Silver Eyes Ch. 8 (RWBY)

A/N: Under the stars it is~

-x-X-x-

Cole watches with a raised brow as Amber contemplates his question for a longer moment than he had expected. Honestly, given how straight laced the Assistant to the Headmistress seemed, he’d mostly just asked because he figured she’d get bright red and immediately tell him they would be ‘doing this’ in private, as Glynda had dictated to them.

Well, Amber certainly gets bright red… but she doesn’t immediately say anything. Instead, she grabs him by the hand after a moment and begins pulling him along.

“C-Come with me…”

Curious now, Cole allows her to direct him. Instead of going to the private room that Glynda said she set aside for his… activities, Amber takes him somewhere else entirely. They do stop at a supply closet though; one filled to the brim with pillows and blankets that are likely meant to supply the dorm rooms on this floor.

Then, Amber takes him up some stairs… and some more stairs. Suddenly, Cole finds himself out on the roof of Beacon, staring at the glittering lights of Vale off in the distance.

“H-Here. If that’s okay…”

Amber’s hesitance piques Cole’s interest. The woman is clearly older than him, but if he didn’t know any better, he’d say she was a virgin. Has she never been with a guy before now? That’s surprising, she’s certainly not unattractive or anything like that. Looking around the roof for a moment and then glancing up at the starlit night sky, Cole shrugs.

“Here is fine.”

Avoiding making eye contact with him, Amber just nods and resolutely starts building them a spot for lovemaking, or rather breeding, right there on the rooftop. Using the pillows and blankets, she soon has something of a bed sans frame or mattress set up. However, despite it being more than good enough, she keeps fiddling with it, as though she’s trying to make it perfect.

The closer they get to doing the deed, the more obvious Amber’s nervousness becomes. Cole can’t say for certain… but she really might be a virgin after all. Finally, getting a little impatient, he reaches out and grabs the brunette by the shoulder, pulling her away from perfecting their makeshift ‘bed’ and turning her to face him.

Before Amber can react, he’s already kissing her as he pulls her to his chest. The brunette freezes up for a moment, but eventually she melts into his chest and the kissing, whimpering softly into his lips. It’s only when they finally have to pull apart for air about a minute later that she bites her lower lip and looks away again.

“W-We don’t… need to do any of that for t-this. After all, this is only… so you can get me pregnant.”

Cole scoffs.

“The more we both enjoy the sex, the higher the likelihood that you’ll get pregnant in the first place.”

That gets a wide-eyed look from Amber.

“Wait… is that true?!”

Fuck if he knows. But he said it with pure confidence and he’s not going to back down now. Rather than answering her with more words though, he answers with actions. Namely, by kissing her again… as well as sliding his hands down and around to her ass to begin groping it and squeezing it heatedly as they makeout.

Amber mewls and moans, relaxing further and further into his embrace. The young woman, albeit still older than him, clearly has absolutely no experience with this kind of thing. Cole will just have to take the lead, in the end.

Although, just as he’s thinking that thought, Amber suddenly tugs at his embrace. He relaxes his hold on her and watches in surprise as she pulls back but also pulls him with her. They arrive at their makeshift bed with just a couple of steps and Amber drops to her knees on the carefully arranged pillows and blankets, her hands going to his crotch while she looks up at him.

“I should… use my mouth and hands to get you r-ready then first, shouldn’t I? That’s how it usually goes…”

That’s how it usually goes in porn, yes. Good lord, this really was a repressed virgin, wasn’t it? Cole grunts but doesn’t say yay or nay one way or the other. And Amber takes that as approval, carefully pulling his cock out of its confines and breathing shakily all over it as she takes him in both hands and begins stroking his dick.

“It’s so big…”

She sounds both awed and terrified at the same time, even as her soft palms glide along his shaft. After a few hesitant strokes of marveling at his heat and hardness, Amber finally leans forward and places a gentle, almost chaste kiss on the tip of his cock. It would have been chaste if it were placed anywhere else on his person.

Then, with a deep breath, the Headmistress’ Assistant parts her lips and takes him into her mouth, her tongue lapping at the head of his dick. Amber’s inexperience is evident in her technique, but she more than makes up for it with enthusiasm as time goes on and she finds her footing.

Soon enough, she’s bobbing her head up and down Cole’s member, taking more and more of him into her mouth with each pass. Her hands, meanwhile, work in tandem with her mouth, stroking whatever she can’t fit past her lips.

As she sucks him off, Amber looks up at him with wide, innocent-seeming eyes. It’s almost like she’s silently seeking his approval and guidance, truth be told. Cole grunts and nods down at her hands.

“You have two hands. Cup the balls while you stroke the shaft.”

Amber takes to the guidance like a fish to water, one of her hands immediately dropping to gently fondle his nut sack, massaging them as she continues her oral ministration.

She was a definite people pleaser, Cole notes. Glynda had likely told her not to get too attached or anything like that, but now that Cole had convinced her that the breeding would be more successful if they made it pleasurable, Amber is going all out. She was just looking for an excuse, really.

He could do a lot with that… if he could wrap her around his finger properly. It’s not something Cole is very experienced at though. He’s a thief, but he’s never been one for stealing hearts. Nor is he much of a leader either. Still… never too late to start, right?

Reaching down, he plants a hand atop Amber’s head and graces her with a smile that isn’t even entirely faked.

“Good girl. You’re doing well so far.”

Amber blushes at his praise, pride positively glowing out of her despite the awkwardness of the situation. She quickly redoubles her efforts too, determined to please him with her inexperienced but altogether eager mouth.

Taking him deeper in, she quickly hits the back of her throat with the tip of his cock. A small gagging sound escapes her as that happens but she doesn’t pull away. Instead, she holds Cole’s dick there for a moment before finally slowly pulling back, her tongue licking and lapping around his shaft.

Meanwhile, Amber’s own body seems to be starting to respond to the intimate act despite her being the one doing all of the work to please HIM at the moment. She shifts her thighs together in a way that makes it clear she’s trying to relieve an ache between them, and she even starts to whimper and moan around his cock, the reverberations of which send shivers up his spine.

Looking up at him again, her eyes are watery but filled with determination. She clearly wants to make him feel good, to prove that she can be a good little breeder for him… or something. Really, it’s not like Cole can read her mind or anything like that. Still, with a sudden surge of renewed vigor, Amber takes him deep once more, sucking hard and hollowing out her cheeks in the process.

At the same time, the further she takes his cock into her mouth, the less the hand stroking his lower shaft has to do. Eventually, it drops into her lap… and from there, works its way into her pants where she clearly starts to touch herself if the muffled moans around his cock is any indication.

Finally, Cole has to pull Amber off of his cock before he can get too close to cumming. His throbbing mast stands at full attention while glistening in the starlight from her slobbering efforts. Amber blinks up at him, while Cole just smirks at her.

“If I’m going to breed you tonight, the only place my cum should go is inside of your womb. Lay back for me.”

Her eyes widen at his words, a mix of nervousness and anticipation flashing across her face. But all the same, she does as she’s told while stripping off her pants. Cole gets out of his own clothes as well, noting that it’s a nice night for stripping naked on Beacon’s rooftop, thankfully. The sky is remarkably clear overhead, and while it’s slightly cold, it’s not so cold as to be frigid or even chilly.

Though… Aura probably has an effect on that as well, pushing back any would-be weather conditions that would otherwise make this experience miserable and untenable.

Regardless, once they’re both naked, Amber lies back on the makeshift nest of pillows and blankets, blushing deeply all the while. She watches him with a mixture of both fear and excitement as he moves between her legs, her body tense but ready. Though, even as she spreads her legs for him and gives him access to her most intimate of areas, she does hesitate for a moment.

“It… it’s my first time. Please b-be gentle.”

Huh, Cole wasn’t entirely expecting her to admit it. Still… he can do that. Nodding at the slightly older woman, he gives her his best reassuring smile. He can tell it catches her off guard, given how standoffish, confrontational, and all around belligerent she saw him being all day today.

He’s not always an asshole though. Just when it feels appropriate. And rebuffing the advances of all those girls today… that had felt appropriate. But hey, maybe he was wrong. Maybe Amber was right and he needed to be a bit more open if he was going to be on a team with some of these people for the next four years.

… They would see, in the end.

For now, Cole places the throbbing tip of his cock against Amber’s slit and begins to slowly, torturously push in. Honestly, it’s better that he’s going slow anyways, given how turned on he is right now. He’ll last longer this way, and he wants to see Amber cum for him at least once before he finishes inside of her.

To that end, Cole takes note of her pert naked breasts heaving up and down in front of him. Her nipples are rock hard and rosy, just begging to be touched. So Cole doesn’t hold back, reaching up and grabbing hold of her breasts, even as he inches his way towards her hymen. Amber gasps and instinctively arches her back into his touch, her eyes widening a little bit as he begins to play with her tits.

She’s probably touched herself before… but it’s obvious she’s never done what he’s doing to her poor, sensitive breasts. His fingers grip down on the soft flesh, and his palms rub intentionally against her rock hard nipples, rolling them against his hands.

Moaning beneath him, Amber shudders even as Cole finds himself arriving at her hymen down below.

“Please C-Cole… make me yours…”

Not exactly what they were here for, but that just went to show that his plan was working. Having Amber on his side would definitely be a boon and it seemed he was making rapid progress in taking the Headmistress’ Assistant down the path of debauchery and depravity. Grinning, he pulls back… and then thrusts forward, driving through her virginity right then and there.

Amber’s eyes, which had started to grow heavily lidded, snap wide open as a squealing cry leaves her lips. She bucks a bit under him… but the pain is fleeting and only lasts for a brief moment at most thanks to all their foreplay. Cole pauses all the same to let her adjust and once he can tell the pain has begun to subside, he starts moving in and out of her.

She looks up at him, her eyes wide and watery, her lips plump and parted on her flushed face. Her hands grip at the blankets beneath her, knuckles white with effort. Her inexperience is obvious here, and Cole likes to imagine the way he’s stretching her out and filling her with his cock is unlike anything she’s ever imagined before.

As he starts to move properly, Amber’s breath hitches in her throat, followed by moans as each thrust seems to send waves of pleasure coursing through her. Her once-untouched inner walls are struggling to accommodate his girth. She whimpers and moans, her hips nevertheless instinctively moving to meet his thrusts.

Her breasts also bounce with each movement, drawing him back to them as the soft flesh jiggles enticingly. He cups her chest once again, fingers pinching and tugging at those stiff peaks. Amber moans all the more wantonly, shuddering under his touch and the feel of his cock stretching her out so deliciously.

There’s no doubt in Cole’s mind that he’s going to drop a huge load of his seed into Amber tonight. Whether that will be enough to breed her or not is still in question, but he’s not worried about it. They have all the time in the world after all, and the more times they fuck, the more he gets paid.

PLAP! PLAP! PLAP!

The wet, obscene sounds of their copulation soon fill the rooftop of Beacon’s tallest tower, mixing with Amber’s increasingly loud moans. But Cole isn’t worried about it because it’s not like anyone is around to hear-

Just as that thought is passing through his head, Cole absently glances up. He can’t even say why he does it… maybe he could sense their presence. Still, because he glances up, he catches them spying from around a corner across the rooftop. Someone he recognizes watching him fuck Amber silly right there on the spot.

As Amber’s eyes roll back, her head tossed back into the pillows as he pounds into her, Cole makes eye contact with that familiar woman, staring her down all the while. It would seem they had a voyeur on their hands…