Kinktober Day Twenty-Nine: Gloryhole

Story by KarlyCommissions on SoFurry

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#20 of Kinktober 2018

Caroo the kangaroo has found himself trapped against a one-way mirror, with a wolf Mistress who had quite the odd fetish for torturing the poor roo on the other side.


Kinktober Commission for Caroo


Everything was a blur, and Caroo knew something was wrong the moment he woke up -- it wasn't because he wasn't tucked under warm blankets, and it wasn't because he was standing up instead of laying down.

His balls ached something fierce, and when he tried to reach down to see what was wrong, he smacked his face and hands against glass. The loud thunk was what caused him to open his eyes, and the bright light that was shining down on him like a spotlight made him blink rapidly, trying to regain his focus.

At first, he had to assume that he was dreaming -- after all, there was no other reason for him to be stuck in a piece of glass with no way out. More than that, whatever had him stuck there had his balls trapped in a vice-like grip, so there was no real struggling, and no real getting out; if he did much, he was afraid he'd rip his 'little roo and pals' straight from his body. He probably should have been more afraid, or at least more worried about what was happening... and he probably would have been, if he weren't so shocked with how strange the entire circumstance was. He was close enough to the flat surface that his breath fogged and left a puff that obscured his vision. He wanted to squirm, wanted to attempt to free himself from his odd restraints... but the worry that he would end up hurting himself trying to remove his body from the glass was enough to give him pause.

Instead, he drew a deep breath and then let his voice carry as loudly as he dared. "Hello?" The sound of his word echoed around the obviously empty room. In front of him, there was a solitary red door, and a plush seat positioned in front of the glass on the other side. It was almost like the room was waiting for something or someone that wasn't him... and Caroo couldn't stop the nervous feeling that began squirming like a living thing in his gut. Something wasn't right here.

"Hello?" He called out again, his voice a little louder this time. He wasn't sure who he was calling for -- his mind was beginning to wake up, and it was telling him that someone had obviously put him here... so the person that he was calling for was more than likely the same person who plucked him from his bed and brought him to wherever in the hell he was... but still, he couldn't simply stand there and do nothing. He squirmed back and forth, but the bar at his chest that had kept him from falling when he was asleep and the feel of the glass pressing against his balls and cock was enough to put a quick halt to the moment. Instead, he brought his hands down and tugged at the restraint across his torso in a careful motion; it didn't budge, or creak, or act like it was going to give way at all.

Unless he figured out some trick to it, there really didn't seem to be much that he could do, and looking around caused the kangaroo to realize that the latches for the bar holding him in place were on the other side of the mirror and completely inaccessible to him in his current state. Still, there had to be something that he could do.

He opened his mouth to shout out another cry for help, or attention, or at least the knowledge that someone else was there... when a light flicked on beneath the slit at the base of the red door... and then with a small screeeeeek, it swung open.

The woman that stepped through gave Caroo pause. She was tall, busty, older -- a complete MILF, if she had any children... and the wolf's red hair was carefully pulled back from her visage. She stalked forward in stiletto heels that came to her thighs, and took a seat in the chair in front of her. With a slow grin, she leaned in close and Caroo's voice rang out.

"Hey, excuse me?" His hand knocked on the glass, and though her eyes tracked up to where the sound had come from, she was still leaning into the glass -- it took him a moment to realize that she wasn't staring at his torso... but fixing the carefully coiffed strands of her hair; it wasn't glass.

It was a one-way mirror, and he was the only one who had a view... which meant that the only part of him that she could see was his cock and balls on display like some kind of fucked up trophy.

After a moment of primping her reflection, her eyes trailed downward to the aforementioned member, and she brought one finger up to stroke along the top of his shaft in delight -- of its own accord, Caroo's body jerked. He wasn't sure if it was all his pleasure, or if they'd done something to him to make him more responsive... but a small sound jerked from his throat before he brought his attention back to the problem at hand.

"Hey, who are you?" His question was half shouted through the glass, and it was only the small quirk of a smile at the corner of her crimson lips that let him know that she'd heard what he'd said at all. Clearly, she wasn't interested in answering his questions, or giving him any kind of answer at all for what was going on. Instead, she leaned in close and let her warm breath play sweet heat over his length until he was hard and aching, though he hated the fact that he was. He didn't want to respond to her unsolicited touches, but he seemed completely and utterly incapable of stopping his frame's reaction... and she seemed completely and utterly delighted with the way that he was responding to her. Her green eyes burned with delight, with utter satisfaction and desire for the twitching cock in front of her, and the way that Caroo let out another helpless moan as she finally brought her hand forward and wrapped gloved digits around his base to give a quick pump.

His entire body jerked, and his cock twitched so hard that he felt it jerk in her fingers. She let out another delighted laugh, curling into a purr of a low moan with her delight at the situation. She licked her lips and leaned forward, so that her breath was playing warm and damp against the head of his prick as she slowly began to pump him as though she was warming up the engine of a car.

He let out another low moan, a whimper of desperation at the fact that he didn't want this to happen -- that he was being used, and the person who was doing it didn't even see him on the other side of the mirror. It was a clearly unhappy sound, wrapped around a base of pleasure that he would have rather ignored, and she seemed to get off on it to the point that she had to shift forward, cross her legs and press her thighs together as a low sound of satisfaction spilled from her throat.

She was getting off on this -- whether it was the anonymity, or the simple fact that Caroo was twitching, helpless, and both enjoying and hating every moment of what was happening... she was enjoying herself far more than she should have. The kangaroo wanted to burst into flames, or melt onto the floor...

Instead, he had to attempt to bite back another moan as she lowered her head and brushed her

lips back and forth across the tip of his cock while pumping him slowly, until he could feel orgasm building and burning inside of him, squeezing his balls tight and threatening to flood forward.

"S-stop!" He stammered the words out, banging his fists against the glass again. He knew that she heard him, and she actually let out a low chuckle before she lowered her head and drew his cock into her mouth, sucking him down hungrily while she shifted her fingers to tickle torture at his balls until Caroo could no longer stand it.

She pulled back, leaving smears of her red lipstick on his prick just as he blew his load in what was surprisingly... a slow trickle.

The pressure of the glass around his cock and balls was the ultimate cock ring -- what should have been his entire load of cum was just a few small spurts that, much to his horror, left him hard and aching.

"Oh, God..."

He moaned the words out as the grin on the wolf's face broadened, and she leaned forward and pulled a feather from her boot.

"That's right -- did you think we were anywhere close to finished yet, Caroo?" She said his name slowly, deliberately, the word being uttered a clear sign that she knew who he was... and she was the reason that he was there in the first place. "Oh, no, we're only just getting started." And there was a warm promise in her voice that told Caroo he wasn't going to enjoy anything from here on out any more than he had to begin with. He let out another low groan, and then squirmed and whimpered as she brought the feather to the tip of his prick and started to dance the soft edges of it slowly along his still sticky tip. The pleasure and teasing were heady, enough that he could have jumped out of his skin just from the sensation of it -- she watched him now, though, her green hues very careful. His first orgasm had been a simple demonstration of the fact that he wasn't going to be able to blow his load and find himself unable to perform... but now, the wolf seemed completely intent on making sure that he realized he wasn't going to get to come at all -- at least, not easily.

She tickled and teased, playing the feather along his tip, his shaft, brushing it between his balls and then sliding her hand along his base until he was trembling and twitching and writhing with it, until he watched his pink head flush to a darker color with his impending orgasm...

And then, she stopped. She sat back on the plush chair and folded her hands into her lap -- though she couldn't see his face, she raised her eyes up and arched one brow, tilting her head to the side and grinning.

"I don't think so, little roo. This is far too much fun for me." The orgasm that was beating and burning at the edge of his senses stayed there, caught in his throat, in his veins, trapped in his clenching balls until Caroo was writhing and twisting with it, suffocating on it, until he could hardly think around it.

"I'm going to make sure that this is all you ever have -- need, want. I'll keep kidnapping you, little kangaroo, and keep teasing your cock while you're helpless." She leaned in close, letting her breath play along his length, keeping him on the edge of orgasm. "I'll put your prick into a milking cage and make you my pet. Would you like that?"

"No!" His voice was strained, his body was burning.

"I couldn't hear you -- if you would, why don't you show me with some cum?" And she stroked her hand along the length of him -- the orgasm that he'd been wanting so badly was suddenly the last thing that he wanted to give. He growled and groaned with it, but it couldn't stop the small burst of cum and the mindblowing pleasure that sizzled through him -- his involuntary yes was more than enough for the wolf. She grinned, and then instantly brought her mouth to him again. This time, she popped just the head of him between her lips, and encircled his shaft with one hand while cupping his balls in the other. There was no reprieve -- no mercy. She made him cum -- and then made him cum again... she milked him until he lost count of how many times his balls squeezed tight and attempted to empty their load, until his head was spinning and he couldn't catch his breath.

It felt like it had gone on for hours, and Caroo honestly wasn't sure how much longer he was going to be able to hold on to his sanity, let alone consciousness. When the wolf, whose eyes were shining with lust and whose shorts had soaked through with her own pleasure by now brought her hand up to encircle his shaft again, he whimpered out.

"Please, no more. Please... oh, please..."

"Shhh... you know you want this." Her first indication of the fact that she could hear him, and clearly -- and that she didn't care what she heard. She pumped his shaft hard and fast this time, and brought her eyes up to raptly focus on the mirror; she watched herself milk him while she stuck her own hand down her shorts, and this time she fucked herself while she fucked him... and Caroo knew that he was damned to this... damned to her whim.

She started to whimper, buck her hips, writhe... she ground her leather shorts against his tip, bringing even more pleasure with her fluid drenched core, while her hand continued to rock and work against him... until he could feel it again -- orgasm building up, threatening to spill over, threatening to milk out one slow, lingering, torturing drop at a time...

His heart thundered, his body ached... and as the sensation burst through him and the wolf threw back her head as her own orgasm overwhelmed her... Caroo couldn't hold on any longer. The kangaroo felt himself slip -- felt his vision fade... there had been too many orgasms, too much stress and strain, too much pressure and pleasure on his body. He lost consciousness to the sight of the wolf Mistress panting, cumming... and to the sound of her aching, pleasured moans that were all there for the fact that she'd been relentlessly torturing him for the past...

However long.

--

He woke slowly. His eyes felt glued shut; his body ached. For a moment, Caroo jumped with a start... and then he felt his sheets slide from his chest.

Relief flooded through him -- had it all been a dream after all. His hands came up instantly; there was no glass, there was no restraint. He was in his bed, in his home... in the familiar lighting of his room.

He let out a soft laugh and pushed the sheets back - his eyes trailed down his body, and something in his gut clenched.

There, pressed to his hip was a single, crimson lipstick print. And written across his light fur were the words.

"Be seeing you soon."