Ruby was slumped over the desk in her room. Even after three hours of working, she barely made a dent in her homework. She wanted to cry at this point. Her grades had been slipping heavily and she was so close to failing. She didn't want to drop the classes out of fear of disappointing her dad and sister. "P-Please…I'll do anything to make this even a bit easier." She muttered to herself as she whipped the forming water from her eyes. Her hands were in her hand, lightly wet from tears of frustration. She was so occupied with herself, she didn't hear the small poof behind her.
"Anything you say? You'd do anything?" An unfamiliar voice asked behind her, making Ruby twist back in shock. The boy, if he could be called that, appeared to be her sister's age. He looked mostly human dressed in jeans and a hoodie, but the red horns poking out of his head, single bat like wing, and long tail showed he was anything but.
"Wha-Who are you?!" Ruby nearly shouted as she scooted back out of her chair until her back hit the desk. Fear filled the young girl. Who was this guy? How did he get here? And what did he want?
"Me? I'm Jaune. Short, sweet, rolls off the tongue, ladies love it." The boy chuckled. "You seem to be struggling with that work of yours?" He peered around the frightened girl at the papers scattered on the desk. "But don't worry, I'm here to help" He seemed genuine, and the fact he wasn't trying to hurt her or anything helped his case.
"H-Help?" Ruby was now incredibly confused. This man looking thing had materialized into her room, but now was offering to help her with homework? That didn't make much sense. Shouldn't he be doing something more nefarious?
"Yep. For a very small price, I can help you with your homework and more. You just have to agree to take it." Jaune took a few steps closer as he spoke until he was standing just a few feet away from the scared girl. He held his hand out to shake, a large trusting smile on his face.
"A-Alright.." Ruby was a bit taken aback by the line, but slowly nodded. This guy seemed friendly, she'd humor him for a bit. Worse comes to worse she'd just scream and her Dad and sister would barge in to save her. They may be a bit over protective sometimes, but the two kickboxers were always ready to fight for her.
Jaune smiled as he reached the desk. There was only one chair but that didn't stop him. He moved to sit down and right before he fell a chair formed in place. "Alright. Where exactly are you struggling?" He started to pick up and look at the papers. "Uhhh... Oh physics." Ruby sat back down into her chair next to him. "I can't seem to wrap my head around this one question here." She pointed towards her homework.
Jaune looked at the question, thinking for a moment before smirking. He flicked his wrist and a piece of paper appeared in his hand. When he sets it down Ruby could see a step by step formula to solve the question, even using her problem as the example.
"Wow! Uh How did you do that?" Ruby asked in mild amazement but largely confusion. She assumed it was the same way he had appeared in her room, but the sight of it still made her head spin.
"Oh don't worry about that. It's just a little trick I picked up. " Jaune playfully waved her off. He kept reading her homework, comparing her scribbled notes to the question itself.
"Alright..." Ruby was still unsure about all this, but she was happy that this man...thing was helping. The situation kept getting weirder and weirder, but she knew it could have been worse. At least this humanish thing was trying to help her get some physics done. Uneasiness aside, Jaune kept pulling magic cheat sheets, not only giving her all the answers but teaching her as well. Ruby can't explain it, but it felt like the information was just pouring into her. Soon her four classes worth of homework were done in less than an hour. Ruby was ecstatic when she was able to put away the homework with no worries. "Thank You! This helped so much!" She beamed at Jaune who merely smiled back.
"No need to thank me...But about payment though." Ruby's heart sank when she remembered that he would be paid for his services. The more she thought about it though, the more the reality of this creature started to click.
"You're...You're a devil right? One just got me to give you my soul, or a decade or two off my life?" Ruby accused. It was a bit obvious, the horns, and wing, and tail, and gods! How did she not figure this out sooner! She knew she could be a bit naive, but not this much!
"Yes and no. I am a devil, the horns and wing prove enough of that." Jaune admitted, pushing back on his hair to reveal more of his bright red horns. "But I'm not gonna make you give up stuff like that. Those are some of the big ticket things, not worth stealing over homework." Jaune explained as Ruby's jaw hit the floor.
"What? But isn't that what you're supposed to do? To trick people like me into giving that stuff up?" Now Ruby was very confused. Here was a devil who had tricked her into a deal, but wouldn't steal the most valuable thing she had. Why couldn't this guy make any sense? Was he here to help her?! Scam her?! What?!
"That is, but me and my family are different. We still recollect our services, but we're not gonna take more than what we give. It's definitely a weird thing to do, but it's fair." Jaune shrugged. He knew he was an oddball of an infernal and was patient with his latest customer. "So what do you want to give up?"
Ruby had to think. He probably doesn't want money, and she doesn't really have any to give him. She couldn't get her family involved either. All she could really think of that had value but not too much was "C-Can I offer up my virginity?" Ruby could barely squeak out. It was super embarrassing, but it was the best option she had. It was the only thing she really had of the level value that was being asked.
"Excuse me?" The devil stood gobsmacked, not expecting that answer at all. He's seen a lot of things given up for his services. If he was human, he could probably live quite handsomely after everything was sold. This however, was defiantly a first. A bit ironic since he was now be this girl's first.
"I said...Can I offer my virginity as payment?" Ruby repeated, scraping up some scrounge of courage in this otherwise confusing and embarrassing situation. Things couldn't get any more awkward, well they defiantly could but she already felt like she hit embarrassment rock bottom.
"I...I think so. I need to check." A large ornate parchment formed in Jaune's hand as he started to read. After some reading he waved it back from where it came. "Alright That is a form of payment I can accept, but are you sure? Isn't that something you humans hold dear?" He knew it was, he just wanted Ruby to be aware of it and to maybe change her mind. He was a creature of sin, and he knew Lust was one of his core principals. He definitely felt lust towards her, but that didn't mean he was just gonna throw himself at her. He was a gentleman.
"Yeah I'm sure. It's my senior year, I'm still only known as the weird nerd at school. No boy ever talks to me so romance is out of the question right now. At least I'm losing it to a boy whos nice to me." She watched the boy clam up, her words pulling at his infernal heartstrings. He had some insight into her life before he arrived, but he didn't know she was that unlucky with guys. He didn't have to worry about stuff like that, but his sympathy still went out for her. Oh the things he does to be nice.
"I'm sorry to hear that. If you really are sure, then sign this and we can finish this deal." Jaune pulled out a contract and quill before setting in on the desk. He still had some reservations about this deal, but he had rules he had to follow. If this was what his client wanted, he guess he better go along with it.
Ruby looked at it anxiously, worried it would use her blood as ink or something. Eventually she nervously picked up the quill and when it didn't do anything painful, picked up the contract and scribbled her name on it quickly before it suddenly disappeared. Now she had really sealed her fate. At least it was on her own terms right? "So what now?" She looked up at her new contractually obligated lover with a mix of anxiety and excitement on her face.
"Well now things get a bit awkward." Jaune explained as he started to pull on his hoodie. Ruby watched with growing excitement as Jaune shed his hoodie before tossing it away into nothing, revealing his muscular chest. She's seen the male physic before, both from movies with watched with her family, and some much more private viewed on a website Yang would tease her about for the rest of their lives. While Jaune wasn't as muscular as the actors in either the family movies nor the private ones, he did have enough give an appealing contrast to his normally boyish appearance.
Jaune kept removing clothing, tossing them away until he was left in nothing but boxers. Ruby herself was still clothed, ogling her partner's form to work herself down. Her breath hitched as Jaune stepped to her, his arms wrapping around her, his skin radiated with heat, not enough to scold, but it does make the heat in her cheeks grow. He pressed his chest into hers, making the heat between them grow even further.
Ruby stared into Jaune's eyes, their faces so close she could feel his breath on hers. She didn't know who moved first,but she felt his lips on hers. She could feel his tongue probe his mouth and she eagerly let him enter. His tongue was hot inside her mouth, like his body. It was like a cookie right out of the oven, pleasantly warm and making her moan into the kiss.
The two shifted, shuffling as Jaune led them until Ruby fell onto the bed. He kept the kiss going all the while, guiding her even as he was laying overtop. Soon though Ruby's mortal needs returned as she pulled back, gasping for air. She looked back up at her partner who was looking at her inquisitively, his mind focused on his next move.
"Arms up please." He asked, his words stern but voice soft. He was intuitive, but wasn't trying to force Ruby one way or another. He wanted this to be as pleasurable a punishment as he could, and was gentle as slowly pulled her shirt off of her chest once her arms weren't in the way.
Ruby's arms instinctively went to cover her bra clad chest, her face filling with embarrassment until she felt Jaune's strong arms gently pull them aside. She didn't stop him when he reached around to unclasp her bra and toss it away to the now growing pile where her shirt landed. She let out a high note when she felt his hands start to touch her chest, rubbing and gently pinching them.
He was further encouraged by Ruby, her small little gaps and moans telling him that what he was doing was exactly what she wanted. He had some experience with this sort of thing. While seduction was more of his sucubus sisters' thing, he was still trained for this stuff, and it showed as Ruby seemed to be very much enjoying his hands all over her body. He was almost sad to hear her disappointment whine when he took his hands off of her, rising back until he was sitting on the back of his thighs on the bed. His hands now started to tug at his boxers.
Ruby noticed, and flipped herself over, now leaning over and watching his crotch intently. She was both shocked and relieved as Jaune pulled down his boxers, revealing his phallus. It was thankfully human shaped, a nice six to seven inches and very appealing, even if the dark red skin of it threw her for a loop. Her hand slowly reached out for it, making her gasp as she brushed her fingers against it. Those movies she watched alone, and even some books she procured from her friend Blake taught her the shape and basic mechanics of sex, but now things were real. This Devil was real, the dick in front of her was real and was soon to enter her. She couldn't help but be filled with nervousness, even as she burned with excitement.
"Do..Do you want me to S-Suck on it?" Ruby stuttered out. She didn't know if she even could, but she knew this was what guys liked and wanted to see if that was where Jaune was leading things. She wouldn't mind it too much. She had a little idea on how to do it, her only experience was from borrowed books from Blake and those Yang teasing videos. She just hopped he wouldn't be disappointed at her lack of skill.
Jaune merely waved her off. "Not unless you want to. I'm trying to pleasure you here. In fact, you mind flipping over.." Ruby nodded attentively and listened, moving back to laying on her back. Jaune followed and moved back on top of her, moving until his head landed near her thighs. His thumb slid under her shorts and panties before pulling them down to her knees, leaving her nearly as bare as him.
Ruby watched, her lust growing until she nearly screamed in shock and pleasure. when she felt Jaune's tongue against her clit. She felt him start to eat her out like a starving man at a feast, licking away in a frenzy. He promised to make this punishment pleasurable, and was intent on keeping his word.
Ruby herself was a lost of them, stuck moaning and making other groans of pleasure. She barely even noticed his dick above her chest, the difference in height making it hover above her breasts. As inexperienced as she was, she knew sex was a too way street, and wanted to give as much as she got. She leaned forward, propping herself up on her elbows, her hands pressing her moderately sized chest together around Jaune's dick. They weren't as big as her sister's, but she hoped he enjoyed them all the same. He certainly did, thrusting his hips as the two worked together to fuck her tits.
The two stayed like that for a while, both getting more into it as they went. Soon all Ruby could really let out was the occasional word mixed between moans. Jaune himself was letting out muffled grunts as he kept eating her out, drinking her juices and teasing her clit until he heard her scream once more and felt his face get painted with sticky stuff. Ruby was left panting, her breath heavy as she came down from her high. She was still trying to wrap her head around the whole situation, but part of her no longer cared. Who cared if this being came from hell and is about to fuck her. He just gave her the greatest orgasum of her life and was promising more. Her attention returned when she saw Jaune smile down at her, having realigned himself as she calmed down. She could feel him gently sliding the first inch into her before waiting.
"You ready Ruby? Cause once I do this…." Jaune asked, a bit nervous. Even if this was her punishment, he still had some reservations about it. It was definitely the most out there request he's gotten from a mortal. He started to slowly push in deeper when Ruby gave him the go ahead with a thumbs up and smile. She was honestly pretty cute, and part of the reason he decided to help her in the first place.
That cuteness was interrupted though when she let out a long moan, then a grunt of pain as he filled her. He made sure to give pause, letting Ruby recover from his punishment. He frowned to himself when he saw a bit of blood flow down from where they were connected and heard a whimper of pain leave Ruby's lips. He leaned down to capture her lips with his, easing her pain as much as he could. He knew this was her punishment, and the one she asked for, but that didn't mean he had to be cruel. She seemed to appreciate it, wrapping her arms around him as she melted into the kiss. Soon Ruby seemed ready enough that Jaune could slide his remaining inches into her. He couldn't help but groan at how tight his partner was. It made sense all things considered, but the feeling of her walls constricting him was ironically heavenly. He started to gently roll his hips, pumping slow yet long thrusts into Ruby. He wanted to take things slow at first, ease her into things.
Ruby moaned as he did. With the pain gone she was able to enjoy the full feeling of his girth fighting against her tightness and winning. He was reaching places her fingers nor any toy she sneakily procured had been able to reach. She started to roll her hips, clumsily trying to match his thrusts. She was still the clearly more inexperienced one of the two, but was getting a crash course. A lesson more enjoyable than anything taught at school, and she got to play with real cars in her mechanics class.
The two fell into a pleasuring rhythm, thrusting into each other, slowly increasing speed. Ruby pushed Jaune to go faster, mixing pleads with moans. He listened and soon the loud sound of flesh slapping flesh filled the room, making him ever grateful for getting those pads on the walls. As nice as hearing Ruby moan loudly was, he rather not have any family of hers interrupt. He didn't fear anything the mortals could do, but it would definitely make things awkward.
Ruby was having the time of her life, never having felt so good. It was like the knowledge from before, just pouring into her. She assumed it was another one of his magic tricks, but as long as it helped her like before, she didn't mind one bit. Soon she felt another climax rush through her and let it ride. Like a wave it flowed through her. So focused on her own pleasure, she barely even noticed Jaune getting close to climax as well until she felt his grip on her tighter and thrusts grew rougher. With a groan he finished inside of her. Ruby was shocked, both at the feeling and small fear of a small Jaune growing inside of her, as cute it would be. She could also feel the tip expand inside of her, almost trapping itself in, a shocking feature of demonic anatomy.
Jaune wasn't phased. Without a word he picked himself up a bit, still trapped inside Ruby, and flipped her. It lead him to be laying on top of Ruby again as her head hung off the edge of the bed. Ruby was just stunned, barely reacting to the new position. The heat inside her core was now at a boiling point. She had to strain her neck to look back at Jaune. His boyish smile was still there, but in his eyes was a fiery look that promised penance. She gasped as she felt him thrust again, much more forcefully than before. The swollen head inside of her made him feel like he doubled in size. She should have complained about the new treatment, but still understood this was her punishment. This was the price for knowledge, to be used like a whore by this boyish incubus.
As much as Jaune enjoyed the cute romantic experience he just gave Ruby, he was a creature full of sin and was born to indulge it. Mercy had fled him, and lust took its place. He slammed into Ruby over and over again, his hips clapping against her surprisingly nice ass. His eyes fell onto them, watching the cheeks bounced with every impact. He released her hip from his tight grip to strike her ass. He expected a gasp or even a whine of pain, but was pleasantly surprised to hear her let out a loud moan. It fueled his lust addled mind to go even rougher.
Ruby knew she shouldn't enjoy this. This was punishment, penance, hell come early for her sins. She was pinned to her own bed as an incubus she only met a bit more than an hour ago, rain slap after slap on her ass, his dick lodged inside its new home. His warmth was as soothing as much as his hands stung, a perfect mix of pain and pleasure to leave her a moaning,rambling, slutty mess! Soon she'd be like the protagonists from Blake's books! Those douj-douji- the ones she hides behind more acceptable books. Ruby would become nothing but a love struck whore addictied to her lover's cock, always pleading to be fucked. As much as it was perverted and unlikely, Ruby honestly didn't mind being used like this. A dark part of her was pleased to be fucked into a toy for her dashing devil.
Ruby was much more aware of Jaune's encroaching climax this time around. His slaps on her ass ceased, but his thrusts became much faster and sporadic. He craned his neck down and lightly bit Ruby's neck, leaving a clear hickey. With a final slam he unloaded inside of her, bringing back the fear and small hope of a little Jaune in her future. Ruby screamed in pleasure, cumming for the fourth time tonight. Ruby panted as Jaune rolled her over, now laying on his chest as the two took a minute to rest. She still felt him inside of her, hard as ever yet not moving much. She slowly rocked her hips, quietly moaning as she gently fucked herself on him. It didn't feel as good as when Jaune thrusted, but still felt nice enough. She could hear Jaune laugh under her, the rumbling of his chest tickling her back. "Hehe. You're really enjoying yourself aren't you?" He asked as his arms wrapped around her and started to tease her chest.
"Y-Yeah! I'm loving it so much!" Ruby cheered, turning her head to smile at Jaune. He could see the effects he was having on her: her face was bright red, a long trail of dried drool hung from her chin, and her hair was a sweaty mess. If he wasn't already hard as steel, he would be immediately.
"I'm glad you like it." He smiled, accenting each word with a small thrust of his hips and pinch of her nipples. He chuckled as Ruby shuddered utop of him. "I have to ask though, do you wish to continue?" He hoped he said yes. His opinion on the deal had changed. He was happy to to have taken Ruby's pruity and would love to keep indulging her in sin and lust.
He doesn't think he's ever seen anyone be so eager for punishment, but Ruby lit up at the offer. "Yes! Please fuck me more!" She started to buck her hips even harder, begging and pleading for more, and Jaune gave her more. So much more. The two went at it for what felt like hours. Unlike normal men, Jaune seemed to have boundless stamina. Ruby lost nearly all sense of time as Jaune rain a train on her, fucking her over and over again in so many positions. He fucked her all around the room, bending over her desk, having her slumped over her tiny couch, and even hang outside the open window.
Each round came a different treatment of her. Jaune was never consistent whether he treated her as a harlot meant to be used, or an Angel to be spoiled. He was rough, soft, kind, mean, and everywhere in between, and Ruby loved it all. She constantly begged to keep going and was eternally grateful when he did. Part of her knew that she'd be oh so sore soon, but she didn't care. She could barely remember what time it was, but she remembered each and every position they did. Her favorite was when he held her off the ground, his legs bent nearly to her ears. He slammed into her over and over again as he stood in front of a mirror, letting Ruby get a front row view of her own fall into debauchery.
Ruby was right in that she would be sore the next morning. She felt like her hips were falling off when she awoke. She groaned as she got up, looking around and being shocked at how pristine the room was. Her and Jaune had made a complete mess, tearing up the whole place last night, but by dawn everything had been fixed. The only thing out of place was an ornate envelope with her name on it resting atop her desk. She tiredly got up and limped over to grab it before flopping on her bed. "Hey Ruby. Sorry I had to bail early. I cleaned up the room a bit as we made a bit of a mess. If you ever need some help, just say my name and I'll be there. If you ever are looking for some more fun, I'll be there on the double. Love Jaune. PS: You probably should take the pill if you don't want any kids yet." Ruby pulled the ornate paper out of the envelope to reveal a morning after pill, the same kind she found in the shared bathroom with her sister.
She'd take the pill, hiding it in her breakfast so her family wouldn't find out, and while she may have walked with a limp, the pep in her step was very much there. She'd happily take on her most annoying and frustrating classes content with the knowledge that help and more importantly relief was only a call away.