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Pirates? 1.1

The door to room eight slid shut behind her, and Vanessa grinned. The twins, Eric and Erica, were nearly indistinguishable tabby cats. They weren't actually related, but both were close to androgynous and they played that similarity up to the hilt. Identical hair style, identical clothing, the only way she could tell them apart was which one had noticeably more curve or bulge in which places. Today that wasn't really necessary.

Per her instructions, they'd done each other up, and were just waiting for a little outside assistance to be completely helpless. Buttplugs in place, ball gags, Eric had his favorite chastity cage on, and Erica's pussy rings had been tied shut with a ribbon. Both of them were wearing thick leather collars and cuffs on wrists and ankles. Attaching each twin's wrists to the others ankles was suitable. They certainly weren't going to be going anywhere like that.

"Well don't look too pleased to see me, you two." Despite gags, she could tell they were both grinning. "You know how it is. I spent a lot of time bottoming yesterday, I need to get back in touch with my top side. Ready to get treated like a couple of masochistic bitches?"

They didn't even pretend to be anything but eager.

That eagerness was very useful. She undid both gags, and settled herself over the pair, with Eric in front and Erica behind, and pulled hair to get them both in place, one rimming her, the other eating her cunt, and just rocked her hips while they worked.

And they were damned good at what they did, too, tongues and mouths and careful teeth teasing and pleasing her, pushing her into ecstasy little by little. Eric was, unsurprisingly, being a brat, and tried to hold her at the edge rather than push her over, but a growl and a further pull on his hair got the point across that this was not going to fly, and he put his effort back in to servicing her.

It only took a few minutes more for the oral service to send orgasm shivering through her, knees weak for a moment as she huffed and growled in pleasure. Then pushed the two away to let hem recover a little, flex and relax tongues and mouths.

"Oooh, we're off to a good start, but you're both in for a long, long day. We're going to play a game." The twins looked at each other with some mix of delight and worry. "

It took most of half an hour to get everything and everyone situated. A nice comfortable chair for Vanessa, a wand vibrator mounted in place, and the two cats, positioned with their respective bits close to touching it.

"So here's how this works. Obviously, the first one to cum loses. If neither of you cums within twenty minutes, you both lose. The only parts you can use to push against the vibrator are your cage and your pussy, respectively. The first five minutes will be on low, but after that it's high all the way."

They nodded, then Erica said, "so what's the prize and the punishment? Or do we get surprised?"

Vanessa paused to think for a moment, then shrugged. "Surprises for you two. Just remember that I can be very, very mean when I want to be, and that I know you two love to hurt for me." She flipped the switch, and the low hum filled the room, followed by a symphony of little moans and huffs of effort and strain. Eric was already straining at the bars of his little cage, cock trying to stiffen but not given enough room to do so. And his sister was grinding away at the head of the vibrator, pushing it against his cock.

Neither of them really had an advantage, Vanessa had played with each of them enough to know what really got them going. Denial, restraint, having to worry about how much failure was going to hurt. She didn't even have a real plan for how to punish the eventual loser, but the way they were shuddering and pushing and trying to get the other one off without popping themselves was what she wanted. Eager to please warring with eager to win. Any way it ended, she was going to be the real winner.

She flicked the switch again, and the buzzing changed pitch. Both cats let out a yelp of surprised pleasure, and she watched Eric draw back, trembling, shuddering, watched him teetering on the edge, struggling not to cum. He succeeded, barely, but knew he wasn't going to be able to push his sister much without losing. The little cat glanced at her, and she shrugged. "If you both cum at the same time, you both win." She didn't plan on it being that easy, though.

Sure enough Erica pushed against the toy more firmly, trying to catch up to Eric's state, both of them trying to edge closer and closer without going over. Just as they both pushed in for the last shove into climax, she turned the vibrator off. "Whoops! Out of time!" Her gleeful exclamation was met with frustrated moans, Eric's hips bucking. Apparently she'd waited a second too long, as a flow of cum dripped out of his cage. No pressure, no force, just dripping out. "Oooh, never mind. Erica wins, and oh boy, kitty boy, you lost and didn't even get the pleasure of a real orgasm. Sucks to be you."

Erica squirmed a little bit, hips shuddering, but there was no similar fall over the edge for her. That was okay. She'd be having one soon enough, and probably howling for mercy shortly after. But there was time for both. "You just sit tight, girl. I'm gonna get your brother all done up so he can enjoy being punished. Then you can enjoy your reward.

On the up side, as far as Eric was concerned, the chastity cage came off. Tying his tail to his collar wasn't so great for him, though. The eventual arrangement was sure to play havoc with him, too. She arranged him on all fours, mounted a big, big dildo on the wall in front of him, and put the tip in his mouth. Then a tight little cock sleeve mounted for him, too.

"You're going to fuck that sleeve until I tell you to stop, Eric. If you gag and choke very nicely for me, I'll tell you to cum. If you cum without being told, you're going to really, really regret it. Understood?" The cat nodded. "Good! Go to it while I get your sister ready.

As the boy started to work his way back and forth, pushing and pushing to get far enough onto the dildo to actually get his dick in the sleeve, Erica shivered in anticipation. She didn't have to wonder long, as the Sybian came out, and the harness attachment was clipped in place. She didn't object or struggle while she was being strapped in, locked on top of the thing with no room to squirm her hips more than a little, certainly not enough to get away from the motor that would soon be humming away. And a different little gag, with a short, thick cock in her mouth, and a bigger, knotted one outside.

Just right for mounting the little cat's face, which Vanessa did without much worry or ceremony. Angles were a little difficult, she didn't want to hurt Erica's neck at all, so she was bent forward, legs splayed, and using a grip on the girl's collar to give her something more steady to grind against. And that was about time to turn on the Sybian. No preamble, no warmup, straight to high, and the muffled yelp behind her made her grin. She had the best spot in the room, riding one face and watching the other in frustrated discomfort as he tried to keep his throat stuffed long enough to do more than edge himself along, but it wasn't working. If he could bend his back a little, he'd have had a chance, but the tail to collar connection forced him to stay mostly straight.

It was easy to forget time, like that. Erica howling and shuddering through orgasm after orgasm, growing from pleasure to unbearable overstimulation. Eric humping futilely at the sleeve, trying to get himself close enough to beg for release, but unable to keep at it long enough to get there. And she was busy grinding at the cat girl's face, other hand rubbing her clit as she worked her way on and off the knot at the base of the toy. Some of her juice joining the drool on the cat's chin, as if she wasn't already a complete mess.

Oops, maybe too much a mess. She recognized the wild, desperate look in the girl's eyes, and undid a quick release on one of Erica's straps. It didn't free her, just let her lean back to get over sensitive bits away from the direct vibrations. After a moment, Vanessa mouthed 'you okay?' to her, and after a nod, went back to grinding away. Eric didn't need to know his sister had been given a reprieve. In fact...

"Boy, I'm not going to let your sister loose until you cum, so if you want her to stop being in hell, you better put some effort in." She saw wide eyes over there, too. A good sign, he was definitely the more compassionate of the two, and would put himself through a lot to relieve her. Even if she didn't actually need it.

In the meantime, Erica kept bobbing her head, working her neck, pushing and pulling that nice, thick toy, much to Vanessa's delight. It left her free to focus on watching the boy struggling with his predicament. He could get his dick into the sleeve, but only by stuffing his throat with the dildo, and it was too thick for him to be able to breathe with it in place. And he could only choke and gag around it for a handful of seconds before he had to pull back to gasp a breath. She could tell he was starting to get close, though. It was easy to tell with him, the scrawny thing. She could read it in the way his stomach tensed, the way his hips shuddered. When she was pretty sure the next round was going to do him in, she pushed Erica back in place, to a renewed yowl of dismay. Still muffled, of course. Wouldn't do to have her not be truly, deeply grateful for her brother's self-sacrifice.

Eric pushed again, stuffing his throat full of cock, gagging and struggling. He got himself in the sleeve again, and frantically moved his hips as much as he could. Finally caught, too, and the bucks went from desperate to euphoric as he spent himself into the sleeve before pulling back to gasp air, coughing and shuddering, cock spurting a few last drops onto the floor. And as promised, once he was all done, she turned the Sybian off. Both of the cats needed a little bit of recovery time, time to catch their breath before any movement. All Vanessa did, for the moment, was take Erica's gag off, and unmount the dildo in front of Eric. She stood by, waiting to see whether they needed additional help.

They didn't, at first, but Eric mumbled something, and when she went over to check on him, slumped against her leg. "Easy boy, easy." Not much to undo, just cuffs at wrist and ankle, and she pulled him into a sit on the floor, leaned against her. "Take a breath, slow. You need some water." Every one of the rooms had a concealed mini fridge, and she left Eric sprawled on the floor while she got a couple bottles. Once he had one, and was moderately coherent, laying on the floor, she undid Erica, and got her into a similarly relaxed position. Then sprawled on the floor next to them.

Conversation was mumbled and slow, none of them worried much. Some discussion about how things could have gone, if Eric had won the initial challenge. Casual fondling, lots of contact and caressing. Kissing too, however rough she treated them, there was plenty of affection going on, they'd been friends for a few years, and this wasn't the first time she'd pushed them hard.