Had to rattle my mind for a new prompt and crack ship to go together between writing other fics. Something I'd enjoy while still making sure it's a rare pair. With that said, I've got not other idea for a possible next chapter in the future.
With a huff, Ruby slumped against the tree she leaned on outside the party. She hadn't known that apparently freshmen were the only exception to this party, since her older sister managed to get in when she was Ruby's age. And she even saw another one go inside with no problem, so why couldn't she? Regardless, Ruby knew her sister would be here and would definitely help as she would be intoxicated at that point. Even with a nympho like Yang, Ruby didn't want to risk the off chance her sister would be taken advantage of.
But with nothing else to do, Ruby just walked away after getting kicked out and found herself at the side of the large house. Some of the windows had lights on or off, but for at least half of the illuminated rooms had some naked girl pressed against the glass with a blurry figure behind them. It didn't take a genius to guess what was going on with their lower half. Honestly, what was the deal with everyone in her school being obsessed with sex? She didn't judge or anything, Ruby just figured she'd go down the path of maturity one step at a time. A simple house party with no parents involved sounded like a good start before losing her v-card.
"Is there some kind of stupid initiation or something?!" She groaned out loud, slumping in place with her head against the tree. Waiting out a whole party without actually being apart of it, and with nobody to keep her company. Nobody she personally knew anyway.
"Maybe I oughta fuck somebody to get it over with, it's not like Jaune would give me the time of day..." She lamented out loud, her isolation from the party gave her freedom to talk to herself with no judgement. Or so she figured.
"Pretty much answered your own question there~" A voice behind her said with a chuckle. She jumped, standing up and looking around. She found a shoulder standing out from the other side of the tree, before the person walked out to reveal himself.
Upon seeing her scared reaction, the boy laughed lightly again before extending his arm for an arm shake. Ruby gave him a questionable look before slowly meeting his hand.
"Whitley Schnee, youngest in the Schnee family, and resident of this house." He said, finishing with his other hand pointing to said house. Ruby perked up, not even realizing there was apparently a third Schnee. He was about her height, and from the look of his face he seemed to be her age as well. Come to think of it, Ruby was more surprised she couldn't recognize the only boy in her school with naturally white hair. Then again, she was able to skip a year.
"Schnee...? Like SDC? You're Weiss' brother?" She asked, wondering why her friend only spoke of Winter and not him. Though, the slight frown on his face that showed for a split second after hearing his sister's name may have been a sign.
"Yes... Though it was my older sister whom orchestrated this whole event you don't seem to know much of." He said, making Ruby raise a brow from his words. What else is there to know about a high school house party?
"What do you mean? Are there rules to a party now...?" She asked, wondering if being so reclusive and socially awkward may have hindered her learning on what people her age really do. Whitley just chuckled.
"Well no, having rules would sort of be against the idea of a party... But, there is a bit of a requirement, you see." Ruby saw a kind smile on his face, not even aware that to Whitley, it was more of a sadistic grin.
"And what wold that be? There weren't any invitations, and I thought having to bring alcohol to a party to get in was some movie cliche. Plus, I saw another freshmen go in there anyway" She said, crossing her arms as she thought about the injustice here.
"Hm, I suppose he might've just been lucky. But there isn't anything you physically need to bring, but more... Something physical you have to do, if that clears it up." He said, hoping she'd be able to catch on. But Ruby just cocked her head to the side. Alright, she may be more naive than he thought.
"Right, you see mrs..." He trailed off, looking at her. Just then Ruby realized she didn't even introduce herself. no wonder she couldn't fit in around here.
"Oh! Right, I'm Ruby. Ruby Rose." She said, feeling just as awkward here than she usually did at school. The one thing she tried to get away from found itself showing up anywhere she went.
"Ah, I thought you looked familiar. I've seen your name on the track leader boards on the school site, quite the reputation you have~" He said, his tone sounding more interested and flirtatious, making her blush.
"Heh heh, I try my best..." She didn't like talking about her time during track, not seeing it much of a big deal as others did.
"I'm sure you do. Anyway, I'm sure you know how the Beacon High parties may have changed over time. It used to be about creating the most rambunctious and ludicrous stories to tell for years to come. But now? It seems more like a place to hook up and share a night together. Which is nothing new, but there have even been games and events about it, all private of course." He explained, gauging her reaction. Ruby just blushed again and looked at the floor.
"R-right... I've heard about it but didn't think it was actually a big deal." She said sheepishly.
"Oh it is, and it's one of the reasons freshmen are hardly allowed in."
"But why? Are they not okay hooking up with our grade?" She asked, not realizing she sounded more interested in the matter than she wanted to until the words left her lips. But Whitley didn't call her out on it, in fact, he chuckled to himself for a bit.
"Oh, of course not. Happens more often than you'd think. It's just the main assumption that freshmen like us aren't that well experienced and are typically too scared to venture as far as our upperclassmen are. What I'm speaking about of course is virginity. They don't usually allow virgins inside as it's better to have a house full of people well versed on sex instead of a handful of those who aren't. A bit of a broad assumption if you ask me, but the point remains none of them will be so easy to let freshmen inside. Especially those some would consider 'goodie two shoes'" He finished, knowing that Ruby for sure understood now.
Her blushing expression and interest in staring at the ground remained, but her eyes widened at the realization on what she'd have to do to get inside. A storm of thoughts rattled in her mind, wondering if it was even worth getting inside.
'C'mon, it's probably going to be my only chance getting in... But how would I even find a guy?'
Even with her thoughts only kept to herself, Whitley knew everything she was thinking. He didn't even suggest the idea and still made it clear to her what she'd have to do. With her eyes away from him, he was free to smile with evil glee as he could tell the gears were turning in her head. After a few seconds, he cleared his throat and she looked back at him. Not a word was spoken but the message was clear.
He was the answer to her little problem. Her blush deepened even more.
"I'd be more than willing to help another freshmen, if you really want to get in the party that is." It was too easy for him.
"I-I, well I don't... Uh, I mean..." She stammered, clearly unsure of the prospect of it. She wasn't really one to care about her first time being special or anything, as long as she would be able to find the one she wanted to do it with for the rest of her life. Still, she just met him. Whitley figured this thought may have gone through her head, and he already had an answer before they even started talking.
"I'm actually quite familiar with sex, being rich has it's perks. Basically I know what I'm doing~" He said with a much more sultry tone, his interest in her made more clear. Ruby hadn't noticed how he slowly closed the distance until he was about two feet away from her. He must've been sidestepping in every minute, she wasn't afraid of their closeness but did feel her resolve break a little.
Before she could respond, Whitley extended a hand and cupped her cheek moving his thumb to caress the soft skin. She was taken back but didn't pull away either, she would if he tried going any further than this.
"Would you like me to help you? Just say yes and you'll be in that party before you know it~" He said, something about the way he talked, how he carried himself, felt genuine and professional. A business strategy he learned from his father, managing to convince naive minds from how they spoke, rather than the actual words they used.
'Screw it, better have my first time being nothing special and learning what to do when I finally get a boyfriend... As long as nobody knows about it.' Once that last line went through her head, Ruby realized she should've asked about that last bit as well.
"You won't tell anyone, r-right?" She asked, a blush making itself evident. Whitley just smiled and chuckled, he was in.
"Of course, we don't kiss and tell around here~" He said, taking another step closer and his other hand being placed on her shoulder.
"Okay, fine... How do we start?" She asked, not wanting to get felt up if nothing was going to come out of it.
"Already ahead of you there." He said right before leaning in and pressing his lips against hers. It caught Ruby off guard but she returned it the best she could, it was her first after all.
Whitley held more control due to his experience and confidence, intensifying their kiss as he wrapped his arms around her dainty body. Ruby would've yelped if she didn't already have her mouth occupied. Her soft lips smacked and kissed his own, doing whatever felt necessary and enjoyable. It was electric and passionate as an amateur could be, all while Whitley's hands were rather busy.
His arms around her waist lowered, and his hands went under her red skirt to grab her ass, so tiny and plump at once it got Whitley fully erect within seconds. Once his hands found their target, he squeezed his hands around her still developing posterior. This caused her to moan in the kiss, never having someone do that to her brought about unrecognizable pleasure she didn't know to handle.
Whitley never relented either, he pressed his body against hers until Ruby was leaning back against the tree. Luckily there wasn't any bark poking at her and she was free to lean back and let him get to work. Though Ruby was able to get a bit adventurous once her nerves relaxed and she embraced the jolts of pleasure she felt on her mouth. Her arms were around his neck with her hands going through his hair to keep their kiss locked. Not that Whitley planned on breaking it anytime soon. For he had pressed his tongue into her mouth once she opened up more, the muscle swirling and sliding along her very own. It was so strangely pleasurable it made Ruby moan more.
Soon enough, their need for oxygen forced them to break away. But Whitley waited for but a second before nuzzling his face into the crook of her neck, kissing every inch of soft skin while rocking his hips along hers. The tree gave enough needed support for him to have Ruby fully pinned against it, letting him push on as much as he wanted. Ruby had her eyes closed for most of the time, feeling as though looking at him would have her flustered and feeling awkward even after what they've done so far. So when she felt his hands removed from her body, she didn't see them going for her bright red sweatshirt zipper and pulling it down.
She heard and felt it all, making her move forward a bit to have her top easily slide off her arms. Leaving her in a slightly darker red tank-top. His hands went under the hem of said tank-top, feeling more of her hot and smooth skin when he gripped her sides. Ruby moaned more as she got felt up, perhaps sex was just as great as her friends made it seem like.
Not wanting to feel like she was being pandered to, Ruby in turn reached for the bottom button for his shirt, undoing it and slowly working her way up. Whitley felt this and smiled, pulling from her now wet neck and returning to her lips. This time Ruby was prepared, eager even, as she pressed her lips firmly onto his, pouring all their lust and passion into their second liplock. Ruby was as horny as she ever had been, her mind felt hazy with a great amount of lust she never thought she could feel. She didn't think twice as she grinded herself against his bulge, only craving more of what she felt. Her hands had gotten too shaky to unbutton his shirt, leaving the freshmen to finish it for her as he tossed it to the ground. Though, what he wanted was for her to be equally topless, seemed fair.
Ruby caught onto this from how he tugged at the bottom of her tank-top, making her pulled back her grasp on him to start removing the top herself. The more skin she exposed, the more the chill night air breezed against her body, making her shiver. Seeing this, Whitley pulled her in against his body by the waist, sharing whatever warmth he could. She smiled, appreciating the gesture and making quick work of her top. It joined his shirt on the ground.
'Two down, one left.' Whitley remarked in his mind, getting more and more eager to see her exposed chest as time passed, but he felt at bay with the added bonus of feeling her partially naked torso and hugging it close to him. Ruby grabbed his chin and went in for another kiss, surprising Whitley with her sudden confidence. But he didn't judge, he was in the same state of mind, barely able to hold onto his wit.
Luckily, Ruby was already fumbling around the straps for her bra, struggling a bit due to their kiss occupying her mind right now. Within the minute, she was able to undo it and slip it off her chest before throwing it to the ground. As quickly as her breasts were revealed, they were covered again with Whitley's hands grabbing both in each hand. Gently pressing it about and squeezing them in his palms, giving just enough stimulation while being as gentle as he could. He didn't want to overstimulate the young girl's mind in one night, she'd need baby steps through it all.
Meanwhile, Ruby was mewling and gasping with every jolt of pleasure sent from her sensitive breasts due to Whitley's kneading. It was so much more than she ever felt before, as she hardly touched her breasts when she played with herself. So she was unused to the foreign sensations, but gratefully accepted them. When Whitley's hands had their fun, one of them went under her skirt and pressed against her covered pussy, rubbing slow and firm. This made her moan louder, surprising herself with sounds she's never made before. But she couldn't help it, his touch was damn near magical.
His other hands felt throughout the rest of the skirt, trying to tell if there was maybe a zipper. Lady luck must've wanted him to have a good time tonight for there was one after some searching, not hesitating to pull it down and help her shake out of the skirt. It dropped to her ankles and Ruby stood in only a pair of red and black panties, with Whitley's hand still pressed against her crotch of course. With Ruby's bottoms coming off, it was now Whitley's turn as he began to use his free hand to undo his pants. Past experience taught him how to do it with one hand, but that's a different story.
Once they were undone, Whitley let his pants and boxers slide to his ankles, his hard on now free from the constrictive prison of his pants. Of course, Whitley pulled Ruby in close once he was done, making her feel his shaft pressed against her belly as they kissed. As soon as she felt the hardness and heat of it, she almost shivered as she finally made contact with a boy's dick for once. But as she went to reach for it, she was again pinned to the tree with Whitley's hands touching her all over. He leaned his head down to take a nipple of hers into his mouth, sucking the already hardened nub, the cold must've been the reason.
One hand held whichever breast he was sucking on, while the other trailed down inside her panties to play with her now soaked pussy. This brought out moans and intelligible noises of pure pleasure she couldn't get enough of. She was hardly able to keep her balance, relying on the tree and her sturdy grasp on Whitley's shoulders as his fingered rubbed up and down her slit. He treated her breasts with his mouth to his heart's content, with Ruby just staying still and enjoying the pleasure. But he was getting a bit impatient with only pleasing her body and not receive any action.
He pulled back a bit and started tugging her panties down, the feeling of it all signaled Ruby to help him by wiggling her hips to let the underwear fall to the ground. She hadn't even realized she had been stripped completely nude outside until Whitley stopped sucking her breasts. The chill night air was balanced with Whitley's warm body so close, as well as herself. Being toyed with got her heated and excited.
Getting closer to his desired goal, Whitley grabbed a leg of hers and raised it, hinting her to wrap it around his waist. She did, and her legs finally spread he positioned his cock to her entrance, pushing his tip in slightly before quickly thrusting himself all the way in. This caused Ruby to actually scream, both the pain and pleasure were a surprise, and she didn't even prepare for it. Whitley hastily pushed his mouth to hers, silencing her loud cry anyone could mistake as a scream of fear and danger. Her muffled groan was gone once she adjusted to the feeling, but the pressure and discomfort remained a bit. Making her gasp when Whitley tried to pull back and repeat.
"See? Pretty great huh~? We're already halfway there, we can make each other cum and you'll be in the party in no time." He said, hoping it'd help her focus on why they did this. It seemed to work, as Ruby perked up at the mention of the party, almost forgetting the earlier circumstances. She took a breath in, looked at him, and gave him a small nod. With this, Whitley began pacing his hips in and out of the former virgin, making her gasp and shiver with every thrust. His arms held her sides tightly, keeping Ruby standing still as she seemed to have some trouble with that. Though her arms around his neck pulling him in to smash their lips together, his tongue pressing against her lips before she opened them for him. He dominated the kiss easily, but kept it gentle for the inexperienced girl.
Speaking of, Whitley wouldn't have been able to really tell that Ruby was inexperienced is she hadn't said so. Sure, the initial pain was there and she's very tight around him, but she quickly embraced the feelings he made her feel, making it clear how much she loved it. And as for her kissing skills, they left a little to be desired. It didn't matter that much, he always took control anyway.
They continued their kissing along with their fucking, a perfect combo they both craved more of. Though Ruby was surprised to feel the pleasure increase even more so when Whitey's hands were placed on her still developing breasts. They felt amazing in his hands, what she lacked in size she made up for in softness, making it fun to play and squeeze them. And of course, drawing more moans from the freshmen girl Whitley silenced with more kissing. The more he toyed with her titties and made her moan his name like sweet music, the more confident Whitley became to keep fucking her so rough yet gentle against the tree outside a rather populated party.
Ruby pondered it all, finding all her anxiety and doubts about sex instantly vanishing as she clung to the body of her fellow freshmen fucking her. It really felt astoundingly good, damn near intoxicating no doubt. It made Ruby crave things she never craved, desiring more of Whitley's kissing, more of Whitley's fucking, and more of Whitley's groping. And before long, Ruby felt her orgasm fast approaching. Whitley knows this, and grunts as he picks up the pace to help her out. Ruby wanted to cry out again, but was too out of breath to keep kissing him. She pulled back and quickly nuzzled into his shoulder, muffling all her erotic yelps as she got close to climax.
Without even thinking, Ruby's other leg wrapped around Whitley's waist and pulled him in, clinging onto his body for dear life's sake while her tight walls contracted around his cock. And in doing so, initiated Whitley's own orgasm, his cock bursting with warm seed that filled Ruby's teenage pussy. He pulls their bodies together as he tenses up, enjoying her vice grip on his body as he gave a few final thrust to drive more of his cum deeper.
When they both went limp and Ruby's legs released him, Whitley slowly pulled his softening cock out of Ruby. Though all that thrusting and pinning Ruby to the tree left him a bit weak, making him lean forward and rest his face nuzzling Ruby's neck. She giggled whenever he kissed her neck, before they both pulled away from each other and redressed.
Once he was fully clothed, Whitley simply told her-
"Hope that helps, have fun~" And with that, he went back into the party. Ruby didn't have the chance to say bye or anything else for that matter before he was gone. She raised an eyebrow, confused as to why he'd leave so fast. Regardless, she shrugged it off as she needed to put her clothes back on. She didn't even notice just how much she stripped, feeling rather dirty to have her first time in public. Even then, she didn't mind it. It was actually kinda fun. With the last piece of clothing back on, she made way to the front of the house.
Only to see the supposed bouncer that kicked her out had disappeared. How long was he gone? Could she have just waited for him to leave so she could come inside? Of all the various questions popping up, a conflicting feeling due to the earlier context of what happened. She probably didn't need to give her virginity away to some stranger, and she almost began to think Whitley may have lied about the alleged requirements to join the party. However, she could probably cheer herself up with what may have happened inside the house.
After her first time having sex, she wasn't as skeptical or nervous about the topic.
In fact, she might just hook up with someone else to have that feeling again.