasm from her.

Oscar had finally deemed that that was enough, so he got up behind her, stroked his cock, and aimed it for the tight brown hole that was starting to close up. He pushed the head inside of her, and she let out a hiss that was a mixture of both pleasure and pain. Oscar stopped moving almost instantly as soon as he heard the noise from Ruby's mouth, and he kept his hands on her sides, rubbing them soothingly as he started to speak again.

"Is... is everything okay?" he asked. "Are you sure that you want to do this?"

Ruby nodded. "Please... take my ass... I've had big toys up there... I think that I can handle your big toy too..."

"Is that all that I am?" Oscar smirked. "Just a toy to you?"

Ruby giggled, again about to speak, and again silenced as Oscar spanked her, sliding more of his cock into her tight ass-hole. His hands stayed on her butt cheeks, keeping them spread as he invaded her rear end. He gave her another spank, causing her to yelp a bit before he started fucking her. He sat back a bit to drive himself into her deep, and she rolled her head back as he began pacing himself inside of her, his hands groping her ass cheeks harshly.

Oscar gave a few more sharp, almost testing thrusts, and then he started to fuck her with deep and hard strokes. Oscar's eyes rolled back in pleasure, the feeling giving way to less pain as he kept pushing in and out of her. He reached a hand down to the back of her head, lightly pulling her hair mostly so that he could pull her upper body up, turning her to kiss her as he kept humping in and out of her ass-hole, their skin slapping together deliciously.

He kept his grip on her hips going, squeezing deeply into them as he drove harder in and out of her ass-hole. To get more leverage, he leaned himself up, pushing himself up and down into her rear hole and moaning as he put a foot next to her head. She kissed his foot as he kept slamming hard into her ass, spanking her pale cheeks to redden them further. Ruby continued to moan at his treatment of her, bucking her hips back against him as he kept fucking her.

The thrusts causes another orgasm to begin building inside of her, and he pulled out to see her cumming hard onto the sheets again. Her juices jetted out behind her to cover his legs and hers both, and he pulled her around and turned her onto her back to see her perky tits again. He moved over to where her head was, and she opened her mouth to accept his cock into it, his hands grabbing her tits as he fucked her mouth once again, her moans sending tingles down his shaft.

Her mouth spat around his cock as he fucked it, one of his hands moving from her tits and reaching over to her pussy. He rubbed her clit, pinching it in his hands, and he soon felt her own hands pulling his hips forward more. He felt her throat close around his cock, and he held it there before pulling out and stroking himself as her head lurched back to suck his balls, soon moving back to lick his ass-hole and causing him to shudder from the contact.

He then stopped stroking his cock, Ruby soon taking that over in conjunction with her rimming as he decided to focus on her cunt. He slid three fingers into it and began pumping them harder into her, soon feeling her juices around his hand. She moaned into his ass as he fingered her, and he used his other hand to slap and strum her clit as she began to gush around his fingers again. He kept rubbing her clit as her body shook, getting more juices out before pulling himself away from her.

Oscar grabbed her hips and pulled her close to him again, shifting them so that she was sideways and facing him. He grabbed one of her legs and swung it over his him, and he sheathed himself back inside of her and began thrusting into her again. Ruby moaned loudly, soon being cut off by Oscar's lips on hers again as he fucked her, and he soon pulled his lips away from hers to hear her moans again as his hands grabbed her tits, squeezing them and kneading them roughly as they bounced softly in his tight grip.

"Oh, fuck!" Ruby moaned loudly. "Oh... god... no one's made me feel like this before..."

Oscar kept fucking her roughly, feeling her juices starting to wash over his cock again. He spread her legs again, rubbing her clit hard as she came and squirted. He smirked at her. "To be honest... nobody's made me feel like you have before either... or has done so much risque stuff with me..."

Ruby blushed. "I'm... sorry... about that... I guess I never got to let go with anyone else like that..."

Oscar panted. "Speaking of letting go... I'm close..."

Ruby smiled. "I want it on my face... as risky as it might be by the time that your parents come back... but eh... I don't care... I feel like such a slut for you already... we may as well cap it off appropriately, right?"

Oscar laughed a bit at that. "Right..."

He then turned her around, her back facing him, and he lifted her leg again, his cock still buried inside of her pussy. He went back to thrusting into her as he opened her legs up, one hand keeping her right leg lifted as his other moved to attack her clit. He palmed her groin and tweaked her clit with his fingers as he kept thrusting into her deep and hard. Ruby turned her face to capture his lips in another kiss, the moans between them intensifying as they moaned and moved together.

He grunted into the kiss too as they kept fucking, and he continued to twist her clit as he felt her cumming again. She gasped in pleasure and moaned as she started to cum, this time pushing him back as she reached her own hands down to rub her pussy and make herself cum, her wet hole spreading and spraying her juices out onto the bed again. Oscar chuckled and leaned over to kiss her tits as she came, sucking a nipple into her mouth as she came down from her orgasm before pulling his head back up to hers to kiss him once more.

Ruby bucked her hips back against him again, and he moved his cock between her ass cheeks and shoved it back up into her butt-hole. She groaned in pleasure again, and he held her legs together as he started fucking her ass-hole hard and deep. Ruby's hands worked over her body, reaching to play with her tits, pinching her own nipples roughly as Oscar's shaft continued to piston in and out of her ass in time with his heavy thrusts. A few more hard slams, and she pushed herself forward again, spreading her legs free from his grip and letting her juices shoot out, splashing onto her stomach and thighs too.

Oscar grabbed her by the hips again and pulled her on top of him in reverse, and she leaned forward to grab the sheets as he found his way back into her ass. He kept swivelling his hips up and down as he thrust into her, his hands grabbing, kneading her ass cheeks, slapping them hard with both hands as he kept hammering into her. Ruby moaned and arched her back, turning an eye back over her shoulder to look at him as he kept fucking her before rubbing her clit, causing her attention to be drawn down to her cunt as she started to cum again.

Oscar kept spanking her as she turned around on his cock, looking to face him before pulling him up into a kiss. Their arms wrapped around each other as he kept thrusting into her ass, and their tongues wrestled once more as Oscar panted against her lips, his thrusts getting a bit sloppier. But he stayed determined, and he tried to focus on giving her pleasure, reaching a hand down to finger her pussy again to make her squirt once more.

"Oh, fuck yes!" Ruby panted as her juices shot out onto Oscar's stomach again. "Fuck! Give me that cum! You plugged my cunt and my ass so good! Paint my face! Please!"

Oscar managed to pull out of her, and he pushed her onto her back on the bed, kneeling next to her head and stroking himself in her direction before his eyes screwed shut. He sent blast after blast of his cum all over her face, moaning hard as he painted her. Ruby happily took it all onto her visage, her mouth open to catch some of it too as she got splattered. As Oscar finished, she sucked out the last of it, panting hotly and letting out pleasured moans.

"Mmm... we still have time before your parents get here?" she asked.

Oscar nodded. "We do... I think that we should clean up..."

"Agreed..."

So, they did just that. They put the sheets away, got showered and changed, and managed to get new sheets on and such too. They even changed the sheets of Oscar's parents, who, when they got back home, thanked their son and this silver-eyed girl for her help. They thanked her more with hugs when they found out that Oscar had gotten into Beacon Academy, to which Oscar thanked all three of the others with his own affectionate gestures.

Oscar and Ruby stood outside of his house as it began to darken, and she smiled. "See you when you get to Beacon!"

Oscar smiled at her. "Thanks... for the letter... and for, you know..."

Ruby winked. "Any time." She leaned to give him a kiss on the cheek before heading out of the farm.

"Oscar!" his mother called. "Time for supper!"

The farmer boy looked as Ruby gave him one last wave, and he waved back before calling to his house. "On my way!"

And that is it. Pretty much one of the three harems that I'll be updating semi-regularly. So... yeah, expect Oscar to have similar dealings with the other girls of the RWBY-verse. The next chapter will probably be Yang. Oh, and before I forget, I think I have only a few more More Toys chapters left in me before I'm done with that series. Next time, though, more Cyber Riders 2. Until then, take care, and stay tuned.