cock rings, anal, watching, double penetration, puppy/master, collar+leash

NOTE: I wrote this in a feverish, bored out of my mind haze at 2am. It makes no sense to me either.


Music echoed off the vaulted ceilings, filling the building with a mess of noise. There were people shoulder to shoulder and wall to wall, all of them jumping and swaying in time with the music. Owen shoved through the crowd of bodies to the bar, and flagged down Marcus. When Marcus saw him, his eyes widened and he dropped the drinks he was serving. He looked like he had seen a ghost.

"What are you doing here?" He mouthed, looking surprised.

"I'm looking for Jester!" Owen shouted, and Marcus shook his head. "Please." Marcus's shoulders sagged and he looked at Owen apologetically. He gestured to a large doorway on the other side of the room. "Thank you!" Owen turned and barreled through the crowd. He reached the door, which was covered by a large red curtain, and was stopped by a large man in a suit. "I'm looking for Jester!" Owen said, and the man furrowed his brow.

"Name."

"Owen!" He stepped to the side and parted the curtain, letting Owen pass.

"Top floor." He said as he passed.

There was a large atrium, full of couches, all of which were occupied by people. The air was thick with smoke, and the lights were low. Everything was red and gold, and silhouettes of people flitted around the room, hazy in the smoke. There was a large space where all the floors above were visible, the balconies spiraling for what looked like dozens of floors. Straight ahead, there was an elevator, and Owen ran towards them. The ride to the top was faster than he expected, and he froze when he stepped out of the elevator. There was a large set of double doors in front of him, and they were cracked open. Red light spilled out, and Owen took a breath and opened up the doors.

The room was bathed in red light, and black swaths of fabric hung from the walls. There were couches lining the walls, and there was a large, overstuffed chair on the far wall across from the doors. There were people all over the floor, rolling around with each other on the hardwood floor and plush carpets strewn about. There was a sickly sweet smell permeating the air, and Owen's head started to spin. In the overstuffed chair was someone, but he couldn't make out who. They had a woman in lingerie on their lap, her shoulders hiding the person's face.

"J-Jes?" Owen coughed out. The smoke was making it hard to breathe. The woman climbed off the chair and sat on the floor next to it. When she saw Owen, she smiled and waved. June. Owen ignored her, praying she wouldn't talk to him. Jester got out of the chair and smiled, walking toward him. They were wearing tight high waisted pants and a white button down, unbuttoned with the sleeves rolled up.

"Hi, starshine." They said. Their voice was quiet but it rang in Owen's ears.

"W- what's going on?" Owen sputtered. He was having trouble thinking straight. Jester held his cheek and smiled.

"This is where I like to come when I'm bored." They smiled and shrugged. "But I'm still kinda bored, honestly." They pulled his face closer and kissed his neck. "Want to help with that?" Owen shivered, and he nodded slowly. "Good boy." Jester sat back down and smiled. "Strip." Owen obeyed, pulling off his clothes until he stood naked in front of Jester.

They raised their hand and beckoned him forward. Owen got on all fours and crawled toward them, stopping and sitting at their feet. They smiled and held their hand out. June put a collar and leash in their hand, and they reached down and tightened it around his neck. Owen leaned into their touch, nuzzling their hand.

"Undress me, puppy." Owen gently unbuckled their belt and pulled their pants off, tossing them to the side. They weren't wearing underwear, and their pussy shone with wet. They pulled off their shirt, and let their tits fall against their chest, enjoying the way Owen watched.

"M-master?" Owen said, looking up at them with wide eyes.

"Yes, puppy?"

"Why are you here? Am I not good enough?" Jester smiled and put their foot on his shoulder, pushing his shoulder back and pulling the leash. Owen whimpered, and they leaned down.

"No, puppy, you're not." They said. Owen whined, and they gently licked up his jaw and bit his ear. "But I can make you better." They said, dragging his ear between their teeth. "Teach you to obey me." They pulled away and took their foot off his shoulder and held it in front of his face. He licked the bottom of their foot, and wrapped his lips around their toes, sucking gently. Jester shivered as he ran his tongue over each one. Drool dripped down Owen's chin and onto his chest, mixing with the sheen of sweat. His head was spinning, all he could think about was Jester. They pulled their foot away and put it back on his shoulder, his spit running down his back. "Turn around and get on all fours." Owen did, putting his face to the floor and arching his back, sticking his ass into the air. He heard them open a drawer, then felt them use one hand to spread his ass cheeks. They pressed something warm against his hole and pushed.

"FffuUCK!" Owen cried as the plug stretched him out. He whimpered incoherently as his hips bucked, unable to think about anything but the way it shifted inside him as he moved. Jester pressed their thumb against the handle, pressing it gently. "Aahnn..ngh! D-don't stop!" Owen moaned. His toes curled and his tongue lolled, drool dripping onto the floor. A loud smack echoed through the room as they brought their hand onto his ass, leaving a burning red hand print.

"You don't tell me what to do, puppy." Jester said. They pulled the collar, forcing Owen to arch his back. "I don't care what you want, you are my fuck toy. You do what I want." Owen pulled against the collar, gasping for air.

"Y-yes master." Jester let the leach slacken, and Owen collapsed back onto the floor. His dick hung between his legs, hard and throbbing. Jester wrapped their fingers around it and slowly stroked, enjoying all the little whines and whimpers Owen was failing to hold back. Jester stopped, and Owen had to bite back a whine of protest.

"Lean back against the chair, puppy." Owen obeyed, keeping his hands on the ground behind him for support. He spread his legs, and Jester smiled. He looked so cute and vulnerable like that. His cheeks were flushed, and his eyes unfocused. His cock twitched between his legs, and he whimpered. He knew he couldn't ask for it, but he was so fucking desperate for them to touch him. Jester reached to the small table next to the chair again, and pulled a smooth silver cock ring out of the top drawer.

"Nnnoooo, mas-" Jester grabbed his face, digging their nails into his cheeks. Owen's stomach sank.

"Excuse me?" Owen shook his head, eyes wide.

"I-I'm sorry! I didn't mean to talk back, master, I'm-" Jester yanked the leash and pushed him so his back was to them, and he was facing the chair, his ass up for them. He heard them grab something else, and felt pain erupt across his ass as they hit him with a belt. He buried his face into the cushion of the chair as they hit him once, twice, three times. They pulled the leash, pulling his head back.

"Let me hear you, I want to hear how sorry you are." They hit him a fourth time, and he yelped.

"I-I'm sorry master! I'm sorry I talked back!" Jester hit him again, and bruises started to spread down his thighs. "It won't happen again! I swear, master!" Jester stopped and sat back. His body was shaking, and sweat was dripping down his arched back. Long, swollen red stripes stood out against his skin, and the bruises were getting darker.

"Good. It had better not." They tossed the belt to the side and grabbed the ring. "Turn around." Owen did slowly, his ass aching as he put his weight on it. Jester slid the ring down his cock, and Owen let out a short breath. Jester continued stroking with one hand, and gently ran their hand over his thigh with the other. They sped up, and Owen jumped a little. They leaned down and wrapped their lips around the head, sucking gently as they jerked him off. His legs started to tremble, and every muscle in his body was tense. His asshole twitched around the plug, every shift in his weight made it press against his prostate.

"M-masterrr.." Owen whined, his head lolling back. "It-ffUCK! Nnh! It feels really good!" Jester stopped immediately, and Owen lifted his head to look at them.

"I should be getting something too, shouldn't I?" Jester said, smiling. Owen nodded, and leaned forward. Jester put a hand on his chest. "Not from you, puppy." They snapped their finger, and from the mass of bodies behind them, someone stood and walked forward. He was tall, with long black hair, and a white mask covering the top half of his face. Seeming to ignore him, Jester got back on their knees and leaned down, gently licking Owen's dick. They arched their back and spread their legs, and the man got on their knees behind them. Owen whimpered as he watched him grab their ass and start thrusting into them, the wet sounds of him inside of them echoing through the room, louder an any of the noise the people behind them were making. Jester moaned against his cock, eyes rolling back as they took Owen into their mouth and started bobbing their head. They gripped his thighs, digging their nails into the soft skin.

Jester's head bobbed in time with the man's thrusts, their moaning sending vibrations down Owen's cock. Jester could feel it throb against their tongue as they rubbed gentle circles against the base. They pulled away and gasped for air, moaning loudly.

"Fffuucking-aahn! Fucking hell!" They screwed their eyes shut and furrowed their brows. "Fuck, that feels good." They pushed against Owen's legs, moving their body in time with the man.

"B-better than me, master?" Owen whimpered. Jester smiled and moaned.

"Fuck, yes. So much better." They moaned, looking through their lashes at him. Owen watched their tits bounce as they were fucked, watched the man dig his nails into their ass and leave dark red crescents on their pale skin. They took a breath and leaned back down, continuing to suck Owen's cock.

Owen couldn't keep his hips from bucking against Jester, fucking their mouth erratically. They gagged as his cock went down their throat, their neck bulging with every thrust. They gurgled around him and pulled away, drool pouring out of their mouth. Their tongue hung out and their eyes rolled back as the man sped up, making loud, wet sloshing sounds.

"I'm-Aaahn! I'm gonna cuuum!" Jester moaned loudly, and their hips bucked against him. He gripped their ass and buried himself into them, throwing his head back and moaning. He pulled out and walked away, and Jester sat back onto their heels. Owen stared between their legs, watching a mixture of their cum and his drip out of them and onto the floor.

They took a second to breathe, their chest rising and falling with every shaky breath. Owen sat forward, and put his hands between his knees.

"Master?" He asked quietly, heart racing. Jester looked up and raised an eyebrow.

"Yes, puppy?" Owen looked at his knees, and fidgeted with his hands.

"Would you like me to clean you up?" Jester smiled and leaned back, their hands behind them. They spread their legs, and a rope of cum stuck to their thigh.

"Yes, puppy." Owen got on all fours and leaned down, gently lapping up the cum off the floor. He gently put his hands on their thighs and spread them a little more. They didn't stop him. He gently licked their slit, savoring the taste. He slowly ate them out, his tongue sloshing inside of them. The smell filled his nose and his dick twitched between his thighs, throbbing against the ring. They moaned quietly and threw their head back when he gently licked their clit. "Fffuck, puppy." They moaned. "Don't stop." He wrapped his lips around the swollen nub and started to suck, enjoying the noises they were making. They laid back onto the ground and lifted their legs, squeezing his head between them. Owen's head ached as they squeezed, keeping his face close and nearly suffocating him.

He could feel their legs trembling, and their grip on his hair tightened. He sped up, and they moaned his name, their hips bucking. He kept going as they came, their pussy squirting cum all over his chin and chest. Once their body stilled and they let their legs part, he sat back and but his hands between his legs.

They sat up and smiled, leaning forward and kissing him, licking their cum off his lips. He gently put his hands on their waist and pulled them in. They sucked on his bottom lip gently, and he whined when they bit down. He felt them shift, and they snapped their fingers. Owen looked up, and someone else was already behind them, reaching for their thighs. Owen's head was swimming, and he didn't bother to look too closely at him. Jester moaned against Owen's mouth, and they gripped his shoulders. The man behind them gripped their thighs, and thrust into them.

"F-fuck!" They cried, scratching deep cuts into Owen's shoulders. He started fucking them, pushing them against Owen. "Yes! Fucking stretch my asshole! FuuUCK!" They cried, eyes rolling back.

"Master?" Owen said, quietly. "Does he feel better than me?" Jester looked as Owen and laughed.

"So much fucking betterrrr" They said between moans. It took them a lot of effort to make a coherent sentence. "He's so much bigger, puppy." Owen Grabbed their hips and shifted his weight, the tip of his cock pressing against their slit. They looked up at him and smiled. "Are you that desperate, puppy? Do you -nnh! w-wanna show me you're better than h-he is?" Owen nodded.

"Yes, master." Jester nuzzled his neck and lowered themselves onto him, the man behind them slowing his thrusts. Jester arched their back and moaned, throwing their head back. They leaned back onto him and Owen watched as he reached around and played with their tits while they rode their cocks. Their stomach was bulging, and Owen could feel them stretching around him. They moaned and leaned into his touch as they ground their hips.

"Keep fucking going." They ordered, and the two men on either side of them obeyed. Owen grabbed their hips and Started thrusting in time with the other man. Owen reached between their legs and pressed their clit gently, rubbing slow circles around it. He could feel it throbbing against his fingers. They screamed a string of incoherent profanity as they came, their body shaking and their hips bucking. The man behind them slowed and pulled out, his cum dripping out of them and onto the floor. Jester collapsed against Owen, breathing heavily. He gripped their ass and kept thrusting, grunting quietly as his vision swam.

"M-masterrr" He mumbled. "C-can I take the ring off?" Jester leaned back and stood, leaving Owen on the floor, his hips bucking in protest. They grabbed the leash and tugged.

"Get up." They sat back into the chair and crossed their legs. Owen stood, his knees threatening to buckle beneath him. "Go ahead and take it off for me." He tugged it off and tossed it to the side. "Now get on all fours facing away from me." He turned and shakily got onto the floor, arching his back for them. They reached forward and pulled on the plug. Owen moaned, and swayed his hips against their hand. Jester pulled it out gently, and Owen's hips bucked. He bit the inside of his cheek, trying not to moan. He heard them reach into the drawer again, then put something on. Owen felt something press against his asshole, and he flinched. Jester put their hand on his back, and pushed gently. The strap they were wearing was bigger than he was used to, and he couldn't suppress a helpless moan as it stretched him out.

"Master, it's too biggg" Owen groaned, his toes curling. Jester pulled the leash, yanking his head back and pressing against his throat. He gasped for air, and Jester sped up their thrusts, slamming into Owen's asshole as hard as they could. Owen's eyes rolled back and he screamed Jester's name, over and over like a prayer. Jester pulled out and slapped his ass, spitting on him. Owen shivered, their spit dripping over their asshole.

"On your back." They ordered. Owen rolled over and spread his legs, holding his knees to his shoulders. His face was red and his body shone with sweat. His cock was swollen and throbbing and his gaping asshole was twitching, begging to be filled. Jester slid the toy back into him, and wrapped their hand around his dick. They jerked him off in time with their thrusts, relishing the moans and mewls Owen was making.

"Master, I-nnnh! I'm close!" Jester smiled and sped up, the wet smacking of their hips against his swollen ass filling the room.

"Cum for me, puppy." Jester said, using their free hand to pull the leash taught and force Owen to sit up. His eyes were rolled back and his mouth was open wide, drool dripping from his tongue onto his chest. They spit into his mouth, and he whimpered, playing with it with his tongue before swallowing it. His thighs trembled and his muscles tightened as he got closer. "Make a mess of yourself, like the disgusting little whore you are. Cum while I fuck you senseless, while I use your body for my own entertainment. C'mon puppy." Owen's back arched and he screamed, ropes of cum squirting out of his throbbing cock and all over his chest and face. Jester pulled out slowly, but kept stroking him as he came, covering their hand with his mess.

Owen collapsed onto the floor, and Jester tugged off the strap on, giving him a second to breathe.

"Baby?" Owen said, sitting up shakily. Jester sat next to him and he leaned against them, head spinning. "I love you." Jester smiled, and helped him get up and sit in the chair.

"I love you too." They said, and leaned in. They gently licked his cum off of him, playing with it in their mouth while they did. They used their fingers to wipe some off his chest, and held it out for him. He wrapped his lips around their fingers and sucked gently, swirling his tongue around their knuckles. "Good boy." They said, and climbed onto his lap.

They nuzzled his neck and stroked his hair gently, the two of them listening to each other breathe.