Adult-FanFiction.org : Cartoons

Black Tie
By : RWBYRemnants
Category: +M through R > RWBY
Views: 1476 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: RWBY is not mine and I make no money from this fic
Chapter List
- 9
- 10
- 11
WARNINGS: gender play, anal play, analingus, prostate orgasm, pegging, masturbation.

=Chapter 10
The usual bag of tricks rested comfortably in the passenger seat of Winter Schnee's car as she neared Qrow's apartment. They had not been set to have a meet-up for a few more days, but she thought she might surprise him with an impromptu visit. A cancelled business meeting left her afternoon wide open, and she would rather check in on him - and hopefully net herself some "afternoon delight" - than find some paperwork that hadn't been done yet, or else go bother Weiss and Yang yet again.
Of course, one of the unspoken reasons she was being so nice and considerate of him lately was because she felt a bit guilty for keeping secrets. It was implicit that when Ruby had contacted her with a few simple-yet-direct questions, she would not tell her uncle. That was a line neither relation wanted to cross, and she full well understood the reasons.
Especially when she had asked Winter if she'd be willing to engage her in what she termed a "practice session"; not a real one, and not one that would end in either of them being stimulated to orgasm, but just one that would sort of walk her through the types of things that could happen in person, rather than reading or talking about it in theory. Winter had of course started out asking why she didn't approach Blake, but when directed to ask her herself, Blake's response-text was pretty curt.
"You really think I want to Dom my ex's little sister?! No WAY, not even for practice; it's just too close to home for me personally. You can if you want to though, I trust you to treat her right"
With that thought in mind, Winter chuckled to herself as she pulled into a parking spot near Qrow's apartment. It was going to be weird, taking on someone as inexperienced as Ruby who was even slightly related by blood to her usual Dom, but she also thought it showed remarkable maturity for her to ask for this type of session rather than jumping straight into the deep end. And, as directed by Blake, she would treat the girl with the utmost of care. That was a lot more important than her other reservations.
Then she was knocking at Qrow's door, so she decided to put all thoughts of Ruby out of her mind until afterward. It was only prudent. The first few seconds of Winter knocking, there was no response. It wasn't until she knocked for a second time that some footsteps could be heard approaching the door, and the latch was heard turning.
"What part of 'give me a week' do you not understa- oh…" The instant the door was thrown open, the angered rant was immediately cut off. An unshaven, unkempt Qrow had opened it, looking rather worse for wear – and smelling of beer a lot worse than usual, as well.
"Oh," was all she had to say at first. Seemed Winter caught him on a bad day. Her excitement over surprising him began to dwindle at an accelerated rate as she took in the look of him… and the smell. It was a combination of liquor and unwashed male that did not become him. "I… sorry, I should have called first. Don't know what I was thinking." Of course, she did, but now it seemed stupid and she didn't want to admit she was hoping to "surprise" him.
"No no I- uh… Sorry, been a hectic day." Although that's all he admitted, it certainly seemed like the wrong word. Taxing, perhaps, but this didn't seem like something caused by a rush of being busy for a single day. Realising he'd left her still standing in the doorway, he stood to one side, gesturing to the living room. "C’mon in."
With a duck of her head, she did so, looking around the room. Everything was a shambles. A few things were in cardboard boxes, and everything else was stacked up randomly, or else stuck in trash bags.
"What… happened to your apartment? Were your robbed?"
"Huh? Oh, uh, right." Shutting and locking the door behind the door behind them both, he ran a hand through his greasier than usual hair in thought. This was particularly strange for Qrow. His place was rarely tidy, but this much was a different story. It clearly wasn't just things the usual day-to-day mess, and unless he suddenly developed a hoarding habit, there seemed no explanation he could give.
"I'm just…” Qrow laughed and shrugged. “Havin' a good oll clear out. Y'know, throwin’ out some trash, organising, all that Queer Eye shit."
"Some trash? This is… just about everything you own!" Then she cleared her throat and attempted to smile, despite being so wrong-footed by the circumstances. "Well, if you'd like a lift to the store, or… to Goodwill… I have my car."
"Not today, thanks. I still need to decide what I can put on eBay, what I can give to the nieces… I guess I got pretty caught up in it all." Again, it seemed like a made up excuse. At this rate, him being robbed would have made the most sense for his behaviour and the strange circumstances she found him in. Still, Qrow was stubborn, and too proud for his own good.
Although there was one thing that was shooting his pride down a little, that was becoming obvious when he held an arm up to quickly sniff, only to curl his nose up. "Right… I should probably have showered today. Just got distracted."
Her own nose curled just as much. "Indeed. In fact, in you get, and then we'll… find you some supplies, or I can help sort. Ah, ah, ah!" she cut him off when he tried to speak, pushing him toward the bathroom. "Shower now, worry about these other things later."
"Alright alright, fine. Just, let me look at stuff before you throw 'em out, alright?"
The instant the water could be heard running, Winter set to work. The coffee table had already been cleared, and was now home to a stack of boxes, each labelled accordingly. With the weight of some of them, it really did seem like it was everything rather than just a charity haul. The rest of the room was more or less cleared, which left the only two alternatives to be the kitchen or the bedroom.
Considering Qrow would still need to use the kitchen, Winter headed to the bedroom instead. A sight that appeared much more like Qrow; an unmade bed, clothes over the top of the sheets, and a messy computer desk. At the very least this didn't look like a looter's treasure trove like the living room did.
"Even in here," she sighed, beginning to straighten up the papers on his desk a bit. There wasn't really anything there that looked like it might need to be sold off, so she focused instead on making it look orderly. However, as she was stacking a few of them up…
She saw the word "overdue" in red. Much more importantly, she saw the "eviction notice" at the top in large, bold letters.
Freezing on the spot, she looked away from the paper as she thought furiously. This wasn't her business. Qrow was not her "boyfriend", or someone that was more permanently part of her life; they didn't have a domestic arrangement of any kind. At the same time, he was a friend, and one she cared very deeply about. She knew she should forget she saw it and pretend that she never had, but concern for his welfare won out over the need to respect his privacy.
As she had feared, he was being evicted. Too many late rent payments seemed to be the main cited reason, although the letter also made sure to mention a few noise violations. Her head dipped guiltily; that was as much her own fault as Qrow's. How could he never have mentioned this? Her curiosity demanded she dig further into the other papers, but she resisted. The one on top had been bad enough, and it was in plain sight.
As she set the papers down, she bumped the laptop and the screen came on. The browser was open to craigslist, showing a few pictures of an apartment above someone's garage. It was a small space that didn't even have its own bathroom; something for a boy fresh out of college to think of for saving money, but nothing for a fully-grown man to call home. Other open tabs were also listings of various different apartments; similar, tiny one room places that didn't even come furnished. One of which even showed a photo of a mattress on the floor being the bed of someone previously. Why was Qrow looking for something this cheap?
Perhaps he could answer those questions in person. The sound of running water had began to fade away, and within a few more minutes, the bathroom door opened. Having forgotten to take a spare set of clothes, he entered the bedroom with only a towel around his waist to cover up.
"Sorry, Snowbird, I just gotta grab-" But he stopped in an instant when noticing the expression on her face, and that the laptop screen was now lit.
"I… apologize," she told him immediately, face carefully neutral now. "It wasn't my intention to snoop, and I hope you can believe me, but you should have told me about this."
There was a deep sigh from him as he ran a hand over his now shaven chin. So she had obviously seen everything, considering how all the bills were sorted into a pile as well as the lit screen. No faking out of this one. "How exactly do I tell ya? With flowers and a smile? Winter, it's fuckin' humiliating admitting I've been late with one payment, let alone four months straight."
"Four months? And you didn't…" Then again, he had just said it was humiliating; obviously he wouldn't want to tell her a single thing for fear of losing face. "Well, I'm… sorry to hear you're having money problems, Qrow, but I assure you that-"
"But nothing," he interrupted, glaring in her direction instead and frowning. "Everyone's got enough to worry about, with Weiss being ready to pop and the media trying to get into all that. The record biz for you and your pops. My income issue’s the last thing you guys should be worried about."
With a heavy sigh, Winter leaned against the desk, staring down at a patch of floor between them. "So, when were you going to let the family know? When they came to call and the landlords told them your forwarding address is under a bridge?"
"C’mon, don't exaggerate." Rolling his eyes for a moment, he went back to what he intended in the first place; find a set of clothes to wear. As he got a set of underwear from the nearby drawer, he was able to see one of the flats on the screen again. One of the worse of the few he had looked at. "So I'm not gonna be setting up in the Hilton… so what? Who needs a personal bathroom anyway? Just more for me to clean."
"Don't be stupid. You're not taking that place, even if you do have to take one of these." Her hand drifted toward the laptop again, but she opted not to touch; she had seen too much already, and he was cross. "Do you… want me to come with you to look?"
"No!" Leaning against the desk, he couldn't even power himself to look at Winter anymore. This was probably the worst she had seen him in a long time, and she'd caught him in some of the roughest patches. As he looked down to the numerous notices again, he found his hand curling into a fist. "Don’t need your damn pity, okay? I don't want people worrying about me! I'm a grown man, I can look after myself. I-I… I should be able to, anyway. Not some big baby."
She started to take a step toward him, then thought better of it and remained where she was. "Yes, but… if that isn't working, you should also feel like you can reach out for help. It's a brave man who does all he can on his own, but the foolish one who keeps trying alone when…" Her sigh was regretful, but she finished her statement anyway. "When clearly, it's not working."
"I don't need the speech, or a pity party." There wasn't much more he could say other then that. Finally turning back around, he sat himself on the end of the desk instead, running a hand through his damp hair. "What's done is done. Unless I somehow win a wad of cash, I can't exactly afford somewhere decent."
"You could stay with Taiyang, couldn't you? Just until you get back on your feet. And I have spare room, and I'm fairly certain Yang and Weiss do, too." A hint of a smile ghosted across her face. "You could be their live-in nanny. Sounds like a sitcom, doesn't it?"
Yet again he found himself rolling his eyes. "Yeah, I'd be a great influence on a kid, ‘specially on the days when I'm so wasted I can't get up. They've already got one mental case in that house, they don't need two."
But the instant that phrase left his lips, he froze up again, eyes beginning to widen when he realised what he'd just implied, and what he was referring to. That was a line that should never have been crossed again, especially not aimed at his own family.
"That was too far. Way too far. Shit."
Winter did laugh, but it was a strained, uncomfortable laughter. "As if I'd blame you. Don't forget, I'm the one that essentially caused her to have a mental illness in the first place."
Yet again, he deeply sighed, looking off outwardly into the distance. He knew he'd said enough, even if the person in question wasn't around to hear it. It still didn't make it fair. "Some surprise this is, huh? You come for some afternoon fun for yourself after a long day and have to be dealing with me being a dick to our family. Feel free to bail now if you want."
"A 'dick', hm? Not to my way of thinking. This… has been worrying you for a long time, hasn't it?" He didn't answer, so she finally walked around the desk and sat next to him, close enough that they could easily touch. "I wish you didn't think you have to walk through this alone."
"But I do have to, Winter. I'm the one that didn't pay my own damn rent, I'm the one that needs to find a new place. As much as I appreciate the company and the thought, I'm not gonna drag anyone down into my own personal swamp of bullshit!"
This wasn't like anything Winter had ever seen before in him. Qrow was usually so full of himself, annoyingly so. It was like he was an entirely different person. After a long minute of silence, she said in a soft voice, "Then… should I leave you be? You didn't invite me over, and clearly I'm just in the way here. When you have this much to think about, I'm…" Her hands made a helpless gesture.
There was still no further response. But it only took looking at him to see that one wasn't needed. The words might have strongly suggested he wanted to be alone, but from the shrugged shoulders and tense expression, it was very obvious he wanted the opposite. He was just far too stubborn to ask.
"Stop being so anal," she teased, bumping his arm with her elbow. "Relax. I know the temptation to be all wound up about this is heavy, but I know from experience, stressing yourself out will not improve a single thing."
"How the hell do you put up with me?" He finally found himself looking up from the floor and toward her. The confidence was still absent, but at the very least, he was able to force a nervous laugh of his own, even if it only lasted a second. "I can't be what you picture of an ideal guy. Alcoholic, unemployed, arrogant; yet you still give me the time of day. Makes me wonder if you're kinda nutty yourself."
"Obviously. Then again… I sometimes think we all are, in our ways. At least, when I said that to my therapist, she agreed that it's probably true - and she's a professional."
"Huh. Didn't think you were the therapy-going type." But after that, there was yet more silence in the room. As much as jokes and comments were Qrow's strong point, this didn't seem the time. But in the end, he rubbed the back of his neck again. "I guess… Well, it's embarrassing enough for me to admit this shit to Tai. And with the baby n' all, I’d be dumping stress on top of stress. I barely know Glynda, didn't feel right even thinking about talking to her. Then you…" Shrugging his shoulders again, he followed that with, "I'd rather not risk the best thing that's happened to me in a looong while."
Winter had no easy response for that. Instead, she merely leaned back against the desk for a few seconds, pondering his comments. Eventually, she whispered, "I'm not going anywhere. Especially not when… it looks like you need me right now."
"Then you really are crazy." He chuckled to himself again, getting up from the desk at last to continue fetching a set of clothes like he'd first intended. But pausing just after he'd pulled out one of the drawers, he looked to her with a smile. "But… I guess I should admit, as miserable as I am right now, I am happy to see you."
"That's good. If you saw me and thought 'Oh shit, it's Winter,' I'd be more concerned." Smirking as he fetched his clothes, she gestured around the room. "And anyway, you've made a good start with packing, wherever you end up. So I don't think you're totally hopeless."
More and more, he was beginning to think about what was said. She had a spare room. He'd noticed it a few times in his moments of staying overnight, but never really got to have a look. If it was anything like her master bedroom, it would be a fair size. Definitely no worse than the very flat he was about to be kicked out of – and a considerable upgrade from any of the ones on craigslist. It also offered good company, in and out the bedroom.
But there was a problem.
"You offering me your spare room though. No offense, but it’s kinda outta my range; I couldn't afford to pay toward rent of that place if I sold everything I had."
Her lips quirked into a slight pout. "Do you really think I'd accept your money if you tried? Not when you're in the position you are, Qrow. I do expect you to help keep the place tidy, buy some of the groceries, things like that, of course. But that's only if you would consent to living there."
"…You're serious?" He had been just about to slide on a pair of boxers before he froze, looking over to her again and raising an eyebrow. "What about your pop? Or Weiss even? Thought you had rules with mixing work and play."
"I do," she sighed heavily. "But this is more important; it's about your survival, your quality of life. I'd still prefer to keep my family from finding out, but they so rarely visit my apartment that it won't likely be an issue."
"Huh." It still seemed such an alien concept to him, that someone was so willing to help him and ask for nothing in return. Apart from paying for groceries of course. "You're actually willing to put up with me in your apartment? Cause I warn you now, I like watching cheesy sitcoms and war movies."
"I tend to watch more documentary programming than anything. However, I'm sure we can find a happy compromise." Then she fixed him with a hard stare. "I would insist that you try finding employment again; I know luck has been against you, but there has to be something out there for you. Just so you don’t think this will be a handout."
"Well, I'm doing that anyways. I do the odd job for cash-in-hand when people call, but other than that most of my day is job hunting." Though when Winter raised an eyebrow in doubt, he spared her a small smile. "And drinking, I guess."
"Well, there will have to be less drinking. I'm not saying give it up, but you have to cut back if you're to be presentable to interviewers; keep it to the evenings."
"Never drink before an interview." The very conversation with Winter was seeming like an interview of its own, but it was far more bearable when the end game was considered. It really would be a solution to his problems, and be far more convenient for them both. In fact… "Does this mean extra play?"
That brought about the most catlike smile he'd ever seen on the businesswoman, but instead of responding verbally, she merely shrugged.
"Oh come on, your big strapping Rooster just down the hall; how can you resist?" There was the Qrow she knew and liked. Over confident and flirty, and still with nothing on. Giving a small smirk, he abandoned that task, and instead sat on the edge of the bed. "And I can tell that's why you came today, right?"
"Well, yes. Not that I knew there would be a problem, of course, but… I had intended to grant you a surprise session with Princess." Her head nodded toward the living room as she added, "And I have the accessories to prove it."
"Then I guess these will be useless for the evening…" He threw the pair of boxers straight back into the drawer, standing up again as his smirk got even more mischievous. "One more noise complaint won't hurt; might as well leave with a bang."
"Pun intended?" she chuckled, walking past him into the living room, where she had left the supplies. In no time at all, she was walking back into the bedroom, eyes flicking to his nude form.
"So, I brought along a pretty fair selection. Nothing big or bulky, but most of the various items we might use are here. Anything you're in the mood for?"
That was a good question. In their months together, there wasn't much left to explore. Most anything dominating with Winter had been tried, and most things with Qrow had also been attempted, apart from those that didn't abide by his rule.
Although, that rule was starting to become less of an issue. The more Qrow thought back to the conversation with Blake that first time, that gesture with her finger, the more he was beginning to seriously consider letting the rule slip. Winter would know what she was doing, and they had safety words. There was very little reason to stop them from experimenting except for his own anxieties.
"Maybe… you could Dom tonight?"
That caused Winter to blink, and quite a few times. "Me? Oh… I had assumed you'd want to be on top." Mostly because his life was so out of control at the moment; she presumed he would want to regain that through play. Quickly she followed up with, "But of course, that's fine by me! What sort of experience are you interested in? Petplay? Spanking the naughty schoolboy?"
"Well, I kinda want your input on this one. Cause… something I wanna try. You remember the rule I set?"
"Which rule was that? Oh - the anal limit? Don't worry, I won't even go back there tonight. We can focus completely on Rooster's rooster." The last was said with a slight lilt of teasing, but mostly, her tone was very gentle with him. She wanted him to know that anything he wanted was his; she was fine with him playing the "power bottom" role for one night.
"Actually… damn, how do I put this?" Yet again he scratched his head. This wasn't going to be a regular session of play. It seemed that Ruby wasn't the only one of this side the family she'd be guiding through certain experiments. "I was wondering if we could, uh… try out some stuff."
"You… wait, wait." She walked over to sit down next to him on the bed. "This is a pretty sudden change, isn't it? Are you… sure? I mean, I have no problem - especially with you freshly showered - but if you're on the fence about this, then perhaps we should talk through it first."
Cheeks the tiniest bit rosy, he answered, "I've been meaning to bring it up a while actually. That first night we went to the club, Blake was tellin’ me about it. I was curious. But… y'know, macho pride, or whatever." He shrugged his shoulders yet again. "But I figure, you've just seen me at my worst, so there ain't exactly any shame anymore."
For a moment, she watched him as he carried the burden inside of himself. Then she leaned in and pressed her lips up against his neck before whispering, "I'll fuck your ass until you're begging for mercy, Qrow. But that won't heal what's inside of you. If you do want to talk later, I'll be around."
It brought a smile to his lips. Turning toward her instead, he looked once again between two things. Her eyes and her lips. Both were fast becoming his favourite thing, even if the relationship wasn't a romantic one. It was a friendship that brought comfort to them both, something that meant it didn't matter what people thought. With that in mind, he asked, "Don't suppose you wanna stay the night?"
"Oh, I could be convinced," she sighed, as if it were some great burden. Then she reached back and gently patted his hindquarters. "Now, as for this… you'd better start thinking about just how much you want to try tonight. I'll give you a good fingering if you want, or we could go even further than that. Up to you."
"Fingers sound like the best start," he agreed, finally undoing the towel and tossing it to one side instead. It seemed pointless to keep it on now. Yet again, he found himself looking to the bag that Winter had prepared. No doubt she would have only brought items to suit her needs in anticipation he'd take charge as normal. The strap on wouldn't be in there. However…
"Hey, what about that vibrator? That in your bag of tricks?"
Her smile was growing wider. "Somebody really is feeling adventurous!" Her hand trailed up his toned chest, through the iron-grey hairs that curled gently there. "How about… you let me take care of you, and worry about what I have with me later? I'll start off wearing a glove and then try some fun things." The hand stilled. "But don't forget our safety signal, and use it if I try something that doesn't sit right."
"Yeah, the chicken noises, got it." Nodding in agreement, he finally shuffled himself further back on the bed, laying back on it. A glove didn't sound so scary, not when Winter would know how to take absolute care. Looking to her from his angle, he smirked. "Have at it, I guess."
"You guess?" she burst out, unable to keep from laughing. Meanwhile, she did stand up from the bed to fetch her bag, out of which she nipped only two things: a small bottle of lube, and a pair of disposable latex gloves. "Now, this doesn't have to have all the 'domming' language if you don't want, but if it is what you want… you know what two words you have to say to start things off."
"Long as you're gentle." He had already began to part his legs, enough to give Winter plenty of room to work with. If it was any other situation, he would have leapt straight in, allowed Winter to call him everything under the sun. But in this instance, he wished for a more gentle start, just till he was used to things. Still, he trusted her enough to do that, and uttered those words: "Begin Play."
Winter paused to smile down at him as she pulled on the second glove before she nodded to convey her understanding. A thoughtful expression passed over her face; there was a route she could take their evening, but wanted to test it out first. See if he was interested.
"Someone's been a bad little girl." Then she raised an eyebrow at him, waiting for a response.
Little girl? That made Qrow raise an eyebrow. Seemed they were going to be experimenting with more than just his back end. Not knowing how else to respond, he lowered his head. "Yes, Princess."
A hand pressed to her lips as she suppressed a laugh. She had been expecting him to gruffly brush off calling him a "girl" in this situation - or any other! But now that he had acquiesced… this might be fun, indeed.
"Poor girl," she sighed, trailing a hand from hip to down along the thigh. "Keeping secrets like this… it won't do. Princess will have to punish you."
"This is gonna be so weird…" he muttered under his breath, yet did nothing to stop her as she toyed and stared at him more and more, finding himself beginning to blush. Her other hand fell to her hip as she gazed down at him, wondering where she might go from there. His anatomy was not erect, but it was fully exposed for her to toy with. But should she?
Not yet. "Turn over, because this little girl has earned herself a spanking."
"Yes, Your Highness." Back to spanking again. Seemed Qrow had discovered what Winter particularly enjoyed when it was her turn to be dominant. As much as he didn't mind, he was rather glad that she didn't have the paddle this time; the last session had him unable to sit properly for a few days. Rolling over as asked, he couldn't resist giving his hips a small shake to entice her.
"Ooh, she wants it," Princess chuckled as she watched her target sway. "We'll see how long that lasts." And without another warning, she reared back and gave it a little SMACK!
"RGH!" Even if it was barely anything compared to what Winter was capable of, it was enough to make him flinch, and clench his backside in response to the pain. But it wasn’t really bad. He could never explain why if someone were to ask, but it was almost an enjoyable sensation.
"Naughty little thing," she breathed, rubbing her hand in a circle over his cheeks. "You know you should have told me about the money. That you wanted to be fingered. This is what happens when you don't tell Princess everything."
Then, another spanking, this one with a smidgen more force. Flinching yet again, he growled under his breath. As much as the money situation was still a worry, Winter had offered enough of a solution for it to be talked about without too much stress. Frowning, he tried to look back toward her.
"S-Sorry, Princess. It won't happen again."
"Of course it won't. My naughty girl is learning her lesson, isn't she?" Another swat, followed by more caresses. "Learning it good."
Another flinch, another grunt, Qrow could only push his head into the pillows. The treatment and name calling still was an alien concept. Not that he got as much out of it as Winter did, but he could handle it. Yet again, he swayed his hips side to side, trying to entice more. Rearing back, she obliged what his hips were telling her, rearing back to thud her hand into him yet again. And again. With one more, she stopped and stroked over his soft hemispheres of flesh, taking a moment to trail down to the dangling sex and rub over everything there, as well.
"Does she like this?"
"Yes…" Perhaps it was the idea of being owned that made the pain so titillating. He could certainly see why Winter enjoyed being dommed so much. But yet again, it couldn't last. One strike hit the same spot too hard, and the pain was too much to ignore. Wincing, he grasped the sheets, breaking his character a moment. "O-Okay, no more. It's good but… argh."
"Agreed, I think you've had enough punishment. Now, it's time for your reward." Instantly, a finger was pushing up against Qrow's tightly-puckered hole. "And I think you've been waiting for this for a long, long time, haven't you?"
"Argh!" Instinctively he was pushing himself further against the bed, eyes snapping open wide as he gripped the sheets yet again. "Easy! Your… girl needs… a little warning. Help me get ready."
"I'll make her ready." But a moment later, there was a cold, wet sensation dribbling down from higher up, and the fingertip began to move from side to side as it coated the opening in wetness.
"Nnnn! Nnnoooo waiting with you, is there?" With this being more of an experimental session, Qrow wasn't too concerned with keeping his character. If anything, it made it more enjoyable, putting him at ease on what was going to happen. Within no time, he was relaxing into the sensation, letting go of the sheets and letting himself fully sprawl out for her. Already he could feel his rear relaxing as well, muscles loosening to let her in.
"Nope," she told him easily as her digit moved back and forth. He seemed to be much more open to this action than last time, and she could already feel the resistance giving way. The other hand drifted back and forth over his package, but not truly stroking; just teasing lightly.
There was a pleased smile on his face all through her actions. The more she prodded, the more he was opening up to her actions. Eventually he even found himself pushing back against them, biting his lips in anticipation for what was to come. He could tell this was going to feel good.
And it did - when she replaced the finger with her tongue, pushing it in to the level the fingertip had penetrated without any hesitation.
"AAaaaahhhh!" For the second time, a tongue was pressed into his tight opening, wedging him open around the wet muscle. Why was someone of her stature so keen on putting her tongue here? It was mad! But it was doing the trick, helping him open up more and more.
"Mmhhh," she breathed into him as she continued the treatment, both hands gripping his backside - and a lot harder than was strictly necessary. Her tongue was deeper than she had pushed last time, waggling from side to side slightly.
"Nnnn! Wint- u-Uh, Princess!" he called out, finally now starting to clench at the sheets as her tongue worked its way deeper, opening him further and preparing him for what was to come. That was if she planned that anymore.
"Is this what y-you like? T-to put your tongue there?!"
Back her face pulled, only for her finger to slide right back where it had been a moment ago. "Do you hear yourself?" she asked him in a confident tone as she easily flew past his lowered defenses. "Why do you think I like doing it? It makes little girls moan."
"Aaah… Hah… Aaaah…" But the moaning didn't begin until he felt the gloved finger return to the area again, until it pushed even firmer past the outer ring. The lubricated latex had finally worked her magic inside his body. Knowing it was his first time going that far, in that area, Winter began to push in and out at a very gradual pace. She knew how wild she could drive him, but there was no sense in scaring him off by jumping the gun.
The noises coming from Qrow were unreal. She was barely even in there and already he was continuously moaning and growling under his breath. How could he have not known how sensitive that area was? How could people in general not know this?! It was no wonder men like Sun would submit themselves if this is what they were feeling.
"Look at this little slut," Winter purred as she increased her pace, watching as the skin dragged against her knuckle on its way back out of him. "She really enjoys what I'm doing. Probably wanted this for a long, long time now… just didn't know how to ask."
"Hhhh!" He continued to growl out against the pillow, finding himself even pushing back against the fingers! For shame, he really did enjoy this more than he wanted to admit.
Especially so when he felt her finger brush against something very particular inside, and ended up suddenly gasping. The little sound caused Winter to hesitate, glancing down at him.
"Ooh, did I find something fun inside of her? What could it be?" Her finger hooked downward again, attempting to tease the same spot. Of course, she knew where it was, but she hadn't been aiming for it so early on.
"Fff-fuck! W-What is…" He could barely string a sentence together anymore. The finger stroked over that something a little more fully now, rubbing up against the oddly ridged little mass inside of him. This wasn't her first time toying with one, but it was the first time she'd touched Qrow in such a deeply sensitive region. His reactions were enough to encourage her to do more.
It was such an intense sensation. He couldn't get enough of it! The tightness of his own muscles around her finger added in with the massaging of the gland was becoming one of the greatest things he'd ever felt, even if it had barely began. In fact, it brought another bout of delicious shame when he could already feel his legs beginning to quiver, as if he was about to finish.
With a giddy little laugh, she stretched down and behind her as she continued to tease his little entrance, having to stretch her arms out but being able to reach. Then she began to shift slightly from side to side as she maintained the pace, not even bothering to explain her actions.
The strangest thing Qrow had ever felt happened. He finished, as he suspected he would, ending up shivering and shuddering at the mercy of Winter's fingers while he growled out loudly. And yet, he could feel nothing had happened with his member. It was barely even hard, but there was nothing aside from the slight glistening of pre. But it had felt like an orgasm.
"Whu…" he panted. "What was that?"
"Ooh, interesting…" Leaning back in, Winter's free hand drifted up and down his thigh as she held her finger still for a moment. "Seems like you have just enjoyed your first internal orgasm. You really are a good girl now."
"Internal… what?" Eyes widening, he took another few breaths to compose himself. "You mean you can have a butt orgasm?!"
Giggling bemusedly, Winter's finger began to move again now that he had a moment to recover. "I can't, not really. But you can in very rare instances. Anatomical differences, you know."
"Jesus…" Qrow laughed to himself, still gripping at the sheet as Winter's finger kept itself buried in his rear end. Amusingly, he could continue. In fact, he welcomed the sensation. This really was something new.
"Is my little butt-slut ready for more?" she asked. There was no further elaboration on what she meant, only the question itself.
More. It was something totally new to Qrow that he could do this multiple times in one sitting, or that he even felt up to that. But the finger buried deep within him was still sending tingles, still made him feel incredible. He certainly did want more. Slowly nodding against the pillow, he muttered, "Yeah."
At this muttered wish, she began to more vigorously move her finger back and forth. In the meantime, there was a snapping sound; the lube bottle being opened again, followed by the wheezing of it being poured… but he could not feel any more lube dripping onto his body. What did she mean to do next, exactly? For now, he didn't care. He was just continuing to enjoy the sensations of the finger pumping in and out of him, pace speeding up faster and faster. He might very well have felt like another one, but it felt like something was missing. He'd need stimulation in another area.
"Highness?" He only just managed to ask. "C-can I… Stroke myself?"
"Not yet. Princess still has a surprise for her girl."
A surprise indeed. Next second, the finger withdrew from inside of Qrow and was replaced with something… rounder, larger. Slightly more blunt. Already, it was edging into his body at an extremely slow pace.
"Wha- ah AH AAAAH!" Something was spreading the backside muscles far more than before. Qrow didn't even know that he was able to open up that wide! When it slid inside an inch, he had to look around to find out what it was…
And there was Winter, towering above him, with a length of her own attached to her hips. A rubber one that was doing it's job penetrating his body.
Noticing his gaze, Winter smiled sweetly down at him. "She's noticed her new friend." Her voice was honeyed and soft, and she paused that slightest amount inside of him, letting him adjust. "Do you like it?"
"You're… You're actually… F-fucking me?" It was stating the obvious, but he still couldn't believe it. Even when it was right there before his eyes, he could barely believe he was letting Winter do this to him. Nor could he believe how good it felt there, how good his backside felt being filled by the new object. He needed more of that. As best he could, he tried to shamelessly push himself back onto it, biting his lip to resist moaning again.
"O-oh!" Winter gasped quietly when she saw him being so eager. "The little slut really seems to be enjoying herself! Well, then… shall we begin in earnest?" Pushing her hips forward slightly, she gave him another full inch of the implement before halting again. "Still good?"
"Ooohhh…" He nodded against the pillow, still growling outward in pleasure. It was still an incredible sensation, just as her fingers were earlier. He wanted to keep going, to let her thrust freely.
But he still needed more if he was going to finish. Unable to help himself, one of his hands released the sheets, and immediately went straight to his soft length. Grasping it, he already began to work at it, trying to get it firm and hard again. Never before had he felt this needy, and it was all caused by a fake dick in his backside!
For another moment, she held still and watched him perform, enjoying the show. Then, deciding he was ready for it now, she leaned forward and pushed herself all the way in to the hilt. He was so tight! Still, tight though he was, his body fully accepted her toy with relish. And it would again, and again, and again.
"AAAHH!"
When Qrow first talked about ending his time in the apartment with another noise complaint, this definitely wasn't what he had in mind! In fact, if anyone would have told him a few months ago that this was going to happen to him, he'd have laughed in their face. Yet as he pumped his hardened member, he continued to moan out loudly, unable to help but clench his muscles around the thick dong in his backside to feel it there.
"Honest question," she sighed as she began to thrust in earnest, in and out of his tight hole. "Would you rather do this on your back? I know we started like this, but… up to you."
It would make it easier to pump his length. And it would let him see just who was doing this to him. That was a factor he didn't mind at all, knowing a woman was bringing him so much pleasure in the only entrance he had. Deep down, he preferred that. There was less shame that way.
"O-on my back," he agreed. "I-if you don't… mind."
"Not at all, cutie." But she had a fun surprise in store for him. Lowering her hips as much as she could, displaying an incredible flexibility as she nearly did the splits behind his end, she began to roll him while the cock was still deep within his backside. It was not an easy task, but she seemed determined to make it work.
There was another strained moan as she moved him around as she pleased, feeling the lubed member swirling inside of his sensitive innards. He ended up on his back, resting his legs onto her shoulders to give her plenty of room to work with. Once more, his hand returned to his member, grasping it to keep it hardened.
When he looked up toward her again, his face was completely red. It was something she'd never seen before in him, an animalistic urge to submit. And it was only her who would ever see him like this. Wrapping her hands around his ankles, she favoured him with a dark little grin as she pressed her hips in a little more and rumbled, "So… are you ready for me to ride you all the way to the finish line, my little mare?"
"I thought… hah… Glynda was the mare?" he managed to pant out. Still stubborn, even when he wasn’t the Dom. But regardless, he was already starting to pump his member again. Slowly, just enough to keep the pressure on before she could continue. Clenching around the shaft inside him, he nodded. "R-ready."
"Tonight," she sighed as her hips drew backward an inch at a time, "you are my fine steed, young lady." Then, with no other forewarning, she thrust forward with twice the speed from before, slamming their bodies together with a soft little thud!
"Aaahh!" Another moan for Winter's mare as he was thrust into again with far more intensity than last time. And it didn't stop there; soon Winter was building up her pace. Quite literally fucking him. He increased his pumping to try and keep up, desperately trying to get himself to get another finish. It was more to prove that he could than anything else. Prove that he could finish with Winter being the one inside him.
Only Winter. Ever.
"That's right!" she crowed out, bending his legs back as she picked up to full speed. "Fuck yourself, little princess! Come all over yourself! Show me how much you like me drilling you!"
"AAAH! HAH! HAAAH! H-holy SHIIT!" It was the last he could take. Everything was all too much, and he found himself giving into her completely. Another shudder of his legs while she grasped his ankles, another few pumps later of himself, and he was done for. The length throbbed in his hand while he felt the muscles in his rear end clamp on the member, pushing him to orgasm for the second time this evening. It was unusual for Qrow to see this much seed he was releasing, and all over his stomach and chest, no less! It truly was a shameful sight. But by this point, he'd completely transcended the boundaries of shame.
Of course, Winter fell silent when she saw the white fluid splattering all over his body, looking down upon him with mingling awe and satisfaction. That was something she never thought she would see the normally-proud man do, but it was most definitely satisfying. Her pace began to slow gradually, but she didn't come to a stop entirely; it was too fun to resist.
Gradually, the moaning was beginning to get slower, quieter, and more strained. His pumping slowed to a stop, and he had to grasp the bedsheets instead. Two was more than enough for one evening, especially in this quick succession. With that in mind, he tried to push himself backward off the member himself, managing to pant a response.
"T-that'll do… M-mare's had enough."
Chuckling quietly to herself, Winter gave one good, hard, final thrust just to get a rise out of him.
"NNNN!" Amusingly, that firm push had pumped a little more seed out of him, only just dotting his abdomen. But he wouldn't let that continue for any longer. "Hey, knock it off, I'm gettin' sore here."
"Party pooper." But the next thing she said was, "I'm going to try to pull out slow and smooth. Are you ready?"
After grasping the sheets to brace himself, he nodded. "Ready as I'll ever be." Nodding her understanding, she drew back and out of him in one fluid motion, an inch at a time. One last shaky moan, and she was free. Already he could feel his muscles beginning to tighten up again, and already there was an odd feeling of emptiness now that she'd gone. Not that he would be asking her to put things back in any time soon.
"So…" He just began to catch his breath again. "This doesn't mean I'm gay now, does it?"
"Perhaps a little, but no more than I am." Her shoulder shrugged as she rubbed up and down his hip once his legs were lying flat again. "And as I keep insisting, I'm straight with some small amount of leeway. It's not an either-or."
"Yeah, guess so." Finally, he gazed down at his chest. Splattered with his own juices, more than he had ever thought he alone was capable of. "Jesus! And I just showered, too!"
"No reason we shouldn't both shower now," she sighed, looking down at the implement she had taken him with. "After taking care of this, I might want to. No offense."
"Hey, you're the one that decided fucking me with a strap on was a good idea! I just wanted fingers!"
Half way through his sentence however, there was a repeated buzzing sound coming from Winter's jacket pocket. It was too late in the day to possibly be a client, and her father said he wouldn't bother her. Who could it be? Stripping off her gloves as fast as she could, so they would be inside-out and not get on anything, she tossed them onto the bed and snatched up her phone to see who it was. When she saw Yang's number, her eyebrows rose as she answered it.
"This is Winter."
"Hey! It's me! Um… Y-y'know how you said to call if anything changed?" Yang was sounding a lot more flustered than normal, talking quickly and stammering the odd word. From the background noise, it sounded as though she was driving.
"Yes?" she put in. "So I take it something has-"
"DON'T TALK ON THE PHONE AND DRIVE AT THE SAME TIME, YOU IMBECILE!" a screeching voice ordered a little further away from the microphone. "WERE YOU RAISED IN THE WOODS?!"
"WELL I COULD HARDLY SET UP THE HANDS-FUCKING-FREE RIGHT NOW, COULD I?! DO YOU WANT FAMILY THERE OR NOT?!"
The yelling was even heard by Qrow, who had just been about to clean himself up with some tissues when he recognised Yang's voice. Stopping for a moment, he listened in.
"Sorry, didn't mean to yell, but yeah! You could say that; I think from the yelling she's in labour!"
"Oh? OH!" Completely stunned by this development, Winter's hand pressed against her face, leaving a very light powdering from the latex glove. "God, this is- SHIT! Shit, does it have to happen NOW?!"
"What? What is it?" Qrow had whispered to ask, still not even close to being clean just yet. He'd been too busy trying to listen to one half of the conversation.
"I know, why couldn't Weiss have held it in for another week like she was suppos-" That thought was beginning to trail off for a short moment. "I'm joking, Winter said something about the timi-"
"IF YOU WANNA PUSH THIS BABY OUT YOUR FUCKING DICKHOLE, BE MY GUEST!"
"Eh heh," Winter said in response to her sister's moaning. "Just… hold on as best you can. Which hospital are you going toward?"
"Vanderbilt. That seemed the best one and it's closest. And will you please STOP FUCKING YELLING AT ME, I'M TRYING MY BEST!"
"Hospital? Wait… are you kidding me?!" Qrow had finally caught on, sitting himself upright at last and actually making more of an effort to clean himself up this time. No doubt Winter would want to leave straight away, and he hadn't even got a fresh pair of clothes ready!
"And I'm wearing THIS!" Winter shouted, gesturing down at her pelvis. Next second, her good sense had come back to her and she told Yang, "I m-mean, I'll be there as soon as I can! Just take care of my baby sister! I trust you!"
"GO FASTER! Run that red light!"
"I ALREADY RAN THREE! O-okay, later!"
It wasn't exactly the most reassuring way to leave a conversation, but there were obviously other things on Yang's mind right now. Just as there were Qrow and Winter's. They would need to skip their shower, and definitely rush the clean-up. Grabbing yet more tissues, Qrow continued to clear away the vast amounts on his chest. "She's a couple weeks early, ain't she?!"
"Tell that to the baby!" Winter grunted, dashing into the bathroom. The only sensible thing in her mind at that moment was to take the strap-on off in there and leave it in the sink, where she could also wash her hands afterward.
Collecting a random shirt from the dirty laundry pile, Qrow took a quick moment to sniff at the pit area. No real stench, it would do. He was hardly going to put on a spotless shirt when he was still barely cleaned. Forcing it over his shoulders and quickly grabbing some underwear and pants, he was trying to rush as quick as possible to get ready.
"Can't she hold it off or something? Clamp her legs together?"
From the bathroom, he could hear a near-outraged, "Don't you know anything about biology?! She can, but not for very long before her body decides she's being stupid and pushes it out anyway!"
"Well how am I supposed to know that?! It thought it was like takin’ a… y'know what? I'm not even gonna finish that." Quickly forcing on a pair of socks, he was more or less finished. "Mind giving me a lift, too? I'm still over the legal limit. Didn’t think I’d need to drive tonight."
"Of course. We'll just… say I picked you up on the way there." Just then, she returned, sans one strap-on and looking much the same as she had when arriving, though a little worse for wear. "Oh, and… try not to be too startled when the inevitable happens."
"And what inevitable is that?" he asked, hurriedly walking to the front door to thrust his shoes on and collect his house keys.
As she passed him to open the door for him, given that he was still struggling into his shoes, she muttered two words under her breath: "Lube fart."
"Lu- oh come on, you gotta be kidding me! Way to make me feel super gay." Finally finished, he quickly dashed out the door, waiting for her to follow first before he locked it and they could get on their way.
"Aww, listen to her; she's so angry about the lube fart!" Winter cackled as they locked up and raced down the hallway. Undignified though it was, she would continue to laugh about lube farts all the way there.
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Black Tie	By : RWBYRemnants Category: +M through R > RWBY Views: 1476 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: RWBY is not mine and I make no money from this fic

Black Tie