They Make Amazing Prostitutes (RWBY) (Patreon)

Poll Winner

Themes: Prostitution, Fivesome, Dom/Sub

Summary: Inspired by these memes. With Roosterteeth shut down, RWBY's journey comes to an end. And the girls from Team RWBY find themselves suddenly needing to find work. Fortunately for them, they have a fallback plan, one inspired by all of that amateur porn of them made over the years. They'll just become whores! Doubly fortunately, there's plenty of rich young men who will pay for their time. But only one is willing to pay for ALL of their time at once~

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“… fuck, I can hardly believe this is real…”

Hands on a pair of hips he never thought he’d get to touch in this way, laying on his back as she rides him, Theo stares up at the ceiling, still a little amazed that this is even happening. Of course, in response to his words, the woman currently bouncing up and down on his cock giggles a little bit.

“Well believe it, silly. You’ve got the great Ruby Rose herself riding your dick. Make the most of it~”

Swallowing thickly, Theo looks up into her silver eyes and finds his resolve, nodding in agreement as he tightens his grip on her hips and begins to thrust up into her from below. She squeaks and then moans, one of her hands resting on his chest while the other goes to her own chest to play with one of her tits.

She’s right. He should make the most of it.

Theo hadn’t come from much. Everything he had now, he’d earned through his own hard work and effort. Well, that and a lot of luck. One could never discount luck. It frankly made the world go round. Still, he hadn’t been born with a silver spoon in his mouth. He’d just made the right decisions at the right time, played things safe when necessary and taken risks at other times… and it had all worked out in his favor.

Suffice to say, that might have been a little bit of an understatement if one merely looked around the room. This was the Master Bedroom of a Penthouse Suite in upstate New York, one of the most expensive places in the entire city. And it was only one of half a dozen homes that Theo owned thanks to his entrepreneurial successes.

Still, it was one thing to be rich. It was another thing entirely to manage to buy a night like this with the four hottest girls in the entire world… or at least, the four he considered to be the hottest girls in the entire world.

Ruby Rose bounces up and down on his cock even as he fucks her from below, her silver eyes threatening to roll back in her head even as she rolls a nipple between her fingertips. Meanwhile, silent but still present, Weiss Schnee is right behind her, arms wrapped around the other woman to hug her waist while she places light kisses along Ruby’s neck. Her own eyes gaze down at him with an arousing intensity as she waits for her turn with his cock.

Meanwhile, all Theo has to do is turn his head to the side to see the last two members of Team RWBY. Yang Xiao-Long and Blake Belladonna had started out wearing their signature outfits the same as Ruby and Weiss, but just like Ruby and Weiss, those outfits hadn’t survived for long.

However, unlike Ruby and Weiss, Yang and Blake weren’t engaging with him at the moment… instead they were engaging with each other for his viewing pleasure, kissing and moaning into one another’s mouths as they rub tits together and finger the other while he watches.

Yeah, Theo was the luckiest guy in the whole wide world. Eleven years ago, when the RWBY show had first come out, he hadn’t even been rich yet. The show and its main cast had hooked him like nothing else, but it was the girls of Team RWBY who had drawn him in above all others. And even as time had gone on, even as his life had changed in so many crazy ways… and even as Roosterteeth had steadily gone downhill, Theo had kept up with RWBY and Team RWBY in particular.

They were, to put it bluntly, his very first ‘waifus’. How could he not fall in love with them? Even as RWBY itself had gone further and further downhill, the plots becoming ridiculous and downright nonsensical, he’d kept watching for the team. Even as they’d jumped the shark completely with that Never After insanity, he’d still watched for Ruby, Weiss, Yang, and Blake.

And then the news came. Roosterteeth was done for. RWBY was done for. It was all over. Theo had to admit, he hadn’t known what to feel when it had finally happened. He’d seen the writing on the wall of course. He’d even toyed, from time to time, with trying to invest in Roosterteeth and use his money to get them back on track or something. But he hadn’t. Maybe because he’d known it was impossible. Maybe because their decline had ultimately seemed inevitable.

Still, he hadn’t initially known what to do about no more RWBY. Until he’d heard some rumors through the grapevine… that the girls of RWBY had made the decision to turn to prostitution. He never would have thought it possible, but everything he’d heard sounded like they were surprisingly enthusiastic about it.

So he’d made some calls. Gotten in touch with some people. And… he’d bought a night with all four members of Team RWBY. The cost was… astronomical, but nothing someone like him couldn’t afford. And now here they were. Here they all were.

With a lustful growl, Theo begins to fuck Ruby Rose even harder from below. Ruby’s eyes widen as he picks up the pace again, surprised by his strength and stamina. But that was the thing about being rich. When you didn’t have money troubles getting in the way, you got to decide precisely how healthy or unhealthy you wanted to be. When you got to set your own schedule and be your own boss, you decided if you had the time to carve out for a workout each day or not.

Theo was in the best shape of his life right now, in part because of the good decisions he’d been making for years now, but also because ever since he’d found out this was happening a month back, he’d redoubled his efforts. As a result, he was stronger, hardier, and just plain better than he’d ever been in his entire life.

Ruby shudders on top of him, her pussy walls clenching down in a way that Theo knows means she’s just cum for him. She looks a little surprised by this, but Theo just grins and grunts.

“Getting… close. Inside, right?”

Moaning a lot more vocally now, not quite as composed anymore, the leader of Team RWBY nods her head shakily.

“T-That’s what you paid for. Don’t worry, w-we’re all on the pill~”

Theo just grunts again, before finishing a few thrusts later. He groans as he fills Ruby with his seed, still almost unable to believe it’s even happening. Only once his balls have emptied does he let go of her hips and allow the silver-eyed woman to pull off of his cock. Of course, the moment she does so, Weiss takes her place.

Kneeling between his legs, running her hands up and down his own body, the beautiful white-haired woman raises an eyebrow at him.

“Well? How would you have this prim and proper heiress… Master?”

Theo flushes a little bit at the address, but he can’t deny how much of a turn on it is to have Weiss Schnee offering herself to him like that. His cock rises back to full mast even as he rises from his position, grabbing Weiss by her ponytail and dragging her into a tongue-filled kiss for a moment as he plays with her body. She doesn’t resist, moaning and pushing her tits into his hands instead.

Finally, he swings her around and puts her on all fours. Nothing hotter than taking a ‘prim and proper heiress’ as she’d called herself and making her his bitch, right? Besides, Weiss was always so bitchy on the show… he’d never hated her or anything like that, but there’d been more than a few times where he’d wanted to put her in his place.

And would you look at that, now he could! Grunting, Theo slams home into Weiss from behind, making her squeak and then moan. She’s more than wet enough that he doesn’t cause her any discomfort, even as her insides are tight enough to give him some pause, forcing him to pull back and thrust in again just to get deeper inside of her.

Weiss shudders and shivers under him, clawing at the bed as he fucks her doggystyle. Ruby, meanwhile, has laid down on her back and is swirling her fingers around inside of her cream-filled pussy. Whenever he glances over at her, she gives him a wicked grin and pulls her cum-covered digits out of her twat and brings them to her mouth, sucking them clean.

The display, along with Yang and Blake’s continual display of lesbian love, only spurs Theo on all the more. He fucks Weiss from behind harder and harder, until his crotch is slapping against her pale ass enough to turn it red. But she takes it like a champ, because under that lithe exterior is a consummate professional.

Her own preparations have also left her more than wet enough to enjoy him regardless of how rough he is with her. Her cunt walls are slick while also clenching down so very tightly around his cock. Theo gets lost in the moment, so he can’t be sure that she cums before he does… but he thinks she has to have had at least one orgasm before he finally empties his balls again, pumping the white-haired woman full of his jizz.

He drops his grip on her hair after he’s done, letting Weiss fall forward onto her stomach as she lays there prone, panting and recovering. Then, climbing off the bed, Theo moves over to get himself a bottle of incredibly expensive water, the kind that was designed to truly replenish someone’s electrolytes.

Taking a small break, the entrepreneur just lets himself enjoy the show. Ruby and Weiss are recovering still, though Ruby definitely looks like she could already go again if he wanted to. However, when she gives him an expectant look, he just shakes his head in response before looking to Yang and Blake.

He hadn’t paid for all of Team RWBY just to ignore half of their members, after all. Striding over to where the two women are going at it on the couch, he considers them for a moment. Then, he moves to their heads and interrupts rather rudely by sticking his dick right between their faces the next time they have to stop their lip lock in order to get some extra air.

To their credit, Blake and Yang are consummate professionals, the same as Ruby and Weiss. They’re actresses after all, and they’re nothing if not good at their jobs. The moment that they see his cock, the two prostitutes eagerly and submissively begin lapping and licking at his dick, only kissing each other around his cock if at all. Their eyes grow lidded and their muffled moans of contentment almost make it seem like they adore his dick and truly enjoy worshipping it with their mouths and tongues.

Soon enough, his cock is spit-polished and cleaned of his last two fucks and Theo pulls away from their faces, stepping around to stand in front of the couch. In response, Yang and Blake rise from their initial positions, sitting there on the couch and looking at him, Yang with a big wide grin on her face and Blake with an expectant gaze.

Theo grins right back as he looks between the two for a moment.

“Sorry for the interruption, ladies.”

Yang just laughs.

“Interruption? No interruption here! We’re all yours, sir~”

Fuck if that isn’t the hottest thing she could say to him. Still…

“Then I want you two right back as you were… but over on the bed.”

They share a glance at that before shrugging in unison and moving over to the bed. Yang on top, Blake on bottom, they go right back to making out with each other and rubbing against one another… until Theo moves into position down below and proceeds to grab Yang by her fine ass, pulling it down so that he can shove his cock right between her and Blake’s grinding cunts.

The two prostitutes moan in surprise at this, even as Theo slides in and out, hot dogging their pussy lips to his heart’s content. Fuck, he’d always been a fan of their ‘pairing’ on the show, but he would be lying if he said it wasn’t at least partially because he’d always had this exact fantasy. He was a red-blooded straight male; how could he not fantasize about having a pair of lesbians dedicated to pleasuring his cock?

Thrusting in between their bodies for a few moments longer, he finally pulls back and thrusts into one of them… Yang to start. He fills her cunt with his cock and starts pumping in and out of her, even as she moans and squeals and yelps into Blake’s lips. Then, after a couple of minutes, he pulls out and thrusts into Blake instead.

Between the two women, Theo is having the time of his life, and they’re certainly making every effort to make it seem like they are too. He knows full well that they’re all whores, of course. They’re only here because he paid for them to be here. But part of him still wants to leave a favorable impression on the four girls. Team RWBY had gotten him through some tough times before he’d become as rich and successful as he was now. In a way, this was him trying to pay them back… as selfish as his method was.

Still, even though it was possible they might be faking it, he’s pretty sure that he gives at least partially as good as he gets. In the end there’s no way for him alone to satisfy all four women in the way they’re satisfying him over and over again, but he makes sure to extract at least one real, legitimate orgasm from each before the night’s done.

Finally, to end things off, Theo finds himself sitting on the edge of the bed, the entirety of Team RWBY surrounding him. Yang and ruby are down on their knees, looking up at him as Yang uses her tits and Ruby uses her mouth on his cock. Blake and Weiss are pressed into his sides, rubbing their bodies against his and laying kisses along his neck and shoulders and muscular chest.

Letting out one last groan, Theo proceeds to cum in Ruby’s mouth. The so-called cinnamon roll of Team RWBY doesn’t let a single drop escape, showing her true nature as a First Class Whore as she drinks down every last drop of his seed.

Finally well and truly spent, Theo just smiles at the four tiredly.

“Let’s go to bed, shall we?”

They smile back at him and wordlessly follow him up onto the bed, crawling and positioning themselves on and around him so that each is touching a different part of his body. Theo falls asleep like that, basking in the afterglow of the reverse gangbang he’d just paid for. Best purchase of his entire life, bar none.